2,5-Dimethyl-3-(4-methyl-phenyl-sulfin-yl)-1-benzofuran.

In the title compound, C(17)H(16)O(2)S, the 4-methyl-phenyl ring makes a dihedral angle of 88.28 (5)° with the mean plane [mean deviation = 0.009 (1) Å] of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C17H16O2S

M = 284.36

Orthorhombic,

a = 13.072 (2) Å

b = 6.1790 (11) Å

c = 17.979 (3) Å

V = 1452.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 173 K

0.37 × 0.23 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.624, T max = 0.746

13920 measured reflections

3587 independent reflections

3101 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.03

3587 reflections

184 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1729 Friedel pairs

Flack parameter: −0.01 (7)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812015450/fy2054sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015450/fy2054Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015450/fy2054Isup3.cml

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

C17H16O2S	F(000) = 600
Mr = 284.36	Dx = 1.301 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4157 reflections
a = 13.072 (2) Å	θ = 2.3–24.8°
b = 6.1790 (11) Å	µ = 0.22 mm−1
c = 17.979 (3) Å	T = 173 K
V = 1452.2 (4) Å3	Block, colourless
Z = 4	0.37 × 0.23 × 0.14 mm

Bruker SMART APEXII CCD diffractometer	3587 independent reflections
Radiation source: rotating anode	3101 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.036
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.3°
φ and ω scans	h = −17→16
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.624, Tmax = 0.746	l = −23→23
13920 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0445P)2 + 0.1605P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3587 reflections	Δρmax = 0.20 e Å−3
184 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 1729 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	0.68387 (4)	0.23443 (8)	0.43774 (3)	0.05093 (14)
O1	0.60322 (10)	0.2839 (2)	0.22842 (8)	0.0447 (3)
O2	0.79502 (12)	0.2480 (3)	0.45451 (10)	0.0708 (5)
C1	0.66469 (12)	0.3081 (3)	0.34471 (11)	0.0379 (4)
C2	0.70684 (12)	0.4873 (2)	0.30262 (10)	0.0332 (3)
C3	0.77327 (12)	0.6586 (3)	0.31664 (11)	0.0372 (4)
H3	0.8017	0.6784	0.3648	0.045*
C4	0.79736 (14)	0.7997 (3)	0.25939 (12)	0.0424 (4)
C5	0.75333 (16)	0.7692 (3)	0.18910 (12)	0.0482 (5)
H5	0.7702	0.8677	0.1504	0.058*
C6	0.68661 (15)	0.6026 (3)	0.17362 (10)	0.0464 (4)
H6	0.6566	0.5850	0.1259	0.056*
C7	0.66586 (12)	0.4626 (3)	0.23164 (10)	0.0373 (4)
C8	0.60458 (13)	0.1927 (3)	0.29798 (12)	0.0419 (4)
C9	0.87197 (17)	0.9835 (3)	0.27175 (15)	0.0580 (6)
H9A	0.8709	1.0260	0.3243	0.087*
H9B	0.8523	1.1073	0.2408	0.087*
H9C	0.9410	0.9362	0.2582	0.087*
C10	0.54077 (15)	−0.0042 (3)	0.30769 (17)	0.0602 (6)
H10A	0.5488	−0.0592	0.3585	0.090*
H10B	0.5626	−0.1152	0.2722	0.090*
H10C	0.4688	0.0320	0.2988	0.090*
C11	0.62497 (13)	0.4678 (3)	0.47906 (10)	0.0407 (4)
C12	0.52077 (14)	0.4978 (3)	0.47194 (11)	0.0455 (4)
H12	0.4809	0.3981	0.4440	0.055*
C13	0.47520 (14)	0.6721 (4)	0.50530 (11)	0.0473 (4)
H13	0.4035	0.6923	0.5000	0.057*
C14	0.53160 (17)	0.8206 (3)	0.54687 (10)	0.0472 (5)
C15	0.63554 (18)	0.7839 (4)	0.55478 (11)	0.0529 (5)
H15	0.6753	0.8810	0.5838	0.063*
C16	0.68289 (14)	0.6082 (4)	0.52116 (11)	0.0486 (5)
H16	0.7543	0.5851	0.5271	0.058*
C17	0.4802 (2)	1.0140 (4)	0.58236 (13)	0.0626 (6)
H17A	0.5321	1.1069	0.6053	0.094*
H17B	0.4320	0.9643	0.6205	0.094*
H17C	0.4431	1.0960	0.5443	0.094*

	U11	U22	U33	U12	U13	U23
S1	0.0432 (2)	0.0524 (3)	0.0572 (3)	0.0094 (2)	0.0020 (2)	0.0228 (2)
O1	0.0372 (7)	0.0416 (7)	0.0554 (8)	0.0033 (5)	−0.0021 (6)	−0.0123 (6)
O2	0.0427 (8)	0.1013 (12)	0.0683 (12)	0.0268 (8)	−0.0071 (7)	0.0186 (9)
C1	0.0299 (8)	0.0329 (8)	0.0510 (10)	0.0048 (6)	0.0042 (7)	0.0049 (7)
C2	0.0281 (7)	0.0322 (7)	0.0393 (9)	0.0079 (6)	0.0039 (6)	0.0027 (7)
C3	0.0280 (8)	0.0372 (8)	0.0463 (10)	0.0022 (6)	0.0015 (7)	0.0002 (7)
C4	0.0330 (10)	0.0349 (9)	0.0592 (12)	0.0053 (7)	0.0113 (8)	0.0065 (8)
C5	0.0470 (12)	0.0485 (11)	0.0491 (12)	0.0105 (8)	0.0163 (9)	0.0134 (8)
C6	0.0486 (11)	0.0535 (11)	0.0372 (10)	0.0151 (9)	0.0034 (8)	0.0018 (8)
C7	0.0311 (8)	0.0378 (8)	0.0429 (9)	0.0078 (7)	0.0009 (7)	−0.0067 (7)
C8	0.0281 (9)	0.0335 (8)	0.0642 (12)	0.0062 (7)	0.0052 (8)	−0.0022 (8)
C9	0.0430 (11)	0.0409 (10)	0.0902 (17)	−0.0045 (9)	0.0144 (10)	0.0083 (10)
C10	0.0396 (10)	0.0380 (10)	0.1032 (19)	−0.0061 (8)	0.0087 (12)	−0.0085 (11)
C11	0.0326 (9)	0.0529 (10)	0.0367 (9)	−0.0013 (7)	0.0003 (7)	0.0173 (8)
C12	0.0329 (9)	0.0591 (11)	0.0445 (10)	−0.0029 (8)	−0.0024 (8)	0.0038 (9)
C13	0.0319 (9)	0.0677 (12)	0.0422 (10)	0.0019 (9)	0.0002 (8)	0.0051 (9)
C14	0.0505 (12)	0.0567 (11)	0.0344 (9)	−0.0048 (9)	0.0035 (8)	0.0120 (8)
C15	0.0536 (13)	0.0640 (13)	0.0411 (10)	−0.0184 (10)	−0.0084 (9)	0.0090 (9)
C16	0.0321 (9)	0.0685 (12)	0.0451 (11)	−0.0071 (9)	−0.0069 (8)	0.0181 (9)
C17	0.0751 (15)	0.0605 (13)	0.0521 (13)	−0.0027 (12)	0.0094 (11)	0.0035 (10)

S1—O2	1.4864 (17)	C9—H9B	0.9800
S1—C1	1.751 (2)	C9—H9C	0.9800
S1—C11	1.795 (2)	C10—H10A	0.9800
O1—C8	1.372 (3)	C10—H10B	0.9800
O1—C7	1.376 (2)	C10—H10C	0.9800
C1—C8	1.354 (3)	C11—C16	1.378 (3)
C1—C2	1.450 (2)	C11—C12	1.381 (3)
C2—C3	1.392 (2)	C12—C13	1.369 (3)
C2—C7	1.392 (3)	C12—H12	0.9500
C3—C4	1.385 (3)	C13—C14	1.394 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.401 (3)	C14—C15	1.385 (3)
C4—C9	1.513 (3)	C14—C17	1.512 (3)
C5—C6	1.378 (3)	C15—C16	1.388 (3)
C5—H5	0.9500	C15—H15	0.9500
C6—C7	1.382 (3)	C16—H16	0.9500
C6—H6	0.9500	C17—H17A	0.9800
C8—C10	1.485 (2)	C17—H17B	0.9800
C9—H9A	0.9800	C17—H17C	0.9800
O2—S1—C1	108.60 (9)	H9A—C9—H9C	109.5
O2—S1—C11	106.86 (10)	H9B—C9—H9C	109.5
C1—S1—C11	97.17 (8)	C8—C10—H10A	109.5
C8—O1—C7	106.49 (14)	C8—C10—H10B	109.5
C8—C1—C2	107.41 (17)	H10A—C10—H10B	109.5
C8—C1—S1	122.59 (14)	C8—C10—H10C	109.5
C2—C1—S1	129.99 (14)	H10A—C10—H10C	109.5
C3—C2—C7	119.29 (16)	H10B—C10—H10C	109.5
C3—C2—C1	136.31 (17)	C16—C11—C12	120.55 (18)
C7—C2—C1	104.40 (15)	C16—C11—S1	119.83 (14)
C4—C3—C2	119.07 (17)	C12—C11—S1	119.51 (15)
C4—C3—H3	120.5	C13—C12—C11	119.63 (19)
C2—C3—H3	120.5	C13—C12—H12	120.2
C3—C4—C5	119.48 (17)	C11—C12—H12	120.2
C3—C4—C9	120.64 (19)	C12—C13—C14	121.49 (18)
C5—C4—C9	119.87 (18)	C12—C13—H13	119.3
C6—C5—C4	122.87 (18)	C14—C13—H13	119.3
C6—C5—H5	118.6	C15—C14—C13	117.8 (2)
C4—C5—H5	118.6	C15—C14—C17	121.5 (2)
C5—C6—C7	116.07 (18)	C13—C14—C17	120.7 (2)
C5—C6—H6	122.0	C14—C15—C16	121.39 (19)
C7—C6—H6	122.0	C14—C15—H15	119.3
O1—C7—C6	125.98 (17)	C16—C15—H15	119.3
O1—C7—C2	110.81 (16)	C11—C16—C15	119.12 (18)
C6—C7—C2	123.22 (17)	C11—C16—H16	120.4
C1—C8—O1	110.90 (15)	C15—C16—H16	120.4
C1—C8—C10	133.2 (2)	C14—C17—H17A	109.5
O1—C8—C10	115.87 (19)	C14—C17—H17B	109.5
C4—C9—H9A	109.5	H17A—C17—H17B	109.5
C4—C9—H9B	109.5	C14—C17—H17C	109.5
H9A—C9—H9B	109.5	H17A—C17—H17C	109.5
C4—C9—H9C	109.5	H17B—C17—H17C	109.5
O2—S1—C1—C8	133.66 (16)	C1—C2—C7—C6	179.67 (15)
C11—S1—C1—C8	−115.81 (15)	C2—C1—C8—O1	−0.62 (18)
O2—S1—C1—C2	−44.98 (18)	S1—C1—C8—O1	−179.53 (11)
C11—S1—C1—C2	65.56 (16)	C2—C1—C8—C10	−179.34 (18)
C8—C1—C2—C3	−178.81 (18)	S1—C1—C8—C10	1.8 (3)
S1—C1—C2—C3	0.0 (3)	C7—O1—C8—C1	0.57 (18)
C8—C1—C2—C7	0.41 (17)	C7—O1—C8—C10	179.54 (14)
S1—C1—C2—C7	179.21 (13)	O2—S1—C11—C16	−4.03 (17)
C7—C2—C3—C4	−0.3 (2)	C1—S1—C11—C16	−115.99 (15)
C1—C2—C3—C4	178.80 (17)	O2—S1—C11—C12	179.77 (14)
C2—C3—C4—C5	1.0 (2)	C1—S1—C11—C12	67.80 (15)
C2—C3—C4—C9	−177.99 (16)	C16—C11—C12—C13	1.8 (3)
C3—C4—C5—C6	−0.4 (3)	S1—C11—C12—C13	178.02 (15)
C9—C4—C5—C6	178.59 (17)	C11—C12—C13—C14	−0.3 (3)
C4—C5—C6—C7	−0.8 (3)	C12—C13—C14—C15	−1.3 (3)
C8—O1—C7—C6	179.98 (16)	C12—C13—C14—C17	179.07 (18)
C8—O1—C7—C2	−0.30 (17)	C13—C14—C15—C16	1.5 (3)
C5—C6—C7—O1	−178.81 (15)	C17—C14—C15—C16	−178.94 (19)
C5—C6—C7—C2	1.5 (3)	C12—C11—C16—C15	−1.7 (3)
C3—C2—C7—O1	179.32 (13)	S1—C11—C16—C15	−177.86 (14)
C1—C2—C7—O1	−0.07 (17)	C14—C15—C16—C11	0.0 (3)
C3—C2—C7—C6	−0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.95	2.60	3.334 (2)	134
C17—H17B···O1ii	0.98	2.52	3.387 (3)	148
C10—H10B···Cgiii	0.98	2.74	3.538 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.95	2.60	3.334 (2)	134
C17—H17B⋯O1ii	0.98	2.52	3.387 (3)	148
C10—H10B⋯Cgiii	0.98	2.74	3.538 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .