(1E)-1-(3-Bromo-phen-yl)ethanone 2,4-di-nitro-phenyl-hydrazone.

The title compound, C(14)H(11)BrN(4)O(4), contains 3-bromo-phenyl and 2,4-dinitro-phenyl groups on opposite sides of a hydrazone unit and crystallizes with two mol-ecules in the asymmetric unit. The dihedral angles between the two ring systems in each mol-ecule are 2.0 (1) and 2.5 (4)°. Weak C-H⋯O hydrogen bonds and weak π-π stacking inter-actions [centroid-centroid distance = 3.7269 (14) Å] help to establish the packing. Intra-molecular N-H⋯O hydrogen bonds are also observed. On one of the rings, the Br atom is disordered over two equivalent positions of the phenyl ring [occupancy ratio 0.8734 (10):0.1266 (10).

Related literature

For background to Schiff bases and their complexes, see: Baughman et al. (2004 ▶); El-Seify et al. (2006 ▶); Liang et al. (2007 ▶); Okabe et al. (1993 ▶); Zare et al. (2005 ▶). For related structures, see: Bolte & Dill, (1998 ▶); Fan et al. (2004 ▶); Ji et al. (2010 ▶); Kia et al. (2009 ▶); Motherwell & Ramsay, (2007 ▶); Shan et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11BrN4O4

M = 379.18

Triclinic,

a = 7.7546 (9) Å

b = 13.4362 (15) Å

c = 14.1884 (16) Å

α = 91.894 (2)°

β = 90.553 (2)°

γ = 97.128 (2)°

V = 1466.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.83 mm−1

T = 100 K

0.55 × 0.55 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.547, T max = 0.746

16795 measured reflections

8581 independent reflections

6680 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.04

8581 reflections

428 parameters

2 restraints

H-atom parameters constrained

Δρmax = 1.44 e Å−3

Δρmin = −0.77 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037980/bv2160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037980/bv2160Isup2.hkl

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

C14H11BrN4O4	Z = 4
Mr = 379.18	F(000) = 760
Triclinic, P1	Dx = 1.718 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7546 (9) Å	Cell parameters from 5432 reflections
b = 13.4362 (15) Å	θ = 2.7–30.8°
c = 14.1884 (16) Å	µ = 2.83 mm−1
α = 91.894 (2)°	T = 100 K
β = 90.553 (2)°	Block, orange
γ = 97.128 (2)°	0.55 × 0.55 × 0.24 mm
V = 1466.0 (3) Å3

Bruker APEXII CCD diffractometer	8581 independent reflections
Radiation source: fine-focus sealed tube	6680 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 31.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.547, Tmax = 0.746	k = −19→19
16795 measured reflections	l = −20→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.049P)2 + 0.9159P] where P = (Fo2 + 2Fc2)/3
8581 reflections	(Δ/σ)max = 0.002
428 parameters	Δρmax = 1.44 e Å−3
2 restraints	Δρmin = −0.77 e Å−3

Experimental. 2010-03-28 # Formatted by publCIF 2010-08-17 # Formatted by IUCr publCIF system

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C11B	0.3320 (3)	0.11977 (16)	0.42870 (18)	0.0279 (5)	0.8734 (10)
C13B	0.4862 (3)	0.17310 (18)	0.56961 (15)	0.0281 (5)	0.8734 (10)
H13B	0.5206	0.1596	0.6319	0.034*	0.8734 (10)
C11C	0.3320 (3)	0.11977 (16)	0.42870 (18)	0.0279 (5)	0.1266 (10)
H11C	0.2387	0.0610	0.3838	0.034*	0.1266 (10)
C13C	0.4862 (3)	0.17310 (18)	0.56961 (15)	0.0281 (5)	0.1266 (10)
Br2B	0.19142 (4)	0.02208 (2)	0.36023 (3)	0.04126 (11)	0.8734 (10)
Br2C	0.5634 (3)	0.13884 (16)	0.68483 (14)	0.0364 (7)	0.1266 (10)
O1B	0.7504 (2)	0.67942 (12)	0.30264 (11)	0.0236 (3)
O2B	0.9336 (2)	0.81206 (12)	0.32857 (12)	0.0291 (4)
O3B	1.2253 (2)	0.88614 (12)	0.61872 (12)	0.0276 (4)
O4B	1.2248 (2)	0.77225 (13)	0.72350 (11)	0.0265 (3)
N1B	0.7215 (2)	0.53546 (13)	0.42320 (12)	0.0171 (3)
H1B	0.6906	0.5510	0.3677	0.021*
N2B	0.6603 (2)	0.44461 (13)	0.45865 (13)	0.0178 (3)
N3B	0.8600 (2)	0.73102 (13)	0.35350 (12)	0.0196 (4)
N4B	1.1765 (2)	0.80244 (14)	0.64777 (13)	0.0198 (4)
C1B	0.8319 (3)	0.60103 (15)	0.47668 (14)	0.0159 (4)
C2B	0.9025 (3)	0.69629 (15)	0.44510 (14)	0.0161 (4)
C3B	1.0139 (3)	0.76242 (15)	0.50129 (15)	0.0172 (4)
H3B	1.0591	0.8263	0.4793	0.021*
C4B	1.0576 (3)	0.73365 (15)	0.58945 (15)	0.0175 (4)
C5B	0.9929 (3)	0.64026 (15)	0.62373 (15)	0.0180 (4)
H5B	1.0254	0.6220	0.6849	0.022*
C6B	0.8825 (3)	0.57554 (15)	0.56820 (14)	0.0171 (4)
H6B	0.8386	0.5120	0.5915	0.021*
C7B	0.5594 (3)	0.38472 (15)	0.40366 (15)	0.0176 (4)
C8B	0.5111 (3)	0.41146 (17)	0.30597 (16)	0.0245 (5)
H6	0.4551	0.4730	0.3090	0.037*
H7	0.4306	0.3566	0.2772	0.037*
H8	0.6161	0.4223	0.2679	0.037*
C9B	0.4959 (3)	0.28630 (15)	0.44326 (16)	0.0189 (4)
C10B	0.3893 (3)	0.21275 (16)	0.39073 (17)	0.0225 (4)
H10B	0.3554	0.2248	0.3295	0.027*
C12B	0.3816 (3)	0.10017 (17)	0.52082 (19)	0.0291 (5)
H12B	0.3434	0.0379	0.5482	0.035*
C14B	0.5455 (3)	0.26506 (16)	0.53498 (16)	0.0226 (4)
H14B	0.6185	0.3133	0.5724	0.027*
Br1A	0.46515 (3)	0.585783 (17)	0.117323 (18)	0.02724 (7)
O1A	1.1072 (2)	1.23013 (12)	0.17885 (11)	0.0250 (3)
O2A	1.2017 (2)	1.38349 (12)	0.14856 (12)	0.0279 (4)
O3A	1.1250 (2)	1.52151 (13)	−0.14936 (13)	0.0300 (4)
O4A	0.9604 (3)	1.43670 (13)	−0.25602 (12)	0.0320 (4)
N1A	0.9017 (2)	1.11916 (13)	0.05847 (13)	0.0191 (3)
H1A	0.9406	1.1219	0.1156	0.023*
N2A	0.8042 (2)	1.03459 (13)	0.02230 (13)	0.0199 (4)
N3A	1.1202 (2)	1.30168 (14)	0.12536 (13)	0.0200 (4)
N4A	1.0306 (3)	1.44583 (15)	−0.17722 (14)	0.0241 (4)
C1A	0.9364 (3)	1.19896 (16)	0.00283 (15)	0.0185 (4)
C2A	1.0392 (3)	1.28937 (16)	0.03282 (15)	0.0179 (4)
C3A	1.0704 (3)	1.37046 (16)	−0.02584 (16)	0.0201 (4)
H3A	1.1401	1.4304	−0.0047	0.024*
C4A	0.9983 (3)	1.36193 (16)	−0.11485 (16)	0.0210 (4)
C5A	0.8957 (3)	1.27486 (17)	−0.14749 (16)	0.0233 (4)
H5A	0.8470	1.2710	−0.2094	0.028*
C6A	0.8655 (3)	1.19486 (17)	−0.09004 (15)	0.0223 (4)
H6A	0.7960	1.1356	−0.1127	0.027*
C7A	0.7589 (3)	0.96430 (16)	0.08055 (15)	0.0204 (4)
C8A	0.8080 (5)	0.9730 (2)	0.18295 (19)	0.0453 (8)
H8A	0.7673	1.0332	0.2114	0.068*
H8B	0.9347	0.9780	0.1898	0.068*
H8C	0.7543	0.9136	0.2148	0.068*
C9A	0.6534 (3)	0.87396 (16)	0.03918 (15)	0.0183 (4)
C10A	0.6164 (3)	0.78681 (16)	0.09002 (15)	0.0200 (4)
H10A	0.6583	0.7845	0.1530	0.024*
C11A	0.5178 (3)	0.70347 (16)	0.04771 (16)	0.0204 (4)
C12A	0.4544 (3)	0.70369 (17)	−0.04363 (16)	0.0237 (4)
H12A	0.3871	0.6460	−0.0713	0.028*
C13A	0.4918 (3)	0.79094 (17)	−0.09411 (16)	0.0232 (4)
H13A	0.4496	0.7928	−0.1570	0.028*
C14A	0.5887 (3)	0.87411 (17)	−0.05387 (15)	0.0212 (4)
H14A	0.6127	0.9328	−0.0894	0.025*

	U11	U22	U33	U12	U13	U23
C11B	0.0214 (11)	0.0159 (10)	0.0454 (15)	−0.0015 (8)	−0.0004 (10)	−0.0014 (9)
C13B	0.0296 (12)	0.0218 (11)	0.0332 (13)	0.0029 (9)	0.0039 (10)	0.0080 (9)
C11C	0.0214 (11)	0.0159 (10)	0.0454 (15)	−0.0015 (8)	−0.0004 (10)	−0.0014 (9)
C13C	0.0296 (12)	0.0218 (11)	0.0332 (13)	0.0029 (9)	0.0039 (10)	0.0080 (9)
Br2B	0.03745 (18)	0.01748 (14)	0.0650 (2)	−0.00971 (11)	−0.01999 (15)	−0.00010 (13)
Br2C	0.0462 (13)	0.0301 (11)	0.0300 (11)	−0.0101 (8)	−0.0098 (9)	0.0181 (8)
O1B	0.0299 (8)	0.0207 (8)	0.0189 (7)	−0.0016 (6)	−0.0053 (6)	0.0013 (6)
O2B	0.0428 (10)	0.0198 (8)	0.0217 (8)	−0.0101 (7)	−0.0024 (7)	0.0078 (6)
O3B	0.0326 (9)	0.0194 (8)	0.0283 (9)	−0.0068 (6)	−0.0036 (7)	−0.0008 (6)
O4B	0.0268 (8)	0.0307 (9)	0.0207 (8)	−0.0016 (7)	−0.0068 (6)	0.0010 (7)
N1B	0.0200 (8)	0.0139 (8)	0.0165 (8)	−0.0017 (6)	−0.0017 (7)	0.0031 (6)
N2B	0.0185 (8)	0.0137 (8)	0.0205 (9)	−0.0011 (6)	0.0012 (7)	0.0023 (6)
N3B	0.0252 (9)	0.0164 (8)	0.0167 (8)	0.0007 (7)	0.0006 (7)	0.0010 (7)
N4B	0.0167 (8)	0.0199 (9)	0.0217 (9)	−0.0012 (6)	−0.0006 (7)	−0.0029 (7)
C1B	0.0162 (9)	0.0152 (9)	0.0159 (9)	0.0004 (7)	0.0021 (7)	0.0004 (7)
C2B	0.0191 (9)	0.0149 (9)	0.0140 (9)	0.0001 (7)	−0.0004 (7)	0.0025 (7)
C3B	0.0174 (9)	0.0140 (9)	0.0197 (10)	−0.0005 (7)	0.0021 (7)	0.0005 (7)
C4B	0.0160 (9)	0.0167 (9)	0.0187 (10)	−0.0012 (7)	−0.0006 (7)	−0.0017 (7)
C5B	0.0189 (9)	0.0177 (9)	0.0173 (9)	0.0015 (7)	0.0000 (7)	0.0023 (7)
C6B	0.0188 (9)	0.0146 (9)	0.0176 (9)	0.0004 (7)	0.0003 (7)	0.0021 (7)
C7B	0.0166 (9)	0.0153 (9)	0.0204 (10)	0.0001 (7)	0.0007 (7)	0.0020 (7)
C8B	0.0285 (11)	0.0208 (11)	0.0221 (11)	−0.0059 (8)	−0.0054 (9)	0.0047 (8)
C9B	0.0160 (9)	0.0152 (9)	0.0255 (11)	0.0012 (7)	0.0027 (8)	0.0009 (8)
C10B	0.0186 (10)	0.0168 (10)	0.0314 (12)	0.0001 (8)	−0.0006 (8)	−0.0012 (8)
C12B	0.0275 (12)	0.0163 (10)	0.0437 (15)	0.0014 (8)	0.0060 (10)	0.0070 (10)
C14B	0.0231 (10)	0.0182 (10)	0.0260 (11)	−0.0001 (8)	0.0016 (9)	0.0017 (8)
Br1A	0.02909 (13)	0.01787 (11)	0.03320 (13)	−0.00395 (8)	−0.00194 (9)	0.00412 (9)
O1A	0.0301 (9)	0.0221 (8)	0.0220 (8)	−0.0007 (6)	−0.0029 (6)	0.0035 (6)
O2A	0.0280 (9)	0.0207 (8)	0.0326 (9)	−0.0055 (6)	−0.0078 (7)	−0.0011 (7)
O3A	0.0301 (9)	0.0219 (8)	0.0375 (10)	−0.0004 (7)	0.0038 (7)	0.0078 (7)
O4A	0.0447 (11)	0.0289 (9)	0.0232 (9)	0.0065 (8)	0.0014 (8)	0.0064 (7)
N1A	0.0214 (9)	0.0170 (8)	0.0177 (8)	−0.0024 (7)	−0.0026 (7)	−0.0003 (7)
N2A	0.0196 (9)	0.0176 (8)	0.0213 (9)	−0.0016 (7)	−0.0006 (7)	−0.0016 (7)
N3A	0.0177 (8)	0.0205 (9)	0.0215 (9)	0.0016 (7)	−0.0003 (7)	−0.0005 (7)
N4A	0.0260 (10)	0.0228 (9)	0.0247 (10)	0.0061 (7)	0.0072 (8)	0.0046 (8)
C1A	0.0183 (9)	0.0169 (9)	0.0201 (10)	0.0016 (7)	0.0033 (8)	0.0003 (8)
C2A	0.0174 (9)	0.0188 (10)	0.0174 (10)	0.0020 (7)	−0.0001 (7)	−0.0007 (7)
C3A	0.0186 (10)	0.0174 (10)	0.0243 (11)	0.0022 (7)	0.0037 (8)	0.0000 (8)
C4A	0.0216 (10)	0.0194 (10)	0.0227 (11)	0.0034 (8)	0.0049 (8)	0.0052 (8)
C5A	0.0254 (11)	0.0249 (11)	0.0195 (10)	0.0026 (8)	0.0014 (8)	0.0007 (8)
C6A	0.0246 (11)	0.0208 (10)	0.0205 (10)	−0.0010 (8)	0.0005 (8)	−0.0008 (8)
C7A	0.0245 (11)	0.0171 (10)	0.0194 (10)	0.0025 (8)	−0.0028 (8)	−0.0003 (8)
C8A	0.088 (2)	0.0196 (12)	0.0236 (13)	−0.0116 (13)	−0.0209 (14)	0.0033 (10)
C9A	0.0182 (9)	0.0169 (9)	0.0198 (10)	0.0025 (7)	−0.0006 (8)	−0.0014 (8)
C10A	0.0206 (10)	0.0194 (10)	0.0197 (10)	0.0016 (8)	−0.0021 (8)	0.0008 (8)
C11A	0.0193 (10)	0.0170 (10)	0.0245 (11)	0.0006 (7)	0.0013 (8)	0.0006 (8)
C12A	0.0203 (10)	0.0230 (11)	0.0268 (11)	0.0001 (8)	−0.0018 (8)	−0.0038 (9)
C13A	0.0235 (11)	0.0279 (11)	0.0175 (10)	0.0016 (8)	−0.0040 (8)	−0.0023 (8)
C14A	0.0248 (10)	0.0203 (10)	0.0185 (10)	0.0024 (8)	−0.0012 (8)	0.0016 (8)

C11B—C10B	1.400 (3)	Br1A—C11A	1.896 (2)
C11B—C12B	1.401 (4)	O1A—N3A	1.239 (2)
C11B—Br2B	1.843 (2)	O2A—N3A	1.231 (2)
C11B—H11C	1.1703	O3A—N4A	1.229 (3)
C13B—C12B	1.358 (3)	O4A—N4A	1.234 (3)
C13B—C14B	1.372 (3)	N1A—C1A	1.354 (3)
C13B—H13B	0.9500	N1A—N2A	1.366 (2)
O1B—N3B	1.238 (2)	N1A—H1A	0.8599
O2B—N3B	1.229 (2)	N2A—C7A	1.294 (3)
O3B—N4B	1.227 (2)	N3A—C2A	1.446 (3)
O4B—N4B	1.232 (2)	N4A—C4A	1.455 (3)
N1B—C1B	1.357 (3)	C1A—C2A	1.418 (3)
N1B—N2B	1.367 (2)	C1A—C6A	1.419 (3)
N1B—H1B	0.8604	C2A—C3A	1.392 (3)
N2B—C7B	1.288 (3)	C3A—C4A	1.372 (3)
N3B—C2B	1.444 (3)	C3A—H3A	0.9500
N4B—C4B	1.454 (3)	C4A—C5A	1.394 (3)
C1B—C2B	1.417 (3)	C5A—C6A	1.369 (3)
C1B—C6B	1.418 (3)	C5A—H5A	0.9500
C2B—C3B	1.386 (3)	C6A—H6A	0.9500
C3B—C4B	1.373 (3)	C7A—C9A	1.478 (3)
C3B—H3B	0.9500	C7A—C8A	1.496 (3)
C4B—C5B	1.397 (3)	C8A—H8A	0.9800
C5B—C6B	1.366 (3)	C8A—H8B	0.9800
C5B—H5B	0.9500	C8A—H8C	0.9800
C6B—H6B	0.9500	C9A—C10A	1.396 (3)
C7B—C9B	1.483 (3)	C9A—C14A	1.408 (3)
C7B—C8B	1.499 (3)	C10A—C11A	1.390 (3)
C8B—H6	0.9800	C10A—H10A	0.9500
C8B—H7	0.9800	C11A—C12A	1.382 (3)
C8B—H8	0.9800	C12A—C13A	1.395 (3)
C9B—C10B	1.397 (3)	C12A—H12A	0.9500
C9B—C14B	1.402 (3)	C13A—C14A	1.372 (3)
C10B—H10B	0.9299	C13A—H13A	0.9500
C12B—H12B	0.9500	C14A—H14A	0.9500
C14B—H14B	0.9500
C10B—C11B—C12B	119.6 (2)	C9B—C14B—H14B	120.7
C10B—C11B—Br2B	121.40 (19)	C1A—N1A—N2A	118.89 (18)
C12B—C11B—Br2B	118.98 (17)	C1A—N1A—H1A	120.3
C10B—C11B—H11C	119.1	N2A—N1A—H1A	120.8
C12B—C11B—H11C	121.2	C7A—N2A—N1A	116.76 (18)
C12B—C13B—C14B	124.4 (2)	O2A—N3A—O1A	121.74 (19)
C12B—C13B—H13B	117.8	O2A—N3A—C2A	118.64 (18)
C14B—C13B—H13B	117.8	O1A—N3A—C2A	119.62 (18)
C1B—N1B—N2B	119.14 (17)	O3A—N4A—O4A	123.5 (2)
C1B—N1B—H1B	120.2	O3A—N4A—C4A	119.0 (2)
N2B—N1B—H1B	120.6	O4A—N4A—C4A	117.6 (2)
C7B—N2B—N1B	116.20 (18)	N1A—C1A—C2A	123.4 (2)
O2B—N3B—O1B	121.78 (18)	N1A—C1A—C6A	119.72 (19)
O2B—N3B—C2B	118.60 (18)	C2A—C1A—C6A	116.92 (19)
O1B—N3B—C2B	119.62 (17)	C3A—C2A—C1A	121.85 (19)
O3B—N4B—O4B	123.68 (18)	C3A—C2A—N3A	116.29 (19)
O3B—N4B—C4B	118.75 (18)	C1A—C2A—N3A	121.84 (18)
O4B—N4B—C4B	117.56 (18)	C4A—C3A—C2A	118.5 (2)
N1B—C1B—C2B	122.79 (18)	C4A—C3A—H3A	120.8
N1B—C1B—C6B	120.28 (18)	C2A—C3A—H3A	120.8
C2B—C1B—C6B	116.93 (18)	C3A—C4A—C5A	121.8 (2)
C3B—C2B—C1B	121.79 (18)	C3A—C4A—N4A	119.2 (2)
C3B—C2B—N3B	116.10 (17)	C5A—C4A—N4A	119.0 (2)
C1B—C2B—N3B	122.10 (18)	C6A—C5A—C4A	119.8 (2)
C4B—C3B—C2B	118.59 (18)	C6A—C5A—H5A	120.1
C4B—C3B—H3B	120.7	C4A—C5A—H5A	120.1
C2B—C3B—H3B	120.7	C5A—C6A—C1A	121.1 (2)
C3B—C4B—C5B	121.95 (19)	C5A—C6A—H6A	119.4
C3B—C4B—N4B	118.55 (18)	C1A—C6A—H6A	119.4
C5B—C4B—N4B	119.49 (19)	N2A—C7A—C9A	115.38 (19)
C6B—C5B—C4B	119.20 (19)	N2A—C7A—C8A	122.9 (2)
C6B—C5B—H5B	120.4	C9A—C7A—C8A	121.8 (2)
C4B—C5B—H5B	120.4	C7A—C8A—H8A	109.5
C5B—C6B—C1B	121.53 (19)	C7A—C8A—H8B	109.5
C5B—C6B—H6B	119.2	H8A—C8A—H8B	109.5
C1B—C6B—H6B	119.2	C7A—C8A—H8C	109.5
N2B—C7B—C9B	115.24 (19)	H8A—C8A—H8C	109.5
N2B—C7B—C8B	122.65 (19)	H8B—C8A—H8C	109.5
C9B—C7B—C8B	122.10 (19)	C10A—C9A—C14A	118.40 (19)
C7B—C8B—H6	109.5	C10A—C9A—C7A	121.57 (19)
C7B—C8B—H7	109.5	C14A—C9A—C7A	120.02 (19)
H6—C8B—H7	109.5	C11A—C10A—C9A	119.4 (2)
C7B—C8B—H8	109.5	C11A—C10A—H10A	120.3
H6—C8B—H8	109.5	C9A—C10A—H10A	120.3
H7—C8B—H8	109.5	C12A—C11A—C10A	122.2 (2)
C10B—C9B—C14B	118.6 (2)	C12A—C11A—Br1A	118.45 (16)
C10B—C9B—C7B	121.6 (2)	C10A—C11A—Br1A	119.39 (17)
C14B—C9B—C7B	119.75 (19)	C11A—C12A—C13A	118.2 (2)
C9B—C10B—C11B	120.9 (2)	C11A—C12A—H12A	120.9
C9B—C10B—H10B	120.3	C13A—C12A—H12A	120.9
C11B—C10B—H10B	118.8	C14A—C13A—C12A	120.7 (2)
C13B—C12B—C11B	117.9 (2)	C14A—C13A—H13A	119.6
C13B—C12B—H12B	121.1	C12A—C13A—H13A	119.6
C11B—C12B—H12B	121.1	C13A—C14A—C9A	121.1 (2)
C13B—C14B—C9B	118.6 (2)	C13A—C14A—H14A	119.4
C13B—C14B—H14B	120.7	C9A—C14A—H14A	119.4
C1B—N1B—N2B—C7B	−178.38 (18)	C1A—N1A—N2A—C7A	−172.92 (19)
N2B—N1B—C1B—C2B	179.47 (18)	N2A—N1A—C1A—C2A	−178.63 (19)
N2B—N1B—C1B—C6B	−0.2 (3)	N2A—N1A—C1A—C6A	2.5 (3)
N1B—C1B—C2B—C3B	179.45 (19)	N1A—C1A—C2A—C3A	−179.2 (2)
C6B—C1B—C2B—C3B	−0.9 (3)	C6A—C1A—C2A—C3A	−0.3 (3)
N1B—C1B—C2B—N3B	0.7 (3)	N1A—C1A—C2A—N3A	2.1 (3)
C6B—C1B—C2B—N3B	−179.63 (18)	C6A—C1A—C2A—N3A	−179.05 (19)
O2B—N3B—C2B—C3B	5.3 (3)	O2A—N3A—C2A—C3A	4.2 (3)
O1B—N3B—C2B—C3B	−174.14 (19)	O1A—N3A—C2A—C3A	−175.28 (19)
O2B—N3B—C2B—C1B	−175.93 (19)	O2A—N3A—C2A—C1A	−176.97 (19)
O1B—N3B—C2B—C1B	4.6 (3)	O1A—N3A—C2A—C1A	3.5 (3)
C1B—C2B—C3B—C4B	0.7 (3)	C1A—C2A—C3A—C4A	0.3 (3)
N3B—C2B—C3B—C4B	179.46 (18)	N3A—C2A—C3A—C4A	179.14 (19)
C2B—C3B—C4B—C5B	−0.1 (3)	C2A—C3A—C4A—C5A	0.0 (3)
C2B—C3B—C4B—N4B	179.09 (18)	C2A—C3A—C4A—N4A	−179.65 (19)
O3B—N4B—C4B—C3B	4.4 (3)	O3A—N4A—C4A—C3A	1.7 (3)
O4B—N4B—C4B—C3B	−174.42 (19)	O4A—N4A—C4A—C3A	−178.3 (2)
O3B—N4B—C4B—C5B	−176.35 (19)	O3A—N4A—C4A—C5A	−178.0 (2)
O4B—N4B—C4B—C5B	4.8 (3)	O4A—N4A—C4A—C5A	2.1 (3)
C3B—C4B—C5B—C6B	−0.2 (3)	C3A—C4A—C5A—C6A	−0.3 (3)
N4B—C4B—C5B—C6B	−179.38 (18)	N4A—C4A—C5A—C6A	179.3 (2)
C4B—C5B—C6B—C1B	−0.1 (3)	C4A—C5A—C6A—C1A	0.3 (3)
N1B—C1B—C6B—C5B	−179.74 (19)	N1A—C1A—C6A—C5A	178.9 (2)
C2B—C1B—C6B—C5B	0.6 (3)	C2A—C1A—C6A—C5A	0.0 (3)
N1B—N2B—C7B—C9B	179.45 (17)	N1A—N2A—C7A—C9A	179.93 (18)
N1B—N2B—C7B—C8B	0.4 (3)	N1A—N2A—C7A—C8A	0.2 (3)
N2B—C7B—C9B—C10B	−178.26 (19)	N2A—C7A—C9A—C10A	170.6 (2)
C8B—C7B—C9B—C10B	0.8 (3)	C8A—C7A—C9A—C10A	−9.7 (4)
N2B—C7B—C9B—C14B	0.7 (3)	N2A—C7A—C9A—C14A	−8.8 (3)
C8B—C7B—C9B—C14B	179.8 (2)	C8A—C7A—C9A—C14A	170.9 (2)
C14B—C9B—C10B—C11B	0.3 (3)	C14A—C9A—C10A—C11A	0.0 (3)
C7B—C9B—C10B—C11B	179.3 (2)	C7A—C9A—C10A—C11A	−179.5 (2)
C12B—C11B—C10B—C9B	0.3 (3)	C9A—C10A—C11A—C12A	0.0 (3)
Br2B—C11B—C10B—C9B	−179.97 (17)	C9A—C10A—C11A—Br1A	−179.19 (16)
C14B—C13B—C12B—C11B	0.5 (4)	C10A—C11A—C12A—C13A	0.1 (3)
C10B—C11B—C12B—C13B	−0.6 (4)	Br1A—C11A—C12A—C13A	179.22 (17)
Br2B—C11B—C12B—C13B	179.58 (18)	C11A—C12A—C13A—C14A	−0.1 (3)
C12B—C13B—C14B—C9B	0.0 (4)	C12A—C13A—C14A—C9A	0.1 (3)
C10B—C9B—C14B—C13B	−0.4 (3)	C10A—C9A—C14A—C13A	0.0 (3)
C7B—C9B—C14B—C13B	−179.4 (2)	C7A—C9A—C14A—C13A	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1B···O1B	0.86	1.99	2.615 (2)	129
N1A—H1A···O1A	0.86	2.00	2.621 (2)	128
C8B—H7···O2Ai	0.98	2.60	3.241 (3)	123
C12B—H12B···O3Bi	0.95	2.38	3.332 (3)	175
C8A—H8A···O3Bii	0.98	2.61	3.369 (3)	135
C13A—H13A···O4Biii	0.95	2.40	3.282 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1B⋯O1B	0.86	1.99	2.615 (2)	129
N1A—H1A⋯O1A	0.86	2.00	2.621 (2)	128
C8B—H7⋯O2Ai	0.98	2.60	3.241 (3)	123
C12B—H12B⋯O3Bi	0.95	2.38	3.332 (3)	175
C8A—H8A⋯O3Bii	0.98	2.61	3.369 (3)	135
C13A—H13A⋯O4Biii	0.95	2.40	3.282 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) .