(Z)-1-(4-Methyl­phen­yl)-2-(phenyl­sulfon­yl)ethanone oxime

Hoong-Kun Fun; Tze Shyang Chia; Khalid A Al-Rashood; Hatem A Abdel-Aziz

doi:10.1107/S1600536812030346

. 2012 Jul 7;68(Pt 8):o2369. doi: 10.1107/S1600536812030346

(Z)-1-(4-Methylphenyl)-2-(phenylsulfonyl)ethanone oxime

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Khalid A Al-Rashood ^b, Hatem A Abdel-Aziz ^b

PMCID: PMC3414300 PMID: 22904833

Abstract

The molecule of the title compound, C₁₅H₁₅NO₃S, has a twisted U-shaped conformation: the twist occurs at the central C—S(=O)₂—C—C—C unit and the benzene ring makes a dihedral angle of 28.74 (7)° with the phenyl ring. The S—C—C=N torsion angle is −88.95 (13)°. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R ₂ ²(6) loops, and C—H⋯O hydrogen bonds connect the dimers into a three-dimensional network.

Related literature

For the biological activity of arylsulphones, see: Stephens et al. (2001 ▶); Abdel-Aziz et al. (2010 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₅H₁₅NO₃S
M _r = 289.34
Monoclinic,
a = 5.2305 (3) Å
b = 17.6073 (11) Å
c = 15.6578 (10) Å
β = 103.782 (2)°
V = 1400.49 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.29 × 0.09 × 0.06 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.934, T _max = 0.985
16727 measured reflections
4349 independent reflections
3578 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.03
4349 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.33 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 datablock(s) global, I. DOI: 10.1107/S1600536812030346/hb6884sup1.cif

e-68-o2369-sup1.cif^{(24KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030346/hb6884Isup2.hkl

e-68-o2369-Isup2.hkl^{(213.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030346/hb6884Isup3.cml

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
O3—H1O3⋯N1ⁱ	0.97 (2)	1.88 (2)	2.7819 (15)	153.8 (18)
C2—H2A⋯O2ⁱⁱ	0.93	2.53	3.2413 (18)	134
C3—H3A⋯O1ⁱⁱⁱ	0.93	2.56	3.4720 (17)	169
C7—H7A⋯O1^iv	0.97	2.34	3.2313 (14)	153
C15—H15B⋯O2^v	0.96	2.54	3.426 (2)	154

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for financial support and facilities.

supplementary crystallographic information

Comment

Arylsulphones possess interesting biological activities (Stephens et al., 2001; Abdel-Aziz et al., 2010). As part of our studies in this area, we report herein the crystal structure of the title compound, (Z)-1-(4-methylphenyl)-2-(phenylsulfonyl)ethanone oxime.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts a twisted U-shaped conformation. The twist occurs at the central C6–S1–C7–C8–C9 unit and the C1–C6 benzene ring makes a dihedral angle of 28.74 (7)° with the C9–C14 phenyl ring.

In the crystal (Fig. 2), the molecules are linked by O3—H1O3···N1, C2—H2A···O2, C3—H3A···O1, C7—H7A···O1 and C15—H15B···O2 hydrogen bonds (Table 1) into a three-dimensional network.

Experimental

A mixture of 2-(phenylsulfonyl)-1-p-tolylethanone (0.274 g, 1 mmol), hydroxylamine hydrochloride (0.11 g, 1.5 mmol) and anhydrous sodium acetate (0.123 g, 1.5 mmol) in ethanol (50 ml) was refluxed for 1 h, then left to cool. The reaction mixture was poured into cold water and the solid product was filtered off, washed with water, dried and finally recrystallized from ethanol to afford the title compound as yellow needles.