2,3-Dibromo-3-(4-chloro-phen-yl)-1-(4-nitro-thio-phen-2-yl)propan-1-one.

The title compound, C(13)H(8)Br(2)ClNO(3)S, exhibits whole-mol-ecule disorder over two orientations in a 0.805 (6):0.195 (6) ratio. The dihedral angles between the thio-phene ring [maximum deviations = 0.017 (4) and 0.033 (9) Å for the major and minor components, respectively] and the chloro-substituted phenyl ring are 32.1 (5) (major component) and 26.3 (18)° (minor component). In the crystal, C-H⋯Cl and C-H⋯O hydrogen bonds link the mol-ecules into sheets lying parallel to the bc plane. Aromatic π-π stacking inter-actions [centroid-centroid distance = 3.550 (7) Å] are also observed.

Related literature

For background to nitro­thio­phene derivatives, see: Holla et al. (1986 ▶); Kalluraya et al. (1994 ▶); Kalluraya & Shetty (1997 ▶); Rai et al. (2008 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H8Br2ClNO3S

M = 453.53

Monoclinic,

a = 28.5425 (17) Å

b = 9.5470 (5) Å

c = 11.4047 (7) Å

β = 103.224 (2)°

V = 3025.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 5.68 mm−1

T = 100 K

0.31 × 0.24 × 0.11 mm

Data collection

Bruker SMART APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.269, T max = 0.564

33329 measured reflections

5031 independent reflections

4272 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.11

5031 reflections

275 parameters

504 restraints

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −0.75 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/S1600536812034551/hb6917sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034551/hb6917Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034551/hb6917Isup3.cml

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

C13H8Br2ClNO3S	F(000) = 1760
Mr = 453.53	Dx = 1.991 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9951 reflections
a = 28.5425 (17) Å	θ = 2.8–31.4°
b = 9.5470 (5) Å	µ = 5.68 mm−1
c = 11.4047 (7) Å	T = 100 K
β = 103.224 (2)°	Block, colourless
V = 3025.3 (3) Å3	0.31 × 0.24 × 0.11 mm
Z = 8

Bruker SMART APEX DUO CCD diffractometer	5031 independent reflections
Radiation source: fine-focus sealed tube	4272 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
φ and ω scans	θmax = 31.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −41→41
Tmin = 0.269, Tmax = 0.564	k = −14→14
33329 measured reflections	l = −16→16

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) = 0.112	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0628P)2 + 5.4597P] where P = (Fo2 + 2Fc2)/3
5031 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 1.33 e Å−3
504 restraints	Δρmin = −0.75 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 100.0 (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)
Br1	0.30443 (7)	0.1934 (2)	0.09470 (18)	0.0220 (2)	0.805 (6)
Br2	0.45859 (4)	0.04291 (14)	0.08975 (14)	0.0328 (3)	0.805 (6)
Cl1	0.46000 (9)	0.7011 (2)	0.3575 (2)	0.0325 (4)	0.805 (6)
S1	0.31346 (12)	−0.2888 (4)	−0.0725 (3)	0.0278 (8)	0.805 (6)
O1	0.35091 (17)	−0.0087 (5)	−0.1008 (4)	0.0250 (8)	0.805 (6)
O2	0.2644 (3)	−0.5160 (6)	0.2173 (6)	0.0280 (10)	0.805 (6)
O3	0.3097 (3)	−0.3704 (7)	0.3399 (4)	0.0359 (11)	0.805 (6)
N1	0.29043 (19)	−0.4130 (6)	0.2375 (4)	0.0219 (9)	0.805 (6)
C9	0.34861 (14)	−0.0298 (3)	0.0020 (3)	0.0196 (7)	0.805 (6)
C10	0.33008 (15)	−0.1624 (4)	0.0378 (3)	0.0186 (8)	0.805 (6)
C11	0.32325 (14)	−0.2035 (4)	0.1496 (4)	0.0191 (8)	0.805 (6)
H11B	0.3313	−0.1501	0.2217	0.023*	0.805 (6)
C12	0.3022 (2)	−0.3397 (6)	0.1375 (4)	0.0199 (9)	0.805 (6)
C13	0.2942 (8)	−0.3972 (12)	0.0240 (6)	0.0211 (14)	0.805 (6)
H13B	0.2797	−0.4860	0.0026	0.025*	0.805 (6)
C1	0.40955 (16)	0.4341 (4)	0.0905 (4)	0.0228 (9)	0.805 (6)
H1BA	0.3958	0.4389	0.0064	0.027*	0.805 (6)
C2	0.4226 (2)	0.5568 (6)	0.1542 (5)	0.0246 (9)	0.805 (6)
H2A	0.4178	0.6452	0.1149	0.029*	0.805 (6)
C3	0.4427 (4)	0.5479 (5)	0.2764 (5)	0.0226 (9)	0.805 (6)
C4	0.44978 (18)	0.4192 (5)	0.3367 (4)	0.0242 (9)	0.805 (6)
H4BA	0.4636	0.4150	0.4207	0.029*	0.805 (6)
C5	0.43608 (16)	0.2978 (4)	0.2707 (4)	0.0239 (7)	0.805 (6)
H5A	0.4403	0.2095	0.3101	0.029*	0.805 (6)
C6	0.41604 (14)	0.3040 (3)	0.1464 (3)	0.0202 (6)	0.805 (6)
C7	0.40208 (11)	0.1763 (3)	0.0704 (3)	0.0195 (6)	0.805 (6)
H7BA	0.3919	0.2052	−0.0159	0.023*	0.805 (6)
C8	0.36384 (11)	0.0820 (3)	0.1003 (3)	0.0186 (6)	0.805 (6)
H8BA	0.3754	0.0376	0.1812	0.022*	0.805 (6)
Br1X	0.3073 (3)	0.1867 (8)	0.1063 (7)	0.0159 (8)*	0.195 (6)
Br2X	0.45697 (15)	0.0543 (4)	0.0743 (4)	0.0118 (6)*	0.195 (6)
Cl1X	0.4684 (3)	0.6876 (9)	0.3684 (9)	0.0225 (15)*	0.195 (6)
S1X	0.3131 (3)	−0.2879 (11)	−0.0739 (10)	0.0085 (17)*	0.195 (6)
O1X	0.3601 (6)	−0.023 (2)	−0.1041 (15)	0.016 (3)*	0.195 (6)
O2X	0.2680 (13)	−0.499 (3)	0.225 (3)	0.035 (5)*	0.195 (6)
O3X	0.3116 (13)	−0.348 (3)	0.343 (2)	0.041 (5)*	0.195 (6)
N1X	0.2988 (10)	−0.408 (3)	0.2442 (19)	0.023 (3)*	0.195 (6)
C9X	0.3611 (6)	−0.0443 (15)	−0.0001 (15)	0.018 (2)*	0.195 (6)
C10X	0.3400 (7)	−0.1710 (17)	0.0376 (15)	0.018 (3)*	0.195 (6)
C11X	0.3338 (7)	−0.208 (2)	0.1501 (16)	0.019 (3)*	0.195 (6)
H11A	0.3440	−0.1547	0.2218	0.023*	0.195 (6)
C12X	0.3095 (12)	−0.338 (3)	0.1411 (19)	0.020 (2)*	0.195 (6)
C13X	0.298 (3)	−0.396 (5)	0.028 (2)	0.021 (3)*	0.195 (6)
H13A	0.2827	−0.4853	0.0091	0.026*	0.195 (6)
C1X	0.4024 (8)	0.4497 (18)	0.0976 (19)	0.022 (3)*	0.195 (6)
H1A	0.3894	0.4634	0.0141	0.027*	0.195 (6)
C2X	0.4233 (8)	0.561 (2)	0.168 (2)	0.025 (3)*	0.195 (6)
H2BA	0.4233	0.6515	0.1337	0.030*	0.195 (6)
C3X	0.4443 (17)	0.539 (2)	0.288 (2)	0.024 (3)*	0.195 (6)
C4X	0.4420 (9)	0.410 (2)	0.343 (2)	0.024 (3)*	0.195 (6)
H4A	0.4535	0.3983	0.4277	0.029*	0.195 (6)
C5X	0.4221 (6)	0.2990 (17)	0.2698 (14)	0.022 (2)*	0.195 (6)
H5BA	0.4232	0.2075	0.3030	0.027*	0.195 (6)
C6X	0.4003 (6)	0.3189 (15)	0.1474 (14)	0.023 (2)*	0.195 (6)
C7X	0.3736 (5)	0.1993 (13)	0.0709 (13)	0.022 (2)*	0.195 (6)
H7A	0.3712	0.2173	−0.0167	0.026*	0.195 (6)
C8X	0.3891 (5)	0.0534 (14)	0.1024 (14)	0.024 (2)*	0.195 (6)
H8A	0.3871	0.0244	0.1854	0.029*	0.195 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0208 (4)	0.0242 (4)	0.0211 (5)	0.0032 (2)	0.0050 (3)	−0.0006 (3)
Br2	0.0255 (2)	0.0390 (4)	0.0325 (6)	0.0105 (2)	0.0038 (3)	−0.0058 (3)
Cl1	0.0392 (10)	0.0234 (6)	0.0339 (8)	−0.0051 (6)	0.0061 (7)	−0.0101 (5)
S1	0.0432 (11)	0.0217 (7)	0.0185 (7)	−0.0039 (3)	0.0069 (4)	−0.0021 (3)
O1	0.030 (2)	0.0236 (15)	0.0216 (14)	0.0009 (14)	0.0072 (13)	0.0021 (10)
O2	0.040 (2)	0.0171 (17)	0.031 (2)	−0.0044 (12)	0.0148 (15)	0.0032 (14)
O3	0.061 (2)	0.035 (2)	0.0115 (13)	−0.0088 (19)	0.0079 (12)	0.0039 (12)
N1	0.027 (2)	0.0211 (14)	0.0198 (14)	0.0022 (16)	0.0091 (14)	0.0028 (11)
C9	0.0198 (15)	0.0191 (13)	0.0197 (14)	0.0005 (11)	0.0043 (12)	−0.0030 (10)
C10	0.0210 (18)	0.0182 (13)	0.0167 (14)	0.0012 (12)	0.0042 (13)	−0.0014 (10)
C11	0.0191 (18)	0.0176 (12)	0.0204 (15)	0.0010 (13)	0.0040 (13)	−0.0006 (10)
C12	0.024 (3)	0.0178 (12)	0.0185 (14)	0.0002 (14)	0.0063 (14)	0.0004 (10)
C13	0.028 (4)	0.0171 (13)	0.0187 (15)	0.0002 (14)	0.0058 (17)	−0.0003 (11)
C1	0.0227 (18)	0.0226 (15)	0.0231 (16)	0.0032 (12)	0.0048 (13)	−0.0021 (12)
C2	0.0262 (15)	0.0213 (14)	0.026 (2)	0.0008 (10)	0.0051 (14)	−0.0017 (13)
C3	0.0257 (16)	0.0191 (14)	0.0224 (19)	−0.0040 (14)	0.0038 (16)	−0.0066 (13)
C4	0.025 (2)	0.0268 (15)	0.0207 (16)	−0.0038 (13)	0.0048 (14)	−0.0034 (12)
C5	0.0247 (17)	0.0219 (13)	0.0238 (16)	−0.0002 (13)	0.0030 (14)	−0.0018 (11)
C6	0.0194 (14)	0.0200 (13)	0.0208 (14)	−0.0001 (10)	0.0041 (12)	−0.0020 (10)
C7	0.0209 (13)	0.0196 (12)	0.0182 (14)	0.0017 (9)	0.0052 (10)	−0.0009 (10)
C8	0.0224 (13)	0.0158 (11)	0.0173 (13)	−0.0007 (10)	0.0042 (10)	0.0005 (10)

Br1—C8	1.990 (4)	Br1X—C7X	2.029 (16)
Br2—C7	2.027 (3)	Br2X—C8X	2.034 (16)
Cl1—C3	1.741 (4)	Cl1X—C3X	1.742 (14)
S1—C13	1.691 (5)	S1X—C13X	1.687 (15)
S1—C10	1.730 (4)	S1X—C10X	1.733 (14)
O1—C9	1.206 (5)	O1X—C9X	1.198 (15)
O2—N1	1.223 (5)	O2X—N1X	1.216 (15)
O3—N1	1.239 (5)	O3X—N1X	1.240 (16)
N1—C12	1.441 (4)	N1X—C12X	1.444 (14)
C9—C10	1.466 (4)	C9X—C10X	1.459 (14)
C9—C8	1.537 (4)	C9X—C8X	1.56 (2)
C10—C11	1.390 (5)	C10X—C11X	1.381 (15)
C11—C12	1.426 (5)	C11X—C12X	1.419 (15)
C11—H11B	0.9500	C11X—H11A	0.9500
C12—C13	1.377 (5)	C12X—C13X	1.376 (15)
C13—H13B	0.9500	C13X—H13A	0.9500
C1—C2	1.384 (5)	C1X—C6X	1.378 (15)
C1—C6	1.389 (5)	C1X—C2X	1.379 (15)
C1—H1BA	0.9500	C1X—H1A	0.9500
C2—C3	1.383 (5)	C2X—C3X	1.378 (15)
C2—H2A	0.9500	C2X—H2BA	0.9500
C3—C4	1.400 (5)	C3X—C4X	1.395 (15)
C4—C5	1.389 (5)	C4X—C5X	1.390 (15)
C4—H4BA	0.9500	C4X—H4A	0.9500
C5—C6	1.403 (5)	C5X—C6X	1.404 (15)
C5—H5A	0.9500	C5X—H5BA	0.9500
C6—C7	1.496 (4)	C6X—C7X	1.531 (19)
C7—C8	1.513 (4)	C7X—C8X	1.480 (19)
C7—H7BA	1.0000	C7X—H7A	1.0000
C8—H8BA	1.0000	C8X—H8A	1.0000
C13—S1—C10	91.7 (3)	C13X—S1X—C10X	91.9 (9)
O2—N1—O3	124.1 (5)	O2X—N1X—O3X	123 (2)
O2—N1—C12	118.8 (4)	O2X—N1X—C12X	117 (2)
O3—N1—C12	116.9 (4)	O3X—N1X—C12X	116.6 (19)
O1—C9—C10	121.2 (4)	O1X—C9X—C10X	121.2 (16)
O1—C9—C8	121.6 (3)	O1X—C9X—C8X	121.9 (15)
C10—C9—C8	117.2 (3)	C10X—C9X—C8X	116.7 (13)
C11—C10—C9	129.4 (3)	C11X—C10X—C9X	129.4 (14)
C11—C10—S1	113.5 (3)	C11X—C10X—S1X	112.8 (11)
C9—C10—S1	117.1 (3)	C9X—C10X—S1X	117.4 (11)
C10—C11—C12	108.2 (3)	C10X—C11X—C12X	108.8 (13)
C10—C11—H11B	125.9	C10X—C11X—H11A	125.6
C12—C11—H11B	125.9	C12X—C11X—H11A	125.6
C13—C12—C11	115.5 (4)	C13X—C12X—C11X	115.6 (14)
C13—C12—N1	122.2 (4)	C13X—C12X—N1X	121.8 (15)
C11—C12—N1	122.4 (4)	C11X—C12X—N1X	122.5 (16)
C12—C13—S1	111.1 (3)	C12X—C13X—S1X	110.5 (13)
C12—C13—H13B	124.5	C12X—C13X—H13A	124.7
S1—C13—H13B	124.5	S1X—C13X—H13A	124.7
C2—C1—C6	121.6 (4)	C6X—C1X—C2X	120.7 (17)
C2—C1—H1BA	119.2	C6X—C1X—H1A	119.6
C6—C1—H1BA	119.2	C2X—C1X—H1A	119.6
C3—C2—C1	118.4 (4)	C3X—C2X—C1X	119.6 (18)
C3—C2—H2A	120.8	C3X—C2X—H2BA	120.2
C1—C2—H2A	120.8	C1X—C2X—H2BA	120.2
C2—C3—C4	122.0 (4)	C2X—C3X—C4X	121.9 (15)
C2—C3—Cl1	119.0 (4)	C2X—C3X—Cl1X	115.6 (14)
C4—C3—Cl1	119.0 (4)	C4X—C3X—Cl1X	122.3 (15)
C5—C4—C3	118.3 (4)	C5X—C4X—C3X	117.1 (16)
C5—C4—H4BA	120.8	C5X—C4X—H4A	121.5
C3—C4—H4BA	120.8	C3X—C4X—H4A	121.5
C4—C5—C6	120.8 (4)	C4X—C5X—C6X	121.6 (15)
C4—C5—H5A	119.6	C4X—C5X—H5BA	119.2
C6—C5—H5A	119.6	C6X—C5X—H5BA	119.2
C1—C6—C5	118.9 (3)	C1X—C6X—C5X	118.7 (14)
C1—C6—C7	118.2 (3)	C1X—C6X—C7X	120.3 (14)
C5—C6—C7	122.9 (3)	C5X—C6X—C7X	121.0 (13)
C6—C7—C8	117.7 (3)	C8X—C7X—C6X	118.8 (12)
C6—C7—Br2	110.4 (2)	C8X—C7X—Br1X	97.8 (10)
C8—C7—Br2	101.46 (19)	C6X—C7X—Br1X	107.2 (10)
C6—C7—H7BA	108.9	C8X—C7X—H7A	110.7
C8—C7—H7BA	108.9	C6X—C7X—H7A	110.7
Br2—C7—H7BA	108.9	Br1X—C7X—H7A	110.7
C7—C8—C9	110.3 (3)	C7X—C8X—C9X	107.9 (12)
C7—C8—Br1	109.2 (2)	C7X—C8X—Br2X	101.5 (9)
C9—C8—Br1	104.5 (2)	C9X—C8X—Br2X	103.1 (10)
C7—C8—H8BA	110.9	C7X—C8X—H8A	114.3
C9—C8—H8BA	110.9	C9X—C8X—H8A	114.3
Br1—C8—H8BA	110.9	Br2X—C8X—H8A	114.3
O1—C9—C10—C11	−177.6 (4)	O1X—C9X—C10X—C11X	−173 (2)
C8—C9—C10—C11	1.1 (6)	C8X—C9X—C10X—C11X	12 (3)
O1—C9—C10—S1	1.9 (6)	O1X—C9X—C10X—S1X	−1 (3)
C8—C9—C10—S1	−179.4 (3)	C8X—C9X—C10X—S1X	−174.9 (13)
C13—S1—C10—C11	2.8 (9)	C13X—S1X—C10X—C11X	−5 (4)
C13—S1—C10—C9	−176.8 (9)	C13X—S1X—C10X—C9X	−179 (4)
C9—C10—C11—C12	177.2 (4)	C9X—C10X—C11X—C12X	177 (2)
S1—C10—C11—C12	−2.3 (5)	S1X—C10X—C11X—C12X	4 (3)
C10—C11—C12—C13	0.5 (12)	C10X—C11X—C12X—C13X	−1 (6)
C10—C11—C12—N1	179.9 (5)	C10X—C11X—C12X—N1X	178 (3)
O2—N1—C12—C13	−14.5 (14)	O2X—N1X—C12X—C13X	−20 (7)
O3—N1—C12—C13	162.0 (13)	O3X—N1X—C12X—C13X	179 (6)
O2—N1—C12—C11	166.2 (7)	O2X—N1X—C12X—C11X	162 (4)
O3—N1—C12—C11	−17.3 (9)	O3X—N1X—C12X—C11X	1 (5)
C11—C12—C13—S1	1.5 (17)	C11X—C12X—C13X—S1X	−3 (8)
N1—C12—C13—S1	−177.9 (8)	N1X—C12X—C13X—S1X	178 (4)
C10—S1—C13—C12	−2.4 (14)	C10X—S1X—C13X—C12X	5 (6)
C6—C1—C2—C3	0.3 (8)	C6X—C1X—C2X—C3X	3 (3)
C1—C2—C3—C4	−0.6 (13)	C1X—C2X—C3X—C4X	−5 (5)
C1—C2—C3—Cl1	179.2 (5)	C1X—C2X—C3X—Cl1X	−178.7 (17)
C2—C3—C4—C5	0.2 (13)	C2X—C3X—C4X—C5X	7 (6)
Cl1—C3—C4—C5	−179.6 (5)	Cl1X—C3X—C4X—C5X	−180 (3)
C3—C4—C5—C6	0.5 (8)	C3X—C4X—C5X—C6X	−7 (4)
C2—C1—C6—C5	0.3 (6)	C2X—C1X—C6X—C5X	−3 (2)
C2—C1—C6—C7	−178.6 (4)	C2X—C1X—C6X—C7X	175.2 (11)
C4—C5—C6—C1	−0.8 (6)	C4X—C5X—C6X—C1X	5 (3)
C4—C5—C6—C7	178.1 (4)	C4X—C5X—C6X—C7X	−173.1 (18)
C1—C6—C7—C8	−119.9 (4)	C1X—C6X—C7X—C8X	152.4 (17)
C5—C6—C7—C8	61.3 (5)	C5X—C6X—C7X—C8X	−29 (2)
C1—C6—C7—Br2	124.3 (3)	C1X—C6X—C7X—Br1X	−98.1 (18)
C5—C6—C7—Br2	−54.5 (4)	C5X—C6X—C7X—Br1X	80.3 (17)
C6—C7—C8—C9	171.2 (3)	C6X—C7X—C8X—C9X	−171.9 (13)
Br2—C7—C8—C9	−68.2 (3)	Br1X—C7X—C8X—C9X	73.4 (12)
C6—C7—C8—Br1	56.9 (3)	C6X—C7X—C8X—Br2X	−63.9 (15)
Br2—C7—C8—Br1	177.45 (15)	Br1X—C7X—C8X—Br2X	−178.6 (6)
O1—C9—C8—C7	−28.4 (5)	O1X—C9X—C8X—C7X	51 (2)
C10—C9—C8—C7	153.0 (3)	C10X—C9X—C8X—C7X	−134.3 (16)
O1—C9—C8—Br1	88.9 (4)	O1X—C9X—C8X—Br2X	−55.5 (18)
C10—C9—C8—Br1	−89.8 (3)	C10X—C9X—C8X—Br2X	118.8 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7BA···Cl1i	1.00	2.82	3.441 (4)	121
C11—H11B···O1ii	0.95	2.49	3.435 (6)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7BA⋯Cl1i	1.00	2.82	3.441 (4)	121
C11—H11B⋯O1ii	0.95	2.49	3.435 (6)	175

Symmetry codes: (i) ; (ii) .