Isopropyl 2-[5-(4-hydroxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran-2-yl]acetate

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

doi:10.1107/S1600536809033492

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2267

doi:10.1107/S1600536809033492

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Isopropyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate

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 21 August 2009; accepted 22 August 2009; online 29 August 2009)

In the title compound, C₂₀H₂₀O₄S, the 4-hydroxyphenyl ring is rotated out of the plane of the benzofuran unit by 32.87 (8)°. The S—C_methyl 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 intermolecular 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_r = 356.42
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.111
S = 1.06
4158 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033492/bt5043sup1.cif

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

checkCIF report

Comment top

Hetero aromatic compounds containing the benzofuran skeleton have attracted particular interest in the view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999), and these compounds are occurring in natural products (Akgul & Anil, 2003; von Reuss & König, 2004). As a part of our ongoing studies of the effect of side chain substituents on the solid state structures of alkyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate analogues (Choi et al., 2006), the crystal structure of the title compound has been determined (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The 4-hydroxyphenyl ring is rotated out of the benzofuran plane, with a dihedral angle of 32.87 (8)°. The crystal packing (Fig. 2) is stabilized by intermolecular O–H···O and C–H···O hydrogen bonds; the first between the H atom of the hydroxy group and the oxygen of the C═O unit, with a O4–H4···O3ⁱ, the second between the methyl H atom of the methylsulfinyl substituent and the H atom of the hydroxy group, with a C13–H13B···O4ⁱⁱ, respectively (Table 1).

Related literature top

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 top

2-[5-(4-Hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetic acid (377 mg, 1.2 mmol) was added to a solution of concentrated sulfuric acid (3 drops) in isopropanol (15 ml), and the mixture was refluxed for 6h, then cooled. The solvent was evaporated and the residue was poured into water. The mixture was extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (benzene-acetone, 9:1 v/v) to afford the title compound as a colorless solid [yield 91%, m.p. 410-411 K; R_f = 0.51 (benzene-acetone, 9:1 v/v)]. Single crystals suitable for X–ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 cycles of arbitrary radius.
	Fig. 2. O–H···O and C–H···O interactions (dotted lines) in the title compound. [Symmetry codes: (i) - x + 1/2, y - 1/2, - z + 3/2; (ii) x - 1/2, - y + 3/2, z - 1/2 (iii) -x + 1/2, y + 1/2, - z+ 3/2.]

Isopropyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate top

Crystal data top

C₂₀H₂₀O₄S	F(000) = 1504
M_r = 356.42	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.5°, θ_min = 1.4°
ϕ and ω scans	h = −39→40
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −10→10
T_min = 0.916, T_max = 0.981	l = −19→19
15589 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)] = 0.042	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(F_o²) + (0.024P)² + 3.8686P] where P = (F_o² + 2F_c²)/3
4158 reflections	(Δ/σ)_max < 0.001
233 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₂₀O₄S	V = 3654.2 (5) Å³
M_r = 356.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 31.375 (3) Å	µ = 0.20 mm⁻¹
b = 8.0055 (7) Å	T = 173 K
c = 15.274 (1) Å	0.45 × 0.40 × 0.10 mm
β = 107.727 (1)°

Data collection top

Bruker SMART CCD diffractometer	4158 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2474 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.981	R_int = 0.051
15589 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
4158 reflections	Δρ_min = −0.25 e Å⁻³
233 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₄S
M_r	356.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	31.375 (3), 8.0055 (7), 15.274 (1)
β (°)	107.727 (1)
V (Å³)	3654.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.45 × 0.40 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.916, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	15589, 4158, 2474
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.06
No. of reflections	4158
No. of parameters	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.25

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O4—H4···O3ⁱ	0.81 (3)	2.02 (3)	2.829 (3)	171 (3)
C13—H13B···O4ⁱⁱ	0.96	2.57	3.325 (3)	135.3

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

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939–943. Web of Science CrossRef PubMed CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Kang, B. W., Seo, P. J., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o5121–o5122. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Reuss, S. H. von & König, W. A. (2004). Phytochemistry, 65, 3113–3118. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 9| September 2009| Page o2267

doi:10.1107/S1600536809033492

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Iso­propyl 2-[5-(4-hy­droxy­phen­yl)-3-methyl­sulfanyl-1-benzo­furan-2-yl]acetate

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organic compounds

Isopropyl 2-[5-(4-hydroxyphenyl)-3-methylsulfanyl-1-benzofuran-2-yl]acetate