(Z)-1-(4-Methyl-phen-yl)-2-(phenyl-sulfon-yl)ethanone oxime.

The mol-ecule of the title compound, C(15)H(15)NO(3)S, 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 = 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

Δρmax = 0.42 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030346/hb6884sup1.cif

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

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

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

C15H15NO3S	F(000) = 608
Mr = 289.34	Dx = 1.372 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5520 reflections
a = 5.2305 (3) Å	θ = 2.3–30.7°
b = 17.6073 (11) Å	µ = 0.24 mm−1
c = 15.6578 (10) Å	T = 100 K
β = 103.782 (2)°	Needle, yellow
V = 1400.49 (15) Å3	0.29 × 0.09 × 0.06 mm
Z = 4

Bruker APEX DUO CCD diffractometer	4349 independent reflections
Radiation source: fine-focus sealed tube	3578 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.934, Tmax = 0.985	k = −21→25
16727 measured reflections	l = −16→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.6281P] where P = (Fo2 + 2Fc2)/3
4349 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.56144 (5)	0.782145 (17)	0.384686 (18)	0.01353 (8)
O1	0.83354 (16)	0.79802 (6)	0.38609 (6)	0.01848 (19)
O2	0.50126 (19)	0.71628 (5)	0.43065 (6)	0.0208 (2)
O3	0.86263 (19)	0.92446 (6)	0.52121 (6)	0.0218 (2)
N1	0.7376 (2)	0.96756 (6)	0.44763 (7)	0.0177 (2)
C1	0.4951 (3)	0.81035 (9)	0.20998 (9)	0.0239 (3)
H1A	0.6457	0.8401	0.2263	0.029*
C2	0.3699 (3)	0.80091 (11)	0.12183 (9)	0.0319 (3)
H2A	0.4350	0.8249	0.0785	0.038*
C3	0.1472 (3)	0.75546 (11)	0.09865 (10)	0.0329 (4)
H3A	0.0655	0.7485	0.0396	0.039*
C4	0.0457 (3)	0.72046 (10)	0.16220 (10)	0.0303 (3)
H4A	−0.1042	0.6905	0.1456	0.036*
C5	0.1662 (2)	0.72973 (8)	0.25099 (9)	0.0214 (3)
H5A	0.0981	0.7066	0.2942	0.026*
C6	0.3915 (2)	0.77457 (7)	0.27336 (8)	0.0164 (2)
C7	0.4295 (2)	0.86214 (7)	0.43094 (8)	0.0154 (2)
H7A	0.2388	0.8605	0.4130	0.018*
H7B	0.4803	0.8586	0.4946	0.018*
C8	0.5234 (2)	0.93671 (7)	0.40293 (8)	0.0153 (2)
C9	0.3773 (2)	0.97524 (7)	0.32203 (8)	0.0168 (2)
C10	0.4854 (3)	1.03660 (9)	0.28673 (11)	0.0303 (3)
H10A	0.6487	1.0555	0.3160	0.036*
C11	0.3522 (3)	1.06969 (10)	0.20849 (11)	0.0349 (4)
H11A	0.4286	1.1106	0.1863	0.042*
C12	0.1092 (3)	1.04366 (8)	0.16238 (9)	0.0255 (3)
C13	0.0000 (3)	0.98351 (10)	0.19822 (11)	0.0325 (3)
H13A	−0.1644	0.9652	0.1690	0.039*
C14	0.1302 (3)	0.94978 (9)	0.27687 (10)	0.0283 (3)
H14A	0.0512	0.9097	0.2996	0.034*
C15	−0.0305 (4)	1.07962 (10)	0.07609 (11)	0.0353 (4)
H15A	0.0951	1.0911	0.0422	0.053*
H15B	−0.1154	1.1256	0.0875	0.053*
H15C	−0.1600	1.0450	0.0439	0.053*
H1O3	1.021 (4)	0.9523 (12)	0.5474 (13)	0.040 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01289 (12)	0.01713 (15)	0.00974 (13)	−0.00179 (9)	0.00102 (9)	−0.00080 (10)
O1	0.0124 (3)	0.0265 (5)	0.0157 (4)	−0.0008 (3)	0.0017 (3)	−0.0018 (4)
O2	0.0274 (5)	0.0191 (5)	0.0158 (4)	−0.0032 (4)	0.0050 (3)	0.0019 (4)
O3	0.0217 (4)	0.0216 (5)	0.0176 (5)	−0.0041 (4)	−0.0045 (3)	0.0019 (4)
N1	0.0169 (4)	0.0175 (5)	0.0162 (5)	−0.0011 (4)	−0.0014 (4)	−0.0007 (4)
C1	0.0232 (6)	0.0341 (8)	0.0139 (6)	−0.0006 (5)	0.0036 (5)	−0.0002 (5)
C2	0.0334 (7)	0.0499 (10)	0.0114 (6)	0.0084 (7)	0.0033 (5)	0.0008 (6)
C3	0.0275 (6)	0.0521 (10)	0.0142 (6)	0.0124 (7)	−0.0047 (5)	−0.0123 (7)
C4	0.0181 (6)	0.0409 (9)	0.0274 (8)	0.0022 (5)	−0.0037 (5)	−0.0171 (7)
C5	0.0159 (5)	0.0267 (7)	0.0206 (6)	−0.0008 (5)	0.0019 (4)	−0.0079 (5)
C6	0.0148 (5)	0.0219 (6)	0.0113 (5)	0.0005 (4)	0.0005 (4)	−0.0032 (5)
C7	0.0143 (4)	0.0191 (6)	0.0128 (5)	−0.0023 (4)	0.0033 (4)	−0.0019 (4)
C8	0.0140 (5)	0.0163 (6)	0.0150 (5)	−0.0008 (4)	0.0025 (4)	−0.0029 (4)
C9	0.0170 (5)	0.0163 (6)	0.0161 (6)	0.0015 (4)	0.0018 (4)	−0.0025 (5)
C10	0.0296 (7)	0.0260 (8)	0.0290 (8)	−0.0092 (6)	−0.0057 (6)	0.0067 (6)
C11	0.0402 (8)	0.0265 (8)	0.0327 (8)	−0.0056 (6)	−0.0021 (6)	0.0115 (7)
C12	0.0322 (7)	0.0206 (7)	0.0201 (6)	0.0107 (5)	−0.0008 (5)	−0.0014 (5)
C13	0.0256 (6)	0.0333 (8)	0.0303 (8)	0.0002 (6)	−0.0099 (5)	0.0050 (7)
C14	0.0209 (6)	0.0286 (8)	0.0299 (8)	−0.0052 (5)	−0.0047 (5)	0.0072 (6)
C15	0.0474 (9)	0.0279 (8)	0.0243 (8)	0.0146 (7)	−0.0037 (6)	0.0014 (6)

S1—O2	1.4386 (10)	C7—C8	1.5034 (17)
S1—O1	1.4454 (9)	C7—H7A	0.9700
S1—C6	1.7630 (12)	C7—H7B	0.9700
S1—C7	1.7951 (13)	C8—C9	1.4791 (17)
O3—N1	1.4042 (14)	C9—C14	1.3913 (17)
O3—H1O3	0.96 (2)	C9—C10	1.393 (2)
N1—C8	1.2910 (15)	C10—C11	1.385 (2)
C1—C2	1.3896 (19)	C10—H10A	0.9300
C1—C6	1.3898 (18)	C11—C12	1.382 (2)
C1—H1A	0.9300	C11—H11A	0.9300
C2—C3	1.388 (2)	C12—C13	1.384 (2)
C2—H2A	0.9300	C12—C15	1.513 (2)
C3—C4	1.380 (2)	C13—C14	1.390 (2)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.3925 (19)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9600
C5—C6	1.3918 (17)	C15—H15B	0.9600
C5—H5A	0.9300	C15—H15C	0.9600
O2—S1—O1	118.71 (6)	S1—C7—H7B	109.1
O2—S1—C6	108.34 (6)	H7A—C7—H7B	107.8
O1—S1—C6	107.00 (6)	N1—C8—C9	118.42 (12)
O2—S1—C7	106.24 (6)	N1—C8—C7	120.73 (11)
O1—S1—C7	108.29 (6)	C9—C8—C7	120.82 (10)
C6—S1—C7	107.85 (6)	C14—C9—C10	117.63 (12)
N1—O3—H1O3	105.0 (12)	C14—C9—C8	121.03 (12)
C8—N1—O3	113.06 (11)	C10—C9—C8	121.31 (11)
C2—C1—C6	118.90 (14)	C11—C10—C9	120.72 (13)
C2—C1—H1A	120.6	C11—C10—H10A	119.6
C6—C1—H1A	120.6	C9—C10—H10A	119.6
C3—C2—C1	119.75 (15)	C12—C11—C10	121.92 (15)
C3—C2—H2A	120.1	C12—C11—H11A	119.0
C1—C2—H2A	120.1	C10—C11—H11A	119.0
C4—C3—C2	120.79 (13)	C11—C12—C13	117.32 (13)
C4—C3—H3A	119.6	C11—C12—C15	121.08 (15)
C2—C3—H3A	119.6	C13—C12—C15	121.60 (14)
C3—C4—C5	120.48 (14)	C12—C13—C14	121.57 (14)
C3—C4—H4A	119.8	C12—C13—H13A	119.2
C5—C4—H4A	119.8	C14—C13—H13A	119.2
C6—C5—C4	118.19 (14)	C13—C14—C9	120.81 (14)
C6—C5—H5A	120.9	C13—C14—H14A	119.6
C4—C5—H5A	120.9	C9—C14—H14A	119.6
C1—C6—C5	121.87 (12)	C12—C15—H15A	109.5
C1—C6—S1	118.76 (10)	C12—C15—H15B	109.5
C5—C6—S1	119.27 (10)	H15A—C15—H15B	109.5
C8—C7—S1	112.57 (8)	C12—C15—H15C	109.5
C8—C7—H7A	109.1	H15A—C15—H15C	109.5
S1—C7—H7A	109.1	H15B—C15—H15C	109.5
C8—C7—H7B	109.1
C6—C1—C2—C3	−0.8 (2)	O3—N1—C8—C7	0.08 (16)
C1—C2—C3—C4	1.1 (2)	S1—C7—C8—N1	−88.95 (13)
C2—C3—C4—C5	−0.4 (2)	S1—C7—C8—C9	89.10 (12)
C3—C4—C5—C6	−0.5 (2)	N1—C8—C9—C14	−172.31 (13)
C2—C1—C6—C5	−0.1 (2)	C7—C8—C9—C14	9.59 (19)
C2—C1—C6—S1	176.35 (12)	N1—C8—C9—C10	9.84 (19)
C4—C5—C6—C1	0.7 (2)	C7—C8—C9—C10	−168.25 (13)
C4—C5—C6—S1	−175.68 (11)	C14—C9—C10—C11	−1.3 (2)
O2—S1—C6—C1	−152.81 (11)	C8—C9—C10—C11	176.65 (15)
O1—S1—C6—C1	−23.72 (13)	C9—C10—C11—C12	−0.1 (3)
C7—S1—C6—C1	92.59 (11)	C10—C11—C12—C13	1.1 (3)
O2—S1—C6—C5	23.70 (12)	C10—C11—C12—C15	−178.77 (16)
O1—S1—C6—C5	152.79 (10)	C11—C12—C13—C14	−0.8 (3)
C7—S1—C6—C5	−90.91 (11)	C15—C12—C13—C14	179.06 (15)
O2—S1—C7—C8	168.32 (8)	C12—C13—C14—C9	−0.5 (3)
O1—S1—C7—C8	39.77 (10)	C10—C9—C14—C13	1.5 (2)
C6—S1—C7—C8	−75.70 (9)	C8—C9—C14—C13	−176.38 (14)
O3—N1—C8—C9	−178.02 (10)

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···O1iv	0.97	2.34	3.2313 (14)	153
C15—H15B···O2v	0.96	2.54	3.426 (2)	154

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⋯O1iv	0.97	2.34	3.2313 (14)	153
C15—H15B⋯O2v	0.96	2.54	3.426 (2)	154

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