5-Chloro-2-methyl-3-(4-methyl-phenyl-sulfon-yl)-1-benzo-furan.

The title compound, C16H13ClO3S, crystallized with two independent mol-ecules in the asymmetric unit. The 4-methyl-phenyl rings make dihedral angles of 75.15 (4)° and 72.18 (4)° with the planes of the benzo-furan ring systems in the two mol-ecules. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C16H13ClO3S

M = 320.77

Triclinic,

a = 7.3725 (2) Å

b = 10.0967 (3) Å

c = 20.8173 (7) Å

α = 98.086 (1)°

β = 99.547 (2)°

γ = 106.547 (1)°

V = 1435.62 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 173 K

0.41 × 0.29 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.670, T max = 0.746

26328 measured reflections

7109 independent reflections

5967 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.04

7109 reflections

383 parameters

H-atom parameters constrained

Δρmax = 0.38 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813015468/pk2485sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015468/pk2485Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015468/pk2485Isup3.cml

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

C16H13ClO3S	Z = 4
Mr = 320.77	F(000) = 664
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Melting point = 461–462 K
a = 7.3725 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0967 (3) Å	Cell parameters from 9961 reflections
c = 20.8173 (7) Å	θ = 2.6–28.3°
α = 98.086 (1)°	µ = 0.42 mm−1
β = 99.547 (2)°	T = 173 K
γ = 106.547 (1)°	Block, colourless
V = 1435.62 (8) Å3	0.41 × 0.29 × 0.23 mm

Bruker SMART APEXII CCD diffractometer	7109 independent reflections
Radiation source: rotating anode	5967 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 1.0°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
Tmin = 0.670, Tmax = 0.746	l = −27→27
26328 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.6008P] where P = (Fo2 + 2Fc2)/3
7109 reflections	(Δ/σ)max = 0.001
383 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.40 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
Cl1	0.24968 (8)	0.40295 (6)	0.68981 (2)	0.04342 (13)
S1	−0.03637 (6)	0.18272 (4)	0.393226 (19)	0.02505 (10)
O1	0.29244 (17)	0.57988 (12)	0.43797 (6)	0.0290 (2)
O2	−0.13514 (17)	0.13204 (12)	0.44305 (6)	0.0310 (3)
O3	−0.14612 (18)	0.18003 (13)	0.32903 (6)	0.0347 (3)
C1	0.1097 (2)	0.35510 (16)	0.42756 (7)	0.0238 (3)
C2	0.1844 (2)	0.41316 (16)	0.49781 (7)	0.0228 (3)
C3	0.1677 (2)	0.36384 (17)	0.55651 (8)	0.0261 (3)
H3	0.0931	0.2699	0.5563	0.031*
C4	0.2657 (2)	0.45931 (19)	0.61515 (8)	0.0296 (4)
C5	0.3744 (2)	0.59807 (19)	0.61716 (8)	0.0328 (4)
H5	0.4377	0.6592	0.6588	0.039*
C6	0.3910 (2)	0.64748 (18)	0.55939 (9)	0.0313 (4)
H6	0.4639	0.7419	0.5597	0.038*
C7	0.2953 (2)	0.55174 (17)	0.50081 (8)	0.0254 (3)
C8	0.1795 (2)	0.45846 (17)	0.39433 (8)	0.0270 (3)
C9	0.1631 (3)	0.4659 (2)	0.32330 (9)	0.0363 (4)
H9A	0.2897	0.4773	0.3119	0.054*
H9B	0.1203	0.5465	0.3149	0.054*
H9C	0.0686	0.3788	0.2960	0.054*
C10	0.1255 (2)	0.08739 (16)	0.38118 (8)	0.0253 (3)
C11	0.1953 (3)	0.08322 (18)	0.32311 (8)	0.0312 (4)
H11	0.1560	0.1310	0.2899	0.037*
C12	0.3231 (3)	0.00823 (19)	0.31462 (9)	0.0345 (4)
H12	0.3732	0.0064	0.2754	0.041*
C13	0.3796 (2)	−0.06433 (18)	0.36201 (9)	0.0327 (4)
C14	0.3082 (3)	−0.05848 (19)	0.41956 (9)	0.0343 (4)
H14	0.3458	−0.1076	0.4525	0.041*
C15	0.1828 (2)	0.01806 (18)	0.42974 (8)	0.0295 (3)
H15	0.1366	0.0229	0.4697	0.035*
S2	0.09432 (6)	0.27584 (4)	0.103954 (18)	0.02438 (9)
Cl2	0.01357 (7)	0.22781 (5)	−0.19394 (2)	0.03793 (11)
O4	0.36056 (16)	0.63145 (12)	0.05479 (5)	0.0276 (2)
O6	−0.06739 (16)	0.18020 (12)	0.05491 (6)	0.0302 (3)
O5	0.06614 (18)	0.33050 (13)	0.16777 (6)	0.0330 (3)
C17	0.1952 (2)	0.41650 (16)	0.06766 (7)	0.0237 (3)
C18	0.1834 (2)	0.41055 (16)	−0.00264 (7)	0.0225 (3)
C19	0.0958 (2)	0.30830 (17)	−0.06083 (8)	0.0259 (3)
H19	0.0237	0.2146	−0.0597	0.031*
C20	0.1199 (2)	0.35085 (18)	−0.11983 (8)	0.0271 (3)
C21	0.2233 (2)	0.48782 (19)	−0.12355 (8)	0.0302 (4)
H21	0.2341	0.5115	−0.1656	0.036*
C22	0.3098 (2)	0.58913 (18)	−0.06623 (8)	0.0292 (3)
H22	0.3808	0.6831	−0.0674	0.035*
C23	0.2875 (2)	0.54624 (16)	−0.00748 (8)	0.0246 (3)
C24	0.3028 (2)	0.54992 (17)	0.09942 (8)	0.0260 (3)
C25	0.3701 (3)	0.62270 (19)	0.16990 (8)	0.0349 (4)
H25A	0.3051	0.5622	0.1977	0.052*
H25B	0.3391	0.7113	0.1754	0.052*
H25C	0.5105	0.6429	0.1834	0.052*
C26	0.2726 (2)	0.19238 (16)	0.11785 (8)	0.0245 (3)
C27	0.2712 (2)	0.08041 (17)	0.07094 (8)	0.0298 (3)
H27	0.1760	0.0494	0.0306	0.036*
C28	0.4102 (3)	0.01391 (18)	0.08349 (9)	0.0345 (4)
H28	0.4080	−0.0643	0.0518	0.041*
C29	0.5527 (2)	0.06008 (18)	0.14183 (9)	0.0326 (4)
C30	0.5542 (3)	0.1749 (2)	0.18749 (9)	0.0342 (4)
H30	0.6524	0.2085	0.2271	0.041*
C31	0.4152 (3)	0.24113 (18)	0.17622 (8)	0.0302 (4)
H31	0.4168	0.3191	0.2080	0.036*
C32	0.7015 (3)	−0.0134 (2)	0.15597 (11)	0.0444 (5)
H32A	0.6896	−0.0838	0.1166	0.067*
H32B	0.6805	−0.0601	0.1935	0.067*
H32C	0.8315	0.0559	0.1670	0.067*
C16	0.5134 (3)	−0.1492 (2)	0.35059 (12)	0.0447 (5)
H16A	0.4374	−0.2440	0.3255	0.067*
H16B	0.5848	−0.1559	0.3935	0.067*
H16C	0.6053	−0.1029	0.3253	0.067*

	U11	U22	U33	U12	U13	U23
Cl1	0.0559 (3)	0.0585 (3)	0.0223 (2)	0.0277 (2)	0.00813 (19)	0.00901 (19)
S1	0.02324 (19)	0.02530 (19)	0.02250 (18)	0.00409 (15)	0.00130 (14)	0.00326 (14)
O1	0.0304 (6)	0.0251 (6)	0.0312 (6)	0.0062 (5)	0.0083 (5)	0.0081 (5)
O2	0.0275 (6)	0.0301 (6)	0.0333 (6)	0.0037 (5)	0.0096 (5)	0.0076 (5)
O3	0.0322 (6)	0.0381 (7)	0.0267 (6)	0.0082 (5)	−0.0054 (5)	0.0031 (5)
C1	0.0226 (7)	0.0242 (7)	0.0231 (7)	0.0066 (6)	0.0031 (6)	0.0034 (6)
C2	0.0203 (7)	0.0253 (7)	0.0232 (7)	0.0085 (6)	0.0044 (6)	0.0035 (6)
C3	0.0266 (8)	0.0279 (8)	0.0245 (7)	0.0097 (6)	0.0053 (6)	0.0055 (6)
C4	0.0309 (8)	0.0401 (9)	0.0215 (7)	0.0180 (7)	0.0041 (6)	0.0053 (7)
C5	0.0288 (8)	0.0354 (9)	0.0291 (8)	0.0125 (7)	−0.0018 (7)	−0.0049 (7)
C6	0.0255 (8)	0.0256 (8)	0.0376 (9)	0.0066 (7)	0.0016 (7)	−0.0017 (7)
C7	0.0220 (7)	0.0264 (8)	0.0288 (8)	0.0085 (6)	0.0064 (6)	0.0054 (6)
C8	0.0266 (8)	0.0279 (8)	0.0270 (8)	0.0093 (6)	0.0052 (6)	0.0066 (6)
C9	0.0424 (10)	0.0425 (10)	0.0281 (8)	0.0138 (8)	0.0106 (7)	0.0159 (8)
C10	0.0261 (8)	0.0208 (7)	0.0244 (7)	0.0029 (6)	0.0032 (6)	0.0017 (6)
C11	0.0367 (9)	0.0297 (8)	0.0230 (7)	0.0062 (7)	0.0047 (7)	0.0026 (6)
C12	0.0380 (10)	0.0311 (9)	0.0295 (8)	0.0049 (7)	0.0113 (7)	−0.0017 (7)
C13	0.0294 (9)	0.0213 (8)	0.0408 (9)	0.0018 (6)	0.0071 (7)	−0.0018 (7)
C14	0.0361 (9)	0.0288 (9)	0.0386 (9)	0.0098 (7)	0.0074 (7)	0.0106 (7)
C15	0.0328 (9)	0.0277 (8)	0.0273 (8)	0.0065 (7)	0.0085 (7)	0.0079 (6)
S2	0.02491 (19)	0.02583 (19)	0.02175 (18)	0.00625 (15)	0.00545 (14)	0.00582 (14)
Cl2	0.0461 (3)	0.0422 (3)	0.02349 (19)	0.0162 (2)	0.00331 (17)	0.00018 (17)
O4	0.0278 (6)	0.0234 (6)	0.0282 (6)	0.0048 (5)	0.0039 (5)	0.0039 (4)
O6	0.0248 (6)	0.0302 (6)	0.0310 (6)	0.0032 (5)	0.0029 (5)	0.0065 (5)
O5	0.0377 (7)	0.0378 (7)	0.0258 (6)	0.0121 (5)	0.0126 (5)	0.0070 (5)
C17	0.0243 (7)	0.0247 (7)	0.0223 (7)	0.0080 (6)	0.0047 (6)	0.0053 (6)
C18	0.0206 (7)	0.0249 (7)	0.0234 (7)	0.0086 (6)	0.0046 (6)	0.0066 (6)
C19	0.0257 (8)	0.0252 (8)	0.0255 (7)	0.0075 (6)	0.0040 (6)	0.0045 (6)
C20	0.0276 (8)	0.0325 (8)	0.0226 (7)	0.0130 (7)	0.0047 (6)	0.0035 (6)
C21	0.0323 (9)	0.0376 (9)	0.0278 (8)	0.0159 (7)	0.0117 (7)	0.0134 (7)
C22	0.0284 (8)	0.0276 (8)	0.0347 (9)	0.0092 (7)	0.0105 (7)	0.0113 (7)
C23	0.0223 (7)	0.0252 (8)	0.0269 (7)	0.0085 (6)	0.0052 (6)	0.0051 (6)
C24	0.0251 (8)	0.0264 (8)	0.0269 (8)	0.0090 (6)	0.0051 (6)	0.0054 (6)
C25	0.0369 (10)	0.0325 (9)	0.0279 (8)	0.0065 (7)	0.0013 (7)	−0.0017 (7)
C26	0.0260 (8)	0.0232 (7)	0.0238 (7)	0.0056 (6)	0.0048 (6)	0.0086 (6)
C27	0.0290 (8)	0.0257 (8)	0.0291 (8)	0.0045 (7)	0.0012 (6)	0.0019 (6)
C28	0.0351 (9)	0.0254 (8)	0.0414 (10)	0.0087 (7)	0.0075 (8)	0.0039 (7)
C29	0.0297 (9)	0.0289 (8)	0.0423 (10)	0.0082 (7)	0.0093 (7)	0.0179 (7)
C30	0.0330 (9)	0.0393 (10)	0.0280 (8)	0.0092 (8)	−0.0001 (7)	0.0119 (7)
C31	0.0351 (9)	0.0309 (8)	0.0222 (7)	0.0087 (7)	0.0025 (6)	0.0056 (6)
C32	0.0368 (10)	0.0415 (11)	0.0621 (13)	0.0171 (9)	0.0106 (9)	0.0243 (10)
C16	0.0392 (11)	0.0286 (9)	0.0641 (13)	0.0088 (8)	0.0160 (9)	0.0002 (9)

Cl1—C4	1.7392 (17)	S2—C26	1.7591 (16)
S1—O2	1.4336 (12)	Cl2—C20	1.7443 (16)
S1—O3	1.4353 (12)	O4—C24	1.367 (2)
S1—C1	1.7397 (16)	O4—C23	1.3789 (18)
S1—C10	1.7607 (16)	C17—C24	1.359 (2)
O1—C8	1.370 (2)	C17—C18	1.443 (2)
O1—C7	1.3751 (19)	C18—C23	1.394 (2)
C1—C8	1.359 (2)	C18—C19	1.400 (2)
C1—C2	1.447 (2)	C19—C20	1.379 (2)
C2—C7	1.392 (2)	C19—H19	0.9500
C2—C3	1.394 (2)	C20—C21	1.396 (2)
C3—C4	1.386 (2)	C21—C22	1.382 (2)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.393 (3)	C22—C23	1.373 (2)
C5—C6	1.376 (3)	C22—H22	0.9500
C5—H5	0.9500	C24—C25	1.479 (2)
C6—C7	1.383 (2)	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C8—C9	1.478 (2)	C25—H25C	0.9800
C9—H9A	0.9800	C26—C27	1.382 (2)
C9—H9B	0.9800	C26—C31	1.392 (2)
C9—H9C	0.9800	C27—C28	1.386 (2)
C10—C15	1.384 (2)	C27—H27	0.9500
C10—C11	1.390 (2)	C28—C29	1.391 (2)
C11—C12	1.384 (3)	C28—H28	0.9500
C11—H11	0.9500	C29—C30	1.389 (3)
C12—C13	1.387 (3)	C29—C32	1.502 (2)
C12—H12	0.9500	C30—C31	1.381 (2)
C13—C14	1.387 (3)	C30—H30	0.9500
C13—C16	1.505 (3)	C31—H31	0.9500
C14—C15	1.387 (2)	C32—H32A	0.9800
C14—H14	0.9500	C32—H32B	0.9800
C15—H15	0.9500	C32—H32C	0.9800
S2—O6	1.4351 (12)	C16—H16A	0.9800
S2—O5	1.4364 (12)	C16—H16B	0.9800
S2—C17	1.7399 (16)	C16—H16C	0.9800
O2—S1—O3	119.75 (8)	C24—O4—C23	106.77 (12)
O2—S1—C1	106.70 (7)	C24—C17—C18	107.37 (14)
O3—S1—C1	108.68 (8)	C24—C17—S2	127.08 (12)
O2—S1—C10	107.90 (8)	C18—C17—S2	125.53 (12)
O3—S1—C10	107.69 (7)	C23—C18—C19	119.07 (14)
C1—S1—C10	105.23 (7)	C23—C18—C17	104.74 (13)
C8—O1—C7	106.81 (12)	C19—C18—C17	136.18 (15)
C8—C1—C2	107.30 (14)	C20—C19—C18	116.46 (15)
C8—C1—S1	127.15 (12)	C20—C19—H19	121.8
C2—C1—S1	125.53 (12)	C18—C19—H19	121.8
C7—C2—C3	119.56 (14)	C19—C20—C21	123.49 (15)
C7—C2—C1	104.64 (14)	C19—C20—Cl2	118.42 (13)
C3—C2—C1	135.79 (15)	C21—C20—Cl2	118.08 (13)
C4—C3—C2	116.34 (15)	C22—C21—C20	120.25 (15)
C4—C3—H3	121.8	C22—C21—H21	119.9
C2—C3—H3	121.8	C20—C21—H21	119.9
C3—C4—C5	123.26 (16)	C23—C22—C21	116.20 (16)
C3—C4—Cl1	118.16 (14)	C23—C22—H22	121.9
C5—C4—Cl1	118.58 (13)	C21—C22—H22	121.9
C6—C5—C4	120.66 (15)	C22—C23—O4	125.08 (15)
C6—C5—H5	119.7	C22—C23—C18	124.52 (15)
C4—C5—H5	119.7	O4—C23—C18	110.39 (13)
C5—C6—C7	116.12 (16)	C17—C24—O4	110.74 (14)
C5—C6—H6	121.9	C17—C24—C25	134.29 (16)
C7—C6—H6	121.9	O4—C24—C25	114.97 (14)
O1—C7—C6	125.33 (15)	C24—C25—H25A	109.5
O1—C7—C2	110.61 (13)	C24—C25—H25B	109.5
C6—C7—C2	124.05 (16)	H25A—C25—H25B	109.5
C1—C8—O1	110.64 (14)	C24—C25—H25C	109.5
C1—C8—C9	134.21 (16)	H25A—C25—H25C	109.5
O1—C8—C9	115.13 (15)	H25B—C25—H25C	109.5
C8—C9—H9A	109.5	C27—C26—C31	120.64 (15)
C8—C9—H9B	109.5	C27—C26—S2	120.14 (12)
H9A—C9—H9B	109.5	C31—C26—S2	119.21 (12)
C8—C9—H9C	109.5	C26—C27—C28	119.28 (15)
H9A—C9—H9C	109.5	C26—C27—H27	120.4
H9B—C9—H9C	109.5	C28—C27—H27	120.4
C15—C10—C11	120.71 (16)	C27—C28—C29	120.96 (16)
C15—C10—S1	119.69 (13)	C27—C28—H28	119.5
C11—C10—S1	119.59 (13)	C29—C28—H28	119.5
C12—C11—C10	118.78 (16)	C30—C29—C28	118.75 (16)
C12—C11—H11	120.6	C30—C29—C32	120.25 (17)
C10—C11—H11	120.6	C28—C29—C32	121.00 (17)
C11—C12—C13	121.53 (16)	C31—C30—C29	121.04 (16)
C11—C12—H12	119.2	C31—C30—H30	119.5
C13—C12—H12	119.2	C29—C30—H30	119.5
C14—C13—C12	118.62 (16)	C30—C31—C26	119.30 (16)
C14—C13—C16	120.84 (18)	C30—C31—H31	120.3
C12—C13—C16	120.53 (17)	C26—C31—H31	120.4
C13—C14—C15	120.90 (17)	C29—C32—H32A	109.5
C13—C14—H14	119.5	C29—C32—H32B	109.5
C15—C14—H14	119.5	H32A—C32—H32B	109.5
C10—C15—C14	119.43 (16)	C29—C32—H32C	109.5
C10—C15—H15	120.3	H32A—C32—H32C	109.5
C14—C15—H15	120.3	H32B—C32—H32C	109.5
O6—S2—O5	119.79 (7)	C13—C16—H16A	109.5
O6—S2—C17	106.81 (7)	C13—C16—H16B	109.5
O5—S2—C17	108.76 (8)	H16A—C16—H16B	109.5
O6—S2—C26	107.88 (7)	C13—C16—H16C	109.5
O5—S2—C26	107.38 (7)	H16A—C16—H16C	109.5
C17—S2—C26	105.33 (7)	H16B—C16—H16C	109.5
O2—S1—C1—C8	−157.13 (14)	O6—S2—C17—C24	155.68 (14)
O3—S1—C1—C8	−26.72 (17)	O5—S2—C17—C24	25.08 (17)
C10—S1—C1—C8	88.40 (16)	C26—S2—C17—C24	−89.78 (15)
O2—S1—C1—C2	25.03 (15)	O6—S2—C17—C18	−26.17 (15)
O3—S1—C1—C2	155.44 (13)	O5—S2—C17—C18	−156.77 (13)
C10—S1—C1—C2	−89.44 (14)	C26—S2—C17—C18	88.37 (14)
C8—C1—C2—C7	0.54 (17)	C24—C17—C18—C23	−0.43 (17)
S1—C1—C2—C7	178.73 (12)	S2—C17—C18—C23	−178.88 (11)
C8—C1—C2—C3	179.77 (17)	C24—C17—C18—C19	−179.32 (17)
S1—C1—C2—C3	−2.0 (3)	S2—C17—C18—C19	2.2 (3)
C7—C2—C3—C4	−0.1 (2)	C23—C18—C19—C20	−0.1 (2)
C1—C2—C3—C4	−179.20 (16)	C17—C18—C19—C20	178.70 (16)
C2—C3—C4—C5	0.7 (2)	C18—C19—C20—C21	−0.6 (2)
C2—C3—C4—Cl1	−179.93 (11)	C18—C19—C20—Cl2	−179.89 (11)
C3—C4—C5—C6	−0.6 (3)	C19—C20—C21—C22	0.6 (2)
Cl1—C4—C5—C6	−179.89 (13)	Cl2—C20—C21—C22	179.89 (13)
C4—C5—C6—C7	−0.3 (2)	C20—C21—C22—C23	0.1 (2)
C8—O1—C7—C6	−178.94 (15)	C21—C22—C23—O4	−179.20 (14)
C8—O1—C7—C2	−0.19 (17)	C21—C22—C23—C18	−0.8 (2)
C5—C6—C7—O1	179.58 (14)	C24—O4—C23—C22	178.55 (15)
C5—C6—C7—C2	1.0 (2)	C24—O4—C23—C18	−0.02 (16)
C3—C2—C7—O1	−179.60 (13)	C19—C18—C23—C22	0.8 (2)
C1—C2—C7—O1	−0.21 (16)	C17—C18—C23—C22	−178.31 (15)
C3—C2—C7—C6	−0.8 (2)	C19—C18—C23—O4	179.40 (13)
C1—C2—C7—C6	178.56 (15)	C17—C18—C23—O4	0.28 (16)
C2—C1—C8—O1	−0.68 (18)	C18—C17—C24—O4	0.44 (17)
S1—C1—C8—O1	−178.84 (11)	S2—C17—C24—O4	178.86 (11)
C2—C1—C8—C9	177.70 (18)	C18—C17—C24—C25	−178.78 (17)
S1—C1—C8—C9	−0.5 (3)	S2—C17—C24—C25	−0.4 (3)
C7—O1—C8—C1	0.55 (17)	C23—O4—C24—C17	−0.27 (17)
C7—O1—C8—C9	−178.17 (14)	C23—O4—C24—C25	179.12 (13)
O2—S1—C10—C15	−19.93 (15)	O6—S2—C26—C27	20.41 (16)
O3—S1—C10—C15	−150.50 (13)	O5—S2—C26—C27	150.81 (14)
C1—S1—C10—C15	93.70 (14)	C17—S2—C26—C27	−93.39 (15)
O2—S1—C10—C11	160.40 (13)	O6—S2—C26—C31	−160.06 (13)
O3—S1—C10—C11	29.84 (15)	O5—S2—C26—C31	−29.66 (15)
C1—S1—C10—C11	−85.96 (14)	C17—S2—C26—C31	86.14 (14)
C15—C10—C11—C12	0.1 (2)	C31—C26—C27—C28	2.0 (3)
S1—C10—C11—C12	179.74 (13)	S2—C26—C27—C28	−178.50 (13)
C10—C11—C12—C13	1.2 (3)	C26—C27—C28—C29	−1.3 (3)
C11—C12—C13—C14	−1.3 (3)	C27—C28—C29—C30	−0.3 (3)
C11—C12—C13—C16	177.91 (17)	C27—C28—C29—C32	179.02 (17)
C12—C13—C14—C15	0.1 (3)	C28—C29—C30—C31	1.2 (3)
C16—C13—C14—C15	−179.11 (17)	C32—C29—C30—C31	−178.07 (17)
C11—C10—C15—C14	−1.2 (2)	C29—C30—C31—C26	−0.6 (3)
S1—C10—C15—C14	179.10 (13)	C27—C26—C31—C30	−1.1 (3)
C13—C14—C15—C10	1.2 (3)	S2—C26—C31—C30	179.42 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2i	0.95	2.56	3.251 (2)	130
C27—H27···O6ii	0.95	2.55	3.248 (2)	131
C30—H30···O3iii	0.95	2.48	3.361 (2)	154
C22—H22···Cgiv	0.95	2.71	3.572 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C26–C31 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.95	2.56	3.251 (2)	130
C27—H27⋯O6ii	0.95	2.55	3.248 (2)	131
C30—H30⋯O3iii	0.95	2.48	3.361 (2)	154
C22—H22⋯Cg iv	0.95	2.71	3.572 (2)	136

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