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Synthesis and structures of six closely related N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides, together with an isolated reaction intermediate: Order versus disorder, molecular conformations and hydrogen bonding in zero, one and two dimensions.

DOI: 10.1107/S2053229618000657

Source and publish data:

Acta Crystallographica Section C: Structural Chemistry p. 203 - 211 (2018)

Update date:2022-08-29

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Authors:

Sagar, Belakavadi K.Sagar, Belakavadi K.

Yathirajan, Hemmige S.Yathirajan, Hemmige S.

Rathore, Ravindranath S.Rathore, Ravindranath S.

Glidewell, ChristopherGlidewell, Christopher

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Article abstract of DOI:10.1107/S2053229618000657

Six closely related N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides have been synthesized and structurally characterized, together with a representative reaction intermediate. In each of N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide, C

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Full text of DOI:10.1107/S2053229618000657

research papers  
Synthesis and structures of six closely related  
N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-  
arylamides, together with an isolated reaction  
intermediate: order versus disorder, molecular  
conformations and hydrogen bonding in zero,  
one and two dimensions  
ISSN 2053-2296  
Received 8 January 2018  
Accepted 10 January 2018  
Belakavadi K. Sagar,a Hemmige S. Yathirajan,a Ravindranath S. Rathoreb and  
Christopher Glidewellc*  
Edited by A. L. Spek, Utrecht University, The  
Netherlands  
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India, bCentre for  
Biological Sciences (Bioinformatics), School of Earth, Biological and Environmental Sciences, Central University of South  
Bihar, Patna 800 014, India, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.  
*Correspondence e-mail: cg@st-andrews.ac.uk  
Keywords: synthesis; thiophene derivatives;  
amides; reaction mechanism; crystal structure;  
disorder; molecular conformation; hydrogen  
bonding; supramolecular assembly.  
Six closely related N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides  
have been synthesized and structurally characterized, together with a repre-  
sentative reaction intermediate. In each of N-[3-(2-chlorobenzoyl)-5-ethylthio-  
phen-2-yl]benzamide, C20H16ClNO2S, (I), N-[3-(2-chlorobenzoyl)-5-ethyl-  
thiophen-2-yl]-4-phenylbenzamide, C26H20ClNO2S, (II), and 2-bromo-N-[3-(2-  
chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide, C20H15BrClNO2S, (III), the  
molecules are disordered over two sets of atomic sites, with occupancies of  
0.894 (8) and 0.106 (8) in (I), 0.832 (5) and 0.168 (5) in (II), and 0.7006 (12) and  
0.2994 (12) in (III). In each of N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-2-  
iodobenzamide, C20H15ClINO2S, (IV), and N-[3-(2-chlorobenzoyl)-5-ethylthio-  
phen-2-yl]-2-methoxybenzamide, C21H18ClNO3S, (V), the molecules are fully  
ordered, but in N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-2,6-difluorobenz-  
amide, C20H14ClF2NO2S, (VI), which crystallizes with Z0 = 2 in the space group  
C2/c, one of the two independent molecules is fully ordered, while the other is  
disordered over two sets of atomic sites having occupancies of 0.916 (3) and  
0.084 (3). All of the molecules in compounds (I)–(VI) exhibit an intramolecular  
N—Hꢁ ꢁ ꢁO hydrogen bond. The molecules of (I) and (VI) are linked by C—  
Hꢁ ꢁ ꢁO hydrogen bonds to form finite zero-dimensional dimers, which are cyclic  
in (I) and acyclic in (VI), those of (III) are linked by C—Hꢁ ꢁ ꢁꢀ(arene) hydrogen  
bonds to form simple chains, and those of (IV) and (V) are linked into different  
types of chains of rings, built in each case from a combination of C—Hꢁ ꢁ ꢁO and  
C—Hꢁ ꢁ ꢁꢀ(arene) hydrogen bonds. Two C—Hꢁ ꢁ ꢁO hydrogen bonds link the  
molecules of (II) into sheets containing three types of ring. In benzotriazol-1-yl  
3,4-dimethoxybenzoate, C15H13N3O4, (VII), the benzoate component is planar  
and makes a dihedral angle of 84.51 (6)ꢂ with the benzotriazole unit.  
Comparisons are made with related compounds.  
CCDC references: 1816131; 1816130;  
1816129; 1816128; 1816127; 1816126;  
1816125  
Supporting information: this article has  
supporting information at journals.iucr.org/c  
1. Introduction  
2-Amino-3-benzoylthiophenes can act (Aurelio et al., 2010) as  
allosteric enhancers at the A1 adenosine receptor, whose role  
in obesity and diabetes has been reviewed fairly recently  
(Dhalia et al., 2009). More broadly, thiophene derivatives have  
been found to exhibit a wide range of biological properties,  
including analgesic activity (Cannito et al., 1990; Molvi et al.,  
2007), anti-inflammatory activity (Cannito et al., 1990; Asha-  
latha et al., 2007; Molvi et al., 2007), antimicrobial activity  
(Ashalatha et al., 2007; Rai et al., 2008) and nitric-oxide-  
# 2018 International Union of Crystallography  
Acta Cryst. (2018). C74  
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Sagar et al.  
Six closely related arylamides 1 of 9  
research papers  
scavenging activity (Molvi et al., 2007). Based on these ob-  
servations, particularly the first, we have now synthesized and  
characterized a series of closely related arylamides derived  
from 2-amino-3-(2-chlorobenzoyl)-5-ethylthiophene, namely  
N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide, (I),  
N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-4-phenylbenz-  
amide, (II), 2-bromo-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-  
2-yl]benzamide, (III), N-[3-(2-chlorobenzoyl)-5-ethylthio-  
phen-2-yl]-2-iodobenzamide, (IV), N-[3-(2-chlorobenzoyl)-5-  
ethylthiophen-2-yl]-2-methoxybenzamide, (V), and N-[3-(2-  
chlorobenzoyl)-5-ethylthiophen-2-yl]-2,6-difluorobenzamide,  
(VI). Compounds (I)–(VI) were all prepared using conden-  
sation reactions between 2-amino-3-(2-chlorobenzoyl)-5-  
ethylthiophene and a substituted benzoic acid in the presence  
of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide as dehy-  
drating agent and 1-hydroxybenzotriazole as the acyl carrier  
using 3,4-dimethoxybenzoic acid, but omitting the addition of  
2-amino-3-(2-chlorobenzoyl)-5-ethylthiophene, yielded (VII).  
¨
(Konig & Geiger, 1970) (see Scheme 1). We have also isolated  
and characterized the reaction intermediate benzotriazol-1-yl  
3,4-dimethoxybenzoate, (VII), by the straightforward expe-  
dient of stopping the reaction sequence before the addition of  
the aminothiophene reactant, confirming this aspect of the  
proposed mechanism. We report here the molecular and  
supramolecular structures of compounds (I)–(VII).  
2. Experimental  
2.1. Synthesis and crystallization  
2-Amino-3-(2-chlorobenzoyl)-5-ethylthiophene was a gift  
from RL Fine Chem Pvt Ltd, Bengaluru, India. All other  
reagents are available commercially and were used as  
received. For the synthesis of compounds (I)–(VI), 1-[3-(di-  
methylamino)propyl]-3-ethylcarbodiimide (173 mg, 0.9 mmol),  
1-hydroxybenzotriazole (126.32 mg, 0.825 mmol) and tri-  
ethylamine (0.5 ml, 3.75 mmol) were added to a solution of the  
appropriately substituted benzoic acid (0.75 mmol) (see  
Scheme 1) in N,N-dimethylformamide (DMF, 5 ml) [i.e.  
benzoic acid for (I), biphenyl-4-carboxylic acid for (II),  
2-bromobenzoic acid for (III), 2-iodobenzoic acid for (IV),  
2-methoxybenzoic acid for (V) and 2,6-difluorobenzoic acid  
for (VI)] at 273 K and the resulting mixtures were stirred for  
20 min at 273 K. A solution of 2-amino-3-(2-chlorobenzoyl)-5-  
ethylthiophene (200 mg, 0.75 mmol) in DMF (5 ml) was then  
added to each of the above mixtures and stirring was  
continued overnight at ambient temperature. The reactions  
were then judged to be complete using thin-layer chromato-  
graphy (TLC). The mixtures were poured into an excess of  
water and extracted exhaustively with ethyl acetate. For each,  
the organic extract was washed first with aqueous hydrochloric  
acid solution (1 mol dmꢃ3) and then with brine, and then dried  
over anhydrous sodium sulfate and concentrated under  
reduced pressure. The crude products of (I)–(VI) were puri-  
fied using silica-gel column chromatography (60:120 mesh)  
using ethyl acetate–hexane (1:4 v/v) as eluent and crystals  
suitable for single-crystal X-ray diffraction were grown by  
slow evaporation, at ambient temperature and in the presence  
of air, of solutions in DMF. An entirely similar procedure,  
2.1.1. Analytical data. Compound (I): yield 85%, m.p.  
1
433 K; H NMR (CDCl3): ꢁ 12.99 (s, NH), 8.11–8.09 (m, 2H,  
Ar—H), 7.60–7.37 (m, 7H, Ar—H), 6.42 (s, 1H, thiophene),  
2.71 (q, J = 7.4 Hz, 2H, CH2), 1.25 (t, J = 7.4 Hz, 3H, CH3).  
Compound (II): yield 85%, m.p. 462–464 K; 1H NMR  
(CDCl3): ꢁ 13.04 (s, NH), 8.18 (m, 2H, Ar—H), 7.50–7.38 (m,  
11H, Ar—H), 6.43 (s, 1H, thiophene), 2.72 (q, J = 7.6 Hz, 2H,  
CH2), 1.27 (t, J = 7.6 Hz, 3H, CH3). Compound (III): yield  
86%, m.p. 373 K; 1H NMR (CDCl3): ꢁ 12.11 (s, NH), 7.81–7.75  
(m, 2H, Ar—H), 7.59–7.47 (m, 6H, Ar—H), 6.45 (s, 1H,  
thiophene), 2.69 (q, J = 7.4 Hz, 2H, CH2), 1.15 (t, J = 7.4 Hz,  
1
3H, CH3). Compound (IV): yield 82%, m.p. 403–405 K; H  
NMR (CDCl3): ꢁ 12.32 (s, NH), 8.00–7.98 (m, 1H, Ar—H),  
7.66–7.64 (m, 1H, Ar—H), 7.49–7.20 (m, 6H, Ar—H), 6.43 (s,  
1H, thiophene), 2.73–2.70 (q, J = 7.6 Hz, 2H, CH2), 1.26 (t, J =  
7.6 Hz, 3H, CH3). Compound (V): yield 83%, m.p. 430–432 K;  
1H NMR (CDCl3): ꢁ 12.64 (s, NH), 7.96–7.93 (m, 2H, Ar—H),  
7.61–7.48 (m, 4H, Ar—H), 7.19–7.16 (m, 2H, Ar—H), 6.39 (s,  
1H, thiophene), 2.68 (q, J = 7.6 Hz, 2H, CH2), 1.14 (t, J =  
7.6 Hz, CH3). Compound (VI): yield 60%, m.p. 410–414 K; 1H  
NMR (CDCl3): ꢁ 12.82 (s, NH), 7.89–7.77 (m, 2H, Ar—H),  
7.56–6.45 (m, 5H, Ar—H), 6.34 (s, 1H, thiophene), 2.69 (q, J =  
7.6 Hz, 2H, CH2), 1.26 (t, J = 7.6 Hz, CH3). Compound (VII):  
yield 86%, m.p. 435 K; 1H NMR (CDCl3): ꢁ 8.10–8.08 (m, 1H,  
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Table 1  
Experimental details.  
(I)  
(II)  
(III)  
(IV)  
Crystal data  
Chemical formula  
Mr  
C20H16ClNO2S  
369.85  
C26H20ClNO2S  
445.94  
C20H15BrClNO2S  
448.74  
C20H15ClINO2S  
495.74  
Crystal system, space group  
Temperature (K)  
Monoclinic, P21/c  
294  
9.7868 (9), 13.9567 (12),  
13.3764 (11)  
90, 101.816 (2), 90  
1788.4 (3)  
Monoclinic, P21/c  
296  
10.7264 (6), 9.1208 (5),  
22.9103 (15)  
90, 94.414 (2), 90  
2234.7 (2)  
Monoclinic, C2/c  
294  
18.8096 (10), 11.5021 (7),  
19.9112 (11)  
90, 118.030 (2), 90  
3802.5 (4)  
Monoclinic, P21/n  
294  
8.1813 (6), 11.8276 (7),  
20.1347 (12)  
90, 94.388 (2), 90  
1942.6 (2)  
˚
a, b, c (A)  
ꢂ, ꢃ, ꢄ (ꢂ)  
3
˚
V (A )  
Z
Radiation type  
4
4
8
4
Mo Kꢂ  
0.34  
0.25 ꢄ 0.20 ꢄ 0.20  
Mo Kꢂ  
0.29  
0.28 ꢄ 0.27 ꢄ 0.22  
Mo Kꢂ  
2.43  
0.25 ꢄ 0.20 ꢄ 0.10  
Mo Kꢂ  
1.91  
0.16 ꢄ 0.14 ꢄ 0.11  
ꢅ (mmꢃ1  
Crystal size (mm)  
)
Data collection  
Diffractometer  
Absorption correction  
Bruker Kappa APEXII  
Multi-scan (SADABS;  
Bruker, 2012)  
Bruker Kappa APEXII  
Multi-scan (SADABS;  
Bruker, 2012)  
Bruker Kappa APEXII  
Multi-scan (SADABS;  
Bruker, 2012)  
Bruker Kappa APEXII  
Multi-scan (SADABS;  
Bruker, 2012)  
Tmin, Tmax  
0.864, 0.934  
26489, 3726, 2092  
0.929, 0.939  
24401, 5148, 3570  
0.614, 0.785  
25510, 4009, 2370  
0.722, 0.811  
20297, 3860, 2525  
No. of measured, indepen-  
dent and observed  
[I > 2ꢆ(I)] reflections  
Rint  
0.058  
0.629  
0.033  
0.651  
0.047  
0.635  
0.034  
0.620  
ꢃ1  
˚
(sin ꢇ/ꢈ)max (A  
)
Refinement  
R[F2 > 2ꢆ(F2)], wR(F2), S  
No. of reflections  
No. of parameters  
No. of restraints  
H-atom treatment  
0.045, 0.131, 1.00  
3726  
304  
0.047, 0.130, 1.04  
5148  
373  
0.045, 0.122, 1.01  
4009  
322  
0.045, 0.128, 1.02  
3860  
236  
0
H-atom parameters  
constrained  
0.53, ꢃ0.71  
72  
89  
64  
H-atom parameters  
constrained  
0.20, ꢃ0.26  
H-atom parameters  
constrained  
0.39, ꢃ0.35  
H-atom parameters  
constrained  
0.40, ꢃ0.50  
ꢃ3  
˚
Áꢉmax, Áꢉmin (e A  
)
(V)  
(VI)  
(VII)  
Crystal data  
Chemical formula  
Mr  
C21H18ClNO3S  
399.87  
C20H14ClF2NO2S  
405.83  
C15H13N3O4  
299.28  
Crystal system, space group  
Temperature (K)  
Triclinic, P1  
294  
7.4798 (3), 11.4237 (5), 12.0933 (5)  
Monoclinic, C2/c  
294  
58.0164 (10), 7.8002 (2),  
16.1365 (3)  
90, 92.105 (1), 90  
Triclinic, P1  
294  
8.1296 (6), 9.5899 (6), 10.8824 (8)  
˚
a, b, c (A)  
ꢂ, ꢃ, ꢄ (ꢂ)  
105.814 (2), 101.959 (3),  
66.840 (4), 71.533 (4),  
99.187 (3)  
946.66 (7)  
2
Mo Kꢂ  
0.33  
71.350 (4)  
721.10 (9)  
2
Mo Kꢂ  
0.10  
3
˚
V (A )  
7297.5 (3)  
16  
Cu Kꢂ  
3.24  
Z
Radiation type  
ꢅ (mmꢃ1  
Crystal size (mm)  
)
0.25 ꢄ 0.20 ꢄ 0.15  
0.15 ꢄ 0.15 ꢄ 0.10  
0.15 ꢄ 0.15 ꢄ 0.10  
Data collection  
Diffractometer  
Absorption correction  
Bruker Kappa APEXII  
Multi-scan (SADABS; Bruker,  
2012)  
Bruker Kappa APEXII  
Multi-scan (SADABS; Bruker,  
2012)  
Bruker Kappa APEXII  
Multi-scan (SADABS; Bruker,  
2012)  
Tmin, Tmax  
0.908, 0.951  
20919, 3959, 2406  
0.601, 0.753  
42600, 6468, 3979  
0.921, 0.990  
15518, 2992, 1667  
No. of measured, independent and  
observed [I > 2ꢆ(I)] reflections  
Rint  
0.047  
0.629  
0.109  
0.596  
0.051  
0.629  
ꢃ1  
˚
(sin ꢇ/ꢈ)max (A  
)
Refinement  
R[F2 > 2ꢆ(F2)], wR(F2), S  
No. of reflections  
No. of parameters  
No. of restraints  
H-atom treatment  
0.045, 0.121, 1.03  
3959  
246  
0
H-atom parameters  
constrained  
0.27, ꢃ0.30  
0.066, 0.159, 1.03  
6468  
572  
0.052, 0.156, 1.03  
2992  
201  
0
H-atom parameters  
constrained  
0.17, ꢃ0.21  
70  
H-atom parameters  
constrained  
0.35, ꢃ0.43  
ꢃ3  
˚
Áꢉmax, Áꢉmin (e A  
)
Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS86 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).  
ꢀ
Acta Cryst. (2018). C74  
Sagar et al.  
Six closely related arylamides 3 of 9  
research papers  
˚
and 0.01 A, respectively. In addition, the anisotropic displa-  
cement parameters of the corresponding pairs of atoms in the  
two disorder forms were constrained to be identical. All H  
atoms were treated as riding atoms in geometrically idealized  
positions, with C—H = 0.93 (aromatic and thienyl), 0.96 (CH3)  
˚
˚
or 0.97 A (CH2) and N—H = 0.86 A, and with Uiso(H) =  
kUeq(carrier), where k = 1.5 for the methyl groups, which were  
permitted to rotate but not to tilt, and 1.2 for all other H  
atoms. Subject to these conditions, the refined occupancies of  
the two disorder forms were 0.894 (8) and 0.106 (8) in (I),  
0.832 (5) and 0.168 (5) in (II), 0.7006 (12) and 0.2994 (12) in  
(III), and 0.916 (3) and 0.084 (3) in molecule 2 of compound  
(VI). One low-angle reflection, i.e. 001, which had been atte-  
nuated by the beam stop was omitted from the final refine-  
ment for (V). The 002 reflection was omitted from the  
refinement of (II). In the final analyses of variance for (I)–(V)  
2
and (VII), there were negative values of K = [mean(Fo )/  
2
mean(Fc )] for the groups of the very weakest reflections  
Figure 1  
The molecular structure of compound (I), showing the atom-labelling  
scheme and the disorder. The major-disorder component is drawn with  
full lines and the minor-disorder component is drawn with broken lines.  
Displacement ellipsoids are drawn at the 30% probability level.  
having low values of Fc/Fc(max): in (I), ꢃ4.417 for 441  
reflections in the Fc/Fc(max) range 0.000–0.005; in (II), ꢃ4.457  
for 532 reflections in the Fc/Fc(max) range 0.000–0.004; in  
(III), ꢃ1.720 for 407 reflections in the Fc/Fc(max) range 0.000–  
0.008; in (IV), ꢃ0.462 for 393 reflections in the Fc/Fc(max)  
range 0.000–0.005; in (V), ꢃ2.853 for 447 reflections in the  
Fc/Fc(max) range 0.000–0.006; in (VII), ꢃ3.669 for 393  
reflections in the Fc/Fc(max) range 0.000–0.004; in (VI), there  
was a large positive value of 11.570 for 756 reflections in the  
Fc/Fc(max) range 0.000–0.006; these are all probably statistical  
artefacts.  
Ar—H), 7.98–7.96 (m, 1H, Ar—H), 7.68–7.67 (m, 1H, Ar—H),  
7.54–7.42 (m, 3H, Ar—H), 7.03–7.01 (m, 1H, Ar—H), 4.01 (s,  
3H, –OCH3), 3.97 (s, 3H, –OCH3).  
2.2. Refinement  
Crystal data, data collection and structure refinement  
details are summarized in Table 1. It was apparent from an  
early stage in the refinements of compounds (I)–(III) that the  
molecules were disordered over two sets of atomic sites having  
different occupancies, as was one of the two independent  
molecules in (VI). For the minor-disorder forms, the bond  
lengths and 1,3 nonbonded distances were restrained to be the  
same as those in the major forms, subject to s.u. values of 0.005  
3. Results and discussion  
The molecules of compounds (I)–(III) are disordered over two  
sets of atomic sites, with occupancies of 0.894 (8) and 0.106 (8)  
Table 2  
Selected torsion angles (ꢂ) for compounds (I)–(VI).  
For compounds (I)–(VI) ꢊ1, ꢊ2, ꢊ3, ꢊ4 and ꢊ5 represent, respectively, the torsion  
angles Sx21—Cx22—Nx1—Cx1, Cx22—Nx1—Cx1—Cx11, Nx1—Cx1—  
Cx11—Cx12, Cx23—Cx37—Cx31—Cx32 and Sx21—Cx25—Cx26—Cx27.  
For (IV) and (V), x = nul; for the major- and minor-disorder components of  
(I), (II) and (III), x = 1 or 2, respectively; for compound (VI), x = 1 for  
molecule 1 and x = 2 or 3 for the major- and minor-disorder components,  
respectively, of molecule 2.  
ꢊ1  
ꢊ2  
ꢊ3  
ꢊ4  
ꢊ5  
(I), major  
(I), minor  
(II), major  
(II), minor  
(III), major  
(III), minor  
(IV)  
ꢃ0.7 (11) ꢃ179.0 (8) ꢃ163.2 (6) ꢃ103.8 (5)  
ꢃ9 (9) ꢃ158 (7) ꢃ158 (5) ꢃ97 (4)  
6.3 (15) 179.1 (4) 179.1 (9)  
ꢃ68.8 (7) ꢃ55.2 (5)  
163 (6) ꢃ157 (5) ꢃ65 (3) 49 (3)  
25.8 (8)  
56 (4)  
14 (8)  
ꢃ2 (3)  
176.9 (18) 146.9 (10) ꢃ71.2 (19) 59 (2)  
14 (8) ꢃ159 (4)  
136 (4) 33 (6)  
142.0 (4)  
ꢃ61 (5)  
ꢃ123.7 (5) ꢃ177.8 (5)  
21.1 (4)  
0.5 (6)  
173.9 (4)  
(V)  
ꢃ4.5 (3) ꢃ170.4 (2) ꢃ16.1 (4)  
3.0 (6) ꢃ174.5 (4) 137.2 (4)  
4.5 (11) ꢃ174.3 (6) 134.6 (7)  
ꢃ111.7 (3)  
(VI), mol. 1  
(VI), mol. 2,  
major  
ꢃ110.7 (5) 160.5 (4)  
ꢃ70.0 (7) ꢃ174.4 (6)  
Figure 2  
The molecular structure of compound (II), showing the atom-labelling  
scheme and the disorder. The major-disorder component is drawn with  
full lines and the minor-disorder component is drawn with broken lines.  
Displacement ellipsoids are drawn at the 30% probability level.  
(VI), mol. 2,  
minor  
16 (11)  
172 (6)  
127 (8)  
ꢃ75 (6)  
105 (5)  
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Table 3  
Hydrogen bonds and short intra- and intermolecular contacts (A, ) for  
compounds (I)–(VII).  
ꢂ
˚
Cg1 and Cg2 represent the centroids of the C131–C136 and C31–C36 rings,  
respectively.  
Compound D—Hꢁ ꢁ ꢁA  
D—H Hꢁ ꢁ ꢁA Dꢁ ꢁ ꢁA  
D—Hꢁ ꢁ ꢁA  
(I)  
N11—H11ꢁ ꢁ ꢁO137  
0.86  
0.86  
0.93  
0.93  
0.86  
0.86  
0.93  
0.93  
0.86  
0.86  
0.93  
0.93  
0.86  
0.93  
0.93  
0.86  
0.86  
0.93  
0.93  
0.86  
0.86  
0.86  
0.86  
0.93  
0.93  
0.93  
0.93  
2.03  
2.12  
2.53  
2.13  
2.08  
2.01  
2.47  
2.56  
2.06  
2.12  
2.82  
2.24  
2.02  
2.44  
2.92  
1.97  
2.08  
2.90  
2.48  
2.13  
2.10  
2.22  
2.60  
2.50  
2.59  
2.58  
2.52  
2.671 (12) 131  
2.73 (10) 129  
3.438 (9) 166  
N21—H21ꢁ ꢁ ꢁO237  
C115—H115ꢁ ꢁ ꢁO137i  
C215—H215ꢁ ꢁ ꢁO237i  
N11—H11ꢁ ꢁ ꢁO137  
N21—H21ꢁ ꢁ ꢁO237  
C112—H112ꢁ ꢁ ꢁO11ii  
C144—H144ꢁ ꢁ ꢁO137iii  
N11—H11ꢁ ꢁ ꢁO137  
N21—H21ꢁ ꢁ ꢁO237  
C114—H114ꢁ ꢁ ꢁCg1iv  
C214—H214ꢁ ꢁ ꢁO237v  
N1—H1ꢁ ꢁ ꢁO37  
3.04 (7)  
2.719 (10) 130  
2.65 (5) 131  
166  
(II)  
(III)  
3.230 (4) 139  
3.397 (6) 150  
2.70 (2)  
2.71 (6)  
131  
126  
3.565 (12) 138  
2.96 (4) 134  
(IV)  
(V)  
2.665 (5) 131  
3.322 (7) 159  
3.453 (6) 118  
2.651 (3) 135  
2.716 (3) 130  
3.782 (4) 158  
3.306 (4) 147  
2.753 (4) 129  
2.733 (11) 129  
2.76 (10) 121  
3.28 (10) 137  
C33—H33ꢁ ꢁ ꢁO37vi  
C15—H15ꢁ ꢁ ꢁCg2vii  
N1—H1ꢁ ꢁ ꢁO12  
Figure 3  
N1—H1ꢁ ꢁ ꢁO37  
The molecular structure of compound (III), showing the atom-labelling  
scheme and the disorder. The major-disorder component is drawn with  
full lines and the minor-disorder component is drawn with broken lines.  
Displacement ellipsoids are drawn at the 30% probability level and, for  
the sake of clarity, some of the atom labels have been omitted.  
C13—H13ꢁ ꢁ ꢁCg2viii  
C36—H36ꢁ ꢁ ꢁO1ix  
N11—H11ꢁ ꢁ ꢁO137  
N21—H21ꢁ ꢁ ꢁO237  
N31—H31ꢁ ꢁ ꢁO337  
N31—H31ꢁ ꢁ ꢁO11  
C114—H114ꢁ ꢁ ꢁO337x  
C214—H214ꢁ ꢁ ꢁO137xi  
C314—H314ꢁ ꢁ ꢁO137xi  
C27—H27ꢁ ꢁ ꢁO14ii  
(VI)  
3.33 (5)  
3.407 (6) 146  
3.42 (4) 150  
3.175 (3) 127  
150  
in (I), 0.832 (5) and 0.168 (5) in (II), and 0.7006 (12) and  
0.2994 (12) in (III). By contrast, compounds (IV) and (V) are  
fully ordered, while in compound (VI), which crystallizes with  
Z0 = 2, molecule 1, containing atom O11, is fully ordered, but  
molecule 2, containing atom O21, is disordered over two sets  
of atomic sites having occupancies of 0.916 (3) and 0.084 (3).  
For each of (I)–(VI), which are all conformationally chiral  
(Figs. 1–6), the reference molecules were selected to have the  
same sign of torsion angle ꢊ4 (Table 2), which defines the  
orientation of the 2-chlorobenzoyl substituent relative to the  
thiophene ring. In each compound, the amide unit is effec-  
tively coplanar with the thiophene ring, as shown by torsion  
angles ꢊ1 and ꢊ2; the relative orientation of the thiophene and  
(VII)  
Symmetry codes: (i) ꢃx, ꢃy + 1, ꢃz + 1; (ii) ꢃx + 1, ꢃy + 2, ꢃz + 1; (iii) ꢃx + 1, y + 12,  
ꢃz + 32; (iv) x, y + 1, z; (v) ꢃx + 23, ꢃy + 23, ꢃz + 1; (vi) ꢃx + 32, y + 12, ꢃz + 21; (vii) ꢃx + 32, y ꢃ ,  
1
2
ꢃz + 12; (viii) ꢃx, ꢃy, ꢃz + 1; (ix) ꢃx, ꢃy + 1, ꢃz + 1; (x) x, ꢃy + 1, ꢃz ꢃ ; (xi) x, ꢃy + 1,  
1
2
ꢃz + 12.  
2-chlorobenzoyl substituents is probably controlled in each  
compound by the short intramolecular N—Hꢁ ꢁ ꢁO contact  
involving the carbonyl O atom (Table 3). It is similarly likely  
that the orientation of the methoxy group in compound (V) is  
controlled by a second intramolecular N—Hꢁ ꢁ ꢁO contact  
Figure 4  
The molecular structure of compound (IV), showing the atom-labelling  
scheme. Displacement ellipsoids are drawn at the 30% probability level.  
Figure 5  
The molecular structure of compound (V), showing the atom-labelling  
scheme. Displacement ellipsoids are drawn at the 30% probability level.  
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that the Br substituent is on opposite edges of the 2-bromo-  
phenyl ring in the two forms (Fig. 3). The orientation of the  
ethyl group relative to the thiophene ring is extremely vari-  
able, as shown by the values of ꢊ5 and as can be seen in  
Figs. 1–6, and this variability extends even to the two disorder  
components in a given compound, most markedly in (I), (II)  
and (VI). Since this substituent plays no role in the supra-  
molecular assembly, it seems likely that it is acting simply as a  
space filler, occupying whatever space is available to it in the  
overall supramolecular structure. The variations in torsion  
angle ꢊ3 (Table 2), which defines the orientation of the  
substituted aryl ring (Cx1–Cx6), may be associated with the  
observation that the C—H units in the ring participate in the  
hydrogen bonds in each of (I)–(VI) (Table 3).  
In each compound, the bond lengths provide evidence for a  
modest delocalization of the lone pair of electrons on the N  
atom, not only into the adjacent carbonyl unit, but also into  
the remote carbonyl unit since atoms Nx1, Cx22, Cx23, Cx37  
and Ox37 (the values of x are defined in Table 2) constitute a  
vinylogous amide system, so that forms (A), (B) and (C)  
(Scheme 2) all contribute to the overall electronic structure.  
The polarization in form (C) enhances the strength of the  
intramolecular N—Hꢁ ꢁ ꢁO interactions. In this connection, we  
note here that, as discussed below, the acyl carbonyl O atom is  
used as an acceptor in intermolecular hydrogen bonds in each  
of compounds (I), (II), (IV) and (VI), while the amide  
carbonyl O atoms act as such an acceptor only in compounds  
(II) and (V); neither of these O atoms participates in the  
supramolecular assembly of compound (III).  
Figure 6  
The structures and atom-labelling schemes of the two independent  
molecules in compound (VI), showing (a) molecule 1 and (b) molecule 2.  
For the disorder in molecule 2, the major-disorder component is drawn  
with full lines and the minor-disorder component is drawn with broken  
lines. Displacement ellipsoids are drawn at the 30% probability level and,  
for the sake of clarity, some of the atom labels in part (b) have been  
omitted.  
(Table 3 and Fig. 5). It is of interest to note that in compound  
(III), the two disorder forms are conformational isomers, in  
In compound (VII) (Fig. 7), the benzoate unit is effectively  
˚
planar, with an r.m.s. deviation of only 0.0192 A from the  
mean plane of atoms C11–C16, C1, O1 and O2, and this plane  
makes a dihedral angle of 84.51 (6)ꢂ with that of the benzo-  
triazole unit; the two methoxy C atoms are effectively  
coplanar with the adjacent ring, with displacements from this  
˚
plane of 0.102 (4) and 0.215 (4) A for atoms C131 and C141,  
respectively. Consistent with this observation, the corre-  
sponding pairs of exocyclic C—C—O angles differ at both C13  
and C14 by ca 10ꢂ, as typically found in planar or near-planar  
alkoxyarenes (Seip & Seip, 1973; Ferguson et al., 1996).  
Figure 7  
The molecular structure of compound (VII), showing the atom-labelling  
scheme. Displacement ellipsoids are drawn at the 30% probability level.  
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relatively low abundances of the minor-disorder forms in  
compounds (I)–(III) and (VI), we discuss here only the  
supramolecular interactions involving the major-disorder  
forms, although those for the minor forms are included in  
Table 3 for the sake of completeness.  
In compound (I), a single C—Hꢁ ꢁ ꢁO hydrogen bond links  
inversion-related pairs of molecules to form a cyclic centro-  
symmetric dimer in which an outer R22(20) (Etter, 1990; Etter  
et al., 1990; Bernstein et al., 1995) ring encloses an inner R24(16)  
ring flanked by two inversion-related S(6) rings (Fig. 8). Two  
dimers of this type, related to one another by the translational  
symmetry elements, are present in each unit cell, but there are  
no direction-specific interactions between adjacent dimers.  
Two independent C—Hꢁ ꢁ ꢁO hydrogen bonds link the  
molecules of compound (II) into sheets, whose formation is  
readily analysed in terms of two simpler substructures  
(Ferguson et al., 1998a,b; Gregson et al., 2000). In the simplest  
of these substructures, inversion-related pairs of molecules are  
linked into cyclic R22(10) dimers, where the reference dimer is  
centred at (12, 1, ). In the second substructure, molecules  
Figure 8  
1
2
Part of the crystal structure of compound (I), showing the formation of a  
cyclic hydrogen-bonded dimer. For the sake of clarity, the unit-cell  
outline, H atoms bonded to C atoms which are not involved in the motif  
shown and the minor-disorder component have all been omitted.  
Hydrogen bonds are shown as dashed lines and atoms marked with an  
asterisk (*) are at the symmetry position (ꢃx, ꢃy + 1, ꢃz + 1).  
related by a 21 screw axis are linked into C21(13) chains running  
parallel to the [010] direction. The action of these chains is to  
1
link the reference dimer centred at (12, 1, ) directly to four  
2
1
2
3
1
2
other such dimers, centred at (12, , 0), (21, , 0), (21, , 1) and  
2
(12, 32, 1), so forming a sheet lying parallel to (100) and  
containing rings of R22(10) and R160(54) types (Fig. 9).  
As noted above, the molecules of (I)–(VI) all contain an  
intramolecular N—Hꢁ ꢁ ꢁO interaction, but the N—H unit  
plays no role in the supramolecular assembly in any of (I)–  
(VI); this assembly depends upon C—Hꢁ ꢁ ꢁO and C—  
Hꢁ ꢁ ꢁꢀ(arene) hydrogen bonds (Table 3). Because of the  
Figure 10  
Part of the crystal structure of compound (III), showing the formation of  
a hydrogen-bonded chain running parallel to [010]. For the sake of clarity,  
H atoms bonded to C atoms which are not involved in the motif shown  
and the minor-disorder component have been omitted. Hydrogen bonds  
are shown as dashed lines and the Br atoms marked with an asterisk (*) or  
a hash (#) are at the symmetry positions (x, y + 1, z) and (x, y ꢃ 1, z),  
respectively.  
Figure 9  
Part of the crystal structure of compound (II), showing the formation of a  
hydrogen-bonded sheet lying parallel to (100). For the sake of clarity, H  
atoms bonded to C atoms which are not involved in the motif shown and  
the minor-disorder component have been omitted. Hydrogen bonds are  
shown as dashed lines.  
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related pairs of molecules, but the very small C—Hꢁ ꢁ ꢁO angle  
suggests that this may not be structurally significant (Wood et  
al., 2009).  
It is of interest briefly to compare the structures of  
compounds (I)–(VII) reported here with those of related  
compounds. The structure of the amine 2-amino-3-(2-chloro-  
benzoyl)-5-ethylthiophene, (VIII) (see Scheme 3), has been  
reported recently (Kubicki et al., 2012). The molecule contains  
an intramolecular N—Hꢁ ꢁ ꢁO hydrogen bond, as found in each  
of (I)–(VI), and the values of torsion angles ꢊ4 and ꢊ5 for the  
conformational enantiomer of (VIII) corresponding to those  
of (I)–(VI) are ꢃ82.2 and 56.7ꢂ, respectively (no s.u. values are  
associated with the deposited atomic coordinates) The value  
of ꢊ4 is very similar to those found here, but that for ꢊ5 again  
suggests a space-filling role for the ethyl substituent. The  
molecules of (VIII) are linked by N—Hꢁ ꢁ ꢁO hydrogen bonds  
into C21(4) chains. The original report on (VIII) also refers to  
three intermolecular C—Hꢁ ꢁ ꢁCl interactions. However, for all  
of these interactions, the reported Hꢁ ꢁ ꢁCl distances are larger  
than the sum of the van der Waals radii for H and Cl (Rowland  
& Taylor, 1996) and, in any event, it has been convincingly  
shown from database analyses that a Cl atom bonded to a C  
atom is a very poor acceptor of hydrogen bonds, even from  
good donors such as O and N, and thus even worse from C  
(Brammer et al., 2001; Thallypally & Nangia, 2001).  
Figure 11  
Part of the crystal structure of compound (IV), showing the formation of  
a chain of rings running parallel to [010] and built from C—Hꢁ ꢁ ꢁO and  
C—Hꢁ ꢁ ꢁꢀ(arene) hydrogen bonds, shown as dashed lines. For the sake of  
clarity, H atoms bonded to C atoms which are not involved in the motif  
shown have been omitted.  
The major components of compound (III) are linked by a  
single C—Hꢁ ꢁ ꢁꢀ(arene) hydrogen bond to form simple chains  
running parallel to the [010] direction in which the component  
molecules are related by translation (Fig. 10). Eight chains of  
this type pass through each unit cell but there are no direction-  
specific interactions between adjacent chains. The molecules  
of compound (IV) which are related by a 21 screw axis are  
linked by a C—Hꢁ ꢁ ꢁO hydrogen bond to form a C(6) chain  
running parallel to the [010] direction; the action of this  
hydrogen bond is weakly reinforced by a C—Hꢁ ꢁ ꢁꢀ(arene)  
hydrogen bond, so forming a chain of rings parallel to the  
[010] direction (Fig. 11). Two chains of this type, related to one  
another by inversion, pass through each unit cell, but there are  
no direction-specific interactions between adjacent chains.  
The crystal structure of compound (V) also contains a chain  
of rings built from C—Hꢁ ꢁ ꢁO and C—Hꢁ ꢁ ꢁꢀ(arene) hydrogen  
bonds and again running parallel to the [010] direction.  
However, this chain contains two types of ring, both centro-  
symmetric, with R22(18) rings containing inversion-related  
pairs of C—Hꢁ ꢁ ꢁO hydrogen bonds centred at (0, n + 12, 21) and  
rings built from inversion-related pairs of C—Hꢁ ꢁ ꢁꢀ(arene)  
The structure of benzotriazol-1-yl benzoate, (IX), was  
reported some 40 years ago (McCarthy et al., 1977) in a study  
focused on determining whether the compound was an O-acyl  
or an N-acyl derivative, based upon the observation that such  
benzotriazole compounds effect acyl transfer to amines at  
rates comparable with those found for N-acylimidazoles. The  
product was indeed found to be a benzoate ester and like  
compound (VII), the benzoate fragment is planar, the two  
rings making a dihedral angle of 84.8ꢂ (no s.u. values are  
associated with the deposited atomic coordinates), almost  
identical to the corresponding value in (VII). However, the  
1
2
hydrogen bonds centred at (0, n, ), where n represents an  
integer in each case (Fig. 12). The two independent molecules  
of compound (VI) are linked by a single C—Hꢁ ꢁ ꢁO hydrogen  
bond, but there are no further direction-specific interactions in  
the structure, which simply contains finite acyclic dimers [cf.  
the cyclic dimer formed in compound (I)]. There is a single  
C—Hꢁ ꢁ ꢁO contact in compound (VII) between inversion-  
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supramolecular assembly in (IX) is entirely different from that  
in (VII); in (IX), four hydrogen bonds, one each of the C—  
Hꢁ ꢁ ꢁO and C—Hꢁ ꢁ ꢁꢀ(arene) types and two of the C—Hꢁ ꢁ ꢁN  
type, all having D—Hꢁ ꢁ ꢁA angles greater than 140ꢂ (cf. Wood  
et al., 2009), link the molecules into a three-dimensional  
framework structure, which is reinforced by aromatic ꢀ–ꢀ  
stacking interactions.  
Acknowledgements  
HSY thanks the University of Mysore for research facilities.  
Funding information  
Funding for this research was provided by: University Grants  
Commission (award of a Rajeev Gandhi Fellowship to BKS).  
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Figure 12  
Part of the crystal structure of compound (V), showing the formation of a  
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Six closely related arylamides 9 of 9  
supporting information  
supporting information  
Acta Cryst. (2018). C74 [https://doi.org/10.1107/S2053229618000657]  
Synthesis and structures of six closely related N-[3-(2-chlorobenzoyl)-5-ethyl-  
thiophen-2-yl]arylamides, together with an isolated reaction intermediate:  
order versus disorder, molecular conformations and hydrogen bonding in zero,  
one and two dimensions  
Belakavadi K. Sagar, Hemmige S. Yathirajan, Ravindranath S. Rathore and Christopher  
Glidewell  
Computing details  
For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT  
(Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure:  
SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for  
publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).  
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide (I)  
Crystal data  
C20H16ClNO2S  
Mr = 369.85  
F(000) = 768  
Dx = 1.374 Mg m−3  
Mo Kα radiation, λ = 0.71073 Å  
Cell parameters from 4162 reflections  
θ = 2.1–27.6°  
Monoclinic, P21/c  
a = 9.7868 (9) Å  
b = 13.9567 (12) Å  
c = 13.3764 (11) Å  
β = 101.816 (2)°  
V = 1788.4 (3) Å3  
Z = 4  
µ = 0.34 mm−1  
T = 294 K  
Block, yellow  
0.25 × 0.20 × 0.20 mm  
Data collection  
Bruker Kappa APEXII  
diffractometer  
Radiation source: fine focus sealed tube  
φ and ω scans  
3726 independent reflections  
2092 reflections with I > 2σ(I)  
Rint = 0.058  
θ
max = 26.6°, θmin = 2.1°  
Absorption correction: multi-scan  
(SADABS; Bruker, 2012)  
h = −12→12  
k = −17→17  
l = −16→16  
T
min = 0.864, Tmax = 0.934  
26489 measured reflections  
Refinement  
Refinement on F2  
S = 1.00  
Least-squares matrix: full  
R[F2 > 2σ(F2)] = 0.045  
wR(F2) = 0.131  
3726 reflections  
304 parameters  
72 restraints  
Acta Cryst. (2018). C74  
sup-1  
supporting information  
Hydrogen site location: inferred from  
neighbouring sites  
H-atom parameters constrained  
w = 1/[σ2(Fo2) + (0.0536P)2 + 0.5759P]  
where P = (Fo2 + 2Fc2)/3  
(Δ/σ)max < 0.001  
Δρmax = 0.20 e Å−3  
Δρmin = −0.26 e Å−3  
Special details  
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance  
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;  
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate  
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.  
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)  
x
y
z
Uiso*/Ueq  
Occ. (<1)  
C11  
O11  
N11  
H11  
0.4662 (5)  
0.5871 (4)  
0.3840 (6)  
0.2994  
0.3996 (4)  
0.4867 (4)  
0.5830  
0.4309 (5)  
0.4898  
0.2884 (5)  
0.2512  
0.2014 (5)  
0.1052  
0.2564 (4)  
0.1968  
0.5895 (2)  
0.4252 (4)  
0.3390 (5)  
0.4093 (5)  
0.3669  
0.5426 (5)  
0.6508 (6)  
0.6042  
0.6863  
0.7653 (6)  
0.8178  
0.8236  
0.7330  
0.1991 (4)  
0.1483 (6)  
0.1082 (4)  
0.0831 (4)  
0.1722 (4)  
−0.0123 (7)  
0.4257 (5)  
0.4022 (3)  
0.3740 (4)  
0.3932  
0.5092 (4)  
0.5772 (4)  
0.5708  
0.6544 (4)  
0.6993  
0.6649 (4)  
0.7177  
0.5981 (5)  
0.6045  
0.5205 (5)  
0.4758  
0.24663 (19)  
0.2938 (4)  
0.2415 (5)  
0.1595 (4)  
0.1158  
0.1516 (4)  
0.0790 (4)  
0.0178  
0.0973  
0.0650 (4)  
0.1234  
0.0153  
0.0467  
0.2729 (3)  
0.3470 (6)  
0.2122 (3)  
0.2350 (2)  
0.32924 (12)  
0.1840 (4)  
0.6023 (6)  
0.6349 (4)  
0.5264 (5)  
0.5055  
0.6421 (5)  
0.6982 (5)  
0.7071  
0.7409 (6)  
0.7791  
0.7270 (6)  
0.7545  
0.6728 (6)  
0.6650  
0.6295 (8)  
0.5917  
0.51192 (17)  
0.4807 (5)  
0.4055 (5)  
0.3766 (4)  
0.3274  
0.4272 (3)  
0.4134 (4)  
0.3985  
0.3535  
0.4936 (4)  
0.5063  
0.4756  
0.5540  
0.3611 (3)  
0.3882 (10)  
0.2808 (3)  
0.1786 (3)  
0.13678 (12)  
0.1081 (3)  
0.0450 (7)  
0.0654 (14)  
0.0469 (9)  
0.056*  
0.0394 (9)  
0.0482 (11)  
0.058*  
0.0567 (11)  
0.068*  
0.0618 (12)  
0.074*  
0.0608 (11)  
0.073*  
0.0509 (10)  
0.061*  
0.0545 (4)  
0.0424 (7)  
0.0430 (8)  
0.0520 (14)  
0.062*  
0.0610 (11)  
0.1070 (15)  
0.128*  
0.128*  
0.118 (2)  
0.178*  
0.178*  
0.178*  
0.0493 (8)  
0.0763 (10)  
0.0471 (8)  
0.0529 (8)  
0.0900 (6)  
0.0660 (10)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
C111  
C112  
H112  
C113  
H113  
C114  
H114  
C115  
H115  
C116  
H116  
S121  
C122  
C123  
C124  
H124  
C125  
C126  
H16A  
H16B  
C127  
H17A  
H17B  
H17C  
C137  
O137  
C131  
C132  
Cl12  
C133  
Acta Cryst. (2018). C74  
sup-2  
supporting information  
H133  
C134  
H134  
C135  
H135  
C136  
H136  
C21  
−0.0291  
−0.0821 (5)  
−0.1470  
−0.0571 (5)  
−0.1035  
0.0383 (7)  
0.0555  
0.458 (4)  
0.584 (3)  
0.379 (5)  
0.3034  
0.382 (3)  
0.461 (3)  
0.5572  
0.397 (4)  
0.4505  
0.253 (5)  
0.2104  
0.175 (4)  
0.0788  
0.238 (3)  
0.1833  
0.566 (2)  
0.411 (3)  
0.329 (3)  
0.404 (4)  
0.3639  
0.538 (4)  
0.641 (4)  
0.6082  
0.2010  
0.1085 (3)  
0.0746  
0.0828 (3)  
0.0308  
0.1348 (4)  
0.1169  
0.432 (4)  
0.423 (3)  
0.384 (4)  
0.4107  
0.504 (3)  
0.576 (3)  
0.5680  
0.658 (3)  
0.7107  
0.663 (4)  
0.7127  
0.594 (4)  
0.6027  
0.512 (5)  
0.4611  
0.2386 (18)  
0.296 (3)  
0.250 (4)  
0.174 (4)  
0.1331  
0.167 (3)  
0.089 (3)  
0.0549  
0.0394  
0.1395 (4)  
0.0921  
0.2396 (4)  
0.2607  
0.3097 (4)  
0.3781  
0.600 (5)  
0.619 (4)  
0.519 (4)  
0.4883  
0.650 (4)  
0.707 (5)  
0.7283  
0.731 (6)  
0.7585  
0.715 (6)  
0.7427  
0.657 (6)  
0.6354  
0.630 (7)  
0.5995  
0.5242 (16)  
0.483 (4)  
0.401 (4)  
0.365 (4)  
0.3115  
0.415 (2)  
0.407 (3)  
0.3431  
0.4023  
0.485 (3)  
0.4716  
0.5490  
0.4891  
0.079*  
0.0696 (13)  
0.084*  
0.0736 (13)  
0.088*  
0.0667 (10)  
0.080*  
0.0450 (7)  
0.0654 (14)  
0.0469 (9)  
0.056*  
0.0394 (9)  
0.0482 (11)  
0.058*  
0.0567 (11)  
0.068*  
0.0618 (12)  
0.074*  
0.0608 (11)  
0.073*  
0.0509 (10)  
0.061*  
0.0545 (4)  
0.0424 (7)  
0.0430 (8)  
0.0520 (14)  
0.062*  
0.0610 (11)  
0.1070 (15)  
0.128*  
0.128*  
0.118 (2)  
0.178*  
0.178*  
0.178*  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.894 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
0.106 (8)  
O21  
N21  
H21  
C211  
C212  
H212  
C213  
H213  
C214  
H214  
C215  
H215  
C216  
H216  
S221  
C222  
C223  
C224  
H224  
C225  
C226  
H26A  
H26B  
C227  
H27A  
H27B  
H27C  
C237  
O237  
C231  
C232  
Cl22  
0.7290  
0.668 (6)  
0.5992  
0.6635  
0.7591  
0.1189  
0.021 (3)  
−0.0291  
0.0513  
−0.0058  
0.271 (2)  
0.348 (5)  
0.207 (2)  
0.2286 (12)  
0.3359 (12)  
0.166 (2)  
0.1801  
0.082 (2)  
0.0411  
0.058 (2)  
0.0007  
0.182 (3)  
0.131 (5)  
0.092 (4)  
0.060 (2)  
0.116 (2)  
−0.015 (6)  
−0.0326  
−0.064 (5)  
−0.1183  
−0.033 (5)  
−0.0646  
0.045 (6)  
0.0667  
0.3688 (17)  
0.388 (9)  
0.2915 (17)  
0.1890 (14)  
0.1463 (12)  
0.119 (2)  
0.0497  
0.152 (3)  
0.1053  
0.253 (3)  
0.2748  
0.0493 (8)  
0.0763 (10)  
0.0471 (8)  
0.0529 (8)  
0.0900 (6)  
0.0660 (10)  
0.079*  
0.0696 (13)  
0.084*  
0.0736 (13)  
0.088*  
C233  
H233  
C234  
H234  
C235  
H235  
C236  
H236  
0.121 (3)  
0.1044  
0.322 (2)  
0.3907  
0.0667 (10)  
0.080*  
Acta Cryst. (2018). C74  
sup-3  
supporting information  
Atomic displacement parameters (Å2)  
U11  
U22  
U33  
U12  
U13  
U23  
C11  
O11  
N11  
0.0384 (17)  
0.0427 (12)  
0.0384 (13)  
0.0350 (17)  
0.043 (2)  
0.060 (3)  
0.067 (4)  
0.047 (2)  
0.042 (2)  
0.0413 (8)  
0.0379 (17)  
0.0367 (15)  
0.0530 (18)  
0.0558 (19)  
0.089 (3)  
0.093 (4)  
0.0412 (18)  
0.049 (2)  
0.0347 (18)  
0.0444 (18)  
0.1077 (16)  
0.060 (2)  
0.046 (2)  
0.061 (3)  
0.0543 (19)  
0.079 (3)  
0.0391 (14)  
0.066 (2)  
0.0437 (16)  
0.0328 (17)  
0.039 (2)  
0.049 (3)  
0.053 (3)  
0.058 (3)  
0.0502 (16)  
0.0446 (7)  
0.0364 (13)  
0.0400 (15)  
0.045 (2)  
0.052 (2)  
0.094 (3)  
0.123 (4)  
0.0483 (16)  
0.0895 (15)  
0.0522 (17)  
0.0534 (17)  
0.0720 (6)  
0.0564 (19)  
0.082 (3)  
−0.0016 (13)  
0.0094 (14)  
0.0060 (12)  
0.0006 (14)  
−0.0073 (17)  
−0.009 (2)  
0.012 (2)  
0.0007 (12)  
−0.0089 (12)  
−0.0049 (10)  
0.0030 (14)  
0.0076 (18)  
0.006 (3)  
0.010 (3)  
0.002 (2)  
0.001 (2)  
−0.0020 (5)  
0.0029 (13)  
0.0009 (11)  
0.0005 (14)  
−0.0041 (15)  
−0.019 (2)  
−0.019 (3)  
0.0019 (13)  
−0.017 (2)  
0.0022 (13)  
0.0020 (14)  
0.0209 (8)  
−0.0056 (17)  
−0.0066 (19)  
0.016 (2)  
0.0065 (18)  
0.0007 (12)  
−0.0089 (12)  
−0.0049 (10)  
0.0030 (14)  
0.0076 (18)  
0.006 (3)  
−0.0015 (14)  
−0.021 (2)  
0.0531 (19)  
0.0488 (16)  
0.0629 (19)  
0.0585 (19)  
0.065 (2)  
0.074 (2)  
0.057 (2)  
0.0731 (7)  
0.0509 (15)  
0.049 (2)  
0.054 (3)  
0.069 (3)  
0.122 (4)  
0.122 (4)  
0.0552 (17)  
0.0768 (15)  
0.0518 (17)  
0.0575 (18)  
0.0914 (7)  
0.074 (3)  
0.072 (3)  
0.063 (3)  
0.064 (3)  
0.0543 (19)  
0.079 (3)  
0.0531 (19)  
0.0488 (16)  
0.0629 (19)  
0.0585 (19)  
0.065 (2)  
0.074 (2)  
0.057 (2)  
0.0731 (7)  
0.0509 (15)  
0.049 (2)  
0.054 (3)  
0.069 (3)  
0.122 (4)  
0.122 (4)  
−0.0070 (16)  
0.0030 (14)  
−0.0010 (14)  
−0.0108 (17)  
−0.0077 (16)  
−0.005 (2)  
−0.0079 (19)  
−0.0082 (5)  
0.0005 (12)  
−0.0026 (15)  
−0.010 (2)  
−0.0120 (18)  
−0.041 (3)  
−0.032 (3)  
−0.0091 (13)  
−0.0348 (12)  
−0.0077 (13)  
−0.0080 (14)  
0.0019 (5)  
C111  
C112  
C113  
C114  
C115  
C116  
S121  
C122  
C123  
C124  
C125  
C126  
C127  
C137  
O137  
C131  
C132  
Cl12  
C133  
C134  
C135  
C136  
C21  
0.013 (2)  
−0.0018 (17)  
0.0114 (7)  
0.0016 (13)  
0.0028 (12)  
0.0065 (15)  
0.0186 (17)  
0.057 (3)  
0.061 (4)  
0.0001 (14)  
0.0200 (16)  
0.0019 (13)  
−0.0037 (14)  
−0.0329 (9)  
0.002 (2)  
−0.003 (2)  
−0.016 (2)  
−0.009 (2)  
−0.0016 (13)  
0.0094 (14)  
0.0060 (12)  
0.0006 (14)  
−0.0073 (17)  
−0.009 (2)  
0.012 (2)  
−0.0107 (18)  
−0.026 (2)  
−0.012 (2)  
0.097 (3)  
0.063 (2)  
0.070 (2)  
0.0004 (17)  
−0.0015 (14)  
−0.021 (2)  
−0.0070 (16)  
0.0030 (14)  
−0.0010 (14)  
−0.0108 (17)  
−0.0077 (16)  
−0.005 (2)  
−0.0079 (19)  
−0.0082 (5)  
0.0005 (12)  
−0.0026 (15)  
−0.010 (2)  
−0.0120 (18)  
−0.041 (3)  
−0.032 (3)  
−0.0091 (13)  
−0.0348 (12)  
−0.0077 (13)  
−0.0080 (14)  
0.0384 (17)  
0.0427 (12)  
0.0384 (13)  
0.0350 (17)  
0.043 (2)  
0.060 (3)  
0.067 (4)  
0.047 (2)  
0.042 (2)  
0.0413 (8)  
0.0379 (17)  
0.0367 (15)  
0.0530 (18)  
0.0558 (19)  
0.089 (3)  
0.093 (4)  
0.0412 (18)  
0.049 (2)  
0.0391 (14)  
0.066 (2)  
0.0437 (16)  
0.0328 (17)  
0.039 (2)  
0.049 (3)  
0.053 (3)  
0.058 (3)  
0.0502 (16)  
0.0446 (7)  
0.0364 (13)  
0.0400 (15)  
0.045 (2)  
0.052 (2)  
0.094 (3)  
0.123 (4)  
O21  
N21  
C211  
C212  
C213  
C214  
C215  
C216  
S221  
C222  
C223  
C224  
C225  
C226  
C227  
C237  
O237  
C231  
C232  
0.010 (3)  
0.002 (2)  
0.001 (2)  
0.013 (2)  
−0.0018 (17)  
0.0114 (7)  
0.0016 (13)  
0.0028 (12)  
0.0065 (15)  
0.0186 (17)  
0.057 (3)  
−0.0020 (5)  
0.0029 (13)  
0.0009 (11)  
0.0005 (14)  
−0.0041 (15)  
−0.019 (2)  
−0.019 (3)  
0.0019 (13)  
−0.017 (2)  
0.0022 (13)  
0.0020 (14)  
0.061 (4)  
0.0552 (17)  
0.0768 (15)  
0.0518 (17)  
0.0575 (18)  
0.0483 (16)  
0.0895 (15)  
0.0522 (17)  
0.0534 (17)  
0.0001 (14)  
0.0200 (16)  
0.0019 (13)  
−0.0037 (14)  
0.0347 (18)  
0.0444 (18)  
Acta Cryst. (2018). C74  
sup-4  
supporting information  
Cl22  
C233  
C234  
C235  
C236  
0.1077 (16)  
0.060 (2)  
0.046 (2)  
0.061 (3)  
0.070 (2)  
0.0914 (7)  
0.074 (3)  
0.072 (3)  
0.063 (3)  
0.064 (3)  
0.0720 (6)  
0.0564 (19)  
0.082 (3)  
0.097 (3)  
0.063 (2)  
−0.0329 (9)  
0.002 (2)  
−0.003 (2)  
−0.016 (2)  
−0.009 (2)  
0.0209 (8)  
0.0019 (5)  
−0.0107 (18)  
−0.026 (2)  
−0.012 (2)  
0.0004 (17)  
−0.0056 (17)  
−0.0066 (19)  
0.016 (2)  
0.0065 (18)  
Geometric parameters (Å, º)  
C11—O11  
1.219 (3)  
C21—O21  
1.219 (6)  
C11—N11  
C11—C111  
N11—C122  
N11—H11  
1.365 (3)  
1.487 (4)  
1.376 (3)  
0.8600  
C21—N21  
C21—C211  
N21—C222  
N21—H21  
1.365 (6)  
1.488 (6)  
1.375 (6)  
0.8600  
C111—C116  
C111—C112  
C112—C113  
C112—H112  
C113—C114  
C113—H113  
C114—C115  
C114—H114  
C115—C116  
C115—H115  
C116—H116  
S121—C122  
S121—C125  
C122—C123  
C123—C124  
C123—C137  
C124—C125  
C124—H124  
C125—C126  
C126—C127  
C126—H16A  
C126—H16B  
C127—H17A  
C127—H17B  
C127—H17C  
C137—O137  
C137—C131  
C131—C136  
C131—C132  
C132—C133  
C132—Cl12  
C133—C134  
C133—H133  
C134—C135  
C134—H134  
1.385 (3)  
1.389 (3)  
1.384 (4)  
0.9300  
1.377 (4)  
0.9300  
1.367 (4)  
0.9300  
1.387 (4)  
0.9300  
C211—C216  
C211—C212  
C212—C213  
C212—H212  
C213—C214  
C213—H213  
C214—C215  
C214—H214  
C215—C216  
C215—H215  
C216—H216  
S221—C222  
S221—C225  
C222—C223  
C223—C224  
C223—C237  
C224—C225  
C224—H224  
C225—C226  
C226—C227  
C226—H26A  
C226—H26B  
C227—H27A  
C227—H27B  
C227—H27C  
C237—O237  
C237—C231  
C231—C236  
C231—C232  
C232—C233  
C232—Cl22  
C233—C234  
C233—H233  
C234—C235  
C234—H234  
1.386 (5)  
1.389 (6)  
1.385 (6)  
0.9300  
1.377 (6)  
0.9300  
1.368 (6)  
0.9300  
1.388 (6)  
0.9300  
0.9300  
0.9300  
1.708 (3)  
1.744 (3)  
1.381 (3)  
1.429 (3)  
1.444 (4)  
1.346 (4)  
0.9300  
1.503 (4)  
1.397 (6)  
0.9700  
0.9700  
0.9600  
0.9600  
0.9600  
1.235 (3)  
1.507 (4)  
1.376 (4)  
1.377 (4)  
1.380 (4)  
1.733 (3)  
1.368 (5)  
0.9300  
1.708 (5)  
1.747 (6)  
1.383 (5)  
1.429 (5)  
1.445 (6)  
1.349 (6)  
0.9300  
1.507 (6)  
1.398 (8)  
0.9700  
0.9700  
0.9600  
0.9600  
0.9600  
1.236 (6)  
1.507 (5)  
1.375 (6)  
1.376 (5)  
1.380 (6)  
1.733 (5)  
1.368 (6)  
0.9300  
1.359 (5)  
0.9300  
1.358 (7)  
0.9300  
Acta Cryst. (2018). C74  
sup-5  
supporting information  
C135—C136  
C135—H135  
C136—H136  
1.386 (4)  
0.9300  
0.9300  
C235—C236  
C235—H235  
C236—H236  
1.386 (6)  
0.9300  
0.9300  
O11—C11—N11  
O11—C11—C111  
N11—C11—C111  
C11—N11—C122  
120.4 (3)  
123.2 (2)  
116.4 (2)  
125.4 (3)  
117.3  
O21—C21—N21  
O21—C21—C211  
N21—C21—C211  
C21—N21—C222  
120.2 (10)  
123.1 (9)  
116.0 (8)  
125.8 (11)  
117.1  
C11—N11—H11  
C21—N21—H21  
C122—N11—H11  
C116—C111—C112  
C116—C111—C11  
C112—C111—C11  
C113—C112—C111  
C113—C112—H112  
C111—C112—H112  
C114—C113—C112  
C114—C113—H113  
C112—C113—H113  
C115—C114—C113  
C115—C114—H114  
C113—C114—H114  
C114—C115—C116  
C114—C115—H115  
C116—C115—H115  
C111—C116—C115  
C111—C116—H116  
C115—C116—H116  
C122—S121—C125  
N11—C122—C123  
N11—C122—S121  
C123—C122—S121  
C122—C123—C124  
C122—C123—C137  
C124—C123—C137  
C125—C124—C123  
C125—C124—H124  
C123—C124—H124  
C124—C125—C126  
C124—C125—S121  
C126—C125—S121  
C127—C126—C125  
C127—C126—H16A  
C125—C126—H16A  
C127—C126—H16B  
C125—C126—H16B  
H16A—C126—H16B  
C126—C127—H17A  
117.3  
C222—N21—H21  
C216—C211—C212  
C216—C211—C21  
C212—C211—C21  
C213—C212—C211  
C213—C212—H212  
C211—C212—H212  
C214—C213—C212  
C214—C213—H213  
C212—C213—H213  
C215—C214—C213  
C215—C214—H214  
C213—C214—H214  
C214—C215—C216  
C214—C215—H215  
C216—C215—H215  
C211—C216—C215  
C211—C216—H216  
C215—C216—H216  
C222—S221—C225  
N21—C222—C223  
N21—C222—S221  
C223—C222—S221  
C222—C223—C224  
C222—C223—C237  
C224—C223—C237  
C225—C224—C223  
C225—C224—H224  
C223—C224—H224  
C224—C225—C226  
C224—C225—S221  
C226—C225—S221  
C227—C226—C225  
C227—C226—H26A  
C225—C226—H26A  
C227—C226—H26B  
C225—C226—H26B  
H26A—C226—H26B  
C226—C227—H27A  
117.1  
118.8 (2)  
123.5 (2)  
117.6 (2)  
120.3 (3)  
119.8  
119.8  
120.1 (3)  
119.9  
119.9  
120.2 (3)  
119.9  
119.9  
120.1 (3)  
119.9  
118.7 (6)  
123.1 (8)  
117.5 (8)  
119.9 (8)  
120.0  
120.0  
119.9 (9)  
120.1  
120.1  
119.8 (9)  
120.1  
120.1  
119.7 (9)  
120.1  
119.9  
120.5 (3)  
119.8  
120.1  
120.4 (8)  
119.8  
119.8  
119.8  
91.45 (15)  
124.2 (2)  
123.5 (2)  
112.2 (2)  
111.4 (2)  
121.7 (2)  
126.8 (2)  
113.6 (3)  
123.2  
91.1 (4)  
124.0 (9)  
123.7 (8)  
111.8 (5)  
111.2 (5)  
121.4 (9)  
126.9 (9)  
113.4 (6)  
123.3  
123.2  
123.3  
128.9 (3)  
111.3 (2)  
119.6 (3)  
118.3 (3)  
107.7  
107.7  
107.7  
107.7  
107.1  
128.0 (9)  
110.5 (7)  
118.6 (7)  
117.5 (9)  
107.9  
107.9  
107.9  
107.9  
107.2  
109.5  
109.5  
Acta Cryst. (2018). C74  
sup-6  
supporting information  
C126—C127—H17B  
H17A—C127—H17B  
C126—C127—H17C  
H17A—C127—H17C  
H17B—C127—H17C  
O137—C137—C123  
O137—C137—C131  
C123—C137—C131  
C136—C131—C132  
C136—C131—C137  
C132—C131—C137  
C131—C132—C133  
C131—C132—Cl12  
C133—C132—Cl12  
C134—C133—C132  
C134—C133—H133  
C132—C133—H133  
C135—C134—C133  
C135—C134—H134  
C133—C134—H134  
C134—C135—C136  
C134—C135—H135  
C136—C135—H135  
C131—C136—C135  
C131—C136—H136  
C135—C136—H136  
109.5  
109.5  
109.5  
109.5  
C226—C227—H27B  
H27A—C227—H27B  
C226—C227—H27C  
H27A—C227—H27C  
H27B—C227—H27C  
O237—C237—C223  
O237—C237—C231  
C223—C237—C231  
C236—C231—C232  
C236—C231—C237  
C232—C231—C237  
C231—C232—C233  
C231—C232—Cl22  
C233—C232—Cl22  
C234—C233—C232  
C234—C233—H233  
C232—C233—H233  
C235—C234—C233  
C235—C234—H234  
C233—C234—H234  
C234—C235—C236  
C234—C235—H235  
C236—C235—H235  
C231—C236—C235  
C231—C236—H236  
C235—C236—H236  
109.5  
109.5  
109.5  
109.5  
109.5  
109.5  
122.6 (3)  
117.7 (3)  
119.7 (2)  
117.5 (3)  
119.8 (3)  
122.5 (3)  
121.2 (3)  
119.8 (2)  
119.0 (2)  
119.8 (3)  
120.1  
120.1  
120.4 (3)  
119.8  
119.8  
119.3 (3)  
120.4  
122.2 (10)  
117.4 (8)  
119.2 (8)  
117.7 (6)  
119.8 (7)  
122.4 (7)  
121.1 (6)  
119.7 (6)  
119.2 (6)  
119.8 (7)  
120.1  
120.1  
120.5 (7)  
119.8  
119.8  
119.2 (7)  
120.4  
120.4  
121.7 (3)  
119.1  
120.4  
121.7 (7)  
119.2  
119.1  
119.2  
O11—C11—N11—C122  
C111—C11—N11—C122  
O11—C11—C111—C116  
N11—C11—C111—C116  
O11—C11—C111—C112  
N11—C11—C111—C112  
C116—C111—C112—C113  
C11—C111—C112—C113  
C111—C112—C113—C114  
C112—C113—C114—C115  
C113—C114—C115—C116  
C112—C111—C116—C115  
C11—C111—C116—C115  
C114—C115—C116—C111  
C11—N11—C122—C123  
C11—N11—C122—S121  
C125—S121—C122—N11  
C125—S121—C122—C123  
N11—C122—C123—C124  
S121—C122—C123—C124  
N11—C122—C123—C137  
0.2 (11)  
O21—C21—N21—C222  
C211—C21—N21—C222  
O21—C21—C211—C216  
N21—C21—C211—C216  
O21—C21—C211—C212  
N21—C21—C211—C212  
C216—C211—C212—C213  
C21—C211—C212—C213  
C211—C212—C213—C214  
C212—C213—C214—C215  
C213—C214—C215—C216  
C212—C211—C216—C215  
C21—C211—C216—C215  
C214—C215—C216—C211  
C21—N21—C222—C223  
C21—N21—C222—S221  
C225—S221—C222—N21  
C225—S221—C222—C223  
N21—C222—C223—C224  
S221—C222—C223—C224  
N21—C222—C223—C237  
32 (9)  
−179.0 (8)  
−159.8 (8)  
19.4 (9)  
17.6 (10)  
−163.2 (6)  
0.3 (8)  
−177.2 (7)  
−0.8 (10)  
1.4 (10)  
−1.6 (11)  
−0.4 (10)  
176.9 (9)  
1.1 (12)  
178.5 (7)  
−0.7 (11)  
176.9 (7)  
−2.4 (5)  
−177.1 (8)  
2.1 (7)  
−158 (7)  
−178 (8)  
12 (8)  
12 (8)  
−158 (5)  
−8 (8)  
162 (7)  
11 (9)  
−13 (10)  
11 (10)  
7 (9)  
−163 (8)  
−9 (11)  
−180 (5)  
−9 (9)  
−160 (6)  
11 (4)  
165 (7)  
−7 (6)  
−23 (8)  
6.1 (10)  
Acta Cryst. (2018). C74  
sup-7  
supporting information  
S121—C122—C123—C137  
C122—C123—C124—C125  
C137—C123—C124—C125  
C123—C124—C125—C126  
C123—C124—C125—S121  
C122—S121—C125—C124  
C122—S121—C125—C126  
C124—C125—C126—C127  
S121—C125—C126—C127  
C122—C123—C137—O137  
C124—C123—C137—O137  
C122—C123—C137—C131  
C124—C123—C137—C131  
O137—C137—C131—C136  
C123—C137—C131—C136  
O137—C137—C131—C132  
C123—C137—C131—C132  
C136—C131—C132—C133  
C137—C131—C132—C133  
C136—C131—C132—Cl12  
C137—C131—C132—Cl12  
C131—C132—C133—C134  
Cl12—C132—C133—C134  
C132—C133—C134—C135  
C133—C134—C135—C136  
C132—C131—C136—C135  
C137—C131—C136—C135  
C134—C135—C136—C131  
−174.6 (7)  
−0.6 (8)  
175.9 (7)  
−176.1 (6)  
−1.1 (7)  
S221—C222—C223—C237  
165 (6)  
−3 (7)  
−175 (6)  
171 (5)  
12 (6)  
−13 (4)  
−175 (3)  
−103 (6)  
56 (4)  
C222—C223—C224—C225  
C237—C223—C224—C225  
C223—C224—C225—C226  
C223—C224—C225—S221  
C222—S221—C225—C224  
C222—S221—C225—C226  
C224—C225—C226—C227  
S221—C225—C226—C227  
C222—C223—C237—O237  
C224—C223—C237—O237  
C222—C223—C237—C231  
C224—C223—C237—C231  
O237—C237—C231—C236  
C223—C237—C231—C236  
O237—C237—C231—C232  
C223—C237—C231—C232  
C236—C231—C232—C233  
C237—C231—C232—C233  
C236—C231—C232—Cl22  
C237—C231—C232—Cl22  
C231—C232—C233—C234  
Cl22—C232—C233—C234  
C232—C233—C234—C235  
C233—C234—C235—C236  
C232—C231—C236—C235  
C237—C231—C236—C235  
C234—C235—C236—C231  
2.0 (5)  
177.5 (5)  
−159.7 (8)  
25.8 (8)  
−0.9 (11)  
−177.1 (12)  
−178.7 (5)  
5.1 (10)  
−96.8 (10)  
81.2 (6)  
78.3 (10)  
−103.8 (5)  
2.2 (5)  
−173.0 (5)  
−177.9 (3)  
7.0 (5)  
−1.0 (7)  
179.0 (4)  
−0.6 (8)  
24 (9)  
−165 (10)  
−169 (3)  
2 (8)  
−113 (8)  
80 (5)  
71 (8)  
−97 (4)  
−1 (3)  
176 (4)  
−180 (2)  
−3 (3)  
3 (5)  
−178 (3)  
−3 (6)  
1.0 (7)  
−1.8 (7)  
173.5 (5)  
0.2 (8)  
1 (6)  
−1 (5)  
−178 (4)  
1 (6)  
Hydrogen-bond geometry (Å, º)  
D—H···A  
D—H  
H···A  
D···A  
D—H···A  
N11—H11···O137  
N21—H21···O237  
C115—H115···O137i  
C215—H215···O237i  
0.86  
0.86  
0.93  
0.93  
2.03  
2.12  
2.53  
2.13  
2.671 (12)  
2.73 (10)  
3.438 (9)  
3.04 (7)  
131  
129  
166  
166  
Symmetry code: (i) −x, −y+1, −z+1.  
N-[3-(2-Chlorobenzoyl)-5-ethylthiophen-2-yl]-4-phenylbenzamide (II)  
Crystal data  
C26H20ClNO2S  
Mr = 445.94  
V = 2234.7 (2) Å3  
Z = 4  
Monoclinic, P21/c  
a = 10.7264 (6) Å  
b = 9.1208 (5) Å  
c = 22.9103 (15) Å  
β = 94.414 (2)°  
F(000) = 928  
Dx = 1.325 Mg m−3  
Mo Kα radiation, λ = 0.71073 Å  
Cell parameters from 7049 reflections  
θ = 1.8–30.9°  
Acta Cryst. (2018). C74  
sup-8  
supporting information  
µ = 0.29 mm−1  
T = 296 K  
Block, colourless  
0.28 × 0.27 × 0.22 mm  
Data collection  
Bruker Kappa APEXII  
diffractometer  
Radiation source: fine focus sealed tube  
φ and ω scans  
5148 independent reflections  
3570 reflections with I > 2σ(I)  
Rint = 0.033  
θ
max = 27.6°, θmin = 2.4°  
Absorption correction: multi-scan  
(SADABS; Bruker, 2012)  
h = −13→13  
k = −11→11  
l = −29→28  
T
min = 0.929, Tmax = 0.939  
24401 measured reflections  
Refinement  
Refinement on F2  
Least-squares matrix: full  
R[F2 > 2σ(F2)] = 0.047  
wR(F2) = 0.130  
S = 1.04  
5148 reflections  
373 parameters  
89 restraints  
Hydrogen site location: inferred from  
neighbouring sites  
H-atom parameters constrained  
w = 1/[σ2(Fo2) + (0.0487P)2 + 1.1314P]  
where P = (Fo2 + 2Fc2)/3  
(Δ/σ)max < 0.001  
Δρmax = 0.39 e Å−3  
Δρmin = −0.35 e Å−3  
Special details  
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance  
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;  
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate  
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.  
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)  
x
y
z
Uiso*/Ueq  
Occ. (<1)  
C11  
O11  
N11  
H11  
0.3958 (6)  
0.40738 (18)  
0.3397 (12)  
0.3373  
0.4457 (9)  
0.5052 (6)  
0.5103  
0.5562 (5)  
0.5946  
0.5519 (14)  
0.4928 (14)  
0.4875  
0.7159 (4)  
0.81059 (17)  
0.5857 (6)  
0.5195  
0.7310 (4)  
0.8626 (4)  
0.9375  
0.8822 (5)  
0.9709  
0.7726 (8)  
0.6418 (7)  
0.5671  
0.49542 (14)  
0.45845 (7)  
0.4797 (3)  
0.5064  
0.55744 (15)  
0.57421 (17)  
0.5470  
0.63050 (16)  
0.6407  
0.6727 (3)  
0.6557 (2)  
0.6831  
0.0388 (11)  
0.0652 (5)  
0.0398 (10)  
0.048*  
0.0352 (11)  
0.0441 (13)  
0.053*  
0.0449 (12)  
0.054*  
0.0391 (5)  
0.0430 (15)  
0.052*  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
C111  
C112  
H112  
C113  
H113  
C114  
C115  
H115  
C116  
H116  
S121  
C122  
C123  
C124  
H124  
0.4418 (11)  
0.4044  
0.6208 (5)  
0.5316  
0.59912 (17)  
0.5888  
0.0410 (15)  
0.049*  
0.2951 (2)  
0.2865 (7)  
0.2174 (7)  
0.1733 (3)  
0.1254  
0.66308 (19)  
0.5520 (5)  
0.4269 (5)  
0.4230 (3)  
0.3464  
0.36452 (9)  
0.42463 (16)  
0.41147 (18)  
0.35089 (14)  
0.3344  
0.0482 (4)  
0.0361 (11)  
0.0374 (11)  
0.0421 (10)  
0.050*  
Acta Cryst. (2018). C74  
sup-9  
supporting information  
C125  
C126  
H16A  
H16B  
C127  
H17A  
H17B  
H17C  
C137  
O137  
C131  
C132  
Cl12  
C133  
H133  
C134  
H134  
C135  
H135  
C136  
H136  
C141  
C142  
H142  
C143  
H143  
C144  
H144  
C145  
H145  
C146  
H146  
C21  
0.2070 (4)  
0.1811 (4)  
0.2592  
0.1272  
0.1202 (6)  
0.0915  
0.5394 (4)  
0.5720 (4)  
0.5691  
0.4960  
0.7183 (5)  
0.7252  
0.32011 (13)  
0.25571 (13)  
0.2371  
0.2381  
0.24404 (19)  
0.2034  
0.0498 (11)  
0.0697 (12)  
0.084*  
0.084*  
0.123 (2)  
0.185*  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.832 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.1797  
0.0505  
0.7948  
0.7285  
0.2537  
0.2676  
0.185*  
0.185*  
0.1907 (3)  
0.2433 (7)  
0.0991 (3)  
−0.0272 (3)  
−0.08524 (14)  
−0.1105 (4)  
−0.1954  
−0.0674 (5)  
−0.1232  
0.0577 (5)  
0.0861  
0.1416 (4)  
0.2260  
0.6107 (9)  
0.7192 (14)  
0.7536  
0.7770 (11)  
0.8501  
0.7267 (4)  
0.7643  
0.6218 (5)  
0.5888  
0.5641 (6)  
0.4926  
0.412 (4)  
0.40738 (18)  
0.347 (6)  
0.3536  
0.458 (5)  
0.482 (4)  
0.4649  
0.530 (3)  
0.5515  
0.549 (7)  
0.502 (8)  
0.5036  
0.455 (6)  
0.4203  
0.2749 (12)  
0.273 (4)  
0.3189 (4)  
0.3199 (7)  
0.1982 (3)  
0.2248 (3)  
0.4023 (2)  
0.1119 (5)  
0.1314  
−0.0279 (5)  
−0.1042  
−0.0580 (4)  
−0.1541  
0.0547 (4)  
0.0342  
0.7926 (10)  
0.8753 (18)  
0.9212  
0.8902 (12)  
0.9448  
0.8248 (7)  
0.8376  
0.7410 (8)  
0.6946  
0.7248 (9)  
0.6673  
0.7075 (17)  
0.81059 (17)  
0.582 (3)  
0.5096  
0.722 (2)  
0.864 (2)  
0.9447  
0.884 (3)  
0.9779  
0.766 (4)  
0.630 (4)  
0.5523  
0.609 (3)  
0.5190  
0.45606 (18)  
0.5056 (2)  
0.4394 (3)  
0.42736 (15)  
0.43201 (9)  
0.4147 (3)  
0.4074  
0.4131 (5)  
0.4042  
0.4244 (5)  
0.4226  
0.4384 (4)  
0.4470  
0.73308 (18)  
0.7432 (3)  
0.7120  
0.7991 (3)  
0.8050  
0.84572 (17)  
0.8833  
0.83703 (17)  
0.8686  
0.7809 (2)  
0.7754  
0.4927 (7)  
0.45845 (7)  
0.4777 (13)  
0.5018  
0.5554 (7)  
0.5769 (8)  
0.5528  
0.6336 (8)  
0.6466  
0.6721 (13)  
0.6532 (11)  
0.6795  
0.5960 (9)  
0.5847  
0.3678 (5)  
0.4264 (8)  
0.0384 (6)  
0.0531 (14)  
0.0427 (5)  
0.0510 (8)  
0.0749 (4)  
0.0758 (14)  
0.091*  
0.0955 (19)  
0.115*  
0.0921 (13)  
0.111*  
0.0625 (10)  
0.075*  
0.0418 (11)  
0.0574 (11)  
0.069*  
0.0649 (12)  
0.078*  
0.0556 (11)  
0.067*  
0.0573 (12)  
0.069*  
0.0515 (15)  
0.062*  
0.0388 (11)  
0.0652 (5)  
0.0398 (10)  
0.048*  
0.0352 (11)  
0.0441 (13)  
0.053*  
0.0449 (12)  
0.054*  
0.0391 (5)  
0.0430 (15)  
0.052*  
0.0410 (15)  
0.049*  
0.0482 (4)  
0.0361 (11)  
O21  
N21  
H21  
C211  
C212  
H212  
C213  
H213  
C214  
C215  
H215  
C216  
H216  
S221  
C222  
0.6821 (11)  
0.565 (3)  
Acta Cryst. (2018). C74  
sup-10  
supporting information  
C223  
C224  
H224  
C225  
C226  
H26A  
H26B  
C227  
H27A  
H27B  
H27C  
C237  
O237  
C231  
C232  
Cl22  
C233  
H233  
C234  
H234  
C235  
H235  
C236  
H236  
C241  
C242  
H242  
C243  
H243  
C244  
H244  
C245  
H245  
C246  
H246  
0.204 (4)  
0.149 (2)  
0.0943  
0.184 (2)  
0.1403 (17)  
0.1046  
0.0747  
0.243 (2)  
0.2090  
0.440 (3)  
0.4448 (19)  
0.3737  
0.561 (2)  
0.606 (2)  
0.5211  
0.6787  
0.668 (3)  
0.6948  
0.4128 (9)  
0.3538 (7)  
0.3381  
0.3232 (5)  
0.2615 (6)  
0.2408  
0.2632  
0.2278 (8)  
0.1893  
0.0374 (11)  
0.0421 (10)  
0.050*  
0.0498 (11)  
0.0697 (12)  
0.084*  
0.084*  
0.123 (2)  
0.185*  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.168 (5)  
0.3066  
0.2776  
0.5950  
0.7524  
0.2248  
0.2477  
0.185*  
0.185*  
0.2050 (16)  
0.263 (4)  
0.1151 (12)  
−0.0129 (12)  
−0.0753 (9)  
−0.0937 (17)  
−0.1797  
−0.046 (2)  
−0.1006  
0.080 (2)  
0.1118  
0.1621 (18)  
0.2480  
0.619 (5)  
0.715 (7)  
0.7375  
0.778 (6)  
0.8355  
0.753 (3)  
0.8077  
0.649 (3)  
0.6225  
0.584 (4)  
0.5144  
0.3146 (18)  
0.317 (4)  
0.1902 (12)  
0.2080 (11)  
0.3806 (11)  
0.0918 (16)  
0.1069  
−0.0447 (17)  
−0.1237  
−0.0673 (16)  
−0.1617  
0.0502 (16)  
0.0352  
0.783 (5)  
0.886 (9)  
0.9411  
0.907 (7)  
0.9828  
0.816 (4)  
0.8137  
0.730 (4)  
0.6840  
0.4529 (9)  
0.5013 (12)  
0.4391 (13)  
0.4390 (7)  
0.4505 (4)  
0.4281 (17)  
0.4254  
0.421 (3)  
0.4148  
0.424 (3)  
0.4202  
0.432 (2)  
0.4327  
0.7301 (9)  
0.7380 (15)  
0.7063  
0.7926 (16)  
0.7984  
0.8380 (10)  
0.8716  
0.0384 (6)  
0.0531 (14)  
0.0427 (5)  
0.0510 (8)  
0.0749 (4)  
0.0758 (14)  
0.091*  
0.0955 (19)  
0.115*  
0.0921 (13)  
0.111*  
0.0625 (10)  
0.075*  
0.0418 (11)  
0.0574 (11)  
0.069*  
0.0649 (12)  
0.078*  
0.0556 (11)  
0.067*  
0.8336 (8)  
0.8667  
0.7794 (11)  
0.7762  
0.0573 (12)  
0.069*  
0.0515 (15)  
0.062*  
0.711 (5)  
0.6497  
Atomic displacement parameters (Å2)  
U11  
U22  
U33  
U12  
U13  
U23  
C11  
O11  
N11  
C111  
C112  
C113  
C114  
C115  
C116  
0.043 (2)  
0.0996 (13)  
0.049 (2)  
0.036 (2)  
0.056 (3)  
0.055 (3)  
0.0417 (14)  
0.051 (3)  
0.047 (3)  
0.0336 (11)  
0.0470 (9)  
0.0364 (9)  
0.0323 (11)  
0.0357 (11)  
0.0367 (11)  
0.0388 (12)  
0.0383 (16)  
0.0320 (13)  
0.0401 (12)  
0.0461 (9)  
−0.0061 (12)  
0.0016 (12)  
−0.0137 (9)  
−0.0008 (12)  
0.0027 (11)  
0.0007 (14)  
0.0043 (15)  
0.0055 (8)  
0.0029 (9)  
0.0143 (7)  
0.0053 (8)  
0.0008 (9)  
0.0061 (9)  
−0.0037 (9)  
−0.0023 (9)  
0.0073 (11)  
0.0015 (10)  
−0.0262 (9)  
−0.0076 (11)  
−0.0027 (13)  
−0.0113 (12)  
−0.0132 (15)  
−0.0002 (11)  
−0.005 (2)  
0.0334 (10)  
0.0374 (11)  
0.0405 (12)  
0.0434 (13)  
0.0371 (11)  
0.0394 (12)  
0.0430 (13)  
0.0016 (15)  
−0.0006 (14)  
−0.0078 (18)  
Acta Cryst. (2018). C74  
sup-11  
supporting information  
S121  
C122  
C123  
C124  
C125  
C126  
C127  
C137  
O137  
C131  
C132  
Cl12  
C133  
C134  
C135  
C136  
C141  
C142  
C143  
C144  
C145  
C146  
C21  
0.0628 (9)  
0.038 (2)  
0.039 (2)  
0.045 (2)  
0.061 (2)  
0.096 (3)  
0.188 (5)  
0.0413 (13)  
0.070 (3)  
0.0480 (14)  
0.0507 (14)  
0.0577 (5)  
0.0593 (19)  
0.102 (3)  
0.120 (4)  
0.068 (2)  
0.0490 (19)  
0.070 (2)  
0.0725 (17)  
0.073 (3)  
0.074 (3)  
0.057 (3)  
0.043 (2)  
0.0996 (13)  
0.049 (2)  
0.036 (2)  
0.056 (3)  
0.055 (3)  
0.0417 (14)  
0.051 (3)  
0.047 (3)  
0.0628 (9)  
0.038 (2)  
0.039 (2)  
0.045 (2)  
0.061 (2)  
0.096 (3)  
0.188 (5)  
0.0413 (13)  
0.070 (3)  
0.0480 (14)  
0.0507 (14)  
0.0577 (5)  
0.0593 (19)  
0.102 (3)  
0.120 (4)  
0.068 (2)  
0.0490 (19)  
0.0437 (6)  
0.0365 (14)  
0.0393 (14)  
0.0449 (15)  
0.0515 (17)  
0.076 (3)  
0.0379 (4)  
0.0337 (10)  
0.0340 (10)  
0.0351 (12)  
0.0357 (12)  
0.0348 (15)  
0.061 (3)  
0.0343 (12)  
0.0364 (12)  
0.0370 (11)  
0.0369 (18)  
0.0845 (11)  
0.067 (4)  
0.101 (5)  
0.115 (3)  
0.076 (3)  
0.0357 (12)  
0.0430 (19)  
0.053 (2)  
0.0384 (16)  
0.0380 (14)  
0.0429 (13)  
0.0401 (12)  
0.0461 (9)  
0.0334 (10)  
0.0374 (11)  
0.0405 (12)  
0.0434 (13)  
0.0371 (11)  
0.0394 (12)  
0.0430 (13)  
0.0379 (4)  
0.0337 (10)  
0.0340 (10)  
0.0351 (12)  
0.0357 (12)  
0.0348 (15)  
0.061 (3)  
0.0343 (12)  
0.0364 (12)  
0.0370 (11)  
0.0369 (18)  
0.0845 (11)  
0.067 (4)  
0.101 (5)  
0.115 (3)  
0.076 (3)  
0.0357 (12)  
−0.0019 (5)  
0.0003 (16)  
0.0002 (16)  
0.0024 (14)  
0.0066 (16)  
0.007 (2)  
0.0022 (5)  
0.0094 (4)  
0.0036 (9)  
0.0028 (10)  
0.0017 (10)  
−0.0021 (12)  
−0.0011 (12)  
−0.0049 (17)  
−0.026 (3)  
0.0041 (10)  
−0.0062 (16)  
0.0069 (12)  
−0.0018 (12)  
0.0036 (7)  
−0.0001 (10)  
−0.0053 (10)  
0.0019 (11)  
0.0089 (15)  
0.032 (2)  
−0.0019 (9)  
0.0080 (9)  
−0.0018 (9)  
0.0008 (12)  
0.0109 (7)  
−0.005 (2)  
−0.023 (3)  
−0.0180 (18)  
−0.0044 (13)  
−0.0064 (11)  
−0.0055 (17)  
−0.013 (2)  
−0.0122 (14)  
0.0025 (13)  
0.0006 (12)  
0.0029 (9)  
0.116 (4)  
0.034 (4)  
0.0398 (11)  
0.0515 (10)  
0.0439 (12)  
0.0647 (16)  
0.0824 (7)  
0.099 (3)  
−0.0030 (10)  
−0.0188 (15)  
−0.0079 (10)  
−0.0097 (12)  
0.0191 (4)  
−0.0310 (18)  
−0.051 (2)  
−0.0192 (19)  
−0.0061 (13)  
0.0056 (15)  
−0.011 (2)  
−0.0057 (17)  
0.008 (3)  
0.036 (3)  
0.084 (3)  
0.0459 (16)  
0.0465 (14)  
0.0407 (17)  
0.058 (3)  
0.066 (4)  
0.0538 (16)  
0.060 (2)  
0.021 (2)  
0.0032 (12)  
−0.0003 (18)  
−0.0123 (19)  
−0.0051 (17)  
0.0091 (15)  
0.0062 (14)  
0.0016 (12)  
−0.0137 (9)  
−0.0008 (12)  
0.0027 (11)  
0.0007 (14)  
0.0043 (15)  
0.0055 (8)  
0.0016 (15)  
−0.0006 (14)  
0.0022 (5)  
0.0028 (10)  
0.0017 (10)  
−0.0021 (12)  
−0.0011 (12)  
−0.0049 (17)  
−0.026 (3)  
−0.006 (2)  
0.024 (2)  
0.017 (2)  
0.003 (2)  
0.055 (2)  
0.0336 (11)  
0.0470 (9)  
0.0364 (9)  
0.0323 (11)  
0.0357 (11)  
0.0367 (11)  
0.0388 (12)  
0.0383 (16)  
0.0320 (13)  
0.0437 (6)  
0.0365 (14)  
0.0393 (14)  
0.0449 (15)  
0.0515 (17)  
0.076 (3)  
−0.0061 (12)  
−0.0262 (9)  
−0.0076 (11)  
−0.0027 (13)  
−0.0113 (12)  
−0.0132 (15)  
−0.0002 (11)  
−0.005 (2)  
−0.0078 (18)  
−0.0019 (5)  
0.0003 (16)  
0.0002 (16)  
0.0024 (14)  
0.0066 (16)  
0.007 (2)  
O21  
N21  
0.0143 (7)  
0.0053 (8)  
0.0008 (9)  
0.0061 (9)  
C211  
C212  
C213  
C214  
C215  
C216  
S221  
C222  
C223  
C224  
C225  
C226  
C227  
C237  
O237  
C231  
C232  
Cl22  
C233  
C234  
C235  
C236  
C241  
−0.0037 (9)  
−0.0023 (9)  
0.0073 (11)  
0.0015 (10)  
0.0094 (4)  
0.0036 (9)  
−0.0001 (10)  
−0.0053 (10)  
0.0019 (11)  
0.0089 (15)  
0.032 (2)  
−0.0019 (9)  
0.0080 (9)  
−0.0018 (9)  
0.0008 (12)  
0.0109 (7)  
0.116 (4)  
0.034 (4)  
0.0398 (11)  
0.0515 (10)  
0.0439 (12)  
0.0647 (16)  
0.0824 (7)  
0.099 (3)  
−0.0030 (10)  
−0.0188 (15)  
−0.0079 (10)  
−0.0097 (12)  
0.0191 (4)  
−0.0310 (18)  
−0.051 (2)  
−0.0192 (19)  
−0.0061 (13)  
0.0056 (15)  
0.0041 (10)  
−0.0062 (16)  
0.0069 (12)  
−0.0018 (12)  
0.0036 (7)  
−0.0057 (17)  
0.008 (3)  
0.036 (3)  
−0.005 (2)  
−0.023 (3)  
−0.0180 (18)  
−0.0044 (13)  
−0.0064 (11)  
0.084 (3)  
0.0459 (16)  
0.0465 (14)  
0.0407 (17)  
0.021 (2)  
0.0032 (12)  
Acta Cryst. (2018). C74  
sup-12  
supporting information  
C242  
C243  
C244  
C245  
C246  
0.070 (2)  
0.0725 (17)  
0.073 (3)  
0.074 (3)  
0.057 (3)  
0.058 (3)  
0.066 (4)  
0.0538 (16)  
0.060 (2)  
0.055 (2)  
0.0430 (19)  
0.053 (2)  
0.0384 (16)  
0.0380 (14)  
0.0429 (13)  
−0.011 (2)  
−0.006 (2)  
0.024 (2)  
0.017 (2)  
0.003 (2)  
−0.0003 (18)  
−0.0123 (19)  
−0.0051 (17)  
0.0091 (15)  
0.0062 (14)  
−0.0055 (17)  
−0.013 (2)  
−0.0122 (14)  
0.0025 (13)  
0.0006 (12)  
Geometric parameters (Å, º)  
C11—O11  
1.223 (3)  
C21—N21  
1.370 (5)  
C11—N11  
C11—C111  
N11—C122  
N11—H11  
1.367 (3)  
1.486 (3)  
1.379 (4)  
0.8600  
1.389 (3)  
1.399 (4)  
1.373 (3)  
0.9300  
1.394 (4)  
0.9300  
1.392 (4)  
1.487 (3)  
1.382 (3)  
0.9300  
C21—C211  
N21—C222  
N21—H21  
1.486 (5)  
1.381 (6)  
0.8600  
1.391 (5)  
1.401 (6)  
1.374 (5)  
0.9300  
1.394 (6)  
0.9300  
1.392 (5)  
1.487 (5)  
1.383 (5)  
0.9300  
C211—C216  
C211—C212  
C212—C213  
C212—H212  
C213—C214  
C213—H213  
C214—C215  
C214—C241  
C215—C216  
C215—H215  
C216—H216  
S221—C222  
S221—C225  
C222—C223  
C223—C224  
C223—C237  
C224—C225  
C224—H224  
C225—C226  
C226—C227  
C226—H26A  
C226—H26B  
C227—H27A  
C227—H27B  
C227—H27C  
C237—O237  
C237—C231  
C231—C232  
C231—C236  
C232—C233  
C232—Cl22  
C233—C234  
C233—H233  
C234—C235  
C234—H234  
C235—C236  
C111—C116  
C111—C112  
C112—C113  
C112—H112  
C113—C114  
C113—H113  
C114—C115  
C114—C141  
C115—C116  
C115—H115  
C116—H116  
S121—C122  
S121—C125  
C122—C123  
C123—C124  
C123—C137  
C124—C125  
C124—H124  
C125—C126  
C126—C127  
C126—H16A  
C126—H16B  
C127—H17A  
C127—H17B  
C127—H17C  
C137—O137  
C137—C131  
C131—C132  
C131—C136  
C132—C133  
C132—Cl12  
C133—C134  
C133—H133  
C134—C135  
C134—H134  
0.9300  
0.9300  
1.719 (4)  
1.748 (5)  
1.382 (5)  
1.431 (5)  
1.464 (6)  
1.341 (5)  
0.9300  
1.511 (5)  
1.500 (7)  
0.9700  
0.9700  
0.9600  
0.9600  
0.9600  
1.230 (5)  
1.506 (5)  
1.382 (5)  
1.387 (5)  
1.380 (5)  
1.739 (5)  
1.358 (6)  
0.9300  
1.718 (2)  
1.747 (3)  
1.381 (3)  
1.432 (3)  
1.463 (4)  
1.340 (3)  
0.9300  
1.510 (3)  
1.501 (6)  
0.9700  
0.9700  
0.9600  
0.9600  
0.9600  
1.228 (3)  
1.506 (3)  
1.382 (3)  
1.387 (4)  
1.380 (4)  
1.741 (3)  
1.358 (5)  
0.9300  
1.374 (7)  
0.9300  
1.388 (6)  
1.375 (5)  
0.9300  
Acta Cryst. (2018). C74  
sup-13  
supporting information  
C135—C136  
C135—H135  
C136—H136  
C141—C146  
C141—C142  
C142—C143  
C142—H142  
C143—C144  
C143—H143  
C144—C145  
C144—H144  
C145—C146  
C145—H145  
C146—H146  
1.388 (4)  
0.9300  
0.9300  
1.385 (3)  
1.392 (4)  
1.385 (4)  
0.9300  
1.370 (6)  
0.9300  
1.363 (4)  
0.9300  
1.391 (4)  
0.9300  
C235—H235  
C236—H236  
C241—C246  
C241—C242  
C242—C243  
C242—H242  
C243—C244  
C243—H243  
C244—C245  
C244—H244  
C245—C246  
C245—H245  
C246—H246  
0.9300  
0.9300  
1.385 (5)  
1.392 (7)  
1.386 (5)  
0.9300  
1.370 (8)  
0.9300  
1.364 (6)  
0.9300  
1.392 (5)  
0.9300  
0.9300  
0.9300  
O11—C11—N11  
O11—C11—C111  
N11—C11—C111  
C11—N11—C122  
C11—N11—H11  
119.8 (2)  
123.3 (2)  
116.8 (2)  
125.2 (2)  
117.4  
C145—C146—H146  
N21—C21—C211  
C21—N21—C222  
119.3  
116.1 (7)  
124.1 (8)  
118.0  
C21—N21—H21  
C222—N21—H21  
C216—C211—C212  
C216—C211—C21  
C212—C211—C21  
C213—C212—C211  
C213—C212—H212  
C211—C212—H212  
C212—C213—C214  
C212—C213—H213  
C214—C213—H213  
C215—C214—C213  
C215—C214—C241  
C213—C214—C241  
C216—C215—C214  
C216—C215—H215  
C214—C215—H215  
C215—C216—C211  
C215—C216—H216  
C211—C216—H216  
C222—S221—C225  
N21—C222—C223  
N21—C222—S221  
C223—C222—S221  
C222—C223—C224  
C222—C223—C237  
C224—C223—C237  
C225—C224—C223  
C225—C224—H224  
C223—C224—H224  
118.0  
C122—N11—H11  
C116—C111—C112  
C116—C111—C11  
C112—C111—C11  
C113—C112—C111  
C113—C112—H112  
C111—C112—H112  
C112—C113—C114  
C112—C113—H113  
C114—C113—H113  
C115—C114—C113  
C115—C114—C141  
C113—C114—C141  
C116—C115—C114  
C116—C115—H115  
C114—C115—H115  
C115—C116—C111  
C115—C116—H116  
C111—C116—H116  
C122—S121—C125  
N11—C122—C123  
N11—C122—S121  
C123—C122—S121  
C122—C123—C124  
C122—C123—C137  
C124—C123—C137  
C125—C124—C123  
C125—C124—H124  
117.4  
117.6 (9)  
123.8 (7)  
117.4 (7)  
120.0 (7)  
120.0  
120.0  
121.4 (7)  
119.3  
118.0 (2)  
124.2 (2)  
117.7 (2)  
120.6 (2)  
119.7  
119.7  
121.7 (2)  
119.1  
119.3  
119.1  
117.5 (6)  
121.1 (8)  
121.4 (6)  
120.9 (6)  
119.5  
119.5  
120.3 (6)  
119.8  
117.4 (2)  
121.1 (2)  
121.5 (2)  
121.3 (3)  
119.3  
119.3  
120.9 (2)  
119.5  
119.8  
119.5  
91.3 (3)  
123.5 (7)  
123.5 (7)  
112.1 (4)  
111.0 (4)  
121.5 (7)  
127.0 (8)  
114.2 (5)  
122.9  
91.49 (12)  
124.1 (2)  
123.93 (18)  
111.91 (17)  
111.4 (2)  
122.3 (2)  
126.3 (2)  
114.1 (2)  
123.0  
122.9  
Acta Cryst. (2018). C74  
sup-14  
supporting information  
C123—C124—H124  
C124—C125—C126  
C124—C125—S121  
C126—C125—S121  
C127—C126—C125  
C127—C126—H16A  
C125—C126—H16A  
C127—C126—H16B  
C125—C126—H16B  
H16A—C126—H16B  
C126—C127—H17A  
C126—C127—H17B  
H17A—C127—H17B  
C126—C127—H17C  
H17A—C127—H17C  
H17B—C127—H17C  
O137—C137—C123  
O137—C137—C131  
C123—C137—C131  
C132—C131—C136  
C132—C131—C137  
C136—C131—C137  
C133—C132—C131  
C133—C132—Cl12  
C131—C132—Cl12  
C134—C133—C132  
C134—C133—H133  
C132—C133—H133  
C133—C134—C135  
C133—C134—H134  
C135—C134—H134  
C134—C135—C136  
C134—C135—H135  
C136—C135—H135  
C131—C136—C135  
C131—C136—H136  
C135—C136—H136  
C146—C141—C142  
C146—C141—C114  
C142—C141—C114  
C143—C142—C141  
C143—C142—H142  
C141—C142—H142  
C144—C143—C142  
C144—C143—H143  
C142—C143—H143  
C145—C144—C143  
C145—C144—H144  
123.0  
C224—C225—C226  
C224—C225—S221  
C226—C225—S221  
C227—C226—C225  
C227—C226—H26A  
C225—C226—H26A  
C227—C226—H26B  
C225—C226—H26B  
H26A—C226—H26B  
C226—C227—H27A  
C226—C227—H27B  
H27A—C227—H27B  
C226—C227—H27C  
H27A—C227—H27C  
H27B—C227—H27C  
O237—C237—C223  
O237—C237—C231  
C223—C237—C231  
C232—C231—C236  
C232—C231—C237  
C236—C231—C237  
C233—C232—C231  
C233—C232—Cl22  
C231—C232—Cl22  
C234—C233—C232  
C234—C233—H233  
C232—C233—H233  
C233—C234—C235  
C233—C234—H234  
C235—C234—H234  
C234—C235—C236  
C234—C235—H235  
C236—C235—H235  
C231—C236—C235  
C231—C236—H236  
C235—C236—H236  
C246—C241—C242  
C246—C241—C214  
C242—C241—C214  
C243—C242—C241  
C243—C242—H242  
C241—C242—H242  
C244—C243—C242  
C244—C243—H243  
C242—C243—H243  
C245—C244—C243  
C245—C244—H244  
C243—C244—H244  
128.5 (7)  
111.0 (4)  
119.7 (6)  
113.2 (8)  
108.9  
108.9  
108.9  
108.9  
107.7  
109.5  
109.5  
109.5  
109.5  
109.5  
109.5  
122.0 (8)  
118.4 (7)  
118.7 (6)  
118.5 (5)  
122.1 (6)  
119.0 (6)  
121.4 (6)  
118.6 (6)  
120.0 (6)  
119.3 (6)  
120.3  
120.3  
120.7 (6)  
119.7  
119.7  
120.2 (6)  
119.9  
129.3 (3)  
111.17 (18)  
119.5 (2)  
113.2 (3)  
108.9  
108.9  
108.9  
108.9  
107.8  
109.5  
109.5  
109.5  
109.5  
109.5  
109.5  
122.7 (2)  
118.9 (2)  
118.3 (2)  
118.8 (2)  
122.2 (2)  
119.0 (2)  
121.3 (3)  
118.6 (2)  
120.0 (2)  
119.4 (3)  
120.3  
120.3  
120.8 (3)  
119.6  
119.6  
120.2 (3)  
119.9  
119.9  
119.7 (6)  
120.1  
119.9  
119.6 (3)  
120.2  
120.1  
120.2  
117.4 (6)  
121.6 (7)  
120.6 (7)  
120.8 (6)  
119.6  
119.6  
119.6 (10)  
120.2  
117.3 (2)  
121.9 (2)  
120.7 (3)  
121.1 (4)  
119.4  
119.4  
120.2 (4)  
119.9  
120.2  
119.7 (8)  
120.1  
119.9  
120.1 (3)  
120.0  
119  
Acta Cryst. (2018). C74  
sup-15  
supporting information  
C143—C144—H144  
C144—C145—C146  
C144—C145—H145  
C146—C145—H145  
C141—C146—C145  
C141—C146—H146  
120.0  
119.9 (3)  
120.1  
120.1  
121.5 (3)  
119.3  
C244—C245—C246  
C244—C245—H245  
C246—C245—H245  
C241—C246—C245  
C241—C246—H246  
C245—C246—H246  
119.4 (7)  
120.3  
120.3  
121.2 (6)  
119.4  
119.4  
O11—C11—N11—C122  
−3.8 (14)  
179.1 (11)  
−175.0 (9)  
1.9 (10)  
C144—C145—C146—C141  
C211—C21—N21—C222  
N21—C21—C211—C216  
N21—C21—C211—C212  
C216—C211—C212—C213  
C21—C211—C212—C213  
C211—C212—C213—C214  
C212—C213—C214—C215  
C212—C213—C214—C241  
C213—C214—C215—C216  
C241—C214—C215—C216  
C214—C215—C216—C211  
C212—C211—C216—C215  
C21—C211—C216—C215  
C21—N21—C222—C223  
C21—N21—C222—S221  
C225—S221—C222—N21  
C225—S221—C222—C223  
N21—C222—C223—C224  
S221—C222—C223—C224  
N21—C222—C223—C237  
S221—C222—C223—C237  
C222—C223—C224—C225  
C237—C223—C224—C225  
C223—C224—C225—C226  
C223—C224—C225—S221  
C222—S221—C225—C224  
C222—S221—C225—C226  
C224—C225—C226—C227  
S221—C225—C226—C227  
C222—C223—C237—O237  
C224—C223—C237—O237  
C222—C223—C237—C231  
C224—C223—C237—C231  
O237—C237—C231—C232  
C223—C237—C231—C232  
O237—C237—C231—C236  
C223—C237—C231—C236  
C236—C231—C232—C233  
C237—C231—C232—C233  
C236—C231—C232—Cl22  
−0.1 (12)  
163 (6)  
10 (6)  
−157 (5)  
16 (6)  
−177 (4)  
−5 (7)  
−7 (8)  
170 (4)  
8 (10)  
−169 (7)  
3 (10)  
−15 (8)  
178 (6)  
−178 (5)  
14 (8)  
169 (4)  
−1 (4)  
−172 (5)  
−2 (5)  
0 (7)  
170 (4)  
5 (5)  
−166 (4)  
−176 (3)  
−6 (4)  
C111—C11—N11—C122  
O11—C11—C111—C116  
N11—C11—C111—C116  
O11—C11—C111—C112  
N11—C11—C111—C112  
C116—C111—C112—C113  
C11—C111—C112—C113  
C111—C112—C113—C114  
C112—C113—C114—C115  
C112—C113—C114—C141  
C113—C114—C115—C116  
C141—C114—C115—C116  
C114—C115—C116—C111  
C112—C111—C116—C115  
C11—C111—C116—C115  
C11—N11—C122—C123  
C11—N11—C122—S121  
C125—S121—C122—N11  
C125—S121—C122—C123  
N11—C122—C123—C124  
S121—C122—C123—C124  
N11—C122—C123—C137  
S121—C122—C123—C137  
C122—C123—C124—C125  
C137—C123—C124—C125  
C123—C124—C125—C126  
C123—C124—C125—S121  
C122—S121—C125—C124  
C122—S121—C125—C126  
C124—C125—C126—C127  
S121—C125—C126—C127  
C122—C123—C137—O137  
C124—C123—C137—O137  
C122—C123—C137—C131  
C124—C123—C137—C131  
O137—C137—C131—C132  
C123—C137—C131—C132  
O137—C137—C131—C136  
C123—C137—C131—C136  
C136—C131—C132—C133  
2.1 (10)  
179.1 (9)  
−1.0 (10)  
−178.3 (6)  
0.6 (12)  
−0.5 (16)  
178.1 (7)  
0.8 (18)  
−177.7 (12)  
−1.3 (19)  
1.4 (14)  
178.5 (11)  
−171.9 (10)  
6.3 (15)  
−179.5 (8)  
−1.0 (6)  
179.3 (8)  
0.9 (8)  
1.9 (13)  
−176.6 (6)  
−0.2 (8)  
177.1 (6)  
178.4 (5)  
−0.5 (6)  
4 (3)  
175 (3)  
−142 (3)  
49 (3)  
0.9 (4)  
−178.2 (4)  
125.9 (5)  
−55.2 (5)  
−11.7 (11)  
171.3 (7)  
171.0 (6)  
−6.0 (10)  
113.7 (7)  
−68.8 (7)  
−63.6 (7)  
113.8 (6)  
0.3 (6)  
3 (6)  
174 (4)  
172 (3)  
−17 (6)  
104 (4)  
−65 (3)  
−69 (4)  
121 (3)  
−5 (3)  
−178 (2)  
177.6 (19)  
Acta Cryst. (2018). C74  
sup-16  
supporting information  
C137—C131—C132—C133  
C136—C131—C132—Cl12  
C137—C131—C132—Cl12  
C131—C132—C133—C134  
Cl12—C132—C133—C134  
C132—C133—C134—C135  
C133—C134—C135—C136  
C132—C131—C136—C135  
C137—C131—C136—C135  
C134—C135—C136—C131  
C115—C114—C141—C146  
C113—C114—C141—C146  
C115—C114—C141—C142  
C113—C114—C141—C142  
C146—C141—C142—C143  
C114—C141—C142—C143  
C141—C142—C143—C144  
C142—C143—C144—C145  
C143—C144—C145—C146  
C142—C141—C146—C145  
C114—C141—C146—C145  
−177.1 (4)  
176.6 (4)  
−0.7 (5)  
−1.2 (8)  
−177.5 (6)  
0.6 (12)  
C237—C231—C232—Cl22  
4 (2)  
5 (4)  
C231—C232—C233—C234  
Cl22—C232—C233—C234  
C232—C233—C234—C235  
C233—C234—C235—C236  
C232—C231—C236—C235  
C237—C231—C236—C235  
C234—C235—C236—C231  
C215—C214—C241—C246  
C213—C214—C241—C246  
C215—C214—C241—C242  
C213—C214—C241—C242  
C246—C241—C242—C243  
C214—C241—C242—C243  
C241—C242—C243—C244  
C242—C243—C244—C245  
C243—C244—C245—C246  
C242—C241—C246—C245  
C214—C241—C246—C245  
C244—C245—C246—C241  
−177 (3)  
−2 (6)  
−2 (7)  
1 (4)  
175 (4)  
2 (6)  
−41 (7)  
142 (7)  
147 (8)  
−30 (8)  
4 (12)  
177 (7)  
6 (12)  
−16 (9)  
14 (6)  
−7 (9)  
−179 (4)  
−2 (7)  
0.8 (13)  
1.1 (9)  
178.6 (7)  
−1.7 (12)  
−31.7 (13)  
149.9 (13)  
145.2 (16)  
−33.3 (16)  
−1 (2)  
−177.7 (13)  
−1 (2)  
2.0 (16)  
−1.6 (10)  
1.2 (16)  
178.2 (8)  
Hydrogen-bond geometry (Å, º)  
D—H···A  
D—H  
H···A  
D···A  
D—H···A  
N11—H11···O137  
N21—H21···O237  
C112—H112···O11i  
C144—H144···O137ii  
0.86  
0.86  
0.93  
0.93  
2.08  
2.01  
2.47  
2.56  
2.719 (10)  
2.65 (5)  
3.230 (4)  
3.397 (6)  
130  
131  
139  
150  
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, y+1/2, −z+3/2.  
2-Bromo-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide (III)  
Crystal data  
C20H15BrClNO2S  
Mr = 448.74  
F(000) = 1808  
Dx = 1.568 Mg m−3  
Monoclinic, C2/c  
a = 18.8096 (10) Å  
b = 11.5021 (7) Å  
c = 19.9112 (11) Å  
β = 118.030 (2)°  
V = 3802.5 (4) Å3  
Z = 8  
Mo Kα radiation, λ = 0.71073 Å  
Cell parameters from 4009 reflections  
θ = 2.2–26.8°  
µ = 2.43 mm−1  
T = 294 K  
Block, yellow  
0.25 × 0.20 × 0.10 mm  
Data collection  
Bruker Kappa APEXII  
diffractometer  
Absorption correction: multi-scan  
(SADABS; Bruker, 2012)  
Radiation source: fine focus sealed tube  
φ and ω scans  
Tmin = 0.614, Tmax = 0.785  
25510 measured reflections  
4009 independent reflections  
Acta Cryst. (2018). C74  
sup-17  
supporting information  
2370 reflections with I > 2σ(I)  
Rint = 0.047  
h = −23→23  
k = −14→14  
l = −24→25  
θ
max = 26.8°, θmin = 2.2°  
Refinement  
Refinement on F2  
Least-squares matrix: full  
R[F2 > 2σ(F2)] = 0.045  
wR(F2) = 0.122  
S = 1.01  
4009 reflections  
322 parameters  
64 restraints  
Hydrogen site location: inferred from  
neighbouring sites  
H-atom parameters constrained  
w = 1/[σ2(Fo2) + (0.0522P)2 + 2.9782P]  
where P = (Fo2 + 2Fc2)/3  
(Δ/σ)max < 0.001  
Δρmax = 0.40 e Å−3  
Δρmin = −0.50 e Å−3  
Special details  
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance  
matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles;  
correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate  
(isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.  
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)  
x
y
z
Uiso*/Ueq  
Occ. (<1)  
C11  
O11  
N11  
H11  
0.5823 (3)  
0.5148 (4)  
0.6219 (6)  
0.6672  
0.6254 (3)  
0.6211 (3)  
0.6670 (4)  
0.6644  
0.7141 (3)  
0.7443  
0.7185 (3)  
0.7512  
0.5906 (4)  
0.5810 (7)  
0.4975 (5)  
0.5118  
0.7051 (3)  
0.7899 (4)  
0.8934 (5)  
0.9522  
0.9067 (5)  
0.9743  
0.8245 (4)  
0.8357  
0.4593 (4)  
0.4072 (8)  
0.5055 (8)  
0.5448  
0.4898 (3)  
0.4387 (3)  
0.4679 (5)  
0.4348  
0.5434 (4)  
0.5615  
0.5931 (3)  
0.6450  
0.0496 (13)  
0.0687 (16)  
0.0482 (17)  
0.058*  
0.0469 (11)  
0.0614 (12)  
0.0871 (18)  
0.105*  
0.0749 (16)  
0.090*  
0.0747 (14)  
0.090*  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
C111  
C112  
C113  
H113  
C114  
H114  
C115  
H115  
C116  
H116  
S121  
C122  
C123  
C124  
H124  
C125  
C126  
H16A  
H16B  
C127  
H17A  
H17B  
H17C  
0.6745 (3)  
0.6777  
0.7236 (4)  
0.6671  
0.5671 (4)  
0.6018  
0.0559 (12)  
0.067*  
0.5058 (4)  
0.5958 (8)  
0.6416 (7)  
0.5995 (6)  
0.6190  
0.5291 (10)  
0.4719 (10)  
0.4217  
0.4945  
0.4548 (12)  
0.5047  
0.4260  
0.4229  
0.3394 (6)  
0.3838 (5)  
0.2913 (6)  
0.1840 (5)  
0.1135  
0.1936 (6)  
0.0994 (9)  
0.1088  
0.0247  
0.100 (2)  
0.0973  
0.1692  
0.0330  
0.4205 (4)  
0.4946 (8)  
0.5371 (8)  
0.5103 (6)  
0.5351  
0.4460 (12)  
0.3996 (10)  
0.4015  
0.4220  
0.3178 (9)  
0.3156  
0.2934  
0.2923  
0.0503 (10)  
0.042 (2)  
0.0467 (15)  
0.0467 (15)  
0.056*  
0.0523 (9)  
0.0660 (10)  
0.079*  
0.079*  
0.120 (6)  
0.180*  
0.180*  
0.180*  
Acta Cryst. (2018). C74  
sup-18  
supporting information  
C137  
O137  
C131  
C132  
Cl12  
C133  
H133  
C134  
H134  
C135  
H135  
C136  
H136  
Br12  
C21  
0.7199 (5)  
0.7551 (8)  
0.7633 (5)  
0.7380 (10)  
0.6507 (7)  
0.7822 (13)  
0.7642  
0.8519 (13)  
0.8829  
0.8777 (13)  
0.9240  
0.3072 (6)  
0.4013 (6)  
0.2024 (7)  
0.1439 (15)  
0.1871 (8)  
0.050 (2)  
0.0092  
0.020 (2)  
−0.0402  
0.076 (2)  
0.0507  
0.6033 (5)  
0.6196 (11)  
0.6494 (6)  
0.695 (2)  
0.6970 (8)  
0.7400 (16)  
0.7694  
0.7397 (17)  
0.7710  
0.6946 (19)  
0.6933  
0.0491 (11)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.7006 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.0694 (13)  
0.0459 (13)  
0.0590 (12)  
0.0916 (12)  
0.0754 (17)  
0.090*  
0.0838 (16)  
0.101*  
0.080 (3)  
0.096*  
0.8354 (12)  
0.8549  
0.170 (2)  
0.2108  
0.6510 (17)  
0.6228  
0.063 (2)  
0.076*  
0.56130 (4)  
0.5651 (9)  
0.4990 (12)  
0.6193 (14)  
0.6683  
0.6065 (7)  
0.5735 (6)  
0.5302  
0.6082 (6)  
0.5938  
0.6616 (8)  
0.6806  
0.7721 (7)  
0.5994 (9)  
0.5722 (17)  
0.5109 (11)  
0.5292  
0.7113 (8)  
0.7690 (8)  
0.7378  
0.878 (2)  
0.9126  
0.9299 (9)  
1.0036  
0.33313 (4)  
0.4558 (8)  
0.4048 (19)  
0.494 (2)  
0.5250  
0.4527 (5)  
0.3833 (6)  
0.3406  
0.3795 (7)  
0.3326  
0.4440 (7)  
0.4415  
0.0997 (3)  
0.0496 (13)  
0.0687 (16)  
0.0482 (17)  
0.058*  
0.0469 (11)  
0.0614 (12)  
0.074*  
0.0871 (18)  
0.105*  
0.0749 (16)  
0.090*  
O21  
N21  
H21  
C211  
C212  
H212  
C213  
H213  
C214  
H214  
C215  
H215  
C216  
S221  
C222  
C223  
C224  
H224  
C225  
C226  
H26A  
H26B  
C227  
H27A  
H27B  
H27C  
C237  
O237  
C231  
C232  
Cl22  
0.6883 (10)  
0.7245  
0.8782 (10)  
0.9171  
0.5119 (7)  
0.5556  
0.0747 (14)  
0.090*  
0.6627 (6)  
0.5091 (11)  
0.5979 (19)  
0.6420 (16)  
0.6063 (14)  
0.6326  
0.531 (2)  
0.475 (2)  
0.4345  
0.5048  
0.433 (3)  
0.4024  
0.4724  
0.3976  
0.7215 (12)  
0.751 (2)  
0.7665 (11)  
0.737 (2)  
0.6515 (17)  
0.782 (3)  
0.7650  
0.7681 (8)  
0.345 (2)  
0.3948 (10)  
0.3068 (10)  
0.1960 (10)  
0.1259  
0.2026 (14)  
0.1052 (19)  
0.0983  
0.0330  
0.123 (5)  
0.0545  
0.1363  
0.1885  
0.327 (2)  
0.4247 (17)  
0.226 (2)  
0.162 (4)  
0.209 (2)  
0.070 (5)  
0.0321  
0.5178 (6)  
0.4115 (10)  
0.485 (2)  
0.5338 (18)  
0.505 (2)  
0.5241  
0.446 (3)  
0.404 (2)  
0.4207  
0.4154  
0.319 (2)  
0.2942  
0.3019  
0.3060  
0.5976 (13)  
0.616 (3)  
0.6470 (14)  
0.688 (3)  
0.6916 (19)  
0.734 (4)  
0.7656  
0.0559 (12)  
0.0503 (10)  
0.042 (2)  
0.043 (4)  
0.0467 (15)  
0.056*  
0.0523 (9)  
0.0660 (10)  
0.079*  
0.079*  
0.120 (6)  
0.180*  
0.180*  
0.180*  
0.0491 (11)  
0.0694 (13)  
0.0459 (13)  
0.0590 (12)  
0.0916 (12)  
0.0754 (17)  
0.090*  
C233  
H233  
Acta Cryst. (2018). C74  
sup-19  
supporting information  
C234  
H234  
C235  
H235  
C236  
H236  
Br26  
0.850 (3)  
0.8766  
0.879 (3)  
0.9275  
0.837 (3)  
0.8552  
0.70489 (8)  
0.035 (5)  
−0.0309  
0.096 (5)  
0.0735  
0.189 (5)  
0.2270  
0.731 (4)  
0.7580  
0.691 (4)  
0.6928  
0.646 (4)  
0.6164  
0.61638 (8)  
0.0838 (16)  
0.101*  
0.080 (3)  
0.096*  
0.063 (2)  
0.076*  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.2994 (12)  
0.7080 (2)  
0.0658 (5)  
Atomic displacement parameters (Å2)  
U11  
U22  
U33  
U12  
U13  
U23  
C11  
O11  
N11  
0.039 (3)  
0.044 (3)  
0.0462 (15)  
0.045 (3)  
0.053 (3)  
0.087 (4)  
0.056 (3)  
0.069 (3)  
0.050 (3)  
0.0446 (7)  
0.0428 (16)  
0.052 (2)  
0.052 (2)  
0.0529 (19)  
0.059 (2)  
0.168 (13)  
0.0540 (18)  
0.060 (2)  
0.0516 (18)  
0.073 (2)  
0.1105 (8)  
0.106 (3)  
0.090 (3)  
0.059 (2)  
0.053 (2)  
0.1039 (5)  
0.039 (3)  
0.044 (3)  
0.0462 (15)  
0.045 (3)  
0.053 (3)  
0.087 (4)  
0.056 (3)  
0.069 (3)  
0.050 (3)  
0.0446 (7)  
0.0428 (16)  
0.0408 (19)  
0.0569 (18)  
0.0374 (19)  
0.0412 (19)  
0.049 (3)  
0.056 (3)  
0.049 (3)  
0.052 (3)  
0.047 (3)  
0.0471 (8)  
0.0407 (19)  
0.0352 (17)  
0.0352 (17)  
0.044 (2)  
0.053 (2)  
0.079 (11)  
0.040 (3)  
0.036 (3)  
0.038 (4)  
0.051 (6)  
0.088 (4)  
0.060 (8)  
0.069 (7)  
0.080 (9)  
0.061 (8)  
0.1178 (6)  
0.0408 (19)  
0.0569 (18)  
0.0374 (19)  
0.0412 (19)  
0.049 (3)  
0.056 (3)  
0.049 (3)  
0.052 (3)  
0.047 (3)  
0.0471 (8)  
0.0407 (19)  
0.074 (2)  
0.0098 (19)  
−0.0024 (16)  
−0.0027 (15)  
0.0048 (19)  
0.002 (2)  
0.030 (2)  
0.010 (3)  
0.0141 (17)  
0.023 (3)  
0.040 (2)  
0.074 (5)  
0.042 (3)  
0.030 (3)  
0.016 (3)  
−0.0003 (17)  
0.0079 (17)  
0.0005 (18)  
0.001 (3)  
0.006 (3)  
0.030 (4)  
−0.013 (3)  
−0.018 (3)  
−0.005 (2)  
−0.0004 (9)  
0.0008 (18)  
0.0012 (15)  
0.0012 (15)  
−0.008 (2)  
−0.0149 (19)  
−0.018 (4)  
0.001 (2)  
0.000 (4)  
0.002 (2)  
0.000 (3)  
0.004 (2)  
0.010 (4)  
0.021 (3)  
0.016 (5)  
0.009 (4)  
0.0816 (18)  
0.051 (5)  
0.055 (3)  
0.090 (4)  
0.143 (5)  
0.120 (5)  
0.095 (4)  
0.060 (4)  
0.0521 (18)  
0.045 (4)  
0.054 (2)  
0.054 (2)  
0.0585 (19)  
0.077 (3)  
0.065 (3)  
0.049 (2)  
0.079 (2)  
0.0402 (17)  
0.053 (4)  
0.113 (2)  
0.056 (5)  
0.058 (7)  
0.080 (4)  
0.062 (4)  
0.0784 (5)  
0.074 (2)  
0.0816 (18)  
0.051 (5)  
0.055 (3)  
0.090 (4)  
0.143 (5)  
0.120 (5)  
0.095 (4)  
0.060 (4)  
0.0521 (18)  
0.045 (4)  
C111  
C112  
C113  
C114  
C115  
C116  
S121  
C122  
C123  
C124  
C125  
C126  
C127  
C137  
O137  
C131  
C132  
Cl12  
C133  
C134  
C135  
C136  
Br12  
C21  
0.020 (3)  
−0.001 (2)  
−0.004 (2)  
0.001 (2)  
−0.0037 (5)  
−0.0039 (18)  
−0.0015 (15)  
−0.0015 (15)  
−0.0060 (18)  
−0.0120 (18)  
−0.043 (9)  
−0.0018 (19)  
−0.005 (3)  
−0.004 (2)  
−0.003 (3)  
−0.002 (2)  
−0.009 (4)  
0.014 (3)  
0.0170 (10)  
0.022 (2)  
0.0254 (18)  
0.0254 (18)  
0.0246 (16)  
0.0243 (19)  
0.016 (6)  
0.0205 (16)  
0.0047 (14)  
0.0151 (14)  
0.030 (2)  
0.0822 (10)  
0.035 (3)  
0.006 (4)  
0.017 (5)  
0.010 (4)  
0.017 (2)  
0.0158 (18)  
0.0437 (4)  
0.030 (2)  
0.010 (3)  
0.0141 (17)  
0.023 (3)  
0.040 (2)  
0.074 (5)  
0.042 (3)  
0.030 (3)  
0.0125 (4)  
0.0098 (19)  
−0.0024 (16)  
−0.0027 (15)  
0.0048 (19)  
0.002 (2)  
0.0350 (4)  
−0.0003 (17)  
0.0079 (17)  
0.0005 (18)  
0.001 (3)  
O21  
N21  
C211  
C212  
C213  
C214  
C215  
C216  
S221  
C222  
0.006 (3)  
0.030 (4)  
0.020 (3)  
−0.001 (2)  
−0.004 (2)  
0.001 (2)  
−0.0037 (5)  
−0.0039 (18)  
−0.013 (3)  
−0.018 (3)  
−0.005 (2)  
−0.0004 (9)  
0.0008 (18)  
0.016 (3)  
0.0170 (10)  
0.022 (2)  
Acta Cryst. (2018). C74  
sup-20  
supporting information  
C223  
C224  
C225  
C226  
C227  
C237  
O237  
C231  
C232  
Cl22  
C233  
C234  
C235  
C236  
Br26  
0.039 (6)  
0.052 (2)  
0.0529 (19)  
0.059 (2)  
0.168 (13)  
0.0540 (18)  
0.060 (2)  
0.0516 (18)  
0.073 (2)  
0.1105 (8)  
0.106 (3)  
0.090 (3)  
0.059 (2)  
0.053 (2)  
0.0641 (8)  
0.035 (7)  
0.0352 (17)  
0.044 (2)  
0.053 (2)  
0.079 (11)  
0.040 (3)  
0.036 (3)  
0.038 (4)  
0.051 (6)  
0.088 (4)  
0.060 (8)  
0.069 (7)  
0.080 (9)  
0.061 (8)  
0.0600 (8)  
0.037 (7)  
0.054 (2)  
0.0585 (19)  
0.077 (3)  
0.065 (3)  
0.049 (2)  
0.079 (2)  
0.0402 (17)  
0.053 (4)  
0.113 (2)  
0.056 (5)  
0.058 (7)  
0.080 (4)  
0.062 (4)  
0.0514 (8)  
−0.002 (6)  
−0.0015 (15)  
−0.0060 (18)  
−0.0120 (18)  
−0.043 (9)  
−0.0018 (19)  
−0.005 (3)  
−0.004 (2)  
−0.003 (3)  
−0.002 (2)  
−0.009 (4)  
0.014 (3)  
0.003 (5)  
−0.005 (7)  
0.0012 (15)  
−0.008 (2)  
−0.0149 (19)  
−0.018 (4)  
0.001 (2)  
0.000 (4)  
0.002 (2)  
0.000 (3)  
0.004 (2)  
0.010 (4)  
0.021 (3)  
0.016 (5)  
0.009 (4)  
−0.0028 (6)  
0.0254 (18)  
0.0246 (16)  
0.0243 (19)  
0.016 (6)  
0.0205 (16)  
0.0047 (14)  
0.0151 (14)  
0.030 (2)  
0.0822 (10)  
0.035 (3)  
0.006 (4)  
0.017 (2)  
0.0158 (18)  
0.0090 (6)  
0.017 (5)  
0.010 (4)  
−0.0015 (6)  
Geometric parameters (Å, º)  
C11—O11  
1.209 (4)  
C21—O21  
1.219 (5)  
C11—N11  
C11—C111  
N11—C122  
N11—H11  
1.380 (5)  
1.516 (5)  
1.377 (4)  
0.8600  
C21—N21  
1.388 (6)  
1.521 (7)  
1.382 (5)  
0.8600  
C21—C211  
N21—C222  
N21—H21  
C111—C112  
C111—C116  
C112—C113  
C112—Br12  
C113—C114  
C113—H113  
C114—C115  
C114—H114  
C115—C116  
C115—H115  
C116—H116  
S121—C122  
S121—C125  
C122—C123  
C123—C124  
C123—C137  
C124—C125  
C124—H124  
C125—C126  
C126—C127  
C126—H16A  
C126—H16B  
C127—H17A  
C127—H17B  
C127—H17C  
1.384 (6)  
1.391 (7)  
1.425 (8)  
1.871 (6)  
1.347 (9)  
0.9300  
1.342 (8)  
0.9300  
1.377 (6)  
0.9300  
C211—C212  
C211—C216  
C212—C213  
C212—H212  
C213—C214  
C213—H213  
C214—C215  
C214—H214  
C215—C216  
C215—H215  
C216—Br26  
S221—C222  
S221—C225  
C222—C223  
C223—C224  
C223—C237  
C224—C225  
C224—H224  
C225—C226  
C226—C227  
C226—H26A  
C226—H26B  
C227—H27A  
C227—H27B  
C227—H27C  
1.388 (7)  
1.391 (8)  
1.432 (9)  
0.9300  
1.343 (10)  
0.9300  
1.341 (9)  
0.9300  
1.380 (7)  
0.9300  
1.870 (10)  
1.721 (4)  
1.748 (6)  
1.378 (6)  
1.430 (6)  
1.455 (6)  
1.346 (7)  
0.9300  
0.9300  
1.720 (3)  
1.747 (4)  
1.380 (5)  
1.428 (5)  
1.454 (5)  
1.345 (5)  
0.9300  
1.500 (4)  
1.504 (9)  
0.9700  
1.501 (5)  
1.504 (9)  
0.9700  
0.9700  
0.9600  
0.9700  
0.9600  
0.9600  
0.9600  
0.9600  
0.9600  
Acta Cryst. (2018). C74  
sup-21  

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Product name:1-(Benzoyloxy)-1H-1,2,3-benzotriazole

Cas No:54769-36-7

54769-36-7

R&D Labs maybe for 54769-36-7

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