Synthesis and crystal structure studies of three n-phenylphthalimide derivatives

Article abstract of DOI:10.1007/s10870-013-0399-9

The three N-phenylphthalimide derivatives, 2-(3,4-dichlorophenyl) isoindoline-1,3-dione (I), 2-(2,4-dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-trichlorophenyl)isoindoline-1,3-dione (III), were synthesized by the condensation of equimolar amounts of phthalic anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline, 2,4,5-trichloroaniline, respectively, under acetic acid reflux and their structures determined by a combination of elemental analysis, FT-IR, ¹H & ¹³C-NMR spectroscopy and single crystal X-ray diffraction studies. Compounds I and II crystallize in a monoclinic crystal system (space group P2₁/c) with cell parameters of a = 5.7414(2), b = 8.0917(6), c = 26.077(1) A and β = 99.4709(12) ^o for compound I, and a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) A and β = 93.210 (2)^o for compound II. On the other hand, compound III crystallizes in a tetragonal crystal system (space group I4 ₁/a) with a = 13.4607(9) and c = 30.100(2) A. The phthalimide moieties of these compounds are essentially planar, while the chloro-substituted phenyl ring of each compound shows consistent twist from the phthalimide plane with dihedral angles of 61.02(3), 69.09(3) and 85.78(5)^o, respectively, for I, II and III. In the crystal structures of these compounds, a few weak C-H···O interactions form double-tape structures of centrosymmetric dimers of graph-set notation R ₂ ² (10) for I and III, and an inversion dimer of graph-set motif R ₂ ² (14) for II. In addition, some short contacts of C···C, C···O and Cl·· ·Cl are observed for I, II and III, respectively.

Full text of DOI:10.1007/s10870-013-0399-9

J Chem Crystallogr (2013) 43:144–150
DOI 10.1007/s10870-013-0399-9
ORIGINAL PAPER
Synthesis and Crystal Structure Studies of Three
N-Phenylphthalimide Derivatives
•
Muhammad Khawar Rauf Rabia Mushtaq Amin Badshah Robert Kingsford-Adaboh
•
•
•
•
Jerry Joe Ebow Kingsley Harrison Hiroyuki Ishida
Received: 22 June 2012 / Accepted: 8 January 2013 / Published online: 18 January 2013
Ó Springer Science+Business Media New York 2013
Abstract The three N-phenylphthalimide derivatives,
2-(3,4-dichlorophenyl)isoindoline-1,3-dione (I), 2-(2,4-
dichlorophenyl)isoindoline-1,3-dione (II) and 2-(2,4,5-tri-
chlorophenyl)isoindoline-1,3-dione (III), were synthesized
by the condensation of equimolar amounts of phthalic
anhydride and 3,4-dichloroaniline, 2,4-dichloroaniline,
2,4,5-trichloroaniline, respectively, under acetic acid reflux
and their structures determined by a combination of ele-
interactions form double-tape structures of centrosymmet-
ric dimers of graph-set notation R22(10) for I and III, and an
inversion dimer of graph-set motif R22(14) for II. In addi-
tion, some short contacts of CÁÁÁC, CÁÁÁO and ClÁÁÁCl are
observed for I, II and III, respectively.
Keywords N-Phenylphthalimide Á Crystal structure Á
Intermolecular contact Á Graph-set
1
mental analysis, FT-IR, H & 13C-NMR spectroscopy and
single crystal X-ray diffraction studies. Compounds I and
II crystallize in a monoclinic crystal system (space group
P21/c) with cell parameters of a = 5.7414(2), b = 8.0917(6),
Introduction
o
˚
c = 26.077(1) A and b = 99.4709(12) for compound I, and
The search for anti-cancer drugs has turned up many
cytotoxic DNA binding and intercalating agents of diverse
structure and function, several of which form the founda-
tion of current chemotherapy. Phthalimides, N-substituted
phthalimides, naphthalimides and bis-naphthalimides are a
class of compounds with high antitumor activity on a
variety of murine and human tumour cells [1]. These
compounds have the ability to bind DNA by intercalation
of the chromophores and two of them, mitonafide and
amonafide, have been used in clinical trials. The thera-
peutic properties of these lead drugs were improved by
designing bis-intercalating agents. One of these, elinafide,
showed intense in vitro and in vivo activity and is currently
being used in clinical trials against solid tumours [2]. It is
thus reasonable to expect that members of this class of
compounds will reach the oncology market in the near
future. Phthalimides are well known cytotoxic DNA
intercalating agents and have shown promise as potential
anti-cancer agents. Its derivatives, such as bis-naphthali-
mides, represent a promising group of DNA-targeted
anticancer agents, and the search for more potent analogues
remains a priority [3–5]. A series of methylthiazo-
naphthalimides were synthesized and quantitatively
˚
a = 12.7133(9), b = 13.4328(9), c = 7.2603(5) A and b =
93.210 (2)o for compound II. On the other hand, compound
III crystallizes in a tetragonal crystal system (space group
˚
I41/a) with a = 13.4607(9) and c = 30.100(2) A. The
phthalimide moieties of these compounds are essentially
planar, while the chloro-substituted phenyl ring of each
compound shows consistent twist from the phthalimide
plane with dihedral angles of 61.02(3), 69.09(3) and
85.78(5)o, respectively, for I, II and III. In the crystal
structures of these compounds, a few weak C–HÁÁÁO
M. K. Rauf Á R. Mushtaq Á A. Badshah
Department of Chemistry, Quaid-i-Azam University,
Islamabad 45320, Pakistan
R. Kingsford-Adaboh Á J. J. E. K. Harrison (&)
Department of Chemistry, Faculty of Science,
University of Ghana, Box LG56, Legon, Accra, Ghana
e-mail: jjekharrison@ug.edu.gh
H. Ishida
Department of Chemistry, Faculty of Science,
Okayama University, Okayama 700-8530, Japan
123

J Chem Crystallogr (2013) 43:144–150
145
Scheme 1 The reaction scheme
for the syntheses of compounds
I, II and III
Table 1 Selected crystal data and experimental details of X-ray diffraction for compounds I, II and III
I: C14H7Cl2NO2
II: C14H7Cl2NO2
III: C14H6Cl3NO2
Crystal data
Formula weight
Crystal system
Space group
292.12
292.12
326.57
Monoclinic
P21/c
Monoclinic
P21/c
Tetragonal
I41/a
˚
a (A)
5.7414 (2)
8.0917 (6)
26.077 (1)
99.4709 (12)
1194.96 (10)
4
12.7133 (9)
13.4328 (9)
7.2603 (5)
93.210 (2)
1237.93 (15)
4
13.4607 (9)
˚
b (A)
–
˚
c (A)
30.100 (2)
b (°)
–
3
˚
V (A )
5453.8 (8)
Z
16
D (Mg m-3
)
1.624
1.567
1.591
F000
l (mm-1
592.00
592.00
2624.00
)
0.54
0.52
0.67
Crystal size (mm)
0.34 9 0.20 9 0.14
0.37 9 0.28 9 0.15
0.44 9 0.29 9 0.26
Data collection
hmax (°)
30.0
30.0
30.0
hmin (°)
3.2
3.0
3.0
h
-8?7
-11?11
-35?36
21160
3459
-17?17
-18?18
-10?10
20941
3592
-15?18
-16?18
-42?37
22165
3987
k
l
Measured reflections
Independent reflections
Cell parameters from reflections
Reflections with I [ 2r(I)
Rint
18063
3103
16725
3122
14960
2871
0.024
0.040
0.035
Refinement
Refinement on
R[F2 [ 2r(F2)]
wR
F2
F2
F2
0.032
0.088
1.05
3459
172
0.038
0.104
1.07
3592
172
0.058
0.179
1.08
3987
181
S
Number of reflections
Number of parameters
Weighting Scheme, w,
P = (Fo2 ? 2Fc2)/3
1/[r2(F2o) ? (0.0446P)2 ?
0.5569P]
1/[r2(F2o) ? (0.0579P)2 ?
0.2431P]
1/[r2(F2o) ? (0.0888P)2 ?
5.0189P]
(D/r)max
0.001
0.001
\0.001
-0.70, 0.75
-3
)
˚
Dqmin, Dqmax (eA
-0.40, 0.48
-0.25, 0.45
123

146
J Chem Crystallogr (2013) 43:144–150
evaluated as efficient DNA intercalators, antitumor agents
and DNA photocleavers [6]. The electronic structures of
several N-substituted phthalimides have been investigated
and reveal the presence of photofragmentation and photo-
elimination processes related to the decay of the aminium
radical cation [7]. Naphthalimide derivatives are also gor-
geous class of electron-deficient organic materials for
OLEDs and are used as a new type of electron-transporting
emitting materials for both small molecule and polymer-
based OLEDs with high performance, good light stability,
high fluorescent quantum yield, and high electron affinity
[8, 9]. Phthalimide derivatives in the wake of the enormous
biochemical and photochemical applicability have become
important class of compounds for crystal structural studies.
In a study of these class of compounds, it was observed that
they are able to inhibit the acute inflammatory response,
measured by inhibition of lipopolysaccharide (LPS)-
induced TNF-a (Tumor necrosis factor-a) and neutrophil
infiltration into mice lungs [10] with the phthalimide
moiety demonstrated to be important for activity. Some
study [11] also suggests phthalimide derivatives possess
inhibitory effect on the HIV-1 reverse transcriptases. It is
important hence for the crystal structures of these com-
pounds to be studied since the structural and conforma-
tional features could affect the activity of these
compounds. This study hence examines the effect of var-
iation of the substitution pattern on the phenyl ring on the
crystal structure of the compounds and the conformational
changes that may take.
recorded on Bio-Rad FTS 3000 MX spectrophotometer
(400–4,000 cm-1). The elemental analyses were conducted
using a LECO-183 CHNS analyzer.
Crystal Structure Determination
X-ray data of the compounds were collected on a Rigaku
RAXIS RAPID-II imaging plate diffractometer with
˚
graphite monochromated Mo Ka radiation (k = 0.71075 A).
The absorption corrections were carried out using a multi-
scan method (ABSCOR) [12]. Cell refinement was carried
out using PROCESS-AUTO and the data was reduced by
using Crystal Structure [13]. Data collections with hmax of
30o were carried out at 190(2) K for all compounds. The
structures were solved using SHELXS97 [14] and the
structures were refined with SHELXL97 [14] by full-
matrix least-squares on F2 against all reflections. H atoms
˚
were treated as riding, with C–H = 0.95 A and with
U
iso(H) = 1.2Ueq(C). Molecular graphics were carried out
using ORTEP-3 [15] and the material for publication pre-
pared using MERCURY [16] and PLATON [17]. A sum-
mary of the crystal data and other details concerning data
collection and structure refinement are given in Table1.
Results and Discussion
Structure Elucidation of Synthesized Compounds
2-(3,4-Dichlorophenyl)isoindoline-1,3-dione (I)
Experimental
Yield 90 %; white solid; Elemental Analysis: Calc. for
C14H7Cl2NO2: C, 57.56; H, 2.42; N, 4.79 Found: C, 57.53;
H, 2.40; N, 4.83. FT-IR (KBr, cm-1): 3080 Ph(CH),
1704(C=O), 1590(C–N), 1567(C–N), 1478, 1466, 1378,
1218, 1172, 1130, 1112, 1096, 1077, 1028, 888, 869, 831,
782 (C–Cl), 748, 711, 692, 679; 1H NMR (300 MHz,
DMSO-d6) d 7.56 (d, 1H, 3JHH = 7.1 Hz, ArH), 7.62 (d, 1H,
3JHH = 7.1 Hz, ArH), 7.72 (s, 1H, ArH), 7.90–8.12 (m, 4H,
ArH); 13C NMR (75.5 MHz, DMSO-d6) d 123.2, 123.6,
127.9(2C), 129.6, 130.8, 131.9, 132.3(2C), 134.5, (Aro-
matic-C), 166.4(2C, C=O);
Synthesis and Physical Measurements
Compounds I–III were synthesized by the addition of
equimolar amounts of phthalic anhydride and the corre-
sponding aniline derivatives under acetic acid reflux for 1 h
with the progress of the reaction monitored by TLC
(Scheme 1). Upon cooling, single crystals of the corre-
sponding phthalimide derivatives suitable for X-ray dif-
fraction were deposited. The crystals were filtered and
washed several times with water. The synthesis is repre-
sented in scheme 1. The H and 13C NMR spectra were
2-(2,4-Dichlorophenyl)isoindoline-1,3-dione) (II)
1
recorded on a Bruker 300 MHz spectrometer using deu-
terated solvents and TMS as a reference operating at 300
Yield 95 %; white solid; Elemental Analysis: Calc. for
C14H7Cl2NO2: C, 57.56; H, 2.42; N, 4.79 Found: C, 57.51;
H, 2.44; N, 4.82. FT-IR (KBr, cm-1): 3084Ph(CH),
1715(C=O), 1585(C–N), 1568(C–N), 1485, 1467, 1373,
1221, 1170, 1145, 1112, 1095, 1084, 1055, 884, 872, 862,
788 (C–Cl), 773, 708, 685, 661; 1H NMR (300 MHz,
DMSO-d6) d 7.66 (d, 1H, 3JHH = 7.1 Hz, ArH), 7.68 (s, 1H,
ArH), 7.91 (d, 1H, 3JHH = 7.1 Hz, ArH), 7.93-8.04 (m, 4H,
1
and 75.5 MHz respectively. H NMR (300 MHz): internal
standard solvent DMSO-d6 (2.49 ppm from TMS), internal
standard TMS; 13C NMR (75.5 MHz): internal standard
solvent DMSO-d6 (39.99 ppm from TMS): internal stan-
dard TMS; the splitting of proton resonances in the
1
reported H NMR spectra are defined as s = singlet, d =
doublet and m = complex pattern. FT-IR spectra were
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J Chem Crystallogr (2013) 43:144–150
147
ArH); 13C NMR (75.5 MHz, DMSO-d6) d 124.3(2C),
128.9, 129.2, 130.0, 131.8(2C), 133.1, 133.9, 135.5,
135.6(2C) (Aromatic-C), 166.6 (2C, C=O).
2-(2,4,5-Trichlorophenyl)isoindoline-1,3-dione) (III)
Yield 90 %; white solid; Elemental Analysis: Calc. for
C14H6Cl3NO2: C, 51.49; H, 1.85; N, 4.29 Found: C, 51.53;
H, 1.86; N, 4.31. FT-IR (KBr, cm-1): 3079 Ph(CH),
1710(C=O), 1588(C–N), 1572(C–N), 1481, 1468, 1375,
1216, 1168, 1132, 1110, 1092, 1074, 1026, 878, 864, 828,
780(C–Cl), 743, 716, 688, 676; 1H NMR (300 MHz,
DMSO-d6) d 7.56 (d, 1H, 3JHH = 6.9 Hz, ArH), 7.62 (d, 1H,
3JHH = 6.9 Hz, ArH), 7.72 (s, 1H, ArH), 7.90–8.12 (m, 4H,
ArH); 13C NMR (75.5 MHz, DMSO-d6) d 124.6,
127.3(2C), 130.2, 130.9, 131.9, 132.2(2C), 132.9(2C),
135.1, 135.5(Aromatic-C), 166.4(2C, C=O).
Crystal Structure Analysis
As summarized in Table 1, compounds I and II crystallize
in a monoclinic crystal system with space group P21/c,
while compound III crystallizes in a tetragonal crystal
system with space group I41/a. Molecular structures of the
compounds are presented in Fig. 1a–c. The three com-
pounds differ with respect to the number and the positions
of chlorine atoms on the phenyl ring. In all the three
compounds, one chlorine atom occupies the para position.
In compound I, there is an additional chlorine atom at the
meta position, while in compound II the additional chlorine
is at the ortho position. In compound III, however, there
are two additional chlorine atoms occupying the ortho and
meta positions. Some bond lengths and angles, and torsion
angles are presented in Table 2. In all compounds, the
nitrogen atoms adopt a near trigonal planar arrangement
and no significant difference in all bond lengths and angles
is observed except for the N1-C9 bond length in which a
little difference is observed between II and meta-chloro-
substituted compounds (I and III).
Fig. 1 Molecular structures of the compound I (a), II (b) and III(c),
showing the atomic labelling scheme. Displacement ellipsoid for non-
hydrogen atoms are plotted at the 50 % probability level
Table 2 Selected geometric parameters in compounds I, II and III
˚
(A, 8)
I
II
1.4068(15)
III
1.403(2)
N1–C1
1.4089(16)
1.4148(15)
1.4214(14)
1.2092(15)
1.2053(16)
124.34(10)
123.42(10)
119.38(11)
119.11(10)
62.91(16)
N1–C2
1.4141(15)
1.4170(16)
1.2057(15)
1.2010(15)
124.71(10)
123.07(10)
121.22(11)
119.83(11)
-72.37(16)
108.88(14)
112.77(13)
-65.98 (16)
1.407(3)
1.423(2)
1.205(3)
1.203(3)
124.03(17)
123.78(16)
121.0(2)
119.6(2)
-89.4(3)
90.6(3)
N1–C9
C1–O1
C2-O2
The phthalimide C1/N1/C2-C8/O1/O2 planes of all the
C1–N1–C9
C2N1–C9
compounds studied are nearly planar with r.m.s. deviations
˚
of 0.025(1), 0.024(1) and 0.025(2) A, respectively, for
N1–C9C10
N1–C9–C14
C1–N1–C9–C10
C1–N1–C9–C14
C2–N1–C9–C10
C2–N1–C9–C14
compounds I, II and III. The maximum deviations from
˚
the mean planes are 0.0407(10) A for O1 in compound I,
˚
˚
0.0435(11) A for N1 in II and 0.029(2) A for O2 in III. The
phenyl rings of all the compounds twist out of the
phthalimide plane with dihedral angles of 61.02(3),
69.09(3) and 85.78(5)o, respectively, for I, II and III, being
comparable with those of 56.71(16)8 [18] and 64.09(15)8
[19] for N-phenylphthalimide. The progressive increase in
the dihedral angle from compound I–III may suggest that
the presence of the Cl at the ortho position leads to a
-118.15(13)
-121.45(13)
57.49(16)
97.5(3)
-82.5(3)
greater degree of twist avoiding repulsion between the
ortho Cl and carbonyl O atoms since I does not have a
substituent in the ortho position. It would have been
123

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J Chem Crystallogr (2013) 43:144–150
˚
Table 3 Hydrogen bond geometries (A, 8) for compounds I, II and III
D–H
HÁÁÁA
DÁÁÁA
D–HÁÁÁA
Compound I
C4–H4ÁÁÁO2i
0.95
0.95
2.53
2.34
3.3535(16)
3.2597(16)
145
162
C14–H14ÁÁÁO1ii
Compound II
C11–H11ÁÁÁO1i
Compound III
C4–H4ÁÁÁO1i
0.95
2.46
3.2229(17)
137
0.95
0.95
0.95
2.37
2.51
2.48
3.195(3)
3.373(3)
3.247(3)
145
151
137
C7–H7ÁÁÁO2ii
C14–H14ÁÁÁO1iii
Symmetry codes: [I] (i) -x, -y, 1 – z, (ii) -1 ? x, y, z; [II] (i) -x, 1 - y, 1 – z; [III] (i) x, -1/2 ? y, 1 - z (ii) x, 1/2 ? y, 1 - z; (iii) 1 - x,
3/2 - y, z
Fig. 2 Crystal packing diagram
of compound I. The C–HÁÁÁO
hydrogen bonds are shown in
broken lines
expected that the presence of bulky groups at the ortho
position hence would increase the degree of twist if intra-
molecular repulsion are the predominant factors. Compar-
ing the dihedral angles around this region between II and
III however, the large difference observed is unexplainable
onlybytheintramolecularrepulsionalludedtoearlier. Infact,
the dihedral angles observed for ortho-substituted N-phen-
ylphthalimide derivatives distribute in a wide range:
70.8(3), 88.24(10), 71.93(8), 59.99(5), 79.13(18),
84.74(13)8, 77.2(1)o, for methyl- [20], animo- [21], hydroxy-
[22], methoxy- [23], bromo- [24], iode- [25] and ethyl-
substituted [26] compounds respectively, which are poorly
correlated with the size of the substituent since both bromine,
iodine and ethyl group are far bigger than chlorine with
the chlorine showing a bigger twist. It is obvious that both
intra- and intermolecular interactions are responsible for the
observed twist.
In the crystal structures of all compounds, the primary
intermolecular interactions are C–HÁÁÁO hydrogen bonds
with the HÁÁÁO contact distances and the C–HÁÁÁO angles
˚
being in the ranges of 2.34-2.53 A and 137–1628, respec-
tively (Table 3). In compound I, the molecules are linked
by a pair of the hydrogen bonds [C4–H4ÁÁÁO2i; symmetry
code (i) in Table 3] into a centrosymmetric dimer with an
R22(10) graph-set motif [27]. The dimers are further con-
nected by another hydrogen bond [C14–H14ÁÁÁO1ii; sym-
metry code (ii) in Table 3], resulting in a double tape
structure along the a axis (Fig. 2). The tapes are stacked
along the b axis in the manner that the phthalimine planes
are stacked anti-parallelly in close distances. The shortest
123

J Chem Crystallogr (2013) 43:144–150
149
Fig. 3 Crystal packing diagram
of compound II. The C–HÁÁÁO
hydrogen bonds and the CÁÁÁO
contacts are indicated by black
and red dashed lines,
respectively. Symmetry codes:
(i) -x, 1 - y, 1 - z; (ii) x, 1/2
- y, 1/2 ? z (Color figure
online)
Fig. 5 Crystal packing diagram of compound III, showing the
arrangement of double-tapes perpendicular to each other. H atoms
have been omitted for clarity
Fig. 4 Crystal packing diagram of compound III, showing a double-
tape structure along the b axis. Dashed lines indicate C–HÁÁÁO
hydrogen bonds
H11ÁÁÁO2i: symmetry code (i) in Table 3] into a centro-
symmetric dimer with an R22(14) graph-set motif. No fur-
ther hydrogen bonding is observed but short CÁÁÁO contacts
[C2ÁÁÁO1(x, 1/2 - y, 1/2 ? z) = 3.0717(16) and C3ÁÁÁO1(x,
CÁÁÁC contact distances in the tape and between the tapes
˚
are C2ÁÁÁC5(1 - x, -y, 1 - z) = 3.3895(19) A and
˚
C1ÁÁÁC7(1 - x, 1 - y, 1 - z) = 3.3263(18) A.
˚
Similar to I, the molecules in compound II are con-
nected by a pair of C–HÁÁÁO hydrogen bonds [C11–
1/2 - y, 1/2 ? z) = 3.1512(16) A] link the dimers into a
layer parallel to the bc plane (Fig. 3).
123

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J Chem Crystallogr (2013) 43:144–150
In compound III, molecules are connected by C–HÁÁÁO
Centre, CDCC No. 885916, 885917 and 885918, respec-
tively. The data can be obtained free of charge from
CDCC, 12 Union Road, Cambridge CB2 1EZ, UK, Fax:
?44 1223 336 033, e-mail: deposit@cdcc.cam.ac.uk or
http: www.ccdc.cam.ac.uk.
hydrogen bonds [C4–H4ÁÁÁO1i and C7–H7ÁÁÁO2ii; symme-
try codes (i) and (ii) in Table 3], which form an R22(10)
graph-set motif, into a tape running along the b axis. The
tapes related by an inversion centre to each other are linked
by another C–HÁÁÁO hydrogen bond [C14–H14ÁÁÁO1iii;
symmetry code (iii) in Table 3], forming a double-tape
structure (Fig. 4). Perpendicular to the tape, a symmetry
equivalent neighboring double-tape related by a fourfold
screw axis runs along the a axis (Fig. 5). Between the
double-tapes, the phthalimide and chlorobenzene planes
are arranged to be approximately parallel to each other
and a ClÁÁÁCl short contact [Cl1ÁÁÁCl2(3/4 - y, 1/4 ? x,
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In this work three chloro-substituted derivatives of N-
phenylphthalimide have been synthesized by refluxing
equimolar amounts of phthalic anhydride and chlorine
substituted anilines in acetic acid and characterized by
elemental analysis, FT-IR and 1H and 13C NMR. The
crystal structures were determined by single-crystal X-ray
diffraction. The phthalimide moiety of all the compounds
are coplanar even though some atoms deviate slightly from
the mean plane when the least square parameters are ana-
lyzed. The phenyl ring in each case twists out of the
phthalimide plane with angles of 61.02(3)o, 69.09(3)o and
85.78(5)o, respectively, for compounds I, II and III. Few
weak C–HÁÁÁO interactions and short CÁÁÁC, CÁÁÁO and
ClÁÁÁCl contacts have been observed. In compound I, the
molecules are linked by a pair of the hydrogen bonds into a
centrosymmetric dimer with an R22(10) graph-set motif with
these dimers further connected by another hydrogen bond
into a double tape structure along the a axis. Compound II
forms a centrosymmetric dimer with an R22(14) graph-set
motif connected by a pair of C–HÁÁÁO hydrogen bonds to
each other. On the other hand, an R22(10) graph-set motif
resulting from C–HÁÁÁO hydrogen bonds and further con-
nected by C–HÁÁÁO hydrogen bonds into a tape running
along the b axis are formed by compound III, molecules.
The tapes related by an inversion centre to each other are
linked by another C–HÁÁÁO hydrogen bond into a double-
tape structure.
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Supplementary Data
Crystallographic data for the compounds I, II and III have
been deposited with the Cambridge Crystallographic
123