3-(4-Bromo-phenyl-sulfin-yl)-5-fluoro-2-methyl-1-benzofuran.

There are two symmetry-independent mol-ecules, A and B, in the asymmetric unit of the title compound, C(15)H(10)BrFO(2)S. The dihedral angle formed by the 4-bromo-phenyl ring and the mean plane of the benzofuran fragment is 88.26 (6)° in mol-ecule A and 88.25 (6)° in mol-ecule B. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯F, C-H⋯O and C-H⋯π inter-actions. The crystal structure also exhibits inter-molecular C-Br⋯π [3.737 (3) Å] inter-actions, and weak π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.557 (3) Å, inter-planar distance = 3.421 (3) Å and slippage = 0.974 (3) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶,c ▶).

Experimental

Crystal data

C15H10BrFO2S

M = 353.20

Triclinic,

a = 9.6576 (1) Å

b = 11.9134 (2) Å

c = 13.5395 (2) Å

α = 94.038 (1)°

β = 101.096 (1)°

γ = 112.610 (1)°

V = 1393.13 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.11 mm−1

T = 173 K

0.34 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.554, T max = 0.746

24788 measured reflections

6444 independent reflections

4958 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.02

6444 reflections

363 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.73 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005715/zs2180sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005715/zs2180Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005715/zs2180Isup3.cml

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

C15H10BrFO2S	Z = 4
Mr = 353.20	F(000) = 704
Triclinic, P1	Dx = 1.684 Mg m−3
Hall symbol: -P 1	Melting point = 382–383 K
a = 9.6576 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.9134 (2) Å	Cell parameters from 8290 reflections
c = 13.5395 (2) Å	θ = 2.2–27.2°
α = 94.038 (1)°	µ = 3.11 mm−1
β = 101.096 (1)°	T = 173 K
γ = 112.610 (1)°	Block, colourless
V = 1393.13 (3) Å3	0.34 × 0.27 × 0.17 mm

Bruker SMART APEXII CCD diffractometer	6444 independent reflections
Radiation source: rotating anode	4958 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.039
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 1.6°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→15
Tmin = 0.554, Tmax = 0.746	l = −17→17
24788 measured reflections

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0348P)2 + 0.8229P] where P = (Fo2 + 2Fc2)/3
6444 reflections	(Δ/σ)max = 0.001
363 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

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
Br1	−0.19888 (4)	0.64684 (3)	0.55467 (2)	0.05801 (11)
S1	0.27869 (7)	0.41871 (5)	0.74250 (5)	0.03725 (14)
O1	0.62608 (18)	0.66639 (14)	0.94699 (13)	0.0358 (4)
O2	0.1845 (2)	0.30693 (15)	0.78067 (15)	0.0497 (5)
F1	0.12944 (19)	0.63331 (15)	1.09105 (13)	0.0607 (5)
C1	0.4009 (3)	0.5329 (2)	0.84628 (17)	0.0305 (5)
C2	0.3666 (3)	0.58567 (19)	0.93269 (16)	0.0282 (4)
C3	0.2340 (3)	0.5723 (2)	0.96518 (18)	0.0359 (5)
H3	0.1341	0.5171	0.9271	0.043*
C4	0.2560 (3)	0.6437 (2)	1.05536 (19)	0.0392 (5)
C5	0.3978 (3)	0.7245 (2)	1.11426 (18)	0.0406 (6)
H5	0.4044	0.7711	1.1762	0.049*
C6	0.5302 (3)	0.7375 (2)	1.08299 (18)	0.0376 (5)
H6	0.6297	0.7920	1.1222	0.045*
C7	0.5101 (3)	0.66719 (19)	0.99181 (17)	0.0309 (5)
C8	0.5566 (3)	0.5840 (2)	0.85873 (18)	0.0335 (5)
C9	0.6600 (3)	0.5691 (3)	0.7962 (2)	0.0472 (6)
H15A	0.7009	0.6429	0.7647	0.071*
H15B	0.6019	0.4970	0.7428	0.071*
H15C	0.7457	0.5577	0.8396	0.071*
C10	0.1497 (3)	0.4894 (2)	0.69659 (16)	0.0312 (5)
C11	−0.0031 (3)	0.4298 (2)	0.69762 (18)	0.0351 (5)
H11	−0.0371	0.3567	0.7269	0.042*
C12	−0.1076 (3)	0.4776 (2)	0.65540 (18)	0.0372 (5)
H12	−0.2135	0.4382	0.6562	0.045*
C13	−0.0552 (3)	0.5827 (2)	0.61246 (17)	0.0366 (5)
C14	0.0986 (3)	0.6429 (2)	0.61141 (18)	0.0417 (6)
H14	0.1325	0.7160	0.5821	0.050*
C15	0.2025 (3)	0.5955 (2)	0.65345 (18)	0.0389 (5)
H15	0.3084	0.6350	0.6528	0.047*
Br2	0.08498 (5)	0.79746 (3)	−0.15733 (2)	0.07262 (12)
S2	0.28070 (7)	1.09998 (5)	0.29462 (5)	0.03822 (15)
O3	0.28658 (18)	0.82877 (14)	0.44327 (12)	0.0327 (3)
O4	0.4310 (2)	1.20632 (15)	0.30530 (15)	0.0517 (5)
F2	0.80169 (17)	0.96487 (15)	0.29759 (12)	0.0505 (4)
C16	0.3202 (3)	0.98537 (19)	0.35506 (17)	0.0297 (5)
C17	0.4479 (2)	0.95086 (18)	0.35492 (16)	0.0275 (4)
C18	0.5797 (3)	0.9915 (2)	0.31620 (17)	0.0316 (5)
H18	0.6039	1.0589	0.2796	0.038*
C19	0.6722 (3)	0.9282 (2)	0.33421 (18)	0.0342 (5)
C20	0.6434 (3)	0.8299 (2)	0.38744 (18)	0.0357 (5)
H20	0.7118	0.7896	0.3965	0.043*
C21	0.5147 (3)	0.7908 (2)	0.42724 (17)	0.0345 (5)
H21	0.4921	0.7240	0.4647	0.041*
C22	0.4202 (2)	0.85308 (19)	0.41017 (16)	0.0287 (5)
C23	0.2295 (2)	0.91161 (19)	0.40823 (17)	0.0307 (5)
C24	0.0814 (3)	0.9007 (2)	0.4318 (2)	0.0407 (6)
H24A	0.0626	0.9736	0.4169	0.061*
H24B	0.0869	0.8945	0.5041	0.061*
H24C	−0.0031	0.8269	0.3900	0.061*
C25	0.2258 (3)	1.0190 (2)	0.16674 (19)	0.0357 (5)
C26	0.0802 (3)	0.9237 (2)	0.1333 (2)	0.0427 (6)
H26	0.0107	0.9038	0.1767	0.051*
C27	0.0376 (3)	0.8582 (2)	0.0363 (2)	0.0495 (7)
H27	−0.0615	0.7925	0.0122	0.059*
C28	0.1403 (3)	0.8894 (2)	−0.0250 (2)	0.0459 (6)
C29	0.2847 (3)	0.9855 (2)	0.0071 (2)	0.0462 (6)
H29	0.3537	1.0057	−0.0367	0.055*
C30	0.3269 (3)	1.0515 (2)	0.1042 (2)	0.0414 (6)
H30	0.4248	1.1188	0.1274	0.050*

	U11	U22	U33	U12	U13	U23
Br1	0.0696 (2)	0.0880 (2)	0.04255 (16)	0.05785 (19)	0.01397 (14)	0.01981 (14)
S1	0.0372 (3)	0.0393 (3)	0.0347 (3)	0.0205 (3)	0.0007 (3)	−0.0048 (2)
O1	0.0243 (8)	0.0350 (8)	0.0434 (9)	0.0086 (7)	0.0046 (7)	0.0069 (7)
O2	0.0450 (11)	0.0296 (8)	0.0623 (12)	0.0122 (8)	−0.0068 (9)	0.0031 (8)
F1	0.0488 (10)	0.0662 (10)	0.0585 (10)	0.0102 (8)	0.0284 (8)	−0.0102 (8)
C1	0.0279 (11)	0.0346 (11)	0.0290 (11)	0.0135 (9)	0.0048 (9)	0.0058 (9)
C2	0.0289 (11)	0.0261 (10)	0.0261 (10)	0.0089 (9)	0.0032 (9)	0.0052 (8)
C3	0.0259 (12)	0.0381 (12)	0.0338 (12)	0.0045 (10)	0.0050 (10)	0.0000 (10)
C4	0.0362 (13)	0.0401 (13)	0.0379 (13)	0.0092 (11)	0.0154 (11)	0.0035 (10)
C5	0.0509 (16)	0.0361 (12)	0.0276 (12)	0.0124 (12)	0.0065 (11)	−0.0001 (10)
C6	0.0374 (13)	0.0305 (11)	0.0336 (12)	0.0075 (10)	−0.0022 (10)	0.0020 (9)
C7	0.0272 (11)	0.0284 (10)	0.0342 (12)	0.0100 (9)	0.0025 (9)	0.0089 (9)
C8	0.0331 (12)	0.0332 (11)	0.0389 (12)	0.0171 (10)	0.0088 (10)	0.0131 (10)
C9	0.0398 (15)	0.0505 (15)	0.0619 (18)	0.0232 (13)	0.0228 (13)	0.0177 (13)
C10	0.0335 (12)	0.0347 (11)	0.0228 (10)	0.0147 (10)	0.0013 (9)	−0.0024 (9)
C11	0.0367 (13)	0.0334 (11)	0.0342 (12)	0.0146 (10)	0.0072 (10)	0.0012 (9)
C12	0.0296 (12)	0.0421 (13)	0.0375 (13)	0.0143 (11)	0.0060 (10)	−0.0016 (10)
C13	0.0452 (14)	0.0496 (14)	0.0235 (11)	0.0304 (12)	0.0043 (10)	0.0036 (10)
C14	0.0516 (16)	0.0463 (14)	0.0338 (13)	0.0231 (13)	0.0155 (12)	0.0137 (11)
C15	0.0362 (13)	0.0467 (14)	0.0347 (12)	0.0167 (11)	0.0105 (10)	0.0073 (11)
Br2	0.0903 (3)	0.0663 (2)	0.03856 (16)	0.01303 (19)	0.00546 (16)	0.00434 (14)
S2	0.0365 (3)	0.0280 (3)	0.0498 (4)	0.0175 (2)	0.0019 (3)	0.0015 (2)
O3	0.0291 (8)	0.0357 (8)	0.0324 (8)	0.0132 (7)	0.0063 (7)	0.0034 (6)
O4	0.0482 (11)	0.0252 (8)	0.0664 (12)	0.0073 (8)	−0.0022 (9)	0.0010 (8)
F2	0.0352 (8)	0.0640 (10)	0.0606 (10)	0.0256 (7)	0.0184 (7)	0.0110 (8)
C16	0.0281 (11)	0.0249 (10)	0.0314 (11)	0.0116 (9)	−0.0018 (9)	−0.0043 (8)
C17	0.0261 (11)	0.0257 (10)	0.0255 (10)	0.0100 (9)	−0.0010 (8)	−0.0054 (8)
C18	0.0276 (12)	0.0311 (11)	0.0331 (12)	0.0113 (9)	0.0034 (9)	0.0008 (9)
C19	0.0246 (11)	0.0410 (12)	0.0340 (12)	0.0131 (10)	0.0039 (9)	−0.0033 (10)
C20	0.0329 (13)	0.0405 (12)	0.0356 (12)	0.0237 (11)	−0.0022 (10)	−0.0045 (10)
C21	0.0370 (13)	0.0344 (11)	0.0316 (12)	0.0179 (10)	0.0004 (10)	0.0030 (9)
C22	0.0265 (11)	0.0301 (10)	0.0255 (10)	0.0109 (9)	0.0009 (9)	−0.0030 (8)
C23	0.0260 (11)	0.0301 (10)	0.0299 (11)	0.0103 (9)	−0.0010 (9)	−0.0066 (9)
C24	0.0279 (12)	0.0470 (14)	0.0439 (14)	0.0140 (11)	0.0078 (11)	−0.0040 (11)
C25	0.0324 (12)	0.0298 (11)	0.0430 (13)	0.0142 (10)	−0.0002 (10)	0.0101 (10)
C26	0.0319 (13)	0.0458 (14)	0.0424 (14)	0.0091 (11)	0.0044 (11)	0.0097 (11)
C27	0.0375 (15)	0.0456 (14)	0.0453 (15)	0.0013 (12)	−0.0023 (12)	0.0077 (12)
C28	0.0537 (17)	0.0392 (13)	0.0371 (13)	0.0148 (12)	0.0006 (12)	0.0097 (11)
C29	0.0460 (16)	0.0464 (14)	0.0451 (15)	0.0154 (13)	0.0120 (12)	0.0181 (12)
C30	0.0328 (13)	0.0327 (12)	0.0518 (15)	0.0073 (10)	0.0052 (12)	0.0129 (11)

Br1—C13	1.898 (2)	Br2—C28	1.897 (3)
S1—O2	1.4881 (19)	S2—O4	1.4876 (19)
S1—C1	1.754 (2)	S2—C16	1.766 (2)
S1—C10	1.797 (2)	S2—C25	1.797 (3)
O1—C8	1.364 (3)	O3—C23	1.374 (3)
O1—C7	1.375 (3)	O3—C22	1.380 (3)
F1—C4	1.365 (3)	F2—C19	1.360 (3)
C1—C8	1.358 (3)	C16—C23	1.341 (3)
C1—C2	1.442 (3)	C16—C17	1.442 (3)
C2—C3	1.388 (3)	C17—C18	1.395 (3)
C2—C7	1.391 (3)	C17—C22	1.396 (3)
C3—C4	1.369 (3)	C18—C19	1.373 (3)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.377 (4)	C19—C20	1.383 (3)
C5—C6	1.379 (4)	C20—C21	1.379 (3)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.379 (3)	C21—C22	1.379 (3)
C6—H6	0.9500	C21—H21	0.9500
C8—C9	1.479 (3)	C23—C24	1.484 (3)
C9—H15A	0.9800	C24—H24A	0.9800
C9—H15B	0.9800	C24—H24B	0.9800
C9—H15C	0.9800	C24—H24C	0.9800
C10—C11	1.373 (3)	C25—C30	1.377 (4)
C10—C15	1.386 (3)	C25—C26	1.388 (3)
C11—C12	1.391 (3)	C26—C27	1.380 (4)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.375 (3)	C27—C28	1.374 (4)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.382 (4)	C28—C29	1.384 (4)
C14—C15	1.382 (4)	C29—C30	1.383 (4)
C14—H14	0.9500	C29—H29	0.9500
C15—H15	0.9500	C30—H30	0.9500
O2—S1—C1	109.43 (11)	O4—S2—C16	107.26 (11)
O2—S1—C10	105.77 (11)	O4—S2—C25	107.02 (12)
C1—S1—C10	98.65 (10)	C16—S2—C25	96.12 (10)
C8—O1—C7	106.70 (17)	C23—O3—C22	106.26 (17)
C8—C1—C2	107.5 (2)	C23—C16—C17	107.87 (19)
C8—C1—S1	121.82 (18)	C23—C16—S2	124.12 (17)
C2—C1—S1	130.60 (17)	C17—C16—S2	127.99 (18)
C3—C2—C7	119.7 (2)	C18—C17—C22	119.4 (2)
C3—C2—C1	135.9 (2)	C18—C17—C16	136.2 (2)
C7—C2—C1	104.4 (2)	C22—C17—C16	104.42 (19)
C4—C3—C2	115.9 (2)	C19—C18—C17	116.0 (2)
C4—C3—H3	122.0	C19—C18—H18	122.0
C2—C3—H3	122.0	C17—C18—H18	122.0
C3—C4—F1	118.2 (2)	F2—C19—C18	117.8 (2)
C3—C4—C5	124.7 (2)	F2—C19—C20	117.6 (2)
F1—C4—C5	117.1 (2)	C18—C19—C20	124.6 (2)
C4—C5—C6	119.8 (2)	C21—C20—C19	119.5 (2)
C4—C5—H5	120.1	C21—C20—H20	120.2
C6—C5—H5	120.1	C19—C20—H20	120.2
C5—C6—C7	116.4 (2)	C20—C21—C22	116.9 (2)
C5—C6—H6	121.8	C20—C21—H21	121.6
C7—C6—H6	121.8	C22—C21—H21	121.6
O1—C7—C6	125.7 (2)	C21—C22—O3	126.0 (2)
O1—C7—C2	110.70 (19)	C21—C22—C17	123.6 (2)
C6—C7—C2	123.6 (2)	O3—C22—C17	110.39 (18)
C1—C8—O1	110.7 (2)	C16—C23—O3	111.06 (19)
C1—C8—C9	133.1 (2)	C16—C23—C24	132.7 (2)
O1—C8—C9	116.3 (2)	O3—C23—C24	116.2 (2)
C8—C9—H15A	109.5	C23—C24—H24A	109.5
C8—C9—H15B	109.5	C23—C24—H24B	109.5
H15A—C9—H15B	109.5	H24A—C24—H24B	109.5
C8—C9—H15C	109.5	C23—C24—H24C	109.5
H15A—C9—H15C	109.5	H24A—C24—H24C	109.5
H15B—C9—H15C	109.5	H24B—C24—H24C	109.5
C11—C10—C15	121.6 (2)	C30—C25—C26	121.3 (2)
C11—C10—S1	118.17 (18)	C30—C25—S2	120.24 (18)
C15—C10—S1	119.95 (18)	C26—C25—S2	118.5 (2)
C10—C11—C12	119.4 (2)	C27—C26—C25	119.3 (3)
C10—C11—H11	120.3	C27—C26—H26	120.3
C12—C11—H11	120.3	C25—C26—H26	120.3
C13—C12—C11	118.9 (2)	C28—C27—C26	119.1 (2)
C13—C12—H12	120.5	C28—C27—H27	120.5
C11—C12—H12	120.5	C26—C27—H27	120.5
C14—C13—C12	121.8 (2)	C27—C28—C29	122.0 (3)
C14—C13—Br1	119.60 (18)	C27—C28—Br2	119.5 (2)
C12—C13—Br1	118.60 (19)	C29—C28—Br2	118.5 (2)
C13—C14—C15	119.3 (2)	C30—C29—C28	118.8 (3)
C13—C14—H14	120.4	C30—C29—H29	120.6
C15—C14—H14	120.4	C28—C29—H29	120.6
C14—C15—C10	119.0 (2)	C25—C30—C29	119.4 (2)
C14—C15—H15	120.5	C25—C30—H30	120.3
C10—C15—H15	120.5	C29—C30—H30	120.3
O2—S1—C1—C8	122.96 (19)	O4—S2—C16—C23	143.29 (19)
C10—S1—C1—C8	−126.85 (19)	C25—S2—C16—C23	−106.7 (2)
O2—S1—C1—C2	−53.8 (2)	O4—S2—C16—C17	−38.7 (2)
C10—S1—C1—C2	56.4 (2)	C25—S2—C16—C17	71.3 (2)
C8—C1—C2—C3	−179.5 (3)	C23—C16—C17—C18	−178.5 (2)
S1—C1—C2—C3	−2.5 (4)	S2—C16—C17—C18	3.2 (4)
C8—C1—C2—C7	0.1 (2)	C23—C16—C17—C22	0.7 (2)
S1—C1—C2—C7	177.15 (17)	S2—C16—C17—C22	−177.64 (16)
C7—C2—C3—C4	0.5 (3)	C22—C17—C18—C19	1.5 (3)
C1—C2—C3—C4	−179.9 (2)	C16—C17—C18—C19	−179.4 (2)
C2—C3—C4—F1	−179.5 (2)	C17—C18—C19—F2	179.93 (19)
C2—C3—C4—C5	−0.6 (4)	C17—C18—C19—C20	−0.4 (3)
C3—C4—C5—C6	0.1 (4)	F2—C19—C20—C21	179.0 (2)
F1—C4—C5—C6	179.0 (2)	C18—C19—C20—C21	−0.7 (4)
C4—C5—C6—C7	0.5 (3)	C19—C20—C21—C22	0.6 (3)
C8—O1—C7—C6	179.6 (2)	C20—C21—C22—O3	−179.97 (19)
C8—O1—C7—C2	0.0 (2)	C20—C21—C22—C17	0.6 (3)
C5—C6—C7—O1	179.9 (2)	C23—O3—C22—C21	−179.3 (2)
C5—C6—C7—C2	−0.6 (3)	C23—O3—C22—C17	0.2 (2)
C3—C2—C7—O1	179.63 (19)	C18—C17—C22—C21	−1.6 (3)
C1—C2—C7—O1	−0.1 (2)	C16—C17—C22—C21	179.0 (2)
C3—C2—C7—C6	0.0 (3)	C18—C17—C22—O3	178.83 (18)
C1—C2—C7—C6	−179.7 (2)	C16—C17—C22—O3	−0.5 (2)
C2—C1—C8—O1	−0.1 (2)	C17—C16—C23—O3	−0.6 (2)
S1—C1—C8—O1	−177.45 (15)	S2—C16—C23—O3	177.83 (14)
C2—C1—C8—C9	−178.9 (2)	C17—C16—C23—C24	−178.0 (2)
S1—C1—C8—C9	3.7 (4)	S2—C16—C23—C24	0.4 (4)
C7—O1—C8—C1	0.0 (2)	C22—O3—C23—C16	0.2 (2)
C7—O1—C8—C9	179.08 (19)	C22—O3—C23—C24	178.11 (18)
O2—S1—C10—C11	−4.0 (2)	O4—S2—C25—C30	7.5 (2)
C1—S1—C10—C11	−117.14 (19)	C16—S2—C25—C30	−102.7 (2)
O2—S1—C10—C15	−178.55 (18)	O4—S2—C25—C26	−172.55 (18)
C1—S1—C10—C15	68.3 (2)	C16—S2—C25—C26	77.3 (2)
C15—C10—C11—C12	−0.7 (3)	C30—C25—C26—C27	1.7 (4)
S1—C10—C11—C12	−175.12 (17)	S2—C25—C26—C27	−178.2 (2)
C10—C11—C12—C13	0.8 (3)	C25—C26—C27—C28	−0.3 (4)
C11—C12—C13—C14	−0.9 (4)	C26—C27—C28—C29	−0.8 (4)
C11—C12—C13—Br1	179.82 (17)	C26—C27—C28—Br2	178.5 (2)
C12—C13—C14—C15	0.8 (4)	C27—C28—C29—C30	0.3 (4)
Br1—C13—C14—C15	−179.88 (18)	Br2—C28—C29—C30	−178.88 (19)
C13—C14—C15—C10	−0.7 (4)	C26—C25—C30—C29	−2.1 (4)
C11—C10—C15—C14	0.6 (3)	S2—C25—C30—C29	177.82 (19)
S1—C10—C15—C14	174.96 (18)	C28—C29—C30—C25	1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···F1i	0.95	2.44	3.316 (3)	154
C15—H15···O4ii	0.95	2.42	3.323 (3)	158
C24—H24C···O2iii	0.98	2.59	3.502 (3)	154
C5—H5···Cg1iv	0.95	2.74	3.612 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯F1i	0.95	2.44	3.316 (3)	154
C15—H15⋯O4ii	0.95	2.42	3.323 (3)	158
C24—H24C⋯O2iii	0.98	2.59	3.502 (3)	154
C5—H5⋯Cg1iv	0.95	2.74	3.612 (3)	154

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