1-[(4,5-Dimethyl-cyclo-hexa-1,4-dien-1-yl)sulfon-yl]-4-methyl-benzene.

In the title mol-ecule, C(15)H(18)O(2)S, the dimethyl-cyclo-hexa-diene unit is slightly non-planar, having a folded conformation with the two double-bond planes forming a dihedral angle of 3.9 (6)°. Methyl groups of the dimethyl-cyclo-hexa-diene ring tilt away from each other, forming inter-nal C-C-C(Me) angles approximately 11° greater than the exterior angles.

Related literature

For related literature, see: Filatov et al. (2007 ▶); Glidewell et al. (2001 ▶); Loudet & Burgess (2007 ▶); Ogura et al. (2001 ▶); Tanui et al. (2008 ▶); Ongayi (2005 ▶); Pomarico (2009 ▶).

Experimental

Crystal data

C15H18O2S

M = 262.35

Monoclinic,

a = 14.1607 (10) Å

b = 7.5766 (5) Å

c = 12.6923 (10) Å

β = 101.658 (5)°

V = 1333.66 (17) Å3

Z = 4

Cu Kα radiation

μ = 2.08 mm−1

T = 90 K

0.37 × 0.29 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.513, T max = 0.669

8185 measured reflections

2414 independent reflections

2388 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.079

S = 1.02

2414 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021260/fl2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021260/fl2208Isup2.hkl

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

C15H18O2S	F000 = 560
Mr = 262.35	Dx = 1.307 Mg m−3
Monoclinic, P21/c	Cu Kα radiation λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 6824 reflections
a = 14.1607 (10) Å	θ = 3.1–69.6º
b = 7.5766 (5) Å	µ = 2.08 mm−1
c = 12.6923 (10) Å	T = 90 K
β = 101.658 (5)º	Needle fragment, colourless
V = 1333.66 (17) Å3	0.37 × 0.29 × 0.21 mm
Z = 4

Bruker Kappa APEXII CCD area-detector diffractometer	2414 independent reflections
Radiation source: fine-focus sealed tube	2388 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 90 K	θmax = 70.0º
φ and ω scans	θmin = 6.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2008)	h = −16→17
Tmin = 0.513, Tmax = 0.669	k = −8→8
8185 measured reflections	l = −14→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0349P)2 + 1.1601P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.079	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.39 e Å−3
2414 reflections	Δρmin = −0.35 e Å−3
167 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (2)
Secondary atom site location: difference Fourier map

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
S1	0.72081 (2)	0.65111 (5)	0.77242 (3)	0.01466 (12)
O1	0.77069 (8)	0.81816 (14)	0.78620 (9)	0.0217 (3)
O2	0.69509 (8)	0.57537 (14)	0.66619 (8)	0.0203 (2)
C1	0.78977 (10)	0.4965 (2)	0.85979 (11)	0.0150 (3)
C2	0.84519 (10)	0.5644 (2)	0.96471 (12)	0.0181 (3)
H2A	0.8013	0.6342	1.0001	0.022*
H2B	0.8964	0.6447	0.9507	0.022*
C3	0.89062 (10)	0.4216 (2)	1.04018 (12)	0.0192 (3)
C4	0.88460 (10)	0.2504 (2)	1.01358 (12)	0.0199 (3)
C5	0.83462 (11)	0.1878 (2)	0.90446 (12)	0.0213 (3)
H5A	0.8827	0.1294	0.8695	0.026*
H5B	0.7863	0.0978	0.9137	0.026*
C6	0.78555 (10)	0.3272 (2)	0.83147 (12)	0.0172 (3)
H6	0.7501	0.2946	0.7625	0.021*
C7	0.93992 (11)	0.4914 (2)	1.14845 (12)	0.0258 (4)
H7A	0.8916	0.5402	1.1857	0.039*
H7B	0.9856	0.5841	1.1388	0.039*
H7C	0.9746	0.3951	1.1913	0.039*
C8	0.92390 (13)	0.1033 (3)	1.09036 (14)	0.0301 (4)
H8A	0.9855	0.1401	1.1352	0.045*
H8B	0.9339	−0.0023	1.0494	0.045*
H8C	0.8779	0.0768	1.1364	0.045*
C9	0.61462 (10)	0.67078 (18)	0.82478 (11)	0.0138 (3)
C10	0.53295 (10)	0.57652 (19)	0.77775 (12)	0.0171 (3)
H10	0.5326	0.5072	0.7153	0.021*
C11	0.45159 (10)	0.58476 (19)	0.82322 (12)	0.0185 (3)
H11	0.3950	0.5229	0.7903	0.022*
C12	0.45178 (11)	0.6823 (2)	0.91624 (12)	0.0178 (3)
C13	0.53499 (11)	0.7747 (2)	0.96241 (11)	0.0177 (3)
H13	0.5361	0.8410	1.0262	0.021*
C14	0.61613 (10)	0.77178 (19)	0.91700 (11)	0.0157 (3)
H14	0.6719	0.8375	0.9482	0.019*
C15	0.36432 (12)	0.6882 (2)	0.96662 (13)	0.0248 (4)
H15A	0.3324	0.8029	0.9519	0.037*
H15B	0.3841	0.6716	1.0445	0.037*
H15C	0.3196	0.5940	0.9363	0.037*

	U11	U22	U33	U12	U13	U23
S1	0.01540 (19)	0.0156 (2)	0.01337 (19)	0.00057 (13)	0.00388 (13)	0.00124 (13)
O1	0.0225 (6)	0.0181 (5)	0.0260 (6)	−0.0034 (4)	0.0087 (4)	0.0027 (4)
O2	0.0232 (5)	0.0250 (6)	0.0128 (5)	0.0045 (4)	0.0039 (4)	0.0005 (4)
C1	0.0121 (6)	0.0188 (7)	0.0144 (7)	0.0010 (6)	0.0034 (5)	0.0008 (6)
C2	0.0149 (7)	0.0216 (8)	0.0172 (7)	0.0000 (6)	0.0018 (6)	−0.0032 (6)
C3	0.0123 (7)	0.0312 (9)	0.0144 (7)	0.0017 (6)	0.0037 (5)	−0.0014 (6)
C4	0.0153 (7)	0.0277 (9)	0.0175 (7)	0.0048 (6)	0.0055 (6)	0.0029 (6)
C5	0.0217 (8)	0.0199 (8)	0.0226 (8)	0.0034 (6)	0.0050 (6)	0.0005 (6)
C6	0.0152 (7)	0.0207 (8)	0.0155 (7)	−0.0004 (6)	0.0030 (6)	−0.0018 (6)
C7	0.0205 (8)	0.0399 (10)	0.0161 (7)	0.0047 (7)	0.0013 (6)	−0.0043 (7)
C8	0.0313 (9)	0.0366 (10)	0.0236 (8)	0.0125 (8)	0.0086 (7)	0.0093 (7)
C9	0.0147 (7)	0.0127 (7)	0.0141 (7)	0.0020 (5)	0.0033 (5)	0.0029 (5)
C10	0.0196 (7)	0.0139 (7)	0.0168 (7)	0.0017 (6)	0.0015 (6)	−0.0002 (6)
C11	0.0156 (7)	0.0143 (7)	0.0244 (8)	−0.0011 (5)	0.0012 (6)	0.0026 (6)
C12	0.0189 (7)	0.0151 (7)	0.0199 (7)	0.0051 (6)	0.0055 (6)	0.0084 (6)
C13	0.0219 (7)	0.0169 (7)	0.0141 (7)	0.0050 (6)	0.0031 (6)	0.0013 (6)
C14	0.0166 (7)	0.0140 (7)	0.0154 (7)	0.0014 (5)	0.0002 (5)	0.0007 (6)
C15	0.0224 (8)	0.0252 (8)	0.0292 (9)	0.0051 (6)	0.0110 (7)	0.0089 (7)

S1—O1	1.4427 (11)	C7—H7C	0.9800
S1—O2	1.4427 (11)	C8—H8A	0.9800
S1—C1	1.7656 (14)	C8—H8B	0.9800
S1—C9	1.7687 (14)	C8—H8C	0.9800
C1—C6	1.331 (2)	C9—C10	1.387 (2)
C1—C2	1.4939 (19)	C9—C14	1.395 (2)
C2—C3	1.501 (2)	C10—C11	1.390 (2)
C2—H2A	0.9900	C10—H10	0.9500
C2—H2B	0.9900	C11—C12	1.392 (2)
C3—C4	1.339 (2)	C11—H11	0.9500
C3—C7	1.506 (2)	C12—C13	1.394 (2)
C4—C5	1.499 (2)	C12—C15	1.505 (2)
C4—C8	1.511 (2)	C13—C14	1.386 (2)
C5—C6	1.482 (2)	C13—H13	0.9500
C5—H5A	0.9900	C14—H14	0.9500
C5—H5B	0.9900	C15—H15A	0.9800
C6—H6	0.9500	C15—H15B	0.9800
C7—H7A	0.9800	C15—H15C	0.9800
C7—H7B	0.9800
O1—S1—O2	119.15 (7)	C3—C7—H7C	109.5
O1—S1—C1	108.10 (7)	H7A—C7—H7C	109.5
O2—S1—C1	109.04 (7)	H7B—C7—H7C	109.5
O1—S1—C9	108.25 (7)	C4—C8—H8A	109.5
O2—S1—C9	108.14 (7)	C4—C8—H8B	109.5
C1—S1—C9	102.96 (6)	H8A—C8—H8B	109.5
C6—C1—C2	124.03 (13)	C4—C8—H8C	109.5
C6—C1—S1	118.76 (11)	H8A—C8—H8C	109.5
C2—C1—S1	117.11 (11)	H8B—C8—H8C	109.5
C1—C2—C3	113.62 (13)	C10—C9—C14	120.90 (13)
C1—C2—H2A	108.8	C10—C9—S1	119.54 (11)
C3—C2—H2A	108.8	C14—C9—S1	119.43 (11)
C1—C2—H2B	108.8	C9—C10—C11	119.14 (13)
C3—C2—H2B	108.8	C9—C10—H10	120.4
H2A—C2—H2B	107.7	C11—C10—H10	120.4
C4—C3—C2	122.71 (13)	C10—C11—C12	121.07 (14)
C4—C3—C7	124.36 (15)	C10—C11—H11	119.5
C2—C3—C7	112.90 (14)	C12—C11—H11	119.5
C3—C4—C5	122.24 (14)	C11—C12—C13	118.66 (14)
C3—C4—C8	123.76 (15)	C11—C12—C15	121.03 (14)
C5—C4—C8	113.97 (14)	C13—C12—C15	120.31 (14)
C6—C5—C4	115.24 (13)	C14—C13—C12	121.22 (14)
C6—C5—H5A	108.5	C14—C13—H13	119.4
C4—C5—H5A	108.5	C12—C13—H13	119.4
C6—C5—H5B	108.5	C13—C14—C9	118.98 (13)
C4—C5—H5B	108.5	C13—C14—H14	120.5
H5A—C5—H5B	107.5	C9—C14—H14	120.5
C1—C6—C5	121.90 (14)	C12—C15—H15A	109.5
C1—C6—H6	119.0	C12—C15—H15B	109.5
C5—C6—H6	119.0	H15A—C15—H15B	109.5
C3—C7—H7A	109.5	C12—C15—H15C	109.5
C3—C7—H7B	109.5	H15A—C15—H15C	109.5
H7A—C7—H7B	109.5	H15B—C15—H15C	109.5
O1—S1—C1—C6	−150.24 (12)	C4—C5—C6—C1	3.0 (2)
O2—S1—C1—C6	−19.33 (14)	O1—S1—C9—C10	147.20 (11)
C9—S1—C1—C6	95.35 (13)	O2—S1—C9—C10	16.82 (13)
O1—S1—C1—C2	33.22 (12)	C1—S1—C9—C10	−98.50 (12)
O2—S1—C1—C2	164.13 (10)	O1—S1—C9—C14	−36.97 (13)
C9—S1—C1—C2	−81.20 (12)	O2—S1—C9—C14	−167.34 (11)
C6—C1—C2—C3	−4.3 (2)	C1—S1—C9—C14	77.34 (12)
S1—C1—C2—C3	172.03 (10)	C14—C9—C10—C11	0.5 (2)
C1—C2—C3—C4	2.4 (2)	S1—C9—C10—C11	176.30 (11)
C1—C2—C3—C7	−175.74 (12)	C9—C10—C11—C12	−1.6 (2)
C2—C3—C4—C5	2.1 (2)	C10—C11—C12—C13	1.1 (2)
C7—C3—C4—C5	−179.99 (14)	C10—C11—C12—C15	−178.78 (13)
C2—C3—C4—C8	−175.78 (14)	C11—C12—C13—C14	0.5 (2)
C7—C3—C4—C8	2.1 (2)	C15—C12—C13—C14	−179.66 (13)
C3—C4—C5—C6	−4.9 (2)	C12—C13—C14—C9	−1.5 (2)
C8—C4—C5—C6	173.25 (13)	C10—C9—C14—C13	1.0 (2)
C2—C1—C6—C5	1.6 (2)	S1—C9—C14—C13	−174.79 (11)
S1—C1—C6—C5	−174.69 (11)