4-Chloro-N-phenyl-benzene-sulfonamide.

In the crystal of the title compound, C(12)H(10)ClNO(2)S, the asymmetric unit contains two independent mol-ecules. The N-C bonds in the C-SO(2)-NH-C segments have gauche torsions with respect to the S=O bonds. The mol-ecules are twisted at the S atoms with C-SO(2)-NH-C torsion angles of -53.8 (3) and -63.4 (3)° in the two mol-ecules. The benzene rings are tilted relative to each other by 69.1 (1) and 82.6 (1)°. The dihedral angle between the sulfonyl benzene rings of the two independent mol-ecules is 23.7 (2)°. The crystal structure features inversion-related dimers linked by N-H⋯O hydrogen bonds.

Related literature

For hydrogen-bonding preferences 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: Shakuntala et al. (2011 ▶); and on the oxidative strengths of N-chloro,N-aryl­sulfonamides, see: Gowda & Kumar (2003 ▶).

Experimental

Crystal data

C12H10ClNO2S

M = 267.72

Triclinic,

a = 10.206 (1) Å

b = 10.900 (1) Å

c = 13.461 (2) Å

α = 68.19 (1)°

β = 87.64 (2)°

γ = 67.08 (1)°

V = 1271.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 293 K

0.40 × 0.36 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.840, T max = 0.876

8487 measured reflections

4831 independent reflections

2470 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 0.93

4831 reflections

313 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.29 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/S1600536811015108/nc2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015108/nc2229Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015108/nc2229Isup3.cml

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

C12H10ClNO2S	Z = 4
Mr = 267.72	F(000) = 552
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.206 (1) Å	Cell parameters from 2291 reflections
b = 10.900 (1) Å	θ = 2.5–28.0°
c = 13.461 (2) Å	µ = 0.45 mm−1
α = 68.19 (1)°	T = 293 K
β = 87.64 (2)°	Prism, colourless
γ = 67.08 (1)°	0.40 × 0.36 × 0.30 mm
V = 1271.1 (3) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4831 independent reflections
Radiation source: fine-focus sealed tube	2470 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans	θmax = 25.7°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→11
Tmin = 0.840, Tmax = 0.876	k = −13→12
8487 measured reflections	l = −16→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0725P)2] where P = (Fo2 + 2Fc2)/3
4831 reflections	(Δ/σ)max = 0.002
313 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.29 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
Cl1	0.38715 (12)	0.51207 (13)	0.41184 (9)	0.1275 (4)
S1	−0.02351 (7)	0.72074 (7)	0.00095 (6)	0.0670 (2)
O1	−0.11578 (19)	0.6455 (2)	0.02316 (17)	0.0804 (6)
O2	−0.0837 (2)	0.87352 (19)	−0.04563 (18)	0.0897 (7)
N1	0.0811 (3)	0.6608 (2)	−0.07990 (19)	0.0692 (6)
H1N	0.089 (3)	0.576 (2)	−0.068 (2)	0.083*
C1	0.0854 (2)	0.6661 (2)	0.1192 (2)	0.0533 (6)
C2	0.1321 (3)	0.7597 (3)	0.1375 (3)	0.0733 (8)
H2	0.1012	0.8548	0.0884	0.088*
C3	0.2241 (4)	0.7129 (4)	0.2279 (3)	0.0848 (9)
H3	0.2559	0.7757	0.2403	0.102*
C4	0.2683 (3)	0.5731 (4)	0.2993 (2)	0.0720 (8)
C5	0.2225 (3)	0.4798 (3)	0.2825 (3)	0.0741 (8)
H5	0.2528	0.3850	0.3323	0.089*
C6	0.1322 (3)	0.5259 (3)	0.1927 (2)	0.0657 (8)
H6	0.1017	0.4619	0.1807	0.079*
C7	0.2053 (3)	0.6890 (3)	−0.1087 (2)	0.0664 (7)
C8	0.2085 (4)	0.8223 (3)	−0.1344 (3)	0.0948 (10)
H8	0.1270	0.8997	−0.1335	0.114*
C9	0.3330 (5)	0.8399 (5)	−0.1615 (3)	0.1103 (12)
H9	0.3356	0.9293	−0.1765	0.132*
C10	0.4510 (5)	0.7316 (6)	−0.1669 (3)	0.1183 (14)
H10	0.5340	0.7459	−0.1866	0.142*
C11	0.4471 (4)	0.6022 (5)	−0.1435 (4)	0.1243 (14)
H11	0.5282	0.5263	−0.1470	0.149*
C12	0.3244 (4)	0.5801 (4)	−0.1142 (3)	0.0973 (11)
H12	0.3236	0.4898	−0.0982	0.117*
Cl2	0.97275 (15)	0.38078 (14)	0.44881 (14)	0.1891 (7)
S2	0.70362 (9)	−0.06953 (8)	0.61492 (8)	0.0866 (3)
O3	0.6774 (3)	−0.1070 (2)	0.5286 (2)	0.1169 (9)
O4	0.7868 (2)	−0.1795 (2)	0.71098 (18)	0.0997 (7)
N2	0.5442 (3)	0.0186 (3)	0.6386 (2)	0.0906 (8)
H2N	0.477 (3)	0.060 (3)	0.583 (2)	0.109*
C13	0.7846 (3)	0.0531 (3)	0.5660 (2)	0.0719 (8)
C14	0.7295 (4)	0.1667 (4)	0.4690 (3)	0.1014 (11)
H14	0.6519	0.1764	0.4283	0.122*
C15	0.7889 (5)	0.2658 (5)	0.4321 (3)	0.1218 (15)
H15	0.7517	0.3433	0.3662	0.146*
C16	0.9025 (5)	0.2509 (4)	0.4917 (4)	0.1077 (13)
C17	0.9598 (4)	0.1372 (5)	0.5872 (4)	0.1026 (11)
H17	1.0384	0.1271	0.6268	0.123*
C18	0.9004 (4)	0.0369 (3)	0.6248 (3)	0.0848 (9)
H18	0.9390	−0.0415	0.6900	0.102*
C19	0.5121 (4)	0.0836 (3)	0.7156 (3)	0.0790 (9)
C20	0.3836 (5)	0.2019 (4)	0.6914 (3)	0.1075 (12)
H20	0.3271	0.2407	0.6259	0.129*
C21	0.3412 (5)	0.2617 (4)	0.7696 (5)	0.1361 (16)
H21	0.2536	0.3397	0.7574	0.163*
C22	0.4284 (6)	0.2053 (5)	0.8630 (4)	0.1273 (15)
H22	0.4002	0.2455	0.9144	0.153*
C23	0.5557 (5)	0.0913 (5)	0.8823 (3)	0.1047 (11)
H23	0.6152	0.0554	0.9460	0.126*
C24	0.5976 (4)	0.0284 (4)	0.8086 (3)	0.0887 (10)
H24	0.6841	−0.0513	0.8226	0.106*

	U11	U22	U33	U12	U13	U23
Cl1	0.1162 (8)	0.1725 (10)	0.1093 (8)	−0.0534 (7)	−0.0125 (6)	−0.0735 (7)
S1	0.0507 (4)	0.0611 (5)	0.0912 (6)	−0.0237 (4)	0.0041 (4)	−0.0300 (4)
O1	0.0537 (11)	0.0874 (13)	0.1169 (17)	−0.0383 (10)	0.0124 (10)	−0.0469 (12)
O2	0.0689 (12)	0.0559 (12)	0.1212 (18)	−0.0118 (10)	−0.0069 (12)	−0.0220 (11)
N1	0.0686 (15)	0.0743 (15)	0.0798 (17)	−0.0378 (14)	0.0106 (13)	−0.0364 (14)
C1	0.0493 (14)	0.0480 (14)	0.0737 (19)	−0.0254 (12)	0.0187 (13)	−0.0304 (13)
C2	0.093 (2)	0.0576 (16)	0.087 (2)	−0.0403 (16)	0.0212 (19)	−0.0370 (16)
C3	0.109 (3)	0.091 (2)	0.098 (3)	−0.062 (2)	0.023 (2)	−0.061 (2)
C4	0.0646 (18)	0.095 (2)	0.074 (2)	−0.0345 (17)	0.0139 (15)	−0.0481 (18)
C5	0.079 (2)	0.0653 (18)	0.079 (2)	−0.0329 (16)	0.0075 (17)	−0.0248 (16)
C6	0.0645 (17)	0.0594 (17)	0.087 (2)	−0.0356 (15)	0.0076 (16)	−0.0315 (16)
C7	0.072 (2)	0.079 (2)	0.0570 (19)	−0.0434 (18)	0.0098 (14)	−0.0228 (15)
C8	0.102 (3)	0.083 (2)	0.107 (3)	−0.052 (2)	0.029 (2)	−0.0298 (19)
C9	0.125 (3)	0.113 (3)	0.119 (3)	−0.085 (3)	0.041 (3)	−0.037 (2)
C10	0.105 (3)	0.142 (4)	0.128 (4)	−0.079 (3)	0.045 (3)	−0.046 (3)
C11	0.096 (3)	0.128 (3)	0.154 (4)	−0.051 (3)	0.058 (3)	−0.059 (3)
C12	0.092 (3)	0.097 (3)	0.122 (3)	−0.052 (2)	0.046 (2)	−0.050 (2)
Cl2	0.1382 (10)	0.1327 (10)	0.2808 (18)	−0.0760 (9)	0.0996 (11)	−0.0487 (10)
S2	0.0843 (6)	0.0634 (5)	0.1069 (7)	−0.0150 (4)	−0.0088 (5)	−0.0407 (5)
O3	0.1039 (17)	0.1019 (16)	0.150 (2)	−0.0112 (14)	−0.0269 (16)	−0.0819 (16)
O4	0.1068 (17)	0.0676 (13)	0.1103 (18)	−0.0200 (12)	−0.0262 (14)	−0.0312 (13)
N2	0.0723 (18)	0.0866 (18)	0.113 (2)	−0.0273 (15)	−0.0021 (15)	−0.0417 (17)
C13	0.0665 (19)	0.0609 (18)	0.077 (2)	−0.0088 (15)	0.0022 (17)	−0.0320 (17)
C14	0.096 (3)	0.083 (2)	0.099 (3)	−0.017 (2)	−0.006 (2)	−0.025 (2)
C15	0.113 (3)	0.092 (3)	0.105 (3)	−0.014 (3)	0.026 (3)	−0.010 (2)
C16	0.087 (3)	0.088 (3)	0.137 (4)	−0.031 (2)	0.053 (3)	−0.040 (3)
C17	0.075 (2)	0.115 (3)	0.128 (4)	−0.041 (2)	0.023 (2)	−0.055 (3)
C18	0.077 (2)	0.076 (2)	0.090 (3)	−0.0201 (19)	0.0030 (19)	−0.0307 (18)
C19	0.083 (2)	0.066 (2)	0.101 (3)	−0.0424 (19)	0.030 (2)	−0.0350 (19)
C20	0.117 (3)	0.075 (2)	0.101 (3)	−0.022 (2)	0.012 (2)	−0.020 (2)
C21	0.147 (4)	0.083 (3)	0.128 (4)	−0.007 (3)	0.022 (4)	−0.029 (3)
C22	0.162 (4)	0.094 (3)	0.110 (4)	−0.033 (3)	0.043 (3)	−0.045 (3)
C23	0.112 (3)	0.113 (3)	0.098 (3)	−0.050 (3)	0.033 (2)	−0.046 (2)
C24	0.081 (2)	0.092 (2)	0.104 (3)	−0.044 (2)	0.015 (2)	−0.039 (2)

Cl1—C4	1.727 (3)	Cl2—C16	1.732 (4)
S1—O2	1.4152 (19)	S2—O4	1.406 (2)
S1—O1	1.4301 (18)	S2—O3	1.432 (2)
S1—N1	1.625 (3)	S2—N2	1.625 (3)
S1—C1	1.746 (3)	S2—C13	1.750 (3)
N1—C7	1.424 (3)	N2—C19	1.422 (4)
N1—H1N	0.844 (16)	N2—H2N	0.889 (17)
C1—C6	1.375 (3)	C13—C18	1.366 (4)
C1—C2	1.380 (3)	C13—C14	1.368 (4)
C2—C3	1.371 (4)	C14—C15	1.367 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.365 (4)	C15—C16	1.359 (5)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.362 (4)	C16—C17	1.358 (5)
C5—C6	1.358 (4)	C17—C18	1.378 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C12	1.351 (4)	C19—C24	1.346 (4)
C7—C8	1.376 (4)	C19—C20	1.376 (5)
C8—C9	1.373 (4)	C20—C21	1.405 (6)
C8—H8	0.9300	C20—H20	0.9300
C9—C10	1.341 (5)	C21—C22	1.357 (6)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.343 (5)	C22—C23	1.353 (5)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.380 (5)	C23—C24	1.371 (5)
C11—H11	0.9300	C23—H23	0.9300
C12—H12	0.9300	C24—H24	0.9300
O2—S1—O1	119.51 (12)	O4—S2—O3	119.25 (14)
O2—S1—N1	108.62 (13)	O4—S2—N2	110.50 (16)
O1—S1—N1	104.49 (12)	O3—S2—N2	103.86 (15)
O2—S1—C1	107.78 (12)	O4—S2—C13	107.49 (15)
O1—S1—C1	109.11 (12)	O3—S2—C13	108.16 (16)
N1—S1—C1	106.65 (12)	N2—S2—C13	106.99 (13)
C7—N1—S1	123.44 (19)	C19—N2—S2	125.8 (2)
C7—N1—H1N	116 (2)	C19—N2—H2N	115 (2)
S1—N1—H1N	109 (2)	S2—N2—H2N	114 (2)
C6—C1—C2	119.1 (3)	C18—C13—C14	120.2 (3)
C6—C1—S1	119.92 (19)	C18—C13—S2	120.4 (2)
C2—C1—S1	120.9 (2)	C14—C13—S2	119.4 (3)
C3—C2—C1	120.2 (3)	C15—C14—C13	119.7 (4)
C3—C2—H2	119.9	C15—C14—H14	120.1
C1—C2—H2	119.9	C13—C14—H14	120.1
C4—C3—C2	119.2 (3)	C16—C15—C14	119.9 (4)
C4—C3—H3	120.4	C16—C15—H15	120.0
C2—C3—H3	120.4	C14—C15—H15	120.0
C5—C4—C3	121.2 (3)	C17—C16—C15	120.9 (4)
C5—C4—Cl1	119.3 (3)	C17—C16—Cl2	118.9 (4)
C3—C4—Cl1	119.5 (2)	C15—C16—Cl2	120.2 (4)
C6—C5—C4	119.6 (3)	C16—C17—C18	119.5 (4)
C6—C5—H5	120.2	C16—C17—H17	120.3
C4—C5—H5	120.2	C18—C17—H17	120.3
C5—C6—C1	120.7 (2)	C13—C18—C17	119.8 (3)
C5—C6—H6	119.7	C13—C18—H18	120.1
C1—C6—H6	119.7	C17—C18—H18	120.1
C12—C7—C8	118.6 (3)	C24—C19—C20	122.3 (3)
C12—C7—N1	118.0 (3)	C24—C19—N2	122.2 (3)
C8—C7—N1	123.3 (3)	C20—C19—N2	115.4 (4)
C9—C8—C7	119.4 (3)	C19—C20—C21	117.4 (4)
C9—C8—H8	120.3	C19—C20—H20	121.3
C7—C8—H8	120.3	C21—C20—H20	121.3
C10—C9—C8	121.8 (4)	C22—C21—C20	119.8 (4)
C10—C9—H9	119.1	C22—C21—H21	120.1
C8—C9—H9	119.1	C20—C21—H21	120.1
C9—C10—C11	118.7 (4)	C23—C22—C21	120.9 (4)
C9—C10—H10	120.6	C23—C22—H22	119.5
C11—C10—H10	120.6	C21—C22—H22	119.5
C10—C11—C12	121.0 (4)	C22—C23—C24	120.4 (4)
C10—C11—H11	119.5	C22—C23—H23	119.8
C12—C11—H11	119.5	C24—C23—H23	119.8
C7—C12—C11	120.4 (3)	C19—C24—C23	119.2 (4)
C7—C12—H12	119.8	C19—C24—H24	120.4
C11—C12—H12	119.8	C23—C24—H24	120.4
O2—S1—N1—C7	62.1 (2)	O4—S2—N2—C19	53.3 (3)
O1—S1—N1—C7	−169.3 (2)	O3—S2—N2—C19	−177.7 (3)
C1—S1—N1—C7	−53.8 (2)	C13—S2—N2—C19	−63.4 (3)
O2—S1—C1—C6	165.8 (2)	O4—S2—C13—C18	−5.0 (3)
O1—S1—C1—C6	34.6 (2)	O3—S2—C13—C18	−135.0 (2)
N1—S1—C1—C6	−77.7 (2)	N2—S2—C13—C18	113.7 (3)
O2—S1—C1—C2	−17.9 (3)	O4—S2—C13—C14	176.0 (3)
O1—S1—C1—C2	−149.1 (2)	O3—S2—C13—C14	46.0 (3)
N1—S1—C1—C2	98.6 (2)	N2—S2—C13—C14	−65.3 (3)
C6—C1—C2—C3	0.0 (4)	C18—C13—C14—C15	−1.4 (5)
S1—C1—C2—C3	−176.3 (2)	S2—C13—C14—C15	177.6 (3)
C1—C2—C3—C4	−0.1 (5)	C13—C14—C15—C16	0.1 (6)
C2—C3—C4—C5	−0.2 (5)	C14—C15—C16—C17	1.1 (6)
C2—C3—C4—Cl1	178.6 (2)	C14—C15—C16—Cl2	−176.7 (3)
C3—C4—C5—C6	0.6 (5)	C15—C16—C17—C18	−1.1 (6)
Cl1—C4—C5—C6	−178.2 (2)	Cl2—C16—C17—C18	176.8 (3)
C4—C5—C6—C1	−0.7 (4)	C14—C13—C18—C17	1.4 (5)
C2—C1—C6—C5	0.4 (4)	S2—C13—C18—C17	−177.6 (2)
S1—C1—C6—C5	176.8 (2)	C16—C17—C18—C13	−0.2 (5)
S1—N1—C7—C12	139.2 (3)	S2—N2—C19—C24	−32.0 (4)
S1—N1—C7—C8	−43.1 (4)	S2—N2—C19—C20	151.6 (3)
C12—C7—C8—C9	−2.1 (5)	C24—C19—C20—C21	−2.1 (5)
N1—C7—C8—C9	−179.9 (3)	N2—C19—C20—C21	174.3 (3)
C7—C8—C9—C10	2.2 (6)	C19—C20—C21—C22	2.1 (6)
C8—C9—C10—C11	−1.1 (7)	C20—C21—C22—C23	−0.4 (7)
C9—C10—C11—C12	0.0 (7)	C21—C22—C23—C24	−1.5 (6)
C8—C7—C12—C11	1.0 (5)	C20—C19—C24—C23	0.3 (5)
N1—C7—C12—C11	178.9 (3)	N2—C19—C24—C23	−175.9 (3)
C10—C11—C12—C7	0.0 (6)	C22—C23—C24—C19	1.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.17 (2)	3.010 (3)	175 (3)
N2—H2N···O3ii	0.89 (2)	1.99 (2)	2.867 (4)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.17 (2)	3.010 (3)	175 (3)
N2—H2N⋯O3ii	0.89 (2)	1.99 (2)	2.867 (4)	167 (3)

Symmetry codes: (i) ; (ii) .