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

In the title compound, C(14)H(14)ClNO(2)S, the angle between the sulfonyl and aniline benzene rings is 65.5 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O hydrogen bonds. The dimethyl-phenyl ring is disordered over two different orientations approximately related by a 180° rotation about the C-N bond, with occupancies of 0.643 (6) and 0.357 (6).

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009 ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H14ClNO2S

M = 295.77

Monoclinic,

a = 13.5000 (9) Å

b = 12.4039 (8) Å

c = 8.7436 (7) Å

β = 104.492 (7)°

V = 1417.55 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 100 K

0.44 × 0.34 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.839, T max = 0.915

5943 measured reflections

2890 independent reflections

2309 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.107

S = 1.07

2890 reflections

194 parameters

28 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.24 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 datablocks I, global. DOI: 10.1107/S1600536810015394/ci5082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015394/ci5082Isup2.hkl

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

C14H14ClNO2S	F(000) = 616
Mr = 295.77	Dx = 1.386 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2451 reflections
a = 13.5000 (9) Å	θ = 2.4–27.3°
b = 12.4039 (8) Å	µ = 0.41 mm−1
c = 8.7436 (7) Å	T = 100 K
β = 104.492 (7)°	Prism, colourless
V = 1417.55 (17) Å3	0.44 × 0.34 × 0.22 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2890 independent reflections
Radiation source: fine-focus sealed tube	2309 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using θ and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −16→16
Tmin = 0.839, Tmax = 0.915	k = −15→13
5943 measured reflections	l = −6→10

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.6002P] where P = (Fo2 + 2Fc2)/3
2890 reflections	(Δ/σ)max = 0.045
194 parameters	Δρmax = 0.31 e Å−3
28 restraints	Δρmin = −0.24 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.90057 (14)	0.96543 (15)	0.2942 (2)	0.0261 (4)
C2	0.91759 (15)	1.07570 (16)	0.2922 (2)	0.0321 (4)
H2	0.9592	1.1047	0.2291	0.039*
C3	0.87384 (16)	1.14279 (16)	0.3821 (2)	0.0327 (5)
H3	0.8856	1.2183	0.3832	0.039*
C4	0.81360 (15)	1.09927 (17)	0.4694 (2)	0.0318 (4)
C5	0.79804 (19)	0.98936 (18)	0.4760 (3)	0.0414 (5)
H5	0.7575	0.9609	0.5409	0.050*
C6	0.84233 (17)	0.92178 (17)	0.3870 (2)	0.0361 (5)
H6	0.8327	0.8460	0.3897	0.043*
C7	0.75973 (16)	0.8915 (2)	−0.0415 (3)	0.0441 (6)
C8	0.69977 (19)	0.9665 (3)	−0.1406 (3)	0.0586 (7)
H8	0.7317	1.0233	−0.1833	0.070*
C9	0.5922 (2)	0.9596 (3)	−0.1791 (4)	0.0778 (10)
H9	0.5524	1.0104	−0.2499	0.093*	0.357 (6)
C10	0.5445 (2)	0.8797 (4)	−0.1148 (5)	0.0887 (13)
C11	0.6051 (3)	0.8072 (3)	−0.0163 (5)	0.0808 (12)
H11	0.5728	0.7518	0.0287	0.097*	0.643 (6)
C12	0.7124 (2)	0.8098 (2)	0.0221 (3)	0.0588 (8)
H12	0.7516	0.7570	0.0899	0.071*
C13A	0.5254 (3)	1.0313 (5)	−0.2823 (6)	0.0755 (17)	0.643 (6)
H13A	0.4543	1.0100	−0.2906	0.091*	0.643 (6)
H13B	0.5392	1.0286	−0.3870	0.091*	0.643 (6)
H13C	0.5364	1.1048	−0.2405	0.091*	0.643 (6)
C14A	0.4264 (5)	0.8913 (8)	−0.1730 (11)	0.098 (3)	0.643 (6)
H14A	0.4056	0.8831	−0.2881	0.117*	0.643 (6)
H14B	0.4057	0.9626	−0.1439	0.117*	0.643 (6)
H14C	0.3933	0.8354	−0.1238	0.117*	0.643 (6)
N1	0.86904 (13)	0.89945 (15)	−0.0097 (2)	0.0360 (4)
H1N	0.8902 (18)	0.9510 (14)	−0.057 (3)	0.043*
O1	1.04407 (10)	0.92002 (12)	0.15306 (17)	0.0381 (4)
O2	0.93722 (13)	0.77276 (12)	0.2139 (2)	0.0474 (4)
Cl1	0.75301 (5)	1.18581 (5)	0.57252 (7)	0.04891 (19)
S1	0.94625 (4)	0.88149 (4)	0.16631 (6)	0.03178 (16)
C13B	0.5471 (7)	0.7346 (8)	0.0226 (12)	0.081 (3)	0.357 (6)
H13D	0.5895	0.6822	0.0938	0.097*	0.357 (6)
H13E	0.5083	0.6976	−0.0727	0.097*	0.357 (6)
H13F	0.4996	0.7690	0.0759	0.097*	0.357 (6)
C14B	0.4335 (8)	0.8452 (11)	−0.1288 (16)	0.068 (3)	0.357 (6)
H14D	0.3982	0.8363	−0.2405	0.082*	0.357 (6)
H14E	0.3986	0.9005	−0.0816	0.082*	0.357 (6)
H14F	0.4328	0.7767	−0.0733	0.082*	0.357 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0273 (9)	0.0242 (9)	0.0267 (9)	0.0021 (7)	0.0063 (7)	0.0004 (8)
C2	0.0347 (10)	0.0279 (10)	0.0360 (11)	−0.0018 (8)	0.0132 (9)	0.0033 (8)
C3	0.0381 (11)	0.0227 (10)	0.0354 (11)	0.0013 (8)	0.0057 (9)	0.0001 (8)
C4	0.0360 (11)	0.0337 (11)	0.0246 (9)	0.0057 (8)	0.0058 (8)	−0.0054 (8)
C5	0.0579 (14)	0.0374 (12)	0.0368 (12)	−0.0042 (10)	0.0265 (11)	−0.0021 (10)
C6	0.0519 (13)	0.0252 (10)	0.0359 (11)	−0.0019 (9)	0.0201 (10)	0.0013 (9)
C7	0.0324 (11)	0.0642 (16)	0.0390 (12)	−0.0098 (10)	0.0153 (9)	−0.0290 (12)
C8	0.0390 (13)	0.096 (2)	0.0401 (13)	0.0017 (13)	0.0079 (11)	−0.0184 (14)
C9	0.0402 (15)	0.130 (3)	0.0553 (17)	0.0094 (18)	−0.0033 (13)	−0.028 (2)
C10	0.0359 (15)	0.141 (4)	0.089 (2)	−0.026 (2)	0.0145 (17)	−0.056 (3)
C11	0.0532 (18)	0.102 (3)	0.099 (3)	−0.0467 (19)	0.0412 (18)	−0.059 (2)
C12	0.0484 (14)	0.0672 (18)	0.0686 (18)	−0.0250 (13)	0.0292 (13)	−0.0355 (15)
C13A	0.043 (2)	0.114 (4)	0.065 (3)	0.005 (2)	0.005 (2)	0.016 (3)
C14A	0.043 (3)	0.123 (6)	0.114 (6)	−0.017 (4)	−0.003 (3)	−0.029 (5)
N1	0.0312 (9)	0.0456 (11)	0.0351 (10)	−0.0043 (8)	0.0158 (7)	−0.0083 (8)
O1	0.0279 (7)	0.0451 (9)	0.0442 (9)	0.0049 (6)	0.0146 (6)	0.0041 (7)
O2	0.0592 (10)	0.0260 (8)	0.0676 (11)	0.0074 (7)	0.0355 (9)	0.0023 (8)
Cl1	0.0579 (4)	0.0490 (4)	0.0418 (3)	0.0103 (3)	0.0163 (3)	−0.0153 (3)
S1	0.0315 (3)	0.0293 (3)	0.0384 (3)	0.0036 (2)	0.0160 (2)	−0.0004 (2)
C13B	0.065 (5)	0.084 (6)	0.097 (6)	−0.031 (4)	0.026 (4)	0.016 (5)
C14B	0.036 (5)	0.094 (7)	0.075 (6)	−0.032 (5)	0.016 (4)	0.012 (5)

C1—C6	1.374 (3)	C10—C14A	1.554 (7)
C1—C2	1.388 (3)	C11—C13B	1.293 (8)
C1—S1	1.7490 (19)	C11—C12	1.403 (4)
C2—C3	1.376 (3)	C11—H11	0.95
C2—H2	0.95	C12—H12	0.95
C3—C4	1.358 (3)	C13A—H13A	0.98
C3—H3	0.95	C13A—H13B	0.98
C4—C5	1.383 (3)	C13A—H13C	0.98
C4—Cl1	1.733 (2)	C14A—H14A	0.98
C5—C6	1.378 (3)	C14A—H14B	0.98
C5—H5	0.95	C14A—H14C	0.98
C6—H6	0.95	N1—S1	1.6439 (19)
C7—C8	1.385 (4)	N1—H1N	0.849 (10)
C7—C12	1.387 (4)	O1—S1	1.4360 (14)
C7—N1	1.435 (3)	O2—S1	1.4255 (16)
C8—C9	1.409 (4)	C13B—H13D	0.98
C8—H8	0.95	C13B—H13E	0.98
C9—C10	1.377 (6)	C13B—H13F	0.98
C9—C13A	1.418 (5)	C14B—H14D	0.98
C9—H9	0.95	C14B—H14E	0.98
C10—C11	1.367 (6)	C14B—H14F	0.98
C10—C14B	1.533 (10)
C6—C1—C2	121.11 (18)	C12—C11—H11	118.1
C6—C1—S1	119.21 (15)	C7—C12—C11	118.2 (3)
C2—C1—S1	119.53 (15)	C7—C12—H12	120.9
C3—C2—C1	119.54 (19)	C11—C12—H12	120.9
C3—C2—H2	120.2	C9—C13A—H13A	109.5
C1—C2—H2	120.2	C9—C13A—H13B	109.5
C4—C3—C2	118.92 (19)	H13A—C13A—H13B	109.5
C4—C3—H3	120.5	C9—C13A—H13C	109.5
C2—C3—H3	120.5	H13A—C13A—H13C	109.5
C3—C4—C5	122.28 (19)	H13B—C13A—H13C	109.5
C3—C4—Cl1	118.22 (16)	C10—C14A—H14A	109.5
C5—C4—Cl1	119.49 (17)	C10—C14A—H14B	109.5
C6—C5—C4	118.9 (2)	H14A—C14A—H14B	109.5
C6—C5—H5	120.5	C10—C14A—H14C	109.5
C4—C5—H5	120.5	H14A—C14A—H14C	109.5
C1—C6—C5	119.14 (19)	H14B—C14A—H14C	109.5
C1—C6—H6	120.4	C7—N1—S1	123.52 (15)
C5—C6—H6	120.4	C7—N1—H1N	114.3 (17)
C8—C7—C12	119.1 (2)	S1—N1—H1N	110.2 (17)
C8—C7—N1	119.1 (2)	O2—S1—O1	119.07 (10)
C12—C7—N1	121.8 (2)	O2—S1—N1	108.71 (11)
C7—C8—C9	121.0 (3)	O1—S1—N1	105.06 (9)
C7—C8—H8	119.5	O2—S1—C1	107.89 (9)
C9—C8—H8	119.5	O1—S1—C1	109.38 (9)
C10—C9—C8	120.4 (3)	N1—S1—C1	105.98 (9)
C10—C9—C13A	115.0 (3)	C11—C13B—H13D	109.5
C8—C9—C13A	124.6 (4)	C11—C13B—H13E	109.5
C10—C9—H9	119.8	H13D—C13B—H13E	109.5
C8—C9—H9	119.8	C11—C13B—H13F	109.5
C11—C10—C9	117.6 (3)	H13D—C13B—H13F	109.5
C11—C10—C14B	106.6 (6)	H13E—C13B—H13F	109.5
C9—C10—C14B	135.8 (6)	C10—C14B—H14D	109.5
C11—C10—C14A	132.1 (5)	C10—C14B—H14E	109.5
C9—C10—C14A	110.3 (5)	H14D—C14B—H14E	109.5
C13B—C11—C10	108.5 (6)	C10—C14B—H14F	109.5
C13B—C11—C12	127.6 (6)	H14D—C14B—H14F	109.5
C10—C11—C12	123.7 (3)	H14E—C14B—H14F	109.5
C10—C11—H11	118.1
C6—C1—C2—C3	−1.3 (3)	C14B—C10—C11—C13B	2.7 (9)
S1—C1—C2—C3	174.13 (15)	C14A—C10—C11—C13B	4.3 (8)
C1—C2—C3—C4	−0.9 (3)	C9—C10—C11—C12	−0.1 (5)
C2—C3—C4—C5	2.7 (3)	C14B—C10—C11—C12	178.0 (7)
C2—C3—C4—Cl1	−176.19 (15)	C14A—C10—C11—C12	179.6 (5)
C3—C4—C5—C6	−2.2 (3)	C8—C7—C12—C11	−0.5 (3)
Cl1—C4—C5—C6	176.64 (17)	N1—C7—C12—C11	−179.3 (2)
C2—C1—C6—C5	1.8 (3)	C13B—C11—C12—C7	175.4 (7)
S1—C1—C6—C5	−173.69 (17)	C10—C11—C12—C7	1.0 (4)
C4—C5—C6—C1	0.0 (3)	C8—C7—N1—S1	138.1 (2)
C12—C7—C8—C9	−1.0 (4)	C12—C7—N1—S1	−43.0 (3)
N1—C7—C8—C9	177.9 (2)	C7—N1—S1—O2	64.1 (2)
C7—C8—C9—C10	1.9 (4)	C7—N1—S1—O1	−167.36 (18)
C7—C8—C9—C13A	−178.5 (4)	C7—N1—S1—C1	−51.6 (2)
C8—C9—C10—C11	−1.4 (5)	C6—C1—S1—O2	−16.05 (19)
C13A—C9—C10—C11	179.0 (4)	C2—C1—S1—O2	168.43 (16)
C8—C9—C10—C14B	−178.7 (9)	C6—C1—S1—O1	−146.96 (16)
C13A—C9—C10—C14B	1.7 (10)	C2—C1—S1—O1	37.52 (18)
C8—C9—C10—C14A	178.8 (4)	C6—C1—S1—N1	100.26 (17)
C13A—C9—C10—C14A	−0.8 (6)	C2—C1—S1—N1	−75.27 (17)
C9—C10—C11—C13B	−175.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.10 (1)	2.949 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.10 (1)	2.949 (2)	174 (2)

Symmetry code: (i) .