N-(3,5-Dimethyl-phen-yl)-2,4-dimethyl-benzene-sulfonamide.

In the title compound, C(16)H(19)NO(2)S, the mol-ecule is twisted about the S-N bond, the C-S(O(2))-N(H)-C torsion angle being 53.9 (2)°. The dihedral angle between the two benzene rings is 82.1 (1)°. The crystal structure features inversion-related dimers linked by N-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C16H19NO2S

M = 289.38

Monoclinic,

a = 23.490 (2) Å

b = 8.1528 (6) Å

c = 16.544 (1) Å

β = 102.690 (8)°

V = 3090.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 299 K

0.40 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.921, T max = 0.975

6232 measured reflections

2751 independent reflections

2009 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.01

2751 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 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 datablocks I, global. DOI: 10.1107/S1600536809050740/tk2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050740/tk2587Isup2.hkl

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

C16H19NO2S	F(000) = 1232
Mr = 289.38	Dx = 1.244 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2194 reflections
a = 23.490 (2) Å	θ = 2.5–27.9°
b = 8.1528 (6) Å	µ = 0.21 mm−1
c = 16.544 (1) Å	T = 299 K
β = 102.690 (8)°	Prism, colourless
V = 3090.9 (4) Å3	0.40 × 0.20 × 0.12 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2751 independent reflections
Radiation source: fine-focus sealed tube	2009 reflections with I > 2σ(I)
graphite	Rint = 0.018
Rotation method data acquisition using ω and φ scans.	θmax = 25.3°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −28→17
Tmin = 0.921, Tmax = 0.975	k = −9→9
6232 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0512P)2 + 3.0162P] where P = (Fo2 + 2Fc2)/3
2751 reflections	(Δ/σ)max = 0.004
188 parameters	Δρmax = 0.19 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
S1	0.05610 (3)	0.54362 (8)	0.39886 (4)	0.0472 (2)
O1	−0.00491 (7)	0.5510 (2)	0.40012 (10)	0.0581 (5)
O2	0.08128 (8)	0.6784 (2)	0.36408 (12)	0.0655 (5)
N1	0.08841 (9)	0.5250 (3)	0.49593 (13)	0.0519 (5)
H1N	0.0648 (10)	0.498 (3)	0.5253 (15)	0.062*
C1	0.07002 (9)	0.3654 (3)	0.34572 (13)	0.0382 (5)
C2	0.05851 (9)	0.2067 (3)	0.37077 (14)	0.0421 (5)
C3	0.06794 (10)	0.0785 (3)	0.32105 (16)	0.0492 (6)
H3	0.0611	−0.0277	0.3372	0.059*
C4	0.08716 (10)	0.0999 (3)	0.24799 (16)	0.0498 (6)
C5	0.09849 (10)	0.2566 (3)	0.22560 (15)	0.0525 (6)
H5	0.1119	0.2739	0.1774	0.063*
C6	0.09019 (10)	0.3886 (3)	0.27382 (15)	0.0480 (6)
H6	0.0982	0.4940	0.2580	0.058*
C7	0.14835 (10)	0.4895 (3)	0.52826 (15)	0.0458 (6)
C8	0.16296 (10)	0.4248 (3)	0.60749 (15)	0.0508 (6)
H8	0.1337	0.4019	0.6357	0.061*
C9	0.22056 (11)	0.3939 (3)	0.64514 (17)	0.0606 (7)
C10	0.26309 (12)	0.4250 (4)	0.60070 (19)	0.0675 (8)
H10	0.3019	0.4029	0.6252	0.081*
C11	0.24971 (11)	0.4873 (4)	0.52134 (18)	0.0612 (8)
C12	0.19150 (11)	0.5218 (3)	0.48498 (17)	0.0564 (7)
H12	0.1817	0.5663	0.4320	0.068*
C13	0.03632 (13)	0.1703 (4)	0.44804 (16)	0.0636 (7)
H13A	0.0022	0.2352	0.4479	0.076*
H13B	0.0660	0.1966	0.4961	0.076*
H13C	0.0266	0.0561	0.4491	0.076*
C14	0.09508 (14)	−0.0463 (4)	0.1958 (2)	0.0796 (9)
H14A	0.0580	−0.0979	0.1752	0.096*
H14B	0.1212	−0.1231	0.2289	0.096*
H14C	0.1111	−0.0109	0.1501	0.096*
C15	0.23625 (14)	0.3267 (5)	0.7320 (2)	0.0931 (11)
H15A	0.2522	0.2184	0.7310	0.112*
H15B	0.2019	0.3220	0.7544	0.112*
H15C	0.2647	0.3968	0.7659	0.112*
C16	0.29662 (13)	0.5197 (5)	0.4739 (2)	0.0881 (11)
H16A	0.3020	0.4238	0.4428	0.106*
H16B	0.3325	0.5457	0.5121	0.106*
H16C	0.2852	0.6102	0.4368	0.106*

	U11	U22	U33	U12	U13	U23
S1	0.0477 (4)	0.0440 (4)	0.0490 (4)	0.0102 (3)	0.0089 (3)	0.0005 (3)
O1	0.0450 (9)	0.0733 (12)	0.0548 (10)	0.0213 (9)	0.0082 (8)	−0.0019 (10)
O2	0.0843 (13)	0.0390 (10)	0.0738 (13)	0.0028 (9)	0.0189 (10)	0.0074 (10)
N1	0.0434 (12)	0.0667 (14)	0.0455 (12)	0.0089 (10)	0.0098 (9)	−0.0063 (11)
C1	0.0364 (11)	0.0397 (13)	0.0386 (12)	0.0039 (9)	0.0083 (9)	0.0025 (10)
C2	0.0403 (13)	0.0429 (13)	0.0435 (12)	0.0022 (10)	0.0103 (10)	0.0042 (11)
C3	0.0502 (14)	0.0397 (13)	0.0576 (15)	0.0004 (11)	0.0114 (12)	0.0040 (12)
C4	0.0441 (13)	0.0535 (16)	0.0507 (14)	0.0080 (11)	0.0078 (11)	−0.0066 (13)
C5	0.0549 (15)	0.0656 (18)	0.0405 (13)	0.0069 (13)	0.0177 (11)	0.0018 (13)
C6	0.0504 (14)	0.0478 (14)	0.0471 (14)	0.0012 (11)	0.0134 (11)	0.0089 (12)
C7	0.0405 (13)	0.0456 (14)	0.0498 (14)	0.0034 (10)	0.0065 (10)	−0.0145 (12)
C8	0.0473 (14)	0.0528 (15)	0.0512 (15)	0.0002 (11)	0.0086 (11)	−0.0078 (13)
C9	0.0523 (16)	0.0623 (17)	0.0615 (17)	−0.0007 (13)	0.0002 (13)	−0.0054 (15)
C10	0.0425 (15)	0.080 (2)	0.074 (2)	0.0033 (14)	−0.0010 (13)	−0.0087 (17)
C11	0.0429 (14)	0.0707 (19)	0.0708 (19)	−0.0047 (13)	0.0140 (13)	−0.0191 (16)
C12	0.0518 (15)	0.0667 (18)	0.0498 (14)	−0.0008 (13)	0.0095 (12)	−0.0092 (14)
C13	0.0804 (19)	0.0584 (17)	0.0598 (17)	−0.0053 (14)	0.0324 (14)	0.0097 (15)
C14	0.089 (2)	0.075 (2)	0.076 (2)	0.0131 (18)	0.0195 (17)	−0.0212 (18)
C15	0.069 (2)	0.116 (3)	0.083 (2)	−0.0011 (19)	−0.0087 (16)	0.024 (2)
C16	0.0550 (18)	0.120 (3)	0.094 (2)	−0.0072 (18)	0.0268 (16)	−0.016 (2)

S1—O2	1.4276 (18)	C8—H8	0.9300
S1—O1	1.4392 (17)	C9—C10	1.388 (4)
S1—N1	1.626 (2)	C9—C15	1.506 (4)
S1—C1	1.766 (2)	C10—C11	1.378 (4)
N1—C7	1.422 (3)	C10—H10	0.9300
N1—H1N	0.844 (16)	C11—C12	1.396 (3)
C1—C6	1.386 (3)	C11—C16	1.510 (4)
C1—C2	1.403 (3)	C12—H12	0.9300
C2—C3	1.378 (3)	C13—H13A	0.9600
C2—C13	1.512 (3)	C13—H13B	0.9600
C3—C4	1.391 (3)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.373 (4)	C14—H14B	0.9600
C4—C14	1.507 (4)	C14—H14C	0.9600
C5—C6	1.379 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.384 (3)	C16—H16A	0.9600
C7—C12	1.389 (3)	C16—H16B	0.9600
C8—C9	1.383 (3)	C16—H16C	0.9600
O2—S1—O1	118.40 (11)	C10—C9—C15	121.2 (3)
O2—S1—N1	108.98 (12)	C11—C10—C9	122.1 (2)
O1—S1—N1	103.88 (11)	C11—C10—H10	118.9
O2—S1—C1	107.12 (11)	C9—C10—H10	118.9
O1—S1—C1	109.61 (10)	C10—C11—C12	118.8 (2)
N1—S1—C1	108.52 (11)	C10—C11—C16	121.3 (3)
C7—N1—S1	126.83 (17)	C12—C11—C16	119.9 (3)
C7—N1—H1N	117.0 (19)	C7—C12—C11	119.8 (3)
S1—N1—H1N	111.7 (19)	C7—C12—H12	120.1
C6—C1—C2	120.2 (2)	C11—C12—H12	120.1
C6—C1—S1	116.78 (18)	C2—C13—H13A	109.5
C2—C1—S1	122.89 (17)	C2—C13—H13B	109.5
C3—C2—C1	117.2 (2)	H13A—C13—H13B	109.5
C3—C2—C13	119.1 (2)	C2—C13—H13C	109.5
C1—C2—C13	123.7 (2)	H13A—C13—H13C	109.5
C2—C3—C4	123.3 (2)	H13B—C13—H13C	109.5
C2—C3—H3	118.3	C4—C14—H14A	109.5
C4—C3—H3	118.3	C4—C14—H14B	109.5
C5—C4—C3	118.1 (2)	H14A—C14—H14B	109.5
C5—C4—C14	121.7 (2)	C4—C14—H14C	109.5
C3—C4—C14	120.2 (3)	H14A—C14—H14C	109.5
C4—C5—C6	120.7 (2)	H14B—C14—H14C	109.5
C4—C5—H5	119.7	C9—C15—H15A	109.5
C6—C5—H5	119.7	C9—C15—H15B	109.5
C5—C6—C1	120.6 (2)	H15A—C15—H15B	109.5
C5—C6—H6	119.7	C9—C15—H15C	109.5
C1—C6—H6	119.7	H15A—C15—H15C	109.5
C8—C7—C12	120.2 (2)	H15B—C15—H15C	109.5
C8—C7—N1	116.9 (2)	C11—C16—H16A	109.5
C12—C7—N1	122.8 (2)	C11—C16—H16B	109.5
C9—C8—C7	120.7 (2)	H16A—C16—H16B	109.5
C9—C8—H8	119.7	C11—C16—H16C	109.5
C7—C8—H8	119.7	H16A—C16—H16C	109.5
C8—C9—C10	118.4 (3)	H16B—C16—H16C	109.5
C8—C9—C15	120.4 (3)
O2—S1—N1—C7	−62.4 (2)	C14—C4—C5—C6	179.1 (2)
O1—S1—N1—C7	170.5 (2)	C4—C5—C6—C1	−0.2 (4)
C1—S1—N1—C7	53.9 (2)	C2—C1—C6—C5	0.8 (3)
O2—S1—C1—C6	−12.4 (2)	S1—C1—C6—C5	−175.71 (18)
O1—S1—C1—C6	117.20 (18)	S1—N1—C7—C8	−158.6 (2)
N1—S1—C1—C6	−129.97 (18)	S1—N1—C7—C12	23.5 (4)
O2—S1—C1—C2	171.16 (18)	C12—C7—C8—C9	1.0 (4)
O1—S1—C1—C2	−59.2 (2)	N1—C7—C8—C9	−177.0 (2)
N1—S1—C1—C2	53.6 (2)	C7—C8—C9—C10	−1.8 (4)
C6—C1—C2—C3	−0.2 (3)	C7—C8—C9—C15	178.8 (3)
S1—C1—C2—C3	176.07 (17)	C8—C9—C10—C11	1.0 (4)
C6—C1—C2—C13	−179.8 (2)	C15—C9—C10—C11	−179.6 (3)
S1—C1—C2—C13	−3.6 (3)	C9—C10—C11—C12	0.6 (4)
C1—C2—C3—C4	−1.0 (3)	C9—C10—C11—C16	−179.8 (3)
C13—C2—C3—C4	178.7 (2)	C8—C7—C12—C11	0.7 (4)
C2—C3—C4—C5	1.5 (4)	N1—C7—C12—C11	178.5 (2)
C2—C3—C4—C14	−178.5 (2)	C10—C11—C12—C7	−1.5 (4)
C3—C4—C5—C6	−0.9 (4)	C16—C11—C12—C7	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.10 (2)	2.945 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.10 (2)	2.945 (3)	176 (3)

Symmetry code: (i) .