4-Chloro-N-(2,3-dimethyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(14)ClNO(2)S, the two aromatic rings are tilted relative to each other by 34.7 (1)°. In the crystal, the mol-ecules form zigzag chains along the c axis via inter-molecular 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. (2009 ▶); Shakuntala et al. (2011 ▶) and on the structures of N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 4.9926 (6) Å

b = 22.296 (3) Å

c = 12.793 (2) Å

β = 90.11 (1)°

V = 1424.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 293 K

0.40 × 0.12 × 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 = 0.853, T max = 0.960

5341 measured reflections

2669 independent reflections

1882 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.116

S = 1.07

2669 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.40 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/S1600536811016321/bt5537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016321/bt5537Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016321/bt5537Isup3.cml

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.380 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1658 reflections
a = 4.9926 (6) Å	θ = 3.2–27.9°
b = 22.296 (3) Å	µ = 0.41 mm−1
c = 12.793 (2) Å	T = 293 K
β = 90.11 (1)°	Needle, colourless
V = 1424.1 (3) Å3	0.40 × 0.12 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2669 independent reflections
Radiation source: fine-focus sealed tube	1882 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω and φ scans	θmax = 25.7°, θmin = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −4→6
Tmin = 0.853, Tmax = 0.960	k = −27→26
5341 measured reflections	l = −13→15

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0284P)2 + 1.6874P] where P = (Fo2 + 2Fc2)/3
2669 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.40 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	−0.0055 (6)	0.22651 (14)	0.3463 (2)	0.0406 (7)
C2	0.1101 (6)	0.21646 (17)	0.2488 (3)	0.0536 (9)
H2	0.2466	0.2413	0.2249	0.064*
C3	0.0209 (7)	0.16946 (18)	0.1881 (3)	0.0573 (9)
H3	0.0973	0.1623	0.1230	0.069*
C4	−0.1806 (7)	0.13352 (15)	0.2240 (3)	0.0516 (9)
C5	−0.2940 (7)	0.14244 (16)	0.3206 (3)	0.0544 (9)
H5	−0.4285	0.1170	0.3443	0.065*
C6	−0.2071 (6)	0.18932 (15)	0.3820 (3)	0.0490 (8)
H6	−0.2837	0.1959	0.4472	0.059*
C7	−0.0479 (6)	0.37146 (15)	0.2783 (2)	0.0426 (8)
C8	0.1300 (6)	0.41952 (15)	0.2693 (2)	0.0425 (7)
C9	0.1703 (6)	0.44421 (16)	0.1699 (3)	0.0487 (8)
C10	0.0308 (8)	0.42138 (18)	0.0854 (3)	0.0612 (10)
H10	0.0579	0.4379	0.0195	0.073*
C11	−0.1469 (8)	0.37484 (19)	0.0965 (3)	0.0656 (11)
H11	−0.2390	0.3603	0.0386	0.079*
C12	−0.1889 (7)	0.34977 (17)	0.1933 (3)	0.0565 (9)
H12	−0.3108	0.3186	0.2014	0.068*
C13	0.2732 (7)	0.44507 (16)	0.3628 (3)	0.0551 (9)
H13A	0.2268	0.4866	0.3706	0.066*
H13B	0.4631	0.4414	0.3531	0.066*
H13C	0.2211	0.4234	0.4244	0.066*
C14	0.3601 (8)	0.49621 (18)	0.1552 (3)	0.0665 (11)
H14A	0.5360	0.4849	0.1783	0.080*
H14B	0.2988	0.5299	0.1953	0.080*
H14C	0.3663	0.5069	0.0825	0.080*
N1	−0.0959 (5)	0.34539 (12)	0.3801 (2)	0.0448 (7)
H1N	−0.2211	0.3596	0.4190	0.054*
O1	0.0057 (5)	0.27818 (11)	0.52703 (17)	0.0567 (6)
O2	0.3577 (4)	0.30355 (11)	0.3984 (2)	0.0584 (7)
Cl1	−0.2989 (3)	0.07532 (5)	0.14708 (8)	0.0827 (4)
S1	0.08490 (15)	0.28949 (4)	0.42182 (7)	0.0439 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0330 (16)	0.0457 (19)	0.0432 (18)	0.0034 (14)	0.0016 (13)	0.0061 (15)
C2	0.0417 (18)	0.066 (2)	0.053 (2)	−0.0004 (18)	0.0105 (16)	0.0081 (19)
C3	0.060 (2)	0.069 (3)	0.042 (2)	0.011 (2)	0.0078 (17)	−0.0032 (19)
C4	0.064 (2)	0.046 (2)	0.045 (2)	0.0038 (18)	−0.0099 (17)	0.0026 (16)
C5	0.062 (2)	0.047 (2)	0.054 (2)	−0.0121 (18)	0.0005 (17)	0.0084 (17)
C6	0.0497 (19)	0.052 (2)	0.0452 (19)	−0.0055 (16)	0.0075 (15)	0.0031 (16)
C7	0.0295 (16)	0.0493 (19)	0.0491 (19)	0.0046 (14)	0.0004 (14)	−0.0009 (16)
C8	0.0359 (17)	0.0448 (18)	0.0467 (19)	0.0048 (15)	0.0003 (14)	−0.0028 (15)
C9	0.0467 (19)	0.050 (2)	0.049 (2)	0.0086 (16)	0.0074 (16)	0.0002 (16)
C10	0.071 (2)	0.069 (3)	0.044 (2)	0.014 (2)	0.0033 (18)	0.0010 (19)
C11	0.064 (2)	0.076 (3)	0.057 (2)	0.008 (2)	−0.0156 (19)	−0.014 (2)
C12	0.044 (2)	0.058 (2)	0.067 (2)	−0.0031 (17)	−0.0097 (17)	−0.010 (2)
C13	0.060 (2)	0.049 (2)	0.057 (2)	−0.0072 (17)	−0.0039 (17)	−0.0010 (18)
C14	0.071 (3)	0.065 (3)	0.063 (2)	0.000 (2)	0.011 (2)	0.013 (2)
N1	0.0317 (13)	0.0481 (16)	0.0547 (17)	0.0026 (12)	0.0102 (12)	0.0003 (13)
O1	0.0572 (14)	0.0675 (16)	0.0453 (13)	−0.0098 (12)	−0.0013 (11)	0.0002 (12)
O2	0.0251 (11)	0.0680 (16)	0.0821 (18)	−0.0066 (11)	−0.0027 (11)	0.0055 (14)
Cl1	0.1197 (10)	0.0646 (7)	0.0637 (7)	−0.0041 (6)	−0.0174 (6)	−0.0123 (5)
S1	0.0286 (4)	0.0523 (5)	0.0510 (5)	−0.0050 (4)	0.0002 (3)	0.0027 (4)

C1—C6	1.382 (4)	C9—C10	1.382 (5)
C1—C2	1.393 (4)	C9—C14	1.509 (5)
C1—S1	1.763 (3)	C10—C11	1.373 (5)
C2—C3	1.378 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.374 (5)
C3—C4	1.366 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.375 (5)	C13—H13A	0.9600
C4—Cl1	1.732 (3)	C13—H13B	0.9600
C5—C6	1.377 (5)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C12	1.382 (4)	C14—H14C	0.9600
C7—C8	1.397 (4)	N1—S1	1.628 (3)
C7—N1	1.447 (4)	N1—H1N	0.8600
C8—C9	1.401 (4)	O1—S1	1.426 (2)
C8—C13	1.505 (4)	O2—S1	1.430 (2)
C6—C1—C2	120.1 (3)	C9—C10—H10	119.3
C6—C1—S1	118.9 (2)	C10—C11—C12	120.1 (4)
C2—C1—S1	120.8 (3)	C10—C11—H11	120.0
C3—C2—C1	119.5 (3)	C12—C11—H11	120.0
C3—C2—H2	120.2	C11—C12—C7	119.2 (3)
C1—C2—H2	120.2	C11—C12—H12	120.4
C4—C3—C2	119.6 (3)	C7—C12—H12	120.4
C4—C3—H3	120.2	C8—C13—H13A	109.5
C2—C3—H3	120.2	C8—C13—H13B	109.5
C3—C4—C5	121.5 (3)	H13A—C13—H13B	109.5
C3—C4—Cl1	119.9 (3)	C8—C13—H13C	109.5
C5—C4—Cl1	118.6 (3)	H13A—C13—H13C	109.5
C4—C5—C6	119.5 (3)	H13B—C13—H13C	109.5
C4—C5—H5	120.2	C9—C14—H14A	109.5
C6—C5—H5	120.2	C9—C14—H14B	109.5
C5—C6—C1	119.7 (3)	H14A—C14—H14B	109.5
C5—C6—H6	120.1	C9—C14—H14C	109.5
C1—C6—H6	120.1	H14A—C14—H14C	109.5
C12—C7—C8	121.8 (3)	H14B—C14—H14C	109.5
C12—C7—N1	118.9 (3)	C7—N1—S1	120.7 (2)
C8—C7—N1	119.3 (3)	C7—N1—H1N	119.7
C7—C8—C9	118.0 (3)	S1—N1—H1N	119.7
C7—C8—C13	121.7 (3)	O1—S1—O2	120.18 (15)
C9—C8—C13	120.3 (3)	O1—S1—N1	106.86 (14)
C10—C9—C8	119.5 (3)	O2—S1—N1	106.92 (14)
C10—C9—C14	120.1 (3)	O1—S1—C1	107.77 (15)
C8—C9—C14	120.4 (3)	O2—S1—C1	107.62 (15)
C11—C10—C9	121.5 (4)	N1—S1—C1	106.81 (14)
C11—C10—H10	119.3
C6—C1—C2—C3	0.4 (5)	C8—C9—C10—C11	−0.1 (5)
S1—C1—C2—C3	−175.1 (3)	C14—C9—C10—C11	−178.8 (3)
C1—C2—C3—C4	0.3 (5)	C9—C10—C11—C12	−0.2 (6)
C2—C3—C4—C5	−1.2 (5)	C10—C11—C12—C7	−0.8 (6)
C2—C3—C4—Cl1	178.7 (3)	C8—C7—C12—C11	2.1 (5)
C3—C4—C5—C6	1.3 (5)	N1—C7—C12—C11	179.2 (3)
Cl1—C4—C5—C6	−178.5 (3)	C12—C7—N1—S1	91.9 (3)
C4—C5—C6—C1	−0.6 (5)	C8—C7—N1—S1	−91.0 (3)
C2—C1—C6—C5	−0.3 (5)	C7—N1—S1—O1	174.6 (2)
S1—C1—C6—C5	175.3 (3)	C7—N1—S1—O2	44.7 (3)
C12—C7—C8—C9	−2.3 (5)	C7—N1—S1—C1	−70.3 (3)
N1—C7—C8—C9	−179.4 (3)	C6—C1—S1—O1	22.9 (3)
C12—C7—C8—C13	176.9 (3)	C2—C1—S1—O1	−161.6 (3)
N1—C7—C8—C13	−0.1 (4)	C6—C1—S1—O2	153.8 (3)
C7—C8—C9—C10	1.3 (5)	C2—C1—S1—O2	−30.6 (3)
C13—C8—C9—C10	−178.0 (3)	C6—C1—S1—N1	−91.7 (3)
C7—C8—C9—C14	180.0 (3)	C2—C1—S1—N1	83.9 (3)
C13—C8—C9—C14	0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.46	2.893 (3)	112

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.46	2.893 (3)	112

Symmetry code: (i) .