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

The title compound, C(15)H(12)O(2)S, was prepared by the oxidation of 3-methyl-sulfanyl-2-phenyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 37.65 (8)° with the plane of the benzofuran fragment. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.549 (2) Å] and by inter-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 3-methyl­sulfinyl-2-phenyl-1-benzofuran compounds, see: Choi et al. (2007a ▶,b ▶).

Experimental

Crystal data

C15H12O2S

M = 256.32

Triclinic,

a = 8.0185 (8) Å

b = 9.4381 (9) Å

c = 9.7749 (9) Å

α = 115.574 (2)°

β = 109.179 (2)°

γ = 94.296 (2)°

V = 609.51 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 173 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

3185 measured reflections

2120 independent reflections

1878 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.10

2120 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.24 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/S1600536808024276/pk2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024276/pk2109Isup2.hkl

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

C15H12O2S	Z = 2
Mr = 256.32	F000 = 268
Triclinic, P1	Dx = 1.397 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.0185 (8) Å	Cell parameters from 2383 reflections
b = 9.4381 (9) Å	θ = 2.5–28.2º
c = 9.7749 (9) Å	µ = 0.26 mm−1
α = 115.574 (2)º	T = 173 (2) K
β = 109.179 (2)º	Block, colorless
γ = 94.296 (2)º	0.30 × 0.10 × 0.10 mm
V = 609.51 (10) Å3

Bruker SMART CCD diffractometer	2120 independent reflections
Radiation source: fine-focus sealed tube	1878 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 25.0º
T = 173(2) K	θmin = 2.5º
φ and ω scans	h = −8→9
Absorption correction: none	k = −11→11
3185 measured reflections	l = −11→5

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0341P)2 + 0.3746P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2120 reflections	Δρmax = 0.32 e Å−3
164 parameters	Δρmin = −0.24 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	0.33893 (6)	0.23694 (6)	0.35764 (6)	0.02368 (16)
O1	−0.05250 (18)	−0.15771 (15)	0.17293 (16)	0.0238 (3)
O2	0.4116 (2)	0.33041 (18)	0.54205 (18)	0.0356 (4)
C1	0.1412 (3)	0.0880 (2)	0.2927 (2)	0.0210 (4)
C2	0.0021 (3)	0.1096 (2)	0.3590 (2)	0.0219 (4)
C3	−0.0353 (3)	0.2390 (3)	0.4755 (3)	0.0280 (5)
H3	0.0420	0.3457	0.5336	0.034*
C4	−0.1883 (3)	0.2063 (3)	0.5031 (3)	0.0321 (5)
H4	−0.2170	0.2928	0.5807	0.039*
C5	−0.3018 (3)	0.0500 (3)	0.4202 (3)	0.0326 (5)
H5	−0.4060	0.0329	0.4425	0.039*
C6	−0.2666 (3)	−0.0807 (3)	0.3064 (3)	0.0291 (5)
H6	−0.3429	−0.1877	0.2500	0.035*
C7	−0.1131 (3)	−0.0453 (2)	0.2802 (2)	0.0226 (4)
C8	0.1044 (2)	−0.0725 (2)	0.1847 (2)	0.0212 (4)
C9	0.1918 (3)	−0.1716 (2)	0.0813 (2)	0.0221 (4)
C10	0.1916 (3)	−0.3292 (2)	0.0565 (3)	0.0299 (5)
H10	0.1393	−0.3695	0.1110	0.036*
C11	0.2669 (3)	−0.4265 (3)	−0.0468 (3)	0.0370 (5)
H11	0.2666	−0.5331	−0.0624	0.044*
C12	0.3428 (3)	−0.3693 (3)	−0.1276 (3)	0.0364 (5)
H12	0.3931	−0.4370	−0.1995	0.044*
C13	0.3451 (3)	−0.2136 (3)	−0.1033 (3)	0.0315 (5)
H13	0.3986	−0.1738	−0.1575	0.038*
C14	0.2695 (3)	−0.1150 (2)	0.0000 (2)	0.0255 (4)
H14	0.2707	−0.0083	0.0154	0.031*
C15	0.2300 (3)	0.3619 (3)	0.2805 (3)	0.0352 (5)
H15A	0.1334	0.3896	0.3203	0.053*
H15B	0.1768	0.3027	0.1592	0.053*
H15C	0.3203	0.4616	0.3200	0.053*

	U11	U22	U33	U12	U13	U23
S	0.0189 (3)	0.0221 (3)	0.0235 (3)	0.00303 (19)	0.0068 (2)	0.0072 (2)
O1	0.0233 (7)	0.0214 (7)	0.0253 (7)	0.0042 (5)	0.0117 (6)	0.0089 (6)
O2	0.0311 (8)	0.0359 (9)	0.0232 (8)	−0.0025 (7)	0.0057 (7)	0.0058 (7)
C1	0.0201 (10)	0.0212 (10)	0.0202 (10)	0.0065 (8)	0.0080 (8)	0.0088 (8)
C2	0.0204 (10)	0.0264 (10)	0.0206 (10)	0.0093 (8)	0.0080 (8)	0.0122 (9)
C3	0.0305 (11)	0.0281 (11)	0.0246 (11)	0.0125 (9)	0.0107 (9)	0.0116 (9)
C4	0.0357 (12)	0.0421 (13)	0.0277 (11)	0.0238 (10)	0.0181 (10)	0.0185 (10)
C5	0.0303 (12)	0.0506 (14)	0.0401 (13)	0.0229 (10)	0.0236 (10)	0.0324 (12)
C6	0.0256 (11)	0.0365 (12)	0.0348 (12)	0.0106 (9)	0.0138 (9)	0.0235 (10)
C7	0.0234 (10)	0.0275 (10)	0.0213 (10)	0.0105 (8)	0.0112 (8)	0.0132 (9)
C8	0.0187 (9)	0.0235 (10)	0.0208 (10)	0.0035 (8)	0.0067 (8)	0.0113 (8)
C9	0.0198 (9)	0.0214 (10)	0.0181 (10)	0.0034 (8)	0.0056 (8)	0.0055 (8)
C10	0.0334 (12)	0.0255 (11)	0.0309 (12)	0.0068 (9)	0.0163 (10)	0.0113 (9)
C11	0.0423 (13)	0.0239 (11)	0.0400 (14)	0.0113 (10)	0.0199 (11)	0.0085 (10)
C12	0.0317 (12)	0.0366 (13)	0.0305 (12)	0.0101 (10)	0.0167 (10)	0.0041 (10)
C13	0.0254 (11)	0.0409 (12)	0.0227 (11)	0.0036 (9)	0.0114 (9)	0.0104 (9)
C14	0.0235 (10)	0.0277 (11)	0.0213 (10)	0.0048 (8)	0.0070 (8)	0.0103 (9)
C15	0.0292 (11)	0.0263 (11)	0.0451 (14)	0.0039 (9)	0.0081 (10)	0.0186 (11)

S—O2	1.492 (2)	C6—H6	0.9500
S—C1	1.769 (2)	C8—C9	1.461 (3)
S—C15	1.792 (2)	C9—C14	1.396 (3)
O1—C7	1.384 (2)	C9—C10	1.400 (3)
O1—C8	1.384 (2)	C10—C11	1.382 (3)
C1—C8	1.358 (3)	C10—H10	0.9500
C1—C2	1.449 (3)	C11—C12	1.386 (3)
C2—C7	1.394 (3)	C11—H11	0.9500
C2—C3	1.398 (3)	C12—C13	1.382 (3)
C3—C4	1.381 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.389 (3)
C4—C5	1.394 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.383 (3)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—C7	1.383 (3)	C15—H15C	0.9800
O2—S—C1	106.42 (9)	C1—C8—C9	134.62 (17)
O2—S—C15	107.19 (10)	O1—C8—C9	114.80 (16)
C1—S—C15	98.28 (10)	C14—C9—C10	118.74 (18)
C7—O1—C8	106.40 (14)	C14—C9—C8	121.25 (17)
C8—C1—C2	107.57 (17)	C10—C9—C8	119.95 (18)
C8—C1—S	125.35 (15)	C11—C10—C9	120.4 (2)
C2—C1—S	126.67 (14)	C11—C10—H10	119.8
C7—C2—C3	118.79 (18)	C9—C10—H10	119.8
C7—C2—C1	104.81 (16)	C10—C11—C12	120.3 (2)
C3—C2—C1	136.38 (19)	C10—C11—H11	119.8
C4—C3—C2	117.8 (2)	C12—C11—H11	119.8
C4—C3—H3	121.1	C13—C12—C11	119.9 (2)
C2—C3—H3	121.1	C13—C12—H12	120.1
C3—C4—C5	121.8 (2)	C11—C12—H12	120.1
C3—C4—H4	119.1	C12—C13—C14	120.2 (2)
C5—C4—H4	119.1	C12—C13—H13	119.9
C6—C5—C4	121.76 (19)	C14—C13—H13	119.9
C6—C5—H5	119.1	C13—C14—C9	120.40 (19)
C4—C5—H5	119.1	C13—C14—H14	119.8
C7—C6—C5	115.5 (2)	C9—C14—H14	119.8
C7—C6—H6	122.3	S—C15—H15A	109.5
C5—C6—H6	122.3	S—C15—H15B	109.5
C6—C7—O1	125.00 (18)	H15A—C15—H15B	109.5
C6—C7—C2	124.38 (18)	S—C15—H15C	109.5
O1—C7—C2	110.62 (16)	H15A—C15—H15C	109.5
C1—C8—O1	110.58 (16)	H15B—C15—H15C	109.5
O2—S—C1—C8	−130.84 (18)	C1—C2—C7—O1	0.4 (2)
C15—S—C1—C8	118.42 (19)	C2—C1—C8—O1	1.2 (2)
O2—S—C1—C2	40.85 (19)	S—C1—C8—O1	174.25 (13)
C15—S—C1—C2	−69.89 (19)	C2—C1—C8—C9	−178.8 (2)
C8—C1—C2—C7	−1.0 (2)	S—C1—C8—C9	−5.8 (3)
S—C1—C2—C7	−173.87 (15)	C7—O1—C8—C1	−1.0 (2)
C8—C1—C2—C3	177.6 (2)	C7—O1—C8—C9	179.06 (16)
S—C1—C2—C3	4.7 (3)	C1—C8—C9—C14	−38.8 (3)
C7—C2—C3—C4	−1.6 (3)	O1—C8—C9—C14	141.18 (18)
C1—C2—C3—C4	179.9 (2)	C1—C8—C9—C10	144.1 (2)
C2—C3—C4—C5	0.8 (3)	O1—C8—C9—C10	−36.0 (3)
C3—C4—C5—C6	0.3 (3)	C14—C9—C10—C11	0.0 (3)
C4—C5—C6—C7	−0.4 (3)	C8—C9—C10—C11	177.18 (19)
C5—C6—C7—O1	179.56 (18)	C9—C10—C11—C12	−0.3 (3)
C5—C6—C7—C2	−0.5 (3)	C10—C11—C12—C13	0.7 (4)
C8—O1—C7—C6	−179.69 (19)	C11—C12—C13—C14	−0.9 (3)
C8—O1—C7—C2	0.3 (2)	C12—C13—C14—C9	0.5 (3)
C3—C2—C7—C6	1.5 (3)	C10—C9—C14—C13	−0.1 (3)
C1—C2—C7—C6	−179.59 (19)	C8—C9—C14—C13	−177.25 (18)
C3—C2—C7—O1	−178.49 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···O2i	0.98	2.34	3.290 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯O2i	0.98	2.34	3.290 (3)	164

Symmetry code: (i) .