4-Methyl-N-(3-methyl-phen-yl)benzene-sulfonamide.

In the title compound, C(14)H(15)NO(2)S, the conformation of the N-C bond in the C-SO(2)-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 mol-ecule is bent at the N atom with a C-SO(2)-NH-C torsion angle of 56.7 (3)°. The dihedral angle between the benzene rings is 83.9 (1)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds pack the mol-ecules into a supra-molecular 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. (2009 ▶); 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 = 261.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.163

S = 1.05

2436 reflections

169 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.42 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049332/lx2127sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H15NO2S	F(000) = 1104
Mr = 261.33	Dx = 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

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

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(Fo2) + (0.0638P)2 + 2.2735P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2436 reflections	Δρmax = 0.42 e Å−3
169 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)

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) .