N-(2,4-Dichloro-phen-yl)benzene-sulfonamide.

The title compound, C(12)H(9)Cl(2)NO(2)S, crystallizes with two independent mol-ecules in the asymmetric unit. The dihedral angles between the two aromatic rings are 70.8 (1) and 74.8 (1)° for the two mol-ecules. The crystal structure features dimers made up of one each of the two asymmetric molecules linked by pairs of N-H⋯O hydrogen bonds. An intra-molecular N-H⋯Cl hydrogen bond is also observed in both mol-ecules.

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. (2008 ▶; 2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C12H9Cl2NO2S

M = 302.16

Monoclinic,

a = 8.2428 (6) Å

b = 19.473 (1) Å

c = 16.873 (1) Å

β = 103.317 (7)°

V = 2635.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.64 mm−1

T = 299 K

0.50 × 0.24 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.740, T max = 0.915

17396 measured reflections

4807 independent reflections

3444 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.106

S = 1.08

4807 reflections

331 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.27 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/S160053680905452X/bt5148sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680905452X/bt5148Isup2.hkl

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

C12H9Cl2NO2S	F(000) = 1232
Mr = 302.16	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6373 reflections
a = 8.2428 (6) Å	θ = 2.4–28.2°
b = 19.473 (1) Å	µ = 0.64 mm−1
c = 16.873 (1) Å	T = 299 K
β = 103.317 (7)°	Rod, colourless
V = 2635.5 (3) Å3	0.50 × 0.24 × 0.14 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4807 independent reflections
Radiation source: fine-focus sealed tube	3444 reflections with I > 2σ(I)
graphite	Rint = 0.029
Rotation method data acquisition using ω and phi scans	θmax = 25.4°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
Tmin = 0.740, Tmax = 0.915	k = −23→20
17396 measured reflections	l = −19→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0259P)2 + 2.4186P] where P = (Fo2 + 2Fc2)/3
4807 reflections	(Δ/σ)max = 0.003
331 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.27 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	0.07684 (12)	0.41223 (4)	0.39801 (6)	0.0729 (3)
Cl2	0.12156 (15)	0.68538 (5)	0.42889 (7)	0.0901 (3)
S1	0.18167 (10)	0.41573 (4)	0.15935 (5)	0.0567 (2)
O1	0.2392 (3)	0.47082 (13)	0.11774 (14)	0.0746 (7)
O2	0.2379 (3)	0.34755 (12)	0.14983 (14)	0.0769 (7)
N1	0.2373 (3)	0.43048 (13)	0.25698 (15)	0.0548 (6)
H1N	0.235 (4)	0.3935 (10)	0.2832 (17)	0.066*
C1	−0.0361 (4)	0.41698 (16)	0.13336 (17)	0.0509 (7)
C2	−0.1220 (5)	0.3600 (2)	0.1486 (2)	0.0739 (10)
H2	−0.0650	0.3212	0.1722	0.089*
C3	−0.2925 (6)	0.3610 (3)	0.1289 (3)	0.0982 (14)
H3	−0.3518	0.3225	0.1387	0.118*
C4	−0.3756 (5)	0.4182 (4)	0.0949 (3)	0.1036 (17)
H4	−0.4915	0.4185	0.0822	0.124*
C5	−0.2897 (6)	0.4757 (3)	0.0791 (2)	0.0952 (14)
H5	−0.3476	0.5144	0.0557	0.114*
C6	−0.1185 (5)	0.47538 (19)	0.0982 (2)	0.0706 (10)
H6	−0.0591	0.5136	0.0878	0.085*
C7	0.2003 (3)	0.49219 (15)	0.29451 (17)	0.0478 (7)
C8	0.1319 (4)	0.49032 (15)	0.36246 (18)	0.0490 (7)
C9	0.1073 (4)	0.54913 (16)	0.40335 (19)	0.0572 (8)
H9	0.0632	0.5467	0.4493	0.069*
C10	0.1487 (4)	0.61158 (16)	0.3756 (2)	0.0595 (8)
C11	0.2117 (5)	0.61546 (17)	0.3073 (2)	0.0692 (10)
H11	0.2359	0.6580	0.2878	0.083*
C12	0.2390 (4)	0.55639 (17)	0.2676 (2)	0.0655 (9)
H12	0.2842	0.5594	0.2220	0.079*
Cl3	0.36502 (15)	0.20468 (5)	0.06873 (6)	0.0908 (3)
Cl4	0.40560 (13)	−0.07047 (5)	0.08844 (6)	0.0814 (3)
S2	0.31006 (11)	0.21769 (4)	0.32166 (5)	0.0617 (2)
O3	0.2519 (3)	0.16658 (13)	0.36835 (14)	0.0768 (7)
O4	0.2532 (3)	0.28666 (12)	0.32451 (15)	0.0851 (8)
N2	0.2533 (4)	0.19672 (14)	0.22530 (17)	0.0633 (7)
H2N	0.261 (4)	0.2319 (11)	0.1965 (18)	0.076*
C13	0.5279 (4)	0.21634 (15)	0.34783 (18)	0.0530 (8)
C14	0.6093 (5)	0.1640 (2)	0.3963 (2)	0.0707 (10)
H14	0.5492	0.1293	0.4145	0.085*
C15	0.7802 (6)	0.1639 (3)	0.4173 (3)	0.1001 (15)
H15	0.8372	0.1289	0.4497	0.120*
C16	0.8680 (6)	0.2161 (4)	0.3898 (3)	0.1076 (18)
H16	0.9839	0.2168	0.4048	0.129*
C17	0.7841 (7)	0.2664 (3)	0.3409 (3)	0.1026 (15)
H17	0.8437	0.3007	0.3217	0.123*
C18	0.6148 (5)	0.26737 (18)	0.3197 (2)	0.0775 (11)
H18	0.5587	0.3021	0.2865	0.093*
C19	0.2931 (4)	0.13263 (16)	0.19385 (19)	0.0546 (8)
C20	0.3432 (4)	0.12956 (16)	0.1208 (2)	0.0595 (8)
C21	0.3763 (4)	0.06739 (17)	0.0877 (2)	0.0638 (9)
H21	0.4081	0.0661	0.0383	0.077*
C22	0.3616 (4)	0.00774 (16)	0.1289 (2)	0.0610 (8)
C23	0.3133 (4)	0.00912 (18)	0.2012 (2)	0.0689 (9)
H23	0.3051	−0.0315	0.2289	0.083*
C24	0.2771 (4)	0.07091 (18)	0.2327 (2)	0.0678 (9)
H24	0.2412	0.0714	0.2811	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.0987 (7)	0.0494 (5)	0.0798 (6)	−0.0115 (4)	0.0397 (5)	−0.0012 (4)
Cl2	0.1147 (8)	0.0507 (5)	0.0958 (7)	0.0072 (5)	0.0053 (6)	−0.0148 (5)
S1	0.0551 (5)	0.0656 (5)	0.0520 (5)	0.0121 (4)	0.0177 (4)	0.0008 (4)
O1	0.0718 (16)	0.0927 (18)	0.0660 (15)	−0.0021 (13)	0.0298 (13)	0.0118 (13)
O2	0.0847 (17)	0.0774 (16)	0.0708 (15)	0.0323 (13)	0.0222 (13)	−0.0079 (13)
N1	0.0551 (16)	0.0541 (16)	0.0532 (16)	0.0088 (13)	0.0082 (13)	0.0053 (12)
C1	0.0545 (19)	0.0586 (19)	0.0400 (16)	0.0047 (15)	0.0118 (14)	−0.0060 (14)
C2	0.073 (3)	0.077 (3)	0.072 (2)	−0.010 (2)	0.016 (2)	−0.0035 (19)
C3	0.079 (3)	0.135 (4)	0.080 (3)	−0.033 (3)	0.017 (2)	−0.005 (3)
C4	0.051 (3)	0.192 (6)	0.068 (3)	0.002 (3)	0.015 (2)	−0.030 (3)
C5	0.076 (3)	0.127 (4)	0.075 (3)	0.040 (3)	0.002 (2)	−0.010 (3)
C6	0.070 (3)	0.075 (2)	0.063 (2)	0.0159 (19)	0.0080 (18)	0.0001 (18)
C7	0.0406 (16)	0.0490 (17)	0.0489 (17)	0.0036 (13)	0.0005 (13)	0.0017 (14)
C8	0.0453 (17)	0.0469 (17)	0.0531 (18)	−0.0034 (13)	0.0074 (14)	0.0021 (14)
C9	0.059 (2)	0.0536 (19)	0.0576 (19)	−0.0005 (15)	0.0108 (16)	−0.0031 (15)
C10	0.060 (2)	0.0493 (18)	0.061 (2)	0.0019 (15)	−0.0032 (16)	−0.0017 (15)
C11	0.083 (3)	0.0471 (19)	0.071 (2)	−0.0058 (17)	0.005 (2)	0.0095 (17)
C12	0.074 (2)	0.064 (2)	0.058 (2)	−0.0045 (17)	0.0152 (18)	0.0104 (17)
Cl3	0.1349 (10)	0.0616 (6)	0.0874 (7)	−0.0052 (6)	0.0490 (7)	0.0099 (5)
Cl4	0.0930 (7)	0.0606 (5)	0.0820 (6)	0.0015 (5)	0.0025 (5)	−0.0108 (5)
S2	0.0679 (6)	0.0615 (5)	0.0598 (5)	0.0156 (4)	0.0229 (4)	0.0039 (4)
O3	0.0781 (17)	0.0868 (17)	0.0751 (16)	0.0024 (13)	0.0372 (13)	0.0106 (13)
O4	0.110 (2)	0.0681 (16)	0.0819 (17)	0.0393 (15)	0.0314 (15)	0.0032 (13)
N2	0.0685 (19)	0.0600 (18)	0.0595 (17)	0.0116 (15)	0.0109 (14)	0.0104 (14)
C13	0.068 (2)	0.0483 (17)	0.0463 (17)	0.0016 (15)	0.0202 (15)	−0.0071 (14)
C14	0.068 (3)	0.084 (3)	0.061 (2)	0.010 (2)	0.0156 (18)	0.0069 (19)
C15	0.076 (3)	0.145 (4)	0.073 (3)	0.030 (3)	0.005 (2)	−0.009 (3)
C16	0.058 (3)	0.175 (6)	0.090 (3)	−0.012 (3)	0.017 (3)	−0.057 (4)
C17	0.099 (4)	0.107 (4)	0.110 (4)	−0.045 (3)	0.040 (3)	−0.039 (3)
C18	0.092 (3)	0.059 (2)	0.086 (3)	−0.015 (2)	0.029 (2)	−0.0129 (19)
C19	0.0486 (19)	0.0563 (19)	0.0548 (19)	0.0012 (15)	0.0034 (15)	0.0011 (15)
C20	0.059 (2)	0.056 (2)	0.061 (2)	−0.0044 (16)	0.0083 (16)	0.0056 (16)
C21	0.065 (2)	0.065 (2)	0.061 (2)	−0.0037 (17)	0.0136 (17)	−0.0050 (17)
C22	0.058 (2)	0.054 (2)	0.063 (2)	−0.0016 (16)	−0.0013 (17)	−0.0025 (16)
C23	0.081 (3)	0.057 (2)	0.064 (2)	−0.0058 (18)	0.0058 (19)	0.0079 (17)
C24	0.076 (2)	0.069 (2)	0.059 (2)	−0.0018 (18)	0.0139 (18)	0.0061 (18)

Cl1—C8	1.733 (3)	Cl3—C20	1.737 (3)
Cl2—C10	1.737 (3)	Cl4—C22	1.741 (3)
S1—O1	1.422 (2)	S2—O3	1.419 (2)
S1—O2	1.428 (2)	S2—O4	1.427 (2)
S1—N1	1.631 (3)	S2—N2	1.637 (3)
S1—C1	1.747 (3)	S2—C13	1.747 (3)
N1—C7	1.424 (4)	N2—C19	1.424 (4)
N1—H1N	0.847 (10)	N2—H2N	0.851 (10)
C1—C2	1.372 (4)	C13—C18	1.373 (4)
C1—C6	1.386 (4)	C13—C14	1.381 (4)
C2—C3	1.367 (5)	C14—C15	1.371 (5)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.362 (6)	C15—C16	1.388 (7)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.384 (7)	C16—C17	1.363 (7)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.373 (5)	C17—C18	1.358 (6)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.390 (4)	C19—C20	1.389 (4)
C7—C12	1.392 (4)	C19—C24	1.390 (4)
C8—C9	1.376 (4)	C20—C21	1.386 (4)
C9—C10	1.374 (4)	C21—C22	1.373 (4)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.370 (5)	C22—C23	1.368 (5)
C11—C12	1.376 (5)	C23—C24	1.376 (5)
C11—H11	0.9300	C23—H23	0.9300
C12—H12	0.9300	C24—H24	0.9300
O1—S1—O2	119.49 (15)	O3—S2—O4	119.04 (16)
O1—S1—N1	108.53 (15)	O3—S2—N2	108.69 (15)
O2—S1—N1	104.74 (14)	O4—S2—N2	104.32 (15)
O1—S1—C1	107.80 (15)	O3—S2—C13	107.94 (15)
O2—S1—C1	109.05 (15)	O4—S2—C13	109.40 (16)
N1—S1—C1	106.55 (14)	N2—S2—C13	106.83 (14)
C7—N1—S1	124.0 (2)	C19—N2—S2	123.4 (2)
C7—N1—H1N	117 (2)	C19—N2—H2N	116 (2)
S1—N1—H1N	110 (2)	S2—N2—H2N	109 (2)
C2—C1—C6	121.3 (3)	C18—C13—C14	121.2 (3)
C2—C1—S1	119.1 (3)	C18—C13—S2	119.3 (3)
C6—C1—S1	119.5 (3)	C14—C13—S2	119.4 (3)
C3—C2—C1	119.3 (4)	C15—C14—C13	118.9 (4)
C3—C2—H2	120.4	C15—C14—H14	120.5
C1—C2—H2	120.4	C13—C14—H14	120.5
C4—C3—C2	120.2 (4)	C14—C15—C16	119.8 (5)
C4—C3—H3	119.9	C14—C15—H15	120.1
C2—C3—H3	119.9	C16—C15—H15	120.1
C3—C4—C5	120.8 (4)	C17—C16—C15	119.9 (4)
C3—C4—H4	119.6	C17—C16—H16	120.1
C5—C4—H4	119.6	C15—C16—H16	120.1
C6—C5—C4	119.7 (4)	C18—C17—C16	121.1 (5)
C6—C5—H5	120.2	C18—C17—H17	119.4
C4—C5—H5	120.2	C16—C17—H17	119.4
C5—C6—C1	118.7 (4)	C17—C18—C13	119.1 (4)
C5—C6—H6	120.7	C17—C18—H18	120.5
C1—C6—H6	120.7	C13—C18—H18	120.5
C8—C7—C12	117.4 (3)	C20—C19—C24	117.5 (3)
C8—C7—N1	120.9 (3)	C20—C19—N2	120.7 (3)
C12—C7—N1	121.6 (3)	C24—C19—N2	121.8 (3)
C9—C8—C7	121.8 (3)	C21—C20—C19	121.4 (3)
C9—C8—Cl1	118.4 (2)	C21—C20—Cl3	118.6 (3)
C7—C8—Cl1	119.8 (2)	C19—C20—Cl3	119.9 (3)
C10—C9—C8	119.3 (3)	C22—C21—C20	119.1 (3)
C10—C9—H9	120.4	C22—C21—H21	120.4
C8—C9—H9	120.4	C20—C21—H21	120.4
C11—C10—C9	120.5 (3)	C23—C22—C21	120.8 (3)
C11—C10—Cl2	120.6 (3)	C23—C22—Cl4	119.8 (3)
C9—C10—Cl2	118.9 (3)	C21—C22—Cl4	119.4 (3)
C10—C11—C12	120.0 (3)	C22—C23—C24	119.7 (3)
C10—C11—H11	120.0	C22—C23—H23	120.2
C12—C11—H11	120.0	C24—C23—H23	120.2
C11—C12—C7	121.1 (3)	C23—C24—C19	121.4 (3)
C11—C12—H12	119.5	C23—C24—H24	119.3
C7—C12—H12	119.5	C19—C24—H24	119.3
O1—S1—N1—C7	53.7 (3)	O3—S2—N2—C19	−55.5 (3)
O2—S1—N1—C7	−177.6 (2)	O4—S2—N2—C19	176.5 (3)
C1—S1—N1—C7	−62.1 (3)	C13—S2—N2—C19	60.7 (3)
O1—S1—C1—C2	163.9 (2)	O3—S2—C13—C18	−170.9 (3)
O2—S1—C1—C2	32.8 (3)	O4—S2—C13—C18	−40.0 (3)
N1—S1—C1—C2	−79.8 (3)	N2—S2—C13—C18	72.4 (3)
O1—S1—C1—C6	−16.4 (3)	O3—S2—C13—C14	9.2 (3)
O2—S1—C1—C6	−147.6 (2)	O4—S2—C13—C14	140.1 (3)
N1—S1—C1—C6	99.9 (3)	N2—S2—C13—C14	−107.5 (3)
C6—C1—C2—C3	−0.1 (5)	C18—C13—C14—C15	0.9 (5)
S1—C1—C2—C3	179.5 (3)	S2—C13—C14—C15	−179.2 (3)
C1—C2—C3—C4	−0.4 (6)	C13—C14—C15—C16	0.2 (6)
C2—C3—C4—C5	0.6 (7)	C14—C15—C16—C17	−1.3 (7)
C3—C4—C5—C6	−0.3 (7)	C15—C16—C17—C18	1.5 (7)
C4—C5—C6—C1	−0.2 (6)	C16—C17—C18—C13	−0.4 (6)
C2—C1—C6—C5	0.4 (5)	C14—C13—C18—C17	−0.8 (5)
S1—C1—C6—C5	−179.2 (3)	S2—C13—C18—C17	179.3 (3)
S1—N1—C7—C8	131.2 (3)	S2—N2—C19—C20	−138.3 (3)
S1—N1—C7—C12	−52.3 (4)	S2—N2—C19—C24	44.4 (4)
C12—C7—C8—C9	−1.8 (4)	C24—C19—C20—C21	−0.1 (5)
N1—C7—C8—C9	174.9 (3)	N2—C19—C20—C21	−177.5 (3)
C12—C7—C8—Cl1	178.7 (2)	C24—C19—C20—Cl3	179.8 (2)
N1—C7—C8—Cl1	−4.6 (4)	N2—C19—C20—Cl3	2.3 (4)
C7—C8—C9—C10	1.2 (5)	C19—C20—C21—C22	−1.0 (5)
Cl1—C8—C9—C10	−179.4 (2)	Cl3—C20—C21—C22	179.2 (3)
C8—C9—C10—C11	0.9 (5)	C20—C21—C22—C23	0.6 (5)
C8—C9—C10—Cl2	−178.6 (2)	C20—C21—C22—Cl4	−179.2 (2)
C9—C10—C11—C12	−2.2 (5)	C21—C22—C23—C24	0.8 (5)
Cl2—C10—C11—C12	177.3 (3)	Cl4—C22—C23—C24	−179.4 (3)
C10—C11—C12—C7	1.5 (5)	C22—C23—C24—C19	−1.9 (5)
C8—C7—C12—C11	0.5 (5)	C20—C19—C24—C23	1.5 (5)
N1—C7—C12—C11	−176.2 (3)	N2—C19—C24—C23	178.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.85 (1)	2.19 (1)	3.015 (3)	165 (3)
N1—H1N···Cl1	0.85 (1)	2.60 (3)	2.998 (3)	110 (2)
N2—H2N···O2	0.85 (1)	2.38 (2)	3.192 (4)	160 (3)
N2—H2N···Cl3	0.85 (1)	2.55 (3)	2.996 (3)	113 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4	0.85 (1)	2.19 (1)	3.015 (3)	165 (3)
N1—H1N⋯Cl1	0.85 (1)	2.60 (3)	2.998 (3)	110 (2)
N2—H2N⋯O2	0.85 (1)	2.38 (2)	3.192 (4)	160 (3)
N2—H2N⋯Cl3	0.85 (1)	2.55 (3)	2.996 (3)	113 (3)