N-{4-[(4-Methyl-phen-yl)sulfamo-yl]phen-yl}acetamide.

The title mol-ecule, C(15)H(16)N(2)O(3)S, has a twisted U-shaped conformation. The twist occurs in the central C-S(=O)(2)N(H)-C unit with the C-S-N-C torsion angle being -58.38 (14)°. The benzene rings lie to the same side of the mol-ecule and form a dihedral angle of 67.03 (10)°. The crystal packing features N-H⋯O hydrogen bonding, which leads to supra-molecular chains with a tubular topology along the b axis. Intra-molecular C-H⋯O inter-actions are also observed.

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

Triclinic,

a = 8.2224 (3) Å

b = 8.3878 (3) Å

c = 13.0796 (5) Å

α = 71.482 (2)°

β = 75.749 (2)°

γ = 61.265 (1)°

V = 745.27 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.23 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.887, T max = 0.951

12704 measured reflections

3374 independent reflections

2918 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.04

3374 reflections

198 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.34 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/S160053681002739X/pv2305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002739X/pv2305Isup2.hkl

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

C15H16N2O3S	Z = 2
Mr = 304.37	F(000) = 320
Triclinic, P1	Dx = 1.356 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2224 (3) Å	Cell parameters from 7070 reflections
b = 8.3878 (3) Å	θ = 2.9–28.3°
c = 13.0796 (5) Å	µ = 0.23 mm−1
α = 71.482 (2)°	T = 293 K
β = 75.749 (2)°	Block, colourless
γ = 61.265 (1)°	0.23 × 0.14 × 0.08 mm
V = 745.27 (5) Å3

Bruker APEXII CCD diffractometer	3374 independent reflections
Radiation source: fine-focus sealed tube	2918 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.887, Tmax = 0.951	k = −10→10
12704 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 = 1.04	w = 1/[σ2(Fo2) + (0.0681P)2 + 0.1946P] where P = (Fo2 + 2Fc2)/3
3374 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.34 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	0.12002 (5)	0.25013 (5)	0.75637 (3)	0.04453 (15)
O1	−0.01522 (16)	0.24530 (17)	0.84756 (11)	0.0578 (3)
O2	0.09188 (18)	0.42467 (16)	0.67943 (11)	0.0581 (3)
O3	0.4166 (2)	−0.2526 (2)	0.37348 (12)	0.0728 (4)
N1	0.31999 (19)	0.17594 (19)	0.79741 (11)	0.0459 (3)
H1N	0.391 (2)	0.214 (3)	0.7440 (11)	0.055*
N2	0.21546 (19)	−0.29178 (19)	0.51939 (11)	0.0437 (3)
H2N	0.164 (2)	−0.365 (2)	0.5573 (13)	0.052*
C1	0.4103 (2)	−0.0054 (2)	0.86613 (12)	0.0429 (3)
C2	0.5858 (3)	−0.1276 (3)	0.83046 (15)	0.0614 (5)
H2	0.6388	−0.0963	0.7601	0.074*
C3	0.6828 (3)	−0.2962 (3)	0.89901 (17)	0.0693 (5)
H3	0.8020	−0.3765	0.8746	0.083*
C4	0.6068 (3)	−0.3481 (3)	1.00264 (16)	0.0596 (5)
C5	0.4290 (3)	−0.2261 (3)	1.03546 (15)	0.0633 (5)
H5	0.3738	−0.2601	1.1047	0.076*
C6	0.3305 (3)	−0.0558 (3)	0.96922 (14)	0.0553 (4)
H6	0.2113	0.0244	0.9938	0.066*
C7	0.7165 (4)	−0.5295 (3)	1.0789 (2)	0.0835 (7)
H7A	0.7837	−0.5081	1.1196	0.125*
H7B	0.8030	−0.6197	1.0377	0.125*
H7C	0.6324	−0.5759	1.1278	0.125*
C8	0.1436 (2)	0.0924 (2)	0.68549 (13)	0.0405 (3)
C9	0.2424 (3)	0.0930 (2)	0.58393 (15)	0.0541 (4)
H9	0.2931	0.1780	0.5537	0.065*
C10	0.2674 (3)	−0.0305 (2)	0.52644 (14)	0.0532 (4)
H10	0.3330	−0.0276	0.4575	0.064*
C11	0.1941 (2)	−0.1593 (2)	0.57195 (12)	0.0387 (3)
C12	0.0926 (2)	−0.1576 (2)	0.67372 (13)	0.0468 (4)
H12	0.0410	−0.2419	0.7040	0.056*
C13	0.0671 (2)	−0.0332 (2)	0.73066 (13)	0.0472 (4)
H13	−0.0010	−0.0335	0.7989	0.057*
C14	0.3207 (2)	−0.3310 (2)	0.42545 (13)	0.0451 (4)
C15	0.3142 (3)	−0.4801 (2)	0.38969 (15)	0.0561 (4)
H15A	0.3141	−0.4457	0.3123	0.084*
H15B	0.2028	−0.4941	0.4240	0.084*
H15C	0.4215	−0.5962	0.4098	0.084*

	U11	U22	U33	U12	U13	U23
S1	0.0380 (2)	0.0362 (2)	0.0593 (3)	−0.01654 (16)	−0.00415 (16)	−0.01162 (17)
O1	0.0426 (6)	0.0572 (7)	0.0737 (8)	−0.0215 (5)	0.0084 (6)	−0.0273 (6)
O2	0.0592 (7)	0.0366 (6)	0.0783 (8)	−0.0216 (5)	−0.0167 (6)	−0.0052 (6)
O3	0.0807 (10)	0.0762 (9)	0.0703 (8)	−0.0511 (8)	0.0268 (7)	−0.0277 (7)
N1	0.0425 (7)	0.0476 (7)	0.0521 (7)	−0.0252 (6)	−0.0035 (6)	−0.0098 (6)
N2	0.0436 (7)	0.0411 (7)	0.0487 (7)	−0.0239 (6)	−0.0029 (5)	−0.0061 (5)
C1	0.0433 (8)	0.0455 (8)	0.0463 (8)	−0.0229 (7)	−0.0056 (6)	−0.0127 (6)
C2	0.0550 (10)	0.0598 (11)	0.0530 (9)	−0.0163 (9)	0.0022 (8)	−0.0132 (8)
C3	0.0625 (12)	0.0567 (11)	0.0703 (12)	−0.0092 (9)	−0.0084 (10)	−0.0185 (9)
C4	0.0733 (12)	0.0496 (10)	0.0644 (11)	−0.0289 (9)	−0.0261 (9)	−0.0068 (8)
C5	0.0692 (12)	0.0741 (13)	0.0490 (9)	−0.0402 (11)	−0.0099 (8)	−0.0003 (9)
C6	0.0471 (9)	0.0671 (11)	0.0497 (9)	−0.0262 (8)	−0.0002 (7)	−0.0130 (8)
C7	0.1059 (19)	0.0585 (13)	0.0869 (15)	−0.0302 (13)	−0.0458 (14)	−0.0009 (11)
C8	0.0349 (7)	0.0340 (7)	0.0512 (8)	−0.0156 (6)	−0.0072 (6)	−0.0056 (6)
C9	0.0579 (10)	0.0488 (9)	0.0631 (10)	−0.0371 (8)	0.0089 (8)	−0.0120 (8)
C10	0.0578 (10)	0.0520 (9)	0.0530 (9)	−0.0345 (8)	0.0110 (7)	−0.0124 (7)
C11	0.0333 (7)	0.0342 (7)	0.0455 (7)	−0.0151 (6)	−0.0079 (6)	−0.0022 (6)
C12	0.0528 (9)	0.0448 (8)	0.0483 (8)	−0.0322 (7)	0.0000 (7)	−0.0043 (7)
C13	0.0525 (9)	0.0460 (8)	0.0458 (8)	−0.0300 (7)	0.0017 (7)	−0.0060 (6)
C14	0.0395 (8)	0.0408 (8)	0.0474 (8)	−0.0137 (6)	−0.0080 (6)	−0.0048 (6)
C15	0.0551 (10)	0.0522 (10)	0.0601 (10)	−0.0186 (8)	−0.0121 (8)	−0.0155 (8)

S1—O1	1.4214 (13)	C5—H5	0.9300
S1—O2	1.4362 (12)	C6—H6	0.9300
S1—N1	1.6178 (14)	C7—H7A	0.9600
S1—C8	1.7581 (16)	C7—H7B	0.9600
O3—C14	1.211 (2)	C7—H7C	0.9600
N1—C1	1.431 (2)	C8—C9	1.376 (2)
N1—H1N	0.877 (9)	C8—C13	1.383 (2)
N2—C14	1.351 (2)	C9—C10	1.376 (2)
N2—C11	1.406 (2)	C9—H9	0.9300
N2—H2N	0.867 (9)	C10—C11	1.388 (2)
C1—C2	1.378 (2)	C10—H10	0.9300
C1—C6	1.377 (2)	C11—C12	1.386 (2)
C2—C3	1.379 (3)	C12—C13	1.376 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.374 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.495 (2)
C4—C5	1.378 (3)	C15—H15A	0.9600
C4—C7	1.511 (3)	C15—H15B	0.9600
C5—C6	1.376 (3)	C15—H15C	0.9600
O1—S1—O2	119.51 (8)	H7A—C7—H7B	109.5
O1—S1—N1	109.54 (8)	C4—C7—H7C	109.5
O2—S1—N1	104.83 (7)	H7A—C7—H7C	109.5
O1—S1—C8	107.30 (7)	H7B—C7—H7C	109.5
O2—S1—C8	107.71 (8)	C9—C8—C13	119.74 (15)
N1—S1—C8	107.41 (7)	C9—C8—S1	119.07 (12)
C1—N1—S1	122.71 (10)	C13—C8—S1	121.19 (12)
C1—N1—H1N	116.6 (13)	C8—C9—C10	121.02 (14)
S1—N1—H1N	108.7 (13)	C8—C9—H9	119.5
C14—N2—C11	128.32 (13)	C10—C9—H9	119.5
C14—N2—H2N	117.5 (13)	C9—C10—C11	119.64 (15)
C11—N2—H2N	113.7 (12)	C9—C10—H10	120.2
C2—C1—C6	119.49 (17)	C11—C10—H10	120.2
C2—C1—N1	119.02 (15)	C12—C11—C10	119.07 (15)
C6—C1—N1	121.37 (15)	C12—C11—N2	117.67 (13)
C1—C2—C3	120.06 (18)	C10—C11—N2	123.25 (14)
C1—C2—H2	120.0	C13—C12—C11	121.06 (14)
C3—C2—H2	120.0	C13—C12—H12	119.5
C4—C3—C2	121.35 (19)	C11—C12—H12	119.5
C4—C3—H3	119.3	C12—C13—C8	119.45 (15)
C2—C3—H3	119.3	C12—C13—H13	120.3
C3—C4—C5	117.56 (18)	C8—C13—H13	120.3
C3—C4—C7	121.1 (2)	O3—C14—N2	122.59 (16)
C5—C4—C7	121.3 (2)	O3—C14—C15	121.55 (16)
C6—C5—C4	122.19 (18)	N2—C14—C15	115.85 (15)
C6—C5—H5	118.9	C14—C15—H15A	109.5
C4—C5—H5	118.9	C14—C15—H15B	109.5
C5—C6—C1	119.30 (17)	H15A—C15—H15B	109.5
C5—C6—H6	120.3	C14—C15—H15C	109.5
C1—C6—H6	120.3	H15A—C15—H15C	109.5
C4—C7—H7A	109.5	H15B—C15—H15C	109.5
C4—C7—H7B	109.5
O1—S1—N1—C1	57.85 (14)	O1—S1—C8—C13	−11.81 (16)
O2—S1—N1—C1	−172.76 (12)	O2—S1—C8—C13	−141.68 (14)
C8—S1—N1—C1	−58.38 (14)	N1—S1—C8—C13	105.88 (14)
S1—N1—C1—C2	121.29 (16)	C13—C8—C9—C10	−0.3 (3)
S1—N1—C1—C6	−62.61 (19)	S1—C8—C9—C10	178.75 (15)
C6—C1—C2—C3	−2.2 (3)	C8—C9—C10—C11	−0.9 (3)
N1—C1—C2—C3	173.98 (18)	C9—C10—C11—C12	1.7 (3)
C1—C2—C3—C4	1.3 (3)	C9—C10—C11—N2	−179.09 (16)
C2—C3—C4—C5	0.6 (3)	C14—N2—C11—C12	−173.58 (15)
C2—C3—C4—C7	−177.6 (2)	C14—N2—C11—C10	7.2 (3)
C3—C4—C5—C6	−1.7 (3)	C10—C11—C12—C13	−1.3 (2)
C7—C4—C5—C6	176.52 (19)	N2—C11—C12—C13	179.41 (15)
C4—C5—C6—C1	0.8 (3)	C11—C12—C13—C8	0.1 (3)
C2—C1—C6—C5	1.2 (3)	C9—C8—C13—C12	0.7 (3)
N1—C1—C6—C5	−174.91 (16)	S1—C8—C13—C12	−178.36 (13)
O1—S1—C8—C9	169.12 (13)	C11—N2—C14—O3	1.1 (3)
O2—S1—C8—C9	39.25 (15)	C11—N2—C14—C15	−179.77 (14)
N1—S1—C8—C9	−73.19 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.93	2.60	3.125 (3)	116
C10—H10···O3	0.93	2.22	2.818 (3)	121
C13—H13···O1	0.93	2.56	2.914 (3)	103
N1—H1n···O3i	0.88 (2)	1.99 (2)	2.853 (3)	169 (2)
N2—H2n···O2ii	0.87 (2)	2.18 (2)	3.029 (2)	165 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.93	2.60	3.125 (3)	116
C10—H10⋯O3	0.93	2.22	2.818 (3)	121
C13—H13⋯O1	0.93	2.56	2.914 (3)	103
N1—H1n⋯O3i	0.88 (2)	1.99 (2)	2.853 (3)	169 (2)
N2—H2n⋯O2ii	0.87 (2)	2.18 (2)	3.029 (2)	165 (2)

Symmetry codes: (i) ; (ii) .