2-(4-Bromo-phen-yl)-N-(5-methyl-pyridin-2-yl)acetamide.

The asymmetric unit of the title compound, C(14)H(13)BrN(2)O, consists of two mol-ecules; the dihedral angles between the pyridine and benzene rings are 87.99 (9) and 84.28 (9)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring in each mol-ecule. In the crystal, mol-ecules are linked via N-H⋯N and C-H⋯O hydrogen bonds into a three-dimensional network. The crystal structure also features weak π-π stacking inter-actrions between the benzene rings [centroid-to-centroid distance = 3.6829 (12) Å].

Related literature

For related structures, see: Fun et al. (2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H13BrN2O

M = 305.17

Monoclinic,

a = 14.0086 (16) Å

b = 9.4215 (11) Å

c = 20.610 (2) Å

β = 109.040 (2)°

V = 2571.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 3.19 mm−1

T = 100 K

0.35 × 0.31 × 0.16 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.404, T max = 0.626

28356 measured reflections

7539 independent reflections

5774 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.068

S = 1.03

7539 reflections

327 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.84 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032631/hb6903sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032631/hb6903Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032631/hb6903Isup3.cml

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

C14H13BrN2O	F(000) = 1232
Mr = 305.17	Dx = 1.577 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7856 reflections
a = 14.0086 (16) Å	θ = 2.4–29.9°
b = 9.4215 (11) Å	µ = 3.19 mm−1
c = 20.610 (2) Å	T = 100 K
β = 109.040 (2)°	Block, colourless
V = 2571.3 (5) Å3	0.35 × 0.31 × 0.16 mm
Z = 8

Bruker APEX DUO CCD diffractometer	7539 independent reflections
Radiation source: fine-focus sealed tube	5774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 30.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.404, Tmax = 0.626	k = −13→11
28356 measured reflections	l = −29→29

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0229P)2 + 0.7284P] where P = (Fo2 + 2Fc2)/3
7539 reflections	(Δ/σ)max = 0.001
327 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.84 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100 (1) K.

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	0.195964 (14)	0.81673 (2)	0.236716 (10)	0.02478 (6)
O1A	0.68992 (10)	0.87227 (17)	0.26779 (7)	0.0239 (3)
N1A	0.88325 (11)	0.63139 (18)	0.19256 (7)	0.0166 (3)
N2A	0.73682 (11)	0.74607 (18)	0.18857 (7)	0.0155 (3)
H1N2	0.7195	0.7183	0.1479	0.019*
C1A	0.97524 (14)	0.5797 (2)	0.22730 (9)	0.0178 (4)
H1AA	1.0100	0.5287	0.2021	0.021*
C2A	1.02300 (14)	0.5955 (2)	0.29725 (9)	0.0170 (4)
C3A	0.97107 (14)	0.6710 (2)	0.33286 (9)	0.0182 (4)
H3AA	1.0015	0.6871	0.3807	0.022*
C4A	0.87506 (14)	0.7233 (2)	0.29916 (9)	0.0176 (4)
H4AA	0.8384	0.7735	0.3233	0.021*
C5A	0.83407 (13)	0.6999 (2)	0.22894 (9)	0.0150 (4)
C6A	0.67342 (13)	0.8314 (2)	0.20897 (9)	0.0161 (4)
C7A	0.57883 (13)	0.8776 (2)	0.15194 (9)	0.0182 (4)
H7AA	0.5863	0.9777	0.1399	0.022*
H7AB	0.5710	0.8189	0.1107	0.022*
C8A	0.48535 (13)	0.8631 (2)	0.17273 (9)	0.0154 (4)
C9A	0.44796 (15)	0.7304 (2)	0.18061 (10)	0.0216 (4)
H9AA	0.4820	0.6482	0.1729	0.026*
C10A	0.36231 (15)	0.7145 (2)	0.19943 (10)	0.0221 (4)
H10A	0.3379	0.6227	0.2049	0.026*
C11A	0.31300 (14)	0.8351 (2)	0.21015 (9)	0.0178 (4)
C12A	0.34796 (14)	0.9688 (2)	0.20254 (10)	0.0206 (4)
H12A	0.3133	1.0507	0.2099	0.025*
C13A	0.43454 (14)	0.9824 (2)	0.18395 (9)	0.0184 (4)
H13A	0.4592	1.0743	0.1789	0.022*
C14A	1.12626 (15)	0.5339 (2)	0.33246 (10)	0.0244 (4)
H14A	1.1567	0.5051	0.2979	0.037*
H14B	1.1202	0.4511	0.3596	0.037*
H14C	1.1690	0.6055	0.3628	0.037*
Br1B	0.362638 (14)	0.54031 (2)	0.494541 (10)	0.02378 (6)
O1B	−0.09186 (10)	0.80166 (16)	0.45686 (6)	0.0230 (3)
N1B	−0.33380 (11)	0.83860 (17)	0.53410 (7)	0.0154 (3)
N2B	−0.16779 (11)	0.82936 (17)	0.53881 (7)	0.0155 (3)
H2N2	−0.1559	0.8362	0.5805	0.019*
C1B	−0.43308 (14)	0.8465 (2)	0.49897 (9)	0.0170 (4)
H1BA	−0.4785	0.8476	0.5246	0.020*
C2B	−0.47401 (13)	0.8532 (2)	0.42804 (9)	0.0162 (4)
C3B	−0.40554 (14)	0.8531 (2)	0.39206 (9)	0.0167 (4)
H3BA	−0.4296	0.8584	0.3434	0.020*
C4B	−0.30301 (14)	0.8453 (2)	0.42630 (9)	0.0154 (4)
H4BA	−0.2561	0.8453	0.4018	0.019*
C5B	−0.27001 (13)	0.8375 (2)	0.49800 (9)	0.0141 (4)
C6B	−0.08622 (14)	0.8118 (2)	0.51717 (9)	0.0162 (4)
C7B	0.01452 (13)	0.8088 (2)	0.57477 (9)	0.0200 (4)
H7BA	0.0340	0.9071	0.5905	0.024*
H7BB	0.0067	0.7548	0.6139	0.024*
C8B	0.09776 (13)	0.7428 (2)	0.55364 (9)	0.0164 (4)
C9B	0.11021 (14)	0.5975 (2)	0.55405 (10)	0.0213 (4)
H9BA	0.0643	0.5381	0.5667	0.026*
C10B	0.18826 (15)	0.5365 (2)	0.53639 (10)	0.0215 (4)
H10B	0.1962	0.4363	0.5370	0.026*
C11B	0.25450 (14)	0.6235 (2)	0.51780 (9)	0.0176 (4)
C12B	0.24397 (15)	0.7683 (2)	0.51692 (11)	0.0250 (5)
H12B	0.2899	0.8274	0.5042	0.030*
C13B	0.16501 (15)	0.8274 (2)	0.53492 (11)	0.0240 (4)
H13B	0.1572	0.9276	0.5343	0.029*
C14B	−0.58628 (14)	0.8603 (2)	0.39206 (10)	0.0218 (4)
H14D	−0.6208	0.8732	0.4261	0.033*
H14E	−0.6092	0.7719	0.3667	0.033*
H14F	−0.6019	0.9405	0.3600	0.033*

	U11	U22	U33	U12	U13	U23
Br1A	0.01468 (9)	0.04023 (14)	0.01992 (9)	−0.00378 (9)	0.00632 (7)	−0.00040 (9)
O1A	0.0213 (7)	0.0316 (9)	0.0176 (6)	0.0071 (6)	0.0048 (5)	−0.0048 (6)
N1A	0.0160 (7)	0.0188 (9)	0.0158 (7)	0.0023 (7)	0.0063 (6)	0.0012 (6)
N2A	0.0140 (7)	0.0203 (9)	0.0122 (7)	0.0003 (7)	0.0041 (6)	−0.0015 (6)
C1A	0.0177 (9)	0.0193 (11)	0.0185 (8)	0.0039 (8)	0.0088 (7)	0.0017 (7)
C2A	0.0158 (9)	0.0173 (11)	0.0176 (8)	0.0003 (8)	0.0051 (7)	0.0038 (7)
C3A	0.0188 (9)	0.0204 (11)	0.0148 (8)	−0.0016 (8)	0.0045 (7)	0.0002 (7)
C4A	0.0186 (9)	0.0193 (11)	0.0157 (8)	0.0018 (8)	0.0066 (7)	−0.0007 (7)
C5A	0.0148 (8)	0.0153 (10)	0.0156 (8)	−0.0013 (7)	0.0058 (7)	0.0002 (7)
C6A	0.0148 (8)	0.0159 (10)	0.0187 (8)	−0.0004 (7)	0.0068 (7)	0.0010 (7)
C7A	0.0167 (9)	0.0212 (11)	0.0169 (8)	0.0042 (8)	0.0058 (7)	0.0034 (7)
C8A	0.0124 (8)	0.0188 (11)	0.0142 (8)	0.0019 (7)	0.0031 (7)	0.0010 (7)
C9A	0.0216 (10)	0.0177 (11)	0.0265 (10)	0.0044 (8)	0.0092 (8)	0.0011 (8)
C10A	0.0231 (10)	0.0175 (11)	0.0254 (10)	−0.0022 (8)	0.0076 (8)	0.0026 (8)
C11A	0.0137 (8)	0.0243 (12)	0.0147 (8)	−0.0021 (8)	0.0034 (7)	0.0000 (8)
C12A	0.0198 (9)	0.0196 (11)	0.0233 (9)	0.0042 (8)	0.0082 (8)	−0.0025 (8)
C13A	0.0186 (9)	0.0140 (11)	0.0218 (9)	−0.0012 (8)	0.0056 (7)	−0.0003 (7)
C14A	0.0207 (10)	0.0280 (13)	0.0227 (9)	0.0080 (9)	0.0048 (8)	0.0043 (9)
Br1B	0.01786 (10)	0.03056 (13)	0.02292 (10)	0.00614 (9)	0.00664 (7)	−0.00641 (8)
O1B	0.0181 (7)	0.0362 (10)	0.0154 (6)	0.0040 (6)	0.0063 (5)	−0.0024 (6)
N1B	0.0140 (7)	0.0177 (9)	0.0145 (7)	0.0014 (6)	0.0047 (6)	0.0001 (6)
N2B	0.0137 (7)	0.0205 (9)	0.0119 (6)	0.0017 (6)	0.0037 (6)	0.0000 (6)
C1B	0.0158 (9)	0.0181 (11)	0.0179 (8)	0.0014 (7)	0.0068 (7)	0.0016 (7)
C2B	0.0149 (9)	0.0141 (10)	0.0177 (8)	0.0015 (7)	0.0027 (7)	0.0006 (7)
C3B	0.0205 (9)	0.0148 (10)	0.0127 (8)	−0.0002 (8)	0.0025 (7)	0.0014 (7)
C4B	0.0181 (9)	0.0142 (10)	0.0144 (8)	0.0005 (7)	0.0058 (7)	0.0004 (7)
C5B	0.0131 (8)	0.0125 (10)	0.0160 (8)	0.0012 (7)	0.0036 (7)	0.0003 (7)
C6B	0.0152 (9)	0.0164 (10)	0.0171 (8)	0.0015 (7)	0.0054 (7)	0.0005 (7)
C7B	0.0140 (9)	0.0288 (12)	0.0167 (8)	0.0013 (8)	0.0045 (7)	−0.0028 (8)
C8B	0.0124 (8)	0.0219 (11)	0.0138 (8)	0.0009 (8)	0.0028 (7)	−0.0002 (7)
C9B	0.0194 (9)	0.0214 (12)	0.0241 (9)	−0.0053 (8)	0.0084 (8)	0.0005 (8)
C10B	0.0230 (10)	0.0146 (11)	0.0260 (10)	0.0002 (8)	0.0065 (8)	−0.0007 (8)
C11B	0.0148 (9)	0.0210 (11)	0.0165 (8)	0.0044 (8)	0.0043 (7)	−0.0026 (7)
C12B	0.0224 (10)	0.0219 (12)	0.0366 (11)	−0.0009 (9)	0.0176 (9)	0.0026 (9)
C13B	0.0241 (10)	0.0153 (11)	0.0368 (11)	0.0021 (8)	0.0156 (9)	0.0016 (9)
C14B	0.0165 (9)	0.0280 (12)	0.0182 (9)	0.0020 (8)	0.0021 (7)	0.0004 (8)

Br1A—C11A	1.8982 (18)	Br1B—C11B	1.9007 (18)
O1A—C6A	1.220 (2)	O1B—C6B	1.223 (2)
N1A—C5A	1.338 (2)	N1B—C5B	1.336 (2)
N1A—C1A	1.345 (2)	N1B—C1B	1.344 (2)
N2A—C6A	1.362 (2)	N2B—C6B	1.365 (2)
N2A—C5A	1.413 (2)	N2B—C5B	1.406 (2)
N2A—H1N2	0.8358	N2B—H2N2	0.8222
C1A—C2A	1.385 (2)	C1B—C2B	1.387 (2)
C1A—H1AA	0.9500	C1B—H1BA	0.9500
C2A—C3A	1.386 (3)	C2B—C3B	1.391 (2)
C2A—C14A	1.507 (3)	C2B—C14B	1.506 (3)
C3A—C4A	1.387 (3)	C3B—C4B	1.380 (3)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.389 (2)	C4B—C5B	1.399 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C6A—C7A	1.520 (3)	C6B—C7B	1.519 (3)
C7A—C8A	1.511 (2)	C7B—C8B	1.506 (2)
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—C9A	1.385 (3)	C8B—C9B	1.380 (3)
C8A—C13A	1.390 (3)	C8B—C13B	1.382 (3)
C9A—C10A	1.384 (3)	C9B—C10B	1.385 (3)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.384 (3)	C10B—C11B	1.383 (3)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.379 (3)	C11B—C12B	1.372 (3)
C12A—C13A	1.392 (3)	C12B—C13B	1.392 (3)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C5A—N1A—C1A	117.09 (15)	C5B—N1B—C1B	117.56 (15)
C6A—N2A—C5A	126.89 (15)	C6B—N2B—C5B	127.49 (15)
C6A—N2A—H1N2	119.3	C6B—N2B—H2N2	116.4
C5A—N2A—H1N2	113.7	C5B—N2B—H2N2	116.1
N1A—C1A—C2A	124.66 (17)	N1B—C1B—C2B	124.73 (16)
N1A—C1A—H1AA	117.7	N1B—C1B—H1BA	117.6
C2A—C1A—H1AA	117.7	C2B—C1B—H1BA	117.6
C1A—C2A—C3A	116.59 (17)	C1B—C2B—C3B	116.25 (16)
C1A—C2A—C14A	121.43 (17)	C1B—C2B—C14B	121.83 (16)
C3A—C2A—C14A	121.98 (17)	C3B—C2B—C14B	121.92 (16)
C2A—C3A—C4A	120.49 (17)	C4B—C3B—C2B	120.74 (16)
C2A—C3A—H3AA	119.8	C4B—C3B—H3BA	119.6
C4A—C3A—H3AA	119.8	C2B—C3B—H3BA	119.6
C3A—C4A—C5A	117.97 (17)	C3B—C4B—C5B	118.22 (16)
C3A—C4A—H4AA	121.0	C3B—C4B—H4BA	120.9
C5A—C4A—H4AA	121.0	C5B—C4B—H4BA	120.9
N1A—C5A—C4A	123.14 (17)	N1B—C5B—C4B	122.49 (16)
N1A—C5A—N2A	113.09 (15)	N1B—C5B—N2B	113.76 (15)
C4A—C5A—N2A	123.77 (16)	C4B—C5B—N2B	123.75 (16)
O1A—C6A—N2A	124.16 (17)	O1B—C6B—N2B	123.91 (17)
O1A—C6A—C7A	120.87 (17)	O1B—C6B—C7B	121.87 (16)
N2A—C6A—C7A	114.96 (15)	N2B—C6B—C7B	114.21 (15)
C8A—C7A—C6A	111.88 (14)	C8B—C7B—C6B	113.03 (15)
C8A—C7A—H7AA	109.2	C8B—C7B—H7BA	109.0
C6A—C7A—H7AA	109.2	C6B—C7B—H7BA	109.0
C8A—C7A—H7AB	109.2	C8B—C7B—H7BB	109.0
C6A—C7A—H7AB	109.2	C6B—C7B—H7BB	109.0
H7AA—C7A—H7AB	107.9	H7BA—C7B—H7BB	107.8
C9A—C8A—C13A	118.47 (17)	C9B—C8B—C13B	118.53 (18)
C9A—C8A—C7A	120.71 (17)	C9B—C8B—C7B	121.10 (17)
C13A—C8A—C7A	120.82 (18)	C13B—C8B—C7B	120.35 (19)
C10A—C9A—C8A	121.74 (19)	C8B—C9B—C10B	121.28 (18)
C10A—C9A—H9AA	119.1	C8B—C9B—H9BA	119.4
C8A—C9A—H9AA	119.1	C10B—C9B—H9BA	119.4
C9A—C10A—C11A	118.64 (19)	C11B—C10B—C9B	119.05 (19)
C9A—C10A—H10A	120.7	C11B—C10B—H10B	120.5
C11A—C10A—H10A	120.7	C9B—C10B—H10B	120.5
C12A—C11A—C10A	121.15 (17)	C12B—C11B—C10B	120.95 (18)
C12A—C11A—Br1A	119.22 (14)	C12B—C11B—Br1B	119.86 (15)
C10A—C11A—Br1A	119.63 (15)	C10B—C11B—Br1B	119.18 (15)
C11A—C12A—C13A	119.29 (18)	C11B—C12B—C13B	119.04 (19)
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.5
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.5
C8A—C13A—C12A	120.71 (19)	C8B—C13B—C12B	121.1 (2)
C8A—C13A—H13A	119.6	C8B—C13B—H13B	119.4
C12A—C13A—H13A	119.6	C12B—C13B—H13B	119.4
C2A—C14A—H14A	109.5	C2B—C14B—H14D	109.5
C2A—C14A—H14B	109.5	C2B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C2A—C14A—H14C	109.5	C2B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C5A—N1A—C1A—C2A	−1.6 (3)	C5B—N1B—C1B—C2B	0.2 (3)
N1A—C1A—C2A—C3A	−0.3 (3)	N1B—C1B—C2B—C3B	−0.7 (3)
N1A—C1A—C2A—C14A	179.84 (19)	N1B—C1B—C2B—C14B	179.30 (19)
C1A—C2A—C3A—C4A	1.8 (3)	C1B—C2B—C3B—C4B	0.6 (3)
C14A—C2A—C3A—C4A	−178.39 (19)	C14B—C2B—C3B—C4B	−179.46 (19)
C2A—C3A—C4A—C5A	−1.2 (3)	C2B—C3B—C4B—C5B	0.1 (3)
C1A—N1A—C5A—C4A	2.3 (3)	C1B—N1B—C5B—C4B	0.5 (3)
C1A—N1A—C5A—N2A	−177.92 (16)	C1B—N1B—C5B—N2B	179.86 (17)
C3A—C4A—C5A—N1A	−0.9 (3)	C3B—C4B—C5B—N1B	−0.6 (3)
C3A—C4A—C5A—N2A	179.32 (18)	C3B—C4B—C5B—N2B	−179.92 (18)
C6A—N2A—C5A—N1A	−172.21 (18)	C6B—N2B—C5B—N1B	172.75 (18)
C6A—N2A—C5A—C4A	7.6 (3)	C6B—N2B—C5B—C4B	−7.9 (3)
C5A—N2A—C6A—O1A	−5.5 (3)	C5B—N2B—C6B—O1B	0.6 (3)
C5A—N2A—C6A—C7A	172.96 (17)	C5B—N2B—C6B—C7B	179.44 (18)
O1A—C6A—C7A—C8A	−47.0 (3)	O1B—C6B—C7B—C8B	−20.2 (3)
N2A—C6A—C7A—C8A	134.48 (18)	N2B—C6B—C7B—C8B	160.96 (17)
C6A—C7A—C8A—C9A	−70.1 (2)	C6B—C7B—C8B—C9B	−83.0 (2)
C6A—C7A—C8A—C13A	110.3 (2)	C6B—C7B—C8B—C13B	98.5 (2)
C13A—C8A—C9A—C10A	−0.2 (3)	C13B—C8B—C9B—C10B	0.2 (3)
C7A—C8A—C9A—C10A	−179.82 (18)	C7B—C8B—C9B—C10B	−178.28 (17)
C8A—C9A—C10A—C11A	0.4 (3)	C8B—C9B—C10B—C11B	−0.2 (3)
C9A—C10A—C11A—C12A	−0.1 (3)	C9B—C10B—C11B—C12B	0.2 (3)
C9A—C10A—C11A—Br1A	−179.49 (14)	C9B—C10B—C11B—Br1B	179.29 (14)
C10A—C11A—C12A—C13A	−0.2 (3)	C10B—C11B—C12B—C13B	−0.2 (3)
Br1A—C11A—C12A—C13A	179.15 (14)	Br1B—C11B—C12B—C13B	−179.23 (16)
C9A—C8A—C13A—C12A	−0.1 (3)	C9B—C8B—C13B—C12B	−0.1 (3)
C7A—C8A—C13A—C12A	179.47 (17)	C7B—C8B—C13B—C12B	178.35 (18)
C11A—C12A—C13A—C8A	0.3 (3)	C11B—C12B—C13B—C8B	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1N2···N1Bi	0.84	2.28	3.114 (2)	175
N2B—H2N2···N1Aii	0.82	2.21	3.035 (2)	176
C3A—H3AA···O1Biii	0.95	2.58	3.208 (2)	124
C4A—H4AA···O1A	0.95	2.22	2.832 (3)	121
C10A—H10A···O1Aiv	0.95	2.49	3.422 (3)	169
C4B—H4BA···O1B	0.95	2.25	2.846 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1N2⋯N1B i	0.84	2.28	3.114 (2)	175
N2B—H2N2⋯N1A ii	0.82	2.21	3.035 (2)	176
C3A—H3AA⋯O1B iii	0.95	2.58	3.208 (2)	124
C4A—H4AA⋯O1A	0.95	2.22	2.832 (3)	121
C10A—H10A⋯O1A iv	0.95	2.49	3.422 (3)	169
C4B—H4BA⋯O1B	0.95	2.25	2.846 (3)	120

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