(E)-3-(4-Bromo-phen-yl)-3-[3-(4-bromo-phen-yl)-1H-pyrazol-1-yl]prop-2-enal.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(18)H(12)Br(2)N(2)O. In each mol-ecule, one of the bromo-phenyl rings lies almost in the plane of pyrazole unit [dihedral angles of 5.8 (3)° in the first mol-ecule and and 5.1 (3)° in the second] while the other ring is approximately perpendicular to it [dihedral angles of 80.3 (3) and 76.5 (3)°]. The crystal packing shows inter-molecular C-H⋯O inter-actions. The crystal studied was a racemic twin.

Related literature

For the pharmacological and medicinal properties of pyrazole derivatives, see: Baraldi et al. (1998 ▶); Bruno et al. (1990 ▶); Cottineau et al. (2002 ▶); Londershausen (1996 ▶); Chen & Li (1998 ▶); Mishra et al. (1998 ▶); Smith et al. (2001 ▶). For a related structure, see: Jin et al. (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H12Br2N2O

M = 432.12

Orthorhombic,

a = 9.2600 (3) Å

b = 9.3782 (3) Å

c = 37.9965 (4) Å

V = 3299.70 (15) Å3

Z = 8

Mo Kα radiation

μ = 4.92 mm−1

T = 293 K

0.30 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.319, T max = 0.455

17654 measured reflections

5353 independent reflections

3562 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.086

S = 1.01

5353 reflections

416 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.68 e Å−3

Absolute structure: Flack (1983 ▶), 1831 Friedel pairs

Flack parameter: 0.226 (12)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, (1997 ▶)); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054749/bt5143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054749/bt5143Isup2.hkl

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

C18H12Br2N2O	F(000) = 1696
Mr = 432.12	Dx = 1.740 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2356 reflections
a = 9.2600 (3) Å	θ = 2.1–26.7°
b = 9.3782 (3) Å	µ = 4.92 mm−1
c = 37.9965 (4) Å	T = 293 K
V = 3299.70 (15) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.16 mm

Bruker Kappa APEXII diffractometer	5353 independent reflections
Radiation source: fine-focus sealed tube	3562 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω and φ scans	θmax = 26.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→11
Tmin = 0.319, Tmax = 0.455	k = −11→8
17654 measured reflections	l = −47→28

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0332P)2 + 2.8025P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
5353 reflections	Δρmax = 0.94 e Å−3
416 parameters	Δρmin = −0.68 e Å−3
2 restraints	Absolute structure: Flack (1983), 1831 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.226 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
Br1A	1.06404 (10)	0.03442 (11)	1.04136 (2)	0.0845 (3)
Br1B	−0.30627 (8)	0.54380 (9)	0.52040 (2)	0.0701 (2)
Br2A	0.53252 (8)	0.16474 (8)	0.66987 (2)	0.0689 (2)
Br2B	0.20118 (8)	0.34086 (8)	0.888391 (19)	0.0687 (2)
O1A	0.4407 (6)	0.3862 (6)	0.94905 (14)	0.0893 (18)
O1B	0.2716 (6)	0.0770 (5)	0.61274 (14)	0.0782 (15)
N1A	0.6924 (5)	0.1737 (5)	0.84642 (15)	0.0441 (13)
N1B	0.0394 (5)	0.3223 (5)	0.71192 (13)	0.0386 (12)
N2A	0.7688 (5)	0.1414 (5)	0.87580 (13)	0.0394 (12)
N2B	−0.0373 (5)	0.3565 (5)	0.68274 (13)	0.0401 (12)
C3A	0.8905 (7)	0.0679 (6)	0.86725 (18)	0.0456 (16)
H3A	0.9595	0.0339	0.8829	0.055*
C3B	−0.1573 (6)	0.4349 (6)	0.69043 (19)	0.0427 (16)
H3B	−0.2241	0.4709	0.6745	0.051*
C4A	0.8933 (7)	0.0536 (6)	0.83279 (19)	0.0451 (16)
H4A	0.9637	0.0077	0.8195	0.054*
C4B	−0.1601 (6)	0.4502 (6)	0.72623 (17)	0.0409 (15)
H4B	−0.2292	0.4972	0.7397	0.049*
C5A	0.7689 (6)	0.1212 (6)	0.82008 (16)	0.0357 (14)
C5B	−0.0348 (7)	0.3788 (6)	0.73838 (16)	0.0358 (14)
C6A	0.7229 (7)	0.1875 (6)	0.90911 (18)	0.0466 (17)
C6B	0.0081 (6)	0.3060 (6)	0.64915 (17)	0.0390 (15)
C7A	0.8119 (7)	0.1444 (7)	0.93918 (16)	0.0429 (16)
C7B	−0.0733 (6)	0.3630 (7)	0.61901 (16)	0.0409 (16)
C8A	0.9017 (7)	0.2424 (7)	0.95476 (18)	0.0520 (17)
H8A	0.9111	0.3333	0.9452	0.062*
C8B	−0.1625 (7)	0.2773 (7)	0.59906 (18)	0.0468 (16)
H8B	−0.1745	0.1818	0.6050	0.056*
C9A	0.9776 (8)	0.2055 (8)	0.9845 (2)	0.063 (2)
H9A	1.0377	0.2725	0.9951	0.076*
C9B	−0.2332 (7)	0.3330 (7)	0.57053 (18)	0.0527 (17)
H9B	−0.2960	0.2759	0.5577	0.063*
C10A	0.9667 (7)	0.0750 (8)	0.99855 (18)	0.0523 (17)
C10B	−0.2125 (7)	0.4713 (7)	0.56087 (19)	0.0478 (17)
C11A	0.8816 (9)	−0.0234 (8)	0.9832 (2)	0.059 (2)
H11A	0.8749	−0.1140	0.9930	0.070*
C11B	−0.1234 (7)	0.5587 (7)	0.58027 (18)	0.0486 (17)
H11B	−0.1100	0.6535	0.5738	0.058*
C12A	0.8043 (8)	0.0080 (7)	0.9532 (3)	0.058 (2)
H12A	0.7477	−0.0615	0.9425	0.069*
C12B	−0.0553 (8)	0.5044 (7)	0.6090 (2)	0.053 (2)
H12B	0.0046	0.5631	0.6223	0.064*
C13A	0.6043 (7)	0.2674 (7)	0.91238 (19)	0.0581 (18)
H13A	0.5540	0.2924	0.8921	0.070*
C13B	0.1155 (7)	0.2129 (6)	0.64759 (17)	0.0480 (16)
H13	0.1556	0.1794	0.6685	0.058*
C14A	0.5513 (8)	0.3163 (7)	0.9454 (2)	0.063 (2)
H14A	0.6039	0.2936	0.9655	0.076*
C14B	0.1728 (8)	0.1613 (7)	0.61425 (19)	0.0554 (18)
H14	0.1320	0.1941	0.5934	0.067*
C15A	0.7154 (6)	0.1352 (6)	0.78364 (17)	0.0375 (15)
C15B	0.0164 (6)	0.3646 (6)	0.77424 (17)	0.0360 (14)
C16A	0.7845 (7)	0.0686 (6)	0.75603 (19)	0.0472 (17)
H16A	0.8673	0.0153	0.7604	0.057*
C16B	−0.0520 (7)	0.4315 (6)	0.80212 (18)	0.0428 (16)
H16B	−0.1355	0.4837	0.7978	0.051*
C17A	0.7334 (7)	0.0793 (6)	0.72186 (18)	0.0464 (16)
H17A	0.7822	0.0361	0.7033	0.056*
C17B	−0.0001 (7)	0.4232 (7)	0.83575 (18)	0.0494 (17)
H17B	−0.0479	0.4695	0.8540	0.059*
C18A	0.6105 (7)	0.1544 (6)	0.71609 (16)	0.0420 (15)
C18B	0.1237 (7)	0.3455 (6)	0.84255 (17)	0.0435 (15)
C19A	0.5396 (6)	0.2233 (7)	0.74279 (19)	0.0456 (16)
H19A	0.4566	0.2758	0.7381	0.055*
C19B	0.1903 (6)	0.2769 (7)	0.81560 (18)	0.0470 (17)
H19B	0.2726	0.2231	0.8201	0.056*
C20A	0.5924 (6)	0.2141 (6)	0.77660 (17)	0.0413 (15)
H20A	0.5451	0.2612	0.7948	0.050*
C20B	0.1383 (7)	0.2854 (6)	0.78198 (18)	0.0398 (15)
H20B	0.1858	0.2372	0.7640	0.048*

	U11	U22	U33	U12	U13	U23
Br1A	0.0906 (6)	0.1116 (6)	0.0512 (5)	0.0180 (5)	−0.0083 (5)	0.0153 (5)
Br1B	0.0723 (5)	0.0778 (5)	0.0601 (6)	0.0001 (4)	−0.0177 (4)	0.0176 (5)
Br2A	0.0836 (5)	0.0759 (5)	0.0474 (4)	0.0057 (4)	−0.0086 (4)	0.0055 (4)
Br2B	0.0748 (5)	0.0871 (5)	0.0442 (4)	0.0013 (5)	−0.0060 (4)	0.0059 (4)
O1A	0.096 (4)	0.116 (4)	0.056 (3)	0.053 (4)	−0.002 (3)	−0.022 (3)
O1B	0.082 (4)	0.077 (3)	0.075 (4)	0.032 (3)	0.016 (3)	−0.012 (3)
N1A	0.037 (3)	0.049 (3)	0.046 (4)	0.004 (3)	0.009 (3)	0.002 (3)
N1B	0.042 (3)	0.044 (3)	0.029 (3)	0.001 (2)	0.001 (2)	−0.001 (2)
N2A	0.040 (3)	0.044 (3)	0.035 (3)	0.003 (2)	0.003 (3)	−0.001 (2)
N2B	0.043 (3)	0.040 (3)	0.038 (3)	0.008 (3)	0.002 (3)	−0.006 (2)
C3A	0.046 (4)	0.044 (4)	0.047 (4)	0.001 (3)	−0.003 (3)	−0.012 (3)
C3B	0.033 (3)	0.036 (4)	0.059 (5)	0.009 (3)	−0.001 (3)	0.002 (3)
C4A	0.049 (4)	0.029 (3)	0.058 (5)	−0.001 (3)	0.003 (4)	−0.013 (4)
C4B	0.033 (3)	0.046 (4)	0.044 (4)	0.005 (3)	0.006 (3)	−0.002 (4)
C5A	0.033 (3)	0.030 (3)	0.044 (4)	−0.002 (3)	0.005 (3)	−0.001 (3)
C5B	0.045 (4)	0.025 (3)	0.038 (4)	−0.007 (3)	0.003 (3)	0.002 (3)
C6A	0.050 (4)	0.044 (4)	0.046 (5)	−0.003 (3)	0.007 (3)	−0.002 (3)
C6B	0.039 (3)	0.041 (4)	0.037 (4)	−0.006 (3)	−0.002 (3)	0.000 (3)
C7A	0.047 (4)	0.045 (4)	0.037 (4)	−0.004 (3)	0.002 (3)	0.002 (3)
C7B	0.045 (4)	0.041 (4)	0.037 (4)	0.004 (3)	0.004 (3)	−0.002 (3)
C8A	0.055 (4)	0.045 (4)	0.055 (4)	−0.004 (3)	−0.012 (4)	0.008 (3)
C8B	0.046 (4)	0.036 (3)	0.058 (4)	−0.009 (3)	−0.004 (3)	−0.002 (3)
C9A	0.057 (4)	0.067 (5)	0.066 (5)	−0.007 (4)	−0.007 (4)	−0.009 (4)
C9B	0.053 (4)	0.053 (4)	0.053 (4)	−0.004 (3)	−0.017 (4)	−0.009 (4)
C10A	0.050 (4)	0.059 (5)	0.048 (4)	0.005 (4)	0.004 (3)	0.006 (4)
C10B	0.046 (4)	0.047 (4)	0.050 (5)	0.002 (3)	−0.007 (3)	0.007 (3)
C11A	0.081 (5)	0.039 (4)	0.056 (5)	0.012 (4)	0.010 (4)	0.017 (4)
C11B	0.058 (4)	0.039 (4)	0.048 (4)	−0.005 (3)	0.000 (4)	0.003 (3)
C12A	0.074 (6)	0.034 (4)	0.064 (6)	−0.007 (3)	−0.001 (5)	0.002 (3)
C12B	0.059 (6)	0.054 (5)	0.046 (5)	−0.010 (3)	−0.013 (4)	−0.001 (3)
C13A	0.059 (5)	0.069 (4)	0.046 (4)	0.011 (4)	0.000 (3)	−0.008 (4)
C13B	0.056 (4)	0.049 (4)	0.039 (4)	0.009 (3)	−0.001 (3)	0.007 (3)
C14A	0.063 (5)	0.078 (5)	0.049 (4)	0.015 (4)	0.000 (3)	−0.012 (4)
C14B	0.063 (5)	0.056 (4)	0.048 (5)	0.010 (4)	0.006 (4)	−0.003 (4)
C15A	0.040 (4)	0.032 (3)	0.041 (4)	−0.008 (3)	0.010 (3)	−0.004 (3)
C15B	0.038 (3)	0.028 (3)	0.042 (4)	−0.003 (3)	0.007 (3)	0.001 (3)
C16A	0.037 (4)	0.046 (4)	0.058 (5)	0.006 (3)	0.003 (3)	−0.006 (4)
C16B	0.043 (4)	0.040 (4)	0.045 (4)	0.004 (3)	−0.002 (3)	−0.004 (4)
C17A	0.052 (4)	0.042 (4)	0.046 (4)	0.004 (3)	0.003 (3)	−0.006 (3)
C17B	0.050 (4)	0.058 (4)	0.040 (4)	0.005 (4)	0.009 (3)	−0.015 (3)
C18A	0.048 (4)	0.035 (3)	0.043 (4)	−0.001 (3)	0.000 (3)	0.007 (3)
C18B	0.045 (4)	0.045 (4)	0.040 (4)	−0.006 (3)	0.000 (3)	0.004 (3)
C19A	0.039 (4)	0.046 (4)	0.052 (5)	0.000 (3)	0.005 (3)	0.003 (3)
C19B	0.039 (4)	0.048 (4)	0.054 (5)	0.006 (3)	0.010 (3)	0.009 (3)
C20A	0.035 (3)	0.047 (4)	0.043 (4)	0.006 (3)	0.009 (3)	−0.001 (3)
C20B	0.046 (3)	0.036 (4)	0.038 (4)	0.002 (3)	0.007 (3)	−0.001 (3)

Br1A—C10A	1.898 (7)	C8B—H8B	0.9300
Br1B—C10B	1.892 (7)	C9A—C10A	1.339 (9)
Br2A—C18A	1.901 (6)	C9A—H9A	0.9300
Br2B—C18B	1.884 (6)	C9B—C10B	1.361 (8)
O1A—C14A	1.224 (8)	C9B—H9B	0.9300
O1B—C14B	1.210 (8)	C10A—C11A	1.347 (10)
N1A—C5A	1.321 (8)	C10B—C11B	1.377 (9)
N1A—N2A	1.356 (7)	C11A—C12A	1.375 (12)
N1B—C5B	1.328 (7)	C11A—H11A	0.9300
N1B—N2B	1.355 (6)	C11B—C12B	1.361 (10)
N2A—N1A	1.356 (7)	C11B—H11B	0.9300
N2A—C3A	1.361 (8)	C12A—H12A	0.9300
N2A—C6A	1.403 (8)	C12B—H12B	0.9300
N2B—N1B	1.355 (6)	C13A—C14A	1.424 (10)
N2B—C3B	1.363 (7)	C13A—H13A	0.9300
N2B—C6B	1.425 (8)	C13B—C14B	1.456 (9)
C3A—C4A	1.316 (9)	C13B—H13	0.9300
C3A—H3A	0.9300	C14A—H14A	0.9300
C3B—C4B	1.368 (8)	C14B—H14	0.9300
C3B—H3B	0.9300	C15A—C16A	1.379 (8)
C4A—C5A	1.401 (9)	C15A—C20A	1.384 (8)
C4A—H4A	0.9300	C15B—C20B	1.382 (8)
C4B—C5B	1.416 (9)	C15B—C16B	1.384 (8)
C4B—H4B	0.9300	C16A—C17A	1.385 (9)
C5A—N1A	1.321 (8)	C16A—H16A	0.9300
C5A—C15A	1.477 (8)	C16B—C17B	1.367 (9)
C5B—N1B	1.328 (7)	C16B—H16B	0.9300
C5B—C15B	1.449 (8)	C17A—C18A	1.356 (8)
C6A—C13A	1.336 (8)	C17A—H17A	0.9300
C6A—C7A	1.465 (9)	C17B—C18B	1.383 (9)
C6B—C13B	1.325 (8)	C17B—H17B	0.9300
C6B—C7B	1.471 (8)	C18A—C19A	1.371 (9)
C7A—C8A	1.374 (9)	C18B—C19B	1.358 (9)
C7A—C12A	1.388 (9)	C19A—C20A	1.377 (9)
C7B—C8B	1.379 (8)	C19A—H19A	0.9300
C7B—C12B	1.389 (9)	C19B—C20B	1.367 (9)
C8A—C9A	1.375 (9)	C19B—H19B	0.9300
C8A—H8A	0.9300	C20A—H20A	0.9300
C8B—C9B	1.370 (9)	C20B—H20B	0.9300
C5A—N1A—N2A	105.1 (5)	C10A—C11A—C12A	121.1 (6)
C5B—N1B—N2B	104.7 (5)	C10A—C11A—H11A	119.4
N1A—N2A—C3A	110.4 (5)	C12A—C11A—H11A	119.4
N1A—N2A—C6A	121.0 (5)	C12B—C11B—C10B	119.0 (6)
C3A—N2A—C6A	128.5 (6)	C12B—C11B—H11B	120.5
N1B—N2B—C3B	112.3 (5)	C10B—C11B—H11B	120.5
N1B—N2B—C6B	120.0 (5)	C11A—C12A—C7A	119.3 (7)
C3B—N2B—C6B	127.7 (5)	C11A—C12A—H12A	120.4
C4A—C3A—N2A	107.8 (6)	C7A—C12A—H12A	120.4
C4A—C3A—H3A	126.1	C11B—C12B—C7B	121.4 (7)
N2A—C3A—H3A	126.1	C11B—C12B—H12B	119.3
N2B—C3B—C4B	106.6 (6)	C7B—C12B—H12B	119.3
N2B—C3B—H3B	126.7	C6A—C13A—C14A	123.1 (7)
C4B—C3B—H3B	126.7	C6A—C13A—H13A	118.5
C3A—C4A—C5A	106.3 (6)	C14A—C13A—H13A	118.5
C3A—C4A—H4A	126.8	C6B—C13B—C14B	122.1 (6)
C5A—C4A—H4A	126.8	C6B—C13B—H13	118.9
C3B—C4B—C5B	105.0 (6)	C14B—C13B—H13	118.9
C3B—C4B—H4B	127.5	O1A—C14A—C13A	124.0 (7)
C5B—C4B—H4B	127.5	O1A—C14A—H14A	118.0
N1A—C5A—C4A	110.4 (6)	C13A—C14A—H14A	118.0
N1A—C5A—C4A	110.4 (6)	O1B—C14B—C13B	122.3 (7)
N1A—C5A—C15A	119.8 (5)	O1B—C14B—H14	118.9
N1A—C5A—C15A	119.8 (5)	C13B—C14B—H14	118.9
C4A—C5A—C15A	129.8 (6)	C16A—C15A—C20A	118.5 (6)
N1B—C5B—C4B	111.4 (6)	C16A—C15A—C5A	121.2 (5)
N1B—C5B—C4B	111.4 (6)	C20A—C15A—C5A	120.3 (6)
N1B—C5B—C15B	120.4 (5)	C20B—C15B—C16B	117.0 (6)
N1B—C5B—C15B	120.4 (5)	C20B—C15B—C5B	121.1 (6)
C4B—C5B—C15B	128.2 (6)	C16B—C15B—C5B	121.9 (6)
C13A—C6A—N2A	120.4 (6)	C15A—C16A—C17A	121.4 (6)
C13A—C6A—C7A	123.0 (6)	C15A—C16A—H16A	119.3
N2A—C6A—C7A	116.6 (5)	C17A—C16A—H16A	119.3
C13B—C6B—N2B	118.7 (6)	C17B—C16B—C15B	121.9 (6)
C13B—C6B—C7B	126.1 (6)	C17B—C16B—H16B	119.1
N2B—C6B—C7B	115.2 (5)	C15B—C16B—H16B	119.1
C8A—C7A—C12A	118.8 (6)	C18A—C17A—C16A	118.4 (6)
C8A—C7A—C6A	119.4 (6)	C18A—C17A—H17A	120.8
C12A—C7A—C6A	121.7 (7)	C16A—C17A—H17A	120.8
C8B—C7B—C12B	118.5 (6)	C16B—C17B—C18B	119.7 (6)
C8B—C7B—C6B	121.5 (6)	C16B—C17B—H17B	120.1
C12B—C7B—C6B	119.8 (6)	C18B—C17B—H17B	120.1
C7A—C8A—C9A	119.7 (6)	C17A—C18A—C19A	121.8 (6)
C7A—C8A—H8A	120.2	C17A—C18A—Br2A	119.7 (5)
C9A—C8A—H8A	120.2	C19A—C18A—Br2A	118.5 (5)
C9B—C8B—C7B	120.0 (6)	C19B—C18B—C17B	119.0 (6)
C9B—C8B—H8B	120.0	C19B—C18B—Br2B	120.9 (5)
C7B—C8B—H8B	120.0	C17B—C18B—Br2B	120.0 (5)
C10A—C9A—C8A	121.3 (7)	C18A—C19A—C20A	119.4 (6)
C10A—C9A—H9A	119.4	C18A—C19A—H19A	120.3
C8A—C9A—H9A	119.4	C20A—C19A—H19A	120.3
C10B—C9B—C8B	120.6 (6)	C18B—C19B—C20B	121.1 (6)
C10B—C9B—H9B	119.7	C18B—C19B—H19B	119.4
C8B—C9B—H9B	119.7	C20B—C19B—H19B	119.4
C9A—C10A—C11A	119.8 (7)	C19A—C20A—C15A	120.4 (6)
C9A—C10A—Br1A	119.3 (6)	C19A—C20A—H20A	119.8
C11A—C10A—Br1A	120.8 (6)	C15A—C20A—H20A	119.8
C9B—C10B—C11B	120.5 (6)	C19B—C20B—C15B	121.2 (6)
C9B—C10B—Br1B	119.8 (5)	C19B—C20B—H20B	119.4
C11B—C10B—Br1B	119.7 (5)	C15B—C20B—H20B	119.4
C5A—N1A—N2A—C3A	−0.8 (6)	C8B—C9B—C10B—Br1B	177.8 (5)
C5A—N1A—N2A—C6A	176.8 (5)	C9A—C10A—C11A—C12A	−0.5 (12)
C5B—N1B—N2B—C3B	0.7 (6)	Br1A—C10A—C11A—C12A	176.3 (6)
C5B—N1B—N2B—C6B	−176.9 (5)	C9B—C10B—C11B—C12B	0.7 (10)
N1A—N2A—C3A—C4A	0.4 (7)	Br1B—C10B—C11B—C12B	−179.1 (6)
N1A—N2A—C3A—C4A	0.4 (7)	C10A—C11A—C12A—C7A	−1.5 (12)
C6A—N2A—C3A—C4A	−176.9 (6)	C8A—C7A—C12A—C11A	2.9 (11)
N1B—N2B—C3B—C4B	−1.1 (6)	C6A—C7A—C12A—C11A	−174.8 (7)
N1B—N2B—C3B—C4B	−1.1 (6)	C10B—C11B—C12B—C7B	0.3 (11)
C6B—N2B—C3B—C4B	176.3 (6)	C8B—C7B—C12B—C11B	0.0 (11)
N2A—C3A—C4A—C5A	0.2 (7)	C6B—C7B—C12B—C11B	176.8 (7)
N2B—C3B—C4B—C5B	0.9 (7)	N2A—C6A—C13A—C14A	179.3 (6)
N2A—N1A—C5A—C4A	0.9 (6)	C7A—C6A—C13A—C14A	−1.2 (10)
N2A—N1A—C5A—C15A	178.9 (5)	N2B—C6B—C13B—C14B	−177.0 (5)
C3A—C4A—C5A—N1A	−0.7 (7)	C7B—C6B—C13B—C14B	4.0 (10)
C3A—C4A—C5A—C15A	−178.5 (6)	C6A—C13A—C14A—O1A	−177.9 (7)
N2B—N1B—C5B—C4B	−0.1 (6)	C6B—C13B—C14B—O1B	179.4 (7)
N2B—N1B—C5B—C15B	−179.4 (5)	N1A—C5A—C15A—C16A	−173.0 (5)
C3B—C4B—C5B—N1B	−0.5 (7)	C4A—C5A—C15A—C16A	4.7 (9)
C3B—C4B—C5B—N1B	−0.5 (7)	N1A—C5A—C15A—C20A	5.9 (8)
C3B—C4B—C5B—C15B	178.7 (6)	C4A—C5A—C15A—C20A	−176.4 (6)
N1A—N2A—C6A—C13A	−1.6 (8)	N1B—C5B—C15B—C20B	−3.8 (8)
C3A—N2A—C6A—C13A	175.4 (6)	C4B—C5B—C15B—C20B	177.0 (6)
N1A—N2A—C6A—C7A	178.9 (5)	N1B—C5B—C15B—C16B	174.8 (5)
C3A—N2A—C6A—C7A	−4.1 (9)	C4B—C5B—C15B—C16B	−4.4 (9)
N1B—N2B—C6B—C13B	7.6 (8)	C20A—C15A—C16A—C17A	0.0 (8)
C3B—N2B—C6B—C13B	−169.6 (6)	C5A—C15A—C16A—C17A	178.9 (6)
N1B—N2B—C6B—C7B	−173.3 (5)	C20B—C15B—C16B—C17B	1.5 (9)
C3B—N2B—C6B—C7B	9.5 (8)	C5B—C15B—C16B—C17B	−177.1 (6)
C13A—C6A—C7A—C8A	−75.2 (8)	C15A—C16A—C17A—C18A	−1.7 (9)
N2A—C6A—C7A—C8A	104.3 (7)	C15B—C16B—C17B—C18B	−0.3 (10)
C13A—C6A—C7A—C12A	102.4 (9)	C16A—C17A—C18A—C19A	2.4 (9)
N2A—C6A—C7A—C12A	−78.1 (8)	C16A—C17A—C18A—Br2A	−177.3 (5)
C13B—C6B—C7B—C8B	67.2 (9)	C16B—C17B—C18B—C19B	−1.1 (9)
N2B—C6B—C7B—C8B	−111.8 (6)	C16B—C17B—C18B—Br2B	177.0 (5)
C13B—C6B—C7B—C12B	−109.5 (8)	C17A—C18A—C19A—C20A	−1.3 (9)
N2B—C6B—C7B—C12B	71.5 (8)	Br2A—C18A—C19A—C20A	178.4 (5)
C12A—C7A—C8A—C9A	−2.4 (10)	C17B—C18B—C19B—C20B	1.1 (9)
C6A—C7A—C8A—C9A	175.4 (6)	Br2B—C18B—C19B—C20B	−176.9 (5)
C12B—C7B—C8B—C9B	−1.3 (10)	C18A—C19A—C20A—C15A	−0.5 (9)
C6B—C7B—C8B—C9B	−178.0 (6)	C16A—C15A—C20A—C19A	1.1 (8)
C7A—C8A—C9A—C10A	0.5 (11)	C5A—C15A—C20A—C19A	−177.8 (5)
C7B—C8B—C9B—C10B	2.4 (10)	C18B—C19B—C20B—C15B	0.2 (9)
C8A—C9A—C10A—C11A	1.0 (11)	C16B—C15B—C20B—C19B	−1.5 (8)
C8A—C9A—C10A—Br1A	−175.8 (5)	C5B—C15B—C20B—C19B	177.2 (5)
C8B—C9B—C10B—C11B	−2.0 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···N1A	0.93	2.43	2.779 (9)	102
C13B—H13···N1B	0.93	2.38	2.743 (8)	103
C8B—H8B···O1Bi	0.93	2.50	3.419 (8)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8B—H8B⋯O1Bi	0.93	2.50	3.419 (8)	172

Symmetry code: (i) .