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ISSN: 2056-9890

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

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[Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600-606.]). For our studies of the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Babitha, K. S. & Fuess, H. (2008). Acta Cryst. E64, o1825.], 2009a[Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o476.],b[Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009b). Acta Cryst. E65, o717.]). For related structures, see: Gelbrich et al. (2007[Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621-632.]); Perlovich et al. (2006[Perlovich, G. L., Tkachev, V. V., Schaper, K.-J. & Raevsky, O. A. (2006). Acta Cryst. E62, o780-o782.]).

[Scheme 1]

Experimental

Crystal data
  • C13H11Cl2NO2S

  • Mr = 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.]) Tmin = 0.812, Tmax = 0.976

  • 5849 measured reflections

  • 2866 independent reflections

  • 1853 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (2) Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

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
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
4-Chloro-N-(3-chlorophenyl)-2-methylbenzenesulfonamide top
Crystal data top
C13H11Cl2NO2SF(000) = 648
Mr = 316.19Dx = 1.491 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2107 reflections
a = 7.9757 (7) Åθ = 2.6–27.8°
b = 11.3472 (8) ŵ = 0.61 mm1
c = 15.569 (1) ÅT = 299 K
β = 91.490 (8)°Plate, colourless
V = 1408.55 (18) Å30.36 × 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 tube1853 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Rotation method data acquisition using ω and phi scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 97
Tmin = 0.812, Tmax = 0.976k = 1414
5849 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0763P)2 + 0.8836P]
where P = (Fo2 + 2Fc2)/3
2866 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.43 e Å3
1 restraintΔρmin = 0.52 e Å3
Crystal data top
C13H11Cl2NO2SV = 1408.55 (18) Å3
Mr = 316.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9757 (7) ŵ = 0.61 mm1
b = 11.3472 (8) ÅT = 299 K
c = 15.569 (1) Å0.36 × 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)
Tmin = 0.812, Tmax = 0.976Rint = 0.017
5849 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.43 e Å3
2866 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/Ueq
C10.3431 (4)0.2031 (3)0.66150 (19)0.0451 (7)
C20.3719 (5)0.2761 (3)0.7319 (2)0.0571 (9)
H20.47930.28180.75630.069*
C30.2436 (6)0.3398 (3)0.7657 (2)0.0642 (10)
H30.26380.38970.81220.077*
C40.0858 (5)0.3293 (3)0.7305 (2)0.0617 (10)
C50.0557 (5)0.2571 (3)0.6608 (3)0.0630 (10)
H50.05300.25070.63830.076*
C60.1829 (4)0.1936 (3)0.6234 (2)0.0508 (8)
C70.6346 (4)0.2765 (3)0.5046 (2)0.0486 (8)
C80.6426 (4)0.3741 (3)0.5575 (2)0.0543 (8)
H80.59400.37290.61110.065*
C90.7240 (5)0.4732 (3)0.5292 (2)0.0585 (9)
C100.7951 (6)0.4781 (4)0.4506 (3)0.0809 (13)
H100.84920.54590.43250.097*
C110.7847 (6)0.3796 (4)0.3983 (3)0.0887 (15)
H110.83190.38150.34440.106*
C120.7061 (5)0.2795 (4)0.4249 (2)0.0641 (10)
H120.70070.21370.38930.077*
C130.1457 (5)0.1168 (3)0.5412 (2)0.0595 (10)
H13A0.18070.03710.55190.071*
H13B0.20600.14810.49370.071*
H13C0.02760.11820.52760.071*
N10.5495 (4)0.1719 (3)0.5270 (2)0.0640 (9)
H1N0.539 (5)0.120 (3)0.488 (2)0.077*
O10.6571 (3)0.1510 (2)0.67778 (17)0.0697 (7)
O20.4690 (3)0.0031 (2)0.61100 (16)0.0660 (7)
Cl10.0771 (2)0.41129 (13)0.77137 (10)0.1162 (6)
Cl20.73479 (16)0.59549 (9)0.59594 (8)0.0858 (4)
S10.51639 (11)0.12421 (7)0.62307 (6)0.0533 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0512 (19)0.0407 (16)0.0432 (17)0.0108 (14)0.0010 (14)0.0041 (13)
C20.062 (2)0.061 (2)0.0488 (19)0.0148 (18)0.0021 (16)0.0027 (17)
C30.087 (3)0.057 (2)0.049 (2)0.011 (2)0.012 (2)0.0088 (17)
C40.070 (3)0.048 (2)0.068 (2)0.0030 (18)0.023 (2)0.0086 (18)
C50.049 (2)0.058 (2)0.082 (3)0.0104 (18)0.0034 (19)0.012 (2)
C60.054 (2)0.0417 (18)0.057 (2)0.0135 (15)0.0006 (16)0.0043 (15)
C70.0451 (18)0.0475 (18)0.0533 (19)0.0033 (15)0.0043 (15)0.0037 (15)
C80.055 (2)0.050 (2)0.058 (2)0.0003 (16)0.0070 (16)0.0008 (16)
C90.059 (2)0.0453 (19)0.070 (2)0.0021 (17)0.0067 (18)0.0079 (17)
C100.098 (3)0.072 (3)0.073 (3)0.031 (2)0.002 (2)0.020 (2)
C110.105 (4)0.100 (4)0.061 (3)0.034 (3)0.021 (2)0.010 (3)
C120.069 (2)0.068 (2)0.055 (2)0.010 (2)0.0066 (19)0.0050 (18)
C130.056 (2)0.058 (2)0.063 (2)0.0245 (17)0.0249 (17)0.0032 (17)
N10.084 (2)0.0510 (18)0.0578 (19)0.0174 (16)0.0191 (16)0.0079 (14)
O10.0540 (15)0.0750 (18)0.0794 (18)0.0031 (13)0.0104 (13)0.0085 (14)
O20.0826 (19)0.0420 (13)0.0738 (17)0.0038 (12)0.0094 (14)0.0032 (11)
Cl10.1189 (12)0.0990 (10)0.1336 (12)0.0235 (8)0.0566 (10)0.0030 (8)
Cl20.1005 (9)0.0488 (6)0.1077 (9)0.0067 (5)0.0032 (7)0.0073 (5)
S10.0557 (5)0.0457 (5)0.0584 (5)0.0046 (4)0.0028 (4)0.0040 (4)
Geometric parameters (Å, º) top
C1—C21.388 (4)C8—H80.9300
C1—C61.399 (5)C9—C101.362 (6)
C1—S11.764 (3)C9—Cl21.734 (4)
C2—C31.369 (5)C10—C111.384 (6)
C2—H20.9300C10—H100.9300
C3—C41.365 (5)C11—C121.366 (5)
C3—H30.9300C11—H110.9300
C4—C51.375 (5)C12—H120.9300
C4—Cl11.733 (4)C13—H13A0.9600
C5—C61.386 (5)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—C131.571 (5)N1—S11.619 (3)
C7—C121.380 (5)N1—H1N0.850 (18)
C7—C81.380 (5)O1—S11.424 (3)
C7—N11.416 (4)O2—S11.436 (2)
C8—C91.377 (5)
C2—C1—C6120.7 (3)C8—C9—Cl2118.5 (3)
C2—C1—S1117.1 (3)C9—C10—C11118.4 (4)
C6—C1—S1122.1 (2)C9—C10—H10120.8
C3—C2—C1120.6 (3)C11—C10—H10120.8
C3—C2—H2119.7C12—C11—C10121.0 (4)
C1—C2—H2119.7C12—C11—H11119.5
C4—C3—C2119.3 (3)C10—C11—H11119.5
C4—C3—H3120.3C11—C12—C7119.7 (4)
C2—C3—H3120.3C11—C12—H12120.1
C3—C4—C5120.6 (4)C7—C12—H12120.1
C3—C4—Cl1119.9 (3)C6—C13—H13A109.5
C5—C4—Cl1119.5 (3)C6—C13—H13B109.5
C4—C5—C6121.8 (4)H13A—C13—H13B109.5
C4—C5—H5119.1C6—C13—H13C109.5
C6—C5—H5119.1H13A—C13—H13C109.5
C5—C6—C1116.9 (3)H13B—C13—H13C109.5
C5—C6—C13120.4 (3)C7—N1—S1126.7 (3)
C1—C6—C13122.7 (3)C7—N1—H1N116 (3)
C12—C7—C8120.2 (3)S1—N1—H1N115 (3)
C12—C7—N1117.0 (3)O1—S1—O2118.89 (17)
C8—C7—N1122.8 (3)O1—S1—N1109.67 (17)
C9—C8—C7118.7 (3)O2—S1—N1104.33 (16)
C9—C8—H8120.7O1—S1—C1107.51 (16)
C7—C8—H8120.7O2—S1—C1108.91 (15)
C10—C9—C8122.1 (4)N1—S1—C1106.97 (16)
C10—C9—Cl2119.4 (3)
C6—C1—C2—C30.4 (5)C8—C9—C10—C110.2 (7)
S1—C1—C2—C3179.7 (3)Cl2—C9—C10—C11179.9 (4)
C1—C2—C3—C41.2 (5)C9—C10—C11—C120.4 (7)
C2—C3—C4—C51.0 (5)C10—C11—C12—C70.5 (7)
C2—C3—C4—Cl1178.9 (3)C8—C7—C12—C110.1 (6)
C3—C4—C5—C60.7 (6)N1—C7—C12—C11177.6 (4)
Cl1—C4—C5—C6177.2 (3)C12—C7—N1—S1155.4 (3)
C4—C5—C6—C12.1 (5)C8—C7—N1—S127.0 (5)
C4—C5—C6—C13177.0 (3)C7—N1—S1—O136.2 (4)
C2—C1—C6—C52.0 (5)C7—N1—S1—O2164.6 (3)
S1—C1—C6—C5178.1 (2)C7—N1—S1—C180.1 (3)
C2—C1—C6—C13177.2 (3)C2—C1—S1—O12.0 (3)
S1—C1—C6—C132.8 (4)C6—C1—S1—O1178.1 (3)
C12—C7—C8—C90.5 (5)C2—C1—S1—O2132.0 (3)
N1—C7—C8—C9178.1 (3)C6—C1—S1—O248.0 (3)
C7—C8—C9—C100.6 (6)C2—C1—S1—N1115.7 (3)
C7—C8—C9—Cl2179.7 (3)C6—C1—S1—N164.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.85 (2)2.08 (2)2.926 (4)175 (4)
Symmetry code: (i) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC13H11Cl2NO2S
Mr316.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)7.9757 (7), 11.3472 (8), 15.569 (1)
β (°) 91.490 (8)
V3)1408.55 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.61
Crystal size (mm)0.36 × 0.28 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.812, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
5849, 2866, 1853
Rint0.017
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.161, 1.04
No. of reflections2866
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1N···O2i0.850 (18)2.08 (2)2.926 (4)175 (4)
Symmetry code: (i) x+1, y, z+1.
 

References

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First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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