3-Chloro-N-(4-sulfamoylphen-yl)propanamide.

In the title compound, C(9)H(11)ClN(2)O(3)S, the dihedral angle between the benzene ring and the amido -NHCO- plane is 15.0 (2)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, the amino NH(2) group is involved in inter-molecular N-H⋯O hydrogen bonds, which connect the mol-ecules into a double layer structure expanding parallel to the bc plane. The layers are further linked by an amido N-H⋯O hydrogen bond. Between the layers, a weak π-π inter-action with a centroid-centroid distance of 3.7447 (12) Å is also observed.

Related literature

For the anti­bacterial and pharmacological properties of sulfonamides and their derivatives, see: Albala et al. (1994 ▶); Mann & Keilin (1940 ▶); Maren (1976 ▶); Pastorekova et al. (2004 ▶); Reynolds (1996 ▶); Silverman (1992 ▶); Supuran & Scozzafava (2001 ▶, 2002 ▶); Supuran et al. (2003 ▶, 2004 ▶); Türkmen et al. (2005 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H11ClN2O3S

M = 262.72

Monoclinic,

a = 7.7554 (4) Å

b = 14.8191 (8) Å

c = 9.7482 (5) Å

β = 94.181 (4)°

V = 1117.36 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.52 mm−1

T = 296 K

0.78 × 0.45 × 0.22 mm

Data collection

Stoe IPDS2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.754, T max = 0.892

6023 measured reflections

2294 independent reflections

2007 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.08

2294 reflections

153 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.44 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA (Stoe & Cie, 2002 ▶); data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020465/is2555sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020465/is2555Isup2.hkl

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

C9H11ClN2O3S	F(000) = 544
Mr = 262.72	Dx = 1.562 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8775 reflections
a = 7.7554 (4) Å	θ = 2.1–28.0°
b = 14.8191 (8) Å	µ = 0.52 mm−1
c = 9.7482 (5) Å	T = 296 K
β = 94.181 (4)°	Prism, colourless
V = 1117.36 (10) Å3	0.78 × 0.45 × 0.22 mm
Z = 4

Stoe IPDS2 diffractometer	2294 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2007 reflections with I > 2σ(I)
plane graphite	Rint = 0.040
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.5°
ω scans	h = −8→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −16→18
Tmin = 0.754, Tmax = 0.892	l = −12→12
6023 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.351P] where P = (Fo2 + 2Fc2)/3
2294 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.44 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
Cl1	0.18392 (12)	−0.00186 (4)	0.38004 (9)	0.0791 (3)
S1	0.31196 (6)	0.73280 (3)	0.40392 (4)	0.0330 (1)
O1	0.2882 (2)	0.75787 (10)	0.54296 (14)	0.0471 (5)
O2	0.4665 (2)	0.76199 (10)	0.34461 (15)	0.0445 (5)
O3	0.1258 (2)	0.28706 (10)	0.52407 (19)	0.0571 (6)
N1	0.1520 (2)	0.77368 (12)	0.31092 (18)	0.0398 (5)
N2	0.3009 (2)	0.33382 (11)	0.36141 (18)	0.0419 (5)
C1	0.3044 (2)	0.61415 (12)	0.39403 (17)	0.0331 (5)
C2	0.2424 (3)	0.56420 (15)	0.4978 (2)	0.0499 (7)
C3	0.2372 (4)	0.47119 (15)	0.4898 (2)	0.0530 (7)
C4	0.2965 (2)	0.42797 (13)	0.37652 (19)	0.0360 (5)
C5	0.3592 (3)	0.47919 (15)	0.2722 (2)	0.0508 (7)
C6	0.3617 (3)	0.57169 (15)	0.2792 (2)	0.0488 (7)
C7	0.2202 (3)	0.27011 (13)	0.4329 (2)	0.0389 (6)
C8	0.2583 (3)	0.17489 (14)	0.3889 (2)	0.0448 (6)
C9	0.1263 (4)	0.10957 (16)	0.4265 (4)	0.0725 (10)
H1A	0.153 (4)	0.7665 (17)	0.2235 (18)	0.053 (7)*
H1B	0.055 (3)	0.7636 (17)	0.342 (3)	0.051 (7)*
H2	0.20340	0.59310	0.57430	0.0600*
H2A	0.36310	0.31400	0.29840	0.0500*
H3	0.19400	0.43770	0.56030	0.0640*
H5	0.40020	0.45050	0.19620	0.0610*
H6	0.40150	0.60550	0.20760	0.0590*
H8A	0.26540	0.17370	0.29000	0.0540*
H8B	0.36990	0.15670	0.43140	0.0540*
H9A	0.01560	0.12520	0.38000	0.0870*
H9B	0.11490	0.11230	0.52490	0.0870*

	U11	U22	U33	U12	U13	U23
Cl1	0.1120 (6)	0.0337 (3)	0.0982 (6)	−0.0094 (3)	0.0520 (5)	−0.0065 (3)
S1	0.0424 (3)	0.0302 (2)	0.0276 (2)	−0.0060 (2)	0.0106 (2)	−0.0011 (2)
O1	0.0702 (10)	0.0434 (8)	0.0294 (7)	−0.0105 (7)	0.0146 (6)	−0.0057 (5)
O2	0.0459 (8)	0.0452 (8)	0.0440 (8)	−0.0140 (6)	0.0142 (6)	0.0000 (6)
O3	0.0628 (10)	0.0383 (8)	0.0757 (11)	−0.0035 (7)	0.0427 (9)	−0.0018 (7)
N1	0.0471 (10)	0.0372 (9)	0.0367 (9)	0.0024 (7)	0.0131 (7)	0.0019 (7)
N2	0.0504 (10)	0.0315 (8)	0.0466 (9)	0.0014 (7)	0.0233 (7)	−0.0011 (7)
C1	0.0382 (10)	0.0295 (9)	0.0323 (8)	0.0002 (7)	0.0075 (7)	0.0012 (6)
C2	0.0740 (15)	0.0352 (10)	0.0443 (11)	0.0005 (10)	0.0310 (10)	0.0001 (8)
C3	0.0814 (16)	0.0348 (11)	0.0473 (11)	0.0008 (11)	0.0354 (11)	0.0060 (9)
C4	0.0383 (10)	0.0315 (9)	0.0394 (9)	0.0021 (8)	0.0116 (8)	0.0022 (7)
C5	0.0732 (15)	0.0387 (10)	0.0447 (11)	−0.0035 (10)	0.0323 (11)	−0.0041 (9)
C6	0.0712 (15)	0.0377 (10)	0.0410 (10)	−0.0061 (10)	0.0278 (10)	0.0009 (8)
C7	0.0385 (10)	0.0335 (10)	0.0461 (11)	−0.0008 (8)	0.0126 (8)	0.0004 (8)
C8	0.0500 (12)	0.0344 (10)	0.0520 (11)	−0.0010 (9)	0.0176 (9)	−0.0027 (8)
C9	0.0714 (18)	0.0328 (11)	0.118 (2)	−0.0020 (12)	0.0382 (17)	−0.0012 (13)

Cl1—C9	1.778 (3)	C3—C4	1.384 (3)
S1—O1	1.4302 (14)	C4—C5	1.385 (3)
S1—O2	1.4349 (16)	C5—C6	1.373 (3)
S1—N1	1.6012 (17)	C7—C8	1.510 (3)
S1—C1	1.7617 (18)	C8—C9	1.475 (4)
O3—C7	1.218 (3)	C2—H2	0.9300
N2—C4	1.404 (3)	C3—H3	0.9300
N2—C7	1.354 (3)	C5—H5	0.9300
N1—H1A	0.859 (18)	C6—H6	0.9300
N1—H1B	0.85 (2)	C8—H8A	0.9700
N2—H2A	0.8600	C8—H8B	0.9700
C1—C2	1.369 (3)	C9—H9A	0.9700
C1—C6	1.385 (3)	C9—H9B	0.9700
C2—C3	1.381 (3)
Cl1···N1i	3.3993 (19)	C3···O3	2.889 (3)
Cl1···C9ii	3.543 (3)	C7···O2vi	3.173 (3)
Cl1···H9Bii	3.0400	C8···O2vi	3.372 (3)
S1···O1iii	3.5128 (14)	C9···Cl1ii	3.543 (3)
O1···N1iv	2.926 (2)	C7···H3	2.7900
O1···S1iv	3.5128 (14)	C8···H6x	3.0400
O1···O2iv	3.171 (2)	H1A···O1iii	2.14 (2)
O2···N2v	2.992 (2)	H1A···H2iii	2.5800
O2···C8vi	3.372 (3)	H1B···O3vii	2.12 (3)
O2···O1iii	3.171 (2)	H2···O1	2.5500
O2···C7vi	3.173 (3)	H2···H1Aiv	2.5800
O3···N1vii	2.923 (2)	H2A···H5	2.2800
O3···C3	2.889 (3)	H2A···H8A	2.2100
O1···H6iv	2.6900	H2A···O2x	2.1300
O1···H1Aiv	2.14 (2)	H3···O3	2.3200
O1···H2	2.5500	H3···C7	2.7900
O2···H8Av	2.8600	H5···H2A	2.2800
O2···H6	2.7100	H6···O2	2.7100
O2···H2Av	2.1300	H6···C8v	3.0400
O2···H8Bvi	2.7200	H6···H8Bv	2.4300
O3···H9A	2.8800	H6···O1iii	2.6900
O3···H9B	2.5900	H8A···H2A	2.2100
O3···H3	2.3200	H8A···O2x	2.8600
O3···H1Bvii	2.12 (3)	H8A···O3xi	2.8000
O3···H8Aviii	2.8000	H8B···H6x	2.4300
N1···Cl1ix	3.3993 (19)	H8B···O2vi	2.7200
N1···O3vii	2.923 (2)	H9A···O3	2.8800
N1···O1iii	2.926 (2)	H9B···O3	2.5900
N2···O2x	2.991 (2)	H9B···Cl1ii	3.0400
O1—S1—O2	118.21 (9)	N2—C7—C8	113.46 (18)
O1—S1—N1	106.87 (9)	O3—C7—C8	122.71 (18)
O1—S1—C1	107.76 (8)	C7—C8—C9	112.9 (2)
O2—S1—N1	107.05 (9)	Cl1—C9—C8	110.8 (2)
O2—S1—C1	107.72 (8)	C1—C2—H2	120.00
N1—S1—C1	108.98 (9)	C3—C2—H2	120.00
C4—N2—C7	128.58 (17)	C2—C3—H3	120.00
S1—N1—H1A	117 (2)	C4—C3—H3	120.00
S1—N1—H1B	113.8 (19)	C4—C5—H5	120.00
H1A—N1—H1B	114 (3)	C6—C5—H5	119.00
C4—N2—H2A	116.00	C1—C6—H6	120.00
C7—N2—H2A	116.00	C5—C6—H6	120.00
S1—C1—C2	120.76 (14)	C7—C8—H8A	109.00
S1—C1—C6	119.09 (14)	C7—C8—H8B	109.00
C2—C1—C6	120.15 (18)	C9—C8—H8A	109.00
C1—C2—C3	120.56 (19)	C9—C8—H8B	109.00
C2—C3—C4	119.8 (2)	H8A—C8—H8B	108.00
N2—C4—C5	117.07 (17)	Cl1—C9—H9A	109.00
C3—C4—C5	119.15 (19)	Cl1—C9—H9B	109.00
N2—C4—C3	123.77 (18)	C8—C9—H9A	110.00
C4—C5—C6	121.01 (19)	C8—C9—H9B	109.00
C1—C6—C5	119.32 (19)	H9A—C9—H9B	108.00
O3—C7—N2	123.84 (18)
O1—S1—C1—C2	14.47 (18)	C2—C1—C6—C5	−1.5 (3)
O2—S1—C1—C2	143.03 (16)	C6—C1—C2—C3	0.4 (3)
N1—S1—C1—C2	−101.16 (17)	C1—C2—C3—C4	0.6 (4)
O1—S1—C1—C6	−165.74 (15)	C2—C3—C4—N2	178.1 (2)
O2—S1—C1—C6	−37.18 (17)	C2—C3—C4—C5	−0.5 (3)
N1—S1—C1—C6	78.63 (17)	N2—C4—C5—C6	−179.24 (19)
C7—N2—C4—C3	15.1 (3)	C3—C4—C5—C6	−0.6 (3)
C7—N2—C4—C5	−166.4 (2)	C4—C5—C6—C1	1.6 (3)
C4—N2—C7—O3	1.0 (3)	O3—C7—C8—C9	21.5 (3)
C4—N2—C7—C8	−178.99 (18)	N2—C7—C8—C9	−158.5 (2)
S1—C1—C2—C3	−179.80 (19)	C7—C8—C9—Cl1	−177.00 (18)
S1—C1—C6—C5	178.75 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1iii	0.859 (18)	2.14 (2)	2.926 (2)	151 (3)
N1—H1B···O3vii	0.85 (2)	2.12 (3)	2.923 (2)	158 (3)
N2—H2A···O2x	0.86	2.13	2.991 (2)	175
C3—H3···O3	0.93	2.32	2.889 (3)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.859 (18)	2.14 (2)	2.926 (2)	151 (3)
N1—H1B⋯O3ii	0.85 (2)	2.12 (3)	2.923 (2)	158 (3)
N2—H2A⋯O2iii	0.86	2.13	2.991 (2)	175
C3—H3⋯O3	0.93	2.32	2.889 (3)	120

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