Acta Cryst. (2009). E65, o2513 [ doi:10.1107/S1600536809037271 ]
In the crystal of the title compound, C7H10N2O2S, the molecules are linked by two strong N-H
O hydrogen bonds. The molecular structure is stabilized by an intramolecular N-HO hydrogen bond. The C/S/N plane makes a dihedral angle of 69.7 (2)° with the aromatic ring plane.
The title compound was synthesized according to method described by Monzani, et al.,1985.The single crystals suitable for X-ray diffraction were obtained by spontaneous evaporation of the solvent.
All the H atoms attached to C atoms were placed in geometrical positions and constrained to ride on their parent atoms with C—H distance in the range 0.93–0.98 Å, They were treated as riding atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./bx2239fig1thm.gif)
| Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
![[Figure 2]](./bx2239fig2thm.gif)
| Fig. 2. A portion of the packing diagram for (I) showing graph-set motif R44(16) ring. For the sake clarity the atoms not involved in the motif shown have been omitted Symmetry codes: (i) x, -y+1/2, z+1/2; (ii)-x,y+1/2,-z+3/2. |
| C7H10N2O2S | F(000) = 392 |
| Mr = 186.23 | Dx = 1.448 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 3354 reflections |
| a = 9.873 (5) Å | θ = 2.2–28.2° |
| b = 9.151 (4) Å | µ = 0.34 mm−1 |
| c = 10.408 (5) Å | T = 273 K |
| β = 114.689 (6)° | Block, colorless |
| V = 854.4 (7) Å3 | 0.16 × 0.13 × 0.10 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 1449 independent reflections |
| Radiation source: fine-focus sealed tube | 1338 reflections with I > 2σ(I) |
| graphite | Rint = 0.017 |
| φ and ω scans | θmax = 25.1°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
| Tmin = 0.948, Tmax = 0.967 | k = −10→10 |
| 4115 measured reflections | l = −12→9 |
| 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)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.701P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.10 | (Δ/σ)max < 0.001 |
| 1449 reflections | Δρmax = 0.56 e Å−3 |
| 110 parameters | Δρmin = −0.41 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (9) |
| C7H10N2O2S | V = 854.4 (7) Å3 |
| Mr = 186.23 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.873 (5) Å | µ = 0.34 mm−1 |
| b = 9.151 (4) Å | T = 273 K |
| c = 10.408 (5) Å | 0.16 × 0.13 × 0.10 mm |
| β = 114.689 (6)° |
| Bruker SMART CCD area-detector diffractometer | 1449 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1338 reflections with I > 2σ(I) |
| Tmin = 0.948, Tmax = 0.967 | Rint = 0.017 |
| 4115 measured reflections | θmax = 25.1° |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.132 | Δρmax = 0.56 e Å−3 |
| S = 1.10 | Δρmin = −0.41 e Å−3 |
| 1449 reflections | Absolute structure: ? |
| 110 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 | 0.13944 (9) | 0.19821 (9) | 0.76214 (8) | 0.0361 (4) | |
| O1 | 0.1511 (3) | 0.0560 (3) | 0.8246 (3) | 0.0533 (8) | |
| O2 | 0.0800 (3) | 0.2040 (4) | 0.6109 (3) | 0.0603 (9) | |
| N1 | 0.2315 (4) | 0.5060 (4) | 0.6773 (4) | 0.0604 (10) | |
| H1A | 0.2566 | 0.5867 | 0.6510 | 0.073* | |
| H1B | 0.1391 | 0.4815 | 0.6450 | 0.073* | |
| N2 | 0.0260 (3) | 0.2896 (3) | 0.8048 (3) | 0.0412 (7) | |
| H2A | −0.0514 | 0.3293 | 0.7402 | 0.049* | |
| H2B | 0.0426 | 0.2990 | 0.8924 | 0.049* | |
| C1 | 0.3488 (4) | 0.4078 (4) | 0.7793 (3) | 0.0357 (7) | |
| C2 | 0.3186 (3) | 0.2754 (4) | 0.8318 (3) | 0.0342 (7) | |
| C3 | 0.4324 (4) | 0.1967 (4) | 0.9361 (4) | 0.0396 (8) | |
| H3 | 0.4098 | 0.1121 | 0.9727 | 0.048* | |
| C4 | 0.5787 (4) | 0.2433 (4) | 0.9859 (4) | 0.0443 (9) | |
| H4 | 0.6543 | 0.1920 | 1.0571 | 0.053* | |
| C5 | 0.6107 (3) | 0.3669 (4) | 0.9282 (4) | 0.0417 (8) | |
| C6 | 0.4979 (4) | 0.4501 (4) | 0.8300 (4) | 0.0406 (8) | |
| H6 | 0.5221 | 0.5362 | 0.7969 | 0.049* | |
| C7 | 0.7610 (3) | 0.4151 (5) | 0.9737 (4) | 0.0497 (9) | |
| H7A | 0.7795 | 0.4947 | 1.0389 | 0.074* | |
| H7B | 0.7771 | 0.4471 | 0.8933 | 0.074* | |
| H7C | 0.8276 | 0.3360 | 1.0193 | 0.074* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0355 (6) | 0.0364 (6) | 0.0356 (6) | −0.0058 (3) | 0.0140 (4) | −0.0071 (3) |
| O1 | 0.0470 (15) | 0.0348 (14) | 0.0722 (18) | −0.0059 (11) | 0.0191 (13) | −0.0030 (12) |
| O2 | 0.0540 (16) | 0.086 (2) | 0.0376 (14) | −0.0211 (14) | 0.0163 (12) | −0.0185 (13) |
| N1 | 0.056 (2) | 0.063 (2) | 0.062 (2) | 0.0026 (16) | 0.0245 (17) | 0.0197 (17) |
| N2 | 0.0373 (16) | 0.0455 (17) | 0.0419 (15) | 0.0014 (12) | 0.0174 (13) | 0.0004 (12) |
| C1 | 0.0368 (16) | 0.0390 (17) | 0.0348 (15) | 0.0007 (13) | 0.0184 (13) | −0.0019 (13) |
| C2 | 0.0329 (16) | 0.0357 (16) | 0.0352 (16) | −0.0012 (12) | 0.0155 (13) | −0.0053 (12) |
| C3 | 0.0414 (18) | 0.0327 (17) | 0.0435 (18) | 0.0024 (13) | 0.0165 (15) | 0.0001 (13) |
| C4 | 0.0360 (18) | 0.0431 (19) | 0.0474 (19) | 0.0067 (14) | 0.0109 (15) | −0.0027 (16) |
| C5 | 0.0313 (17) | 0.047 (2) | 0.0467 (18) | −0.0029 (14) | 0.0165 (14) | −0.0113 (15) |
| C6 | 0.0395 (17) | 0.0420 (18) | 0.0443 (18) | −0.0051 (14) | 0.0213 (15) | −0.0005 (15) |
| C7 | 0.0246 (16) | 0.058 (2) | 0.062 (2) | −0.0056 (15) | 0.0139 (16) | −0.0010 (18) |
| S1—O2 | 1.433 (3) | C2—C3 | 1.393 (5) |
| S1—O1 | 1.438 (3) | C3—C4 | 1.383 (5) |
| S1—N2 | 1.602 (3) | C3—H3 | 0.9300 |
| S1—C2 | 1.756 (3) | C4—C5 | 1.378 (6) |
| N1—C1 | 1.500 (5) | C4—H4 | 0.9300 |
| N1—H1A | 0.8600 | C5—C6 | 1.383 (5) |
| N1—H1B | 0.8600 | C5—C7 | 1.426 (4) |
| N2—H2A | 0.8600 | C6—H6 | 0.9300 |
| N2—H2B | 0.8600 | C7—H7A | 0.9600 |
| C1—C6 | 1.395 (5) | C7—H7B | 0.9600 |
| C1—C2 | 1.412 (5) | C7—H7C | 0.9600 |
| O2—S1—O1 | 116.68 (18) | C4—C3—C2 | 120.6 (3) |
| O2—S1—N2 | 105.80 (18) | C4—C3—H3 | 119.7 |
| O1—S1—N2 | 106.29 (16) | C2—C3—H3 | 119.7 |
| O2—S1—C2 | 108.58 (16) | C5—C4—C3 | 118.9 (3) |
| O1—S1—C2 | 107.49 (16) | C5—C4—H4 | 120.5 |
| N2—S1—C2 | 112.08 (16) | C3—C4—H4 | 120.5 |
| C1—N1—H1A | 120.0 | C4—C5—C6 | 120.9 (3) |
| C1—N1—H1B | 120.0 | C4—C5—C7 | 120.3 (3) |
| H1A—N1—H1B | 120.0 | C6—C5—C7 | 118.7 (4) |
| S1—N2—H2A | 120.0 | C5—C6—C1 | 121.5 (3) |
| S1—N2—H2B | 120.0 | C5—C6—H6 | 119.2 |
| H2A—N2—H2B | 120.0 | C1—C6—H6 | 119.2 |
| C6—C1—C2 | 116.9 (3) | C5—C7—H7A | 109.5 |
| C6—C1—N1 | 118.9 (3) | C5—C7—H7B | 109.5 |
| C2—C1—N1 | 124.3 (3) | H7A—C7—H7B | 109.5 |
| C3—C2—C1 | 120.9 (3) | C5—C7—H7C | 109.5 |
| C3—C2—S1 | 117.4 (3) | H7A—C7—H7C | 109.5 |
| C1—C2—S1 | 121.6 (3) | H7B—C7—H7C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2B···O2i | 0.86 | 2.15 | 3.003 (4) | 174 |
| N2—H2A···O1ii | 0.86 | 2.27 | 2.975 (4) | 139 |
| N1—H1B···O2 | 0.86 | 2.60 | 3.080 (5) | 117 |
| Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+3/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2B···O2i | 0.86 | 2.15 | 3.003 (4) | 174 |
| N2—H2A···O1ii | 0.86 | 2.27 | 2.975 (4) | 139 |
| N1—H1B···O2 | 0.86 | 2.60 | 3.080 (5) | 117 |
| Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+3/2. |
This project was sponsored by ShanDong Province Science & Technology Innovation Foundation.
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The title compound (I), Figure1, was prepared and tested for anticonvulsant activity in mice, (Monzani, et al.,1985). In addition, its derivatives was studied using indomethacin as a reference drug (Tait, et al.,1993). We report here its crystal and molecular structure. The molecules are linked by two strong N—H···O generating a graph-set motif R44(16) ring (Bernstein, et al., 1995) and is stabilized by one N—H···O intramolecular hydrogen bonds (Table1, Figure 2). The C2/S1/N2 plane makes a dihedral angle of 69.7 (2)° with the aromatic ring plane.