2-[4-(Methyl-sulfon-yl)phen-yl]acetonitrile.

In the title compound, C(9)H(9)NO(2)S, the benzene ring and the acetonitrile group are approximately coplanar, with a C-C-C-C torsion angle of 1.1 (3)° between them. In the crystal, mol-ecules are linked via inter-molecular C-H⋯O hydrogen bonds into layers parallel to (001).

Related literature

For general background to and the biological activity of COX-2 inhibitors, see: Orjales et al. (2008 ▶); Zarghi et al. (2008 ▶); Shah et al. (2010 ▶); Arico et al. (2002 ▶); Davies et al. (2002 ▶); Sawaoka et al. (1998 ▶); Liu et al. (2000 ▶); Pasinetti (2001 ▶); Norman et al. (1995 ▶). For a related structure, see: Charlier et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H9NO2S

M = 195.23

Triclinic,

a = 5.5599 (2) Å

b = 8.0942 (3) Å

c = 10.9006 (4) Å

α = 81.162 (2)°

β = 85.347 (2)°

γ = 74.458 (2)°

V = 466.60 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.51 × 0.28 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.810, T max = 0.957

5970 measured reflections

1826 independent reflections

1673 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.110

S = 1.09

1826 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003837/is2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003837/is2671Isup2.hkl

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

C9H9NO2S	Z = 2
Mr = 195.23	F(000) = 204
Triclinic, P1	Dx = 1.390 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5599 (2) Å	Cell parameters from 4240 reflections
b = 8.0942 (3) Å	θ = 2.6–33.0°
c = 10.9006 (4) Å	µ = 0.31 mm−1
α = 81.162 (2)°	T = 296 K
β = 85.347 (2)°	Block, colourless
γ = 74.458 (2)°	0.51 × 0.28 × 0.14 mm
V = 466.60 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	1826 independent reflections
Radiation source: fine-focus sealed tube	1673 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.810, Tmax = 0.957	k = −9→9
5970 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.054P)2 + 0.1771P] where P = (Fo2 + 2Fc2)/3
1826 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.42 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
S1	0.64766 (8)	0.30347 (6)	0.36428 (4)	0.04502 (19)
O1	0.6714 (4)	0.45775 (18)	0.28743 (16)	0.0728 (5)
O2	0.4011 (3)	0.2889 (2)	0.40261 (19)	0.0773 (5)
N1	1.5750 (4)	−0.2897 (2)	−0.02043 (19)	0.0638 (5)
C1	1.1353 (3)	−0.0135 (2)	0.15700 (17)	0.0427 (4)
H1A	1.2799	−0.0114	0.1081	0.051*
C2	1.0162 (3)	0.1282 (2)	0.21644 (17)	0.0429 (4)
H2A	1.0801	0.2246	0.2080	0.051*
C3	0.8008 (3)	0.1237 (2)	0.28841 (15)	0.0365 (4)
C4	0.7055 (3)	−0.0194 (2)	0.30170 (17)	0.0439 (4)
H4A	0.5607	−0.0212	0.3505	0.053*
C5	0.8260 (3)	−0.1598 (2)	0.24231 (18)	0.0445 (4)
H5A	0.7620	−0.2561	0.2512	0.053*
C6	1.0422 (3)	−0.1580 (2)	0.16938 (15)	0.0370 (4)
C7	1.1679 (4)	−0.3160 (2)	0.10645 (18)	0.0464 (4)
H7A	1.2073	−0.4167	0.1694	0.056*
H7B	1.0511	−0.3343	0.0517	0.056*
C8	1.3966 (4)	−0.3021 (2)	0.03441 (18)	0.0468 (4)
C9	0.8180 (4)	0.2777 (3)	0.4977 (2)	0.0586 (5)
H9A	0.7482	0.3732	0.5433	0.088*
H9B	0.9891	0.2744	0.4738	0.088*
H9C	0.8100	0.1716	0.5490	0.088*

	U11	U22	U33	U12	U13	U23
S1	0.0405 (3)	0.0414 (3)	0.0506 (3)	−0.00199 (19)	−0.00442 (19)	−0.0129 (2)
O1	0.1054 (14)	0.0367 (8)	0.0691 (10)	−0.0059 (8)	−0.0101 (9)	−0.0042 (7)
O2	0.0381 (8)	0.0876 (12)	0.1116 (14)	−0.0088 (7)	0.0091 (8)	−0.0496 (11)
N1	0.0653 (12)	0.0591 (11)	0.0703 (12)	−0.0208 (9)	0.0182 (10)	−0.0217 (9)
C1	0.0428 (9)	0.0427 (10)	0.0458 (10)	−0.0169 (7)	0.0069 (7)	−0.0099 (7)
C2	0.0466 (10)	0.0382 (9)	0.0479 (10)	−0.0185 (7)	0.0028 (8)	−0.0079 (7)
C3	0.0367 (8)	0.0361 (8)	0.0354 (8)	−0.0072 (7)	−0.0024 (6)	−0.0042 (6)
C4	0.0390 (9)	0.0468 (10)	0.0474 (10)	−0.0153 (8)	0.0042 (7)	−0.0070 (8)
C5	0.0471 (10)	0.0393 (9)	0.0519 (10)	−0.0200 (8)	−0.0002 (8)	−0.0062 (8)
C6	0.0395 (9)	0.0366 (8)	0.0351 (8)	−0.0094 (7)	−0.0051 (7)	−0.0050 (7)
C7	0.0500 (10)	0.0394 (9)	0.0516 (11)	−0.0119 (8)	−0.0004 (8)	−0.0123 (8)
C8	0.0567 (12)	0.0381 (9)	0.0463 (10)	−0.0094 (8)	−0.0016 (9)	−0.0138 (8)
C9	0.0550 (12)	0.0689 (14)	0.0505 (11)	−0.0037 (10)	−0.0073 (9)	−0.0231 (10)

S1—O1	1.4239 (16)	C4—C5	1.381 (3)
S1—O2	1.4306 (16)	C4—H4A	0.9300
S1—C9	1.755 (2)	C5—C6	1.388 (2)
S1—C3	1.7657 (17)	C5—H5A	0.9300
N1—C8	1.136 (3)	C6—C7	1.519 (2)
C1—C6	1.385 (2)	C7—C8	1.461 (3)
C1—C2	1.387 (2)	C7—H7A	0.9700
C1—H1A	0.9300	C7—H7B	0.9700
C2—C3	1.383 (2)	C9—H9A	0.9600
C2—H2A	0.9300	C9—H9B	0.9600
C3—C4	1.382 (3)	C9—H9C	0.9600
O1—S1—O2	117.73 (12)	C4—C5—H5A	119.8
O1—S1—C9	108.35 (11)	C6—C5—H5A	119.8
O2—S1—C9	108.32 (12)	C1—C6—C5	119.12 (16)
O1—S1—C3	108.95 (9)	C1—C6—C7	122.56 (16)
O2—S1—C3	108.26 (9)	C5—C6—C7	118.32 (15)
C9—S1—C3	104.42 (9)	C8—C7—C6	113.81 (15)
C6—C1—C2	120.95 (16)	C8—C7—H7A	108.8
C6—C1—H1A	119.5	C6—C7—H7A	108.8
C2—C1—H1A	119.5	C8—C7—H7B	108.8
C3—C2—C1	118.95 (16)	C6—C7—H7B	108.8
C3—C2—H2A	120.5	H7A—C7—H7B	107.7
C1—C2—H2A	120.5	N1—C8—C7	179.0 (2)
C4—C3—C2	120.80 (16)	S1—C9—H9A	109.5
C4—C3—S1	119.91 (13)	S1—C9—H9B	109.5
C2—C3—S1	119.28 (13)	H9A—C9—H9B	109.5
C5—C4—C3	119.72 (16)	S1—C9—H9C	109.5
C5—C4—H4A	120.1	H9A—C9—H9C	109.5
C3—C4—H4A	120.1	H9B—C9—H9C	109.5
C4—C5—C6	120.45 (16)
C6—C1—C2—C3	−0.3 (3)	C2—C3—C4—C5	−0.1 (3)
C1—C2—C3—C4	0.3 (3)	S1—C3—C4—C5	−179.93 (13)
C1—C2—C3—S1	−179.94 (13)	C3—C4—C5—C6	0.0 (3)
O1—S1—C3—C4	−145.12 (16)	C2—C1—C6—C5	0.1 (3)
O2—S1—C3—C4	−15.97 (18)	C2—C1—C6—C7	−179.65 (16)
C9—S1—C3—C4	99.29 (17)	C4—C5—C6—C1	0.0 (3)
O1—S1—C3—C2	35.06 (17)	C4—C5—C6—C7	179.80 (16)
O2—S1—C3—C2	164.22 (15)	C1—C6—C7—C8	1.1 (3)
C9—S1—C3—C2	−80.53 (17)	C5—C6—C7—C8	−178.67 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1i	0.93	2.47	3.384 (2)	169
C9—H9B···O2ii	0.96	2.39	3.343 (3)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1i	0.93	2.47	3.384 (2)	169
C9—H9B⋯O2ii	0.96	2.39	3.343 (3)	175

Symmetry codes: (i) ; (ii) .