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

In the title compound, C(11)H(16)N(2)O(3)S, the S atom has a distorted tetra-hedral geometry [maximum deviation: O-S-O = 119.48 (15)°]. The dihedral angles between the benzene ring and its propyl-sulfonamide and methyl-amide substituents are 71.8 (2) and 5.8 (1)°, respectively. In the crystal, mol-ecules are linked by N(m)-H⋯O(s) (m = methyl-amide and s = sulfonamide) hydrogen bonds, forming C(8) chains along the a axis. The two mol-ecule chains are connected by N-H⋯O hydrogen bonds, generating R(3) (2)(18) rings. The crystal packing is further stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to sulfonamides, see: Adams (2001 ▶); Ahrens (1996 ▶); Betts et al. (2003 ▶); Faryal et al. (2011 ▶); Mayers (2009 ▶); Root (1999 ▶). For related structures, see: Faryal et al. (2011 ▶); Ahmad et al. (2011a ▶,b ▶). For computation of ring patterns formed by hydrogen bonds in crystal structures, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Motherwell et al. (1999 ▶).

Experimental

Crystal data

C11H16N2O3S

M = 256.33

Orthorhombic,

a = 8.7791 (6) Å

b = 14.1747 (11) Å

c = 20.1577 (14) Å

V = 2508.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.13 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

22013 measured reflections

3103 independent reflections

1579 reflections with I > 2σ(I)

R int = 0.077

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.173

S = 1.01

3103 reflections

164 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055528/xu5426sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055528/xu5426Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055528/xu5426Isup3.cml

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

C11H16N2O3S	F(000) = 1088
Mr = 256.33	Dx = 1.357 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1934 reflections
a = 8.7791 (6) Å	θ = 2.9–21.9°
b = 14.1747 (11) Å	µ = 0.26 mm−1
c = 20.1577 (14) Å	T = 296 K
V = 2508.5 (3) Å3	Block, colourless
Z = 8	0.13 × 0.12 × 0.10 mm

Bruker APEXII CCD diffractometer	1579 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.077
graphite	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −10→11
22013 measured reflections	k = −18→18
3103 independent reflections	l = −26→23

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0795P)2 + 0.2926P] where P = (Fo2 + 2Fc2)/3
3103 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.08384 (8)	0.62424 (6)	0.34117 (4)	0.0520 (3)
O1	0.0871 (3)	0.55742 (16)	0.28801 (9)	0.0662 (8)
O2	−0.0349 (2)	0.61902 (17)	0.38968 (11)	0.0702 (9)
O3	0.6209 (3)	0.63450 (16)	0.58686 (10)	0.0681 (9)
N1	0.0734 (3)	0.7275 (2)	0.30872 (12)	0.0530 (9)
N2	0.6813 (3)	0.61300 (18)	0.47900 (11)	0.0492 (9)
C1	0.2273 (4)	0.8744 (3)	0.1670 (2)	0.0893 (16)
C2	0.1289 (4)	0.8443 (3)	0.22353 (19)	0.0803 (16)
C3	0.1785 (3)	0.7554 (2)	0.25581 (13)	0.0557 (10)
C4	0.2588 (3)	0.61648 (19)	0.38364 (13)	0.0431 (10)
C5	0.2664 (3)	0.6361 (2)	0.45047 (14)	0.0532 (10)
C6	0.4031 (3)	0.6343 (2)	0.48376 (14)	0.0546 (10)
C7	0.5362 (3)	0.61413 (19)	0.44927 (13)	0.0419 (9)
C8	0.5275 (3)	0.5935 (2)	0.38184 (13)	0.0474 (10)
C9	0.3906 (3)	0.5945 (2)	0.34959 (13)	0.0492 (10)
C10	0.7159 (4)	0.6219 (2)	0.54421 (15)	0.0494 (11)
C11	0.8829 (3)	0.6153 (2)	0.56009 (17)	0.0667 (14)
H1A	0.32730	0.88930	0.18310	0.1340*
H1B	0.18390	0.92900	0.14620	0.1340*
H1C	0.23410	0.82410	0.13520	0.1340*
H1N	0.071 (3)	0.7722 (14)	0.3372 (10)	0.047 (9)*
H2A	0.12780	0.89410	0.25650	0.0960*
H2B	0.02550	0.83630	0.20750	0.0960*
H2N	0.754 (2)	0.604 (2)	0.4517 (12)	0.060 (10)*
H3A	0.18360	0.70560	0.22290	0.0670*
H3B	0.27970	0.76380	0.27420	0.0670*
H5	0.17760	0.65070	0.47350	0.0640*
H6	0.40650	0.64660	0.52910	0.0660*
H8	0.61580	0.57900	0.35850	0.0570*
H9	0.38620	0.58020	0.30460	0.0590*
H11A	0.92890	0.67640	0.55550	0.1000*
H11B	0.93090	0.57180	0.53010	0.1000*
H11C	0.89560	0.59340	0.60480	0.1000*

	U11	U22	U33	U12	U13	U23
S1	0.0345 (4)	0.0769 (6)	0.0447 (4)	−0.0061 (4)	−0.0052 (3)	0.0085 (4)
O1	0.0641 (15)	0.0778 (16)	0.0568 (12)	−0.0094 (12)	−0.0178 (11)	−0.0047 (12)
O2	0.0343 (12)	0.116 (2)	0.0604 (13)	−0.0096 (12)	0.0010 (10)	0.0234 (13)
O3	0.0522 (14)	0.1056 (19)	0.0465 (12)	−0.0005 (12)	−0.0017 (11)	−0.0090 (12)
N1	0.0418 (15)	0.0712 (19)	0.0461 (14)	0.0069 (13)	−0.0014 (12)	0.0017 (13)
N2	0.0309 (14)	0.0773 (18)	0.0395 (13)	0.0056 (12)	0.0018 (11)	0.0019 (12)
C1	0.051 (2)	0.117 (3)	0.100 (3)	−0.003 (2)	0.003 (2)	0.049 (2)
C2	0.055 (2)	0.103 (3)	0.083 (3)	0.014 (2)	0.008 (2)	0.037 (2)
C3	0.0451 (18)	0.075 (2)	0.0471 (16)	−0.0035 (17)	0.0025 (14)	0.0057 (16)
C4	0.0339 (16)	0.0585 (19)	0.0370 (14)	−0.0018 (13)	−0.0012 (11)	0.0061 (13)
C5	0.0311 (16)	0.085 (2)	0.0436 (16)	0.0025 (15)	0.0065 (13)	0.0038 (15)
C6	0.0385 (17)	0.092 (2)	0.0334 (14)	0.0001 (16)	0.0019 (13)	0.0000 (14)
C7	0.0328 (15)	0.0541 (18)	0.0388 (14)	0.0023 (13)	0.0016 (12)	0.0059 (13)
C8	0.0353 (16)	0.063 (2)	0.0438 (16)	0.0039 (14)	0.0058 (12)	0.0025 (14)
C9	0.0422 (18)	0.069 (2)	0.0363 (15)	0.0029 (14)	0.0004 (13)	−0.0001 (14)
C10	0.0410 (18)	0.056 (2)	0.0512 (18)	−0.0010 (15)	−0.0058 (14)	0.0038 (14)
C11	0.043 (2)	0.092 (3)	0.065 (2)	−0.0018 (17)	−0.0138 (16)	0.0075 (18)

S1—O1	1.431 (2)	C8—C9	1.367 (4)
S1—O2	1.431 (2)	C10—C11	1.504 (4)
S1—N1	1.606 (3)	C1—H1A	0.9600
S1—C4	1.762 (3)	C1—H1B	0.9600
O3—C10	1.211 (4)	C1—H1C	0.9600
N1—C3	1.465 (4)	C2—H2A	0.9700
N2—C7	1.408 (4)	C2—H2B	0.9700
N2—C10	1.355 (4)	C3—H3A	0.9700
N1—H1N	0.86 (2)	C3—H3B	0.9700
N2—H2N	0.85 (2)	C5—H5	0.9300
C1—C2	1.492 (5)	C6—H6	0.9300
C2—C3	1.484 (5)	C8—H8	0.9300
C4—C9	1.381 (4)	C9—H9	0.9300
C4—C5	1.377 (4)	C11—H11A	0.9600
C5—C6	1.375 (4)	C11—H11B	0.9600
C6—C7	1.389 (4)	C11—H11C	0.9600
C7—C8	1.392 (4)
O1—S1—O2	119.48 (15)	C2—C1—H1C	109.00
O1—S1—N1	107.43 (13)	H1A—C1—H1B	109.00
O1—S1—C4	107.77 (14)	H1A—C1—H1C	109.00
O2—S1—N1	106.49 (14)	H1B—C1—H1C	109.00
O2—S1—C4	107.44 (13)	C1—C2—H2A	109.00
N1—S1—C4	107.73 (13)	C1—C2—H2B	109.00
S1—N1—C3	120.5 (2)	C3—C2—H2A	109.00
C7—N2—C10	127.9 (3)	C3—C2—H2B	109.00
S1—N1—H1N	113.8 (13)	H2A—C2—H2B	108.00
C3—N1—H1N	107.7 (16)	N1—C3—H3A	109.00
C7—N2—H2N	113.9 (15)	N1—C3—H3B	109.00
C10—N2—H2N	118.2 (15)	C2—C3—H3A	109.00
C1—C2—C3	114.1 (3)	C2—C3—H3B	109.00
N1—C3—C2	111.3 (2)	H3A—C3—H3B	108.00
C5—C4—C9	119.4 (2)	C4—C5—H5	119.00
S1—C4—C5	120.3 (2)	C6—C5—H5	119.00
S1—C4—C9	120.2 (2)	C5—C6—H6	120.00
C4—C5—C6	121.1 (3)	C7—C6—H6	120.00
C5—C6—C7	119.6 (3)	C7—C8—H8	120.00
N2—C7—C6	123.4 (2)	C9—C8—H8	120.00
N2—C7—C8	117.6 (2)	C4—C9—H9	120.00
C6—C7—C8	119.1 (2)	C8—C9—H9	120.00
C7—C8—C9	120.7 (2)	C10—C11—H11A	109.00
C4—C9—C8	120.2 (2)	C10—C11—H11B	109.00
O3—C10—C11	122.0 (3)	C10—C11—H11C	109.00
N2—C10—C11	114.8 (3)	H11A—C11—H11B	109.00
O3—C10—N2	123.2 (3)	H11A—C11—H11C	109.00
C2—C1—H1A	110.00	H11B—C11—H11C	109.00
C2—C1—H1B	110.00
O1—S1—N1—C3	−49.8 (3)	C7—N2—C10—O3	−1.6 (5)
O2—S1—N1—C3	−178.9 (2)	C1—C2—C3—N1	−177.3 (3)
C4—S1—N1—C3	66.1 (2)	S1—C4—C5—C6	−177.2 (2)
N1—S1—C4—C9	−82.9 (3)	S1—C4—C9—C8	176.5 (2)
N1—S1—C4—C5	94.4 (2)	C5—C4—C9—C8	−0.9 (4)
O1—S1—C4—C5	−149.9 (2)	C9—C4—C5—C6	0.1 (4)
O2—S1—C4—C5	−20.0 (3)	C4—C5—C6—C7	1.2 (4)
O1—S1—C4—C9	32.8 (3)	C5—C6—C7—N2	178.4 (3)
O2—S1—C4—C9	162.8 (2)	C5—C6—C7—C8	−1.8 (4)
S1—N1—C3—C2	167.9 (2)	N2—C7—C8—C9	−179.2 (3)
C10—N2—C7—C6	6.5 (5)	C6—C7—C8—C9	1.1 (4)
C7—N2—C10—C11	178.6 (3)	C7—C8—C9—C4	0.3 (4)
C10—N2—C7—C8	−173.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86 (2)	2.07 (2)	2.904 (3)	165 (2)
N2—H2N···O2ii	0.85 (2)	2.25 (2)	3.075 (3)	164 (2)
C9—H9···O1iii	0.93	2.59	3.308 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86 (2)	2.07 (2)	2.904 (3)	165 (2)
N2—H2N⋯O2ii	0.85 (2)	2.25 (2)	3.075 (3)	164 (2)
C9—H9⋯O1iii	0.93	2.59	3.308 (3)	135

Symmetry codes: (i) ; (ii) ; (iii) .