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ISSN: 2414-3146

3,5-Di­chloro-N-(4-methyl­phen­yl)benzene­sulfonamide

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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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 5 March 2017; accepted 8 March 2017; online 10 March 2017)

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.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

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[Mohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem, 2, 722-729.]). As part of our ongoing studies on sulfonamides (Shakuntala et al., 2017[Shakuntala, K., Kumari, V., Lokanath, N. K., Naveen, S. & Suchetan, P. A. (2017). IUCrData, 2, x170311.]), we report herein on the synthesis and crystal structure of the title compound.

The mol­ecule of the title compound, Fig. 1[link], 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)°.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, mol­ecules are linked via N—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [100]; see Table 1[link] and Fig. 2[link]. The chains are linked by C—H⋯π inter­actions, forming a three-dimensional supra­molecular structure (Fig. 3[link] and Table 1[link]). The shortest Cl⋯Cl separation is 3.438 (1) Å (Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 aniline ring

D—H⋯A D—H H⋯A DA 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-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) x-1, y, z; (iii) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}].
[Figure 2]
Figure 2
A partial view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1[link]) and only the H atoms (grey balls) that are involved in hydrogen bonding are shown.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds and C—H⋯π inter­actions are shown as dashed lines (see Table 1[link]) and only the H atoms (grey balls) that are involved in these inter­actions are shown.

Synthesis and crystallization

The title compound was prepared according to a literature method (Rodrigues et al., 2015[Rodrigues, V. Z., Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Der Pharma Chem. 7, 299-307.]). 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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C13H11Cl2NO2S
Mr 316.19
Crystal system, space group Orthorhombic, P212121
Temperature (K) 100
a, b, c (Å) 6.1673 (3), 13.0059 (7), 17.6433 (9)
V3) 1415.19 (13)
Z 4
Radiation type Cu Kα
μ (mm−1) 5.49
Crystal size (mm) 0.29 × 0.24 × 0.22
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.258, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections 7822, 2292, 2210
Rint 0.060
(sin θ/λ)max−1) 0.584
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.138, 0.99
No. of reflections 2292
No. of parameters 177
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.42, −0.59
Absolute structure Flack x determined using 855 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter 0.101 (13)
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT2016 (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

3,5-Dichloro-N-(4-methylphenyl)benzenesulfonamide top
Crystal data top
C13H11Cl2NO2SDx = 1.484 Mg m3
Mr = 316.19Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 143 reflections
a = 6.1673 (3) Åθ = 6.1–64.2°
b = 13.0059 (7) ŵ = 5.49 mm1
c = 17.6433 (9) ÅT = 100 K
V = 1415.19 (13) Å3Prism, colourless
Z = 40.29 × 0.24 × 0.22 mm
F(000) = 648
Data collection top
Bruker APEXII CCD
diffractometer
2210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.060
ω and φ scansθmax = 64.2°, θmin = 6.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 77
Tmin = 0.258, Tmax = 0.299k = 1414
7822 measured reflectionsl = 1820
2292 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H 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 reflectionsΔρmax = 0.42 e Å3
177 parametersΔρmin = 0.59 e Å3
1 restraintAbsolute structure: Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.101 (13)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
CL10.4625 (2)0.27187 (11)0.71332 (6)0.0310 (4)
CL20.9584 (2)0.59855 (10)0.78818 (7)0.0365 (4)
S11.17445 (18)0.35953 (9)0.54747 (6)0.0191 (4)
O11.3636 (5)0.4224 (3)0.55489 (18)0.0236 (8)
O21.1925 (6)0.2491 (3)0.54433 (18)0.0256 (8)
C40.7242 (9)0.4340 (4)0.7437 (3)0.0281 (12)
H40.6288930.4498820.7844070.034*
C50.9032 (9)0.4936 (4)0.7298 (3)0.0250 (11)
C61.0463 (9)0.4729 (4)0.6700 (3)0.0260 (11)
H61.1701700.5145150.6610250.031*
C10.9987 (8)0.3891 (4)0.6248 (2)0.0193 (10)
N11.0491 (7)0.3909 (3)0.4694 (2)0.0213 (9)
C71.0053 (8)0.4973 (4)0.4532 (2)0.0200 (10)
C120.8004 (9)0.5373 (4)0.4662 (3)0.0271 (11)
H120.6896900.4954580.4874850.032*
C110.7588 (9)0.6397 (5)0.4478 (3)0.0312 (12)
H110.6181690.6673460.4561500.037*
C100.9196 (10)0.7019 (4)0.4174 (3)0.0304 (13)
C130.8682 (13)0.8123 (4)0.3951 (3)0.0437 (16)
H13A0.7886980.8126790.3469610.066*
H13B1.0036090.8509360.3892530.066*
H13C0.7792220.8443440.4345480.066*
C30.6852 (8)0.3502 (4)0.6972 (3)0.0235 (11)
C20.8198 (8)0.3268 (4)0.6371 (3)0.0231 (11)
H20.7906060.2697020.6050790.028*
C91.1261 (9)0.6600 (4)0.4053 (3)0.0259 (11)
H91.2376900.7018550.3847600.031*
C81.1697 (8)0.5578 (4)0.4231 (2)0.0236 (10)
H81.3100230.5298690.4148370.028*
H10.944 (7)0.348 (3)0.460 (3)0.022 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
CL10.0262 (6)0.0443 (8)0.0225 (6)0.0092 (6)0.0011 (5)0.0037 (5)
CL20.0462 (8)0.0292 (7)0.0340 (7)0.0001 (6)0.0017 (6)0.0137 (5)
S10.0187 (6)0.0187 (6)0.0199 (6)0.0012 (5)0.0017 (4)0.0006 (4)
O10.0188 (16)0.0291 (19)0.0231 (16)0.0022 (15)0.0015 (14)0.0001 (14)
O20.0279 (19)0.0195 (18)0.0293 (17)0.0056 (15)0.0035 (15)0.0003 (14)
C40.028 (3)0.037 (3)0.020 (2)0.005 (2)0.002 (2)0.006 (2)
C50.031 (3)0.022 (2)0.022 (2)0.001 (2)0.002 (2)0.001 (2)
C60.028 (3)0.022 (3)0.029 (2)0.002 (2)0.003 (2)0.000 (2)
C10.020 (2)0.023 (2)0.015 (2)0.004 (2)0.0004 (18)0.0020 (17)
N10.0230 (19)0.020 (2)0.020 (2)0.0035 (19)0.0014 (17)0.0001 (16)
C70.026 (2)0.021 (2)0.0126 (19)0.002 (2)0.006 (2)0.0027 (17)
C120.024 (2)0.038 (3)0.019 (2)0.002 (2)0.001 (2)0.002 (2)
C110.030 (3)0.040 (3)0.024 (3)0.012 (3)0.000 (2)0.003 (2)
C100.047 (3)0.026 (3)0.019 (2)0.011 (3)0.007 (2)0.003 (2)
C130.076 (5)0.026 (3)0.029 (3)0.015 (3)0.011 (3)0.001 (2)
C30.024 (2)0.026 (3)0.021 (2)0.000 (2)0.005 (2)0.0057 (19)
C20.027 (3)0.024 (3)0.019 (2)0.002 (2)0.004 (2)0.0010 (18)
C90.029 (3)0.027 (3)0.021 (2)0.007 (2)0.003 (2)0.005 (2)
C80.023 (2)0.028 (3)0.020 (2)0.003 (2)0.0027 (19)0.002 (2)
Geometric parameters (Å, º) top
CL1—C31.734 (5)C7—C81.389 (7)
CL2—C51.743 (5)C12—C111.396 (8)
S1—O11.430 (4)C12—H120.9500
S1—O21.442 (4)C11—C101.387 (9)
S1—N11.631 (4)C11—H110.9500
S1—C11.784 (5)C10—C91.402 (8)
C4—C51.371 (8)C10—C131.523 (7)
C4—C31.386 (8)C13—H13A0.9800
C4—H40.9500C13—H13B0.9800
C5—C61.402 (8)C13—H13C0.9800
C6—C11.383 (7)C3—C21.381 (7)
C6—H60.9500C2—H20.9500
C1—C21.386 (7)C9—C81.391 (8)
N1—C71.439 (6)C9—H90.9500
N1—H10.87 (3)C8—H80.9500
C7—C121.386 (7)
O1—S1—O2120.7 (2)C11—C12—H12120.4
O1—S1—N1108.7 (2)C10—C11—C12121.0 (5)
O2—S1—N1104.7 (2)C10—C11—H11119.5
O1—S1—C1107.6 (2)C12—C11—H11119.5
O2—S1—C1106.9 (2)C11—C10—C9118.8 (5)
N1—S1—C1107.7 (2)C11—C10—C13120.1 (6)
C5—C4—C3118.6 (5)C9—C10—C13121.1 (6)
C5—C4—H4120.7C10—C13—H13A109.5
C3—C4—H4120.7C10—C13—H13B109.5
C4—C5—C6122.2 (5)H13A—C13—H13B109.5
C4—C5—CL2119.6 (4)C10—C13—H13C109.5
C6—C5—CL2118.2 (4)H13A—C13—H13C109.5
C1—C6—C5116.9 (5)H13B—C13—H13C109.5
C1—C6—H6121.5C2—C3—C4121.6 (5)
C5—C6—H6121.5C2—C3—CL1118.2 (4)
C6—C1—C2122.6 (5)C4—C3—CL1120.2 (4)
C6—C1—S1118.9 (4)C3—C2—C1118.0 (4)
C2—C1—S1118.5 (4)C3—C2—H2121.0
C7—N1—S1119.8 (3)C1—C2—H2121.0
C7—N1—H1116 (4)C8—C9—C10120.9 (5)
S1—N1—H1111 (4)C8—C9—H9119.6
C12—C7—C8121.1 (5)C10—C9—H9119.6
C12—C7—N1119.9 (5)C9—C8—C7119.1 (5)
C8—C7—N1119.0 (4)C9—C8—H8120.4
C7—C12—C11119.2 (5)C7—C8—H8120.4
C7—C12—H12120.4
C3—C4—C5—C60.5 (8)C8—C7—C12—C110.9 (7)
C3—C4—C5—CL2179.2 (4)N1—C7—C12—C11177.9 (4)
C4—C5—C6—C10.2 (7)C7—C12—C11—C100.6 (7)
CL2—C5—C6—C1179.9 (4)C12—C11—C10—C90.1 (8)
C5—C6—C1—C20.4 (7)C12—C11—C10—C13177.8 (5)
C5—C6—C1—S1179.7 (4)C5—C4—C3—C21.0 (7)
O1—S1—C1—C610.0 (4)C5—C4—C3—CL1179.3 (4)
O2—S1—C1—C6141.0 (4)C4—C3—C2—C10.8 (7)
N1—S1—C1—C6107.0 (4)CL1—C3—C2—C1179.4 (3)
O1—S1—C1—C2169.9 (3)C6—C1—C2—C30.1 (7)
O2—S1—C1—C239.0 (4)S1—C1—C2—C3179.8 (4)
N1—S1—C1—C273.0 (4)C11—C10—C9—C80.2 (7)
O1—S1—N1—C749.1 (4)C13—C10—C9—C8177.4 (4)
O2—S1—N1—C7179.3 (4)C10—C9—C8—C70.0 (7)
C1—S1—N1—C767.2 (4)C12—C7—C8—C90.6 (6)
S1—N1—C7—C12100.5 (5)N1—C7—C8—C9178.2 (4)
S1—N1—C7—C880.6 (5)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C7–C12 aniline ring
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.87 (4)2.00 (4)2.866 (6)171 (5)
C12—H12···O1ii0.952.523.455 (6)167
C4—H4···Cgiii0.952.803.602 (6)143
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x1, 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.

References

First citationBruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationMohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem, 2, 722–729.  Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationRodrigues, V. Z., Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Der Pharma Chem. 7, 299–307.  CAS Google Scholar
First citationShakuntala, K., Kumari, V., Lokanath, N. K., Naveen, S. & Suchetan, P. A. (2017). IUCrData, 2, x170311.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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