N-Ethyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

The title compound, C(15)H(17)NO(2)S, is twisted at the S-N bond with a C-S-N-C torsion angle of 73.90 (14)°. The dihedral angle between the aromatic rings is 36.76 (11)°.

Related literature

For related structures, see: Ahmad et al. (2011 ▶); Nirmala et al. (2011 ▶). For applications of sulfonamides, see: Faidallah et al. (2007 ▶); Gauss & Weinstein (1946 ▶); Korolkovas (1988 ▶); Laurence (2009 ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.37

Orthorhombic,

a = 15.6737 (5) Å

b = 8.2831 (2) Å

c = 22.3326 (7) Å

V = 2899.37 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.20 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

26615 measured reflections

3592 independent reflections

2558 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.02

3592 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000177/is5044sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000177/is5044Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000177/is5044Isup3.cml

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

C15H17NO2S	F(000) = 1168
Mr = 275.37	Dx = 1.262 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 8605 reflections
a = 15.6737 (5) Å	θ = 2.2–27.8°
b = 8.2831 (2) Å	µ = 0.22 mm−1
c = 22.3326 (7) Å	T = 296 K
V = 2899.37 (15) Å3	Prism, colourless
Z = 8	0.20 × 0.19 × 0.15 mm

Bruker APEXII CCD diffractometer	2558 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.024
graphite	θmax = 28.3°, θmin = 2.6°
φ and ω scans	h = −20→20
26615 measured reflections	k = −11→10
3592 independent reflections	l = −29→28

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) = 0.136	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0634P)2 + 0.8829P] where P = (Fo2 + 2Fc2)/3
3592 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.99560 (3)	0.12782 (6)	0.34475 (2)	0.0552 (2)
O1	0.99210 (11)	−0.01640 (16)	0.37951 (7)	0.0776 (6)
O2	1.07355 (8)	0.1734 (2)	0.31684 (8)	0.0823 (6)
N1	0.96703 (9)	0.27682 (16)	0.38880 (7)	0.0493 (4)
C1	0.69051 (18)	0.1542 (4)	0.55144 (12)	0.1005 (11)
C2	0.76285 (14)	0.1879 (3)	0.50850 (9)	0.0639 (7)
C3	0.84503 (14)	0.1397 (2)	0.52122 (9)	0.0638 (7)
C4	0.91137 (12)	0.1692 (2)	0.48250 (8)	0.0535 (6)
C5	0.89614 (10)	0.24632 (18)	0.42854 (8)	0.0453 (5)
C6	0.81402 (11)	0.2959 (2)	0.41530 (9)	0.0568 (6)
C7	0.74880 (12)	0.2675 (3)	0.45512 (9)	0.0641 (7)
C8	0.97391 (15)	0.4412 (2)	0.36295 (9)	0.0634 (6)
C9	0.97675 (16)	0.5671 (2)	0.41062 (11)	0.0748 (8)
C10	0.91654 (11)	0.11661 (19)	0.28917 (8)	0.0486 (5)
C11	0.92329 (12)	0.2099 (2)	0.23824 (8)	0.0581 (6)
C12	0.85857 (16)	0.2085 (3)	0.19712 (10)	0.0785 (9)
C13	0.78769 (16)	0.1158 (4)	0.20632 (12)	0.0901 (10)
C14	0.78161 (17)	0.0215 (4)	0.25675 (13)	0.0975 (10)
C15	0.84602 (15)	0.0210 (3)	0.29854 (10)	0.0759 (8)
H1A	0.64400	0.22620	0.54320	0.1510*
H1B	0.70980	0.17040	0.59180	0.1510*
H1C	0.67180	0.04460	0.54660	0.1510*
H3	0.85590	0.08580	0.55700	0.0770*
H4	0.96650	0.13750	0.49250	0.0640*
H6	0.80290	0.34860	0.37940	0.0680*
H7	0.69400	0.30280	0.44590	0.0770*
H8A	0.92540	0.46110	0.33700	0.0760*
H8B	1.02520	0.44810	0.33880	0.0760*
H9A	0.92480	0.56410	0.43330	0.1120*
H9B	0.98310	0.67160	0.39260	0.1120*
H9C	1.02420	0.54670	0.43670	0.1120*
H11	0.97140	0.27330	0.23190	0.0700*
H12	0.86290	0.27110	0.16270	0.0940*
H13	0.74360	0.11660	0.17850	0.1080*
H14	0.73360	−0.04250	0.26270	0.1170*
H15	0.84200	−0.04300	0.33260	0.0910*

	U11	U22	U33	U12	U13	U23
S1	0.0479 (3)	0.0516 (3)	0.0661 (3)	0.0083 (2)	−0.0039 (2)	−0.0070 (2)
O1	0.1042 (12)	0.0495 (7)	0.0790 (10)	0.0247 (7)	−0.0153 (8)	−0.0011 (7)
O2	0.0418 (7)	0.1055 (12)	0.0996 (11)	0.0043 (7)	0.0069 (8)	−0.0201 (10)
N1	0.0498 (8)	0.0415 (7)	0.0567 (8)	−0.0032 (6)	−0.0028 (7)	−0.0023 (6)
C1	0.0921 (19)	0.125 (2)	0.0843 (17)	−0.0261 (16)	0.0305 (15)	−0.0100 (16)
C2	0.0706 (13)	0.0640 (11)	0.0571 (11)	−0.0154 (9)	0.0070 (10)	−0.0114 (9)
C3	0.0817 (14)	0.0591 (11)	0.0505 (10)	−0.0076 (9)	−0.0047 (10)	0.0046 (8)
C4	0.0569 (10)	0.0487 (9)	0.0550 (10)	−0.0009 (7)	−0.0140 (8)	0.0004 (8)
C5	0.0460 (8)	0.0370 (7)	0.0528 (9)	−0.0030 (6)	−0.0055 (7)	−0.0031 (6)
C6	0.0520 (10)	0.0608 (10)	0.0575 (10)	0.0024 (8)	−0.0085 (8)	0.0065 (8)
C7	0.0475 (9)	0.0712 (12)	0.0736 (13)	0.0002 (9)	−0.0037 (9)	−0.0068 (10)
C8	0.0719 (12)	0.0460 (9)	0.0724 (12)	−0.0116 (8)	0.0050 (10)	0.0038 (9)
C9	0.0884 (15)	0.0459 (10)	0.0902 (15)	−0.0077 (10)	0.0048 (13)	−0.0074 (10)
C10	0.0463 (8)	0.0466 (8)	0.0529 (9)	0.0011 (7)	0.0031 (7)	−0.0073 (7)
C11	0.0565 (10)	0.0588 (10)	0.0591 (11)	0.0046 (8)	0.0087 (9)	−0.0019 (9)
C12	0.0863 (16)	0.0874 (16)	0.0619 (13)	0.0235 (13)	−0.0069 (12)	−0.0038 (11)
C13	0.0702 (15)	0.125 (2)	0.0750 (16)	0.0118 (15)	−0.0198 (12)	−0.0314 (16)
C14	0.0711 (15)	0.128 (2)	0.0934 (18)	−0.0409 (15)	−0.0007 (13)	−0.0304 (18)
C15	0.0788 (14)	0.0820 (14)	0.0668 (12)	−0.0338 (12)	0.0015 (11)	−0.0052 (11)

S1—O1	1.4257 (15)	C14—C15	1.375 (4)
S1—O2	1.4226 (15)	C1—H1A	0.9600
S1—N1	1.6406 (15)	C1—H1B	0.9600
S1—C10	1.7564 (18)	C1—H1C	0.9600
N1—C5	1.444 (2)	C3—H3	0.9300
N1—C8	1.483 (2)	C4—H4	0.9300
C1—C2	1.511 (4)	C6—H6	0.9300
C2—C3	1.378 (3)	C7—H7	0.9300
C2—C7	1.380 (3)	C8—H8A	0.9700
C3—C4	1.374 (3)	C8—H8B	0.9700
C4—C5	1.385 (2)	C9—H9A	0.9600
C5—C6	1.383 (2)	C9—H9B	0.9600
C6—C7	1.375 (3)	C9—H9C	0.9600
C8—C9	1.491 (3)	C11—H11	0.9300
C10—C11	1.379 (2)	C12—H12	0.9300
C10—C15	1.376 (3)	C13—H13	0.9300
C11—C12	1.368 (3)	C14—H14	0.9300
C12—C13	1.366 (4)	C15—H15	0.9300
C13—C14	1.374 (4)
O1—S1—O2	119.60 (10)	H1A—C1—H1C	110.00
O1—S1—N1	107.06 (8)	H1B—C1—H1C	110.00
O1—S1—C10	108.26 (9)	C2—C3—H3	119.00
O2—S1—N1	107.31 (9)	C4—C3—H3	119.00
O2—S1—C10	108.08 (9)	C3—C4—H4	120.00
N1—S1—C10	105.72 (8)	C5—C4—H4	120.00
S1—N1—C5	116.54 (11)	C5—C6—H6	120.00
S1—N1—C8	115.94 (12)	C7—C6—H6	120.00
C5—N1—C8	117.12 (14)	C2—C7—H7	119.00
C1—C2—C3	121.1 (2)	C6—C7—H7	119.00
C1—C2—C7	121.1 (2)	N1—C8—H8A	109.00
C3—C2—C7	117.75 (19)	N1—C8—H8B	109.00
C2—C3—C4	121.73 (18)	C9—C8—H8A	109.00
C3—C4—C5	119.95 (17)	C9—C8—H8B	109.00
N1—C5—C4	118.87 (15)	H8A—C8—H8B	108.00
N1—C5—C6	122.18 (16)	C8—C9—H9A	109.00
C4—C5—C6	118.91 (16)	C8—C9—H9B	110.00
C5—C6—C7	120.18 (18)	C8—C9—H9C	109.00
C2—C7—C6	121.45 (18)	H9A—C9—H9B	109.00
N1—C8—C9	111.50 (16)	H9A—C9—H9C	109.00
S1—C10—C11	119.94 (13)	H9B—C9—H9C	109.00
S1—C10—C15	119.33 (15)	C10—C11—H11	120.00
C11—C10—C15	120.64 (18)	C12—C11—H11	120.00
C10—C11—C12	119.46 (18)	C11—C12—H12	120.00
C11—C12—C13	120.5 (2)	C13—C12—H12	120.00
C12—C13—C14	120.0 (2)	C12—C13—H13	120.00
C13—C14—C15	120.5 (3)	C14—C13—H13	120.00
C10—C15—C14	119.0 (2)	C13—C14—H14	120.00
C2—C1—H1A	109.00	C15—C14—H14	120.00
C2—C1—H1B	109.00	C10—C15—H15	120.00
C2—C1—H1C	109.00	C14—C15—H15	121.00
H1A—C1—H1B	109.00
O1—S1—N1—C5	−41.37 (15)	C1—C2—C3—C4	179.8 (2)
O2—S1—N1—C5	−170.93 (13)	C7—C2—C3—C4	0.1 (3)
C10—S1—N1—C5	73.90 (14)	C3—C2—C7—C6	1.0 (3)
O1—S1—N1—C8	174.57 (14)	C1—C2—C7—C6	−178.8 (2)
O2—S1—N1—C8	45.02 (16)	C2—C3—C4—C5	−1.3 (3)
C10—S1—N1—C8	−70.16 (15)	C3—C4—C5—N1	179.61 (15)
N1—S1—C10—C11	87.16 (15)	C3—C4—C5—C6	1.5 (2)
O1—S1—C10—C11	−158.39 (14)	C4—C5—C6—C7	−0.5 (3)
O2—S1—C10—C11	−27.48 (17)	N1—C5—C6—C7	−178.50 (17)
N1—S1—C10—C15	−89.31 (17)	C5—C6—C7—C2	−0.8 (3)
O1—S1—C10—C15	25.14 (19)	S1—C10—C11—C12	−175.60 (16)
O2—S1—C10—C15	156.05 (17)	C15—C10—C11—C12	0.8 (3)
C5—N1—C8—C9	56.2 (2)	S1—C10—C15—C14	175.5 (2)
S1—N1—C5—C4	83.55 (17)	C11—C10—C15—C14	−0.9 (3)
C8—N1—C5—C4	−132.82 (17)	C10—C11—C12—C13	0.1 (3)
S1—N1—C5—C6	−98.45 (17)	C11—C12—C13—C14	−0.9 (4)
C8—N1—C5—C6	45.2 (2)	C12—C13—C14—C15	0.8 (5)
S1—N1—C8—C9	−159.94 (15)	C13—C14—C15—C10	0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2	0.97	2.45	2.902 (2)	108
C15—H15···O1	0.93	2.58	2.934 (3)	103