N-(3,4-Dimethyl-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

In the title compound, C(16)H(19)NO(2)S, the dihedral angle between the aromatic rings is 47.2 (2)°. The crystal structure features zigzag C(4) chains linked by N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our study on the effect of substituents on the structures of N-(ar­yl)aryl­sulfonamides, see: Gowda et al. (2009a ▶,b ▶); Nirmala et al. (2010 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C16H19NO2S

M = 289.38

Monoclinic,

a = 9.732 (1) Å

b = 15.045 (2) Å

c = 10.425 (1) Å

β = 100.10 (1)°

V = 1502.8 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.92 mm−1

T = 299 K

0.45 × 0.38 × 0.28 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.479, T max = 0.616

2858 measured reflections

2672 independent reflections

2265 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.338

S = 1.59

2672 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.71 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/S1600536810014418/bt5248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014418/bt5248Isup2.hkl

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

C16H19NO2S	F(000) = 616
Mr = 289.38	Dx = 1.279 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.732 (1) Å	θ = 4.6–22.4°
b = 15.045 (2) Å	µ = 1.92 mm−1
c = 10.425 (1) Å	T = 299 K
β = 100.10 (1)°	Prism, yellow
V = 1502.8 (3) Å3	0.45 × 0.38 × 0.28 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2265 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
graphite	θmax = 67.0°, θmin = 4.6°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −17→0
Tmin = 0.479, Tmax = 0.616	l = −12→1
2858 measured reflections	3 standard reflections every 120 min
2672 independent reflections	intensity decay: 1.0%

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.338	H-atom parameters constrained
S = 1.59	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2672 reflections	(Δ/σ)max = 0.042
185 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

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.

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
S1	−0.01170 (9)	0.29486 (6)	0.42947 (8)	0.0414 (5)
O1	−0.1509 (3)	0.3027 (2)	0.3594 (3)	0.0581 (9)
O2	0.0109 (3)	0.2694 (2)	0.5633 (3)	0.0539 (9)
N1	0.0626 (3)	0.2187 (2)	0.3527 (3)	0.0420 (8)
H1N	0.0143	0.1909	0.2880	0.050*
C1	0.0835 (4)	0.3947 (2)	0.4209 (4)	0.0407 (9)
C2	0.0551 (4)	0.4535 (3)	0.3159 (4)	0.0462 (10)
C3	0.1420 (5)	0.5271 (3)	0.3193 (5)	0.0551 (11)
H3	0.1251	0.5673	0.2507	0.066*
C4	0.2520 (5)	0.5435 (3)	0.4192 (5)	0.0571 (12)
C5	0.2745 (6)	0.4854 (3)	0.5202 (6)	0.0658 (13)
H5	0.3478	0.4954	0.5889	0.079*
C6	0.1904 (5)	0.4114 (3)	0.5229 (4)	0.0547 (11)
H6	0.2062	0.3729	0.5938	0.066*
C7	0.2084 (4)	0.1981 (2)	0.3928 (4)	0.0406 (9)
C8	0.2517 (4)	0.1470 (3)	0.5026 (4)	0.0460 (10)
H8	0.1860	0.1251	0.5494	0.055*
C9	0.3919 (5)	0.1279 (3)	0.5439 (4)	0.0501 (10)
C10	0.4903 (5)	0.1578 (3)	0.4705 (5)	0.0541 (11)
C11	0.4431 (5)	0.2072 (3)	0.3588 (5)	0.0578 (12)
H11	0.5072	0.2266	0.3084	0.069*
C12	0.3043 (5)	0.2284 (3)	0.3204 (4)	0.0492 (10)
H12	0.2757	0.2628	0.2464	0.059*
C13	−0.0607 (6)	0.4423 (4)	0.2013 (5)	0.0685 (14)
H13A	−0.1470	0.4619	0.2245	0.082*
H13B	−0.0683	0.3808	0.1767	0.082*
H13C	−0.0408	0.4770	0.1295	0.082*
C14	0.3438 (7)	0.6239 (4)	0.4164 (9)	0.094 (2)
H14A	0.2915	0.6702	0.3666	0.113*
H14B	0.4227	0.6084	0.3772	0.113*
H14C	0.3756	0.6444	0.5038	0.113*
C15	0.4395 (6)	0.0747 (3)	0.6666 (5)	0.0719 (15)
H15A	0.4804	0.0199	0.6449	0.086*
H15B	0.3609	0.0622	0.7080	0.086*
H15C	0.5075	0.1083	0.7250	0.086*
C16	0.6417 (6)	0.1387 (4)	0.5107 (7)	0.0804 (18)
H16A	0.6534	0.0807	0.5496	0.096*
H16B	0.6828	0.1825	0.5729	0.096*
H16C	0.6865	0.1406	0.4358	0.096*

	U11	U22	U33	U12	U13	U23
S1	0.0466 (7)	0.0476 (7)	0.0298 (7)	−0.0046 (3)	0.0060 (4)	0.0006 (3)
O1	0.0496 (19)	0.065 (2)	0.058 (2)	−0.0046 (13)	0.0062 (15)	0.0016 (14)
O2	0.075 (2)	0.0593 (18)	0.0301 (16)	−0.0065 (14)	0.0176 (14)	0.0018 (11)
N1	0.0517 (19)	0.0441 (17)	0.0270 (15)	−0.0076 (13)	−0.0018 (13)	−0.0048 (12)
C1	0.046 (2)	0.0384 (19)	0.0377 (19)	0.0013 (14)	0.0077 (15)	−0.0023 (14)
C2	0.052 (2)	0.043 (2)	0.043 (2)	0.0089 (16)	0.0090 (17)	−0.0022 (16)
C3	0.065 (3)	0.044 (2)	0.060 (3)	0.0053 (19)	0.020 (2)	0.0052 (19)
C4	0.061 (3)	0.042 (2)	0.074 (3)	−0.0055 (18)	0.025 (2)	−0.017 (2)
C5	0.063 (3)	0.066 (3)	0.064 (3)	−0.011 (2)	0.000 (2)	−0.019 (2)
C6	0.058 (2)	0.054 (2)	0.047 (2)	−0.0079 (19)	−0.0055 (18)	−0.0016 (19)
C7	0.053 (2)	0.0352 (18)	0.0312 (18)	−0.0039 (14)	0.0021 (16)	−0.0068 (13)
C8	0.060 (2)	0.041 (2)	0.0369 (19)	0.0011 (16)	0.0080 (17)	−0.0016 (15)
C9	0.068 (3)	0.0382 (19)	0.039 (2)	0.0048 (17)	−0.0056 (18)	−0.0041 (16)
C10	0.060 (3)	0.041 (2)	0.057 (2)	−0.0015 (17)	−0.0011 (19)	−0.0083 (18)
C11	0.061 (3)	0.057 (3)	0.056 (3)	0.0009 (19)	0.012 (2)	−0.0007 (19)
C12	0.062 (2)	0.049 (2)	0.036 (2)	−0.0008 (18)	0.0076 (18)	0.0022 (17)
C13	0.084 (3)	0.059 (3)	0.053 (3)	0.005 (2)	−0.011 (2)	0.015 (2)
C14	0.089 (4)	0.063 (3)	0.138 (6)	−0.023 (3)	0.041 (4)	−0.026 (4)
C15	0.100 (4)	0.057 (3)	0.050 (3)	0.016 (3)	−0.009 (3)	0.009 (2)
C16	0.069 (3)	0.065 (3)	0.098 (4)	0.003 (2)	−0.012 (3)	−0.006 (3)

S1—O2	1.426 (3)	C8—H8	0.9300
S1—O1	1.427 (3)	C9—C10	1.401 (7)
S1—N1	1.636 (3)	C9—C15	1.511 (6)
S1—C1	1.775 (4)	C10—C11	1.391 (7)
N1—C7	1.441 (5)	C10—C16	1.487 (7)
N1—H1N	0.8600	C11—C12	1.377 (6)
C1—C6	1.374 (5)	C11—H11	0.9300
C1—C2	1.397 (6)	C12—H12	0.9300
C2—C3	1.389 (6)	C13—H13A	0.9600
C2—C13	1.501 (6)	C13—H13B	0.9600
C3—C4	1.378 (7)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.357 (8)	C14—H14B	0.9600
C4—C14	1.507 (7)	C14—H14C	0.9600
C5—C6	1.385 (7)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C12	1.377 (6)	C16—H16A	0.9600
C7—C8	1.382 (5)	C16—H16B	0.9600
C8—C9	1.387 (6)	C16—H16C	0.9600
O2—S1—O1	119.5 (2)	C10—C9—C15	119.6 (4)
O2—S1—N1	106.57 (18)	C11—C10—C9	118.2 (4)
O1—S1—N1	105.59 (18)	C11—C10—C16	120.3 (5)
O2—S1—C1	106.50 (19)	C9—C10—C16	121.5 (5)
O1—S1—C1	111.18 (18)	C12—C11—C10	122.0 (5)
N1—S1—C1	106.75 (17)	C12—C11—H11	119.0
C7—N1—S1	120.4 (2)	C10—C11—H11	119.0
C7—N1—H1N	119.8	C11—C12—C7	119.3 (4)
S1—N1—H1N	119.8	C11—C12—H12	120.4
C6—C1—C2	120.6 (4)	C7—C12—H12	120.4
C6—C1—S1	116.5 (3)	C2—C13—H13A	109.5
C2—C1—S1	122.9 (3)	C2—C13—H13B	109.5
C3—C2—C1	116.6 (4)	H13A—C13—H13B	109.5
C3—C2—C13	118.6 (4)	C2—C13—H13C	109.5
C1—C2—C13	124.7 (4)	H13A—C13—H13C	109.5
C4—C3—C2	123.4 (4)	H13B—C13—H13C	109.5
C4—C3—H3	118.3	C4—C14—H14A	109.5
C2—C3—H3	118.3	C4—C14—H14B	109.5
C5—C4—C3	118.0 (4)	H14A—C14—H14B	109.5
C5—C4—C14	121.1 (5)	C4—C14—H14C	109.5
C3—C4—C14	120.9 (5)	H14A—C14—H14C	109.5
C4—C5—C6	121.2 (5)	H14B—C14—H14C	109.5
C4—C5—H5	119.4	C9—C15—H15A	109.5
C6—C5—H5	119.4	C9—C15—H15B	109.5
C1—C6—C5	120.1 (4)	H15A—C15—H15B	109.5
C1—C6—H6	120.0	C9—C15—H15C	109.5
C5—C6—H6	120.0	H15A—C15—H15C	109.5
C12—C7—C8	120.0 (4)	H15B—C15—H15C	109.5
C12—C7—N1	119.8 (4)	C10—C16—H16A	109.5
C8—C7—N1	120.1 (4)	C10—C16—H16B	109.5
C7—C8—C9	120.9 (4)	H16A—C16—H16B	109.5
C7—C8—H8	119.6	C10—C16—H16C	109.5
C9—C8—H8	119.6	H16A—C16—H16C	109.5
C8—C9—C10	119.6 (4)	H16B—C16—H16C	109.5
C8—C9—C15	120.8 (4)
O2—S1—N1—C7	−56.1 (3)	C2—C1—C6—C5	−2.3 (7)
O1—S1—N1—C7	175.8 (3)	S1—C1—C6—C5	176.5 (4)
C1—S1—N1—C7	57.4 (3)	C4—C5—C6—C1	1.3 (8)
O2—S1—C1—C6	21.0 (4)	S1—N1—C7—C12	−104.3 (4)
O1—S1—C1—C6	152.8 (3)	S1—N1—C7—C8	76.6 (4)
N1—S1—C1—C6	−92.5 (3)	C12—C7—C8—C9	2.1 (6)
O2—S1—C1—C2	−160.2 (3)	N1—C7—C8—C9	−178.8 (3)
O1—S1—C1—C2	−28.4 (4)	C7—C8—C9—C10	−2.5 (6)
N1—S1—C1—C2	86.2 (3)	C7—C8—C9—C15	177.8 (4)
C6—C1—C2—C3	1.6 (6)	C8—C9—C10—C11	1.0 (6)
S1—C1—C2—C3	−177.2 (3)	C15—C9—C10—C11	−179.4 (4)
C6—C1—C2—C13	−178.8 (5)	C8—C9—C10—C16	−179.9 (4)
S1—C1—C2—C13	2.5 (6)	C15—C9—C10—C16	−0.2 (7)
C1—C2—C3—C4	0.2 (6)	C9—C10—C11—C12	1.1 (7)
C13—C2—C3—C4	−179.5 (5)	C16—C10—C11—C12	−178.1 (5)
C2—C3—C4—C5	−1.2 (7)	C10—C11—C12—C7	−1.6 (7)
C2—C3—C4—C14	179.2 (4)	C8—C7—C12—C11	0.0 (6)
C3—C4—C5—C6	0.5 (8)	N1—C7—C12—C11	−179.2 (4)
C14—C4—C5—C6	−180.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.86	2.41	2.976 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.86	2.41	2.976 (4)	124

Symmetry code: (i) .