2-Meth-oxy-4-methyl-1-[1-(phenyl-sulfon-yl)propan-2-yl]benzene.

The title mol-ecule, C(17)H(20)O(3)S, displays a U-shaped structure; the two benzene rings are nearly parallel and partially overlapped to each other, the dihedral angle and centroid-to-centroid distance being 15.0 (2)° and 3.723 (2) Å. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules, forming supra-molecular chains running along the a axis.

Related literature

For propargylic sulfides as precusors of indene derivatives, see: Peng et al. (2007 ▶). For a related structure, see: Xi et al. (2004 ▶).

Experimental

Crystal data

C17H20O3S

M = 304.39

Monoclinic,

a = 9.101 (1) Å

b = 12.2579 (14) Å

c = 15.9251 (17) Å

β = 118.307 (1)°

V = 1564.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.42 × 0.27 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.915, T max = 0.973

7654 measured reflections

2754 independent reflections

1641 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.187

S = 1.08

2754 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035987/xu5314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035987/xu5314Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035987/xu5314Isup3.cml

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

C17H20O3S	F(000) = 648
Mr = 304.39	Dx = 1.293 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1375 reflections
a = 9.101 (1) Å	θ = 2.5–23.0°
b = 12.2579 (14) Å	µ = 0.21 mm−1
c = 15.9251 (17) Å	T = 298 K
β = 118.307 (1)°	Block, colorless
V = 1564.1 (3) Å3	0.42 × 0.27 × 0.13 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2754 independent reflections
Radiation source: fine-focus sealed tube	1641 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.915, Tmax = 0.973	k = −14→14
7654 measured reflections	l = −11→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0032P)2 + 0.4143P] where P = (Fo2 + 2Fc2)/3
2754 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
O1	0.9829 (3)	0.3534 (2)	0.33678 (17)	0.0512 (7)
O2	0.3680 (3)	0.4052 (2)	0.16790 (19)	0.0622 (8)
O3	0.4268 (4)	0.2682 (2)	0.2938 (2)	0.0677 (9)
S1	0.48398 (11)	0.33304 (8)	0.23977 (7)	0.0450 (3)
C1	0.6540 (4)	0.4104 (3)	0.3246 (2)	0.0419 (9)
H1A	0.6215	0.4415	0.3693	0.050*
H1B	0.7460	0.3608	0.3601	0.050*
C2	0.7182 (4)	0.5027 (3)	0.2863 (3)	0.0431 (9)
H2	0.6230	0.5508	0.2496	0.052*
C3	0.7823 (4)	0.4663 (3)	0.2192 (2)	0.0372 (9)
C4	0.9128 (4)	0.3909 (3)	0.2449 (3)	0.0394 (9)
C5	0.9644 (4)	0.3587 (3)	0.1804 (3)	0.0434 (9)
H5	1.0517	0.3091	0.1993	0.052*
C6	0.8891 (4)	0.3985 (3)	0.0877 (3)	0.0429 (9)
C7	0.7631 (4)	0.4745 (3)	0.0628 (3)	0.0470 (10)
H7	0.7123	0.5040	0.0016	0.056*
C8	0.7120 (4)	0.5070 (3)	0.1277 (3)	0.0453 (10)
H8	0.6270	0.5583	0.1091	0.054*
C9	0.8460 (5)	0.5702 (3)	0.3700 (3)	0.0619 (12)
H9A	0.9400	0.5253	0.4095	0.093*
H9B	0.7955	0.5973	0.4069	0.093*
H9C	0.8825	0.6305	0.3460	0.093*
C10	1.1077 (5)	0.2713 (4)	0.3645 (3)	0.0709 (13)
H10A	1.0622	0.2083	0.3246	0.106*
H10B	1.1445	0.2514	0.4298	0.106*
H10C	1.2005	0.2987	0.3579	0.106*
C11	0.9425 (5)	0.3583 (4)	0.0172 (3)	0.0630 (12)
H11A	0.9019	0.2854	−0.0021	0.095*
H11B	1.0621	0.3586	0.0463	0.095*
H11C	0.8975	0.4053	−0.0376	0.095*
C12	0.5631 (4)	0.2425 (3)	0.1847 (3)	0.0381 (9)
C13	0.6598 (5)	0.1548 (3)	0.2355 (3)	0.0529 (10)
H13	0.6851	0.1441	0.2987	0.063*
C14	0.7178 (6)	0.0837 (3)	0.1916 (4)	0.0674 (13)
H14	0.7839	0.0248	0.2255	0.081*
C15	0.6790 (6)	0.0988 (4)	0.0979 (4)	0.0694 (13)
H15	0.7183	0.0496	0.0687	0.083*
C16	0.5828 (5)	0.1856 (4)	0.0468 (3)	0.0628 (12)
H16	0.5575	0.1958	−0.0165	0.075*
C17	0.5239 (5)	0.2579 (3)	0.0910 (3)	0.0481 (10)
H17	0.4578	0.3168	0.0572	0.058*

	U11	U22	U33	U12	U13	U23
O1	0.0449 (15)	0.0676 (16)	0.0393 (15)	0.0191 (13)	0.0185 (13)	0.0142 (13)
O2	0.0437 (16)	0.0711 (17)	0.0598 (18)	0.0197 (13)	0.0147 (15)	0.0003 (15)
O3	0.074 (2)	0.0761 (18)	0.077 (2)	−0.0205 (16)	0.0555 (18)	−0.0102 (17)
S1	0.0406 (6)	0.0526 (6)	0.0480 (6)	−0.0027 (4)	0.0259 (5)	−0.0040 (5)
C1	0.044 (2)	0.0461 (19)	0.039 (2)	0.0018 (16)	0.0228 (18)	−0.0041 (17)
C2	0.045 (2)	0.0388 (19)	0.047 (2)	0.0029 (16)	0.0223 (19)	0.0027 (17)
C3	0.0347 (19)	0.0327 (17)	0.043 (2)	−0.0027 (15)	0.0171 (18)	0.0024 (16)
C4	0.036 (2)	0.043 (2)	0.037 (2)	−0.0035 (16)	0.0158 (18)	0.0027 (17)
C5	0.036 (2)	0.045 (2)	0.048 (2)	0.0028 (16)	0.0190 (19)	0.0011 (18)
C6	0.040 (2)	0.046 (2)	0.044 (2)	−0.0085 (16)	0.0200 (18)	−0.0016 (17)
C7	0.046 (2)	0.054 (2)	0.036 (2)	−0.0035 (18)	0.0164 (19)	0.0102 (18)
C8	0.042 (2)	0.041 (2)	0.051 (2)	0.0014 (16)	0.021 (2)	0.0116 (18)
C9	0.069 (3)	0.054 (2)	0.065 (3)	−0.009 (2)	0.034 (3)	−0.012 (2)
C10	0.058 (3)	0.095 (3)	0.063 (3)	0.039 (2)	0.032 (2)	0.035 (3)
C11	0.067 (3)	0.082 (3)	0.046 (2)	−0.005 (2)	0.031 (2)	−0.008 (2)
C12	0.035 (2)	0.0393 (18)	0.040 (2)	−0.0058 (15)	0.0178 (17)	−0.0037 (17)
C13	0.054 (2)	0.057 (2)	0.049 (2)	0.0062 (19)	0.025 (2)	0.008 (2)
C14	0.067 (3)	0.047 (2)	0.097 (4)	0.013 (2)	0.046 (3)	0.007 (3)
C15	0.079 (3)	0.058 (3)	0.085 (4)	0.000 (2)	0.050 (3)	−0.017 (3)
C16	0.070 (3)	0.072 (3)	0.052 (3)	−0.004 (2)	0.033 (2)	−0.012 (2)
C17	0.049 (2)	0.051 (2)	0.043 (2)	−0.0013 (18)	0.021 (2)	0.0019 (19)

O1—C4	1.369 (4)	C8—H8	0.9300
O1—C10	1.422 (4)	C9—H9A	0.9600
O2—S1	1.435 (3)	C9—H9B	0.9600
O3—S1	1.438 (3)	C9—H9C	0.9600
S1—C12	1.766 (4)	C10—H10A	0.9600
S1—C1	1.771 (3)	C10—H10B	0.9600
C1—C2	1.527 (5)	C10—H10C	0.9600
C1—H1A	0.9700	C11—H11A	0.9600
C1—H1B	0.9700	C11—H11B	0.9600
C2—C3	1.507 (5)	C11—H11C	0.9600
C2—C9	1.530 (5)	C12—C17	1.372 (5)
C2—H2	0.9800	C12—C13	1.382 (5)
C3—C8	1.378 (5)	C13—C14	1.370 (6)
C3—C4	1.404 (5)	C13—H13	0.9300
C4—C5	1.375 (5)	C14—C15	1.374 (6)
C5—C6	1.389 (5)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.373 (6)
C6—C7	1.382 (5)	C15—H15	0.9300
C6—C11	1.501 (5)	C16—C17	1.388 (5)
C7—C8	1.379 (5)	C16—H16	0.9300
C7—H7	0.9300	C17—H17	0.9300
C4—O1—C10	117.9 (3)	C2—C9—H9A	109.5
O2—S1—O3	118.67 (18)	C2—C9—H9B	109.5
O2—S1—C12	108.05 (17)	H9A—C9—H9B	109.5
O3—S1—C12	107.38 (16)	C2—C9—H9C	109.5
O2—S1—C1	108.94 (16)	H9A—C9—H9C	109.5
O3—S1—C1	105.84 (17)	H9B—C9—H9C	109.5
C12—S1—C1	107.48 (17)	O1—C10—H10A	109.5
C2—C1—S1	117.0 (2)	O1—C10—H10B	109.5
C2—C1—H1A	108.0	H10A—C10—H10B	109.5
S1—C1—H1A	108.0	O1—C10—H10C	109.5
C2—C1—H1B	108.0	H10A—C10—H10C	109.5
S1—C1—H1B	108.0	H10B—C10—H10C	109.5
H1A—C1—H1B	107.3	C6—C11—H11A	109.5
C3—C2—C1	114.4 (3)	C6—C11—H11B	109.5
C3—C2—C9	112.8 (3)	H11A—C11—H11B	109.5
C1—C2—C9	109.2 (3)	C6—C11—H11C	109.5
C3—C2—H2	106.6	H11A—C11—H11C	109.5
C1—C2—H2	106.6	H11B—C11—H11C	109.5
C9—C2—H2	106.6	C17—C12—C13	120.6 (4)
C8—C3—C4	116.8 (4)	C17—C12—S1	119.8 (3)
C8—C3—C2	120.0 (3)	C13—C12—S1	119.6 (3)
C4—C3—C2	123.2 (3)	C14—C13—C12	119.3 (4)
O1—C4—C5	123.4 (3)	C14—C13—H13	120.4
O1—C4—C3	115.7 (3)	C12—C13—H13	120.4
C5—C4—C3	120.9 (3)	C13—C14—C15	120.4 (4)
C4—C5—C6	121.5 (3)	C13—C14—H14	119.8
C4—C5—H5	119.3	C15—C14—H14	119.8
C6—C5—H5	119.3	C16—C15—C14	120.7 (4)
C7—C6—C5	117.8 (4)	C16—C15—H15	119.6
C7—C6—C11	121.7 (4)	C14—C15—H15	119.6
C5—C6—C11	120.5 (3)	C15—C16—C17	119.1 (4)
C8—C7—C6	120.6 (4)	C15—C16—H16	120.5
C8—C7—H7	119.7	C17—C16—H16	120.5
C6—C7—H7	119.7	C12—C17—C16	119.9 (4)
C3—C8—C7	122.4 (3)	C12—C17—H17	120.0
C3—C8—H8	118.8	C16—C17—H17	120.0
C7—C8—H8	118.8
O2—S1—C1—C2	−39.9 (3)	C5—C6—C7—C8	−1.6 (5)
O3—S1—C1—C2	−168.6 (3)	C11—C6—C7—C8	177.5 (3)
C12—S1—C1—C2	76.9 (3)	C4—C3—C8—C7	1.4 (5)
S1—C1—C2—C3	−60.9 (4)	C2—C3—C8—C7	−178.4 (3)
S1—C1—C2—C9	171.6 (3)	C6—C7—C8—C3	−0.1 (5)
C1—C2—C3—C8	121.4 (3)	O2—S1—C12—C17	7.0 (3)
C9—C2—C3—C8	−112.9 (4)	O3—S1—C12—C17	136.1 (3)
C1—C2—C3—C4	−58.5 (4)	C1—S1—C12—C17	−110.4 (3)
C9—C2—C3—C4	67.2 (4)	O2—S1—C12—C13	−171.0 (3)
C10—O1—C4—C5	−4.4 (5)	O3—S1—C12—C13	−41.9 (3)
C10—O1—C4—C3	175.7 (3)	C1—S1—C12—C13	71.6 (3)
C8—C3—C4—O1	178.7 (3)	C17—C12—C13—C14	0.7 (6)
C2—C3—C4—O1	−1.4 (5)	S1—C12—C13—C14	178.7 (3)
C8—C3—C4—C5	−1.2 (5)	C12—C13—C14—C15	−0.7 (6)
C2—C3—C4—C5	178.7 (3)	C13—C14—C15—C16	0.5 (7)
O1—C4—C5—C6	179.6 (3)	C14—C15—C16—C17	−0.5 (7)
C3—C4—C5—C6	−0.5 (5)	C13—C12—C17—C16	−0.7 (5)
C4—C5—C6—C7	1.9 (5)	S1—C12—C17—C16	−178.6 (3)
C4—C5—C6—C11	−177.3 (3)	C15—C16—C17—C12	0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2i	0.96	2.59	3.503 (6)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2i	0.96	2.59	3.503 (6)	159

Symmetry code: (i) .