4-Chloro-N-(3-methyl-phen-yl)benzene-sulfonamide.

In the crystal of the title compound, C(13)H(12)ClNO(2)S, the N-H bond is anti to the meta-methyl group in the aniline ring. The C-SO(2)-NH-C torsion angle is -57.6 (2)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding modes of sulfonamides, see; Adsmond & Grant (2001 ▶). For our study of the effect of substituents on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶), on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2010 ▶); Nirmala et al. (2009 ▶); Shakuntala et al. (2011 ▶) and on the structures of N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C13H12ClNO2S

M = 281.75

Monoclinic,

a = 14.202 (1) Å

b = 14.561 (1) Å

c = 13.271 (1) Å

β = 97.292 (9)°

V = 2722.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.48 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.821, T max = 0.848

5706 measured reflections

2777 independent reflections

2186 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.05

2777 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019416/ds2114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019416/ds2114Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019416/ds2114Isup3.cml

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

C13H12ClNO2S	F(000) = 1168
Mr = 281.75	Dx = 1.375 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2392 reflections
a = 14.202 (1) Å	θ = 2.7–27.8°
b = 14.561 (1) Å	µ = 0.43 mm−1
c = 13.271 (1) Å	T = 293 K
β = 97.292 (9)°	Prism, colourless
V = 2722.2 (3) Å3	0.48 × 0.44 × 0.40 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2777 independent reflections
Radiation source: fine-focus sealed tube	2186 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −17→16
Tmin = 0.821, Tmax = 0.848	k = −18→18
5706 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0632P)2 + 1.8143P] where P = (Fo2 + 2Fc2)/3
2777 reflections	(Δ/σ)max = 0.008
167 parameters	Δρmax = 0.44 e Å−3
1 restraint	Δρmin = −0.45 e Å−3

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	0.53559 (14)	0.23409 (14)	0.05005 (15)	0.0406 (5)
C2	0.57647 (15)	0.31911 (14)	0.04598 (18)	0.0491 (5)
H2	0.6336	0.3256	0.0194	0.059*
C3	0.53266 (18)	0.39513 (17)	0.0813 (2)	0.0593 (6)
H3	0.5600	0.4530	0.0788	0.071*
C4	0.44869 (19)	0.3845 (2)	0.11999 (18)	0.0605 (7)
C5	0.40852 (18)	0.3008 (2)	0.1274 (2)	0.0730 (8)
H5	0.3523	0.2950	0.1560	0.088*
C6	0.45174 (18)	0.2240 (2)	0.0922 (2)	0.0644 (7)
H6	0.4247	0.1662	0.0967	0.077*
C7	0.67268 (14)	0.08513 (13)	0.18508 (15)	0.0388 (4)
C8	0.73805 (14)	0.15662 (14)	0.19410 (16)	0.0442 (5)
H8	0.7430	0.1949	0.1389	0.053*
C9	0.79595 (16)	0.17110 (16)	0.28509 (18)	0.0522 (5)
C10	0.78847 (19)	0.11271 (18)	0.36573 (19)	0.0617 (6)
H10	0.8272	0.1215	0.4269	0.074*
C11	0.72408 (19)	0.04155 (17)	0.35625 (19)	0.0611 (6)
H11	0.7202	0.0024	0.4110	0.073*
C12	0.66545 (16)	0.02758 (15)	0.26704 (18)	0.0500 (5)
H12	0.6214	−0.0200	0.2616	0.060*
C13	0.8658 (2)	0.2492 (2)	0.2948 (2)	0.0907 (10)
H13A	0.8476	0.2935	0.3423	0.109*
H13B	0.8664	0.2779	0.2297	0.109*
H13C	0.9281	0.2262	0.3184	0.109*
N1	0.61358 (14)	0.06654 (12)	0.09302 (14)	0.0510 (5)
H1N	0.5746 (16)	0.0231 (14)	0.092 (2)	0.061*
O1	0.67240 (11)	0.16746 (10)	−0.03772 (11)	0.0512 (4)
O2	0.51716 (12)	0.09095 (11)	−0.06921 (12)	0.0610 (5)
Cl1	0.38998 (7)	0.48058 (7)	0.15793 (7)	0.1027 (4)
S1	0.58782 (4)	0.13761 (3)	−0.00050 (4)	0.04315 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0383 (10)	0.0444 (11)	0.0372 (10)	−0.0031 (8)	−0.0019 (8)	0.0028 (9)
C2	0.0448 (11)	0.0439 (12)	0.0593 (13)	−0.0027 (9)	0.0093 (10)	−0.0030 (10)
C3	0.0589 (14)	0.0483 (13)	0.0702 (16)	0.0051 (11)	0.0061 (12)	−0.0041 (12)
C4	0.0637 (15)	0.0735 (17)	0.0444 (12)	0.0243 (13)	0.0070 (11)	0.0019 (12)
C5	0.0540 (15)	0.103 (2)	0.0668 (16)	0.0160 (15)	0.0266 (13)	0.0172 (16)
C6	0.0540 (14)	0.0701 (17)	0.0708 (16)	−0.0093 (13)	0.0150 (12)	0.0166 (14)
C7	0.0395 (10)	0.0315 (9)	0.0440 (11)	0.0032 (8)	−0.0004 (8)	−0.0019 (8)
C8	0.0463 (11)	0.0412 (11)	0.0433 (11)	−0.0026 (9)	−0.0017 (9)	0.0033 (9)
C9	0.0493 (12)	0.0527 (12)	0.0508 (12)	−0.0051 (10)	−0.0086 (10)	−0.0008 (11)
C10	0.0654 (15)	0.0674 (16)	0.0470 (13)	0.0000 (12)	−0.0129 (11)	0.0024 (12)
C11	0.0754 (16)	0.0580 (14)	0.0482 (13)	0.0013 (13)	0.0012 (12)	0.0140 (12)
C12	0.0521 (12)	0.0405 (11)	0.0570 (13)	−0.0014 (9)	0.0049 (10)	0.0048 (10)
C13	0.089 (2)	0.100 (2)	0.0737 (19)	−0.0454 (18)	−0.0238 (16)	0.0067 (18)
N1	0.0607 (12)	0.0336 (9)	0.0535 (11)	−0.0148 (8)	−0.0127 (9)	0.0027 (8)
O1	0.0560 (9)	0.0485 (8)	0.0505 (9)	−0.0052 (7)	0.0128 (7)	−0.0060 (7)
O2	0.0759 (11)	0.0490 (9)	0.0514 (9)	−0.0178 (8)	−0.0183 (8)	−0.0017 (7)
Cl1	0.1129 (7)	0.1136 (7)	0.0848 (6)	0.0634 (6)	0.0249 (5)	−0.0053 (5)
S1	0.0500 (3)	0.0366 (3)	0.0402 (3)	−0.0082 (2)	−0.0044 (2)	−0.0017 (2)

C1—C2	1.371 (3)	C8—H8	0.9300
C1—C6	1.386 (3)	C9—C10	1.381 (3)
C1—S1	1.761 (2)	C9—C13	1.505 (3)
C2—C3	1.381 (3)	C10—C11	1.377 (4)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.366 (4)	C11—C12	1.373 (3)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.354 (4)	C12—H12	0.9300
C4—Cl1	1.736 (3)	C13—H13A	0.9600
C5—C6	1.386 (4)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—H6	0.9300	N1—S1	1.6216 (19)
C7—C12	1.387 (3)	N1—H1N	0.839 (16)
C7—C8	1.390 (3)	O1—S1	1.4236 (15)
C7—N1	1.418 (3)	O2—S1	1.4380 (15)
C8—C9	1.388 (3)
C2—C1—C6	120.1 (2)	C8—C9—C13	120.0 (2)
C2—C1—S1	120.29 (16)	C11—C10—C9	120.5 (2)
C6—C1—S1	119.59 (18)	C11—C10—H10	119.7
C1—C2—C3	119.9 (2)	C9—C10—H10	119.7
C1—C2—H2	120.0	C12—C11—C10	120.9 (2)
C3—C2—H2	120.0	C12—C11—H11	119.6
C4—C3—C2	119.3 (2)	C10—C11—H11	119.6
C4—C3—H3	120.4	C11—C12—C7	119.3 (2)
C2—C3—H3	120.4	C11—C12—H12	120.4
C5—C4—C3	121.7 (2)	C7—C12—H12	120.4
C5—C4—Cl1	118.8 (2)	C9—C13—H13A	109.5
C3—C4—Cl1	119.5 (2)	C9—C13—H13B	109.5
C4—C5—C6	119.5 (2)	H13A—C13—H13B	109.5
C4—C5—H5	120.2	C9—C13—H13C	109.5
C6—C5—H5	120.2	H13A—C13—H13C	109.5
C5—C6—C1	119.4 (2)	H13B—C13—H13C	109.5
C5—C6—H6	120.3	C7—N1—S1	126.09 (14)
C1—C6—H6	120.3	C7—N1—H1N	118.7 (18)
C12—C7—C8	120.01 (19)	S1—N1—H1N	112.3 (18)
C12—C7—N1	117.75 (18)	O1—S1—O2	118.42 (10)
C8—C7—N1	122.22 (18)	O1—S1—N1	110.01 (10)
C9—C8—C7	120.3 (2)	O2—S1—N1	104.79 (9)
C9—C8—H8	119.9	O1—S1—C1	107.66 (9)
C7—C8—H8	119.9	O2—S1—C1	108.95 (10)
C10—C9—C8	119.0 (2)	N1—S1—C1	106.42 (10)
C10—C9—C13	120.9 (2)
C6—C1—C2—C3	−1.8 (4)	C9—C10—C11—C12	−0.6 (4)
S1—C1—C2—C3	176.87 (18)	C10—C11—C12—C7	1.2 (4)
C1—C2—C3—C4	0.0 (4)	C8—C7—C12—C11	−0.7 (3)
C2—C3—C4—C5	2.0 (4)	N1—C7—C12—C11	177.6 (2)
C2—C3—C4—Cl1	−176.41 (19)	C12—C7—N1—S1	161.80 (17)
C3—C4—C5—C6	−2.0 (4)	C8—C7—N1—S1	−19.9 (3)
Cl1—C4—C5—C6	176.4 (2)	C7—N1—S1—O1	58.7 (2)
C4—C5—C6—C1	0.1 (4)	C7—N1—S1—O2	−172.95 (19)
C2—C1—C6—C5	1.8 (4)	C7—N1—S1—C1	−57.6 (2)
S1—C1—C6—C5	−176.92 (19)	C2—C1—S1—O1	1.6 (2)
C12—C7—C8—C9	−0.4 (3)	C6—C1—S1—O1	−179.70 (18)
N1—C7—C8—C9	−178.6 (2)	C2—C1—S1—O2	−127.99 (18)
C7—C8—C9—C10	0.9 (3)	C6—C1—S1—O2	50.7 (2)
C7—C8—C9—C13	−179.3 (2)	C2—C1—S1—N1	119.52 (19)
C8—C9—C10—C11	−0.4 (4)	C6—C1—S1—N1	−61.8 (2)
C13—C9—C10—C11	179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.11 (2)	2.942 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.11 (2)	2.942 (2)	172 (2)

Symmetry code: (i) .