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

In the crystal of the title compound, C(12)H(9)Cl(2)NO(2)S, the mol-ecule is twisted at the S atom with a C-SO(2)-NH-C torsion angle of -58.4 (3)°. Furthermore, the N-H bond in this segment is anti to the meta-chloro group. The dihedral angle between the aromatic rings is 77.1 (1)°. The crystal structure features inversion-related dimers linked by N-H⋯O hydrogen bonds.

Related literature

For our study on the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2005 ▶); Shakuntala et al. (2011 ▶). For the effect of substituents on the oxidative strengths of N-chloro,N-aryl­sulfonamides, see: Gowda & Shetty (2004 ▶) and for the effect of substituents on the NQR spectra of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶).

Experimental

Crystal data

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 9.378 (2) Å

b = 13.478 (3) Å

c = 10.251 (2) Å

β = 90.48°

V = 1295.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.65 mm−1

T = 293 K

0.48 × 0.44 × 0.44 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.745, T max = 0.762

4232 measured reflections

2115 independent reflections

1572 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.129

S = 1.08

2115 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.49 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/S1600536811011366/ds2101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011366/ds2101Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 616
Mr = 302.16	Dx = 1.549 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 959 reflections
a = 9.378 (2) Å	θ = 2.9–27.8°
b = 13.478 (3) Å	µ = 0.65 mm−1
c = 10.251 (2) Å	T = 293 K
β = 90.48°	Prism, colourless
V = 1295.6 (5) Å3	0.48 × 0.44 × 0.44 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2115 independent reflections
Radiation source: fine-focus sealed tube	1572 reflections with I > 2σ(I)
graphite	Rint = 0.014
Rotation method data acquisition using ω and phi scans.	θmax = 24.7°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→10
Tmin = 0.745, Tmax = 0.762	k = −15→15
4232 measured reflections	l = −11→11

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) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.047P)2 + 1.4846P] where P = (Fo2 + 2Fc2)/3
2115 reflections	(Δ/σ)max = 0.006
166 parameters	Δρmax = 0.54 e Å−3
1 restraint	Δρmin = −0.49 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	0.1825 (3)	−0.0615 (3)	0.0799 (3)	0.0508 (9)
C2	0.0654 (4)	−0.0812 (4)	0.1546 (4)	0.0729 (12)
H2	0.0440	−0.0410	0.2255	0.087*
C3	−0.0207 (4)	−0.1612 (4)	0.1236 (5)	0.0825 (14)
H3	−0.0999	−0.1755	0.1743	0.099*
C4	0.0106 (4)	−0.2191 (3)	0.0188 (4)	0.0679 (11)
C5	0.1265 (4)	−0.1999 (3)	−0.0564 (4)	0.0689 (11)
H5	0.1468	−0.2399	−0.1278	0.083*
C6	0.2127 (4)	−0.1211 (3)	−0.0256 (4)	0.0596 (10)
H6	0.2923	−0.1078	−0.0763	0.072*
C7	0.4235 (4)	−0.0627 (2)	0.3131 (4)	0.0505 (8)
C8	0.3302 (4)	−0.0357 (3)	0.4113 (3)	0.0516 (8)
H8	0.2676	0.0172	0.4000	0.062*
C9	0.3323 (4)	−0.0887 (3)	0.5251 (4)	0.0584 (9)
C10	0.4236 (5)	−0.1658 (3)	0.5465 (5)	0.0743 (12)
H10	0.4237	−0.2000	0.6254	0.089*
C11	0.5151 (5)	−0.1916 (3)	0.4491 (5)	0.0784 (13)
H11	0.5784	−0.2438	0.4620	0.094*
C12	0.5152 (4)	−0.1415 (3)	0.3323 (4)	0.0631 (10)
H12	0.5769	−0.1607	0.2664	0.076*
O1	0.3569 (3)	0.07335 (19)	−0.0026 (2)	0.0640 (7)
O2	0.2238 (3)	0.1039 (2)	0.1997 (3)	0.0728 (8)
N1	0.4324 (3)	−0.0091 (2)	0.1956 (3)	0.0562 (8)
H1N	0.491 (3)	−0.030 (3)	0.139 (3)	0.067*
Cl1	−0.09656 (14)	−0.31895 (11)	−0.01890 (13)	0.1052 (5)
Cl2	0.21587 (13)	−0.05483 (10)	0.64754 (11)	0.0900 (4)
S1	0.29685 (10)	0.03746 (7)	0.11668 (9)	0.0552 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0405 (17)	0.060 (2)	0.052 (2)	0.0058 (15)	−0.0001 (15)	0.0121 (18)
C2	0.052 (2)	0.108 (3)	0.059 (2)	0.000 (2)	0.0080 (19)	−0.003 (2)
C3	0.047 (2)	0.124 (4)	0.077 (3)	−0.018 (2)	0.006 (2)	0.021 (3)
C4	0.058 (2)	0.077 (3)	0.069 (3)	−0.016 (2)	−0.0094 (19)	0.016 (2)
C5	0.067 (2)	0.066 (3)	0.074 (3)	−0.012 (2)	0.005 (2)	−0.002 (2)
C6	0.055 (2)	0.062 (2)	0.062 (2)	−0.0103 (18)	0.0159 (17)	0.003 (2)
C7	0.0478 (18)	0.0433 (18)	0.060 (2)	−0.0041 (15)	−0.0076 (16)	−0.0038 (17)
C8	0.0511 (19)	0.0509 (19)	0.053 (2)	0.0036 (16)	−0.0068 (16)	−0.0009 (17)
C9	0.061 (2)	0.059 (2)	0.055 (2)	−0.0050 (18)	−0.0063 (18)	0.0001 (19)
C10	0.077 (3)	0.060 (3)	0.086 (3)	−0.002 (2)	−0.018 (2)	0.014 (2)
C11	0.075 (3)	0.049 (2)	0.112 (4)	0.012 (2)	−0.018 (3)	0.005 (2)
C12	0.059 (2)	0.051 (2)	0.079 (3)	0.0060 (18)	−0.003 (2)	−0.013 (2)
O1	0.0741 (17)	0.0581 (15)	0.0598 (16)	−0.0056 (13)	0.0076 (13)	0.0121 (12)
O2	0.090 (2)	0.0604 (16)	0.0680 (17)	0.0245 (15)	0.0041 (14)	−0.0037 (14)
N1	0.0513 (18)	0.0630 (19)	0.054 (2)	0.0002 (15)	0.0007 (14)	−0.0036 (16)
Cl1	0.0940 (9)	0.1148 (11)	0.1066 (10)	−0.0559 (8)	−0.0191 (7)	0.0267 (8)
Cl2	0.0911 (8)	0.1135 (10)	0.0657 (7)	0.0044 (7)	0.0125 (6)	0.0095 (7)
S1	0.0592 (5)	0.0493 (5)	0.0572 (6)	0.0048 (4)	0.0031 (4)	0.0025 (4)

C1—C2	1.370 (5)	C7—N1	1.407 (5)
C1—C6	1.379 (5)	C8—C9	1.367 (5)
C1—S1	1.751 (4)	C8—H8	0.9300
C2—C3	1.383 (6)	C9—C10	1.364 (5)
C2—H2	0.9300	C9—Cl2	1.732 (4)
C3—C4	1.362 (6)	C10—C11	1.367 (6)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.362 (5)	C11—C12	1.374 (6)
C4—Cl1	1.722 (4)	C11—H11	0.9300
C5—C6	1.370 (5)	C12—H12	0.9300
C5—H5	0.9300	O1—S1	1.434 (2)
C6—H6	0.9300	O2—S1	1.416 (3)
C7—C12	1.380 (5)	N1—S1	1.627 (3)
C7—C8	1.387 (5)	N1—H1N	0.846 (18)
C2—C1—C6	119.8 (4)	C7—C8—H8	120.7
C2—C1—S1	121.3 (3)	C10—C9—C8	122.7 (4)
C6—C1—S1	118.9 (3)	C10—C9—Cl2	118.9 (3)
C1—C2—C3	119.5 (4)	C8—C9—Cl2	118.4 (3)
C1—C2—H2	120.3	C9—C10—C11	118.2 (4)
C3—C2—H2	120.3	C9—C10—H10	120.9
C4—C3—C2	119.9 (4)	C11—C10—H10	120.9
C4—C3—H3	120.0	C10—C11—C12	121.1 (4)
C2—C3—H3	120.0	C10—C11—H11	119.4
C3—C4—C5	121.1 (4)	C12—C11—H11	119.4
C3—C4—Cl1	119.7 (3)	C11—C12—C7	119.8 (4)
C5—C4—Cl1	119.2 (4)	C11—C12—H12	120.1
C4—C5—C6	119.3 (4)	C7—C12—H12	120.1
C4—C5—H5	120.4	C7—N1—S1	124.9 (2)
C6—C5—H5	120.4	C7—N1—H1N	117 (3)
C5—C6—C1	120.5 (3)	S1—N1—H1N	107 (3)
C5—C6—H6	119.8	O2—S1—O1	119.65 (17)
C1—C6—H6	119.8	O2—S1—N1	108.95 (17)
C12—C7—C8	119.6 (4)	O1—S1—N1	104.09 (16)
C12—C7—N1	118.4 (3)	O2—S1—C1	108.23 (17)
C8—C7—N1	121.9 (3)	O1—S1—C1	108.50 (16)
C9—C8—C7	118.5 (3)	N1—S1—C1	106.73 (16)
C9—C8—H8	120.7
C6—C1—C2—C3	0.4 (6)	C9—C10—C11—C12	−0.2 (6)
S1—C1—C2—C3	−178.8 (3)	C10—C11—C12—C7	1.2 (6)
C1—C2—C3—C4	−0.6 (6)	C8—C7—C12—C11	−1.1 (5)
C2—C3—C4—C5	0.4 (7)	N1—C7—C12—C11	176.1 (3)
C2—C3—C4—Cl1	179.7 (3)	C12—C7—N1—S1	143.4 (3)
C3—C4—C5—C6	0.0 (6)	C8—C7—N1—S1	−39.5 (5)
Cl1—C4—C5—C6	−179.3 (3)	C7—N1—S1—O2	58.2 (3)
C4—C5—C6—C1	−0.3 (6)	C7—N1—S1—O1	−173.1 (3)
C2—C1—C6—C5	0.0 (6)	C7—N1—S1—C1	−58.4 (3)
S1—C1—C6—C5	179.3 (3)	C2—C1—S1—O2	−18.4 (4)
C12—C7—C8—C9	0.1 (5)	C6—C1—S1—O2	162.4 (3)
N1—C7—C8—C9	−177.0 (3)	C2—C1—S1—O1	−149.6 (3)
C7—C8—C9—C10	1.0 (6)	C6—C1—S1—O1	31.2 (3)
C7—C8—C9—Cl2	179.9 (3)	C2—C1—S1—N1	98.8 (3)
C8—C9—C10—C11	−0.9 (6)	C6—C1—S1—N1	−80.5 (3)
Cl2—C9—C10—C11	−179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.09 (2)	2.939 (4)	176 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.09 (2)	2.939 (4)	176 (4)

Symmetry code: (i) .