2-[4-(Methyl­sulfon­yl)phen­yl]acetonitrile

Hoong-Kun Fun; Ching Kheng Quah; V Sumangala; D Jagadeesh Prasad; Boja Poojary

doi:10.1107/S1600536811003837

. 2011 Feb 5;67(Pt 3):o574. doi: 10.1107/S1600536811003837

2-[4-(Methylsulfonyl)phenyl]acetonitrile

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, V Sumangala ^b, D Jagadeesh Prasad ^b, Boja Poojary ^b

PMCID: PMC3052001 PMID: 21522336

Abstract

In the title compound, C₉H₉NO₂S, 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, molecules are linked via intermolecular 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 _r = 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
Δρ_max = 0.29 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

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

e-67-0o574-sup1.cif^{(15.4KB, cif)}

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

e-67-0o574-Isup2.hkl^{(89.9KB, hkl)}

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

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

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Compounds bearing the 4-methylsulfonylphenyl moiety are found to possess diverse biological properties. They are found to be highly potent and specific COX-2 inhibitors (Orjales et al., 2008; Zarghi et al., 2008; Shah et al., 2010). Recent studies have shown that selective COX-2 inhibitors can induce apoptosis in colon, stomach, prostate, and breast cancer cell lines (Arico et al., 2002; Davies et al., 2002; Sawaoka et al., 1998; Liu et al., 2000). Selective COX-2 inhibitors offer potential treatment for the prophylactic prevention of inflammatory neurodegerative disorders such as Alzheimer's disease (Pasinetti, 2001). They are also found to be anti-inflammatory agents (Norman et al., 1995). The crystal structure of a methylsulfonylphenyl derivative has been reported (Charlier et al., 2004).

The molecular structure is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzene ring (C1–C6) and the acetonitrile group (C7/C8/N1) are approximately coplanar [torsion angles C1—C6—C7—C8 = 1.1 (3) and C5—C6—C7—C8 = -178.67 (16) °]. In the crystal packing (Fig. 2), the molecules are linked via intermolecular C5–H5A···O1 and C9–H9B···O2 (Table 1) hydrogen bonds into infinite two-dimensional planes parallel to (001).

Experimental

4-Methylthiophenylacetonitrile (0.1 mol) was taken in 3 mL of acetic anhydride and cooled to 5°C. To the reaction mixture sodium tungstate (0.02 mol) was added followed by 30% hydrogen peroxide (0.2 mol) in 1.2 mL of acetic acid and water mixture (in 2:1 ratio). The temperature of the reaction mixture was slowly brought to room temperature. The completion of reaction was monitored by TLC. The solid precipitate was filtered and washed with water until the pH became neutral. The product was dried at 65 °C for 10-12 h. The product was then recrystallized in methanol (m. p.: 120–124 °C).