organic compounds
3,5-Dichloro-N-(4-methylphenyl)benzenesulfonamide
aDepartment of Chemistry, Sri Bhuvanendra College, Karkala 574 104, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India, and dDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India
*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, pasuchetan@yahoo.co.in
The molecule of the title compound, C13H11Cl2NO2S, is U-shaped with the central C—S—N—C segment having a torsion angle of 67.2 (4)°. The dihedral angle between the benzene rings is 57.0 (2)°. In the crystal, molecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure.
Keywords: crystal structure; sulfonamides; N—H⋯O hydrogen bonding; C—H⋯O hydrogen bonding; C—H⋯π interactions.
Structure description
In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety (Mohan et al., 2013). As part of our ongoing studies on (Shakuntala et al., 2017), we report herein on the synthesis and of the title compound.
The molecule of the title compound, Fig. 1, is U-shaped with the central C1—S1—N1—C7 segment having a torsion angle of 67.2 (4)°. The dihedral angle between the benzene rings is 57.0 (2)°.
In the crystal, molecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [100]; see Table 1 and Fig. 2. The chains are linked by C—H⋯π interactions, forming a three-dimensional supramolecular structure (Fig. 3 and Table 1). The shortest Cl⋯Cl separation is 3.438 (1) Å (Fig. 3).
Synthesis and crystallization
The title compound was prepared according to a literature method (Rodrigues et al., 2015). The purity of the compound was checked by determining its melting point. Colourless prismatic crystals were obtained by slow evaporation of a solution in ethanol, at room temperature, m.p. = 453 K.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
https://doi.org/10.1107/S2414314617003753/su4140sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003753/su4140Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617003753/su4140Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXT2016 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b) and PLATON (Spek, 2009).C13H11Cl2NO2S | Dx = 1.484 Mg m−3 |
Mr = 316.19 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, P212121 | Cell parameters from 143 reflections |
a = 6.1673 (3) Å | θ = 6.1–64.2° |
b = 13.0059 (7) Å | µ = 5.49 mm−1 |
c = 17.6433 (9) Å | T = 100 K |
V = 1415.19 (13) Å3 | Prism, colourless |
Z = 4 | 0.29 × 0.24 × 0.22 mm |
F(000) = 648 |
Bruker APEXII CCD diffractometer | 2210 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
ω and φ scans | θmax = 64.2°, θmin = 6.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −7→7 |
Tmin = 0.258, Tmax = 0.299 | k = −14→14 |
7822 measured reflections | l = −18→20 |
2292 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.115P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
2292 reflections | Δρmax = 0.42 e Å−3 |
177 parameters | Δρmin = −0.59 e Å−3 |
1 restraint | Absolute structure: Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.101 (13) |
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. |
x | y | z | Uiso*/Ueq | ||
CL1 | 0.4625 (2) | 0.27187 (11) | 0.71332 (6) | 0.0310 (4) | |
CL2 | 0.9584 (2) | 0.59855 (10) | 0.78818 (7) | 0.0365 (4) | |
S1 | 1.17445 (18) | 0.35953 (9) | 0.54747 (6) | 0.0191 (4) | |
O1 | 1.3636 (5) | 0.4224 (3) | 0.55489 (18) | 0.0236 (8) | |
O2 | 1.1925 (6) | 0.2491 (3) | 0.54433 (18) | 0.0256 (8) | |
C4 | 0.7242 (9) | 0.4340 (4) | 0.7437 (3) | 0.0281 (12) | |
H4 | 0.628893 | 0.449882 | 0.784407 | 0.034* | |
C5 | 0.9032 (9) | 0.4936 (4) | 0.7298 (3) | 0.0250 (11) | |
C6 | 1.0463 (9) | 0.4729 (4) | 0.6700 (3) | 0.0260 (11) | |
H6 | 1.170170 | 0.514515 | 0.661025 | 0.031* | |
C1 | 0.9987 (8) | 0.3891 (4) | 0.6248 (2) | 0.0193 (10) | |
N1 | 1.0491 (7) | 0.3909 (3) | 0.4694 (2) | 0.0213 (9) | |
C7 | 1.0053 (8) | 0.4973 (4) | 0.4532 (2) | 0.0200 (10) | |
C12 | 0.8004 (9) | 0.5373 (4) | 0.4662 (3) | 0.0271 (11) | |
H12 | 0.689690 | 0.495458 | 0.487485 | 0.032* | |
C11 | 0.7588 (9) | 0.6397 (5) | 0.4478 (3) | 0.0312 (12) | |
H11 | 0.618169 | 0.667346 | 0.456150 | 0.037* | |
C10 | 0.9196 (10) | 0.7019 (4) | 0.4174 (3) | 0.0304 (13) | |
C13 | 0.8682 (13) | 0.8123 (4) | 0.3951 (3) | 0.0437 (16) | |
H13A | 0.788698 | 0.812679 | 0.346961 | 0.066* | |
H13B | 1.003609 | 0.850936 | 0.389253 | 0.066* | |
H13C | 0.779222 | 0.844344 | 0.434548 | 0.066* | |
C3 | 0.6852 (8) | 0.3502 (4) | 0.6972 (3) | 0.0235 (11) | |
C2 | 0.8198 (8) | 0.3268 (4) | 0.6371 (3) | 0.0231 (11) | |
H2 | 0.790606 | 0.269702 | 0.605079 | 0.028* | |
C9 | 1.1261 (9) | 0.6600 (4) | 0.4053 (3) | 0.0259 (11) | |
H9 | 1.237690 | 0.701855 | 0.384760 | 0.031* | |
C8 | 1.1697 (8) | 0.5578 (4) | 0.4231 (2) | 0.0236 (10) | |
H8 | 1.310023 | 0.529869 | 0.414837 | 0.028* | |
H1 | 0.944 (7) | 0.348 (3) | 0.460 (3) | 0.022 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
CL1 | 0.0262 (6) | 0.0443 (8) | 0.0225 (6) | −0.0092 (6) | 0.0011 (5) | 0.0037 (5) |
CL2 | 0.0462 (8) | 0.0292 (7) | 0.0340 (7) | −0.0001 (6) | 0.0017 (6) | −0.0137 (5) |
S1 | 0.0187 (6) | 0.0187 (6) | 0.0199 (6) | 0.0012 (5) | 0.0017 (4) | −0.0006 (4) |
O1 | 0.0188 (16) | 0.0291 (19) | 0.0231 (16) | −0.0022 (15) | −0.0015 (14) | −0.0001 (14) |
O2 | 0.0279 (19) | 0.0195 (18) | 0.0293 (17) | 0.0056 (15) | 0.0035 (15) | −0.0003 (14) |
C4 | 0.028 (3) | 0.037 (3) | 0.020 (2) | 0.005 (2) | 0.002 (2) | 0.006 (2) |
C5 | 0.031 (3) | 0.022 (2) | 0.022 (2) | −0.001 (2) | −0.002 (2) | −0.001 (2) |
C6 | 0.028 (3) | 0.022 (3) | 0.029 (2) | −0.002 (2) | −0.003 (2) | 0.000 (2) |
C1 | 0.020 (2) | 0.023 (2) | 0.015 (2) | 0.004 (2) | 0.0004 (18) | 0.0020 (17) |
N1 | 0.0230 (19) | 0.020 (2) | 0.020 (2) | −0.0035 (19) | −0.0014 (17) | 0.0001 (16) |
C7 | 0.026 (2) | 0.021 (2) | 0.0126 (19) | −0.002 (2) | −0.006 (2) | −0.0027 (17) |
C12 | 0.024 (2) | 0.038 (3) | 0.019 (2) | −0.002 (2) | 0.001 (2) | −0.002 (2) |
C11 | 0.030 (3) | 0.040 (3) | 0.024 (3) | 0.012 (3) | 0.000 (2) | 0.003 (2) |
C10 | 0.047 (3) | 0.026 (3) | 0.019 (2) | 0.011 (3) | −0.007 (2) | −0.003 (2) |
C13 | 0.076 (5) | 0.026 (3) | 0.029 (3) | 0.015 (3) | −0.011 (3) | 0.001 (2) |
C3 | 0.024 (2) | 0.026 (3) | 0.021 (2) | 0.000 (2) | −0.005 (2) | 0.0057 (19) |
C2 | 0.027 (3) | 0.024 (3) | 0.019 (2) | −0.002 (2) | −0.004 (2) | −0.0010 (18) |
C9 | 0.029 (3) | 0.027 (3) | 0.021 (2) | −0.007 (2) | −0.003 (2) | 0.005 (2) |
C8 | 0.023 (2) | 0.028 (3) | 0.020 (2) | −0.003 (2) | −0.0027 (19) | −0.002 (2) |
CL1—C3 | 1.734 (5) | C7—C8 | 1.389 (7) |
CL2—C5 | 1.743 (5) | C12—C11 | 1.396 (8) |
S1—O1 | 1.430 (4) | C12—H12 | 0.9500 |
S1—O2 | 1.442 (4) | C11—C10 | 1.387 (9) |
S1—N1 | 1.631 (4) | C11—H11 | 0.9500 |
S1—C1 | 1.784 (5) | C10—C9 | 1.402 (8) |
C4—C5 | 1.371 (8) | C10—C13 | 1.523 (7) |
C4—C3 | 1.386 (8) | C13—H13A | 0.9800 |
C4—H4 | 0.9500 | C13—H13B | 0.9800 |
C5—C6 | 1.402 (8) | C13—H13C | 0.9800 |
C6—C1 | 1.383 (7) | C3—C2 | 1.381 (7) |
C6—H6 | 0.9500 | C2—H2 | 0.9500 |
C1—C2 | 1.386 (7) | C9—C8 | 1.391 (8) |
N1—C7 | 1.439 (6) | C9—H9 | 0.9500 |
N1—H1 | 0.87 (3) | C8—H8 | 0.9500 |
C7—C12 | 1.386 (7) | ||
O1—S1—O2 | 120.7 (2) | C11—C12—H12 | 120.4 |
O1—S1—N1 | 108.7 (2) | C10—C11—C12 | 121.0 (5) |
O2—S1—N1 | 104.7 (2) | C10—C11—H11 | 119.5 |
O1—S1—C1 | 107.6 (2) | C12—C11—H11 | 119.5 |
O2—S1—C1 | 106.9 (2) | C11—C10—C9 | 118.8 (5) |
N1—S1—C1 | 107.7 (2) | C11—C10—C13 | 120.1 (6) |
C5—C4—C3 | 118.6 (5) | C9—C10—C13 | 121.1 (6) |
C5—C4—H4 | 120.7 | C10—C13—H13A | 109.5 |
C3—C4—H4 | 120.7 | C10—C13—H13B | 109.5 |
C4—C5—C6 | 122.2 (5) | H13A—C13—H13B | 109.5 |
C4—C5—CL2 | 119.6 (4) | C10—C13—H13C | 109.5 |
C6—C5—CL2 | 118.2 (4) | H13A—C13—H13C | 109.5 |
C1—C6—C5 | 116.9 (5) | H13B—C13—H13C | 109.5 |
C1—C6—H6 | 121.5 | C2—C3—C4 | 121.6 (5) |
C5—C6—H6 | 121.5 | C2—C3—CL1 | 118.2 (4) |
C6—C1—C2 | 122.6 (5) | C4—C3—CL1 | 120.2 (4) |
C6—C1—S1 | 118.9 (4) | C3—C2—C1 | 118.0 (4) |
C2—C1—S1 | 118.5 (4) | C3—C2—H2 | 121.0 |
C7—N1—S1 | 119.8 (3) | C1—C2—H2 | 121.0 |
C7—N1—H1 | 116 (4) | C8—C9—C10 | 120.9 (5) |
S1—N1—H1 | 111 (4) | C8—C9—H9 | 119.6 |
C12—C7—C8 | 121.1 (5) | C10—C9—H9 | 119.6 |
C12—C7—N1 | 119.9 (5) | C9—C8—C7 | 119.1 (5) |
C8—C7—N1 | 119.0 (4) | C9—C8—H8 | 120.4 |
C7—C12—C11 | 119.2 (5) | C7—C8—H8 | 120.4 |
C7—C12—H12 | 120.4 | ||
C3—C4—C5—C6 | 0.5 (8) | C8—C7—C12—C11 | 0.9 (7) |
C3—C4—C5—CL2 | −179.2 (4) | N1—C7—C12—C11 | −177.9 (4) |
C4—C5—C6—C1 | 0.2 (7) | C7—C12—C11—C10 | −0.6 (7) |
CL2—C5—C6—C1 | 179.9 (4) | C12—C11—C10—C9 | 0.1 (8) |
C5—C6—C1—C2 | −0.4 (7) | C12—C11—C10—C13 | 177.8 (5) |
C5—C6—C1—S1 | 179.7 (4) | C5—C4—C3—C2 | −1.0 (7) |
O1—S1—C1—C6 | 10.0 (4) | C5—C4—C3—CL1 | 179.3 (4) |
O2—S1—C1—C6 | 141.0 (4) | C4—C3—C2—C1 | 0.8 (7) |
N1—S1—C1—C6 | −107.0 (4) | CL1—C3—C2—C1 | −179.4 (3) |
O1—S1—C1—C2 | −169.9 (3) | C6—C1—C2—C3 | −0.1 (7) |
O2—S1—C1—C2 | −39.0 (4) | S1—C1—C2—C3 | 179.8 (4) |
N1—S1—C1—C2 | 73.0 (4) | C11—C10—C9—C8 | 0.2 (7) |
O1—S1—N1—C7 | −49.1 (4) | C13—C10—C9—C8 | −177.4 (4) |
O2—S1—N1—C7 | −179.3 (4) | C10—C9—C8—C7 | 0.0 (7) |
C1—S1—N1—C7 | 67.2 (4) | C12—C7—C8—C9 | −0.6 (6) |
S1—N1—C7—C12 | −100.5 (5) | N1—C7—C8—C9 | 178.2 (4) |
S1—N1—C7—C8 | 80.6 (5) |
Cg is the centroid of the C7–C12 aniline ring |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.87 (4) | 2.00 (4) | 2.866 (6) | 171 (5) |
C12—H12···O1ii | 0.95 | 2.52 | 3.455 (6) | 167 |
C4—H4···Cgiii | 0.95 | 2.80 | 3.602 (6) | 143 |
Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x−1, y, z; (iii) −x+3/2, −y+1, z+1/2. |
Acknowledgements
The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data. KS is grateful to the University Grants Commission (UGC), New Delhi, for the financial assistance under its MRP scheme.
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