Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides: Order versus disorder, and similar molecular conformations but different modes of supramolecular aggregation, with a new disordered refinement of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene

Article abstract of DOI:10.1107/S2053229617017326

Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides, bearing different substituents on the benzamide ring, have been synthesized and structurally characterized. In each of N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide, C₂₂H₁₈FNO₂S, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide, C₂₂H₁₈ClNO₂S, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide, C₂₂H₁₇F₂NO₂S, (III), and N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide, C₂₃H₂₁NO₃S, (IV), the last of which crystallizes with Z′ = 2 in the space group P, the fused six-membered ring adopts a half-chair conformation. In each of (I)-(III), this ring is disordered over two sets of atomic sites having occupancies of 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and 0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III), such that the two disorder components of the ring are almost enantiomeric. Molecules of (I) are linked into chains by π-π stacking interactions, and those of (II) are linked into chains by a C - H···π hydrogen bond. A combination of two C - H···O hydrogen bonds and two C - H···π hydrogen bonds links the molecules of (III) into complex sheets, but the molecules of (IV) are linked by a combination of two hydrogen bonds, one each of the C - H···O and C - H···π types, to form centrosymmetric tetramers. The structures of (I)-(IV) are compared with that of the unsubstituted analogue N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide and a new refinement of the parent amine 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene, using the original data set, has found that here too the fused six-membered ring exhibits conformational disorder, with occupancies of 0.887 (9) and 0.113 (9). Comparisons are made with some related compounds.

Full text of DOI:10.1107/S2053229617017326

research papers
Four closely related N-(3-benzoyl-4,5,6,7-tetra-
hydrobenzo[b]thiophen-2-yl)benzamides: order
versus disorder, and similar molecular conforma-
tions but different modes of supramolecular
aggregation, with a new disordered refinement of
2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]-
thiophene
ISSN 2053-2296
Received 20 October 2017
Accepted 3 December 2017
Edited by A. G. Oliver, University of Notre
Dame, USA
Belakavadi K. Sagar,a Hemmige S. Yathirajan,a Ravindranath S. Rathoreb and
Christopher Glidewellc*
Keywords: synthesis; benzo[b]thiophenes;
crystal structure; molecular conformation;
conformational disorder; hydrogen bonding;
supramolecular assembly; ꢀ–ꢀ stacking.
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
CCDC references: 1588989; 1588988;
1588987; 1588986; 1588985
Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benz-
amides, bearing different substituents on the benzamide ring, have been
synthesized and structurally characterized. In each of N-(3-benzoyl-4,5,6,7-
tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide, C22H18FNO2S, (I), N-(3-
benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide, C22H18-
ClNO2S, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-di-
fluorobenzamide, C22H17F2NO2S, (III), and N-(3-benzoyl-4,5,6,7-tetrahydro-
benzo[b]thiophen-2-yl)-2-methoxybenzamide, C23H21NO3S, (IV), the last of
which crystallizes with Z0 = 2 in the space group P1, the fused six-membered ring
adopts a half-chair conformation. In each of (I)–(III), this ring is disordered over
two sets of atomic sites having occupancies of 0.811 (6) and 0.189 (6) in (I),
0.645 (7) and 0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III), such that the
two disorder components of the ring are almost enantiomeric. Molecules of (I)
are linked into chains by ꢀ–ꢀ stacking interactions, and those of (II) are linked
into chains by a C—Hꢀ ꢀ ꢀꢀ hydrogen bond. A combination of two C—Hꢀ ꢀ ꢀO
hydrogen bonds and two C—Hꢀ ꢀ ꢀꢀ hydrogen bonds links the molecules of (III)
into complex sheets, but the molecules of (IV) are linked by a combination of
two hydrogen bonds, one each of the C—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀꢀ types, to form
centrosymmetric tetramers. The structures of (I)–(IV) are compared with that of
the unsubstituted analogue N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-
yl)benzamide and a new refinement of the parent amine 2-amino-3-benzoyl-
4,5,6,7-tetrahydrobenzo[b]thiophene, using the original data set, has found that
here too the fused six-membered ring exhibits conformational disorder, with
occupancies of 0.887 (9) and 0.113 (9). Comparisons are made with some related
compounds.
Supporting information: this article has
supporting information at journals.iucr.org/c
1. Introduction
Thiophene derivatives 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; Ashalatha et al., 2007; Molvi et al., 2007), antimicrobial
activity (Ashalatha et al., 2007; Rai et al., 2008) and NO-
scavenging activity (Molvi et al., 2007); in addition, 2-amino-3-
benzoylthiophenes can act as allosteric enhancers at the A1
adenosine receptor (Aurelio et al., 2010). With this in mind, we
synthesized and characterized a series of four variously sub-
# 2018 International Union of Crystallography
Acta Cryst. (2018). C74, 45–53
https://doi.org/10.1107/S2053229617017326 45

research papers
stituted N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-
benzamides (Scheme 1), whose structures we report here,
namely N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-
3-fluorobenzamide, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo-
[b]thiophen-2-yl)-4-chlorobenzamide, (II), N-(3-benzoyl-
4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzam-
ide, (III), and N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thio-
phen-2-yl)-2-methoxybenzamide, (IV), and we compare the
structures of (I)–(IV) with those of the recently reported
analogue N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-
yl)benzamide, (V) (Scheme 2) (Kaur, Jasinski, Yathirajan et
al., 2014), and the parent amine 2-amino-3-benzoyl-4,5,6,7-
tetrahydrobenzo[b]thiophene, (VI) (Kubicki et al., 2012).
7.23 (m, 9H), 2.68 (dd, J = 6.4, 12.0 Hz, 2H), 2.23 (dd, J = 6.0,
11.6 Hz, 2H), 1.75–1.72 (m, 2H), 1.60–1.57 (m, 2H). Com-
pound (II): yield 87%, m.p. 428 K; IR (KBr): 3290 (NH2),
2932, 1663 (C O, keto), 1592 (C O, amide), 1527, 1442,
1025, 750; 1H NMR (DMSO-d6): ꢁ 11.31 (s, NH), 7.63–7.44 (m,
9H), 2.68 (dd, J = 5.6, 11.6 Hz, 2H), 2.18 (dd, J = 5.6, 11.6 Hz,
2H), 1.75–1.72 (m, 2H), 1.59–1.56 (m, 2H). Compound (III):
yield 81%, m.p. 445 K; IR (KBr): 3220 (NH2), 2930, 1682
(C O, keto), 1623 (C O, amide), 1528, 1462, 1251, 1051; 1H
NMR (DMSO-d6): ꢁ 11.97 (s, NH), 7.57–7.40 (m, 8H), 2.71
(dd, J = 6.4, 12.8 Hz, 2H), 1.97 (dd, J = 6.0, 12.0 Hz, 2H), 1.82–
1.76 (m, 2H), 1.56–1.50 (m, 2H). Compound (IV): yield 88%,
m.p. 447 K; IR (KBr): 3223 (NH2), 2945, 1645 (C O, keto),
1
1623 (C O, amide), 1598, 1466, 1331, 1249, 1045; H NMR
(DMSO-d6): ꢁ 12.94 (s, NH), 7.62 (d, J = 7.6 Hz, 2H), 7.53–7.48
(m, 2H), 7.47–7.41 (m, 2H), 7.09 (dd, J = 8, 15.2 Hz, 2H), 7.01
(d, J = 8.1 Hz, 1H), 4.17 (s, 3H, OMe), 2.71 (dd, J = 6.4,
12.4 Hz, 2H), 1.94 (dd, J = 6, 12 Hz, 2H), 1.79–1.74 (m, 2H),
1.55–1.51 (m, 2H).
2. Experimental
2.1. Synthesis and crystallization
2-Amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene 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)–(IV), the
appropriately substituted benzoyl chloride (0.78 mmol), viz.
3-fluorobenzoyl chloride for (I), 4-chlorobenzoyl chloride for
(II), 2,6-difluorobenzoyl chloride for (III) and 2-methoxy-
benzoyl chloride for (IV), was added dropwise with stirring to
a mixture of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thio-
phene (0.78 mmol) and triethylamine (2.34 mmol) in di-
chloromethane (20 ml), and the resulting solutions were
stirred at 273 K for 6 h. Each solution was poured into ice-cold
aqueous hydrochloric acid (1 M, 100 ml), and the aqueous
mixtures were then exhaustively extracted with dichloro-
methane. The organic extracts were washed first with a satu-
rated solution of sodium hydrogen carbonate and then with
brine, before removal of the solvent under reduced pressure.
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 dimethylformamide.
2.3. 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 each of compounds (I)–(III)
that the atoms of the –(CH2)4– fragments were disordered
over two sets of sites having unequal occupancies. For the
minor-disorder forms, the bonded distances and the 1,3
nonbonded distances were restrained to be the same as those
2.2. Analytical and spectroscopic data
˚
Compound (I): yield 85%, m.p. 390–391 K; IR (KBr): 3070
(NH2), 2929, 1668 (C O, keto), 1595 (C O, amide), 1585,
1445, 1354, 1081; 1H NMR (DMSO-d6): ꢁ 11.20 (s, NH), 7.64–
in the major forms, subject to s.u. values of 0.005 and 0.01 A,
respectively. In addition, the anisotropic displacement para-
meters for the corresponding pairs of atoms in the two
ꢁ
46 Sagar et al.
Four closely related N-(benzo[b]thiophen-2-yl)benzamides
Acta Cryst. (2018). C74, 45–53

research papers
Table 1
Experimental details.
(I)
(II)
(III)
Crystal data
Chemical formula
Mr
C22H18FNO2S
379.43
C22H18ClNO2S
395.88
C22H17F2NO2S
397.43
Crystal system, space group
Temperature (K)
Monoclinic, P21/c
296
15.9489 (11), 7.2739 (4),
15.9222 (10)
90, 95.813 (4), 90
1837.6 (2)
Monoclinic, P21/n
296
Triclinic, P1
296
7.6718 (3), 9.8833 (3), 13.5925 (5)
˚
a, b, c (A)
11.6776 (6), 14.2461 (8),
12.2957 (7)
90, 109.336 (2), 90
1930.13 (18)
4
Mo Kꢂ
0.32
0.25 ꢄ 0.20 ꢄ 0.20
ꢂ, ꢃ, ꢄ (ꢂ)
104.925 (4), 95.476 (2), 103.633 (3)
954.32 (6)
2
Mo Kꢂ
0.21
0.20 ꢄ 0.20 ꢄ 0.15
3
˚
V (A )
Z
Radiation type
4
Mo Kꢂ
0.20
0.15 ꢄ 0.10 ꢄ 0.10
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)
Tmin, Tmax
0.895, 0.980
21151, 3809, 2343
0.882, 0.937
28361, 3743, 2127
0.942, 0.970
21940, 4375, 2814
No. of measured, independent and
observed [I > 2ꢆ(I)] reflections
Rint
0.052
0.629
0.047
0.615
0.041
0.650
ꢃ1
˚
(sin ꢇ/ꢈ)max (A
)
Refinement
R[F2 > 2ꢆ(F2)], wR(F2), S
No. of reflections
0.046, 0.122, 1.02
3809
0.047, 0.142, 1.03
3743
0.041, 0.108, 1.02
4375
No. of parameters
No. of restraints
H-atom treatment
258
12
257
12
267
12
H-atom parameters constrained
0.16, ꢃ0.20
H-atom parameters constrained
0.30, ꢃ0.28
H-atom parameters constrained
0.23, ꢃ0.25
ꢃ3
˚
Áꢉmax, Áꢉmin (e A
)
(IV)
(VI)
Crystal data
Chemical formula
Mr
C23H21NO3S
391.47
Triclinic, P1
296
8.5129 (9), 12.9230 (14), 19.031 (2)
96.811 (5), 102.665 (6), 105.321 (5)
1935.1 (4)
4
Mo Kꢂ
0.19
0.20 ꢄ 0.15 ꢄ 0.15
C15H15NOS
257.34
Orthorhombic, Pna21
295
9.2080 (4), 14.0485 (7), 10.3826 (6)
90, 90, 90
1343.08 (12)
4
Mo Kꢂ
0.23
Crystal system, space group
Temperature (K)
˚
a, b, c (A)
ꢂ, ꢃ, ꢄ (ꢂ)
3
˚
V (A )
Z
Radiation type
ꢅ (mmꢃ1
Crystal size (mm)
)
0.30 ꢄ 0.15 ꢄ 0.15
Data collection
Diffractometer
Absorption correction
Bruker Kappa APEXII
Multi-scan (SADABS; Bruker,
2012)
Agilent Eos Gemini
Multi-scan (CrysAlis RED; Agilent,
2012)
Tmin, Tmax
No. of measured, independent and observed [I >
0.935, 0.972
37373, 8015, 4159
0.948, 0.966
3556, 1984, 1720
2ꢆ(I)] reflections
Rint
0.072
0.628
0.021
0.664
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
0.052, 0.151, 0.97
8015
511
0
H atoms treated by a mixture of independent
0.036, 0.086, 1.04
1984
176
13
H-atom parameters constrained
and constrained refinement
0.23, ꢃ0.36
ꢃ3
˚
Áꢉmax, Áꢉmin (e A
Absolute structure
)
0.13, ꢃ0.23
–
Flack x determined using 422 quotients
[(I+) ꢃ (Iꢃ)]/[(I+) + (Iꢃ)] (Parsons et al., 2013)
ꢃ0.03 (6)
Absolute structure parameter
–
Computer programs: APEX2 (Bruker, 2012), CrysAlis PRO (Agilent, 2012), SAINT-Plus (Bruker, 2012), CrysAlis RED (Agilent, 2012), SHELXS86 (Sheldrick, 2008), SHELXL2014
(Sheldrick, 2015) and PLATON (Spek, 2009).
ꢁ
Acta Cryst. (2018). C74, 45–53
Sagar et al.
Four closely related N-(benzo[b]thiophen-2-yl)benzamides 47

research papers
Table 2
Selected geometric parameters (A, ) for compounds (I)–(VI).
Fc/Fc(max) < 0.004, respectively. The disorder in compound
(VI), which was refined using the original data set (Kubicki et
al., 2012), was handled exactly as in compounds (I)–(III),
giving refined occupancies for the two disorder components of
0.887 (9) and 0.113 (9). The correct orientation of the struc-
ture of compound (VI) with respect to the polar-axis direction
was established using the Flack x parameter (Flack, 1983),
calculated (Parsons et al., 2013) as x = ꢃ0.03 (6) by the use of
422 quotients of the type [(I+) ꢃ (Iꢃ)]/[(I+) + (Iꢃ)].
ꢂ
˚
For the major- and minor-disorder components in compounds (I)–(III) and
(VI), the ring-puckering parameters are calculated for the atom sequences
C13A–C14–C15–C16–C17–C17A and C13A–C24–C25–C26–C27–C17A, res-
pectively. For molecules 1 and 2 in compound (IV), the parameters are
calculated for the atom sequences C13A–C114–C115–C116–C117–C17A and
C23A–C24–C25–C26–C27–C27A, respectively. The parameters for compound
(V) were calculated using the published atomic coordinates (Kaur, Jasinski,
Yathirajan et al., 2014), but with the atom labels and the enantiomorph
adjusted to match those of the major-disorder components in compounds (I)–
(III) and (VI). For compounds (I)–(V), ꢊ1, ꢊ2, ꢊ3 and ꢊ4 represent, respectively,
the torsion angles Sx11—Cx12—Nx1—Cx7, Cx12—Nx1—Cx7—Cx1, Nx1—
Cx7—Cx1—Cx2 and Cx13—Cx37—Cx31—Cx32, where x is nul for (I)–(III)
and (V), and x = 1 or 2 for molecules 1 and 2 in compound (IV). For compound
(VI), ꢊ4 represents the torsion angle C3—C37—C31—C32.
3. Results and discussion
The reference molecules were all chosen to have the same sign
for the torsion angle ꢊ4 (Table 2), defining the orientation of
the 3-benzoyl group relative to the thiophene ring. Compound
(IV) crystallizes with Z0 = 2 in the space group P1, but a search
for possible additional crystallographic symmetry found none;
it will be convenient to refer to the molecules of (IV)
containing atoms S111 and S211 as molecules of types 1 and 2,
respectively.
In each of (I)–(III), the –(CH2)4– portion of the fused six-
membered ring exhibits disorder over two sets of sites with
occupancies of 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and
0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III). This ring
adopts a half-chair conformation in each of (I)–(IV)
(Figs. 1–4), as shown by the ring-puckering angles (Cremer &
Pople, 1975) in Table 2, as calculated using PLATON (Spek,
2009); for an idealized half-chair conformation, the values of
the puckering angles are ꢇ = 50.8ꢂ and ’ = (60k + 30)ꢂ, where k
represents an integer (Boeyens, 1978). Thus, in each of (I)–
(III), the conformations of the two disorder components of
this ring are nearly enantiomeric, as shown by the puckering
angles, which for genuine enantiomers are related by ꢇ0 =
(180 ꢃ ꢇ) and ’0 = (180 + ’) (Fig. 5). The energies of the two
conformations in each compound must be very similar, and it
(a) Ring-puckering parameters
Q
ꢇ
’
(I), major
(I), minor
0.516 (5)
0.50 (2)
49.0 (6)
145.5 (8)
332 (4)
150.4 (17)
330 (3)
138.7 (8)
327 (4)
150.5 (5)
143.5 (5)
142.2 (2)
148.9 (9)
331 (6)
139 (2)
48.3 (11)
134 (2)
50.0 (6)
143 (2)
50.7 (4)
51.5 (4)
53.3 (2)
49.7 (7)
135 (3)
(II), major
(II), minor
(III), major
(III), minor
(IV), molecule 1
(IV), molecule 2
(V)
0.514 (9)
0.538 (18)
0.507 (5)
0.489 (19)
0.467 (3)
0.486 (4)
0.5098 (19)
0.517 (6)
0.51 (3)
(VI), major
(VI), minor
(b) Torsion angles
ꢊ1
0.0 (3)
6.6 (4)
ꢃ7.3 (3)
ꢃ1.9 (3)
ꢃ2.5 (3)
ꢃ2.1 (2)
ꢊ2
ꢊ3
ꢊ4
(I)
(II)
(III)
(IV), molecule 1
(IV), molecule 2
(V)
179.60 (18) ꢃ158.70 (19) ꢃ132.4 (2)
ꢃ175.9 (3)
ꢃ170.5 (3)
ꢃ110.7 (4)
ꢃ147.78 (19)
ꢃ141.1 (3)
ꢃ150.8 (2)
178.76 (18) ꢃ134.5 (2)
ꢃ176.7 (2)
ꢃ178.2 (2)
5.6 (4)
5.0 (4)
ꢃ179.62 (14) ꢃ172.35 (14) ꢃ148.30 (15)
ꢃ137.6 (3)
(VI)
disorder forms were constrained to be identical. All H atoms
were treated as riding atoms in geometrically idealized posi-
˚
tions, with C—H = 0.93 (aromatic), 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 in (IV), which were
permitted to rotate but not to tilt, and 1.2 for all other H
atoms. Refinement of the atomic coordinates for the H atoms
bonded to N atoms resulted in N—H distances ranging from
˚
0.74 (4) to 0.90 (3) A; hence, the riding model was preferred.
Several low-angle reflections which had been attenuated by
the beam stop were omitted from the refinements, i.e. 100 for
(I), 001 for (III), and 010 and 001 for (IV). Subject to these
conditions, the refined occupancies for the two disorder forms
were 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and 0.355 (7) in
(II), and 0.784 (6) and 0.216 (6) in (III). In the final analysis of
variance for (I), there was a negative value, ꢃ1.093, of K =
2
2
[mean(Fo )/mean(Fc )] for the group of 443 very weak
reflections having Fc/Fc(max) in the range 0.000 < Fc/Fc(max)
< 0.005. In (II)–(IV), the corresponding values were ꢃ10.734
for 430 reflections in the range 0.000 < Fc/Fc(max) < 0.003,
ꢃ3.962 for 481 reflections in the range 0.000 < Fc/Fc(max) <
0.005 and ꢃ6.754 for 992 reflections in the range 0.000 <
Figure 1
The molecular structure of compound (I), showing the atom-labelling
scheme and the disorder in the fused six-membered ring. The major
conformer is drawn with full lines, the minor conformer with broken lines
and displacement ellipsoids at the 30% probability level.
ꢁ
48 Sagar et al.
Four closely related N-(benzo[b]thiophen-2-yl)benzamides
Acta Cryst. (2018). C74, 45–53

research papers
Figure 2
The molecular structure of compound (II), showing the atom-labelling
scheme and the disorder in the fused six-membered ring. The major
conformer is drawn with full lines, the minor conformer with broken lines
and displacement ellipsoids at the 30% probability level.
is quite possible that the exact ratios of the two forms may
vary slightly from one crystal to another.
Apart from the absence of disorder in compound (IV), the
overall conformations of the molecules in (I)–(IV) are fairly
similar (Table 2). The relative orientations of the benzoyl and
thiophene units are very similar, and this may be due, at least
in part, to the presence in each case of a short intramolecular
N—Hꢀ ꢀ ꢀO contact (Table 3). The orientations of the substi-
tuted aryl rings differ between compounds (I) and (IV), in
terms of the location of the substituents (Figs. 1 and 4), which,
in the case of (IV) may be controlled by a second intra-
molecular N—Hꢀ ꢀ ꢀO contact involving the methoxy O atoms
(Table 3).
Figure 4
The structures of the two independent molecules of compound (IV),
showing the atom-labelling scheme and the C—Hꢀ ꢀ ꢀO hydrogen bond
(dashed line) linking the two molecules within the selected asymmetric
unit. Displacement ellipsoids are drawn at the 30% probability level.
adopted by the fused six-membered ring is described variously
as ‘envelope’ and ‘half-chair’ in the original report (Kaur,
Jasinski, Yathirajan et al., 2014), the conformation is
undoubtedly a half-chair form; there is no indication of any
disorder in this ring.
The molecules of the unsubstituted analogue N-(3-benzoyl-
4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide, (V), adopt
a conformation which is very similar to that found here in
compounds (I)–(IV) (Table 2); although the conformation
The structures reported here all exhibit different modes of
supramolecular assembly and no two exhibit the same selec-
tion of direction-specific intermolecular interactions. The
Figure 5
Part of the crystal structure of compound (II), showing the nearly
enantiomeric nature of the two disorder components in the fused six-
membered ring. Atoms not forming part of the benzothiophene unit have
been omitted for the sake of clarity, as have many of the atom labels. The
major component is drawn with full lines and the minor component is
drawn with broken lines.
Figure 3
The molecular structure of compound (III), showing the atom-labelling
scheme and the disorder in the fused six-membered ring. The major
conformer is drawn with full lines, the minor conformer with broken lines
and displacement ellipsoids at the 30% probability level.
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Acta Cryst. (2018). C74, 45–53
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Four closely related N-(benzo[b]thiophen-2-yl)benzamides 49

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Table 3
Hydrogen bonds and short intramolecular contacts (A, ) for compounds
(I)–(IV) and (VI).
ꢂ
˚
Cg1, Cg2 and Cg3 represent the centroids of the C31–C36, S11/C12/C13/C13A/
C17A and S211/C212/C213/C23A/C27A rings, respectively.
Compound D—Hꢀ ꢀ ꢀA
D—H Hꢀ ꢀ ꢀA Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
(I)
(II)
N1—H1ꢀ ꢀ ꢀO37
0.86
0.86
0.93
0.97
0.97
0.86
0.93
0.97
0.93
0.93
0.86
0.86
0.86
0.86
0.93
0.93
0.86
0.86
2.01
1.99
2.76
2.96
2.73
2.08
2.50
2.59
2.85
2.75
1.95
2.11
1.93
2.13
2.49
2.95
2.07
2.03
2.650 (3) 130
N1—H1ꢀ ꢀ ꢀO37
2.641 (3) 132
3.676 (4) 169
3.475 (9) 114
3.530 (17) 140
2.718 (2) 130
3.326 (3) 148
3.494 (12) 156
3.635 (2) 143
3.520 (2) 141
2.630 (3) 136
2.731 (3) 128
2.616 (3) 136
2.748 (3) 129
3.232 (4) 137
3.869 (3) 170
2.666 (3) 125
2.831 (3) 156
C3—H3ꢀ ꢀ ꢀCg1i
C14—H14Aꢀ ꢀ ꢀCg1
C24—H24Aꢀ ꢀ ꢀCg1
N1—H1ꢀ ꢀ ꢀO37
(III)
(IV)
C3—H3ꢀ ꢀ ꢀO37ii
C17—H17Aꢀ ꢀ ꢀO7iii
C4—H4ꢀ ꢀ ꢀCg1iv
C35—H35ꢀ ꢀ ꢀCg2v
N11—H11ꢀ ꢀ ꢀO12
N11—H11ꢀ ꢀ ꢀO137
N21—H21ꢀ ꢀ ꢀO22
N21—H21ꢀ ꢀ ꢀO237
C134—H134ꢀ ꢀ ꢀO27
C235—H235ꢀ ꢀ ꢀCg3vi
N2—H2Aꢀ ꢀ ꢀO37
N2—H2Bꢀ ꢀ ꢀO37vii
(VI)
Symmetry codes: (i) ꢃx + 12, y ꢃ , ꢃz + 21; (ii) ꢃx + 1, ꢃy, ꢃz + 1; (iii) ꢃx + 1, ꢃy, ꢃz; (iv)
1
2
ꢃx, ꢃy, ꢃz + 1; (v) x ꢃ 1, y, z; (vi) ꢃx, ꢃy + 1, ꢃz + 2; (vii) x ꢃ 12, ꢃy + 23, z.
Figure 7
Part of the crystal structure of compound (II), showing the formation of a
chain along [010] built from C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds, shown as
dashed lines. The minor-disorder component and H atoms not involved in
the motif shown have been omitted for the sake of clarity. Cl atoms
marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the
supramolecular assembly in compound (I) depends upon two
ꢀ–ꢀ stacking interactions. The thiophene ring in the molecule
at (x, y, z) makes dihedral angles of 1.36 (11)ꢂ with the
substituted C1–C6 phenyl rings in the two molecules at (ꢃx + 1,
1
symmetry positions (ꢃx + 12, y ꢃ , ꢃz + 21), (ꢃx + 12, y + 21, ꢃz + 12) and (x,
2
y + 1, z), respectively.
1
2
1
2
1
2
1
2
y ꢃ , ꢃz + ) and (ꢃx + 1, y + , ꢃz + ); the ring-centroid
˚
separations are 3.6043 (13) and 3.8362 (13) A, respectively,
and the shortest perpendicular distances from the plane of one
ring in each pair to the centroid of the other are 3.5740 (9) and
˚
offsets of ca 0.47 and 1.51 A. The co-operative effect of these
two interactions leads to the formation of a ꢀ-stacked chain
running parallel to the [010] direction (Fig. 6). The supra-
molecular assembly in compound (II) depends on a single C—
Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond (Table 3), which links molecules
˚
3.5254 (9) A, respectively, corresponding to ring-centroid
1
related by the 21 screw axis along (14, y, ) to form a chain
4
running parallel to [010] (Fig. 7).
A combination of two C—Hꢀ ꢀ ꢀO hydrogen bonds and two
C—Hꢀ ꢀ ꢀꢀ hydrogen bonds (Table 3) links the molecules of
compound (III) into complex sheets, whose formation can be
analysed readily in terms of two one-dimensional substruc-
tures (Ferguson et al., 1998a,b; Gregson et al., 2000). The two
C—Hꢀ ꢀ ꢀO hydrogen bonds link the molecules into a chain of
centrosymmetric rings running parallel to the [001] direction,
in which R22(16) (Etter, 1990; Etter et al., 1990; Bernstein et al.,
1995) rings centred at (21, 0, n) alternate with R22(20) rings
1
centred at (12, 0, + n), where n represents an integer in each
2
case (Fig. 8). In the second substructure, the two C—Hꢀ ꢀ ꢀꢀ
hydrogen bonds combine to form a chain of centrosymmetric
rings, in which two types of ring alternate, running parallel to
the [100] direction. Rings containing two hydrogen bonds and
centred at (n, 0, 12) alternate with rings centred at (21 + n, 0, 12),
where n represents an integer in each case (Fig. 9). The
combination of these two chain motifs along [100] and [001]
generates a complex sheet lying parallel to (010), but there are
no direction-specific interactions between adjacent sheets.
The supramolecular assembly in compound (IV), by
contrast, is very simple. A single C—Hꢀ ꢀ ꢀꢀ hydrogen bond
Figure 6
Part of the crystal structure of compound (I), showing the formation of a
ꢀ-stacked chain parallel to [010]. The minor-disorder component and all
H atoms have been omitted for the sake of clarity. S atoms marked with
an asterisk (*) or a hash (#) are at the symmetry positions (ꢃx + 1, y + 12,
1
2
1
2
1
2
ꢃz + ) and (ꢃx + 1, y ꢃ , ꢃz + ), respectively.
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50 Sagar et al.
Four closely related N-(benzo[b]thiophen-2-yl)benzamides
Acta Cryst. (2018). C74, 45–53

research papers
type 1 molecules are pendent, so forming a finite zero-
dimensional four-molecule aggregate (Fig. 10). There are no
direction-specific interactions between adjacent tetramers.
Although the original report on the structure of compound
(V) (Kaur, Jasinski, Yathirajan et al., 2014) noted the forma-
tion of ꢀ-stacked chains running parallel to the [010] direction,
there is also, in fact, a C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond which
links inversion-related molecules into centrosymmetric dimers
(Fig. 11), so that the supramolecular assembly takes the form
of a chain of ꢀ-stacked hydrogen-bonded dimers along [010].
Although compounds (I)–(V) all have very similar consti-
tutions and very similar molecular conformations, they all
exhibit different patterns of intermolecular hydrogen bonds.
The single donor in (II) forms part of the aryl substituent (cf.
Scheme 1), as does one of the donors in (III), while the
3-benzoyl substituent provides donors in each of (III)–(V).
The connection between molecular structure and supra-
molecular aggregation remains unpredictable and the details
of the connection remain elusive.
It is of interest briefly to consider the structures of some
related compounds. The structure of parent amine (VI)
(see Scheme 2), namely 2-amino-3-benzoyl-4,5,6,7-tetra-
hydrobenzo[b]thiophene, has been reported recently (Kubicki
et al., 2012) and the anisotropic displacement parameters
suggest that there is disorder in the fused six-membered ring
which was not accounted for in the original refinement.
Accordingly, we undertook a new refinement of this structure,
using the original data set, and found that there is indeed
disorder in this ring, exactly comparable to the disorder found
in compounds (I)–(III), with the two conformations having
occupancies of 0.887 (9) and 0.113 (9) (Fig. 12 and Table 2).
Figure 8
Part of the crystal structure of compound (III), showing the formation of
a chain of centrosymmetric rings built from C—Hꢀ ꢀ ꢀO hydrogen bonds
(dashed lines) and running parallel to [001]. The unit-cell outline and H
atoms not involved in the motifs shown have been omitted for the sake of
clarity. O atoms marked with an asterisk (*), a hash (#), a dollar sign ($)
or an ampersand (&) are at the symmetry positions (ꢃx + 1, ꢃy, ꢃz + 1),
(ꢃx + 1, ꢃ y, ꢃz), (x, y, z + 1) and (x, y, z ꢃ 1), respectively.
links inversion related pairs of type 2 molecules into a cyclic
centrosymmetric dimer, from which two inversion-related
Figure 10
Figure 9
Part of the crystal structure of compound (IV), showing the formation of
a centrosymmetric tetramer built from C—Hꢀ ꢀ ꢀꢀ and C—Hꢀ ꢀ ꢀO
hydrogen bonds (dashed lines) and running parallel to [100]. The unit-
cell outline and H atoms not involved in the motifs shown have been
omitted for the sake of clarity.
Part of the crystal structure of compound (III), showing the formation of
a chain of centrosymmetric rings built from C—Hꢀ ꢀ ꢀꢀ hydrogen bonds
(dashed lines) and running parallel to [100]. H atoms not involved in the
motifs shown have been omitted for the sake of clarity.
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Acta Cryst. (2018). C74, 45–53
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Four closely related N-(benzo[b]thiophen-2-yl)benzamides 51

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approximately 180ꢂ about the exocylic C—C bond, supporting
the idea that the intramolecular N—Hꢀ ꢀ ꢀO interaction in (I)–
(VI) has a role in determining the orientation of this substi-
tuent. In each of salts (IX) and (X), the fused six-membered
ring again adopts a half-chair conformation (Sagar et al.,
2017). Both half-chair rings exhibit conformational disorder,
but with different proportions for the two conformers, i.e.
0.721 (5) and 0.279 (5) in (IX), and 0.575 (4) and 0.425 (4) in
(X).
It is somewhat disappointing to note that structures with
unmodelled disorder, such as compound (VI) (Kubicki et al.,
2012), are still being published and thus incorporated into the
Cambridge Structural Database (Groom et al., 2016). In this
connection, we have recently noted (Rajam et al., 2017) an
example of unmodelled conformational disorder involving a
simple thiophene group (Rajam et al., 2015). While enanti-
omeric and positional disorder are usually easy to detect,
although not always straightforward to unravel in cases of
multiple disorder across special positions (Zakaria et al., 2003;
Cobo et al., 2009), the detection of conformational disorder
usually requires careful inspection of the refined bond
distances and anisotropic displacement parameters, as well as
attention to any unexpected features in the difference maps.
Figure 11
Part of the crystal structure of compound (V), showing the formation of a
hydrogen-bonded dimer (dashed lines) containing the molecules at (x, y,
z) and (ꢃx + 2, ꢃy, ꢃz + 1). The original atomic coordinates (Kaur,
Jasinski, Yathirajan et al., 2014) have been used and, for the sake of
clarity, the unit-cell outline and H atoms not involved in the motif shown
have been omitted.
Acknowledgements
BKS thanks UGC, India, for the award of a Rajeev Gandhi
Fellowship. HSY thanks the University of Mysore for research
facilities.
Crystal structures have also been described for compounds
(VII) (Kumar et al., 2005) and (VIII) (Kaur, Jasinski, Kavitha
et al., 2014) (Scheme 2). In each of these compounds, the fused
six-membered ring adopts a half-chair conformation, as in (I)–
(VI) above, but with no evidence for conformational disorder
in either of them. The orientation of the 3-benzoyl group in
(VIII), however, differs from that in (I)–(VI) by a rotation of
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Four closely related N-(benzo[b]thiophen-2-yl)benzamides 53

supporting information
supporting information
Acta Cryst. (2018). C74, 45-53 [https://doi.org/10.1107/S2053229617017326]
Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-
yl)benzamides: order versus disorder, and similar molecular conformations but
different modes of supramolecular aggregation, with a new disordered
refinement of 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene
Belakavadi K. Sagar, Hemmige S. Yathirajan, Ravindranath S. Rathore and Christopher
Glidewell
Computing details
Data collection: APEX2 (Bruker, 2012) for (I), (II), (III), (IV); CrysAlis PRO (Agilent, 2012) for (VI). Cell refinement:
APEX2 (Bruker, 2012) for (I), (II), (III), (IV); CrysAlis PRO (Agilent, 2012) for (VI). Data reduction: SAINT-Plus
(Bruker, 2012) for (I), (II), (III), (IV); CrysAlis RED (Agilent, 2012) for (VI). For all structures, 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-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide (I)
Crystal data
C22H18FNO2S
Mr = 379.43
F(000) = 792
Dx = 1.371 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 5442 reflections
θ = 1.3–30.3°
Monoclinic, P21/c
a = 15.9489 (11) Å
b = 7.2739 (4) Å
c = 15.9222 (10) Å
β = 95.813 (4)°
V = 1837.6 (2) Å3
Z = 4
µ = 0.20 mm−1
T = 296 K
Block, colourless
0.15 × 0.10 × 0.10 mm
Data collection
Bruker Kappa APEXII
diffractometer
Radiation source: fine focus sealed tube
φ and ω scans
3809 independent reflections
2343 reflections with I > 2σ(I)
Rint = 0.052
θ
max = 26.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = −20→20
k = −9→9
T
min = 0.895, Tmax = 0.980
l = −20→20
21151 measured reflections
Acta Cryst. (2018). C74, 45-53
sup-1

supporting information
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.046
wR(F2) = 0.122
S = 1.02
3809 reflections
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0475P)2 + 0.4981P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.16 e Å−3
Δρmin = −0.20 e Å−3
258 parameters
12 restraints
Hydrogen site location: inferred from
neighbouring sites
Extinction correction: SHELXL,
Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.0080 (9)
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)
C7
O7
C1
C2
0.47949 (13)
0.44771 (10)
0.42894 (13)
0.34324 (14)
0.3192
0.6101 (3)
0.6398 (3)
0.6016 (3)
0.5665 (3)
0.5467
0.23133 (15)
0.15993 (11)
0.30528 (14)
0.28845 (16)
0.2335
0.0465 (6)
0.0692 (5)
0.0429 (5)
0.0532 (6)
0.064*
H2
C3
F3
C4
H4
0.29523 (14)
0.21131 (9)
0.32656 (16)
0.2920
0.5618 (3)
0.5261 (3)
0.5938 (3)
0.5897
0.35488 (19)
0.33825 (12)
0.43705 (18)
0.4806
0.0583 (7)
0.0938 (6)
0.0589 (7)
0.071*
C5
H5
0.41083 (15)
0.4341
0.6321 (3)
0.6563
0.45229 (17)
0.5071
0.0587 (7)
0.070*
C6
H6
0.46162 (14)
0.5188
0.6352 (3)
0.6603
0.38704 (15)
0.3986
0.0514 (6)
0.062*
N1
H1
0.56415 (10)
0.5837
0.5827 (2)
0.5629
0.24788 (11)
0.2994
0.0451 (5)
0.054*
S11
C12
C13
C13A
C14
H14A
H14B
C15
H15A
H15B
C16
H16A
H16B
0.59028 (4)
0.62066 (14)
0.70640 (13)
0.74750 (14)
0.8387 (2)
0.8575
0.8726
0.8513 (2)
0.9110
0.62223 (8)
0.5844 (3)
0.5546 (3)
0.5566 (3)
0.5147 (13)
0.4166
0.6227
0.4569 (6)
0.4503
0.08302 (4)
0.18772 (13)
0.20427 (13)
0.12712 (14)
0.1187 (2)
0.1574
0.1339
0.0284 (2)
0.0218
0.0539 (2)
0.0409 (5)
0.0395 (5)
0.0434 (5)
0.0586 (11)
0.070*
0.070*
0.0694 (12)
0.083*
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.8269
0.8092 (3)
0.8227
0.3362
0.5961 (6)
0.5677
0.0168
−0.0331 (2)
−0.0897
0.083*
0.0761 (13)
0.091*
0.8307
0.7179
−0.0186
0.091*
Acta Cryst. (2018). C74, 45-53
sup-2

supporting information
C17
0.7135 (3)
0.6889
0.6899
0.69285 (15)
0.74750 (14)
0.8348 (9)
0.8384
0.8762
0.8558 (7)
0.8645
0.9078
0.7861 (8)
0.7748
0.5940 (16)
0.7017
0.4857
0.5931 (3)
0.5566 (3)
0.495 (6)
0.3624
0.5469
0.555 (3)
0.6867
0.4961
0.505 (2)
0.3736
−0.0311 (2)
−0.0599
−0.0601
0.05883 (14)
0.12712 (14)
0.1092 (7)
0.1134
0.1516
0.0216 (8)
0.0213
0.0093
−0.0465 (7)
−0.0447
0.0714 (10)
0.086*
0.086*
0.0506 (6)
0.0434 (5)
0.0586 (11)
0.070*
0.070*
0.0694 (12)
0.083*
0.083*
0.0761 (13)
0.091*
0.811 (6)
0.811 (6)
0.811 (6)
0.811 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
0.189 (6)
H17A
H17B
C17A
C23A
C24
H24A
H24B
C25
H25A
H25B
C26
H26A
H26B
C27
H27A
H27B
C27A
C37
O37
C31
0.8034
0.7063 (13)
0.7132
0.5337
0.613 (7)
0.7411
−0.1017
−0.0321 (6)
−0.0461
0.091*
0.0714 (10)
0.086*
0.6583
0.5642
−0.0675
0.086*
0.69285 (15)
0.74366 (14)
0.69952 (10)
0.83655 (14)
0.87614 (17)
0.8457
0.5931 (3)
0.5196 (3)
0.4827 (3)
0.5287 (3)
0.3885 (4)
0.2854
0.05883 (14)
0.29015 (14)
0.34774 (10)
0.31342 (14)
0.36015 (17)
0.3735
0.0506 (6)
0.0456 (5)
0.0662 (5)
0.0490 (6)
0.0771 (9)
0.093*
C32
H32
C33
H33
0.9610 (2)
0.9878
0.4007 (6)
0.3052
0.3872 (2)
0.4182
0.1091 (13)
0.131*
C34
H34
1.0054 (2)
1.0625
0.5528 (7)
0.5604
0.3686 (2)
0.3869
0.1112 (14)
0.133*
C35
H35
0.96709 (19)
0.9978
0.6936 (6)
0.7974
0.3235 (2)
0.3116
0.0901 (11)
0.108*
C36
H36
0.88298 (16)
0.8569
0.6819 (4)
0.7779
0.29559 (16)
0.2644
0.0633 (7)
0.076*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C7
O7
C1
C2
C3
F3
C4
C5
C6
N1
S11
C12
C13
0.0376 (13)
0.0486 (10)
0.0333 (12)
0.0380 (13)
0.0309 (13)
0.0362 (8)
0.0507 (15)
0.0536 (16)
0.0373 (13)
0.0354 (10)
0.0551 (4)
0.0440 (13)
0.0385 (12)
0.0436 (13)
0.0989 (14)
0.0363 (12)
0.0541 (14)
0.0537 (15)
0.1247 (14)
0.0548 (15)
0.0597 (16)
0.0534 (14)
0.0538 (11)
0.0550 (4)
0.0566 (15)
0.0582 (11)
0.0578 (14)
0.0658 (16)
0.091 (2)
0.1210 (14)
0.0740 (18)
0.0629 (16)
0.0625 (16)
0.0451 (11)
0.0494 (4)
0.0428 (12)
0.0415 (12)
0.0011 (10)
0.0068 (10)
0.0029 (9)
−0.0027 (11)
−0.0046 (8)
−0.0017 (10)
−0.0026 (12)
0.0084 (13)
0.0103 (9)
0.0201 (14)
0.0067 (13)
0.0002 (11)
−0.0001 (8)
−0.0051 (3)
0.0029 (10)
0.0043 (10)
0.0005 (11)
0.0119 (10)
−0.0025 (10)
−0.0075 (12)
−0.0069 (14)
−0.0185 (11)
−0.0036 (13)
−0.0094 (12)
−0.0063 (12)
−0.0001 (9)
0.0073 (3)
0.0034 (11)
0.0032 (11)
−0.0057 (9)
0.0080 (12)
0.0043 (13)
−0.0019 (11)
−0.0001 (8)
−0.0035 (3)
−0.0034 (9)
−0.0032 (9)
0.0354 (11)
0.0385 (12)
−0.0009 (9)
−0.0021 (9)
Acta Cryst. (2018). C74, 45-53
sup-3

supporting information
C13A
C14
C15
C16
C17
C17A
C23A
C24
C25
C26
C27
C27A
C37
O37
C31
C32
C33
C34
C35
C36
0.0491 (14)
0.0567 (17)
0.072 (2)
0.105 (3)
0.091 (2)
0.0610 (15)
0.0491 (14)
0.0567 (17)
0.072 (2)
0.105 (3)
0.091 (2)
0.0610 (15)
0.0417 (13)
0.0436 (10)
0.0402 (13)
0.0546 (17)
0.060 (2)
0.0412 (18)
0.0554 (19)
0.0523 (16)
0.0389 (12)
0.069 (2)
0.081 (3)
0.073 (3)
0.079 (3)
0.0470 (13)
0.0389 (12)
0.069 (2)
0.081 (3)
0.073 (3)
0.0430 (13)
0.0538 (17)
0.0596 (19)
0.056 (2)
0.0439 (15)
0.0438 (13)
0.0430 (13)
0.0538 (17)
0.0596 (19)
0.056 (2)
0.0439 (15)
0.0438 (13)
0.0449 (13)
0.0458 (10)
0.0364 (12)
0.0678 (18)
0.084 (2)
−0.0039 (10)
0.0025 (14)
−0.006 (2)
0.0083 (11)
0.0213 (14)
0.0288 (16)
0.033 (2)
0.0082 (14)
0.0054 (11)
0.0083 (11)
0.0213 (14)
0.0288 (16)
0.033 (2)
0.0082 (14)
0.0054 (11)
0.0069 (11)
0.0081 (8)
0.0056 (10)
0.0090 (14)
0.0046 (18)
0.0046 (16)
0.0091 (16)
0.0066 (12)
−0.0010 (10)
−0.0051 (17)
−0.013 (2)
0.008 (2)
0.0074 (14)
0.0013 (11)
−0.0010 (10)
−0.0051 (17)
−0.013 (2)
0.008 (2)
0.0074 (14)
0.0013 (11)
−0.0020 (11)
0.0106 (9)
0.0010 (11)
0.0293 (17)
0.044 (3)
−0.006 (2)
−0.0127 (19)
−0.0063 (11)
−0.0039 (10)
0.0025 (14)
−0.006 (2)
−0.006 (2)
0.079 (3)
−0.0127 (19)
−0.0063 (11)
−0.0004 (11)
−0.0053 (9)
0.0043 (12)
0.0135 (17)
0.036 (2)
0.003 (2)
−0.031 (2)
−0.0114 (14)
0.0470 (13)
0.0507 (13)
0.1099 (15)
0.0706 (16)
0.109 (2)
0.183 (4)
0.220 (5)
0.147 (3)
0.0833 (19)
0.072 (2)
0.068 (2)
0.0546 (15)
0.001 (3)
−0.020 (2)
−0.0084 (14)
Geometric parameters (Å, º)
C7—O7
1.216 (3)
C16—H16A
0.9700
C7—N1
C7—C1
C1—C6
C1—C2
C2—C3
C2—H2
C3—F3
C3—C4
C4—C5
C4—H4
C5—C6
C5—H5
C6—H6
N1—C12
N1—H1
S11—C12
S11—C17A
C12—C13
C13—C13A
C13—C37
C13A—C17A
C13A—C14
C14—C15
C14—H14A
1.364 (3)
1.494 (3)
1.374 (3)
1.390 (3)
1.368 (3)
0.9300
1.363 (3)
1.372 (4)
1.370 (3)
0.9300
1.381 (3)
0.9300
0.9300
1.380 (3)
0.8600
1.711 (2)
1.731 (2)
1.383 (3)
1.450 (3)
1.457 (3)
1.349 (3)
1.505 (3)
1.531 (5)
0.9700
C16—H16B
C17—C17A
C17—H17A
C17—H17B
C24—C25
C24—H24A
C24—H24B
C25—C26
C25—H25A
C25—H25B
C26—C27
C26—H26A
C26—H26B
C27—H27A
C27—H27B
C37—O37
C37—C31
C31—C32
C31—C36
C32—C33
C32—H32
C33—C34
C33—H33
C34—C35
0.9700
1.502 (3)
0.9700
0.9700
1.529 (7)
0.9700
0.9700
1.517 (6)
0.9700
0.9700
1.532 (8)
0.9700
0.9700
0.9700
0.9700
1.241 (2)
1.492 (3)
1.377 (3)
1.383 (3)
1.380 (4)
0.9300
1.363 (5)
0.9300
1.360 (5)
Acta Cryst. (2018). C74, 45-53
sup-4

supporting information
C14—H14B
C15—C16
C15—H15A
C15—H15B
C16—C17
0.9700
1.517 (5)
0.9700
0.9700
1.530 (7)
C34—H34
C35—C36
C35—H35
C36—H36
0.9300
1.372 (4)
0.9300
0.9300
O7—C7—N1
O7—C7—C1
N1—C7—C1
C6—C1—C2
C6—C1—C7
C2—C1—C7
C3—C2—C1
C3—C2—H2
C1—C2—H2
F3—C3—C2
F3—C3—C4
C2—C3—C4
C5—C4—C3
C5—C4—H4
C3—C4—H4
C4—C5—C6
C4—C5—H5
C6—C5—H5
C1—C6—C5
C1—C6—H6
C5—C6—H6
C7—N1—C12
C7—N1—H1
C12—N1—H1
C12—S11—C17A
N1—C12—C13
N1—C12—S11
C13—C12—S11
C12—C13—C13A
C12—C13—C37
C13A—C13—C37
C17A—C13A—C13
C17A—C13A—C14
C13—C13A—C14
C13A—C14—C15
C13A—C14—H14A
C15—C14—H14A
C13A—C14—H14B
C15—C14—H14B
H14A—C14—H14B
C16—C15—C14
C16—C15—H15A
121.2 (2)
122.5 (2)
116.4 (2)
119.1 (2)
123.8 (2)
117.0 (2)
118.2 (2)
120.9
C17—C16—H16B
H16A—C16—H16B
C17A—C17—C16
C17A—C17—H17A
C16—C17—H17A
C17A—C17—H17B
C16—C17—H17B
H17A—C17—H17B
C13A—C17A—C17
C13A—C17A—S11
C17—C17A—S11
C25—C24—H24A
C25—C24—H24B
H24A—C24—H24B
C26—C25—C24
C26—C25—H25A
C24—C25—H25A
C26—C25—H25B
C24—C25—H25B
H25A—C25—H25B
C25—C26—C27
C25—C26—H26A
C27—C26—H26A
C25—C26—H26B
C27—C26—H26B
H26A—C26—H26B
C26—C27—H27A
C26—C27—H27B
H27A—C27—H27B
O37—C37—C13
O37—C37—C31
C13—C37—C31
C32—C31—C36
C32—C31—C37
C36—C31—C37
C31—C32—C33
C31—C32—H32
C33—C32—H32
C34—C33—C32
C34—C33—H33
C32—C33—H33
C35—C34—C33
109.5
108.0
109.6 (4)
109.8
109.8
109.8
109.8
108.2
125.7 (2)
113.12 (17)
121.0 (2)
109.2
109.2
107.9
111.9 (8)
109.2
109.2
109.2
109.2
107.9
109.2 (9)
109.8
109.8
109.8
109.8
108.3
110.2
110.2
120.9
118.0 (2)
118.2 (2)
123.7 (2)
117.3 (2)
121.3
121.3
120.6 (2)
119.7
119.7
121.0 (2)
119.5
119.5
124.59 (19)
117.7
117.7
90.94 (11)
124.67 (19)
122.51 (17)
112.82 (16)
111.11 (19)
120.50 (18)
128.3 (2)
112.0 (2)
121.3 (2)
126.7 (2)
111.0 (3)
109.4
109.4
109.4
109.4
108.0
109.4 (4)
109.8
108.5
121.6 (2)
116.7 (2)
121.72 (19)
118.8 (2)
119.4 (2)
121.6 (2)
120.1 (3)
119.9
119.9
119.9 (3)
120.0
120.0
120.7 (3)
Acta Cryst. (2018). C74, 45-53
sup-5

supporting information
C14—C15—H15A
C16—C15—H15B
C14—C15—H15B
H15A—C15—H15B
C15—C16—C17
C15—C16—H16A
C17—C16—H16A
C15—C16—H16B
109.8
109.8
109.8
108.2
110.9 (5)
109.5
109.5
109.5
C35—C34—H34
C33—C34—H34
C34—C35—C36
C34—C35—H35
C36—C35—H35
C35—C36—C31
C35—C36—H36
C31—C36—H36
119.6
119.6
119.7 (3)
120.1
120.1
120.6 (3)
119.7
119.7
O7—C7—C1—C6
N1—C7—C1—C6
O7—C7—C1—C2
N1—C7—C1—C2
C6—C1—C2—C3
C7—C1—C2—C3
C1—C2—C3—F3
C1—C2—C3—C4
F3—C3—C4—C5
C2—C3—C4—C5
C3—C4—C5—C6
C2—C1—C6—C5
C7—C1—C6—C5
C4—C5—C6—C1
O7—C7—N1—C12
C1—C7—N1—C12
C7—N1—C12—C13
C7—N1—C12—S11
C17A—S11—C12—N1
C17A—S11—C12—C13
N1—C12—C13—C13A
S11—C12—C13—C13A
N1—C12—C13—C37
S11—C12—C13—C37
C12—C13—C13A—C17A
C37—C13—C13A—C17A
C12—C13—C13A—C14
C37—C13—C13A—C14
C17A—C13A—C14—C15
−155.4 (2)
24.6 (3)
21.3 (3)
−158.70 (19)
−1.8 (3)
−178.6 (2)
−179.54 (19)
1.5 (4)
−179.1 (2)
−0.1 (4)
−0.9 (4)
0.8 (3)
177.4 (2)
0.6 (4)
C13—C13A—C14—C15
C13A—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C17A
C13—C13A—C17A—C17
C14—C13A—C17A—C17
C13—C13A—C17A—S11
C14—C13A—C17A—S11
C16—C17—C17A—C13A
C16—C17—C17A—S11
C12—S11—C17A—C13A
C12—S11—C17A—C17
C24—C25—C26—C27
C12—C13—C37—O37
C13A—C13—C37—O37
C12—C13—C37—C31
C13A—C13—C37—C31
O37—C37—C31—C32
C13—C37—C31—C32
O37—C37—C31—C36
C13—C37—C31—C36
C36—C31—C32—C33
C37—C31—C32—C33
C31—C32—C33—C34
C32—C33—C34—C35
C33—C34—C35—C36
C34—C35—C36—C31
C32—C31—C36—C35
C37—C31—C36—C35
157.6 (4)
50.1 (9)
−65.8 (9)
45.8 (10)
−176.0 (6)
1.1 (9)
−1.1 (2)
176.0 (5)
−14.3 (11)
171.1 (4)
−0.08 (18)
175.1 (6)
64.7 (15)
13.2 (3)
−0.4 (3)
−164.1 (2)
−166.0 (2)
16.7 (3)
179.60 (18)
−179.27 (19)
0.0 (3)
−178.05 (17)
1.32 (16)
177.20 (17)
−2.2 (2)
−0.5 (3)
−179.90 (16)
2.1 (3)
48.4 (3)
−132.4 (2)
−125.9 (2)
53.4 (3)
−1.0 (4)
−175.5 (3)
0.8 (5)
0.1 (6)
−0.7 (5)
0.5 (4)
179.6 (2)
−174.8 (5)
2.7 (6)
0.4 (4)
174.7 (2)
−19.0 (9)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
0.86
H···A
D···A
2.650 (3)
D—H···A
130
N1—H1···O37
2.01
Acta Cryst. (2018). C74, 45-53
sup-6

supporting information
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide (II)
Crystal data
C22H18ClNO2S
Mr = 395.88
F(000) = 824
Dx = 1.362 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3743 reflections
θ = 2.3–25.9°
Monoclinic, P21/n
a = 11.6776 (6) Å
b = 14.2461 (8) Å
c = 12.2957 (7) Å
β = 109.336 (2)°
V = 1930.13 (18) Å3
Z = 4
µ = 0.32 mm−1
T = 296 K
Block, colourless
0.25 × 0.20 × 0.20 mm
Data collection
Bruker Kappa APEXII
diffractometer
Radiation source: fine focus sealed tube
φ and ω scans
3743 independent reflections
2127 reflections with I > 2σ(I)
Rint = 0.047
θ
max = 25.9°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = −13→14
k = −17→17
l = −14→15
T
min = 0.882, Tmax = 0.937
28361 measured reflections
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.047
wR(F2) = 0.142
S = 1.03
3743 reflections
257 parameters
12 restraints
Hydrogen site location: inferred from
neighbouring sites
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0477P)2 + 1.4106P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.30 e Å−3
Δρmin = −0.28 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)
C7
O7
C1
C2
H2
C3
H3
C4
Cl4
C5
0.3052 (3)
0.32402 (18)
0.1822 (2)
0.0837 (3)
0.0960
−0.0329 (3)
−0.0988
−0.0506 (3)
−0.19694 (8)
0.0452 (3)
0.1590 (2)
0.07451 (16)
0.1999 (2)
0.1403 (2)
0.0763
0.1740 (2)
0.1333
0.2678 (2)
0.31045 (8)
0.3286 (2)
0.3054 (3)
0.3102 (2)
0.2546 (2)
0.2274 (3)
0.2420
0.1790 (3)
0.1613
0.1575 (3)
0.09347 (9)
0.1820 (3)
0.0537 (8)
0.0725 (7)
0.0489 (7)
0.0650 (9)
0.078*
0.0677 (9)
0.081*
0.0594 (8)
0.0892 (4)
0.0653 (9)
Acta Cryst. (2018). C74, 45-53
sup-7

supporting information
H5
0.0321
0.3924
0.1663
0.078*
C6
H6
0.1611 (3)
0.2265
0.2943 (2)
0.3354
0.2301 (3)
0.2466
0.0623 (9)
0.075*
N1
H1
0.39838 (19)
0.3796
0.22082 (17)
0.2793
0.3469 (2)
0.3453
0.0533 (6)
0.064*
S11
C12
C13
C13A
C14
0.57075 (7)
0.5191 (2)
0.6120 (2)
0.7289 (2)
0.8512 (4)
0.8458
0.8748
0.9492 (4)
1.0291
0.9359
0.9424 (5)
1.0097
0.9487
0.8221 (5)
0.8114
0.08612 (6)
0.1988 (2)
0.2646 (2)
0.2195 (2)
0.2670 (4)
0.3215
0.2883
0.1985 (4)
0.2258
0.1881
0.1075 (5)
0.0678
0.1187
0.0579 (3)
0.0051
0.41343 (8)
0.3909 (2)
0.4221 (3)
0.4669 (3)
0.512 (2)
0.5569
0.4470
0.5870 (6)
0.6030
0.6599
0.5256 (8)
0.5684
0.4500
0.513 (2)
0.4606
0.0635 (3)
0.0490 (7)
0.0494 (7)
0.0508 (7)
0.0704 (12)
0.084*
0.084*
0.073 (2)
0.088*
0.088*
0.098 (4)
0.117*
0.117*
0.0762 (16)
0.091*
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.645 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
0.355 (7)
H14A
H14B
C15
H15A
H15B
C16
H16A
H16B
C17
H17A
H17B
C17A
C23A
C24
H24B
H24A
C25
H25A
H25B
C26
H26A
H26B
C27
H27A
H27B
C27A
C37
0.8232
0.0341
0.5871
0.091*
0.7193 (3)
0.7289 (2)
0.8530 (6)
0.8638
0.8594
0.9537 (7)
0.9514
1.0328
0.9341 (8)
0.9248
1.0036
0.8192 (8)
0.8335
0.1256 (2)
0.2195 (2)
0.2643 (5)
0.2872
0.3173
0.1911 (8)
0.1761
0.2174
0.1042 (9)
0.1201
0.0628
0.0548 (5)
0.0287
0.4670 (3)
0.4669 (3)
0.517 (4)
0.5941
0.4699
0.5217 (11)
0.4441
0.5631
0.5808 (13)
0.6541
0.5954
0.503 (4)
0.4359
0.0577 (8)
0.0508 (7)
0.0704 (12)
0.084*
0.084*
0.073 (2)
0.088*
0.088*
0.098 (4)
0.117*
0.117*
0.0762 (16)
0.091*
0.7971
0.0039
0.5448
0.091*
0.7193 (3)
0.5843 (3)
0.4800 (2)
0.6826 (2)
0.7229 (3)
0.6887
0.1256 (2)
0.3642 (2)
0.39474 (16)
0.4328 (2)
0.4937 (3)
0.4934
0.4670 (3)
0.4080 (3)
0.3860 (3)
0.4160 (3)
0.5060 (3)
0.5644
0.0577 (8)
0.0572 (8)
0.0874 (8)
0.0512 (7)
0.0753 (10)
0.090*
O37
C31
C32
H32
C33
H33
0.8159 (4)
0.8455
0.5564 (3)
0.5969
0.5100 (5)
0.5724
0.1018 (15)
0.122*
C34
H34
0.8628 (4)
0.9237
0.5585 (3)
0.6013
0.4238 (5)
0.4261
0.0999 (15)
0.120*
C35
H35
0.8222 (4)
0.8550
0.4993 (4)
0.5011
0.3349 (4)
0.2756
0.1031 (15)
0.124*
C36
0.7326 (3)
0.4361 (3)
0.3309 (3)
0.0810 (11)
Acta Cryst. (2018). C74, 45-53
sup-8

supporting information
H36
0.7056
0.3948
0.2690
0.097*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C7
O7
C1
C2
C3
C4
Cl4
C5
0.0484 (17)
0.0522 (13)
0.0429 (16)
0.0530 (19)
0.0455 (18)
0.0462 (17)
0.0557 (5)
0.057 (2)
0.0493 (18)
0.0385 (13)
0.0506 (5)
0.0434 (15)
0.0435 (15)
0.0399 (15)
0.0395 (16)
0.042 (2)
0.058 (2)
0.0532 (15)
0.0499 (18)
0.057 (2)
0.068 (2)
0.073 (2)
0.1037 (8)
0.060 (2)
0.057 (2)
0.0463 (14)
0.0498 (5)
0.0482 (17)
0.0469 (17)
0.0500 (19)
0.063 (2)
0.075 (3)
0.083 (3)
0.065 (2)
0.056 (2)
0.0500 (19)
0.063 (2)
0.075 (3)
0.083 (3)
0.065 (2)
0.056 (2)
0.0541 (19)
0.0564 (14)
0.0512 (19)
0.083 (3)
0.077 (3)
0.073 (3)
0.133 (4)
0.116 (3)
0.0569 (19)
0.1014 (18)
0.0536 (17)
0.079 (2)
0.082 (2)
0.0562 (19)
0.0976 (7)
0.075 (2)
0.077 (2)
0.0746 (17)
0.0864 (6)
0.0576 (18)
0.0601 (18)
0.0626 (19)
0.100 (3)
0.093 (6)
0.124 (9)
0.097 (4)
0.068 (2)
0.0626 (19)
0.100 (3)
0.093 (6)
0.124 (9)
0.097 (4)
0.068 (2)
0.071 (2)
0.155 (2)
0.0553 (18)
0.072 (2)
0.122 (4)
0.154 (5)
0.105 (3)
0.067 (2)
−0.0049 (15)
−0.0018 (10)
−0.0011 (13)
−0.0055 (15)
−0.0083 (16)
0.0082 (16)
0.0217 (5)
0.0078 (16)
−0.0060 (15)
−0.0016 (11)
0.0004 (4)
−0.0018 (13)
−0.0009 (13)
0.0030 (13)
0.0026 (15)
0.005 (2)
0.0201 (14)
0.0109 (12)
0.0156 (13)
0.0133 (16)
0.0109 (16)
0.0132 (14)
0.0110 (5)
0.0181 (17)
0.0171 (16)
0.0180 (12)
0.0176 (4)
0.0198 (13)
0.0204 (13)
0.0171 (13)
0.0122 (17)
0.009 (3)
−0.0003 (15)
0.0012 (12)
0.0025 (14)
0.0044 (17)
−0.0026 (19)
−0.0036 (17)
−0.0074 (6)
0.0029 (17)
0.0007 (17)
0.0005 (12)
−0.0018 (4)
−0.0001 (14)
0.0003 (14)
−0.0024 (14)
−0.005 (2)
−0.008 (4)
−0.031 (5)
−0.004 (2)
−0.0026 (16)
−0.0024 (14)
−0.005 (2)
−0.008 (4)
−0.031 (5)
−0.004 (2)
−0.0026 (16)
−0.0027 (16)
−0.0010 (15)
−0.0002 (15)
−0.014 (2)
−0.040 (3)
0.013 (3)
C6
N1
S11
C12
C13
C13A
C14
C15
C16
C17
C17A
C23A
C24
C25
C26
C27
C27A
C37
O37
C31
C32
C33
C34
C35
C36
0.058 (3)
0.056 (2)
0.0476 (17)
0.0399 (15)
0.0395 (16)
0.042 (2)
0.028 (2)
−0.007 (4)
0.011 (2)
0.0169 (15)
0.0171 (13)
0.0122 (17)
0.009 (3)
0.0137 (17)
0.0058 (14)
0.0030 (13)
0.0026 (15)
0.005 (2)
0.058 (3)
0.056 (2)
0.028 (2)
−0.007 (4)
0.011 (2)
0.0137 (17)
0.0058 (14)
0.0009 (14)
0.0055 (11)
0.0026 (13)
−0.004 (2)
−0.011 (2)
−0.014 (2)
−0.025 (3)
−0.022 (2)
0.0476 (17)
0.0455 (17)
0.0502 (13)
0.0432 (16)
0.067 (2)
0.082 (3)
0.061 (3)
0.074 (3)
0.062 (2)
0.0169 (15)
0.0181 (15)
0.0335 (14)
0.0110 (14)
0.0176 (18)
0.002 (3)
0.020 (3)
0.032 (2)
0.0238 (19)
0.024 (3)
−0.009 (2)
Geometric parameters (Å, º)
C7—O7
C7—N1
C7—C1
C1—C2
C1—C6
C2—C3
C2—H2
1.222 (3)
C16—H16A
0.9700
0.9700
1.497 (5)
0.9700
0.9700
1.361 (4)
1.483 (4)
1.380 (4)
1.382 (4)
1.379 (4)
0.9300
C16—H16B
C17—C17A
C17—H17A
C17—H17B
C24—C25
1.557 (11)
0.9700
C24—H24B
Acta Cryst. (2018). C74, 45-53
sup-9

supporting information
C3—C4
C3—H3
C4—C5
C4—Cl4
C5—C6
C5—H5
C6—H6
N1—C12
N1—H1
S11—C12
S11—C17A
C12—C13
C13—C13A
C13—C37
C13A—C17A
C13A—C14
C14—C15
C14—H14A
C14—H14B
C15—C16
C15—H15A
C15—H15B
C16—C17
1.364 (4)
0.9300
1.367 (4)
1.738 (3)
1.375 (4)
0.9300
0.9300
1.369 (3)
0.8600
1.705 (3)
1.732 (3)
1.388 (4)
1.444 (4)
1.452 (4)
1.343 (4)
1.511 (4)
1.556 (11)
0.9700
C24—H24A
C25—C26
C25—H25A
C25—H25B
C26—C27
C26—H26A
C26—H26B
C27—H27A
C27—H27B
C37—O37
C37—C31
C31—C36
C31—C32
C32—C33
C32—H32
C33—C34
C33—H33
C34—C35
C34—H34
C35—C36
C35—H35
C36—H36
0.9700
1.491 (8)
0.9700
0.9700
1.537 (12)
0.9700
0.9700
0.9700
0.9700
1.235 (3)
1.487 (4)
1.357 (4)
1.362 (4)
1.394 (6)
0.9300
1.345 (6)
0.9300
1.337 (6)
0.9300
0.9700
1.489 (8)
0.9700
0.9700
1.534 (11)
1.369 (5)
0.9300
0.9300
O7—C7—N1
O7—C7—C1
N1—C7—C1
C2—C1—C6
C2—C1—C7
C6—C1—C7
C3—C2—C1
C3—C2—H2
C1—C2—H2
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C5
C3—C4—Cl4
C5—C4—Cl4
C4—C5—C6
C4—C5—H5
C6—C5—H5
C5—C6—C1
C5—C6—H6
C1—C6—H6
C7—N1—C12
C7—N1—H1
C12—N1—H1
120.7 (3)
122.8 (3)
116.5 (3)
118.2 (3)
118.3 (3)
123.5 (3)
121.0 (3)
119.5
C17—C16—H16B
H16A—C16—H16B
C17A—C17—C16
C17A—C17—H17A
C16—C17—H17A
C17A—C17—H17B
C16—C17—H17B
H17A—C17—H17B
C13A—C17A—C17
C13A—C17A—S11
C17—C17A—S11
C25—C24—H24B
C25—C24—H24A
H24B—C24—H24A
C26—C25—C24
C26—C25—H25A
C24—C25—H25A
C26—C25—H25B
C24—C25—H25B
H25A—C25—H25B
C25—C26—C27
C25—C26—H26A
C27—C26—H26A
C25—C26—H26B
109.6
108.1
109.5 (6)
109.8
109.8
109.8
109.8
108.2
125.8 (3)
113.4 (2)
120.8 (3)
109.7
109.7
108.2
109.8 (11)
109.7
109.7
109.7
109.7
119.5
119.3 (3)
120.3
120.3
121.2 (3)
119.5 (3)
119.2 (3)
119.1 (3)
120.5
120.5
121.3 (3)
119.4
108.2
108.7 (12)
109.9
109.9
109.9
119.4
126.3 (3)
116.9
116.9
Acta Cryst. (2018). C74, 45-53
sup-10

supporting information
C12—S11—C17A
N1—C12—C13
N1—C12—S11
90.68 (14)
124.2 (3)
122.8 (2)
112.9 (2)
111.0 (3)
120.3 (2)
128.8 (3)
112.1 (3)
121.1 (3)
126.9 (3)
110.8 (6)
109.5
109.5
109.5
109.5
108.1
109.8 (9)
109.7
109.7
109.7
109.7
C27—C26—H26B
H26A—C26—H26B
C26—C27—H27A
C26—C27—H27B
H27A—C27—H27B
O37—C37—C13
O37—C37—C31
C13—C37—C31
C36—C31—C32
C36—C31—C37
C32—C31—C37
C31—C32—C33
C31—C32—H32
C33—C32—H32
C34—C33—C32
C34—C33—H33
C32—C33—H33
C35—C34—C33
C35—C34—H34
C33—C34—H34
C34—C35—C36
C34—C35—H35
C36—C35—H35
C31—C36—C35
C31—C36—H36
C35—C36—H36
109.9
108.3
110.1
110.1
C13—C12—S11
C12—C13—C13A
C12—C13—C37
C13A—C13—C37
C17A—C13A—C13
C17A—C13A—C14
C13—C13A—C14
C13A—C14—C15
C13A—C14—H14A
C15—C14—H14A
C13A—C14—H14B
C15—C14—H14B
H14A—C14—H14B
C16—C15—C14
C16—C15—H15A
C14—C15—H15A
C16—C15—H15B
C14—C15—H15B
H15A—C15—H15B
C15—C16—C17
C15—C16—H16A
C17—C16—H16A
C15—C16—H16B
108.4
122.3 (3)
117.8 (3)
119.8 (2)
118.9 (3)
119.5 (3)
121.5 (3)
119.5 (4)
120.3
120.3
120.2 (4)
119.9
119.9
120.2 (4)
119.9
119.9
120.3 (4)
119.9
119.9
120.9 (4)
119.5
108.2
110.3 (10)
109.6
109.6
109.6
119.5
O7—C7—C1—C2
N1—C7—C1—C2
O7—C7—C1—C6
N1—C7—C1—C6
C6—C1—C2—C3
C7—C1—C2—C3
C1—C2—C3—C4
C2—C3—C4—C5
C2—C3—C4—Cl4
C3—C4—C5—C6
Cl4—C4—C5—C6
C4—C5—C6—C1
C2—C1—C6—C5
C7—C1—C6—C5
O7—C7—N1—C12
C1—C7—N1—C12
C7—N1—C12—C13
C7—N1—C12—S11
C17A—S11—C12—N1
C17A—S11—C12—C13
N1—C12—C13—C13A
9.9 (5)
C13—C13A—C14—C15
C13A—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C17A
C13—C13A—C17A—C17
C14—C13A—C17A—C17
C13—C13A—C17A—S11
C14—C13A—C17A—S11
C16—C17—C17A—C13A
C16—C17—C17A—S11
C12—S11—C17A—C13A
C12—S11—C17A—C17
C24—C25—C26—C27
C12—C13—C37—O37
C13A—C13—C37—O37
C12—C13—C37—C31
C13A—C13—C37—C31
O37—C37—C31—C36
C13—C37—C31—C36
O37—C37—C31—C32
C13—C37—C31—C32
161.7 (8)
49 (2)
−66.2 (18)
49 (2)
−176.9 (14)
2 (2)
0.1 (4)
−170.5 (3)
−168.4 (3)
11.3 (4)
−1.1 (5)
−179.4 (3)
0.2 (5)
0.6 (5)
179.4 (13)
−17 (2)
178.5 (3)
−0.6 (5)
−178.5 (2)
−0.4 (5)
1.1 (5)
165.8 (10)
−0.4 (3)
176.8 (13)
69.1 (18)
11.6 (5)
−168.1 (3)
−166.2 (3)
14.2 (5)
179.4 (3)
3.7 (5)
−175.9 (3)
173.6 (3)
−6.6 (4)
−179.3 (3)
0.6 (2)
−107.6 (4)
70.2 (4)
71.4 (4)
179.2 (3)
−110.7 (4)
Acta Cryst. (2018). C74, 45-53
sup-11

supporting information
S11—C12—C13—C13A
N1—C12—C13—C37
−0.6 (3)
−0.5 (5)
179.7 (2)
0.3 (4)
180.0 (3)
−179.0 (14)
0.7 (14)
−17 (2)
C36—C31—C32—C33
−1.3 (5)
179.6 (3)
1.9 (6)
−1.3 (7)
0.0 (7)
0.1 (5)
179.1 (3)
0.6 (7)
C37—C31—C32—C33
C31—C32—C33—C34
C32—C33—C34—C35
C33—C34—C35—C36
C32—C31—C36—C35
C37—C31—C36—C35
C34—C35—C36—C31
S11—C12—C13—C37
C12—C13—C13A—C17A
C37—C13—C13A—C17A
C12—C13—C13A—C14
C37—C13—C13A—C14
C17A—C13A—C14—C15
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N1—H1···O37
0.86
0.93
0.97
0.97
1.99
2.76
2.96
2.73
2.641 (3)
3.676 (4)
3.475 (9)
3.530 (17)
132
169
114
140
C3—H3···Cg1i
C14—H14A···Cg1
C24—H24A···Cg1
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide (III)
Crystal data
C22H17F2NO2S
Mr = 397.43
Triclinic, P1
a = 7.6718 (3) Å
b = 9.8833 (3) Å
c = 13.5925 (5) Å
α = 104.925 (4)°
β = 95.476 (2)°
γ = 103.633 (3)°
V = 954.32 (6) Å3
Z = 2
F(000) = 412
Dx = 1.383 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4414 reflections
θ = 1.6–27.6°
µ = 0.21 mm−1
T = 296 K
Block, colourless
0.20 × 0.20 × 0.15 mm
Data collection
Bruker Kappa APEXII
diffractometer
Radiation source: fine focus sealed tube
φ and ω scans
4375 independent reflections
2814 reflections with I > 2σ(I)
Rint = 0.041
θ
max = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = −9→9
k = −12→12
l = −17→17
T
min = 0.942, Tmax = 0.970
21940 measured reflections
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.041
wR(F2) = 0.108
S = 1.01
4375 reflections
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0379P)2 + 0.3345P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.23 e Å−3
Δρmin = −0.25 e Å−3
267 parameters
12 restraints
Hydrogen site location: inferred from
neighbouring sites
Extinction correction: SHELXL,
Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.0131 (17)
Acta Cryst. (2018). C74, 45-53
sup-12

supporting information
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)
C7
O7
C1
C2
F2
C3
H3
0.2985 (3)
0.3232 (2)
0.3154 (3)
0.4588 (3)
0.5870 (2)
0.4795 (4)
0.5779
−0.1093 (2)
−0.18513 (16)
−0.1458 (2)
−0.1956 (2)
−0.20460 (18)
−0.2323 (2)
−0.2661
0.25624 (16)
0.17654 (11)
0.35650 (15)
0.38729 (17)
0.32721 (11)
0.47761 (19)
0.4953
0.0428 (5)
0.0596 (4)
0.0413 (5)
0.0513 (5)
0.0828 (5)
0.0631 (7)
0.076*
C4
H4
0.3530 (4)
0.3657
−0.2184 (2)
−0.2426
0.54089 (18)
0.6024
0.0645 (7)
0.077*
C5
H5
0.2073 (4)
0.1212
−0.1690 (3)
−0.1591
0.51490 (18)
0.5581
0.0620 (6)
0.074*
C6
F6
N1
H1
0.1921 (3)
0.04692 (19)
0.2570 (2)
0.2418
−0.1348 (2)
−0.08836 (18)
0.01864 (17)
0.0668
0.42373 (17)
0.39741 (12)
0.26251 (12)
0.3220
0.0513 (5)
0.0821 (5)
0.0430 (4)
0.052*
S11
0.28668 (7)
0.2370 (2)
0.1764 (3)
0.1798 (3)
0.1373 (9)
0.1786
0.0069
0.2319 (6)
0.1923
0.3624
0.1877 (6)
0.2378
0.0567
0.2639 (16)
0.2036
0.00737 (6)
0.0786 (2)
0.2008 (2)
0.2408 (2)
0.3748 (4)
0.4556
0.3567
0.4131 (4)
0.4911
0.4467
0.2814 (4)
0.3097
0.2449
0.1612 (6)
0.0698
0.06263 (4)
0.18196 (14)
0.18835 (14)
0.09357 (15)
0.0747 (3)
0.1373
0.0560
−0.0120 (3)
−0.0301
0.0111
−0.1058 (3)
−0.1626
−0.1262
−0.0845 (3)
−0.1365
0.04521 (16)
0.0376 (4)
0.0384 (4)
0.0408 (5)
0.0538 (13)
0.065*
0.065*
0.0719 (13)
0.086*
0.086*
0.0721 (12)
0.087*
0.087*
0.0596 (8)
0.071*
C12
C13
C13A
C14
H14A
H14B
C15
H15A
H15B
C16
H16A
H16B
C17
H17B
H17A
C17A
C23A
C24
H24A
H24B
C25
H25A
H25B
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.784 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.3928
0.1833
−0.0881
0.071*
0.2358 (3)
0.1798 (3)
0.178 (4)
0.2917
0.0798
0.1530 (18)
0.0303
0.1471 (2)
0.2408 (2)
0.3878 (13)
0.4590
0.4197
0.3780 (16)
0.3209
0.02047 (15)
0.09357 (15)
0.0789 (10)
0.1140
0.1091
−0.0355 (10)
−0.0678
0.0430 (5)
0.0408 (5)
0.0538 (13)
0.065*
0.065*
0.0719 (13)
0.086*
0.1685
0.4749
−0.0431
0.086*
Acta Cryst. (2018). C74, 45-53
sup-13

supporting information
C26
0.2875 (19)
0.4104
0.2748
0.255 (6)
0.1448
0.3558
0.2358 (3)
0.1167 (3)
0.1794 (2)
−0.0315 (3)
−0.0286 (3)
0.0702
−0.1713 (3)
−0.1680
−0.3193 (3)
−0.4159
0.3092 (14)
0.3637
0.3122
0.152 (2)
0.0920
0.1150
0.1471 (2)
0.2722 (2)
0.26502 (18)
0.34488 (19)
0.4664 (2)
0.5062
0.5282 (2)
0.6106
0.4684 (2)
0.5103
−0.0896 (10)
−0.0558
−0.1606
−0.0873 (11)
−0.1346
−0.1084
0.02047 (15)
0.28286 (15)
0.36795 (11)
0.27706 (14)
0.35635 (16)
0.4098
0.35617 (19)
0.4090
0.27803 (19)
0.2784
0.0721 (12)
0.087*
0.087*
0.0596 (8)
0.071*
0.071*
0.0430 (5)
0.0421 (5)
0.0648 (5)
0.0371 (4)
0.0496 (5)
0.060*
0.0594 (6)
0.071*
0.0564 (6)
0.068*
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
0.216 (6)
H26A
H26B
C27
H27A
H27B
C27A
C37
O37
C31
C32
H32
C33
H33
C34
H34
C35
H35
C36
−0.3245 (3)
−0.4252
−0.1803 (3)
−0.1833
0.3475 (2)
0.3066
0.2864 (2)
0.2052
0.19989 (17)
0.1476
0.19885 (15)
0.1451
0.0506 (5)
0.061*
0.0436 (5)
0.052*
H36
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C7
O7
C1
C2
F2
C3
C4
C5
0.0445 (12)
0.0837 (12)
0.0490 (12)
0.0582 (14)
0.0810 (10)
0.0720 (17)
0.0820 (19)
0.0734 (17)
0.0539 (13)
0.0696 (10)
0.0573 (11)
0.0528 (3)
0.0373 (11)
0.0380 (11)
0.0361 (11)
0.055 (3)
0.0452 (11)
0.0613 (9)
0.0376 (10)
0.0505 (12)
0.1194 (12)
0.0602 (14)
0.0572 (14)
0.0640 (15)
0.0525 (12)
0.1271 (13)
0.0476 (9)
0.0506 (3)
0.0435 (10)
0.0447 (10)
0.0501 (11)
0.0614 (15)
0.084 (3)
0.0463 (12)
0.0483 (9)
0.0434 (11)
0.0540 (13)
0.0805 (10)
0.0618 (15)
0.0531 (14)
0.0552 (14)
0.0583 (14)
0.0931 (11)
0.0354 (9)
0.0391 (3)
0.0367 (10)
0.0382 (10)
0.0436 (11)
0.0632 (15)
0.105 (3)
0.0214 (9)
0.0107 (9)
0.0203 (8)
0.0079 (9)
0.0099 (11)
0.0281 (8)
−0.0077 (13)
−0.0050 (13)
0.0207 (12)
0.0134 (11)
0.0414 (8)
0.0115 (8)
0.0131 (2)
0.0073 (8)
0.0061 (8)
0.0073 (9)
0.0151 (16)
0.044 (2)
0.0168 (9)
0.0172 (7)
0.0157 (9)
0.0175 (10)
0.0394 (9)
0.0234 (12)
0.0299 (12)
0.0295 (12)
0.0263 (11)
0.0669 (10)
0.0170 (7)
0.0146 (2)
0.0141 (8)
0.0149 (8)
0.0219 (9)
0.0373 (13)
0.068 (2)
0.0418 (9)
0.0190 (9)
0.0283 (11)
0.0712 (10)
0.0279 (13)
0.0079 (13)
0.0138 (13)
0.0219 (11)
0.0595 (9)
0.0285 (8)
0.0232 (2)
0.0169 (9)
0.0184 (9)
0.0159 (9)
0.0265 (17)
0.036 (2)
C6
F6
N1
S11
C12
C13
C13A
C14
C15
C16
C17
C17A
C23A
C24
C25
C26
0.065 (3)
0.073 (3)
0.0620 (18)
0.0385 (11)
0.0361 (11)
0.055 (3)
0.104 (3)
0.064 (2)
0.032 (3)
0.022 (2)
0.056 (2)
0.0813 (19)
0.0563 (12)
0.0501 (11)
0.0614 (15)
0.084 (3)
0.0489 (13)
0.0405 (11)
0.0436 (11)
0.0632 (15)
0.105 (3)
0.0252 (15)
0.0157 (9)
0.0159 (9)
0.0265 (17)
0.036 (2)
0.0207 (12)
0.0079 (9)
0.0073 (9)
0.0151 (16)
0.044 (2)
0.0327 (13)
0.0219 (10)
0.0219 (9)
0.0373 (13)
0.068 (2)
0.065 (3)
0.073 (3)
0.104 (3)
0.064 (2)
0.032 (3)
0.022 (2)
0.056 (2)
Acta Cryst. (2018). C74, 45-53
sup-14

supporting information
C27
C27A
C37
O37
C31
C32
C33
C34
C35
C36
0.0620 (18)
0.0385 (11)
0.0500 (12)
0.0888 (12)
0.0431 (11)
0.0544 (13)
0.0646 (15)
0.0506 (14)
0.0402 (12)
0.0492 (12)
0.0813 (19)
0.0563 (12)
0.0421 (10)
0.0849 (11)
0.0380 (10)
0.0453 (11)
0.0453 (12)
0.0554 (13)
0.0583 (13)
0.0427 (11)
0.0489 (13)
0.0405 (11)
0.0392 (11)
0.0370 (8)
0.0362 (10)
0.0471 (12)
0.0690 (16)
0.0777 (17)
0.0568 (13)
0.0394 (11)
0.0252 (15)
0.0157 (9)
0.0202 (9)
0.0588 (10)
0.0169 (9)
0.0201 (10)
0.0276 (11)
0.0304 (11)
0.0155 (10)
0.0169 (9)
0.0207 (12)
0.0079 (9)
0.0072 (9)
0.0047 (8)
0.0086 (9)
0.0033 (10)
0.0132 (13)
0.0192 (12)
0.0026 (10)
0.0060 (9)
0.0327 (13)
0.0219 (10)
0.0134 (9)
0.0159 (8)
0.0152 (8)
0.0059 (9)
0.0052 (11)
0.0267 (12)
0.0226 (11)
0.0093 (9)
Geometric parameters (Å, º)
C7—O7
1.208 (2)
C16—H16A
0.9700
C7—N1
C7—C1
C1—C2
C1—C6
C2—F2
C2—C3
C3—C4
C3—H3
C4—C5
C4—H4
C5—C6
C5—H5
C6—F6
N1—C12
N1—H1
S11—C12
S11—C17A
C12—C13
C13—C13A
C13—C37
C13A—C17A
C13A—C14
C14—C15
C14—H14A
C14—H14B
C15—C16
C15—H15A
C15—H15B
C16—C17
1.359 (2)
1.499 (3)
1.379 (3)
1.380 (3)
1.341 (2)
1.373 (3)
1.365 (3)
0.9300
1.372 (3)
0.9300
1.368 (3)
0.9300
C16—H16B
C17—C17A
C17—H17B
C17—H17A
C24—C25
C24—H24A
C24—H24B
C25—C26
C25—H25A
C25—H25B
C26—C27
C26—H26A
C26—H26B
C27—H27A
C27—H27B
C37—O37
C37—C31
C31—C36
C31—C32
C32—C33
C32—H32
C33—C34
C33—H33
C34—C35
C34—H34
C35—C36
C35—H35
C36—H36
0.9700
1.499 (3)
0.9700
0.9700
1.522 (6)
0.9700
0.9700
1.512 (6)
0.9700
0.9700
1.523 (7)
0.9700
1.353 (2)
1.385 (2)
0.8600
0.9700
0.9700
0.9700
1.7111 (19)
1.7338 (19)
1.379 (2)
1.443 (3)
1.468 (3)
1.351 (3)
1.513 (3)
1.525 (4)
0.9700
0.9700
1.513 (4)
0.9700
0.9700
1.520 (6)
1.236 (2)
1.487 (3)
1.381 (3)
1.386 (3)
1.374 (3)
0.9300
1.377 (3)
0.9300
1.369 (3)
0.9300
1.379 (3)
0.9300
0.9300
O7—C7—N1
O7—C7—C1
N1—C7—C1
C2—C1—C6
122.35 (18)
123.19 (17)
114.45 (17)
114.98 (18)
C17—C16—H16B
H16A—C16—H16B
C17A—C17—C16
C17A—C17—H17B
109.3
107.9
110.1 (3)
109.6
Acta Cryst. (2018). C74, 45-53
sup-15

supporting information
C2—C1—C7
C6—C1—C7
F2—C2—C3
F2—C2—C1
C3—C2—C1
C4—C3—C2
C4—C3—H3
C2—C3—H3
C3—C4—C5
C3—C4—H4
C5—C4—H4
C6—C5—C4
C6—C5—H5
C4—C5—H5
F6—C6—C5
F6—C6—C1
120.96 (18)
124.06 (18)
118.5 (2)
118.20 (18)
123.3 (2)
118.7 (2)
120.6
120.6
120.9 (2)
119.6
C16—C17—H17B
C17A—C17—H17A
C16—C17—H17A
H17B—C17—H17A
C13A—C17A—C17
C13A—C17A—S11
C17—C17A—S11
C25—C24—H24A
C25—C24—H24B
H24A—C24—H24B
C26—C25—C24
C26—C25—H25A
C24—C25—H25A
C26—C25—H25B
C24—C25—H25B
H25A—C25—H25B
C25—C26—C27
C25—C26—H26A
C27—C26—H26A
C25—C26—H26B
C27—C26—H26B
H26A—C26—H26B
C26—C27—H27A
C26—C27—H27B
H27A—C27—H27B
O37—C37—C13
O37—C37—C31
C13—C37—C31
C36—C31—C32
C36—C31—C37
C32—C31—C37
C33—C32—C31
C33—C32—H32
C31—C32—H32
C32—C33—C34
C32—C33—H33
C34—C33—H33
C35—C34—C33
C35—C34—H34
C33—C34—H34
C34—C35—C36
C34—C35—H35
C36—C35—H35
C35—C36—C31
C35—C36—H36
C31—C36—H36
109.6
109.6
109.6
108.1
125.9 (2)
112.59 (14)
121.4 (2)
109.6
109.6
108.1
111.7 (7)
109.3
109.3
109.3
109.3
107.9
110.3 (8)
109.6
109.6
109.6
119.6
118.1 (2)
120.9
120.9
118.1 (2)
117.93 (18)
124.0 (2)
126.00 (16)
117.0
C5—C6—C1
C7—N1—C12
C7—N1—H1
C12—N1—H1
117.0
C12—S11—C17A
C13—C12—N1
C13—C12—S11
N1—C12—S11
C12—C13—C13A
C12—C13—C37
C13A—C13—C37
C17A—C13A—C13
C17A—C13A—C14
C13—C13A—C14
C13A—C14—C15
C13A—C14—H14A
C15—C14—H14A
C13A—C14—H14B
C15—C14—H14B
H14A—C14—H14B
C16—C15—C14
C16—C15—H15A
C14—C15—H15A
C16—C15—H15B
C14—C15—H15B
H15A—C15—H15B
C15—C16—C17
C15—C16—H16A
C17—C16—H16A
C15—C16—H16B
91.04 (9)
124.46 (17)
112.65 (14)
122.90 (13)
111.36 (16)
120.60 (16)
128.04 (16)
112.28 (16)
121.3 (2)
126.4 (2)
109.7 (3)
109.7
109.7
109.7
109.7
108.2
110.2 (4)
109.6
109.6
109.6
109.6
109.6
108.1
110.0
110.0
108.4
120.90 (17)
118.50 (17)
120.43 (16)
119.09 (18)
121.26 (17)
119.41 (17)
120.2 (2)
119.9
119.9
120.2 (2)
119.9
119.9
120.1 (2)
119.9
119.9
119.9 (2)
120.1
120.1
120.51 (19)
119.7
108.1
111.7 (4)
109.3
109.3
109.3
119.7
O7—C7—C1—C2
44.1 (3)
C37—C13—C13A—C14
5.8 (4)
Acta Cryst. (2018). C74, 45-53
sup-16

supporting information
N1—C7—C1—C2
O7—C7—C1—C6
N1—C7—C1—C6
C6—C1—C2—F2
C7—C1—C2—F2
C6—C1—C2—C3
C7—C1—C2—C3
F2—C2—C3—C4
C1—C2—C3—C4
C2—C3—C4—C5
C3—C4—C5—C6
C4—C5—C6—F6
C4—C5—C6—C1
C2—C1—C6—F6
C7—C1—C6—F6
C2—C1—C6—C5
−134.5 (2)
−135.1 (2)
46.3 (3)
−177.94 (19)
2.8 (3)
C17A—C13A—C14—C15
−21.2 (6)
155.4 (3)
52.0 (6)
−65.0 (8)
41.7 (10)
−176.6 (6)
0.4 (8)
C13—C13A—C14—C15
C13A—C14—C15—C16
C14—C15—C16—C17
C15—C16—C17—C17A
C13—C13A—C17A—C17
C14—C13A—C17A—C17
C13—C13A—C17A—S11
C14—C13A—C17A—S11
C16—C17—C17A—C13A
C16—C17—C17A—S11
C12—S11—C17A—C13A
C12—S11—C17A—C17
C24—C25—C26—C27
C12—C13—C37—O37
C13A—C13—C37—O37
C12—C13—C37—C31
C13A—C13—C37—C31
O37—C37—C31—C36
C13—C37—C31—C36
O37—C37—C31—C32
C13—C37—C31—C32
C36—C31—C32—C33
C37—C31—C32—C33
C31—C32—C33—C34
C32—C33—C34—C35
C33—C34—C35—C36
C34—C35—C36—C31
C32—C31—C36—C35
C37—C31—C36—C35
0.2 (3)
−179.1 (2)
177.7 (2)
−0.4 (4)
0.2 (4)
0.2 (4)
179.0 (2)
−0.5 (4)
−179.17 (19)
0.1 (3)
0.3 (3)
179.6 (2)
0.2 (3)
178.76 (18)
172.90 (19)
−7.3 (3)
2.51 (16)
−177.29 (17)
176.82 (18)
−3.0 (2)
−3.9 (3)
176.34 (15)
1.9 (2)
−0.1 (2)
177.0 (3)
−10.4 (11)
173.3 (4)
−1.37 (16)
175.4 (6)
64.1 (14)
28.0 (3)
−152.8 (2)
−147.08 (19)
32.1 (3)
−137.2 (2)
38.0 (3)
37.0 (3)
−147.78 (19)
−0.7 (3)
−175.0 (2)
1.0 (3)
C7—C1—C6—C5
O7—C7—N1—C12
C1—C7—N1—C12
C7—N1—C12—C13
C7—N1—C12—S11
C17A—S11—C12—C13
C17A—S11—C12—N1
N1—C12—C13—C13A
S11—C12—C13—C13A
N1—C12—C13—C37
S11—C12—C13—C37
C12—C13—C13A—C17A
C37—C13—C13A—C17A
C12—C13—C13A—C14
−0.3 (4)
−0.7 (3)
1.0 (3)
−0.4 (3)
−177.31 (19)
−174.9 (4)
173.88 (18)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
N1—H1···O37
0.86
0.93
0.97
0.93
0.93
2.08
2.50
2.59
2.85
2.75
2.718 (2)
3.326 (3)
3.494 (12)
3.635 (2)
3.520 (2)
130
148
156
143
141
C3—H3···O37i
C17—H17A···O7ii
C4—H4···Cg1iii
C35—H35···Cg2iv
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z; (iii) −x, −y, −z+1; (iv) x−1, y, z.
N-(3-Benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide (IV)
Crystal data
C23H21NO3S
b = 12.9230 (14) Å
c = 19.031 (2) Å
α = 96.811 (5)°
Mr = 391.47
Triclinic, P1
a = 8.5129 (9) Å
β = 102.665 (6)°
Acta Cryst. (2018). C74, 45-53
sup-17

supporting information
γ = 105.321 (5)°
V = 1935.1 (4) Å3
Z = 4
F(000) = 824
Dx = 1.344 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 8692 reflections
θ = 1.1–27.4°
µ = 0.19 mm−1
T = 296 K
Block, colourless
0.20 × 0.15 × 0.15 mm
Data collection
Bruker Kappa APEXII
diffractometer
Radiation source: fine focus sealed tube
φ and ω scans
8015 independent reflections
4159 reflections with I > 2σ(I)
Rint = 0.072
θ
max = 26.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = −10→10
k = −16→16
l = −23→23
T
min = 0.935, Tmax = 0.972
37373 measured reflections
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.052
wR(F2) = 0.151
S = 0.97
8015 reflections
511 parameters
0 restraints
Hydrogen site location: mixed
H atoms treated by a mixture of independent
and constrained refinement
w = 1/[σ2(Fo2) + (0.0707P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.23 e Å−3
Δρmin = −0.36 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
C17
O17
C11
C12
C13
H13
C14
H14
C15
H15
C16
H16
O12
C18
H18A
H18B
0.7291 (3)
0.6890 (2)
0.8727 (3)
0.9407 (3)
1.0831 (4)
1.135 (4)
1.1547 (4)
1.2494
1.0888 (4)
1.1372
0.9503 (4)
0.9066
0.4920 (2)
0.46367 (16)
0.5902 (2)
0.6250 (2)
0.7148 (3)
0.735 (2)
0.7718 (2)
0.8325
0.7406 (3)
0.7799
0.6504 (2)
0.6287
0.42332 (17)
0.35654 (11)
0.46126 (16)
0.53685 (16)
0.56369 (19)
0.6153 (16)
0.5164 (2)
0.5350
0.4423 (2)
0.4106
0.41536 (17)
0.3649
0.0432 (7)
0.0583 (6)
0.0415 (7)
0.0445 (7)
0.0558 (8)
0.067*
0.0623 (9)
0.075*
0.0616 (9)
0.074*
0.0520 (8)
0.062*
0.0574 (5)
0.0706 (10)
0.106*
0.8629 (2)
0.9289 (4)
1.0436
0.56645 (16)
0.5935 (3)
0.5917
0.58071 (11)
0.65822 (16)
0.6708
0.8624
0.5417
0.6805
0.106*
Acta Cryst. (2018). C74, 45-53
sup-18

supporting information
H18C
N11
H11
0.9253
0.6436 (3)
0.6726
0.44061 (9)
0.5132 (3)
0.4327 (3)
0.3002 (3)
0.1737 (3)
0.1351
0.6655
0.43260 (17)
0.4563
0.28363 (6)
0.3366 (2)
0.2715 (2)
0.1774 (2)
0.0934 (2)
0.1293
0.0429
0.0303 (3)
−0.0340
0.0754
−0.0040 (2)
−0.0467
0.6757
0.46496 (14)
0.5115
0.34524 (4)
0.43732 (14)
0.47888 (14)
0.43310 (14)
0.45662 (15)
0.4942
0.4778
0.39350 (16)
0.4081
0.3825
0.32617 (17)
0.2882
0.106*
0.0420 (6)
0.071 (11)*
0.0479 (2)
0.0376 (6)
0.0349 (6)
0.0366 (6)
0.0465 (7)
0.056*
0.056*
0.0585 (8)
0.070*
0.070*
0.0617 (9)
0.074*
S111
C112
C113
C13A
C114
H11A
H11B
C115
H11C
H11D
C116
H11E
H11F
C117
H11G
H11H
C17A
C137
O137
C131
C132
H132
C133
H133
C134
H134
C135
H135
C136
H136
C27
0.2278
0.0235 (4)
−0.0395
−0.0501
0.0732 (4)
−0.0271
0.1452
0.1663 (4)
0.2236
0.0862
0.2920 (3)
0.4843 (3)
0.5584 (3)
0.4570 (3)
0.4077 (3)
0.3825
0.3958 (4)
0.3608
0.4347 (4)
0.4270
0.4853 (3)
0.5134
0.4944 (3)
0.5258
0.6652 (3)
0.6146 (2)
0.5718 (3)
0.6084 (3)
0.5056 (4)
0.5293
−0.0502
0.0936 (2)
0.0694
0.3368
0.29797 (16)
0.2634
0.074*
0.0556 (8)
0.067*
0.1269
0.2728
0.067*
0.1753 (2)
0.2989 (2)
0.39291 (16)
0.2123 (2)
0.2322 (2)
0.2968
0.1579 (3)
0.1717
0.0635 (3)
0.0136
0.0422 (2)
−0.0216
0.1162 (2)
0.1010
−0.0187 (2)
−0.01895 (17)
−0.1027 (2)
−0.1044 (2)
−0.1841 (3)
−0.1847
0.36089 (15)
0.55881 (15)
0.59155 (11)
0.60386 (14)
0.66724 (15)
0.6791
0.71268 (17)
0.7549
0.69670 (19)
0.7281
0.6344 (2)
0.6238
0.58719 (16)
0.5442
0.90359 (16)
0.83797 (11)
0.93938 (16)
1.01425 (17)
1.04075 (19)
1.0908
0.0421 (7)
0.0394 (7)
0.0584 (6)
0.0384 (6)
0.0493 (7)
0.059*
0.0661 (9)
0.079*
0.0676 (10)
0.081*
0.0596 (9)
0.072*
0.0480 (7)
0.058*
0.0422 (7)
0.0642 (6)
0.0414 (7)
0.0446 (7)
0.0615 (9)
0.074*
O27
C21
C22
C23
H23
C24
H24
0.3689 (4)
0.3013
−0.2621 (3)
−0.3156
0.9936 (2)
1.0119
0.0708 (10)
0.085*
C25
H25
0.3312 (4)
0.2380
−0.2623 (3)
−0.3153
0.9203 (2)
0.8887
0.0709 (10)
0.085*
C26
H26
0.4318 (4)
0.4059
−0.1833 (2)
−0.1838
0.89307 (18)
0.8429
0.0584 (8)
0.070*
O22
C28
H28A
0.7458 (2)
0.7914 (4)
0.7028
−0.02601 (16)
−0.0238 (3)
−0.0121
1.05790 (11)
1.13475 (16)
1.1553
0.0558 (5)
0.0661 (9)
0.099*
Acta Cryst. (2018). C74, 45-53
sup-19

supporting information
H28B
H28C
N21
0.8937
0.8085
0.8057 (3)
0.8377
0.0344
1.1573
1.1435
0.94501 (12)
0.9907
0.099*
0.099*
0.0395 (5)
0.047*
−0.0921
0.05953 (16)
0.0567
H21
S211
0.85579 (9)
0.9009 (3)
1.0392 (3)
1.1148 (3)
1.2753 (3)
1.3573
1.2525
1.3484 (4)
1.4384
1.3963
1.2157 (4)
1.2678
1.1669
1.0772 (4)
0.9790
0.15549 (6)
0.1431 (2)
0.2265 (2)
0.2983 (2)
0.3921 (2)
0.3730
0.4556
0.4203 (3)
0.4890
0.3641
0.4297 (3)
0.4529
0.4852
0.3228 (2)
0.3363
0.82917 (4)
0.91981 (14)
0.96251 (14)
0.91849 (14)
0.94344 (15)
0.9795
0.9667
0.87987 (17)
0.8958
0.8642
0.81655 (17)
0.7783
0.8326
0.78561 (16)
0.7559
0.0450 (2)
0.0361 (6)
0.0345 (6)
0.0365 (6)
0.0485 (7)
0.058*
0.058*
0.0628 (9)
0.075*
0.075*
0.0649 (9)
0.078*
0.078*
0.0523 (8)
0.063*
C212
C213
C23A
C214
H21A
H21B
C215
H21C
H21D
C216
H21E
H21F
C217
H21G
H21H
C27A
C237
O237
C231
C232
H232
C233
H233
C234
H234
C235
H235
C236
H236
1.1154
0.2752
0.7544
0.063*
1.0301 (3)
1.0898 (3)
1.0632 (2)
1.1630 (3)
1.2766 (3)
1.3126
1.3360 (4)
1.4131
1.2813 (4)
1.3205
0.2683 (2)
0.2345 (2)
0.15246 (15)
0.3431 (2)
0.3540 (2)
0.2949
0.4516 (3)
0.4587
0.5386 (3)
0.6044
0.84655 (15)
1.04255 (15)
1.07003 (10)
1.09194 (14)
1.15913 (15)
1.1711
1.20796 (16)
1.2525
1.19082 (17)
1.2241
0.0419 (7)
0.0387 (6)
0.0558 (5)
0.0362 (6)
0.0450 (7)
0.054*
0.0550 (8)
0.066*
0.0553 (8)
0.066*
1.1685 (3)
1.1315
1.1106 (3)
1.0356
0.5288 (2)
0.5878
0.4314 (2)
0.4252
1.12438 (16)
1.1129
1.07503 (14)
1.0300
0.0483 (7)
0.058*
0.0407 (7)
0.049*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C17
O17
C11
C12
C13
C14
C15
C16
O12
C18
0.0435 (17)
0.0615 (13)
0.0411 (16)
0.0451 (17)
0.0477 (19)
0.0450 (19)
0.054 (2)
0.0503 (18)
0.0589 (13)
0.071 (2)
0.0418 (17)
0.0640 (14)
0.0343 (16)
0.0414 (17)
0.047 (2)
0.0430 (19)
0.054 (2)
0.0481 (18)
0.0593 (13)
0.085 (3)
0.049 (2)
0.0417 (13)
0.0530 (19)
0.052 (2)
0.068 (2)
0.092 (3)
0.078 (3)
0.061 (2)
0.0435 (13)
0.047 (2)
0.0131 (14)
0.0025 (11)
0.0115 (13)
0.0145 (14)
0.0107 (16)
0.0005 (15)
0.0049 (17)
0.0100 (16)
0.0011 (11)
0.010 (2)
0.0166 (15)
0.0148 (10)
0.0162 (14)
0.0194 (15)
0.0124 (17)
0.0214 (19)
0.0275 (19)
0.0211 (16)
0.0131 (10)
0.0170 (18)
0.0177 (15)
0.0154 (11)
0.0161 (14)
0.0125 (15)
0.0033 (18)
0.0108 (19)
0.0261 (19)
0.0213 (16)
0.0079 (11)
0.0030 (19)
Acta Cryst. (2018). C74, 45-53
sup-20

supporting information
N11
0.0439 (14)
0.0529 (5)
0.0342 (15)
0.0368 (15)
0.0391 (15)
0.0429 (17)
0.0527 (19)
0.057 (2)
0.0374 (13)
0.0507 (5)
0.0396 (16)
0.0321 (15)
0.0356 (15)
0.0464 (17)
0.058 (2)
0.0422 (16)
0.0370 (4)
0.0397 (16)
0.0353 (16)
0.0380 (17)
0.0443 (18)
0.052 (2)
0.0061 (11)
0.0070 (4)
0.0118 (11)
0.0127 (3)
0.0104 (12)
0.0135 (4)
S111
C112
C113
C13A
C114
C115
C116
C117
C17A
C137
O137
C131
C132
C133
C134
C135
C136
C27
O27
C21
C22
C23
C24
C25
C26
O22
0.0116 (13)
0.0077 (12)
0.0122 (13)
0.0028 (14)
−0.0011 (16)
−0.0008 (16)
0.0054 (16)
0.0085 (13)
0.0107 (14)
0.0050 (11)
0.0054 (13)
0.0099 (15)
0.001 (2)
−0.0005 (19)
0.0113 (15)
0.0117 (14)
0.0108 (14)
−0.0058 (11)
0.0125 (13)
0.0167 (14)
0.0189 (18)
0.0067 (18)
−0.0028 (16)
0.0068 (16)
0.0027 (11)
0.0231 (19)
0.0070 (11)
0.0085 (4)
0.0123 (13)
0.0108 (12)
0.0109 (13)
0.0067 (14)
−0.0002 (17)
0.0062 (19)
0.0134 (16)
0.0144 (14)
0.0121 (13)
0.0107 (10)
0.0077 (12)
0.0097 (14)
0.0049 (17)
0.0040 (16)
0.0199 (15)
0.0152 (14)
0.0093 (12)
0.0108 (12)
0.0130 (13)
0.0135 (14)
0.0125 (16)
0.0158 (17)
0.0075 (15)
0.0096 (13)
0.0142 (13)
0.0188 (11)
0.0061 (12)
0.0125 (14)
0.0105 (16)
−0.0025 (17)
0.0009 (17)
0.0095 (14)
0.0077 (14)
−0.0010 (11)
0.0135 (14)
0.0171 (15)
0.0327 (19)
0.037 (2)
0.0102 (13)
0.0080 (13)
0.0100 (13)
0.0066 (14)
0.0047 (16)
−0.0027 (17)
0.0019 (15)
0.0059 (13)
0.0069 (14)
0.0035 (10)
0.0062 (13)
0.0096 (15)
0.0200 (19)
0.037 (2)
0.0280 (19)
0.0114 (16)
0.0070 (14)
0.0110 (11)
0.0115 (14)
0.0156 (15)
0.0316 (19)
0.026 (2)
0.057 (2)
0.056 (2)
0.060 (2)
0.0520 (19)
0.0386 (16)
0.0387 (17)
0.0413 (13)
0.0428 (17)
0.0560 (19)
0.083 (3)
0.0429 (19)
0.0397 (17)
0.0368 (17)
0.0447 (13)
0.0309 (16)
0.0365 (17)
0.042 (2)
0.0444 (16)
0.0434 (16)
0.0811 (15)
0.0362 (15)
0.0522 (18)
0.061 (2)
0.058 (2)
0.078 (3)
0.050 (2)
0.053 (2)
0.082 (3)
0.0419 (18)
0.0420 (17)
0.0414 (17)
0.0591 (13)
0.0379 (16)
0.0424 (17)
0.062 (2)
0.0532 (19)
0.0390 (17)
0.0657 (15)
0.0377 (16)
0.0389 (17)
0.055 (2)
0.0469 (18)
0.0436 (19)
0.0460 (14)
0.0511 (19)
0.059 (2)
0.080 (3)
0.108 (3)
0.100 (3)
0.066 (2)
0.059 (2)
0.053 (2)
0.050 (2)
0.047 (2)
0.018 (2)
0.009 (2)
0.0520 (19)
0.0563 (13)
0.071 (2)
0.0408 (13)
0.0495 (4)
0.0388 (15)
0.0376 (15)
0.0398 (15)
0.0449 (17)
0.057 (2)
0.0461 (19)
0.0579 (13)
0.086 (3)
0.0384 (13)
0.0447 (4)
0.0351 (15)
0.0305 (15)
0.0326 (15)
0.0453 (18)
0.064 (2)
0.0067 (17)
0.0089 (10)
0.0141 (17)
0.0073 (11)
0.0105 (3)
0.0024 (17)
0.0170 (10)
0.0247 (18)
0.0087 (11)
0.0063 (3)
0.0445 (13)
0.044 (2)
C28
N21
0.0355 (13)
0.0367 (4)
0.0373 (16)
0.0351 (16)
0.0379 (17)
0.0529 (19)
0.062 (2)
S211
C212
C213
C23A
C214
C215
C216
C217
C27A
C237
O237
C231
C232
C233
C234
C235
C236
0.0130 (13)
0.0089 (12)
0.0129 (13)
0.0170 (15)
0.0284 (18)
0.0299 (19)
0.0260 (16)
0.0174 (14)
0.0093 (13)
0.0034 (10)
0.0107 (12)
0.0074 (14)
0.0058 (14)
0.0181 (16)
0.0192 (15)
0.0098 (13)
0.0088 (13)
0.0051 (12)
0.0040 (13)
0.0075 (15)
0.0125 (18)
0.0231 (18)
0.0122 (15)
0.0065 (14)
0.0099 (14)
0.0160 (10)
0.0096 (13)
0.0141 (15)
0.0090 (16)
−0.0013 (16)
0.0085 (16)
0.0087 (14)
0.071 (2)
0.063 (2)
0.062 (2)
0.062 (2)
0.051 (2)
0.0466 (18)
0.0396 (16)
0.0385 (16)
0.0410 (12)
0.0392 (16)
0.0466 (18)
0.066 (2)
0.0483 (19)
0.0462 (18)
0.0439 (17)
0.0472 (16)
0.0365 (15)
0.0694 (14)
0.0350 (15)
0.0474 (17)
0.0528 (19)
0.060 (2)
0.0423 (18)
0.0418 (17)
0.0494 (13)
0.0338 (16)
0.0383 (17)
0.0354 (18)
0.049 (2)
0.0531 (18)
0.0438 (16)
0.0510 (19)
0.0355 (16)
Acta Cryst. (2018). C74, 45-53
sup-21