N-{4-[(3-Methyl-phen-yl)sulfamo-yl]phen-yl}acetamide.

In the title compound, C(15)H(16)N(2)O(3)S, the central C-S(=O)(2)N(H)-C unit is twisted, with a C-S-N-C torsion angle of -56.4 (2)°. The benzene rings form a dihedral angle of 49.65 (15)° with each other. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to sulfonamides, see: Ahmad et al. (2011a ▶,b ▶); Faryal et al. (2011 ▶); Pandya et al. (2003 ▶); Singh & Bansal (2004 ▶). For the crystal structure of the isomeric compound, N–{4–[(4–methyl­phen­yl)sulfamo­yl]phen­yl}acetamide, see: John et al. (2010 ▶).

Experimental

Crystal data

C15H16N2O3S

M = 304.37

Orthorhombic,

a = 12.4072 (4) Å

b = 9.8528 (4) Å

c = 24.7872 (10) Å

V = 3030.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.13 × 0.10 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

27585 measured reflections

3766 independent reflections

2018 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.146

S = 1.02

3766 reflections

200 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812001274/lx2224sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001274/lx2224Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001274/lx2224Isup3.cml

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

C15H16N2O3S	F(000) = 1280
Mr = 304.37	Dx = 1.334 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2598 reflections
a = 12.4072 (4) Å	θ = 2.8–26.1°
b = 9.8528 (4) Å	µ = 0.23 mm−1
c = 24.7872 (10) Å	T = 296 K
V = 3030.1 (2) Å3	Plates, colourless
Z = 8	0.13 × 0.10 × 0.05 mm

Bruker APEXII CCD diffractometer	2018 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.089
graphite	θmax = 28.3°, θmin = 2.8°
φ and ω scans	h = −16→15
27585 measured reflections	k = −13→13
3766 independent reflections	l = −32→32

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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0559P)2 + 1.2606P] where P = (Fo2 + 2Fc2)/3
3766 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.44 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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	0.75972 (5)	0.46076 (6)	0.12164 (3)	0.0386 (2)
O1	0.82358 (15)	0.3853 (2)	0.08468 (9)	0.0510 (7)
O2	0.79502 (15)	0.59357 (18)	0.13737 (9)	0.0477 (7)
O3	0.25638 (16)	0.27762 (18)	0.04342 (10)	0.0573 (8)
N1	0.75422 (19)	0.3683 (2)	0.17624 (10)	0.0407 (8)
N2	0.30625 (19)	0.4969 (2)	0.05052 (11)	0.0424 (8)
C1	0.1211 (2)	0.4459 (3)	0.03050 (14)	0.0536 (10)
C2	0.2336 (2)	0.3979 (3)	0.04182 (11)	0.0400 (9)
C3	0.4142 (2)	0.4837 (2)	0.06584 (11)	0.0362 (9)
C4	0.4594 (2)	0.5905 (3)	0.09375 (13)	0.0505 (12)
C5	0.5659 (2)	0.5860 (3)	0.10976 (13)	0.0501 (10)
C6	0.6270 (2)	0.4738 (3)	0.09778 (11)	0.0362 (9)
C7	0.5827 (2)	0.3668 (3)	0.06968 (12)	0.0448 (10)
C8	0.4762 (2)	0.3707 (3)	0.05379 (12)	0.0442 (10)
C9	0.6853 (2)	0.4104 (3)	0.21957 (12)	0.0425 (10)
C10	0.7132 (2)	0.5202 (3)	0.25144 (13)	0.0494 (11)
C11	0.6485 (3)	0.5624 (4)	0.29349 (13)	0.0593 (12)
C12	0.5563 (3)	0.4898 (4)	0.30367 (16)	0.0723 (16)
C13	0.5285 (3)	0.3793 (4)	0.27305 (18)	0.0780 (16)
C14	0.5919 (2)	0.3389 (3)	0.23047 (15)	0.0596 (13)
C15	0.6791 (4)	0.6837 (4)	0.32666 (16)	0.0900 (19)
H1A	0.10860	0.44510	−0.00770	0.0800*
H1B	0.11240	0.53650	0.04400	0.0800*
H1C	0.07050	0.38670	0.04790	0.0800*
H1N	0.746 (2)	0.2849 (18)	0.1672 (10)	0.034 (7)*
H2N	0.283 (2)	0.5766 (19)	0.0497 (11)	0.041 (8)*
H4	0.41780	0.66630	0.10190	0.0610*
H5	0.59610	0.65850	0.12850	0.0600*
H7	0.62490	0.29160	0.06140	0.0540*
H8	0.44620	0.29800	0.03510	0.0530*
H10	0.77690	0.56660	0.24440	0.0590*
H12	0.51180	0.51610	0.33200	0.0870*
H13	0.46600	0.33130	0.28110	0.0930*
H14	0.57240	0.26480	0.20940	0.0710*
H15A	0.65440	0.76480	0.30910	0.1350*
H15B	0.75610	0.68710	0.33050	0.1350*
H15C	0.64650	0.67700	0.36170	0.1350*

	U11	U22	U33	U12	U13	U23
S1	0.0279 (3)	0.0296 (3)	0.0582 (5)	0.0008 (3)	0.0013 (3)	−0.0014 (3)
O1	0.0385 (11)	0.0465 (12)	0.0679 (14)	0.0097 (10)	0.0113 (10)	−0.0046 (10)
O2	0.0364 (10)	0.0307 (10)	0.0759 (15)	−0.0076 (9)	−0.0033 (10)	−0.0003 (10)
O3	0.0501 (13)	0.0258 (11)	0.0960 (18)	−0.0051 (10)	−0.0081 (12)	0.0021 (10)
N1	0.0356 (13)	0.0279 (12)	0.0586 (16)	0.0013 (11)	0.0000 (12)	−0.0011 (11)
N2	0.0339 (13)	0.0240 (12)	0.0694 (17)	0.0010 (10)	−0.0097 (12)	0.0005 (11)
C1	0.0382 (16)	0.0475 (18)	0.075 (2)	−0.0051 (15)	−0.0110 (16)	0.0012 (16)
C2	0.0397 (16)	0.0319 (15)	0.0485 (18)	−0.0043 (13)	−0.0039 (13)	0.0016 (13)
C3	0.0316 (15)	0.0260 (13)	0.0509 (18)	−0.0009 (12)	−0.0003 (13)	0.0017 (12)
C4	0.0342 (16)	0.0254 (14)	0.092 (3)	0.0053 (13)	−0.0061 (16)	−0.0113 (15)
C5	0.0397 (16)	0.0277 (14)	0.083 (2)	−0.0017 (13)	−0.0079 (15)	−0.0133 (14)
C6	0.0267 (13)	0.0298 (14)	0.0521 (18)	0.0010 (12)	0.0003 (12)	0.0001 (12)
C7	0.0384 (17)	0.0301 (14)	0.066 (2)	0.0063 (13)	−0.0031 (15)	−0.0093 (13)
C8	0.0412 (16)	0.0304 (14)	0.061 (2)	0.0004 (13)	−0.0070 (14)	−0.0103 (13)
C9	0.0302 (15)	0.0436 (16)	0.0537 (19)	0.0049 (13)	−0.0024 (13)	0.0037 (14)
C10	0.0444 (18)	0.0487 (18)	0.055 (2)	0.0035 (15)	−0.0033 (15)	0.0024 (16)
C11	0.062 (2)	0.066 (2)	0.050 (2)	0.0162 (19)	−0.0014 (17)	−0.0035 (17)
C12	0.058 (2)	0.096 (3)	0.063 (3)	0.015 (2)	0.0167 (19)	0.002 (2)
C13	0.045 (2)	0.091 (3)	0.098 (3)	−0.004 (2)	0.019 (2)	0.006 (3)
C14	0.0399 (18)	0.058 (2)	0.081 (3)	−0.0041 (16)	0.0054 (18)	−0.0009 (18)
C15	0.107 (4)	0.100 (3)	0.063 (3)	0.016 (3)	−0.001 (2)	−0.022 (2)

S1—O1	1.421 (2)	C10—C11	1.380 (5)
S1—O2	1.4339 (19)	C11—C12	1.373 (5)
S1—N1	1.633 (2)	C11—C15	1.500 (5)
S1—C6	1.754 (3)	C12—C13	1.371 (6)
O3—C2	1.219 (3)	C13—C14	1.375 (5)
N1—C9	1.434 (4)	C1—H1A	0.9600
N2—C2	1.346 (4)	C1—H1B	0.9600
N2—C3	1.398 (3)	C1—H1C	0.9600
N1—H1N	0.858 (18)	C4—H4	0.9300
N2—H2N	0.84 (2)	C5—H5	0.9300
C1—C2	1.500 (4)	C7—H7	0.9300
C3—C8	1.386 (4)	C8—H8	0.9300
C3—C4	1.379 (4)	C10—H10	0.9300
C4—C5	1.380 (4)	C12—H12	0.9300
C5—C6	1.373 (4)	C13—H13	0.9300
C6—C7	1.378 (4)	C14—H14	0.9300
C7—C8	1.379 (4)	C15—H15A	0.9600
C9—C14	1.383 (4)	C15—H15B	0.9600
C9—C10	1.384 (4)	C15—H15C	0.9600
O1—S1—O2	118.84 (12)	C11—C12—C13	121.4 (4)
O1—S1—N1	105.41 (12)	C12—C13—C14	120.7 (3)
O1—S1—C6	110.14 (13)	C9—C14—C13	118.8 (3)
O2—S1—N1	107.25 (12)	C2—C1—H1A	109.00
O2—S1—C6	108.15 (13)	C2—C1—H1B	109.00
N1—S1—C6	106.32 (13)	C2—C1—H1C	109.00
S1—N1—C9	118.97 (18)	H1A—C1—H1B	109.00
C2—N2—C3	128.2 (2)	H1A—C1—H1C	109.00
S1—N1—H1N	108.8 (17)	H1B—C1—H1C	110.00
C9—N1—H1N	113.7 (17)	C3—C4—H4	120.00
C2—N2—H2N	116.5 (17)	C5—C4—H4	120.00
C3—N2—H2N	115.1 (17)	C4—C5—H5	120.00
O3—C2—N2	123.0 (2)	C6—C5—H5	120.00
O3—C2—C1	121.9 (2)	C6—C7—H7	120.00
N2—C2—C1	115.1 (2)	C8—C7—H7	120.00
N2—C3—C4	117.1 (2)	C3—C8—H8	120.00
C4—C3—C8	119.7 (2)	C7—C8—H8	120.00
N2—C3—C8	123.2 (2)	C9—C10—H10	119.00
C3—C4—C5	120.6 (3)	C11—C10—H10	119.00
C4—C5—C6	119.5 (3)	C11—C12—H12	119.00
C5—C6—C7	120.3 (2)	C13—C12—H12	119.00
S1—C6—C5	120.3 (2)	C12—C13—H13	120.00
S1—C6—C7	119.3 (2)	C14—C13—H13	120.00
C6—C7—C8	120.3 (3)	C9—C14—H14	121.00
C3—C8—C7	119.5 (3)	C13—C14—H14	121.00
N1—C9—C14	119.9 (3)	C11—C15—H15A	110.00
C10—C9—C14	119.8 (3)	C11—C15—H15B	110.00
N1—C9—C10	120.3 (2)	C11—C15—H15C	110.00
C9—C10—C11	121.4 (3)	H15A—C15—H15B	109.00
C10—C11—C12	117.8 (3)	H15A—C15—H15C	109.00
C10—C11—C15	120.5 (3)	H15B—C15—H15C	109.00
C12—C11—C15	121.7 (3)
O1—S1—N1—C9	−173.3 (2)	C8—C3—C4—C5	0.1 (4)
O2—S1—N1—C9	59.1 (2)	C3—C4—C5—C6	−0.1 (5)
C6—S1—N1—C9	−56.4 (2)	C4—C5—C6—C7	0.4 (4)
O2—S1—C6—C7	166.2 (2)	C4—C5—C6—S1	−175.7 (2)
N1—S1—C6—C7	−78.9 (2)	S1—C6—C7—C8	175.5 (2)
O2—S1—C6—C5	−17.6 (3)	C5—C6—C7—C8	−0.7 (4)
N1—S1—C6—C5	97.3 (3)	C6—C7—C8—C3	0.6 (4)
O1—S1—C6—C5	−149.0 (2)	N1—C9—C10—C11	−179.8 (3)
O1—S1—C6—C7	34.9 (3)	C14—C9—C10—C11	−1.4 (5)
S1—N1—C9—C10	−73.2 (3)	N1—C9—C14—C13	178.4 (3)
S1—N1—C9—C14	108.4 (3)	C10—C9—C14—C13	0.1 (5)
C2—N2—C3—C4	−153.2 (3)	C9—C10—C11—C12	1.5 (5)
C3—N2—C2—O3	−4.5 (5)	C9—C10—C11—C15	−178.6 (3)
C2—N2—C3—C8	27.5 (5)	C10—C11—C12—C13	−0.4 (6)
C3—N2—C2—C1	174.8 (3)	C15—C11—C12—C13	179.7 (4)
N2—C3—C4—C5	−179.2 (3)	C11—C12—C13—C14	−0.9 (6)
C4—C3—C8—C7	−0.3 (4)	C12—C13—C14—C9	1.1 (5)
N2—C3—C8—C7	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86 (2)	2.09 (2)	2.938 (3)	171 (2)
N2—H2N···O3ii	0.84 (2)	2.05 (2)	2.878 (3)	173 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86 (2)	2.09 (2)	2.938 (3)	171 (2)
N2—H2N⋯O3ii	0.84 (2)	2.05 (2)	2.878 (3)	173 (3)

Symmetry codes: (i) ; (ii) .