Acta Cryst. (2009). E65, o1204 [ doi:10.1107/S160053680901616X ]
The title compound, C9H11NO4S, is of interest as a precursor to biologically active benzothiazines. The crystal structure is stabilized by intermolecular N-H
O and C-HO interactions.
A mixture of benzene sulfonic acid (4.14 g, 23.44 mmoles), glycine methyl ester hydrochloride (2.94 g, 23.44 mmol.) and distilled water (50.0 ml) was stirred for half an hour. pH of the reaction mixture was adjusted to 8.0 with an aqueous sodium carbonate solution. After completion of the reaction, a white solid product was isolated, washed, dried and recrystallized in methanol to get the crystals suitable for for X-ray studies; m.p. 332 K.
H atoms were placed in geometric positions (C—H = 0.93-0.97 Å; N—H = 0.86 Å) using a riding model with Uiso(H) = 1.2 Ueq(C,N) or Uiso(H) = 1.5 Ueq(Cmethyl).
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, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.
![[Figure 1]](./bt2940fig1thm.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]](./bt2940fig2thm.gif)
| Fig. 2. Part of the crystal structure, showing hydrogen bond interactions (dashed lines). along the [0 0 1] direction. H atoms not involved in hydrogen bonding have been omitted for clarity. |
| C9H11NO4S | F000 = 240 |
| Mr = 229.26 | Dx = 1.433 Mg m−3 |
| Monoclinic, P21 | Melting point: 332 K |
| Hall symbol: P 2yb | Mo Kα radiation λ = 0.71073 Å |
| a = 9.7268 (8) Å | Cell parameters from 2710 reflections |
| b = 5.0781 (4) Å | θ = 2.6–26.6º |
| c = 10.9286 (9) Å | µ = 0.30 mm−1 |
| β = 100.087 (3)º | T = 296 K |
| V = 531.46 (7) Å3 | Plates, colourless |
| Z = 2 | 0.23 × 0.11 × 0.08 mm |
| Bruker APEXII CCD area-detector diffractometer | 2216 independent reflections |
| Radiation source: fine-focus sealed tube | 1944 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.028 |
| T = 296 K | θmax = 29.3º |
| φ and ω scans | θmin = 2.6º |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −12→13 |
| Tmin = 0.935, Tmax = 0.977 | k = −4→6 |
| 6159 measured reflections | l = −11→15 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.036 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.0105P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.092 | (Δ/σ)max < 0.001 |
| S = 1.07 | Δρmax = 0.25 e Å−3 |
| 2216 reflections | Δρmin = −0.26 e Å−3 |
| 137 parameters | Extinction correction: none |
| 1 restraint | Absolute structure: Flack (1983), 394 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.089 (8) |
| Secondary atom site location: difference Fourier map |
| C9H11NO4S | V = 531.46 (7) Å3 |
| Mr = 229.26 | Z = 2 |
| Monoclinic, P21 | Mo Kα |
| a = 9.7268 (8) Å | µ = 0.30 mm−1 |
| b = 5.0781 (4) Å | T = 296 K |
| c = 10.9286 (9) Å | 0.23 × 0.11 × 0.08 mm |
| β = 100.087 (3)º |
| Bruker APEXII CCD area-detector diffractometer | 2216 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | 1944 reflections with I > 2σ(I) |
| Tmin = 0.935, Tmax = 0.977 | Rint = 0.028 |
| 6159 measured reflections |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.092 | Δρmax = 0.25 e Å−3 |
| S = 1.07 | Δρmin = −0.26 e Å−3 |
| 2216 reflections | Absolute structure: Flack (1983), 394 Friedel pairs |
| 137 parameters | Flack parameter: 0.089 (8) |
| 1 restraint |
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 | 0.61607 (5) | 0.09862 (10) | 0.21011 (5) | 0.03580 (15) | |
| O1 | 0.52527 (16) | −0.0799 (4) | 0.25831 (16) | 0.0482 (4) | |
| O2 | 0.72360 (15) | 0.0024 (4) | 0.14799 (15) | 0.0468 (4) | |
| O3 | 0.27134 (16) | 0.0012 (4) | 0.03143 (16) | 0.0469 (4) | |
| O4 | 0.16275 (17) | 0.2366 (4) | 0.15812 (18) | 0.0589 (5) | |
| N1 | 0.51744 (17) | 0.2853 (4) | 0.11147 (16) | 0.0389 (5) | |
| H1 | 0.5423 | 0.3294 | 0.0426 | 0.047* | |
| C1 | 0.6962 (2) | 0.2993 (5) | 0.3344 (2) | 0.0366 (5) | |
| C2 | 0.6546 (3) | 0.2854 (7) | 0.4486 (2) | 0.0537 (7) | |
| H2 | 0.5847 | 0.1687 | 0.4614 | 0.064* | |
| C3 | 0.7181 (3) | 0.4473 (8) | 0.5441 (2) | 0.0669 (9) | |
| H3 | 0.6913 | 0.4382 | 0.6216 | 0.080* | |
| C4 | 0.8199 (3) | 0.6206 (8) | 0.5249 (3) | 0.0646 (8) | |
| H4 | 0.8612 | 0.7303 | 0.5891 | 0.078* | |
| C5 | 0.8614 (3) | 0.6333 (7) | 0.4113 (3) | 0.0602 (7) | |
| H5 | 0.9317 | 0.7494 | 0.3992 | 0.072* | |
| C6 | 0.7990 (2) | 0.4739 (5) | 0.3148 (2) | 0.0481 (6) | |
| H6 | 0.8259 | 0.4843 | 0.2374 | 0.058* | |
| C7 | 0.3858 (2) | 0.3768 (5) | 0.1419 (2) | 0.0365 (5) | |
| H7B | 0.3610 | 0.5437 | 0.1008 | 0.044* | |
| H7A | 0.3966 | 0.4050 | 0.2309 | 0.044* | |
| C8 | 0.2709 (2) | 0.1813 (5) | 0.10223 (19) | 0.0346 (5) | |
| C9 | 0.0435 (3) | 0.0566 (10) | 0.1303 (3) | 0.0886 (12) | |
| H9A | 0.0132 | 0.0469 | 0.0419 | 0.133* | |
| H9B | −0.0315 | 0.1204 | 0.1687 | 0.133* | |
| H9C | 0.0709 | −0.1155 | 0.1619 | 0.133* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0316 (2) | 0.0341 (3) | 0.0417 (3) | −0.0008 (3) | 0.00653 (19) | 0.0014 (3) |
| O1 | 0.0446 (9) | 0.0426 (10) | 0.0565 (10) | −0.0084 (8) | 0.0069 (8) | 0.0094 (9) |
| O2 | 0.0390 (8) | 0.0496 (11) | 0.0525 (10) | 0.0075 (8) | 0.0099 (7) | −0.0064 (8) |
| O3 | 0.0415 (9) | 0.0443 (10) | 0.0559 (10) | −0.0052 (8) | 0.0114 (7) | −0.0095 (9) |
| O4 | 0.0329 (8) | 0.0774 (14) | 0.0701 (11) | −0.0025 (9) | 0.0194 (8) | −0.0181 (11) |
| N1 | 0.0333 (9) | 0.0445 (12) | 0.0393 (10) | −0.0014 (9) | 0.0074 (8) | 0.0040 (9) |
| C1 | 0.0292 (10) | 0.0377 (13) | 0.0412 (11) | 0.0037 (9) | 0.0014 (8) | 0.0020 (10) |
| C2 | 0.0461 (14) | 0.0662 (19) | 0.0502 (14) | −0.0020 (14) | 0.0123 (11) | −0.0009 (14) |
| C3 | 0.0632 (17) | 0.091 (3) | 0.0467 (15) | 0.0050 (18) | 0.0092 (13) | −0.0126 (16) |
| C4 | 0.0643 (16) | 0.064 (2) | 0.0587 (15) | 0.0052 (18) | −0.0098 (12) | −0.0190 (18) |
| C5 | 0.0537 (14) | 0.051 (2) | 0.0701 (16) | −0.0110 (15) | −0.0044 (12) | −0.0030 (16) |
| C6 | 0.0469 (13) | 0.0451 (16) | 0.0518 (14) | −0.0052 (12) | 0.0071 (11) | 0.0017 (12) |
| C7 | 0.0352 (11) | 0.0327 (13) | 0.0423 (11) | 0.0031 (10) | 0.0082 (9) | 0.0019 (10) |
| C8 | 0.0295 (10) | 0.0394 (14) | 0.0342 (10) | 0.0059 (9) | 0.0038 (8) | 0.0031 (10) |
| C9 | 0.0397 (14) | 0.116 (3) | 0.114 (3) | −0.0180 (19) | 0.0257 (16) | −0.015 (3) |
| S1—O1 | 1.4290 (16) | C3—C4 | 1.369 (4) |
| S1—O2 | 1.4291 (15) | C3—H3 | 0.9300 |
| S1—N1 | 1.618 (2) | C4—C5 | 1.372 (4) |
| S1—C1 | 1.767 (2) | C4—H4 | 0.9300 |
| O3—C8 | 1.198 (3) | C5—C6 | 1.383 (4) |
| O4—C8 | 1.336 (2) | C5—H5 | 0.9300 |
| O4—C9 | 1.466 (4) | C6—H6 | 0.9300 |
| N1—C7 | 1.454 (3) | C7—C8 | 1.501 (3) |
| N1—H1 | 0.8600 | C7—H7B | 0.9700 |
| C1—C2 | 1.380 (3) | C7—H7A | 0.9700 |
| C1—C6 | 1.381 (3) | C9—H9A | 0.9600 |
| C2—C3 | 1.386 (4) | C9—H9B | 0.9600 |
| C2—H2 | 0.9300 | C9—H9C | 0.9600 |
| O1—S1—O2 | 120.61 (11) | C4—C5—C6 | 120.2 (3) |
| O1—S1—N1 | 106.53 (9) | C4—C5—H5 | 119.9 |
| O2—S1—N1 | 106.36 (9) | C6—C5—H5 | 119.9 |
| O1—S1—C1 | 107.48 (10) | C1—C6—C5 | 119.4 (2) |
| O2—S1—C1 | 107.55 (10) | C1—C6—H6 | 120.3 |
| N1—S1—C1 | 107.73 (10) | C5—C6—H6 | 120.3 |
| C8—O4—C9 | 115.6 (2) | N1—C7—C8 | 111.31 (18) |
| C7—N1—S1 | 118.54 (14) | N1—C7—H7B | 109.4 |
| C7—N1—H1 | 120.7 | C8—C7—H7B | 109.4 |
| S1—N1—H1 | 120.7 | N1—C7—H7A | 109.4 |
| C2—C1—C6 | 120.6 (2) | C8—C7—H7A | 109.4 |
| C2—C1—S1 | 120.4 (2) | H7B—C7—H7A | 108.0 |
| C6—C1—S1 | 119.01 (17) | O3—C8—O4 | 123.2 (2) |
| C1—C2—C3 | 119.2 (3) | O3—C8—C7 | 127.20 (19) |
| C1—C2—H2 | 120.4 | O4—C8—C7 | 109.60 (19) |
| C3—C2—H2 | 120.4 | O4—C9—H9A | 109.5 |
| C4—C3—C2 | 120.3 (3) | O4—C9—H9B | 109.5 |
| C4—C3—H3 | 119.8 | H9A—C9—H9B | 109.5 |
| C2—C3—H3 | 119.8 | O4—C9—H9C | 109.5 |
| C3—C4—C5 | 120.3 (3) | H9A—C9—H9C | 109.5 |
| C3—C4—H4 | 119.9 | H9B—C9—H9C | 109.5 |
| C5—C4—H4 | 119.9 | ||
| O1—S1—N1—C7 | 40.2 (2) | C1—C2—C3—C4 | 0.6 (5) |
| O2—S1—N1—C7 | 170.05 (17) | C2—C3—C4—C5 | −0.8 (5) |
| C1—S1—N1—C7 | −74.87 (19) | C3—C4—C5—C6 | 1.0 (5) |
| O1—S1—C1—C2 | −7.1 (2) | C2—C1—C6—C5 | 0.8 (4) |
| O2—S1—C1—C2 | −138.4 (2) | S1—C1—C6—C5 | 179.5 (2) |
| N1—S1—C1—C2 | 107.3 (2) | C4—C5—C6—C1 | −1.0 (4) |
| O1—S1—C1—C6 | 174.20 (18) | S1—N1—C7—C8 | −86.9 (2) |
| O2—S1—C1—C6 | 42.9 (2) | C9—O4—C8—O3 | 1.7 (3) |
| N1—S1—C1—C6 | −71.3 (2) | C9—O4—C8—C7 | −178.5 (2) |
| C6—C1—C2—C3 | −0.6 (4) | N1—C7—C8—O3 | −15.8 (3) |
| S1—C1—C2—C3 | −179.2 (2) | N1—C7—C8—O4 | 164.42 (18) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3i | 0.86 | 2.28 | 2.998 (2) | 141 |
| C7—H7B···O3ii | 0.97 | 2.55 | 3.503 (4) | 168 |
| Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···O3i | 0.86 | 2.28 | 2.998 (2) | 141 |
| C7—H7B···O3ii | 0.97 | 2.55 | 3.503 (4) | 168 |
| Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y+1, z. |
The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer. MNA acknowledges the Higher Education Commission, Pakistan, for providing a PhD Scholarship under PIN 042- 120607-PS2–183.
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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 (Soledade et al., 2006; Esteve & Bidal, 2002; Xiao & Timberlake, 2000; Martinez et al., 2000; Berredjem et al., 2000; Lee & Lee, 2002). 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, 2009). In the molecule of (I) (Fig. 1), bond lengths and bond angles are almost similar to those in related sulfonamide molecules (Gowda et al., 2007a, 2007b, 2007c) and the bond lengths are within normal ranges. In the crystal structure, each molecule is linked to an adjacent one through C7—H7B···O3 contacts giving rise to chains along b-axis. Each molecule of the chain is further linked to the one of its neighbouring chain along a through intermolecular N—H···O interactions.