Hydrogen-bonded sheet structures in methyl 4-(4-chloroanilino)-3- nitrobenzoate and methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5- carboxylate

Article abstract of DOI:10.1107/S0108270112049669

In methyl 4-(4-chloroanilino)-3-nitrobenzoate, C₁₄H11ClN ₂O4, (I), there is an intramolecular N - H...O hydrogen bond and the intramolecular distances provide evidence for electronic polarization of the o-quinonoid type. The molecules are linked into sheets built from N - H...O, C - H...O and C - H...π(arene) hydrogen bonds, together with an aromatic π-π stacking interaction. The molecules of methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate, C22H ₁₇ClN₂O₂, (II), are also linked into sheets, this time by a combination of C - H...π(arene) hydrogen bonds and aromatic π-π stacking interactions.

Full text of DOI:10.1107/S0108270112049669

organic compounds
Acta Crystallographica Section C
Crystal Structure
benzimidazoles bearing the 4-chlorophenyl or quinolin-2-one
pharmacophores at position 2, which exhibit high activity
Communications
´
against a range of cancer cell lines (Abonıa et al., 2011). As
ISSN 0108-2701
part of our current synthetic programme aimed at the devel-
opment of potential antitumour agents, we have now prepared
the benzimidazole derivative, (II), using a two-step synthesis
involving the in situ reduction of the nitroaniline precursor,
(I), followed by cyclocondensation with 4-chlorobenzaldehyde.
Hydrogen-bonded sheet structures in
methyl 4-(4-chloroanilino)-3-nitro-
benzoate and methyl 1-benzyl-2-(4-
chlorophenyl)-1H-benzimidazole-5-
carboxylate
a
a
b
´
´
Edwar Cortes, Rodrigo Abonıa, Justo Cobo and
Christopher Glidewellc*
a
´
Departamento de Quımica, Universidad de Valle, AA 25360 Cali, Colombia,
b
´
´
´
´
Departamento de Quımica Inorganica y Organica, Universidad de Jaen, 23071
Jaen, Spain, and cSchool of Chemistry, University of St Andrews, Fife KY16 9ST,
´
Scotland
Correspondence e-mail: cg@st-andrews.ac.uk
Received 3 December 2012
Accepted 3 December 2012
Online 13 December 2012
In methyl 4-(4-chloroanilino)-3-nitrobenzoate, C14H11ClN2O4,
(I), there is an intramolecular N—Hꢀ ꢀ ꢀO hydrogen bond and
the intramolecular distances provide evidence for electronic
polarization of the o-quinonoid type. The molecules are linked
into sheets built from N—Hꢀ ꢀ ꢀO, C—Hꢀ ꢀ ꢀO and C—
Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds, together with an aromatic
ꢀ–ꢀ stacking interaction. The molecules of methyl 1-benzyl-2-
(4-chlorophenyl)-1H-benzimidazole-5-carboxylate, C22H17Cl-
N2O2, (II), are also linked into sheets, this time by a
combination of C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds and
aromatic ꢀ–ꢀ stacking interactions.
Comment
We report here the molecular structures and the supra-
molecular assembly of the two title compounds, (I) (Fig. 1) and
(II) (Fig. 2). Benzimidazoles are compounds of wide interest
because of their diverse biological activities and clinical
applications (Ansari & Lal, 2009). They are regarded as a
promising class of bioactive heterocyclic compounds, exhi-
biting a wide range of biological properties such as antifungal,
antiparasitic and antiviral activity. They are also active as
analgesics, anticoagulants, anticonvulsants, antihistamines and
anti-inflammatory agents, and they show anticancer, anti-
hypertensive and anti-ulcer activity, as well as acting as
proton-pump inhibitors (Bansal & Silakari, 2012). Conse-
quently, substituted benzimidazoles have attracted interest,
especially since it has been reported that the influence of the
substitution at the 1-, 2- and 5-positions of the benzimidazole
framework is important for their pharmacological effects
(Kılcıgil & Altanlar, 2006). We have recently reported the
design of a four-step synthesis of novel 1,2,5-trisubstituted
Within the molecule of (I), the plane of the nitro group
makes a dihedral angle of only 9.4 (2)ꢁ with that of the adja-
cent aryl ring, and this may be associated with the presence of
an intramolecular N—Hꢀ ꢀ ꢀO hydrogen bond (Fig. 1 and
Table 2) which gives rise to an S(6) motif (Bernstein et al.,
1995). On the other hand, the two rings within the molecule
make a dihedral angle of 49.8 (2)ꢁ.
The bond lengths in the molecule of (I) provide evidence
for polarization of the electronic structure. Thus, the C12—C13
and C15—C16 bond lengths are significantly shorter than the
other C—C bond lengths in the C11–C16 ring (Table 1); the
C13—N31 bond is short for its type [mean value (Allen et al.,
˚
˚
1987) = 1.468 A, lower quartile value = 1.460 A], while the
C14—N41 bond is significantly shorter than the N41—C41
bond; and the N31—O31 and N31—O32 bonds are both long
˚
for their type (mean value = 1.217 A, upper quartile value =
˚
1.225 A). These observations, taken as a whole, indicate that
the polarized form, (Ia) (see Scheme), makes a significant
Acta Cryst. (2013). C69, 77–81
doi:10.1107/S0108270112049669
# 2013 International Union of Crystallography 77

organic compounds
Figure 1
Figure 3
The molecular structure of (I), showing the atom-labelling scheme and
the intramolecular N—Hꢀ ꢀ ꢀO hydrogen bond (dashed line). Displace-
ment ellipsoids are drawn at the 30% probability level.
A stereoview of part of the crystal structure of (I), showing the formation
of a chain of alternating R22(4) and R22(10) rings running parallel to the
[010] direction. For the sake of clarity, H atoms not involved in the motifs
shown have been omitted.
contribution to the overall electronic structure, alongside the
classically delocalized form, (I). Polarization of this type has
been observed previously both in simple 2-nitroanilines
containing unsubstituted amino groups (Cannon et al., 2001;
Glidewell et al., 2001) and in N-(2-nitrophenyl)aniline
(McWilliam et al., 2001).
As noted above, the molecules of (I) contain an intra-
molecular N—Hꢀ ꢀ ꢀO hydrogen bond. In addition, the mol-
ecules are linked by a combination of intermolecular N—
Hꢀ ꢀ ꢀO, C—Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds
(Table 2), augmented by an aromatic ꢀ–ꢀ stacking interaction.
The resulting rather complex sheet structure can be readily
analysed in terms of two one-dimensional substructures
(Ferguson et al., 1998a,b; Gregson et al., 2000).
related by inversion to form a chain of rings running parallel
to the [010] direction. Pairs of inversion-related N—Hꢀ ꢀ ꢀO
hydrogen bonds generate R22(4) rings centred at (21, n, 12), where
n represents an integer, and pairs of inversion-related C—
Hꢀ ꢀ ꢀO hydrogen bonds generate R22(10) rings centred at
1
2
(12, n + 12, ), where n again represents an integer (Fig. 3).
The second substructure in (I) is built from the combination
of a C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond and an aromatic ꢀ–ꢀ
stacking interaction. Aryl atom C46 in the molecule at (x, y, z)
acts as hydrogen-bond donor to the C41–C46 aryl ring in the
1
molecule at (x, ꢂy + 12, z ꢂ ), so linking molecules related by
2
1
the c-glide plane at y = into a chain running parallel to the
4
[001] direction (Fig. 4). In addition, the plane of the tri-
substituted C11–C16 ring in the molecule at (x, y, z) makes a
dihedral angle of only 2.0 (2)ꢁ with the planes of the corre-
The first substructure is built from a combination of N—
Hꢀ ꢀ ꢀO and C—Hꢀ ꢀ ꢀO hydrogen bonds, which link molecules
1
sponding rings of the two molecules at (x, ꢂy + 12, z ꢂ ) and (x,
2
ꢂy + 12, z + 12). The shortest ring-centroid separation is
˚
3.722 (2) A and the shortest perpendicular distance between
Figure 4
A stereoview of part of the crystal structure of (I), showing the formation
of a chain running parallel to the [001] direction and built from C—
Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds augmented by aromatic ꢀ–ꢀ stacking
interactions. For the sake of clarity, H atoms not involved in the motifs
shown have been omitted.
Figure 2
The molecular structure of (II), showing the atom-labelling scheme
Displacement ellipsoids are drawn at the 30% probability level.
ꢃ
´
78 Cortes et al.
C14H11ClN2O4 and C22H17ClN2O2
Acta Cryst. (2013). C69, 77–81

organic compounds
Figure 5
Part of the crystal structure of (II), showing the formation of a ꢀ-stacked
1
1
dimer centred at (12, , ). For the sake of clarity, all H atoms have been
omitted. The atom marked with an asterisk (*) is at the symmetry position
Figure 6
2
2
A stereoview of part of the crystal structure of (II), showing the
formation of a chain running parallel to the [001] direction and built from
C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bonds. For the sake of clarity, H atoms not
involved in the motif shown have been omitted.
(ꢂx + 1, ꢂy + 1, ꢂz + 1).
˚
the ring planes is ca 3.34 A, corresponding to a ring-centroid
˚
offset of ca 1.64 A. The effect of this stacking interaction is to
at (12, 0, 0), (21, 1, 0), (21, 0, 1) and (12, 1, 1), so forming a sheet lying
parallel to (100) (Fig. 7).
reinforce the chain formation along [001] generated by the
C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond (Fig. 4). The combination of
the [010] and [001] chains generates a complex sheet lying
parallel to (100).
The details of the supramolecular assembly in (I) and (II)
provide some interesting comparisons. In each compound, the
supramolecular assembly leads to the formation of a sheet
parallel to (100) in the space group P21/c, and in both
compounds it is the ring carrying the ester function which
participates in the ꢀ–ꢀ stacking interaction. However, the
acceptor in the C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond is the
chlorinated aryl ring in (I) but the fused aryl ring in (II), while
the donor in this interaction forms part of the chlorinated aryl
ring in (I) as opposed to the benzyl ring in (II). Finally, the
ester function participates in the assembly in (I), where the
ester carbonyl O atom acts as the acceptor in the C—Hꢀ ꢀ ꢀO
The crystal structure of (I) also contains a rather short
˚
intermolecular Clꢀ ꢀ ꢀO contact of 2.924 (3) A between atom
Cl44 in the molecule at (x, y, z) and atom O31 in the molecule
at (x + 1, y + 1, z + 1). This contact distance is certainly shorter
˚
than the sum of the van der Waals radii (3.2 A; Bondi, 1964),
but it is unclear whether the contact is attractive, or, as seems
more likely, repulsive.
In the molecule of (II) (Fig. 2), the bond lengths within the
fused bicyclic system (Table 3) indicate strong bond fixation in
the imidazole portion, with typical aromatic delocalization in
the carbocyclic ring. The plane of the chlorinated aryl ring
makes a dihedral angle of 50.2 (2)ꢁ with that of the adjacent
imidazole ring, while the benzyl ring plane is almost ortho-
gonal to that of the imidazole ring, with a dihedral angle of
81.7 (2)ꢁ.
The supramolecular assembly in (II) depends on the
combination of a C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond (Table 4)
and an aromatic ꢀ–ꢀ stacking interaction, both of which
involve the fused aryl ring. In the ꢀ-stacking interaction, the
fused rings of the molecules at (x, y, z) and (ꢂx + 1, ꢂy + 1,
ꢂz + 1), which are strictly parallel, have an interplanar spacing
˚
˚
of 3.481 (2) A and a ring-centroid separation of 3.568 (2) A,
˚
corresponding to a ring-centroid offset of ca 0.78 A (Fig. 5).
The C—Hꢀ ꢀ ꢀꢀ(arene) hydrogen bond links molecules related
3
4
by the 21 screw axis along (0, , z) to form a chain running
parallel to the [001] direction (Fig. 6).
The combination of these two interactions generates a sheet
structure in which, for example, the reference ꢀ-stacked dimer
Figure 7
A stereoview of part of the crystal structure of (II), showing the
formation of a sheet lying parallel to (100). For the sake of clarity, H
atoms not involved in the motifs shown have been omitted.
1
1
centred at (12, , ) is directly linked by C—Hꢀ ꢀ ꢀꢀ(arene)
2
2
hydrogen bonds to the four symmetry-related dimers centred
ꢃ
´
Acta Cryst. (2013). C69, 77–81
Cortes et al.
C14H11ClN2O4 and C22H17ClN2O2 79

organic compounds
Table 3
Selected geometric parameters (A, ) for (II).
hydrogen bond, while in (II) the ester function plays no part in
the supramolecular assembly.
ꢁ
˚
N1—C2
C2—N3
N3—C3a
C3a—C4
C4—C5
1.381 (2)
1.322 (2)
1.392 (2)
1.394 (3)
1.393 (3)
C5—C6
C6—C7
C7—C7a
C7a—N1
C3a—C7a
1.417 (3)
1.383 (3)
1.399 (3)
1.383 (2)
1.406 (2)
Experimental
For the synthesis of (I), a mixture of methyl 4-fluoro-3-nitrobenzoate
(0.199 g, 1 mmol) and 4-chloroaniline (1 mmol) in dimethyl sulfoxide
(2 ml) was stirred at ambient temperature for 2 h. After complete
disappearance of the starting materials [as monitored by thin-layer
chromatography (TLC)], the solid thus formed was collected by
filtration and washed with a methanol–water mixture (1:2 v/v; 3 ꢄ
2 ml) to afford (I) (yield 84%; orange crystals, m.p. 421 K). FT–IR
(KBr, ꢁ, cmꢂ1): 3312 (NH), 1770 (C O), 1718 (C C), 1622 (C N),
1524, 1324 (NO2). MS (70 eV) m/z (%): 308/306 (100/34) [M+], 277/
275 (15/5) [M ꢂ OCH3], 243/241 (29/9), 230/228 (38/13), 201 (30),
111 (3).
C2—N1—C17—C11
N1—C17—C11—C12
N1—C2—C21—C22
ꢂ115.9 (2)
21.2 (3)
51.5 (3)
C4—C5—C51—O51
C4—C5—C51—O52
C5—C51—O52—C52
ꢂ8.5 (3)
171.38 (17)
179.72 (16)
Table 4
Hydrogen-bond geometry (A, ) for (II).
ꢁ
˚
Cg2 represents the centroid of the C3a/C4–C7/C7a ring.
For the synthesis of (II), a mixture of intermediate (A) (see
Scheme) (0.306 g, 1 mmol), which had been prepared in a manner
analogous to that for (I) but using benzylamine in place of
4-choloroaniline, acetic acid (2 ml) and zinc powder (5 equivalents)
was stirred at ambient temperature for 15 min. After complete
disappearance of starting compound (I) (as monitored by TLC), the
by-product zinc acetate and excess zinc were removed by filtration.
The resulting solution was then heated with 4-chlorobenzaldehyde
(1.05 mmol) at 373 K for 1 h. After complete disappearance of the
starting materials (as monitored by TLC), the solution was allowed to
cool to ambient temperature and the excess of acetic acid was
removed under reduced pressure. The solid product was washed with
ethanol (2 ꢄ 1 ml) to afford (II) (yield 88%; colourless crystals, m.p.
437 K). FT–IR (KBr, ꢁ, cmꢂ1): 3028, 2951, 1719 (C O), 1612
(C C), 1521 (C N), 1438, 1287 (C—O). MS (70 eV) m/z (%): 378/
376 (3/12) [M+], 345 (1) [M ꢂ 28], 137 (3), 91 (28).
D—Hꢀ ꢀ ꢀA
C16—H16ꢀ ꢀ ꢀCg2i
Symmetry code: (i) x; ꢂy þ ; z ꢂ .
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
0.95
2.52
3.388 (2)
153
3
2
1
2
Compound (I)
Crystal data
3
˚
C14H11ClN2O4
Mr = 306.70
Monoclinic, P21=c
V = 1376.1 (3) A
Z = 4
Mo Kꢃ radiation
ꢄ = 0.30 mmꢂ1
T = 120 K
˚
a = 12.4413 (10) A
˚
b = 15.8116 (18) A
˚
c = 7.1805 (10) A
0.32 ꢄ 0.16 ꢄ 0.08 mm
ꢂ = 103.037 (9)ꢁ
Crystals of (I) and (II) suitable for single-crystal X-ray diffraction
were grown by slow evaporation, at ambient temperature and in air,
from solutions in ethanol.
Data collection
Bruker–Nonius KappaCCD area-
detector diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.912, Tmax = 0.977
20301 measured reflections
2572 independent reflections
1600 reflections with I > 2ꢅ(I)
Rint = 0.111
Table 1
Selected geometric parameters (A, ) for (I).
ꢁ
˚
Refinement
R[F2 > 2ꢅ(F2)] = 0.059
wR(F2) = 0.163
S = 1.04
191 parameters
H-atom parameteꢂrs3 constrained
C11—C12
C12—C13
C13—C14
C14—C15
C15—C16
C16—C11
1.380 (5)
1.397 (5)
1.418 (5)
1.426 (5)
1.366 (5)
1.412 (5)
C13—N31
N31—O31
N31—O32
C14—N41
N41—C41
1.447 (4)
1.231 (4)
1.242 (4)
1.364 (4)
1.420 (4)
˚
Áꢆmax = 0.37 e A
ꢂ3
˚
2572 reflections
Áꢆmin = ꢂ0.35 e A
C11—C1—O2—C2
O1—C1—C11—C12
O2—C1—C11—C12
C12—C13—N31—O31
178.9 (3)
167.0 (4)
ꢂ13.9 (5)
8.9 (5)
C12—C13—N31—O32
C13—C14—N41—C41
C14—N41—C41—C42
ꢂ171.0 (3)
174.9 (3)
135.8 (4)
Compound (II)
Crystal data
3
˚
V = 1822.9 (4) A
Z = 4
C22H17ClN2O2
Mr = 376.83
Monoclinic, P21=c
Mo Kꢃ radiation
ꢄ = 0.23 mmꢂ1
T = 120 K
0.31 ꢄ 0.28 ꢄ 0.20 mm
Table 2
Hydrogen-bond geometry (A, ) for (I).
˚
a = 14.214 (2) A
b = 11.7391 (10) A
ꢁ
˚
˚
˚
c = 11.0580 (14) A
ꢂ = 98.908 (10)ꢁ
Cg1 represents the centroid of the C41–C46 ring.
D—Hꢀ ꢀ ꢀA
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Data collection
N41—H41ꢀ ꢀ ꢀO32
N41—H41ꢀ ꢀ ꢀO32i
C16—H16ꢀ ꢀ ꢀO1ii
C46—H46ꢀ ꢀ ꢀCg1iii
0.88
0.88
0.95
0.95
1.93
2.37
2.49
2.72
2.617 (4)
3.158 (4)
3.302 (4)
3.560 (4)
133
149
144
147
Bruker–Nonius KappaCCD area-
detector diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.932, Tmax = 0.956
24459 measured reflections
4183 independent reflections
3040 reflections with I > 2ꢅ(I)
Rint = 0.065
1
2
Symmetry codes: (i) ꢂx þ 1; ꢂy; ꢂz þ 1; (ii) ꢂx þ 1; ꢂy þ 1; ꢂz þ 1; (iii) x; ꢂy þ ,
1
z ꢂ .
2
ꢃ
´
80 Cortes et al.
C14H11ClN2O4 and C22H17ClN2O2
Acta Cryst. (2013). C69, 77–81

organic compounds
Refinement
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: SK3463). Services for accessing these data are
described at the back of the journal.
R[F2 > 2ꢅ(F2)] = 0.046
wR(F2) = 0.117
S = 1.05
4183 reflections
245 parameters
H-atom parameteꢂrs3 constrained
˚
Áꢆmax = 0.32 e A
ꢂ3
˚
Áꢆmin = ꢂ0.43 e A
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´
´
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˚
˚
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´
´
The authors thank the Centro de Instrumentacion Cientı-
´
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´
´
´
Consejerıa de Innovacion, Ciencia y Empresa (Junta de
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´
ꢃ
´
Acta Cryst. (2013). C69, 77–81
Cortes et al.
C14H11ClN2O4 and C22H17ClN2O2 81

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 77-81 [doi:10.1107/S0108270112049669]
Hydrogen-bonded sheet structures in methyl 4-(4-chloroanilino)-3-nitro-
benzoate and methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-
carboxylate
Edwar Cortés, Rodrigo Abonía, Justo Cobo and Christopher Glidewell
(I) Methyl 4-(4-chloroanilino)-3-nitrobenzoate
Crystal data
C14H11ClN2O4
Mr = 306.70
F(000) = 632
Dx = 1.480 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3170 reflections
θ = 3.1–27.5°
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 12.4413 (10) Å
b = 15.8116 (18) Å
c = 7.1805 (10) Å
β = 103.037 (9)°
V = 1376.1 (3) Å3
Z = 4
µ = 0.30 mm−1
T = 120 K
Plate, orange
0.32 × 0.16 × 0.08 mm
Data collection
Bruker Nonius KappaCCD area-detector
diffractometer
Radiation source: Bruker–Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.912, Tmax = 0.977
20301 measured reflections
2572 independent reflections
1600 reflections with I > 2σ(I)
Rint = 0.111
θ
max = 25.6°, θmin = 3.1°
h = −15→15
k = −19→19
l = −8→8
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.059
wR(F2) = 0.163
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.04
2572 reflections
191 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0792P)2 + 1.1147P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.37 e Å−3
Δρmin = −0.35 e Å−3
Acta Cryst. (2013). C69, 77-81
sup-1

supplementary materials
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
C1
0.3117 (3)
0.3299 (2)
0.22506 (19)
0.1486 (3)
0.1074
0.4227 (2)
0.49519 (15)
0.39896 (15)
0.4650 (2)
0.4837
0.2714 (5)
0.3259 (4)
0.1329 (3)
0.0504 (6)
0.1444
0.0278 (8)
0.0347 (7)
0.0303 (6)
0.0367 (10)
0.055*
O1
O2
C2
H2A
H2B
H2C
C11
C12
H12
C13
C14
C15
H15
C16
H16
N31
O31
O32
N41
H41
C41
C42
H42
C43
H43
C44
Cl44
C45
H45
C46
H46
0.0970
0.4431
−0.0632
0.055*
0.1895
0.5129
0.0141
0.055*
0.3824 (3)
0.3467 (3)
0.2753
0.3493 (2)
0.2672 (2)
0.2568
0.3463 (5)
0.3069 (5)
0.2298
0.0238 (8)
0.0252 (8)
0.030*
0.4153 (3)
0.5244 (3)
0.5571 (3)
0.6284
0.1993 (2)
0.2110 (2)
0.2966 (2)
0.3080
0.3798 (5)
0.4889 (5)
0.5303 (5)
0.6072
0.0225 (8)
0.0235 (8)
0.0238 (8)
0.029*
0.4887 (3)
0.5133
0.3627 (2)
0.4188
0.4624 (5)
0.4939
0.0245 (8)
0.029*
0.3685 (2)
0.2797 (2)
0.41931 (19)
0.5935 (2)
0.5645
0.11608 (18)
0.10904 (15)
0.05350 (15)
0.14530 (18)
0.0944
0.3335 (4)
0.2170 (4)
0.4133 (4)
0.5553 (4)
0.5351
0.0259 (7)
0.0323 (6)
0.0343 (7)
0.0250 (7)
0.030*
0.7062 (3)
0.7405 (3)
0.6881
0.1486 (2)
0.0972 (2)
0.0635
0.6529 (5)
0.8112 (5)
0.8553
0.0236 (8)
0.0246 (8)
0.029*
0.8501 (3)
0.8732
0.0945 (2)
0.0589
0.9056 (5)
1.0137
0.0274 (8)
0.033*
0.9259 (3)
1.06412 (7)
0.8938 (3)
0.9466
0.1438 (2)
0.14155 (6)
0.1960 (2)
0.2300
0.8419 (5)
0.96463 (14)
0.6835 (5)
0.6413
0.0271 (8)
0.0371 (3)
0.0289 (9)
0.035*
0.7837 (3)
0.7609
0.1978 (2)
0.2323
0.5876 (5)
0.4775
0.0280 (8)
0.034*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
C1
0.029 (2)
0.025 (2)
0.030 (2)
0.0033 (16)
0.0026 (12)
0.0050 (11)
0.0094 (18)
0.0031 (15)
0.0002 (16)
0.0004 (15)
0.0011 (15)
−0.0033 (15)
−0.0022 (15)
0.0007 (13)
0.0075 (16)
0.0057 (12)
0.0027 (11)
0.0003 (18)
0.0107 (15)
0.0055 (15)
0.0032 (14)
0.0070 (14)
0.0070 (15)
0.0087 (15)
0.0040 (13)
0.0026 (16)
−0.0007 (12)
0.0025 (11)
0.0092 (18)
0.0004 (14)
−0.0001 (15)
0.0016 (15)
0.0009 (15)
−0.0023 (15)
0.0000 (15)
−0.0018 (13)
O1
0.0418 (17)
0.0268 (13)
0.032 (2)
0.0223 (14)
0.0261 (14)
0.032 (2)
0.0385 (16)
0.0360 (15)
0.042 (2)
O2
C2
C11
C12
C13
C14
C15
C16
N31
0.0295 (19)
0.0232 (18)
0.0185 (17)
0.0236 (18)
0.0218 (18)
0.0274 (18)
0.0249 (16)
0.0183 (18)
0.030 (2)
0.0257 (19)
0.0229 (19)
0.0223 (18)
0.0234 (19)
0.0246 (19)
0.0286 (19)
0.0289 (17)
0.0260 (19)
0.0241 (19)
0.0257 (19)
0.0187 (17)
0.0231 (16)
Acta Cryst. (2013). C69, 77-81
sup-2

supplementary materials
O31
O32
N41
C41
C42
C43
C44
Cl44
C45
C46
0.0258 (14)
0.0287 (14)
0.0240 (15)
0.0191 (17)
0.0275 (18)
0.0288 (19)
0.0218 (18)
0.0222 (5)
0.0272 (14)
0.0186 (13)
0.0180 (15)
0.0212 (18)
0.0182 (18)
0.0221 (19)
0.0251 (19)
0.0411 (6)
0.026 (2)
0.0379 (15)
0.0500 (17)
0.0307 (17)
0.0292 (19)
0.029 (2)
−0.0013 (11)
0.0010 (11)
−0.0003 (13)
0.0006 (15)
0.0026 (15)
0.0062 (16)
0.0035 (16)
0.0045 (4)
−0.0052 (12)
−0.0030 (12)
0.0013 (12)
0.0025 (14)
0.0078 (15)
0.0012 (16)
−0.0004 (15)
−0.0013 (4)
0.0100 (16)
0.0028 (15)
−0.0001 (11)
0.0048 (12)
−0.0028 (12)
−0.0003 (15)
−0.0004 (15)
0.0003 (15)
−0.0069 (16)
−0.0023 (5)
−0.0005 (16)
0.0028 (16)
0.029 (2)
0.031 (2)
0.0439 (6)
0.035 (2)
0.0264 (19)
0.0268 (19)
−0.0026 (16)
−0.0013 (16)
0.028 (2)
0.027 (2)
Geometric parameters (Å, º)
C1—O1
1.216 (4)
N31—O32
1.242 (4)
C1—O2
1.344 (4)
1.482 (5)
1.446 (4)
0.9800
C14—N41
N41—C41
N41—H41
C16—H16
C41—C42
C41—C46
C42—C43
C42—H42
C43—C44
C43—H43
C44—C45
C44—Cl44
C45—C46
C45—H45
C46—H46
1.364 (4)
1.420 (4)
0.8800
C1—C11
O2—C2
C2—H2A
C2—H2B
C2—H2C
C11—C12
C12—C13
C12—H12
C13—C14
C14—C15
C15—C16
C15—H15
C16—C11
C13—N31
N31—O31
0.9500
0.9800
1.384 (5)
1.399 (5)
1.380 (5)
0.9500
0.9800
1.380 (5)
1.397 (5)
0.9500
1.379 (5)
0.9500
1.418 (5)
1.426 (5)
1.366 (5)
0.9500
1.389 (5)
1.747 (3)
1.388 (5)
0.9500
1.412 (5)
1.447 (4)
1.231 (4)
0.9500
O1—C1—O2
124.1 (3)
124.7 (3)
111.2 (3)
116.4 (3)
109.5
C15—C16—H16
C11—C16—H16
O31—N31—O32
O31—N31—C13
O32—N31—C13
C14—N41—C41
C14—N41—H41
C41—N41—H41
C42—C41—C46
C42—C41—N41
C46—C41—N41
C43—C42—C41
C43—C42—H42
C41—C42—H42
C44—C43—C42
C44—C43—H43
C42—C43—H43
C43—C44—C45
C43—C44—Cl44
119.3
O1—C1—C11
O2—C1—C11
C1—O2—C2
119.3
121.8 (3)
119.4 (3)
118.8 (3)
128.2 (3)
115.9
O2—C2—H2A
O2—C2—H2B
H2A—C2—H2B
O2—C2—H2C
H2A—C2—H2C
H2B—C2—H2C
C12—C11—C16
C12—C11—C1
C16—C11—C1
C11—C12—C13
C11—C12—H12
C13—C12—H12
C12—C13—C14
C12—C13—N31
C14—C13—N31
109.5
109.5
109.5
115.9
109.5
119.6 (3)
118.1 (3)
122.2 (3)
120.6 (3)
119.7
109.5
118.5 (3)
121.7 (3)
119.8 (3)
120.3 (3)
119.8
119.7
119.6 (3)
120.2
119.8
122.3 (3)
115.6 (3)
122.1 (3)
120.2
121.1 (3)
119.3 (3)
Acta Cryst. (2013). C69, 77-81
sup-3

supplementary materials
N41—C14—C13
N41—C14—C15
C13—C14—C15
C16—C15—C14
C16—C15—H15
C14—C15—H15
C15—C16—C11
122.9 (3)
121.5 (3)
115.6 (3)
121.7 (3)
119.1
C45—C44—Cl44
C46—C45—C44
C46—C45—H45
C44—C45—H45
C45—C46—C41
C45—C46—H46
C41—C46—H46
119.6 (3)
119.2 (3)
120.4
120.4
120.0 (3)
120.0
119.1
121.5 (3)
120.0
O1—C1—O2—C2
−1.9 (5)
178.9 (3)
167.0 (4)
−13.9 (5)
−12.5 (5)
166.6 (3)
−0.4 (5)
−179.9 (3)
−2.7 (5)
178.5 (3)
−177.7 (3)
1.0 (5)
C12—C13—N31—O31
C14—C13—N31—O31
C12—C13—N31—O32
C14—C13—N31—O32
C13—C14—N41—C41
C15—C14—N41—C41
C14—N41—C41—C42
C14—N41—C41—C46
C46—C41—C42—C43
N41—C41—C42—C43
C41—C42—C43—C44
C42—C43—C44—C45
C42—C43—C44—Cl44
C43—C44—C45—C46
Cl44—C44—C45—C46
C44—C45—C46—C41
C42—C41—C46—C45
N41—C41—C46—C45
8.9 (5)
C11—C1—O2—C2
−170.0 (3)
−171.0 (3)
10.2 (5)
174.9 (3)
−7.0 (5)
135.8 (4)
−48.3 (5)
0.5 (5)
O1—C1—C11—C12
O2—C1—C11—C12
O1—C1—C11—C16
O2—C1—C11—C16
C16—C11—C12—C13
C1—C11—C12—C13
C11—C12—C13—C14
C11—C12—C13—N31
C12—C13—C14—N41
N31—C13—C14—N41
C12—C13—C14—C15
N31—C13—C14—C15
N41—C14—C15—C16
C13—C14—C15—C16
C14—C15—C16—C11
C12—C11—C16—C15
C1—C11—C16—C15
176.6 (3)
0.3 (5)
−0.3 (5)
178.8 (3)
−0.4 (5)
−179.6 (3)
1.2 (5)
4.1 (5)
−177.2 (3)
179.3 (3)
−2.4 (5)
−0.5 (5)
2.0 (5)
−1.2 (5)
−177.2 (3)
−178.5 (3)
Hydrogen-bond geometry (Å, º)
Cg1 represents the centroid of the C41–C46 ring.
D—H···A
D—H
H···A
D···A
D—H···A
N41—H41···O32
N41—H41···O32i
C16—H16···O1ii
C46—H46···Cg1iii
0.88
0.88
0.95
0.95
1.93
2.37
2.49
2.72
2.617 (4)
3.158 (4)
3.302 (4)
3.560 (4)
133
149
144
147
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z−1/2.
(II) Methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate
Crystal data
C22H17ClN2O2
Mr = 376.83
F(000) = 784
Dx = 1.373 Mg m−3
Monoclinic, P21/c
Hall symbol: -P 2ybc
a = 14.214 (2) Å
b = 11.7391 (10) Å
c = 11.0580 (14) Å
β = 98.908 (10)°
V = 1822.9 (4) Å3
Z = 4
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 4183 reflections
θ = 2.8–27.5°
µ = 0.23 mm−1
T = 120 K
Block, colourless
0.31 × 0.28 × 0.20 mm
Acta Cryst. (2013). C69, 77-81
sup-4

supplementary materials
Data collection
Bruker Nonius KappaCCD area-detector
diffractometer
Radiation source: Bruker Nonius FR591
rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
Tmin = 0.932, Tmax = 0.956
24459 measured reflections
4183 independent reflections
3040 reflections with I > 2σ(I)
Rint = 0.065
θ
max = 27.5°, θmin = 2.8°
h = −18→18
k = −15→15
l = −14→14
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.046
wR(F2) = 0.117
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.05
4183 reflections
245 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0449P)2 + 1.0641P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.32 e Å−3
Δρmin = −0.43 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x
y
z
Uiso*/Ueq
N1
0.69848 (11)
0.73360 (13)
0.69613 (11)
0.63269 (13)
0.57395 (13)
0.5718
0.57451 (13)
0.46478 (15)
0.40547 (13)
0.48000 (15)
0.46255 (15)
0.3907
0.45316 (14)
0.46699 (17)
0.54929 (14)
0.59228 (16)
0.68054 (17)
0.7196
0.0219 (3)
0.0215 (4)
0.0240 (4)
0.0218 (4)
0.0230 (4)
0.028*
C2
N3
C3a
C4
H4
C5
0.51849 (13)
0.52074 (14)
0.4823
0.55328 (15)
0.65955 (16)
0.7202
0.70979 (17)
0.64954 (17)
0.6712
0.0225 (4)
0.0240 (4)
0.029*
C6
H6
C7
0.57724 (14)
0.5779
0.67767 (15)
0.7487
0.56017 (17)
0.5192
0.0241 (4)
0.029*
H7
C7a
C17
H17A
H17B
C11
C12
H12
C13
H13
C14
H14
C15
H15
C16
H16
0.63340 (13)
0.71419 (14)
0.6517
0.58599 (15)
0.66023 (15)
0.6839
0.53325 (16)
0.36200 (16)
0.3166
0.0218 (4)
0.0239 (4)
0.029*
0.7508
0.6249
0.3025
0.029*
0.76685 (13)
0.82367 (15)
0.8296
0.76488 (15)
0.76704 (17)
0.7007
0.41551 (16)
0.52964 (18)
0.5795
0.0217 (4)
0.0269 (4)
0.032*
0.87194 (16)
0.9107
0.86605 (18)
0.8669
0.57100 (19)
0.6491
0.0324 (5)
0.039*
0.86405 (16)
0.8977
0.96298 (18)
1.0301
0.4997 (2)
0.5282
0.0345 (5)
0.041*
0.80687 (16)
0.8008
0.96185 (17)
1.0286
0.3867 (2)
0.3375
0.0343 (5)
0.041*
0.75846 (15)
0.7189
0.86392 (16)
0.8641
0.34512 (18)
0.2675
0.0274 (4)
0.033*
Acta Cryst. (2013). C69, 77-81
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supplementary materials
C21
C22
H22
C23
H23
C24
Cl24
C25
H25
C26
H26
C51
O51
O52
C52
H52A
H52B
H52C
0.80203 (14)
0.88719 (14)
0.9031
0.41651 (16)
0.47085 (17)
0.5414
0.39352 (17)
0.37947 (18)
0.4195
0.0234 (4)
0.0274 (4)
0.033*
0.94890 (15)
1.0072
0.42279 (18)
0.4593
0.30757 (19)
0.2993
0.0301 (5)
0.036*
0.92384 (15)
0.99602 (4)
0.84068 (15)
0.8247
0.32070 (17)
0.26432 (5)
0.26460 (17)
0.1945
0.24829 (18)
0.14922 (5)
0.26202 (18)
0.2210
0.0281 (4)
0.03969 (17)
0.0285 (4)
0.034*
0.78075 (15)
0.7246
0.31173 (16)
0.2722
0.33641 (18)
0.3486
0.0271 (4)
0.032*
0.45824 (14)
0.44658 (10)
0.41778 (10)
0.35773 (16)
0.3075
0.53386 (16)
0.44172 (11)
0.62973 (11)
0.61510 (18)
0.5597
0.80648 (17)
0.85107 (12)
0.84006 (12)
0.93410 (19)
0.9062
0.0235 (4)
0.0300 (3)
0.0288 (3)
0.0329 (5)
0.049*
0.3288
0.6883
0.9500
0.049*
0.3964
0.5875
1.0095
0.049*
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
N1
0.0277 (9)
0.0247 (10)
0.0284 (9)
0.0257 (10)
0.0273 (10)
0.0255 (10)
0.0282 (10)
0.0302 (11)
0.0256 (10)
0.0319 (11)
0.0249 (10)
0.0343 (11)
0.0371 (12)
0.0391 (13)
0.0420 (13)
0.0325 (11)
0.0281 (10)
0.0304 (11)
0.0272 (11)
0.0323 (11)
0.0467 (3)
0.0363 (12)
0.0310 (11)
0.0253 (10)
0.0382 (8)
0.0358 (8)
0.0393 (12)
0.0146 (7)
0.0140 (8)
0.0156 (8)
0.0136 (8)
0.0144 (8)
0.0156 (9)
0.0162 (9)
0.0132 (9)
0.0164 (9)
0.0168 (9)
0.0167 (9)
0.0213 (10)
0.0313 (11)
0.0229 (11)
0.0184 (10)
0.0197 (10)
0.0188 (9)
0.0206 (10)
0.0294 (11)
0.0241 (10)
0.0333 (3)
0.0187 (9)
0.0188 (9)
0.0169 (9)
0.0177 (7)
0.0201 (7)
0.0293 (11)
0.0236 (8)
−0.0007 (6)
−0.0001 (7)
−0.0008 (6)
−0.0008 (7)
−0.0021 (8)
−0.0023 (7)
0.0011 (8)
0.0011 (8)
−0.0021 (7)
0.0000 (8)
−0.0005 (7)
0.0002 (8)
−0.0036 (9)
−0.0084 (9)
−0.0020 (9)
0.0000 (8)
0.0028 (8)
−0.0044 (8)
−0.0030 (9)
0.0077 (9)
0.0125 (2)
0.0033 (8)
−0.0016 (8)
−0.0009 (8)
−0.0006 (6)
0.0042 (6)
0.0074 (9)
0.0046 (6)
0.0020 (7)
0.0064 (7)
0.0013 (7)
0.0033 (8)
0.0015 (8)
0.0021 (8)
0.0017 (8)
0.0031 (8)
0.0028 (8)
0.0065 (8)
0.0055 (8)
0.0028 (9)
0.0079 (10)
0.0068 (10)
0.0010 (8)
0.0034 (8)
0.0044 (8)
0.0069 (8)
0.0092 (8)
0.0234 (3)
0.0081 (9)
0.0075 (8)
−0.0003 (8)
0.0120 (6)
0.0135 (6)
0.0141 (9)
0.0011 (6)
−0.0006 (7)
0.0002 (6)
−0.0003 (7)
−0.0001 (7)
−0.0021 (7)
−0.0025 (7)
0.0005 (7)
−0.0004 (7)
0.0032 (7)
−0.0004 (7)
0.0028 (8)
−0.0045 (9)
−0.0074 (9)
0.0063 (9)
0.0036 (8)
0.0024 (7)
−0.0004 (8)
0.0062 (9)
0.0072 (8)
0.0071 (2)
0.0019 (8)
0.0023 (8)
−0.0043 (7)
0.0000 (6)
0.0006 (6)
0.0025 (9)
C2
0.0252 (9)
0.0286 (8)
0.0253 (9)
0.0270 (9)
0.0257 (9)
0.0271 (10)
0.0280 (10)
0.0233 (9)
0.0226 (9)
0.0243 (9)
0.0253 (10)
0.0281 (10)
0.0420 (12)
0.0425 (12)
0.0287 (10)
0.0231 (9)
0.0310 (10)
0.0345 (11)
0.0294 (10)
0.0443 (3)
0.0316 (10)
0.0322 (10)
0.0269 (10)
0.0361 (8)
0.0330 (7)
0.0328 (11)
N3
C3a
C4
C5
C6
C7
C7a
C17
C11
C12
C13
C14
C15
C16
C21
C22
C23
C24
Cl24
C25
C26
C51
O51
O52
C52
Acta Cryst. (2013). C69, 77-81
sup-6

supplementary materials
Geometric parameters (Å, º)
N1—C2
1.381 (2)
1.322 (2)
1.392 (2)
1.394 (3)
1.393 (3)
0.9500
C13—H13
C14—C15
C14—H14
C15—C16
C15—H15
C16—H16
C21—C26
C21—C22
C22—C23
C22—H22
C23—C24
C23—H23
C24—C25
C24—Cl24
C25—C26
C25—H25
C26—H26
C51—O51
C51—O52
O52—C52
C52—H52A
C52—H52B
C52—H52C
0.9500
C2—N3
1.381 (3)
0.9500
N3—C3a
C3a—C4
C4—C5
1.382 (3)
0.9500
C4—H4
0.9500
C5—C6
1.417 (3)
0.9500
1.394 (3)
1.398 (3)
1.391 (3)
0.9500
C6—H6
C6—C7
1.383 (3)
1.399 (3)
0.9500
C7—C7a
C7—H7
1.386 (3)
0.9500
C7a—N1
C3a—C7a
N1—C17
C2—C21
C5—C51
C17—C11
C17—H17A
C17—H17B
C11—C12
C11—C16
C12—C13
C12—H12
C13—C14
1.383 (2)
1.406 (2)
1.466 (2)
1.474 (3)
1.487 (3)
1.511 (3)
0.9900
1.382 (3)
1.743 (2)
1.388 (3)
0.9500
0.9500
1.211 (2)
1.342 (2)
1.454 (2)
0.9800
0.9900
1.389 (3)
1.394 (3)
1.391 (3)
0.9500
0.9800
0.9800
1.379 (3)
C2—N1—C7a
C2—N1—C17
C7a—N1—C17
N3—C2—N1
N3—C2—C21
N1—C2—C21
C2—N3—C3a
N3—C3a—C4
N3—C3a—C7a
C4—C3a—C7a
C5—C4—C3a
C5—C4—H4
C3a—C4—H4
C4—C5—C6
C4—C5—C51
C6—C5—C51
C7—C6—C5
C7—C6—H6
C5—C6—H6
C6—C7—C7a
C6—C7—H7
C7a—C7—H7
N1—C7a—C7
106.63 (15)
128.71 (16)
124.19 (15)
112.97 (16)
123.22 (16)
123.75 (16)
104.80 (15)
129.53 (17)
110.26 (16)
120.21 (17)
118.17 (17)
120.9
C12—C13—H13
C13—C14—C15
C13—C14—H14
C15—C14—H14
C14—C15—C16
C14—C15—H15
C16—C15—H15
C15—C16—C11
C15—C16—H16
C11—C16—H16
C26—C21—C22
C26—C21—C2
C22—C21—C2
C23—C22—C21
C23—C22—H22
C21—C22—H22
C24—C23—C22
C24—C23—H23
C22—C23—H23
C25—C24—C23
C25—C24—Cl24
C23—C24—Cl24
C24—C25—C26
119.7
119.58 (19)
120.2
120.2
120.15 (19)
119.9
119.9
120.86 (18)
119.6
119.6
118.89 (18)
118.25 (18)
122.86 (17)
120.78 (18)
119.6
120.9
120.62 (18)
117.35 (16)
122.03 (17)
121.96 (17)
119.0
119.6
118.84 (19)
120.6
119.0
120.6
116.57 (17)
121.7
121.45 (19)
119.00 (16)
119.50 (16)
119.29 (19)
121.7
132.19 (17)
Acta Cryst. (2013). C69, 77-81
sup-7

supplementary materials
N1—C7a—C3a
105.34 (16)
122.46 (17)
114.08 (15)
108.7
C24—C25—H25
C26—C25—H25
C25—C26—C21
C25—C26—H26
C21—C26—H26
O51—C51—O52
O51—C51—C5
O52—C51—C5
C51—O52—C52
O52—C52—H52A
O52—C52—H52B
120.4
C7—C7a—C3a
120.4
N1—C17—C11
N1—C17—H17A
C11—C17—H17A
N1—C17—H17B
C11—C17—H17B
H17A—C17—H17B
C12—C11—C16
C12—C11—C17
C16—C11—C17
C11—C12—C13
C11—C12—H12
C13—C12—H12
C14—C13—C12
C14—C13—H13
120.67 (19)
119.7
108.7
119.7
108.7
123.02 (18)
124.06 (17)
112.92 (16)
115.02 (15)
109.5
108.7
107.6
118.65 (17)
123.62 (17)
117.72 (16)
120.12 (18)
119.9
109.5
H52A—C52—H52B
O52—C52—H52C
H52A—C52—H52C
H52B—C52—H52C
109.5
109.5
109.5
109.5
119.9
120.63 (19)
119.7
C7a—N1—C2—N3
C17—N1—C2—N3
C7a—N1—C2—C21
C17—N1—C2—C21
N1—C2—N3—C3a
C21—C2—N3—C3a
C2—N3—C3a—C4
C2—N3—C3a—C7a
N3—C3a—C4—C5
C7a—C3a—C4—C5
C3a—C4—C5—C6
C3a—C4—C5—C51
C4—C5—C6—C7
0.0 (2)
C16—C11—C12—C13
C17—C11—C12—C13
C11—C12—C13—C14
C12—C13—C14—C15
C13—C14—C15—C16
C14—C15—C16—C11
C12—C11—C16—C15
C17—C11—C16—C15
N3—C2—C21—C26
N1—C2—C21—C26
N3—C2—C21—C22
N1—C2—C21—C22
C26—C21—C22—C23
C2—C21—C22—C23
C21—C22—C23—C24
C22—C23—C24—C25
C22—C23—C24—Cl24
C23—C24—C25—C26
Cl24—C24—C25—C26
C24—C25—C26—C21
C22—C21—C26—C25
C2—C21—C26—C25
C4—C5—C51—O51
C6—C5—C51—O51
C4—C5—C51—O52
C6—C5—C51—O52
O51—C51—O52—C52
C5—C51—O52—C52
−0.9 (3)
−172.18 (17)
177.12 (17)
4.9 (3)
178.22 (19)
0.1 (3)
0.6 (3)
0.0 (2)
−0.4 (3)
−177.07 (17)
−179.70 (19)
−0.1 (2)
−0.4 (3)
1.1 (3)
−178.08 (19)
47.9 (3)
178.13 (18)
−1.5 (3)
−128.9 (2)
−131.7 (2)
51.5 (3)
1.1 (3)
−178.42 (17)
0.1 (3)
1.4 (3)
C51—C5—C6—C7
C5—C6—C7—C7a
C2—N1—C7a—C7
C17—N1—C7a—C7
C2—N1—C7a—C3a
C17—N1—C7a—C3a
C6—C7—C7a—N1
C6—C7—C7a—C3a
N3—C3a—C7a—N1
C4—C3a—C7a—N1
N3—C3a—C7a—C7
C4—C3a—C7a—C7
C2—N1—C17—C11
C7a—N1—C17—C11
N1—C17—C11—C12
N1—C17—C11—C16
179.60 (17)
−0.9 (3)
−178.98 (18)
1.0 (3)
178.9 (2)
−8.4 (3)
−1.9 (3)
175.46 (15)
0.3 (3)
−0.09 (19)
172.58 (16)
−178.33 (19)
0.6 (3)
−177.09 (15)
2.3 (3)
−3.1 (3)
0.1 (2)
177.30 (17)
−8.5 (3)
179.77 (16)
−179.04 (17)
0.6 (3)
171.99 (18)
171.38 (17)
−8.2 (3)
−115.9 (2)
73.1 (2)
−0.4 (3)
21.2 (3)
179.72 (16)
−159.68 (17)
Acta Cryst. (2013). C69, 77-81
sup-8

supplementary materials
Hydrogen-bond geometry (Å, º)
Cg2 represents the centroid of the C3a/C4–C7/C7a ring.
D—H···A
D—H
H···A
D···A
D—H···A
C16—H16···Cg2i
0.95
2.52
3.388 (2)
153
Symmetry code: (i) x, −y+3/2, z−1/2.
Acta Cryst. (2013). C69, 77-81
sup-9