2,5,7-Trimethyl-3-phenyl-sulfinyl-1-benzo-furan.

The title compound, C(17)H(16)O(2)S, was prepared by the oxidation of 2,5,7-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 plane of the benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [88.30 (9)°] and is tilted slightly towards it. No π-π or C-H⋯π inter-actions are observed between neighbouring mol-ecules in the crystal structure because of steric hindrance induced by the three methyl groups.

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 = 18.393 (2) Å

b = 6.1515 (6) Å

c = 13.054 (1) Å

β = 93.024 (2)°

V = 1474.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 298 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8615 measured reflections

3215 independent reflections

1611 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.163

S = 1.01

3215 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 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/S1600536808019302/rn2045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019302/rn2045Isup2.hkl

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

C17H16O2S	F000 = 600
Mr = 284.36	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 1802 reflections
a = 18.393 (2) Å	θ = 3.1–24.3º
b = 6.1515 (6) Å	µ = 0.22 mm−1
c = 13.054 (1) Å	T = 298 (2) K
β = 93.024 (2)º	Block, colorless
V = 1474.9 (2) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3215 independent reflections
Radiation source: fine-focus sealed tube	1611 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.066
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 298(2) K	θmin = 1.1º
φ and ω scans	h = −18→23
Absorption correction: none	k = −6→7
8615 measured reflections	l = −16→13

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.2115P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3215 reflections	Δρmax = 0.17 e Å−3
184 parameters	Δρmin = −0.20 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	0.33491 (5)	0.75793 (15)	0.41600 (7)	0.0730 (3)
O1	0.12972 (11)	0.7187 (3)	0.31945 (14)	0.0536 (5)
O2	0.34960 (15)	0.7328 (5)	0.52790 (19)	0.1133 (11)
C1	0.24341 (15)	0.6884 (5)	0.3874 (2)	0.0481 (7)
C2	0.20160 (15)	0.5094 (4)	0.42636 (19)	0.0438 (7)
C3	0.21511 (17)	0.3364 (5)	0.4936 (2)	0.0517 (7)
H3	0.2611	0.3158	0.5251	0.062*
C4	0.15868 (19)	0.1960 (5)	0.5125 (2)	0.0577 (8)
C5	0.09051 (19)	0.2308 (5)	0.4641 (2)	0.0653 (9)
H5	0.0534	0.1338	0.4775	0.078*
C6	0.07447 (16)	0.4016 (5)	0.3972 (2)	0.0571 (8)
C7	0.13246 (15)	0.5374 (4)	0.38166 (19)	0.0450 (7)
C8	0.19788 (17)	0.8067 (5)	0.3253 (2)	0.0517 (7)
C9	0.37498 (15)	0.5292 (5)	0.3559 (2)	0.0552 (8)
C10	0.36512 (17)	0.5067 (6)	0.2517 (3)	0.0727 (10)
H10	0.3375	0.6073	0.2134	0.087*
C11	0.3964 (2)	0.3347 (9)	0.2050 (3)	0.0974 (14)
H11	0.3891	0.3161	0.1345	0.117*
C12	0.4385 (2)	0.1893 (8)	0.2609 (5)	0.1024 (14)
H12	0.4588	0.0715	0.2281	0.123*
C13	0.4510 (2)	0.2152 (7)	0.3637 (4)	0.0973 (14)
H13	0.4807	0.1179	0.4009	0.117*
C14	0.41888 (19)	0.3882 (7)	0.4128 (3)	0.0779 (11)
H14	0.4270	0.4084	0.4831	0.094*
C15	0.1696 (2)	0.0106 (6)	0.5874 (3)	0.0864 (11)
H15A	0.2207	−0.0077	0.6043	0.130*
H15B	0.1503	−0.1207	0.5569	0.130*
H15C	0.1449	0.0422	0.6486	0.130*
C16	0.00061 (18)	0.4398 (7)	0.3461 (3)	0.0873 (12)
H16A	−0.0161	0.5825	0.3631	0.131*
H16B	−0.0329	0.3332	0.3695	0.131*
H16C	0.0035	0.4280	0.2731	0.131*
C17	0.2083 (2)	1.0024 (5)	0.2620 (2)	0.0760 (10)
H17A	0.2548	1.0662	0.2803	0.114*
H17B	0.1704	1.1056	0.2737	0.114*
H17C	0.2063	0.9624	0.1908	0.114*

	U11	U22	U33	U12	U13	U23
S	0.0663 (6)	0.0763 (7)	0.0762 (6)	−0.0265 (5)	0.0011 (4)	−0.0218 (5)
O1	0.0570 (13)	0.0537 (13)	0.0496 (12)	0.0046 (10)	−0.0005 (9)	−0.0029 (10)
O2	0.0903 (18)	0.178 (3)	0.0700 (17)	−0.0144 (18)	−0.0154 (14)	−0.0556 (17)
C1	0.0577 (18)	0.0457 (17)	0.0409 (16)	−0.0104 (14)	0.0017 (13)	−0.0058 (12)
C2	0.0541 (17)	0.0419 (16)	0.0356 (14)	−0.0058 (13)	0.0054 (12)	−0.0090 (12)
C3	0.067 (2)	0.0490 (17)	0.0387 (16)	0.0014 (15)	0.0030 (14)	−0.0008 (13)
C4	0.082 (2)	0.0468 (19)	0.0457 (18)	−0.0085 (16)	0.0177 (16)	−0.0021 (13)
C5	0.073 (2)	0.061 (2)	0.064 (2)	−0.0234 (18)	0.0229 (17)	−0.0057 (17)
C6	0.0527 (19)	0.064 (2)	0.0554 (19)	−0.0108 (16)	0.0085 (15)	−0.0140 (16)
C7	0.0528 (18)	0.0443 (17)	0.0379 (15)	−0.0011 (14)	0.0025 (13)	−0.0060 (13)
C8	0.069 (2)	0.0433 (18)	0.0434 (16)	−0.0031 (15)	0.0072 (14)	−0.0056 (13)
C9	0.0415 (17)	0.072 (2)	0.0522 (18)	−0.0146 (15)	0.0024 (14)	0.0029 (16)
C10	0.051 (2)	0.108 (3)	0.058 (2)	0.0070 (19)	−0.0011 (16)	−0.012 (2)
C11	0.061 (2)	0.144 (4)	0.088 (3)	0.006 (3)	0.006 (2)	−0.033 (3)
C12	0.082 (3)	0.096 (3)	0.132 (4)	−0.004 (3)	0.038 (3)	−0.022 (3)
C13	0.074 (3)	0.089 (3)	0.131 (4)	0.008 (2)	0.023 (3)	0.033 (3)
C14	0.067 (2)	0.100 (3)	0.067 (2)	−0.013 (2)	0.0089 (19)	0.018 (2)
C15	0.132 (3)	0.063 (2)	0.066 (2)	−0.006 (2)	0.026 (2)	0.0133 (18)
C16	0.054 (2)	0.107 (3)	0.100 (3)	−0.014 (2)	0.001 (2)	−0.017 (2)
C17	0.112 (3)	0.052 (2)	0.065 (2)	−0.0031 (19)	0.015 (2)	0.0073 (16)

S—O2	1.480 (3)	C9—C14	1.376 (4)
S—C1	1.757 (3)	C10—C11	1.364 (5)
S—C9	1.789 (3)	C10—H10	0.9300
O1—C8	1.364 (3)	C11—C12	1.368 (6)
O1—C7	1.379 (3)	C11—H11	0.9300
C1—C8	1.347 (4)	C12—C13	1.360 (6)
C1—C2	1.450 (4)	C12—H12	0.9300
C2—C7	1.382 (4)	C13—C14	1.390 (6)
C2—C3	1.393 (4)	C13—H13	0.9300
C3—C4	1.383 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.390 (5)	C15—H15B	0.9600
C4—C15	1.509 (4)	C15—H15C	0.9600
C5—C6	1.388 (4)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.378 (4)	C16—H16C	0.9600
C6—C16	1.500 (4)	C17—H17A	0.9600
C8—C17	1.479 (4)	C17—H17B	0.9600
C9—C10	1.369 (4)	C17—H17C	0.9600
O2—S—C1	107.90 (15)	C11—C10—H10	120.5
O2—S—C9	107.03 (16)	C9—C10—H10	120.5
C1—S—C9	97.32 (13)	C10—C11—C12	120.6 (4)
C8—O1—C7	106.4 (2)	C10—C11—H11	119.7
C8—C1—C2	107.3 (2)	C12—C11—H11	119.7
C8—C1—S	123.7 (2)	C13—C12—C11	120.8 (4)
C2—C1—S	129.0 (2)	C13—C12—H12	119.6
C7—C2—C3	119.4 (3)	C11—C12—H12	119.6
C7—C2—C1	104.5 (2)	C12—C13—C14	119.4 (4)
C3—C2—C1	136.1 (3)	C12—C13—H13	120.3
C4—C3—C2	118.6 (3)	C14—C13—H13	120.3
C4—C3—H3	120.7	C9—C14—C13	119.0 (4)
C2—C3—H3	120.7	C9—C14—H14	120.5
C3—C4—C5	119.4 (3)	C13—C14—H14	120.5
C3—C4—C15	120.8 (3)	C4—C15—H15A	109.5
C5—C4—C15	119.8 (3)	C4—C15—H15B	109.5
C6—C5—C4	124.0 (3)	H15A—C15—H15B	109.5
C6—C5—H5	118.0	C4—C15—H15C	109.5
C4—C5—H5	118.0	H15A—C15—H15C	109.5
C7—C6—C5	114.3 (3)	H15B—C15—H15C	109.5
C7—C6—C16	122.0 (3)	C6—C16—H16A	109.5
C5—C6—C16	123.7 (3)	C6—C16—H16B	109.5
C6—C7—O1	124.9 (3)	H16A—C16—H16B	109.5
C6—C7—C2	124.4 (3)	C6—C16—H16C	109.5
O1—C7—C2	110.7 (2)	H16A—C16—H16C	109.5
C1—C8—O1	111.1 (2)	H16B—C16—H16C	109.5
C1—C8—C17	132.9 (3)	C8—C17—H17A	109.5
O1—C8—C17	115.9 (3)	C8—C17—H17B	109.5
C10—C9—C14	121.1 (3)	H17A—C17—H17B	109.5
C10—C9—S	118.6 (3)	C8—C17—H17C	109.5
C14—C9—S	120.2 (3)	H17A—C17—H17C	109.5
C11—C10—C9	119.1 (4)	H17B—C17—H17C	109.5
O2—S—C1—C8	134.5 (3)	C3—C2—C7—C6	−1.3 (4)
C9—S—C1—C8	−114.9 (3)	C1—C2—C7—C6	179.7 (3)
O2—S—C1—C2	−42.3 (3)	C3—C2—C7—O1	178.9 (2)
C9—S—C1—C2	68.3 (3)	C1—C2—C7—O1	−0.1 (3)
C8—C1—C2—C7	0.5 (3)	C2—C1—C8—O1	−0.6 (3)
S—C1—C2—C7	177.7 (2)	S—C1—C8—O1	−178.05 (18)
C8—C1—C2—C3	−178.3 (3)	C2—C1—C8—C17	−178.2 (3)
S—C1—C2—C3	−1.1 (5)	S—C1—C8—C17	4.4 (5)
C7—C2—C3—C4	0.8 (4)	C7—O1—C8—C1	0.6 (3)
C1—C2—C3—C4	179.4 (3)	C7—O1—C8—C17	178.6 (2)
C2—C3—C4—C5	0.1 (4)	O2—S—C9—C10	176.0 (2)
C2—C3—C4—C15	−177.9 (3)	C1—S—C9—C10	64.7 (3)
C3—C4—C5—C6	−0.5 (5)	O2—S—C9—C14	−8.4 (3)
C15—C4—C5—C6	177.5 (3)	C1—S—C9—C14	−119.7 (3)
C4—C5—C6—C7	0.0 (4)	C14—C9—C10—C11	3.5 (5)
C4—C5—C6—C16	−179.3 (3)	S—C9—C10—C11	179.0 (3)
C5—C6—C7—O1	−179.3 (2)	C9—C10—C11—C12	−1.5 (6)
C16—C6—C7—O1	0.0 (4)	C10—C11—C12—C13	−1.1 (7)
C5—C6—C7—C2	0.9 (4)	C11—C12—C13—C14	1.8 (6)
C16—C6—C7—C2	−179.8 (3)	C10—C9—C14—C13	−2.8 (5)
C8—O1—C7—C6	180.0 (3)	S—C9—C14—C13	−178.2 (3)
C8—O1—C7—C2	−0.2 (3)	C12—C13—C14—C9	0.2 (6)