2-(5-Cyclo-hexyl-3-isopropyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

In the title compound, C(19)H(24)O(3)S, the cylohexyl ring adopts a chair conformation. In the crystal, molecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. These dimers are further stabilized by weak inter-molecular C-H⋯π inter-actions, and by slipped π-π inter-actions between the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.557 (2) Å, inter-planar distance = 3.301 (2) Å and slippage = 1.325 (2) Å].

Related literature

For the biological 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 the crystal structure of related compound, see: Seo et al. (2011 ▶).

Experimental

Crystal data

C19H24O3S

M = 332.44

Triclinic,

a = 9.1261 (2) Å

b = 9.5308 (2) Å

c = 10.5577 (2) Å

α = 72.228 (1)°

β = 79.702 (1)°

γ = 85.724 (1)°

V = 860.19 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.36 × 0.27 × 0.23 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.931, T max = 0.955

16313 measured reflections

4297 independent reflections

3683 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.098

S = 1.05

4297 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055152/ff2049sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055152/ff2049Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055152/ff2049Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H24O3S	Z = 2
Mr = 332.44	F(000) = 356
Triclinic, P1	Dx = 1.284 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1261 (2) Å	Cell parameters from 6099 reflections
b = 9.5308 (2) Å	θ = 2.6–28.4°
c = 10.5577 (2) Å	µ = 0.20 mm−1
α = 72.228 (1)°	T = 173 K
β = 79.702 (1)°	Block, colourless
γ = 85.724 (1)°	0.36 × 0.27 × 0.23 mm
V = 860.19 (3) Å3

Bruker SMART APEXII CCD diffractometer	4297 independent reflections
Radiation source: rotating anode	3683 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.931, Tmax = 0.955	l = −14→14
16313 measured reflections

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.2514P] where P = (Fo2 + 2Fc2)/3
4297 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.77443 (3)	0.08125 (4)	0.20862 (3)	0.02569 (10)
O1	0.41530 (10)	−0.09376 (9)	0.16072 (9)	0.02482 (19)
O2	0.49565 (11)	−0.32309 (10)	0.42671 (10)	0.0303 (2)
O3	0.62246 (13)	−0.48943 (11)	0.33781 (12)	0.0398 (3)
H3O	0.583 (2)	−0.549 (2)	0.414 (2)	0.063 (6)*
C3	0.43798 (13)	0.27862 (13)	0.16349 (12)	0.0225 (2)
H3	0.5125	0.3395	0.1697	0.027*
C1	0.60123 (13)	0.03588 (13)	0.18486 (12)	0.0219 (2)
C2	0.47208 (13)	0.13333 (13)	0.16428 (12)	0.0211 (2)
C4	0.29330 (13)	0.33348 (13)	0.15341 (12)	0.0226 (2)
C5	0.18669 (14)	0.24291 (14)	0.13832 (13)	0.0252 (3)
H5	0.0891	0.2821	0.1288	0.030*
C6	0.21845 (14)	0.09865 (14)	0.13680 (13)	0.0253 (3)
H6	0.1458	0.0387	0.1260	0.030*
C7	0.36164 (14)	0.04727 (13)	0.15196 (12)	0.0219 (2)
C8	0.55972 (13)	−0.09689 (14)	0.18353 (12)	0.0236 (3)
C9	0.24973 (13)	0.48216 (13)	0.17527 (13)	0.0230 (2)
H9	0.3408	0.5437	0.1451	0.028*
C10	0.20154 (14)	0.45933 (14)	0.32704 (13)	0.0262 (3)
H10A	0.1163	0.3920	0.3607	0.031*
H10B	0.2847	0.4119	0.3747	0.031*
C11	0.15678 (15)	0.60348 (15)	0.35951 (14)	0.0289 (3)
H11A	0.1191	0.5821	0.4573	0.035*
H11B	0.2454	0.6657	0.3374	0.035*
C12	0.03734 (15)	0.68695 (15)	0.28067 (15)	0.0316 (3)
H12A	0.0154	0.7828	0.2992	0.038*
H12B	−0.0553	0.6297	0.3100	0.038*
C13	0.08862 (16)	0.71312 (14)	0.13001 (14)	0.0303 (3)
H13A	0.1767	0.7769	0.0995	0.036*
H13B	0.0083	0.7649	0.0804	0.036*
C14	0.12848 (16)	0.56783 (14)	0.09797 (14)	0.0289 (3)
H14A	0.1637	0.5882	−0.0001	0.035*
H14B	0.0384	0.5072	0.1223	0.035*
C15	0.63734 (15)	−0.24245 (14)	0.20305 (14)	0.0274 (3)
H15A	0.7446	−0.2299	0.2007	0.033*
H15B	0.6281	−0.2804	0.1274	0.033*
C16	0.57635 (14)	−0.35434 (13)	0.33429 (13)	0.0247 (3)
C17	0.73084 (15)	0.08854 (16)	0.38308 (14)	0.0292 (3)
H17	0.6358	0.1463	0.3937	0.035*
C18	0.7115 (2)	−0.06369 (19)	0.48197 (15)	0.0445 (4)
H18A	0.8041	−0.1215	0.4727	0.067*
H18B	0.6303	−0.1124	0.4635	0.067*
H18C	0.6876	−0.0562	0.5740	0.067*
C19	0.85552 (19)	0.1697 (2)	0.40621 (18)	0.0453 (4)
H19A	0.8377	0.1720	0.4999	0.068*
H19B	0.8588	0.2707	0.3453	0.068*
H19C	0.9507	0.1188	0.3884	0.068*

	U11	U22	U33	U12	U13	U23
S1	0.02160 (15)	0.02993 (17)	0.02262 (16)	−0.00101 (11)	−0.00132 (11)	−0.00472 (13)
O1	0.0289 (4)	0.0194 (4)	0.0266 (5)	0.0012 (3)	−0.0066 (4)	−0.0067 (4)
O2	0.0376 (5)	0.0218 (4)	0.0271 (5)	0.0013 (4)	0.0008 (4)	−0.0046 (4)
O3	0.0553 (7)	0.0199 (5)	0.0346 (6)	0.0067 (4)	0.0054 (5)	−0.0031 (4)
C3	0.0246 (6)	0.0209 (6)	0.0220 (6)	−0.0014 (4)	−0.0042 (5)	−0.0061 (5)
C1	0.0229 (5)	0.0227 (6)	0.0177 (5)	0.0006 (4)	−0.0021 (4)	−0.0034 (5)
C2	0.0234 (5)	0.0223 (6)	0.0164 (5)	−0.0001 (4)	−0.0029 (4)	−0.0043 (5)
C4	0.0263 (6)	0.0207 (5)	0.0201 (6)	0.0006 (4)	−0.0032 (5)	−0.0057 (5)
C5	0.0236 (6)	0.0256 (6)	0.0275 (6)	0.0021 (4)	−0.0060 (5)	−0.0092 (5)
C6	0.0269 (6)	0.0241 (6)	0.0266 (6)	−0.0018 (5)	−0.0069 (5)	−0.0084 (5)
C7	0.0277 (6)	0.0190 (5)	0.0188 (5)	0.0007 (4)	−0.0041 (5)	−0.0053 (5)
C8	0.0256 (6)	0.0235 (6)	0.0188 (6)	0.0020 (4)	−0.0023 (5)	−0.0034 (5)
C9	0.0249 (6)	0.0198 (5)	0.0253 (6)	0.0008 (4)	−0.0051 (5)	−0.0078 (5)
C10	0.0309 (6)	0.0239 (6)	0.0252 (6)	0.0040 (5)	−0.0092 (5)	−0.0077 (5)
C11	0.0343 (7)	0.0277 (6)	0.0271 (7)	0.0024 (5)	−0.0063 (5)	−0.0116 (6)
C12	0.0324 (7)	0.0275 (6)	0.0345 (7)	0.0068 (5)	−0.0042 (6)	−0.0111 (6)
C13	0.0365 (7)	0.0225 (6)	0.0313 (7)	0.0070 (5)	−0.0105 (6)	−0.0060 (5)
C14	0.0375 (7)	0.0241 (6)	0.0267 (6)	0.0049 (5)	−0.0120 (5)	−0.0072 (5)
C15	0.0307 (6)	0.0216 (6)	0.0260 (6)	0.0036 (5)	−0.0015 (5)	−0.0040 (5)
C16	0.0255 (6)	0.0206 (6)	0.0273 (6)	0.0018 (4)	−0.0071 (5)	−0.0049 (5)
C17	0.0280 (6)	0.0347 (7)	0.0277 (7)	−0.0011 (5)	−0.0017 (5)	−0.0148 (6)
C18	0.0580 (10)	0.0496 (9)	0.0229 (7)	−0.0175 (8)	−0.0037 (7)	−0.0045 (7)
C19	0.0461 (9)	0.0517 (10)	0.0461 (9)	−0.0131 (7)	−0.0070 (7)	−0.0239 (8)

S1—C1	1.7488 (12)	C10—H10B	0.9900
S1—C17	1.8351 (14)	C11—C12	1.5182 (18)
O1—C7	1.3774 (14)	C11—H11A	0.9900
O1—C8	1.3781 (14)	C11—H11B	0.9900
O2—C16	1.2128 (16)	C12—C13	1.523 (2)
O3—C16	1.3160 (15)	C12—H12A	0.9900
O3—H3O	0.87 (2)	C12—H12B	0.9900
C3—C4	1.3934 (16)	C13—C14	1.5268 (18)
C3—C2	1.3942 (17)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C1—C8	1.3525 (17)	C14—H14A	0.9900
C1—C2	1.4505 (16)	C14—H14B	0.9900
C2—C7	1.3932 (17)	C15—C16	1.5092 (18)
C4—C5	1.4077 (17)	C15—H15A	0.9900
C4—C9	1.5173 (16)	C15—H15B	0.9900
C5—C6	1.3882 (17)	C17—C18	1.508 (2)
C5—H5	0.9500	C17—C19	1.5160 (19)
C6—C7	1.3800 (17)	C17—H17	1.0000
C6—H6	0.9500	C18—H18A	0.9800
C8—C15	1.4832 (17)	C18—H18B	0.9800
C9—C14	1.5292 (17)	C18—H18C	0.9800
C9—C10	1.5355 (18)	C19—H19A	0.9800
C9—H9	1.0000	C19—H19B	0.9800
C10—C11	1.5250 (18)	C19—H19C	0.9800
C10—H10A	0.9900
C1—S1—C17	100.95 (6)	C11—C12—C13	110.51 (11)
C7—O1—C8	105.84 (9)	C11—C12—H12A	109.5
C16—O3—H3O	108.6 (14)	C13—C12—H12A	109.5
C4—C3—C2	119.24 (11)	C11—C12—H12B	109.5
C4—C3—H3	120.4	C13—C12—H12B	109.5
C2—C3—H3	120.4	H12A—C12—H12B	108.1
C8—C1—C2	106.07 (11)	C12—C13—C14	111.07 (11)
C8—C1—S1	127.22 (10)	C12—C13—H13A	109.4
C2—C1—S1	126.70 (9)	C14—C13—H13A	109.4
C7—C2—C3	119.29 (11)	C12—C13—H13B	109.4
C7—C2—C1	105.52 (11)	C14—C13—H13B	109.4
C3—C2—C1	135.04 (11)	H13A—C13—H13B	108.0
C3—C4—C5	119.17 (11)	C13—C14—C9	111.25 (11)
C3—C4—C9	119.17 (11)	C13—C14—H14A	109.4
C5—C4—C9	121.27 (11)	C9—C14—H14A	109.4
C6—C5—C4	122.64 (11)	C13—C14—H14B	109.4
C6—C5—H5	118.7	C9—C14—H14B	109.4
C4—C5—H5	118.7	H14A—C14—H14B	108.0
C7—C6—C5	116.17 (11)	C8—C15—C16	112.95 (11)
C7—C6—H6	121.9	C8—C15—H15A	109.0
C5—C6—H6	121.9	C16—C15—H15A	109.0
O1—C7—C6	126.11 (11)	C8—C15—H15B	109.0
O1—C7—C2	110.44 (10)	C16—C15—H15B	109.0
C6—C7—C2	123.43 (11)	H15A—C15—H15B	107.8
C1—C8—O1	112.09 (11)	O2—C16—O3	123.83 (12)
C1—C8—C15	132.97 (12)	O2—C16—C15	123.84 (11)
O1—C8—C15	114.94 (11)	O3—C16—C15	112.32 (11)
C4—C9—C14	115.11 (10)	C18—C17—C19	112.04 (13)
C4—C9—C10	108.57 (10)	C18—C17—S1	111.38 (10)
C14—C9—C10	110.10 (10)	C19—C17—S1	107.38 (10)
C4—C9—H9	107.6	C18—C17—H17	108.6
C14—C9—H9	107.6	C19—C17—H17	108.6
C10—C9—H9	107.6	S1—C17—H17	108.6
C11—C10—C9	112.52 (10)	C17—C18—H18A	109.5
C11—C10—H10A	109.1	C17—C18—H18B	109.5
C9—C10—H10A	109.1	H18A—C18—H18B	109.5
C11—C10—H10B	109.1	C17—C18—H18C	109.5
C9—C10—H10B	109.1	H18A—C18—H18C	109.5
H10A—C10—H10B	107.8	H18B—C18—H18C	109.5
C12—C11—C10	111.41 (11)	C17—C19—H19A	109.5
C12—C11—H11A	109.3	C17—C19—H19B	109.5
C10—C11—H11A	109.3	H19A—C19—H19B	109.5
C12—C11—H11B	109.3	C17—C19—H19C	109.5
C10—C11—H11B	109.3	H19A—C19—H19C	109.5
H11A—C11—H11B	108.0	H19B—C19—H19C	109.5
C17—S1—C1—C8	−104.25 (12)	C2—C1—C8—C15	−177.78 (13)
C17—S1—C1—C2	74.88 (12)	S1—C1—C8—C15	1.5 (2)
C4—C3—C2—C7	1.42 (18)	C7—O1—C8—C1	−2.16 (14)
C4—C3—C2—C1	−173.37 (13)	C7—O1—C8—C15	177.18 (10)
C8—C1—C2—C7	−0.07 (14)	C3—C4—C9—C14	150.58 (12)
S1—C1—C2—C7	−179.35 (9)	C5—C4—C9—C14	−36.65 (16)
C8—C1—C2—C3	175.22 (13)	C3—C4—C9—C10	−85.52 (13)
S1—C1—C2—C3	−4.1 (2)	C5—C4—C9—C10	87.25 (14)
C2—C3—C4—C5	−2.77 (18)	C4—C9—C10—C11	179.46 (10)
C2—C3—C4—C9	170.16 (11)	C14—C9—C10—C11	−53.70 (14)
C3—C4—C5—C6	1.88 (19)	C9—C10—C11—C12	54.49 (14)
C9—C4—C5—C6	−170.89 (12)	C10—C11—C12—C13	−55.52 (15)
C4—C5—C6—C7	0.42 (19)	C11—C12—C13—C14	57.35 (15)
C8—O1—C7—C6	−176.30 (12)	C12—C13—C14—C9	−57.68 (15)
C8—O1—C7—C2	2.07 (13)	C4—C9—C14—C13	178.08 (11)
C5—C6—C7—O1	176.30 (11)	C10—C9—C14—C13	54.99 (14)
C5—C6—C7—C2	−1.87 (19)	C1—C8—C15—C16	109.45 (16)
C3—C2—C7—O1	−177.44 (10)	O1—C8—C15—C16	−69.71 (14)
C1—C2—C7—O1	−1.26 (14)	C8—C15—C16—O2	−14.72 (18)
C3—C2—C7—C6	0.98 (19)	C8—C15—C16—O3	166.22 (11)
C1—C2—C7—C6	177.17 (12)	C1—S1—C17—C18	73.38 (11)
C2—C1—C8—O1	1.39 (14)	C1—S1—C17—C19	−163.61 (11)
S1—C1—C8—O1	−179.34 (9)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.87 (2)	1.81 (2)	2.6745 (14)	179 (2)
C15—H15B···Cg1ii	0.99	2.77	3.578 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.87 (2)	1.81 (2)	2.6745 (14)	179 (2)
C15—H15B⋯Cg1ii	0.99	2.77	3.578 (2)	140

Symmetry codes: (i) ; (ii) .