4-Chloro-2-methyl-N-(2-methyl­phen­yl)­benzene­sulfonamide

Gowda, B.T.; Foro, S.; Nirmala, P.G.; Terao, H.; Fuess, H.

doi:10.1107/S1600536809009623

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o800

doi:10.1107/S1600536809009623

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4-Chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala,^a Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 10 March 2009; accepted 16 March 2009; online 19 March 2009)

In the crystal structure of the title compound, C₁₄H₁₄ClNO₂S, the two aromatic rings are tilted relative to each other by 45.8 (1)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur.

Related literature

For related structures, see: Gelbrich et al. (2007 ); Gowda et al. (2009a ,b ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₄ClNO₂S
M_r = 295.77
Triclinic, $[P \overline 1]$
a = 8.1200 (8) Å
b = 8.1832 (8) Å
c = 10.985 (1) Å
α = 95.81 (1)°
β = 96.92 (1)°
γ = 106.82 (1)°
V = 686.46 (11) Å³
Z = 2
Cu Kα radiation
μ = 3.86 mm⁻¹
T = 299 K
0.50 × 0.48 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.228, T_max = 0.500
2572 measured reflections
2366 independent reflections
2194 reflections with I > 2σ(I)
R_int = 0.054
3 standard reflections frequency: 120 min intensity decay: 2.5%

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.235
S = 1.10
2366 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.87 (4)	2.14 (4)	2.993 (4)	167 (3)
Symmetry code: (i) -x+1, -y, -z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ); 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/S1600536809009623/bt2900sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009623/bt2900Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of substituent effects on the structures of N-(aryl)-arylsulfonamides, the structure of 4-chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide has been determined (Gowda et al. 2009a,b). The conformations of the N—C bonds in the C—SO₂—NH—C segment have trans and gauche torsion angles with the S=O bonds (Fig. 1). The molecule is bent at the S atom with the C—SO₂—NH—C torsion angle of 73.0 (2). The ortho-methyl group in the sulfonyl benzene ring is oriented away from the S=O bonds and so also the ortho-methyl group in the anilino benzene ring from the N—H bond. The two benzene rings are tilted relative to each other by 45.8 (1)°, compared with the values of 86.6 (2)° (molecule 1) and 83.0 (2)° (molecule 2), in the two independent molecules of 4-chloro-2-methyl- N-(phenyl)benzenesulfonamide (Gowda et al., 2009a). The other bond parameters in the title compound are similar to those observed in 2,4-dimethyl-N-(phenyl)benzenesulfonamide (Gowda et al., 2009b) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing of the molecules is characterized by N—H···O(S) hydrogen bonds (Table 1, Fig.2) .

Related literature top

For related structures, see: Gelbrich et al. (2007); Gowda et al. (2009a,b); Perlovich et al. (2006).

Experimental top

A solution of m-chlorotoluene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) 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 4-chloro-2-methylbenzenesulfonylchloride was treated with o-toluidine 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 4-chloro-2-methyl-N- (2-methylphenyl)benzenesulfonamide 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. The single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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 the title compound showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of of the title compound with hydrogen bonding shown as dashed lines.

4-Chloro-2-methyl-N-(2-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₄ClNO₂S	Z = 2
M_r = 295.77	F(000) = 308
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.1200 (8) Å	Cell parameters from 25 reflections
b = 8.1832 (8) Å	θ = 5.7–25.2°
c = 10.985 (1) Å	µ = 3.86 mm⁻¹
α = 95.81 (1)°	T = 299 K
β = 96.92 (1)°	Prism, colourless
γ = 106.82 (1)°	0.50 × 0.48 × 0.18 mm
V = 686.46 (11) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	2194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 66.9°, θ_min = 4.1°
ω/2θ scans	h = −9→1
Absorption correction: psi-scan (North et al., 1968)	k = −9→9
T_min = 0.228, T_max = 0.500	l = −13→13
2572 measured reflections	3 standard reflections every 120 min
2366 independent reflections	intensity decay: 2.5%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.235	w = 1/[σ²(F_o²) + (0.1867P)² + 0.2192P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.003
2366 reflections	Δρ_max = 0.82 e Å⁻³
178 parameters	Δρ_min = −0.63 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (4)

Crystal data top

C₁₄H₁₄ClNO₂S	γ = 106.82 (1)°
M_r = 295.77	V = 686.46 (11) Å³
Triclinic, P1	Z = 2
a = 8.1200 (8) Å	Cu Kα radiation
b = 8.1832 (8) Å	µ = 3.86 mm⁻¹
c = 10.985 (1) Å	T = 299 K
α = 95.81 (1)°	0.50 × 0.48 × 0.18 mm
β = 96.92 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2194 reflections with I > 2σ(I)
Absorption correction: psi-scan (North et al., 1968)	R_int = 0.054
T_min = 0.228, T_max = 0.500	3 standard reflections every 120 min
2572 measured reflections	intensity decay: 2.5%
2366 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.235	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.82 e Å⁻³
2366 reflections	Δρ_min = −0.63 e Å⁻³
178 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
Cl1	0.35649 (13)	0.29943 (14)	0.56281 (9)	0.0698 (5)
S1	0.70711 (9)	−0.00610 (8)	0.15793 (6)	0.0388 (4)
O1	0.8587 (3)	−0.0468 (3)	0.2078 (2)	0.0511 (6)
O2	0.5669 (3)	−0.1383 (3)	0.0812 (2)	0.0518 (7)
N1	0.7667 (3)	0.1454 (3)	0.0718 (2)	0.0408 (6)
H1N	0.678 (5)	0.160 (5)	0.026 (3)	0.049*
C1	0.6176 (4)	0.0795 (4)	0.2802 (3)	0.0381 (7)
C2	0.7184 (4)	0.1738 (4)	0.3914 (3)	0.0446 (8)
C3	0.6322 (5)	0.2414 (4)	0.4757 (3)	0.0492 (8)
H3	0.6954	0.3075	0.5496	0.059*
C4	0.4541 (5)	0.2123 (4)	0.4518 (3)	0.0471 (8)
C5	0.3557 (4)	0.1194 (4)	0.3436 (3)	0.0483 (8)
H5	0.2361	0.1015	0.3284	0.058*
C6	0.4388 (4)	0.0529 (4)	0.2572 (3)	0.0445 (7)
H6	0.3743	−0.0105	0.1828	0.053*
C7	0.9159 (4)	0.2918 (4)	0.1137 (2)	0.0370 (7)
C8	0.8982 (4)	0.4545 (4)	0.1516 (3)	0.0417 (7)
C9	1.0502 (6)	0.5921 (4)	0.1866 (3)	0.0580 (9)
H9	1.0420	0.7016	0.2100	0.070*
C10	1.2117 (6)	0.5710 (5)	0.1876 (4)	0.0654 (11)
H10	1.3113	0.6648	0.2132	0.078*
C11	1.2262 (5)	0.4090 (6)	0.1501 (4)	0.0655 (11)
H11	1.3357	0.3943	0.1511	0.079*
C12	1.0791 (5)	0.2706 (5)	0.1118 (3)	0.0516 (8)
H12	1.0889	0.1629	0.0846	0.062*
C13	0.9139 (5)	0.2097 (6)	0.4271 (3)	0.0607 (10)
H13A	0.9401	0.1025	0.4258	0.073*
H13B	0.9513	0.2741	0.5088	0.073*
H13C	0.9736	0.2753	0.3691	0.073*
C14	0.7233 (5)	0.4810 (4)	0.1522 (4)	0.0570 (10)
H14A	0.6460	0.4174	0.0787	0.068*
H14B	0.7352	0.6015	0.1546	0.068*
H14C	0.6767	0.4410	0.2239	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0723 (8)	0.0846 (8)	0.0629 (7)	0.0384 (6)	0.0258 (5)	−0.0018 (5)
S1	0.0430 (6)	0.0280 (5)	0.0466 (5)	0.0131 (3)	0.0107 (3)	−0.0002 (3)
O1	0.0554 (14)	0.0426 (12)	0.0650 (14)	0.0270 (10)	0.0156 (11)	0.0088 (10)
O2	0.0570 (15)	0.0327 (11)	0.0614 (14)	0.0106 (10)	0.0117 (11)	−0.0058 (9)
N1	0.0440 (15)	0.0362 (13)	0.0422 (13)	0.0137 (11)	0.0079 (10)	−0.0001 (10)
C1	0.0431 (17)	0.0308 (14)	0.0427 (15)	0.0129 (11)	0.0114 (12)	0.0052 (11)
C2	0.0422 (18)	0.0510 (17)	0.0449 (16)	0.0191 (13)	0.0091 (13)	0.0103 (13)
C3	0.052 (2)	0.0490 (18)	0.0446 (16)	0.0155 (14)	0.0073 (14)	−0.0003 (13)
C4	0.053 (2)	0.0497 (18)	0.0484 (17)	0.0255 (15)	0.0195 (14)	0.0119 (14)
C5	0.0429 (18)	0.0519 (18)	0.0543 (18)	0.0202 (14)	0.0119 (14)	0.0052 (14)
C6	0.0441 (18)	0.0426 (16)	0.0473 (16)	0.0147 (13)	0.0081 (13)	0.0037 (12)
C7	0.0427 (16)	0.0365 (14)	0.0328 (13)	0.0119 (12)	0.0113 (11)	0.0043 (10)
C8	0.058 (2)	0.0339 (14)	0.0338 (14)	0.0128 (13)	0.0117 (12)	0.0031 (11)
C9	0.075 (3)	0.0388 (17)	0.0516 (18)	0.0032 (15)	0.0113 (16)	0.0070 (13)
C10	0.059 (2)	0.058 (2)	0.062 (2)	−0.0077 (17)	0.0005 (17)	0.0193 (17)
C11	0.041 (2)	0.082 (3)	0.073 (2)	0.0107 (18)	0.0111 (16)	0.032 (2)
C12	0.049 (2)	0.0553 (19)	0.0581 (19)	0.0217 (15)	0.0186 (15)	0.0146 (15)
C13	0.043 (2)	0.080 (3)	0.0544 (19)	0.0199 (17)	−0.0005 (15)	−0.0072 (17)
C14	0.074 (2)	0.0400 (17)	0.069 (2)	0.0274 (17)	0.0329 (19)	0.0081 (15)

Geometric parameters (Å, º) top

Cl1—C4	1.734 (3)	C7—C12	1.388 (5)
S1—O1	1.427 (2)	C7—C8	1.407 (4)
S1—O2	1.431 (2)	C8—C9	1.390 (5)
S1—N1	1.633 (3)	C8—C14	1.498 (5)
S1—C1	1.778 (3)	C9—C10	1.370 (6)
N1—C7	1.424 (4)	C9—H9	0.9300
N1—H1N	0.87 (4)	C10—C11	1.391 (7)
C1—C6	1.392 (5)	C10—H10	0.9300
C1—C2	1.400 (4)	C11—C12	1.373 (5)
C2—C3	1.389 (5)	C11—H11	0.9300
C2—C13	1.522 (5)	C12—H12	0.9300
C3—C4	1.383 (5)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.366 (5)	C13—H13C	0.9600
C5—C6	1.383 (5)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600

O1—S1—O2	119.17 (14)	C8—C7—N1	121.0 (3)
O1—S1—N1	108.06 (14)	C9—C8—C7	117.4 (3)
O2—S1—N1	105.21 (14)	C9—C8—C14	120.8 (3)
O1—S1—C1	109.71 (14)	C7—C8—C14	121.9 (3)
O2—S1—C1	106.93 (14)	C10—C9—C8	121.9 (3)
N1—S1—C1	107.12 (13)	C10—C9—H9	119.1
C7—N1—S1	121.1 (2)	C8—C9—H9	119.1
C7—N1—H1N	118 (2)	C9—C10—C11	119.8 (3)
S1—N1—H1N	112 (3)	C9—C10—H10	120.1
C6—C1—C2	121.0 (3)	C11—C10—H10	120.1
C6—C1—S1	115.7 (2)	C12—C11—C10	120.1 (4)
C2—C1—S1	123.3 (2)	C12—C11—H11	119.9
C3—C2—C1	116.9 (3)	C10—C11—H11	119.9
C3—C2—C13	117.4 (3)	C11—C12—C7	119.8 (3)
C1—C2—C13	125.6 (3)	C11—C12—H12	120.1
C4—C3—C2	121.3 (3)	C7—C12—H12	120.1
C4—C3—H3	119.4	C2—C13—H13A	109.5
C2—C3—H3	119.4	C2—C13—H13B	109.5
C5—C4—C3	121.7 (3)	H13A—C13—H13B	109.5
C5—C4—Cl1	120.0 (3)	C2—C13—H13C	109.5
C3—C4—Cl1	118.3 (3)	H13A—C13—H13C	109.5
C4—C5—C6	118.1 (3)	H13B—C13—H13C	109.5
C4—C5—H5	120.9	C8—C14—H14A	109.5
C6—C5—H5	120.9	C8—C14—H14B	109.5
C5—C6—C1	120.9 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.6	C8—C14—H14C	109.5
C1—C6—H6	119.6	H14A—C14—H14C	109.5
C12—C7—C8	121.0 (3)	H14B—C14—H14C	109.5
C12—C7—N1	118.0 (3)

O1—S1—N1—C7	−45.5 (2)	Cl1—C4—C5—C6	179.7 (2)
O2—S1—N1—C7	−173.8 (2)	C4—C5—C6—C1	0.2 (5)
C1—S1—N1—C7	72.7 (2)	C2—C1—C6—C5	0.2 (5)
O1—S1—C1—C6	−152.0 (2)	S1—C1—C6—C5	−177.4 (2)
O2—S1—C1—C6	−21.4 (3)	S1—N1—C7—C12	75.9 (3)
N1—S1—C1—C6	90.9 (2)	S1—N1—C7—C8	−106.4 (3)
O1—S1—C1—C2	30.4 (3)	C12—C7—C8—C9	0.1 (4)
O2—S1—C1—C2	161.0 (3)	N1—C7—C8—C9	−177.5 (3)
N1—S1—C1—C2	−86.6 (3)	C12—C7—C8—C14	178.9 (3)
C6—C1—C2—C3	−1.1 (5)	N1—C7—C8—C14	1.3 (4)
S1—C1—C2—C3	176.3 (2)	C7—C8—C9—C10	−1.6 (5)
C6—C1—C2—C13	179.4 (3)	C14—C8—C9—C10	179.5 (3)
S1—C1—C2—C13	−3.1 (5)	C8—C9—C10—C11	1.5 (6)
C1—C2—C3—C4	1.8 (5)	C9—C10—C11—C12	0.3 (6)
C13—C2—C3—C4	−178.7 (3)	C10—C11—C12—C7	−1.8 (5)
C2—C3—C4—C5	−1.5 (5)	C8—C7—C12—C11	1.6 (5)
C2—C3—C4—Cl1	179.3 (2)	N1—C7—C12—C11	179.3 (3)
C3—C4—C5—C6	0.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.87 (4)	2.14 (4)	2.993 (4)	167 (3)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄ClNO₂S
M_r	295.77
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.1200 (8), 8.1832 (8), 10.985 (1)
α, β, γ (°)	95.81 (1), 96.92 (1), 106.82 (1)
V (Å³)	686.46 (11)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.86
Crystal size (mm)	0.50 × 0.48 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Psi-scan (North et al., 1968)
T_min, T_max	0.228, 0.500
No. of measured, independent and observed [I > 2σ(I)] reflections	2572, 2366, 2194
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.235, 1.10
No. of reflections	2366
No. of parameters	178
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.63

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), 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···O2ⁱ	0.87 (4)	2.14 (4)	2.993 (4)	167 (3)

Symmetry code: (i) −x+1, −y, −z.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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Volume 65| Part 4| April 2009| Page o800

doi:10.1107/S1600536809009623

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