Isopropyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran-2-yl]acetate.

In the title compound, C(20)H(20)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the plane of the benzofuran unit by 32.87 (8)°. The S-C(meth-yl) bond is almost perpendicular to the plane of the benzofuran fragment [77.8 (1)°] and is slightly tilted towards it. The crystal structure is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds.

Related literature

For the crystal structure of a similar alkyl 2-[5-(4-hydroxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran-2-yl]acetate derivative, see: Choi et al. (2006 ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products containing the benzofuran unit, see: Akgul & Anil (2003 ▶); von Reuss & König (2004 ▶).

Experimental

Crystal data

C20H20O4S

M = 356.42

Monoclinic,

a = 31.375 (3) Å

b = 8.0055 (7) Å

c = 15.274 (1) Å

β = 107.727 (1)°

V = 3654.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 173 K

0.45 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.916, T max = 0.981

15589 measured reflections

4158 independent reflections

2474 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.06

4158 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809033492/bt5043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033492/bt5043Isup2.hkl

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

C20H20O4S	F(000) = 1504
Mr = 356.42	Dx = 1.296 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4594 reflections
a = 31.375 (3) Å	θ = 2.6–27.3°
b = 8.0055 (7) Å	µ = 0.20 mm−1
c = 15.274 (1) Å	T = 173 K
β = 107.727 (1)°	Block, colorless
V = 3654.2 (5) Å3	0.45 × 0.40 × 0.10 mm
Z = 8

Bruker SMART CCD diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.4°
φ and ω scans	h = −39→40
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −10→10
Tmin = 0.916, Tmax = 0.981	l = −19→19
15589 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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.024P)2 + 3.8686P] where P = (Fo2 + 2Fc2)/3
4158 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.17 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
S	0.15080 (2)	0.69811 (7)	0.43431 (4)	0.0571 (2)
O1	0.11004 (5)	0.2623 (2)	0.49946 (11)	0.0540 (4)
O2	0.00249 (5)	0.6432 (2)	0.36507 (10)	0.0547 (4)
O3	0.04570 (5)	0.6124 (2)	0.51076 (10)	0.0588 (5)
O4	0.43182 (6)	0.2543 (2)	0.81139 (14)	0.0639 (5)
H4	0.4366 (11)	0.204 (4)	0.860 (2)	0.097 (12)*
C1	0.14460 (8)	0.4954 (3)	0.47235 (15)	0.0471 (6)
C2	0.17779 (8)	0.3928 (3)	0.53678 (14)	0.0430 (5)
C3	0.22327 (7)	0.4045 (3)	0.58158 (14)	0.0427 (5)
H3	0.2393	0.4973	0.5728	0.051*
C4	0.24484 (7)	0.2758 (3)	0.64005 (14)	0.0421 (5)
C5	0.21960 (8)	0.1362 (3)	0.65124 (16)	0.0501 (6)
H5	0.2341	0.0503	0.6899	0.060*
C6	0.17442 (8)	0.1219 (3)	0.60733 (16)	0.0531 (6)
H6	0.1582	0.0293	0.6156	0.064*
C7	0.15455 (8)	0.2522 (3)	0.55045 (16)	0.0475 (6)
C8	0.10569 (8)	0.4117 (3)	0.45225 (16)	0.0517 (6)
C9	0.06007 (8)	0.4503 (3)	0.39027 (16)	0.0571 (6)
H9A	0.0427	0.3480	0.3775	0.069*
H9B	0.0625	0.4924	0.3324	0.069*
C10	0.03578 (7)	0.5767 (3)	0.43027 (15)	0.0459 (5)
C11	−0.02201 (8)	0.7816 (3)	0.39016 (17)	0.0596 (7)
H11	−0.0251	0.7615	0.4512	0.072*
C12	−0.06727 (9)	0.7810 (4)	0.31955 (19)	0.0779 (9)
H12A	−0.0640	0.7979	0.2597	0.117*
H12B	−0.0852	0.8692	0.3327	0.117*
H12C	−0.0816	0.6756	0.3211	0.117*
C13	0.00498 (10)	0.9398 (4)	0.3919 (2)	0.0810 (9)
H13A	0.0336	0.9296	0.4379	0.121*
H13B	−0.0108	1.0337	0.4060	0.121*
H13C	0.0092	0.9561	0.3328	0.121*
C14	0.29366 (7)	0.2806 (2)	0.68845 (14)	0.0412 (5)
C15	0.31181 (8)	0.2046 (3)	0.77431 (15)	0.0482 (6)
H15	0.2927	0.1583	0.8037	0.058*
C16	0.35724 (8)	0.1966 (3)	0.81618 (15)	0.0489 (6)
H16	0.3684	0.1444	0.8730	0.059*
C17	0.38628 (8)	0.2652 (3)	0.77459 (15)	0.0462 (5)
C18	0.36918 (8)	0.3480 (3)	0.69133 (15)	0.0472 (5)
H18	0.3885	0.3992	0.6640	0.057*
C19	0.32372 (7)	0.3543 (2)	0.64927 (14)	0.0429 (5)
H19	0.3128	0.4091	0.5932	0.051*
C20	0.18438 (10)	0.6628 (3)	0.3595 (2)	0.0753 (8)
H20A	0.2132	0.6210	0.3947	0.113*
H20B	0.1880	0.7659	0.3306	0.113*
H20C	0.1699	0.5825	0.3134	0.113*

	U11	U22	U33	U12	U13	U23
S	0.0746 (5)	0.0372 (3)	0.0542 (4)	0.0154 (3)	0.0118 (3)	0.0026 (3)
O1	0.0501 (10)	0.0527 (10)	0.0582 (10)	0.0071 (8)	0.0151 (8)	0.0052 (8)
O2	0.0574 (10)	0.0634 (10)	0.0371 (8)	0.0202 (8)	0.0051 (7)	−0.0031 (7)
O3	0.0536 (10)	0.0758 (12)	0.0392 (9)	0.0075 (9)	0.0023 (8)	−0.0064 (8)
O4	0.0525 (11)	0.0710 (12)	0.0578 (12)	−0.0048 (9)	0.0013 (9)	0.0086 (10)
C1	0.0551 (15)	0.0395 (12)	0.0441 (13)	0.0103 (11)	0.0113 (11)	−0.0003 (10)
C2	0.0521 (14)	0.0363 (11)	0.0416 (12)	0.0091 (10)	0.0157 (10)	0.0003 (9)
C3	0.0533 (14)	0.0339 (11)	0.0420 (12)	0.0062 (10)	0.0162 (11)	0.0003 (9)
C4	0.0509 (13)	0.0382 (11)	0.0396 (12)	0.0093 (10)	0.0176 (10)	0.0027 (9)
C5	0.0528 (15)	0.0460 (13)	0.0554 (14)	0.0114 (11)	0.0223 (12)	0.0146 (11)
C6	0.0553 (16)	0.0467 (13)	0.0628 (15)	0.0053 (11)	0.0262 (13)	0.0137 (12)
C7	0.0440 (14)	0.0493 (13)	0.0505 (13)	0.0080 (10)	0.0162 (11)	0.0023 (11)
C8	0.0576 (16)	0.0459 (13)	0.0490 (14)	0.0128 (12)	0.0124 (12)	−0.0014 (11)
C9	0.0569 (15)	0.0560 (15)	0.0518 (14)	0.0118 (12)	0.0066 (12)	−0.0075 (12)
C10	0.0420 (13)	0.0497 (13)	0.0405 (13)	0.0015 (10)	0.0043 (10)	−0.0011 (10)
C11	0.0624 (16)	0.0686 (17)	0.0468 (14)	0.0251 (14)	0.0150 (12)	−0.0004 (12)
C12	0.0672 (19)	0.096 (2)	0.0622 (17)	0.0311 (17)	0.0075 (14)	0.0046 (16)
C13	0.092 (2)	0.0672 (19)	0.078 (2)	0.0169 (17)	0.0178 (18)	−0.0034 (15)
C14	0.0531 (14)	0.0326 (11)	0.0390 (11)	0.0071 (10)	0.0154 (10)	0.0007 (9)
C15	0.0576 (15)	0.0453 (12)	0.0441 (12)	0.0056 (11)	0.0190 (11)	0.0084 (11)
C16	0.0592 (15)	0.0457 (13)	0.0381 (12)	0.0053 (11)	0.0090 (11)	0.0048 (10)
C17	0.0494 (14)	0.0392 (12)	0.0444 (12)	0.0006 (10)	0.0059 (11)	−0.0040 (10)
C18	0.0560 (15)	0.0417 (12)	0.0447 (13)	−0.0034 (11)	0.0164 (11)	−0.0004 (10)
C19	0.0558 (15)	0.0349 (11)	0.0373 (11)	0.0057 (10)	0.0133 (11)	0.0033 (9)
C20	0.099 (2)	0.0535 (16)	0.0803 (19)	0.0075 (15)	0.0382 (18)	0.0049 (14)

S—C1	1.754 (2)	C9—H9B	0.9700
S—C20	1.796 (3)	C11—C12	1.499 (3)
O1—C7	1.379 (3)	C11—C13	1.519 (4)
O1—C8	1.381 (3)	C11—H11	0.9800
O2—C10	1.316 (3)	C12—H12A	0.9600
O2—C11	1.465 (3)	C12—H12B	0.9600
O3—C10	1.207 (2)	C12—H12C	0.9600
O4—C17	1.370 (3)	C13—H13A	0.9600
O4—H4	0.81 (3)	C13—H13B	0.9600
C1—C8	1.344 (3)	C13—H13C	0.9600
C1—C2	1.450 (3)	C14—C19	1.393 (3)
C2—C3	1.385 (3)	C14—C15	1.400 (3)
C2—C7	1.391 (3)	C15—C16	1.374 (3)
C3—C4	1.396 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.374 (3)
C4—C5	1.409 (3)	C16—H16	0.9300
C4—C14	1.485 (3)	C17—C18	1.389 (3)
C5—C6	1.376 (3)	C18—C19	1.375 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.379 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—H20A	0.9600
C8—C9	1.489 (3)	C20—H20B	0.9600
C9—C10	1.504 (3)	C20—H20C	0.9600
C9—H9A	0.9700
C1—S—C20	102.15 (11)	O2—C11—H11	109.7
C7—O1—C8	105.56 (18)	C12—C11—H11	109.7
C10—O2—C11	117.84 (17)	C13—C11—H11	109.7
C17—O4—H4	106 (2)	C11—C12—H12A	109.5
C8—C1—C2	106.7 (2)	C11—C12—H12B	109.5
C8—C1—S	124.77 (18)	H12A—C12—H12B	109.5
C2—C1—S	128.29 (18)	C11—C12—H12C	109.5
C3—C2—C7	119.2 (2)	H12A—C12—H12C	109.5
C3—C2—C1	135.7 (2)	H12B—C12—H12C	109.5
C7—C2—C1	105.0 (2)	C11—C13—H13A	109.5
C2—C3—C4	119.5 (2)	C11—C13—H13B	109.5
C2—C3—H3	120.3	H13A—C13—H13B	109.5
C4—C3—H3	120.3	C11—C13—H13C	109.5
C3—C4—C5	118.8 (2)	H13A—C13—H13C	109.5
C3—C4—C14	121.7 (2)	H13B—C13—H13C	109.5
C5—C4—C14	119.53 (19)	C19—C14—C15	116.8 (2)
C6—C5—C4	122.7 (2)	C19—C14—C4	121.87 (19)
C6—C5—H5	118.6	C15—C14—C4	121.2 (2)
C4—C5—H5	118.6	C16—C15—C14	121.6 (2)
C5—C6—C7	116.4 (2)	C16—C15—H15	119.2
C5—C6—H6	121.8	C14—C15—H15	119.2
C7—C6—H6	121.8	C17—C16—C15	120.4 (2)
O1—C7—C6	125.9 (2)	C17—C16—H16	119.8
O1—C7—C2	110.76 (19)	C15—C16—H16	119.8
C6—C7—C2	123.3 (2)	O4—C17—C16	122.7 (2)
C1—C8—O1	112.0 (2)	O4—C17—C18	118.0 (2)
C1—C8—C9	132.3 (2)	C16—C17—C18	119.2 (2)
O1—C8—C9	115.8 (2)	C19—C18—C17	120.1 (2)
C8—C9—C10	112.92 (19)	C19—C18—H18	119.9
C8—C9—H9A	109.0	C17—C18—H18	119.9
C10—C9—H9A	109.0	C18—C19—C14	121.7 (2)
C8—C9—H9B	109.0	C18—C19—H19	119.2
C10—C9—H9B	109.0	C14—C19—H19	119.2
H9A—C9—H9B	107.8	S—C20—H20A	109.5
O3—C10—O2	125.0 (2)	S—C20—H20B	109.5
O3—C10—C9	124.6 (2)	H20A—C20—H20B	109.5
O2—C10—C9	110.39 (19)	S—C20—H20C	109.5
O2—C11—C12	105.5 (2)	H20A—C20—H20C	109.5
O2—C11—C13	107.5 (2)	H20B—C20—H20C	109.5
C12—C11—C13	114.6 (2)
C20—S—C1—C8	−113.8 (2)	C7—O1—C8—C1	−1.1 (2)
C20—S—C1—C2	72.8 (2)	C7—O1—C8—C9	179.05 (19)
C8—C1—C2—C3	178.3 (2)	C1—C8—C9—C10	−77.0 (3)
S—C1—C2—C3	−7.3 (4)	O1—C8—C9—C10	102.7 (2)
C8—C1—C2—C7	−0.6 (2)	C11—O2—C10—O3	5.8 (4)
S—C1—C2—C7	173.76 (17)	C11—O2—C10—C9	−173.8 (2)
C7—C2—C3—C4	−0.5 (3)	C8—C9—C10—O3	−18.4 (4)
C1—C2—C3—C4	−179.3 (2)	C8—C9—C10—O2	161.2 (2)
C2—C3—C4—C5	0.5 (3)	C10—O2—C11—C12	−155.9 (2)
C2—C3—C4—C14	178.91 (19)	C10—O2—C11—C13	81.4 (3)
C3—C4—C5—C6	−0.4 (3)	C3—C4—C14—C19	−33.2 (3)
C14—C4—C5—C6	−178.9 (2)	C5—C4—C14—C19	145.2 (2)
C4—C5—C6—C7	0.3 (3)	C3—C4—C14—C15	149.6 (2)
C8—O1—C7—C6	−178.9 (2)	C5—C4—C14—C15	−32.0 (3)
C8—O1—C7—C2	0.7 (2)	C19—C14—C15—C16	−2.7 (3)
C5—C6—C7—O1	179.3 (2)	C4—C14—C15—C16	174.6 (2)
C5—C6—C7—C2	−0.3 (3)	C14—C15—C16—C17	0.6 (3)
C3—C2—C7—O1	−179.24 (18)	C15—C16—C17—O4	−177.1 (2)
C1—C2—C7—O1	−0.1 (2)	C15—C16—C17—C18	2.3 (3)
C3—C2—C7—C6	0.4 (3)	O4—C17—C18—C19	176.5 (2)
C1—C2—C7—C6	179.5 (2)	C16—C17—C18—C19	−2.9 (3)
C2—C1—C8—O1	1.1 (3)	C17—C18—C19—C14	0.7 (3)
S—C1—C8—O1	−173.51 (15)	C15—C14—C19—C18	2.1 (3)
C2—C1—C8—C9	−179.1 (2)	C4—C14—C19—C18	−175.23 (19)
S—C1—C8—C9	6.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.81 (3)	2.02 (3)	2.829 (3)	171 (3)
C13—H13B···O4ii	0.96	2.57	3.325 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.81 (3)	2.02 (3)	2.829 (3)	171 (3)
C13—H13B⋯O4ii	0.96	2.57	3.325 (3)	135

Symmetry codes: (i) ; (ii) .