2,4-Dichloro-N-(2,6-dimethyl-phen-yl)benzene-sulfonamide.

In the crystal of the title compound, C(14)H(13)Cl(2)NO(2)S, the N-H bond in the C-SO(2)-NH-C segment orients itself away from the two ortho-methyl groups in the aniline benzene ring and towards the ortho-chloro group of the sulfonyl benzene ring. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of -100.48 (18)°. The sulfonyl and aniline benzene rings are tilted relative to each other by 69.6 (1)°. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For the hydrogen-bonding preferences of sulfonamides, see: Adsmond & Grant (2001 ▶). For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Gowda et al. (2001 ▶); of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶); and of N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶); Gowda et al. (2003 ▶); Rodrigues et al. (2011 ▶).

Experimental

Crystal data

C14H13Cl2NO2S

M = 330.21

Monoclinic,

a = 12.021 (1) Å

b = 7.5458 (7) Å

c = 16.837 (1) Å

β = 92.324 (7)°

V = 1526.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 K

0.40 × 0.36 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.807, T max = 0.877

6113 measured reflections

3107 independent reflections

2188 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.03

3107 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.30 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 datablock(s) I, global. DOI: 10.1107/S1600536811037767/bq2306sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037767/bq2306Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037767/bq2306Isup3.cml

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

C14H13Cl2NO2S	F(000) = 680
Mr = 330.21	Dx = 1.437 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2095 reflections
a = 12.021 (1) Å	θ = 2.9–27.9°
b = 7.5458 (7) Å	µ = 0.56 mm−1
c = 16.837 (1) Å	T = 293 K
β = 92.324 (7)°	Prism, light pink
V = 1526.0 (2) Å3	0.40 × 0.36 × 0.24 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3107 independent reflections
Radiation source: fine-focus sealed tube	2188 reflections with I > 2σ(I)
graphite	Rint = 0.016
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −15→12
Tmin = 0.807, Tmax = 0.877	k = −4→9
6113 measured reflections	l = −15→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.1526P] where P = (Fo2 + 2Fc2)/3
3107 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.30 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	−0.00339 (18)	0.0423 (3)	0.17532 (11)	0.0447 (5)
C2	−0.03633 (18)	0.1047 (3)	0.24905 (11)	0.0488 (5)
C3	−0.14639 (19)	0.1301 (3)	0.26339 (13)	0.0567 (6)
H3	−0.1675	0.1718	0.3125	0.068*
C4	−0.2252 (2)	0.0933 (3)	0.20448 (15)	0.0610 (6)
C5	−0.1960 (2)	0.0313 (3)	0.13147 (15)	0.0631 (6)
H5	−0.2505	0.0066	0.0922	0.076*
C6	−0.0852 (2)	0.0062 (3)	0.11709 (12)	0.0529 (5)
H6	−0.0649	−0.0355	0.0678	0.063*
C7	0.23032 (18)	0.2999 (3)	0.09672 (11)	0.0518 (5)
C8	0.1656 (2)	0.4451 (3)	0.07794 (15)	0.0658 (7)
C9	0.1977 (3)	0.5519 (4)	0.01570 (19)	0.0947 (10)
H9	0.1554	0.6509	0.0014	0.114*
C10	0.2916 (4)	0.5121 (5)	−0.02503 (19)	0.1055 (13)
H10	0.3120	0.5846	−0.0667	0.127*
C11	0.3539 (3)	0.3704 (5)	−0.00542 (17)	0.0915 (10)
H11	0.4170	0.3462	−0.0337	0.110*
C12	0.3262 (2)	0.2592 (4)	0.05622 (13)	0.0692 (7)
C13	0.0657 (3)	0.4921 (4)	0.1248 (2)	0.0961 (10)
H13A	0.0863	0.4924	0.1805	0.115*
H13B	0.0079	0.4063	0.1146	0.115*
H13C	0.0392	0.6075	0.1093	0.115*
C14	0.3972 (3)	0.1014 (6)	0.0786 (2)	0.1130 (13)
H14A	0.3617	−0.0047	0.0588	0.136*
H14B	0.4065	0.0947	0.1354	0.136*
H14C	0.4687	0.1135	0.0558	0.136*
N1	0.20289 (15)	0.1885 (3)	0.16252 (9)	0.0543 (5)
H1N	0.2250 (19)	0.219 (3)	0.2076 (10)	0.065*
O1	0.13715 (14)	−0.0438 (2)	0.07160 (8)	0.0590 (4)
O2	0.18112 (15)	−0.1142 (2)	0.21241 (9)	0.0718 (5)
Cl1	0.06147 (5)	0.15315 (10)	0.32422 (3)	0.0749 (2)
Cl2	−0.36486 (6)	0.12532 (12)	0.22362 (6)	0.0975 (3)
S1	0.13772 (5)	0.00526 (7)	0.15342 (3)	0.04943 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0554 (12)	0.0439 (11)	0.0343 (9)	−0.0036 (9)	−0.0050 (8)	0.0050 (8)
C2	0.0552 (13)	0.0541 (12)	0.0367 (10)	−0.0081 (10)	−0.0030 (9)	0.0006 (9)
C3	0.0597 (14)	0.0589 (14)	0.0518 (12)	−0.0064 (11)	0.0080 (11)	0.0003 (11)
C4	0.0523 (14)	0.0563 (14)	0.0741 (16)	−0.0061 (11)	−0.0007 (12)	0.0086 (12)
C5	0.0608 (15)	0.0642 (15)	0.0626 (14)	−0.0112 (12)	−0.0193 (12)	0.0043 (12)
C6	0.0662 (15)	0.0524 (12)	0.0390 (10)	−0.0064 (11)	−0.0102 (10)	−0.0001 (10)
C7	0.0554 (13)	0.0648 (14)	0.0352 (10)	−0.0136 (12)	0.0025 (9)	−0.0116 (10)
C8	0.0829 (18)	0.0504 (13)	0.0647 (15)	−0.0088 (13)	0.0105 (13)	−0.0117 (12)
C9	0.144 (3)	0.0562 (16)	0.084 (2)	−0.0063 (18)	0.012 (2)	0.0024 (15)
C10	0.169 (4)	0.084 (2)	0.0656 (18)	−0.034 (2)	0.040 (2)	−0.0043 (17)
C11	0.104 (2)	0.112 (3)	0.0610 (17)	−0.028 (2)	0.0366 (17)	−0.0190 (18)
C12	0.0623 (15)	0.0968 (19)	0.0492 (13)	−0.0059 (15)	0.0105 (11)	−0.0123 (13)
C13	0.094 (2)	0.0641 (17)	0.132 (3)	0.0111 (16)	0.031 (2)	−0.0061 (18)
C14	0.0634 (18)	0.177 (4)	0.100 (2)	0.035 (2)	0.0149 (17)	0.007 (2)
N1	0.0569 (11)	0.0752 (13)	0.0304 (8)	−0.0107 (10)	−0.0024 (7)	−0.0089 (8)
O1	0.0749 (11)	0.0631 (9)	0.0388 (8)	0.0026 (8)	0.0006 (7)	−0.0118 (7)
O2	0.0827 (12)	0.0793 (11)	0.0525 (9)	0.0227 (10)	−0.0090 (8)	0.0118 (8)
Cl1	0.0654 (4)	0.1225 (6)	0.0366 (3)	−0.0108 (4)	−0.0019 (2)	−0.0188 (3)
Cl2	0.0536 (4)	0.1048 (6)	0.1342 (7)	−0.0020 (4)	0.0035 (4)	−0.0047 (5)
S1	0.0586 (3)	0.0562 (3)	0.0330 (3)	0.0065 (3)	−0.0041 (2)	−0.0020 (2)

C1—C6	1.387 (3)	C9—C10	1.378 (5)
C1—C2	1.400 (3)	C9—H9	0.9300
C1—S1	1.773 (2)	C10—C11	1.339 (5)
C2—C3	1.368 (3)	C10—H10	0.9300
C2—Cl1	1.731 (2)	C11—C12	1.386 (4)
C3—C4	1.372 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C14	1.504 (4)
C4—C5	1.374 (3)	C13—H13A	0.9600
C4—Cl2	1.739 (2)	C13—H13B	0.9600
C5—C6	1.377 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.373 (3)	C14—H14C	0.9600
C7—C12	1.396 (3)	N1—S1	1.593 (2)
C7—N1	1.440 (3)	N1—H1N	0.825 (15)
C8—C9	1.389 (4)	O1—S1	1.4262 (14)
C8—C13	1.506 (4)	O2—S1	1.4247 (16)
C6—C1—C2	118.4 (2)	C9—C10—H10	119.6
C6—C1—S1	118.59 (16)	C10—C11—C12	121.3 (3)
C2—C1—S1	123.03 (16)	C10—C11—H11	119.4
C3—C2—C1	120.9 (2)	C12—C11—H11	119.4
C3—C2—Cl1	118.32 (16)	C11—C12—C7	117.4 (3)
C1—C2—Cl1	120.75 (17)	C11—C12—C14	121.0 (3)
C2—C3—C4	119.3 (2)	C7—C12—C14	121.5 (2)
C2—C3—H3	120.4	C8—C13—H13A	109.5
C4—C3—H3	120.4	C8—C13—H13B	109.5
C3—C4—C5	121.4 (2)	H13A—C13—H13B	109.5
C3—C4—Cl2	118.8 (2)	C8—C13—H13C	109.5
C5—C4—Cl2	119.78 (19)	H13A—C13—H13C	109.5
C4—C5—C6	119.2 (2)	H13B—C13—H13C	109.5
C4—C5—H5	120.4	C12—C14—H14A	109.5
C6—C5—H5	120.4	C12—C14—H14B	109.5
C5—C6—C1	120.8 (2)	H14A—C14—H14B	109.5
C5—C6—H6	119.6	C12—C14—H14C	109.5
C1—C6—H6	119.6	H14A—C14—H14C	109.5
C8—C7—C12	122.3 (2)	H14B—C14—H14C	109.5
C8—C7—N1	119.84 (19)	C7—N1—S1	124.04 (13)
C12—C7—N1	117.8 (2)	C7—N1—H1N	118.1 (17)
C7—C8—C9	117.7 (3)	S1—N1—H1N	117.8 (17)
C7—C8—C13	121.6 (2)	O2—S1—O1	119.76 (10)
C9—C8—C13	120.7 (3)	O2—S1—N1	108.50 (10)
C10—C9—C8	120.5 (3)	O1—S1—N1	107.53 (9)
C10—C9—H9	119.7	O2—S1—C1	106.34 (10)
C8—C9—H9	119.7	O1—S1—C1	105.95 (10)
C11—C10—C9	120.8 (3)	N1—S1—C1	108.30 (10)
C11—C10—H10	119.6
C6—C1—C2—C3	−0.3 (3)	C8—C9—C10—C11	−0.2 (5)
S1—C1—C2—C3	−179.53 (17)	C9—C10—C11—C12	0.1 (5)
C6—C1—C2—Cl1	−179.77 (16)	C10—C11—C12—C7	0.4 (4)
S1—C1—C2—Cl1	1.0 (3)	C10—C11—C12—C14	−179.3 (3)
C1—C2—C3—C4	0.1 (3)	C8—C7—C12—C11	−0.8 (4)
Cl1—C2—C3—C4	179.67 (17)	N1—C7—C12—C11	−178.0 (2)
C2—C3—C4—C5	0.1 (4)	C8—C7—C12—C14	178.9 (3)
C2—C3—C4—Cl2	179.73 (17)	N1—C7—C12—C14	1.7 (3)
C3—C4—C5—C6	−0.2 (4)	C8—C7—N1—S1	99.6 (2)
Cl2—C4—C5—C6	−179.87 (17)	C12—C7—N1—S1	−83.2 (2)
C4—C5—C6—C1	0.1 (3)	C7—N1—S1—O2	144.48 (18)
C2—C1—C6—C5	0.1 (3)	C7—N1—S1—O1	13.6 (2)
S1—C1—C6—C5	179.42 (17)	C7—N1—S1—C1	−100.48 (18)
C12—C7—C8—C9	0.7 (4)	C6—C1—S1—O2	−123.30 (17)
N1—C7—C8—C9	177.8 (2)	C2—C1—S1—O2	56.0 (2)
C12—C7—C8—C13	−176.9 (3)	C6—C1—S1—O1	5.14 (19)
N1—C7—C8—C13	0.2 (4)	C2—C1—S1—O1	−175.59 (17)
C7—C8—C9—C10	−0.2 (5)	C6—C1—S1—N1	120.25 (17)
C13—C8—C9—C10	177.4 (3)	C2—C1—S1—N1	−60.47 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.14 (2)	2.891 (2)	152 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.14 (2)	2.891 (2)	152 (2)

Symmetry code: (i) .