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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2283–o2284.
Published online 2008 November 8. doi:  10.1107/S1600536808035721
PMCID: PMC2959830

2-(Benzene­sulfonamido)acetic acid

Abstract

The title compound, C8H9NO4S, is of inter­est as a precursor to biologically active sulfur-containing heterocyclic cmpounds. The crystal structure displays the classical O—H(...)O inter­molecular hydrogen bonding typical for carboxylic acids forming dimers. Symmetry-related dimers are, in turn, linked through head-to-tail pairs of inter­molecular N—H(...)O inter­actions, 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 [triangle], 2006 [triangle], 2007 [triangle], 2008 [triangle]); Wen et al. (2005 [triangle]). For related structures, see: Wen et al. (2006 [triangle]); Zhang et al. (2006 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For background information, see: Berredjem et al. (2000 [triangle]); Esteve & Bidal (2002 [triangle]); La Roche & Co (1967a,b); Lee & Lee (2002 [triangle]); Martinez et al. (2000 [triangle]); Soledade et al. (2006 [triangle]); Xiao & Timberlake (2000 [triangle]). For related literature, see: Gowda et al. (2007a [triangle],b [triangle],c [triangle]); Kayser et al. (2004 [triangle]); La Roche & Co (1967 [triangle]); Vaichulis (1977 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2283-scheme1.jpg

Experimental

Crystal data

  • C8H9NO4S
  • M r = 215.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2283-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for their grant to purchase the diffractometer.

supplementary crystallographic information

Comment

Sulfonamide is an important functionality found in many naturally occurring as well as synthetic compounds which possess numerous types of biological activities e.g., anticonvulsant, antihypertensive, herbicidal and antimalarial (Soledade et al., 2006; Esteve & Bidal, 2002; Xiao & Timberlake, 2000; Martinez et al., 2000; Berredjem et al., 2000; Lee & Lee, 2002) activities. In addition, these are found useful as anticancer (La Roche & Co, 1967) and antitubercular (Vaichulis, 1977) agents. These are also assumed as safe antibiotics during Pregnancy (Kayser et al., 2004).

In the present paper, the structure of the title compound has been determined as a part of our ongoing research on the synthesis and biological evaluation of sulfur containing heterocyclic compounds (Zia-ur-Rehman et al., 2005, 2006, 2007, 2008). In the molecule of (I) (Fig. 1), bond lengths and bond angles are almost similar to those in the related sulfonamide molecules (Gowda et al., 2007a,b,c) and the bond lengths are within normal ranges (Allen et al., 1987). In the crystal structure, each molecule is linked to an inersion related one through head-to-tail pairs of O—H···O intermolecular hydrogen bonds giving rise to dimeric motifs typical for carboxylic acids. Neighbouring dimers are further arranged into zigzag chains along c axis through head-to-tail pairs of N—H···O intermolecular interactions.

Experimental

A mixture of N-benzenesulfonyl glycine methyl ester (1.0 g; 4.5 mmoles) and aqueous sodium hydroxide solution (10%; 10.0 ml) was refluxed for a peiod of one hour, cooled and acidified with 1 N hydrochloric acid. A white precipitate obtained was washed with water, dried and recrystallized from methanol to obtain colourless crystals suitable for X-ray studies; m.p. 435-436K.

Refinement

All H atoms were placed in idealized positions, (C-H = 0.93-97 Å, O-H = 0.82Å, and N-H = 0.86Å), and included in the refinement in a riding-model approximation, with Uiso(H) = 1.2Ueq(C and N) and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Part of the crystal structure, viewed approximately along the b axis, showing hydrogen bond interactions (dashed lines) along the [0 0 1] direction. H atoms not involved in hydrogen bonding have been omitted for clarity. Symmetry codes as given in Table ...

Crystal data

C8H9NO4SF000 = 448
Mr = 215.23Dx = 1.535 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2708 reflections
a = 8.5181 (3) Åθ = 2.8–26.2º
b = 11.1302 (4) ŵ = 0.34 mm1
c = 10.6414 (4) ÅT = 296 (2) K
β = 112.600 (2)ºCubes, colourless
V = 931.42 (6) Å30.36 × 0.16 × 0.15 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer2338 independent reflections
Radiation source: fine-focus sealed tube1644 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.037
T = 296(2) Kθmax = 28.4º
[var phi] and ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.889, Tmax = 0.952k = −14→13
10301 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-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 reflectionsΔρmax = 0.33 e Å3
128 parametersΔρmin = −0.47 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.16488 (6)0.67470 (5)0.09397 (5)0.04003 (18)
O10.1794 (2)0.77973 (15)0.17404 (17)0.0549 (4)
O20.01764 (18)0.65761 (17)−0.02937 (16)0.0570 (5)
O30.2307 (2)0.51175 (18)0.53583 (15)0.0586 (5)
H80.16310.50170.57280.088*
O4−0.0061 (2)0.52365 (18)0.34770 (15)0.0573 (5)
N10.1740 (3)0.56105 (19)0.18822 (18)0.0518 (5)
H10.12230.49650.14970.062*
C10.3436 (2)0.66945 (18)0.04972 (19)0.0319 (4)
C20.5008 (3)0.7030 (2)0.1452 (2)0.0474 (6)
H20.51190.72900.23130.057*
C30.6406 (3)0.6970 (2)0.1100 (3)0.0575 (7)
H30.74760.71740.17360.069*
C40.6226 (3)0.6612 (2)−0.0184 (3)0.0519 (6)
H40.71710.6593−0.04180.062*
C50.4666 (3)0.6282 (2)−0.1123 (2)0.0463 (5)
H50.45580.6039−0.19880.056*
C60.3255 (2)0.6309 (2)−0.07854 (19)0.0386 (5)
H60.21970.6070−0.14130.046*
C70.2639 (3)0.5602 (2)0.3340 (2)0.0456 (5)
H7A0.31430.63850.36400.055*
H7B0.35500.50150.35850.055*
C80.1465 (3)0.5299 (2)0.4048 (2)0.0429 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0364 (3)0.0515 (4)0.0382 (3)−0.0005 (2)0.0210 (2)−0.0011 (2)
O10.0665 (11)0.0495 (10)0.0606 (10)0.0057 (8)0.0376 (9)−0.0035 (8)
O20.0327 (7)0.0894 (14)0.0493 (9)−0.0016 (8)0.0161 (7)0.0003 (9)
O30.0539 (10)0.0876 (14)0.0368 (8)−0.0090 (9)0.0200 (7)0.0061 (9)
O40.0496 (9)0.0886 (14)0.0364 (8)−0.0138 (9)0.0196 (7)0.0028 (8)
N10.0702 (13)0.0551 (13)0.0395 (10)−0.0230 (10)0.0314 (9)−0.0075 (9)
C10.0307 (9)0.0338 (11)0.0337 (9)−0.0008 (8)0.0153 (8)0.0032 (8)
C20.0428 (11)0.0554 (15)0.0445 (12)−0.0114 (10)0.0171 (9)−0.0138 (11)
C30.0350 (11)0.0646 (17)0.0718 (17)−0.0140 (11)0.0195 (11)−0.0136 (14)
C40.0448 (12)0.0513 (15)0.0737 (16)0.0012 (10)0.0384 (12)0.0036 (12)
C50.0544 (13)0.0525 (14)0.0430 (12)0.0104 (11)0.0308 (10)0.0079 (10)
C60.0359 (10)0.0494 (13)0.0309 (10)0.0026 (9)0.0135 (8)0.0044 (9)
C70.0501 (12)0.0490 (14)0.0441 (12)−0.0058 (10)0.0251 (10)0.0018 (10)
C80.0550 (13)0.0431 (13)0.0344 (10)−0.0059 (10)0.0213 (10)−0.0010 (9)

Geometric parameters (Å, °)

S1—O11.4237 (17)C2—H20.9300
S1—O21.4376 (16)C3—C41.374 (4)
S1—N11.598 (2)C3—H30.9300
S1—C11.7590 (19)C4—C51.370 (3)
O3—C81.316 (2)C4—H40.9300
O3—H80.8200C5—C61.381 (3)
O4—C81.207 (3)C5—H50.9300
N1—C71.443 (3)C6—H60.9300
N1—H10.8600C7—C81.502 (3)
C1—C61.382 (3)C7—H7A0.9700
C1—C21.385 (3)C7—H7B0.9700
C2—C31.380 (3)
O1—S1—O2119.98 (11)C5—C4—C3120.6 (2)
O1—S1—N1107.60 (10)C5—C4—H4119.7
O2—S1—N1106.46 (10)C3—C4—H4119.7
O1—S1—C1107.60 (10)C4—C5—C6120.1 (2)
O2—S1—C1107.00 (9)C4—C5—H5119.9
N1—S1—C1107.66 (10)C6—C5—H5119.9
C8—O3—H8109.5C5—C6—C1119.04 (19)
C7—N1—S1123.95 (16)C5—C6—H6120.5
C7—N1—H1118.0C1—C6—H6120.5
S1—N1—H1118.0N1—C7—C8111.13 (18)
C6—C1—C2121.18 (19)N1—C7—H7A109.4
C6—C1—S1119.67 (15)C8—C7—H7A109.4
C2—C1—S1119.14 (15)N1—C7—H7B109.4
C3—C2—C1118.7 (2)C8—C7—H7B109.4
C3—C2—H2120.7H7A—C7—H7B108.0
C1—C2—H2120.7O4—C8—O3124.5 (2)
C4—C3—C2120.3 (2)O4—C8—C7123.80 (19)
C4—C3—H3119.8O3—C8—C7111.68 (19)
C2—C3—H3119.8
O1—S1—N1—C7−28.4 (2)S1—C1—C2—C3179.16 (19)
O2—S1—N1—C7−158.27 (18)C1—C2—C3—C41.5 (4)
C1—S1—N1—C787.27 (19)C2—C3—C4—C5−1.6 (4)
O1—S1—C1—C6−141.46 (18)C3—C4—C5—C60.1 (4)
O2—S1—C1—C6−11.3 (2)C4—C5—C6—C11.3 (4)
N1—S1—C1—C6102.82 (18)C2—C1—C6—C5−1.3 (3)
O1—S1—C1—C239.3 (2)S1—C1—C6—C5179.46 (17)
O2—S1—C1—C2169.46 (18)S1—N1—C7—C8121.9 (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—O3170.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.203.054 (3)174
O3—H8···O4ii0.821.862.678 (2)178

Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2721).

References

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