N-Benzyl-N-ethyl-4-methyl­benzene­sulfonamide

Khan, I.U.; Ahmad, W.; Arshad, M.N.; Sharif, S.; Ahmed, J.

doi:10.1107/S1600536810035105

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2507

doi:10.1107/S1600536810035105

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N-Benzyl-N-ethyl-4-methylbenzenesulfonamide

Islam Ullah Khan,^a ^* Waqar Ahmad,^a Muhammad Nadeem Arshad,^a Shahzad Sharif ^a and Jamil Ahmed ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 24 August 2010; accepted 31 August 2010; online 4 September 2010)

In the title compound, C₁₆H₁₉NO₂S, the dihedral angle between the two aromatic rings is 84.78 (7)°. Weak intermolecular C—H⋯O interactions stabilize the crystal structure by the formation of a 16-membered R₂²(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_r = 289.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.125
S = 1.02
3489 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035105/bt5337sup1.cif

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

checkCIF report

Comment top

Sulfonamides have extensively been reported for their wide variety of pharmacological activities such as antibacterial (Maren, 1976) and diuretic (Boyd, 1988). The present structure is countinous to our previous reported derivative of sulfonamide (Khan et al., 2010).

The two aromatic rings in the title sulfonamide molecule are inclined to each other at an angle of 84.78(0.07)°. The C–H···O type weak intermolecular hydrogen bonding between the C–H of methyl group and oxygen of the SO₂ forms the dimers which result in the formation of 16 membered ring motif which can be represented as R₂²(16) in graph set patterns (Bernstein et al., 1995).

Related literature top

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

Experimental top

A mixture of N-benzyl-4-methylbenzenesulfonamide (0.5 g, 2.02mmol) and sodium hydride (0.2 g, 8.333 mmol) in N, N dimethylformamide (10 ml) was stirred at room temperature for 30 minutes followed by the addition of ethyl iodide (0.62 ml 2.02mmol) After the consumption of reactants (as monitored by TLC), the contents were poured over crushed ice. The precipitated product was isolated, washed, dried and recrystallized from methanol solution to yield colorless blocks of title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Unit cell packing with hydrogen bonding shown as dashed lines.

N-Benzyl-N-ethyl-4-methylbenzenesulfonamide top

Crystal data top

C₁₆H₁₉NO₂S	F(000) = 616
M_r = 289.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0529P)² + 0.2532P] where P = (F_o² + 2F_c²)/3
3489 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₆H₁₉NO₂S	V = 1526.11 (9) Å³
M_r = 289.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8144 (3) Å	µ = 0.21 mm⁻¹
b = 19.7677 (6) Å	T = 296 K
c = 9.8914 (4) Å	0.41 × 0.25 × 0.19 mm
β = 117.689 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3489 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2168 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.961	R_int = 0.036
13763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
3489 reflections	Δρ_min = −0.21 e Å⁻³
183 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NO₂S
M_r	289.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.8144 (3), 19.7677 (6), 9.8914 (4)
β (°)	117.689 (1)
V (Å³)	1526.11 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.41 × 0.25 × 0.19

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.918, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	13763, 3489, 2168
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.125, 1.02
No. of reflections	3489
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···O1ⁱ	0.96	2.58	3.354 (3)	137.6

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

References

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