4-Methyl-N-(3-methyl­phen­yl)benzene­sulfonamide

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

doi:10.1107/S1600536809049332

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3208

doi:10.1107/S1600536809049332

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4-Methyl-N-(3-methylphenyl)benzenesulfonamide

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

^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 15 November 2009; accepted 18 November 2009; online 25 November 2009)

In the title compound, C₁₄H₁₅NO₂S, the conformation of the N—C bond in the C—SO₂—NH—C segment has gauche torsion angles with respect to the S=O bonds. Further, the conformation of the N—H bond is anti to the 3-methyl group in the aniline benzene ring. The molecule is bent at the N atom with a C—SO₂—NH—C torsion angle of 56.7 (3)°. The dihedral angle between the benzene rings is 83.9 (1)°. In the crystal, intermolecular N—H⋯O hydrogen bonds pack the molecules into a supramolecular structure.

Related literature

For the preparation of the title compound, see: Gowda et al. (2005 ). For a study of the effect of substituents on the crystal structures of N-(aryl)-arylsulfonamides, see: Gowda et al. (2009a ,b ); Nirmala et al.(2009 ). For bond lengths in other aryl sulfonamides, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₅NO₂S
M_r = 261.33
Monoclinic, C 2/c
a = 14.076 (3) Å
b = 14.519 (3) Å
c = 13.482 (2) Å
β = 98.10 (2)°
V = 2727.8 (9) Å³
Z = 8
Cu Kα radiation
μ = 2.06 mm⁻¹
T = 299 K
0.50 × 0.45 × 0.35 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.426, T_max = 0.533
5405 measured reflections
2436 independent reflections
2285 reflections with I > 2σ(I)
R_int = 0.148
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.163
S = 1.05
2436 reflections
169 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.839 (18)	2.10 (2)	2.914 (3)	163 (3)
Symmetry code: (i) -x, -y+1, -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/S1600536809049332/lx2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049332/lx2127Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of substituents on the crystal structures of N–(aryl)–arylsulfonamides (Gowda et al., 2009a,b; Nirmala et al., 2009), in the present work, the structure of 4–methyl–N–(3–methylphenyl)benzenesulfonamide (I) has been determined.

The conformation of the N—C bond in the C1—SO₂—NH—C7 segment of the structure has gauche torsions with respect to the SO bonds (Fig. 1). Further, the conformation of the N—H bond is anti to the 3–methyl group in the aniline benzene ring. The molecule is bent at the N atom with the C1—SO₂—NH—C7 torsion angle of 56.7 (3)°, compared to the values of -51.6 (3)° in 4–methyl–N–(phenyl)–benzenesulfonamide (II)(Gowda et al., 2009b), 60.0 (2)° in 4–methyl–N–(2–methylphenyl)benzenesulfonamide (III) (Nirmala et al., 2009) and -61.8 (2)° in 4–methyl–N–(3,4–dimethylphenyl)benzenesulfonamide (IV) (Gowda et al., 2009a). The two benzene rings in (I) are tilted relative to each other by 83.9 (1)°, compared to the values of 68.4 (1)° in (II), 49.7 (1)° in (III) and 47.8 (1)° in (IV). The other bond parameters are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007). The crystal packing stabilized by intermolecular N—H···O hydrogen bonds (Table 1) is shown in Fig.2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2005). For a study of the effect of substituents on the crystal structures of N–(aryl)–arylsulfonamides, see: Gowda et al. (2009a,b); Nirmala et al.(2009). For bond lengths in other aryl sulfonamides, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of toluene (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 benzenesulfonylchloride was treated with m–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 ml). The resultant solid 4–methyl–N–(3–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 (Gowda et al., 2005). The 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: 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 (I), showing the atom labelling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

4-Methyl-N-(3-methylphenyl)benzenesulfonamide top

Crystal data top

C₁₄H₁₅NO₂S	F(000) = 1104
M_r = 261.33	D_x = 1.273 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2yc	Cell parameters from 25 reflections
a = 14.076 (3) Å	θ = 5.2–23.5°
b = 14.519 (3) Å	µ = 2.06 mm⁻¹
c = 13.482 (2) Å	T = 299 K
β = 98.10 (2)°	Prism, colourless
V = 2727.8 (9) Å³	0.50 × 0.45 × 0.35 mm
Z = 8

Data collection top

Enraf–Nonius CAD-4 diffractometer	2285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.148
Graphite monochromator	θ_max = 67.0°, θ_min = 4.4°
ω/2θ scans	h = −16→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→17
T_min = 0.426, T_max = 0.533	l = −16→16
5405 measured reflections	3 standard reflections every 120 min
2436 independent reflections	intensity decay: 1.5%

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.163	w = 1/[σ²(F_o²) + (0.0638P)² + 2.2735P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2436 reflections	Δρ_max = 0.42 e Å⁻³
169 parameters	Δρ_min = −0.42 e Å⁻³
13 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: 0.0092 (7)

Crystal data top

C₁₄H₁₅NO₂S	V = 2727.8 (9) Å³
M_r = 261.33	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 14.076 (3) Å	µ = 2.06 mm⁻¹
b = 14.519 (3) Å	T = 299 K
c = 13.482 (2) Å	0.50 × 0.45 × 0.35 mm
β = 98.10 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2285 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.148
T_min = 0.426, T_max = 0.533	3 standard reflections every 120 min
5405 measured reflections	intensity decay: 1.5%
2436 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	13 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.42 e Å⁻³
2436 reflections	Δρ_min = −0.42 e Å⁻³
169 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	0.03543 (17)	0.26890 (18)	0.04684 (16)	0.0478 (6)
C2	−0.0487 (2)	0.2802 (3)	0.0874 (3)	0.0769 (9)
H2	−0.0754	0.3384	0.0915	0.092*
C3	−0.0921 (2)	0.2041 (4)	0.1217 (3)	0.0927 (13)
H3	−0.1487	0.2117	0.1490	0.111*
C4	−0.0551 (3)	0.1180 (3)	0.1169 (2)	0.0767 (10)
C5	0.0301 (2)	0.1079 (3)	0.0788 (2)	0.0706 (8)
H5	0.0576	0.0499	0.0768	0.085*
C6	0.0746 (2)	0.1826 (2)	0.0439 (2)	0.0576 (7)
H6	0.1319	0.1748	0.0180	0.069*
C7	0.17516 (16)	0.41609 (16)	0.18078 (17)	0.0450 (5)
C8	0.24019 (18)	0.34436 (19)	0.19055 (18)	0.0509 (6)
H8	0.2450	0.3058	0.1364	0.061*
C9	0.2985 (2)	0.3297 (2)	0.2811 (2)	0.0584 (7)
C10	0.2903 (2)	0.3882 (3)	0.3600 (2)	0.0690 (8)
H10	0.3293	0.3793	0.4208	0.083*
C11	0.2259 (2)	0.4588 (2)	0.3501 (2)	0.0695 (8)
H11	0.2217	0.4975	0.4043	0.083*
C12	0.1671 (2)	0.47364 (19)	0.2610 (2)	0.0561 (6)
H12	0.1227	0.5215	0.2548	0.067*
C13	−0.1073 (4)	0.0352 (4)	0.1498 (3)	0.1229 (19)
H13A	−0.1598	0.0199	0.0990	0.148*
H13B	−0.1314	0.0491	0.2112	0.148*
H13C	−0.0639	−0.0160	0.1601	0.148*
C14	0.3672 (3)	0.2506 (3)	0.2921 (3)	0.0958 (13)
H14A	0.3922	0.2412	0.2302	0.115*
H14B	0.3346	0.1959	0.3088	0.115*
H14C	0.4191	0.2638	0.3444	0.115*
N1	0.11662 (17)	0.43561 (15)	0.08911 (16)	0.0578 (6)
H1N	0.0746 (19)	0.475 (2)	0.096 (3)	0.069*
O1	0.17370 (14)	0.33270 (13)	−0.03761 (13)	0.0573 (5)
O2	0.01925 (16)	0.41182 (14)	−0.07129 (14)	0.0680 (6)
S1	0.08931 (4)	0.36406 (4)	−0.00253 (4)	0.0483 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0524 (12)	0.0520 (14)	0.0383 (11)	0.0040 (11)	0.0037 (9)	−0.0048 (10)
C2	0.0713 (18)	0.087 (2)	0.0776 (19)	0.0045 (18)	0.0286 (15)	−0.0209 (18)
C3	0.0718 (19)	0.137 (4)	0.076 (2)	−0.022 (2)	0.0362 (16)	−0.023 (2)
C4	0.088 (2)	0.095 (2)	0.0472 (14)	−0.033 (2)	0.0092 (14)	−0.0032 (15)
C5	0.0826 (19)	0.0594 (17)	0.0694 (18)	−0.0097 (17)	0.0089 (15)	0.0091 (15)
C6	0.0628 (14)	0.0497 (14)	0.0613 (15)	0.0025 (13)	0.0125 (11)	0.0044 (12)
C7	0.0516 (12)	0.0368 (11)	0.0452 (12)	−0.0016 (10)	0.0020 (9)	0.0014 (9)
C8	0.0592 (14)	0.0476 (13)	0.0442 (12)	0.0045 (12)	0.0014 (10)	−0.0033 (10)
C9	0.0624 (14)	0.0568 (16)	0.0521 (14)	0.0069 (13)	−0.0054 (11)	0.0012 (12)
C10	0.0826 (19)	0.0710 (19)	0.0478 (14)	0.0012 (17)	−0.0098 (13)	−0.0047 (14)
C11	0.0908 (19)	0.0649 (18)	0.0508 (14)	0.0009 (17)	0.0033 (13)	−0.0156 (13)
C12	0.0669 (14)	0.0449 (14)	0.0563 (14)	0.0021 (12)	0.0078 (11)	−0.0050 (11)
C13	0.141 (4)	0.152 (5)	0.078 (2)	−0.078 (4)	0.023 (2)	0.011 (3)
C14	0.102 (3)	0.100 (3)	0.076 (2)	0.042 (2)	−0.0205 (19)	−0.007 (2)
N1	0.0746 (14)	0.0409 (11)	0.0528 (12)	0.0174 (11)	−0.0088 (10)	−0.0052 (9)
O1	0.0713 (11)	0.0513 (10)	0.0504 (9)	0.0047 (9)	0.0127 (8)	0.0068 (8)
O2	0.0909 (14)	0.0553 (11)	0.0502 (10)	0.0221 (11)	−0.0162 (9)	0.0009 (8)
S1	0.0622 (5)	0.0406 (4)	0.0400 (4)	0.0101 (2)	0.0004 (3)	0.0017 (2)

Geometric parameters (Å, º) top

C1—C6	1.372 (4)	C9—C10	1.378 (4)
C1—C2	1.382 (4)	C9—C14	1.496 (5)
C1—S1	1.752 (3)	C10—C11	1.362 (5)
C2—C3	1.375 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.377 (4)
C3—C4	1.358 (7)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.378 (5)	C13—H13A	0.9600
C4—C13	1.508 (5)	C13—H13B	0.9600
C5—C6	1.369 (4)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.380 (4)	C14—H14C	0.9600
C7—C12	1.384 (4)	N1—S1	1.619 (2)
C7—N1	1.414 (3)	N1—H1N	0.839 (18)
C8—C9	1.388 (3)	O1—S1	1.414 (2)
C8—H8	0.9300	O2—S1	1.4335 (18)

C6—C1—C2	119.4 (3)	C9—C10—H10	119.5
C6—C1—S1	120.79 (19)	C10—C11—C12	120.8 (3)
C2—C1—S1	119.8 (2)	C10—C11—H11	119.6
C3—C2—C1	119.0 (3)	C12—C11—H11	119.6
C3—C2—H2	120.5	C11—C12—C7	118.8 (3)
C1—C2—H2	120.5	C11—C12—H12	120.6
C4—C3—C2	122.1 (3)	C7—C12—H12	120.6
C4—C3—H3	118.9	C4—C13—H13A	109.5
C2—C3—H3	118.9	C4—C13—H13B	109.5
C3—C4—C5	118.4 (4)	H13A—C13—H13B	109.5
C3—C4—C13	120.9 (4)	C4—C13—H13C	109.5
C5—C4—C13	120.7 (4)	H13A—C13—H13C	109.5
C6—C5—C4	120.6 (4)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C9—C14—H14A	109.5
C4—C5—H5	119.7	C9—C14—H14B	109.5
C5—C6—C1	120.5 (3)	H14A—C14—H14B	109.5
C5—C6—H6	119.7	C9—C14—H14C	109.5
C1—C6—H6	119.7	H14A—C14—H14C	109.5
C8—C7—C12	120.5 (2)	H14B—C14—H14C	109.5
C8—C7—N1	122.1 (2)	C7—N1—S1	125.80 (17)
C12—C7—N1	117.4 (2)	C7—N1—H1N	112 (2)
C7—C8—C9	120.1 (2)	S1—N1—H1N	115 (2)
C7—C8—H8	119.9	O1—S1—O2	118.24 (12)
C9—C8—H8	119.9	O1—S1—N1	109.97 (12)
C10—C9—C8	118.7 (3)	O2—S1—N1	104.53 (12)
C10—C9—C14	121.4 (3)	O1—S1—C1	107.58 (11)
C8—C9—C14	119.9 (3)	O2—S1—C1	109.39 (13)
C11—C10—C9	121.1 (3)	N1—S1—C1	106.57 (12)
C11—C10—H10	119.5

C6—C1—C2—C3	−1.5 (4)	C9—C10—C11—C12	0.1 (5)
S1—C1—C2—C3	177.1 (2)	C10—C11—C12—C7	−0.8 (5)
C1—C2—C3—C4	0.0 (5)	C8—C7—C12—C11	0.9 (4)
C2—C3—C4—C5	1.8 (5)	N1—C7—C12—C11	−177.3 (3)
C2—C3—C4—C13	−176.6 (4)	C8—C7—N1—S1	21.5 (4)
C3—C4—C5—C6	−1.9 (5)	C12—C7—N1—S1	−160.3 (2)
C13—C4—C5—C6	176.4 (3)	C7—N1—S1—O1	−59.6 (3)
C4—C5—C6—C1	0.4 (5)	C7—N1—S1—O2	172.5 (2)
C2—C1—C6—C5	1.4 (4)	C7—N1—S1—C1	56.7 (3)
S1—C1—C6—C5	−177.3 (2)	C6—C1—S1—O1	−1.9 (2)
C12—C7—C8—C9	−0.3 (4)	C2—C1—S1—O1	179.5 (2)
N1—C7—C8—C9	177.8 (3)	C6—C1—S1—O2	127.7 (2)
C7—C8—C9—C10	−0.4 (4)	C2—C1—S1—O2	−50.9 (3)
C7—C8—C9—C14	178.6 (3)	C6—C1—S1—N1	−119.8 (2)
C8—C9—C10—C11	0.5 (5)	C2—C1—S1—N1	61.6 (2)
C14—C9—C10—C11	−178.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.10 (2)	2.914 (3)	163 (3)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₂S
M_r	261.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	299
a, b, c (Å)	14.076 (3), 14.519 (3), 13.482 (2)
β (°)	98.10 (2)
V (Å³)	2727.8 (9)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.06
Crystal size (mm)	0.50 × 0.45 × 0.35

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.426, 0.533
No. of measured, independent and observed [I > 2σ(I)] reflections	5405, 2436, 2285
R_int	0.148
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.163, 1.05
No. of reflections	2436
No. of parameters	169
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.42

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	0.839 (18)	2.10 (2)	2.914 (3)	163 (3)

Symmetry code: (i) −x, −y+1, −z.

References

Enraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 65| Part 12| December 2009| Page o3208

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