3-Cyclo­hexyl­sulfonyl-5-isopropyl-2-methyl-1-benzofuran

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

doi:10.1107/S1600536811007215

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o749

doi:10.1107/S1600536811007215

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3-Cyclohexylsulfonyl-5-isopropyl-2-methyl-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 17 February 2011; accepted 25 February 2011; online 2 March 2011)

In the title compound, C₁₈H₂₄O₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, molecules are linked through weak non-classical intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

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 structural studies of related 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008 , 2010 ).

Experimental

Crystal data

C₁₈H₂₄O₃S
M_r = 320.44
Monoclinic, P 2₁ /c
a = 5.7117 (1) Å
b = 23.5045 (4) Å
c = 12.7980 (2) Å
β = 102.080 (1)°
V = 1680.09 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.26 × 0.25 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.949, T_max = 0.957
15706 measured reflections
3870 independent reflections
3124 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 1.05
3870 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	1.00	2.33	3.3030 (19)	165
C14—H14A⋯O3ⁱⁱ	0.99	2.58	3.424 (2)	143
C10—H10C⋯Cgⁱ	0.98	2.71	3.548 (2)	144
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007215/rk2267sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007215/rk2267Isup2.hkl

checkCIF report

Comment top

Many compounds having a benzofuran skeleton exhibit diverse pharmacological properties such as antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2006; Galal et al., 2009; Khan et al., 2005). These compounds occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of the substituent effect on the solid state structures of 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran analogues (Choi et al., 2008, 2010), we report herein the molecular and crystal structures of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.009 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The molecular packing (Fig. 2) is stabilized by weak non-classical intermolecular C–H···O hydrogen bonds; the first one between a cyclohexyl H atom and the oxygen of the O═S═O unit (Table 1; C13—H13···O2ⁱ), the second one between a cyclohexyl H atom and the oxygen of the O═S═O unit (Table 1; C14—H14A···O3ⁱⁱ). The crystal packing (Fig. 2) is further stabilized by intermolecular C–H···π interactions between a methyl H atom of the isopropyl group and the benzene ring.

Related literature top

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 structural studies of related 3-arylsulfonyl-5-isopropyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2008, 2010).

Experimental top

The 3-chloroperoxybenzoic acid (77%, 560 mg, 2.5 mmol) was added in small portions to a stirred solution of 3-cyclohexylsulfanyl-5-isopropyl-2-methyl-1-benzofuran (346 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 6h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 4:1 v/v) to afford the title compound as a colourless solid [yield 78%, m.p. 467–468 K; R_f = 0.66 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Symmetry codes: (i) x-1 , y, z; (ii) x, -y+1/2, z+1/2 (iii) x+1, y, z; (iv) x, -y+1/2, z-1/2.

3-Cyclohexylsulfonyl-5-isopropyl-2-methyl-1-benzofuran top

Crystal data top

C₁₈H₂₄O₃S	F(000) = 688
M_r = 320.44	D_x = 1.267 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 467–468 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7117 (1) Å	Cell parameters from 7210 reflections
b = 23.5045 (4) Å	θ = 2.4–27.3°
c = 12.7980 (2) Å	µ = 0.20 mm⁻¹
β = 102.080 (1)°	T = 173 K
V = 1680.09 (5) Å³	Block, colourless
Z = 4	0.26 × 0.25 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3870 independent reflections
Radiation source: rotating anode	3124 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.034
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.7°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −22→30
T_min = 0.949, T_max = 0.957	l = −16→16
15706 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0595P)² + 0.3753P] where P = (F_o² + 2F_c²)/3
3870 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₈H₂₄O₃S	V = 1680.09 (5) Å³
M_r = 320.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7117 (1) Å	µ = 0.20 mm⁻¹
b = 23.5045 (4) Å	T = 173 K
c = 12.7980 (2) Å	0.26 × 0.25 × 0.22 mm
β = 102.080 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3870 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3124 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.957	R_int = 0.034
15706 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
3870 reflections	Δρ_min = −0.49 e Å⁻³
202 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 > 2σ(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
S1	0.79640 (7)	0.253935 (16)	0.35223 (3)	0.02755 (13)
O1	0.8519 (2)	0.14326 (5)	0.58586 (9)	0.0413 (3)
O2	1.0380 (2)	0.27516 (5)	0.37375 (10)	0.0411 (3)
O3	0.6959 (2)	0.23391 (5)	0.24608 (9)	0.0377 (3)
C1	0.7751 (3)	0.19902 (6)	0.44030 (12)	0.0296 (3)
C2	0.5856 (3)	0.15696 (6)	0.42805 (12)	0.0304 (3)
C3	0.3829 (3)	0.14321 (7)	0.35150 (13)	0.0327 (4)
H3	0.3395	0.1653	0.2883	0.039*
C4	0.2436 (3)	0.09669 (7)	0.36817 (14)	0.0367 (4)
C5	0.3105 (4)	0.06562 (7)	0.46338 (15)	0.0444 (5)
H5	0.2137	0.0343	0.4750	0.053*
C6	0.5089 (4)	0.07834 (7)	0.54037 (15)	0.0448 (5)
H6	0.5514	0.0567	0.6042	0.054*
C7	0.6431 (3)	0.12389 (7)	0.52048 (13)	0.0366 (4)
C8	0.9275 (3)	0.18916 (7)	0.53575 (13)	0.0353 (4)
C9	0.0319 (3)	0.07963 (8)	0.28150 (16)	0.0457 (5)
H9	−0.0566	0.1152	0.2548	0.055*
C10	−0.1454 (4)	0.03966 (8)	0.31629 (19)	0.0565 (6)
H10A	−0.0694	0.0026	0.3349	0.085*
H10B	−0.2851	0.0349	0.2577	0.085*
H10C	−0.1964	0.0556	0.3787	0.085*
C11	0.1175 (4)	0.05314 (12)	0.18821 (17)	0.0678 (7)
H11A	0.2218	0.0800	0.1612	0.102*
H11B	−0.0208	0.0440	0.1312	0.102*
H11C	0.2068	0.0182	0.2119	0.102*
C12	1.1480 (3)	0.21675 (9)	0.59454 (15)	0.0477 (5)
H12A	1.2862	0.1926	0.5913	0.072*
H12B	1.1371	0.2222	0.6693	0.072*
H12C	1.1672	0.2538	0.5621	0.072*
C13	0.6056 (3)	0.30757 (6)	0.38532 (12)	0.0258 (3)
H13	0.4401	0.2915	0.3746	0.031*
C14	0.6805 (3)	0.32676 (7)	0.50149 (12)	0.0368 (4)
H14A	0.6821	0.2937	0.5496	0.044*
H14B	0.8441	0.3430	0.5144	0.044*
C15	0.5051 (4)	0.37148 (8)	0.52512 (15)	0.0466 (5)
H15A	0.3454	0.3539	0.5191	0.056*
H15B	0.5590	0.3852	0.5994	0.056*
C16	0.4846 (4)	0.42147 (8)	0.44964 (18)	0.0556 (5)
H16A	0.6385	0.4423	0.4624	0.067*
H16B	0.3596	0.4478	0.4637	0.067*
C17	0.4210 (4)	0.40189 (8)	0.33352 (16)	0.0510 (5)
H17A	0.2583	0.3852	0.3185	0.061*
H17B	0.4198	0.4351	0.2859	0.061*
C18	0.5991 (3)	0.35795 (7)	0.30975 (13)	0.0369 (4)
H18A	0.7604	0.3752	0.3195	0.044*
H18B	0.5505	0.3449	0.2348	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0263 (2)	0.0315 (2)	0.0264 (2)	−0.00097 (14)	0.00923 (16)	−0.00148 (14)
O1	0.0547 (8)	0.0371 (7)	0.0309 (6)	0.0125 (6)	0.0067 (6)	0.0045 (5)
O2	0.0258 (6)	0.0519 (7)	0.0481 (7)	−0.0035 (5)	0.0136 (5)	−0.0003 (6)
O3	0.0509 (8)	0.0380 (6)	0.0257 (6)	−0.0039 (5)	0.0114 (5)	−0.0038 (5)
C1	0.0311 (8)	0.0296 (8)	0.0290 (8)	0.0061 (6)	0.0079 (7)	−0.0002 (6)
C2	0.0386 (9)	0.0239 (8)	0.0316 (8)	0.0059 (6)	0.0137 (7)	0.0014 (6)
C3	0.0381 (9)	0.0259 (8)	0.0353 (8)	0.0028 (6)	0.0106 (7)	0.0048 (6)
C4	0.0419 (10)	0.0261 (8)	0.0460 (10)	0.0020 (7)	0.0177 (8)	0.0024 (7)
C5	0.0652 (13)	0.0259 (9)	0.0494 (11)	−0.0007 (8)	0.0286 (10)	0.0042 (7)
C6	0.0719 (14)	0.0298 (9)	0.0365 (9)	0.0080 (9)	0.0203 (9)	0.0076 (7)
C7	0.0531 (11)	0.0282 (8)	0.0302 (8)	0.0114 (7)	0.0129 (8)	0.0014 (7)
C8	0.0383 (9)	0.0369 (9)	0.0321 (8)	0.0119 (7)	0.0104 (7)	−0.0006 (7)
C9	0.0407 (10)	0.0320 (9)	0.0653 (13)	−0.0056 (8)	0.0131 (9)	0.0057 (8)
C10	0.0537 (12)	0.0407 (11)	0.0843 (16)	−0.0120 (9)	0.0353 (11)	−0.0130 (11)
C11	0.0508 (13)	0.1066 (19)	0.0474 (12)	−0.0300 (13)	0.0135 (10)	−0.0090 (12)
C12	0.0380 (10)	0.0636 (13)	0.0375 (10)	0.0114 (9)	−0.0010 (8)	−0.0016 (9)
C13	0.0226 (7)	0.0271 (7)	0.0280 (8)	−0.0010 (6)	0.0058 (6)	0.0000 (6)
C14	0.0450 (10)	0.0387 (9)	0.0271 (8)	0.0071 (7)	0.0084 (7)	−0.0029 (7)
C15	0.0551 (12)	0.0444 (11)	0.0426 (10)	0.0081 (9)	0.0151 (9)	−0.0105 (8)
C16	0.0661 (14)	0.0319 (10)	0.0688 (14)	0.0063 (9)	0.0139 (11)	−0.0103 (9)
C17	0.0616 (13)	0.0346 (10)	0.0542 (12)	0.0126 (9)	0.0067 (10)	0.0081 (8)
C18	0.0459 (10)	0.0318 (9)	0.0316 (8)	−0.0020 (7)	0.0051 (7)	0.0048 (7)

Geometric parameters (Å, º) top

S1—O3	1.4389 (12)	C10—H10C	0.9800
S1—O2	1.4389 (12)	C11—H11A	0.9800
S1—C1	1.7345 (16)	C11—H11B	0.9800
S1—C13	1.7747 (15)	C11—H11C	0.9800
O1—C8	1.370 (2)	C12—H12A	0.9800
O1—C7	1.383 (2)	C12—H12B	0.9800
C1—C8	1.363 (2)	C12—H12C	0.9800
C1—C2	1.450 (2)	C13—C18	1.524 (2)
C2—C3	1.389 (2)	C13—C14	1.527 (2)
C2—C7	1.396 (2)	C13—H13	1.0000
C3—C4	1.395 (2)	C14—C15	1.526 (2)
C3—H3	0.9500	C14—H14A	0.9900
C4—C5	1.403 (2)	C14—H14B	0.9900
C4—C9	1.514 (3)	C15—C16	1.510 (3)
C5—C6	1.370 (3)	C15—H15A	0.9900
C5—H5	0.9500	C15—H15B	0.9900
C6—C7	1.371 (3)	C16—C17	1.525 (3)
C6—H6	0.9500	C16—H16A	0.9900
C8—C12	1.475 (3)	C16—H16B	0.9900
C9—C10	1.515 (2)	C17—C18	1.524 (3)
C9—C11	1.515 (3)	C17—H17A	0.9900
C9—H9	1.0000	C17—H17B	0.9900
C10—H10A	0.9800	C18—H18A	0.9900
C10—H10B	0.9800	C18—H18B	0.9900

O3—S1—O2	118.13 (7)	C9—C11—H11C	109.5
O3—S1—C1	107.55 (7)	H11A—C11—H11C	109.5
O2—S1—C1	109.19 (8)	H11B—C11—H11C	109.5
O3—S1—C13	108.30 (7)	C8—C12—H12A	109.5
O2—S1—C13	108.69 (7)	C8—C12—H12B	109.5
C1—S1—C13	104.09 (7)	H12A—C12—H12B	109.5
C8—O1—C7	107.01 (12)	C8—C12—H12C	109.5
C8—C1—C2	107.65 (14)	H12A—C12—H12C	109.5
C8—C1—S1	126.16 (13)	H12B—C12—H12C	109.5
C2—C1—S1	126.13 (12)	C18—C13—C14	110.67 (13)
C3—C2—C7	118.78 (15)	C18—C13—S1	109.58 (11)
C3—C2—C1	136.71 (15)	C14—C13—S1	112.41 (11)
C7—C2—C1	104.49 (15)	C18—C13—H13	108.0
C2—C3—C4	119.51 (15)	C14—C13—H13	108.0
C2—C3—H3	120.2	S1—C13—H13	108.0
C4—C3—H3	120.2	C15—C14—C13	109.55 (14)
C3—C4—C5	118.71 (16)	C15—C14—H14A	109.8
C3—C4—C9	119.30 (15)	C13—C14—H14A	109.8
C5—C4—C9	121.93 (16)	C15—C14—H14B	109.8
C6—C5—C4	123.01 (17)	C13—C14—H14B	109.8
C6—C5—H5	118.5	H14A—C14—H14B	108.2
C4—C5—H5	118.5	C16—C15—C14	112.06 (16)
C5—C6—C7	116.56 (16)	C16—C15—H15A	109.2
C5—C6—H6	121.7	C14—C15—H15A	109.2
C7—C6—H6	121.7	C16—C15—H15B	109.2
C6—C7—O1	126.13 (15)	C14—C15—H15B	109.2
C6—C7—C2	123.41 (17)	H15A—C15—H15B	107.9
O1—C7—C2	110.46 (15)	C15—C16—C17	111.05 (15)
C1—C8—O1	110.38 (15)	C15—C16—H16A	109.4
C1—C8—C12	134.37 (17)	C17—C16—H16A	109.4
O1—C8—C12	115.25 (15)	C15—C16—H16B	109.4
C4—C9—C10	115.43 (17)	C17—C16—H16B	109.4
C4—C9—C11	110.26 (16)	H16A—C16—H16B	108.0
C10—C9—C11	108.82 (16)	C18—C17—C16	111.48 (15)
C4—C9—H9	107.3	C18—C17—H17A	109.3
C10—C9—H9	107.3	C16—C17—H17A	109.3
C11—C9—H9	107.3	C18—C17—H17B	109.3
C9—C10—H10A	109.5	C16—C17—H17B	109.3
C9—C10—H10B	109.5	H17A—C17—H17B	108.0
H10A—C10—H10B	109.5	C17—C18—C13	109.17 (14)
C9—C10—H10C	109.5	C17—C18—H18A	109.8
H10A—C10—H10C	109.5	C13—C18—H18A	109.8
H10B—C10—H10C	109.5	C17—C18—H18B	109.8
C9—C11—H11A	109.5	C13—C18—H18B	109.8
C9—C11—H11B	109.5	H18A—C18—H18B	108.3
H11A—C11—H11B	109.5

O3—S1—C1—C8	149.94 (14)	C2—C1—C8—O1	0.67 (18)
O2—S1—C1—C8	20.63 (17)	S1—C1—C8—O1	177.99 (11)
C13—S1—C1—C8	−95.29 (15)	C2—C1—C8—C12	−178.92 (18)
O3—S1—C1—C2	−33.21 (15)	S1—C1—C8—C12	−1.6 (3)
O2—S1—C1—C2	−162.53 (13)	C7—O1—C8—C1	−0.73 (17)
C13—S1—C1—C2	81.56 (14)	C7—O1—C8—C12	178.94 (14)
C8—C1—C2—C3	−179.01 (18)	C3—C4—C9—C10	−164.47 (16)
S1—C1—C2—C3	3.7 (3)	C5—C4—C9—C10	18.3 (2)
C8—C1—C2—C7	−0.33 (17)	C3—C4—C9—C11	71.7 (2)
S1—C1—C2—C7	−177.66 (12)	C5—C4—C9—C11	−105.5 (2)
C7—C2—C3—C4	−0.6 (2)	O3—S1—C13—C18	−63.30 (12)
C1—C2—C3—C4	177.97 (17)	O2—S1—C13—C18	66.20 (12)
C2—C3—C4—C5	1.2 (2)	C1—S1—C13—C18	−177.53 (11)
C2—C3—C4—C9	−176.17 (15)	O3—S1—C13—C14	173.20 (11)
C3—C4—C5—C6	−1.0 (3)	O2—S1—C13—C14	−57.30 (13)
C9—C4—C5—C6	176.28 (18)	C1—S1—C13—C14	58.97 (13)
C4—C5—C6—C7	0.1 (3)	C18—C13—C14—C15	58.75 (18)
C5—C6—C7—O1	−178.51 (16)	S1—C13—C14—C15	−178.37 (12)
C5—C6—C7—C2	0.5 (3)	C13—C14—C15—C16	−56.1 (2)
C8—O1—C7—C6	179.64 (16)	C14—C15—C16—C17	54.4 (2)
C8—O1—C7—C2	0.51 (17)	C15—C16—C17—C18	−55.1 (2)
C3—C2—C7—C6	−0.3 (2)	C16—C17—C18—C13	57.4 (2)
C1—C2—C7—C6	−179.27 (16)	C14—C13—C18—C17	−59.57 (18)
C3—C2—C7—O1	178.86 (14)	S1—C13—C18—C17	175.92 (12)
C1—C2—C7—O1	−0.11 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	1.00	2.33	3.3030 (19)	165
C14—H14A···O3ⁱⁱ	0.99	2.58	3.424 (2)	143
C10—H10C···Cgⁱ	0.98	2.71	3.548 (2)	144

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₄O₃S
M_r	320.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	5.7117 (1), 23.5045 (4), 12.7980 (2)
β (°)	102.080 (1)
V (Å³)	1680.09 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.26 × 0.25 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.949, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	15706, 3870, 3124
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 1.05
No. of reflections	3870
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.49

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	1.00	2.33	3.3030 (19)	165
C14—H14A···O3ⁱⁱ	0.99	2.58	3.424 (2)	143
C10—H10C···Cgⁱ	0.98	2.71	3.548 (2)	144

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

References

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Volume 67| Part 4| April 2011| Page o749

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