organic compounds
N-(2-Chlorophenyl)-2,4-dimethylbenzenesulfonamide
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
In the title compound, C14H14ClNO2S, the conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S=O bonds. The molecule is bent at the S atom with a C—SO2—NH—C torsion angle of −54.9 (2)°. The sulfonyl and aniline benzene rings are rotated relative to each other by 75.7 (1)°. An intramolecular N—H⋯Cl hydrogen bond is present. In the crystal, intermolecular N—H⋯O hydrogen-bonding interactions are observed and the molecules are packed into chains parallel to the b axis.
Related literature
For the preparation of the title compound, see: Savitha & Gowda (2006). For related structures, see: Gelbrich et al. (2007); Gowda et al. (2009a,b, 2010); Nirmala et al. (2009); Perlovich et al. (2006).
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis RED (Oxford Diffraction, 2009); 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
https://doi.org/10.1107/S1600536810015916/rz2441sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015916/rz2441Isup2.hkl
A solution of 1,3-xylene (1,3-dimethylbenzene) (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 2,4-dimethylbenzenesulfonylchloride was treated with 2-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 2,4-dimethyl-N-(2-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 prism like colourless single crystals used in X-ray diffraction studies were grown by slow evaporation of an ethanol solution at room temperature.
The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (1) %A. 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).
As part of a study of the substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al. , 2009a,b, 2010), in the present work the structure of 2,4-dimethyl-N-(2-chlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is bent at the S atom with the C1—SO2—NH—C7 torsion angle of -54.9 (2)°, compared to the values of 71.6 (1)° in 2,4-dimethyl-N-(2-methylphenyl)benzenesulfonamide (II) (Nirmala et al., 2009), 74.8 (4)° in 4-chloro-2-methyl-N-(2-chlorophenyl)benzenesulfonamide (III) (Gowda et al., 2009b), -46.1 (3)° (molecule 1) and 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV) (Gowda et al., 2009a) and -54.8 (2)° in N-(2-chlorophenyl)-4-methylbenzenesulfonamide (V) (Gowda et al., 2010).
The two benzene rings in (I) are tilted relative to each other by 75.7 (1)°, compared to the values of 47.0 (1)° (II), 45.5 (2)° in (III), 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (IV), and 71.6 (1)° in (V). The other bond parameters in (I) are similar to those observed in (II), (III), (IV), (V) and other aryl
(Perlovich et al., 2006; Gelbrich et al., 2007).The structure shows simultaneous N—H···Cl intramolecular and N—H···O intermolecular H-bonding (Table 1). The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds is shown in Fig.2.
For the preparation of the title compound, see: Savitha & Gowda (2006). For related structures, see: Gelbrich et al. (2007); Gowda et al. (2009a,b, 2010); Nirmala et al. (2009); Perlovich et al. (2006)
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
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).C14H14ClNO2S | F(000) = 1232 |
Mr = 295.77 | Dx = 1.355 Mg m−3 |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 2348 reflections |
a = 10.574 (1) Å | θ = 2.6–27.8° |
b = 16.269 (2) Å | µ = 0.40 mm−1 |
c = 16.859 (2) Å | T = 299 K |
V = 2900.2 (6) Å3 | Prism, colourless |
Z = 8 | 0.38 × 0.34 × 0.24 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2922 independent reflections |
Radiation source: fine-focus sealed tube | 2330 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
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 = −8→13 |
Tmin = 0.862, Tmax = 0.909 | k = −19→19 |
18999 measured reflections | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0452P)2 + 1.1956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.003 |
2922 reflections | Δρmax = 0.23 e Å−3 |
178 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0063 (6) |
C14H14ClNO2S | V = 2900.2 (6) Å3 |
Mr = 295.77 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 10.574 (1) Å | µ = 0.40 mm−1 |
b = 16.269 (2) Å | T = 299 K |
c = 16.859 (2) Å | 0.38 × 0.34 × 0.24 mm |
Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector | 2922 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 2330 reflections with I > 2σ(I) |
Tmin = 0.862, Tmax = 0.909 | Rint = 0.026 |
18999 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 1 restraint |
wR(F2) = 0.102 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.23 e Å−3 |
2922 reflections | Δρmin = −0.27 e Å−3 |
178 parameters |
Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.31380 (18) | 0.39372 (11) | 0.32739 (11) | 0.0470 (4) | |
C2 | 0.2828 (2) | 0.47702 (12) | 0.31522 (12) | 0.0543 (5) | |
C3 | 0.3721 (2) | 0.53467 (14) | 0.33864 (15) | 0.0707 (6) | |
H3 | 0.3530 | 0.5900 | 0.3318 | 0.085* | |
C4 | 0.4873 (3) | 0.51455 (17) | 0.37137 (16) | 0.0809 (7) | |
C5 | 0.5148 (3) | 0.43261 (18) | 0.38187 (19) | 0.0872 (8) | |
H5 | 0.5921 | 0.4175 | 0.4038 | 0.105* | |
C6 | 0.4290 (2) | 0.37243 (15) | 0.36013 (15) | 0.0670 (6) | |
H6 | 0.4490 | 0.3173 | 0.3676 | 0.080* | |
C7 | 0.10341 (18) | 0.31392 (11) | 0.44692 (10) | 0.0465 (4) | |
C8 | 0.0207 (2) | 0.35953 (11) | 0.49298 (11) | 0.0499 (5) | |
C9 | 0.0269 (3) | 0.35663 (14) | 0.57551 (12) | 0.0660 (6) | |
H9 | −0.0305 | 0.3863 | 0.6059 | 0.079* | |
C10 | 0.1184 (3) | 0.30960 (14) | 0.61177 (12) | 0.0712 (7) | |
H10 | 0.1237 | 0.3083 | 0.6668 | 0.085* | |
C11 | 0.2011 (3) | 0.26496 (15) | 0.56722 (13) | 0.0687 (6) | |
H11 | 0.2633 | 0.2338 | 0.5921 | 0.082* | |
C12 | 0.1932 (2) | 0.26568 (14) | 0.48522 (12) | 0.0629 (6) | |
H12 | 0.2485 | 0.2336 | 0.4555 | 0.076* | |
C13 | 0.1609 (2) | 0.50496 (15) | 0.27754 (16) | 0.0766 (7) | |
H13A | 0.0907 | 0.4846 | 0.3078 | 0.092* | |
H13B | 0.1560 | 0.4841 | 0.2244 | 0.092* | |
H13C | 0.1583 | 0.5639 | 0.2764 | 0.092* | |
C14 | 0.5812 (3) | 0.5810 (2) | 0.3941 (3) | 0.1248 (13) | |
H14A | 0.5396 | 0.6217 | 0.4260 | 0.150* | |
H14B | 0.6140 | 0.6063 | 0.3470 | 0.150* | |
H14C | 0.6494 | 0.5570 | 0.4237 | 0.150* | |
N1 | 0.09250 (16) | 0.31599 (11) | 0.36289 (9) | 0.0538 (4) | |
H1N | 0.0245 (14) | 0.3331 (13) | 0.3411 (12) | 0.065* | |
O1 | 0.15450 (14) | 0.32896 (10) | 0.22493 (7) | 0.0610 (4) | |
O2 | 0.27871 (14) | 0.23745 (8) | 0.31126 (9) | 0.0625 (4) | |
Cl1 | −0.09351 (6) | 0.42128 (4) | 0.44867 (3) | 0.0714 (2) | |
S1 | 0.21116 (5) | 0.31295 (3) | 0.30076 (3) | 0.04739 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0497 (11) | 0.0479 (10) | 0.0435 (9) | 0.0042 (8) | 0.0033 (8) | −0.0029 (8) |
C2 | 0.0586 (12) | 0.0515 (11) | 0.0528 (11) | 0.0071 (9) | 0.0096 (9) | −0.0013 (9) |
C3 | 0.0839 (17) | 0.0502 (12) | 0.0779 (16) | −0.0034 (12) | 0.0141 (14) | −0.0051 (11) |
C4 | 0.0782 (17) | 0.0775 (17) | 0.0872 (18) | −0.0189 (14) | −0.0004 (15) | −0.0105 (14) |
C5 | 0.0599 (14) | 0.0923 (19) | 0.109 (2) | −0.0086 (14) | −0.0208 (15) | 0.0019 (16) |
C6 | 0.0587 (13) | 0.0597 (13) | 0.0825 (16) | 0.0057 (11) | −0.0130 (12) | 0.0024 (11) |
C7 | 0.0548 (11) | 0.0488 (10) | 0.0358 (9) | −0.0121 (9) | −0.0039 (8) | 0.0009 (8) |
C8 | 0.0643 (12) | 0.0432 (9) | 0.0423 (9) | −0.0129 (9) | −0.0035 (9) | −0.0022 (8) |
C9 | 0.0950 (18) | 0.0603 (13) | 0.0428 (11) | −0.0148 (12) | 0.0070 (11) | −0.0098 (9) |
C10 | 0.112 (2) | 0.0645 (14) | 0.0372 (10) | −0.0271 (14) | −0.0138 (12) | 0.0084 (10) |
C11 | 0.0886 (17) | 0.0681 (14) | 0.0494 (12) | −0.0103 (13) | −0.0191 (12) | 0.0122 (10) |
C12 | 0.0715 (14) | 0.0687 (14) | 0.0487 (11) | 0.0044 (11) | −0.0093 (10) | 0.0056 (10) |
C13 | 0.0767 (16) | 0.0623 (14) | 0.0907 (18) | 0.0212 (13) | −0.0013 (14) | 0.0076 (12) |
C14 | 0.110 (3) | 0.110 (3) | 0.154 (3) | −0.048 (2) | −0.006 (2) | −0.023 (2) |
N1 | 0.0493 (10) | 0.0769 (12) | 0.0352 (8) | 0.0021 (9) | −0.0043 (7) | 0.0025 (8) |
O1 | 0.0647 (9) | 0.0840 (10) | 0.0342 (7) | 0.0007 (8) | −0.0022 (6) | −0.0054 (6) |
O2 | 0.0747 (10) | 0.0478 (8) | 0.0650 (9) | 0.0094 (7) | −0.0006 (8) | −0.0098 (6) |
Cl1 | 0.0827 (4) | 0.0706 (4) | 0.0610 (3) | 0.0138 (3) | −0.0051 (3) | −0.0124 (3) |
S1 | 0.0538 (3) | 0.0511 (3) | 0.0372 (2) | 0.0036 (2) | −0.0007 (2) | −0.00583 (18) |
C1—C6 | 1.381 (3) | C9—C10 | 1.376 (3) |
C1—C2 | 1.409 (3) | C9—H9 | 0.9300 |
C1—S1 | 1.7624 (19) | C10—C11 | 1.363 (3) |
C2—C3 | 1.388 (3) | C10—H10 | 0.9300 |
C2—C13 | 1.508 (3) | C11—C12 | 1.385 (3) |
C3—C4 | 1.377 (4) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.376 (4) | C13—H13A | 0.9600 |
C4—C14 | 1.518 (4) | C13—H13B | 0.9600 |
C5—C6 | 1.385 (3) | C13—H13C | 0.9600 |
C5—H5 | 0.9300 | C14—H14A | 0.9600 |
C6—H6 | 0.9300 | C14—H14B | 0.9600 |
C7—C8 | 1.385 (3) | C14—H14C | 0.9600 |
C7—C12 | 1.391 (3) | N1—S1 | 1.6352 (17) |
C7—N1 | 1.422 (2) | N1—H1N | 0.854 (9) |
C8—C9 | 1.394 (3) | O1—S1 | 1.4357 (14) |
C8—Cl1 | 1.739 (2) | O2—S1 | 1.4319 (14) |
C6—C1—C2 | 120.29 (19) | C9—C10—H10 | 119.9 |
C6—C1—S1 | 117.24 (16) | C10—C11—C12 | 120.5 (2) |
C2—C1—S1 | 122.47 (15) | C10—C11—H11 | 119.8 |
C3—C2—C1 | 116.8 (2) | C12—C11—H11 | 119.8 |
C3—C2—C13 | 119.8 (2) | C11—C12—C7 | 120.6 (2) |
C1—C2—C13 | 123.37 (19) | C11—C12—H12 | 119.7 |
C4—C3—C2 | 123.7 (2) | C7—C12—H12 | 119.7 |
C4—C3—H3 | 118.1 | C2—C13—H13A | 109.5 |
C2—C3—H3 | 118.1 | C2—C13—H13B | 109.5 |
C5—C4—C3 | 118.0 (2) | H13A—C13—H13B | 109.5 |
C5—C4—C14 | 121.3 (3) | C2—C13—H13C | 109.5 |
C3—C4—C14 | 120.7 (3) | H13A—C13—H13C | 109.5 |
C4—C5—C6 | 120.8 (2) | H13B—C13—H13C | 109.5 |
C4—C5—H5 | 119.6 | C4—C14—H14A | 109.5 |
C6—C5—H5 | 119.6 | C4—C14—H14B | 109.5 |
C1—C6—C5 | 120.4 (2) | H14A—C14—H14B | 109.5 |
C1—C6—H6 | 119.8 | C4—C14—H14C | 109.5 |
C5—C6—H6 | 119.8 | H14A—C14—H14C | 109.5 |
C8—C7—C12 | 118.24 (17) | H14B—C14—H14C | 109.5 |
C8—C7—N1 | 119.64 (17) | C7—N1—S1 | 125.12 (14) |
C12—C7—N1 | 122.10 (18) | C7—N1—H1N | 120.3 (16) |
C7—C8—C9 | 120.8 (2) | S1—N1—H1N | 112.4 (15) |
C7—C8—Cl1 | 120.47 (14) | O2—S1—O1 | 118.28 (9) |
C9—C8—Cl1 | 118.77 (17) | O2—S1—N1 | 109.24 (9) |
C10—C9—C8 | 119.7 (2) | O1—S1—N1 | 104.16 (9) |
C10—C9—H9 | 120.1 | O2—S1—C1 | 107.52 (9) |
C8—C9—H9 | 120.1 | O1—S1—C1 | 110.40 (9) |
C11—C10—C9 | 120.2 (2) | N1—S1—C1 | 106.67 (9) |
C11—C10—H10 | 119.9 | ||
C6—C1—C2—C3 | −0.9 (3) | Cl1—C8—C9—C10 | −178.55 (16) |
S1—C1—C2—C3 | −179.84 (16) | C8—C9—C10—C11 | −1.1 (3) |
C6—C1—C2—C13 | 178.1 (2) | C9—C10—C11—C12 | −0.7 (4) |
S1—C1—C2—C13 | −0.9 (3) | C10—C11—C12—C7 | 2.0 (4) |
C1—C2—C3—C4 | 0.9 (3) | C8—C7—C12—C11 | −1.4 (3) |
C13—C2—C3—C4 | −178.1 (2) | N1—C7—C12—C11 | −179.9 (2) |
C2—C3—C4—C5 | −0.5 (4) | C8—C7—N1—S1 | 144.02 (16) |
C2—C3—C4—C14 | 178.8 (3) | C12—C7—N1—S1 | −37.6 (3) |
C3—C4—C5—C6 | 0.0 (4) | C7—N1—S1—O2 | 61.07 (19) |
C14—C4—C5—C6 | −179.3 (3) | C7—N1—S1—O1 | −171.66 (16) |
C2—C1—C6—C5 | 0.5 (3) | C7—N1—S1—C1 | −54.86 (19) |
S1—C1—C6—C5 | 179.5 (2) | C6—C1—S1—O2 | −6.68 (19) |
C4—C5—C6—C1 | 0.0 (4) | C2—C1—S1—O2 | 172.29 (15) |
C12—C7—C8—C9 | −0.4 (3) | C6—C1—S1—O1 | −137.03 (17) |
N1—C7—C8—C9 | 178.06 (18) | C2—C1—S1—O1 | 41.94 (19) |
C12—C7—C8—Cl1 | 179.82 (15) | C6—C1—S1—N1 | 110.40 (17) |
N1—C7—C8—Cl1 | −1.7 (2) | C2—C1—S1—N1 | −70.63 (18) |
C7—C8—C9—C10 | 1.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.85 (1) | 2.20 (1) | 3.010 (2) | 159 (2) |
N1—H1N···Cl1 | 0.85 (1) | 2.63 (2) | 2.9822 (18) | 106 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H14ClNO2S |
Mr | 295.77 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 299 |
a, b, c (Å) | 10.574 (1), 16.269 (2), 16.859 (2) |
V (Å3) | 2900.2 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.38 × 0.34 × 0.24 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.862, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18999, 2922, 2330 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.102, 1.05 |
No. of reflections | 2922 |
No. of parameters | 178 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.27 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.854 (9) | 2.197 (12) | 3.010 (2) | 159 (2) |
N1—H1N···Cl1 | 0.854 (9) | 2.63 (2) | 2.9822 (18) | 106.3 (17) |
Symmetry code: (i) −x, y, −z+1/2. |
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., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009a). Acta Cryst. E65, o576. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Babitha, K. S. & Fuess, H. (2009b). Acta Cryst. E65, o717. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o188. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nirmala, P. G., Gowda, B. T., Foro, S. & Fuess, H. (2009). Acta Cryst. E65, o3210. 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
Savitha, M. B. & Gowda, B. T. (2006). Z. Naturforsch. Teil A, 60, 600–606. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of a study of the substituent effects on the structures of N-(aryl)-arylsulfonamides (Gowda et al. , 2009a,b, 2010), in the present work the structure of 2,4-dimethyl-N-(2-chlorophenyl)benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO2—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is bent at the S atom with the C1—SO2—NH—C7 torsion angle of -54.9 (2)°, compared to the values of 71.6 (1)° in 2,4-dimethyl-N-(2-methylphenyl)benzenesulfonamide (II) (Nirmala et al., 2009), 74.8 (4)° in 4-chloro-2-methyl-N-(2-chlorophenyl)benzenesulfonamide (III) (Gowda et al., 2009b), -46.1 (3)° (molecule 1) and 47.7 (3)° (molecule 2) in the two molecules of 2,4-dimethyl-N-(phenyl)benzenesulfonamide (IV) (Gowda et al., 2009a) and -54.8 (2)° in N-(2-chlorophenyl)-4-methylbenzenesulfonamide (V) (Gowda et al., 2010).
The two benzene rings in (I) are tilted relative to each other by 75.7 (1)°, compared to the values of 47.0 (1)° (II), 45.5 (2)° in (III), 67.5 (1)° in molecule 1 and 72.9 (1)° in molecule 2 of (IV), and 71.6 (1)° in (V). The other bond parameters in (I) are similar to those observed in (II), (III), (IV), (V) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).
The structure shows simultaneous N—H···Cl intramolecular and N—H···O intermolecular H-bonding (Table 1). The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds is shown in Fig.2.