2,4-Dichloro-N-(4-chloro­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536810010494

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o918

doi:10.1107/S1600536810010494

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2,4-Dichloro-N-(4-chlorophenyl)benzenesulfonamide

P. G. Nirmala,^a B. Thimme Gowda,^a ^* Sabine Foro ^b 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 20 March 2010; accepted 20 March 2010; online 24 March 2010)

The molecule of the title compound, C₁₂H₈Cl₃NO₂S, is twisted at the S atom, the C—SO₂—NH—C torsion angle being 67.8 (2)°. The dihedral angle between the two benzene rings is 65.0 (1)°. The crystal structure features inversion dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). 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

C₁₂H₈Cl₃NO₂S
M_r = 336.60
Triclinic, $[P \overline 1]$
a = 6.3925 (9) Å
b = 10.524 (2) Å
c = 11.684 (2) Å
α = 69.51 (1)°
β = 77.96 (1)°
γ = 77.30 (1)°
V = 710.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.79 mm⁻¹
T = 299 K
0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur single-crystal X-ray 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 = 0.744, T_max = 0.798
4462 measured reflections
2873 independent reflections
2514 reflections with I > 2σ(I)
R_int = 0.008

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.091
S = 1.04
2873 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (2)	2.20 (2)	3.014 (3)	163 (2)
Symmetry code: (i) -x+1, -y, -z.

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/S1600536810010494/ci5064sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010494/ci5064Isup2.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., 2009, 2010), the structure of 2,4-dichloro-N-(4-chlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The molecule is twisted at the S—N bond with the C—SO₂—NH—C torsion angle being 67.8 (2)° compared to the values of 60.6 (4)° (molecule 1), -59.7 (3)° (molecule 2), 63.9 (4)° (molecule 3) and 53.0 (4)° (molecule 4), in the four molecules of 2,4-dichloro-N- (4-methylphenyl)benzenesulfonamide (II) (Gowda et al., 2010) and -48.2 (2)° in 2,4-dichloro-N-(3,4-dichlorophenyl)benzenesulfonamide (III) (Gowda et al., 2009).

The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 65.0 (1)°, compared to the values of 85.2 (1)° (molecule 1), 80.5 (2)° (molecule 2, disordered orientation A), 80.1 (2)° (molecule 2, orientation B), 87.5 (7) (molecule 3, disordered orientation A), 87.0 (6)° (molecule 3, orienation B) and 72.4 (1)° (molecule 4) in the four molecules of (II) and 68.9 (1)° in (III). The other bond parameters in (I) are similar to those observed in (II), (III) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the molecules to form inversion-related dimers as shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). 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 top

The solution of 1,3-dichlorobenzene (10 ml) in chloroform (40 ml) was treated drop-wise with chlorosulfonic acid (25 ml) at 273 K. 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 2,4-dichlorobenzenesulfonylchloride was treated with a stoichiometric amount of p-chloroaniline 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 2,4-dichloro-N- (4-chlorophenyl)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 (Savitha & Gowda, 2006). The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation 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 scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dichloro-N-(4-chlorophenyl)benzenesulfonamide top

Crystal data top

C₁₂H₈Cl₃NO₂S	Z = 2
M_r = 336.60	F(000) = 340
Triclinic, P1	D_x = 1.573 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3925 (9) Å	Cell parameters from 2802 reflections
b = 10.524 (2) Å	θ = 3.2–27.7°
c = 11.684 (2) Å	µ = 0.79 mm⁻¹
α = 69.51 (1)°	T = 299 K
β = 77.96 (1)°	Prism, colourless
γ = 77.30 (1)°	0.40 × 0.40 × 0.30 mm
V = 710.8 (2) Å³

Data collection top

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector	2873 independent reflections
Radiation source: fine-focus sealed tube	2514 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.008
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→7
T_min = 0.744, T_max = 0.798	k = −13→13
4462 measured reflections	l = −14→12

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0386P)² + 0.4934P] where P = (F_o² + 2F_c²)/3
2873 reflections	(Δ/σ)_max = 0.001
175 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₂H₈Cl₃NO₂S	γ = 77.30 (1)°
M_r = 336.60	V = 710.8 (2) Å³
Triclinic, P1	Z = 2
a = 6.3925 (9) Å	Mo Kα radiation
b = 10.524 (2) Å	µ = 0.79 mm⁻¹
c = 11.684 (2) Å	T = 299 K
α = 69.51 (1)°	0.40 × 0.40 × 0.30 mm
β = 77.96 (1)°

Data collection top

Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector	2873 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2514 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.798	R_int = 0.008
4462 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.41 e Å⁻³
2873 reflections	Δρ_min = −0.47 e Å⁻³
175 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.2300 (3)	−0.1157 (2)	0.30386 (18)	0.0362 (4)
C2	0.1233 (3)	−0.1828 (2)	0.25451 (18)	0.0370 (4)
C3	−0.0339 (4)	−0.2602 (2)	0.3281 (2)	0.0449 (5)
H3	−0.1049	−0.3044	0.2949	0.054*
C4	−0.0835 (4)	−0.2707 (2)	0.4523 (2)	0.0504 (5)
C5	0.0190 (4)	−0.2058 (3)	0.5036 (2)	0.0553 (6)
H5	−0.0168	−0.2136	0.5869	0.066*
C6	0.1766 (4)	−0.1286 (2)	0.4290 (2)	0.0477 (5)
H6	0.2472	−0.0850	0.4629	0.057*
C7	0.1442 (3)	0.2193 (2)	0.13604 (18)	0.0357 (4)
C8	0.1996 (3)	0.3448 (2)	0.1231 (2)	0.0430 (5)
H8	0.3429	0.3588	0.0971	0.052*
C9	0.0426 (4)	0.4488 (2)	0.1487 (2)	0.0473 (5)
H9	0.0792	0.5329	0.1397	0.057*
C10	−0.1696 (3)	0.4259 (2)	0.1880 (2)	0.0421 (5)
C11	−0.2275 (3)	0.3009 (2)	0.2035 (2)	0.0420 (5)
H11	−0.3703	0.2865	0.2317	0.050*
C12	−0.0694 (3)	0.1975 (2)	0.17658 (19)	0.0397 (4)
H12	−0.1065	0.1135	0.1857	0.048*
N1	0.3104 (3)	0.11422 (18)	0.10621 (17)	0.0432 (4)
H1N	0.312 (4)	0.100 (3)	0.0395 (18)	0.052*
O1	0.4832 (3)	0.04803 (18)	0.29394 (16)	0.0551 (4)
O2	0.5937 (2)	−0.08756 (17)	0.14887 (15)	0.0529 (4)
Cl1	0.17630 (10)	−0.16945 (7)	0.09860 (5)	0.05343 (17)
Cl2	−0.28179 (14)	−0.36791 (9)	0.54410 (7)	0.0830 (3)
Cl3	−0.36952 (11)	0.55863 (7)	0.21560 (8)	0.0699 (2)
S1	0.42695 (8)	−0.00974 (5)	0.21258 (5)	0.03973 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0351 (10)	0.0349 (10)	0.0358 (10)	−0.0039 (8)	−0.0043 (8)	−0.0094 (8)
C2	0.0393 (10)	0.0357 (10)	0.0334 (10)	−0.0018 (8)	−0.0043 (8)	−0.0109 (8)
C3	0.0463 (12)	0.0424 (11)	0.0464 (12)	−0.0104 (9)	−0.0050 (9)	−0.0138 (9)
C4	0.0497 (13)	0.0499 (13)	0.0429 (12)	−0.0139 (10)	0.0019 (10)	−0.0056 (10)
C5	0.0659 (15)	0.0634 (15)	0.0325 (11)	−0.0148 (12)	−0.0011 (10)	−0.0112 (10)
C6	0.0557 (13)	0.0513 (13)	0.0384 (11)	−0.0118 (10)	−0.0073 (10)	−0.0149 (10)
C7	0.0369 (10)	0.0344 (10)	0.0335 (9)	−0.0039 (8)	−0.0044 (8)	−0.0095 (8)
C8	0.0365 (10)	0.0412 (11)	0.0480 (12)	−0.0122 (9)	−0.0032 (9)	−0.0081 (9)
C9	0.0525 (13)	0.0337 (10)	0.0574 (13)	−0.0131 (9)	−0.0071 (10)	−0.0134 (9)
C10	0.0425 (11)	0.0373 (10)	0.0454 (11)	−0.0003 (9)	−0.0070 (9)	−0.0152 (9)
C11	0.0340 (10)	0.0450 (11)	0.0483 (12)	−0.0082 (9)	−0.0047 (9)	−0.0159 (9)
C12	0.0402 (10)	0.0365 (10)	0.0462 (11)	−0.0098 (8)	−0.0065 (9)	−0.0154 (9)
N1	0.0445 (10)	0.0402 (9)	0.0379 (9)	−0.0001 (8)	−0.0002 (8)	−0.0113 (8)
O1	0.0531 (9)	0.0575 (10)	0.0612 (10)	−0.0182 (8)	−0.0146 (8)	−0.0175 (8)
O2	0.0368 (8)	0.0504 (9)	0.0592 (10)	0.0036 (7)	0.0019 (7)	−0.0141 (8)
Cl1	0.0641 (4)	0.0632 (4)	0.0384 (3)	−0.0168 (3)	0.0000 (2)	−0.0230 (3)
Cl2	0.0816 (5)	0.0924 (6)	0.0669 (5)	−0.0470 (4)	0.0183 (4)	−0.0121 (4)
Cl3	0.0592 (4)	0.0491 (3)	0.0987 (5)	0.0051 (3)	0.0000 (4)	−0.0350 (4)
S1	0.0324 (3)	0.0389 (3)	0.0448 (3)	−0.0049 (2)	−0.0031 (2)	−0.0116 (2)

Geometric parameters (Å, º) top

C1—C6	1.395 (3)	C7—N1	1.440 (3)
C1—C2	1.398 (3)	C8—C9	1.384 (3)
C1—S1	1.787 (2)	C8—H8	0.93
C2—C3	1.387 (3)	C9—C10	1.384 (3)
C2—Cl1	1.743 (2)	C9—H9	0.93
C3—C4	1.389 (3)	C10—C11	1.384 (3)
C3—H3	0.93	C10—Cl3	1.746 (2)
C4—C5	1.380 (4)	C11—C12	1.389 (3)
C4—Cl2	1.743 (2)	C11—H11	0.93
C5—C6	1.391 (3)	C12—H12	0.93
C5—H5	0.93	N1—S1	1.6203 (19)
C6—H6	0.93	N1—H1N	0.839 (16)
C7—C12	1.391 (3)	O1—S1	1.4305 (17)
C7—C8	1.391 (3)	O2—S1	1.4398 (16)

C6—C1—C2	118.88 (19)	C7—C8—H8	119.8
C6—C1—S1	118.25 (16)	C10—C9—C8	119.11 (19)
C2—C1—S1	122.84 (15)	C10—C9—H9	120.4
C3—C2—C1	120.79 (18)	C8—C9—H9	120.4
C3—C2—Cl1	117.32 (16)	C9—C10—C11	121.48 (19)
C1—C2—Cl1	121.87 (15)	C9—C10—Cl3	119.21 (17)
C2—C3—C4	118.9 (2)	C11—C10—Cl3	119.30 (16)
C2—C3—H3	120.6	C10—C11—C12	119.08 (19)
C4—C3—H3	120.6	C10—C11—H11	120.5
C5—C4—C3	121.7 (2)	C12—C11—H11	120.5
C5—C4—Cl2	119.76 (18)	C11—C12—C7	120.12 (18)
C3—C4—Cl2	118.58 (19)	C11—C12—H12	119.9
C4—C5—C6	119.0 (2)	C7—C12—H12	119.9
C4—C5—H5	120.5	C7—N1—S1	121.38 (14)
C6—C5—H5	120.5	C7—N1—H1N	117.2 (18)
C5—C6—C1	120.8 (2)	S1—N1—H1N	117.4 (18)
C5—C6—H6	119.6	O1—S1—O2	119.68 (10)
C1—C6—H6	119.6	O1—S1—N1	108.21 (10)
C12—C7—C8	119.89 (18)	O2—S1—N1	105.97 (10)
C12—C7—N1	121.13 (18)	O1—S1—C1	105.62 (10)
C8—C7—N1	118.99 (18)	O2—S1—C1	109.05 (10)
C9—C8—C7	120.31 (19)	N1—S1—C1	107.86 (10)
C9—C8—H8	119.8

C6—C1—C2—C3	0.4 (3)	C8—C9—C10—Cl3	−177.94 (18)
S1—C1—C2—C3	−177.75 (16)	C9—C10—C11—C12	−1.4 (3)
C6—C1—C2—Cl1	178.71 (16)	Cl3—C10—C11—C12	177.38 (17)
S1—C1—C2—Cl1	0.6 (2)	C10—C11—C12—C7	0.8 (3)
C1—C2—C3—C4	−0.3 (3)	C8—C7—C12—C11	0.3 (3)
Cl1—C2—C3—C4	−178.66 (17)	N1—C7—C12—C11	−179.30 (19)
C2—C3—C4—C5	0.2 (4)	C12—C7—N1—S1	−81.8 (2)
C2—C3—C4—Cl2	179.86 (17)	C8—C7—N1—S1	98.6 (2)
C3—C4—C5—C6	−0.3 (4)	C7—N1—S1—O1	−46.02 (19)
Cl2—C4—C5—C6	−179.93 (19)	C7—N1—S1—O2	−175.53 (16)
C4—C5—C6—C1	0.4 (4)	C7—N1—S1—C1	67.79 (18)
C2—C1—C6—C5	−0.5 (3)	C6—C1—S1—O1	−2.80 (19)
S1—C1—C6—C5	177.76 (19)	C2—C1—S1—O1	175.37 (16)
C12—C7—C8—C9	−0.9 (3)	C6—C1—S1—O2	127.02 (17)
N1—C7—C8—C9	178.7 (2)	C2—C1—S1—O2	−54.81 (19)
C7—C8—C9—C10	0.3 (3)	C6—C1—S1—N1	−118.33 (17)
C8—C9—C10—C11	0.8 (3)	C2—C1—S1—N1	59.84 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.20 (2)	3.014 (3)	163 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₂H₈Cl₃NO₂S
M_r	336.60
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.3925 (9), 10.524 (2), 11.684 (2)
α, β, γ (°)	69.51 (1), 77.96 (1), 77.30 (1)
V (Å³)	710.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.79
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur single-crystal X-ray diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.744, 0.798
No. of measured, independent and observed [I > 2σ(I)] reflections	4462, 2873, 2514
R_int	0.008
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.091, 1.04
No. of reflections	2873
No. of parameters	175
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.47

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.20 (2)	3.014 (3)	163 (2)

Symmetry code: (i) −x+1, −y, −z.

References

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o918

doi:10.1107/S1600536810010494

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