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

In the crystal structure of the title compound, C(14)H(15)NO(2)S, the mol-ecule is bent at the S atom with a C-SO(2)-NH-C torsion angle of 67.9 (2)°. The two benzene rings are tilted by 54.6 (1)° relative to each other. In the crystal, inter-molecular N-H⋯O hydrogen bonds pack the mol-ecules into a supra-molecular structure.

Related literature

For preparation of the title compound, see: Gowda et al. (2005 ▶). For our study of the effects of substituents on the structures of N-(ar­yl)-aryl­sulfonamides, see: Gowda et al. (2008 ▶; 2009 ▶). For related structures, see: Gelbrich et al. (2007 ▶); Perlovich et al. (2006 ▶).

Experimental

Crystal data

C14H15NO2S

M = 261.33

Monoclinic,

a = 11.192 (1) Å

b = 7.3543 (7) Å

c = 16.672 (2) Å

β = 101.62 (1)°

V = 1344.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 299 K

0.48 × 0.40 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.896, T max = 0.959

5063 measured reflections

2742 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.05

2742 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.31 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/S1600536809050089/bx2251sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050089/bx2251Isup2.hkl

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

C14H15NO2S	F(000) = 552
Mr = 261.33	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.192 (1) Å	θ = 2.5–27.8°
b = 7.3543 (7) Å	µ = 0.23 mm−1
c = 16.672 (2) Å	T = 299 K
β = 101.62 (1)°	Prism, colourless
V = 1344.1 (2) Å3	0.48 × 0.40 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2742 independent reflections
Radiation source: fine-focus sealed tube	2187 reflections with I > 2σ(I)
graphite	Rint = 0.015
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.896, Tmax = 0.959	k = −6→9
5063 measured reflections	l = −9→20

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.3783P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.004
2742 reflections	Δρmax = 0.31 e Å−3
169 parameters	Δρmin = −0.31 e Å−3
0 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: 0.0115 (18)

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.41245 (16)	0.1889 (3)	0.59746 (11)	0.0434 (4)
C2	0.52681 (19)	0.2478 (3)	0.59053 (14)	0.0618 (6)
H2	0.5873	0.2668	0.6369	0.074*
C3	0.5495 (3)	0.2780 (4)	0.51321 (17)	0.0816 (8)
H3	0.6266	0.3161	0.5074	0.098*
C4	0.4597 (3)	0.2524 (4)	0.44490 (15)	0.0790 (8)
H4	0.4764	0.2716	0.3931	0.095*
C5	0.3458 (3)	0.1986 (4)	0.45274 (14)	0.0805 (8)
H5	0.2846	0.1846	0.4063	0.097*
C6	0.3209 (2)	0.1650 (3)	0.52926 (13)	0.0620 (6)
H6	0.2438	0.1268	0.5347	0.074*
C7	0.20322 (14)	0.3865 (2)	0.68610 (10)	0.0354 (4)
C8	0.18940 (16)	0.5491 (2)	0.64340 (10)	0.0410 (4)
H8	0.2578	0.6162	0.6381	0.049*
C9	0.07428 (18)	0.6121 (3)	0.60856 (12)	0.0479 (5)
C10	−0.02579 (17)	0.5069 (3)	0.61670 (12)	0.0514 (5)
H10	−0.1035	0.5477	0.5929	0.062*
C11	−0.01416 (16)	0.3444 (3)	0.65873 (12)	0.0489 (5)
C12	0.10215 (16)	0.2850 (3)	0.69465 (11)	0.0430 (4)
H12	0.1122	0.1772	0.7244	0.052*
C13	0.0577 (2)	0.7909 (3)	0.56388 (16)	0.0733 (7)
H13A	0.1323	0.8239	0.5476	0.088*
H13B	0.0364	0.8830	0.5993	0.088*
H13C	−0.0063	0.7799	0.5162	0.088*
C14	−0.12452 (19)	0.2338 (4)	0.66755 (16)	0.0755 (7)
H14A	−0.1717	0.2058	0.6142	0.091*
H14B	−0.1735	0.3023	0.6978	0.091*
H14C	−0.0985	0.1229	0.6962	0.091*
N1	0.32271 (13)	0.3272 (2)	0.72571 (9)	0.0395 (4)
H1N	0.3739 (18)	0.406 (3)	0.7338 (12)	0.047*
O1	0.49861 (12)	0.12569 (19)	0.75071 (8)	0.0526 (4)
O2	0.29563 (13)	0.00239 (19)	0.68847 (10)	0.0590 (4)
S1	0.38310 (4)	0.14444 (6)	0.69537 (3)	0.04071 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0437 (10)	0.0417 (10)	0.0431 (9)	0.0098 (8)	0.0043 (8)	−0.0040 (8)
C2	0.0500 (12)	0.0781 (15)	0.0577 (13)	0.0046 (11)	0.0119 (10)	0.0035 (11)
C3	0.0782 (18)	0.100 (2)	0.0758 (17)	0.0074 (16)	0.0366 (14)	0.0110 (16)
C4	0.110 (2)	0.0806 (18)	0.0512 (14)	0.0199 (16)	0.0283 (15)	0.0035 (12)
C5	0.104 (2)	0.0826 (18)	0.0466 (13)	0.0137 (16)	−0.0035 (13)	−0.0090 (12)
C6	0.0616 (14)	0.0681 (14)	0.0509 (12)	0.0016 (11)	−0.0019 (10)	−0.0081 (10)
C7	0.0323 (8)	0.0407 (9)	0.0330 (8)	0.0014 (7)	0.0063 (6)	−0.0033 (7)
C8	0.0411 (9)	0.0395 (9)	0.0419 (9)	−0.0038 (8)	0.0074 (7)	−0.0010 (7)
C9	0.0507 (11)	0.0427 (10)	0.0458 (10)	0.0040 (8)	−0.0008 (8)	−0.0007 (8)
C10	0.0365 (10)	0.0596 (12)	0.0539 (11)	0.0079 (9)	−0.0012 (8)	−0.0014 (10)
C11	0.0354 (9)	0.0621 (12)	0.0495 (11)	−0.0036 (8)	0.0093 (8)	0.0006 (9)
C12	0.0393 (9)	0.0463 (10)	0.0441 (10)	−0.0018 (8)	0.0101 (7)	0.0058 (8)
C13	0.0773 (16)	0.0504 (13)	0.0804 (17)	0.0035 (12)	−0.0119 (13)	0.0119 (12)
C14	0.0411 (12)	0.100 (2)	0.0858 (17)	−0.0124 (12)	0.0142 (11)	0.0160 (15)
N1	0.0326 (8)	0.0392 (8)	0.0450 (8)	−0.0012 (6)	0.0038 (6)	−0.0030 (6)
O1	0.0436 (7)	0.0577 (8)	0.0510 (7)	0.0142 (6)	−0.0032 (6)	0.0062 (6)
O2	0.0556 (8)	0.0410 (7)	0.0798 (10)	−0.0062 (6)	0.0123 (7)	−0.0002 (7)
S1	0.0367 (3)	0.0373 (3)	0.0457 (3)	0.00433 (18)	0.00246 (18)	0.00225 (18)

C1—C2	1.378 (3)	C9—C10	1.390 (3)
C1—C6	1.380 (3)	C9—C13	1.505 (3)
C1—S1	1.7594 (19)	C10—C11	1.378 (3)
C2—C3	1.381 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.389 (2)
C3—C4	1.372 (4)	C11—C14	1.511 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.366 (4)	C13—H13A	0.9600
C4—H4	0.9300	C13—H13B	0.9600
C5—C6	1.382 (3)	C13—H13C	0.9600
C5—H5	0.9300	C14—H14A	0.9600
C6—H6	0.9300	C14—H14B	0.9600
C7—C8	1.384 (2)	C14—H14C	0.9600
C7—C12	1.386 (2)	N1—S1	1.6302 (15)
C7—N1	1.435 (2)	N1—H1N	0.81 (2)
C8—C9	1.382 (2)	O1—S1	1.4356 (13)
C8—H8	0.9300	O2—S1	1.4204 (14)
C2—C1—C6	121.3 (2)	C9—C10—H10	118.8
C2—C1—S1	119.10 (15)	C10—C11—C12	118.44 (17)
C6—C1—S1	119.64 (16)	C10—C11—C14	121.40 (19)
C1—C2—C3	118.5 (2)	C12—C11—C14	120.15 (19)
C1—C2—H2	120.7	C7—C12—C11	119.97 (17)
C3—C2—H2	120.7	C7—C12—H12	120.0
C4—C3—C2	120.7 (2)	C11—C12—H12	120.0
C4—C3—H3	119.6	C9—C13—H13A	109.5
C2—C3—H3	119.6	C9—C13—H13B	109.5
C5—C4—C3	120.2 (2)	H13A—C13—H13B	109.5
C5—C4—H4	119.9	C9—C13—H13C	109.5
C3—C4—H4	119.9	H13A—C13—H13C	109.5
C4—C5—C6	120.4 (2)	H13B—C13—H13C	109.5
C4—C5—H5	119.8	C11—C14—H14A	109.5
C6—C5—H5	119.8	C11—C14—H14B	109.5
C1—C6—C5	118.9 (2)	H14A—C14—H14B	109.5
C1—C6—H6	120.5	C11—C14—H14C	109.5
C5—C6—H6	120.5	H14A—C14—H14C	109.5
C8—C7—C12	120.60 (16)	H14B—C14—H14C	109.5
C8—C7—N1	119.75 (15)	C7—N1—S1	120.92 (12)
C12—C7—N1	119.56 (16)	C7—N1—H1N	115.0 (15)
C9—C8—C7	120.24 (16)	S1—N1—H1N	108.7 (15)
C9—C8—H8	119.9	O2—S1—O1	119.88 (9)
C7—C8—H8	119.9	O2—S1—N1	108.03 (8)
C8—C9—C10	118.28 (18)	O1—S1—N1	104.82 (8)
C8—C9—C13	120.85 (19)	O2—S1—C1	108.42 (9)
C10—C9—C13	120.87 (18)	O1—S1—C1	107.56 (9)
C11—C10—C9	122.46 (17)	N1—S1—C1	107.53 (8)
C11—C10—H10	118.8
C6—C1—C2—C3	−1.8 (3)	C8—C7—C12—C11	1.4 (3)
S1—C1—C2—C3	178.45 (19)	N1—C7—C12—C11	177.90 (16)
C1—C2—C3—C4	0.9 (4)	C10—C11—C12—C7	−1.5 (3)
C2—C3—C4—C5	0.8 (4)	C14—C11—C12—C7	179.70 (19)
C3—C4—C5—C6	−1.7 (4)	C8—C7—N1—S1	−114.44 (16)
C2—C1—C6—C5	0.9 (3)	C12—C7—N1—S1	69.0 (2)
S1—C1—C6—C5	−179.33 (19)	C7—N1—S1—O2	−48.89 (16)
C4—C5—C6—C1	0.9 (4)	C7—N1—S1—O1	−177.81 (13)
C12—C7—C8—C9	−0.1 (3)	C7—N1—S1—C1	67.93 (15)
N1—C7—C8—C9	−176.67 (16)	C2—C1—S1—O2	−148.57 (17)
C7—C8—C9—C10	−0.9 (3)	C6—C1—S1—O2	31.65 (19)
C7—C8—C9—C13	178.38 (19)	C2—C1—S1—O1	−17.56 (19)
C8—C9—C10—C11	0.7 (3)	C6—C1—S1—O1	162.66 (16)
C13—C9—C10—C11	−178.5 (2)	C2—C1—S1—N1	94.86 (17)
C9—C10—C11—C12	0.5 (3)	C6—C1—S1—N1	−84.93 (18)
C9—C10—C11—C14	179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.81 (2)	2.14 (2)	2.942 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.81 (2)	2.14 (2)	2.942 (2)	176 (2)

Symmetry code: (i) .