5-Ethyl-2-methyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(17)H(16)O(3)S, was prepared by the oxidation of 5-ethyl-2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 75.94 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by π-π inter-actions between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.620 (4) Å]. In addition, the crystal structure exhibits C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C17H16O3S

M = 300.36

Monoclinic,

a = 8.7009 (4) Å

b = 8.2019 (4) Å

c = 20.682 (1) Å

β = 97.301 (1)°

V = 1463.98 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

8693 measured reflections

3194 independent reflections

2264 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.148

S = 1.03

3194 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.49 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/S1600536808012877/cf2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012877/cf2194Isup2.hkl

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

C17H16O3S	F000 = 632
Mr = 300.36	Dx = 1.363 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P_2yn	Cell parameters from 2779 reflections
a = 8.7009 (4) Å	θ = 2.4–27.9º
b = 8.2019 (4) Å	µ = 0.23 mm−1
c = 20.682 (1) Å	T = 173 (2) K
β = 97.301 (1)º	Block, colorless
V = 1463.98 (12) Å3	0.40 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	3194 independent reflections
Radiation source: fine-focus sealed tube	2264 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.4º
φ and ω scans	h = −8→11
Absorption correction: none	k = −8→10
8693 measured reflections	l = −24→26

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0725P)2 + 0.989P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3194 reflections	Δρmax = 0.42 e Å−3
192 parameters	Δρmin = −0.49 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	0.22072 (7)	0.75221 (8)	0.07999 (3)	0.01957 (19)
O1	0.6098 (2)	0.7989 (3)	0.00433 (10)	0.0340 (5)
O2	0.1125 (2)	0.7474 (2)	0.02135 (9)	0.0302 (5)
O3	0.1953 (2)	0.8653 (2)	0.13092 (9)	0.0256 (4)
C1	0.4056 (3)	0.7908 (3)	0.06010 (12)	0.0206 (6)
C2	0.5331 (3)	0.8631 (3)	0.10261 (13)	0.0219 (6)
C3	0.5561 (3)	0.9250 (3)	0.16565 (13)	0.0253 (6)
H3	0.4738	0.9264	0.1918	0.030*
C4	0.7023 (3)	0.9852 (4)	0.18992 (15)	0.0318 (7)
C5	0.8208 (3)	0.9848 (4)	0.15001 (17)	0.0362 (8)
H5	0.9195	1.0266	0.1671	0.043*
C6	0.8006 (3)	0.9267 (4)	0.08721 (16)	0.0361 (8)
H6	0.8817	0.9286	0.0605	0.043*
C7	0.6548 (3)	0.8648 (4)	0.06503 (14)	0.0286 (6)
C8	0.4583 (3)	0.7531 (3)	0.00219 (13)	0.0283 (6)
C9	0.2322 (3)	0.5547 (3)	0.11444 (12)	0.0184 (5)
C10	0.3091 (3)	0.5341 (3)	0.17728 (13)	0.0246 (6)
H10	0.3552	0.6245	0.2010	0.030*
C11	0.3172 (3)	0.3800 (4)	0.20437 (13)	0.0280 (6)
H11	0.3697	0.3637	0.2470	0.034*
C12	0.2487 (3)	0.2487 (3)	0.16934 (14)	0.0294 (6)
H12	0.2542	0.1429	0.1882	0.035*
C13	0.1722 (3)	0.2713 (3)	0.10688 (14)	0.0280 (6)
H13	0.1255	0.1809	0.0833	0.034*
C14	0.1637 (3)	0.4242 (3)	0.07899 (13)	0.0236 (6)
H14	0.1119	0.4400	0.0362	0.028*
C15	0.3901 (4)	0.6744 (4)	−0.05890 (14)	0.0389 (8)
H15A	0.2823	0.6446	−0.0556	0.058*
H15B	0.4494	0.5762	−0.0664	0.058*
H15C	0.3933	0.7503	−0.0953	0.058*
C16	0.7384 (4)	1.0484 (5)	0.25879 (18)	0.0546 (10)
H16A	0.8332	0.9924	0.2791	0.066*
H16B	0.7639	1.1657	0.2561	0.066*
C17	0.6211 (5)	1.0323 (6)	0.30328 (18)	0.0597 (11)
H17A	0.5272	1.0912	0.2855	0.090*
H17B	0.6612	1.0782	0.3459	0.090*
H17C	0.5965	0.9168	0.3083	0.090*

	U11	U22	U33	U12	U13	U23
S	0.0181 (3)	0.0187 (3)	0.0212 (3)	0.0015 (2)	−0.0004 (2)	0.0000 (3)
O1	0.0302 (11)	0.0407 (13)	0.0338 (12)	0.0061 (9)	0.0137 (9)	0.0073 (10)
O2	0.0274 (10)	0.0313 (11)	0.0295 (10)	0.0013 (8)	−0.0058 (8)	0.0035 (9)
O3	0.0231 (10)	0.0222 (10)	0.0323 (11)	0.0004 (8)	0.0063 (8)	−0.0056 (8)
C1	0.0222 (13)	0.0177 (13)	0.0225 (13)	0.0017 (10)	0.0049 (10)	0.0029 (11)
C2	0.0177 (13)	0.0195 (13)	0.0289 (14)	0.0024 (10)	0.0045 (11)	0.0070 (11)
C3	0.0202 (14)	0.0259 (15)	0.0299 (15)	−0.0016 (11)	0.0037 (11)	0.0014 (12)
C4	0.0241 (15)	0.0291 (16)	0.0404 (17)	−0.0061 (12)	−0.0025 (12)	0.0039 (13)
C5	0.0175 (14)	0.0372 (18)	0.052 (2)	−0.0044 (12)	−0.0009 (13)	0.0117 (16)
C6	0.0208 (15)	0.0384 (18)	0.051 (2)	0.0047 (12)	0.0116 (14)	0.0179 (16)
C7	0.0264 (15)	0.0277 (15)	0.0329 (15)	0.0067 (12)	0.0082 (12)	0.0084 (13)
C8	0.0306 (15)	0.0293 (15)	0.0256 (14)	0.0069 (12)	0.0058 (12)	0.0089 (13)
C9	0.0171 (12)	0.0192 (13)	0.0191 (13)	−0.0002 (10)	0.0037 (10)	−0.0006 (10)
C10	0.0263 (14)	0.0255 (15)	0.0212 (13)	−0.0015 (11)	−0.0001 (11)	−0.0037 (11)
C11	0.0324 (16)	0.0306 (16)	0.0198 (13)	0.0005 (12)	−0.0008 (11)	0.0012 (12)
C12	0.0373 (16)	0.0208 (14)	0.0317 (15)	0.0006 (12)	0.0104 (13)	0.0044 (13)
C13	0.0333 (15)	0.0224 (15)	0.0289 (15)	−0.0044 (11)	0.0062 (12)	−0.0055 (12)
C14	0.0258 (14)	0.0239 (14)	0.0209 (13)	−0.0016 (11)	0.0023 (11)	−0.0019 (11)
C15	0.052 (2)	0.0423 (19)	0.0232 (15)	0.0102 (16)	0.0090 (14)	−0.0009 (14)
C16	0.0393 (19)	0.066 (3)	0.058 (2)	−0.0246 (18)	0.0013 (17)	−0.017 (2)
C17	0.059 (2)	0.077 (3)	0.042 (2)	−0.018 (2)	−0.0003 (18)	−0.019 (2)

S—O2	1.4386 (19)	C9—C10	1.395 (3)
S—O3	1.4417 (19)	C10—C11	1.381 (4)
S—C1	1.740 (3)	C10—H10	0.950
S—C9	1.767 (3)	C11—C12	1.389 (4)
O1—C8	1.367 (3)	C11—H11	0.950
O1—C7	1.377 (4)	C12—C13	1.388 (4)
C1—C8	1.371 (4)	C12—H12	0.950
C1—C2	1.451 (4)	C13—C14	1.379 (4)
C2—C3	1.390 (4)	C13—H13	0.950
C2—C7	1.391 (4)	C14—H14	0.950
C3—C4	1.397 (4)	C15—H15A	0.980
C3—H3	0.950	C15—H15B	0.980
C4—C5	1.400 (4)	C15—H15C	0.980
C4—C16	1.511 (5)	C16—C17	1.464 (5)
C5—C6	1.374 (5)	C16—H16A	0.990
C5—H5	0.950	C16—H16B	0.990
C6—C7	1.389 (4)	C17—H17A	0.980
C6—H6	0.950	C17—H17B	0.980
C8—C15	1.474 (4)	C17—H17C	0.980
C9—C14	1.388 (4)
O2—S—O3	119.24 (12)	C11—C10—C9	118.9 (2)
O2—S—C1	109.38 (12)	C11—C10—H10	120.6
O3—S—C1	106.76 (12)	C9—C10—H10	120.6
O2—S—C9	108.19 (12)	C10—C11—C12	120.1 (3)
O3—S—C9	107.54 (11)	C10—C11—H11	119.9
C1—S—C9	104.81 (12)	C12—C11—H11	119.9
C8—O1—C7	107.4 (2)	C11—C12—C13	120.3 (3)
C8—C1—C2	107.9 (2)	C11—C12—H12	119.8
C8—C1—S	126.0 (2)	C13—C12—H12	119.8
C2—C1—S	126.13 (19)	C14—C13—C12	120.3 (3)
C3—C2—C7	119.4 (2)	C14—C13—H13	119.9
C3—C2—C1	136.5 (2)	C12—C13—H13	119.9
C7—C2—C1	104.1 (2)	C13—C14—C9	118.9 (2)
C2—C3—C4	118.8 (3)	C13—C14—H14	120.5
C2—C3—H3	120.6	C9—C14—H14	120.5
C4—C3—H3	120.6	C8—C15—H15A	109.5
C3—C4—C5	119.5 (3)	C8—C15—H15B	109.5
C3—C4—C16	122.0 (3)	H15A—C15—H15B	109.5
C5—C4—C16	118.4 (3)	C8—C15—H15C	109.5
C6—C5—C4	122.9 (3)	H15A—C15—H15C	109.5
C6—C5—H5	118.6	H15B—C15—H15C	109.5
C4—C5—H5	118.6	C17—C16—C4	118.9 (3)
C5—C6—C7	116.2 (3)	C17—C16—H16A	107.6
C5—C6—H6	121.9	C4—C16—H16A	107.6
C7—C6—H6	121.9	C17—C16—H16B	107.6
O1—C7—C6	125.9 (3)	C4—C16—H16B	107.6
O1—C7—C2	110.9 (2)	H16A—C16—H16B	107.0
C6—C7—C2	123.2 (3)	C16—C17—H17A	109.5
O1—C8—C1	109.7 (2)	C16—C17—H17B	109.5
O1—C8—C15	115.4 (2)	H17A—C17—H17B	109.5
C1—C8—C15	134.8 (3)	C16—C17—H17C	109.5
C14—C9—C10	121.5 (2)	H17A—C17—H17C	109.5
C14—C9—S	119.7 (2)	H17B—C17—H17C	109.5
C10—C9—S	118.85 (19)
O2—S—C1—C8	−26.7 (3)	C1—C2—C7—C6	179.3 (3)
O3—S—C1—C8	−157.0 (2)	C7—O1—C8—C1	0.8 (3)
C9—S—C1—C8	89.1 (3)	C7—O1—C8—C15	−178.2 (2)
O2—S—C1—C2	155.7 (2)	C2—C1—C8—O1	−1.1 (3)
O3—S—C1—C2	25.4 (3)	S—C1—C8—O1	−179.00 (19)
C9—S—C1—C2	−88.5 (2)	C2—C1—C8—C15	177.7 (3)
C8—C1—C2—C3	−179.7 (3)	S—C1—C8—C15	−0.2 (5)
S—C1—C2—C3	−1.8 (5)	O2—S—C9—C14	10.3 (2)
C8—C1—C2—C7	0.9 (3)	O3—S—C9—C14	140.3 (2)
S—C1—C2—C7	178.8 (2)	C1—S—C9—C14	−106.4 (2)
C7—C2—C3—C4	−1.0 (4)	O2—S—C9—C10	−169.12 (19)
C1—C2—C3—C4	179.6 (3)	O3—S—C9—C10	−39.1 (2)
C2—C3—C4—C5	1.3 (4)	C1—S—C9—C10	74.3 (2)
C2—C3—C4—C16	−177.6 (3)	C14—C9—C10—C11	0.2 (4)
C3—C4—C5—C6	−0.3 (5)	S—C9—C10—C11	179.6 (2)
C16—C4—C5—C6	178.6 (3)	C9—C10—C11—C12	−0.4 (4)
C4—C5—C6—C7	−0.9 (5)	C10—C11—C12—C13	0.2 (4)
C8—O1—C7—C6	−179.9 (3)	C11—C12—C13—C14	0.1 (4)
C8—O1—C7—C2	−0.2 (3)	C12—C13—C14—C9	−0.3 (4)
C5—C6—C7—O1	−179.2 (3)	C10—C9—C14—C13	0.1 (4)
C5—C6—C7—C2	1.2 (4)	S—C9—C14—C13	−179.2 (2)
C3—C2—C7—O1	−179.9 (2)	C3—C4—C16—C17	5.8 (6)
C1—C2—C7—O1	−0.4 (3)	C5—C4—C16—C17	−173.1 (3)
C3—C2—C7—C6	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15C···Cg2i	0.98	2.80	3.592 (4)	139
C16—H16B···Cg2ii	0.98	3.21	3.903 (4)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15C⋯Cg2i	0.98	2.80	3.592 (4)	139
C16—H16B⋯Cg2ii	0.98	3.21	3.903 (4)	128

Symmetry codes: (i) ; (ii) .