N-(2,6-Dimethyl-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

Mol-ecules of the title compound, C(16)H(19)NO(2)S, are bent at the S atom with a C-SO(2)-NH-C torsion angle of -60.0 (2)°. The dihedral angle between the phenyl-sulfonyl and aniline rings is 41.7 (1)°. In the crystal, mol-ecules are packed into centrosymmetric dimers through pairs of N-H⋯O(S) hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). 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. (2000 ▶), on N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007 ▶), on N-(ar­yl)-aryl­sulfonamides, see: Gelbrich et al. (2007 ▶); Nirmala et al. (2010 ▶); Perlovich et al. (2006 ▶), and on N-chloro-aryl­sulfonamides, see: Gowda et al. (2003 ▶).

Experimental

Crystal data

C16H19NO2S

M = 289.38

Monoclinic,

a = 11.119 (2) Å

b = 8.312 (1) Å

c = 16.043 (2) Å

β = 97.27 (1)°

V = 1470.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.48 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.901, T max = 0.957

5256 measured reflections

2685 independent reflections

2107 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.04

2685 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031102/bt5591sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031102/bt5591Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031102/bt5591Isup3.cml

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

C16H19NO2S	F(000) = 616
Mr = 289.38	Dx = 1.307 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 922 reflections
a = 11.119 (2) Å	θ = 2.5–27.7°
b = 8.312 (1) Å	µ = 0.22 mm−1
c = 16.043 (2) Å	T = 293 K
β = 97.27 (1)°	Prism, colourless
V = 1470.8 (4) Å3	0.48 × 0.36 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2685 independent reflections
Radiation source: fine-focus sealed tube	2107 reflections with I > 2σ(I)
graphite	Rint = 0.021
Rotation method data acquisition using ω and φ scans	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −12→13
Tmin = 0.901, Tmax = 0.957	k = −6→10
5256 measured reflections	l = −19→11

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.5567P] where P = (Fo2 + 2Fc2)/3
2685 reflections	(Δ/σ)max = 0.005
188 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

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	0.21154 (19)	0.9601 (3)	0.45025 (12)	0.0397 (5)
C2	0.1037 (2)	0.9068 (3)	0.40278 (14)	0.0461 (6)
C3	0.0200 (2)	1.0252 (3)	0.37507 (17)	0.0566 (7)
H3	−0.0520	0.9933	0.3435	0.068*
C4	0.0369 (2)	1.1871 (3)	0.39137 (16)	0.0541 (6)
C5	0.1448 (2)	1.2349 (3)	0.43770 (15)	0.0529 (6)
H5	0.1590	1.3434	0.4493	0.063*
C6	0.2309 (2)	1.1225 (3)	0.46654 (14)	0.0444 (5)
H6	0.3030	1.1559	0.4974	0.053*
C7	0.37589 (17)	0.7507 (3)	0.33206 (12)	0.0355 (5)
C8	0.37653 (19)	0.5848 (3)	0.31960 (14)	0.0432 (5)
C9	0.3293 (2)	0.5267 (3)	0.24105 (15)	0.0540 (6)
H9	0.3260	0.4163	0.2317	0.065*
C10	0.2874 (2)	0.6298 (3)	0.17701 (15)	0.0563 (7)
H10	0.2551	0.5888	0.1250	0.068*
C11	0.2929 (2)	0.7931 (3)	0.18931 (14)	0.0484 (6)
H11	0.2665	0.8615	0.1449	0.058*
C12	0.33732 (19)	0.8582 (3)	0.26703 (13)	0.0400 (5)
C13	0.0733 (2)	0.7344 (3)	0.38090 (19)	0.0631 (7)
H13A	0.0683	0.6743	0.4315	0.076*
H13B	0.1354	0.6892	0.3515	0.076*
H13C	−0.0032	0.7295	0.3457	0.076*
C14	−0.0588 (3)	1.3083 (4)	0.3596 (2)	0.0775 (9)
H14A	−0.1099	1.3288	0.4024	0.093*
H14B	−0.1068	1.2668	0.3104	0.093*
H14C	−0.0205	1.4067	0.3458	0.093*
C15	0.4295 (2)	0.4694 (3)	0.38653 (16)	0.0560 (6)
H15A	0.3750	0.4581	0.4280	0.067*
H15B	0.5060	0.5099	0.4126	0.067*
H15C	0.4414	0.3665	0.3616	0.067*
C16	0.3431 (2)	1.0378 (3)	0.27633 (15)	0.0517 (6)
H16A	0.4105	1.0663	0.3171	0.062*
H16B	0.2694	1.0761	0.2946	0.062*
H16C	0.3532	1.0857	0.2232	0.062*
N1	0.42138 (16)	0.8124 (2)	0.41422 (10)	0.0386 (4)
H1N	0.466 (2)	0.894 (2)	0.4152 (15)	0.046*
O1	0.28375 (16)	0.6738 (2)	0.50137 (10)	0.0517 (4)
O2	0.40451 (14)	0.9080 (2)	0.55574 (9)	0.0496 (4)
S1	0.33235 (5)	0.82853 (7)	0.48727 (3)	0.04002 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0382 (11)	0.0462 (13)	0.0339 (11)	−0.0007 (10)	0.0014 (9)	0.0020 (9)
C2	0.0381 (12)	0.0505 (14)	0.0486 (13)	−0.0031 (11)	0.0011 (10)	0.0001 (11)
C3	0.0361 (12)	0.0683 (18)	0.0624 (15)	−0.0012 (12)	−0.0053 (11)	0.0030 (13)
C4	0.0458 (14)	0.0574 (16)	0.0592 (15)	0.0104 (12)	0.0067 (12)	0.0063 (12)
C5	0.0579 (15)	0.0475 (14)	0.0533 (14)	0.0033 (12)	0.0070 (12)	−0.0027 (11)
C6	0.0447 (12)	0.0478 (14)	0.0396 (12)	−0.0007 (11)	0.0006 (10)	−0.0038 (10)
C7	0.0288 (10)	0.0451 (12)	0.0306 (10)	0.0006 (9)	−0.0037 (8)	−0.0007 (9)
C8	0.0362 (11)	0.0452 (14)	0.0464 (12)	0.0010 (10)	−0.0016 (9)	−0.0017 (10)
C9	0.0522 (14)	0.0509 (15)	0.0562 (15)	−0.0032 (12)	−0.0036 (12)	−0.0148 (12)
C10	0.0496 (14)	0.0730 (18)	0.0425 (13)	−0.0029 (13)	−0.0091 (11)	−0.0152 (12)
C11	0.0434 (13)	0.0666 (17)	0.0327 (11)	0.0052 (12)	−0.0049 (10)	0.0016 (11)
C12	0.0347 (11)	0.0502 (14)	0.0341 (11)	0.0022 (10)	0.0004 (9)	0.0002 (9)
C13	0.0477 (14)	0.0585 (16)	0.0784 (18)	−0.0082 (13)	−0.0109 (13)	−0.0060 (14)
C14	0.0596 (17)	0.075 (2)	0.096 (2)	0.0187 (16)	0.0015 (16)	0.0111 (17)
C15	0.0622 (15)	0.0474 (14)	0.0562 (15)	0.0072 (13)	−0.0008 (12)	0.0045 (11)
C16	0.0613 (15)	0.0502 (15)	0.0425 (12)	0.0019 (12)	0.0027 (11)	0.0079 (11)
N1	0.0387 (10)	0.0431 (11)	0.0317 (9)	−0.0037 (8)	−0.0039 (7)	−0.0021 (8)
O1	0.0561 (10)	0.0492 (10)	0.0493 (9)	−0.0023 (8)	0.0044 (8)	0.0109 (7)
O2	0.0516 (9)	0.0622 (11)	0.0313 (8)	0.0006 (8)	−0.0089 (7)	−0.0041 (7)
S1	0.0414 (3)	0.0467 (3)	0.0300 (3)	−0.0006 (2)	−0.0033 (2)	0.0015 (2)

C1—C6	1.387 (3)	C10—H10	0.9300
C1—C2	1.408 (3)	C11—C12	1.391 (3)
C1—S1	1.775 (2)	C11—H11	0.9300
C2—C3	1.388 (3)	C12—C16	1.500 (3)
C2—C13	1.504 (4)	C13—H13A	0.9600
C3—C4	1.379 (4)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.387 (4)	C14—H14A	0.9600
C4—C14	1.506 (4)	C14—H14B	0.9600
C5—C6	1.375 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.394 (3)	C15—H15C	0.9600
C7—C12	1.399 (3)	C16—H16A	0.9600
C7—N1	1.445 (2)	C16—H16B	0.9600
C8—C9	1.389 (3)	C16—H16C	0.9600
C8—C15	1.503 (3)	N1—S1	1.6325 (19)
C9—C10	1.373 (4)	N1—H1N	0.834 (16)
C9—H9	0.9300	O1—S1	1.4242 (17)
C10—C11	1.372 (4)	O2—S1	1.4364 (15)
C6—C1—C2	120.6 (2)	C7—C12—C16	123.77 (19)
C6—C1—S1	116.35 (17)	C2—C13—H13A	109.5
C2—C1—S1	122.97 (18)	C2—C13—H13B	109.5
C3—C2—C1	116.1 (2)	H13A—C13—H13B	109.5
C3—C2—C13	118.7 (2)	C2—C13—H13C	109.5
C1—C2—C13	125.2 (2)	H13A—C13—H13C	109.5
C4—C3—C2	124.2 (2)	H13B—C13—H13C	109.5
C4—C3—H3	117.9	C4—C14—H14A	109.5
C2—C3—H3	117.9	C4—C14—H14B	109.5
C3—C4—C5	117.9 (2)	H14A—C14—H14B	109.5
C3—C4—C14	121.0 (3)	C4—C14—H14C	109.5
C5—C4—C14	121.0 (3)	H14A—C14—H14C	109.5
C6—C5—C4	120.3 (2)	H14B—C14—H14C	109.5
C6—C5—H5	119.9	C8—C15—H15A	109.5
C4—C5—H5	119.9	C8—C15—H15B	109.5
C5—C6—C1	120.9 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.6	C8—C15—H15C	109.5
C1—C6—H6	119.6	H15A—C15—H15C	109.5
C8—C7—C12	122.12 (19)	H15B—C15—H15C	109.5
C8—C7—N1	118.32 (18)	C12—C16—H16A	109.5
C12—C7—N1	119.50 (19)	C12—C16—H16B	109.5
C9—C8—C7	117.8 (2)	H16A—C16—H16B	109.5
C9—C8—C15	119.7 (2)	C12—C16—H16C	109.5
C7—C8—C15	122.5 (2)	H16A—C16—H16C	109.5
C10—C9—C8	121.0 (2)	H16B—C16—H16C	109.5
C10—C9—H9	119.5	C7—N1—S1	120.67 (14)
C8—C9—H9	119.5	C7—N1—H1N	116.2 (16)
C11—C10—C9	120.3 (2)	S1—N1—H1N	109.3 (17)
C11—C10—H10	119.8	O1—S1—O2	118.69 (10)
C9—C10—H10	119.8	O1—S1—N1	108.46 (10)
C10—C11—C12	121.2 (2)	O2—S1—N1	104.84 (9)
C10—C11—H11	119.4	O1—S1—C1	108.85 (10)
C12—C11—H11	119.4	O2—S1—C1	107.37 (10)
C11—C12—C7	117.4 (2)	N1—S1—C1	108.20 (9)
C11—C12—C16	118.8 (2)
C6—C1—C2—C3	−0.6 (3)	C8—C9—C10—C11	0.8 (4)
S1—C1—C2—C3	−177.08 (18)	C9—C10—C11—C12	−2.0 (4)
C6—C1—C2—C13	179.7 (2)	C10—C11—C12—C7	−0.1 (3)
S1—C1—C2—C13	3.2 (3)	C10—C11—C12—C16	179.0 (2)
C1—C2—C3—C4	−0.1 (4)	C8—C7—C12—C11	3.3 (3)
C13—C2—C3—C4	179.6 (3)	N1—C7—C12—C11	−179.25 (19)
C2—C3—C4—C5	0.7 (4)	C8—C7—C12—C16	−175.7 (2)
C2—C3—C4—C14	−179.5 (3)	N1—C7—C12—C16	1.7 (3)
C3—C4—C5—C6	−0.5 (4)	C8—C7—N1—S1	−86.7 (2)
C14—C4—C5—C6	179.7 (2)	C12—C7—N1—S1	95.8 (2)
C4—C5—C6—C1	−0.2 (4)	C7—N1—S1—O1	57.93 (19)
C2—C1—C6—C5	0.8 (3)	C7—N1—S1—O2	−174.33 (16)
S1—C1—C6—C5	177.48 (18)	C7—N1—S1—C1	−59.99 (19)
C12—C7—C8—C9	−4.4 (3)	C6—C1—S1—O1	153.48 (17)
N1—C7—C8—C9	178.15 (19)	C2—C1—S1—O1	−29.9 (2)
C12—C7—C8—C15	173.6 (2)	C6—C1—S1—O2	23.8 (2)
N1—C7—C8—C15	−3.8 (3)	C2—C1—S1—O2	−159.61 (18)
C7—C8—C9—C10	2.3 (4)	C6—C1—S1—N1	−88.85 (18)
C15—C8—C9—C10	−175.8 (2)	C2—C1—S1—N1	87.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.83 (2)	2.20 (2)	3.024 (3)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.83 (2)	2.20 (2)	3.024 (3)	168 (2)

Symmetry code: (i) .