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

The N-H bond in the title compound, C(14)H(14)ClNO(2)S, the dihedral angle between the two benzene rings is 75.5 (1)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation, see: Savitha & Gowda (2006 ▶). For our study of the effect of substituents on the crystal structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 7.8830 (7) Å

b = 11.602 (1) Å

c = 15.645 (2) Å

β = 90.593 (8)°

V = 1430.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 299 K

0.48 × 0.28 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.828, T max = 0.953

5563 measured reflections

2925 independent reflections

1980 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.156

S = 1.03

2925 reflections

177 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.44 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/S1600536809051083/ci2978sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051083/ci2978Isup2.hkl

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2116 reflections
a = 7.8830 (7) Å	θ = 2.6–27.9°
b = 11.602 (1) Å	µ = 0.41 mm−1
c = 15.645 (2) Å	T = 299 K
β = 90.593 (8)°	Prism, colourless
V = 1430.8 (3) Å3	0.48 × 0.28 × 0.12 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2925 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→6
Tmin = 0.828, Tmax = 0.953	k = −11→14
5563 measured reflections	l = −19→18

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0757P)2 + 0.6262P] where P = (Fo2 + 2Fc2)/3
2925 reflections	(Δ/σ)max = 0.020
177 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.44 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	0.6521 (3)	0.1989 (2)	0.83780 (16)	0.0484 (6)
C2	0.8133 (4)	0.1933 (2)	0.87588 (18)	0.0552 (7)
C3	0.9404 (4)	0.2588 (3)	0.8394 (2)	0.0679 (8)
H3	1.0494	0.2563	0.8627	0.081*
C4	0.9084 (4)	0.3278 (3)	0.7692 (2)	0.0675 (8)
C5	0.7500 (5)	0.3331 (3)	0.7328 (2)	0.0725 (9)
H5	0.7292	0.3802	0.6858	0.087*
C6	0.6223 (4)	0.2679 (3)	0.76688 (18)	0.0616 (8)
H6	0.5145	0.2700	0.7421	0.074*
C7	0.3599 (3)	0.2701 (2)	0.99538 (18)	0.0509 (6)
C8	0.3539 (3)	0.3658 (2)	0.94325 (19)	0.0584 (7)
H8	0.4012	0.3622	0.8891	0.070*
C9	0.2787 (4)	0.4672 (3)	0.9703 (2)	0.0630 (8)
C10	0.2096 (5)	0.4692 (3)	1.0506 (2)	0.0882 (11)
H10	0.1577	0.5362	1.0700	0.106*
C11	0.2159 (5)	0.3740 (4)	1.1028 (2)	0.0929 (12)
H11	0.1698	0.3776	1.1572	0.111*
C12	0.2895 (4)	0.2737 (3)	1.07543 (19)	0.0663 (8)
H12	0.2919	0.2090	1.1105	0.080*
C13	0.8530 (4)	0.1198 (3)	0.9571 (2)	0.0703 (9)
H13A	0.8313	0.0400	0.9451	0.084*
H13B	0.7823	0.1448	1.0032	0.084*
H13C	0.9701	0.1295	0.9732	0.084*
C14	0.2762 (5)	0.5716 (3)	0.9131 (3)	0.0857 (11)
H14A	0.2078	0.5560	0.8634	0.103*
H14B	0.3898	0.5896	0.8961	0.103*
H14C	0.2293	0.6359	0.9435	0.103*
N1	0.4428 (4)	0.1662 (2)	0.97214 (17)	0.0692 (8)
H1N	0.445 (4)	0.118 (3)	1.011 (2)	0.083*
O1	0.3367 (3)	0.1432 (2)	0.82291 (15)	0.0752 (6)
O2	0.5297 (3)	0.00166 (16)	0.88893 (14)	0.0708 (6)
Cl1	1.07032 (16)	0.41278 (11)	0.72879 (9)	0.1237 (5)
S1	0.47841 (9)	0.11958 (6)	0.87689 (5)	0.0572 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0546 (15)	0.0446 (13)	0.0461 (14)	0.0116 (12)	−0.0020 (11)	−0.0040 (12)
C2	0.0599 (16)	0.0479 (15)	0.0576 (16)	0.0147 (13)	−0.0036 (13)	−0.0032 (13)
C3	0.0566 (17)	0.0603 (19)	0.087 (2)	0.0091 (15)	0.0030 (16)	−0.0136 (17)
C4	0.077 (2)	0.0543 (17)	0.071 (2)	0.0048 (15)	0.0271 (17)	−0.0090 (16)
C5	0.099 (3)	0.066 (2)	0.0528 (17)	0.0143 (19)	0.0131 (17)	0.0072 (15)
C6	0.0692 (19)	0.0651 (18)	0.0504 (16)	0.0146 (15)	−0.0034 (14)	0.0023 (14)
C7	0.0479 (14)	0.0486 (15)	0.0563 (16)	−0.0009 (11)	0.0032 (12)	−0.0036 (12)
C8	0.0590 (16)	0.0532 (17)	0.0631 (18)	0.0017 (13)	0.0068 (14)	−0.0016 (14)
C9	0.0591 (18)	0.0513 (16)	0.078 (2)	0.0032 (13)	−0.0098 (15)	−0.0089 (15)
C10	0.104 (3)	0.081 (3)	0.080 (3)	0.036 (2)	−0.004 (2)	−0.022 (2)
C11	0.107 (3)	0.108 (3)	0.064 (2)	0.036 (2)	0.015 (2)	−0.009 (2)
C12	0.0658 (18)	0.073 (2)	0.0604 (18)	0.0085 (15)	0.0035 (15)	0.0038 (15)
C13	0.0676 (19)	0.0651 (19)	0.078 (2)	0.0248 (15)	−0.0330 (16)	0.0020 (16)
C14	0.094 (3)	0.0524 (19)	0.111 (3)	0.0071 (18)	−0.014 (2)	0.0019 (19)
N1	0.095 (2)	0.0514 (15)	0.0613 (16)	0.0169 (14)	0.0169 (14)	0.0085 (12)
O1	0.0598 (12)	0.0789 (15)	0.0866 (16)	0.0024 (11)	−0.0155 (11)	−0.0093 (12)
O2	0.0932 (15)	0.0446 (11)	0.0749 (14)	0.0048 (10)	0.0039 (11)	−0.0041 (10)
Cl1	0.1293 (10)	0.1064 (9)	0.1367 (11)	−0.0264 (7)	0.0632 (8)	−0.0064 (7)
S1	0.0630 (5)	0.0485 (4)	0.0600 (5)	0.0044 (3)	−0.0008 (3)	−0.0033 (3)

C1—C6	1.387 (4)	C9—C10	1.375 (5)
C1—C2	1.399 (4)	C9—C14	1.506 (5)
C1—S1	1.764 (3)	C10—C11	1.375 (5)
C2—C3	1.386 (4)	C10—H10	0.93
C2—C13	1.560 (4)	C11—C12	1.371 (5)
C3—C4	1.380 (5)	C11—H11	0.93
C3—H3	0.93	C12—H12	0.93
C4—C5	1.369 (5)	C13—H13A	0.96
C4—Cl1	1.737 (3)	C13—H13B	0.96
C5—C6	1.371 (4)	C13—H13C	0.96
C5—H5	0.93	C14—H14A	0.96
C6—H6	0.93	C14—H14B	0.96
C7—C12	1.375 (4)	C14—H14C	0.96
C7—C8	1.378 (4)	N1—S1	1.613 (3)
C7—N1	1.420 (3)	N1—H1N	0.82 (4)
C8—C9	1.386 (4)	O1—S1	1.420 (2)
C8—H8	0.93	O2—S1	1.438 (2)
C6—C1—C2	120.9 (3)	C9—C10—H10	119.4
C6—C1—S1	116.9 (2)	C12—C11—C10	120.6 (3)
C2—C1—S1	122.2 (2)	C12—C11—H11	119.7
C3—C2—C1	117.2 (3)	C10—C11—H11	119.7
C3—C2—C13	119.7 (3)	C11—C12—C7	119.1 (3)
C1—C2—C13	123.1 (3)	C11—C12—H12	120.4
C4—C3—C2	121.2 (3)	C7—C12—H12	120.4
C4—C3—H3	119.4	C2—C13—H13A	109.5
C2—C3—H3	119.4	C2—C13—H13B	109.5
C5—C4—C3	121.0 (3)	H13A—C13—H13B	109.5
C5—C4—Cl1	119.6 (3)	C2—C13—H13C	109.5
C3—C4—Cl1	119.3 (3)	H13A—C13—H13C	109.5
C4—C5—C6	119.0 (3)	H13B—C13—H13C	109.5
C4—C5—H5	120.5	C9—C14—H14A	109.5
C6—C5—H5	120.5	C9—C14—H14B	109.5
C5—C6—C1	120.7 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.7	C9—C14—H14C	109.5
C1—C6—H6	119.7	H14A—C14—H14C	109.5
C12—C7—C8	120.2 (3)	H14B—C14—H14C	109.5
C12—C7—N1	116.7 (3)	C7—N1—S1	127.3 (2)
C8—C7—N1	123.0 (3)	C7—N1—H1N	114 (3)
C7—C8—C9	121.0 (3)	S1—N1—H1N	116 (3)
C7—C8—H8	119.5	O1—S1—O2	118.67 (14)
C9—C8—H8	119.5	O1—S1—N1	109.96 (14)
C10—C9—C8	117.9 (3)	O2—S1—N1	104.43 (13)
C10—C9—C14	121.7 (3)	O1—S1—C1	107.55 (13)
C8—C9—C14	120.3 (3)	O2—S1—C1	108.88 (13)
C11—C10—C9	121.1 (3)	N1—S1—C1	106.78 (14)
C11—C10—H10	119.4
C6—C1—C2—C3	−0.3 (4)	C8—C9—C10—C11	0.5 (5)
S1—C1—C2—C3	179.6 (2)	C14—C9—C10—C11	−178.6 (4)
C6—C1—C2—C13	178.3 (3)	C9—C10—C11—C12	−0.9 (6)
S1—C1—C2—C13	−1.7 (4)	C10—C11—C12—C7	1.1 (6)
C1—C2—C3—C4	0.8 (4)	C8—C7—C12—C11	−0.9 (5)
C13—C2—C3—C4	−177.8 (3)	N1—C7—C12—C11	176.6 (3)
C2—C3—C4—C5	−0.5 (5)	C12—C7—N1—S1	157.2 (2)
C2—C3—C4—Cl1	177.3 (2)	C8—C7—N1—S1	−25.5 (4)
C3—C4—C5—C6	−0.5 (5)	C7—N1—S1—O1	−39.2 (3)
Cl1—C4—C5—C6	−178.2 (2)	C7—N1—S1—O2	−167.5 (3)
C4—C5—C6—C1	1.0 (4)	C7—N1—S1—C1	77.2 (3)
C2—C1—C6—C5	−0.5 (4)	C6—C1—S1—O1	1.2 (2)
S1—C1—C6—C5	179.5 (2)	C2—C1—S1—O1	−178.8 (2)
C12—C7—C8—C9	0.5 (4)	C6—C1—S1—O2	130.9 (2)
N1—C7—C8—C9	−176.8 (3)	C2—C1—S1—O2	−49.0 (3)
C7—C8—C9—C10	−0.2 (4)	C6—C1—S1—N1	−116.8 (2)
C7—C8—C9—C14	178.9 (3)	C2—C1—S1—N1	63.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.82 (4)	2.10 (4)	2.925 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.82 (4)	2.10 (4)	2.925 (3)	176 (3)

Symmetry code: (i) .