2-Methyl-3-phenyl-sulfinyl-1-benzofuran.

The title compound, C(15)H(12)O(2)S, was prepared by the oxidation of 2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring makes a dihedral angle of 78.76 (4)° with the benzofuran mean plane. The crystal structure is stabilized by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 4.017 (3) Å]. In addition, the crystal structure exhibits inter-molecular C-H⋯π and C-H⋯O inter-actions.

Related literature

For the crystal structures of similar substituted benzofuran compounds, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C15H12O2S

M = 256.31

Monoclinic,

a = 12.946 (2) Å

b = 9.466 (1) Å

c = 10.294 (1) Å

β = 103.887 (2)°

V = 1224.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 173 (2) K

0.60 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

6763 measured reflections

2405 independent reflections

2192 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.11

2405 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.52 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/S1600536808021107/gk2156sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021107/gk2156Isup2.hkl

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

C15H12O2S	F000 = 536
Mr = 256.31	Dx = 1.390 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 5415 reflections
a = 12.946 (2) Å	θ = 2.7–28.2º
b = 9.466 (1) Å	µ = 0.25 mm−1
c = 10.294 (1) Å	T = 173 (2) K
β = 103.887 (2)º	Block, colorless
V = 1224.6 (3) Å3	0.60 × 0.40 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	2192 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 1.6º
φ and ω scans	h = −15→15
Absorption correction: none	k = −11→7
6763 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.4838P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
2405 reflections	Δρmax = 0.25 e Å−3
164 parameters	Δρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.21943 (3)	0.67373 (4)	0.24290 (4)	0.02584 (14)
O1	0.42892 (9)	0.63644 (14)	0.58590 (11)	0.0324 (3)
O2	0.23114 (10)	0.57743 (14)	0.13205 (11)	0.0372 (3)
C1	0.30363 (12)	0.61722 (17)	0.39339 (15)	0.0239 (3)
C2	0.31131 (11)	0.48127 (17)	0.45930 (14)	0.0244 (3)
C3	0.26168 (13)	0.35014 (17)	0.43207 (16)	0.0287 (3)
H3	0.2089	0.3341	0.3517	0.034*
C4	0.29212 (14)	0.24396 (19)	0.52657 (18)	0.0353 (4)
H4	0.2590	0.1540	0.5107	0.042*
C5	0.37026 (15)	0.2664 (2)	0.64428 (18)	0.0394 (4)
H5	0.3885	0.1916	0.7071	0.047*
C6	0.42179 (14)	0.3951 (2)	0.67166 (17)	0.0379 (4)
H6	0.4760	0.4104	0.7507	0.045*
C7	0.38969 (12)	0.49963 (19)	0.57741 (15)	0.0291 (4)
C8	0.37502 (12)	0.70491 (18)	0.47218 (15)	0.0277 (3)
C9	0.09419 (12)	0.62970 (16)	0.27953 (14)	0.0235 (3)
C10	0.02207 (13)	0.55290 (18)	0.18570 (16)	0.0317 (4)
H10	0.0412	0.5168	0.1086	0.038*
C11	−0.07920 (14)	0.5289 (2)	0.20534 (19)	0.0374 (4)
H11	−0.1296	0.4765	0.1412	0.045*
C12	−0.10656 (13)	0.58118 (19)	0.31772 (19)	0.0362 (4)
H12	−0.1759	0.5651	0.3306	0.043*
C13	−0.03302 (14)	0.65707 (19)	0.41178 (18)	0.0359 (4)
H13	−0.0519	0.6921	0.4894	0.043*
C14	0.06790 (13)	0.68229 (17)	0.39348 (16)	0.0295 (4)
H14	0.1183	0.7347	0.4578	0.035*
C15	0.40351 (14)	0.85446 (19)	0.45966 (19)	0.0364 (4)
H15A	0.3707	0.8880	0.3691	0.055*
H15B	0.4810	0.8633	0.4766	0.055*
H15C	0.3778	0.9113	0.5250	0.055*

	U11	U22	U33	U12	U13	U23
S	0.0309 (2)	0.0267 (2)	0.0210 (2)	−0.00105 (15)	0.00834 (16)	0.00241 (14)
O1	0.0259 (6)	0.0415 (7)	0.0281 (6)	−0.0028 (5)	0.0033 (5)	−0.0067 (5)
O2	0.0444 (7)	0.0478 (8)	0.0227 (6)	0.0018 (6)	0.0143 (5)	−0.0049 (5)
C1	0.0239 (7)	0.0266 (8)	0.0227 (7)	−0.0017 (6)	0.0083 (6)	−0.0008 (6)
C2	0.0223 (7)	0.0298 (8)	0.0225 (7)	0.0032 (6)	0.0082 (6)	0.0006 (6)
C3	0.0291 (8)	0.0281 (8)	0.0300 (8)	0.0009 (6)	0.0094 (6)	−0.0002 (6)
C4	0.0382 (9)	0.0290 (9)	0.0431 (9)	0.0080 (7)	0.0184 (8)	0.0058 (7)
C5	0.0419 (10)	0.0439 (11)	0.0363 (9)	0.0196 (8)	0.0171 (8)	0.0148 (8)
C6	0.0333 (9)	0.0535 (11)	0.0260 (8)	0.0157 (8)	0.0056 (7)	0.0036 (8)
C7	0.0244 (7)	0.0381 (9)	0.0260 (8)	0.0029 (7)	0.0082 (6)	−0.0034 (7)
C8	0.0234 (7)	0.0340 (9)	0.0278 (8)	−0.0023 (6)	0.0103 (6)	−0.0051 (7)
C9	0.0270 (8)	0.0215 (7)	0.0211 (7)	0.0020 (6)	0.0041 (6)	0.0024 (6)
C10	0.0346 (8)	0.0323 (9)	0.0257 (8)	0.0012 (7)	0.0026 (6)	−0.0051 (7)
C11	0.0301 (9)	0.0344 (9)	0.0422 (9)	−0.0027 (7)	−0.0023 (7)	−0.0063 (8)
C12	0.0264 (8)	0.0342 (9)	0.0480 (10)	0.0003 (7)	0.0086 (7)	0.0015 (8)
C13	0.0353 (9)	0.0392 (10)	0.0358 (9)	0.0014 (7)	0.0141 (7)	−0.0051 (7)
C14	0.0303 (8)	0.0317 (9)	0.0263 (8)	−0.0020 (6)	0.0062 (6)	−0.0061 (6)
C15	0.0356 (9)	0.0336 (9)	0.0441 (10)	−0.0114 (7)	0.0175 (8)	−0.0116 (8)

S—O2	1.496 (1)	C6—H6	0.9500
S—C1	1.750 (2)	C8—C15	1.476 (2)
S—C9	1.800 (2)	C9—C10	1.378 (2)
O1—C8	1.373 (2)	C9—C14	1.390 (2)
O1—C7	1.386 (2)	C10—C11	1.392 (2)
C1—C8	1.357 (2)	C10—H10	0.9500
C1—C2	1.447 (2)	C11—C12	1.380 (3)
C2—C3	1.395 (2)	C11—H11	0.9500
C2—C7	1.395 (2)	C12—C13	1.385 (3)
C3—C4	1.388 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.385 (2)
C4—C5	1.396 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.385 (3)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.378 (2)	C15—H15C	0.9800
O2—S—C1	109.46 (7)	C1—C8—C15	133.1 (2)
O2—S—C9	106.26 (7)	O1—C8—C15	116.1 (1)
C1—S—C9	98.33 (7)	C10—C9—C14	121.2 (2)
C8—O1—C7	106.5 (1)	C10—C9—S	117.9 (1)
C8—C1—C2	107.7 (1)	C14—C9—S	120.6 (1)
C8—C1—S	122.2 (1)	C9—C10—C11	119.2 (2)
C2—C1—S	130.2 (1)	C9—C10—H10	120.4
C3—C2—C7	119.2 (2)	C11—C10—H10	120.4
C3—C2—C1	136.1 (1)	C12—C11—C10	120.2 (2)
C7—C2—C1	104.6 (1)	C12—C11—H11	119.9
C4—C3—C2	117.6 (2)	C10—C11—H11	119.9
C4—C3—H3	121.2	C11—C12—C13	120.0 (2)
C2—C3—H3	121.2	C11—C12—H12	120.0
C3—C4—C5	121.5 (2)	C13—C12—H12	120.0
C3—C4—H4	119.2	C14—C13—C12	120.5 (2)
C5—C4—H4	119.2	C14—C13—H13	119.8
C6—C5—C4	121.6 (2)	C12—C13—H13	119.8
C6—C5—H5	119.2	C13—C14—C9	118.9 (2)
C4—C5—H5	119.2	C13—C14—H14	120.6
C7—C6—C5	116.1 (2)	C9—C14—H14	120.6
C7—C6—H6	122.0	C8—C15—H15A	109.5
C5—C6—H6	122.0	C8—C15—H15B	109.5
C6—C7—O1	125.6 (2)	H15A—C15—H15B	109.5
C6—C7—C2	123.9 (2)	C8—C15—H15C	109.5
O1—C7—C2	110.5 (1)	H15A—C15—H15C	109.5
C1—C8—O1	110.8 (2)	H15B—C15—H15C	109.5
O2—S—C1—C8	126.3 (1)	C1—C2—C7—O1	−0.1 (2)
C9—S—C1—C8	−123.2 (1)	C2—C1—C8—O1	−0.3 (2)
O2—S—C1—C2	−55.6 (2)	S—C1—C8—O1	178.2 (1)
C9—S—C1—C2	55.0 (2)	C2—C1—C8—C15	−179.5 (2)
C8—C1—C2—C3	−179.9 (2)	S—C1—C8—C15	−1.0 (3)
S—C1—C2—C3	1.7 (3)	C7—O1—C8—C1	0.3 (2)
C8—C1—C2—C7	0.2 (2)	C7—O1—C8—C15	179.6 (1)
S—C1—C2—C7	−178.1 (1)	O2—S—C9—C10	−17.0 (2)
C7—C2—C3—C4	1.1 (2)	C1—S—C9—C10	−130.2 (1)
C1—C2—C3—C4	−178.7 (2)	O2—S—C9—C14	168.5 (1)
C2—C3—C4—C5	−0.6 (2)	C1—S—C9—C14	55.3 (1)
C3—C4—C5—C6	−0.7 (3)	C14—C9—C10—C11	0.6 (2)
C4—C5—C6—C7	1.3 (2)	S—C9—C10—C11	−173.9 (1)
C5—C6—C7—O1	178.7 (1)	C9—C10—C11—C12	−0.2 (3)
C5—C6—C7—C2	−0.8 (2)	C10—C11—C12—C13	−0.3 (3)
C8—O1—C7—C6	−179.6 (2)	C11—C12—C13—C14	0.6 (3)
C8—O1—C7—C2	−0.1 (2)	C12—C13—C14—C9	−0.3 (3)
C3—C2—C7—C6	−0.4 (2)	C10—C9—C14—C13	−0.3 (2)
C1—C2—C7—C6	179.4 (2)	S—C9—C14—C13	174.0 (1)
C3—C2—C7—O1	−179.9 (1)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2i	0.95	2.59	3.387 (2)	142
C15—H15C···O2ii	0.98	2.42	3.232 (2)	141
C12—H12···Cg2iii	0.95	3.20	3.629 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2i	0.95	2.59	3.387 (2)	142
C15—H15C⋯O2ii	0.98	2.42	3.232 (2)	141
C12—H12⋯Cg2iii	0.95	3.20	3.629 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C2–C7 benzene ring.