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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jul 23;67(Pt 8):o2136. doi: 10.1107/S1600536811029084

1,3-Dibenzyl-5-chloro-1H-benzimidazol-2(3H)-one

Rachida Dardouri a, Youssef Kandri Rodi a, Sonia Ladeira b, El Mokhtar Essassi c, Seik Weng Ng d,e,*
PMCID: PMC3213576  PMID: 22091153

Abstract

In both independent mol­ecules of the title compound, C21H17ClN2O, the aromatic rings of the benzyl substituents are located on opposite sides of the benzimidazole ring systems. In one mol­ecule, the rings are aligned at 77.0 (1) and 78.1 (1)° with respect to the fused-ring system, whereas in the other mol­ecule the rings are aligned at 76.0 (1) and 76.9 (1)°. There is an inter­molecular Cl⋯O contact of 3.086 (1) Å.

Related literature

For the structure of monobenzyl-benzimidazol-3-one, see: Ouzidan et al. (2011).graphic file with name e-67-o2136-scheme1.jpg

Experimental

Crystal data

  • C21H17ClN2O

  • M r = 348.82

  • Monoclinic, Inline graphic

  • a = 11.0380 (4) Å

  • b = 9.2863 (3) Å

  • c = 33.2679 (13) Å

  • β = 92.297 (2)°

  • V = 3407.3 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 293 K

  • 0.08 × 0.04 × 0.03 mm

Data collection

  • Bruker X8 APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T min = 0.981, T max = 0.993

  • 22403 measured reflections

  • 5950 independent reflections

  • 3942 reflections with I > 2σ(I)

  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058

  • wR(F 2) = 0.159

  • S = 1.03

  • 5950 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029084/bt6817sup1.cif

e-67-o2136-sup1.cif (28.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029084/bt6817Isup2.hkl

e-67-o2136-Isup2.hkl (291.3KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811029084/bt6817Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Université Sidi Mohamed Ben Abdallah, Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

A recent study reported the synthesis of monobenzyl-benzimidazol-3-one by the reaction of benzyl chloride on benzimidazol-3-one (Ouzidan et al., 2011). The use of double the molar quantity of benzyl choride on 5-chlorobenzimidazol-3-one yielded the expected title dibenzyl analog (Scheme I, Fig. 1). In both independent molecules, the aromatic rings of the benzyl substituent lie of opposite sides of the planar benzimidazole fused-ring. In one molecule, the rings are aligned at 77.0 (1)° and 78.1 (1)° with respect to the fused-ring whereas in the other, the rings are aligned at 76.0 (1)° and 76.9 (1)°.

Experimental

To 5-chloro-1H-benzimidazol-2(3H)-one (0.2 g, 1.18 mmol), potassium carbonate (0.40 g, 2.80 mmol), and tetra-n-butylammonium bromide (0.08 g, 0.23 mmol) in DMF (15 ml) was added benzyl chloride (0.33 g, 2.6 mmol). Stirring was continued at room temperature for 6 h. The salts were removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. The compound was recrystallized from hexane.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

Omitted from the refinement were (-1 0 2), (1 0 2), (0 1 2), (0 0 2), (0 1 1) and (-1 1 2) owing to bad agreement between observed and calculated structure factors.

Figures

Fig. 1.

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two molecules of C21H17ClN2O at the 70% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.

Crystal data

C21H17ClN2O F(000) = 1456
Mr = 348.82 Dx = 1.360 Mg m3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 2455 reflections
a = 11.0380 (4) Å θ = 2.5–24.4°
b = 9.2863 (3) Å µ = 0.24 mm1
c = 33.2679 (13) Å T = 293 K
β = 92.297 (2)° Prism, colorless
V = 3407.3 (2) Å3 0.08 × 0.04 × 0.03 mm
Z = 8

Data collection

Bruker X8 APEXII diffractometer 5950 independent reflections
Radiation source: fine-focus sealed tube 3942 reflections with I > 2σ(I)
graphite Rint = 0.073
φ and ω scans θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −13→13
Tmin = 0.981, Tmax = 0.993 k = −11→10
22403 measured reflections l = −39→39

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.071P)2 + 2.3735P] where P = (Fo2 + 2Fc2)/3
5950 reflections (Δ/σ)max = 0.001
451 parameters Δρmax = 0.77 e Å3
0 restraints Δρmin = −0.36 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl1 0.34242 (8) 0.76198 (10) 0.10621 (3) 0.0370 (3)
Cl2 −0.16981 (8) 1.64706 (10) 0.03835 (3) 0.0392 (3)
O1 0.6486 (2) 0.2235 (3) 0.23982 (7) 0.0360 (6)
O2 0.1395 (2) 0.9431 (3) 0.06445 (8) 0.0391 (7)
N1 0.5083 (2) 0.3850 (3) 0.21135 (8) 0.0290 (7)
N2 0.6912 (2) 0.3771 (3) 0.18714 (9) 0.0286 (7)
N3 −0.0049 (2) 1.1228 (3) 0.05254 (9) 0.0287 (7)
N4 0.1826 (2) 1.1884 (3) 0.06987 (9) 0.0299 (7)
C1 0.5083 (3) 0.4824 (4) 0.17969 (10) 0.0277 (8)
C2 0.4193 (3) 0.5703 (4) 0.16282 (10) 0.0297 (8)
H2 0.3415 0.5730 0.1725 0.036*
C3 0.4529 (3) 0.6548 (4) 0.13040 (10) 0.0282 (8)
C4 0.5684 (3) 0.6555 (4) 0.11589 (11) 0.0332 (9)
H4 0.5868 0.7160 0.0947 0.040*
C5 0.6573 (3) 0.5652 (4) 0.13307 (11) 0.0324 (9)
H5 0.7353 0.5636 0.1235 0.039*
C6 0.6258 (3) 0.4786 (4) 0.16458 (10) 0.0256 (8)
C7 0.6200 (3) 0.3167 (4) 0.21566 (10) 0.0288 (8)
C8 0.4026 (3) 0.3441 (4) 0.23430 (10) 0.0325 (9)
H8A 0.3534 0.4287 0.2387 0.039*
H8B 0.4300 0.3070 0.2604 0.039*
C9 0.3263 (3) 0.2313 (4) 0.21252 (10) 0.0264 (8)
C10 0.2142 (3) 0.2636 (4) 0.19518 (11) 0.0320 (9)
H10 0.1824 0.3557 0.1977 0.038*
C11 0.1489 (3) 0.1595 (4) 0.17398 (11) 0.0350 (9)
H11 0.0736 0.1825 0.1622 0.042*
C12 0.1940 (3) 0.0227 (4) 0.17016 (11) 0.0364 (9)
H12 0.1501 −0.0465 0.1556 0.044*
C13 0.3058 (3) −0.0117 (4) 0.18826 (11) 0.0355 (9)
H13 0.3364 −0.1047 0.1863 0.043*
C14 0.3710 (3) 0.0919 (4) 0.20903 (10) 0.0326 (9)
H14 0.4461 0.0687 0.2210 0.039*
C15 0.8138 (3) 0.3320 (4) 0.17933 (11) 0.0316 (9)
H15A 0.8174 0.3031 0.1514 0.038*
H15B 0.8342 0.2487 0.1959 0.038*
C16 0.9066 (3) 0.4487 (4) 0.18787 (10) 0.0254 (8)
C17 0.9235 (3) 0.5040 (5) 0.22652 (11) 0.0429 (10)
H17 0.8761 0.4707 0.2471 0.051*
C18 1.0100 (4) 0.6077 (5) 0.23439 (13) 0.0555 (13)
H18 1.0211 0.6436 0.2604 0.067*
C19 1.0807 (3) 0.6594 (4) 0.20421 (12) 0.0419 (10)
H19 1.1393 0.7292 0.2098 0.050*
C20 1.0637 (3) 0.6071 (4) 0.16622 (11) 0.0359 (9)
H20 1.1104 0.6420 0.1457 0.043*
C21 0.9772 (3) 0.5022 (4) 0.15803 (11) 0.0320 (9)
H21 0.9664 0.4671 0.1319 0.038*
C22 −0.0032 (3) 1.2731 (4) 0.05389 (10) 0.0252 (8)
C23 −0.0928 (3) 1.3738 (4) 0.04580 (10) 0.0285 (8)
H23 −0.1721 1.3468 0.0390 0.034*
C24 −0.0587 (3) 1.5167 (4) 0.04828 (10) 0.0269 (8)
C25 0.0588 (3) 1.5596 (4) 0.05836 (10) 0.0307 (8)
H25 0.0784 1.6570 0.0595 0.037*
C26 0.1466 (3) 1.4569 (4) 0.06670 (10) 0.0301 (8)
H26 0.2257 1.4841 0.0738 0.036*
C27 0.1156 (3) 1.3146 (4) 0.06442 (10) 0.0268 (8)
C28 0.1094 (3) 1.0696 (4) 0.06260 (10) 0.0299 (8)
C29 −0.1116 (3) 1.0311 (4) 0.04639 (10) 0.0301 (8)
H29A −0.0863 0.9373 0.0370 0.036*
H29B −0.1649 1.0730 0.0257 0.036*
C30 −0.1805 (3) 1.0127 (4) 0.08438 (10) 0.0280 (8)
C31 −0.1280 (3) 0.9383 (4) 0.11718 (12) 0.0390 (10)
H31 −0.0511 0.8989 0.1152 0.047*
C32 −0.1877 (4) 0.9221 (4) 0.15238 (12) 0.0450 (10)
H32 −0.1513 0.8723 0.1739 0.054*
C33 −0.3026 (4) 0.9806 (5) 0.15555 (13) 0.0489 (11)
H33 −0.3434 0.9706 0.1793 0.059*
C34 −0.3563 (4) 1.0533 (5) 0.12353 (13) 0.0475 (11)
H34 −0.4336 1.0918 0.1256 0.057*
C35 −0.2953 (3) 1.0695 (4) 0.08817 (12) 0.0371 (9)
H35 −0.3321 1.1192 0.0667 0.045*
C36 0.3085 (3) 1.1791 (4) 0.08465 (11) 0.0316 (9)
H36A 0.3262 1.0804 0.0924 0.038*
H36B 0.3192 1.2386 0.1085 0.038*
C37 0.3976 (3) 1.2263 (4) 0.05408 (10) 0.0275 (8)
C38 0.4760 (3) 1.3383 (4) 0.06241 (11) 0.0314 (9)
H38 0.4722 1.3870 0.0868 0.038*
C39 0.5609 (3) 1.3799 (4) 0.03490 (12) 0.0387 (10)
H39 0.6130 1.4566 0.0407 0.046*
C40 0.5674 (4) 1.3065 (4) −0.00092 (12) 0.0411 (10)
H40 0.6247 1.3327 −0.0193 0.049*
C41 0.4894 (4) 1.1950 (5) −0.00948 (12) 0.0416 (10)
H41 0.4943 1.1458 −0.0337 0.050*
C42 0.4036 (3) 1.1548 (4) 0.01745 (11) 0.0352 (9)
H42 0.3500 1.0801 0.0111 0.042*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.0347 (5) 0.0362 (6) 0.0402 (5) 0.0082 (4) 0.0016 (4) 0.0039 (4)
Cl2 0.0399 (5) 0.0284 (6) 0.0497 (6) 0.0047 (4) 0.0066 (4) 0.0039 (4)
O1 0.0320 (14) 0.0387 (16) 0.0369 (14) −0.0017 (12) −0.0031 (11) 0.0085 (12)
O2 0.0315 (14) 0.0280 (16) 0.0577 (18) 0.0055 (12) 0.0008 (12) 0.0016 (13)
N1 0.0250 (15) 0.0309 (18) 0.0312 (16) −0.0041 (13) 0.0011 (12) 0.0009 (13)
N2 0.0198 (14) 0.0301 (18) 0.0356 (17) −0.0008 (13) −0.0011 (12) 0.0049 (13)
N3 0.0226 (15) 0.0261 (18) 0.0374 (17) −0.0011 (13) 0.0002 (12) −0.0005 (13)
N4 0.0205 (15) 0.0319 (19) 0.0373 (17) 0.0009 (13) 0.0014 (12) 0.0021 (13)
C1 0.0258 (18) 0.025 (2) 0.0323 (19) −0.0032 (16) 0.0009 (15) −0.0028 (16)
C2 0.0228 (18) 0.030 (2) 0.036 (2) 0.0030 (16) 0.0009 (15) −0.0078 (17)
C3 0.0293 (19) 0.019 (2) 0.036 (2) 0.0039 (15) −0.0029 (15) −0.0025 (16)
C4 0.034 (2) 0.032 (2) 0.034 (2) −0.0004 (17) 0.0013 (16) 0.0058 (17)
C5 0.0253 (19) 0.035 (2) 0.037 (2) −0.0041 (17) 0.0012 (15) 0.0005 (17)
C6 0.0199 (17) 0.026 (2) 0.0308 (19) −0.0032 (15) −0.0039 (14) −0.0029 (15)
C7 0.028 (2) 0.029 (2) 0.0294 (19) −0.0061 (16) −0.0041 (15) −0.0024 (17)
C8 0.032 (2) 0.038 (2) 0.0282 (19) −0.0009 (17) 0.0045 (15) −0.0019 (17)
C9 0.0237 (18) 0.028 (2) 0.0284 (19) −0.0016 (15) 0.0091 (14) 0.0002 (15)
C10 0.0276 (19) 0.031 (2) 0.038 (2) 0.0022 (17) 0.0055 (16) 0.0024 (17)
C11 0.0220 (18) 0.044 (3) 0.039 (2) −0.0030 (17) 0.0007 (16) 0.0032 (18)
C12 0.039 (2) 0.035 (2) 0.035 (2) −0.0101 (18) 0.0020 (17) −0.0018 (17)
C13 0.045 (2) 0.025 (2) 0.037 (2) −0.0007 (18) 0.0072 (18) 0.0018 (17)
C14 0.0296 (19) 0.037 (2) 0.031 (2) 0.0005 (17) 0.0014 (15) 0.0065 (17)
C15 0.0218 (18) 0.033 (2) 0.039 (2) 0.0016 (16) −0.0010 (15) 0.0000 (17)
C16 0.0170 (16) 0.029 (2) 0.0297 (18) −0.0004 (15) 0.0006 (14) −0.0001 (15)
C17 0.038 (2) 0.060 (3) 0.031 (2) −0.021 (2) 0.0109 (17) −0.0048 (19)
C18 0.050 (3) 0.077 (3) 0.040 (2) −0.029 (2) 0.008 (2) −0.024 (2)
C19 0.032 (2) 0.042 (3) 0.052 (3) −0.0153 (19) 0.0048 (18) −0.008 (2)
C20 0.0266 (19) 0.040 (2) 0.042 (2) −0.0051 (18) 0.0062 (16) 0.0070 (18)
C21 0.0224 (18) 0.044 (2) 0.0298 (19) 0.0029 (17) −0.0001 (15) 0.0023 (17)
C22 0.0250 (18) 0.025 (2) 0.0261 (18) −0.0022 (16) 0.0072 (14) 0.0016 (15)
C23 0.0221 (18) 0.034 (2) 0.0293 (19) −0.0020 (16) 0.0018 (14) −0.0025 (16)
C24 0.0302 (19) 0.028 (2) 0.0230 (17) 0.0006 (16) 0.0089 (14) 0.0019 (15)
C25 0.035 (2) 0.027 (2) 0.031 (2) −0.0110 (17) 0.0089 (16) 0.0000 (16)
C26 0.0259 (18) 0.033 (2) 0.032 (2) −0.0083 (17) 0.0056 (15) 0.0019 (16)
C27 0.0250 (18) 0.028 (2) 0.0274 (18) 0.0008 (16) 0.0063 (14) 0.0004 (15)
C28 0.0233 (18) 0.034 (2) 0.033 (2) −0.0017 (17) 0.0062 (15) 0.0008 (17)
C29 0.0276 (19) 0.025 (2) 0.037 (2) −0.0024 (16) −0.0019 (15) −0.0032 (16)
C30 0.0288 (19) 0.020 (2) 0.035 (2) −0.0052 (15) −0.0018 (15) −0.0013 (15)
C31 0.030 (2) 0.041 (3) 0.046 (2) 0.0028 (18) −0.0019 (17) 0.0043 (19)
C32 0.051 (3) 0.043 (3) 0.040 (2) −0.006 (2) −0.0014 (19) 0.0093 (19)
C33 0.055 (3) 0.049 (3) 0.044 (2) −0.010 (2) 0.014 (2) −0.001 (2)
C34 0.034 (2) 0.048 (3) 0.061 (3) 0.003 (2) 0.014 (2) 0.001 (2)
C35 0.030 (2) 0.035 (2) 0.047 (2) −0.0013 (17) 0.0017 (17) 0.0068 (18)
C36 0.0208 (18) 0.040 (2) 0.034 (2) 0.0010 (16) 0.0002 (15) 0.0036 (17)
C37 0.0177 (17) 0.029 (2) 0.036 (2) 0.0032 (15) 0.0010 (14) 0.0019 (16)
C38 0.0260 (19) 0.032 (2) 0.037 (2) 0.0043 (17) 0.0013 (15) −0.0012 (17)
C39 0.027 (2) 0.028 (2) 0.060 (3) 0.0050 (17) 0.0038 (18) 0.0095 (19)
C40 0.038 (2) 0.043 (3) 0.044 (2) 0.008 (2) 0.0166 (18) 0.013 (2)
C41 0.045 (2) 0.046 (3) 0.034 (2) 0.010 (2) 0.0107 (18) −0.0003 (18)
C42 0.031 (2) 0.031 (2) 0.043 (2) 0.0032 (17) −0.0011 (17) −0.0048 (18)

Geometric parameters (Å, °)

Cl1—C3 1.745 (3) C17—H17 0.9300
Cl2—C24 1.745 (3) C18—C19 1.382 (6)
O1—C7 1.214 (4) C18—H18 0.9300
O2—C28 1.222 (4) C19—C20 1.360 (5)
N1—C7 1.389 (4) C19—H19 0.9300
N1—C1 1.389 (4) C20—C21 1.384 (5)
N1—C8 1.470 (4) C20—H20 0.9300
N2—C7 1.376 (4) C21—H21 0.9300
N2—C6 1.389 (4) C22—C23 1.380 (5)
N2—C15 1.450 (4) C22—C27 1.397 (5)
N3—C28 1.384 (4) C23—C24 1.380 (5)
N3—C22 1.396 (4) C23—H23 0.9300
N3—C29 1.461 (4) C24—C25 1.386 (5)
N4—C28 1.383 (5) C25—C26 1.380 (5)
N4—C27 1.393 (4) C25—H25 0.9300
N4—C36 1.459 (4) C26—C27 1.367 (5)
C1—C2 1.379 (5) C26—H26 0.9300
C1—C6 1.410 (5) C29—C30 1.511 (5)
C2—C3 1.396 (5) C29—H29A 0.9700
C2—H2 0.9300 C29—H29B 0.9700
C3—C4 1.381 (5) C30—C35 1.383 (5)
C4—C5 1.396 (5) C30—C31 1.398 (5)
C4—H4 0.9300 C31—C32 1.375 (5)
C5—C6 1.377 (5) C31—H31 0.9300
C5—H5 0.9300 C32—C33 1.388 (6)
C8—C9 1.511 (5) C32—H32 0.9300
C8—H8A 0.9700 C33—C34 1.375 (6)
C8—H8B 0.9700 C33—H33 0.9300
C9—C10 1.377 (5) C34—C35 1.387 (5)
C9—C14 1.392 (5) C34—H34 0.9300
C10—C11 1.382 (5) C35—H35 0.9300
C10—H10 0.9300 C36—C37 1.508 (5)
C11—C12 1.373 (5) C36—H36A 0.9700
C11—H11 0.9300 C36—H36B 0.9700
C12—C13 1.388 (5) C37—C38 1.375 (5)
C12—H12 0.9300 C37—C42 1.392 (5)
C13—C14 1.372 (5) C38—C39 1.391 (5)
C13—H13 0.9300 C38—H38 0.9300
C14—H14 0.9300 C39—C40 1.377 (6)
C15—C16 1.510 (5) C39—H39 0.9300
C15—H15A 0.9700 C40—C41 1.369 (6)
C15—H15B 0.9700 C40—H40 0.9300
C16—C21 1.379 (5) C41—C42 1.381 (5)
C16—C17 1.390 (5) C41—H41 0.9300
C17—C18 1.374 (5) C42—H42 0.9300
C7—N1—C1 110.4 (3) C19—C20—C21 120.2 (3)
C7—N1—C8 123.3 (3) C19—C20—H20 119.9
C1—N1—C8 125.9 (3) C21—C20—H20 119.9
C7—N2—C6 110.5 (3) C16—C21—C20 121.1 (3)
C7—N2—C15 124.7 (3) C16—C21—H21 119.4
C6—N2—C15 124.6 (3) C20—C21—H21 119.4
C28—N3—C22 109.7 (3) C23—C22—N3 131.5 (3)
C28—N3—C29 123.2 (3) C23—C22—C27 121.3 (3)
C22—N3—C29 126.7 (3) N3—C22—C27 107.2 (3)
C28—N4—C27 110.2 (3) C22—C23—C24 116.6 (3)
C28—N4—C36 123.6 (3) C22—C23—H23 121.7
C27—N4—C36 126.0 (3) C24—C23—H23 121.7
C2—C1—N1 132.2 (3) C23—C24—C25 122.8 (3)
C2—C1—C6 121.3 (3) C23—C24—Cl2 117.9 (3)
N1—C1—C6 106.4 (3) C25—C24—Cl2 119.3 (3)
C1—C2—C3 116.1 (3) C26—C25—C24 119.5 (3)
C1—C2—H2 121.9 C26—C25—H25 120.2
C3—C2—H2 121.9 C24—C25—H25 120.2
C4—C3—C2 123.4 (3) C27—C26—C25 119.0 (3)
C4—C3—Cl1 118.3 (3) C27—C26—H26 120.5
C2—C3—Cl1 118.4 (3) C25—C26—H26 120.5
C3—C4—C5 119.9 (3) C26—C27—N4 132.5 (3)
C3—C4—H4 120.1 C26—C27—C22 120.7 (3)
C5—C4—H4 120.1 N4—C27—C22 106.8 (3)
C6—C5—C4 117.9 (3) O2—C28—N4 127.1 (3)
C6—C5—H5 121.1 O2—C28—N3 126.8 (3)
C4—C5—H5 121.1 N4—C28—N3 106.1 (3)
C5—C6—N2 131.8 (3) N3—C29—C30 112.3 (3)
C5—C6—C1 121.4 (3) N3—C29—H29A 109.2
N2—C6—C1 106.9 (3) C30—C29—H29A 109.2
O1—C7—N2 127.4 (3) N3—C29—H29B 109.2
O1—C7—N1 126.8 (3) C30—C29—H29B 109.2
N2—C7—N1 105.8 (3) H29A—C29—H29B 107.9
N1—C8—C9 111.6 (3) C35—C30—C31 118.0 (3)
N1—C8—H8A 109.3 C35—C30—C29 121.8 (3)
C9—C8—H8A 109.3 C31—C30—C29 120.2 (3)
N1—C8—H8B 109.3 C32—C31—C30 121.4 (4)
C9—C8—H8B 109.3 C32—C31—H31 119.3
H8A—C8—H8B 108.0 C30—C31—H31 119.3
C10—C9—C14 118.9 (3) C31—C32—C33 119.5 (4)
C10—C9—C8 121.6 (3) C31—C32—H32 120.2
C14—C9—C8 119.5 (3) C33—C32—H32 120.2
C9—C10—C11 120.2 (3) C34—C33—C32 120.0 (4)
C9—C10—H10 119.9 C34—C33—H33 120.0
C11—C10—H10 119.9 C32—C33—H33 120.0
C12—C11—C10 120.7 (3) C33—C34—C35 120.1 (4)
C12—C11—H11 119.6 C33—C34—H34 119.9
C10—C11—H11 119.6 C35—C34—H34 119.9
C11—C12—C13 119.5 (4) C30—C35—C34 120.9 (4)
C11—C12—H12 120.3 C30—C35—H35 119.5
C13—C12—H12 120.3 C34—C35—H35 119.5
C14—C13—C12 119.7 (4) N4—C36—C37 113.2 (3)
C14—C13—H13 120.1 N4—C36—H36A 108.9
C12—C13—H13 120.1 C37—C36—H36A 108.9
C13—C14—C9 120.9 (3) N4—C36—H36B 108.9
C13—C14—H14 119.5 C37—C36—H36B 108.9
C9—C14—H14 119.5 H36A—C36—H36B 107.8
N2—C15—C16 112.9 (3) C38—C37—C42 119.1 (3)
N2—C15—H15A 109.0 C38—C37—C36 120.4 (3)
C16—C15—H15A 109.0 C42—C37—C36 120.5 (3)
N2—C15—H15B 109.0 C37—C38—C39 120.8 (3)
C16—C15—H15B 109.0 C37—C38—H38 119.6
H15A—C15—H15B 107.8 C39—C38—H38 119.6
C21—C16—C17 118.3 (3) C40—C39—C38 119.5 (4)
C21—C16—C15 121.4 (3) C40—C39—H39 120.3
C17—C16—C15 120.2 (3) C38—C39—H39 120.3
C18—C17—C16 120.1 (3) C41—C40—C39 120.0 (4)
C18—C17—H17 120.0 C41—C40—H40 120.0
C16—C17—H17 120.0 C39—C40—H40 120.0
C17—C18—C19 120.9 (4) C40—C41—C42 120.8 (4)
C17—C18—H18 119.6 C40—C41—H41 119.6
C19—C18—H18 119.6 C42—C41—H41 119.6
C20—C19—C18 119.4 (4) C41—C42—C37 119.8 (4)
C20—C19—H19 120.3 C41—C42—H42 120.1
C18—C19—H19 120.3 C37—C42—H42 120.1
C7—N1—C1—C2 177.0 (4) C28—N3—C22—C23 178.8 (3)
C8—N1—C1—C2 4.2 (6) C29—N3—C22—C23 −8.1 (6)
C7—N1—C1—C6 −2.1 (4) C28—N3—C22—C27 1.0 (4)
C8—N1—C1—C6 −174.9 (3) C29—N3—C22—C27 174.0 (3)
N1—C1—C2—C3 −179.5 (3) N3—C22—C23—C24 −177.0 (3)
C6—C1—C2—C3 −0.4 (5) C27—C22—C23—C24 0.6 (5)
C1—C2—C3—C4 −1.4 (5) C22—C23—C24—C25 −0.1 (5)
C1—C2—C3—Cl1 177.0 (3) C22—C23—C24—Cl2 −179.8 (2)
C2—C3—C4—C5 2.0 (6) C23—C24—C25—C26 −0.6 (5)
Cl1—C3—C4—C5 −176.5 (3) Cl2—C24—C25—C26 179.2 (3)
C3—C4—C5—C6 −0.6 (5) C24—C25—C26—C27 0.7 (5)
C4—C5—C6—N2 178.6 (3) C25—C26—C27—N4 178.0 (3)
C4—C5—C6—C1 −1.2 (5) C25—C26—C27—C22 −0.1 (5)
C7—N2—C6—C5 −179.6 (4) C28—N4—C27—C26 −177.6 (4)
C15—N2—C6—C5 −4.8 (6) C36—N4—C27—C26 7.7 (6)
C7—N2—C6—C1 0.2 (4) C28—N4—C27—C22 0.7 (4)
C15—N2—C6—C1 175.0 (3) C36—N4—C27—C22 −174.0 (3)
C2—C1—C6—C5 1.7 (5) C23—C22—C27—C26 −0.5 (5)
N1—C1—C6—C5 −179.0 (3) N3—C22—C27—C26 177.6 (3)
C2—C1—C6—N2 −178.1 (3) C23—C22—C27—N4 −179.1 (3)
N1—C1—C6—N2 1.2 (4) N3—C22—C27—N4 −1.0 (4)
C6—N2—C7—O1 178.9 (3) C27—N4—C28—O2 179.6 (3)
C15—N2—C7—O1 4.0 (6) C36—N4—C28—O2 −5.6 (6)
C6—N2—C7—N1 −1.5 (4) C27—N4—C28—N3 −0.1 (4)
C15—N2—C7—N1 −176.3 (3) C36—N4—C28—N3 174.7 (3)
C1—N1—C7—O1 −178.1 (3) C22—N3—C28—O2 179.8 (3)
C8—N1—C7—O1 −5.1 (5) C29—N3—C28—O2 6.4 (5)
C1—N1—C7—N2 2.2 (4) C22—N3—C28—N4 −0.5 (4)
C8—N1—C7—N2 175.3 (3) C29—N3—C28—N4 −173.9 (3)
C7—N1—C8—C9 −90.5 (4) C28—N3—C29—C30 92.6 (4)
C1—N1—C8—C9 81.5 (4) C22—N3—C29—C30 −79.6 (4)
N1—C8—C9—C10 −108.5 (4) N3—C29—C30—C35 112.5 (4)
N1—C8—C9—C14 70.1 (4) N3—C29—C30—C31 −66.6 (4)
C14—C9—C10—C11 −1.4 (5) C35—C30—C31—C32 −0.3 (6)
C8—C9—C10—C11 177.2 (3) C29—C30—C31—C32 178.8 (3)
C9—C10—C11—C12 0.5 (5) C30—C31—C32—C33 0.1 (6)
C10—C11—C12—C13 0.8 (5) C31—C32—C33—C34 0.4 (6)
C11—C12—C13—C14 −1.3 (5) C32—C33—C34—C35 −0.6 (6)
C12—C13—C14—C9 0.5 (5) C31—C30—C35—C34 0.2 (5)
C10—C9—C14—C13 0.9 (5) C29—C30—C35—C34 −179.0 (3)
C8—C9—C14—C13 −177.8 (3) C33—C34—C35—C30 0.3 (6)
C7—N2—C15—C16 −116.9 (4) C28—N4—C36—C37 112.1 (4)
C6—N2—C15—C16 68.9 (4) C27—N4—C36—C37 −73.9 (4)
N2—C15—C16—C21 −118.9 (4) N4—C36—C37—C38 120.9 (4)
N2—C15—C16—C17 61.7 (4) N4—C36—C37—C42 −60.6 (4)
C21—C16—C17—C18 −1.0 (6) C42—C37—C38—C39 −0.4 (5)
C15—C16—C17—C18 178.4 (4) C36—C37—C38—C39 178.1 (3)
C16—C17—C18—C19 0.5 (7) C37—C38—C39—C40 −0.8 (5)
C17—C18—C19—C20 0.3 (7) C38—C39—C40—C41 0.9 (6)
C18—C19—C20—C21 −0.6 (6) C39—C40—C41—C42 0.1 (6)
C17—C16—C21—C20 0.7 (5) C40—C41—C42—C37 −1.3 (6)
C15—C16—C21—C20 −178.7 (3) C38—C37—C42—C41 1.4 (5)
C19—C20—C21—C16 0.1 (6) C36—C37—C42—C41 −177.0 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6817).

References

  1. Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
  2. Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822. [DOI] [PMC free article] [PubMed]
  4. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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  6. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029084/bt6817sup1.cif

e-67-o2136-sup1.cif (28.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029084/bt6817Isup2.hkl

e-67-o2136-Isup2.hkl (291.3KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811029084/bt6817Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


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