2-(Benzene-sulfonamido)acetic acid.

The title compound, C(8)H(9)NO(4)S, is of inter-est as a precursor to biologically active sulfur-containing heterocyclic cmpounds. The crystal structure displays the classical O-H⋯O inter-molecular hydrogen bonding typical for carboxylic acids forming dimers. Symmetry-related dimers are, in turn, linked through head-to-tail pairs of inter-molecular N-H⋯O inter-actions, giving rise to a zigzag chain along the c axis.

Related literature

For the synthesis and biological evaluation of sulfur-containing heterocyclic compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶, 2008 ▶); Wen et al. (2005 ▶). For related structures, see: Wen et al. (2006 ▶); Zhang et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background information, see: Berredjem et al. (2000 ▶); Esteve & Bidal (2002 ▶); La Roche & Co (1967a,b); Lee & Lee (2002 ▶); Martinez et al. (2000 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶). For related literature, see: Gowda et al. (2007a ▶,b ▶,c ▶); Kayser et al. (2004 ▶); La Roche & Co (1967 ▶); Vaichulis (1977 ▶).

Experimental

Crystal data

C8H9NO4S

M = 215.23

Monoclinic,

a = 8.5181 (3) Å

b = 11.1302 (4) Å

c = 10.6414 (4) Å

β = 112.600 (2)°

V = 931.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 296 (2) K

0.36 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.889, T max = 0.952

10301 measured reflections

2338 independent reflections

1644 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.116

S = 1.03

2338 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.47 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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035721/lh2721sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035721/lh2721Isup2.hkl

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

C8H9NO4S	F000 = 448
Mr = 215.23	Dx = 1.535 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2708 reflections
a = 8.5181 (3) Å	θ = 2.8–26.2º
b = 11.1302 (4) Å	µ = 0.34 mm−1
c = 10.6414 (4) Å	T = 296 (2) K
β = 112.600 (2)º	Cubes, colourless
V = 931.42 (6) Å3	0.36 × 0.16 × 0.15 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2338 independent reflections
Radiation source: fine-focus sealed tube	1644 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 296(2) K	θmax = 28.4º
φ and ω scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.889, Tmax = 0.952	k = −14→13
10301 measured reflections	l = −14→14

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3567P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2338 reflections	Δρmax = 0.33 e Å−3
128 parameters	Δρmin = −0.47 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.16488 (6)	0.67470 (5)	0.09397 (5)	0.04003 (18)
O1	0.1794 (2)	0.77973 (15)	0.17404 (17)	0.0549 (4)
O2	0.01764 (18)	0.65761 (17)	−0.02937 (16)	0.0570 (5)
O3	0.2307 (2)	0.51175 (18)	0.53583 (15)	0.0586 (5)
H8	0.1631	0.5017	0.5728	0.088*
O4	−0.0061 (2)	0.52365 (18)	0.34770 (15)	0.0573 (5)
N1	0.1740 (3)	0.56105 (19)	0.18822 (18)	0.0518 (5)
H1	0.1223	0.4965	0.1497	0.062*
C1	0.3436 (2)	0.66945 (18)	0.04972 (19)	0.0319 (4)
C2	0.5008 (3)	0.7030 (2)	0.1452 (2)	0.0474 (6)
H2	0.5119	0.7290	0.2313	0.057*
C3	0.6406 (3)	0.6970 (2)	0.1100 (3)	0.0575 (7)
H3	0.7476	0.7174	0.1736	0.069*
C4	0.6226 (3)	0.6612 (2)	−0.0184 (3)	0.0519 (6)
H4	0.7171	0.6593	−0.0418	0.062*
C5	0.4666 (3)	0.6282 (2)	−0.1123 (2)	0.0463 (5)
H5	0.4558	0.6039	−0.1988	0.056*
C6	0.3255 (2)	0.6309 (2)	−0.07854 (19)	0.0386 (5)
H6	0.2197	0.6070	−0.1413	0.046*
C7	0.2639 (3)	0.5602 (2)	0.3340 (2)	0.0456 (5)
H7A	0.3143	0.6385	0.3640	0.055*
H7B	0.3550	0.5015	0.3585	0.055*
C8	0.1465 (3)	0.5299 (2)	0.4048 (2)	0.0429 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0364 (3)	0.0515 (4)	0.0382 (3)	−0.0005 (2)	0.0210 (2)	−0.0011 (2)
O1	0.0665 (11)	0.0495 (10)	0.0606 (10)	0.0057 (8)	0.0376 (9)	−0.0035 (8)
O2	0.0327 (7)	0.0894 (14)	0.0493 (9)	−0.0016 (8)	0.0161 (7)	0.0003 (9)
O3	0.0539 (10)	0.0876 (14)	0.0368 (8)	−0.0090 (9)	0.0200 (7)	0.0061 (9)
O4	0.0496 (9)	0.0886 (14)	0.0364 (8)	−0.0138 (9)	0.0196 (7)	0.0028 (8)
N1	0.0702 (13)	0.0551 (13)	0.0395 (10)	−0.0230 (10)	0.0314 (9)	−0.0075 (9)
C1	0.0307 (9)	0.0338 (11)	0.0337 (9)	−0.0008 (8)	0.0153 (8)	0.0032 (8)
C2	0.0428 (11)	0.0554 (15)	0.0445 (12)	−0.0114 (10)	0.0171 (9)	−0.0138 (11)
C3	0.0350 (11)	0.0646 (17)	0.0718 (17)	−0.0140 (11)	0.0195 (11)	−0.0136 (14)
C4	0.0448 (12)	0.0513 (15)	0.0737 (16)	0.0012 (10)	0.0384 (12)	0.0036 (12)
C5	0.0544 (13)	0.0525 (14)	0.0430 (12)	0.0104 (11)	0.0308 (10)	0.0079 (10)
C6	0.0359 (10)	0.0494 (13)	0.0309 (10)	0.0026 (9)	0.0135 (8)	0.0044 (9)
C7	0.0501 (12)	0.0490 (14)	0.0441 (12)	−0.0058 (10)	0.0251 (10)	0.0018 (10)
C8	0.0550 (13)	0.0431 (13)	0.0344 (10)	−0.0059 (10)	0.0213 (10)	−0.0010 (9)

S1—O1	1.4237 (17)	C2—H2	0.9300
S1—O2	1.4376 (16)	C3—C4	1.374 (4)
S1—N1	1.598 (2)	C3—H3	0.9300
S1—C1	1.7590 (19)	C4—C5	1.370 (3)
O3—C8	1.316 (2)	C4—H4	0.9300
O3—H8	0.8200	C5—C6	1.381 (3)
O4—C8	1.207 (3)	C5—H5	0.9300
N1—C7	1.443 (3)	C6—H6	0.9300
N1—H1	0.8600	C7—C8	1.502 (3)
C1—C6	1.382 (3)	C7—H7A	0.9700
C1—C2	1.385 (3)	C7—H7B	0.9700
C2—C3	1.380 (3)
O1—S1—O2	119.98 (11)	C5—C4—C3	120.6 (2)
O1—S1—N1	107.60 (10)	C5—C4—H4	119.7
O2—S1—N1	106.46 (10)	C3—C4—H4	119.7
O1—S1—C1	107.60 (10)	C4—C5—C6	120.1 (2)
O2—S1—C1	107.00 (9)	C4—C5—H5	119.9
N1—S1—C1	107.66 (10)	C6—C5—H5	119.9
C8—O3—H8	109.5	C5—C6—C1	119.04 (19)
C7—N1—S1	123.95 (16)	C5—C6—H6	120.5
C7—N1—H1	118.0	C1—C6—H6	120.5
S1—N1—H1	118.0	N1—C7—C8	111.13 (18)
C6—C1—C2	121.18 (19)	N1—C7—H7A	109.4
C6—C1—S1	119.67 (15)	C8—C7—H7A	109.4
C2—C1—S1	119.14 (15)	N1—C7—H7B	109.4
C3—C2—C1	118.7 (2)	C8—C7—H7B	109.4
C3—C2—H2	120.7	H7A—C7—H7B	108.0
C1—C2—H2	120.7	O4—C8—O3	124.5 (2)
C4—C3—C2	120.3 (2)	O4—C8—C7	123.80 (19)
C4—C3—H3	119.8	O3—C8—C7	111.68 (19)
C2—C3—H3	119.8
O1—S1—N1—C7	−28.4 (2)	S1—C1—C2—C3	179.16 (19)
O2—S1—N1—C7	−158.27 (18)	C1—C2—C3—C4	1.5 (4)
C1—S1—N1—C7	87.27 (19)	C2—C3—C4—C5	−1.6 (4)
O1—S1—C1—C6	−141.46 (18)	C3—C4—C5—C6	0.1 (4)
O2—S1—C1—C6	−11.3 (2)	C4—C5—C6—C1	1.3 (4)
N1—S1—C1—C6	102.82 (18)	C2—C1—C6—C5	−1.3 (3)
O1—S1—C1—C2	39.3 (2)	S1—C1—C6—C5	179.46 (17)
O2—S1—C1—C2	169.46 (18)	S1—N1—C7—C8	121.9 (2)
N1—S1—C1—C2	−76.44 (19)	N1—C7—C8—O4	−9.4 (3)
C6—C1—C2—C3	−0.1 (3)	N1—C7—C8—O3	170.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.20	3.054 (3)	174
O3—H8···O4ii	0.82	1.86	2.678 (2)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.20	3.054 (3)	174
O3—H8⋯O4ii	0.82	1.86	2.678 (2)	178

Symmetry codes: (i) ; (ii) .