2,3-Dibromo-1-(4-methyl-phen-yl)-3-(5-nitro-furan-2-yl)propan-1-one.

In the title compound, C(14)H(11)Br(2)NO(4), the whole mol-ecule is disordered over two positions with a refined occupancy ratio of 0.539 (9):0.461 (9). The 2-nitro-furan and toluene groups are approximately planar, with maximum deviations of 0.176 (11) and 0.121 (14) Å, respectively, in the major component and 0.208 (11) and 0.30 (17) Å in the minor component. The dihedral angles between the 2-nitro-furan and toluene groups are 8.7 (5) and 8.0 (9)° for the major and minor components, respectively. In the crystal, weak inter-molecular C-H⋯O inter-actions connect mol-ecules into a three-dimensional network, generating R(2) (1)(6) ring motifs.

Related literature

For the biological activity of nitrofurans, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶); Hegde et al. (2006 ▶); Rai et al. (2008 ▶). For a related structure, see: Fun et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H11Br2NO4

M = 417.06

Triclinic,

a = 8.7766 (3) Å

b = 9.0386 (3) Å

c = 10.4841 (3) Å

α = 87.601 (2)°

β = 75.505 (2)°

γ = 69.554 (2)°

V = 753.53 (4) Å3

Z = 2

Mo Kα radiation

μ = 5.39 mm−1

T = 100 K

0.47 × 0.21 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.184, T max = 0.550

10357 measured reflections

3465 independent reflections

2729 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.19

3465 reflections

274 parameters

658 restraints

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −0.40 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 datablocks global, I. DOI: 10.1107/S1600536810050488/lh5178sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050488/lh5178Isup2.hkl

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

C14H11Br2NO4	Z = 2
Mr = 417.06	F(000) = 408
Triclinic, P1	Dx = 1.838 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7766 (3) Å	Cell parameters from 4461 reflections
b = 9.0386 (3) Å	θ = 2.8–29.8°
c = 10.4841 (3) Å	µ = 5.39 mm−1
α = 87.601 (2)°	T = 100 K
β = 75.505 (2)°	Block, colourless
γ = 69.554 (2)°	0.47 × 0.21 × 0.13 mm
V = 753.53 (4) Å3

Bruker APEXII DUO CCD area-detector diffractometer	3465 independent reflections
Radiation source: fine-focus sealed tube	2729 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.184, Tmax = 0.550	k = −11→11
10357 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0366P)2 + 1.118P] where P = (Fo2 + 2Fc2)/3
3465 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.88 e Å−3
658 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (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	Occ. (<1)
O1A	0.3252 (8)	0.1907 (8)	0.2855 (6)	0.0247 (12)	0.539 (9)
O2A	0.7200 (11)	0.4559 (10)	0.3552 (8)	0.0263 (15)	0.539 (9)
O3A	0.0607 (10)	−0.0275 (11)	0.3127 (8)	0.0353 (18)	0.539 (9)
O4A	0.2823 (12)	−0.0290 (13)	0.1606 (10)	0.029 (2)	0.539 (9)
N1A	0.188 (3)	0.009 (3)	0.2706 (15)	0.025 (3)	0.539 (9)
C1A	0.1954 (16)	0.1367 (19)	0.3437 (13)	0.024 (2)	0.539 (9)
C2A	0.0942 (13)	0.2160 (16)	0.4548 (12)	0.024 (2)	0.539 (9)
H2AA	−0.0059	0.2062	0.5033	0.029*	0.539 (9)
C3A	0.1735 (15)	0.3187 (18)	0.4824 (14)	0.026 (3)	0.539 (9)
H3AA	0.1409	0.3841	0.5579	0.031*	0.539 (9)
C5A	0.3058 (10)	0.3035 (9)	0.3781 (8)	0.0256 (15)	0.539 (9)
C8A	0.7314 (16)	0.3690 (17)	0.2649 (12)	0.028 (2)	0.539 (9)
C9A	0.8760 (16)	0.322 (2)	0.1492 (12)	0.024 (3)	0.539 (9)
C10A	1.009 (2)	0.374 (4)	0.148 (2)	0.023 (3)	0.539 (9)
H10A	1.0027	0.4368	0.2193	0.028*	0.539 (9)
C11A	1.1495 (18)	0.334 (2)	0.0434 (16)	0.027 (2)	0.539 (9)
H11A	1.2350	0.3720	0.0449	0.032*	0.539 (9)
C12A	1.1681 (14)	0.2394 (19)	−0.0645 (13)	0.027 (2)	0.539 (9)
C13A	1.0316 (14)	0.1904 (19)	−0.0648 (12)	0.028 (3)	0.539 (9)
H13A	1.0379	0.1293	−0.1364	0.033*	0.539 (9)
C14A	0.8896 (14)	0.2312 (18)	0.0384 (11)	0.031 (3)	0.539 (9)
H14A	0.8015	0.1982	0.0348	0.037*	0.539 (9)
C15A	1.3292 (18)	0.177 (2)	−0.1713 (17)	0.049 (4)	0.539 (9)
H15A	1.4031	0.2314	−0.1629	0.073*	0.539 (9)
H15B	1.3048	0.1948	−0.2561	0.073*	0.539 (9)
H15C	1.3823	0.0660	−0.1629	0.073*	0.539 (9)
Br1A	0.6688 (5)	0.1302 (5)	0.4219 (5)	0.0395 (7)	0.539 (9)
Br2A	0.3626 (5)	0.5504 (4)	0.2175 (5)	0.0414 (6)	0.539 (9)
C6A	0.4234 (8)	0.3896 (8)	0.3487 (7)	0.0309 (16)	0.539 (9)
H6AA	0.4189	0.4424	0.4301	0.037*	0.539 (9)
C7A	0.5995 (9)	0.2863 (9)	0.2889 (7)	0.0312 (15)	0.539 (9)
H7AA	0.6066	0.2322	0.2074	0.037*	0.539 (9)
O1B	0.3468 (10)	0.1563 (9)	0.3082 (8)	0.024 (2)*	0.461 (9)
O2B	0.6979 (14)	0.4869 (11)	0.3410 (10)	0.022 (2)*	0.461 (9)
O3B	0.1011 (13)	−0.0594 (12)	0.2947 (11)	0.037 (3)*	0.461 (9)
O4B	0.3032 (19)	−0.0313 (19)	0.1354 (13)	0.037 (3)*	0.461 (9)
N1B	0.197 (4)	0.012 (4)	0.241 (2)	0.025 (3)	0.461 (9)
C1B	0.206 (2)	0.122 (2)	0.3321 (16)	0.025 (3)*	0.461 (9)
C2B	0.1002 (19)	0.194 (2)	0.4467 (16)	0.030 (3)*	0.461 (9)
H2BA	0.0011	0.1790	0.4910	0.036*	0.461 (9)
C3B	0.171 (2)	0.298 (2)	0.4858 (17)	0.031 (4)*	0.461 (9)
H3BA	0.1208	0.3734	0.5552	0.037*	0.461 (9)
C5B	0.3271 (12)	0.2658 (10)	0.4029 (9)	0.021 (2)*	0.461 (9)
C8B	0.713 (2)	0.393 (2)	0.2559 (14)	0.025 (3)*	0.461 (9)
C9B	0.860 (2)	0.340 (3)	0.1418 (16)	0.025 (4)*	0.461 (9)
C10B	1.003 (3)	0.374 (5)	0.145 (3)	0.030 (5)*	0.461 (9)
H10B	1.0002	0.4344	0.2156	0.036*	0.461 (9)
C11B	1.149 (2)	0.320 (3)	0.0433 (19)	0.029 (3)*	0.461 (9)
H11B	1.2444	0.3393	0.0480	0.035*	0.461 (9)
C12B	1.1500 (17)	0.235 (2)	−0.0665 (15)	0.026 (3)*	0.461 (9)
C13B	1.0072 (18)	0.203 (2)	−0.0705 (16)	0.029 (4)*	0.461 (9)
H13B	1.0071	0.1493	−0.1440	0.035*	0.461 (9)
C14B	0.8655 (18)	0.252 (2)	0.0331 (14)	0.028 (3)*	0.461 (9)
H14B	0.7728	0.2254	0.0308	0.033*	0.461 (9)
C15B	1.306 (2)	0.188 (2)	−0.1803 (17)	0.028 (3)*	0.461 (9)
H15D	1.4029	0.1346	−0.1477	0.043*	0.461 (9)
H15E	1.3172	0.2816	−0.2225	0.043*	0.461 (9)
H15F	1.2962	0.1196	−0.2428	0.043*	0.461 (9)
Br1B	0.6416 (5)	0.1406 (5)	0.4607 (4)	0.0297 (5)	0.461 (9)
Br2B	0.4087 (6)	0.5267 (6)	0.1895 (6)	0.0438 (8)	0.461 (9)
C6B	0.4744 (8)	0.3165 (8)	0.3932 (6)	0.0174 (16)*	0.461 (9)
H6BA	0.4387	0.4117	0.4505	0.021*	0.461 (9)
C7B	0.5614 (9)	0.3472 (9)	0.2554 (7)	0.0208 (17)*	0.461 (9)
H7BA	0.5963	0.2535	0.1965	0.025*	0.461 (9)

	U11	U22	U33	U12	U13	U23
O1A	0.025 (3)	0.024 (3)	0.035 (3)	−0.015 (2)	−0.015 (2)	0.000 (2)
O2A	0.030 (4)	0.024 (3)	0.033 (3)	−0.015 (3)	−0.014 (3)	0.002 (3)
O3A	0.028 (4)	0.044 (4)	0.044 (4)	−0.029 (4)	0.000 (3)	−0.015 (3)
O4A	0.025 (4)	0.040 (4)	0.024 (5)	−0.018 (3)	0.000 (3)	−0.017 (3)
N1A	0.035 (3)	0.0307 (16)	0.021 (7)	−0.0187 (17)	−0.020 (4)	0.008 (5)
C1A	0.021 (3)	0.025 (4)	0.038 (4)	−0.015 (3)	−0.017 (2)	−0.001 (2)
C2A	0.021 (3)	0.025 (4)	0.038 (4)	−0.015 (3)	−0.017 (2)	−0.001 (2)
C3A	0.024 (4)	0.021 (5)	0.041 (4)	−0.016 (3)	−0.013 (3)	−0.004 (3)
C5A	0.030 (3)	0.022 (3)	0.033 (4)	−0.014 (3)	−0.014 (3)	0.003 (3)
C8A	0.024 (4)	0.028 (5)	0.043 (4)	−0.016 (4)	−0.016 (3)	0.000 (4)
C9A	0.025 (4)	0.025 (5)	0.029 (4)	−0.014 (4)	−0.014 (3)	0.001 (3)
C10A	0.030 (4)	0.027 (4)	0.026 (4)	−0.018 (3)	−0.018 (3)	0.004 (2)
C11A	0.025 (3)	0.026 (3)	0.037 (3)	−0.013 (2)	−0.015 (2)	0.005 (2)
C12A	0.025 (3)	0.026 (3)	0.037 (3)	−0.013 (2)	−0.015 (2)	0.005 (2)
C13A	0.027 (4)	0.030 (5)	0.030 (4)	−0.008 (4)	−0.016 (3)	−0.009 (3)
C14A	0.025 (4)	0.037 (6)	0.044 (4)	−0.017 (4)	−0.021 (3)	−0.005 (4)
C15A	0.033 (6)	0.059 (7)	0.044 (6)	−0.010 (5)	0.001 (5)	−0.020 (5)
Br1A	0.0302 (12)	0.0365 (8)	0.0632 (18)	−0.0172 (8)	−0.0264 (13)	0.0195 (12)
Br2A	0.0509 (16)	0.0327 (8)	0.0597 (17)	−0.0246 (10)	−0.0357 (13)	0.0189 (8)
C6A	0.033 (3)	0.031 (3)	0.037 (4)	−0.017 (3)	−0.017 (3)	0.002 (3)
C7A	0.031 (3)	0.030 (3)	0.039 (4)	−0.017 (3)	−0.012 (3)	0.001 (3)
N1B	0.035 (3)	0.0307 (16)	0.021 (7)	−0.0187 (17)	−0.020 (4)	0.008 (5)
Br1B	0.0228 (10)	0.0363 (6)	0.0371 (12)	−0.0145 (7)	−0.0151 (9)	0.0096 (9)
Br2B	0.0455 (16)	0.0513 (16)	0.0555 (18)	−0.0310 (13)	−0.0328 (14)	0.0264 (12)

O1A—C5A	1.375 (7)	O1B—C1B	1.343 (10)
O1A—C1A	1.387 (8)	O1B—C5B	1.368 (9)
O2A—C8A	1.218 (8)	O2B—C8B	1.207 (11)
O3A—N1A	1.243 (10)	O3B—N1B	1.251 (12)
O4A—N1A	1.222 (9)	O4B—N1B	1.228 (11)
N1A—C1A	1.439 (9)	N1B—C1B	1.436 (11)
C1A—C2A	1.329 (9)	C1B—C2B	1.347 (10)
C2A—C3A	1.416 (9)	C2B—C3B	1.413 (11)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C5A	1.352 (9)	C3B—C5B	1.364 (11)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C5A—C6A	1.465 (9)	C5B—C6B	1.496 (11)
C8A—C9A	1.469 (9)	C8B—C9B	1.472 (10)
C8A—C7A	1.550 (13)	C8B—C7B	1.527 (18)
C9A—C10A	1.405 (9)	C9B—C10B	1.399 (11)
C9A—C14A	1.406 (8)	C9B—C14B	1.401 (11)
C10A—C11A	1.380 (9)	C10B—C11B	1.391 (11)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.390 (9)	C11B—C12B	1.406 (10)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.416 (10)	C12B—C13B	1.388 (11)
C12A—C15A	1.508 (9)	C12B—C15B	1.515 (10)
C13A—C14A	1.377 (9)	C13B—C14B	1.379 (11)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
Br1A—C7A	1.992 (10)	Br1B—C6B	1.994 (8)
Br2A—C6A	1.987 (8)	Br2B—C7B	1.938 (10)
C6A—C7A	1.486 (10)	C6B—C7B	1.520 (10)
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C5A—O1A—C1A	101.7 (6)	O3B—N1B—C1B	111.7 (12)
O4A—N1A—O3A	124.4 (10)	O1B—C1B—C2B	110.1 (8)
O4A—N1A—C1A	118.0 (9)	O1B—C1B—N1B	117.5 (10)
O3A—N1A—C1A	115.5 (10)	C2B—C1B—N1B	132.3 (10)
C2A—C1A—O1A	114.5 (7)	C1B—C2B—C3B	105.8 (9)
C2A—C1A—N1A	130.6 (8)	C1B—C2B—H2BA	127.1
O1A—C1A—N1A	114.8 (8)	C3B—C2B—H2BA	127.1
C1A—C2A—C3A	104.2 (7)	C5B—C3B—C2B	107.5 (10)
C1A—C2A—H2AA	127.9	C5B—C3B—H3BA	126.3
C3A—C2A—H2AA	127.9	C2B—C3B—H3BA	126.3
C5A—C3A—C2A	106.9 (7)	C3B—C5B—O1B	107.6 (8)
C5A—C3A—H3AA	126.5	C3B—C5B—C6B	136.7 (9)
C2A—C3A—H3AA	126.5	O1B—C5B—C6B	115.8 (7)
C3A—C5A—O1A	112.1 (6)	O2B—C8B—C9B	123.2 (13)
C3A—C5A—C6A	130.6 (7)	O2B—C8B—C7B	118.0 (12)
O1A—C5A—C6A	117.3 (6)	C9B—C8B—C7B	118.1 (10)
O2A—C8A—C9A	122.9 (9)	C10B—C9B—C14B	118.6 (10)
O2A—C8A—C7A	115.9 (9)	C10B—C9B—C8B	118.5 (11)
C9A—C8A—C7A	120.4 (8)	C14B—C9B—C8B	122.9 (11)
C10A—C9A—C14A	117.7 (8)	C11B—C10B—C9B	121.1 (12)
C10A—C9A—C8A	117.3 (8)	C11B—C10B—H10B	119.5
C14A—C9A—C8A	125.0 (9)	C9B—C10B—H10B	119.5
C11A—C10A—C9A	120.5 (9)	C10B—C11B—C12B	119.3 (12)
C11A—C10A—H10A	119.7	C10B—C11B—H11B	120.3
C9A—C10A—H10A	119.7	C12B—C11B—H11B	120.3
C10A—C11A—C12A	122.6 (9)	C13B—C12B—C11B	119.5 (10)
C10A—C11A—H11A	118.7	C13B—C12B—C15B	122.3 (11)
C12A—C11A—H11A	118.7	C11B—C12B—C15B	118.1 (10)
C11A—C12A—C13A	116.6 (8)	C14B—C13B—C12B	120.8 (12)
C11A—C12A—C15A	123.1 (10)	C14B—C13B—H13B	119.6
C13A—C12A—C15A	120.1 (10)	C12B—C13B—H13B	119.6
C14A—C13A—C12A	121.6 (8)	C13B—C14B—C9B	120.6 (12)
C14A—C13A—H13A	119.2	C13B—C14B—H14B	119.7
C12A—C13A—H13A	119.2	C9B—C14B—H14B	119.7
C13A—C14A—C9A	120.9 (8)	C12B—C15B—H15D	109.5
C13A—C14A—H14A	119.5	C12B—C15B—H15E	109.5
C9A—C14A—H14A	119.5	H15D—C15B—H15E	109.5
C5A—C6A—C7A	113.1 (6)	C12B—C15B—H15F	109.5
C5A—C6A—Br2A	110.2 (5)	H15D—C15B—H15F	109.5
C7A—C6A—Br2A	105.6 (6)	H15E—C15B—H15F	109.5
C5A—C6A—H6AA	109.3	C5B—C6B—C7B	115.9 (6)
C7A—C6A—H6AA	109.3	C5B—C6B—Br1B	106.1 (5)
Br2A—C6A—H6AA	109.3	C7B—C6B—Br1B	107.6 (5)
C6A—C7A—C8A	115.3 (7)	C5B—C6B—H6BA	109.0
C6A—C7A—Br1A	106.7 (5)	C7B—C6B—H6BA	109.0
C8A—C7A—Br1A	102.9 (7)	Br1B—C6B—H6BA	109.0
C6A—C7A—H7AA	110.5	C6B—C7B—C8B	111.7 (8)
C8A—C7A—H7AA	110.5	C6B—C7B—Br2B	109.3 (6)
Br1A—C7A—H7AA	110.5	C8B—C7B—Br2B	105.6 (8)
C1B—O1B—C5B	108.3 (8)	C6B—C7B—H7BA	110.0
O4B—N1B—O3B	124.1 (14)	C8B—C7B—H7BA	110.0
O4B—N1B—C1B	121.7 (12)	Br2B—C7B—H7BA	110.0
C5A—O1A—C1A—C2A	5.5 (14)	C5B—O1B—C1B—C2B	−5.7 (17)
C5A—O1A—C1A—N1A	−177.3 (19)	C5B—O1B—C1B—N1B	178 (2)
O4A—N1A—C1A—C2A	169 (2)	O4B—N1B—C1B—O1B	−10 (5)
O3A—N1A—C1A—C2A	5(4)	O3B—N1B—C1B—O1B	153 (2)
O4A—N1A—C1A—O1A	−7(4)	O4B—N1B—C1B—C2B	175 (2)
O3A—N1A—C1A—O1A	−172 (2)	O3B—N1B—C1B—C2B	−23 (5)
O1A—C1A—C2A—C3A	−7.5 (16)	O1B—C1B—C2B—C3B	8.7 (19)
N1A—C1A—C2A—C3A	176 (3)	N1B—C1B—C2B—C3B	−175 (3)
C1A—C2A—C3A—C5A	6.3 (17)	C1B—C2B—C3B—C5B	−8(2)
C2A—C3A—C5A—O1A	−3.3 (17)	C2B—C3B—C5B—O1B	5(2)
C2A—C3A—C5A—C6A	174.7 (11)	C2B—C3B—C5B—C6B	−173.2 (13)
C1A—O1A—C5A—C3A	−1.1 (14)	C1B—O1B—C5B—C3B	0.1 (17)
C1A—O1A—C5A—C6A	−179.3 (11)	C1B—O1B—C5B—C6B	178.9 (13)
O2A—C8A—C9A—C10A	3(3)	O2B—C8B—C9B—C10B	13 (4)
C7A—C8A—C9A—C10A	−166 (2)	C7B—C8B—C9B—C10B	−176 (3)
O2A—C8A—C9A—C14A	−175.3 (16)	O2B—C8B—C9B—C14B	−170 (2)
C7A—C8A—C9A—C14A	15 (3)	C7B—C8B—C9B—C14B	1(3)
C14A—C9A—C10A—C11A	−2(4)	C14B—C9B—C10B—C11B	−1(5)
C8A—C9A—C10A—C11A	180 (2)	C8B—C9B—C10B—C11B	176 (3)
C9A—C10A—C11A—C12A	−1(4)	C9B—C10B—C11B—C12B	3(5)
C10A—C11A—C12A—C13A	3(3)	C10B—C11B—C12B—C13B	−1(4)
C10A—C11A—C12A—C15A	−172 (3)	C10B—C11B—C12B—C15B	175 (3)
C11A—C12A—C13A—C14A	−2(2)	C11B—C12B—C13B—C14B	−1(3)
C15A—C12A—C13A—C14A	172.9 (17)	C15B—C12B—C13B—C14B	−177.8 (19)
C12A—C13A—C14A—C9A	−1(3)	C12B—C13B—C14B—C9B	3(3)
C10A—C9A—C14A—C13A	2(3)	C10B—C9B—C14B—C13B	−2(4)
C8A—C9A—C14A—C13A	−178.9 (17)	C8B—C9B—C14B—C13B	−179 (2)
C3A—C5A—C6A—C7A	140.5 (14)	C3B—C5B—C6B—C7B	−138.9 (18)
O1A—C5A—C6A—C7A	−41.6 (10)	O1B—C5B—C6B—C7B	42.8 (10)
C3A—C5A—C6A—Br2A	−101.6 (14)	C3B—C5B—C6B—Br1B	101.8 (18)
O1A—C5A—C6A—Br2A	76.3 (8)	O1B—C5B—C6B—Br1B	−76.5 (8)
C5A—C6A—C7A—C8A	−175.9 (8)	C5B—C6B—C7B—C8B	−178.2 (9)
Br2A—C6A—C7A—C8A	63.6 (8)	Br1B—C6B—C7B—C8B	−59.7 (9)
C5A—C6A—C7A—Br1A	−62.3 (6)	C5B—C6B—C7B—Br2B	65.3 (7)
Br2A—C6A—C7A—Br1A	177.1 (3)	Br1B—C6B—C7B—Br2B	−176.3 (4)
O2A—C8A—C7A—C6A	45.1 (16)	O2B—C8B—C7B—C6B	−43.9 (18)
C9A—C8A—C7A—C6A	−144.9 (13)	C9B—C8B—C7B—C6B	145.4 (16)
O2A—C8A—C7A—Br1A	−70.7 (13)	O2B—C8B—C7B—Br2B	74.8 (16)
C9A—C8A—C7A—Br1A	99.4 (14)	C9B—C8B—C7B—Br2B	−95.9 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2AA···O3Ai	0.93	2.53	3.210 (15)	131
C3A—H3AA···O2Aii	0.93	2.51	3.216 (12)	133
C6A—H6AA···O2Aii	0.98	2.33	3.217 (10)	151
C13A—H13A···O3Aiii	0.93	2.55	3.434 (13)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2A—H2AA⋯O3Ai	0.93	2.53	3.210 (15)	131
C3A—H3AA⋯O2Aii	0.93	2.51	3.216 (12)	133
C6A—H6AA⋯O2Aii	0.98	2.33	3.217 (10)	151
C13A—H13A⋯O3Aiii	0.93	2.55	3.434 (13)	158

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