2,4,6,7-Tetra-methyl-3-phenyl-sulfinyl-1-benzofuran.

In the title compound, C(18)H(18)O(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the planar benzofuran fragment. The phenyl ring is nearly perpendicular to the benzofuran system [88.56 (7)°] and is tilted slightly towards it. Molecules form pseudo-helices along the a axis. The crystal structure is stabilized by a C-H⋯π inter-action between a methyl H atom and the phenyl ring of the phenyl-sulfinyl substituent, and by intra- and inter-molecular C-H⋯O inter-actions.

Related literature

For details of the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ▶); Ward (1997 ▶). For the structures of other benzofuran derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C18H18O2S

M = 298.38

Orthorhombic,

a = 12.0402 (6) Å

b = 19.673 (1) Å

c = 6.4399 (3) Å

V = 1525.40 (13) 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

9082 measured reflections

2486 independent reflections

2339 reflections with I > 2σ(I)

R int = 0.102

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.138

S = 1.08

2486 reflections

194 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.43 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/S1600536808015031/fl2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015031/fl2196Isup2.hkl

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

C18H18O2S	F000 = 632
Mr = 298.38	Dx = 1.299 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: p_2c_-2n	Cell parameters from 5414 reflections
a = 12.0402 (6) Å	θ = 2.7–28.2º
b = 19.673 (1) Å	µ = 0.21 mm−1
c = 6.4399 (3) Å	T = 173 (2) K
V = 1525.40 (13) Å3	Block, colorless
Z = 4	0.40 × 0.40 × 0.30 mm

Bruker SMART CCD diffractometer	2486 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.102
Detector resolution: 10.0 pixels mm-1	θmax = 27.0º
T = 173(2) K	θmin = 2.7º
φ and ω scans	h = −14→15
Absorption correction: none	k = −25→24
9082 measured reflections	l = −8→4

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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0864P)2 + 0.5202P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2486 reflections	Δρmax = 0.51 e Å−3
194 parameters	Δρmin = −0.43 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
S	0.60317 (5)	0.74039 (3)	0.74685 (15)	0.0220 (2)
O1	0.33116 (17)	0.63540 (10)	0.8280 (4)	0.0229 (5)
O2	0.71121 (16)	0.70681 (11)	0.6963 (4)	0.0308 (6)
C1	0.4924 (2)	0.68198 (13)	0.7252 (5)	0.0200 (6)
C2	0.4634 (2)	0.63018 (13)	0.5731 (5)	0.0199 (6)
C3	0.5073 (3)	0.60387 (14)	0.3879 (6)	0.0237 (6)
C4	0.4461 (3)	0.55262 (15)	0.2916 (5)	0.0274 (7)
H4	0.4744	0.5336	0.1668	0.033*
C5	0.3448 (3)	0.52741 (14)	0.3689 (6)	0.0277 (7)
C6	0.3011 (2)	0.55259 (14)	0.5539 (6)	0.0245 (7)
C7	0.3638 (2)	0.60360 (14)	0.6471 (5)	0.0207 (6)
C8	0.4118 (2)	0.68331 (14)	0.8720 (5)	0.0205 (6)
C9	0.5685 (2)	0.79514 (14)	0.5322 (5)	0.0204 (6)
C10	0.4647 (3)	0.82691 (15)	0.5279 (6)	0.0274 (7)
H10	0.4101	0.8171	0.6300	0.033*
C11	0.4437 (3)	0.87313 (16)	0.3706 (7)	0.0339 (8)
H11	0.3734	0.8950	0.3640	0.041*
C12	0.5237 (3)	0.88799 (16)	0.2224 (7)	0.0344 (8)
H12	0.5081	0.9202	0.1163	0.041*
C13	0.6266 (3)	0.85595 (15)	0.2287 (7)	0.0290 (7)
H13	0.6811	0.8658	0.1264	0.035*
C14	0.6494 (2)	0.80925 (14)	0.3858 (6)	0.0235 (7)
H14	0.7196	0.7874	0.3923	0.028*
C15	0.6131 (3)	0.62939 (17)	0.2903 (6)	0.0281 (8)
H15A	0.6436	0.5943	0.1986	0.042*
H15B	0.6672	0.6400	0.3994	0.042*
H15C	0.5975	0.6705	0.2095	0.042*
C16	0.2833 (3)	0.47364 (15)	0.2454 (9)	0.0399 (9)
H16A	0.2898	0.4297	0.3160	0.060*
H16B	0.3156	0.4703	0.1061	0.060*
H16C	0.2047	0.4862	0.2344	0.060*
C17	0.1937 (3)	0.52894 (17)	0.6488 (7)	0.0337 (8)
H17A	0.1314	0.5521	0.5812	0.051*
H17B	0.1935	0.5396	0.7975	0.051*
H17C	0.1862	0.4797	0.6296	0.051*
C18	0.3902 (3)	0.72565 (17)	1.0569 (6)	0.0270 (7)
H18A	0.4556	0.7536	1.0868	0.041*
H18B	0.3743	0.6963	1.1761	0.041*
H18C	0.3262	0.7552	1.0304	0.041*

	U11	U22	U33	U12	U13	U23
S	0.0194 (3)	0.0245 (3)	0.0222 (4)	−0.0027 (2)	−0.0002 (3)	−0.0011 (4)
O1	0.0215 (10)	0.0254 (10)	0.0219 (12)	−0.0032 (8)	0.0032 (9)	0.0003 (9)
O2	0.0200 (10)	0.0354 (11)	0.0369 (16)	0.0011 (8)	−0.0010 (10)	0.0046 (10)
C1	0.0186 (12)	0.0206 (12)	0.0208 (17)	−0.0016 (9)	−0.0004 (12)	0.0020 (13)
C2	0.0207 (14)	0.0170 (12)	0.0219 (16)	0.0013 (10)	−0.0010 (13)	0.0037 (12)
C3	0.0248 (14)	0.0217 (14)	0.0245 (17)	0.0062 (10)	0.0002 (13)	0.0007 (13)
C4	0.0332 (16)	0.0252 (14)	0.0239 (19)	0.0066 (11)	−0.0020 (14)	−0.0058 (12)
C5	0.0322 (17)	0.0164 (12)	0.034 (2)	0.0029 (11)	−0.0089 (15)	−0.0041 (14)
C6	0.0234 (14)	0.0177 (12)	0.0323 (19)	0.0013 (10)	−0.0036 (14)	0.0047 (13)
C7	0.0201 (12)	0.0185 (12)	0.0234 (17)	0.0022 (10)	0.0002 (13)	0.0037 (12)
C8	0.0194 (13)	0.0212 (13)	0.0210 (16)	−0.0017 (10)	0.0018 (13)	0.0036 (12)
C9	0.0205 (13)	0.0170 (13)	0.0237 (16)	0.0009 (10)	−0.0002 (12)	−0.0011 (12)
C10	0.0232 (15)	0.0250 (14)	0.0340 (19)	−0.0003 (11)	0.0061 (14)	−0.0015 (13)
C11	0.0251 (16)	0.0282 (16)	0.048 (2)	0.0039 (11)	0.0034 (16)	0.0082 (16)
C12	0.0428 (18)	0.0261 (14)	0.034 (2)	−0.0007 (12)	0.0011 (17)	0.0064 (16)
C13	0.0305 (15)	0.0271 (14)	0.029 (2)	−0.0045 (11)	0.0062 (17)	0.0021 (16)
C14	0.0204 (14)	0.0217 (12)	0.0282 (18)	0.0002 (10)	0.0054 (13)	−0.0048 (13)
C15	0.0266 (15)	0.0333 (15)	0.025 (2)	0.0041 (11)	0.0058 (14)	−0.0023 (13)
C16	0.0422 (18)	0.0277 (15)	0.050 (2)	−0.0004 (12)	−0.007 (2)	−0.012 (2)
C17	0.0294 (16)	0.0307 (16)	0.041 (2)	−0.0080 (12)	−0.0016 (16)	0.0059 (16)
C18	0.0251 (16)	0.0323 (15)	0.0236 (18)	−0.0001 (12)	0.0020 (14)	−0.0031 (14)

S—O2	1.495 (2)	C10—H10	0.9500
S—C1	1.766 (3)	C11—C12	1.387 (5)
S—C9	1.801 (3)	C11—H11	0.9500
O1—C7	1.379 (4)	C12—C13	1.391 (5)
O1—C8	1.383 (3)	C12—H12	0.9500
C1—C8	1.355 (4)	C13—C14	1.394 (5)
C1—C2	1.456 (4)	C13—H13	0.9500
C2—C7	1.393 (4)	C14—H14	0.9500
C2—C3	1.403 (5)	C15—H15A	0.9800
C3—C4	1.394 (4)	C15—H15B	0.9800
C3—C15	1.507 (4)	C15—H15C	0.9800
C4—C5	1.408 (5)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.393 (5)	C16—H16C	0.9800
C5—C16	1.516 (5)	C17—H17A	0.9800
C6—C7	1.392 (4)	C17—H17B	0.9800
C6—C17	1.504 (5)	C17—H17C	0.9800
C8—C18	1.476 (5)	C18—H18A	0.9800
C9—C14	1.383 (5)	C18—H18B	0.9800
C9—C10	1.398 (4)	C18—H18C	0.9800
C10—C11	1.385 (5)
O2—S—C1	110.63 (13)	C10—C11—H11	119.5
O2—S—C9	107.37 (15)	C12—C11—H11	119.5
C1—S—C9	98.84 (14)	C11—C12—C13	120.2 (3)
C7—O1—C8	106.4 (2)	C11—C12—H12	119.9
C8—C1—C2	108.1 (2)	C13—C12—H12	119.9
C8—C1—S	118.2 (2)	C12—C13—C14	119.7 (3)
C2—C1—S	133.6 (2)	C12—C13—H13	120.2
C7—C2—C3	118.5 (3)	C14—C13—H13	120.2
C7—C2—C1	103.8 (3)	C9—C14—C13	119.2 (3)
C3—C2—C1	137.7 (3)	C9—C14—H14	120.4
C4—C3—C2	116.5 (3)	C13—C14—H14	120.4
C4—C3—C15	120.1 (3)	C3—C15—H15A	109.5
C2—C3—C15	123.4 (3)	C3—C15—H15B	109.5
C3—C4—C5	123.7 (3)	H15A—C15—H15B	109.5
C3—C4—H4	118.1	C3—C15—H15C	109.5
C5—C4—H4	118.1	H15A—C15—H15C	109.5
C6—C5—C4	120.3 (3)	H15B—C15—H15C	109.5
C6—C5—C16	120.8 (3)	C5—C16—H16A	109.5
C4—C5—C16	118.9 (3)	C5—C16—H16B	109.5
C7—C6—C5	114.9 (3)	H16A—C16—H16B	109.5
C7—C6—C17	120.9 (3)	C5—C16—H16C	109.5
C5—C6—C17	124.2 (3)	H16A—C16—H16C	109.5
O1—C7—C6	122.5 (3)	H16B—C16—H16C	109.5
O1—C7—C2	111.3 (3)	C6—C17—H17A	109.5
C6—C7—C2	126.2 (3)	C6—C17—H17B	109.5
C1—C8—O1	110.3 (3)	H17A—C17—H17B	109.5
C1—C8—C18	134.4 (3)	C6—C17—H17C	109.5
O1—C8—C18	115.2 (3)	H17A—C17—H17C	109.5
C14—C9—C10	121.7 (3)	H17B—C17—H17C	109.5
C14—C9—S	118.7 (2)	C8—C18—H18A	109.5
C10—C9—S	119.3 (3)	C8—C18—H18B	109.5
C11—C10—C9	118.1 (3)	H18A—C18—H18B	109.5
C11—C10—H10	120.9	C8—C18—H18C	109.5
C9—C10—H10	120.9	H18A—C18—H18C	109.5
C10—C11—C12	121.0 (3)	H18B—C18—H18C	109.5
O2—S—C1—C8	138.4 (2)	C5—C6—C7—C2	−0.3 (4)
C9—S—C1—C8	−109.2 (3)	C17—C6—C7—C2	−179.2 (3)
O2—S—C1—C2	−43.7 (3)	C3—C2—C7—O1	−179.1 (2)
C9—S—C1—C2	68.7 (3)	C1—C2—C7—O1	0.4 (3)
C8—C1—C2—C7	−0.5 (3)	C3—C2—C7—C6	−0.4 (5)
S—C1—C2—C7	−178.5 (2)	C1—C2—C7—C6	179.2 (3)
C8—C1—C2—C3	179.0 (3)	C2—C1—C8—O1	0.3 (3)
S—C1—C2—C3	0.9 (6)	S—C1—C8—O1	178.72 (19)
C7—C2—C3—C4	0.2 (4)	C2—C1—C8—C18	−176.4 (3)
C1—C2—C3—C4	−179.2 (3)	S—C1—C8—C18	2.0 (5)
C7—C2—C3—C15	178.8 (3)	C7—O1—C8—C1	0.0 (3)
C1—C2—C3—C15	−0.6 (6)	C7—O1—C8—C18	177.4 (3)
C2—C3—C4—C5	0.6 (5)	O2—S—C9—C14	−13.1 (3)
C15—C3—C4—C5	−178.0 (3)	C1—S—C9—C14	−128.1 (3)
C3—C4—C5—C6	−1.4 (5)	O2—S—C9—C10	172.6 (2)
C3—C4—C5—C16	177.4 (3)	C1—S—C9—C10	57.6 (3)
C4—C5—C6—C7	1.2 (4)	C14—C9—C10—C11	0.5 (5)
C16—C5—C6—C7	−177.6 (3)	S—C9—C10—C11	174.7 (3)
C4—C5—C6—C17	−180.0 (3)	C9—C10—C11—C12	−0.6 (5)
C16—C5—C6—C17	1.3 (5)	C10—C11—C12—C13	0.6 (6)
C8—O1—C7—C6	−179.1 (3)	C11—C12—C13—C14	−0.6 (5)
C8—O1—C7—C2	−0.3 (3)	C10—C9—C14—C13	−0.5 (5)
C5—C6—C7—O1	178.3 (3)	S—C9—C14—C13	−174.7 (2)
C17—C6—C7—O1	−0.6 (5)	C12—C13—C14—C9	0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cgi	0.98	2.68	3.565 (5)	151
C10—H10···O2i	0.95	2.48	3.306 (4)	146
C15—H15B···O2	0.98	2.38	3.248 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cgi	0.98	2.68	3.565 (5)	151
C10—H10⋯O2i	0.95	2.48	3.306 (4)	146
C15—H15B⋯O2	0.98	2.38	3.248 (4)	147

Symmetry code: (i) . Cg is the centroid of the C9–C14 phenyl ring.