1-Cyclo­hexyl­sulfinyl-2-methyl­naphtho­[2,1-b]furan

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

doi:10.1107/S1600536811010981

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o1002

doi:10.1107/S1600536811010981

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1-Cyclohexylsulfinyl-2-methylnaphtho[2,1-b]furan

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 27 February 2011; accepted 24 March 2011; online 31 March 2011)

In the title compound, C₁₉H₂₀O₂S, the cyclohexyl ring adopts a chair conformation and the arylsulfinyl unit is positioned equatorial relative to the cyclohexyl group. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations with site-occupancy factors of 0.923 (3) and 0.077 (3).

Related literature

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984 ); Hranjec et al. (2003 ); Mahadevan & Vaidya (2003 ). For structural studies of related 2-methylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2006 , 2007 ).

Experimental

Crystal data

C₁₉H₂₀O₂S
M_r = 312.41
Monoclinic, P 2₁ /n
a = 5.8424 (1) Å
b = 19.5900 (3) Å
c = 13.4314 (2) Å
β = 92.649 (1)°
V = 1535.62 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.42 × 0.34 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.916, T_max = 0.946
14260 measured reflections
3527 independent reflections
3026 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.06
3527 reflections
210 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O2Bⁱ	0.98	2.12	2.848 (6)	130
C14—H14⋯O2Aⁱⁱ	1.00	2.38	3.2947 (19)	152
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z.

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/S1600536811010981/fl2340sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010981/fl2340Isup2.hkl

checkCIF report

Comment top

Many compounds containing a naphthofuran ring have attracted much attention owing to their potent pharmacological properties such as antibacterial, antitumor and anthelmintic activities (Einhorn et al. , 1984, Hranjec et al., 2003, Mahadevan & Vaidya, 2003). As a part of our ongoing studies of the substituent effect on the solid state structures of 2-methylnaphtho[2,1-b]furan analogues (Choi et al., 2006, 2007), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.014 (1) Å from the least-squares plane defined by the thirteen constituent atoms. The cyclohexyl ring is in the chair form and arylsulfinyl moiety is positioned equatorial relative to the cyclohexyl group. The O atom of the sulfinyl group is disordered over two positions with site-occupancy factors, from refinement, of 0.923 (3) (part A) and 0.077 (3) (part B). The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and and one of the disordered sulfinyl oxygen atoms(Table 1; C13—H13B···O2Bⁱ), and the second one between a cyclohexyl H atom and the other disordered sulfinyl oxygen (Table 1; C14—H14···O2Aⁱⁱ).

Related literature top

For the pharmacological activity of naphthofuran compounds, see: Einhorn et al. (1984); Hranjec et al. (2003); Mahadevan & Vaidya (2003). For structural studies of related 2-methylnaphtho[2,1-b]furan derivatives, see: Choi et al. (2006, 2007).

Experimental top

77% 3-chloroperoxybenzoic acid (291 mg, 1.3 mmol) was added in small portions to a stirred solution of 1-cyclohexylsulfanyl-2-methylnaphtho[2,1-b] furan (355 mg, 1.2 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 8h, the mixture was washed with a 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 colorless solid [yield 74%, m.p. 429–430 K; R_f = 0.61 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation frroomm 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. The O atom of sulfinyl group is disordered over two positions with site-occupancy factors, from refinement of 0.923 (3) (part A) and 0.077 (3) (part B).
	Fig. 2. A view of the C—H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1/2, -y + 3/2,z - 1/2; (ii) x + 1, y, z; (iii) x + 1/2, - y + 3/2, z + 1/2 ; (iv) x - 1, y, z.]

1-Cyclohexylsulfinyl-2-methylnaphtho[2,1-b]furan top

Crystal data top

C₁₉H₂₀O₂S	F(000) = 664
M_r = 312.41	D_x = 1.351 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6431 reflections
a = 5.8424 (1) Å	θ = 2.6–27.5°
b = 19.5900 (3) Å	µ = 0.22 mm⁻¹
c = 13.4314 (2) Å	T = 173 K
β = 92.649 (1)°	Block, colourless
V = 1535.62 (4) Å³	0.42 × 0.34 × 0.26 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3527 independent reflections
Radiation source: rotating anode	3026 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.037
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −21→25
T_min = 0.916, T_max = 0.946	l = −17→13
14260 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0439P)² + 0.6943P] where P = (F_o² + 2F_c²)/3
3527 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.56 e Å⁻³
4 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₉H₂₀O₂S	V = 1535.62 (4) Å³
M_r = 312.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8424 (1) Å	µ = 0.22 mm⁻¹
b = 19.5900 (3) Å	T = 173 K
c = 13.4314 (2) Å	0.42 × 0.34 × 0.26 mm
β = 92.649 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3527 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3026 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.946	R_int = 0.037
14260 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.06	Δρ_max = 0.56 e Å⁻³
3527 reflections	Δρ_min = −0.49 e Å⁻³
210 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.41951 (7)	0.69277 (2)	0.70702 (3)	0.02494 (12)
O1	0.37126 (19)	0.80010 (6)	0.45636 (8)	0.0279 (3)
O2A	0.1985 (2)	0.65645 (7)	0.69667 (10)	0.0324 (4)	0.923 (3)
O2B	0.428 (3)	0.7216 (7)	0.8085 (4)	0.032 (4)	0.077 (3)
C1	0.4458 (3)	0.74856 (8)	0.60361 (11)	0.0217 (3)
C2	0.6184 (3)	0.80058 (8)	0.59149 (11)	0.0223 (3)
C3	0.8144 (3)	0.82508 (8)	0.64850 (12)	0.0240 (3)
C4	0.8863 (3)	0.80032 (9)	0.74330 (12)	0.0275 (4)
H4	0.8002	0.7656	0.7738	0.033*
C5	1.0795 (3)	0.82587 (10)	0.79219 (13)	0.0349 (4)
H5	1.1264	0.8085	0.8559	0.042*
C6	1.2078 (3)	0.87735 (10)	0.74869 (15)	0.0394 (5)
H6	1.3410	0.8947	0.7831	0.047*
C7	1.1428 (3)	0.90261 (9)	0.65739 (15)	0.0363 (4)
H7	1.2316	0.9375	0.6288	0.044*
C8	0.9452 (3)	0.87778 (8)	0.60411 (13)	0.0287 (4)
C9	0.8795 (3)	0.90357 (9)	0.50783 (14)	0.0346 (4)
H9	0.9706	0.9381	0.4796	0.042*
C10	0.6905 (3)	0.88046 (9)	0.45488 (14)	0.0338 (4)
H10	0.6470	0.8981	0.3909	0.041*
C11	0.5645 (3)	0.82935 (8)	0.49987 (12)	0.0261 (3)
C12	0.3020 (3)	0.75066 (8)	0.52147 (12)	0.0245 (3)
C13	0.0955 (3)	0.71211 (9)	0.48597 (13)	0.0312 (4)
H13A	0.1376	0.6791	0.4351	0.047*
H13B	−0.0190	0.7439	0.4572	0.047*
H13C	0.0315	0.6878	0.5421	0.047*
C14	0.6408 (3)	0.63113 (8)	0.67666 (11)	0.0218 (3)
H14	0.7919	0.6552	0.6773	0.026*
C15	0.5947 (3)	0.59934 (8)	0.57445 (12)	0.0266 (3)
H15A	0.6037	0.6350	0.5226	0.032*
H15B	0.4381	0.5799	0.5702	0.032*
C16	0.7685 (3)	0.54320 (9)	0.55551 (13)	0.0298 (4)
H16A	0.7305	0.5217	0.4901	0.036*
H16B	0.9232	0.5635	0.5530	0.036*
C17	0.7697 (3)	0.48904 (9)	0.63642 (14)	0.0337 (4)
H17A	0.8868	0.4541	0.6232	0.040*
H17B	0.6184	0.4663	0.6359	0.040*
C18	0.8223 (3)	0.52122 (9)	0.73821 (13)	0.0331 (4)
H18A	0.9786	0.5408	0.7403	0.040*
H18B	0.8175	0.4856	0.7904	0.040*
C19	0.6489 (3)	0.57741 (9)	0.75944 (12)	0.0294 (4)
H19A	0.4950	0.5569	0.7647	0.035*
H19B	0.6920	0.5995	0.8239	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0245 (2)	0.0235 (2)	0.0274 (2)	0.00162 (15)	0.00739 (15)	0.00115 (15)
O1	0.0266 (6)	0.0291 (6)	0.0277 (6)	0.0003 (5)	−0.0021 (5)	0.0036 (5)
O2A	0.0207 (7)	0.0343 (8)	0.0425 (8)	−0.0019 (5)	0.0062 (5)	0.0037 (6)
O2B	0.030 (8)	0.022 (8)	0.045 (7)	0.003 (6)	0.003 (6)	0.014 (6)
C1	0.0208 (7)	0.0193 (7)	0.0251 (7)	0.0015 (6)	0.0029 (6)	−0.0013 (6)
C2	0.0225 (7)	0.0188 (7)	0.0259 (7)	0.0019 (6)	0.0042 (6)	−0.0017 (6)
C3	0.0224 (8)	0.0200 (7)	0.0297 (8)	0.0003 (6)	0.0039 (6)	−0.0065 (6)
C4	0.0264 (8)	0.0275 (8)	0.0287 (8)	−0.0014 (7)	0.0018 (6)	−0.0066 (6)
C5	0.0320 (9)	0.0392 (10)	0.0331 (9)	0.0013 (8)	−0.0027 (7)	−0.0119 (8)
C6	0.0266 (9)	0.0409 (11)	0.0504 (11)	−0.0073 (8)	−0.0003 (8)	−0.0200 (9)
C7	0.0291 (9)	0.0293 (9)	0.0510 (11)	−0.0079 (7)	0.0080 (8)	−0.0116 (8)
C8	0.0272 (8)	0.0211 (8)	0.0384 (9)	−0.0012 (7)	0.0078 (7)	−0.0060 (7)
C9	0.0369 (10)	0.0245 (9)	0.0434 (10)	−0.0058 (7)	0.0112 (8)	0.0024 (7)
C10	0.0381 (10)	0.0280 (9)	0.0356 (9)	0.0004 (7)	0.0058 (8)	0.0076 (7)
C11	0.0245 (8)	0.0242 (8)	0.0297 (8)	0.0014 (6)	0.0018 (6)	−0.0004 (6)
C12	0.0235 (8)	0.0229 (8)	0.0274 (8)	0.0024 (6)	0.0033 (6)	−0.0010 (6)
C13	0.0258 (8)	0.0359 (10)	0.0315 (9)	−0.0028 (7)	−0.0015 (7)	−0.0034 (7)
C14	0.0192 (7)	0.0203 (7)	0.0260 (7)	0.0001 (6)	0.0020 (6)	−0.0012 (6)
C15	0.0295 (8)	0.0243 (8)	0.0260 (8)	0.0041 (7)	−0.0007 (6)	−0.0015 (6)
C16	0.0317 (9)	0.0251 (8)	0.0327 (9)	0.0044 (7)	0.0023 (7)	−0.0043 (7)
C17	0.0328 (9)	0.0227 (8)	0.0454 (10)	0.0048 (7)	0.0009 (8)	0.0005 (7)
C18	0.0338 (9)	0.0292 (9)	0.0362 (9)	0.0051 (7)	−0.0013 (7)	0.0074 (7)
C19	0.0314 (9)	0.0289 (9)	0.0279 (8)	0.0019 (7)	0.0023 (7)	0.0034 (7)

Geometric parameters (Å, º) top

S1—O2B	1.4741 (16)	C10—C11	1.397 (2)
S1—O2A	1.4752 (13)	C10—H10	0.9500
S1—C1	1.7796 (16)	C12—C13	1.483 (2)
S1—C14	1.8287 (15)	C13—H13A	0.9800
O1—C11	1.372 (2)	C13—H13B	0.9800
O1—C12	1.3782 (19)	C13—H13C	0.9800
C1—C12	1.356 (2)	C14—C15	1.520 (2)
C1—C2	1.448 (2)	C14—C19	1.530 (2)
C2—C11	1.377 (2)	C14—H14	1.0000
C2—C3	1.431 (2)	C15—C16	1.526 (2)
C3—C4	1.408 (2)	C15—H15A	0.9900
C3—C8	1.431 (2)	C15—H15B	0.9900
C4—C5	1.374 (2)	C16—C17	1.519 (2)
C4—H4	0.9500	C16—H16A	0.9900
C5—C6	1.400 (3)	C16—H16B	0.9900
C5—H5	0.9500	C17—C18	1.524 (3)
C6—C7	1.360 (3)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C7—C8	1.416 (2)	C18—C19	1.532 (2)
C7—H7	0.9500	C18—H18A	0.9900
C8—C9	1.424 (3)	C18—H18B	0.9900
C9—C10	1.363 (3)	C19—H19A	0.9900
C9—H9	0.9500	C19—H19B	0.9900

O2B—S1—O2A	105.2 (6)	C12—C13—H13A	109.5
O2B—S1—C1	119.1 (6)	C12—C13—H13B	109.5
O2A—S1—C1	109.24 (8)	H13A—C13—H13B	109.5
O2B—S1—C14	117.8 (6)	C12—C13—H13C	109.5
O2A—S1—C14	106.57 (7)	H13A—C13—H13C	109.5
C1—S1—C14	98.29 (7)	H13B—C13—H13C	109.5
C11—O1—C12	106.44 (12)	C15—C14—C19	111.88 (13)
C12—C1—C2	107.20 (14)	C15—C14—S1	111.98 (11)
C12—C1—S1	125.51 (12)	C19—C14—S1	106.89 (10)
C2—C1—S1	127.28 (12)	C15—C14—H14	108.7
C11—C2—C3	119.04 (14)	C19—C14—H14	108.7
C11—C2—C1	104.89 (14)	S1—C14—H14	108.7
C3—C2—C1	136.07 (15)	C14—C15—C16	110.75 (13)
C4—C3—C2	124.48 (15)	C14—C15—H15A	109.5
C4—C3—C8	118.85 (15)	C16—C15—H15A	109.5
C2—C3—C8	116.67 (15)	C14—C15—H15B	109.5
C5—C4—C3	120.71 (16)	C16—C15—H15B	109.5
C5—C4—H4	119.6	H15A—C15—H15B	108.1
C3—C4—H4	119.6	C17—C16—C15	111.43 (14)
C4—C5—C6	120.46 (18)	C17—C16—H16A	109.3
C4—C5—H5	119.8	C15—C16—H16A	109.3
C6—C5—H5	119.8	C17—C16—H16B	109.3
C7—C6—C5	120.37 (17)	C15—C16—H16B	109.3
C7—C6—H6	119.8	H16A—C16—H16B	108.0
C5—C6—H6	119.8	C16—C17—C18	110.31 (14)
C6—C7—C8	121.19 (17)	C16—C17—H17A	109.6
C6—C7—H7	119.4	C18—C17—H17A	109.6
C8—C7—H7	119.4	C16—C17—H17B	109.6
C7—C8—C9	121.08 (16)	C18—C17—H17B	109.6
C7—C8—C3	118.42 (16)	H17A—C17—H17B	108.1
C9—C8—C3	120.49 (16)	C17—C18—C19	110.89 (14)
C10—C9—C8	122.26 (16)	C17—C18—H18A	109.5
C10—C9—H9	118.9	C19—C18—H18A	109.5
C8—C9—H9	118.9	C17—C18—H18B	109.5
C9—C10—C11	116.30 (16)	C19—C18—H18B	109.5
C9—C10—H10	121.9	H18A—C18—H18B	108.1
C11—C10—H10	121.9	C14—C19—C18	110.95 (13)
O1—C11—C2	111.06 (14)	C14—C19—H19A	109.5
O1—C11—C10	123.70 (15)	C18—C19—H19A	109.5
C2—C11—C10	125.22 (16)	C14—C19—H19B	109.5
C1—C12—O1	110.39 (14)	C18—C19—H19B	109.5
C1—C12—C13	135.26 (15)	H19A—C19—H19B	108.0
O1—C12—C13	114.34 (14)

O2B—S1—C1—C12	−129.3 (7)	C12—O1—C11—C2	−0.83 (17)
O2A—S1—C1—C12	−8.48 (16)	C12—O1—C11—C10	177.79 (15)
C14—S1—C1—C12	102.38 (15)	C3—C2—C11—O1	−179.51 (13)
O2B—S1—C1—C2	49.3 (7)	C1—C2—C11—O1	1.20 (17)
O2A—S1—C1—C2	170.18 (13)	C3—C2—C11—C10	1.9 (2)
C14—S1—C1—C2	−78.96 (14)	C1—C2—C11—C10	−177.40 (16)
C12—C1—C2—C11	−1.11 (17)	C9—C10—C11—O1	−179.38 (15)
S1—C1—C2—C11	−179.96 (12)	C9—C10—C11—C2	−1.0 (3)
C12—C1—C2—C3	179.78 (17)	C2—C1—C12—O1	0.64 (17)
S1—C1—C2—C3	0.9 (3)	S1—C1—C12—O1	179.53 (10)
C11—C2—C3—C4	179.47 (15)	C2—C1—C12—C13	179.33 (17)
C1—C2—C3—C4	−1.5 (3)	S1—C1—C12—C13	−1.8 (3)
C11—C2—C3—C8	−1.3 (2)	C11—O1—C12—C1	0.08 (17)
C1—C2—C3—C8	177.71 (16)	C11—O1—C12—C13	−178.90 (13)
C2—C3—C4—C5	178.74 (15)	O2B—S1—C14—C15	173.0 (7)
C8—C3—C4—C5	−0.5 (2)	O2A—S1—C14—C15	55.20 (13)
C3—C4—C5—C6	0.3 (3)	C1—S1—C14—C15	−57.80 (12)
C4—C5—C6—C7	−0.1 (3)	O2B—S1—C14—C19	50.1 (7)
C5—C6—C7—C8	0.0 (3)	O2A—S1—C14—C19	−67.66 (12)
C6—C7—C8—C9	−179.00 (17)	C1—S1—C14—C19	179.35 (11)
C6—C7—C8—C3	−0.1 (3)	C19—C14—C15—C16	−54.42 (18)
C4—C3—C8—C7	0.3 (2)	S1—C14—C15—C16	−174.40 (11)
C2—C3—C8—C7	−178.92 (14)	C14—C15—C16—C17	56.20 (18)
C4—C3—C8—C9	179.24 (15)	C15—C16—C17—C18	−57.71 (19)
C2—C3—C8—C9	0.0 (2)	C16—C17—C18—C19	57.25 (19)
C7—C8—C9—C10	179.84 (17)	C15—C14—C19—C18	54.40 (18)
C3—C8—C9—C10	1.0 (3)	S1—C14—C19—C18	177.31 (12)
C8—C9—C10—C11	−0.5 (3)	C17—C18—C19—C14	−55.59 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2Bⁱ	0.98	2.12	2.848 (6)	130
C14—H14···O2Aⁱⁱ	1.00	2.38	3.2947 (19)	152

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₂S
M_r	312.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	5.8424 (1), 19.5900 (3), 13.4314 (2)
β (°)	92.649 (1)
V (Å³)	1535.62 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.42 × 0.34 × 0.26

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.916, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	14260, 3527, 3026
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.06
No. of reflections	3527
No. of parameters	210
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −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

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O2Bⁱ	0.98	2.12	2.848 (6)	130
C14—H14···O2Aⁱⁱ	1.00	2.38	3.2947 (19)	152

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1731–o1732. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Woo, H. M., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o3881–o3882. Web of Science CSD CrossRef IUCr Journals Google Scholar
Einhorn, J., Demerseman, P., Royer, R., Cavier, R. & Gayral, P. (1984). Eur. J. Med. Chem. 19, 405–410. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hranjec, M., Grdisa, M., Pavelic, K., Boykin, D. W. & Karminski-Zamola, G. (2003). IL Farmaco, 58, 1319–1324. CrossRef PubMed CAS Google Scholar
Mahadevan, K. M. & Vaidya, V. P. (2003). Indian J. Pharm. Sci. 65, 128–134. CAS 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 67| Part 4| April 2011| Page o1002

doi:10.1107/S1600536811010981

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