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

Shakuntala, K.; Naveen, S.; Lokanath, N.K.; Suchetan, P.A.

doi:10.1107/S2414314617003753

organic compounds

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Volume 2| Part 3| March 2017| x170375

https://doi.org/10.1107/S2414314617003753

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

K. Shakuntala,^a S. Naveen,^b N. K. Lokanath ^c ^* and P. A. Suchetan ^d ^*

^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.

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 sulfonamides (Shakuntala et al., 2017 ), we report herein on the synthesis and crystal structure 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)°.

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 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).

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x-1, y, z; (iii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
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

) and only the H atoms (grey balls) that are involved in hydrogen bonding are shown.

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

) 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 ). 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.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₁₁Cl₂NO₂S
M_r	316.19
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.1673 (3), 13.0059 (7), 17.6433 (9)
V (Å³)	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 )
T_min, T_max	0.258, 0.299
No. of measured, independent and observed [I > 2σ(I)] reflections	7822, 2292, 2210
R_int	0.060
(sin θ/λ)_max (Å⁻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
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.59
Absolute structure	Flack x determined using 855 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.101 (13)
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009), SHELXT2016 (Sheldrick, 2015a ), Mercury (Macrae et al., 2008 ), SHELXL2016 (Sheldrick, 2015b ) and PLATON (Spek, 2009 ).

Structural data

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314617003753/su4140sup1.cif

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

checkCIF report

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

C₁₃H₁₁Cl₂NO₂S	D_x = 1.484 Mg m⁻³
M_r = 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

Data collection top

Bruker APEXII CCD diffractometer	2210 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
ω and φ scans	θ_max = 64.2°, θ_min = 6.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.258, T_max = 0.299	k = −14→14
7822 measured reflections	l = −18→20
2292 independent reflections

Refinement top

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(F_o²) + (0.115P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
2292 reflections	Δρ_max = 0.42 e Å⁻³
177 parameters	Δρ_min = −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)

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

References

Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds

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