N-(4-Chloro-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

Mol-ecules of the title compound, C(14)H(14)ClNO(2)S, are bent at the S atom with a C-SO(2)-NH-C torsion angle of 57.7 (2)°. The benzene rings are rotated relative to each other by 68.1 (1)°. In the crystal, N-H⋯O(S) hydrogen bonds pack the mol-ecules into infinite chains parallel to the b axis.

Related literature

For the hydrogen-bonding preferences of n class="Chemical">sulfonamides, see: Adsmond & Grant (2001 ▶). For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (1999 ▶); for N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶); and for N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Gowda et al. (2010 ▶); Perlovich et al. (2006 ▶); Shakuntala et al. (2011 ▶). For the preparation of the title compound, see: Savitha & Gowda (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 9.1093 (8) Å

b = 9.9106 (9) Å

c = 16.142 (1) Å

β = 96.505 (9)°

V = 1447.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.888, T max = 0.961

5342 measured reflections

2934 independent reflections

2219 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.121

S = 1.08

2934 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data n class="Disease">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 datablock(s) I, global. DOI: 10.1107/S1600536811029795/bt5589sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029795/bt5589Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029795/bt5589Isup3.cml

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.357 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2044 reflections
a = 9.1093 (8) Å	θ = 2.5–27.7°
b = 9.9106 (9) Å	µ = 0.41 mm−1
c = 16.142 (1) Å	T = 293 K
β = 96.505 (9)°	Prism, colourless
V = 1447.9 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2934 independent reflections
Radiation source: fine-focus sealed tube	2219 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→11
Tmin = 0.888, Tmax = 0.961	k = −8→12
5342 measured reflections	l = −20→19

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.9349P] where P = (Fo2 + 2Fc2)/3
2934 reflections	(Δ/σ)max = 0.002
177 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.32 e Å−3

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	0.6057 (3)	0.0526 (2)	0.39055 (15)	0.0469 (6)
C2	0.6430 (3)	0.1450 (3)	0.45485 (16)	0.0542 (6)
C3	0.7412 (3)	0.1003 (3)	0.52140 (17)	0.0641 (7)
H3	0.7676	0.1602	0.5649	0.077*
C4	0.8019 (3)	−0.0276 (3)	0.52681 (17)	0.0618 (7)
C5	0.7618 (3)	−0.1160 (3)	0.46227 (19)	0.0643 (7)
H5	0.8004	−0.2029	0.4644	0.077*
C6	0.6650 (3)	−0.0771 (3)	0.39452 (18)	0.0575 (7)
H6	0.6392	−0.1377	0.3513	0.069*
C7	0.7258 (3)	0.1399 (2)	0.21393 (14)	0.0458 (6)
C8	0.7325 (4)	0.0198 (3)	0.1716 (2)	0.0709 (8)
H8	0.6500	−0.0361	0.1639	0.085*
C9	0.8622 (4)	−0.0178 (3)	0.1404 (2)	0.0817 (10)
H9	0.8674	−0.0994	0.1125	0.098*
C10	0.9820 (4)	0.0654 (3)	0.15092 (19)	0.0696 (8)
C11	0.9774 (3)	0.1839 (3)	0.19339 (18)	0.0685 (8)
H11	1.0600	0.2396	0.2006	0.082*
C12	0.8494 (3)	0.2206 (3)	0.22558 (16)	0.0587 (7)
H12	0.8465	0.3006	0.2554	0.070*
C13	0.5833 (4)	0.2867 (3)	0.4561 (2)	0.0760 (9)
H13A	0.4795	0.2838	0.4616	0.091*
H13B	0.5985	0.3316	0.4050	0.091*
H13C	0.6338	0.3351	0.5023	0.091*
C14	0.9094 (4)	−0.0683 (4)	0.6002 (2)	0.0841 (10)
H14A	0.8563	−0.1060	0.6428	0.101*
H14B	0.9637	0.0094	0.6218	0.101*
H14C	0.9766	−0.1344	0.5829	0.101*
N1	0.5919 (2)	0.1852 (2)	0.24225 (13)	0.0504 (5)
H1N	0.587 (3)	0.2672 (18)	0.2515 (16)	0.061*
O1	0.3758 (2)	0.18577 (19)	0.31728 (13)	0.0667 (5)
O2	0.4524 (2)	−0.02597 (17)	0.25512 (12)	0.0638 (5)
Cl1	1.14202 (12)	0.01793 (12)	0.10872 (7)	0.1119 (4)
S1	0.49106 (7)	0.09643 (6)	0.29924 (4)	0.04969 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0499 (14)	0.0414 (12)	0.0497 (14)	−0.0080 (10)	0.0070 (11)	0.0040 (11)
C2	0.0632 (16)	0.0511 (14)	0.0504 (14)	−0.0098 (12)	0.0154 (12)	−0.0028 (12)
C3	0.0742 (18)	0.073 (2)	0.0456 (14)	−0.0171 (16)	0.0078 (13)	−0.0035 (14)
C4	0.0549 (16)	0.078 (2)	0.0523 (15)	−0.0122 (15)	0.0074 (12)	0.0172 (15)
C5	0.0646 (17)	0.0546 (16)	0.0729 (19)	0.0027 (14)	0.0044 (14)	0.0148 (15)
C6	0.0664 (17)	0.0424 (14)	0.0621 (16)	−0.0032 (12)	0.0006 (13)	0.0024 (12)
C7	0.0602 (15)	0.0353 (12)	0.0405 (12)	0.0029 (11)	0.0000 (11)	0.0061 (10)
C8	0.079 (2)	0.0476 (16)	0.088 (2)	−0.0072 (14)	0.0195 (17)	−0.0116 (15)
C9	0.104 (3)	0.0538 (18)	0.092 (2)	0.0131 (18)	0.032 (2)	−0.0058 (17)
C10	0.0696 (19)	0.076 (2)	0.0644 (18)	0.0251 (17)	0.0137 (15)	0.0246 (16)
C11	0.0613 (18)	0.081 (2)	0.0620 (17)	−0.0025 (16)	0.0021 (14)	0.0097 (16)
C12	0.0706 (18)	0.0540 (16)	0.0496 (15)	−0.0057 (14)	−0.0011 (13)	−0.0013 (12)
C13	0.100 (2)	0.0541 (18)	0.074 (2)	−0.0043 (16)	0.0123 (18)	−0.0156 (15)
C14	0.0680 (19)	0.114 (3)	0.0679 (19)	−0.0132 (19)	−0.0022 (16)	0.0274 (19)
N1	0.0649 (13)	0.0290 (10)	0.0575 (13)	0.0021 (10)	0.0074 (10)	0.0023 (9)
O1	0.0522 (11)	0.0563 (11)	0.0919 (14)	0.0044 (9)	0.0100 (10)	0.0039 (10)
O2	0.0695 (12)	0.0422 (10)	0.0751 (13)	−0.0126 (9)	−0.0118 (10)	−0.0014 (9)
Cl1	0.0955 (7)	0.1262 (9)	0.1214 (8)	0.0489 (6)	0.0447 (6)	0.0358 (7)
S1	0.0499 (3)	0.0361 (3)	0.0616 (4)	−0.0040 (3)	−0.0001 (3)	0.0016 (3)

C1—C6	1.392 (4)	C9—C10	1.363 (5)
C1—C2	1.397 (4)	C9—H9	0.9300
C1—S1	1.762 (3)	C10—C11	1.363 (5)
C2—C3	1.390 (4)	C10—Cl1	1.742 (3)
C2—C13	1.508 (4)	C11—C12	1.378 (4)
C3—C4	1.382 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (4)	C13—H13A	0.9600
C4—C14	1.504 (4)	C13—H13B	0.9600
C5—C6	1.380 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C12	1.377 (4)	C14—H14C	0.9600
C7—C8	1.377 (4)	N1—S1	1.630 (2)
C7—N1	1.423 (3)	N1—H1N	0.828 (17)
C8—C9	1.387 (4)	O1—S1	1.429 (2)
C8—H8	0.9300	O2—S1	1.430 (2)
C6—C1—C2	120.7 (2)	C11—C10—Cl1	120.3 (3)
C6—C1—S1	117.1 (2)	C10—C11—C12	119.5 (3)
C2—C1—S1	122.1 (2)	C10—C11—H11	120.2
C3—C2—C1	116.5 (3)	C12—C11—H11	120.2
C3—C2—C13	119.2 (3)	C7—C12—C11	120.6 (3)
C1—C2—C13	124.2 (3)	C7—C12—H12	119.7
C4—C3—C2	124.0 (3)	C11—C12—H12	119.7
C4—C3—H3	118.0	C2—C13—H13A	109.5
C2—C3—H3	118.0	C2—C13—H13B	109.5
C5—C4—C3	117.7 (3)	H13A—C13—H13B	109.5
C5—C4—C14	121.2 (3)	C2—C13—H13C	109.5
C3—C4—C14	121.1 (3)	H13A—C13—H13C	109.5
C4—C5—C6	120.8 (3)	H13B—C13—H13C	109.5
C4—C5—H5	119.6	C4—C14—H14A	109.5
C6—C5—H5	119.6	C4—C14—H14B	109.5
C5—C6—C1	120.3 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.9	C4—C14—H14C	109.5
C1—C6—H6	119.9	H14A—C14—H14C	109.5
C12—C7—C8	119.2 (3)	H14B—C14—H14C	109.5
C12—C7—N1	119.4 (2)	C7—N1—S1	124.70 (17)
C8—C7—N1	121.4 (2)	C7—N1—H1N	115.6 (19)
C7—C8—C9	120.0 (3)	S1—N1—H1N	112.6 (19)
C7—C8—H8	120.0	O1—S1—O2	118.81 (12)
C9—C8—H8	120.0	O1—S1—N1	104.76 (12)
C10—C9—C8	119.7 (3)	O2—S1—N1	107.43 (12)
C10—C9—H9	120.2	O1—S1—C1	111.24 (12)
C8—C9—H9	120.2	O2—S1—C1	107.25 (12)
C9—C10—C11	120.9 (3)	N1—S1—C1	106.67 (11)
C9—C10—Cl1	118.8 (3)
C6—C1—C2—C3	0.2 (4)	C8—C9—C10—Cl1	−178.3 (3)
S1—C1—C2—C3	−176.34 (19)	C9—C10—C11—C12	−0.5 (4)
C6—C1—C2—C13	−179.5 (3)	Cl1—C10—C11—C12	179.3 (2)
S1—C1—C2—C13	4.0 (4)	C8—C7—C12—C11	1.8 (4)
C1—C2—C3—C4	0.0 (4)	N1—C7—C12—C11	−175.2 (2)
C13—C2—C3—C4	179.7 (3)	C10—C11—C12—C7	−1.2 (4)
C2—C3—C4—C5	−0.3 (4)	C12—C7—N1—S1	−130.2 (2)
C2—C3—C4—C14	179.1 (3)	C8—C7—N1—S1	52.9 (3)
C3—C4—C5—C6	0.4 (4)	C7—N1—S1—O1	175.7 (2)
C14—C4—C5—C6	−178.9 (3)	C7—N1—S1—O2	−57.0 (2)
C4—C5—C6—C1	−0.3 (4)	C7—N1—S1—C1	57.7 (2)
C2—C1—C6—C5	0.0 (4)	C6—C1—S1—O1	146.0 (2)
S1—C1—C6—C5	176.6 (2)	C2—C1—S1—O1	−37.4 (2)
C12—C7—C8—C9	−0.8 (4)	C6—C1—S1—O2	14.5 (2)
N1—C7—C8—C9	176.1 (3)	C2—C1—S1—O2	−168.8 (2)
C7—C8—C9—C10	−0.9 (5)	C6—C1—S1—N1	−100.3 (2)
C8—C9—C10—C11	1.5 (5)	C2—C1—S1—N1	76.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.08 (2)	2.891 (4)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.08 (2)	2.891 (4)	166 (3)

Symmetry code: (i) .