N-(2,4-Dichloro­phen­yl)benzene­sulfonamide

Gowda, B.T.; Foro, S.; Nirmala, P.G.; Fuess, H.

doi:10.1107/S160053680905452X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o229

doi:10.1107/S160053680905452X

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N-(2,4-Dichlorophenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 17 December 2009; accepted 17 December 2009; online 24 December 2009)

The title compound, C₁₂H₉Cl₂NO₂S, crystallizes with two independent molecules in the asymmetric unit. The dihedral angles between the two aromatic rings are 70.8 (1) and 74.8 (1)° for the two molecules. 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 intramolecular N—H⋯Cl hydrogen bond is also observed in both molecules.

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_r = 302.16
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.106
S = 1.08
4807 reflections
331 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.27 e Å⁻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)

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680905452X/bt5148sup1.cif

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

checkCIF report

Comment top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al., 2008; Gowda et al., 2010), the structure of N-(2,4-Dichlorophenyl)benzenesulfonamide (I) has been determined. The asymmetric unit of the structure contains two independent molecules.

The sulfonyl benzene and the aniline benzene rings in the two molecules of (I) are tilted relative to each other by 70.8 (1)° (molecule 1) and 74.8 (1)° (molecule 2). The other bond parameters in (I) are similar to those observed in other aryl sulfonamides (Gowda et al., 2010; Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, both the intramolecular N—H···Cl and intermolecular N—H···O hydrogen bonds are observed. The pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers (Fig. 2).

Related literature top

For the preparation of the 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 top

The solution of benzene (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual benzenesulfonylchloride was treated with 2,4-dichloroaniline in the stoichiometric amounts and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 ml). The resultant solid N-(2,4-dichlorophenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Shetty & Gowda, 2005). The rod like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by evaporating it at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008.

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-(2,4-Dichlorophenyl)benzenesulfonamide top

Crystal data top

C₁₂H₉Cl₂NO₂S	F(000) = 1232
M_r = 302.16	D_x = 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

Data collection top

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 monochromator	R_int = 0.029
Rotation method data acquisition using ω and phi scans	θ_max = 25.4°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→8
T_min = 0.740, T_max = 0.915	k = −23→20
17396 measured reflections	l = −19→20

Refinement top

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(F_o²) + (0.0259P)² + 2.4186P] where P = (F_o² + 2F_c²)/3
4807 reflections	(Δ/σ)_max = 0.003
331 parameters	Δρ_max = 0.29 e Å⁻³
2 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₂H₉Cl₂NO₂S	V = 2635.5 (3) Å³
M_r = 302.16	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.2428 (6) Å	µ = 0.64 mm⁻¹
b = 19.473 (1) Å	T = 299 K
c = 16.873 (1) Å	0.50 × 0.24 × 0.14 mm
β = 103.317 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4807 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3444 reflections with I > 2σ(I)
T_min = 0.740, T_max = 0.915	R_int = 0.029
17396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.29 e Å⁻³
4807 reflections	Δρ_min = −0.27 e Å⁻³
331 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₂H₉Cl₂NO₂S
M_r	302.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	8.2428 (6), 19.473 (1), 16.873 (1)
β (°)	103.317 (7)
V (Å³)	2635.5 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.50 × 0.24 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.740, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	17396, 4807, 3444
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.106, 1.08
No. of reflections	4807
No. of parameters	331
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4	0.847 (10)	2.189 (13)	3.015 (3)	165 (3)
N1—H1N···Cl1	0.847 (10)	2.60 (3)	2.998 (3)	110 (2)
N2—H2N···O2	0.851 (10)	2.378 (15)	3.192 (4)	160 (3)
N2—H2N···Cl3	0.851 (10)	2.55 (3)	2.996 (3)	113 (3)

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o2190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o190. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780–o782. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shetty, M. & Gowda, B. T. (2005). Z. Naturforsch. Teil A, 60, 113–120. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 1| January 2010| Page o229

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