organic compounds
3,5-Dichloro-N-(2,4-dichlorophenyl)benzenesulfonamide
aDepartment of Chemistry, Sri Bhuvanendra College, Karkala 574 104, India, bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India, cInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, and dDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India
*Correspondence e-mail: naveen@ioe.uni-mysore.ac.in, pasuchetan@yahoo.co.in
The molecule of the title compound, C12H7Cl4NO2S, is U-shaped, with the central C—S—N—C segment having a torsion angle of −58.7 (3)°. The dihedral angle between the benzene rings is 40.23 (2)°. Further, the ortho Cl atom on the aniline ring is syn to the N—H bond in the central –C—S(O2)—NH—C– segment. In the crystal, molecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers that enclose R22(8) loops. These dimers are linked by C—H⋯O hydrogen bonds that form a double C(7) chain propagating along the b-axis direction. These chains are further consolidated by Cl⋯Cl halogen bonds [3.4331 (2) Å]. π–π contacts [centroid–centroid distance = 3.6574 (19) Å] between the aniline rings link adjacent chains into a three-dimensional supramolecular network with molecules stacked along the b-axis direction.
Keywords: crystal structure; sulfonamides; N—H⋯O hydrogen bonds; C—H⋯O interactions; Cl⋯Cl contacts; π–π interactions.
CCDC reference: 1536597
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 of (Shakuntala et al., 2017), we report herein the of the title sulfonamide derivative.
The molecule of the title compound (Fig. 1) is U shaped with the central C1—S1—N1—C7 segment displaying a torsion angle of −58.7 (3)°. The dihedral angle between the benzene rings is 40.23 (2)°. Further, the ortho chlorine atom on the aniline ring is syn to the N—H bond in the central –C—S(O2)-NH—C– segment of the molecule.
In the crystal, pairs of molecules are linked by N1—H1⋯O2i hydrogen bonds, forming inversion dimers that enclose R22(8) loops (Table 1 and Fig. 2). These dimers are joined through C9—H9⋯O1ii hydrogen bonds that form a double C(7) chain propagating along the b-axis direction. These chains are further consolidated by Cl3⋯Cl3iii halogen bonds [3.4331 (2) Å; symmetry code: (iii) −x, −y + 1, −z + 1]. π–π contacts [centroid–centroid distance = 3.6574 (19) Å; symmetry code: 1 − x, 1 − y, 1 − z] between the C7–C12 rings, Fig. 3, link adjacent chains into a three-dimensional supramolecular network with molecules stacked along the b-axis direction.
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. Prismatic single crystals suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol solution of the compound at room temperature.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1536597
https://doi.org/10.1107/S2414314617003728/sj4094sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003728/sj4094Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617003728/sj4094Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
APEX2 and 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).C12H7Cl4NO2S | Z = 2 |
Mr = 371.05 | F(000) = 372 |
Triclinic, P1 | prism |
Hall symbol: -P 1 | Dx = 1.746 Mg m−3 |
a = 8.1107 (4) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.2615 (4) Å | Cell parameters from 154 reflections |
c = 11.2048 (5) Å | θ = 5.4–64.2° |
α = 86.791 (2)° | µ = 9.01 mm−1 |
β = 70.625 (2)° | T = 100 K |
γ = 85.783 (2)° | Prism, colourless |
V = 705.96 (6) Å3 | 0.26 × 0.23 × 0.20 mm |
Bruker APEXII CCD area detector diffractometer | 2295 independent reflections |
Radiation source: fine-focus sealed tube | 2152 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 64.2°, θmin = 5.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −9→9 |
Tmin = 0.144, Tmax = 0.165 | k = −9→9 |
6182 measured reflections | l = −12→13 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.190 | w = 1/[σ2(Fo2) + (0.153P)2 + 0.3492P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2295 reflections | Δρmax = 1.15 e Å−3 |
185 parameters | Δρmin = −1.04 e Å−3 |
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 | ||
C1 | −0.0147 (4) | 0.9271 (4) | 0.7955 (3) | 0.0146 (7) | |
C2 | 0.0650 (4) | 0.8534 (4) | 0.8789 (3) | 0.0137 (7) | |
H2 | 0.185287 | 0.865134 | 0.866524 | 0.016* | |
C3 | −0.0373 (5) | 0.7626 (4) | 0.9805 (3) | 0.0169 (8) | |
C4 | −0.2119 (5) | 0.7464 (4) | 1.0011 (3) | 0.0202 (8) | |
H4 | −0.279938 | 0.684198 | 1.071779 | 0.024* | |
C5 | −0.2867 (5) | 0.8225 (5) | 0.9167 (4) | 0.0208 (8) | |
C6 | −0.1911 (5) | 0.9131 (4) | 0.8122 (3) | 0.0183 (8) | |
H6 | −0.243662 | 0.963513 | 0.754287 | 0.022* | |
C7 | 0.3233 (4) | 0.7602 (4) | 0.5954 (3) | 0.0132 (7) | |
C8 | 0.2658 (4) | 0.6040 (4) | 0.6286 (3) | 0.0123 (7) | |
C9 | 0.3685 (4) | 0.4808 (4) | 0.6637 (3) | 0.0140 (7) | |
H9 | 0.329198 | 0.373986 | 0.683842 | 0.017* | |
C10 | 0.5287 (5) | 0.5179 (4) | 0.6686 (3) | 0.0157 (8) | |
C11 | 0.5914 (5) | 0.6721 (4) | 0.6362 (3) | 0.0160 (8) | |
H11 | 0.703132 | 0.694572 | 0.639253 | 0.019* | |
C12 | 0.4883 (4) | 0.7922 (4) | 0.5996 (3) | 0.0154 (8) | |
H12 | 0.530101 | 0.897891 | 0.576927 | 0.018* | |
N1 | 0.2191 (4) | 0.8860 (3) | 0.5578 (3) | 0.0142 (6) | |
O1 | 0.2543 (3) | 1.0985 (3) | 0.6941 (2) | 0.0167 (6) | |
O2 | 0.0145 (3) | 1.1270 (3) | 0.6002 (2) | 0.0198 (6) | |
S1 | 0.12158 (10) | 1.02925 (9) | 0.65887 (8) | 0.0129 (3) | |
CL1 | 0.05978 (11) | 0.66634 (11) | 1.08447 (8) | 0.0222 (3) | |
CL2 | −0.50807 (12) | 0.80140 (14) | 0.94357 (9) | 0.0313 (4) | |
CL3 | 0.06355 (10) | 0.55785 (10) | 0.62220 (8) | 0.0180 (3) | |
CL4 | 0.65852 (11) | 0.36568 (10) | 0.71396 (8) | 0.0215 (3) | |
H1 | 0.149 (4) | 0.853 (5) | 0.523 (4) | 0.012 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0141 (17) | 0.0164 (17) | 0.0120 (17) | −0.0025 (13) | −0.0024 (13) | 0.0005 (13) |
C2 | 0.0123 (15) | 0.0140 (17) | 0.0142 (18) | −0.0004 (13) | −0.0032 (13) | −0.0038 (14) |
C3 | 0.0211 (19) | 0.0191 (19) | 0.0114 (19) | −0.0003 (15) | −0.0068 (15) | 0.0008 (15) |
C4 | 0.0206 (19) | 0.0231 (19) | 0.0123 (18) | −0.0086 (15) | 0.0022 (15) | 0.0005 (15) |
C5 | 0.0125 (17) | 0.029 (2) | 0.0195 (19) | −0.0047 (15) | −0.0029 (14) | −0.0018 (16) |
C6 | 0.0179 (18) | 0.023 (2) | 0.0143 (18) | −0.0005 (14) | −0.0062 (15) | −0.0023 (14) |
C7 | 0.0149 (17) | 0.0174 (18) | 0.0055 (16) | 0.0002 (13) | −0.0014 (13) | −0.0006 (13) |
C8 | 0.0094 (15) | 0.0191 (18) | 0.0077 (15) | −0.0042 (13) | −0.0012 (13) | −0.0008 (13) |
C9 | 0.0176 (17) | 0.0131 (17) | 0.0098 (17) | −0.0018 (13) | −0.0025 (13) | 0.0006 (13) |
C10 | 0.0170 (17) | 0.0192 (18) | 0.0095 (17) | 0.0017 (14) | −0.0036 (14) | 0.0030 (14) |
C11 | 0.0123 (16) | 0.0219 (19) | 0.0133 (18) | −0.0043 (14) | −0.0030 (13) | 0.0005 (14) |
C12 | 0.0135 (17) | 0.0173 (18) | 0.0128 (17) | −0.0046 (13) | −0.0008 (13) | 0.0036 (13) |
N1 | 0.0150 (14) | 0.0159 (15) | 0.0133 (15) | −0.0034 (11) | −0.0068 (12) | 0.0024 (12) |
O1 | 0.0172 (12) | 0.0158 (12) | 0.0172 (13) | −0.0052 (10) | −0.0052 (10) | 0.0027 (10) |
O2 | 0.0215 (13) | 0.0180 (13) | 0.0201 (14) | 0.0022 (10) | −0.0084 (11) | 0.0032 (10) |
S1 | 0.0132 (5) | 0.0127 (5) | 0.0124 (5) | −0.0028 (4) | −0.0038 (4) | 0.0030 (4) |
CL1 | 0.0241 (5) | 0.0271 (6) | 0.0155 (5) | −0.0033 (4) | −0.0076 (4) | 0.0072 (4) |
CL2 | 0.0129 (5) | 0.0571 (8) | 0.0232 (6) | −0.0112 (4) | −0.0037 (4) | 0.0027 (5) |
CL3 | 0.0142 (5) | 0.0201 (5) | 0.0225 (6) | −0.0070 (4) | −0.0094 (4) | 0.0045 (4) |
CL4 | 0.0189 (5) | 0.0227 (6) | 0.0247 (6) | 0.0014 (4) | −0.0110 (4) | 0.0057 (4) |
C1—C6 | 1.393 (5) | C7—N1 | 1.424 (4) |
C1—C2 | 1.393 (5) | C8—C9 | 1.391 (5) |
C1—S1 | 1.774 (4) | C8—CL3 | 1.736 (3) |
C2—C3 | 1.385 (5) | C9—C10 | 1.376 (5) |
C2—H2 | 0.9500 | C9—H9 | 0.9500 |
C3—C4 | 1.372 (5) | C10—C11 | 1.391 (5) |
C3—CL1 | 1.738 (3) | C10—CL4 | 1.742 (3) |
C4—C5 | 1.384 (6) | C11—C12 | 1.383 (5) |
C4—H4 | 0.9500 | C11—H11 | 0.9500 |
C5—C6 | 1.385 (5) | C12—H12 | 0.9500 |
C5—CL2 | 1.740 (4) | N1—S1 | 1.651 (3) |
C6—H6 | 0.9500 | N1—H1 | 0.858 (19) |
C7—C8 | 1.393 (5) | O1—S1 | 1.428 (3) |
C7—C12 | 1.400 (5) | O2—S1 | 1.433 (3) |
C6—C1—C2 | 122.3 (3) | C7—C8—CL3 | 119.9 (3) |
C6—C1—S1 | 120.4 (3) | C10—C9—C8 | 118.1 (3) |
C2—C1—S1 | 117.2 (3) | C10—C9—H9 | 120.9 |
C3—C2—C1 | 117.6 (3) | C8—C9—H9 | 120.9 |
C3—C2—H2 | 121.2 | C9—C10—C11 | 122.0 (3) |
C1—C2—H2 | 121.2 | C9—C10—CL4 | 118.9 (3) |
C4—C3—C2 | 122.0 (3) | C11—C10—CL4 | 119.1 (3) |
C4—C3—CL1 | 119.4 (3) | C12—C11—C10 | 118.9 (3) |
C2—C3—CL1 | 118.6 (3) | C12—C11—H11 | 120.6 |
C3—C4—C5 | 118.7 (3) | C10—C11—H11 | 120.6 |
C3—C4—H4 | 120.7 | C11—C12—C7 | 120.9 (3) |
C5—C4—H4 | 120.7 | C11—C12—H12 | 119.6 |
C4—C5—C6 | 122.2 (3) | C7—C12—H12 | 119.6 |
C4—C5—CL2 | 118.3 (3) | C7—N1—S1 | 118.4 (2) |
C6—C5—CL2 | 119.4 (3) | C7—N1—H1 | 115 (3) |
C5—C6—C1 | 117.1 (3) | S1—N1—H1 | 111 (3) |
C5—C6—H6 | 121.4 | O1—S1—O2 | 121.08 (15) |
C1—C6—H6 | 121.4 | O1—S1—N1 | 107.18 (15) |
C8—C7—C12 | 118.3 (3) | O2—S1—N1 | 105.43 (15) |
C8—C7—N1 | 121.8 (3) | O1—S1—C1 | 107.19 (15) |
C12—C7—N1 | 119.9 (3) | O2—S1—C1 | 109.28 (16) |
C9—C8—C7 | 121.8 (3) | N1—S1—C1 | 105.69 (15) |
C9—C8—CL3 | 118.3 (3) | ||
C6—C1—C2—C3 | 0.6 (5) | C8—C9—C10—C11 | −1.8 (5) |
S1—C1—C2—C3 | −175.0 (3) | C8—C9—C10—CL4 | 179.4 (3) |
C1—C2—C3—C4 | −1.0 (5) | C9—C10—C11—C12 | 0.8 (5) |
C1—C2—C3—CL1 | 178.8 (3) | CL4—C10—C11—C12 | 179.6 (3) |
C2—C3—C4—C5 | 0.5 (6) | C10—C11—C12—C7 | 0.3 (5) |
CL1—C3—C4—C5 | −179.4 (3) | C8—C7—C12—C11 | −0.3 (5) |
C3—C4—C5—C6 | 0.5 (6) | N1—C7—C12—C11 | 179.7 (3) |
C3—C4—C5—CL2 | −180.0 (3) | C8—C7—N1—S1 | 105.4 (3) |
C4—C5—C6—C1 | −0.9 (6) | C12—C7—N1—S1 | −74.6 (4) |
CL2—C5—C6—C1 | 179.6 (3) | C7—N1—S1—O1 | 55.4 (3) |
C2—C1—C6—C5 | 0.3 (6) | C7—N1—S1—O2 | −174.4 (2) |
S1—C1—C6—C5 | 175.8 (3) | C7—N1—S1—C1 | −58.7 (3) |
C12—C7—C8—C9 | −0.8 (5) | C6—C1—S1—O1 | 150.1 (3) |
N1—C7—C8—C9 | 179.2 (3) | C2—C1—S1—O1 | −34.1 (3) |
C12—C7—C8—CL3 | −178.9 (3) | C6—C1—S1—O2 | 17.2 (4) |
N1—C7—C8—CL3 | 1.1 (5) | C2—C1—S1—O2 | −167.0 (3) |
C7—C8—C9—C10 | 1.8 (5) | C6—C1—S1—N1 | −95.8 (3) |
CL3—C8—C9—C10 | 180.0 (3) | C2—C1—S1—N1 | 79.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.20 | 3.0026 | 155 |
C9—H9···O1ii | 0.95 | 2.39 | 3.324 (4) | 170 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y−1, z. |
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 thankful to the University Grants Commission (UGC), New Delhi for the financial assistance under its MRP scheme.
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