2,4,6-Trimethyl-3-phenyl-sulfinyl-1-benzofuran.

The title compound, C(17)H(16)O(2)S, was prepared by the oxidation of 2,4,6-trimethyl-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 planar benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [89.88 (8)°] and is tilted slightly towards it. The crystal structure is stabilized by C-H⋯π inter-actions between a phenyl H atoms and the phenyl and furan rings of neighbouring mol-ecules. In addition, the crystal structure exhibits inter-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 3-phenyl­sulfinyl-1-benzofuran derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C17H16O2S

M = 284.36

Monoclinic,

a = 13.493 (2) Å

b = 6.0154 (8) Å

c = 17.269 (2) Å

β = 90.909 (3)°

V = 1401.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

7482 measured reflections

2731 independent reflections

2291 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.151

S = 1.18

2731 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.43 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/S1600536808021090/bx2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021090/bx2157Isup2.hkl

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

C17H16O2S	F000 = 600
Mr = 284.36	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 3769 reflections
a = 13.493 (2) Å	θ = 2.4–28.3º
b = 6.0154 (8) Å	µ = 0.23 mm−1
c = 17.269 (2) Å	T = 173 (2) K
β = 90.909 (3)º	Block, colorless
V = 1401.5 (3) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	2731 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.067
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 1.5º
φ and ω scans	h = −16→13
Absorption correction: none	k = −7→7
7482 measured reflections	l = −21→21

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.044P)2 + 2.2792P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
2731 reflections	Δρmax = 0.76 e Å−3
184 parameters	Δρmin = −0.43 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	0.27007 (6)	0.17129 (13)	0.60901 (4)	0.0260 (2)
O1	0.25645 (15)	0.1919 (3)	0.38328 (11)	0.0233 (5)
O2	0.17960 (18)	0.1863 (4)	0.65645 (13)	0.0381 (6)
C1	0.2432 (2)	0.2412 (5)	0.51168 (16)	0.0207 (6)
C2	0.1875 (2)	0.4202 (5)	0.47392 (15)	0.0187 (6)
C3	0.1297 (2)	0.6036 (5)	0.49618 (16)	0.0195 (6)
C4	0.0910 (2)	0.7354 (5)	0.43702 (16)	0.0205 (6)
H4	0.0517	0.8599	0.4508	0.025*
C5	0.1066 (2)	0.6950 (5)	0.35773 (16)	0.0220 (6)
C6	0.1615 (2)	0.5103 (5)	0.33600 (15)	0.0210 (6)
H6	0.1720	0.4754	0.2831	0.025*
C7	0.1998 (2)	0.3805 (5)	0.39487 (16)	0.0199 (6)
C8	0.2813 (2)	0.1107 (5)	0.45543 (18)	0.0228 (6)
C9	0.3464 (2)	0.4068 (5)	0.63557 (16)	0.0235 (7)
C10	0.3202 (2)	0.5406 (6)	0.69695 (17)	0.0310 (8)
H10	0.2594	0.5171	0.7227	0.037*
C11	0.3838 (3)	0.7098 (6)	0.7205 (2)	0.0384 (9)
H11	0.3653	0.8069	0.7612	0.046*
C12	0.4737 (3)	0.7374 (6)	0.6850 (2)	0.0415 (9)
H12	0.5176	0.8516	0.7019	0.050*
C13	0.5001 (3)	0.5990 (6)	0.6247 (2)	0.0361 (8)
H13	0.5624	0.6179	0.6006	0.043*
C14	0.4362 (2)	0.4331 (6)	0.59928 (18)	0.0278 (7)
H14	0.4539	0.3389	0.5576	0.033*
C15	0.1085 (2)	0.6565 (6)	0.57950 (16)	0.0269 (7)
H15A	0.1651	0.7359	0.6026	0.040*
H15B	0.0974	0.5181	0.6080	0.040*
H15C	0.0492	0.7500	0.5821	0.040*
C16	0.0615 (2)	0.8484 (6)	0.29790 (18)	0.0300 (7)
H16A	0.0769	0.7938	0.2460	0.045*
H16B	0.0889	0.9982	0.3047	0.045*
H16C	−0.0105	0.8530	0.3041	0.045*
C17	0.3438 (3)	−0.0921 (6)	0.4550 (2)	0.0342 (8)
H17A	0.3529	−0.1465	0.5081	0.051*
H17B	0.4084	−0.0567	0.4331	0.051*
H17C	0.3112	−0.2070	0.4235	0.051*

	U11	U22	U33	U12	U13	U23
S	0.0282 (4)	0.0237 (4)	0.0258 (4)	−0.0067 (3)	−0.0038 (3)	0.0092 (3)
O1	0.0217 (10)	0.0217 (11)	0.0265 (11)	−0.0011 (9)	0.0024 (8)	−0.0063 (9)
O2	0.0366 (13)	0.0508 (16)	0.0271 (12)	−0.0123 (12)	0.0029 (10)	0.0099 (11)
C1	0.0198 (14)	0.0202 (15)	0.0221 (14)	−0.0066 (12)	−0.0014 (11)	0.0027 (11)
C2	0.0188 (14)	0.0197 (15)	0.0176 (13)	−0.0042 (12)	0.0001 (11)	0.0010 (11)
C3	0.0194 (14)	0.0218 (15)	0.0174 (14)	−0.0064 (12)	0.0015 (11)	−0.0033 (11)
C4	0.0179 (14)	0.0205 (15)	0.0232 (15)	−0.0012 (12)	0.0013 (11)	−0.0014 (11)
C5	0.0194 (14)	0.0253 (16)	0.0212 (14)	−0.0043 (12)	−0.0005 (11)	0.0019 (12)
C6	0.0216 (15)	0.0283 (16)	0.0130 (13)	−0.0039 (13)	−0.0002 (11)	−0.0012 (12)
C7	0.0184 (14)	0.0182 (15)	0.0231 (14)	−0.0036 (11)	0.0001 (11)	−0.0049 (11)
C8	0.0192 (14)	0.0164 (15)	0.0329 (17)	−0.0061 (11)	0.0003 (12)	0.0008 (12)
C9	0.0267 (16)	0.0241 (16)	0.0193 (14)	−0.0033 (13)	−0.0073 (12)	0.0055 (12)
C10	0.0309 (17)	0.041 (2)	0.0210 (15)	0.0025 (15)	−0.0058 (13)	0.0047 (14)
C11	0.050 (2)	0.035 (2)	0.0296 (18)	0.0064 (17)	−0.0146 (16)	−0.0049 (15)
C12	0.047 (2)	0.033 (2)	0.044 (2)	−0.0130 (17)	−0.0219 (17)	0.0051 (16)
C13	0.0270 (17)	0.041 (2)	0.0399 (19)	−0.0118 (15)	−0.0070 (14)	0.0100 (16)
C14	0.0233 (16)	0.0304 (17)	0.0297 (16)	−0.0012 (14)	−0.0025 (13)	0.0007 (14)
C15	0.0338 (17)	0.0292 (17)	0.0179 (14)	−0.0005 (14)	0.0023 (12)	−0.0054 (13)
C16	0.0267 (16)	0.0355 (19)	0.0277 (16)	−0.0005 (14)	−0.0034 (13)	0.0086 (14)
C17	0.0304 (18)	0.0227 (17)	0.050 (2)	0.0015 (14)	0.0054 (15)	0.0032 (15)

S—O2	1.484 (2)	C9—C14	1.382 (4)
S—C1	1.765 (3)	C10—C11	1.388 (5)
S—C9	1.806 (3)	C10—H10	0.9500
O1—C8	1.375 (4)	C11—C12	1.378 (6)
O1—C7	1.385 (4)	C11—H11	0.9500
C1—C8	1.356 (4)	C12—C13	1.384 (5)
C1—C2	1.461 (4)	C12—H12	0.9500
C2—C7	1.398 (4)	C13—C14	1.385 (5)
C2—C3	1.407 (4)	C13—H13	0.9500
C3—C4	1.389 (4)	C14—H14	0.9500
C3—C15	1.506 (4)	C15—H15A	0.9800
C4—C5	1.410 (4)	C15—H15B	0.9800
C4—H4	0.9500	C15—H15C	0.9800
C5—C6	1.390 (4)	C16—H16A	0.9800
C5—C16	1.506 (4)	C16—H16B	0.9800
C6—C7	1.376 (4)	C16—H16C	0.9800
C6—H6	0.9500	C17—H17A	0.9800
C8—C17	1.483 (4)	C17—H17B	0.9800
C9—C10	1.382 (5)	C17—H17C	0.9800
O2—S—C1	110.69 (14)	C9—C10—H10	120.4
O2—S—C9	106.44 (15)	C11—C10—H10	120.4
C1—S—C9	99.35 (13)	C12—C11—C10	120.1 (3)
C8—O1—C7	106.7 (2)	C12—C11—H11	119.9
C8—C1—C2	107.8 (2)	C10—C11—H11	119.9
C8—C1—S	118.0 (2)	C11—C12—C13	120.1 (3)
C2—C1—S	134.2 (2)	C11—C12—H12	119.9
C7—C2—C3	118.4 (3)	C13—C12—H12	119.9
C7—C2—C1	104.0 (2)	C12—C13—C14	120.3 (3)
C3—C2—C1	137.6 (3)	C12—C13—H13	119.8
C4—C3—C2	116.7 (3)	C14—C13—H13	119.8
C4—C3—C15	120.5 (3)	C9—C14—C13	119.0 (3)
C2—C3—C15	122.8 (3)	C9—C14—H14	120.5
C3—C4—C5	123.8 (3)	C13—C14—H14	120.5
C3—C4—H4	118.1	C3—C15—H15A	109.5
C5—C4—H4	118.1	C3—C15—H15B	109.5
C6—C5—C4	119.2 (3)	H15A—C15—H15B	109.5
C6—C5—C16	121.0 (3)	C3—C15—H15C	109.5
C4—C5—C16	119.7 (3)	H15A—C15—H15C	109.5
C7—C6—C5	116.7 (3)	H15B—C15—H15C	109.5
C7—C6—H6	121.6	C5—C16—H16A	109.5
C5—C6—H6	121.6	C5—C16—H16B	109.5
C6—C7—O1	124.0 (3)	H16A—C16—H16B	109.5
C6—C7—C2	125.1 (3)	C5—C16—H16C	109.5
O1—C7—C2	110.8 (2)	H16A—C16—H16C	109.5
C1—C8—O1	110.7 (3)	H16B—C16—H16C	109.5
C1—C8—C17	134.5 (3)	C8—C17—H17A	109.5
O1—C8—C17	114.7 (3)	C8—C17—H17B	109.5
C10—C9—C14	121.2 (3)	H17A—C17—H17B	109.5
C10—C9—S	120.0 (2)	C8—C17—H17C	109.5
C14—C9—S	118.4 (2)	H17A—C17—H17C	109.5
C9—C10—C11	119.2 (3)	H17B—C17—H17C	109.5
O2—S—C1—C8	−135.5 (2)	C3—C2—C7—C6	1.5 (4)
C9—S—C1—C8	112.9 (2)	C1—C2—C7—C6	−178.8 (3)
O2—S—C1—C2	45.8 (3)	C3—C2—C7—O1	−178.6 (2)
C9—S—C1—C2	−65.8 (3)	C1—C2—C7—O1	1.0 (3)
C8—C1—C2—C7	−1.3 (3)	C2—C1—C8—O1	1.1 (3)
S—C1—C2—C7	177.5 (2)	S—C1—C8—O1	−177.90 (18)
C8—C1—C2—C3	178.3 (3)	C2—C1—C8—C17	179.6 (3)
S—C1—C2—C3	−2.9 (5)	S—C1—C8—C17	0.6 (5)
C7—C2—C3—C4	−1.5 (4)	C7—O1—C8—C1	−0.5 (3)
C1—C2—C3—C4	179.0 (3)	C7—O1—C8—C17	−179.3 (2)
C7—C2—C3—C15	177.6 (3)	O2—S—C9—C10	7.6 (3)
C1—C2—C3—C15	−1.9 (5)	C1—S—C9—C10	122.5 (3)
C2—C3—C4—C5	−0.1 (4)	O2—S—C9—C14	−179.8 (2)
C15—C3—C4—C5	−179.3 (3)	C1—S—C9—C14	−64.9 (3)
C3—C4—C5—C6	1.8 (4)	C14—C9—C10—C11	2.5 (5)
C3—C4—C5—C16	−179.9 (3)	S—C9—C10—C11	174.8 (2)
C4—C5—C6—C7	−1.8 (4)	C9—C10—C11—C12	−2.6 (5)
C16—C5—C6—C7	179.9 (3)	C10—C11—C12—C13	1.2 (5)
C5—C6—C7—O1	−179.6 (3)	C11—C12—C13—C14	0.5 (5)
C5—C6—C7—C2	0.2 (4)	C10—C9—C14—C13	−0.8 (5)
C8—O1—C7—C6	179.4 (3)	S—C9—C14—C13	−173.3 (2)
C8—O1—C7—C2	−0.4 (3)	C12—C13—C14—C9	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1i	0.95	2.88	3.673 (5)	142
C13—H13···Cg2ii	0.95	2.95	3.882 (5)	168
C16—H16C···O2iii	0.98	2.40	3.366 (4)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1i	0.95	2.88	3.673 (5)	142
C13—H13⋯Cg2ii	0.95	2.95	3.882 (5)	168
C16—H16C⋯O2iii	0.98	2.40	3.366 (4)	167

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C9–C14 phenyl ring and the C1/C2/C7/O1/C8 furan ring, respectively.