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

In the crystal structure of the title compound, C(16)H(19)NO(2)S, the mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 66.5 (2)°. The dihedral angle between the sulfonyl and aniline benzene rings in the mol-ecule is 41.0 (1)°. The crystal structure features inversion dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ▶). For our studies of 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

Triclinic,

a = 8.225 (1) Å

b = 8.423 (1) Å

c = 10.992 (2) Å

α = 85.58 (2)°

β = 88.97 (2)°

γ = 84.43 (1)°

V = 755.62 (19) Å3

Z = 2

Cu Kα radiation

μ = 1.91 mm−1

T = 299 K

0.40 × 0.38 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.516, T max = 0.647

2899 measured reflections

2689 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.026

3 standard reflections every 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.282

S = 1.36

2689 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.50 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/S1600536810012663/bq2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012663/bq2205Isup2.hkl

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

C16H19NO2S	Z = 2
Mr = 289.38	F(000) = 308
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 8.225 (1) Å	Cell parameters from 25 reflections
b = 8.423 (1) Å	θ = 7.8–18.8°
c = 10.992 (2) Å	µ = 1.91 mm−1
α = 85.58 (2)°	T = 299 K
β = 88.97 (2)°	Prism, brown
γ = 84.43 (1)°	0.40 × 0.38 × 0.25 mm
V = 755.62 (19) Å3

Enraf–Nonius CAD-4 diffractometer	2419 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 67.1°, θmin = 4.0°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.516, Tmax = 0.647	l = −13→1
2899 measured reflections	3 standard reflections every 120 min
2689 independent reflections	intensity decay: 1.5%

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.282	H atoms treated by a mixture of independent and constrained refinement
S = 1.36	w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
2689 reflections	(Δ/σ)max = 0.002
188 parameters	Δρmax = 0.48 e Å−3
1 restraint	Δρmin = −0.50 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
C1	0.4299 (4)	0.5647 (3)	0.7203 (3)	0.0402 (7)
C2	0.3552 (4)	0.6498 (4)	0.6195 (3)	0.0452 (8)
C3	0.4587 (5)	0.7247 (5)	0.5349 (3)	0.0558 (9)
H3	0.4125	0.7809	0.4658	0.067*
C4	0.6233 (5)	0.7190 (5)	0.5491 (3)	0.0544 (9)
C5	0.6937 (5)	0.6310 (5)	0.6489 (3)	0.0555 (9)
H5	0.8064	0.6230	0.6586	0.067*
C6	0.5975 (4)	0.5549 (4)	0.7343 (3)	0.0482 (8)
H6	0.6455	0.4965	0.8019	0.058*
C7	0.1553 (3)	0.7468 (3)	0.9002 (2)	0.0349 (7)
C8	0.2064 (4)	0.8968 (3)	0.8660 (3)	0.0376 (7)
C9	0.0873 (4)	1.0200 (4)	0.8323 (3)	0.0440 (7)
H9	0.1186	1.1217	0.8109	0.053*
C10	−0.0762 (4)	0.9960 (4)	0.8295 (3)	0.0466 (8)
C11	−0.1231 (4)	0.8477 (4)	0.8650 (3)	0.0507 (8)
H11	−0.2332	0.8310	0.8649	0.061*
C12	−0.0100 (4)	0.7242 (4)	0.9006 (3)	0.0462 (8)
H12	−0.0436	0.6243	0.9253	0.055*
C13	0.1763 (5)	0.6667 (6)	0.5928 (4)	0.0643 (10)
H13A	0.1163	0.7044	0.6623	0.077*
H13B	0.1430	0.5648	0.5755	0.077*
H13C	0.1549	0.7419	0.5235	0.077*
C14	0.7272 (7)	0.8078 (6)	0.4575 (4)	0.0820 (14)
H14A	0.6587	0.8646	0.3956	0.098*
H14B	0.8048	0.7329	0.4206	0.098*
H14C	0.7843	0.8823	0.4981	0.098*
C15	0.3816 (4)	0.9290 (4)	0.8660 (3)	0.0517 (9)
H15A	0.4333	0.8978	0.7913	0.062*
H15B	0.4356	0.8689	0.9339	0.062*
H15C	0.3887	1.0411	0.8725	0.062*
C16	−0.1989 (5)	1.1362 (5)	0.7893 (4)	0.0717 (12)
H16A	−0.1420	1.2219	0.7519	0.086*
H16B	−0.2595	1.1723	0.8591	0.086*
H16C	−0.2726	1.1029	0.7317	0.086*
N1	0.2700 (3)	0.6121 (3)	0.9369 (2)	0.0397 (7)
H1N	0.363 (3)	0.632 (4)	0.966 (3)	0.048*
O1	0.4329 (3)	0.3611 (3)	0.9106 (2)	0.0548 (7)
O2	0.1751 (3)	0.4227 (3)	0.7989 (2)	0.0556 (7)
S1	0.32074 (8)	0.47490 (7)	0.84308 (6)	0.0403 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0449 (16)	0.0342 (15)	0.0406 (15)	0.0018 (12)	0.0016 (12)	−0.0038 (12)
C2	0.0482 (17)	0.0451 (17)	0.0413 (16)	0.0014 (13)	−0.0062 (13)	−0.0042 (13)
C3	0.068 (2)	0.059 (2)	0.0377 (16)	0.0034 (17)	−0.0005 (15)	0.0034 (14)
C4	0.059 (2)	0.059 (2)	0.0459 (17)	−0.0082 (16)	0.0117 (15)	−0.0051 (15)
C5	0.0485 (18)	0.063 (2)	0.055 (2)	−0.0048 (16)	0.0004 (15)	−0.0073 (17)
C6	0.0426 (16)	0.054 (2)	0.0461 (17)	0.0023 (13)	−0.0020 (13)	−0.0024 (14)
C7	0.0395 (14)	0.0278 (13)	0.0361 (14)	0.0007 (10)	−0.0008 (11)	0.0006 (10)
C8	0.0445 (16)	0.0305 (14)	0.0379 (14)	−0.0048 (11)	−0.0019 (11)	−0.0021 (11)
C9	0.0565 (18)	0.0344 (15)	0.0394 (15)	−0.0006 (13)	−0.0021 (13)	0.0030 (12)
C10	0.0490 (17)	0.0496 (18)	0.0382 (15)	0.0114 (14)	−0.0028 (13)	−0.0039 (13)
C11	0.0373 (15)	0.060 (2)	0.0546 (19)	−0.0009 (14)	0.0004 (13)	−0.0073 (15)
C12	0.0450 (17)	0.0396 (16)	0.0548 (18)	−0.0091 (13)	0.0068 (14)	−0.0035 (13)
C13	0.051 (2)	0.083 (3)	0.057 (2)	0.0006 (18)	−0.0143 (16)	0.0042 (19)
C14	0.093 (3)	0.085 (3)	0.068 (3)	−0.021 (3)	0.028 (2)	0.003 (2)
C15	0.0484 (18)	0.0418 (18)	0.066 (2)	−0.0129 (14)	−0.0079 (15)	0.0005 (15)
C16	0.066 (2)	0.071 (3)	0.069 (2)	0.027 (2)	−0.0035 (19)	0.011 (2)
N1	0.0447 (14)	0.0315 (13)	0.0412 (13)	0.0011 (11)	−0.0033 (10)	0.0035 (10)
O1	0.0646 (15)	0.0334 (12)	0.0617 (15)	0.0110 (11)	−0.0033 (12)	0.0080 (10)
O2	0.0544 (14)	0.0451 (13)	0.0700 (16)	−0.0142 (11)	−0.0020 (11)	−0.0086 (11)
S1	0.0460 (6)	0.0271 (6)	0.0469 (6)	−0.0010 (3)	−0.0018 (4)	0.0014 (3)

C1—C6	1.384 (4)	C10—C16	1.520 (4)
C1—C2	1.391 (4)	C11—C12	1.365 (5)
C1—S1	1.769 (3)	C11—H11	0.9300
C2—C3	1.404 (5)	C12—H12	0.9300
C2—C13	1.497 (5)	C13—H13A	0.9600
C3—C4	1.362 (6)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.380 (5)	C14—H14A	0.9600
C4—C14	1.510 (5)	C14—H14B	0.9600
C5—C6	1.378 (5)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C12	1.390 (4)	C15—H15C	0.9600
C7—C8	1.392 (4)	C16—H16A	0.9600
C7—N1	1.441 (3)	C16—H16B	0.9600
C8—C9	1.389 (4)	C16—H16C	0.9600
C8—C15	1.492 (4)	N1—S1	1.627 (3)
C9—C10	1.380 (5)	N1—H1N	0.869 (19)
C9—H9	0.9300	O1—S1	1.436 (2)
C10—C11	1.369 (5)	O2—S1	1.421 (3)
C6—C1—C2	121.0 (3)	C7—C12—H12	119.8
C6—C1—S1	115.3 (2)	C2—C13—H13A	109.5
C2—C1—S1	123.6 (2)	C2—C13—H13B	109.5
C1—C2—C3	116.4 (3)	H13A—C13—H13B	109.5
C1—C2—C13	126.0 (3)	C2—C13—H13C	109.5
C3—C2—C13	117.6 (3)	H13A—C13—H13C	109.5
C4—C3—C2	123.2 (3)	H13B—C13—H13C	109.5
C4—C3—H3	118.4	C4—C14—H14A	109.5
C2—C3—H3	118.4	C4—C14—H14B	109.5
C3—C4—C5	118.8 (3)	H14A—C14—H14B	109.5
C3—C4—C14	120.7 (4)	C4—C14—H14C	109.5
C5—C4—C14	120.5 (4)	H14A—C14—H14C	109.5
C6—C5—C4	120.2 (3)	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	120.4 (3)	H15A—C15—H15B	109.5
C5—C6—H6	119.8	C8—C15—H15C	109.5
C1—C6—H6	119.8	H15A—C15—H15C	109.5
C12—C7—C8	120.2 (3)	H15B—C15—H15C	109.5
C12—C7—N1	118.3 (3)	C10—C16—H16A	109.5
C8—C7—N1	121.5 (3)	C10—C16—H16B	109.5
C9—C8—C7	117.7 (3)	H16A—C16—H16B	109.5
C9—C8—C15	119.7 (3)	C10—C16—H16C	109.5
C7—C8—C15	122.6 (3)	H16A—C16—H16C	109.5
C10—C9—C8	122.0 (3)	H16B—C16—H16C	109.5
C10—C9—H9	119.0	C7—N1—S1	120.14 (19)
C8—C9—H9	119.0	C7—N1—H1N	118 (3)
C11—C10—C9	119.0 (3)	S1—N1—H1N	103 (2)
C11—C10—C16	122.1 (3)	O2—S1—O1	118.85 (15)
C9—C10—C16	118.9 (3)	O2—S1—N1	108.21 (14)
C12—C11—C10	120.7 (3)	O1—S1—N1	104.49 (13)
C12—C11—H11	119.6	O2—S1—C1	109.49 (15)
C10—C11—H11	119.6	O1—S1—C1	107.90 (14)
C11—C12—C7	120.4 (3)	N1—S1—C1	107.29 (13)
C11—C12—H12	119.8
C6—C1—C2—C3	−0.4 (5)	C8—C9—C10—C11	2.3 (5)
S1—C1—C2—C3	174.9 (2)	C8—C9—C10—C16	−178.9 (3)
C6—C1—C2—C13	178.8 (3)	C9—C10—C11—C12	−1.2 (5)
S1—C1—C2—C13	−5.9 (5)	C16—C10—C11—C12	−180.0 (3)
C1—C2—C3—C4	−1.1 (5)	C10—C11—C12—C7	−0.6 (5)
C13—C2—C3—C4	179.6 (4)	C8—C7—C12—C11	1.5 (5)
C2—C3—C4—C5	2.4 (6)	N1—C7—C12—C11	−179.1 (3)
C2—C3—C4—C14	−177.4 (3)	C12—C7—N1—S1	77.6 (3)
C3—C4—C5—C6	−2.1 (6)	C8—C7—N1—S1	−103.0 (3)
C14—C4—C5—C6	177.7 (4)	C7—N1—S1—O2	−51.5 (3)
C4—C5—C6—C1	0.6 (5)	C7—N1—S1—O1	−179.1 (2)
C2—C1—C6—C5	0.7 (5)	C7—N1—S1—C1	66.5 (2)
S1—C1—C6—C5	−175.0 (2)	C6—C1—S1—O2	−151.7 (3)
C12—C7—C8—C9	−0.4 (4)	C2—C1—S1—O2	32.7 (3)
N1—C7—C8—C9	−179.8 (2)	C6—C1—S1—O1	−21.0 (3)
C12—C7—C8—C15	178.9 (3)	C2—C1—S1—O1	163.4 (3)
N1—C7—C8—C15	−0.6 (4)	C6—C1—S1—N1	91.0 (3)
C7—C8—C9—C10	−1.5 (4)	C2—C1—S1—N1	−84.5 (3)
C15—C8—C9—C10	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (2)	2.19 (2)	3.024 (4)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (2)	2.19 (2)	3.024 (4)	161 (3)

Symmetry code: (i) .