5-Cyclo­hexyl-2-methyl-3-phenyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536811013705

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1157

doi:10.1107/S1600536811013705

Open

access

5-Cyclohexyl-2-methyl-3-phenylsulfinyl-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 11 April 2011; accepted 12 April 2011; online 16 April 2011)

In the title compound, C₂₁H₂₂O₂S, the cyclohexyl ring adopts a chair conformation. The phenyl ring makes a dihedral angle of 84.80 (4)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ); 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-arylsulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010 , 2011 ).

Experimental

Crystal data

C₂₁H₂₂O₂S
M_r = 338.45
Triclinic, $[P \overline 1]$
a = 8.8532 (2) Å
b = 10.2011 (2) Å
c = 10.4752 (3) Å
α = 90.734 (1)°
β = 111.568 (1)°
γ = 97.127 (1)°
V = 871.25 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 173 K
0.35 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.650, T_max = 0.746
15560 measured reflections
4012 independent reflections
3481 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.07
4012 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2ⁱ	0.98	2.52	3.4516 (19)	159
C21—H21⋯O2ⁱⁱ	0.95	2.47	3.2793 (18)	144
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y, -z+1.

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/S1600536811013705/zl2365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013705/zl2365Isup2.hkl

checkCIF report

Comment top

Many compounds having a benzofuran ring system have attracted much attention owing to their diverse pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009, Galal et al., 2009, Khan et al., 2005). These compounds widely occur in nature (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our study of the substituent effect on the solid state structures of 3-arylsulfinyl-2-methyl-1-benzofuran analogues (Choi et al., 2010, 2011), we report here on the crystal structure of the title compound

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.004 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle formed by the mean plane of the benzofuran ring and the phenyl ring is 84.80 (4)° . The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a methyl H atom and the O atom of the sulfinyl group (Table 1; C15—H15B···O2ⁱ), and the second one between a phenyl H atom and the O atom of the sulfinyl group (Table 1; C21—H21···O2ⁱⁱ).

Related literature top

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); 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-arylsulfinyl-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (269 mg, 1.2 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-methyl-3-phenylsulfanyl-1-benzofuran (354 mg, 1.1 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 406–407 K; R_f = 0.68 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate 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 hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 1, - y, - z; (ii) - x + 1, - y, -z + 1.]

5-Cyclohexyl-2-methyl-3-phenylsulfinyl-1-benzofuran top

Crystal data top

C₂₁H₂₂O₂S	Z = 2
M_r = 338.45	F(000) = 360
Triclinic, P1	D_x = 1.290 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8532 (2) Å	Cell parameters from 6502 reflections
b = 10.2011 (2) Å	θ = 2.6–27.5°
c = 10.4752 (3) Å	µ = 0.20 mm⁻¹
α = 90.734 (1)°	T = 173 K
β = 111.568 (1)°	Block, colourless
γ = 97.127 (1)°	0.35 × 0.25 × 0.16 mm
V = 871.25 (4) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	4012 independent reflections
Radiation source: rotating anode	3481 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.0°
ϕ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.650, T_max = 0.746	l = −13→13
15560 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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0528P)² + 0.2372P] where P = (F_o² + 2F_c²)/3
4012 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₂₂O₂S	γ = 97.127 (1)°
M_r = 338.45	V = 871.25 (4) Å³
Triclinic, P1	Z = 2
a = 8.8532 (2) Å	Mo Kα radiation
b = 10.2011 (2) Å	µ = 0.20 mm⁻¹
c = 10.4752 (3) Å	T = 173 K
α = 90.734 (1)°	0.35 × 0.25 × 0.16 mm
β = 111.568 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4012 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3481 reflections with I > 2σ(I)
T_min = 0.650, T_max = 0.746	R_int = 0.028
15560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.07	Δρ_max = 0.44 e Å⁻³
4012 reflections	Δρ_min = −0.26 e Å⁻³
218 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
S1	0.33404 (4)	0.01587 (3)	0.18991 (3)	0.02947 (11)
O1	0.52084 (12)	0.32470 (10)	0.04883 (10)	0.0334 (2)
O2	0.45627 (13)	−0.04998 (10)	0.29798 (11)	0.0388 (3)
C1	0.43524 (16)	0.16549 (13)	0.16271 (14)	0.0279 (3)
C2	0.55010 (16)	0.26393 (13)	0.26444 (14)	0.0264 (3)
C3	0.61465 (16)	0.28037 (13)	0.40727 (14)	0.0265 (3)
H3	0.5837	0.2160	0.4611	0.032*
C4	0.72549 (16)	0.39299 (13)	0.46990 (14)	0.0273 (3)
C5	0.76898 (17)	0.48649 (14)	0.38824 (15)	0.0328 (3)
H5	0.8443	0.5631	0.4321	0.039*
C6	0.70636 (18)	0.47162 (15)	0.24594 (16)	0.0347 (3)
H6	0.7366	0.5356	0.1914	0.042*
C7	0.59801 (17)	0.35912 (14)	0.18809 (14)	0.0291 (3)
C8	0.42408 (17)	0.20589 (14)	0.03698 (14)	0.0310 (3)
C9	0.79606 (17)	0.41638 (13)	0.62465 (14)	0.0284 (3)
H9	0.8821	0.4958	0.6485	0.034*
C10	0.6659 (2)	0.44576 (18)	0.68066 (16)	0.0416 (4)
H10A	0.6177	0.5245	0.6381	0.050*
H10B	0.5769	0.3698	0.6551	0.050*
C11	0.7379 (2)	0.47091 (17)	0.83653 (16)	0.0423 (4)
H11A	0.8200	0.5516	0.8617	0.051*
H11B	0.6496	0.4863	0.8694	0.051*
C12	0.81830 (19)	0.35505 (15)	0.90597 (15)	0.0368 (3)
H12A	0.7339	0.2767	0.8892	0.044*
H12B	0.8697	0.3763	1.0065	0.044*
C13	0.94782 (19)	0.32296 (16)	0.85200 (15)	0.0364 (3)
H13A	0.9925	0.2429	0.8941	0.044*
H13B	1.0391	0.3972	0.8792	0.044*
C14	0.87798 (18)	0.29943 (14)	0.69594 (14)	0.0315 (3)
H14A	0.7965	0.2184	0.6695	0.038*
H14B	0.9674	0.2850	0.6642	0.038*
C15	0.3295 (2)	0.14926 (17)	−0.10566 (15)	0.0405 (4)
H15A	0.2767	0.0596	−0.1031	0.061*
H15B	0.4039	0.1459	−0.1552	0.061*
H15C	0.2456	0.2049	−0.1528	0.061*
C16	0.20788 (16)	0.08189 (12)	0.26836 (14)	0.0268 (3)
C17	0.06675 (19)	0.12795 (16)	0.18436 (16)	0.0387 (3)
H17	0.0404	0.1284	0.0879	0.046*
C18	−0.0358 (2)	0.17341 (18)	0.2422 (2)	0.0471 (4)
H18	−0.1330	0.2058	0.1854	0.057*
C19	0.0022 (2)	0.17188 (18)	0.3815 (2)	0.0483 (4)
H19	−0.0685	0.2035	0.4209	0.058*
C20	0.1428 (2)	0.12449 (18)	0.46414 (17)	0.0462 (4)
H20	0.1686	0.1236	0.5605	0.055*
C21	0.24659 (19)	0.07815 (15)	0.40774 (15)	0.0344 (3)
H21	0.3428	0.0444	0.4644	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0328 (2)	0.02712 (18)	0.02898 (19)	0.00368 (13)	0.01233 (15)	−0.00168 (13)
O1	0.0350 (5)	0.0415 (6)	0.0285 (5)	0.0062 (4)	0.0171 (4)	0.0062 (4)
O2	0.0405 (6)	0.0351 (5)	0.0433 (6)	0.0142 (5)	0.0154 (5)	0.0074 (5)
C1	0.0279 (7)	0.0319 (7)	0.0263 (6)	0.0064 (5)	0.0123 (5)	0.0004 (5)
C2	0.0245 (6)	0.0276 (6)	0.0300 (7)	0.0064 (5)	0.0126 (5)	0.0031 (5)
C3	0.0264 (6)	0.0267 (6)	0.0279 (7)	0.0047 (5)	0.0114 (5)	0.0039 (5)
C4	0.0238 (6)	0.0269 (6)	0.0314 (7)	0.0062 (5)	0.0097 (5)	0.0031 (5)
C5	0.0287 (7)	0.0294 (7)	0.0402 (8)	0.0010 (5)	0.0133 (6)	0.0041 (6)
C6	0.0337 (7)	0.0353 (7)	0.0395 (8)	0.0030 (6)	0.0189 (6)	0.0108 (6)
C7	0.0276 (7)	0.0355 (7)	0.0284 (7)	0.0076 (5)	0.0142 (6)	0.0055 (5)
C8	0.0304 (7)	0.0377 (7)	0.0295 (7)	0.0091 (6)	0.0152 (6)	0.0016 (6)
C9	0.0261 (6)	0.0260 (6)	0.0300 (7)	0.0015 (5)	0.0076 (5)	−0.0001 (5)
C10	0.0355 (8)	0.0534 (9)	0.0348 (8)	0.0191 (7)	0.0080 (7)	−0.0060 (7)
C11	0.0402 (9)	0.0513 (9)	0.0352 (8)	0.0160 (7)	0.0111 (7)	−0.0082 (7)
C12	0.0377 (8)	0.0427 (8)	0.0318 (7)	0.0024 (6)	0.0162 (6)	−0.0022 (6)
C13	0.0371 (8)	0.0437 (8)	0.0305 (7)	0.0133 (7)	0.0127 (6)	0.0059 (6)
C14	0.0343 (7)	0.0335 (7)	0.0301 (7)	0.0099 (6)	0.0143 (6)	0.0040 (5)
C15	0.0449 (9)	0.0518 (9)	0.0279 (7)	0.0110 (7)	0.0159 (7)	−0.0011 (6)
C16	0.0288 (7)	0.0236 (6)	0.0288 (7)	0.0018 (5)	0.0122 (6)	0.0021 (5)
C17	0.0371 (8)	0.0458 (9)	0.0342 (8)	0.0116 (7)	0.0122 (7)	0.0108 (6)
C18	0.0377 (9)	0.0493 (9)	0.0593 (11)	0.0173 (7)	0.0199 (8)	0.0125 (8)
C19	0.0471 (10)	0.0476 (9)	0.0611 (11)	0.0077 (8)	0.0326 (9)	−0.0047 (8)
C20	0.0530 (10)	0.0547 (10)	0.0352 (8)	0.0020 (8)	0.0234 (8)	−0.0054 (7)
C21	0.0338 (7)	0.0393 (8)	0.0282 (7)	0.0028 (6)	0.0099 (6)	0.0009 (6)

Geometric parameters (Å, º) top

S1—O2	1.4843 (11)	C11—H11A	0.9900
S1—C1	1.7529 (14)	C11—H11B	0.9900
S1—C16	1.7955 (14)	C12—C13	1.519 (2)
O1—C8	1.3706 (17)	C12—H12A	0.9900
O1—C7	1.3829 (17)	C12—H12B	0.9900
C1—C8	1.3574 (19)	C13—C14	1.5239 (19)
C1—C2	1.4494 (18)	C13—H13A	0.9900
C2—C7	1.3891 (19)	C13—H13B	0.9900
C2—C3	1.3908 (18)	C14—H14A	0.9900
C3—C4	1.3931 (18)	C14—H14B	0.9900
C3—H3	0.9500	C15—H15A	0.9800
C4—C5	1.4006 (19)	C15—H15B	0.9800
C4—C9	1.5112 (19)	C15—H15C	0.9800
C5—C6	1.385 (2)	C16—C21	1.374 (2)
C5—H5	0.9500	C16—C17	1.380 (2)
C6—C7	1.373 (2)	C17—C18	1.382 (2)
C6—H6	0.9500	C17—H17	0.9500
C8—C15	1.485 (2)	C18—C19	1.372 (3)
C9—C10	1.530 (2)	C18—H18	0.9500
C9—C14	1.5317 (19)	C19—C20	1.379 (3)
C9—H9	1.0000	C19—H19	0.9500
C10—C11	1.524 (2)	C20—C21	1.385 (2)
C10—H10A	0.9900	C20—H20	0.9500
C10—H10B	0.9900	C21—H21	0.9500
C11—C12	1.511 (2)

O2—S1—C1	107.74 (6)	C10—C11—H11B	109.4
O2—S1—C16	106.99 (6)	H11A—C11—H11B	108.0
C1—S1—C16	98.62 (6)	C11—C12—C13	111.07 (13)
C8—O1—C7	106.49 (10)	C11—C12—H12A	109.4
C8—C1—C2	107.37 (12)	C13—C12—H12A	109.4
C8—C1—S1	124.25 (11)	C11—C12—H12B	109.4
C2—C1—S1	128.29 (10)	C13—C12—H12B	109.4
C7—C2—C3	119.49 (12)	H12A—C12—H12B	108.0
C7—C2—C1	104.63 (12)	C12—C13—C14	111.68 (12)
C3—C2—C1	135.87 (12)	C12—C13—H13A	109.3
C2—C3—C4	118.76 (12)	C14—C13—H13A	109.3
C2—C3—H3	120.6	C12—C13—H13B	109.3
C4—C3—H3	120.6	C14—C13—H13B	109.3
C3—C4—C5	119.53 (13)	H13A—C13—H13B	107.9
C3—C4—C9	120.59 (12)	C13—C14—C9	111.88 (12)
C5—C4—C9	119.87 (12)	C13—C14—H14A	109.2
C6—C5—C4	122.53 (13)	C9—C14—H14A	109.2
C6—C5—H5	118.7	C13—C14—H14B	109.2
C4—C5—H5	118.7	C9—C14—H14B	109.2
C7—C6—C5	116.21 (13)	H14A—C14—H14B	107.9
C7—C6—H6	121.9	C8—C15—H15A	109.5
C5—C6—H6	121.9	C8—C15—H15B	109.5
C6—C7—O1	125.85 (12)	H15A—C15—H15B	109.5
C6—C7—C2	123.48 (13)	C8—C15—H15C	109.5
O1—C7—C2	110.67 (12)	H15A—C15—H15C	109.5
C1—C8—O1	110.83 (12)	H15B—C15—H15C	109.5
C1—C8—C15	133.47 (14)	C21—C16—C17	121.28 (13)
O1—C8—C15	115.70 (12)	C21—C16—S1	120.21 (11)
C4—C9—C10	111.77 (11)	C17—C16—S1	118.37 (11)
C4—C9—C14	112.05 (11)	C16—C17—C18	119.21 (15)
C10—C9—C14	109.62 (12)	C16—C17—H17	120.4
C4—C9—H9	107.7	C18—C17—H17	120.4
C10—C9—H9	107.7	C19—C18—C17	120.21 (16)
C14—C9—H9	107.7	C19—C18—H18	119.9
C11—C10—C9	111.62 (13)	C17—C18—H18	119.9
C11—C10—H10A	109.3	C18—C19—C20	120.03 (15)
C9—C10—H10A	109.3	C18—C19—H19	120.0
C11—C10—H10B	109.3	C20—C19—H19	120.0
C9—C10—H10B	109.3	C19—C20—C21	120.49 (16)
H10A—C10—H10B	108.0	C19—C20—H20	119.8
C12—C11—C10	111.23 (13)	C21—C20—H20	119.8
C12—C11—H11A	109.4	C16—C21—C20	118.77 (15)
C10—C11—H11A	109.4	C16—C21—H21	120.6
C12—C11—H11B	109.4	C20—C21—H21	120.6

O2—S1—C1—C8	131.22 (12)	C7—O1—C8—C1	1.01 (15)
C16—S1—C1—C8	−117.76 (13)	C7—O1—C8—C15	−179.63 (12)
O2—S1—C1—C2	−45.06 (13)	C3—C4—C9—C10	−68.63 (16)
C16—S1—C1—C2	65.96 (13)	C5—C4—C9—C10	110.04 (15)
C8—C1—C2—C7	0.77 (15)	C3—C4—C9—C14	54.86 (16)
S1—C1—C2—C7	177.55 (11)	C5—C4—C9—C14	−126.47 (14)
C8—C1—C2—C3	−179.30 (15)	C4—C9—C10—C11	−179.32 (13)
S1—C1—C2—C3	−2.5 (2)	C14—C9—C10—C11	55.83 (17)
C7—C2—C3—C4	0.36 (19)	C9—C10—C11—C12	−56.99 (19)
C1—C2—C3—C4	−179.57 (14)	C10—C11—C12—C13	55.67 (18)
C2—C3—C4—C5	0.07 (19)	C11—C12—C13—C14	−54.82 (17)
C2—C3—C4—C9	178.73 (11)	C12—C13—C14—C9	55.03 (17)
C3—C4—C5—C6	−0.3 (2)	C4—C9—C14—C13	−179.56 (12)
C9—C4—C5—C6	−178.94 (13)	C10—C9—C14—C13	−54.87 (16)
C4—C5—C6—C7	0.0 (2)	O2—S1—C16—C21	6.99 (13)
C5—C6—C7—O1	179.83 (12)	C1—S1—C16—C21	−104.63 (12)
C5—C6—C7—C2	0.4 (2)	O2—S1—C16—C17	−168.86 (11)
C8—O1—C7—C6	−179.94 (14)	C1—S1—C16—C17	79.52 (12)
C8—O1—C7—C2	−0.49 (15)	C21—C16—C17—C18	1.2 (2)
C3—C2—C7—C6	−0.6 (2)	S1—C16—C17—C18	177.02 (13)
C1—C2—C7—C6	179.30 (13)	C16—C17—C18—C19	−0.4 (3)
C3—C2—C7—O1	179.89 (11)	C17—C18—C19—C20	−0.2 (3)
C1—C2—C7—O1	−0.16 (14)	C18—C19—C20—C21	0.0 (3)
C2—C1—C8—O1	−1.12 (15)	C17—C16—C21—C20	−1.4 (2)
S1—C1—C8—O1	−178.06 (9)	S1—C16—C21—C20	−177.15 (12)
C2—C1—C8—C15	179.67 (15)	C19—C20—C21—C16	0.8 (2)
S1—C1—C8—C15	2.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2ⁱ	0.98	2.52	3.4516 (19)	159
C21—H21···O2ⁱⁱ	0.95	2.47	3.2793 (18)	144

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂O₂S
M_r	338.45
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.8532 (2), 10.2011 (2), 10.4752 (3)
α, β, γ (°)	90.734 (1), 111.568 (1), 97.127 (1)
V (Å³)	871.25 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.35 × 0.25 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.650, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15560, 4012, 3481
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.07
No. of reflections	4012
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.26

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
C15—H15B···O2ⁱ	0.98	2.52	3.4516 (19)	159
C21—H21···O2ⁱⁱ	0.95	2.47	3.2793 (18)	144

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

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191–195. Web of Science CrossRef PubMed CAS Google Scholar
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. (2010). Acta Cryst. E66, o2551. CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o768. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420–2428. Web of Science CrossRef PubMed CAS Google Scholar
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796–4805. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831–834. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1157

doi:10.1107/S1600536811013705

Open

access