2-Methyl-3-phenyl-sulfonyl-5-propyl-1-benzofuran.

The title compound, C(18)H(18)O(3)S, was prepared by the oxidation of 2-methyl-3-phenyl-sulfanyl-5-propyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 81.74 (6)° with the plane of the benzofuran fragment. The crystal structure is stabilized by C-H⋯π inter-actions between a methyl H atom and the phenyl ring of the phenyl-sulfonyl substituent from a neighbouring mol-ecule, and by inter-molecular C-H⋯O inter-actions.

Related literature

For the crystal structures of similar 2-methyl-3-phenyl­sulfonyl-1-benzofuran compounds, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C18H18O3S

M = 314.38

Monoclinic,

a = 7.2712 (9) Å

b = 17.583 (2) Å

c = 12.788 (2) Å

β = 102.669 (2)°

V = 1595.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 173 (2) K

0.40 × 0.40 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8966 measured reflections

3125 independent reflections

2606 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.135

S = 1.12

3125 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.37 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/S1600536808025786/gw2046sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025786/gw2046Isup2.hkl

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

C18H18O3S	F000 = 664
Mr = 314.38	Dx = 1.309 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 3769 reflections
a = 7.2712 (9) Å	θ = 2.4–28.3º
b = 17.583 (2) Å	µ = 0.21 mm−1
c = 12.788 (2) Å	T = 173 (2) K
β = 102.669 (2)º	Block, colourless
V = 1595.1 (4) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	3125 independent reflections
Radiation source: fine-focus sealed tube	2606 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.053
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 173(2) K	θmin = 2.0º
φ and ω scans	h = −8→5
Absorption correction: none	k = −21→21
8966 measured reflections	l = −13→15

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.5558P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
3125 reflections	Δρmax = 0.36 e Å−3
200 parameters	Δρmin = −0.37 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	0.61553 (7)	0.71791 (3)	0.30885 (4)	0.02750 (18)
O1	0.7452 (2)	0.52071 (8)	0.44838 (12)	0.0335 (4)
O2	0.7324 (2)	0.76700 (8)	0.38556 (12)	0.0367 (4)
O3	0.4196 (2)	0.73668 (9)	0.27128 (12)	0.0359 (4)
C1	0.6276 (3)	0.62641 (11)	0.36076 (15)	0.0258 (4)
C2	0.4937 (3)	0.56569 (11)	0.32516 (16)	0.0266 (4)
C3	0.3214 (3)	0.55783 (13)	0.25182 (16)	0.0310 (5)
H3	0.2625	0.6007	0.2131	0.037*
C4	0.2374 (3)	0.48657 (13)	0.23632 (17)	0.0347 (5)
C5	0.3257 (3)	0.42403 (13)	0.29533 (19)	0.0403 (6)
H5	0.2669	0.3756	0.2839	0.048*
C6	0.4948 (3)	0.43051 (12)	0.36937 (19)	0.0380 (5)
H6	0.5528	0.3880	0.4094	0.046*
C7	0.5749 (3)	0.50211 (12)	0.38205 (16)	0.0300 (5)
C8	0.7750 (3)	0.59641 (12)	0.43314 (16)	0.0304 (5)
C9	0.7172 (3)	0.71003 (11)	0.19608 (16)	0.0276 (4)
C10	0.6070 (3)	0.68438 (12)	0.09947 (17)	0.0327 (5)
H10	0.4781	0.6717	0.0939	0.039*
C11	0.6880 (4)	0.67762 (13)	0.01194 (18)	0.0403 (6)
H11	0.6144	0.6603	−0.0546	0.048*
C12	0.8757 (4)	0.69593 (13)	0.0204 (2)	0.0407 (6)
H12	0.9304	0.6910	−0.0402	0.049*
C13	0.9842 (3)	0.72143 (13)	0.1167 (2)	0.0393 (5)
H13	1.1129	0.7341	0.1218	0.047*
C14	0.9063 (3)	0.72851 (12)	0.20576 (18)	0.0339 (5)
H14	0.9804	0.7457	0.2722	0.041*
C15	0.0537 (3)	0.47675 (16)	0.1550 (2)	0.0445 (6)
H15A	0.0473	0.5158	0.0986	0.053*
H15B	0.0549	0.4264	0.1205	0.053*
C16	−0.1198 (4)	0.4823 (2)	0.1979 (2)	0.0575 (8)
H16A	−0.1251	0.5334	0.2296	0.069*
H16B	−0.1129	0.4444	0.2558	0.069*
C17	−0.2983 (3)	0.46938 (15)	0.1141 (2)	0.0463 (6)
H17A	−0.2957	0.4185	0.0833	0.056*
H17B	−0.3080	0.5076	0.0573	0.056*
H17C	−0.4074	0.4737	0.1472	0.056*
C18	0.9566 (3)	0.62697 (14)	0.4949 (2)	0.0458 (6)
H18A	1.0596	0.6087	0.4633	0.069*
H18B	0.9770	0.6097	0.5695	0.069*
H18C	0.9532	0.6827	0.4929	0.069*

	U11	U22	U33	U12	U13	U23
S	0.0294 (3)	0.0218 (3)	0.0307 (3)	0.00328 (19)	0.0053 (2)	−0.00131 (19)
O1	0.0344 (8)	0.0271 (7)	0.0364 (8)	0.0002 (6)	0.0022 (6)	0.0050 (6)
O2	0.0446 (9)	0.0263 (7)	0.0377 (8)	−0.0017 (7)	0.0059 (7)	−0.0062 (6)
O3	0.0323 (9)	0.0338 (8)	0.0409 (9)	0.0094 (7)	0.0069 (7)	0.0003 (7)
C1	0.0277 (10)	0.0236 (9)	0.0264 (10)	0.0004 (8)	0.0063 (8)	−0.0003 (8)
C2	0.0277 (10)	0.0266 (10)	0.0274 (10)	−0.0005 (8)	0.0099 (8)	−0.0029 (8)
C3	0.0278 (11)	0.0360 (11)	0.0302 (11)	0.0009 (9)	0.0088 (8)	−0.0021 (9)
C4	0.0314 (12)	0.0418 (12)	0.0340 (11)	−0.0063 (9)	0.0143 (9)	−0.0110 (9)
C5	0.0435 (14)	0.0326 (11)	0.0490 (14)	−0.0125 (10)	0.0193 (11)	−0.0104 (10)
C6	0.0452 (14)	0.0271 (11)	0.0440 (13)	−0.0023 (10)	0.0148 (11)	0.0019 (9)
C7	0.0314 (11)	0.0293 (10)	0.0302 (10)	−0.0010 (8)	0.0088 (9)	−0.0002 (8)
C8	0.0327 (11)	0.0259 (10)	0.0312 (10)	0.0002 (9)	0.0042 (9)	0.0008 (8)
C9	0.0314 (11)	0.0202 (9)	0.0309 (11)	0.0037 (8)	0.0065 (8)	0.0043 (8)
C10	0.0315 (11)	0.0325 (11)	0.0327 (11)	−0.0003 (9)	0.0040 (9)	0.0041 (9)
C11	0.0518 (15)	0.0368 (12)	0.0314 (11)	−0.0026 (11)	0.0074 (10)	0.0025 (9)
C12	0.0534 (15)	0.0316 (11)	0.0427 (13)	0.0031 (11)	0.0228 (11)	0.0062 (10)
C13	0.0343 (12)	0.0323 (11)	0.0545 (14)	0.0007 (9)	0.0165 (11)	0.0067 (10)
C14	0.0324 (12)	0.0280 (10)	0.0399 (12)	−0.0006 (9)	0.0045 (9)	0.0018 (9)
C15	0.0374 (13)	0.0589 (15)	0.0392 (13)	−0.0113 (11)	0.0130 (10)	−0.0187 (11)
C16	0.0352 (14)	0.096 (2)	0.0409 (14)	0.0089 (14)	0.0068 (11)	−0.0107 (14)
C17	0.0322 (13)	0.0517 (15)	0.0532 (15)	0.0029 (11)	0.0057 (11)	−0.0032 (12)
C18	0.0391 (13)	0.0368 (12)	0.0523 (14)	−0.0034 (10)	−0.0103 (11)	0.0062 (11)

S—O2	1.437 (2)	C10—C11	1.380 (3)
S—O3	1.438 (2)	C10—H10	0.9500
S—C1	1.735 (2)	C11—C12	1.384 (4)
S—C9	1.765 (2)	C11—H11	0.9500
O1—C8	1.369 (2)	C12—C13	1.384 (4)
O1—C7	1.378 (3)	C12—H12	0.9500
C1—C8	1.360 (3)	C13—C14	1.384 (3)
C1—C2	1.449 (3)	C13—H13	0.9500
C2—C7	1.392 (3)	C14—H14	0.9500
C2—C3	1.398 (3)	C15—C16	1.485 (4)
C3—C4	1.389 (3)	C15—H15A	0.9900
C3—H3	0.9500	C15—H15B	0.9900
C4—C5	1.407 (3)	C16—C17	1.508 (3)
C4—C15	1.512 (3)	C16—H16A	0.9900
C5—C6	1.382 (3)	C16—H16B	0.9900
C5—H5	0.9500	C17—H17A	0.9800
C6—C7	1.382 (3)	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C8—C18	1.483 (3)	C18—H18A	0.9800
C9—C14	1.391 (3)	C18—H18B	0.9800
C9—C10	1.392 (3)	C18—H18C	0.9800
O2—S—O3	118.98 (9)	C10—C11—C12	120.4 (2)
O2—S—C1	108.86 (9)	C10—C11—H11	119.8
O3—S—C1	107.68 (10)	C12—C11—H11	119.8
O2—S—C9	108.30 (10)	C13—C12—C11	120.4 (2)
O3—S—C9	107.87 (9)	C13—C12—H12	119.8
C1—S—C9	104.17 (9)	C11—C12—H12	119.8
C8—O1—C7	106.97 (15)	C12—C13—C14	120.3 (2)
C8—C1—C2	107.64 (18)	C12—C13—H13	119.8
C8—C1—S	125.89 (16)	C14—C13—H13	119.8
C2—C1—S	126.07 (15)	C13—C14—C9	118.7 (2)
C7—C2—C3	119.09 (19)	C13—C14—H14	120.6
C7—C2—C1	104.40 (18)	C9—C14—H14	120.6
C3—C2—C1	136.49 (19)	C16—C15—C4	115.6 (2)
C4—C3—C2	119.1 (2)	C16—C15—H15A	108.4
C4—C3—H3	120.4	C4—C15—H15A	108.4
C2—C3—H3	120.4	C16—C15—H15B	108.4
C3—C4—C5	119.6 (2)	C4—C15—H15B	108.4
C3—C4—C15	119.7 (2)	H15A—C15—H15B	107.4
C5—C4—C15	120.7 (2)	C15—C16—C17	113.4 (2)
C6—C5—C4	122.4 (2)	C15—C16—H16A	108.9
C6—C5—H5	118.8	C17—C16—H16A	108.9
C4—C5—H5	118.8	C15—C16—H16B	108.9
C7—C6—C5	116.4 (2)	C17—C16—H16B	108.9
C7—C6—H6	121.8	H16A—C16—H16B	107.7
C5—C6—H6	121.8	C16—C17—H17A	109.5
O1—C7—C6	126.0 (2)	C16—C17—H17B	109.5
O1—C7—C2	110.60 (18)	H17A—C17—H17B	109.5
C6—C7—C2	123.4 (2)	C16—C17—H17C	109.5
C1—C8—O1	110.39 (18)	H17A—C17—H17C	109.5
C1—C8—C18	134.4 (2)	H17B—C17—H17C	109.5
O1—C8—C18	115.24 (18)	C8—C18—H18A	109.5
C14—C9—C10	121.3 (2)	C8—C18—H18B	109.5
C14—C9—S	119.47 (16)	H18A—C18—H18B	109.5
C10—C9—S	119.19 (17)	C8—C18—H18C	109.5
C11—C10—C9	118.9 (2)	H18A—C18—H18C	109.5
C11—C10—H10	120.6	H18B—C18—H18C	109.5
C9—C10—H10	120.6
O2—S—C1—C8	−27.3 (2)	C1—C2—C7—C6	−177.9 (2)
O3—S—C1—C8	−157.57 (18)	C2—C1—C8—O1	−0.9 (2)
C9—S—C1—C8	88.1 (2)	S—C1—C8—O1	−173.94 (14)
O2—S—C1—C2	160.91 (17)	C2—C1—C8—C18	177.5 (2)
O3—S—C1—C2	30.7 (2)	S—C1—C8—C18	4.4 (4)
C9—S—C1—C2	−83.72 (19)	C7—O1—C8—C1	1.0 (2)
C8—C1—C2—C7	0.4 (2)	C7—O1—C8—C18	−177.68 (19)
S—C1—C2—C7	173.44 (15)	O2—S—C9—C14	19.23 (19)
C8—C1—C2—C3	−177.8 (2)	O3—S—C9—C14	149.23 (16)
S—C1—C2—C3	−4.7 (3)	C1—S—C9—C14	−96.53 (17)
C7—C2—C3—C4	−1.1 (3)	O2—S—C9—C10	−161.66 (16)
C1—C2—C3—C4	176.9 (2)	O3—S—C9—C10	−31.66 (18)
C2—C3—C4—C5	0.7 (3)	C1—S—C9—C10	82.58 (17)
C2—C3—C4—C15	−178.30 (18)	C14—C9—C10—C11	−0.2 (3)
C3—C4—C5—C6	0.1 (3)	S—C9—C10—C11	−179.34 (16)
C15—C4—C5—C6	179.2 (2)	C9—C10—C11—C12	0.1 (3)
C4—C5—C6—C7	−0.6 (3)	C10—C11—C12—C13	−0.2 (3)
C8—O1—C7—C6	177.3 (2)	C11—C12—C13—C14	0.3 (3)
C8—O1—C7—C2	−0.7 (2)	C12—C13—C14—C9	−0.4 (3)
C5—C6—C7—O1	−177.6 (2)	C10—C9—C14—C13	0.4 (3)
C5—C6—C7—C2	0.2 (3)	S—C9—C14—C13	179.49 (16)
C3—C2—C7—O1	178.77 (17)	C3—C4—C15—C16	−94.1 (3)
C1—C2—C7—O1	0.2 (2)	C5—C4—C15—C16	86.9 (3)
C3—C2—C7—C6	0.6 (3)	C4—C15—C16—C17	−178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.95	2.60	3.355 (3)	137
C18—H18C···Cgii	0.98	3.29	3.947 (4)	126

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.95	2.60	3.355 (3)	137
C18—H18C⋯Cgii	0.98	3.29	3.947 (4)	126

Symmetry codes: (i) ; (ii) .