N-[4-(Benzyl-sulfamo-yl)phen-yl]acetamide.

A folded conformation is found for the title compound, C(15)H(16)N(2)O(3)S, whereby the benzene rings come into close proximity [centroid-centroid distance = 4.0357 (12) Å and the dihedral angle between them = 24.37 (10)°]. The amide group is coplanar with the benzene ring to which it is bound [C-C-N-C torsion angle = 11.1 (3)°]. In the crystal packing, two-dimensional arrays in the (101) plane are formed via N-H⋯O hydrogen bonding.

Related literature

For background to the pharmacological uses of sulfonamides, see: Beate et al. (1998 ▶); Kazmierski et al. (2004 ▶). For related structures, see: Khan et al. (2010 ▶); Sharif et al. (2010 ▶).

Experimental

Crystal data

C15H16N2O3S

M = 304.37

Monoclinic,

a = 9.0646 (9) Å

b = 13.6888 (14) Å

c = 12.1651 (12) Å

β = 98.635 (5)°

V = 1492.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.19 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.868, T max = 0.948

13777 measured reflections

3577 independent reflections

2689 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.02

3577 reflections

197 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.24 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027698/jj2043sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027698/jj2043Isup2.hkl

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

C15H16N2O3S	F(000) = 640
Mr = 304.37	Dx = 1.355 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4154 reflections
a = 9.0646 (9) Å	θ = 2.6–27.9°
b = 13.6888 (14) Å	µ = 0.23 mm−1
c = 12.1651 (12) Å	T = 293 K
β = 98.635 (5)°	Prism, colourless
V = 1492.4 (3) Å3	0.19 × 0.09 × 0.07 mm
Z = 4

Bruker APEXII CCD diffractometer	3577 independent reflections
Radiation source: fine-focus sealed tube	2689 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 28.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.868, Tmax = 0.948	k = −18→17
13777 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.3076P] where P = (Fo2 + 2Fc2)/3
3577 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.25 e Å−3
2 restraints	Δρmin = −0.24 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	0.11090 (5)	0.33181 (3)	0.82483 (3)	0.03999 (15)
O1	0.21873 (16)	0.27094 (10)	0.88809 (10)	0.0536 (4)
O2	−0.04454 (15)	0.31532 (11)	0.82667 (12)	0.0594 (4)
O3	0.02478 (16)	0.40834 (11)	0.26180 (11)	0.0596 (4)
N1	0.14186 (17)	0.44201 (11)	0.86867 (12)	0.0448 (4)
H1N	0.0786 (18)	0.4846 (12)	0.8311 (15)	0.054*
N2	0.20419 (16)	0.31175 (10)	0.35277 (11)	0.0399 (3)
H2N	0.2876 (15)	0.2778 (12)	0.3473 (16)	0.048*
C1	0.2944 (2)	0.47687 (16)	0.90443 (16)	0.0559 (5)
H1A	0.3409	0.4347	0.9638	0.067*
H1B	0.2888	0.5418	0.9355	0.067*
C2	0.3944 (2)	0.48133 (13)	0.81674 (15)	0.0464 (4)
C3	0.3606 (2)	0.54229 (14)	0.72574 (17)	0.0532 (5)
H3	0.2748	0.5805	0.7184	0.064*
C4	0.4533 (3)	0.54678 (16)	0.6461 (2)	0.0661 (6)
H4	0.4295	0.5880	0.5852	0.079*
C5	0.5799 (3)	0.49141 (18)	0.6555 (2)	0.0732 (7)
H5	0.6416	0.4945	0.6011	0.088*
C6	0.6154 (3)	0.43158 (18)	0.7452 (2)	0.0745 (7)
H6	0.7021	0.3943	0.7523	0.089*
C7	0.5230 (2)	0.42612 (15)	0.8254 (2)	0.0611 (6)
H7	0.5477	0.3848	0.8860	0.073*
C8	0.13636 (18)	0.32476 (11)	0.68406 (13)	0.0354 (3)
C9	0.0308 (2)	0.36444 (16)	0.60359 (15)	0.0499 (5)
H9	−0.0539	0.3934	0.6238	0.060*
C10	0.0494 (2)	0.36167 (15)	0.49303 (15)	0.0496 (5)
H10	−0.0223	0.3888	0.4390	0.059*
C11	0.17580 (18)	0.31823 (11)	0.46307 (13)	0.0343 (3)
C12	0.2803 (2)	0.27757 (14)	0.54465 (14)	0.0436 (4)
H12	0.3647	0.2477	0.5250	0.052*
C13	0.26102 (19)	0.28078 (13)	0.65483 (14)	0.0426 (4)
H13	0.3321	0.2533	0.7091	0.051*
C14	0.1335 (2)	0.35627 (13)	0.26110 (14)	0.0418 (4)
C15	0.1978 (3)	0.33645 (17)	0.15660 (16)	0.0605 (6)
H15A	0.1635	0.2741	0.1270	0.091*
H15B	0.3048	0.3360	0.1730	0.091*
H15C	0.1664	0.3865	0.1029	0.091*

	U11	U22	U33	U12	U13	U23
S1	0.0444 (3)	0.0476 (3)	0.0295 (2)	−0.00397 (18)	0.01067 (17)	0.00348 (17)
O1	0.0718 (10)	0.0527 (7)	0.0358 (6)	0.0085 (6)	0.0066 (6)	0.0080 (6)
O2	0.0492 (8)	0.0830 (10)	0.0502 (8)	−0.0168 (7)	0.0209 (6)	0.0030 (7)
O3	0.0599 (9)	0.0774 (10)	0.0420 (7)	0.0218 (7)	0.0096 (6)	0.0121 (7)
N1	0.0510 (9)	0.0497 (9)	0.0341 (7)	0.0033 (7)	0.0079 (6)	−0.0005 (6)
N2	0.0407 (8)	0.0491 (8)	0.0312 (7)	0.0066 (6)	0.0094 (6)	−0.0011 (6)
C1	0.0667 (13)	0.0620 (12)	0.0363 (9)	−0.0135 (10)	−0.0015 (9)	−0.0055 (9)
C2	0.0470 (10)	0.0429 (9)	0.0467 (10)	−0.0085 (8)	−0.0014 (8)	−0.0028 (8)
C3	0.0547 (12)	0.0492 (10)	0.0555 (11)	0.0010 (8)	0.0081 (9)	0.0034 (9)
C4	0.0772 (16)	0.0596 (13)	0.0634 (14)	−0.0104 (11)	0.0167 (12)	0.0071 (11)
C5	0.0672 (15)	0.0670 (14)	0.0917 (18)	−0.0175 (12)	0.0319 (14)	−0.0142 (13)
C6	0.0467 (13)	0.0666 (14)	0.109 (2)	−0.0009 (10)	0.0096 (13)	−0.0133 (14)
C7	0.0554 (13)	0.0516 (11)	0.0706 (14)	−0.0016 (9)	−0.0091 (11)	0.0039 (10)
C8	0.0362 (9)	0.0418 (8)	0.0290 (7)	−0.0043 (6)	0.0079 (6)	0.0004 (6)
C9	0.0395 (10)	0.0759 (13)	0.0357 (9)	0.0162 (9)	0.0105 (7)	0.0016 (9)
C10	0.0420 (10)	0.0736 (12)	0.0329 (9)	0.0161 (9)	0.0050 (7)	0.0031 (9)
C11	0.0351 (8)	0.0379 (8)	0.0305 (7)	−0.0024 (6)	0.0074 (6)	−0.0015 (6)
C12	0.0397 (9)	0.0541 (10)	0.0383 (9)	0.0122 (8)	0.0098 (7)	0.0001 (8)
C13	0.0408 (10)	0.0523 (10)	0.0341 (8)	0.0080 (8)	0.0038 (7)	0.0044 (7)
C14	0.0461 (10)	0.0468 (9)	0.0327 (8)	−0.0030 (8)	0.0063 (7)	−0.0006 (7)
C15	0.0711 (14)	0.0797 (15)	0.0328 (9)	0.0057 (11)	0.0145 (9)	0.0024 (9)

S1—O1	1.4199 (13)	C5—C6	1.363 (4)
S1—O2	1.4304 (14)	C5—H5	0.9300
S1—N1	1.6105 (16)	C6—C7	1.380 (3)
S1—C8	1.7647 (16)	C6—H6	0.9300
O3—C14	1.217 (2)	C7—H7	0.9300
N1—C1	1.466 (2)	C8—C9	1.374 (2)
N1—H1N	0.893 (9)	C8—C13	1.373 (2)
N2—C14	1.346 (2)	C9—C10	1.381 (2)
N2—C11	1.4064 (19)	C9—H9	0.9300
N2—H2N	0.899 (9)	C10—C11	1.387 (2)
C1—C2	1.501 (3)	C10—H10	0.9300
C1—H1A	0.9700	C11—C12	1.382 (2)
C1—H1B	0.9700	C12—C13	1.378 (2)
C2—C7	1.380 (3)	C12—H12	0.9300
C2—C3	1.383 (3)	C13—H13	0.9300
C3—C4	1.376 (3)	C14—C15	1.501 (2)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.366 (3)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
O1—S1—O2	119.90 (9)	C7—C6—H6	119.9
O1—S1—N1	107.38 (8)	C2—C7—C6	120.8 (2)
O2—S1—N1	105.41 (9)	C2—C7—H7	119.6
O1—S1—C8	108.31 (8)	C6—C7—H7	119.6
O2—S1—C8	106.21 (8)	C9—C8—C13	120.05 (15)
N1—S1—C8	109.33 (8)	C9—C8—S1	119.43 (13)
C1—N1—S1	120.86 (14)	C13—C8—S1	120.52 (13)
C1—N1—H1N	116.3 (13)	C8—C9—C10	120.62 (16)
S1—N1—H1N	112.0 (13)	C8—C9—H9	119.7
C14—N2—C11	129.01 (14)	C10—C9—H9	119.7
C14—N2—H2N	118.3 (13)	C9—C10—C11	119.62 (16)
C11—N2—H2N	112.4 (13)	C9—C10—H10	120.2
N1—C1—C2	116.46 (15)	C11—C10—H10	120.2
N1—C1—H1A	108.2	C12—C11—C10	119.21 (15)
C2—C1—H1A	108.2	C12—C11—N2	117.12 (14)
N1—C1—H1B	108.2	C10—C11—N2	123.66 (15)
C2—C1—H1B	108.2	C13—C12—C11	120.82 (15)
H1A—C1—H1B	107.3	C13—C12—H12	119.6
C7—C2—C3	118.3 (2)	C11—C12—H12	119.6
C7—C2—C1	121.10 (19)	C8—C13—C12	119.68 (16)
C3—C2—C1	120.57 (18)	C8—C13—H13	120.2
C4—C3—C2	120.4 (2)	C12—C13—H13	120.2
C4—C3—H3	119.8	O3—C14—N2	123.00 (16)
C2—C3—H3	119.8	O3—C14—C15	121.99 (17)
C5—C4—C3	120.7 (2)	N2—C14—C15	115.01 (16)
C5—C4—H4	119.7	C14—C15—H15A	109.5
C3—C4—H4	119.7	C14—C15—H15B	109.5
C6—C5—C4	119.7 (2)	H15A—C15—H15B	109.5
C6—C5—H5	120.2	C14—C15—H15C	109.5
C4—C5—H5	120.2	H15A—C15—H15C	109.5
C5—C6—C7	120.2 (2)	H15B—C15—H15C	109.5
C5—C6—H6	119.9
O1—S1—N1—C1	35.74 (15)	O1—S1—C8—C13	−11.08 (17)
O2—S1—N1—C1	164.65 (14)	O2—S1—C8—C13	−141.10 (15)
C8—S1—N1—C1	−81.56 (15)	N1—S1—C8—C13	105.63 (15)
S1—N1—C1—C2	64.4 (2)	C13—C8—C9—C10	−0.8 (3)
N1—C1—C2—C7	−118.2 (2)	S1—C8—C9—C10	178.69 (16)
N1—C1—C2—C3	62.7 (2)	C8—C9—C10—C11	0.1 (3)
C7—C2—C3—C4	0.4 (3)	C9—C10—C11—C12	0.6 (3)
C1—C2—C3—C4	179.41 (19)	C9—C10—C11—N2	179.85 (18)
C2—C3—C4—C5	−0.1 (3)	C14—N2—C11—C12	−169.65 (17)
C3—C4—C5—C6	−0.5 (4)	C14—N2—C11—C10	11.1 (3)
C4—C5—C6—C7	0.7 (4)	C10—C11—C12—C13	−0.8 (3)
C3—C2—C7—C6	−0.1 (3)	N2—C11—C12—C13	179.98 (16)
C1—C2—C7—C6	−179.14 (19)	C9—C8—C13—C12	0.6 (3)
C5—C6—C7—C2	−0.5 (3)	S1—C8—C13—C12	−178.81 (14)
O1—S1—C8—C9	169.47 (15)	C11—C12—C13—C8	0.1 (3)
O2—S1—C8—C9	39.45 (17)	C11—N2—C14—O3	−3.2 (3)
N1—S1—C8—C9	−73.82 (16)	C11—N2—C14—C15	177.27 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3i	0.894 (17)	1.996 (17)	2.877 (2)	168.2 (16)
N2—H2n···O2ii	0.898 (15)	2.029 (15)	2.921 (2)	171.5 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3i	0.89 (2)	2.00 (2)	2.877 (2)	168 (2)
N2—H2n⋯O2ii	0.90 (2)	2.03 (2)	2.921 (2)	172 (2)

Symmetry codes: (i) ; (ii) .