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

There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(17)ClO(2)S, in each of which the cyclo-hexyl rings adopt chair conformations. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

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 the structure of 5-bromo-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011 ▶).

Experimental

Crystal data

C15H17ClO2S

M = 296.80

Monoclinic,

a = 12.0755 (2) Å

b = 9.0033 (2) Å

c = 13.9112 (2) Å

β = 108.667 (1)°

V = 1432.86 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 173 K

0.28 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.896, T max = 0.932

14184 measured reflections

6583 independent reflections

6143 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.084

S = 1.03

6583 reflections

345 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 2822 Friedel pairs

Flack parameter: 0.03 (4)

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 I. DOI: 10.1107/S1600536811007859/hg5004sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007859/hg5004Isup2.hkl

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

C15H17ClO2S	F(000) = 624
Mr = 296.80	Dx = 1.376 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 6118 reflections
a = 12.0755 (2) Å	θ = 2.7–28.0°
b = 9.0033 (2) Å	µ = 0.41 mm−1
c = 13.9112 (2) Å	T = 173 K
β = 108.667 (1)°	Block, colourless
V = 1432.86 (4) Å3	0.28 × 0.24 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6583 independent reflections
Radiation source: rotating anode	6143 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.026
Detector resolution: 10.0 pixels mm-1	θmax = 28.2°, θmin = 1.6°
φ and ω scans	h = −12→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.896, Tmax = 0.932	l = −18→16
14184 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.1747P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6583 reflections	Δρmax = 0.40 e Å−3
345 parameters	Δρmin = −0.37 e Å−3
1 restraint	Absolute structure: Flack (1983), 2822 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (4)

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
S1	0.16903 (4)	−0.32206 (5)	0.81418 (3)	0.02606 (10)
S2	0.64550 (4)	0.64961 (5)	0.83739 (3)	0.02826 (10)
Cl1	0.89697 (5)	0.15052 (8)	0.68607 (4)	0.04851 (15)
Cl2	0.38281 (5)	0.23270 (7)	0.69511 (4)	0.04830 (15)
O1	0.09876 (12)	0.04307 (17)	0.93970 (10)	0.0328 (3)
O2	0.28828 (11)	−0.33014 (19)	0.80366 (11)	0.0378 (3)
O3	0.60633 (12)	0.25359 (17)	0.94106 (9)	0.0301 (3)
O4	0.75245 (12)	0.67789 (19)	0.80949 (11)	0.0394 (3)
C25	0.52029 (14)	0.6537 (2)	0.72146 (12)	0.0245 (3)
H25	0.4493	0.6236	0.7389	0.029*
C1	0.15225 (15)	−0.1419 (2)	0.85605 (12)	0.0232 (4)
C2	0.19911 (16)	−0.0065 (2)	0.83065 (12)	0.0231 (4)
C3	0.26704 (16)	0.0312 (2)	0.76970 (13)	0.0265 (4)
H3	0.2921	−0.0413	0.7315	0.032*
C4	0.29587 (16)	0.1790 (3)	0.76777 (13)	0.0312 (4)
C5	0.26014 (19)	0.2885 (2)	0.82263 (16)	0.0371 (5)
H5	0.2820	0.3890	0.8184	0.045*
C6	0.19328 (19)	0.2514 (2)	0.88290 (17)	0.0373 (5)
H6	0.1685	0.3239	0.9212	0.045*
C7	0.16438 (17)	0.1037 (2)	0.88456 (14)	0.0272 (4)
C8	0.09347 (16)	−0.1064 (2)	0.92107 (13)	0.0274 (4)
C9	0.02454 (18)	−0.1967 (3)	0.97107 (15)	0.0367 (5)
H9A	0.0522	−0.2997	0.9773	0.055*
H9B	−0.0583	−0.1936	0.9302	0.055*
H9C	0.0343	−0.1563	1.0387	0.055*
C10	0.06561 (15)	−0.3065 (2)	0.68610 (13)	0.0273 (4)
H10	0.0837	−0.2148	0.6534	0.033*
C11	0.0809 (2)	−0.4417 (3)	0.62566 (17)	0.0464 (6)
H11A	0.0717	−0.5336	0.6614	0.056*
H11B	0.1603	−0.4414	0.6195	0.056*
C12	−0.0104 (3)	−0.4381 (4)	0.52011 (19)	0.0577 (7)
H12A	0.0033	−0.3500	0.4828	0.069*
H12B	−0.0017	−0.5277	0.4819	0.069*
C13	−0.1333 (2)	−0.4322 (3)	0.52604 (18)	0.0524 (7)
H13A	−0.1902	−0.4280	0.4567	0.063*
H13B	−0.1490	−0.5234	0.5593	0.063*
C14	−0.14857 (19)	−0.2984 (3)	0.58510 (17)	0.0507 (7)
H14A	−0.2279	−0.2996	0.5914	0.061*
H14B	−0.1411	−0.2073	0.5479	0.061*
C15	−0.05747 (17)	−0.2951 (3)	0.69140 (15)	0.0415 (6)
H15A	−0.0656	−0.2015	0.7259	0.050*
H15B	−0.0720	−0.3788	0.7320	0.050*
C16	0.64528 (16)	0.4596 (2)	0.86753 (13)	0.0252 (4)
C17	0.70239 (16)	0.3378 (2)	0.83536 (13)	0.0240 (4)
C18	0.77230 (16)	0.3203 (2)	0.77357 (13)	0.0272 (4)
H18	0.7936	0.4025	0.7405	0.033*
C19	0.80929 (15)	0.1776 (3)	0.76261 (13)	0.0315 (4)
C20	0.77837 (19)	0.0540 (2)	0.80917 (16)	0.0358 (5)
H20	0.8042	−0.0421	0.7979	0.043*
C21	0.71070 (19)	0.0711 (2)	0.87124 (16)	0.0345 (5)
H21	0.6897	−0.0113	0.9044	0.041*
C22	0.67472 (16)	0.2129 (2)	0.88309 (13)	0.0279 (4)
C23	0.59106 (17)	0.4040 (2)	0.93076 (13)	0.0283 (4)
C24	0.52066 (19)	0.4726 (3)	0.98873 (15)	0.0405 (5)
H24A	0.4389	0.4796	0.9455	0.061*
H24B	0.5507	0.5723	1.0108	0.061*
H24C	0.5258	0.4114	1.0482	0.061*
C26	0.53191 (17)	0.5501 (2)	0.63839 (13)	0.0274 (4)
H26A	0.5381	0.4460	0.6624	0.033*
H26B	0.6038	0.5746	0.6220	0.033*
C27	0.42505 (18)	0.5671 (3)	0.54340 (14)	0.0346 (5)
H27A	0.4342	0.5024	0.4889	0.042*
H27B	0.3542	0.5348	0.5588	0.042*
C28	0.4101 (2)	0.7270 (3)	0.50687 (15)	0.0385 (5)
H28A	0.4782	0.7570	0.4864	0.046*
H28B	0.3391	0.7355	0.4468	0.046*
C29	0.39932 (19)	0.8293 (3)	0.58943 (15)	0.0374 (5)
H29A	0.3272	0.8048	0.6054	0.045*
H29B	0.3927	0.9332	0.5649	0.045*
C30	0.50495 (17)	0.8157 (2)	0.68588 (14)	0.0319 (4)
H30A	0.4932	0.8792	0.7399	0.038*
H30B	0.5763	0.8499	0.6720	0.038*

	U11	U22	U33	U12	U13	U23
S1	0.0268 (2)	0.0196 (2)	0.0307 (2)	0.00028 (18)	0.00769 (16)	0.00088 (17)
S2	0.0304 (2)	0.0215 (2)	0.0281 (2)	−0.00027 (18)	0.00275 (16)	−0.00124 (18)
Cl1	0.0433 (3)	0.0614 (4)	0.0446 (3)	0.0168 (3)	0.0194 (2)	−0.0047 (3)
Cl2	0.0514 (3)	0.0471 (3)	0.0473 (3)	−0.0212 (3)	0.0171 (2)	0.0081 (2)
O1	0.0322 (7)	0.0364 (8)	0.0313 (7)	0.0029 (6)	0.0121 (6)	−0.0073 (6)
O2	0.0282 (7)	0.0361 (8)	0.0478 (7)	0.0054 (7)	0.0102 (6)	−0.0047 (7)
O3	0.0315 (7)	0.0319 (8)	0.0278 (6)	−0.0040 (6)	0.0106 (5)	0.0038 (6)
O4	0.0300 (7)	0.0308 (8)	0.0520 (8)	−0.0038 (7)	0.0057 (6)	0.0082 (7)
C25	0.0213 (7)	0.0260 (9)	0.0248 (7)	0.0015 (7)	0.0055 (6)	−0.0004 (7)
C1	0.0213 (8)	0.0227 (9)	0.0246 (8)	0.0002 (7)	0.0058 (7)	0.0012 (7)
C2	0.0226 (9)	0.0206 (9)	0.0230 (8)	0.0006 (7)	0.0031 (7)	−0.0018 (6)
C3	0.0261 (9)	0.0253 (10)	0.0264 (8)	−0.0021 (7)	0.0059 (7)	0.0002 (7)
C4	0.0296 (9)	0.0308 (10)	0.0290 (8)	−0.0055 (9)	0.0036 (7)	0.0054 (8)
C5	0.0379 (12)	0.0201 (10)	0.0435 (11)	−0.0024 (8)	−0.0009 (10)	0.0018 (8)
C6	0.0363 (11)	0.0256 (11)	0.0448 (12)	0.0038 (9)	0.0055 (9)	−0.0095 (9)
C7	0.0251 (9)	0.0267 (10)	0.0277 (9)	0.0023 (7)	0.0054 (7)	−0.0025 (7)
C8	0.0253 (9)	0.0316 (10)	0.0236 (8)	0.0013 (8)	0.0056 (7)	0.0008 (7)
C9	0.0314 (10)	0.0496 (14)	0.0301 (9)	−0.0014 (10)	0.0113 (8)	0.0075 (9)
C10	0.0277 (9)	0.0253 (10)	0.0283 (8)	−0.0013 (7)	0.0083 (7)	−0.0033 (7)
C11	0.0475 (13)	0.0450 (14)	0.0436 (11)	0.0055 (11)	0.0099 (10)	−0.0172 (10)
C12	0.0657 (17)	0.0612 (18)	0.0415 (13)	0.0002 (14)	0.0105 (12)	−0.0215 (12)
C13	0.0524 (15)	0.0524 (16)	0.0398 (12)	−0.0197 (12)	−0.0031 (10)	−0.0041 (11)
C14	0.0266 (10)	0.073 (2)	0.0454 (12)	−0.0056 (11)	0.0022 (9)	−0.0035 (12)
C15	0.0268 (10)	0.0604 (17)	0.0372 (10)	−0.0027 (10)	0.0103 (8)	−0.0071 (10)
C16	0.0277 (9)	0.0224 (9)	0.0229 (8)	−0.0001 (7)	0.0045 (7)	−0.0010 (7)
C17	0.0239 (9)	0.0208 (9)	0.0242 (8)	−0.0004 (7)	0.0034 (7)	0.0006 (7)
C18	0.0262 (9)	0.0286 (10)	0.0248 (8)	0.0010 (8)	0.0055 (7)	0.0020 (7)
C19	0.0260 (8)	0.0382 (11)	0.0282 (8)	0.0071 (9)	0.0056 (7)	−0.0021 (9)
C20	0.0367 (12)	0.0236 (10)	0.0394 (11)	0.0055 (9)	0.0017 (9)	−0.0021 (8)
C21	0.0378 (12)	0.0220 (10)	0.0384 (10)	−0.0032 (8)	0.0050 (9)	0.0048 (8)
C22	0.0256 (9)	0.0305 (11)	0.0247 (8)	−0.0043 (8)	0.0041 (7)	0.0036 (7)
C23	0.0263 (9)	0.0321 (10)	0.0229 (8)	−0.0022 (8)	0.0029 (7)	−0.0027 (7)
C24	0.0330 (12)	0.0583 (16)	0.0319 (10)	−0.0009 (10)	0.0128 (8)	−0.0094 (10)
C26	0.0311 (10)	0.0235 (9)	0.0274 (8)	0.0008 (7)	0.0089 (7)	−0.0016 (7)
C27	0.0363 (11)	0.0354 (12)	0.0270 (9)	0.0011 (9)	0.0030 (8)	−0.0049 (8)
C28	0.0405 (12)	0.0407 (13)	0.0280 (9)	0.0041 (10)	0.0021 (8)	0.0046 (9)
C29	0.0369 (11)	0.0328 (12)	0.0362 (10)	0.0100 (9)	0.0029 (8)	0.0047 (9)
C30	0.0333 (10)	0.0243 (10)	0.0330 (9)	0.0055 (8)	0.0036 (8)	−0.0005 (8)

S1—O2	1.4951 (13)	C12—H12B	0.9900
S1—C1	1.7569 (19)	C13—C14	1.502 (4)
S1—C10	1.8246 (17)	C13—H13A	0.9900
S2—O4	1.4847 (15)	C13—H13B	0.9900
S2—C16	1.762 (2)	C14—C15	1.535 (3)
S2—C25	1.8241 (16)	C14—H14A	0.9900
Cl1—C19	1.7424 (18)	C14—H14B	0.9900
Cl2—C4	1.7427 (19)	C15—H15A	0.9900
O1—C8	1.368 (3)	C15—H15B	0.9900
O1—C7	1.380 (2)	C16—C23	1.350 (3)
O3—C23	1.368 (3)	C16—C17	1.441 (3)
O3—C22	1.376 (2)	C17—C18	1.393 (3)
C25—C26	1.526 (2)	C17—C22	1.400 (3)
C25—C30	1.532 (3)	C18—C19	1.385 (3)
C25—H25	1.0000	C18—H18	0.9500
C1—C8	1.355 (2)	C19—C20	1.397 (3)
C1—C2	1.435 (3)	C20—C21	1.374 (3)
C2—C7	1.387 (3)	C20—H20	0.9500
C2—C3	1.397 (3)	C21—C22	1.376 (3)
C3—C4	1.377 (3)	C21—H21	0.9500
C3—H3	0.9500	C23—C24	1.481 (3)
C4—C5	1.397 (3)	C24—H24A	0.9800
C5—C6	1.378 (3)	C24—H24B	0.9800
C5—H5	0.9500	C24—H24C	0.9800
C6—C7	1.377 (3)	C26—C27	1.531 (2)
C6—H6	0.9500	C26—H26A	0.9900
C8—C9	1.486 (3)	C26—H26B	0.9900
C9—H9A	0.9800	C27—C28	1.518 (3)
C9—H9B	0.9800	C27—H27A	0.9900
C9—H9C	0.9800	C27—H27B	0.9900
C10—C15	1.515 (3)	C28—C29	1.510 (3)
C10—C11	1.523 (3)	C28—H28A	0.9900
C10—H10	1.0000	C28—H28B	0.9900
C11—C12	1.528 (3)	C29—C30	1.532 (3)
C11—H11A	0.9900	C29—H29A	0.9900
C11—H11B	0.9900	C29—H29B	0.9900
C12—C13	1.514 (4)	C30—H30A	0.9900
C12—H12A	0.9900	C30—H30B	0.9900
O2—S1—C1	107.11 (9)	C15—C14—H14A	109.3
O2—S1—C10	106.72 (8)	C13—C14—H14B	109.3
C1—S1—C10	97.91 (8)	C15—C14—H14B	109.3
O4—S2—C16	107.24 (9)	H14A—C14—H14B	108.0
O4—S2—C25	108.04 (8)	C10—C15—C14	111.32 (17)
C16—S2—C25	99.55 (9)	C10—C15—H15A	109.4
C8—O1—C7	106.52 (14)	C14—C15—H15A	109.4
C23—O3—C22	106.75 (14)	C10—C15—H15B	109.4
C26—C25—C30	111.59 (14)	C14—C15—H15B	109.4
C26—C25—S2	113.96 (12)	H15A—C15—H15B	108.0
C30—C25—S2	106.56 (13)	C23—C16—C17	107.50 (17)
C26—C25—H25	108.2	C23—C16—S2	123.58 (15)
C30—C25—H25	108.2	C17—C16—S2	128.89 (14)
S2—C25—H25	108.2	C18—C17—C22	119.04 (18)
C8—C1—C2	107.22 (17)	C18—C17—C16	136.28 (18)
C8—C1—S1	125.45 (15)	C22—C17—C16	104.67 (16)
C2—C1—S1	127.32 (13)	C19—C18—C17	116.97 (18)
C7—C2—C3	119.46 (18)	C19—C18—H18	121.5
C7—C2—C1	105.27 (16)	C17—C18—H18	121.5
C3—C2—C1	135.26 (17)	C18—C19—C20	122.98 (18)
C4—C3—C2	116.61 (18)	C18—C19—Cl1	118.53 (16)
C4—C3—H3	121.7	C20—C19—Cl1	118.49 (17)
C2—C3—H3	121.7	C21—C20—C19	120.23 (19)
C3—C4—C5	123.14 (18)	C21—C20—H20	119.9
C3—C4—Cl2	118.84 (16)	C19—C20—H20	119.9
C5—C4—Cl2	118.02 (17)	C20—C21—C22	116.94 (19)
C6—C5—C4	120.3 (2)	C20—C21—H21	121.5
C6—C5—H5	119.8	C22—C21—H21	121.5
C4—C5—H5	119.8	C21—C22—O3	126.10 (17)
C7—C6—C5	116.4 (2)	C21—C22—C17	123.81 (18)
C7—C6—H6	121.8	O3—C22—C17	110.08 (17)
C5—C6—H6	121.8	C16—C23—O3	110.98 (17)
C6—C7—O1	125.83 (18)	C16—C23—C24	133.1 (2)
C6—C7—C2	124.0 (2)	O3—C23—C24	115.93 (18)
O1—C7—C2	110.13 (17)	C23—C24—H24A	109.5
C1—C8—O1	110.86 (17)	C23—C24—H24B	109.5
C1—C8—C9	132.5 (2)	H24A—C24—H24B	109.5
O1—C8—C9	116.66 (17)	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	C25—C26—C27	109.65 (15)
C8—C9—H9C	109.5	C25—C26—H26A	109.7
H9A—C9—H9C	109.5	C27—C26—H26A	109.7
H9B—C9—H9C	109.5	C25—C26—H26B	109.7
C15—C10—C11	112.03 (18)	C27—C26—H26B	109.7
C15—C10—S1	109.46 (13)	H26A—C26—H26B	108.2
C11—C10—S1	108.18 (14)	C28—C27—C26	111.15 (17)
C15—C10—H10	109.0	C28—C27—H27A	109.4
C11—C10—H10	109.0	C26—C27—H27A	109.4
S1—C10—H10	109.0	C28—C27—H27B	109.4
C10—C11—C12	109.6 (2)	C26—C27—H27B	109.4
C10—C11—H11A	109.7	H27A—C27—H27B	108.0
C12—C11—H11A	109.7	C29—C28—C27	110.74 (17)
C10—C11—H11B	109.7	C29—C28—H28A	109.5
C12—C11—H11B	109.7	C27—C28—H28A	109.5
H11A—C11—H11B	108.2	C29—C28—H28B	109.5
C13—C12—C11	111.5 (2)	C27—C28—H28B	109.5
C13—C12—H12A	109.3	H28A—C28—H28B	108.1
C11—C12—H12A	109.3	C28—C29—C30	111.53 (17)
C13—C12—H12B	109.3	C28—C29—H29A	109.3
C11—C12—H12B	109.3	C30—C29—H29A	109.3
H12A—C12—H12B	108.0	C28—C29—H29B	109.3
C14—C13—C12	110.6 (2)	C30—C29—H29B	109.3
C14—C13—H13A	109.5	H29A—C29—H29B	108.0
C12—C13—H13A	109.5	C29—C30—C25	109.89 (17)
C14—C13—H13B	109.5	C29—C30—H30A	109.7
C12—C13—H13B	109.5	C25—C30—H30A	109.7
H13A—C13—H13B	108.1	C29—C30—H30B	109.7
C13—C14—C15	111.5 (2)	C25—C30—H30B	109.7
C13—C14—H14A	109.3	H30A—C30—H30B	108.2
O4—S2—C25—C26	53.45 (16)	C12—C13—C14—C15	−55.9 (3)
C16—S2—C25—C26	−58.32 (15)	C11—C10—C15—C14	−54.0 (3)
O4—S2—C25—C30	−70.08 (14)	S1—C10—C15—C14	−174.00 (17)
C16—S2—C25—C30	178.15 (12)	C13—C14—C15—C10	54.1 (3)
O2—S1—C1—C8	−144.40 (16)	O4—S2—C16—C23	153.83 (16)
C10—S1—C1—C8	105.31 (17)	C25—S2—C16—C23	−93.78 (17)
O2—S1—C1—C2	34.12 (18)	O4—S2—C16—C17	−23.87 (19)
C10—S1—C1—C2	−76.16 (17)	C25—S2—C16—C17	88.52 (18)
C8—C1—C2—C7	0.3 (2)	C23—C16—C17—C18	−178.8 (2)
S1—C1—C2—C7	−178.40 (14)	S2—C16—C17—C18	−0.8 (3)
C8—C1—C2—C3	179.4 (2)	C23—C16—C17—C22	1.0 (2)
S1—C1—C2—C3	0.6 (3)	S2—C16—C17—C22	178.94 (14)
C7—C2—C3—C4	0.3 (3)	C22—C17—C18—C19	0.7 (3)
C1—C2—C3—C4	−178.63 (19)	C16—C17—C18—C19	−179.6 (2)
C2—C3—C4—C5	−0.3 (3)	C17—C18—C19—C20	0.8 (3)
C2—C3—C4—Cl2	178.79 (13)	C17—C18—C19—Cl1	−179.97 (13)
C3—C4—C5—C6	0.4 (3)	C18—C19—C20—C21	−1.7 (3)
Cl2—C4—C5—C6	−178.68 (16)	Cl1—C19—C20—C21	179.09 (15)
C4—C5—C6—C7	−0.5 (3)	C19—C20—C21—C22	1.0 (3)
C5—C6—C7—O1	179.82 (17)	C20—C21—C22—O3	179.60 (17)
C5—C6—C7—C2	0.5 (3)	C20—C21—C22—C17	0.5 (3)
C8—O1—C7—C6	−178.7 (2)	C23—O3—C22—C21	−179.5 (2)
C8—O1—C7—C2	0.7 (2)	C23—O3—C22—C17	−0.34 (19)
C3—C2—C7—C6	−0.4 (3)	C18—C17—C22—C21	−1.4 (3)
C1—C2—C7—C6	178.8 (2)	C16—C17—C22—C21	178.85 (19)
C3—C2—C7—O1	−179.83 (16)	C18—C17—C22—O3	179.42 (15)
C1—C2—C7—O1	−0.6 (2)	C16—C17—C22—O3	−0.37 (19)
C2—C1—C8—O1	0.0 (2)	C17—C16—C23—O3	−1.2 (2)
S1—C1—C8—O1	178.82 (13)	S2—C16—C23—O3	−179.34 (13)
C2—C1—C8—C9	178.08 (19)	C17—C16—C23—C24	178.90 (19)
S1—C1—C8—C9	−3.1 (3)	S2—C16—C23—C24	0.8 (3)
C7—O1—C8—C1	−0.4 (2)	C22—O3—C23—C16	1.0 (2)
C7—O1—C8—C9	−178.81 (16)	C22—O3—C23—C24	−179.11 (16)
O2—S1—C10—C15	−179.02 (15)	C30—C25—C26—C27	−56.8 (2)
C1—S1—C10—C15	−68.41 (16)	S2—C25—C26—C27	−177.59 (14)
O2—S1—C10—C11	58.67 (17)	C25—C26—C27—C28	57.1 (2)
C1—S1—C10—C11	169.27 (15)	C26—C27—C28—C29	−57.4 (2)
C15—C10—C11—C12	55.3 (3)	C27—C28—C29—C30	56.8 (3)
S1—C10—C11—C12	175.99 (18)	C28—C29—C30—C25	−55.9 (2)
C10—C11—C12—C13	−57.2 (3)	C26—C25—C30—C29	56.2 (2)
C11—C12—C13—C14	58.1 (3)	S2—C25—C30—C29	−178.84 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.54	3.469 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.54	3.469 (3)	166

Symmetry code: (i) .