5-Bromo-3-cyclo-hexyl-sulfinyl-2-methyl-1-benzofuran.

In the asymmetric unit of the title compound, C(15)H(17)BrO(3)S, there are two independent mol-ecules. The cyclo-hexane rings in each adopt classic chair conformations. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and aromatic π-π inter-actions between the furan rings of symmetry-related mol-ecules [centroid-centroid distance = 3.555 (2) Å].

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For related structures, see: Choi et al. (2007 ▶); Seo et al. (2009 ▶).

Experimental

Crystal data

C15H17BrO2S

M = 341.26

Monoclinic,

a = 12.1842 (2) Å

b = 9.0281 (1) Å

c = 26.6191 (4) Å

β = 97.702 (1)°

V = 2901.69 (7) Å3

Z = 8

Mo Kα radiation

μ = 2.97 mm−1

T = 173 K

0.31 × 0.22 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.579, T max = 0.746

26831 measured reflections

6674 independent reflections

4944 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.088

S = 1.04

6674 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.56 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 datablocks global, I. DOI: 10.1107/S1600536811003242/lh5201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003242/lh5201Isup2.hkl

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

C15H17BrO2S	F(000) = 1392
Mr = 341.26	Dx = 1.562 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7002 reflections
a = 12.1842 (2) Å	θ = 2.4–24.9°
b = 9.0281 (1) Å	µ = 2.97 mm−1
c = 26.6191 (4) Å	T = 173 K
β = 97.702 (1)°	Block, colourless
V = 2901.69 (7) Å3	0.31 × 0.22 × 0.18 mm
Z = 8

Bruker SMART APEXII CCD diffractometer	6674 independent reflections
Radiation source: rotating anode	4944 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→11
Tmin = 0.579, Tmax = 0.746	l = −32→34
26831 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) = 0.088	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1726P] where P = (Fo2 + 2Fc2)/3
6674 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.56 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	0.46756 (2)	0.86266 (3)	0.592298 (11)	0.04012 (9)
Br2	−0.07658 (2)	−0.22211 (3)	0.590592 (11)	0.04406 (10)
S1	0.73629 (5)	0.29635 (6)	0.65910 (2)	0.02434 (14)
S2	0.27538 (5)	0.26776 (7)	0.66785 (2)	0.02864 (15)
O1	0.87123 (13)	0.65573 (18)	0.72524 (6)	0.0277 (4)
O2	0.61309 (14)	0.28891 (19)	0.65360 (7)	0.0350 (4)
O3	0.36105 (14)	−0.13307 (18)	0.71689 (6)	0.0313 (4)
O4	0.15602 (15)	0.3032 (2)	0.65511 (7)	0.0401 (5)
C1	0.77497 (18)	0.4739 (2)	0.68179 (8)	0.0211 (5)
C2	0.71675 (18)	0.6108 (2)	0.66932 (8)	0.0202 (5)
C3	0.62204 (19)	0.6512 (3)	0.63733 (8)	0.0230 (5)
H3	0.5777	0.5803	0.6175	0.028*
C4	0.59557 (19)	0.8007 (3)	0.63584 (9)	0.0250 (5)
C5	0.6577 (2)	0.9072 (3)	0.66440 (9)	0.0299 (6)
H5	0.6357	1.0082	0.6619	0.036*
C6	0.7517 (2)	0.8665 (3)	0.69656 (9)	0.0294 (6)
H6	0.7951	0.9371	0.7169	0.035*
C7	0.77938 (19)	0.7179 (3)	0.69753 (9)	0.0239 (5)
C8	0.86624 (19)	0.5065 (3)	0.71497 (8)	0.0249 (5)
C9	0.9604 (2)	0.4162 (3)	0.73881 (10)	0.0353 (6)
H9A	0.9366	0.3131	0.7413	0.053*
H9B	0.9860	0.4546	0.7728	0.053*
H9C	1.0210	0.4210	0.7181	0.053*
C10	0.77442 (19)	0.3168 (3)	0.59584 (9)	0.0234 (5)
H10	0.7406	0.4100	0.5805	0.028*
C11	0.8996 (2)	0.3278 (3)	0.59887 (10)	0.0394 (7)
H11A	0.9343	0.2411	0.6174	0.047*
H11B	0.9257	0.4182	0.6179	0.047*
C12	0.9348 (3)	0.3334 (4)	0.54597 (12)	0.0561 (9)
H12A	0.9079	0.4266	0.5290	0.067*
H12B	1.0166	0.3327	0.5489	0.067*
C13	0.8886 (3)	0.2023 (4)	0.51411 (12)	0.0612 (10)
H13A	0.9092	0.2113	0.4795	0.073*
H13B	0.9211	0.1094	0.5293	0.073*
C14	0.7638 (3)	0.1964 (3)	0.51127 (10)	0.0487 (8)
H14A	0.7354	0.1095	0.4909	0.058*
H14B	0.7313	0.2866	0.4941	0.058*
C15	0.7284 (2)	0.1857 (3)	0.56366 (10)	0.0380 (6)
H15A	0.7561	0.0920	0.5801	0.046*
H15B	0.6465	0.1853	0.5608	0.046*
C16	0.28708 (19)	0.0766 (3)	0.68148 (8)	0.0242 (5)
C17	0.2120 (2)	−0.0437 (3)	0.66480 (9)	0.0245 (5)
C18	0.11013 (19)	−0.0572 (3)	0.63480 (8)	0.0255 (5)
H18	0.0730	0.0264	0.6189	0.031*
C19	0.0653 (2)	−0.1977 (3)	0.62917 (9)	0.0294 (6)
C20	0.1191 (2)	−0.3231 (3)	0.65164 (10)	0.0344 (6)
H20	0.0860	−0.4180	0.6461	0.041*
C21	0.2188 (2)	−0.3094 (3)	0.68142 (10)	0.0343 (6)
H21	0.2562	−0.3930	0.6972	0.041*
C22	0.2629 (2)	−0.1690 (3)	0.68765 (9)	0.0264 (5)
C23	0.3726 (2)	0.0180 (3)	0.71287 (9)	0.0280 (5)
C24	0.4728 (2)	0.0833 (3)	0.74241 (10)	0.0409 (7)
H24A	0.5345	0.0792	0.7223	0.061*
H24B	0.4921	0.0272	0.7739	0.061*
H24C	0.4581	0.1867	0.7505	0.061*
C25	0.33763 (19)	0.2705 (2)	0.60925 (8)	0.0228 (5)
H25	0.4133	0.2260	0.6165	0.027*
C26	0.3509 (2)	0.4326 (3)	0.59471 (9)	0.0308 (6)
H26A	0.2773	0.4808	0.5888	0.037*
H26B	0.3963	0.4853	0.6228	0.037*
C27	0.4067 (2)	0.4425 (3)	0.54673 (9)	0.0332 (6)
H27A	0.4125	0.5476	0.5369	0.040*
H27B	0.4825	0.4015	0.5536	0.040*
C28	0.3413 (2)	0.3575 (3)	0.50351 (10)	0.0354 (6)
H28A	0.3803	0.3627	0.4732	0.043*
H28B	0.2675	0.4035	0.4948	0.043*
C29	0.3274 (2)	0.1960 (3)	0.51799 (9)	0.0320 (6)
H29A	0.4009	0.1474	0.5233	0.038*
H29B	0.2813	0.1442	0.4899	0.038*
C30	0.2729 (2)	0.1827 (3)	0.56638 (9)	0.0268 (5)
H30A	0.1960	0.2204	0.5599	0.032*
H30B	0.2700	0.0772	0.5763	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.03958 (16)	0.03535 (16)	0.04353 (17)	0.01601 (13)	−0.00135 (12)	0.00518 (12)
Br2	0.03332 (16)	0.0532 (2)	0.04619 (18)	−0.01426 (14)	0.00714 (13)	−0.00397 (14)
S1	0.0269 (3)	0.0171 (3)	0.0293 (3)	−0.0007 (2)	0.0049 (2)	0.0014 (2)
S2	0.0371 (4)	0.0203 (3)	0.0308 (3)	−0.0019 (3)	0.0129 (3)	−0.0023 (3)
O1	0.0235 (9)	0.0308 (9)	0.0279 (9)	−0.0036 (7)	0.0006 (7)	−0.0047 (7)
O2	0.0271 (9)	0.0309 (10)	0.0486 (11)	−0.0076 (8)	0.0112 (8)	−0.0029 (8)
O3	0.0353 (10)	0.0293 (10)	0.0293 (9)	0.0065 (8)	0.0042 (8)	0.0044 (7)
O4	0.0382 (11)	0.0323 (10)	0.0534 (12)	0.0061 (9)	0.0198 (9)	0.0080 (9)
C1	0.0218 (11)	0.0199 (12)	0.0220 (12)	−0.0012 (9)	0.0039 (9)	0.0018 (9)
C2	0.0228 (11)	0.0183 (11)	0.0208 (11)	0.0000 (9)	0.0082 (9)	0.0006 (9)
C3	0.0247 (12)	0.0204 (12)	0.0241 (12)	0.0001 (10)	0.0042 (10)	−0.0001 (10)
C4	0.0259 (13)	0.0246 (13)	0.0254 (12)	0.0037 (10)	0.0072 (10)	0.0033 (10)
C5	0.0348 (14)	0.0185 (12)	0.0387 (15)	0.0010 (11)	0.0134 (12)	−0.0005 (11)
C6	0.0327 (14)	0.0230 (13)	0.0335 (14)	−0.0071 (11)	0.0084 (11)	−0.0091 (11)
C7	0.0210 (12)	0.0294 (13)	0.0216 (12)	−0.0024 (10)	0.0042 (9)	−0.0036 (10)
C8	0.0259 (12)	0.0292 (13)	0.0199 (12)	0.0012 (10)	0.0044 (9)	0.0018 (10)
C9	0.0253 (13)	0.0486 (16)	0.0312 (14)	0.0070 (12)	0.0008 (11)	0.0059 (12)
C10	0.0250 (12)	0.0206 (12)	0.0248 (12)	0.0030 (10)	0.0039 (10)	−0.0004 (9)
C11	0.0257 (14)	0.0558 (18)	0.0375 (15)	0.0042 (13)	0.0071 (12)	−0.0041 (13)
C12	0.0397 (17)	0.086 (2)	0.0462 (19)	0.0061 (18)	0.0204 (14)	0.0000 (18)
C13	0.085 (3)	0.065 (2)	0.0386 (18)	0.024 (2)	0.0271 (18)	−0.0063 (16)
C14	0.076 (2)	0.0350 (16)	0.0340 (16)	0.0026 (16)	0.0017 (15)	−0.0115 (13)
C15	0.0502 (17)	0.0280 (14)	0.0344 (15)	−0.0021 (13)	0.0009 (13)	−0.0073 (12)
C16	0.0299 (13)	0.0203 (12)	0.0240 (12)	−0.0002 (10)	0.0091 (10)	−0.0014 (10)
C17	0.0309 (13)	0.0211 (12)	0.0235 (12)	0.0006 (10)	0.0110 (10)	0.0026 (10)
C18	0.0289 (13)	0.0240 (13)	0.0247 (13)	0.0003 (10)	0.0074 (10)	0.0036 (10)
C19	0.0293 (13)	0.0330 (14)	0.0273 (13)	−0.0056 (11)	0.0089 (10)	−0.0039 (11)
C20	0.0456 (17)	0.0212 (13)	0.0396 (16)	−0.0063 (12)	0.0168 (13)	−0.0025 (11)
C21	0.0450 (16)	0.0210 (13)	0.0397 (16)	0.0053 (12)	0.0163 (13)	0.0062 (11)
C22	0.0292 (13)	0.0255 (13)	0.0255 (13)	0.0035 (11)	0.0077 (10)	0.0014 (10)
C23	0.0300 (13)	0.0291 (13)	0.0264 (13)	−0.0010 (11)	0.0097 (10)	−0.0024 (11)
C24	0.0311 (14)	0.0576 (18)	0.0338 (15)	−0.0026 (14)	0.0037 (12)	−0.0087 (14)
C25	0.0241 (12)	0.0208 (12)	0.0243 (12)	−0.0005 (10)	0.0056 (10)	0.0000 (10)
C26	0.0340 (14)	0.0230 (13)	0.0373 (15)	−0.0050 (11)	0.0115 (11)	−0.0014 (11)
C27	0.0388 (15)	0.0271 (14)	0.0354 (15)	−0.0052 (12)	0.0107 (12)	0.0047 (11)
C28	0.0452 (16)	0.0323 (15)	0.0292 (14)	−0.0009 (13)	0.0065 (12)	0.0069 (11)
C29	0.0430 (16)	0.0286 (14)	0.0239 (13)	−0.0014 (12)	0.0028 (11)	−0.0005 (11)
C30	0.0303 (13)	0.0208 (12)	0.0290 (13)	−0.0037 (10)	0.0027 (10)	−0.0011 (10)

Br1—C4	1.899 (2)	C13—H13B	0.9900
Br2—C19	1.902 (3)	C14—C15	1.517 (4)
S1—O2	1.4901 (18)	C14—H14A	0.9900
S1—C1	1.755 (2)	C14—H14B	0.9900
S1—C10	1.815 (2)	C15—H15A	0.9900
S2—O4	1.483 (2)	C15—H15B	0.9900
S2—C16	1.765 (2)	C16—C23	1.353 (3)
S2—C25	1.824 (2)	C16—C17	1.451 (3)
O1—C8	1.374 (3)	C17—C18	1.388 (3)
O1—C7	1.375 (3)	C17—C22	1.390 (3)
O3—C22	1.376 (3)	C18—C19	1.382 (3)
O3—C23	1.377 (3)	C18—H18	0.9500
C1—C8	1.357 (3)	C19—C20	1.401 (4)
C1—C2	1.442 (3)	C20—C21	1.364 (4)
C2—C3	1.388 (3)	C20—H20	0.9500
C2—C7	1.388 (3)	C21—C22	1.378 (3)
C3—C4	1.387 (3)	C21—H21	0.9500
C3—H3	0.9500	C23—C24	1.483 (3)
C4—C5	1.386 (3)	C24—H24A	0.9800
C5—C6	1.385 (4)	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800
C6—C7	1.383 (3)	C25—C30	1.521 (3)
C6—H6	0.9500	C25—C26	1.528 (3)
C8—C9	1.480 (3)	C25—H25	1.0000
C9—H9A	0.9800	C26—C27	1.528 (3)
C9—H9B	0.9800	C26—H26A	0.9900
C9—H9C	0.9800	C26—H26B	0.9900
C10—C11	1.520 (3)	C27—C28	1.517 (4)
C10—C15	1.524 (3)	C27—H27A	0.9900
C10—H10	1.0000	C27—H27B	0.9900
C11—C12	1.527 (4)	C28—C29	1.523 (3)
C11—H11A	0.9900	C28—H28A	0.9900
C11—H11B	0.9900	C28—H28B	0.9900
C12—C13	1.519 (5)	C29—C30	1.532 (3)
C12—H12A	0.9900	C29—H29A	0.9900
C12—H12B	0.9900	C29—H29B	0.9900
C13—C14	1.513 (5)	C30—H30A	0.9900
C13—H13A	0.9900	C30—H30B	0.9900
O2—S1—C1	107.19 (10)	C10—C15—H15A	109.7
O2—S1—C10	107.04 (11)	C14—C15—H15B	109.7
C1—S1—C10	97.81 (11)	C10—C15—H15B	109.7
O4—S2—C16	107.92 (11)	H15A—C15—H15B	108.2
O4—S2—C25	107.99 (11)	C23—C16—C17	107.3 (2)
C16—S2—C25	99.08 (10)	C23—C16—S2	122.95 (19)
C8—O1—C7	106.39 (17)	C17—C16—S2	129.71 (18)
C22—O3—C23	106.25 (18)	C18—C17—C22	119.5 (2)
C8—C1—C2	107.4 (2)	C18—C17—C16	136.0 (2)
C8—C1—S1	125.56 (18)	C22—C17—C16	104.4 (2)
C2—C1—S1	127.08 (17)	C19—C18—C17	116.9 (2)
C3—C2—C7	120.1 (2)	C19—C18—H18	121.6
C3—C2—C1	135.2 (2)	C17—C18—H18	121.6
C7—C2—C1	104.76 (19)	C18—C19—C20	122.7 (2)
C4—C3—C2	116.4 (2)	C18—C19—Br2	118.84 (19)
C4—C3—H3	121.8	C20—C19—Br2	118.43 (19)
C2—C3—H3	121.8	C21—C20—C19	120.2 (2)
C5—C4—C3	123.5 (2)	C21—C20—H20	119.9
C5—C4—Br1	118.29 (18)	C19—C20—H20	119.9
C3—C4—Br1	118.24 (18)	C20—C21—C22	117.1 (2)
C6—C5—C4	120.1 (2)	C20—C21—H21	121.4
C6—C5—H5	120.0	C22—C21—H21	121.4
C4—C5—H5	120.0	O3—C22—C21	125.5 (2)
C7—C6—C5	116.6 (2)	O3—C22—C17	111.0 (2)
C7—C6—H6	121.7	C21—C22—C17	123.5 (2)
C5—C6—H6	121.7	C16—C23—O3	111.0 (2)
O1—C7—C6	125.8 (2)	C16—C23—C24	133.1 (2)
O1—C7—C2	110.8 (2)	O3—C23—C24	116.0 (2)
C6—C7—C2	123.4 (2)	C23—C24—H24A	109.5
C1—C8—O1	110.7 (2)	C23—C24—H24B	109.5
C1—C8—C9	132.9 (2)	H24A—C24—H24B	109.5
O1—C8—C9	116.4 (2)	C23—C24—H24C	109.5
C8—C9—H9A	109.5	H24A—C24—H24C	109.5
C8—C9—H9B	109.5	H24B—C24—H24C	109.5
H9A—C9—H9B	109.5	C30—C25—C26	111.8 (2)
C8—C9—H9C	109.5	C30—C25—S2	113.65 (16)
H9A—C9—H9C	109.5	C26—C25—S2	107.45 (15)
H9B—C9—H9C	109.5	C30—C25—H25	107.9
C11—C10—C15	111.8 (2)	C26—C25—H25	107.9
C11—C10—S1	109.71 (17)	S2—C25—H25	107.9
C15—C10—S1	108.77 (17)	C27—C26—C25	110.0 (2)
C11—C10—H10	108.8	C27—C26—H26A	109.7
C15—C10—H10	108.8	C25—C26—H26A	109.7
S1—C10—H10	108.8	C27—C26—H26B	109.7
C10—C11—C12	110.9 (2)	C25—C26—H26B	109.7
C10—C11—H11A	109.5	H26A—C26—H26B	108.2
C12—C11—H11A	109.5	C28—C27—C26	110.9 (2)
C10—C11—H11B	109.5	C28—C27—H27A	109.4
C12—C11—H11B	109.5	C26—C27—H27A	109.4
H11A—C11—H11B	108.0	C28—C27—H27B	109.4
C13—C12—C11	111.1 (3)	C26—C27—H27B	109.4
C13—C12—H12A	109.4	H27A—C27—H27B	108.0
C11—C12—H12A	109.4	C27—C28—C29	110.9 (2)
C13—C12—H12B	109.4	C27—C28—H28A	109.5
C11—C12—H12B	109.4	C29—C28—H28A	109.5
H12A—C12—H12B	108.0	C27—C28—H28B	109.5
C14—C13—C12	110.5 (2)	C29—C28—H28B	109.5
C14—C13—H13A	109.6	H28A—C28—H28B	108.0
C12—C13—H13A	109.6	C28—C29—C30	111.3 (2)
C14—C13—H13B	109.6	C28—C29—H29A	109.4
C12—C13—H13B	109.6	C30—C29—H29A	109.4
H13A—C13—H13B	108.1	C28—C29—H29B	109.4
C13—C14—C15	111.4 (2)	C30—C29—H29B	109.4
C13—C14—H14A	109.4	H29A—C29—H29B	108.0
C15—C14—H14A	109.4	C25—C30—C29	110.5 (2)
C13—C14—H14B	109.4	C25—C30—H30A	109.6
C15—C14—H14B	109.4	C29—C30—H30A	109.6
H14A—C14—H14B	108.0	C25—C30—H30B	109.6
C14—C15—C10	109.8 (2)	C29—C30—H30B	109.6
C14—C15—H15A	109.7	H30A—C30—H30B	108.1
O2—S1—C1—C8	144.0 (2)	O4—S2—C16—C23	−152.5 (2)
C10—S1—C1—C8	−105.3 (2)	C25—S2—C16—C23	95.1 (2)
O2—S1—C1—C2	−35.5 (2)	O4—S2—C16—C17	25.0 (2)
C10—S1—C1—C2	75.1 (2)	C25—S2—C16—C17	−87.4 (2)
C8—C1—C2—C3	177.8 (2)	C23—C16—C17—C18	177.1 (3)
S1—C1—C2—C3	−2.5 (4)	S2—C16—C17—C18	−0.7 (4)
C8—C1—C2—C7	−0.7 (2)	C23—C16—C17—C22	−1.5 (2)
S1—C1—C2—C7	178.90 (17)	S2—C16—C17—C22	−179.34 (18)
C7—C2—C3—C4	−0.2 (3)	C22—C17—C18—C19	−0.5 (3)
C1—C2—C3—C4	−178.6 (2)	C16—C17—C18—C19	−179.0 (2)
C2—C3—C4—C5	−0.5 (3)	C17—C18—C19—C20	−0.9 (4)
C2—C3—C4—Br1	179.47 (16)	C17—C18—C19—Br2	177.68 (16)
C3—C4—C5—C6	0.0 (4)	C18—C19—C20—C21	1.4 (4)
Br1—C4—C5—C6	−179.90 (18)	Br2—C19—C20—C21	−177.15 (19)
C4—C5—C6—C7	1.0 (3)	C19—C20—C21—C22	−0.5 (4)
C8—O1—C7—C6	−179.9 (2)	C23—O3—C22—C21	−179.3 (2)
C8—O1—C7—C2	−0.7 (2)	C23—O3—C22—C17	0.4 (3)
C5—C6—C7—O1	177.4 (2)	C20—C21—C22—O3	178.7 (2)
C5—C6—C7—C2	−1.6 (4)	C20—C21—C22—C17	−0.9 (4)
C3—C2—C7—O1	−177.94 (19)	C18—C17—C22—O3	−178.2 (2)
C1—C2—C7—O1	0.9 (2)	C16—C17—C22—O3	0.7 (2)
C3—C2—C7—C6	1.3 (4)	C18—C17—C22—C21	1.4 (4)
C1—C2—C7—C6	−179.9 (2)	C16—C17—C22—C21	−179.6 (2)
C2—C1—C8—O1	0.3 (3)	C17—C16—C23—O3	1.9 (3)
S1—C1—C8—O1	−179.31 (15)	S2—C16—C23—O3	179.85 (15)
C2—C1—C8—C9	−175.8 (2)	C17—C16—C23—C24	−178.5 (2)
S1—C1—C8—C9	4.5 (4)	S2—C16—C23—C24	−0.5 (4)
C7—O1—C8—C1	0.2 (2)	C22—O3—C23—C16	−1.4 (3)
C7—O1—C8—C9	177.06 (19)	C22—O3—C23—C24	178.9 (2)
O2—S1—C10—C11	179.02 (18)	O4—S2—C25—C30	−48.50 (19)
C1—S1—C10—C11	68.28 (19)	C16—S2—C25—C30	63.80 (19)
O2—S1—C10—C15	−58.37 (19)	O4—S2—C25—C26	75.73 (18)
C1—S1—C10—C15	−169.11 (17)	C16—S2—C25—C26	−171.97 (17)
C15—C10—C11—C12	54.9 (3)	C30—C25—C26—C27	−56.7 (3)
S1—C10—C11—C12	175.7 (2)	S2—C25—C26—C27	177.98 (17)
C10—C11—C12—C13	−54.7 (4)	C25—C26—C27—C28	57.1 (3)
C11—C12—C13—C14	56.2 (4)	C26—C27—C28—C29	−57.3 (3)
C12—C13—C14—C15	−58.1 (3)	C27—C28—C29—C30	56.1 (3)
C13—C14—C15—C10	57.5 (3)	C26—C25—C30—C29	55.7 (3)
C11—C10—C15—C14	−56.0 (3)	S2—C25—C30—C29	177.52 (16)
S1—C10—C15—C14	−177.3 (2)	C28—C29—C30—C25	−55.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.56	3.495 (3)	170
C25—H25···O2	1.00	2.57	3.409 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.56	3.495 (3)	170
C25—H25⋯O2	1.00	2.57	3.409 (3)	142

Symmetry code: (i) .