N-(2,5-Dichloro-phen-yl)benzene-sulfonamide.

In the title compound, C(12)H(9)Cl(2)NO(2)S, the conformation of the N-H bond is syn to the 2-chloro group and anti to the 3-chloro group of the aniline benzene ring. The mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 66.4 (2)°. The two rings form a dihedral angle of 73.3 (1)° and an intra-molecular N-H⋯Cl hydrogen bond occurs. The crystal structure features chains linked by N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Shetty & Gowda (2005 ▶). For our study 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

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 9.595 (1) Å

b = 14.188 (2) Å

c = 10.424 (1) Å

β = 114.42 (2)°

V = 1292.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 299 K

0.44 × 0.40 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.761, T max = 0.818

5199 measured reflections

2638 independent reflections

2225 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.086

S = 1.05

2638 reflections

167 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.34 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/S1600536810004769/fl2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004769/fl2289Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 616
Mr = 302.16	Dx = 1.553 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2765 reflections
a = 9.595 (1) Å	θ = 2.7–27.8°
b = 14.188 (2) Å	µ = 0.66 mm−1
c = 10.424 (1) Å	T = 299 K
β = 114.42 (2)°	Prism, colourless
V = 1292.1 (3) Å3	0.44 × 0.40 × 0.32 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD Detector	2638 independent reflections
Radiation source: fine-focus sealed tube	2225 reflections with I > 2σ(I)
graphite	Rint = 0.010
Rotation method data acquisition using ω and phi scans.	θmax = 26.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→11
Tmin = 0.761, Tmax = 0.818	k = −13→17
5199 measured reflections	l = −7→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.4815P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2638 reflections	Δρmax = 0.23 e Å−3
167 parameters	Δρmin = −0.34 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0316 (18)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
C1	−0.10881 (19)	0.57873 (12)	0.71058 (18)	0.0342 (4)
C2	−0.0940 (2)	0.61982 (15)	0.8359 (2)	0.0482 (5)
H2	−0.0255	0.5957	0.9217	0.058*
C3	−0.1826 (3)	0.69707 (18)	0.8311 (3)	0.0665 (7)
H3	−0.1732	0.7259	0.9145	0.080*
C4	−0.2852 (3)	0.73206 (17)	0.7038 (3)	0.0690 (7)
H4	−0.3452	0.7840	0.7016	0.083*
C5	−0.2991 (3)	0.69043 (18)	0.5800 (3)	0.0675 (7)
H5	−0.3688	0.7143	0.4943	0.081*
C6	−0.2105 (2)	0.61368 (15)	0.5821 (2)	0.0501 (5)
H6	−0.2188	0.5858	0.4984	0.060*
C7	0.27503 (19)	0.56534 (12)	0.85564 (18)	0.0338 (4)
C8	0.3535 (2)	0.64497 (13)	0.8424 (2)	0.0403 (4)
C9	0.4606 (2)	0.68914 (15)	0.9591 (2)	0.0515 (5)
H9	0.5129	0.7414	0.9479	0.062*
C10	0.4906 (2)	0.65644 (16)	1.0922 (2)	0.0528 (5)
H10	0.5621	0.6865	1.1713	0.063*
C11	0.4128 (2)	0.57828 (14)	1.10589 (19)	0.0429 (4)
C12	0.3074 (2)	0.53198 (13)	0.99013 (18)	0.0386 (4)
H12	0.2581	0.4785	1.0022	0.046*
N1	0.17095 (17)	0.51827 (11)	0.73345 (15)	0.0363 (3)
H1N	0.166 (2)	0.5403 (13)	0.6564 (14)	0.044*
O1	−0.05974 (16)	0.43413 (9)	0.58100 (13)	0.0443 (3)
O2	0.02450 (15)	0.42616 (9)	0.83833 (13)	0.0462 (3)
Cl1	0.31855 (6)	0.68832 (4)	0.67634 (6)	0.05849 (18)
Cl2	0.44864 (7)	0.53545 (5)	1.27273 (5)	0.06258 (19)
S1	0.00256 (5)	0.47941 (3)	0.71548 (4)	0.03304 (14)

	U11	U22	U33	U12	U13	U23
C1	0.0319 (9)	0.0366 (9)	0.0350 (9)	−0.0051 (7)	0.0147 (7)	−0.0037 (7)
C2	0.0452 (11)	0.0609 (13)	0.0406 (10)	−0.0044 (9)	0.0200 (9)	−0.0115 (9)
C3	0.0580 (14)	0.0735 (16)	0.0783 (17)	−0.0084 (12)	0.0385 (13)	−0.0330 (14)
C4	0.0510 (13)	0.0540 (14)	0.109 (2)	0.0053 (11)	0.0400 (14)	−0.0137 (14)
C5	0.0563 (14)	0.0647 (15)	0.0737 (16)	0.0185 (12)	0.0190 (12)	0.0078 (13)
C6	0.0473 (11)	0.0551 (12)	0.0418 (11)	0.0082 (9)	0.0125 (9)	−0.0003 (9)
C7	0.0272 (8)	0.0366 (9)	0.0352 (9)	0.0026 (7)	0.0106 (7)	−0.0005 (7)
C8	0.0344 (9)	0.0397 (10)	0.0434 (10)	0.0020 (7)	0.0126 (8)	0.0064 (8)
C9	0.0441 (11)	0.0457 (11)	0.0587 (13)	−0.0129 (9)	0.0152 (9)	−0.0018 (9)
C10	0.0427 (11)	0.0575 (13)	0.0477 (11)	−0.0115 (9)	0.0083 (9)	−0.0106 (10)
C11	0.0342 (9)	0.0540 (12)	0.0351 (9)	0.0011 (8)	0.0090 (7)	−0.0019 (8)
C12	0.0333 (9)	0.0421 (10)	0.0376 (9)	−0.0028 (7)	0.0118 (8)	0.0004 (8)
N1	0.0340 (8)	0.0450 (9)	0.0306 (7)	−0.0030 (6)	0.0140 (6)	−0.0007 (6)
O1	0.0510 (8)	0.0428 (7)	0.0338 (7)	−0.0064 (6)	0.0123 (6)	−0.0099 (5)
O2	0.0507 (8)	0.0454 (7)	0.0357 (7)	−0.0107 (6)	0.0112 (6)	0.0078 (6)
Cl1	0.0530 (3)	0.0621 (3)	0.0535 (3)	−0.0064 (2)	0.0152 (2)	0.0205 (3)
Cl2	0.0564 (3)	0.0871 (4)	0.0342 (3)	−0.0090 (3)	0.0085 (2)	0.0007 (3)
S1	0.0356 (2)	0.0331 (2)	0.0272 (2)	−0.00569 (17)	0.00974 (17)	−0.00172 (16)

C1—C6	1.383 (3)	C7—N1	1.419 (2)
C1—C2	1.383 (2)	C8—C9	1.377 (3)
C1—S1	1.7565 (18)	C8—Cl1	1.7343 (19)
C2—C3	1.375 (3)	C9—C10	1.375 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.377 (4)	C10—C11	1.377 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.375 (4)	C11—C12	1.379 (2)
C4—H4	0.9300	C11—Cl2	1.737 (2)
C5—C6	1.376 (3)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.6430 (15)
C6—H6	0.9300	N1—H1N	0.844 (9)
C7—C12	1.388 (2)	O1—S1	1.4292 (13)
C7—C8	1.396 (2)	O2—S1	1.4254 (13)
C6—C1—C2	121.31 (18)	C7—C8—Cl1	119.74 (14)
C6—C1—S1	119.54 (14)	C10—C9—C8	120.44 (19)
C2—C1—S1	119.15 (15)	C10—C9—H9	119.8
C3—C2—C1	118.8 (2)	C8—C9—H9	119.8
C3—C2—H2	120.6	C9—C10—C11	118.67 (18)
C1—C2—H2	120.6	C9—C10—H10	120.7
C2—C3—C4	120.4 (2)	C11—C10—H10	120.7
C2—C3—H3	119.8	C10—C11—C12	121.72 (18)
C4—C3—H3	119.8	C10—C11—Cl2	119.63 (15)
C5—C4—C3	120.2 (2)	C12—C11—Cl2	118.65 (15)
C5—C4—H4	119.9	C11—C12—C7	119.90 (17)
C3—C4—H4	119.9	C11—C12—H12	120.1
C4—C5—C6	120.4 (2)	C7—C12—H12	120.1
C4—C5—H5	119.8	C7—N1—S1	123.65 (12)
C6—C5—H5	119.8	C7—N1—H1N	115.0 (15)
C5—C6—C1	118.9 (2)	S1—N1—H1N	110.3 (15)
C5—C6—H6	120.6	O2—S1—O1	119.31 (8)
C1—C6—H6	120.6	O2—S1—N1	107.60 (8)
C12—C7—C8	118.11 (16)	O1—S1—N1	104.80 (8)
C12—C7—N1	121.79 (16)	O2—S1—C1	108.27 (8)
C8—C7—N1	120.03 (15)	O1—S1—C1	109.23 (8)
C9—C8—C7	121.14 (18)	N1—S1—C1	106.97 (8)
C9—C8—Cl1	119.11 (15)
C6—C1—C2—C3	−0.1 (3)	C9—C10—C11—Cl2	179.98 (17)
S1—C1—C2—C3	−179.45 (16)	C10—C11—C12—C7	−1.5 (3)
C1—C2—C3—C4	0.7 (3)	Cl2—C11—C12—C7	179.16 (13)
C2—C3—C4—C5	−0.5 (4)	C8—C7—C12—C11	1.0 (3)
C3—C4—C5—C6	−0.2 (4)	N1—C7—C12—C11	178.02 (17)
C4—C5—C6—C1	0.7 (4)	C12—C7—N1—S1	45.9 (2)
C2—C1—C6—C5	−0.5 (3)	C8—C7—N1—S1	−137.14 (15)
S1—C1—C6—C5	178.75 (18)	C7—N1—S1—O2	−49.78 (17)
C12—C7—C8—C9	0.3 (3)	C7—N1—S1—O1	−177.73 (14)
N1—C7—C8—C9	−176.78 (18)	C7—N1—S1—C1	66.36 (16)
C12—C7—C8—Cl1	179.19 (13)	C6—C1—S1—O2	−146.50 (15)
N1—C7—C8—Cl1	2.1 (2)	C2—C1—S1—O2	32.81 (16)
C7—C8—C9—C10	−1.2 (3)	C6—C1—S1—O1	−15.12 (18)
Cl1—C8—C9—C10	179.95 (17)	C2—C1—S1—O1	164.19 (14)
C8—C9—C10—C11	0.7 (3)	C6—C1—S1—N1	97.79 (16)
C9—C10—C11—C12	0.6 (3)	C2—C1—S1—N1	−82.90 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (1)	2.28 (1)	3.074 (2)	156 (2)
N1—H1N···Cl1	0.84 (1)	2.52 (2)	2.9795 (16)	115 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (1)	2.28 (1)	3.074 (2)	156 (2)
N1—H1N⋯Cl1	0.84 (1)	2.52 (2)	2.9795 (16)	115 (2)

Symmetry code: (i) .