2,5,7-Trimethyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(17)H(16)O(3)S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring exhibits a dihedral angle of 81.16 (4)° with the plane of the benzofuran fragment. The crystal structure is stabilized by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.874 (2) Å] and by C-H⋯π inter-actions between a phenyl H atom of the phenyl-sulfonyl substituent and the furan ring of adjacent mol-ecules. In addition, the crystal structure exhibits intra- and inter-molecular C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C17H16O3S

M = 300.36

Monoclinic,

a = 9.2468 (7) Å

b = 8.4238 (7) Å

c = 18.963 (2) Å

β = 91.535 (2)°

V = 1476.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.40 × 0.40 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8704 measured reflections

3212 independent reflections

2544 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.03

3212 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.38 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/S1600536808008477/zl2106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008477/zl2106Isup2.hkl

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

C17H16O3S	F000 = 632
Mr = 300.36	Dx = 1.351 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 4291 reflections
a = 9.2468 (7) Å	θ = 2.5–28.3º
b = 8.4238 (7) Å	µ = 0.23 mm−1
c = 18.963 (2) Å	T = 173 (2) K
β = 91.535 (2)º	Block, colorless
V = 1476.6 (2) Å3	0.40 × 0.40 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	3212 independent reflections
Radiation source: fine-focus sealed tube	2544 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.5º
φ and ω scans	h = −11→11
Absorption correction: none	k = −7→10
8704 measured reflections	l = −24→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0467P)2 + 0.6422P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3212 reflections	Δρmax = 0.30 e Å−3
193 parameters	Δρmin = −0.38 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	0.71396 (5)	0.59940 (5)	0.11202 (2)	0.02746 (13)
O1	1.04792 (13)	0.77976 (15)	0.01610 (7)	0.0331 (3)
O2	0.77401 (15)	0.57958 (16)	0.18201 (6)	0.0386 (3)
O3	0.63915 (14)	0.46890 (14)	0.07823 (7)	0.0346 (3)
C1	0.84920 (18)	0.6601 (2)	0.05599 (9)	0.0270 (4)
C2	0.84265 (18)	0.6499 (2)	−0.02041 (9)	0.0260 (4)
C3	0.74772 (19)	0.5861 (2)	−0.07118 (9)	0.0290 (4)
H3	0.6625	0.5321	−0.0579	0.035*
C4	0.7809 (2)	0.6035 (2)	−0.14184 (9)	0.0330 (4)
C5	0.9071 (2)	0.6844 (2)	−0.16049 (10)	0.0346 (4)
H5	0.9266	0.6957	−0.2092	0.042*
C6	1.00483 (19)	0.7488 (2)	−0.11156 (10)	0.0328 (4)
C7	0.96763 (19)	0.7270 (2)	−0.04190 (9)	0.0291 (4)
C8	0.97377 (19)	0.7376 (2)	0.07465 (9)	0.0304 (4)
C9	0.59363 (18)	0.7624 (2)	0.11293 (9)	0.0263 (4)
C10	0.48964 (19)	0.7768 (2)	0.05910 (9)	0.0318 (4)
H10	0.4830	0.7005	0.0223	0.038*
C11	0.3956 (2)	0.9051 (2)	0.06032 (11)	0.0402 (5)
H11	0.3232	0.9165	0.0242	0.048*
C12	0.4063 (2)	1.0159 (2)	0.11345 (12)	0.0450 (5)
H12	0.3416	1.1035	0.1137	0.054*
C13	0.5111 (2)	1.0004 (2)	0.16670 (11)	0.0428 (5)
H13	0.5180	1.0776	0.2032	0.051*
C14	0.6058 (2)	0.8729 (2)	0.16692 (10)	0.0329 (4)
H14	0.6777	0.8615	0.2033	0.040*
C15	0.6791 (2)	0.5378 (3)	−0.19827 (10)	0.0461 (5)
H15A	0.6497	0.4301	−0.1853	0.069*
H15B	0.7282	0.5348	−0.2434	0.069*
H15C	0.5934	0.6058	−0.2027	0.069*
C16	1.1407 (2)	0.8345 (2)	−0.13129 (12)	0.0438 (5)
H16A	1.1486	0.9339	−0.1046	0.066*
H16B	1.1370	0.8581	−0.1819	0.066*
H16C	1.2249	0.7675	−0.1202	0.066*
C17	1.0431 (2)	0.7849 (2)	0.14286 (10)	0.0398 (5)
H17A	0.9787	0.7586	0.1814	0.060*
H17B	1.0614	0.8994	0.1427	0.060*
H17C	1.1348	0.7278	0.1495	0.060*

	U11	U22	U33	U12	U13	U23
S	0.0317 (2)	0.0259 (2)	0.0248 (2)	0.00101 (17)	0.00055 (16)	0.00232 (17)
O1	0.0278 (6)	0.0313 (7)	0.0401 (7)	−0.0011 (5)	0.0010 (5)	−0.0019 (6)
O2	0.0440 (8)	0.0429 (8)	0.0287 (7)	0.0047 (6)	−0.0027 (6)	0.0058 (6)
O3	0.0403 (7)	0.0252 (6)	0.0383 (7)	−0.0040 (5)	0.0022 (6)	−0.0008 (5)
C1	0.0264 (8)	0.0274 (9)	0.0273 (8)	0.0029 (7)	−0.0003 (6)	−0.0001 (7)
C2	0.0276 (8)	0.0229 (8)	0.0276 (8)	0.0051 (7)	0.0019 (6)	0.0015 (7)
C3	0.0301 (9)	0.0280 (9)	0.0289 (9)	0.0026 (7)	0.0005 (7)	0.0000 (7)
C4	0.0383 (10)	0.0317 (9)	0.0289 (9)	0.0091 (8)	−0.0003 (7)	0.0010 (8)
C5	0.0430 (10)	0.0332 (10)	0.0281 (9)	0.0124 (8)	0.0082 (8)	0.0045 (8)
C6	0.0334 (10)	0.0260 (9)	0.0395 (10)	0.0081 (7)	0.0098 (8)	0.0050 (8)
C7	0.0287 (8)	0.0238 (8)	0.0348 (9)	0.0043 (7)	0.0007 (7)	−0.0003 (7)
C8	0.0294 (9)	0.0274 (9)	0.0343 (9)	0.0047 (7)	−0.0008 (7)	−0.0013 (7)
C9	0.0253 (8)	0.0252 (8)	0.0286 (8)	−0.0030 (7)	0.0045 (7)	0.0023 (7)
C10	0.0320 (9)	0.0308 (9)	0.0324 (9)	−0.0035 (7)	0.0006 (7)	0.0012 (8)
C11	0.0303 (10)	0.0424 (11)	0.0480 (12)	0.0021 (8)	0.0011 (8)	0.0113 (9)
C12	0.0404 (11)	0.0350 (11)	0.0605 (13)	0.0097 (9)	0.0177 (10)	0.0049 (10)
C13	0.0488 (12)	0.0338 (10)	0.0465 (12)	0.0003 (9)	0.0147 (9)	−0.0076 (9)
C14	0.0339 (9)	0.0345 (10)	0.0307 (9)	−0.0040 (8)	0.0066 (7)	−0.0033 (8)
C15	0.0492 (12)	0.0601 (14)	0.0285 (10)	0.0059 (11)	−0.0055 (8)	−0.0026 (9)
C16	0.0401 (11)	0.0361 (11)	0.0561 (13)	0.0031 (9)	0.0161 (10)	0.0097 (9)
C17	0.0359 (10)	0.0416 (11)	0.0413 (11)	0.0006 (9)	−0.0096 (8)	−0.0055 (9)

S—O2	1.4346 (13)	C9—C10	1.389 (2)
S—O3	1.4401 (13)	C10—C11	1.388 (3)
S—C1	1.7394 (17)	C10—H10	0.9500
S—C9	1.7674 (17)	C11—C12	1.375 (3)
O1—C8	1.367 (2)	C11—H11	0.9500
O1—C7	1.384 (2)	C12—C13	1.387 (3)
C1—C8	1.363 (2)	C12—H12	0.9500
C1—C2	1.451 (2)	C13—C14	1.386 (3)
C2—C3	1.393 (2)	C13—H13	0.9500
C2—C7	1.396 (2)	C14—H14	0.9500
C3—C4	1.390 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C4—C5	1.405 (3)	C15—H15C	0.9800
C4—C15	1.511 (3)	C16—H16A	0.9800
C5—C6	1.388 (3)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.386 (2)	C17—H17A	0.9800
C6—C16	1.505 (3)	C17—H17B	0.9800
C8—C17	1.483 (2)	C17—H17C	0.9800
C9—C14	1.386 (2)
O2—S—O3	119.48 (8)	C11—C10—C9	118.54 (17)
O2—S—C1	109.43 (8)	C11—C10—H10	120.7
O3—S—C1	107.29 (8)	C9—C10—H10	120.7
O2—S—C9	108.03 (8)	C12—C11—C10	120.53 (19)
O3—S—C9	107.59 (8)	C12—C11—H11	119.7
C1—S—C9	103.94 (8)	C10—C11—H11	119.7
C8—O1—C7	106.96 (13)	C11—C12—C13	120.35 (19)
C8—C1—C2	107.46 (15)	C11—C12—H12	119.8
C8—C1—S	126.78 (14)	C13—C12—H12	119.8
C2—C1—S	125.53 (13)	C14—C13—C12	120.26 (19)
C3—C2—C7	119.27 (16)	C14—C13—H13	119.9
C3—C2—C1	136.18 (16)	C12—C13—H13	119.9
C7—C2—C1	104.55 (15)	C13—C14—C9	118.66 (18)
C4—C3—C2	118.31 (17)	C13—C14—H14	120.7
C4—C3—H3	120.8	C9—C14—H14	120.7
C2—C3—H3	120.8	C4—C15—H15A	109.5
C3—C4—C5	119.98 (17)	C4—C15—H15B	109.5
C3—C4—C15	119.65 (18)	H15A—C15—H15B	109.5
C5—C4—C15	120.36 (17)	C4—C15—H15C	109.5
C6—C5—C4	123.47 (17)	H15A—C15—H15C	109.5
C6—C5—H5	118.3	H15B—C15—H15C	109.5
C4—C5—H5	118.3	C6—C16—H16A	109.5
C7—C6—C5	114.32 (17)	C6—C16—H16B	109.5
C7—C6—C16	122.04 (18)	H16A—C16—H16B	109.5
C5—C6—C16	123.64 (17)	C6—C16—H16C	109.5
O1—C7—C6	124.99 (16)	H16A—C16—H16C	109.5
O1—C7—C2	110.38 (15)	H16B—C16—H16C	109.5
C6—C7—C2	124.63 (17)	C8—C17—H17A	109.5
C1—C8—O1	110.64 (15)	C8—C17—H17B	109.5
C1—C8—C17	134.26 (17)	H17A—C17—H17B	109.5
O1—C8—C17	115.10 (15)	C8—C17—H17C	109.5
C14—C9—C10	121.66 (17)	H17A—C17—H17C	109.5
C14—C9—S	119.35 (14)	H17B—C17—H17C	109.5
C10—C9—S	118.98 (13)
O2—S—C1—C8	−24.52 (19)	C3—C2—C7—O1	−179.24 (14)
O3—S—C1—C8	−155.54 (16)	C1—C2—C7—O1	0.79 (18)
C9—S—C1—C8	90.68 (17)	C3—C2—C7—C6	1.4 (3)
O2—S—C1—C2	161.63 (14)	C1—C2—C7—C6	−178.60 (16)
O3—S—C1—C2	30.61 (17)	C2—C1—C8—O1	0.6 (2)
C9—S—C1—C2	−83.18 (16)	S—C1—C8—O1	−174.20 (12)
C8—C1—C2—C3	179.23 (19)	C2—C1—C8—C17	−179.81 (19)
S—C1—C2—C3	−5.9 (3)	S—C1—C8—C17	5.4 (3)
C8—C1—C2—C7	−0.81 (19)	C7—O1—C8—C1	−0.07 (19)
S—C1—C2—C7	174.03 (13)	C7—O1—C8—C17	−179.78 (15)
C7—C2—C3—C4	−0.7 (2)	O2—S—C9—C14	20.07 (16)
C1—C2—C3—C4	179.30 (18)	O3—S—C9—C14	150.32 (14)
C2—C3—C4—C5	−0.3 (3)	C1—S—C9—C14	−96.11 (15)
C2—C3—C4—C15	−179.10 (17)	O2—S—C9—C10	−160.35 (13)
C3—C4—C5—C6	0.8 (3)	O3—S—C9—C10	−30.10 (15)
C15—C4—C5—C6	179.52 (17)	C1—S—C9—C10	83.47 (15)
C4—C5—C6—C7	−0.1 (3)	C14—C9—C10—C11	−0.5 (3)
C4—C5—C6—C16	179.55 (17)	S—C9—C10—C11	179.95 (13)
C8—O1—C7—C6	178.91 (16)	C9—C10—C11—C12	0.5 (3)
C8—O1—C7—C2	−0.48 (18)	C10—C11—C12—C13	−0.2 (3)
C5—C6—C7—O1	179.76 (15)	C11—C12—C13—C14	−0.1 (3)
C16—C6—C7—O1	0.1 (3)	C12—C13—C14—C9	0.2 (3)
C5—C6—C7—C2	−0.9 (3)	C10—C9—C14—C13	0.1 (3)
C16—C6—C7—C2	179.37 (16)	S—C9—C14—C13	179.70 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg1i	0.95	2.81	3.747 (3)	169
C16—H16C···O3ii	0.98	2.48	3.403 (2)	158
C17—H17A···O2	0.98	2.42	3.135 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg1i	0.95	2.81	3.747 (3)	169
C16—H16C⋯O3ii	0.98	2.48	3.403 (2)	158
C17—H17A⋯O2	0.98	2.42	3.135 (3)	129

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the O1/C8/C1/C2/C7 furan ring.