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

In the crystal structure of the title compound, C(12)H(9)Cl(2)NO(2)S, the N-C bond in the C-SO(2)-NH-C segment has gauche torsions with respect to the S=O bonds. The mol-ecule is twisted at the S atom with an C-SO(2)-NH-C torsion angle of 57.6 (3)°. The N-H bond is syn to the ortho-chloro group in the anilino benzene ring. The two benzene rings are tilted relative to each other by 84.7 (1)°. The crystal structure features inversion dimers linked by N-H⋯O(S) hydrogen bonds. An intra-molecular N-H⋯Cl hydrogen bond is also observed.

Related literature

For our study of the effect of substituents on the oxidative strengths of N-chloro,N-aryl­sulfonamides, see: Gowda & Shetty (2004 ▶), and on the structures of N-(ar­yl)-amides, see: Gowda et al. (2004 ▶), N-(ar­yl)-aryl­sulfonamides, see: Shakuntala et al. (2011 ▶) and N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶).

Experimental

Crystal data

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 14.950 (2) Å

b = 12.888 (2) Å

c = 14.568 (2) Å

β = 111.41 (1)°

V = 2613.2 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.65 mm−1

T = 293 K

0.44 × 0.42 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.764, T max = 0.820

5453 measured reflections

2671 independent reflections

2049 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.03

2671 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.38 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/S1600536811010828/tk2731sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010828/tk2731Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 1232
Mr = 302.16	Dx = 1.536 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2370 reflections
a = 14.950 (2) Å	θ = 2.8–27.7°
b = 12.888 (2) Å	µ = 0.65 mm−1
c = 14.568 (2) Å	T = 293 K
β = 111.41 (1)°	Prism, colourless
V = 2613.2 (6) Å3	0.44 × 0.42 × 0.32 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD	2671 independent reflections
Radiation source: fine-focus sealed tube	2049 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −18→13
Tmin = 0.764, Tmax = 0.820	k = −16→9
5453 measured reflections	l = −18→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0576P)2 + 2.4691P] where P = (Fo2 + 2Fc2)/3
2671 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.38 e Å−3

Experimental. 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	0.47546 (14)	0.24207 (18)	0.44604 (15)	0.0382 (5)
C2	0.45846 (18)	0.3414 (2)	0.4102 (2)	0.0552 (6)
H2	0.4028	0.3758	0.4071	0.066*
C3	0.5242 (2)	0.3898 (2)	0.3789 (2)	0.0636 (7)
H3	0.5138	0.4574	0.3549	0.076*
C4	0.60507 (18)	0.3372 (2)	0.38344 (18)	0.0538 (6)
C5	0.62200 (18)	0.2385 (2)	0.4181 (2)	0.0547 (6)
H5	0.6773	0.2040	0.4202	0.066*
C6	0.55683 (16)	0.18986 (19)	0.45023 (19)	0.0473 (6)
H6	0.5678	0.1224	0.4745	0.057*
C7	0.28930 (15)	0.11084 (18)	0.30448 (17)	0.0418 (5)
C8	0.20809 (17)	0.12287 (19)	0.21954 (17)	0.0453 (5)
C9	0.1974 (2)	0.0696 (2)	0.13415 (19)	0.0575 (7)
H9	0.1418	0.0782	0.0787	0.069*
C10	0.2680 (2)	0.0043 (2)	0.1304 (2)	0.0650 (8)
H10	0.2613	−0.0308	0.0725	0.078*
C11	0.3492 (2)	−0.0086 (2)	0.2135 (2)	0.0616 (7)
H11	0.3977	−0.0526	0.2113	0.074*
C12	0.35983 (18)	0.0428 (2)	0.3001 (2)	0.0531 (6)
H12	0.4146	0.0317	0.3559	0.064*
N1	0.29597 (13)	0.16494 (18)	0.39002 (15)	0.0509 (5)
H1N	0.2514 (16)	0.199 (2)	0.392 (2)	0.061*
O1	0.43100 (13)	0.08327 (17)	0.52862 (14)	0.0651 (5)
O2	0.36333 (12)	0.25214 (19)	0.54668 (13)	0.0696 (6)
Cl1	0.68971 (6)	0.39830 (8)	0.34678 (7)	0.0926 (3)
Cl2	0.11621 (5)	0.20293 (8)	0.22150 (6)	0.0787 (3)
S1	0.39197 (4)	0.18111 (5)	0.48790 (4)	0.04654 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0337 (10)	0.0455 (12)	0.0368 (10)	0.0025 (9)	0.0147 (8)	−0.0003 (9)
C2	0.0461 (13)	0.0534 (15)	0.0642 (16)	0.0149 (12)	0.0178 (12)	0.0087 (13)
C3	0.0659 (17)	0.0492 (16)	0.0667 (17)	0.0025 (13)	0.0134 (14)	0.0208 (13)
C4	0.0533 (14)	0.0599 (16)	0.0506 (14)	−0.0160 (12)	0.0220 (11)	0.0032 (12)
C5	0.0455 (13)	0.0527 (15)	0.0770 (17)	−0.0031 (11)	0.0357 (13)	−0.0058 (13)
C6	0.0410 (12)	0.0394 (12)	0.0684 (15)	0.0019 (10)	0.0280 (11)	0.0019 (11)
C7	0.0399 (11)	0.0424 (12)	0.0509 (13)	−0.0072 (9)	0.0258 (10)	−0.0039 (10)
C8	0.0481 (12)	0.0448 (13)	0.0493 (13)	−0.0039 (10)	0.0254 (10)	0.0020 (11)
C9	0.0653 (16)	0.0621 (17)	0.0493 (14)	−0.0150 (14)	0.0258 (12)	−0.0041 (13)
C10	0.084 (2)	0.0568 (16)	0.0720 (18)	−0.0214 (15)	0.0499 (17)	−0.0228 (14)
C11	0.0672 (17)	0.0485 (15)	0.086 (2)	−0.0042 (13)	0.0478 (16)	−0.0142 (14)
C12	0.0469 (13)	0.0514 (15)	0.0688 (16)	−0.0006 (11)	0.0303 (12)	−0.0044 (13)
N1	0.0315 (9)	0.0706 (14)	0.0533 (11)	0.0050 (9)	0.0188 (9)	−0.0145 (11)
O1	0.0529 (10)	0.0805 (14)	0.0681 (12)	0.0049 (10)	0.0293 (9)	0.0315 (11)
O2	0.0449 (9)	0.1162 (18)	0.0546 (10)	−0.0005 (10)	0.0264 (8)	−0.0272 (11)
Cl1	0.0793 (5)	0.1133 (7)	0.0893 (6)	−0.0409 (5)	0.0355 (5)	0.0226 (5)
Cl2	0.0598 (4)	0.1065 (7)	0.0623 (4)	0.0306 (4)	0.0135 (3)	−0.0056 (4)
S1	0.0338 (3)	0.0699 (4)	0.0412 (3)	0.0022 (3)	0.0200 (2)	0.0005 (3)

C1—C2	1.371 (3)	C7—N1	1.399 (3)
C1—C6	1.372 (3)	C8—C9	1.378 (3)
C1—S1	1.761 (2)	C8—Cl2	1.727 (2)
C2—C3	1.375 (4)	C9—C10	1.367 (4)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.367 (4)	C10—C11	1.376 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.357 (4)	C11—C12	1.381 (4)
C4—Cl1	1.732 (2)	C11—H11	0.9300
C5—C6	1.376 (3)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.625 (2)
C6—H6	0.9300	N1—H1N	0.807 (17)
C7—C8	1.390 (3)	O1—S1	1.425 (2)
C7—C12	1.391 (3)	O2—S1	1.4221 (19)
C2—C1—C6	120.9 (2)	C7—C8—Cl2	119.58 (18)
C2—C1—S1	119.47 (17)	C10—C9—C8	120.4 (3)
C6—C1—S1	119.66 (18)	C10—C9—H9	119.8
C1—C2—C3	119.6 (2)	C8—C9—H9	119.8
C1—C2—H2	120.2	C9—C10—C11	119.0 (3)
C3—C2—H2	120.2	C9—C10—H10	120.5
C4—C3—C2	119.0 (2)	C11—C10—H10	120.5
C4—C3—H3	120.5	C10—C11—C12	121.1 (3)
C2—C3—H3	120.5	C10—C11—H11	119.5
C5—C4—C3	121.6 (2)	C12—C11—H11	119.5
C5—C4—Cl1	118.9 (2)	C11—C12—C7	120.5 (3)
C3—C4—Cl1	119.5 (2)	C11—C12—H12	119.7
C4—C5—C6	119.6 (2)	C7—C12—H12	119.7
C4—C5—H5	120.2	C7—N1—S1	126.74 (16)
C6—C5—H5	120.2	C7—N1—H1N	121 (2)
C1—C6—C5	119.2 (2)	S1—N1—H1N	112 (2)
C1—C6—H6	120.4	O2—S1—O1	119.12 (13)
C5—C6—H6	120.4	O2—S1—N1	104.32 (10)
C8—C7—C12	117.4 (2)	O1—S1—N1	110.37 (13)
C8—C7—N1	119.5 (2)	O2—S1—C1	109.18 (12)
C12—C7—N1	123.1 (2)	O1—S1—C1	107.73 (10)
C9—C8—C7	121.6 (2)	N1—S1—C1	105.30 (10)
C9—C8—Cl2	118.8 (2)
C6—C1—C2—C3	−0.6 (4)	C8—C9—C10—C11	1.0 (4)
S1—C1—C2—C3	179.0 (2)	C9—C10—C11—C12	0.4 (4)
C1—C2—C3—C4	0.5 (4)	C10—C11—C12—C7	−1.5 (4)
C2—C3—C4—C5	−0.1 (4)	C8—C7—C12—C11	1.3 (3)
C2—C3—C4—Cl1	−178.6 (2)	N1—C7—C12—C11	179.9 (2)
C3—C4—C5—C6	−0.4 (4)	C8—C7—N1—S1	−165.93 (19)
Cl1—C4—C5—C6	178.1 (2)	C12—C7—N1—S1	15.4 (4)
C2—C1—C6—C5	0.2 (4)	C7—N1—S1—O2	172.5 (2)
S1—C1—C6—C5	−179.4 (2)	C7—N1—S1—O1	−58.4 (2)
C4—C5—C6—C1	0.3 (4)	C7—N1—S1—C1	57.6 (2)
C12—C7—C8—C9	0.1 (3)	C2—C1—S1—O2	−44.3 (2)
N1—C7—C8—C9	−178.7 (2)	C6—C1—S1—O2	135.3 (2)
C12—C7—C8—Cl2	177.84 (18)	C2—C1—S1—O1	−175.0 (2)
N1—C7—C8—Cl2	−0.9 (3)	C6—C1—S1—O1	4.6 (2)
C7—C8—C9—C10	−1.2 (4)	C2—C1—S1—N1	67.2 (2)
Cl2—C8—C9—C10	−179.0 (2)	C6—C1—S1—N1	−113.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.81 (2)	2.29 (2)	3.044 (2)	155 (3)
N1—H1N···Cl2	0.81 (2)	2.57 (3)	2.945 (2)	110 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.81 (2)	2.29 (2)	3.044 (2)	155 (3)
N1—H1N⋯Cl2	0.81 (2)	2.57 (3)	2.945 (2)	110 (2)

Symmetry code: (i) .