4-Chloro-N-(3-chloro­phen­yl)-2-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536810022968

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1702

doi:10.1107/S1600536810022968

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4-Chloro-N-(3-chlorophenyl)-2-methylbenzenesulfonamide

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 3 June 2010; accepted 14 June 2010; online 18 June 2010)

In the title compound, C₁₃H₁₁Cl₂NO₂S, the conformation of the N—H bond in the C—SO₂—NH—C segment is anti to the meta-Cl atom on the aniline ring and syn to the ortho-methyl group on the sulfonylbenzene ring. Furthermore, the torsion angle of the C—SO₂—NH—C segment in the molecule is 80.1 (3)°. The two benzene rings are tilted relative to each other by 70.9 (1)°. In the crystal, pairs of intermolecular N—H⋯O hydrogen bonds link the molecules via inversion-related dimers into infinite column-like chains.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008 , 2009a ,b ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₁Cl₂NO₂S
M_r = 316.19
Monoclinic, P 2₁ /c
a = 7.9757 (7) Å
b = 11.3472 (8) Å
c = 15.569 (1) Å
β = 91.490 (8)°
V = 1408.55 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 299 K
0.36 × 0.28 × 0.04 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 = 0.812, T_max = 0.976
5849 measured reflections
2866 independent reflections
1853 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.161
S = 1.04
2866 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.85 (2)	2.08 (2)	2.926 (4)	175 (4)
Symmetry code: (i) -x+1, -y, -z+1.

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/S1600536810022968/vm2031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022968/vm2031Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of N-(aryl)-arylsulfonamides (Gowda et al., 2008; Gowda et al., 2009a,b), in the present work, the structure of 4-chloro-2-methyl-N-(3-chlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond on the C—SO₂—NH—C segment is anti to the meta-Cl on the aniline ring and syn to the ortho-methyl group in the sulfonyl benzene ring.

The torsion angle of the segment C—SO₂—NH—C in (I) is 80.1 (3)°, compared to the values of -61.9 (4)° and 69.7 (4)° in the two independent molecules of 4-chloro-2-methyl-N-(phenyl)-benzenesulfonamide(II) (Gowda et al., 2009a), 74.8 (4)° in 4-chloro-2-methyl-N-(2-chlorophenyl)-benzenesulfonamide (III) (Gowda et al., 2009b) and -60.1 (2)° in N-(3-chlorophenyl)-benzenesulfonamide (IV)(Gowda et al., 2008).

The sulfonyl and the aniline benzene rings in (I) are tilted relative to each other by 70.9 (1)°, compared to the values of 86.6 (2)° and 83.0 (2)° in the two independent molecules of (II), 45.5 (2)° in (III) and 65.4 (1)° in (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules into inversion-related dimers, which are further linked into infinite column like chains through C—H···π and C—Cl···π interactions. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2008, 2009a,b). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of m-chlorotoluene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 2-methyl-4-chlorobenzenesulfonylchloride was treated with 3-chloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 cc). The resultant solid 4-chloro-2-methyl-N- (3-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 plate like colourless 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 and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Chloro-N-(3-chlorophenyl)-2-methylbenzenesulfonamide top

Crystal data top

C₁₃H₁₁Cl₂NO₂S	F(000) = 648
M_r = 316.19	D_x = 1.491 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2107 reflections
a = 7.9757 (7) Å	θ = 2.6–27.8°
b = 11.3472 (8) Å	µ = 0.61 mm⁻¹
c = 15.569 (1) Å	T = 299 K
β = 91.490 (8)°	Plate, colourless
V = 1408.55 (18) Å³	0.36 × 0.28 × 0.04 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2866 independent reflections
Radiation source: fine-focus sealed tube	1853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→7
T_min = 0.812, T_max = 0.976	k = −14→14
5849 measured reflections	l = −19→19

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0763P)² + 0.8836P] where P = (F_o² + 2F_c²)/3
2866 reflections	(Δ/σ)_max = 0.001
176 parameters	Δρ_max = 0.43 e Å⁻³
1 restraint	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₃H₁₁Cl₂NO₂S	V = 1408.55 (18) Å³
M_r = 316.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9757 (7) Å	µ = 0.61 mm⁻¹
b = 11.3472 (8) Å	T = 299 K
c = 15.569 (1) Å	0.36 × 0.28 × 0.04 mm
β = 91.490 (8)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2866 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1853 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.976	R_int = 0.017
5849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	1 restraint
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
2866 reflections	Δρ_min = −0.52 e Å⁻³
176 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
C1	0.3431 (4)	0.2031 (3)	0.66150 (19)	0.0451 (7)
C2	0.3719 (5)	0.2761 (3)	0.7319 (2)	0.0571 (9)
H2	0.4793	0.2818	0.7563	0.069*
C3	0.2436 (6)	0.3398 (3)	0.7657 (2)	0.0642 (10)
H3	0.2638	0.3897	0.8122	0.077*
C4	0.0858 (5)	0.3293 (3)	0.7305 (2)	0.0617 (10)
C5	0.0557 (5)	0.2571 (3)	0.6608 (3)	0.0630 (10)
H5	−0.0530	0.2507	0.6383	0.076*
C6	0.1829 (4)	0.1936 (3)	0.6234 (2)	0.0508 (8)
C7	0.6346 (4)	0.2765 (3)	0.5046 (2)	0.0486 (8)
C8	0.6426 (4)	0.3741 (3)	0.5575 (2)	0.0543 (8)
H8	0.5940	0.3729	0.6111	0.065*
C9	0.7240 (5)	0.4732 (3)	0.5292 (2)	0.0585 (9)
C10	0.7951 (6)	0.4781 (4)	0.4506 (3)	0.0809 (13)
H10	0.8492	0.5459	0.4325	0.097*
C11	0.7847 (6)	0.3796 (4)	0.3983 (3)	0.0887 (15)
H11	0.8319	0.3815	0.3444	0.106*
C12	0.7061 (5)	0.2795 (4)	0.4249 (2)	0.0641 (10)
H12	0.7007	0.2137	0.3893	0.077*
C13	0.1457 (5)	0.1168 (3)	0.5412 (2)	0.0595 (10)
H13A	0.1807	0.0371	0.5519	0.071*
H13B	0.2060	0.1481	0.4937	0.071*
H13C	0.0276	0.1182	0.5276	0.071*
N1	0.5495 (4)	0.1719 (3)	0.5270 (2)	0.0640 (9)
H1N	0.539 (5)	0.120 (3)	0.488 (2)	0.077*
O1	0.6571 (3)	0.1510 (2)	0.67778 (17)	0.0697 (7)
O2	0.4690 (3)	0.0031 (2)	0.61100 (16)	0.0660 (7)
Cl1	−0.0771 (2)	0.41129 (13)	0.77137 (10)	0.1162 (6)
Cl2	0.73479 (16)	0.59549 (9)	0.59594 (8)	0.0858 (4)
S1	0.51639 (11)	0.12421 (7)	0.62307 (6)	0.0533 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0512 (19)	0.0407 (16)	0.0432 (17)	−0.0108 (14)	0.0010 (14)	0.0041 (13)
C2	0.062 (2)	0.061 (2)	0.0488 (19)	−0.0148 (18)	−0.0021 (16)	−0.0027 (17)
C3	0.087 (3)	0.057 (2)	0.049 (2)	−0.011 (2)	0.012 (2)	−0.0088 (17)
C4	0.070 (3)	0.048 (2)	0.068 (2)	−0.0030 (18)	0.023 (2)	0.0086 (18)
C5	0.049 (2)	0.058 (2)	0.082 (3)	−0.0104 (18)	0.0034 (19)	0.012 (2)
C6	0.054 (2)	0.0417 (18)	0.057 (2)	−0.0135 (15)	0.0006 (16)	0.0043 (15)
C7	0.0451 (18)	0.0475 (18)	0.0533 (19)	−0.0033 (15)	0.0043 (15)	0.0037 (15)
C8	0.055 (2)	0.050 (2)	0.058 (2)	−0.0003 (16)	0.0070 (16)	0.0008 (16)
C9	0.059 (2)	0.0453 (19)	0.070 (2)	−0.0021 (17)	−0.0067 (18)	0.0079 (17)
C10	0.098 (3)	0.072 (3)	0.073 (3)	−0.031 (2)	0.002 (2)	0.020 (2)
C11	0.105 (4)	0.100 (4)	0.061 (3)	−0.034 (3)	0.021 (2)	0.010 (3)
C12	0.069 (2)	0.068 (2)	0.055 (2)	−0.010 (2)	0.0066 (19)	−0.0050 (18)
C13	0.056 (2)	0.058 (2)	0.063 (2)	−0.0245 (17)	−0.0249 (17)	−0.0032 (17)
N1	0.084 (2)	0.0510 (18)	0.0578 (19)	−0.0174 (16)	0.0191 (16)	−0.0079 (14)
O1	0.0540 (15)	0.0750 (18)	0.0794 (18)	−0.0031 (13)	−0.0104 (13)	0.0085 (14)
O2	0.0826 (19)	0.0420 (13)	0.0738 (17)	−0.0038 (12)	0.0094 (14)	0.0032 (11)
Cl1	0.1189 (12)	0.0990 (10)	0.1336 (12)	0.0235 (8)	0.0566 (10)	0.0030 (8)
Cl2	0.1005 (9)	0.0488 (6)	0.1077 (9)	−0.0067 (5)	−0.0032 (7)	−0.0073 (5)
S1	0.0557 (5)	0.0457 (5)	0.0584 (5)	−0.0046 (4)	0.0028 (4)	0.0040 (4)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C8—H8	0.9300
C1—C6	1.399 (5)	C9—C10	1.362 (6)
C1—S1	1.764 (3)	C9—Cl2	1.734 (4)
C2—C3	1.369 (5)	C10—C11	1.384 (6)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.365 (5)	C11—C12	1.366 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.375 (5)	C12—H12	0.9300
C4—Cl1	1.733 (4)	C13—H13A	0.9600
C5—C6	1.386 (5)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—C13	1.571 (5)	N1—S1	1.619 (3)
C7—C12	1.380 (5)	N1—H1N	0.850 (18)
C7—C8	1.380 (5)	O1—S1	1.424 (3)
C7—N1	1.416 (4)	O2—S1	1.436 (2)
C8—C9	1.377 (5)

C2—C1—C6	120.7 (3)	C8—C9—Cl2	118.5 (3)
C2—C1—S1	117.1 (3)	C9—C10—C11	118.4 (4)
C6—C1—S1	122.1 (2)	C9—C10—H10	120.8
C3—C2—C1	120.6 (3)	C11—C10—H10	120.8
C3—C2—H2	119.7	C12—C11—C10	121.0 (4)
C1—C2—H2	119.7	C12—C11—H11	119.5
C4—C3—C2	119.3 (3)	C10—C11—H11	119.5
C4—C3—H3	120.3	C11—C12—C7	119.7 (4)
C2—C3—H3	120.3	C11—C12—H12	120.1
C3—C4—C5	120.6 (4)	C7—C12—H12	120.1
C3—C4—Cl1	119.9 (3)	C6—C13—H13A	109.5
C5—C4—Cl1	119.5 (3)	C6—C13—H13B	109.5
C4—C5—C6	121.8 (4)	H13A—C13—H13B	109.5
C4—C5—H5	119.1	C6—C13—H13C	109.5
C6—C5—H5	119.1	H13A—C13—H13C	109.5
C5—C6—C1	116.9 (3)	H13B—C13—H13C	109.5
C5—C6—C13	120.4 (3)	C7—N1—S1	126.7 (3)
C1—C6—C13	122.7 (3)	C7—N1—H1N	116 (3)
C12—C7—C8	120.2 (3)	S1—N1—H1N	115 (3)
C12—C7—N1	117.0 (3)	O1—S1—O2	118.89 (17)
C8—C7—N1	122.8 (3)	O1—S1—N1	109.67 (17)
C9—C8—C7	118.7 (3)	O2—S1—N1	104.33 (16)
C9—C8—H8	120.7	O1—S1—C1	107.51 (16)
C7—C8—H8	120.7	O2—S1—C1	108.91 (15)
C10—C9—C8	122.1 (4)	N1—S1—C1	106.97 (16)
C10—C9—Cl2	119.4 (3)

C6—C1—C2—C3	0.4 (5)	C8—C9—C10—C11	−0.2 (7)
S1—C1—C2—C3	−179.7 (3)	Cl2—C9—C10—C11	−179.9 (4)
C1—C2—C3—C4	1.2 (5)	C9—C10—C11—C12	−0.4 (7)
C2—C3—C4—C5	−1.0 (5)	C10—C11—C12—C7	0.5 (7)
C2—C3—C4—Cl1	−178.9 (3)	C8—C7—C12—C11	−0.1 (6)
C3—C4—C5—C6	−0.7 (6)	N1—C7—C12—C11	177.6 (4)
Cl1—C4—C5—C6	177.2 (3)	C12—C7—N1—S1	155.4 (3)
C4—C5—C6—C1	2.1 (5)	C8—C7—N1—S1	−27.0 (5)
C4—C5—C6—C13	−177.0 (3)	C7—N1—S1—O1	−36.2 (4)
C2—C1—C6—C5	−2.0 (5)	C7—N1—S1—O2	−164.6 (3)
S1—C1—C6—C5	178.1 (2)	C7—N1—S1—C1	80.1 (3)
C2—C1—C6—C13	177.2 (3)	C2—C1—S1—O1	2.0 (3)
S1—C1—C6—C13	−2.8 (4)	C6—C1—S1—O1	−178.1 (3)
C12—C7—C8—C9	−0.5 (5)	C2—C1—S1—O2	132.0 (3)
N1—C7—C8—C9	−178.1 (3)	C6—C1—S1—O2	−48.0 (3)
C7—C8—C9—C10	0.6 (6)	C2—C1—S1—N1	−115.7 (3)
C7—C8—C9—Cl2	−179.7 (3)	C6—C1—S1—N1	64.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.85 (2)	2.08 (2)	2.926 (4)	175 (4)

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁Cl₂NO₂S
M_r	316.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	7.9757 (7), 11.3472 (8), 15.569 (1)
β (°)	91.490 (8)
V (Å³)	1408.55 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.36 × 0.28 × 0.04

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	0.812, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	5849, 2866, 1853
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.161, 1.04
No. of reflections	2866
No. of parameters	176
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)	0.43, −0.52

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	0.850 (18)	2.08 (2)	2.926 (4)	175 (4)

Symmetry code: (i) −x+1, −y, −z+1.

References

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Volume 66| Part 7| July 2010| Page o1702

doi:10.1107/S1600536810022968

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