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

In the title compound, C(18)H(16)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52 (6)°. The methyl group of the methyl-sulfanyl substituent is almost perpendicular to the plane of the benzofuran fragment [100.90 (8)°] and is slightly tilted towards it. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds, and by inter-molecular C-H⋯π inter-actions between a methyl H atom of the methyl-sulfanyl substituent and the 4-hydroxy-phenyl ring.

Related literature

For the crystal structures of similar alkyl 2-[5-(4-hydroxy­phen­yl)-3-methyl­sulfanyl-1-benzofuran-2-yl]acetate derivatives, see: Choi et al. (2006 ▶, 2009 ▶). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products involving a benzofuran ring, see: Akgul & Anil (2003 ▶); von Reuss & König (2004 ▶).

Experimental

Crystal data

C18H16O4S

M = 328.37

Monoclinic,

a = 13.6661 (6) Å

b = 7.6643 (3) Å

c = 15.6344 (7) Å

β = 95.4731 (6)°

V = 1630.10 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.45 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.940, T max = 0.961

13917 measured reflections

3703 independent reflections

2894 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.097

S = 1.08

3703 reflections

213 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 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/S1600536809037763/si2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037763/si2201Isup2.hkl

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

C18H16O4S	F(000) = 688
Mr = 328.37	Dx = 1.338 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6226 reflections
a = 13.6661 (6) Å	θ = 2.6–27.3°
b = 7.6643 (3) Å	µ = 0.22 mm−1
c = 15.6344 (7) Å	T = 173 K
β = 95.4731 (6)°	Block, colorless
V = 1630.10 (12) Å3	0.45 × 0.25 × 0.25 mm
Z = 4

Bruker SMART CCD diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	2894 reflections with I > 2σ(I)
graphite	Rint = 0.046
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 1.5°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −9→9
Tmin = 0.940, Tmax = 0.961	l = −20→20
13917 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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.038P)2 + 0.664P] where P = (Fo2 + 2Fc2)/3
3703 reflections	(Δ/σ)max < 0.001
213 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.25 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	0.69956 (3)	0.01335 (5)	0.51042 (3)	0.02878 (12)
O1	0.80580 (8)	0.44720 (15)	0.62041 (7)	0.0290 (3)
O2	1.05303 (8)	0.08785 (16)	0.60370 (7)	0.0330 (3)
O3	0.94920 (8)	0.15452 (18)	0.70121 (8)	0.0379 (3)
O4	0.09318 (9)	0.48769 (18)	0.64861 (9)	0.0377 (3)
H4	0.0789 (17)	0.535 (3)	0.6922 (17)	0.061 (8)*
C1	0.72205 (11)	0.2164 (2)	0.55937 (9)	0.0244 (3)
C2	0.65254 (11)	0.33024 (19)	0.59592 (9)	0.0227 (3)
C3	0.55110 (11)	0.3275 (2)	0.60033 (9)	0.0229 (3)
H3	0.5133	0.2362	0.5759	0.027*
C4	0.50698 (11)	0.4634 (2)	0.64192 (9)	0.0236 (3)
C5	0.56623 (11)	0.6008 (2)	0.67804 (10)	0.0277 (3)
H5	0.5365	0.6911	0.7057	0.033*
C6	0.66711 (12)	0.6063 (2)	0.67373 (10)	0.0291 (3)
H6	0.7054	0.6977	0.6974	0.035*
C7	0.70754 (11)	0.4684 (2)	0.63246 (10)	0.0254 (3)
C8	0.81116 (11)	0.2933 (2)	0.57520 (10)	0.0268 (3)
C9	0.91070 (11)	0.2406 (2)	0.55381 (10)	0.0289 (3)
H9A	0.9450	0.3428	0.5354	0.035*
H9B	0.9040	0.1591	0.5062	0.035*
C10	0.97139 (11)	0.1573 (2)	0.62834 (10)	0.0266 (3)
C11	1.11920 (14)	0.0120 (3)	0.67179 (13)	0.0460 (5)
H11A	1.0857	−0.0787	0.6997	0.055*
H11B	1.1403	0.1006	0.7129	0.055*
H11C	1.1754	−0.0362	0.6478	0.055*
C12	0.39861 (11)	0.46601 (19)	0.64631 (10)	0.0227 (3)
C13	0.33451 (11)	0.4013 (2)	0.57879 (10)	0.0246 (3)
H13	0.3604	0.3531	0.5312	0.030*
C14	0.23358 (12)	0.4071 (2)	0.58084 (10)	0.0272 (3)
H14	0.1925	0.3618	0.5354	0.033*
C15	0.19364 (11)	0.4809 (2)	0.65104 (10)	0.0267 (3)
C16	0.25574 (12)	0.5440 (2)	0.71976 (10)	0.0289 (3)
H16	0.2296	0.5919	0.7673	0.035*
C17	0.35686 (12)	0.5352 (2)	0.71715 (10)	0.0273 (3)
H17	0.3979	0.5765	0.7637	0.033*
C18	0.62715 (13)	0.0771 (2)	0.41243 (12)	0.0365 (4)
H18A	0.5645	0.1201	0.4260	0.055*
H18B	0.6176	−0.0220	0.3750	0.055*
H18C	0.6610	0.1671	0.3843	0.055*

	U11	U22	U33	U12	U13	U23
S1	0.0320 (2)	0.0222 (2)	0.0323 (2)	0.00435 (16)	0.00399 (16)	−0.00155 (16)
O1	0.0219 (5)	0.0333 (6)	0.0313 (6)	0.0002 (5)	0.0002 (4)	−0.0056 (5)
O2	0.0240 (6)	0.0455 (7)	0.0299 (6)	0.0094 (5)	0.0041 (4)	0.0007 (5)
O3	0.0297 (6)	0.0546 (8)	0.0309 (6)	0.0048 (6)	0.0105 (5)	0.0091 (6)
O4	0.0244 (6)	0.0501 (8)	0.0394 (7)	−0.0021 (5)	0.0082 (5)	−0.0150 (6)
C1	0.0250 (8)	0.0242 (7)	0.0241 (7)	0.0036 (6)	0.0028 (6)	0.0005 (6)
C2	0.0246 (7)	0.0218 (7)	0.0218 (7)	0.0030 (6)	0.0023 (6)	0.0008 (6)
C3	0.0238 (7)	0.0210 (7)	0.0239 (7)	0.0001 (6)	0.0020 (6)	−0.0002 (6)
C4	0.0253 (7)	0.0241 (8)	0.0212 (7)	0.0030 (6)	0.0011 (6)	0.0011 (6)
C5	0.0279 (8)	0.0268 (8)	0.0277 (8)	0.0059 (6)	−0.0004 (6)	−0.0059 (6)
C6	0.0299 (8)	0.0275 (8)	0.0289 (8)	−0.0013 (7)	−0.0031 (6)	−0.0064 (6)
C7	0.0210 (7)	0.0300 (8)	0.0246 (8)	0.0020 (6)	−0.0006 (6)	−0.0003 (6)
C8	0.0259 (8)	0.0305 (8)	0.0240 (7)	0.0033 (6)	0.0019 (6)	−0.0001 (6)
C9	0.0227 (8)	0.0370 (9)	0.0274 (8)	0.0022 (7)	0.0039 (6)	0.0001 (7)
C10	0.0204 (7)	0.0295 (8)	0.0304 (8)	−0.0025 (6)	0.0055 (6)	−0.0002 (6)
C11	0.0311 (9)	0.0670 (14)	0.0392 (10)	0.0158 (9)	0.0007 (8)	0.0111 (10)
C12	0.0255 (7)	0.0190 (7)	0.0238 (7)	0.0035 (6)	0.0033 (6)	0.0010 (6)
C13	0.0290 (8)	0.0223 (7)	0.0232 (7)	0.0026 (6)	0.0061 (6)	−0.0021 (6)
C14	0.0279 (8)	0.0276 (8)	0.0257 (8)	−0.0010 (6)	0.0006 (6)	−0.0038 (6)
C15	0.0240 (7)	0.0268 (8)	0.0299 (8)	0.0001 (6)	0.0057 (6)	−0.0007 (6)
C16	0.0311 (8)	0.0314 (8)	0.0252 (8)	0.0018 (7)	0.0080 (6)	−0.0054 (7)
C17	0.0295 (8)	0.0284 (8)	0.0239 (8)	0.0017 (6)	0.0015 (6)	−0.0039 (6)
C18	0.0385 (10)	0.0337 (9)	0.0361 (9)	0.0017 (8)	−0.0020 (7)	−0.0023 (7)

S1—C1	1.7488 (16)	C8—C9	1.487 (2)
S1—C18	1.8099 (18)	C9—C10	1.506 (2)
O1—C8	1.3810 (19)	C9—H9A	0.9700
O1—C7	1.3833 (18)	C9—H9B	0.9700
O2—C10	1.3260 (18)	C11—H11A	0.9600
O2—C11	1.451 (2)	C11—H11B	0.9600
O3—C10	1.2067 (19)	C11—H11C	0.9600
O4—C15	1.3708 (19)	C12—C13	1.397 (2)
O4—H4	0.81 (3)	C12—C17	1.398 (2)
C1—C8	1.354 (2)	C13—C14	1.383 (2)
C1—C2	1.447 (2)	C13—H13	0.9300
C2—C7	1.390 (2)	C14—C15	1.392 (2)
C2—C3	1.395 (2)	C14—H14	0.9300
C3—C4	1.395 (2)	C15—C16	1.391 (2)
C3—H3	0.9300	C16—C17	1.388 (2)
C4—C5	1.413 (2)	C16—H16	0.9300
C4—C12	1.489 (2)	C17—H17	0.9300
C5—C6	1.387 (2)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.380 (2)	C18—H18C	0.9600
C6—H6	0.9300
C1—S1—C18	100.90 (8)	O3—C10—O2	124.16 (15)
C8—O1—C7	105.64 (12)	O3—C10—C9	124.63 (14)
C10—O2—C11	115.50 (13)	O2—C10—C9	111.21 (13)
C15—O4—H4	108.3 (17)	O2—C11—H11A	109.5
C8—C1—C2	106.18 (14)	O2—C11—H11B	109.5
C8—C1—S1	125.76 (12)	H11A—C11—H11B	109.5
C2—C1—S1	127.94 (12)	O2—C11—H11C	109.5
C7—C2—C3	119.49 (14)	H11A—C11—H11C	109.5
C7—C2—C1	105.79 (13)	H11B—C11—H11C	109.5
C3—C2—C1	134.71 (14)	C13—C12—C17	117.36 (14)
C2—C3—C4	119.18 (14)	C13—C12—C4	121.01 (13)
C2—C3—H3	120.4	C17—C12—C4	121.63 (14)
C4—C3—H3	120.4	C14—C13—C12	121.72 (14)
C3—C4—C5	119.09 (14)	C14—C13—H13	119.1
C3—C4—C12	120.49 (14)	C12—C13—H13	119.1
C5—C4—C12	120.41 (13)	C13—C14—C15	119.89 (14)
C6—C5—C4	122.50 (14)	C13—C14—H14	120.1
C6—C5—H5	118.8	C15—C14—H14	120.1
C4—C5—H5	118.8	O4—C15—C16	122.95 (14)
C7—C6—C5	116.33 (15)	O4—C15—C14	117.44 (14)
C7—C6—H6	121.8	C16—C15—C14	119.61 (14)
C5—C6—H6	121.8	C17—C16—C15	119.76 (14)
C6—C7—O1	126.20 (14)	C17—C16—H16	120.1
C6—C7—C2	123.41 (14)	C15—C16—H16	120.1
O1—C7—C2	110.39 (13)	C16—C17—C12	121.63 (15)
C1—C8—O1	111.98 (13)	C16—C17—H17	119.2
C1—C8—C9	131.83 (15)	C12—C17—H17	119.2
O1—C8—C9	116.18 (14)	S1—C18—H18A	109.5
C8—C9—C10	112.89 (13)	S1—C18—H18B	109.5
C8—C9—H9A	109.0	H18A—C18—H18B	109.5
C10—C9—H9A	109.0	S1—C18—H18C	109.5
C8—C9—H9B	109.0	H18A—C18—H18C	109.5
C10—C9—H9B	109.0	H18B—C18—H18C	109.5
H9A—C9—H9B	107.8
C18—S1—C1—C8	−114.97 (15)	S1—C1—C8—C9	3.7 (3)
C18—S1—C1—C2	69.48 (15)	C7—O1—C8—C1	−0.77 (17)
C8—C1—C2—C7	−0.71 (17)	C7—O1—C8—C9	179.94 (13)
S1—C1—C2—C7	175.53 (12)	C1—C8—C9—C10	−99.8 (2)
C8—C1—C2—C3	178.91 (17)	O1—C8—C9—C10	79.33 (18)
S1—C1—C2—C3	−4.8 (3)	C11—O2—C10—O3	−2.6 (2)
C7—C2—C3—C4	−0.4 (2)	C11—O2—C10—C9	176.96 (15)
C1—C2—C3—C4	−179.96 (16)	C8—C9—C10—O3	−10.1 (2)
C2—C3—C4—C5	0.4 (2)	C8—C9—C10—O2	170.26 (14)
C2—C3—C4—C12	178.85 (13)	C3—C4—C12—C13	−34.2 (2)
C3—C4—C5—C6	0.1 (2)	C5—C4—C12—C13	144.26 (15)
C12—C4—C5—C6	−178.41 (14)	C3—C4—C12—C17	146.78 (15)
C4—C5—C6—C7	−0.5 (2)	C5—C4—C12—C17	−34.8 (2)
C5—C6—C7—O1	179.75 (14)	C17—C12—C13—C14	0.8 (2)
C5—C6—C7—C2	0.5 (2)	C4—C12—C13—C14	−178.21 (14)
C8—O1—C7—C6	−179.09 (15)	C12—C13—C14—C15	0.8 (2)
C8—O1—C7—C2	0.28 (17)	C13—C14—C15—O4	178.18 (15)
C3—C2—C7—C6	0.0 (2)	C13—C14—C15—C16	−1.8 (2)
C1—C2—C7—C6	179.65 (15)	O4—C15—C16—C17	−178.96 (16)
C3—C2—C7—O1	−179.43 (13)	C14—C15—C16—C17	1.0 (2)
C1—C2—C7—O1	0.26 (17)	C15—C16—C17—C12	0.8 (3)
C2—C1—C8—O1	0.92 (18)	C13—C12—C17—C16	−1.7 (2)
S1—C1—C8—O1	−175.42 (11)	C4—C12—C17—C16	177.40 (15)
C2—C1—C8—C9	−179.93 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.81 (3)	1.97 (3)	2.7826 (18)	177 (2)
C18—H18C···Cgii	0.96	2.88	3.762 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.81 (3)	1.97 (3)	2.7826 (18)	177 (2)
C18—H18C⋯Cgii	0.96	2.88	3.762 (2)	153

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C12–C17 phenyl ring.