5-Chloro-2-methyl-3-phenyl­sulfonyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808015699

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1190

doi:10.1107/S1600536808015699

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5-Chloro-2-methyl-3-phenylsulfonyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 20 May 2008; accepted 25 May 2008; online 7 June 2008)

The title compound, C₁₅H₁₁ClO₃S, was prepared by the oxidation of 5-chloro-2-methyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. There are two symmetry-independent molecules in the asymmetric unit. The dihedral angles formed by the phenyl ring and the plane of the benzofuran system are 77.80 (8) and 78.34 (8)°. The crystal structure is stabilized by aromatic π–π stacking interactions between the furan ring and the benzene rings of neighbouring benzofuran fragments from two symmetry-independent molecules; the centroid–centroid distances within the stacks are 3.689 (4), 3.702 (4), 3.825 (4) and 3.826 (4) Å. Additionally, the stacked molecules exhibit inter- and intramolecular C—H⋯O interactions.

Related literature

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₅H₁₁ClO₃S
M_r = 306.76
Triclinic, $[P \overline 1]$
a = 7.4029 (7) Å
b = 9.2669 (9) Å
c = 20.889 (2) Å
α = 100.953 (2)°
β = 95.626 (2)°
γ = 104.212 (2)°
V = 1348.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 173 (2) K
0.50 × 0.50 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.795, T_max = 0.870
9232 measured reflections
4555 independent reflections
4119 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.116
S = 1.16
4555 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2	0.98	2.44	3.153 (4)	130
C14—H14⋯O3ⁱ	0.95	2.51	3.429 (4)	164
C29—H29⋯O5ⁱⁱ	0.95	2.51	3.453 (4)	170
C30—H30A⋯O6	0.98	2.42	3.141 (4)	130
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015699/rk2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015699/rk2091Isup2.hkl

checkCIF report

Comment top

This work is related to our communications on the synthesis and structure of 2-methyl-3-phenylsulfonyl-1-benzofuran analogues, viz. 5-bromo-2-methyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008a) and 2,5-dimethyl-3-phenylsulfonyl-1-benzofuran (Choi et al., 2008b). Herein we report the crystal and molecular structure of the title compound, 5-chloro-2-methyl-3-phenylsulfonyl-1-benzofuran C₁₅H₁₁ClO₃S, (I), (Fig. 1).

The benzofuran unit is essentially planar, with a max deviation of 0.015 (2) Å for unit A, and 0.020 (2) Å for unit B, respectively, from the least-squares plane defined by the nine constituent atoms. In the title compound, the dihedral angles formed by the benzofuran fragment and the plane of the phenyl ring are 77.80 (8)° in unit A and 78.34 (8)° in unit B, respectively. The crystal packing (Fig. 2) is stabilized by four different π–π interactions within each stack of molecules; one between the furan ring (Cg1) and an adjacent benzene ring (Cg2ⁱ) [distance 3.702 (4) Å], a second between the furan ring (Cg1) and an adjacent benzene ring (Cg2ⁱⁱ) [distance 3.826 (4) Å], a third between the furan ring (Cg3) and an adjacent benzene ring (Cg4ⁱⁱⁱ) [distance 3.689 (4) Å], a fourth between the furan ring (Cg3) and an adjacent benzene ring (Cg4^iv) [distance 3.825 (4) Å], (Cg1, Cg2, Cg3, and Cg4 are the centroids of the O1/C8/C1/C2/C7 furan ring, the C2/C3/C4/C5/C6/C7 benzene ring, the O4/C23/C16/C17/C22 furan ring, the C17/C18/C19/C20/C21/C22 benzene ring, respectively, symmetry code as in Fig. 2). The molecular packing is further stabilized by inter- and intramolecular C—H···O hydrogen bonds (Fig. 3 and Table; symmetry codes as in Fig. 3).

Related literature top

For the crystal structures of similar 2-methyl-3-phenylsulfonyl-1-benzofuran derivatives, see: Choi et al. (2008a,b).

Experimental top

77% 3-chloroperoxybenzoic acid (471 mg, 2.1 mmol) was added in small portions to a stirred solution of 5-chloro-2-methyl-3-phenylsulfanyl-1-benzofuran (275 mg, 1.0 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 4 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane–ethylacetate, 2:1 v/v) to afford the I as a colorless solid [yield 81%, m.p. 468–469 K; R_f = 0.61 (hexane–ethylacetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the I in chloroform at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.80 (s, 3H), 7.28 (d, J = 2.16 Hz, 1H), 7.33 (s, 1H), 7.51–7.55 (m, 2H), 7.58–7.61 (m, 1H), 7.88 (d, J = 2.20 Hz, 1H), 7.98–8.04 (m, 2H); EI-MS 308 [M+2], 306 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The π–π interactions (dotted lines) in the title compound. Cg denotes the ring centroids. Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z; (iv) -x, -y, -z.
	Fig. 3. C—H···O interactions (dotted lines) in the title compound. Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -z.

5-Chloro-2-methyl-3-phenylsulfonyl-1-benzofuran top

Crystal data top

C₁₅H₁₁ClO₃S	Z = 4
M_r = 306.76	F(000) = 632
Triclinic, P1	D_x = 1.512 Mg m⁻³
Hall symbol: -P 1	Melting point = 468–469 K
a = 7.4029 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2669 (9) Å	Cell parameters from 7490 reflections
c = 20.889 (2) Å	θ = 2.3–28.2°
α = 100.953 (2)°	µ = 0.44 mm⁻¹
β = 95.626 (2)°	T = 173 K
γ = 104.212 (2)°	Block, colourless
V = 1348.0 (2) Å³	0.50 × 0.50 × 0.30 mm

Data collection top

Bruker SMART CCD diffractometer	4555 independent reflections
Radiation source: fine-focus sealed tube	4119 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 1.0°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −11→11
T_min = 0.795, T_max = 0.870	l = −24→24
9232 measured reflections

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0289P)² + 1.6847P] where P = (F_o² + 2F_c²)/3
4555 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₅H₁₁ClO₃S	γ = 104.212 (2)°
M_r = 306.76	V = 1348.0 (2) Å³
Triclinic, P1	Z = 4
a = 7.4029 (7) Å	Mo Kα radiation
b = 9.2669 (9) Å	µ = 0.44 mm⁻¹
c = 20.889 (2) Å	T = 173 K
α = 100.953 (2)°	0.50 × 0.50 × 0.30 mm
β = 95.626 (2)°

Data collection top

Bruker SMART CCD diffractometer	4555 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	4119 reflections with I > 2σ(I)
T_min = 0.795, T_max = 0.870	R_int = 0.036
9232 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.16	Δρ_max = 0.36 e Å⁻³
4555 reflections	Δρ_min = −0.43 e Å⁻³
363 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.94027 (12)	0.83729 (9)	0.68782 (4)	0.0390 (2)
S1	0.89392 (10)	0.73758 (8)	0.38915 (3)	0.02487 (18)
O1	0.6676 (3)	0.3633 (2)	0.44767 (10)	0.0285 (4)
O2	0.9367 (3)	0.6705 (3)	0.32655 (10)	0.0344 (5)
O3	1.0381 (3)	0.8528 (2)	0.43567 (10)	0.0327 (5)
C1	0.8078 (4)	0.5920 (3)	0.42946 (13)	0.0235 (6)
C2	0.8110 (4)	0.6091 (3)	0.50012 (13)	0.0219 (6)
C3	0.8793 (4)	0.7294 (3)	0.55589 (13)	0.0242 (6)
H3	0.9389	0.8302	0.5524	0.029*
C4	0.8551 (4)	0.6929 (3)	0.61626 (14)	0.0265 (6)
C5	0.7692 (4)	0.5459 (4)	0.62322 (14)	0.0297 (6)
H5	0.7575	0.5271	0.6660	0.036*
C6	0.7012 (4)	0.4275 (3)	0.56827 (15)	0.0303 (7)
H6	0.6421	0.3266	0.5718	0.036*
C7	0.7242 (4)	0.4643 (3)	0.50790 (14)	0.0242 (6)
C8	0.7201 (4)	0.4438 (3)	0.40081 (14)	0.0262 (6)
C9	0.7018 (4)	0.8137 (3)	0.37439 (14)	0.0246 (6)
C10	0.5757 (4)	0.7514 (4)	0.31622 (15)	0.0311 (7)
H10	0.5941	0.6705	0.2843	0.037*
C11	0.4221 (5)	0.8097 (4)	0.30559 (18)	0.0406 (8)
H11	0.3351	0.7694	0.2659	0.049*
C12	0.3958 (5)	0.9256 (4)	0.3524 (2)	0.0445 (9)
H12	0.2897	0.9641	0.3449	0.053*
C13	0.5210 (5)	0.9865 (4)	0.40995 (19)	0.0421 (8)
H13	0.5015	1.0672	0.4417	0.051*
C14	0.6760 (4)	0.9309 (3)	0.42202 (16)	0.0316 (7)
H14	0.7624	0.9719	0.4619	0.038*
C15	0.6662 (5)	0.3533 (4)	0.33182 (15)	0.0352 (7)
H15A	0.7152	0.4174	0.3017	0.053*
H15B	0.5285	0.3172	0.3212	0.053*
H15C	0.7193	0.2655	0.3270	0.053*
Cl2	0.24348 (13)	0.14348 (9)	−0.18646 (4)	0.0400 (2)
S2	0.49179 (10)	0.35480 (8)	0.11049 (3)	0.02486 (18)
O4	0.2303 (3)	−0.0834 (2)	0.05447 (10)	0.0303 (5)
O5	0.5910 (3)	0.4231 (2)	0.06317 (10)	0.0315 (5)
O6	0.5927 (3)	0.3559 (3)	0.17302 (10)	0.0339 (5)
C16	0.3752 (4)	0.1665 (3)	0.07152 (14)	0.0236 (6)
C17	0.3089 (4)	0.1109 (3)	0.00122 (13)	0.0225 (6)
C18	0.3154 (4)	0.1733 (3)	−0.05452 (13)	0.0241 (6)
H18	0.3716	0.2787	−0.0515	0.029*
C19	0.2356 (4)	0.0736 (3)	−0.11451 (14)	0.0274 (6)
C20	0.1522 (4)	−0.0821 (3)	−0.12108 (15)	0.0309 (7)
H20	0.1012	−0.1456	−0.1635	0.037*
C21	0.1440 (4)	−0.1436 (3)	−0.06597 (15)	0.0315 (7)
H21	0.0877	−0.2489	−0.0690	0.038*
C22	0.2222 (4)	−0.0437 (3)	−0.00587 (14)	0.0244 (6)
C23	0.3230 (4)	0.0464 (3)	0.10065 (14)	0.0276 (6)
C24	0.3087 (4)	0.4413 (3)	0.12603 (14)	0.0254 (6)
C25	0.2273 (4)	0.4267 (3)	0.18244 (15)	0.0317 (7)
H25	0.2729	0.3742	0.2126	0.038*
C26	0.0798 (5)	0.4891 (4)	0.19426 (17)	0.0408 (8)
H26	0.0228	0.4797	0.2326	0.049*
C27	0.0152 (5)	0.5653 (4)	0.15001 (19)	0.0447 (9)
H27	−0.0866	0.6083	0.1582	0.054*
C28	0.0965 (5)	0.5797 (4)	0.0943 (2)	0.0442 (9)
H28	0.0508	0.6328	0.0645	0.053*
C29	0.2448 (4)	0.5171 (3)	0.08137 (17)	0.0348 (7)
H29	0.3010	0.5262	0.0428	0.042*
C30	0.3420 (5)	0.0266 (4)	0.16940 (16)	0.0396 (8)
H30A	0.4237	0.1205	0.1984	0.059*
H30B	0.3975	−0.0583	0.1720	0.059*
H30C	0.2173	0.0044	0.1833	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0524 (5)	0.0418 (5)	0.0215 (4)	0.0176 (4)	0.0002 (3)	−0.0001 (3)
S1	0.0231 (4)	0.0292 (4)	0.0215 (4)	0.0035 (3)	0.0058 (3)	0.0071 (3)
O1	0.0314 (11)	0.0232 (10)	0.0290 (11)	0.0051 (9)	0.0025 (9)	0.0052 (8)
O2	0.0362 (12)	0.0446 (13)	0.0254 (11)	0.0126 (10)	0.0133 (9)	0.0088 (9)
O3	0.0260 (11)	0.0348 (12)	0.0316 (12)	−0.0031 (9)	0.0010 (9)	0.0100 (9)
C1	0.0207 (14)	0.0289 (15)	0.0217 (14)	0.0066 (11)	0.0044 (11)	0.0070 (11)
C2	0.0173 (13)	0.0282 (14)	0.0217 (14)	0.0063 (11)	0.0039 (11)	0.0084 (11)
C3	0.0222 (14)	0.0257 (14)	0.0239 (14)	0.0057 (11)	0.0023 (11)	0.0054 (11)
C4	0.0273 (15)	0.0319 (16)	0.0218 (14)	0.0123 (12)	0.0035 (12)	0.0040 (12)
C5	0.0320 (16)	0.0381 (17)	0.0239 (15)	0.0135 (13)	0.0068 (13)	0.0125 (13)
C6	0.0304 (16)	0.0303 (16)	0.0351 (17)	0.0089 (13)	0.0093 (13)	0.0160 (13)
C7	0.0221 (14)	0.0243 (14)	0.0259 (15)	0.0074 (11)	0.0003 (11)	0.0051 (11)
C8	0.0241 (14)	0.0311 (15)	0.0242 (15)	0.0091 (12)	0.0036 (12)	0.0062 (12)
C9	0.0252 (14)	0.0237 (14)	0.0234 (14)	0.0007 (11)	0.0057 (12)	0.0085 (11)
C10	0.0324 (16)	0.0324 (16)	0.0271 (16)	0.0032 (13)	0.0025 (13)	0.0116 (13)
C11	0.0331 (17)	0.0439 (19)	0.046 (2)	0.0026 (15)	−0.0019 (15)	0.0262 (16)
C12	0.0329 (18)	0.0394 (19)	0.073 (3)	0.0131 (15)	0.0128 (18)	0.0329 (19)
C13	0.043 (2)	0.0264 (16)	0.062 (2)	0.0106 (15)	0.0213 (18)	0.0140 (16)
C14	0.0316 (16)	0.0244 (15)	0.0336 (17)	−0.0012 (12)	0.0078 (13)	0.0039 (12)
C15	0.0387 (18)	0.0331 (17)	0.0288 (16)	0.0081 (14)	−0.0004 (14)	−0.0004 (13)
Cl2	0.0602 (5)	0.0376 (4)	0.0227 (4)	0.0147 (4)	0.0028 (4)	0.0079 (3)
S2	0.0220 (4)	0.0284 (4)	0.0208 (4)	0.0028 (3)	0.0013 (3)	0.0037 (3)
O4	0.0357 (12)	0.0243 (10)	0.0332 (11)	0.0074 (9)	0.0082 (9)	0.0119 (9)
O5	0.0284 (11)	0.0342 (12)	0.0263 (11)	−0.0016 (9)	0.0059 (9)	0.0053 (9)
O6	0.0291 (11)	0.0441 (13)	0.0258 (11)	0.0092 (10)	−0.0025 (9)	0.0057 (9)
C16	0.0195 (14)	0.0266 (14)	0.0247 (14)	0.0060 (11)	0.0040 (11)	0.0054 (11)
C17	0.0191 (13)	0.0224 (14)	0.0255 (14)	0.0060 (11)	0.0042 (11)	0.0033 (11)
C18	0.0246 (14)	0.0217 (14)	0.0245 (14)	0.0040 (11)	0.0029 (12)	0.0051 (11)
C19	0.0316 (16)	0.0287 (15)	0.0229 (15)	0.0099 (12)	0.0046 (12)	0.0057 (12)
C20	0.0308 (16)	0.0271 (15)	0.0286 (16)	0.0059 (13)	−0.0029 (13)	−0.0023 (12)
C21	0.0296 (16)	0.0244 (15)	0.0378 (17)	0.0057 (12)	0.0035 (13)	0.0031 (13)
C22	0.0233 (14)	0.0239 (14)	0.0278 (15)	0.0075 (11)	0.0060 (12)	0.0074 (12)
C23	0.0282 (15)	0.0306 (16)	0.0282 (15)	0.0125 (12)	0.0084 (12)	0.0085 (12)
C24	0.0204 (14)	0.0215 (14)	0.0290 (15)	0.0004 (11)	−0.0008 (12)	0.0018 (11)
C25	0.0331 (16)	0.0329 (16)	0.0251 (15)	0.0065 (13)	0.0018 (13)	0.0011 (12)
C26	0.0364 (18)	0.0406 (19)	0.0387 (19)	0.0082 (15)	0.0091 (15)	−0.0068 (15)
C27	0.0289 (17)	0.0283 (17)	0.068 (3)	0.0069 (14)	0.0010 (17)	−0.0062 (16)
C28	0.0361 (18)	0.0215 (16)	0.072 (3)	0.0024 (14)	−0.0053 (18)	0.0160 (16)
C29	0.0304 (16)	0.0282 (16)	0.0431 (19)	−0.0012 (13)	0.0009 (14)	0.0155 (14)
C30	0.054 (2)	0.0414 (19)	0.0314 (17)	0.0169 (16)	0.0119 (15)	0.0183 (14)

Geometric parameters (Å, º) top

Cl1—C4	1.750 (3)	Cl2—C19	1.746 (3)
S1—O3	1.437 (2)	S2—O6	1.437 (2)
S1—O2	1.437 (2)	S2—O5	1.438 (2)
S1—C1	1.746 (3)	S2—C16	1.742 (3)
S1—C9	1.762 (3)	S2—C24	1.762 (3)
O1—C8	1.369 (3)	O4—C23	1.368 (4)
O1—C7	1.375 (3)	O4—C22	1.378 (3)
C1—C8	1.357 (4)	C16—C23	1.361 (4)
C1—C2	1.451 (4)	C16—C17	1.452 (4)
C2—C7	1.386 (4)	C17—C22	1.392 (4)
C2—C3	1.404 (4)	C17—C18	1.395 (4)
C3—C4	1.383 (4)	C18—C19	1.386 (4)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.396 (4)	C19—C20	1.398 (4)
C5—C6	1.383 (4)	C20—C21	1.378 (4)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.383 (4)	C21—C22	1.386 (4)
C6—H6	0.9500	C21—H21	0.9500
C8—C15	1.484 (4)	C23—C30	1.480 (4)
C9—C10	1.388 (4)	C24—C29	1.383 (4)
C9—C14	1.391 (4)	C24—C25	1.389 (4)
C10—C11	1.391 (4)	C25—C26	1.377 (4)
C10—H10	0.9500	C25—H25	0.9500
C11—C12	1.375 (5)	C26—C27	1.382 (5)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.374 (5)	C27—C28	1.374 (5)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.389 (5)	C28—C29	1.388 (5)
C13—H13	0.9500	C28—H28	0.9500
C14—H14	0.9500	C29—H29	0.9500
C15—H15A	0.9800	C30—H30A	0.9800
C15—H15B	0.9800	C30—H30B	0.9800
C15—H15C	0.9800	C30—H30C	0.9800

O3—S1—O2	119.89 (13)	O6—S2—O5	119.93 (13)
O3—S1—C1	106.92 (13)	O6—S2—C16	108.60 (13)
O2—S1—C1	108.61 (13)	O5—S2—C16	107.16 (13)
O3—S1—C9	107.87 (13)	O6—S2—C24	107.79 (13)
O2—S1—C9	108.20 (13)	O5—S2—C24	108.08 (13)
C1—S1—C9	104.28 (13)	C16—S2—C24	104.18 (13)
C8—O1—C7	106.9 (2)	C23—O4—C22	106.9 (2)
C8—C1—C2	107.3 (2)	C23—C16—C17	107.4 (2)
C8—C1—S1	126.7 (2)	C23—C16—S2	127.1 (2)
C2—C1—S1	126.0 (2)	C17—C16—S2	125.5 (2)
C7—C2—C3	119.6 (2)	C22—C17—C18	119.4 (3)
C7—C2—C1	104.7 (2)	C22—C17—C16	104.4 (2)
C3—C2—C1	135.7 (3)	C18—C17—C16	136.2 (3)
C4—C3—C2	116.2 (3)	C19—C18—C17	116.5 (3)
C4—C3—H3	121.9	C19—C18—H18	121.7
C2—C3—H3	121.9	C17—C18—H18	121.7
C3—C4—C5	123.4 (3)	C18—C19—C20	123.5 (3)
C3—C4—Cl1	118.5 (2)	C18—C19—Cl2	118.9 (2)
C5—C4—Cl1	118.1 (2)	C20—C19—Cl2	117.6 (2)
C6—C5—C4	120.4 (3)	C21—C20—C19	120.0 (3)
C6—C5—H5	119.8	C21—C20—H20	120.0
C4—C5—H5	119.8	C19—C20—H20	120.0
C5—C6—C7	116.2 (3)	C20—C21—C22	116.5 (3)
C5—C6—H6	121.9	C20—C21—H21	121.7
C7—C6—H6	121.9	C22—C21—H21	121.7
O1—C7—C6	125.2 (3)	O4—C22—C21	125.3 (3)
O1—C7—C2	110.6 (2)	O4—C22—C17	110.7 (2)
C6—C7—C2	124.2 (3)	C21—C22—C17	124.0 (3)
C1—C8—O1	110.5 (2)	C16—C23—O4	110.6 (2)
C1—C8—C15	134.8 (3)	C16—C23—C30	134.7 (3)
O1—C8—C15	114.7 (3)	O4—C23—C30	114.7 (3)
C10—C9—C14	121.5 (3)	C29—C24—C25	121.4 (3)
C10—C9—S1	119.0 (2)	C29—C24—S2	120.0 (2)
C14—C9—S1	119.5 (2)	C25—C24—S2	118.5 (2)
C9—C10—C11	118.7 (3)	C26—C25—C24	119.4 (3)
C9—C10—H10	120.7	C26—C25—H25	120.3
C11—C10—H10	120.7	C24—C25—H25	120.3
C12—C11—C10	120.2 (3)	C25—C26—C27	119.6 (3)
C12—C11—H11	119.9	C25—C26—H26	120.2
C10—C11—H11	119.9	C27—C26—H26	120.2
C13—C12—C11	120.8 (3)	C28—C27—C26	120.8 (3)
C13—C12—H12	119.6	C28—C27—H27	119.6
C11—C12—H12	119.6	C26—C27—H27	119.6
C12—C13—C14	120.5 (3)	C27—C28—C29	120.5 (3)
C12—C13—H13	119.8	C27—C28—H28	119.7
C14—C13—H13	119.8	C29—C28—H28	119.7
C13—C14—C9	118.4 (3)	C24—C29—C28	118.3 (3)
C13—C14—H14	120.8	C24—C29—H29	120.9
C9—C14—H14	120.8	C28—C29—H29	120.9
C8—C15—H15A	109.5	C23—C30—H30A	109.5
C8—C15—H15B	109.5	C23—C30—H30B	109.5
H15A—C15—H15B	109.5	H30A—C30—H30B	109.5
C8—C15—H15C	109.5	C23—C30—H30C	109.5
H15A—C15—H15C	109.5	H30A—C30—H30C	109.5
H15B—C15—H15C	109.5	H30B—C30—H30C	109.5

O3—S1—C1—C8	−156.6 (2)	O6—S2—C16—C23	23.3 (3)
O2—S1—C1—C8	−25.9 (3)	O5—S2—C16—C23	154.3 (2)
C9—S1—C1—C8	89.3 (3)	C24—S2—C16—C23	−91.3 (3)
O3—S1—C1—C2	25.9 (3)	O6—S2—C16—C17	−159.3 (2)
O2—S1—C1—C2	156.6 (2)	O5—S2—C16—C17	−28.4 (3)
C9—S1—C1—C2	−88.2 (3)	C24—S2—C16—C17	86.0 (2)
C8—C1—C2—C7	0.8 (3)	C23—C16—C17—C22	−0.9 (3)
S1—C1—C2—C7	178.7 (2)	S2—C16—C17—C22	−178.7 (2)
C8—C1—C2—C3	179.8 (3)	C23—C16—C17—C18	179.9 (3)
S1—C1—C2—C3	−2.3 (5)	S2—C16—C17—C18	2.1 (5)
C7—C2—C3—C4	0.4 (4)	C22—C17—C18—C19	−1.0 (4)
C1—C2—C3—C4	−178.5 (3)	C16—C17—C18—C19	178.1 (3)
C2—C3—C4—C5	0.4 (4)	C17—C18—C19—C20	−0.2 (4)
C2—C3—C4—Cl1	179.1 (2)	C17—C18—C19—Cl2	−178.6 (2)
C3—C4—C5—C6	−0.7 (4)	C18—C19—C20—C21	0.9 (5)
Cl1—C4—C5—C6	−179.4 (2)	Cl2—C19—C20—C21	179.3 (2)
C4—C5—C6—C7	0.1 (4)	C19—C20—C21—C22	−0.3 (4)
C8—O1—C7—C6	−178.5 (3)	C23—O4—C22—C21	178.1 (3)
C8—O1—C7—C2	0.5 (3)	C23—O4—C22—C17	−0.2 (3)
C5—C6—C7—O1	179.6 (3)	C20—C21—C22—O4	−179.1 (3)
C5—C6—C7—C2	0.7 (4)	C20—C21—C22—C17	−1.0 (4)
C3—C2—C7—O1	−180.0 (2)	C18—C17—C22—O4	180.0 (2)
C1—C2—C7—O1	−0.8 (3)	C16—C17—C22—O4	0.6 (3)
C3—C2—C7—C6	−1.0 (4)	C18—C17—C22—C21	1.7 (4)
C1—C2—C7—C6	178.2 (3)	C16—C17—C22—C21	−177.7 (3)
C2—C1—C8—O1	−0.5 (3)	C17—C16—C23—O4	0.8 (3)
S1—C1—C8—O1	−178.42 (19)	S2—C16—C23—O4	178.58 (19)
C2—C1—C8—C15	177.8 (3)	C17—C16—C23—C30	−178.2 (3)
S1—C1—C8—C15	−0.1 (5)	S2—C16—C23—C30	−0.4 (5)
C7—O1—C8—C1	0.0 (3)	C22—O4—C23—C16	−0.4 (3)
C7—O1—C8—C15	−178.6 (2)	C22—O4—C23—C30	178.8 (2)
O3—S1—C9—C10	157.2 (2)	O6—S2—C24—C29	150.9 (2)
O2—S1—C9—C10	26.1 (3)	O5—S2—C24—C29	19.9 (3)
C1—S1—C9—C10	−89.4 (2)	C16—S2—C24—C29	−93.8 (3)
O3—S1—C9—C14	−25.0 (3)	O6—S2—C24—C25	−31.2 (3)
O2—S1—C9—C14	−156.0 (2)	O5—S2—C24—C25	−162.2 (2)
C1—S1—C9—C14	88.5 (2)	C16—S2—C24—C25	84.0 (2)
C14—C9—C10—C11	0.8 (4)	C29—C24—C25—C26	0.0 (4)
S1—C9—C10—C11	178.6 (2)	S2—C24—C25—C26	−177.8 (2)
C9—C10—C11—C12	−0.7 (4)	C24—C25—C26—C27	−0.1 (5)
C10—C11—C12—C13	0.6 (5)	C25—C26—C27—C28	0.0 (5)
C11—C12—C13—C14	−0.5 (5)	C26—C27—C28—C29	0.3 (5)
C12—C13—C14—C9	0.6 (5)	C25—C24—C29—C28	0.3 (4)
C10—C9—C14—C13	−0.7 (4)	S2—C24—C29—C28	178.0 (2)
S1—C9—C14—C13	−178.5 (2)	C27—C28—C29—C24	−0.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.44	3.153 (4)	130
C14—H14···O3ⁱ	0.95	2.51	3.429 (4)	164
C29—H29···O5ⁱⁱ	0.95	2.51	3.453 (4)	170
C30—H30A···O6	0.98	2.42	3.141 (4)	130

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClO₃S
M_r	306.76
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.4029 (7), 9.2669 (9), 20.889 (2)
α, β, γ (°)	100.953 (2), 95.626 (2), 104.212 (2)
V (Å³)	1348.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.50 × 0.50 × 0.30

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.795, 0.870
No. of measured, independent and observed [I > 2σ(I)] reflections	9232, 4555, 4119
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.116, 1.16
No. of reflections	4555
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.43

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2	0.98	2.44	3.153 (4)	129.5
C14—H14···O3ⁱ	0.95	2.51	3.429 (4)	163.7
C29—H29···O5ⁱⁱ	0.95	2.51	3.453 (4)	169.8
C30—H30A···O6	0.98	2.42	3.141 (4)	130.4

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+1, −z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o793. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o850. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 7| July 2008| Page o1190

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