N-(2,6-Dichloro-phen-yl)benzene-sulfonamide.

In the title compound, C(12)H(9)Cl(2)NO(2)S, the mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 82.5 (2)°. The benzene rings are tilted relative to each other by 43.5 (1)°. The crystal structure features chains linked by N-H⋯O hydrogen bonds.

Related literature

For our study of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2008a ▶,b ▶, 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 5.059 (1) Å

b = 17.143 (4) Å

c = 15.351 (3) Å

β = 90.43 (2)°

V = 1331.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.883, T max = 0.939

4603 measured reflections

2423 independent reflections

1389 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.088

S = 0.85

2423 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 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/S160053681004420X/bq2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004420X/bq2247Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 616
Mr = 302.16	Dx = 1.508 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1612 reflections
a = 5.059 (1) Å	θ = 2.9–27.9°
b = 17.143 (4) Å	µ = 0.64 mm−1
c = 15.351 (3) Å	T = 293 K
β = 90.43 (2)°	Prism, colourless
V = 1331.3 (5) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2423 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
graphite	Rint = 0.031
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→6
Tmin = 0.883, Tmax = 0.939	k = −20→20
4603 measured reflections	l = −18→17

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3
2423 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.26 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

Experimental. Absorption correction: 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
C1	−0.0324 (5)	0.27365 (16)	0.83013 (17)	0.0403 (7)
C2	−0.2352 (5)	0.22113 (18)	0.8401 (2)	0.0619 (9)
H2	−0.3479	0.2095	0.7937	0.074*
C3	−0.2686 (8)	0.1860 (2)	0.9200 (3)	0.0893 (13)
H3	−0.4066	0.1509	0.9277	0.107*
C4	−0.1019 (9)	0.2020 (3)	0.9883 (3)	0.0926 (14)
H4	−0.1254	0.1775	1.0417	0.111*
C5	0.0986 (8)	0.2541 (3)	0.9776 (2)	0.0850 (12)
H5	0.2113	0.2654	1.0241	0.102*
C6	0.1354 (6)	0.2900 (2)	0.89885 (19)	0.0610 (9)
H6	0.2732	0.3253	0.8918	0.073*
C7	−0.0445 (5)	0.46992 (17)	0.76239 (19)	0.0444 (7)
C8	−0.1209 (5)	0.49608 (17)	0.8443 (2)	0.0507 (8)
C9	−0.0221 (7)	0.5630 (2)	0.8804 (3)	0.0782 (11)
H9	−0.0799	0.5794	0.9348	0.094*
C10	0.1620 (9)	0.6057 (2)	0.8364 (4)	0.0954 (14)
H10	0.2337	0.6503	0.8616	0.115*
C11	0.2409 (8)	0.5827 (2)	0.7553 (4)	0.0965 (14)
H11	0.3652	0.6121	0.7254	0.116*
C12	0.1356 (6)	0.5151 (2)	0.7169 (2)	0.0657 (9)
N1	−0.1455 (4)	0.40045 (13)	0.72490 (14)	0.0410 (6)
H1N	−0.306 (3)	0.3913 (15)	0.7287 (17)	0.049*
O1	0.2938 (3)	0.33879 (11)	0.72465 (12)	0.0504 (5)
O2	−0.0928 (4)	0.26891 (12)	0.66336 (12)	0.0588 (6)
Cl1	−0.35415 (17)	0.44425 (5)	0.90206 (6)	0.0749 (3)
Cl2	0.2244 (2)	0.49191 (6)	0.61194 (7)	0.1076 (4)
S1	0.02094 (12)	0.31832 (4)	0.72850 (4)	0.0389 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0385 (14)	0.0401 (17)	0.0423 (16)	0.0057 (13)	0.0055 (12)	−0.0008 (14)
C2	0.0525 (18)	0.060 (2)	0.073 (2)	−0.0069 (17)	0.0083 (16)	0.0062 (19)
C3	0.087 (3)	0.076 (3)	0.106 (3)	0.002 (2)	0.040 (3)	0.032 (3)
C4	0.116 (4)	0.096 (4)	0.066 (3)	0.038 (3)	0.040 (3)	0.033 (3)
C5	0.102 (3)	0.104 (3)	0.049 (2)	0.025 (3)	−0.009 (2)	0.009 (2)
C6	0.067 (2)	0.073 (2)	0.0428 (18)	−0.0008 (18)	−0.0073 (15)	0.0026 (18)
C7	0.0396 (15)	0.0379 (17)	0.056 (2)	0.0038 (14)	−0.0061 (14)	0.0021 (16)
C8	0.0505 (17)	0.0408 (19)	0.061 (2)	0.0048 (15)	−0.0099 (15)	−0.0073 (16)
C9	0.089 (3)	0.059 (3)	0.086 (3)	0.006 (2)	−0.016 (2)	−0.016 (2)
C10	0.097 (3)	0.049 (3)	0.140 (4)	−0.012 (2)	−0.024 (3)	−0.013 (3)
C11	0.084 (3)	0.050 (3)	0.156 (4)	−0.016 (2)	0.010 (3)	0.028 (3)
C12	0.064 (2)	0.049 (2)	0.084 (3)	0.0000 (18)	0.0077 (18)	0.018 (2)
N1	0.0307 (12)	0.0445 (15)	0.0478 (14)	0.0024 (11)	−0.0032 (11)	0.0009 (12)
O1	0.0306 (10)	0.0601 (14)	0.0606 (13)	0.0023 (9)	0.0049 (8)	0.0080 (11)
O2	0.0684 (12)	0.0622 (14)	0.0456 (12)	0.0019 (11)	−0.0103 (10)	−0.0189 (11)
Cl1	0.0761 (6)	0.0825 (7)	0.0664 (6)	0.0001 (5)	0.0221 (4)	−0.0150 (5)
Cl2	0.1395 (9)	0.0857 (8)	0.0984 (8)	0.0114 (7)	0.0556 (7)	0.0354 (7)
S1	0.0372 (4)	0.0437 (4)	0.0358 (4)	0.0029 (3)	−0.0003 (3)	−0.0040 (4)

C1—C2	1.374 (4)	C7—N1	1.417 (3)
C1—C6	1.378 (4)	C8—C9	1.368 (4)
C1—S1	1.761 (3)	C8—Cl1	1.728 (3)
C2—C3	1.378 (4)	C9—C10	1.367 (5)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.367 (5)	C10—C11	1.368 (5)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.363 (5)	C11—C12	1.402 (5)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.370 (4)	C12—Cl2	1.723 (4)
C5—H5	0.9300	N1—S1	1.641 (2)
C6—H6	0.9300	N1—H1N	0.832 (16)
C7—C12	1.388 (4)	O1—S1	1.4259 (17)
C7—C8	1.392 (4)	O2—S1	1.4284 (19)
C2—C1—C6	120.3 (3)	C7—C8—Cl1	119.6 (2)
C2—C1—S1	120.2 (2)	C10—C9—C8	119.8 (4)
C6—C1—S1	119.5 (2)	C10—C9—H9	120.1
C1—C2—C3	118.8 (3)	C8—C9—H9	120.1
C1—C2—H2	120.6	C9—C10—C11	120.0 (4)
C3—C2—H2	120.6	C9—C10—H10	120.0
C4—C3—C2	121.0 (4)	C11—C10—H10	120.0
C4—C3—H3	119.5	C10—C11—C12	120.5 (4)
C2—C3—H3	119.5	C10—C11—H11	119.8
C5—C4—C3	119.7 (4)	C12—C11—H11	119.8
C5—C4—H4	120.2	C7—C12—C11	119.9 (3)
C3—C4—H4	120.2	C7—C12—Cl2	121.2 (3)
C4—C5—C6	120.4 (4)	C11—C12—Cl2	118.8 (3)
C4—C5—H5	119.8	C7—N1—S1	121.60 (17)
C6—C5—H5	119.8	C7—N1—H1N	118.7 (19)
C5—C6—C1	119.8 (3)	S1—N1—H1N	109.7 (19)
C5—C6—H6	120.1	O1—S1—O2	120.14 (11)
C1—C6—H6	120.1	O1—S1—N1	106.50 (12)
C12—C7—C8	117.5 (3)	O2—S1—N1	106.33 (12)
C12—C7—N1	120.1 (3)	O1—S1—C1	107.38 (12)
C8—C7—N1	122.4 (3)	O2—S1—C1	107.38 (13)
C9—C8—C7	122.2 (3)	N1—S1—C1	108.71 (12)
C9—C8—Cl1	118.2 (3)
C6—C1—C2—C3	0.7 (4)	N1—C7—C12—C11	−178.2 (3)
S1—C1—C2—C3	178.8 (3)	C8—C7—C12—Cl2	−175.1 (2)
C1—C2—C3—C4	−0.8 (5)	N1—C7—C12—Cl2	4.2 (4)
C2—C3—C4—C5	0.8 (6)	C10—C11—C12—C7	−1.8 (5)
C3—C4—C5—C6	−0.6 (6)	C10—C11—C12—Cl2	175.8 (3)
C4—C5—C6—C1	0.4 (6)	C12—C7—N1—S1	81.8 (3)
C2—C1—C6—C5	−0.5 (5)	C8—C7—N1—S1	−98.9 (3)
S1—C1—C6—C5	−178.5 (3)	C7—N1—S1—O1	−32.9 (2)
C12—C7—C8—C9	−0.9 (4)	C7—N1—S1—O2	−162.2 (2)
N1—C7—C8—C9	179.7 (3)	C7—N1—S1—C1	82.5 (2)
C12—C7—C8—Cl1	177.5 (2)	C2—C1—S1—O1	−153.7 (2)
N1—C7—C8—Cl1	−1.9 (4)	C6—C1—S1—O1	24.4 (3)
C7—C8—C9—C10	−1.3 (5)	C2—C1—S1—O2	−23.2 (3)
Cl1—C8—C9—C10	−179.8 (3)	C6—C1—S1—O2	154.9 (2)
C8—C9—C10—C11	2.0 (6)	C2—C1—S1—N1	91.5 (2)
C9—C10—C11—C12	−0.5 (6)	C6—C1—S1—N1	−90.4 (2)
C8—C7—C12—C11	2.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.83 (2)	2.21 (2)	3.027 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.83 (2)	2.21 (2)	3.027 (3)	166 (3)

Symmetry code: (i) .