N-(3-Chloro­phen­yl)-2,4-dimethyl­benzene­sulfonamide

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811029400

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2178

doi:10.1107/S1600536811029400

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N-(3-Chlorophenyl)-2,4-dimethylbenzenesulfonamide

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 20 July 2011; accepted 20 July 2011; online 30 July 2011)

In the molecule of the title compound, C₁₄H₁₄ClNO₂S, the N—H bond is in a syn position with respect to the meta-Cl atom in the aniline ring. The molecule is twisted about the N—S bond with a C—SO₂—NH—C torsion angle of 44.55 (17)°. The two aromatic rings are inclined relative to each other by 66.2 (1)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains parallel to the b axis.

Related literature

For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001 ). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004 ); Gowda et al. (1999 ), on N-(aryl)methanesulfonamides, see: Gowda et al. (2007 ) and on N-(aryl)arylsulfonamides, see: Gelbrich et al. (2007 ); Gowda et al. (2010 ); Perlovich et al. (2006 ). For the preparation of the title compound, See: Savitha & Gowda (2006 )

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 295.77
Monoclinic, P 2₁ /c
a = 9.0385 (7) Å
b = 9.7830 (7) Å
c = 15.897 (1) Å
β = 97.284 (7)°
V = 1394.33 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.44 × 0.40 × 0.32 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.837, T_max = 0.877
5245 measured reflections
2841 independent reflections
2438 reflections with I > 2σ(I)
R_int = 0.009

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.103
S = 1.06
2841 reflections
177 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.84 (2)	2.32 (2)	3.117 (2)	158 (2)
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029400/bt5582sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029400/bt5582Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029400/bt5582Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically important compounds. The hydrogen bonding preferences of sulfonamides have been investigated (Adsmond & Grant, 2001). As part of our work on the substituent effects on the structures and other aspects of N-(aryl)-amides (Arjunan et al., 2004; Gowda et al., 1999), N-(aryl)-methanesulfonamides (Gowda et al., 2007) and N-(aryl)-arylsulfonamides (Gowda et al., 2010), in the present work, the crystal structure of N-(3-chlorophenyl)-2,4-dimethylbenzene- sulfonamide (I) has been determined (Fig. 1). The conformation of the N—C bond in the C—SO₂—NH—C segment has gauche torsions with respect to the S═O bonds. The molecule is bent at the S atom with the C1—SO₂—NH—C7 torsion angle of 44.6 (2)°, compared to the values of -54.9 (2)° in N-(2-chlorophenyl)-2,4-dimethylbenzenesulfonamide (II) (Gowda et al., 2010). Further, the conformation of the N—H bond in (I) is syn to the meta-chloro group in the anilino ring.

The two benzene rings in (I) are tilted relative to each other by 75.7 (1)°, compared to the value of 66.2 (1)° (II). The other bond parameters in (I) are similar to those observed in (II) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

The crystal packing of molecules in (I) via N—H···O(S) hydrogen bonds (Table 1) is shown in Fig.2.

Related literature top

For hydrogen bonding modes of sulfonamides, see: Adsmond & Grant (2001). For studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Arjunan et al. (2004); Gowda et al. (1999), on N-(aryl)-methanesulfonamides, see: Gowda et al. (2007) and on N-(aryl)-arylsulfonamides, see: Gelbrich et al. (2007); Gowda et al. (2010); Perlovich et al. (2006). For the preparation of the title compound, See: Savitha & Gowda (2006)

Experimental top

The solution of 1,3-xylene (1,3-dimethylbenzene) (10 ml) in chloroform (40 ml) was treated dropwise with chlorosulfonic acid (25 ml) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dimethylbenzenesulfonylchloride was treated with 3-chloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 cc). The resultant solid N-(3-chlorophenyl)-2,4-dimethylbenzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006).

The prism like colourless single crystals used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

N-(3-Chlorophenyl)-2,4-dimethylbenzenesulfonamide top

Crystal data top

C₁₄H₁₄ClNO₂S	F(000) = 616
M_r = 295.77	D_x = 1.409 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2954 reflections
a = 9.0385 (7) Å	θ = 2.6–27.8°
b = 9.7830 (7) Å	µ = 0.42 mm⁻¹
c = 15.897 (1) Å	T = 293 K
β = 97.284 (7)°	Prism, colourless
V = 1394.33 (17) Å³	0.44 × 0.40 × 0.32 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2841 independent reflections
Radiation source: fine-focus sealed tube	2438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.009
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→5
T_min = 0.837, T_max = 0.877	k = −12→5
5245 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0568P)² + 0.5258P] where P = (F_o² + 2F_c²)/3
2841 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.28 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₄ClNO₂S	V = 1394.33 (17) Å³
M_r = 295.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.0385 (7) Å	µ = 0.42 mm⁻¹
b = 9.7830 (7) Å	T = 293 K
c = 15.897 (1) Å	0.44 × 0.40 × 0.32 mm
β = 97.284 (7)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2841 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2438 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.877	R_int = 0.009
5245 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.28 e Å⁻³
2841 reflections	Δρ_min = −0.36 e Å⁻³
177 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.89077 (18)	0.14785 (17)	0.62875 (11)	0.0313 (4)
C2	0.90726 (19)	0.19319 (18)	0.54672 (11)	0.0359 (4)
C3	0.8365 (2)	0.1167 (2)	0.47948 (12)	0.0407 (4)
H3	0.8471	0.1439	0.4245	0.049*
C4	0.7512 (2)	0.0022 (2)	0.49045 (12)	0.0413 (4)
C5	0.7383 (2)	−0.0396 (2)	0.57271 (13)	0.0453 (5)
H5	0.6825	−0.1170	0.5816	0.054*
C6	0.8074 (2)	0.03244 (19)	0.64125 (12)	0.0385 (4)
H6	0.7980	0.0035	0.6960	0.046*
C7	0.73064 (18)	0.40051 (18)	0.70252 (11)	0.0328 (4)
C8	0.67615 (19)	0.50629 (19)	0.64977 (12)	0.0371 (4)
H8	0.7410	0.5643	0.6259	0.045*
C9	0.5229 (2)	0.5243 (2)	0.63306 (12)	0.0402 (4)
C10	0.4248 (2)	0.4403 (2)	0.66791 (13)	0.0459 (5)
H10	0.3224	0.4542	0.6563	0.055*
C11	0.4810 (2)	0.3354 (2)	0.72028 (14)	0.0467 (5)
H11	0.4157	0.2778	0.7440	0.056*
C12	0.6335 (2)	0.3141 (2)	0.73829 (13)	0.0410 (4)
H12	0.6703	0.2430	0.7738	0.049*
C13	0.9916 (3)	0.3198 (2)	0.52740 (15)	0.0575 (6)
H13A	1.0910	0.3159	0.5569	0.069*
H13B	0.9415	0.3991	0.5455	0.069*
H13C	0.9960	0.3252	0.4675	0.069*
C14	0.6723 (3)	−0.0736 (3)	0.41520 (15)	0.0614 (6)
H14A	0.7398	−0.0875	0.3740	0.074*
H14B	0.5881	−0.0212	0.3904	0.074*
H14C	0.6387	−0.1606	0.4334	0.074*
N1	0.88789 (16)	0.38382 (16)	0.72030 (11)	0.0376 (4)
H1N	0.943 (2)	0.4465 (19)	0.7057 (13)	0.045*
O1	0.93966 (15)	0.15746 (14)	0.79211 (8)	0.0437 (3)
O2	1.12517 (14)	0.26929 (15)	0.71487 (9)	0.0469 (4)
Cl1	0.45335 (6)	0.65483 (6)	0.56450 (4)	0.06029 (19)
S1	0.97232 (4)	0.23553 (4)	0.72011 (3)	0.03353 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0310 (8)	0.0294 (8)	0.0333 (8)	0.0027 (6)	0.0027 (6)	0.0007 (7)
C2	0.0360 (9)	0.0325 (9)	0.0395 (9)	0.0025 (7)	0.0061 (7)	0.0050 (7)
C3	0.0440 (10)	0.0439 (10)	0.0339 (9)	0.0081 (8)	0.0037 (7)	0.0030 (8)
C4	0.0393 (9)	0.0408 (10)	0.0427 (10)	0.0060 (8)	0.0005 (8)	−0.0079 (8)
C5	0.0475 (11)	0.0349 (10)	0.0534 (12)	−0.0084 (8)	0.0064 (9)	−0.0023 (8)
C6	0.0422 (9)	0.0347 (9)	0.0386 (9)	−0.0038 (8)	0.0055 (7)	0.0041 (7)
C7	0.0273 (8)	0.0326 (8)	0.0384 (9)	−0.0005 (7)	0.0042 (7)	−0.0097 (7)
C8	0.0346 (9)	0.0342 (9)	0.0432 (10)	−0.0012 (7)	0.0074 (7)	−0.0047 (8)
C9	0.0373 (9)	0.0402 (10)	0.0419 (10)	0.0053 (8)	0.0006 (7)	−0.0080 (8)
C10	0.0284 (9)	0.0547 (12)	0.0540 (12)	0.0006 (8)	0.0032 (8)	−0.0118 (10)
C11	0.0338 (9)	0.0515 (12)	0.0563 (12)	−0.0088 (8)	0.0110 (9)	−0.0037 (10)
C12	0.0367 (9)	0.0386 (10)	0.0483 (11)	−0.0019 (8)	0.0077 (8)	0.0010 (8)
C13	0.0710 (14)	0.0507 (13)	0.0517 (13)	−0.0151 (11)	0.0110 (11)	0.0133 (10)
C14	0.0632 (14)	0.0641 (15)	0.0537 (13)	−0.0016 (12)	−0.0052 (11)	−0.0189 (12)
N1	0.0270 (7)	0.0298 (8)	0.0558 (10)	−0.0027 (6)	0.0037 (7)	−0.0041 (7)
O1	0.0500 (8)	0.0452 (8)	0.0348 (7)	0.0053 (6)	0.0014 (6)	0.0012 (6)
O2	0.0261 (6)	0.0531 (8)	0.0605 (9)	0.0008 (6)	0.0013 (6)	−0.0101 (7)
Cl1	0.0576 (3)	0.0566 (3)	0.0637 (4)	0.0163 (3)	−0.0036 (3)	0.0070 (3)
S1	0.0284 (2)	0.0337 (2)	0.0376 (2)	0.00265 (16)	0.00062 (16)	−0.00264 (17)

Geometric parameters (Å, º) top

C1—C6	1.386 (2)	C9—C10	1.376 (3)
C1—C2	1.403 (2)	C9—Cl1	1.744 (2)
C1—S1	1.7655 (17)	C10—C11	1.378 (3)
C2—C3	1.392 (3)	C10—H10	0.9300
C2—C13	1.506 (3)	C11—C12	1.388 (3)
C3—C4	1.383 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.389 (3)	C13—H13A	0.9600
C4—C14	1.508 (3)	C13—H13B	0.9600
C5—C6	1.379 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.383 (3)	C14—H14C	0.9600
C7—C12	1.391 (3)	N1—S1	1.6394 (15)
C7—N1	1.423 (2)	N1—H1N	0.844 (15)
C8—C9	1.388 (2)	O1—S1	1.4375 (14)
C8—H8	0.9300	O2—S1	1.4331 (13)

C6—C1—C2	120.98 (16)	C11—C10—H10	120.6
C6—C1—S1	117.11 (13)	C10—C11—C12	121.16 (18)
C2—C1—S1	121.91 (13)	C10—C11—H11	119.4
C3—C2—C1	116.81 (16)	C12—C11—H11	119.4
C3—C2—C13	118.72 (17)	C11—C12—C7	119.09 (18)
C1—C2—C13	124.44 (18)	C11—C12—H12	120.5
C4—C3—C2	123.20 (17)	C7—C12—H12	120.5
C4—C3—H3	118.4	C2—C13—H13A	109.5
C2—C3—H3	118.4	C2—C13—H13B	109.5
C3—C4—C5	118.18 (17)	H13A—C13—H13B	109.5
C3—C4—C14	120.90 (19)	C2—C13—H13C	109.5
C5—C4—C14	120.92 (19)	H13A—C13—H13C	109.5
C6—C5—C4	120.60 (18)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C4—C14—H14A	109.5
C4—C5—H5	119.7	C4—C14—H14B	109.5
C5—C6—C1	120.23 (17)	H14A—C14—H14B	109.5
C5—C6—H6	119.9	C4—C14—H14C	109.5
C1—C6—H6	119.9	H14A—C14—H14C	109.5
C8—C7—C12	120.54 (16)	H14B—C14—H14C	109.5
C8—C7—N1	118.44 (16)	C7—N1—S1	123.69 (12)
C12—C7—N1	121.01 (17)	C7—N1—H1N	118.4 (15)
C7—C8—C9	118.76 (17)	S1—N1—H1N	110.5 (15)
C7—C8—H8	120.6	O2—S1—O1	117.75 (9)
C9—C8—H8	120.6	O2—S1—N1	104.39 (8)
C10—C9—C8	121.73 (18)	O1—S1—N1	109.03 (8)
C10—C9—Cl1	119.26 (15)	O2—S1—C1	111.66 (8)
C8—C9—Cl1	119.00 (15)	O1—S1—C1	106.89 (8)
C9—C10—C11	118.72 (17)	N1—S1—C1	106.59 (8)
C9—C10—H10	120.6

C6—C1—C2—C3	−0.1 (3)	C8—C9—C10—C11	−0.4 (3)
S1—C1—C2—C3	−179.26 (13)	Cl1—C9—C10—C11	178.36 (15)
C6—C1—C2—C13	177.94 (19)	C9—C10—C11—C12	0.3 (3)
S1—C1—C2—C13	−1.2 (3)	C10—C11—C12—C7	−0.1 (3)
C1—C2—C3—C4	1.0 (3)	C8—C7—C12—C11	0.0 (3)
C13—C2—C3—C4	−177.20 (19)	N1—C7—C12—C11	179.00 (17)
C2—C3—C4—C5	−1.3 (3)	C8—C7—N1—S1	−136.09 (15)
C2—C3—C4—C14	177.68 (18)	C12—C7—N1—S1	44.9 (2)
C3—C4—C5—C6	0.8 (3)	C7—N1—S1—O2	162.85 (15)
C14—C4—C5—C6	−178.21 (19)	C7—N1—S1—O1	−70.50 (17)
C4—C5—C6—C1	0.0 (3)	C7—N1—S1—C1	44.55 (17)
C2—C1—C6—C5	−0.3 (3)	C6—C1—S1—O2	133.91 (14)
S1—C1—C6—C5	178.83 (15)	C2—C1—S1—O2	−46.93 (17)
C12—C7—C8—C9	−0.2 (3)	C6—C1—S1—O1	3.82 (16)
N1—C7—C8—C9	−179.16 (16)	C2—C1—S1—O1	−177.03 (14)
C7—C8—C9—C10	0.4 (3)	C6—C1—S1—N1	−112.67 (14)
C7—C8—C9—Cl1	−178.42 (13)	C2—C1—S1—N1	66.48 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.32 (2)	3.117 (2)	158 (2)

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO₂S
M_r	295.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.0385 (7), 9.7830 (7), 15.897 (1)
β (°)	97.284 (7)
V (Å³)	1394.33 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.44 × 0.40 × 0.32

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.837, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	5245, 2841, 2438
R_int	0.009
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.103, 1.06
No. of reflections	2841
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)	0.28, −0.36

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.844 (15)	2.317 (17)	3.117 (2)	158 (2)

Symmetry code: (i) −x+2, y+1/2, −z+3/2.

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

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