2-(2,5-Dichloro-benzene-sulfonamido)-3-methyl-butanoic acid.

The structure of the title compound, C(11)H(13)Cl(2)NO(4)S, shows one sulfonamide-O atom to lie almost in the plane of the benzene ring [C-C-S-O = -178.7 (2) °] and the other to one side [C-C-S-O = -49.4 (3)°]. Lying to the other side is the amine residue, which occupies a position almost perpendicular to the plane [C-S-N-C = 70.2 (2)°]; the carb-oxy-lic acid group is orientated to lie over the benzene ring. In the crystal, the appearance of an 11-membered {⋯OH⋯OCOH⋯OC(2)NH} synthon, which features the hy-droxy group forming both donor (to a carbonyl-O) and acceptor (from the amine-H) inter-actions, leads to the formation of a supra-molecular chain along the a axis. Chains are connected in the crystal structure by C-H⋯O contacts.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2010 ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C11H13Cl2NO4S

M = 326.18

Orthorhombic,

a = 5.4584 (2) Å

b = 14.0623 (6) Å

c = 19.4545 (8) Å

V = 1493.28 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.58 mm−1

T = 293 K

0.19 × 0.13 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.805, T max = 0.921

14542 measured reflections

3405 independent reflections

2876 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.127

S = 1.00

3405 reflections

180 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.51 e Å−3

Absolute structure: Flack (1983 ▶), 1415 Friedel pairs

Flack parameter: 0.09 (8)

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 n class="Disease">DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041620/hg2730sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041620/hg2730Isup2.hkl

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

C11H13Cl2NO4S	F(000) = 672
Mr = 326.18	Dx = 1.451 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4852 reflections
a = 5.4584 (2) Å	θ = 2.6–25.1°
b = 14.0623 (6) Å	µ = 0.58 mm−1
c = 19.4545 (8) Å	T = 293 K
V = 1493.28 (10) Å3	Prism, colourless
Z = 4	0.19 × 0.13 × 0.07 mm

Bruker APEXII CCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→7
Tmin = 0.805, Tmax = 0.921	k = −18→18
14542 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0887P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3405 reflections	Δρmax = 0.61 e Å−3
180 parameters	Δρmin = −0.51 e Å−3
2 restraints	Absolute structure: Flack (1983), 1415 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (8)

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
Cl1	0.36922 (17)	0.23427 (6)	0.14486 (5)	0.0617 (3)
Cl2	1.2300 (2)	0.15728 (10)	0.34471 (6)	0.0952 (4)
S1	0.59333 (11)	0.01761 (4)	0.15989 (3)	0.03515 (17)
O1	0.3334 (3)	0.01414 (15)	0.16803 (12)	0.0491 (5)
O2	0.7383 (4)	−0.06093 (14)	0.18173 (11)	0.0485 (5)
O3	1.1937 (3)	0.12919 (13)	0.00395 (12)	0.0465 (5)
H3O	1.231 (8)	0.1812 (14)	−0.0118 (19)	0.070*
O4	0.8427 (4)	0.19737 (14)	0.03380 (13)	0.0554 (6)
N1	0.6435 (4)	0.03271 (15)	0.07885 (11)	0.0359 (5)
H1N	0.528 (4)	0.0668 (18)	0.0625 (15)	0.043*
C1	0.7060 (5)	0.11804 (19)	0.20583 (13)	0.0375 (6)
C2	0.6085 (6)	0.2087 (2)	0.19980 (15)	0.0475 (7)
C3	0.6997 (8)	0.2826 (2)	0.23875 (19)	0.0671 (10)
H3	0.6316	0.3430	0.2348	0.080*
C4	0.8904 (8)	0.2675 (3)	0.28335 (19)	0.0740 (12)
H4	0.9526	0.3172	0.3096	0.089*
C5	0.9879 (7)	0.1778 (3)	0.28870 (16)	0.0615 (10)
C6	0.8996 (5)	0.1019 (2)	0.25120 (14)	0.0453 (6)
H6	0.9673	0.0416	0.2560	0.054*
C7	0.8902 (5)	0.02917 (16)	0.05012 (13)	0.0336 (5)
H7	1.0025	0.0063	0.0858	0.040*
C8	0.9042 (6)	−0.0395 (2)	−0.01197 (18)	0.0525 (8)
H8	1.0741	−0.0392	−0.0283	0.063*
C9	0.7472 (9)	−0.0072 (3)	−0.0703 (2)	0.0855 (13)
H9A	0.7767	−0.0468	−0.1097	0.128*
H9B	0.7860	0.0576	−0.0815	0.128*
H9C	0.5778	−0.0117	−0.0574	0.128*
C10	0.8466 (11)	−0.1396 (2)	0.0105 (3)	0.103 (2)
H10A	0.6806	−0.1426	0.0266	0.155*
H10B	0.9559	−0.1578	0.0468	0.155*
H10C	0.8666	−0.1821	−0.0278	0.155*
C11	0.9694 (5)	0.12818 (16)	0.02879 (14)	0.0352 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0687 (5)	0.0524 (4)	0.0638 (5)	0.0192 (4)	0.0005 (4)	0.0038 (4)
Cl2	0.0659 (6)	0.1600 (11)	0.0597 (6)	−0.0443 (7)	−0.0190 (5)	0.0070 (7)
S1	0.0295 (3)	0.0337 (3)	0.0422 (3)	−0.0026 (2)	0.0021 (3)	0.0031 (3)
O1	0.0314 (9)	0.0567 (11)	0.0593 (13)	−0.0080 (9)	0.0077 (9)	−0.0015 (10)
O2	0.0518 (11)	0.0383 (10)	0.0553 (12)	0.0021 (9)	−0.0007 (10)	0.0110 (8)
O3	0.0367 (10)	0.0367 (10)	0.0661 (13)	−0.0051 (8)	0.0044 (10)	0.0114 (9)
O4	0.0589 (13)	0.0357 (9)	0.0717 (15)	0.0117 (9)	0.0111 (11)	0.0116 (10)
N1	0.0282 (11)	0.0421 (11)	0.0375 (12)	0.0024 (9)	−0.0012 (9)	0.0013 (9)
C1	0.0346 (13)	0.0432 (14)	0.0347 (13)	−0.0069 (11)	0.0054 (11)	−0.0010 (11)
C2	0.0564 (19)	0.0437 (14)	0.0423 (16)	−0.0038 (15)	0.0099 (14)	−0.0035 (11)
C3	0.097 (3)	0.0490 (17)	0.055 (2)	−0.0171 (19)	0.011 (2)	−0.0090 (15)
C4	0.093 (3)	0.074 (2)	0.055 (2)	−0.042 (2)	0.002 (2)	−0.0117 (18)
C5	0.0509 (19)	0.094 (3)	0.0393 (16)	−0.0319 (18)	0.0020 (15)	−0.0026 (17)
C6	0.0367 (14)	0.0618 (16)	0.0375 (14)	−0.0073 (14)	0.0050 (12)	0.0050 (12)
C7	0.0283 (12)	0.0323 (11)	0.0402 (13)	0.0020 (10)	−0.0001 (10)	0.0013 (10)
C8	0.0497 (17)	0.0456 (15)	0.0623 (19)	−0.0054 (14)	0.0187 (16)	−0.0146 (13)
C9	0.086 (3)	0.115 (3)	0.056 (2)	−0.018 (3)	−0.005 (2)	−0.036 (2)
C10	0.150 (5)	0.0403 (17)	0.119 (4)	−0.019 (2)	0.050 (4)	−0.026 (2)
C11	0.0336 (13)	0.0321 (12)	0.0399 (13)	0.0004 (10)	−0.0042 (11)	0.0024 (10)

Cl1—C2	1.725 (3)	C4—C5	1.372 (6)
Cl2—C5	1.737 (4)	C4—H4	0.9300
S1—O2	1.424 (2)	C5—C6	1.380 (5)
S1—O1	1.4286 (19)	C6—H6	0.9300
S1—N1	1.614 (2)	C7—C11	1.516 (3)
S1—C1	1.781 (3)	C7—C8	1.549 (4)
O3—C11	1.317 (3)	C7—H7	0.9800
O3—H3o	0.82 (3)	C8—C9	1.494 (6)
O4—C11	1.197 (3)	C8—C10	1.506 (5)
N1—C7	1.459 (3)	C8—H8	0.9800
N1—H1n	0.853 (10)	C9—H9A	0.9600
C1—C2	1.387 (4)	C9—H9B	0.9600
C1—C6	1.395 (4)	C9—H9C	0.9600
C2—C3	1.379 (5)	C10—H10A	0.9600
C3—C4	1.372 (6)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
O2—S1—O1	119.51 (12)	N1—C7—C11	109.66 (19)
O2—S1—N1	107.41 (12)	N1—C7—C8	111.5 (2)
O1—S1—N1	106.34 (13)	C11—C7—C8	110.2 (2)
O2—S1—C1	105.87 (13)	N1—C7—H7	108.5
O1—S1—C1	108.33 (13)	C11—C7—H7	108.5
N1—S1—C1	109.10 (12)	C8—C7—H7	108.5
C11—O3—H3O	112 (3)	C9—C8—C10	112.6 (4)
C7—N1—S1	121.76 (17)	C9—C8—C7	112.0 (3)
C7—N1—H1N	124 (2)	C10—C8—C7	110.3 (3)
S1—N1—H1N	108 (2)	C9—C8—H8	107.2
C2—C1—C6	119.6 (3)	C10—C8—H8	107.2
C2—C1—S1	123.7 (2)	C7—C8—H8	107.2
C6—C1—S1	116.8 (2)	C8—C9—H9A	109.5
C3—C2—C1	120.5 (3)	C8—C9—H9B	109.5
C3—C2—Cl1	117.2 (3)	H9A—C9—H9B	109.5
C1—C2—Cl1	122.3 (2)	C8—C9—H9C	109.5
C4—C3—C2	120.3 (4)	H9A—C9—H9C	109.5
C4—C3—H3	119.8	H9B—C9—H9C	109.5
C2—C3—H3	119.8	C8—C10—H10A	109.5
C3—C4—C5	119.0 (3)	C8—C10—H10B	109.5
C3—C4—H4	120.5	H10A—C10—H10B	109.5
C5—C4—H4	120.5	C8—C10—H10C	109.5
C6—C5—C4	122.3 (3)	H10A—C10—H10C	109.5
C6—C5—Cl2	118.0 (3)	H10B—C10—H10C	109.5
C4—C5—Cl2	119.7 (3)	O4—C11—O3	123.9 (2)
C5—C6—C1	118.3 (3)	O4—C11—C7	124.0 (2)
C5—C6—H6	120.9	O3—C11—C7	112.0 (2)
C1—C6—H6	120.9
O2—S1—N1—C7	−44.1 (2)	C3—C4—C5—C6	−0.6 (6)
O1—S1—N1—C7	−173.12 (18)	C3—C4—C5—Cl2	179.8 (3)
C1—S1—N1—C7	70.2 (2)	C4—C5—C6—C1	0.8 (5)
O2—S1—C1—C2	−178.7 (2)	Cl2—C5—C6—C1	−179.6 (2)
O1—S1—C1—C2	−49.4 (3)	C2—C1—C6—C5	−0.1 (4)
N1—S1—C1—C2	66.0 (3)	S1—C1—C6—C5	−178.7 (2)
O2—S1—C1—C6	−0.2 (2)	S1—N1—C7—C11	−108.9 (2)
O1—S1—C1—C6	129.1 (2)	S1—N1—C7—C8	128.8 (2)
N1—S1—C1—C6	−115.5 (2)	N1—C7—C8—C9	63.4 (3)
C6—C1—C2—C3	−0.7 (4)	C11—C7—C8—C9	−58.6 (3)
S1—C1—C2—C3	177.8 (3)	N1—C7—C8—C10	−62.8 (4)
C6—C1—C2—Cl1	−180.0 (2)	C11—C7—C8—C10	175.2 (3)
S1—C1—C2—Cl1	−1.6 (4)	N1—C7—C11—O4	−1.6 (4)
C1—C2—C3—C4	0.8 (5)	C8—C7—C11—O4	121.4 (3)
Cl1—C2—C3—C4	−179.8 (3)	N1—C7—C11—O3	178.5 (2)
C2—C3—C4—C5	−0.2 (6)	C8—C7—C11—O3	−58.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O4i	0.82 (3)	1.86 (2)	2.674 (3)	171 (3)
N1—H1n···O3ii	0.85 (2)	2.32 (2)	3.161 (3)	167 (3)
C7—H7···O1iii	0.98	2.42	3.341 (3)	157
C4—H4···O2iv	0.93	2.41	3.223 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯O4i	0.82 (3)	1.86 (2)	2.674 (3)	171 (3)
N1—H1n⋯O3ii	0.85 (2)	2.32 (2)	3.161 (3)	167 (3)
C7—H7⋯O1iii	0.98	2.42	3.341 (3)	157
C4—H4⋯O2iv	0.93	2.41	3.223 (5)	146

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