2-(4-Acetamido-benzene-sulfonamido)-3-methyl-butanoic acid.

In the title compound, C(13)H(18)N(2)O(5)S, the benzene ring and the acetamide group are almost coplanar [dihedral angle = 5.6 (3)°], and the amine group projects almost vertically from this plane [C-C-S-N = -84.5 (7)°]. A short intra-molecular C-H⋯O contact occurs. In the crystal, O-H⋯O, N-H⋯O and N-H⋯(O,O) hydrogen bonds lead to a three-dimensional network. One of the methyl groups of the isopropyl residue is disordered over two orientations in a 0.747 (16):0.253 (16) ratio.

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

C13H18N2O5S

M = 314.35

Orthorhombic,

a = 5.1649 (13) Å

b = 14.724 (5) Å

c = 20.688 (7) Å

V = 1573.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.39 × 0.09 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

7356 measured reflections

1647 independent reflections

1083 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.209

S = 1.16

1647 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.52 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/S1600536810016119/hb5434sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016119/hb5434Isup2.hkl

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

C13H18N2O5S	F(000) = 664
Mr = 314.35	Dx = 1.327 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 815 reflections
a = 5.1649 (13) Å	θ = 3.0–18.5°
b = 14.724 (5) Å	µ = 0.23 mm−1
c = 20.688 (7) Å	T = 293 K
V = 1573.2 (8) Å3	Prism, colourless
Z = 4	0.39 × 0.09 × 0.07 mm

Bruker APEXII CCD diffractometer	1083 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
graphite	θmax = 25.0°, θmin = 1.7°
φ and ω scans	h = −6→5
7356 measured reflections	k = −14→17
1647 independent reflections	l = −24→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.1138P)2] where P = (Fo2 + 2Fc2)/3
1647 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.49 e Å−3
2 restraints	Δρmin = −0.52 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	Occ. (<1)
S1	0.6472 (3)	0.98522 (14)	0.24127 (8)	0.0374 (6)
O1	0.7761 (10)	0.9900 (4)	0.3028 (2)	0.0474 (15)
O2	0.3793 (9)	1.0094 (4)	0.2371 (3)	0.0484 (14)
O3	0.4852 (13)	0.6006 (4)	0.0597 (3)	0.0627 (19)
O4	1.0931 (11)	0.9940 (5)	0.0904 (3)	0.068 (2)
O5	0.7406 (11)	0.9868 (5)	0.0302 (3)	0.0618 (19)
H5O	0.8216	0.9540	−0.0023	0.093*
N1	0.8024 (12)	0.6160 (5)	0.1338 (3)	0.0423 (17)
H1N	0.947 (8)	0.593 (5)	0.146 (4)	0.051*
N2	0.8017 (12)	1.0547 (4)	0.1940 (3)	0.0347 (15)
H2N	0.963 (4)	1.041 (5)	0.194 (3)	0.042*
C1	0.6850 (14)	0.8749 (5)	0.2107 (4)	0.0341 (17)
C2	0.5207 (16)	0.8443 (6)	0.1626 (4)	0.044 (2)
H2	0.3858	0.8810	0.1483	0.053*
C3	0.5570 (17)	0.7596 (6)	0.1360 (4)	0.051 (2)
H3	0.4462	0.7395	0.1036	0.061*
C4	0.7560 (14)	0.7038 (5)	0.1568 (4)	0.0381 (19)
C5	0.9198 (15)	0.7362 (6)	0.2053 (4)	0.045 (2)
H5	1.0537	0.6994	0.2201	0.054*
C6	0.8875 (16)	0.8207 (6)	0.2314 (4)	0.047 (2)
H6	1.0011	0.8417	0.2629	0.056*
C7	0.6686 (18)	0.5689 (6)	0.0892 (4)	0.045 (2)
C8	0.7567 (19)	0.4720 (5)	0.0793 (4)	0.057 (2)
H8A	0.6125	0.4316	0.0850	0.086*
H8B	0.8891	0.4575	0.1102	0.086*
H8C	0.8245	0.4652	0.0364	0.086*
C9	0.7105 (16)	1.0683 (6)	0.1282 (3)	0.0403 (19)
H9	0.5295	1.0486	0.1256	0.048*
C10	0.8709 (15)	1.0112 (6)	0.0812 (3)	0.0429 (19)
C11	0.724 (2)	1.1699 (7)	0.1107 (5)	0.071 (3)	0.747 (16)
H11	0.9013	1.1893	0.1209	0.086*	0.747 (16)
C12	0.550 (3)	1.2240 (7)	0.1542 (6)	0.103 (5)	0.747 (16)
H12A	0.5831	1.2876	0.1483	0.154*	0.747 (16)
H12B	0.5821	1.2077	0.1984	0.154*	0.747 (16)
H12C	0.3724	1.2113	0.1437	0.154*	0.747 (16)
C13	0.683 (4)	1.1929 (11)	0.0441 (7)	0.109 (7)	0.747 (16)
H13A	0.5309	1.1626	0.0286	0.164*	0.747 (16)
H13B	0.8302	1.1742	0.0190	0.164*	0.747 (16)
H13C	0.6608	1.2574	0.0402	0.164*	0.747 (16)
C11A	0.724 (2)	1.1699 (7)	0.1107 (5)	0.071 (3)	0.253 (16)
H11A	0.6178	1.1695	0.0715	0.086*	0.253 (16)
C12A	0.550 (3)	1.2240 (7)	0.1542 (6)	0.103 (5)	0.253 (16)
H12D	0.6523	1.2566	0.1851	0.154*	0.253 (16)
H12E	0.4339	1.1837	0.1764	0.154*	0.253 (16)
H12F	0.4513	1.2663	0.1288	0.154*	0.253 (16)
C13A	0.928 (14)	1.213 (3)	0.088 (2)	0.109 (7)	0.253 (16)
H13D	0.9508	1.1990	0.0433	0.164*	0.253 (16)
H13E	1.0795	1.1945	0.1118	0.164*	0.253 (16)
H13F	0.9041	1.2774	0.0933	0.164*	0.253 (16)

	U11	U22	U33	U12	U13	U23
S1	0.0357 (10)	0.0429 (11)	0.0336 (9)	−0.0026 (9)	0.0032 (8)	−0.0080 (8)
O1	0.055 (3)	0.058 (4)	0.029 (3)	−0.006 (3)	−0.001 (2)	−0.008 (3)
O2	0.032 (3)	0.058 (4)	0.055 (3)	0.003 (3)	0.006 (2)	−0.013 (3)
O3	0.078 (4)	0.049 (4)	0.061 (4)	0.014 (4)	−0.028 (4)	−0.016 (3)
O4	0.047 (4)	0.104 (6)	0.054 (4)	0.028 (4)	−0.001 (3)	−0.015 (4)
O5	0.052 (4)	0.080 (5)	0.053 (3)	0.006 (3)	−0.001 (3)	−0.034 (4)
N1	0.045 (4)	0.034 (4)	0.048 (4)	0.008 (3)	−0.007 (3)	−0.001 (3)
N2	0.032 (4)	0.033 (3)	0.039 (3)	−0.002 (3)	0.004 (3)	−0.002 (3)
C1	0.031 (4)	0.035 (4)	0.036 (4)	−0.003 (3)	0.000 (3)	−0.002 (3)
C2	0.036 (4)	0.040 (5)	0.056 (5)	0.005 (4)	−0.011 (4)	−0.006 (4)
C3	0.048 (5)	0.045 (5)	0.059 (6)	0.003 (4)	−0.020 (4)	−0.014 (5)
C4	0.037 (4)	0.034 (4)	0.043 (4)	0.004 (4)	0.001 (4)	0.000 (4)
C5	0.044 (5)	0.043 (5)	0.047 (5)	0.006 (4)	−0.013 (4)	0.008 (4)
C6	0.048 (5)	0.047 (5)	0.044 (5)	−0.003 (4)	−0.018 (4)	−0.004 (4)
C7	0.060 (6)	0.037 (5)	0.038 (4)	−0.004 (4)	0.006 (5)	−0.006 (4)
C8	0.077 (6)	0.039 (5)	0.054 (5)	0.010 (5)	−0.008 (5)	−0.011 (5)
C9	0.042 (5)	0.044 (5)	0.035 (4)	0.008 (4)	0.006 (3)	−0.001 (4)
C10	0.035 (5)	0.049 (5)	0.045 (4)	0.000 (4)	0.012 (4)	0.004 (4)
C11	0.108 (9)	0.041 (6)	0.064 (6)	0.021 (6)	0.020 (6)	0.014 (5)
C12	0.154 (13)	0.053 (7)	0.102 (9)	0.052 (8)	0.004 (9)	−0.011 (7)
C13	0.21 (2)	0.057 (9)	0.064 (10)	0.008 (12)	−0.005 (11)	0.004 (8)
C11A	0.108 (9)	0.041 (6)	0.064 (6)	0.021 (6)	0.020 (6)	0.014 (5)
C12A	0.154 (13)	0.053 (7)	0.102 (9)	0.052 (8)	0.004 (9)	−0.011 (7)
C13A	0.21 (2)	0.057 (9)	0.064 (10)	0.008 (12)	−0.005 (11)	0.004 (8)

S1—O2	1.431 (5)	C8—H8B	0.9600
S1—O1	1.438 (5)	C8—H8C	0.9600
S1—N2	1.625 (6)	C9—C10	1.530 (10)
S1—C1	1.754 (8)	C9—C11A	1.541 (12)
O3—C7	1.220 (10)	C9—C11	1.541 (12)
O4—C10	1.191 (9)	C9—H9	0.9800
O5—C10	1.301 (9)	C11—C13	1.434 (17)
O5—H5O	0.9275	C11—C12	1.503 (14)
N1—C7	1.345 (10)	C11—H11	0.9800
N1—C4	1.398 (10)	C12—H12A	0.9600
N1—H1N	0.86 (5)	C12—H12B	0.9600
N2—C9	1.454 (9)	C12—H12C	0.9600
N2—H2N	0.86 (3)	C13—H13A	0.9600
C1—C6	1.383 (10)	C13—H13B	0.9600
C1—C2	1.383 (10)	C13—H13C	0.9600
C2—C3	1.377 (11)	C11A—C13A	1.32 (7)
C2—H2	0.9300	C11A—C12A	1.503 (14)
C3—C4	1.385 (11)	C11A—H11A	0.9800
C3—H3	0.9300	C12A—H12D	0.9600
C4—C5	1.395 (10)	C12A—H12E	0.9600
C5—C6	1.368 (11)	C12A—H12F	0.9600
C5—H5	0.9300	C13A—H13D	0.9600
C6—H6	0.9300	C13A—H13E	0.9600
C7—C8	1.512 (12)	C13A—H13F	0.9600
C8—H8A	0.9600
O2—S1—O1	119.3 (3)	H8A—C8—H8C	109.5
O2—S1—N2	106.4 (4)	H8B—C8—H8C	109.5
O1—S1—N2	105.9 (3)	N2—C9—C10	110.1 (6)
O2—S1—C1	108.4 (3)	N2—C9—C11A	109.8 (7)
O1—S1—C1	108.2 (4)	C10—C9—C11A	111.0 (7)
N2—S1—C1	108.1 (3)	N2—C9—C11	109.8 (7)
C10—O5—H5O	119.8	C10—C9—C11	111.0 (7)
C7—N1—C4	128.6 (7)	N2—C9—H9	108.6
C7—N1—H1N	116 (6)	C10—C9—H9	108.6
C4—N1—H1N	114 (6)	C11A—C9—H9	108.6
C9—N2—S1	119.4 (5)	C11—C9—H9	108.6
C9—N2—H2N	110 (5)	O4—C10—O5	124.8 (7)
S1—N2—H2N	109 (5)	O4—C10—C9	122.4 (8)
C6—C1—C2	119.9 (7)	O5—C10—C9	112.8 (7)
C6—C1—S1	120.4 (6)	C13—C11—C12	111.1 (12)
C2—C1—S1	119.5 (6)	C13—C11—C9	116.7 (10)
C1—C2—C3	119.9 (8)	C12—C11—C9	110.2 (9)
C1—C2—H2	120.0	C13—C11—H11	106.0
C3—C2—H2	120.0	C12—C11—H11	106.0
C4—C3—C2	120.9 (8)	C9—C11—H11	106.0
C4—C3—H3	119.5	C13A—C11A—C12A	116 (2)
C2—C3—H3	119.5	C13A—C11A—C9	126 (3)
C3—C4—C5	118.1 (7)	C12A—C11A—C9	110.2 (9)
C3—C4—N1	124.7 (7)	C13A—C11A—H11A	99.3
C5—C4—N1	117.2 (7)	C12A—C11A—H11A	99.3
C6—C5—C4	121.4 (7)	C9—C11A—H11A	99.3
C6—C5—H5	119.3	C11A—C12A—H12D	109.5
C4—C5—H5	119.3	C11A—C12A—H12E	109.5
C5—C6—C1	119.7 (7)	H12D—C12A—H12E	109.5
C5—C6—H6	120.2	C11A—C12A—H12F	109.5
C1—C6—H6	120.2	H12D—C12A—H12F	109.5
O3—C7—N1	122.9 (8)	H12E—C12A—H12F	109.5
O3—C7—C8	121.8 (8)	C11A—C13A—H13D	109.5
N1—C7—C8	115.2 (8)	C11A—C13A—H13E	109.5
C7—C8—H8A	109.5	H13D—C13A—H13E	109.5
C7—C8—H8B	109.5	C11A—C13A—H13F	109.5
H8A—C8—H8B	109.5	H13D—C13A—H13F	109.5
C7—C8—H8C	109.5	H13E—C13A—H13F	109.5
O2—S1—N2—C9	−49.5 (6)	C4—N1—C7—C8	−174.9 (8)
O1—S1—N2—C9	−177.4 (6)	S1—N2—C9—C10	−99.4 (7)
C1—S1—N2—C9	66.8 (6)	S1—N2—C9—C11A	138.0 (7)
O2—S1—C1—C6	−153.6 (6)	S1—N2—C9—C11	138.0 (7)
O1—S1—C1—C6	−22.9 (7)	N2—C9—C10—O4	−31.3 (11)
N2—S1—C1—C6	91.4 (7)	C11A—C9—C10—O4	90.5 (11)
O2—S1—C1—C2	30.5 (7)	C11—C9—C10—O4	90.5 (11)
O1—S1—C1—C2	161.2 (6)	N2—C9—C10—O5	150.7 (7)
N2—S1—C1—C2	−84.5 (7)	C11A—C9—C10—O5	−87.5 (9)
C6—C1—C2—C3	0.8 (12)	C11—C9—C10—O5	−87.5 (9)
S1—C1—C2—C3	176.7 (7)	N2—C9—C11—C13	169.7 (13)
C1—C2—C3—C4	0.2 (13)	C10—C9—C11—C13	47.7 (16)
C2—C3—C4—C5	−0.4 (13)	C11A—C9—C11—C13	0(100)
C2—C3—C4—N1	178.2 (8)	N2—C9—C11—C12	−62.3 (12)
C7—N1—C4—C3	−0.9 (13)	C10—C9—C11—C12	175.7 (9)
C7—N1—C4—C5	177.7 (8)	C11A—C9—C11—C12	0(100)
C3—C4—C5—C6	−0.5 (12)	N2—C9—C11A—C13A	85 (3)
N1—C4—C5—C6	−179.2 (7)	C10—C9—C11A—C13A	−37 (3)
C4—C5—C6—C1	1.5 (12)	C11—C9—C11A—C13A	0(100)
C2—C1—C6—C5	−1.7 (12)	N2—C9—C11A—C12A	−62.3 (12)
S1—C1—C6—C5	−177.6 (6)	C10—C9—C11A—C12A	175.7 (9)
C4—N1—C7—O3	3.5 (13)	C11—C9—C11A—C12A	0(100)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3	0.93	2.25	2.848 (11)	122
O5—H5o···O3i	0.93	1.66	2.591 (9)	176
N1—H1n···O1ii	0.86 (5)	2.34 (7)	3.147 (9)	157 (6)
N2—H2n···O2iii	0.86 (3)	2.37 (3)	3.184 (8)	158 (6)
N2—H2n···O4	0.86 (3)	2.35 (6)	2.767 (9)	110 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3	0.93	2.25	2.848 (11)	122
O5—H5o⋯O3i	0.93	1.66	2.591 (9)	176
N1—H1n⋯O1ii	0.86 (5)	2.34 (7)	3.147 (9)	157 (6)
N2—H2n⋯O2iii	0.86 (3)	2.37 (3)	3.184 (8)	158 (6)
N2—H2n⋯O4	0.86 (3)	2.35 (6)	2.767 (9)	110 (5)

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