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ISSN: 2056-9890

2,4-Di­chloro-N-(3-methyl­phen­yl)benzene­sulfonamide

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 27 May 2010; accepted 27 May 2010; online 5 June 2010)

In the title compound, C13H11Cl2NO2S, the conformations of the N—C bonds in the C—SO2—NH—C segments have gauche torsions with respect to the S=O bonds. The dihedral angle between the two benzene rings is 68.6 (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[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. (2010a[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010a). Acta Cryst. E66, o434.],b[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010b). Acta Cryst. E66, o190.],c[Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010c). Private communication (refcode CCDC 691312). CCDC, Union Road, Cambridge, England.]). 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 = 7.9031 (7) Å

  • b = 14.507 (1) Å

  • c = 12.715 (1) Å

  • β = 99.895 (8)°

  • V = 1436.1 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.59 mm−1

  • T = 299 K

  • 0.36 × 0.24 × 0.20 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 = 0.815, Tmax = 0.891

  • 5737 measured reflections

  • 2915 independent reflections

  • 2389 reflections with I > 2σ(I)

  • Rint = 0.012

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.03

  • 2915 reflections

  • 176 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.85 (1) 2.17 (1) 2.940 (2) 151 (2)
Symmetry code: (i) -x+1, -y+1, -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[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 structures of N-(aryl)arylsulfonamides (Gowda et al. , 2010a,b,c), the structure of 2,4-dichloro-N-(3-methylphenyl)-benzenesulfonamide (I) has been determined. The conformations of the N—C bonds in the C—SO2—NH—C segment have gauche torsions with respect to the SO bonds (Fig. 1).

The molecule is twisted at the S atom with the C1—SO2—NH—C7 torsion angle of -60.2 (2)°, compared to the values of 60.6 (4)°, -59.7 (3)°, 63.9 (4)° and 53.0 (4)°, in the four molecules of 2,4-dichloro-N-(4-methylphenyl)benzenesulfonamide (II) (Gowda et al., 2010b), 55.1 (3)° (molecule 1) and -48.3 (3)° (molecule 2) in 2,4-dichloro-N-(phenyl)-benzenesulfonamide (III) (Gowda et al., 2010c) and 55.8 (2)° and -58.4 (3)°, in the 2 molecules of N-(3-methylphenyl)- benzenesulfonamide (IV) (Gowda et al., 2010a).

The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 68.6 (1)°, compared to the values of 85.2 (1)° (molecule 1), 80.5 (2)° (molecule 2 A), 80.1 (2)° (molecule 2B), 87.5 (7) (molecule 3 A), 87.0 (6)° (molecule 3B) and 72.4 (1)° (molecule 4) in (II), 80.5 (2)° in the molecule 1 and 64.9 (1)° in molecule 2 of (III), and 67.9 (1)° in molecule 1 and 68.6 (1)° in molecule 2 of (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, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers into infinite zigzag sequences running parallel to the c-axis. 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. (2010a,b,c). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-dichlorobenzene (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 2,4-dichlorobenzenesulfonylchloride was treated with m-toluidine 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 2,4-dichloro-N-(3-methylphenyl)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). Prism like colorless 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 (1)Å. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.96Å. 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 labeling 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.
2,4-Dichloro-N-(3-methylphenyl)benzenesulfonamide top
Crystal data top
C13H11Cl2NO2SF(000) = 648
Mr = 316.19Dx = 1.462 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3053 reflections
a = 7.9031 (7) Åθ = 2.6–27.8°
b = 14.507 (1) ŵ = 0.59 mm1
c = 12.715 (1) ÅT = 299 K
β = 99.895 (8)°Prism, colorless
V = 1436.1 (2) Å30.36 × 0.24 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2915 independent reflections
Radiation source: fine-focus sealed tube2389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Rotation method data acquisition using ω and phi scans.θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 97
Tmin = 0.815, Tmax = 0.891k = 1815
5737 measured reflectionsl = 1415
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0451P)2 + 0.717P]
where P = (Fo2 + 2Fc2)/3
2915 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.41 e Å3
1 restraintΔρmin = 0.49 e Å3
Crystal data top
C13H11Cl2NO2SV = 1436.1 (2) Å3
Mr = 316.19Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.9031 (7) ŵ = 0.59 mm1
b = 14.507 (1) ÅT = 299 K
c = 12.715 (1) Å0.36 × 0.24 × 0.20 mm
β = 99.895 (8)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2915 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2389 reflections with I > 2σ(I)
Tmin = 0.815, Tmax = 0.891Rint = 0.012
5737 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0371 restraint
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.41 e Å3
2915 reflectionsΔρmin = 0.49 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
C10.6418 (2)0.33869 (13)0.20486 (15)0.0350 (4)
C20.8068 (2)0.36037 (14)0.18846 (16)0.0402 (4)
C30.9482 (3)0.31950 (15)0.24999 (18)0.0509 (5)
H31.05860.33360.23890.061*
C40.9232 (3)0.25777 (15)0.32759 (18)0.0520 (5)
C50.7617 (3)0.23604 (15)0.34720 (17)0.0502 (5)
H50.74750.19480.40100.060*
C60.6213 (3)0.27706 (14)0.28493 (16)0.0420 (4)
H60.51140.26310.29700.050*
C70.4604 (3)0.53438 (14)0.24891 (17)0.0442 (5)
C80.3109 (3)0.53560 (16)0.2914 (2)0.0549 (6)
H80.21170.50890.25380.066*
C90.3078 (4)0.57624 (18)0.3896 (2)0.0714 (8)
C100.4569 (5)0.6157 (2)0.4429 (2)0.0811 (9)
H100.45700.64280.50920.097*
C110.6042 (4)0.6158 (2)0.4005 (2)0.0768 (8)
H110.70260.64390.43730.092*
C120.6080 (3)0.57441 (17)0.3031 (2)0.0589 (6)
H120.70870.57360.27450.071*
C130.1436 (6)0.5793 (3)0.4345 (4)0.1194 (15)
H13A0.06570.53340.40000.143*
H13B0.09220.63920.42230.143*
H13C0.16820.56720.50980.143*
N10.4582 (2)0.49567 (12)0.14485 (14)0.0433 (4)
H1N0.516 (3)0.5237 (15)0.1041 (16)0.052*
O10.46312 (19)0.37240 (11)0.01548 (11)0.0509 (4)
O20.31399 (17)0.34804 (11)0.16821 (13)0.0538 (4)
S10.45443 (6)0.38552 (3)0.12621 (4)0.03929 (14)
Cl10.84366 (7)0.44023 (5)0.09354 (5)0.06074 (19)
Cl21.10203 (10)0.20696 (6)0.40428 (7)0.0889 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0317 (9)0.0341 (9)0.0383 (10)0.0004 (7)0.0031 (7)0.0038 (8)
C20.0354 (9)0.0417 (10)0.0439 (11)0.0010 (8)0.0076 (8)0.0012 (8)
C30.0337 (10)0.0520 (12)0.0659 (14)0.0041 (9)0.0056 (9)0.0013 (11)
C40.0461 (12)0.0456 (12)0.0579 (13)0.0081 (9)0.0093 (10)0.0004 (10)
C50.0605 (13)0.0409 (11)0.0462 (12)0.0013 (10)0.0006 (10)0.0059 (9)
C60.0418 (10)0.0390 (10)0.0448 (11)0.0047 (8)0.0068 (8)0.0016 (8)
C70.0510 (12)0.0348 (10)0.0459 (11)0.0067 (9)0.0059 (9)0.0047 (9)
C80.0598 (14)0.0464 (12)0.0615 (14)0.0002 (10)0.0194 (11)0.0008 (11)
C90.100 (2)0.0550 (15)0.0682 (17)0.0041 (14)0.0391 (16)0.0008 (13)
C100.126 (3)0.0642 (17)0.0560 (16)0.0059 (18)0.0231 (17)0.0095 (14)
C110.093 (2)0.0638 (17)0.0661 (17)0.0007 (15)0.0074 (16)0.0131 (14)
C120.0566 (14)0.0536 (13)0.0639 (15)0.0025 (11)0.0033 (11)0.0041 (11)
C130.143 (4)0.114 (3)0.125 (3)0.007 (3)0.089 (3)0.019 (2)
N10.0453 (9)0.0410 (9)0.0441 (10)0.0038 (7)0.0092 (7)0.0050 (7)
O10.0512 (9)0.0578 (9)0.0401 (8)0.0029 (7)0.0021 (6)0.0060 (7)
O20.0320 (7)0.0580 (9)0.0711 (10)0.0050 (7)0.0083 (7)0.0028 (8)
S10.0313 (2)0.0429 (3)0.0420 (3)0.00170 (19)0.00161 (18)0.0009 (2)
Cl10.0471 (3)0.0713 (4)0.0669 (4)0.0056 (3)0.0187 (3)0.0193 (3)
Cl20.0670 (4)0.0819 (5)0.1043 (6)0.0210 (4)0.0233 (4)0.0194 (4)
Geometric parameters (Å, º) top
C1—C61.385 (3)C8—H80.9300
C1—C21.392 (3)C9—C101.379 (5)
C1—S11.7734 (18)C9—C131.505 (4)
C2—C31.383 (3)C10—C111.365 (5)
C2—Cl11.733 (2)C10—H100.9300
C3—C41.372 (3)C11—C121.381 (4)
C3—H30.9300C11—H110.9300
C4—C51.379 (3)C12—H120.9300
C4—Cl21.737 (2)C13—H13A0.9600
C5—C61.382 (3)C13—H13B0.9600
C5—H50.9300C13—H13C0.9600
C6—H60.9300N1—S11.6150 (18)
C7—C121.377 (3)N1—H1N0.852 (10)
C7—C81.381 (3)O1—S11.4340 (15)
C7—N11.435 (3)O2—S11.4201 (15)
C8—C91.385 (4)
C6—C1—C2119.14 (17)C8—C9—C13120.3 (3)
C6—C1—S1118.04 (14)C11—C10—C9121.4 (3)
C2—C1—S1122.82 (15)C11—C10—H10119.3
C3—C2—C1120.37 (19)C9—C10—H10119.3
C3—C2—Cl1117.66 (16)C10—C11—C12120.3 (3)
C1—C2—Cl1121.96 (15)C10—C11—H11119.8
C4—C3—C2118.96 (19)C12—C11—H11119.8
C4—C3—H3120.5C7—C12—C11119.0 (3)
C2—C3—H3120.5C7—C12—H12120.5
C3—C4—C5122.14 (19)C11—C12—H12120.5
C3—C4—Cl2118.47 (18)C9—C13—H13A109.5
C5—C4—Cl2119.39 (18)C9—C13—H13B109.5
C4—C5—C6118.4 (2)H13A—C13—H13B109.5
C4—C5—H5120.8C9—C13—H13C109.5
C6—C5—H5120.8H13A—C13—H13C109.5
C5—C6—C1121.01 (19)H13B—C13—H13C109.5
C5—C6—H6119.5C7—N1—S1121.30 (14)
C1—C6—H6119.5C7—N1—H1N116.9 (16)
C12—C7—C8120.5 (2)S1—N1—H1N112.4 (16)
C12—C7—N1120.1 (2)O2—S1—O1119.39 (9)
C8—C7—N1119.3 (2)O2—S1—N1108.64 (9)
C7—C8—C9120.5 (3)O1—S1—N1105.82 (9)
C7—C8—H8119.8O2—S1—C1105.78 (9)
C9—C8—H8119.8O1—S1—C1109.07 (9)
C10—C9—C8118.3 (3)N1—S1—C1107.68 (9)
C10—C9—C13121.4 (3)
C6—C1—C2—C31.2 (3)C8—C9—C10—C110.6 (4)
S1—C1—C2—C3177.90 (16)C13—C9—C10—C11177.7 (3)
C6—C1—C2—Cl1177.39 (15)C9—C10—C11—C121.3 (5)
S1—C1—C2—Cl13.5 (2)C8—C7—C12—C110.0 (4)
C1—C2—C3—C40.3 (3)N1—C7—C12—C11176.4 (2)
Cl1—C2—C3—C4178.37 (17)C10—C11—C12—C71.0 (4)
C2—C3—C4—C50.9 (3)C12—C7—N1—S1107.6 (2)
C2—C3—C4—Cl2180.00 (17)C8—C7—N1—S176.0 (2)
C3—C4—C5—C61.1 (3)C7—N1—S1—O253.93 (18)
Cl2—C4—C5—C6179.77 (16)C7—N1—S1—O1176.73 (15)
C4—C5—C6—C10.1 (3)C7—N1—S1—C160.20 (18)
C2—C1—C6—C51.0 (3)C6—C1—S1—O21.58 (18)
S1—C1—C6—C5178.18 (16)C2—C1—S1—O2179.27 (16)
C12—C7—C8—C90.7 (3)C6—C1—S1—O1128.01 (16)
N1—C7—C8—C9177.1 (2)C2—C1—S1—O151.14 (18)
C7—C8—C9—C100.4 (4)C6—C1—S1—N1117.60 (16)
C7—C8—C9—C13178.6 (3)C2—C1—S1—N163.25 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.85 (1)2.17 (1)2.940 (2)151 (2)
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H11Cl2NO2S
Mr316.19
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)7.9031 (7), 14.507 (1), 12.715 (1)
β (°) 99.895 (8)
V3)1436.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.36 × 0.24 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.815, 0.891
No. of measured, independent and
observed [I > 2σ(I)] reflections
5737, 2915, 2389
Rint0.012
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.097, 1.03
No. of reflections2915
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.41, 0.49

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···O1i0.852 (10)2.166 (14)2.940 (2)151 (2)
Symmetry code: (i) x+1, y+1, z.
 

References

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