organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

3,5-Di­chloro-N-(2,4-di­chloro­phen­yl)benzene­sulfonamide

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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

Edited by J. Simpson, University of Otago, New Zealand (Received 6 March 2017; accepted 8 March 2017; online 10 March 2017)

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]. ππ 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.

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 of sulfonamides (Shakuntala et al., 2017[Shakuntala, K., Kumari, V., Lokanath, N. K., Naveen, S. & Suchetan, P. A. (2017). IUCrData, 2, x170311.]), we report herein the crystal structure of the title sulfonamide derivative.

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

[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, pairs of mol­ecules are linked by N1—H1⋯O2i hydrogen bonds, forming inversion dimers that enclose R22(8) loops (Table 1[link] and Fig. 2[link]). 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]. ππ contacts [centroid–centroid distance = 3.6574 (19) Å; symmetry code: 1 − x, 1 − y, 1 − z] between the C7–C12 rings, Fig. 3[link], link adjacent chains into a three-dimensional supra­molecular network with mol­ecules stacked along the b-axis direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.
[Figure 2]
Figure 2
Double-chain architecture displayed in the crystal structure of the title compound, propagating along the b axis and formed by N—H⋯O and C—H⋯O hydrogen bonds (see Table 1[link]). Cl⋯Cl contacts are also shown.
[Figure 3]
Figure 3
πar­ylπar­yl contacts in the title compound viewed along a.

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. 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 refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C12H7Cl4NO2S
Mr 371.05
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 8.1107 (4), 8.2615 (4), 11.2048 (5)
α, β, γ (°) 86.791 (2), 70.625 (2), 85.783 (2)
V3) 705.96 (6)
Z 2
Radiation type Cu Kα
μ (mm−1) 9.01
Crystal size (mm) 0.26 × 0.23 × 0.20
 
Data collection
Diffractometer Bruker APEXII CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.144, 0.165
No. of measured, independent and observed [I > 2σ(I)] reflections 6182, 2295, 2152
Rint 0.049
(sin θ/λ)max−1) 0.584
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.190, 1.08
No. of reflections 2295
No. of parameters 185
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.15, −1.04
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.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and 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.]).

Structural data


Computing details top

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

3,5-Dichloro-N-(2,4-dichlorophenyl)benzenesulfonamide top
Crystal data top
C12H7Cl4NO2SZ = 2
Mr = 371.05F(000) = 372
Triclinic, P1prism
Hall symbol: -P 1Dx = 1.746 Mg m3
a = 8.1107 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.2615 (4) ÅCell parameters from 154 reflections
c = 11.2048 (5) Åθ = 5.4–64.2°
α = 86.791 (2)°µ = 9.01 mm1
β = 70.625 (2)°T = 100 K
γ = 85.783 (2)°Prism, colourless
V = 705.96 (6) Å30.26 × 0.23 × 0.20 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
2295 independent reflections
Radiation source: fine-focus sealed tube2152 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 64.2°, θmin = 5.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 99
Tmin = 0.144, Tmax = 0.165k = 99
6182 measured reflectionsl = 1213
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.063H 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 reflectionsΔρmax = 1.15 e Å3
185 parametersΔρmin = 1.04 e Å3
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
C10.0147 (4)0.9271 (4)0.7955 (3)0.0146 (7)
C20.0650 (4)0.8534 (4)0.8789 (3)0.0137 (7)
H20.1852870.8651340.8665240.016*
C30.0373 (5)0.7626 (4)0.9805 (3)0.0169 (8)
C40.2119 (5)0.7464 (4)1.0011 (3)0.0202 (8)
H40.2799380.6841981.0717790.024*
C50.2867 (5)0.8225 (5)0.9167 (4)0.0208 (8)
C60.1911 (5)0.9131 (4)0.8122 (3)0.0183 (8)
H60.2436620.9635130.7542870.022*
C70.3233 (4)0.7602 (4)0.5954 (3)0.0132 (7)
C80.2658 (4)0.6040 (4)0.6286 (3)0.0123 (7)
C90.3685 (4)0.4808 (4)0.6637 (3)0.0140 (7)
H90.3291980.3739860.6838420.017*
C100.5287 (5)0.5179 (4)0.6686 (3)0.0157 (8)
C110.5914 (5)0.6721 (4)0.6362 (3)0.0160 (8)
H110.7031320.6945720.6392530.019*
C120.4883 (4)0.7922 (4)0.5996 (3)0.0154 (8)
H120.5301010.8978910.5769270.018*
N10.2191 (4)0.8860 (3)0.5578 (3)0.0142 (6)
O10.2543 (3)1.0985 (3)0.6941 (2)0.0167 (6)
O20.0145 (3)1.1270 (3)0.6002 (2)0.0198 (6)
S10.12158 (10)1.02925 (9)0.65887 (8)0.0129 (3)
CL10.05978 (11)0.66634 (11)1.08447 (8)0.0222 (3)
CL20.50807 (12)0.80140 (14)0.94357 (9)0.0313 (4)
CL30.06355 (10)0.55785 (10)0.62220 (8)0.0180 (3)
CL40.65852 (11)0.36568 (10)0.71396 (8)0.0215 (3)
H10.149 (4)0.853 (5)0.523 (4)0.012 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0141 (17)0.0164 (17)0.0120 (17)0.0025 (13)0.0024 (13)0.0005 (13)
C20.0123 (15)0.0140 (17)0.0142 (18)0.0004 (13)0.0032 (13)0.0038 (14)
C30.0211 (19)0.0191 (19)0.0114 (19)0.0003 (15)0.0068 (15)0.0008 (15)
C40.0206 (19)0.0231 (19)0.0123 (18)0.0086 (15)0.0022 (15)0.0005 (15)
C50.0125 (17)0.029 (2)0.0195 (19)0.0047 (15)0.0029 (14)0.0018 (16)
C60.0179 (18)0.023 (2)0.0143 (18)0.0005 (14)0.0062 (15)0.0023 (14)
C70.0149 (17)0.0174 (18)0.0055 (16)0.0002 (13)0.0014 (13)0.0006 (13)
C80.0094 (15)0.0191 (18)0.0077 (15)0.0042 (13)0.0012 (13)0.0008 (13)
C90.0176 (17)0.0131 (17)0.0098 (17)0.0018 (13)0.0025 (13)0.0006 (13)
C100.0170 (17)0.0192 (18)0.0095 (17)0.0017 (14)0.0036 (14)0.0030 (14)
C110.0123 (16)0.0219 (19)0.0133 (18)0.0043 (14)0.0030 (13)0.0005 (14)
C120.0135 (17)0.0173 (18)0.0128 (17)0.0046 (13)0.0008 (13)0.0036 (13)
N10.0150 (14)0.0159 (15)0.0133 (15)0.0034 (11)0.0068 (12)0.0024 (12)
O10.0172 (12)0.0158 (12)0.0172 (13)0.0052 (10)0.0052 (10)0.0027 (10)
O20.0215 (13)0.0180 (13)0.0201 (14)0.0022 (10)0.0084 (11)0.0032 (10)
S10.0132 (5)0.0127 (5)0.0124 (5)0.0028 (4)0.0038 (4)0.0030 (4)
CL10.0241 (5)0.0271 (6)0.0155 (5)0.0033 (4)0.0076 (4)0.0072 (4)
CL20.0129 (5)0.0571 (8)0.0232 (6)0.0112 (4)0.0037 (4)0.0027 (5)
CL30.0142 (5)0.0201 (5)0.0225 (6)0.0070 (4)0.0094 (4)0.0045 (4)
CL40.0189 (5)0.0227 (6)0.0247 (6)0.0014 (4)0.0110 (4)0.0057 (4)
Geometric parameters (Å, º) top
C1—C61.393 (5)C7—N11.424 (4)
C1—C21.393 (5)C8—C91.391 (5)
C1—S11.774 (4)C8—CL31.736 (3)
C2—C31.385 (5)C9—C101.376 (5)
C2—H20.9500C9—H90.9500
C3—C41.372 (5)C10—C111.391 (5)
C3—CL11.738 (3)C10—CL41.742 (3)
C4—C51.384 (6)C11—C121.383 (5)
C4—H40.9500C11—H110.9500
C5—C61.385 (5)C12—H120.9500
C5—CL21.740 (4)N1—S11.651 (3)
C6—H60.9500N1—H10.858 (19)
C7—C81.393 (5)O1—S11.428 (3)
C7—C121.400 (5)O2—S11.433 (3)
C6—C1—C2122.3 (3)C7—C8—CL3119.9 (3)
C6—C1—S1120.4 (3)C10—C9—C8118.1 (3)
C2—C1—S1117.2 (3)C10—C9—H9120.9
C3—C2—C1117.6 (3)C8—C9—H9120.9
C3—C2—H2121.2C9—C10—C11122.0 (3)
C1—C2—H2121.2C9—C10—CL4118.9 (3)
C4—C3—C2122.0 (3)C11—C10—CL4119.1 (3)
C4—C3—CL1119.4 (3)C12—C11—C10118.9 (3)
C2—C3—CL1118.6 (3)C12—C11—H11120.6
C3—C4—C5118.7 (3)C10—C11—H11120.6
C3—C4—H4120.7C11—C12—C7120.9 (3)
C5—C4—H4120.7C11—C12—H12119.6
C4—C5—C6122.2 (3)C7—C12—H12119.6
C4—C5—CL2118.3 (3)C7—N1—S1118.4 (2)
C6—C5—CL2119.4 (3)C7—N1—H1115 (3)
C5—C6—C1117.1 (3)S1—N1—H1111 (3)
C5—C6—H6121.4O1—S1—O2121.08 (15)
C1—C6—H6121.4O1—S1—N1107.18 (15)
C8—C7—C12118.3 (3)O2—S1—N1105.43 (15)
C8—C7—N1121.8 (3)O1—S1—C1107.19 (15)
C12—C7—N1119.9 (3)O2—S1—C1109.28 (16)
C9—C8—C7121.8 (3)N1—S1—C1105.69 (15)
C9—C8—CL3118.3 (3)
C6—C1—C2—C30.6 (5)C8—C9—C10—C111.8 (5)
S1—C1—C2—C3175.0 (3)C8—C9—C10—CL4179.4 (3)
C1—C2—C3—C41.0 (5)C9—C10—C11—C120.8 (5)
C1—C2—C3—CL1178.8 (3)CL4—C10—C11—C12179.6 (3)
C2—C3—C4—C50.5 (6)C10—C11—C12—C70.3 (5)
CL1—C3—C4—C5179.4 (3)C8—C7—C12—C110.3 (5)
C3—C4—C5—C60.5 (6)N1—C7—C12—C11179.7 (3)
C3—C4—C5—CL2180.0 (3)C8—C7—N1—S1105.4 (3)
C4—C5—C6—C10.9 (6)C12—C7—N1—S174.6 (4)
CL2—C5—C6—C1179.6 (3)C7—N1—S1—O155.4 (3)
C2—C1—C6—C50.3 (6)C7—N1—S1—O2174.4 (2)
S1—C1—C6—C5175.8 (3)C7—N1—S1—C158.7 (3)
C12—C7—C8—C90.8 (5)C6—C1—S1—O1150.1 (3)
N1—C7—C8—C9179.2 (3)C2—C1—S1—O134.1 (3)
C12—C7—C8—CL3178.9 (3)C6—C1—S1—O217.2 (4)
N1—C7—C8—CL31.1 (5)C2—C1—S1—O2167.0 (3)
C7—C8—C9—C101.8 (5)C6—C1—S1—N195.8 (3)
CL3—C8—C9—C10180.0 (3)C2—C1—S1—N179.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.203.0026155
C9—H9···O1ii0.952.393.324 (4)170
Symmetry codes: (i) x, y+2, z+1; (ii) x, y1, 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.

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 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

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