Acta Cryst. (2008). E64, o2283-o2284 [ doi:10.1107/S1600536808035721 ]
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-HO interactions, giving rise to a zigzag chain along the c axis.
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.
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).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2003).
![[Figure 1]](./lh2721fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. |
![[Figure 2]](./lh2721fig2thm.gif)
| 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 1. |
| C8H9NO4S | F(000) = 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 = 2.8–26.2° |
| b = 11.1302 (4) Å | µ = 0.34 mm−1 |
| c = 10.6414 (4) Å | T = 296 K |
| β = 112.600 (2)° | 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) |
| graphite | Rint = 0.037 |
| φ and ω scans | θmax = 28.4°, θmin = 2.6° |
| 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 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.116 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.3567P] where P = (Fo2 + 2Fc2)/3 |
| 2338 reflections | (Δ/σ)max = 0.001 |
| 128 parameters | Δρmax = 0.33 e Å−3 |
| 0 restraints | Δρmin = −0.47 e Å−3 |
| C8H9NO4S | V = 931.42 (6) Å3 |
| Mr = 215.23 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 8.5181 (3) Å | µ = 0.34 mm−1 |
| b = 11.1302 (4) Å | T = 296 K |
| c = 10.6414 (4) Å | 0.36 × 0.16 × 0.15 mm |
| β = 112.600 (2)° |
| Bruker APEXII CCD area-detector diffractometer | 2338 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1644 reflections with I > 2σ(I) |
| Tmin = 0.889, Tmax = 0.952 | Rint = 0.037 |
| 10301 measured reflections | θmax = 28.4° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.116 | Δρmax = 0.33 e Å−3 |
| S = 1.03 | Δρmin = −0.47 e Å−3 |
| 2338 reflections | Absolute structure: ? |
| 128 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 |
| Symmetry codes: (i) −x, −y+1, −z; (ii) −x, −y+1, −z+1. |
| 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) −x, −y+1, −z; (ii) −x, −y+1, −z+1. |
The authors are grateful to the Higher Education Commission of Pakistan for their grant to purchase the diffractometer.
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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.