N-Benzyl-N-ethyl-4-methyl-benzene-sulfonamide.

In the title compound, C(16)H(19)NO(2)S, the dihedral angle between the two aromatic rings is 84.78 (7)°. Weak inter-molecular C-H⋯O inter-actions stabilize the crystal structure by the formation of a 16-membered R(2) (2)(16) ring motif.

Related literature

For biological activity of sulfonamides, see: Maren (1976 ▶); Boyd (1988 ▶). For a related structure, see: Khan et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H19NO2S

M = 289.38

Monoclinic,

a = 8.8144 (3) Å

b = 19.7677 (6) Å

c = 9.8914 (4) Å

β = 117.689 (1)°

V = 1526.11 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.41 × 0.25 × 0.19 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.918, T max = 0.961

13763 measured reflections

3489 independent reflections

2168 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.02

3489 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 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/S1600536810035105/bt5337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035105/bt5337Isup2.hkl

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

C16H19NO2S	F(000) = 616
Mr = 289.38	Dx = 1.259 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3170 reflections
a = 8.8144 (3) Å	θ = 2.5–22.0°
b = 19.7677 (6) Å	µ = 0.21 mm−1
c = 9.8914 (4) Å	T = 296 K
β = 117.689 (1)°	Needle, colorless
V = 1526.11 (9) Å3	0.41 × 0.25 × 0.19 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3489 independent reflections
Radiation source: fine-focus sealed tube	2168 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.918, Tmax = 0.961	k = −25→24
13763 measured reflections	l = −11→12

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.2532P] where P = (Fo2 + 2Fc2)/3
3489 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.70800 (8)	0.37535 (3)	0.46668 (7)	0.0682 (2)
O1	0.6074 (2)	0.39018 (8)	0.30736 (18)	0.0865 (5)
O2	0.8768 (2)	0.40136 (9)	0.5483 (2)	0.1020 (6)
N1	0.7241 (2)	0.29352 (8)	0.48024 (18)	0.0612 (4)
C1	0.5929 (2)	0.40249 (9)	0.5623 (2)	0.0517 (5)
C2	0.4177 (3)	0.40689 (11)	0.4843 (2)	0.0692 (6)
H2	0.3605	0.3980	0.3801	0.083*
C3	0.3266 (3)	0.42449 (12)	0.5602 (3)	0.0716 (6)
H3	0.2078	0.4270	0.5063	0.086*
C4	0.4073 (3)	0.43849 (9)	0.7140 (2)	0.0581 (5)
C5	0.5832 (3)	0.43392 (10)	0.7901 (2)	0.0618 (5)
H5	0.6405	0.4431	0.8942	0.074*
C6	0.6766 (3)	0.41622 (10)	0.7163 (2)	0.0599 (5)
H6	0.7954	0.4135	0.7701	0.072*
C7	0.3065 (3)	0.45867 (12)	0.7953 (3)	0.0836 (7)
H7A	0.3692	0.4465	0.9011	0.125*
H7B	0.1981	0.4358	0.7501	0.125*
H7C	0.2880	0.5067	0.7867	0.125*
C8	0.8382 (3)	0.26352 (12)	0.6291 (2)	0.0743 (6)
H8A	0.7710	0.2490	0.6785	0.089*
H8B	0.9191	0.2974	0.6934	0.089*
C9	0.9347 (2)	0.20401 (10)	0.6128 (2)	0.0564 (5)
C10	1.0400 (3)	0.21151 (12)	0.5454 (2)	0.0667 (6)
H10	1.0521	0.2537	0.5099	0.080*
C11	1.1276 (3)	0.15629 (14)	0.5306 (3)	0.0765 (7)
H11	1.1990	0.1617	0.4856	0.092*
C12	1.1105 (3)	0.09461 (13)	0.5810 (3)	0.0761 (7)
H12	1.1692	0.0578	0.5697	0.091*
C13	1.0084 (3)	0.08631 (12)	0.6478 (3)	0.0735 (6)
H13	0.9975	0.0439	0.6830	0.088*
C14	0.9203 (3)	0.14070 (12)	0.6639 (2)	0.0667 (6)
H14	0.8502	0.1346	0.7098	0.080*
C15	0.5806 (3)	0.25212 (11)	0.3735 (2)	0.0660 (6)
H15A	0.6267	0.2131	0.3454	0.079*
H15B	0.5157	0.2783	0.2814	0.079*
C16	0.4591 (3)	0.22731 (13)	0.4301 (3)	0.0914 (8)
H16A	0.3641	0.2047	0.3487	0.137*
H16B	0.4178	0.2650	0.4648	0.137*
H16C	0.5177	0.1963	0.5130	0.137*

	U11	U22	U33	U12	U13	U23
S1	0.0794 (4)	0.0589 (3)	0.0904 (4)	−0.0003 (3)	0.0599 (3)	−0.0035 (3)
O1	0.1339 (15)	0.0741 (10)	0.0837 (11)	0.0164 (9)	0.0777 (11)	0.0182 (8)
O2	0.0814 (11)	0.0933 (13)	0.1601 (17)	−0.0224 (10)	0.0802 (12)	−0.0314 (12)
N1	0.0701 (11)	0.0557 (10)	0.0617 (10)	0.0093 (8)	0.0339 (9)	−0.0037 (8)
C1	0.0571 (11)	0.0439 (10)	0.0604 (12)	0.0018 (8)	0.0325 (10)	−0.0018 (9)
C2	0.0655 (14)	0.0854 (16)	0.0522 (11)	0.0167 (11)	0.0236 (11)	−0.0053 (10)
C3	0.0549 (12)	0.0855 (16)	0.0723 (14)	0.0125 (11)	0.0278 (11)	−0.0083 (12)
C4	0.0703 (13)	0.0458 (11)	0.0710 (13)	0.0002 (9)	0.0436 (11)	−0.0032 (9)
C5	0.0741 (14)	0.0562 (12)	0.0551 (11)	−0.0053 (10)	0.0300 (11)	−0.0099 (9)
C6	0.0533 (11)	0.0537 (12)	0.0702 (13)	−0.0035 (9)	0.0266 (10)	−0.0108 (10)
C7	0.1066 (19)	0.0724 (15)	0.1055 (18)	−0.0004 (13)	0.0777 (16)	−0.0079 (13)
C8	0.0868 (16)	0.0822 (16)	0.0593 (13)	0.0194 (13)	0.0386 (12)	−0.0065 (11)
C9	0.0559 (11)	0.0698 (13)	0.0473 (10)	0.0052 (10)	0.0272 (9)	−0.0012 (9)
C10	0.0695 (13)	0.0730 (14)	0.0675 (13)	0.0003 (11)	0.0402 (12)	0.0072 (11)
C11	0.0620 (13)	0.1046 (19)	0.0791 (15)	0.0116 (13)	0.0465 (12)	0.0010 (14)
C12	0.0651 (14)	0.0816 (17)	0.0751 (15)	0.0202 (12)	0.0269 (12)	−0.0006 (13)
C13	0.0690 (14)	0.0671 (15)	0.0748 (15)	0.0079 (11)	0.0253 (12)	0.0121 (11)
C14	0.0596 (12)	0.0867 (16)	0.0601 (12)	0.0024 (11)	0.0332 (11)	0.0094 (11)
C15	0.0831 (15)	0.0625 (13)	0.0650 (13)	0.0064 (11)	0.0450 (12)	0.0010 (10)
C16	0.107 (2)	0.0864 (18)	0.108 (2)	−0.0098 (15)	0.0732 (18)	−0.0064 (14)

S1—O2	1.4192 (18)	C8—C9	1.504 (3)
S1—O1	1.4342 (17)	C8—H8A	0.9700
S1—N1	1.6239 (17)	C8—H8B	0.9700
S1—C1	1.7614 (18)	C9—C14	1.378 (3)
N1—C15	1.464 (3)	C9—C10	1.379 (3)
N1—C8	1.468 (3)	C10—C11	1.384 (3)
C1—C2	1.372 (3)	C10—H10	0.9300
C1—C6	1.376 (3)	C11—C12	1.352 (3)
C2—C3	1.374 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.352 (3)
C3—C4	1.375 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.378 (3)
C4—C5	1.376 (3)	C13—H13	0.9300
C4—C7	1.503 (3)	C14—H14	0.9300
C5—C6	1.375 (3)	C15—C16	1.503 (3)
C5—H5	0.9300	C15—H15A	0.9700
C6—H6	0.9300	C15—H15B	0.9700
C7—H7A	0.9600	C16—H16A	0.9600
C7—H7B	0.9600	C16—H16B	0.9600
C7—H7C	0.9600	C16—H16C	0.9600
O2—S1—O1	120.04 (11)	C9—C8—H8A	109.3
O2—S1—N1	106.58 (10)	N1—C8—H8B	109.3
O1—S1—N1	106.27 (9)	C9—C8—H8B	109.3
O2—S1—C1	107.28 (10)	H8A—C8—H8B	108.0
O1—S1—C1	108.16 (10)	C14—C9—C10	118.19 (19)
N1—S1—C1	108.01 (9)	C14—C9—C8	121.22 (18)
C15—N1—C8	117.21 (18)	C10—C9—C8	120.6 (2)
C15—N1—S1	118.93 (14)	C9—C10—C11	120.0 (2)
C8—N1—S1	118.57 (14)	C9—C10—H10	120.0
C2—C1—C6	119.62 (18)	C11—C10—H10	120.0
C2—C1—S1	119.75 (15)	C12—C11—C10	120.6 (2)
C6—C1—S1	120.56 (15)	C12—C11—H11	119.7
C1—C2—C3	119.99 (19)	C10—C11—H11	119.7
C1—C2—H2	120.0	C11—C12—C13	120.2 (2)
C3—C2—H2	120.0	C11—C12—H12	119.9
C2—C3—C4	121.5 (2)	C13—C12—H12	119.9
C2—C3—H3	119.3	C12—C13—C14	120.0 (2)
C4—C3—H3	119.3	C12—C13—H13	120.0
C3—C4—C5	117.64 (18)	C14—C13—H13	120.0
C3—C4—C7	121.0 (2)	C9—C14—C13	120.92 (19)
C5—C4—C7	121.4 (2)	C9—C14—H14	119.5
C6—C5—C4	121.76 (19)	C13—C14—H14	119.5
C6—C5—H5	119.1	N1—C15—C16	116.12 (17)
C4—C5—H5	119.1	N1—C15—H15A	108.3
C5—C6—C1	119.52 (19)	C16—C15—H15A	108.3
C5—C6—H6	120.2	N1—C15—H15B	108.3
C1—C6—H6	120.2	C16—C15—H15B	108.3
C4—C7—H7A	109.5	H15A—C15—H15B	107.4
C4—C7—H7B	109.5	C15—C16—H16A	109.5
H7A—C7—H7B	109.5	C15—C16—H16B	109.5
C4—C7—H7C	109.5	H16A—C16—H16B	109.5
H7A—C7—H7C	109.5	C15—C16—H16C	109.5
H7B—C7—H7C	109.5	H16A—C16—H16C	109.5
N1—C8—C9	111.52 (15)	H16B—C16—H16C	109.5
N1—C8—H8A	109.3
O2—S1—N1—C15	−162.75 (15)	C7—C4—C5—C6	−179.28 (19)
O1—S1—N1—C15	−33.63 (16)	C4—C5—C6—C1	−0.1 (3)
C1—S1—N1—C15	82.24 (15)	C2—C1—C6—C5	0.3 (3)
O2—S1—N1—C8	43.62 (18)	S1—C1—C6—C5	−176.62 (15)
O1—S1—N1—C8	172.75 (15)	C15—N1—C8—C9	65.8 (2)
C1—S1—N1—C8	−71.39 (17)	S1—N1—C8—C9	−140.15 (16)
O2—S1—C1—C2	156.23 (18)	N1—C8—C9—C14	−120.8 (2)
O1—S1—C1—C2	25.4 (2)	N1—C8—C9—C10	58.9 (3)
N1—S1—C1—C2	−89.22 (18)	C14—C9—C10—C11	0.0 (3)
O2—S1—C1—C6	−26.89 (19)	C8—C9—C10—C11	−179.8 (2)
O1—S1—C1—C6	−157.72 (16)	C9—C10—C11—C12	0.4 (3)
N1—S1—C1—C6	87.66 (17)	C10—C11—C12—C13	−0.6 (4)
C6—C1—C2—C3	−0.4 (3)	C11—C12—C13—C14	0.4 (3)
S1—C1—C2—C3	176.47 (17)	C10—C9—C14—C13	−0.1 (3)
C1—C2—C3—C4	0.5 (4)	C8—C9—C14—C13	179.61 (19)
C2—C3—C4—C5	−0.3 (3)	C12—C13—C14—C9	−0.1 (3)
C2—C3—C4—C7	179.1 (2)	C8—N1—C15—C16	57.2 (2)
C3—C4—C5—C6	0.2 (3)	S1—N1—C15—C16	−96.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O1i	0.96	2.58	3.354 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯O1i	0.96	2.58	3.354 (3)	138

Symmetry code: (i) .