2-(5-Cyclo­hexyl-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid

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

doi:10.1107/S1600536811026298

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1957

doi:10.1107/S1600536811026298

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2-(5-Cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid

Pil Ja Seo,^a Hong Dae Choi,^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 30 June 2011; accepted 2 July 2011; online 9 July 2011)

In the title compound, C₁₇H₂₀O₃S, the cyclohexyl ring adopts a chair conformation. In the crystal, the carboxyl groups are involved in intermolecular O—H⋯O hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further stabilized by weak intermolecular C—H⋯O hydrogen bonds. In addition, the crystal structure also exhibits aromatic π–π interactions between the furan rings of adjacent molecules [centroid–centroid distance = 3.505 (2) Å, interplanar distance = 3.385 (2) Å and slippage = 0.909 (2) Å], and intermolecular C—H⋯π interactions.

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 2-(5-alkyl-3-methylsulfanyl-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009a ,b ); Seo et al. (2007 ).

Experimental

Crystal data

C₁₇H₂₀O₃S
M_r = 304.40
Triclinic, $[P \overline 1]$
a = 7.3434 (2) Å
b = 9.0765 (3) Å
c = 11.6009 (4) Å
α = 86.086 (2)°
β = 86.083 (2)°
γ = 86.690 (2)°
V = 768.53 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.32 × 0.21 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.934, T_max = 0.978
14240 measured reflections
3864 independent reflections
3255 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.100
S = 1.05
3864 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3ⁱ	0.95	2.59	3.4777 (17)	157
O3—H3O⋯O2ⁱⁱ	0.84	1.80	2.6347 (15)	176
C13—H13A⋯Cg1ⁱⁱⁱ	0.99	2.82	3.581 (2)	134
C14—H14B⋯Cg2ⁱⁱⁱ	0.99	2.85	3.678 (2)	147
C15—H15A⋯Cg2^iv	0.99	2.67	3.501 (2)	142
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z; (iii) -x+1, -y+1, -z+1; (iv) x, 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/S1600536811026298/rk2282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026298/rk2282Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026298/rk2282Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a benzofuran moiety have drawn much attention in view of their valuable 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 benzofuran derivatives 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 2-(5-alkyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid analogues (Choi et al., 2009a,b, Seo et al., 2007), we report herein the crystal structure of the title compound.

In the title molecule, Fig. 1, the benzofuran unit is essentially planar, with a mean deviation of 0.006 (1)Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring has the chair-conformation. In the crystal structure, the carboxyl groups are involved in intermolecular O—H···O hydrogen bonds (Fig. 2 & Table 1), which link the molecules into centrosymmetric dimers. These dimers are further stabilized by weak intermolecular C—H···O hydrogen bonds between a benzene H atom and the O atom of the hydroxy group (Fig. 2 & Table 1; C6—H6···O3ⁱ). The crystal packing, Fig. 3, also exhibits aromatic π–π interactions between the furan rings of the adjacent molecules, with a Cg1···Cg1^iv distance of 3.505 (2)Å and an interplanar distance of 3.385 (2)Å resulting in a slippage of 0.909 (2)Å (Cg1 is the centroid of C1/C2/C7/O1/C8 furan ring). Additionally, the crystal packing (Fig. 3) shows intermolecular C—H···π interactions; the first one between a cyclohexyl H atom and the furan ring (Table 1; C13—H13A···Cg1ⁱⁱⁱ), the second one between a cyclohexyl H atom and the benzene ring (Table 1; C14—H14B···Cg2ⁱⁱⁱ), and the third one between an H atom of the benzylic methylene group and the benzene ring (Table 1; C15—H15A···Cg2^iv, Cg2 is the centroid of the C2–C7 benzene ring). Symmetry codes as in the Table 1 and Fig. 2 and Fig. 3.

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 2-(5-alkyl-3-methylsulfanyl-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009a,b); Seo et al. (2007).

Experimental top

Ethyl 2-(5-cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (398 mg, 1.2 mmol) was added to a solution of potassium hydroxide (337 mg, mmol) in water (10 ml) and methanol (10 ml), and the mixture was refluxed for 5h, then cooled. Water was added, and the solution was extracted with dichloromethane. The aqueous layer was acidified to pH = 1 with concentrated hydrochloric acid and then extracted with chloroform, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colourless solid [yield 83%, m.p. 423–424 K; R_f = 0.45 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in diisopropyl ether 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 O—H···O and C—H···O inetractions (dotted lines) in the crystal structure of the title compound. Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z.
	Fig. 3. A view of the π–π and C—H···π inetractions (dotted lines) in the crystal structure of the title compound. Symmetry codes: (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z; (v) x, y, z-1.

2-(5-Cyclohexyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid top

Crystal data top

C₁₇H₂₀O₃S	Z = 2
M_r = 304.40	F(000) = 324
Triclinic, P1	D_x = 1.315 Mg m⁻³
Hall symbol: -P 1	Melting point = 423–424 K
a = 7.3434 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.0765 (3) Å	Cell parameters from 6244 reflections
c = 11.6009 (4) Å	θ = 2.3–28.4°
α = 86.086 (2)°	µ = 0.22 mm⁻¹
β = 86.083 (2)°	T = 173 K
γ = 86.690 (2)°	Block, colourless
V = 768.53 (4) Å³	0.32 × 0.21 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3864 independent reflections
Radiation source: rotating anode	3255 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.030
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.6°, θ_min = 1.8°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→12
T_min = 0.934, T_max = 0.978	l = −15→15
14240 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)] = 0.038	Hydrogen site location: difference Fourier map
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0444P)² + 0.2671P] where P = (F_o² + 2F_c²)/3
3864 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₇H₂₀O₃S	γ = 86.690 (2)°
M_r = 304.40	V = 768.53 (4) Å³
Triclinic, P1	Z = 2
a = 7.3434 (2) Å	Mo Kα radiation
b = 9.0765 (3) Å	µ = 0.22 mm⁻¹
c = 11.6009 (4) Å	T = 173 K
α = 86.086 (2)°	0.32 × 0.21 × 0.10 mm
β = 86.083 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3864 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3255 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.978	R_int = 0.030
14240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3864 reflections	Δρ_min = −0.26 e Å⁻³
191 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	0.39556 (5)	0.81571 (4)	0.07230 (3)	0.02882 (11)
O1	0.75966 (12)	0.47823 (10)	0.08350 (8)	0.0242 (2)
O2	0.88107 (14)	0.86762 (12)	0.06964 (8)	0.0308 (2)
O3	0.96423 (14)	0.89156 (11)	−0.11894 (8)	0.0304 (2)
H3O	1.0120	0.9672	−0.0995	0.046*
C1	0.52945 (18)	0.65343 (14)	0.09979 (11)	0.0211 (3)
C2	0.49420 (17)	0.53545 (14)	0.18707 (11)	0.0201 (3)
C3	0.35767 (17)	0.50941 (14)	0.27432 (11)	0.0209 (3)
H3	0.2577	0.5794	0.2852	0.025*
C4	0.36936 (18)	0.37992 (14)	0.34536 (11)	0.0218 (3)
C5	0.51779 (19)	0.27762 (15)	0.32655 (12)	0.0267 (3)
H5	0.5243	0.1889	0.3749	0.032*
C6	0.65490 (19)	0.30100 (15)	0.24036 (12)	0.0271 (3)
H6	0.7544	0.2309	0.2283	0.032*
C7	0.63899 (18)	0.43164 (14)	0.17300 (11)	0.0220 (3)
C8	0.68847 (18)	0.61388 (14)	0.04136 (11)	0.0222 (3)
C9	0.22459 (18)	0.35080 (15)	0.44187 (11)	0.0226 (3)
H9	0.1408	0.4416	0.4441	0.027*
C10	0.1076 (2)	0.22267 (17)	0.42058 (13)	0.0308 (3)
H10A	0.1860	0.1305	0.4167	0.037*
H10B	0.0519	0.2423	0.3453	0.037*
C11	−0.0433 (2)	0.20246 (17)	0.51702 (13)	0.0329 (3)
H11A	−0.1295	0.2905	0.5152	0.039*
H11B	−0.1123	0.1154	0.5035	0.039*
C12	0.0348 (2)	0.18098 (17)	0.63539 (13)	0.0339 (3)
H12A	−0.0666	0.1757	0.6960	0.041*
H12B	0.1085	0.0862	0.6406	0.041*
C13	0.1536 (2)	0.30655 (19)	0.65673 (13)	0.0330 (3)
H13A	0.2099	0.2854	0.7316	0.040*
H13B	0.0765	0.3993	0.6617	0.040*
C14	0.3035 (2)	0.32710 (19)	0.56051 (12)	0.0331 (3)
H14A	0.3889	0.2386	0.5614	0.040*
H14B	0.3734	0.4135	0.5746	0.040*
C15	0.79618 (19)	0.68726 (15)	−0.05668 (12)	0.0250 (3)
H15A	0.7147	0.7137	−0.1203	0.030*
H15B	0.8927	0.6157	−0.0855	0.030*
C16	0.88468 (17)	0.82431 (14)	−0.02779 (11)	0.0221 (3)
C17	0.4488 (2)	0.91892 (17)	0.19209 (14)	0.0352 (3)
H17A	0.4242	0.8600	0.2649	0.053*
H17B	0.3729	1.0113	0.1924	0.053*
H17C	0.5781	0.9414	0.1840	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0332 (2)	0.02291 (18)	0.0301 (2)	0.00036 (13)	−0.00535 (14)	0.00250 (13)
O1	0.0233 (5)	0.0225 (5)	0.0260 (5)	−0.0032 (4)	0.0036 (4)	0.0003 (4)
O2	0.0374 (6)	0.0353 (6)	0.0211 (5)	−0.0181 (4)	0.0030 (4)	−0.0037 (4)
O3	0.0382 (6)	0.0302 (5)	0.0235 (5)	−0.0169 (4)	0.0045 (4)	−0.0020 (4)
C1	0.0225 (6)	0.0191 (6)	0.0223 (6)	−0.0060 (5)	−0.0021 (5)	−0.0004 (5)
C2	0.0222 (6)	0.0191 (6)	0.0197 (6)	−0.0061 (5)	−0.0025 (5)	−0.0013 (5)
C3	0.0204 (6)	0.0210 (6)	0.0215 (6)	−0.0034 (5)	−0.0011 (5)	−0.0021 (5)
C4	0.0236 (6)	0.0223 (6)	0.0201 (6)	−0.0067 (5)	−0.0013 (5)	−0.0012 (5)
C5	0.0305 (7)	0.0226 (6)	0.0262 (7)	−0.0026 (5)	−0.0007 (6)	0.0036 (5)
C6	0.0264 (7)	0.0233 (7)	0.0304 (7)	0.0017 (5)	0.0007 (6)	0.0006 (6)
C7	0.0216 (6)	0.0230 (6)	0.0215 (6)	−0.0057 (5)	0.0008 (5)	−0.0011 (5)
C8	0.0257 (6)	0.0200 (6)	0.0215 (6)	−0.0069 (5)	−0.0019 (5)	−0.0012 (5)
C9	0.0237 (6)	0.0233 (6)	0.0208 (6)	−0.0061 (5)	0.0000 (5)	0.0008 (5)
C10	0.0330 (8)	0.0339 (8)	0.0270 (7)	−0.0150 (6)	0.0009 (6)	−0.0044 (6)
C11	0.0315 (8)	0.0336 (8)	0.0346 (8)	−0.0160 (6)	0.0034 (6)	−0.0037 (6)
C12	0.0361 (8)	0.0329 (8)	0.0310 (8)	−0.0076 (6)	0.0071 (6)	0.0055 (6)
C13	0.0322 (8)	0.0452 (9)	0.0217 (7)	−0.0085 (6)	−0.0013 (6)	0.0012 (6)
C14	0.0285 (7)	0.0485 (9)	0.0233 (7)	−0.0132 (6)	−0.0018 (6)	0.0002 (6)
C15	0.0288 (7)	0.0239 (6)	0.0227 (7)	−0.0088 (5)	0.0024 (5)	−0.0023 (5)
C16	0.0196 (6)	0.0233 (6)	0.0233 (6)	−0.0038 (5)	0.0000 (5)	0.0008 (5)
C17	0.0402 (9)	0.0269 (7)	0.0388 (9)	0.0018 (6)	−0.0023 (7)	−0.0063 (6)

Geometric parameters (Å, º) top

S1—C1	1.7463 (13)	C9—H9	1.0000
S1—C17	1.8044 (16)	C10—C11	1.530 (2)
O1—C7	1.3783 (15)	C10—H10A	0.9900
O1—C8	1.3808 (16)	C10—H10B	0.9900
O2—C16	1.2200 (16)	C11—C12	1.520 (2)
O3—C16	1.3041 (16)	C11—H11A	0.9900
O3—H3O	0.8400	C11—H11B	0.9900
C1—C8	1.3523 (19)	C12—C13	1.518 (2)
C1—C2	1.4446 (17)	C12—H12A	0.9900
C2—C7	1.3880 (18)	C12—H12B	0.9900
C2—C3	1.3934 (17)	C13—C14	1.523 (2)
C3—C4	1.3906 (18)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.4058 (19)	C14—H14A	0.9900
C4—C9	1.5109 (18)	C14—H14B	0.9900
C5—C6	1.3844 (19)	C15—C16	1.5040 (18)
C5—H5	0.9500	C15—H15A	0.9900
C6—C7	1.3786 (19)	C15—H15B	0.9900
C6—H6	0.9500	C17—H17A	0.9800
C8—C15	1.4823 (18)	C17—H17B	0.9800
C9—C14	1.5268 (19)	C17—H17C	0.9800
C9—C10	1.5280 (19)

C1—S1—C17	100.05 (7)	C12—C11—C10	111.44 (12)
C7—O1—C8	105.90 (10)	C12—C11—H11A	109.3
C16—O3—H3O	109.5	C10—C11—H11A	109.3
C8—C1—C2	106.46 (11)	C12—C11—H11B	109.3
C8—C1—S1	125.80 (10)	C10—C11—H11B	109.3
C2—C1—S1	127.74 (10)	H11A—C11—H11B	108.0
C7—C2—C3	119.29 (12)	C13—C12—C11	111.38 (12)
C7—C2—C1	105.62 (11)	C13—C12—H12A	109.4
C3—C2—C1	135.08 (12)	C11—C12—H12A	109.4
C4—C3—C2	119.28 (12)	C13—C12—H12B	109.4
C4—C3—H3	120.4	C11—C12—H12B	109.4
C2—C3—H3	120.4	H12A—C12—H12B	108.0
C3—C4—C5	119.13 (12)	C12—C13—C14	111.49 (13)
C3—C4—C9	120.14 (12)	C12—C13—H13A	109.3
C5—C4—C9	120.73 (12)	C14—C13—H13A	109.3
C6—C5—C4	122.61 (13)	C12—C13—H13B	109.3
C6—C5—H5	118.7	C14—C13—H13B	109.3
C4—C5—H5	118.7	H13A—C13—H13B	108.0
C7—C6—C5	116.27 (13)	C13—C14—C9	111.51 (12)
C7—C6—H6	121.9	C13—C14—H14A	109.3
C5—C6—H6	121.9	C9—C14—H14A	109.3
O1—C7—C6	126.17 (12)	C13—C14—H14B	109.3
O1—C7—C2	110.43 (11)	C9—C14—H14B	109.3
C6—C7—C2	123.40 (12)	H14A—C14—H14B	108.0
C1—C8—O1	111.59 (11)	C8—C15—C16	114.63 (11)
C1—C8—C15	132.48 (13)	C8—C15—H15A	108.6
O1—C8—C15	115.93 (11)	C16—C15—H15A	108.6
C4—C9—C14	112.67 (11)	C8—C15—H15B	108.6
C4—C9—C10	112.85 (11)	C16—C15—H15B	108.6
C14—C9—C10	110.37 (12)	H15A—C15—H15B	107.6
C4—C9—H9	106.8	O2—C16—O3	124.13 (12)
C14—C9—H9	106.8	O2—C16—C15	123.70 (12)
C10—C9—H9	106.8	O3—C16—C15	112.17 (11)
C9—C10—C11	111.07 (12)	S1—C17—H17A	109.5
C9—C10—H10A	109.4	S1—C17—H17B	109.5
C11—C10—H10A	109.4	H17A—C17—H17B	109.5
C9—C10—H10B	109.4	S1—C17—H17C	109.5
C11—C10—H10B	109.4	H17A—C17—H17C	109.5
H10A—C10—H10B	108.0	H17B—C17—H17C	109.5

C17—S1—C1—C8	−104.94 (13)	S1—C1—C8—O1	−179.32 (9)
C17—S1—C1—C2	75.49 (13)	C2—C1—C8—C15	−179.89 (13)
C8—C1—C2—C7	−0.22 (14)	S1—C1—C8—C15	0.5 (2)
S1—C1—C2—C7	179.42 (10)	C7—O1—C8—C1	−0.29 (14)
C8—C1—C2—C3	179.08 (14)	C7—O1—C8—C15	179.88 (11)
S1—C1—C2—C3	−1.3 (2)	C3—C4—C9—C14	−122.24 (14)
C7—C2—C3—C4	−0.06 (18)	C5—C4—C9—C14	57.33 (17)
C1—C2—C3—C4	−179.28 (13)	C3—C4—C9—C10	111.93 (14)
C2—C3—C4—C5	−0.68 (19)	C5—C4—C9—C10	−68.49 (16)
C2—C3—C4—C9	178.90 (11)	C4—C9—C10—C11	−176.96 (12)
C3—C4—C5—C6	0.6 (2)	C14—C9—C10—C11	55.98 (16)
C9—C4—C5—C6	−178.95 (13)	C9—C10—C11—C12	−55.76 (17)
C4—C5—C6—C7	0.2 (2)	C10—C11—C12—C13	54.84 (17)
C8—O1—C7—C6	179.81 (13)	C11—C12—C13—C14	−54.64 (18)
C8—O1—C7—C2	0.14 (14)	C12—C13—C14—C9	55.54 (18)
C5—C6—C7—O1	179.39 (12)	C4—C9—C14—C13	176.83 (12)
C5—C6—C7—C2	−1.0 (2)	C10—C9—C14—C13	−56.01 (17)
C3—C2—C7—O1	−179.39 (11)	C1—C8—C15—C16	69.12 (19)
C1—C2—C7—O1	0.04 (14)	O1—C8—C15—C16	−111.10 (13)
C3—C2—C7—C6	0.9 (2)	C8—C15—C16—O2	5.1 (2)
C1—C2—C7—C6	−179.63 (13)	C8—C15—C16—O3	−174.44 (12)
C2—C1—C8—O1	0.32 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.59	3.4777 (17)	157
O3—H3O···O2ⁱⁱ	0.84	1.80	2.6347 (15)	176
C13—H13A···Cg1ⁱⁱⁱ	0.99	2.82	3.581 (2)	134
C14—H14B···Cg2ⁱⁱⁱ	0.99	2.85	3.678 (2)	147
C15—H15A···Cg2^iv	0.99	2.67	3.501 (2)	142

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

Experimental details

Crystal data
Chemical formula	C₁₇H₂₀O₃S
M_r	304.40
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3434 (2), 9.0765 (3), 11.6009 (4)
α, β, γ (°)	86.086 (2), 86.083 (2), 86.690 (2)
V (Å³)	768.53 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.32 × 0.21 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.934, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14240, 3864, 3255
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.100, 1.05
No. of reflections	3864
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −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

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and C2–C7 benzene ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3ⁱ	0.95	2.59	3.4777 (17)	157
O3—H3O···O2ⁱⁱ	0.84	1.80	2.6347 (15)	176
C13—H13A···Cg1ⁱⁱⁱ	0.99	2.82	3.581 (2)	134
C14—H14B···Cg2ⁱⁱⁱ	0.99	2.85	3.678 (2)	147
C15—H15A···Cg2^iv	0.99	2.67	3.501 (2)	142

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+1, −z+1; (iv) x, 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. (2009a). Acta Cryst. E65, o998. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1527. 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
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o2048–o2049. Web of Science CSD CrossRef IUCr Journals 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

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Volume 67| Part 8| August 2011| Page o1957

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