N-Ethyl-N-phenyl-p-toluene-sulfonamide.

In the title compound, C(15)H(17)NO(2)S, the aromatic rings are oriented at a dihedral angle of 32.8 (1)°. The ethyl group and phenyl ring on the N atom adopt a staggered conformation with respect to the O atoms.

Related literature

For related structures, see: Gowda et al. (2009 ▶); Nirmala et al. (2009a ▶,b ▶).

Experimental

Crystal data

C15H17NO2S

M = 275.36

Orthorhombic,

a = 14.1248 (6) Å

b = 10.4126 (5) Å

c = 19.7639 (10) Å

V = 2906.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.32 × 0.19 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.951, T max = 0.966

15016 measured reflections

3599 independent reflections

1759 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.00

3597 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.31 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011219/ng2749sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011219/ng2749Isup2.hkl

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

C15H17NO2S	F(000) = 1168
Mr = 275.36	Dx = 1.258 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2488 reflections
a = 14.1248 (6) Å	θ = 2.6–23.4°
b = 10.4126 (5) Å	µ = 0.22 mm−1
c = 19.7639 (10) Å	T = 296 K
V = 2906.8 (2) Å3	Needle, colorless
Z = 8	0.32 × 0.19 × 0.16 mm

Bruker Kappa APEXII CCD diffractometer	3599 independent reflections
Radiation source: fine-focus sealed tube	1759 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→10
Tmin = 0.951, Tmax = 0.966	k = −13→13
15016 measured reflections	l = −26→26

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0707P)2 + 0.2464P] where P = (Fo2 + 2Fc2)/3
3597 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.31 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
S1	0.12290 (5)	0.31259 (6)	0.45059 (3)	0.0736 (3)
O1	0.03439 (13)	0.34190 (19)	0.48260 (10)	0.0982 (6)
O2	0.14610 (15)	0.18289 (15)	0.43417 (9)	0.0940 (6)
N1	0.12528 (13)	0.39272 (17)	0.37947 (10)	0.0670 (5)
C1	0.21256 (17)	0.3761 (2)	0.50190 (10)	0.0605 (6)
C2	0.19340 (18)	0.4774 (2)	0.54450 (11)	0.0678 (6)
H2	0.1320	0.5089	0.5481	0.081*
C3	0.2651 (2)	0.5321 (2)	0.58177 (12)	0.0759 (7)
H3	0.2514	0.6004	0.6105	0.091*
C4	0.35649 (19)	0.4880 (3)	0.57751 (12)	0.0739 (7)
C5	0.3742 (2)	0.3868 (3)	0.53525 (15)	0.0852 (8)
H5	0.4357	0.3554	0.5319	0.102*
C6	0.3044 (2)	0.3305 (2)	0.49782 (13)	0.0773 (7)
H6	0.3186	0.2617	0.4696	0.093*
C7	0.09842 (18)	0.5301 (2)	0.38163 (13)	0.0760 (7)
H7A	0.1544	0.5825	0.3749	0.091*
H7B	0.0727	0.5502	0.4259	0.091*
C8	0.0268 (2)	0.5621 (3)	0.32876 (15)	0.0934 (9)
H8A	−0.0287	0.5106	0.3354	0.140*
H8B	0.0528	0.5450	0.2848	0.140*
H8C	0.0103	0.6513	0.3320	0.140*
C9	0.19267 (18)	0.3535 (2)	0.32926 (11)	0.0625 (6)
C10	0.2805 (2)	0.4097 (2)	0.32511 (13)	0.0773 (7)
H10	0.2975	0.4741	0.3554	0.093*
C11	0.3428 (2)	0.3706 (3)	0.27619 (15)	0.0926 (9)
H11	0.4022	0.4086	0.2735	0.111*
C12	0.3186 (3)	0.2762 (3)	0.23123 (15)	0.0975 (10)
H12	0.3614	0.2502	0.1982	0.117*
C13	0.2316 (3)	0.2209 (3)	0.23514 (14)	0.0941 (9)
H13	0.2148	0.1569	0.2046	0.113*
C14	0.1683 (2)	0.2588 (2)	0.28389 (13)	0.0782 (7)
H14	0.1090	0.2204	0.2863	0.094*
C15	0.4350 (2)	0.5510 (3)	0.61724 (16)	0.1138 (11)
H15A	0.4907	0.4982	0.6154	0.171*
H15B	0.4156	0.5613	0.6635	0.171*
H15C	0.4487	0.6337	0.5981	0.171*

	U11	U22	U33	U12	U13	U23
S1	0.0876 (5)	0.0553 (4)	0.0779 (4)	−0.0172 (3)	0.0110 (4)	−0.0053 (3)
O1	0.0785 (13)	0.1021 (15)	0.1139 (15)	−0.0314 (10)	0.0304 (11)	−0.0179 (11)
O2	0.1434 (18)	0.0504 (10)	0.0881 (12)	−0.0189 (9)	0.0111 (11)	−0.0017 (8)
N1	0.0766 (13)	0.0560 (11)	0.0683 (12)	−0.0052 (9)	−0.0052 (10)	−0.0110 (9)
C1	0.0756 (17)	0.0524 (14)	0.0535 (12)	0.0029 (11)	0.0093 (11)	0.0042 (10)
C2	0.0684 (16)	0.0730 (16)	0.0621 (14)	0.0101 (12)	0.0143 (13)	−0.0062 (12)
C3	0.087 (2)	0.0846 (18)	0.0561 (13)	0.0084 (14)	0.0035 (13)	−0.0139 (12)
C4	0.0785 (19)	0.0872 (18)	0.0561 (13)	0.0058 (14)	−0.0046 (13)	0.0069 (13)
C5	0.080 (2)	0.094 (2)	0.0811 (18)	0.0276 (16)	−0.0046 (15)	0.0030 (15)
C6	0.097 (2)	0.0627 (16)	0.0723 (16)	0.0241 (14)	0.0094 (15)	−0.0060 (12)
C7	0.0835 (18)	0.0557 (15)	0.0887 (17)	0.0020 (11)	−0.0085 (15)	−0.0107 (12)
C8	0.100 (2)	0.093 (2)	0.0877 (19)	0.0131 (16)	−0.0141 (17)	0.0042 (15)
C9	0.0775 (17)	0.0494 (12)	0.0605 (13)	−0.0044 (11)	−0.0115 (12)	−0.0005 (10)
C10	0.094 (2)	0.0703 (16)	0.0677 (15)	−0.0120 (14)	−0.0053 (15)	0.0000 (12)
C11	0.090 (2)	0.107 (2)	0.0802 (19)	−0.0051 (17)	0.0048 (17)	0.0132 (18)
C12	0.117 (3)	0.107 (2)	0.0684 (19)	0.030 (2)	0.0103 (18)	0.0146 (17)
C13	0.132 (3)	0.082 (2)	0.0681 (18)	0.0105 (19)	−0.0103 (19)	−0.0157 (14)
C14	0.097 (2)	0.0623 (16)	0.0749 (17)	−0.0058 (13)	−0.0119 (15)	−0.0113 (13)
C15	0.099 (2)	0.148 (3)	0.094 (2)	−0.008 (2)	−0.0250 (19)	−0.006 (2)

S1—O2	1.4271 (18)	C7—H7B	0.9700
S1—O1	1.4339 (19)	C8—H8A	0.9600
S1—N1	1.635 (2)	C8—H8B	0.9600
S1—C1	1.752 (2)	C8—H8C	0.9600
N1—C9	1.434 (3)	C9—C10	1.374 (3)
N1—C7	1.481 (3)	C9—C14	1.377 (3)
C1—C2	1.377 (3)	C10—C11	1.370 (4)
C1—C6	1.384 (3)	C10—H10	0.9300
C2—C3	1.375 (3)	C11—C12	1.368 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.373 (3)	C12—C13	1.360 (4)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.368 (4)	C13—C14	1.372 (4)
C4—C15	1.509 (4)	C13—H13	0.9300
C5—C6	1.365 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—H15A	0.9600
C6—H6	0.9300	C15—H15B	0.9600
C7—C8	1.492 (3)	C15—H15C	0.9600
C7—H7A	0.9700
O2—S1—O1	120.13 (12)	H7A—C7—H7B	107.9
O2—S1—N1	106.42 (10)	C7—C8—H8A	109.5
O1—S1—N1	106.78 (12)	C7—C8—H8B	109.5
O2—S1—C1	108.83 (12)	H8A—C8—H8B	109.5
O1—S1—C1	107.13 (11)	C7—C8—H8C	109.5
N1—S1—C1	106.87 (10)	H8A—C8—H8C	109.5
C9—N1—C7	117.72 (19)	H8B—C8—H8C	109.5
C9—N1—S1	117.59 (15)	C10—C9—C14	119.5 (3)
C7—N1—S1	117.58 (16)	C10—C9—N1	121.3 (2)
C2—C1—C6	118.9 (2)	C14—C9—N1	119.3 (2)
C2—C1—S1	120.07 (19)	C11—C10—C9	119.7 (3)
C6—C1—S1	120.97 (19)	C11—C10—H10	120.2
C3—C2—C1	120.0 (2)	C9—C10—H10	120.2
C3—C2—H2	120.0	C12—C11—C10	120.8 (3)
C1—C2—H2	120.0	C12—C11—H11	119.6
C4—C3—C2	121.4 (2)	C10—C11—H11	119.6
C4—C3—H3	119.3	C13—C12—C11	119.5 (3)
C2—C3—H3	119.3	C13—C12—H12	120.2
C5—C4—C3	117.9 (3)	C11—C12—H12	120.2
C5—C4—C15	121.2 (3)	C12—C13—C14	120.4 (3)
C3—C4—C15	120.9 (3)	C12—C13—H13	119.8
C6—C5—C4	122.0 (3)	C14—C13—H13	119.8
C6—C5—H5	119.0	C13—C14—C9	120.1 (3)
C4—C5—H5	119.0	C13—C14—H14	120.0
C5—C6—C1	119.9 (2)	C9—C14—H14	120.0
C5—C6—H6	120.0	C4—C15—H15A	109.5
C1—C6—H6	120.0	C4—C15—H15B	109.5
N1—C7—C8	111.7 (2)	H15A—C15—H15B	109.5
N1—C7—H7A	109.3	C4—C15—H15C	109.5
C8—C7—H7A	109.3	H15A—C15—H15C	109.5
N1—C7—H7B	109.3	H15B—C15—H15C	109.5
C8—C7—H7B	109.3
O2—S1—N1—C9	−33.36 (19)	C15—C4—C5—C6	−178.5 (3)
O1—S1—N1—C9	−162.81 (16)	C4—C5—C6—C1	0.2 (4)
C1—S1—N1—C9	82.81 (18)	C2—C1—C6—C5	−0.6 (4)
O2—S1—N1—C7	176.76 (17)	S1—C1—C6—C5	175.9 (2)
O1—S1—N1—C7	47.31 (19)	C9—N1—C7—C8	80.0 (3)
C1—S1—N1—C7	−67.08 (19)	S1—N1—C7—C8	−130.2 (2)
O2—S1—C1—C2	−155.91 (18)	C7—N1—C9—C10	56.3 (3)
O1—S1—C1—C2	−24.6 (2)	S1—N1—C9—C10	−93.6 (2)
N1—S1—C1—C2	89.5 (2)	C7—N1—C9—C14	−122.9 (2)
O2—S1—C1—C6	27.6 (2)	S1—N1—C9—C14	87.2 (2)
O1—S1—C1—C6	158.92 (19)	C14—C9—C10—C11	−0.3 (4)
N1—S1—C1—C6	−86.9 (2)	N1—C9—C10—C11	−179.5 (2)
C6—C1—C2—C3	0.4 (3)	C9—C10—C11—C12	0.2 (4)
S1—C1—C2—C3	−176.14 (18)	C10—C11—C12—C13	0.1 (5)
C1—C2—C3—C4	0.1 (4)	C11—C12—C13—C14	−0.2 (5)
C2—C3—C4—C5	−0.5 (4)	C12—C13—C14—C9	0.1 (4)
C2—C3—C4—C15	178.4 (2)	C10—C9—C14—C13	0.2 (4)
C3—C4—C5—C6	0.3 (4)	N1—C9—C14—C13	179.4 (2)