2-(2-Chloro­phen­yl)-4,5-diphenyl-1H-imidazole

The asymmetric unit of the title compound, C₂₁H₁₅ClN₂, contains two crystallographically independent molocules. In one of the mol­ecules, the chloro­phenyl ring is disordered over two orientations; these are approximately related by a rotation through 180° about its bond with the imidazole ring. The independent mol­ecules are linked into a chain along the a axis by N—H...N inter­molecular hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.162
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C24C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C21C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C23C
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C46A   ..  Cl1C    ..       3.24 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

2-(2-Chlorophenyl)-4,5-diphenyl-1H-imidazole

Crystal data

C21H15ClN2	Z = 4
Mr = 330.80	F(000) = 688
Triclinic, P1	Dx = 1.287 Mg m^−3
Hall symbol: -P 1	Melting point = 513–515 K
a = 9.0505 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9501 (3) Å	Cell parameters from 20822 reflections
c = 18.0232 (5) Å	θ = 3.5–17.8°
α = 81.763 (2)°	µ = 0.23 mm^−1
β = 80.146 (2)°	T = 293 K
γ = 77.499 (2)°	Block, colourless
V = 1707.59 (8) Å^3	0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX2 diffractometer	6026 independent reflections
Radiation source: fine-focus sealed tube	4645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.2°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −13→13
Tmin = 0.956, Tmax = 0.978	l = −21→21
33526 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0877P)^2 + 0.5016P] where P = (Fo^2 + 2Fc^2)/3
6026 reflections	(Δ/σ)max = 0.001
481 parameters	Δρmax = 0.58 e Å^−3
48 restraints	Δρmin = −0.59 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1B	0.13047 (14)	0.74866 (10)	0.45177 (6)	0.0792 (4)	0.831 (2)
N1B	0.4507 (2)	0.87765 (17)	0.27137 (11)	0.0420 (6)
N3B	0.20589 (18)	0.93986 (16)	0.31267 (10)	0.0400 (6)
C2B	0.3192 (2)	0.84155 (19)	0.30383 (12)	0.0404 (7)
C4B	0.2695 (2)	1.04425 (18)	0.28458 (11)	0.0368 (6)
C5B	0.4224 (2)	1.00638 (19)	0.25931 (12)	0.0386 (7)
C21B	0.3127 (2)	0.70712 (14)	0.31758 (12)	0.0377 (10)	0.831 (2)
C22B	0.2295 (2)	0.65775 (17)	0.38279 (10)	0.0477 (10)	0.831 (2)
C23B	0.2247 (3)	0.53033 (19)	0.39369 (11)	0.0622 (14)	0.831 (2)
C24B	0.3032 (3)	0.45227 (14)	0.33937 (14)	0.0720 (16)	0.831 (2)
C25B	0.3864 (3)	0.50164 (18)	0.27416 (13)	0.0676 (11)	0.831 (2)
C26B	0.3911 (3)	0.62906 (19)	0.26325 (11)	0.0537 (14)	0.831 (2)
C41B	0.1723 (2)	1.17066 (19)	0.28302 (12)	0.0391 (7)
C42B	0.1896 (3)	1.2622 (2)	0.22246 (13)	0.0490 (8)
C43B	0.0941 (3)	1.3793 (2)	0.22176 (15)	0.0609 (9)
C44B	−0.0187 (3)	1.4072 (2)	0.28157 (16)	0.0617 (9)
C45B	−0.0375 (3)	1.3179 (2)	0.34175 (15)	0.0586 (9)
C46B	0.0560 (3)	1.2004 (2)	0.34255 (13)	0.0484 (8)
C51B	0.5459 (2)	1.0755 (2)	0.22740 (13)	0.0456 (7)
C52B	0.6449 (3)	1.0422 (3)	0.16255 (15)	0.0591 (9)
C53B	0.7632 (3)	1.1055 (3)	0.1350 (2)	0.0821 (11)
C54B	0.7848 (3)	1.2003 (3)	0.1709 (3)	0.0937 (16)
C55B	0.6876 (4)	1.2336 (3)	0.2345 (3)	0.0899 (14)
C56B	0.5689 (3)	1.1720 (3)	0.26325 (18)	0.0658 (10)
Cl1C	0.4448 (8)	0.5928 (6)	0.2435 (4)	0.092 (3)	0.169 (2)
C21C	0.2610 (12)	0.7186 (8)	0.3519 (6)	0.039 (4)	0.169 (2)
C22C	0.3208 (12)	0.6039 (10)	0.3232 (6)	0.072 (5)	0.169 (2)
C23C	0.2731 (14)	0.4954 (8)	0.3596 (7)	0.048 (4)	0.169 (2)
C24C	0.1657 (14)	0.5014 (9)	0.4248 (7)	0.076 (5)	0.169 (2)
C25C	0.1059 (12)	0.6160 (11)	0.4535 (5)	0.068 (4)	0.169 (2)
C26C	0.1536 (12)	0.7246 (9)	0.4171 (6)	0.054 (5)	0.169 (2)
Cl1A	0.65550 (10)	0.62938 (8)	0.40788 (4)	0.0805 (3)
N1A	0.96250 (19)	0.84786 (18)	0.25913 (10)	0.0416 (6)
N3A	0.77095 (18)	0.75790 (16)	0.25154 (9)	0.0391 (5)
C2A	0.8311 (2)	0.8148 (2)	0.29552 (12)	0.0384 (7)
C4A	0.8703 (2)	0.7532 (2)	0.18413 (11)	0.0385 (7)
C5A	0.9913 (2)	0.8078 (2)	0.18856 (12)	0.0391 (7)
C21A	0.7688 (2)	0.8464 (2)	0.37248 (12)	0.0449 (7)
C22A	0.6898 (3)	0.7702 (3)	0.42702 (14)	0.0545 (8)
C23A	0.6388 (3)	0.8045 (3)	0.49939 (15)	0.0732 (10)
C24A	0.6675 (4)	0.9120 (4)	0.51896 (18)	0.0834 (13)
C25A	0.7444 (3)	0.9886 (3)	0.46663 (19)	0.0807 (11)
C26A	0.7932 (3)	0.9569 (3)	0.39436 (16)	0.0613 (9)
C41A	0.8369 (2)	0.6993 (2)	0.12024 (12)	0.0414 (7)
C42A	0.8724 (3)	0.7500 (3)	0.04598 (13)	0.0564 (9)
C43A	0.8430 (3)	0.6967 (3)	−0.01340 (15)	0.0706 (10)
C44A	0.7755 (3)	0.5943 (3)	−0.00006 (18)	0.0752 (11)
C45A	0.7369 (3)	0.5437 (3)	0.07320 (18)	0.0695 (11)
C46A	0.7666 (3)	0.5957 (2)	0.13292 (15)	0.0531 (8)
C51A	1.1318 (2)	0.8225 (2)	0.13698 (12)	0.0438 (7)
C52A	1.1887 (3)	0.9319 (3)	0.12966 (14)	0.0545 (8)
C53A	1.3265 (3)	0.9411 (3)	0.08488 (17)	0.0729 (11)
C54A	1.4071 (3)	0.8441 (4)	0.04620 (17)	0.0796 (13)
C55A	1.3509 (3)	0.7347 (3)	0.05156 (17)	0.0740 (10)
C56A	1.2145 (3)	0.7243 (3)	0.09664 (15)	0.0586 (9)
H43B	0.10638	1.43958	0.18045	0.0730*
H44B	−0.08196	1.48639	0.28119	0.0741*
H45B	−0.11382	1.33647	0.38242	0.0703*
H46B	0.04100	1.14014	0.38356	0.0582*
H52B	0.63180	0.97741	0.13764	0.0709*
H53B	0.82894	1.08302	0.09131	0.0987*
H54B	0.86503	1.24195	0.15214	0.1124*
H55B	0.70155	1.29871	0.25892	0.1081*
H56B	0.50395	1.19535	0.30692	0.0791*
H1B	0.538 (3)	0.831 (2)	0.2619 (13)	0.050 (7)*
H23B	0.16908	0.49730	0.43733	0.0746*	0.831 (2)
H24B	0.29997	0.36701	0.34667	0.0862*	0.831 (2)
H25B	0.43883	0.44941	0.23781	0.0810*	0.831 (2)
H26B	0.44680	0.66210	0.21962	0.0645*	0.831 (2)
H42B	0.26640	1.24473	0.18179	0.0587*
H23C	0.31315	0.41868	0.34039	0.0575*	0.169 (2)
H24C	0.13381	0.42872	0.44912	0.0909*	0.169 (2)
H25C	0.03401	0.62000	0.49707	0.0807*	0.169 (2)
H26C	0.11354	0.80124	0.43629	0.0644*	0.169 (2)
H1A	1.022 (3)	0.879 (2)	0.2781 (13)	0.045 (6)*
H23A	0.58471	0.75391	0.53490	0.0876*
H24A	0.63468	0.93342	0.56803	0.1003*
H25A	0.76341	1.06198	0.48015	0.0969*
H26A	0.84377	1.01022	0.35906	0.0735*
H42A	0.91654	0.82095	0.03607	0.0676*
H43A	0.86950	0.73083	−0.06296	0.0848*
H44A	0.75558	0.55892	−0.04033	0.0903*
H45A	0.69045	0.47398	0.08249	0.0835*
H46A	0.73946	0.56110	0.18230	0.0637*
H52A	1.13376	0.99949	0.15506	0.0653*
H53A	1.36459	1.01446	0.08109	0.0876*
H54A	1.49993	0.85115	0.01619	0.0956*
H55A	1.40523	0.66854	0.02477	0.0887*
H56A	1.17699	0.65068	0.10021	0.0702*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1B	0.1089 (8)	0.0671 (6)	0.0532 (6)	−0.0201 (5)	0.0147 (5)	−0.0063 (5)
N1B	0.0332 (9)	0.0383 (10)	0.0554 (12)	−0.0031 (8)	−0.0105 (8)	−0.0094 (8)
N3B	0.0370 (9)	0.0368 (10)	0.0474 (10)	−0.0093 (7)	−0.0086 (7)	−0.0026 (8)
C2B	0.0388 (11)	0.0358 (12)	0.0493 (13)	−0.0082 (9)	−0.0143 (9)	−0.0032 (9)
C4B	0.0376 (10)	0.0362 (11)	0.0391 (11)	−0.0096 (8)	−0.0089 (8)	−0.0046 (9)
C5B	0.0390 (11)	0.0368 (12)	0.0425 (12)	−0.0093 (9)	−0.0091 (9)	−0.0056 (9)
C21B	0.0358 (15)	0.0341 (17)	0.0446 (18)	−0.0064 (12)	−0.0092 (13)	−0.0055 (14)
C22B	0.0553 (17)	0.0429 (18)	0.0474 (18)	−0.0160 (14)	−0.0120 (14)	0.0018 (14)
C23B	0.076 (3)	0.055 (2)	0.058 (2)	−0.0276 (19)	−0.0103 (19)	0.0088 (19)
C24B	0.102 (3)	0.037 (2)	0.084 (3)	−0.0171 (19)	−0.029 (2)	−0.0059 (19)
C25B	0.090 (2)	0.0398 (18)	0.075 (2)	−0.0125 (16)	−0.0111 (18)	−0.0149 (16)
C26B	0.061 (2)	0.037 (2)	0.063 (3)	−0.0079 (17)	−0.0114 (19)	−0.0054 (19)
C41B	0.0409 (11)	0.0358 (12)	0.0434 (12)	−0.0089 (9)	−0.0106 (9)	−0.0062 (9)
C42B	0.0553 (13)	0.0462 (13)	0.0430 (13)	−0.0058 (10)	−0.0077 (10)	−0.0028 (10)
C43B	0.0815 (18)	0.0430 (14)	0.0548 (16)	−0.0047 (12)	−0.0193 (13)	0.0053 (11)
C44B	0.0723 (17)	0.0422 (14)	0.0669 (18)	0.0097 (12)	−0.0222 (14)	−0.0111 (13)
C45B	0.0561 (14)	0.0568 (16)	0.0573 (16)	0.0059 (12)	−0.0061 (12)	−0.0162 (13)
C46B	0.0498 (13)	0.0447 (13)	0.0483 (13)	−0.0065 (10)	−0.0041 (10)	−0.0047 (10)
C51B	0.0370 (11)	0.0445 (13)	0.0555 (14)	−0.0108 (9)	−0.0107 (10)	0.0031 (10)
C52B	0.0469 (13)	0.0625 (16)	0.0617 (16)	−0.0092 (11)	−0.0019 (12)	0.0043 (13)
C53B	0.0501 (16)	0.086 (2)	0.093 (2)	−0.0116 (15)	0.0084 (15)	0.0222 (19)
C54B	0.0515 (17)	0.076 (2)	0.148 (4)	−0.0293 (16)	−0.013 (2)	0.030 (2)
C55B	0.069 (2)	0.070 (2)	0.143 (3)	−0.0362 (16)	−0.027 (2)	−0.004 (2)
C56B	0.0576 (15)	0.0611 (17)	0.087 (2)	−0.0256 (13)	−0.0129 (14)	−0.0114 (14)
Cl1C	0.108 (5)	0.061 (4)	0.108 (5)	−0.010 (3)	−0.005 (4)	−0.033 (3)
C21C	0.034 (6)	0.045 (7)	0.036 (7)	0.008 (6)	−0.010 (6)	−0.019 (6)
C22C	0.071 (8)	0.063 (8)	0.087 (9)	−0.010 (6)	−0.033 (7)	−0.005 (7)
C23C	0.055 (7)	0.029 (7)	0.060 (9)	−0.016 (6)	−0.008 (7)	0.006 (7)
C24C	0.087 (9)	0.064 (9)	0.083 (9)	−0.032 (7)	−0.021 (7)	0.005 (7)
C25C	0.062 (7)	0.075 (8)	0.068 (8)	−0.026 (6)	−0.009 (6)	0.002 (6)
C26C	0.064 (8)	0.053 (8)	0.050 (8)	−0.014 (6)	−0.028 (7)	0.001 (7)
Cl1A	0.1029 (6)	0.0775 (5)	0.0624 (5)	−0.0372 (4)	−0.0012 (4)	0.0050 (4)
N1A	0.0336 (9)	0.0506 (11)	0.0444 (11)	−0.0133 (8)	−0.0082 (8)	−0.0075 (8)
N3A	0.0325 (8)	0.0466 (10)	0.0383 (10)	−0.0087 (7)	−0.0050 (7)	−0.0039 (8)
C2A	0.0313 (10)	0.0450 (12)	0.0389 (12)	−0.0062 (8)	−0.0070 (8)	−0.0045 (9)
C4A	0.0349 (10)	0.0421 (12)	0.0375 (12)	−0.0062 (8)	−0.0054 (8)	−0.0031 (9)
C5A	0.0348 (10)	0.0441 (12)	0.0384 (12)	−0.0087 (9)	−0.0048 (8)	−0.0038 (9)
C21A	0.0333 (10)	0.0593 (14)	0.0420 (12)	−0.0041 (9)	−0.0092 (9)	−0.0085 (10)
C22A	0.0481 (13)	0.0676 (16)	0.0438 (14)	−0.0044 (11)	−0.0082 (10)	−0.0020 (12)
C23A	0.0704 (18)	0.099 (2)	0.0417 (15)	−0.0063 (16)	−0.0019 (12)	−0.0030 (15)
C24A	0.078 (2)	0.122 (3)	0.0481 (17)	−0.0021 (19)	−0.0070 (15)	−0.0316 (18)
C25A	0.0706 (19)	0.100 (2)	0.081 (2)	−0.0137 (17)	−0.0096 (16)	−0.0477 (19)
C26A	0.0526 (14)	0.0737 (18)	0.0623 (17)	−0.0149 (12)	−0.0028 (12)	−0.0264 (14)
C41A	0.0348 (10)	0.0457 (12)	0.0432 (12)	−0.0046 (9)	−0.0058 (9)	−0.0086 (10)
C42A	0.0569 (14)	0.0731 (17)	0.0435 (14)	−0.0232 (12)	−0.0052 (11)	−0.0077 (12)
C43A	0.0685 (17)	0.103 (2)	0.0431 (15)	−0.0202 (16)	−0.0028 (12)	−0.0189 (14)
C44A	0.0774 (19)	0.092 (2)	0.065 (2)	−0.0105 (16)	−0.0176 (15)	−0.0386 (17)
C45A	0.0790 (19)	0.0594 (17)	0.081 (2)	−0.0181 (14)	−0.0264 (16)	−0.0190 (15)
C46A	0.0564 (14)	0.0515 (14)	0.0547 (15)	−0.0140 (11)	−0.0133 (11)	−0.0052 (11)
C51A	0.0359 (11)	0.0553 (14)	0.0404 (12)	−0.0119 (10)	−0.0058 (9)	−0.0014 (10)
C52A	0.0551 (14)	0.0658 (16)	0.0475 (14)	−0.0269 (12)	−0.0061 (11)	−0.0013 (12)
C53A	0.0696 (18)	0.094 (2)	0.0631 (18)	−0.0478 (17)	−0.0050 (14)	0.0081 (16)
C54A	0.0494 (15)	0.124 (3)	0.0624 (19)	−0.0309 (17)	0.0077 (13)	0.0023 (19)
C55A	0.0502 (15)	0.098 (2)	0.0658 (19)	−0.0099 (15)	0.0109 (13)	−0.0133 (16)
C56A	0.0451 (13)	0.0635 (16)	0.0636 (16)	−0.0105 (11)	0.0027 (11)	−0.0086 (13)

Geometric parameters (Å, º)

Cl1B—C22B	1.711 (2)	C26B—H26B	0.93
Cl1C—C22C	1.666 (13)	C26C—H26C	0.93
Cl1A—C22A	1.729 (3)	C42B—H42B	0.93
N1B—C5B	1.369 (3)	C43B—H43B	0.93
N1B—C2B	1.347 (3)	C44B—H44B	0.93
N3B—C4B	1.383 (3)	C45B—H45B	0.93
N3B—C2B	1.323 (3)	C46B—H46B	0.93
N1B—H1B	0.85 (3)	C52B—H52B	0.93
N1A—C5A	1.369 (3)	C53B—H53B	0.93
N1A—C2A	1.352 (3)	C54B—H54B	0.93
N3A—C2A	1.323 (3)	C55B—H55B	0.93
N3A—C4A	1.383 (3)	C56B—H56B	0.93
N1A—H1A	0.84 (3)	C2A—C21A	1.465 (3)
C2B—C21C	1.630 (10)	C4A—C41A	1.469 (3)
C2B—C21B	1.470 (3)	C4A—C5A	1.375 (3)
C4B—C5B	1.373 (3)	C5A—C51A	1.466 (3)
C4B—C41B	1.470 (3)	C21A—C26A	1.397 (4)
C5B—C51B	1.475 (3)	C21A—C22A	1.399 (3)
C21B—C26B	1.390 (3)	C22A—C23A	1.384 (4)
C21B—C22B	1.390 (3)	C23A—C24A	1.364 (5)
C21C—C26C	1.391 (15)	C24A—C25A	1.371 (5)
C21C—C22C	1.391 (14)	C25A—C26A	1.371 (4)
C22B—C23B	1.390 (3)	C41A—C42A	1.386 (3)
C22C—C23C	1.389 (15)	C41A—C46A	1.390 (3)
C23B—C24B	1.390 (3)	C42A—C43A	1.379 (4)
C23C—C24C	1.391 (18)	C43A—C44A	1.363 (4)
C24B—C25B	1.390 (3)	C44A—C45A	1.374 (4)
C24C—C25C	1.390 (15)	C45A—C46A	1.377 (4)
C25B—C26B	1.390 (3)	C51A—C56A	1.391 (4)
C25C—C26C	1.390 (15)	C51A—C52A	1.384 (4)
C41B—C42B	1.384 (3)	C52A—C53A	1.380 (4)
C41B—C46B	1.389 (3)	C53A—C54A	1.360 (5)
C42B—C43B	1.382 (3)	C54A—C55A	1.385 (5)
C43B—C44B	1.371 (4)	C55A—C56A	1.374 (4)
C44B—C45B	1.366 (4)	C23A—H23A	0.93
C45B—C46B	1.378 (3)	C24A—H24A	0.93
C51B—C52B	1.387 (4)	C25A—H25A	0.93
C51B—C56B	1.384 (4)	C26A—H26A	0.93
C52B—C53B	1.384 (4)	C42A—H42A	0.93
C53B—C54B	1.363 (5)	C43A—H43A	0.93
C54B—C55B	1.363 (7)	C44A—H44A	0.93
C55B—C56B	1.379 (5)	C45A—H45A	0.93
C23B—H23B	0.93	C46A—H46A	0.93
C23C—H23C	0.93	C52A—H52A	0.93
C24B—H24B	0.93	C53A—H53A	0.93
C24C—H24C	0.93	C54A—H54A	0.93
C25B—H25B	0.93	C55A—H55A	0.93
C25C—H25C	0.93	C56A—H56A	0.93
Cl1A···N3A	3.0830 (18)	C24C···H25C^vii	2.5800
Cl1A···C21B	3.631 (2)	C25C···H25C^vii	3.0700
Cl1A···C24C^i	3.632 (12)	C25C···H24C^vii	2.6300
Cl1B···N3B	3.109 (2)	C25C···H45B^iv	3.0900
Cl1B···C26A^ii	3.603 (3)	C26A···H1A	2.77 (2)
Cl1C···N1B	3.243 (7)	C26B···H1B	2.81 (2)
Cl1C···C56A^ii	3.595 (8)	C26C···H1A^ii	3.08 (3)
Cl1C···C46A	3.239 (8)	C41A···H56A	2.9800
Cl1B···H25A^iii	2.9500	C41B···H24B^viii	3.0800
Cl1B···H45B^iv	2.9900	C42A···H56A	3.0100
Cl1C···H1B	2.99 (2)	C42B···H43A^ix	3.0000
Cl1C···H46A	2.6700	C42B···H24B^viii	3.0500
N1A···C21C^v	3.363 (11)	C45B···H55B^ii	3.0600
N1A···N3B^v	2.961 (2)	C45B···H25C^iv	3.0800
N1A···C2B^v	3.443 (3)	C46A···H26B	3.0400
N1B···N3A	2.895 (3)	C46B···H26A^ii	3.0800
N1B···Cl1C	3.243 (7)	C51A···H42A	2.8900
N3A···C52B	3.350 (4)	C51B···H42B	2.9600
N3A···N1B	2.895 (3)	C52A···H1A	2.89 (2)
N3A···Cl1A	3.0830 (18)	C52B···H1B	2.95 (2)
N3B···N1A^ii	2.961 (2)	C55B···H25B^viii	2.8900
N3B···Cl1B	3.109 (2)	C56A···H42A	3.0000
N3B···C52A^ii	3.343 (3)	C56B···H25B^viii	3.0100
N1A···H52A	2.8100	H1A···C21B^v	3.01 (3)
N1A···H26A	2.6400	H1A···N3B^v	2.14 (3)
N1B···H52B	2.8900	H1A···H26A	2.3600
N1B···H26B	2.6700	H1A···C26A	2.77 (2)
N3A···H1B	2.07 (3)	H1A···C52A	2.89 (2)
N3A···H46A	2.7300	H1A···C26C^v	3.08 (3)
N3B···H1A^ii	2.14 (3)	H1A···H52A	2.5800
N3B···H46B	2.7200	H1A···C2B^v	2.74 (3)
N3B···H26C	2.6300	H1A···C21C^v	2.86 (3)
C2A···C52B	3.555 (4)	H1B···H26B	2.4400
C2B···C52A^ii	3.479 (3)	H1B···C26B	2.81 (2)
C2B···N1A^ii	3.443 (3)	H1B···N3A	2.07 (3)
C4A···C52B	3.384 (4)	H1B···C4A	3.09 (3)
C4B···C52A^ii	3.452 (3)	H1B···C2A	2.78 (3)
C5A···C53B	3.562 (4)	H1B···Cl1C	2.99 (2)
C21B···Cl1A	3.631 (2)	H1B···C52B	2.95 (2)
C21C···N1A^ii	3.363 (11)	H23A···C24B^i	3.1000
C23C···C44B^vi	3.557 (13)	H23A···H24B^i	2.6000
C24A···C24A^iii	3.343 (6)	H24A···C4B^iii	2.9900
C24B···C43B^vi	3.351 (4)	H24B···H56B^vi	2.4300
C24B···C44B^vi	3.410 (4)	H24B···H23A^i	2.6000
C24B···C42B^vi	3.571 (3)	H24B···C42B^vi	3.0500
C24C···C25C^vii	3.350 (16)	H24B···C41B^vi	3.0800
C24C···Cl1A^i	3.632 (12)	H24C···C25C^vii	2.6300
C25B···C43B^vi	3.527 (4)	H24C···H25C^vii	1.8000
C25C···C24C^vii	3.350 (16)	H24C···C23A^i	3.0500
C25C···C25C^vii	3.567 (16)	H25A···Cl1B^iii	2.9500
C26A···Cl1B^v	3.603 (3)	H25B···C55B^vi	2.8900
C26B···C56A^ii	3.561 (4)	H25B···C56B^vi	3.0100
C41A···C56A	3.436 (3)	H25C···C45B^iv	3.0800
C41B···C56B	3.549 (3)	H25C···C24C^vii	2.5800
C42A···C56A	3.319 (4)	H25C···H45B^iv	2.5400
C42A···C51A	3.366 (3)	H25C···C25C^vii	3.0700
C42B···C24B^viii	3.571 (3)	H25C···H24C^vii	1.8000
C42B···C51B	3.432 (3)	H26A···H1A	2.3600
C42B···C56B	3.534 (4)	H26A···C46B^v	3.0800
C43B···C25B^viii	3.527 (4)	H26A···N1A	2.6400
C43B···C24B^viii	3.351 (4)	H26B···H1B	2.4400
C44B···C24B^viii	3.410 (4)	H26B···N1B	2.6700
C44B···C23C^viii	3.557 (13)	H26B···C46A	3.0400
C46A···Cl1C	3.239 (8)	H26C···N3B	2.6300
C51A···C42A	3.366 (3)	H42A···C56A	3.0000
C51B···C42B	3.432 (3)	H42A···C5A	2.9200
C52A···N3B^v	3.343 (3)	H42A···C51A	2.8900
C52A···C4B^v	3.452 (3)	H42B···C51B	2.9600
C52A···C2B^v	3.479 (3)	H42B···C5B	2.9700
C52B···C2A	3.555 (4)	H43A···C42B^ix	3.0000
C52B···N3A	3.350 (4)	H44A···H56A^x	2.5900
C52B···C4A	3.384 (4)	H44B···H46A^xi	2.5400
C53B···C5A	3.562 (4)	H45B···H25C^iv	2.5400
C56A···C41A	3.436 (3)	H45B···C25C^iv	3.0900
C56A···C42A	3.319 (4)	H45B···Cl1B^iv	2.9900
C56A···Cl1C^v	3.595 (8)	H46A···H44B^xii	2.5400
C56A···C26B^v	3.561 (4)	H46A···Cl1C	2.6700
C56B···C42B	3.534 (4)	H46A···N3A	2.7300
C56B···C41B	3.549 (3)	H46B···N3B	2.7200
C2A···H1B	2.78 (3)	H52A···H1A	2.5800
C2B···H1A^ii	2.74 (3)	H52A···C4B^v	2.9600
C4A···H52B	3.0200	H52A···N1A	2.8100
C4A···H56A	2.9900	H52B···C4A	3.0200
C4A···H1B	3.09 (3)	H52B···N1B	2.8900
C4B···H56B	3.0700	H53A···H54A^xiii	2.4600
C4B···H52A^ii	2.9600	H54A···H53A^xiii	2.4600
C4B···H24A^iii	2.9900	H55B···C45B^v	3.0600
C5A···H42A	2.9200	H56A···C4A	2.9900
C5B···H42B	2.9700	H56A···C41A	2.9800
C21B···H1A^ii	3.01 (3)	H56A···C42A	3.0100
C21C···H1A^ii	2.86 (3)	H56A···H44A^x	2.5900
C23A···H24C^i	3.0500	H56B···C4B	3.0700
C24B···H23A^i	3.1000	H56B···C24B^viii	3.0700
C24B···H56B^vi	3.0700	H56B···H24B^viii	2.4300
C2B—N1B—C5B	108.06 (17)	C46B—C45B—H45B	120.00
C2B—N3B—C4B	105.61 (16)	C44B—C45B—H45B	120.00
C2B—N1B—H1B	127.4 (16)	C45B—C46B—H46B	119.00
C5B—N1B—H1B	124.4 (16)	C41B—C46B—H46B	120.00
C2A—N1A—C5A	108.26 (17)	C51B—C52B—H52B	120.00
C2A—N3A—C4A	105.74 (17)	C53B—C52B—H52B	120.00
C2A—N1A—H1A	126.0 (16)	C52B—C53B—H53B	119.00
C5A—N1A—H1A	125.3 (16)	C54B—C53B—H53B	120.00
N3B—C2B—C21B	128.56 (18)	C55B—C54B—H54B	120.00
N3B—C2B—C21C	107.8 (4)	C53B—C54B—H54B	120.00
N1B—C2B—N3B	111.21 (18)	C56B—C55B—H55B	120.00
N1B—C2B—C21B	119.92 (18)	C54B—C55B—H55B	120.00
N1B—C2B—C21C	139.4 (4)	C51B—C56B—H56B	120.00
N3B—C4B—C5B	109.53 (17)	C55B—C56B—H56B	120.00
C5B—C4B—C41B	130.55 (18)	N1A—C2A—N3A	110.94 (18)
N3B—C4B—C41B	119.89 (17)	N1A—C2A—C21A	121.17 (18)
C4B—C5B—C51B	133.08 (19)	N3A—C2A—C21A	127.84 (18)
N1B—C5B—C51B	121.29 (18)	N3A—C4A—C5A	109.71 (18)
N1B—C5B—C4B	105.60 (17)	C5A—C4A—C41A	129.35 (18)
C2B—C21B—C26B	118.50 (18)	N3A—C4A—C41A	120.91 (17)
C22B—C21B—C26B	120.00 (16)	C4A—C5A—C51A	133.3 (2)
C2B—C21B—C22B	121.50 (17)	N1A—C5A—C51A	121.29 (18)
C2B—C21C—C26C	123.4 (7)	N1A—C5A—C4A	105.32 (17)
C22C—C21C—C26C	120.0 (9)	C2A—C21A—C22A	124.0 (2)
C2B—C21C—C22C	116.6 (8)	C2A—C21A—C26A	118.8 (2)
Cl1B—C22B—C23B	117.67 (15)	C22A—C21A—C26A	117.3 (2)
Cl1B—C22B—C21B	122.32 (14)	Cl1A—C22A—C21A	121.91 (19)
C21B—C22B—C23B	120.01 (17)	C21A—C22A—C23A	120.6 (3)
Cl1C—C22C—C23C	118.2 (9)	Cl1A—C22A—C23A	117.5 (2)
C21C—C22C—C23C	120.0 (10)	C22A—C23A—C24A	120.4 (3)
Cl1C—C22C—C21C	121.7 (9)	C23A—C24A—C25A	120.3 (3)
C22B—C23B—C24B	119.98 (19)	C24A—C25A—C26A	119.9 (3)
C22C—C23C—C24C	120.0 (9)	C21A—C26A—C25A	121.6 (3)
C23B—C24B—C25B	120.01 (17)	C4A—C41A—C42A	121.6 (2)
C23C—C24C—C25C	120.0 (10)	C42A—C41A—C46A	117.9 (2)
C24B—C25B—C26B	120.00 (19)	C4A—C41A—C46A	120.5 (2)
C24C—C25C—C26C	120.0 (10)	C41A—C42A—C43A	120.8 (3)
C21B—C26B—C25B	120.0 (2)	C42A—C43A—C44A	120.5 (3)
C21C—C26C—C25C	120.0 (9)	C43A—C44A—C45A	119.7 (3)
C4B—C41B—C42B	122.04 (19)	C44A—C45A—C46A	120.3 (3)
C4B—C41B—C46B	120.10 (19)	C41A—C46A—C45A	120.7 (2)
C42B—C41B—C46B	117.8 (2)	C5A—C51A—C52A	121.0 (2)
C41B—C42B—C43B	120.8 (2)	C52A—C51A—C56A	118.5 (2)
C42B—C43B—C44B	120.4 (2)	C5A—C51A—C56A	120.5 (2)
C43B—C44B—C45B	119.6 (2)	C51A—C52A—C53A	120.3 (3)
C44B—C45B—C46B	120.4 (2)	C52A—C53A—C54A	120.7 (3)
C41B—C46B—C45B	121.0 (2)	C53A—C54A—C55A	119.9 (3)
C52B—C51B—C56B	118.6 (2)	C54A—C55A—C56A	119.7 (3)
C5B—C51B—C56B	120.5 (2)	C51A—C56A—C55A	120.8 (3)
C5B—C51B—C52B	120.8 (2)	C22A—C23A—H23A	120.00
C51B—C52B—C53B	119.9 (3)	C24A—C23A—H23A	120.00
C52B—C53B—C54B	121.0 (3)	C23A—C24A—H24A	120.00
C53B—C54B—C55B	119.4 (3)	C25A—C24A—H24A	120.00
C54B—C55B—C56B	120.9 (3)	C24A—C25A—H25A	120.00
C51B—C56B—C55B	120.3 (3)	C26A—C25A—H25A	120.00
C24B—C23B—H23B	120.00	C21A—C26A—H26A	119.00
C22B—C23B—H23B	120.00	C25A—C26A—H26A	119.00
C24C—C23C—H23C	120.00	C41A—C42A—H42A	120.00
C22C—C23C—H23C	120.00	C43A—C42A—H42A	120.00
C23B—C24B—H24B	120.00	C42A—C43A—H43A	120.00
C25B—C24B—H24B	120.00	C44A—C43A—H43A	120.00
C23C—C24C—H24C	120.00	C43A—C44A—H44A	120.00
C25C—C24C—H24C	120.00	C45A—C44A—H44A	120.00
C24B—C25B—H25B	120.00	C44A—C45A—H45A	120.00
C26B—C25B—H25B	120.00	C46A—C45A—H45A	120.00
C26C—C25C—H25C	120.00	C41A—C46A—H46A	120.00
C24C—C25C—H25C	120.00	C45A—C46A—H46A	120.00
C21B—C26B—H26B	120.00	C51A—C52A—H52A	120.00
C25B—C26B—H26B	120.00	C53A—C52A—H52A	120.00
C25C—C26C—H26C	120.00	C52A—C53A—H53A	120.00
C21C—C26C—H26C	120.00	C54A—C53A—H53A	120.00
C43B—C42B—H42B	120.00	C53A—C54A—H54A	120.00
C41B—C42B—H42B	120.00	C55A—C54A—H54A	120.00
C44B—C43B—H43B	120.00	C54A—C55A—H55A	120.00
C42B—C43B—H43B	120.00	C56A—C55A—H55A	120.00
C43B—C44B—H44B	120.00	C51A—C56A—H56A	120.00
C45B—C44B—H44B	120.00	C55A—C56A—H56A	120.00
C5B—N1B—C2B—N3B	0.9 (2)	C56B—C51B—C52B—C53B	−0.2 (4)
C5B—N1B—C2B—C21B	174.99 (19)	C5B—C51B—C56B—C55B	177.9 (3)
C2B—N1B—C5B—C4B	−1.0 (2)	C52B—C51B—C56B—C55B	0.3 (4)
C2B—N1B—C5B—C51B	177.23 (19)	C5B—C51B—C52B—C53B	−177.8 (2)
C4B—N3B—C2B—N1B	−0.4 (2)	C51B—C52B—C53B—C54B	0.3 (5)
C4B—N3B—C2B—C21B	−173.8 (2)	C52B—C53B—C54B—C55B	−0.5 (6)
C2B—N3B—C4B—C5B	−0.3 (2)	C53B—C54B—C55B—C56B	0.6 (6)
C2B—N3B—C4B—C41B	177.60 (18)	C54B—C55B—C56B—C51B	−0.5 (6)
C2A—N1A—C5A—C51A	−175.95 (19)	N1A—C2A—C21A—C22A	−146.0 (2)
C2A—N1A—C5A—C4A	1.6 (2)	N1A—C2A—C21A—C26A	31.8 (3)
C5A—N1A—C2A—N3A	−1.5 (2)	N3A—C2A—C21A—C22A	36.8 (3)
C5A—N1A—C2A—C21A	−179.21 (19)	N3A—C2A—C21A—C26A	−145.5 (2)
C4A—N3A—C2A—N1A	0.8 (2)	N3A—C4A—C5A—N1A	−1.1 (2)
C4A—N3A—C2A—C21A	178.3 (2)	N3A—C4A—C5A—C51A	176.0 (2)
C2A—N3A—C4A—C5A	0.2 (2)	C41A—C4A—C5A—N1A	176.9 (2)
C2A—N3A—C4A—C41A	−177.95 (19)	C41A—C4A—C5A—C51A	−6.1 (4)
N1B—C2B—C21B—C22B	141.8 (2)	N3A—C4A—C41A—C42A	142.9 (2)
N1B—C2B—C21B—C26B	−38.8 (3)	N3A—C4A—C41A—C46A	−36.5 (3)
N3B—C2B—C21B—C22B	−45.3 (3)	C5A—C4A—C41A—C42A	−34.9 (4)
N3B—C2B—C21B—C26B	134.2 (2)	C5A—C4A—C41A—C46A	145.7 (2)
N3B—C4B—C5B—C51B	−177.1 (2)	N1A—C5A—C51A—C52A	−41.5 (3)
C41B—C4B—C5B—N1B	−176.8 (2)	N1A—C5A—C51A—C56A	135.7 (2)
C41B—C4B—C5B—C51B	5.3 (4)	C4A—C5A—C51A—C52A	141.8 (3)
N3B—C4B—C41B—C42B	−139.7 (2)	C4A—C5A—C51A—C56A	−41.0 (4)
N3B—C4B—C41B—C46B	38.5 (3)	C2A—C21A—C22A—Cl1A	−0.8 (3)
C5B—C4B—C41B—C42B	37.7 (3)	C2A—C21A—C22A—C23A	177.8 (2)
C5B—C4B—C41B—C46B	−144.1 (2)	C26A—C21A—C22A—Cl1A	−178.6 (2)
N3B—C4B—C5B—N1B	0.8 (2)	C26A—C21A—C22A—C23A	0.0 (4)
C4B—C5B—C51B—C52B	−133.0 (3)	C2A—C21A—C26A—C25A	−176.8 (2)
N1B—C5B—C51B—C52B	49.4 (3)	C22A—C21A—C26A—C25A	1.2 (4)
N1B—C5B—C51B—C56B	−128.2 (3)	Cl1A—C22A—C23A—C24A	177.4 (3)
C4B—C5B—C51B—C56B	49.5 (4)	C21A—C22A—C23A—C24A	−1.3 (5)
C2B—C21B—C26B—C25B	−179.5 (2)	C22A—C23A—C24A—C25A	1.4 (5)
C2B—C21B—C22B—Cl1B	−0.5 (3)	C23A—C24A—C25A—C26A	−0.2 (5)
C2B—C21B—C22B—C23B	179.4 (2)	C24A—C25A—C26A—C21A	−1.1 (5)
C26B—C21B—C22B—Cl1B	−179.97 (18)	C4A—C41A—C42A—C43A	178.7 (2)
C22B—C21B—C26B—C25B	−0.1 (3)	C46A—C41A—C42A—C43A	−2.0 (4)
C26B—C21B—C22B—C23B	0.0 (3)	C4A—C41A—C46A—C45A	−179.1 (2)
C21B—C22B—C23B—C24B	0.0 (3)	C42A—C41A—C46A—C45A	1.6 (4)
Cl1B—C22B—C23B—C24B	−180.00 (19)	C41A—C42A—C43A—C44A	1.3 (4)
C22B—C23B—C24B—C25B	0.0 (4)	C42A—C43A—C44A—C45A	−0.2 (5)
C23B—C24B—C25B—C26B	0.0 (4)	C43A—C44A—C45A—C46A	−0.2 (4)
C24B—C25B—C26B—C21B	0.1 (4)	C44A—C45A—C46A—C41A	−0.5 (4)
C4B—C41B—C42B—C43B	178.4 (2)	C5A—C51A—C52A—C53A	175.5 (2)
C46B—C41B—C42B—C43B	0.2 (4)	C56A—C51A—C52A—C53A	−1.8 (4)
C4B—C41B—C46B—C45B	−179.2 (2)	C5A—C51A—C56A—C55A	−176.2 (2)
C42B—C41B—C46B—C45B	−1.0 (4)	C52A—C51A—C56A—C55A	1.1 (4)
C41B—C42B—C43B—C44B	0.7 (4)	C51A—C52A—C53A—C54A	1.2 (4)
C42B—C43B—C44B—C45B	−0.7 (4)	C52A—C53A—C54A—C55A	0.0 (5)
C43B—C44B—C45B—C46B	0.0 (4)	C53A—C54A—C55A—C56A	−0.7 (5)
C44B—C45B—C46B—C41B	0.9 (4)	C54A—C55A—C56A—C51A	0.1 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z+1; (v) x+1, y, z; (vi) x, y−1, z; (vii) −x, −y+1, −z+1; (viii) x, y+1, z; (ix) −x+1, −y+2, −z; (x) −x+2, −y+1, −z; (xi) x−1, y+1, z; (xii) x+1, y−1, z; (xiii) −x+3, −y+2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N3B^v	0.84 (3)	2.14 (3)	2.961 (2)	170 (2)
N1B—H1B···N3A	0.85 (3)	2.07 (3)	2.895 (3)	163 (2)

Symmetry code: (v) x+1, y, z.