2,5-Dimethyl-3-phenyl-sulfonyl-1-benzofuran.

The title compound, C(16)H(14)O(3)S, was prepared by the oxidation of 2,5-dimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 76.98 (9)° with the plane of the benzofuran fragment. The crystal structure is stabilized by π-π inter-actions between furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.775 (4) Å]. In addition, the crystal structure exhibits intra- and inter-molecular C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C16H14O3S

M = 286.33

Triclinic,

a = 7.476 (4) Å

b = 9.448 (5) Å

c = 11.283 (6) Å

α = 110.834 (8)°

β = 95.651 (9)°

γ = 106.122 (9)°

V = 698.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.24 mm−1

T = 298 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

4916 measured reflections

2560 independent reflections

1967 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.165

S = 1.08

2560 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.33 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/S1600536808009811/sj2482sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009811/sj2482Isup2.hkl

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

C16H14O3S	Z = 2
Mr = 286.33	F000 = 300
Triclinic, P1	Dx = 1.362 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.476 (4) Å	Cell parameters from 2576 reflections
b = 9.448 (5) Å	θ = 2.5–28.2º
c = 11.283 (6) Å	µ = 0.24 mm−1
α = 110.834 (8)º	T = 298 (2) K
β = 95.651 (9)º	Block, colorless
γ = 106.122 (9)º	0.40 × 0.40 × 0.20 mm
V = 698.0 (6) Å3

Bruker SMART CCD diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	1967 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.077
Detector resolution: 10.0 pixels mm-1	θmax = 25.5º
T = 298(2) K	θmin = 2.0º
φ and ω scans	h = −9→9
Absorption correction: none	k = −11→11
4916 measured reflections	l = −13→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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.3092P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2560 reflections	Δρmax = 0.33 e Å−3
181 parameters	Δρmin = −0.32 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	0.48253 (10)	0.09684 (9)	0.28377 (7)	0.0479 (3)
O1	0.7729 (3)	0.5526 (2)	0.3996 (2)	0.0621 (6)
O2	0.3828 (3)	0.0486 (3)	0.37248 (19)	0.0587 (6)
O3	0.3765 (3)	0.0689 (3)	0.1608 (2)	0.0660 (6)
C1	0.6127 (4)	0.2991 (3)	0.3636 (3)	0.0469 (7)
C2	0.6846 (4)	0.3858 (3)	0.5024 (3)	0.0457 (7)
C3	0.6797 (4)	0.3508 (3)	0.6115 (3)	0.0492 (7)
H3	0.6177	0.2466	0.6032	0.059*
C4	0.7678 (5)	0.4719 (4)	0.7328 (3)	0.0585 (8)
C5	0.8626 (5)	0.6271 (4)	0.7433 (4)	0.0672 (9)
H5	0.9217	0.7078	0.8254	0.081*
C6	0.8716 (5)	0.6647 (4)	0.6369 (4)	0.0679 (10)
H6	0.9349	0.7686	0.6452	0.082*
C7	0.7827 (4)	0.5416 (3)	0.5174 (3)	0.0523 (8)
C8	0.6696 (4)	0.4052 (4)	0.3078 (3)	0.0551 (8)
C9	0.6558 (4)	0.0025 (3)	0.2563 (3)	0.0453 (7)
C10	0.7288 (5)	−0.0414 (4)	0.3494 (3)	0.0573 (8)
H10	0.6869	−0.0227	0.4266	0.069*
C11	0.8658 (6)	−0.1138 (4)	0.3250 (5)	0.0807 (12)
H11	0.9164	−0.1452	0.3862	0.097*
C12	0.9277 (6)	−0.1397 (4)	0.2115 (5)	0.0897 (14)
H12	1.0212	−0.1875	0.1965	0.108*
C13	0.8531 (6)	−0.0959 (5)	0.1201 (4)	0.0846 (13)
H13	0.8956	−0.1144	0.0430	0.102*
C14	0.7170 (5)	−0.0252 (4)	0.1413 (3)	0.0609 (9)
H14	0.6658	0.0042	0.0789	0.073*
C15	0.7617 (6)	0.4376 (5)	0.8531 (3)	0.0803 (11)
H15A	0.8192	0.3571	0.8480	0.096*
H15B	0.6315	0.3995	0.8596	0.096*
H15C	0.8307	0.5343	0.9283	0.096*
C16	0.6474 (6)	0.3918 (5)	0.1724 (4)	0.0784 (11)
H16A	0.7708	0.4175	0.1517	0.094*
H16B	0.5864	0.4652	0.1627	0.094*
H16C	0.5708	0.2839	0.1146	0.094*

	U11	U22	U33	U12	U13	U23
S	0.0448 (4)	0.0527 (4)	0.0352 (4)	0.0039 (3)	0.0014 (3)	0.0167 (3)
O1	0.0632 (13)	0.0498 (12)	0.0805 (17)	0.0183 (10)	0.0197 (12)	0.0338 (12)
O2	0.0548 (12)	0.0617 (13)	0.0447 (13)	0.0014 (10)	0.0117 (10)	0.0183 (10)
O3	0.0587 (12)	0.0829 (16)	0.0470 (14)	0.0146 (12)	−0.0054 (11)	0.0268 (12)
C1	0.0428 (14)	0.0491 (16)	0.0488 (18)	0.0137 (12)	0.0075 (13)	0.0217 (14)
C2	0.0395 (13)	0.0424 (15)	0.0505 (18)	0.0135 (11)	0.0072 (13)	0.0141 (13)
C3	0.0510 (15)	0.0442 (15)	0.0435 (18)	0.0126 (13)	0.0034 (14)	0.0118 (13)
C4	0.0577 (17)	0.0580 (19)	0.050 (2)	0.0242 (15)	0.0027 (15)	0.0097 (15)
C5	0.0649 (19)	0.0506 (18)	0.060 (2)	0.0172 (16)	−0.0003 (17)	−0.0023 (16)
C6	0.0588 (19)	0.0379 (16)	0.089 (3)	0.0111 (14)	0.0075 (19)	0.0111 (17)
C7	0.0473 (15)	0.0450 (16)	0.066 (2)	0.0183 (13)	0.0126 (15)	0.0221 (15)
C8	0.0525 (17)	0.0607 (19)	0.061 (2)	0.0214 (15)	0.0129 (15)	0.0324 (17)
C9	0.0481 (14)	0.0387 (13)	0.0333 (15)	0.0015 (11)	−0.0006 (12)	0.0089 (11)
C10	0.0599 (18)	0.0500 (17)	0.0522 (19)	0.0051 (15)	−0.0004 (15)	0.0228 (15)
C11	0.075 (2)	0.052 (2)	0.103 (3)	0.0119 (18)	−0.013 (2)	0.032 (2)
C12	0.074 (2)	0.051 (2)	0.121 (4)	0.0243 (19)	0.013 (3)	0.007 (2)
C13	0.092 (3)	0.064 (2)	0.076 (3)	0.023 (2)	0.030 (2)	0.002 (2)
C14	0.072 (2)	0.0576 (19)	0.0381 (17)	0.0135 (16)	0.0081 (16)	0.0098 (14)
C15	0.098 (3)	0.080 (3)	0.047 (2)	0.034 (2)	−0.003 (2)	0.0103 (18)
C16	0.087 (3)	0.089 (3)	0.078 (3)	0.028 (2)	0.020 (2)	0.056 (2)

S—O3	1.425 (2)	C8—C16	1.476 (4)
S—O2	1.431 (2)	C9—C10	1.376 (4)
S—C1	1.726 (3)	C9—C14	1.380 (4)
S—C9	1.758 (3)	C10—C11	1.380 (5)
O1—C8	1.353 (4)	C10—H10	0.9300
O1—C7	1.366 (4)	C11—C12	1.367 (6)
C1—C8	1.359 (4)	C11—H11	0.9300
C1—C2	1.446 (4)	C12—C13	1.366 (6)
C2—C3	1.385 (4)	C12—H12	0.9300
C2—C7	1.389 (4)	C13—C14	1.360 (6)
C3—C4	1.381 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.396 (5)	C15—H15A	0.9600
C4—C15	1.505 (5)	C15—H15B	0.9600
C5—C6	1.370 (5)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.375 (5)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
O3—S—O2	118.96 (14)	C10—C9—C14	121.2 (3)
O3—S—C1	109.04 (14)	C10—C9—S	119.9 (2)
O2—S—C1	107.44 (13)	C14—C9—S	119.0 (3)
O3—S—C9	108.12 (14)	C9—C10—C11	118.3 (3)
O2—S—C9	107.90 (14)	C9—C10—H10	120.9
C1—S—C9	104.45 (14)	C11—C10—H10	120.9
C8—O1—C7	107.4 (2)	C12—C11—C10	120.5 (4)
C8—C1—C2	107.5 (3)	C12—C11—H11	119.8
C8—C1—S	126.5 (3)	C10—C11—H11	119.8
C2—C1—S	126.0 (2)	C13—C12—C11	120.4 (4)
C3—C2—C7	119.1 (3)	C13—C12—H12	119.8
C3—C2—C1	136.9 (3)	C11—C12—H12	119.8
C7—C2—C1	104.0 (3)	C14—C13—C12	120.3 (4)
C4—C3—C2	119.4 (3)	C14—C13—H13	119.8
C4—C3—H3	120.3	C12—C13—H13	119.8
C2—C3—H3	120.3	C13—C14—C9	119.4 (4)
C3—C4—C5	119.4 (3)	C13—C14—H14	120.3
C3—C4—C15	120.5 (3)	C9—C14—H14	120.3
C5—C4—C15	120.1 (3)	C4—C15—H15A	109.5
C6—C5—C4	122.4 (3)	C4—C15—H15B	109.5
C6—C5—H5	118.8	H15A—C15—H15B	109.5
C4—C5—H5	118.8	C4—C15—H15C	109.5
C5—C6—C7	116.9 (3)	H15A—C15—H15C	109.5
C5—C6—H6	121.6	H15B—C15—H15C	109.5
C7—C6—H6	121.6	C8—C16—H16A	109.5
O1—C7—C6	126.5 (3)	C8—C16—H16B	109.5
O1—C7—C2	110.7 (3)	H16A—C16—H16B	109.5
C6—C7—C2	122.8 (3)	C8—C16—H16C	109.5
O1—C8—C1	110.4 (3)	H16A—C16—H16C	109.5
O1—C8—C16	115.5 (3)	H16B—C16—H16C	109.5
C1—C8—C16	134.1 (3)
O3—S—C1—C8	−24.0 (3)	C3—C2—C7—C6	−1.8 (5)
O2—S—C1—C8	−154.2 (3)	C1—C2—C7—C6	178.9 (3)
C9—S—C1—C8	91.3 (3)	C7—O1—C8—C1	0.0 (3)
O3—S—C1—C2	157.4 (2)	C7—O1—C8—C16	−178.4 (3)
O2—S—C1—C2	27.2 (3)	C2—C1—C8—O1	0.3 (4)
C9—S—C1—C2	−87.2 (3)	S—C1—C8—O1	−178.5 (2)
C8—C1—C2—C3	−179.4 (3)	C2—C1—C8—C16	178.2 (4)
S—C1—C2—C3	−0.6 (5)	S—C1—C8—C16	−0.6 (6)
C8—C1—C2—C7	−0.4 (3)	O3—S—C9—C10	−156.0 (2)
S—C1—C2—C7	178.4 (2)	O2—S—C9—C10	−26.2 (2)
C7—C2—C3—C4	1.7 (4)	C1—S—C9—C10	87.9 (2)
C1—C2—C3—C4	−179.4 (3)	O3—S—C9—C14	24.4 (3)
C2—C3—C4—C5	−0.9 (5)	O2—S—C9—C14	154.3 (2)
C2—C3—C4—C15	179.0 (3)	C1—S—C9—C14	−91.6 (2)
C3—C4—C5—C6	0.2 (6)	C14—C9—C10—C11	0.2 (4)
C15—C4—C5—C6	−179.8 (3)	S—C9—C10—C11	−179.4 (2)
C4—C5—C6—C7	−0.2 (5)	C9—C10—C11—C12	0.5 (5)
C8—O1—C7—C6	−178.7 (3)	C10—C11—C12—C13	−0.8 (6)
C8—O1—C7—C2	−0.2 (3)	C11—C12—C13—C14	0.3 (6)
C5—C6—C7—O1	179.4 (3)	C12—C13—C14—C9	0.3 (5)
C5—C6—C7—C2	1.1 (5)	C10—C9—C14—C13	−0.6 (4)
C3—C2—C7—O1	179.6 (2)	S—C9—C14—C13	179.0 (2)
C1—C2—C7—O1	0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.93	2.45	3.345 (4)	160
C14—H14···O3ii	0.93	2.50	3.263 (4)	139
C16—H16C···O3	0.96	2.40	3.108 (4)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.93	2.45	3.345 (4)	160
C14—H14⋯O3ii	0.93	2.50	3.263 (4)	139
C16—H16C⋯O3	0.96	2.40	3.108 (4)	130

Symmetry codes: (i) ; (ii) .