Acta Cryst. (2009). E65, o2161 [ doi:10.1107/S160053680903164X ]
In the title compound, C10H10N2OS, the benzene ring is nearly co-planar with the thiazole ring, making a dihedral angle of 2.1 (2)°. The crystal structure is stabilized by intermolecular N-H
O hydrogen bonds. An intramolecular O-HN hydrogen bond is also present.
A solution with 0.005 mol of thiourea and 0.005 mol of 2-bromo-1-(2-hydroxyphenyl)-1-propanone in 50 ml of ethanol was refluxed for 10 h. After finishing the reaction, added 10 ml ammonia and continues to stir the solution 2 h. Then the solution was cooled and the precipitate formed was filtered out, dried, giving white crystals of title compound, yield 60.3%. m.p. 388–389 K. The crystals for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.
The hydroxy H atom was positioned geometrically (O–H = 0.84 Å) and refined as riding [Uiso(H) = 1.5 Ueq(O)]. Methyl H atoms were positioned geometrically (C–H = 0.98 Å) and torsion angles refined to fit the electron density [Uiso(H) = 1.5 Ueq(C)]. Other H atoms were placed in calculated positions (N–H 0.88 Å and aromatic C–H = 0.95 Å) and refined as riding [Uiso(H) = 1.2 Ueq(C, N)]. The highest peak in the final difference Fourier map is 0.79 Å apart from H8 atom.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./xu2563fig1thm.gif)
| Fig. 1. The molecular structure of (I), showing the atom-labelling scheme and 50% probability displacement ellipsoid (arbitrary spheres for H atoms). |
| C10H10N2OS | F(000) = 864 |
| Mr = 206.27 | Dx = 1.425 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 7684 reflections |
| a = 12.9391 (5) Å | θ = 2.4–27.0° |
| b = 10.3967 (4) Å | µ = 0.30 mm−1 |
| c = 14.2938 (6) Å | T = 173 K |
| V = 1922.86 (13) Å3 | Block, yellow |
| Z = 8 | 0.48 × 0.42 × 0.39 mm |
| Bruker SMART 1000 CCD diffractometer | 1881 independent reflections |
| Radiation source: fine-focus sealed tube | 1706 reflections with I > 2σ(I) |
| graphite | Rint = 0.027 |
| ω scans | θmax = 26.0°, θmin = 2.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −15→14 |
| Tmin = 0.869, Tmax = 0.891 | k = −12→12 |
| 11037 measured reflections | l = −17→17 |
| 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.150 | H-atom parameters constrained |
| S = 0.98 | w = 1/[σ2(Fo2) + (0.0885P)2 + 3.3976P] where P = (Fo2 + 2Fc2)/3 |
| 1881 reflections | (Δ/σ)max < 0.001 |
| 129 parameters | Δρmax = 1.20 e Å−3 |
| 0 restraints | Δρmin = −0.33 e Å−3 |
| C10H10N2OS | V = 1922.86 (13) Å3 |
| Mr = 206.27 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 12.9391 (5) Å | µ = 0.30 mm−1 |
| b = 10.3967 (4) Å | T = 173 K |
| c = 14.2938 (6) Å | 0.48 × 0.42 × 0.39 mm |
| Bruker SMART 1000 CCD diffractometer | 1881 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1706 reflections with I > 2σ(I) |
| Tmin = 0.869, Tmax = 0.891 | Rint = 0.027 |
| 11037 measured reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
| wR(F2) = 0.150 | Δρmax = 1.20 e Å−3 |
| S = 0.98 | Δρmin = −0.33 e Å−3 |
| 1881 reflections | Absolute structure: ? |
| 129 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Experimental. 1H NMR (CDCl3, 400 MHz): 2.48 (s, 3H, CH3), 4.97 (br, 2H, NH2), 6.86–7.42(m, 4H, phenyl-H). |
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 | 0.29069 (5) | 0.23322 (6) | 0.58881 (4) | 0.0269 (2) | |
| C1 | 0.2598 (2) | 0.3782 (2) | 0.64120 (16) | 0.0242 (5) | |
| C2 | 0.43091 (18) | 0.4000 (2) | 0.61774 (16) | 0.0232 (5) | |
| C3 | 0.4199 (2) | 0.2792 (2) | 0.58181 (17) | 0.0266 (6) | |
| C4 | 0.52468 (18) | 0.4802 (2) | 0.62670 (16) | 0.0241 (5) | |
| C5 | 0.52103 (19) | 0.6026 (2) | 0.66966 (17) | 0.0263 (5) | |
| C6 | 0.6103 (2) | 0.6770 (3) | 0.67875 (18) | 0.0315 (6) | |
| H6 | 0.6066 | 0.7589 | 0.7081 | 0.038* | |
| C7 | 0.7037 (2) | 0.6329 (3) | 0.64567 (19) | 0.0344 (6) | |
| H7 | 0.7642 | 0.6840 | 0.6526 | 0.041* | |
| C8 | 0.7095 (2) | 0.5136 (3) | 0.6021 (2) | 0.0369 (7) | |
| H8 | 0.7738 | 0.4829 | 0.5790 | 0.044* | |
| C9 | 0.6212 (2) | 0.4398 (3) | 0.59266 (18) | 0.0314 (6) | |
| H9 | 0.6261 | 0.3590 | 0.5620 | 0.038* | |
| C10 | 0.4945 (2) | 0.1822 (3) | 0.5439 (2) | 0.0413 (7) | |
| H10A | 0.5252 | 0.2149 | 0.4859 | 0.062* | |
| H10B | 0.4579 | 0.1016 | 0.5309 | 0.062* | |
| H10C | 0.5491 | 0.1665 | 0.5899 | 0.062* | |
| N1 | 0.33898 (16) | 0.45419 (19) | 0.65168 (14) | 0.0243 (5) | |
| N2 | 0.16111 (17) | 0.4091 (2) | 0.66472 (16) | 0.0316 (5) | |
| H2A | 0.1473 | 0.4850 | 0.6889 | 0.038* | |
| H2B | 0.1110 | 0.3531 | 0.6558 | 0.038* | |
| O1 | 0.43180 (14) | 0.65465 (18) | 0.70442 (15) | 0.0359 (5) | |
| H1 | 0.3833 | 0.6015 | 0.6985 | 0.054* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0270 (4) | 0.0238 (4) | 0.0301 (4) | −0.0019 (2) | −0.0005 (2) | −0.0051 (2) |
| C1 | 0.0263 (12) | 0.0229 (12) | 0.0234 (11) | −0.0001 (9) | −0.0006 (9) | −0.0005 (9) |
| C2 | 0.0234 (12) | 0.0238 (12) | 0.0225 (11) | 0.0026 (9) | 0.0002 (9) | 0.0014 (9) |
| C3 | 0.0258 (12) | 0.0266 (13) | 0.0274 (12) | 0.0006 (10) | 0.0004 (9) | −0.0009 (9) |
| C4 | 0.0236 (12) | 0.0264 (12) | 0.0223 (11) | 0.0008 (9) | −0.0014 (9) | 0.0036 (9) |
| C5 | 0.0243 (12) | 0.0270 (12) | 0.0277 (12) | 0.0022 (10) | −0.0017 (9) | 0.0022 (10) |
| C6 | 0.0313 (14) | 0.0312 (13) | 0.0321 (13) | −0.0040 (11) | −0.0043 (11) | 0.0010 (10) |
| C7 | 0.0285 (14) | 0.0421 (16) | 0.0328 (13) | −0.0106 (11) | −0.0026 (10) | 0.0045 (12) |
| C8 | 0.0250 (14) | 0.0473 (17) | 0.0385 (14) | −0.0006 (12) | 0.0061 (11) | 0.0019 (13) |
| C9 | 0.0274 (13) | 0.0335 (14) | 0.0333 (13) | 0.0010 (11) | 0.0047 (10) | −0.0017 (11) |
| C10 | 0.0338 (15) | 0.0321 (15) | 0.0581 (18) | 0.0044 (12) | 0.0047 (13) | −0.0131 (13) |
| N1 | 0.0221 (10) | 0.0226 (10) | 0.0282 (10) | 0.0003 (8) | 0.0016 (8) | −0.0015 (8) |
| N2 | 0.0228 (11) | 0.0298 (11) | 0.0422 (12) | −0.0017 (9) | 0.0024 (9) | −0.0075 (10) |
| O1 | 0.0242 (9) | 0.0275 (10) | 0.0561 (12) | 0.0006 (7) | −0.0007 (8) | −0.0113 (9) |
| S1—C1 | 1.730 (2) | C6—H6 | 0.9500 |
| S1—C3 | 1.742 (3) | C7—C8 | 1.390 (4) |
| C1—N1 | 1.302 (3) | C7—H7 | 0.9500 |
| C1—N2 | 1.359 (3) | C8—C9 | 1.382 (4) |
| C2—C3 | 1.364 (4) | C8—H8 | 0.9500 |
| C2—N1 | 1.403 (3) | C9—H9 | 0.9500 |
| C2—C4 | 1.477 (3) | C10—H10A | 0.9800 |
| C3—C10 | 1.498 (4) | C10—H10B | 0.9800 |
| C4—C9 | 1.405 (3) | C10—H10C | 0.9800 |
| C4—C5 | 1.414 (4) | N2—H2A | 0.8800 |
| C5—O1 | 1.368 (3) | N2—H2B | 0.8800 |
| C5—C6 | 1.397 (4) | O1—H1 | 0.8400 |
| C6—C7 | 1.376 (4) | ||
| C1—S1—C3 | 90.41 (12) | C6—C7—H7 | 120.1 |
| N1—C1—N2 | 124.6 (2) | C8—C7—H7 | 120.1 |
| N1—C1—S1 | 113.39 (19) | C7—C8—C9 | 119.6 (3) |
| N2—C1—S1 | 121.98 (19) | C7—C8—H8 | 120.2 |
| C3—C2—N1 | 114.3 (2) | C9—C8—H8 | 120.2 |
| C3—C2—C4 | 129.6 (2) | C8—C9—C4 | 122.4 (3) |
| N1—C2—C4 | 116.1 (2) | C8—C9—H9 | 118.8 |
| C2—C3—C10 | 133.6 (2) | C4—C9—H9 | 118.8 |
| C2—C3—S1 | 109.35 (19) | C3—C10—H10A | 109.5 |
| C10—C3—S1 | 117.0 (2) | C3—C10—H10B | 109.5 |
| C9—C4—C5 | 116.7 (2) | H10A—C10—H10B | 109.5 |
| C9—C4—C2 | 122.1 (2) | C3—C10—H10C | 109.5 |
| C5—C4—C2 | 121.2 (2) | H10A—C10—H10C | 109.5 |
| O1—C5—C6 | 116.4 (2) | H10B—C10—H10C | 109.5 |
| O1—C5—C4 | 122.8 (2) | C1—N1—C2 | 112.6 (2) |
| C6—C5—C4 | 120.8 (2) | C1—N2—H2A | 120.0 |
| C7—C6—C5 | 120.6 (3) | C1—N2—H2B | 120.0 |
| C7—C6—H6 | 119.7 | H2A—N2—H2B | 120.0 |
| C5—C6—H6 | 119.7 | C5—O1—H1 | 109.5 |
| C6—C7—C8 | 119.9 (2) | ||
| C3—S1—C1—N1 | 0.48 (19) | C9—C4—C5—C6 | −1.2 (3) |
| C3—S1—C1—N2 | 177.9 (2) | C2—C4—C5—C6 | 179.3 (2) |
| N1—C2—C3—C10 | −175.7 (3) | O1—C5—C6—C7 | −179.8 (2) |
| C4—C2—C3—C10 | 3.6 (5) | C4—C5—C6—C7 | 0.3 (4) |
| N1—C2—C3—S1 | 1.0 (3) | C5—C6—C7—C8 | 0.5 (4) |
| C4—C2—C3—S1 | −179.6 (2) | C6—C7—C8—C9 | −0.2 (4) |
| C1—S1—C3—C2 | −0.85 (19) | C7—C8—C9—C4 | −0.8 (4) |
| C1—S1—C3—C10 | 176.5 (2) | C5—C4—C9—C8 | 1.5 (4) |
| C3—C2—C4—C9 | 3.0 (4) | C2—C4—C9—C8 | −179.0 (2) |
| N1—C2—C4—C9 | −177.7 (2) | N2—C1—N1—C2 | −177.3 (2) |
| C3—C2—C4—C5 | −177.6 (2) | S1—C1—N1—C2 | 0.0 (3) |
| N1—C2—C4—C5 | 1.8 (3) | C3—C2—N1—C1 | −0.7 (3) |
| C9—C4—C5—O1 | 178.9 (2) | C4—C2—N1—C1 | 179.9 (2) |
| C2—C4—C5—O1 | −0.6 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.84 | 1.77 | 2.521 (3) | 148 |
| N2—H2B···O1i | 0.88 | 2.25 | 2.961 (3) | 138 |
| Symmetry codes: (i) −x+1/2, y−1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.84 | 1.77 | 2.521 (3) | 148 |
| N2—H2B···O1i | 0.88 | 2.25 | 2.961 (3) | 138 |
| Symmetry codes: (i) −x+1/2, y−1/2, z. |
This research was performed with the support of the doctoral start-up Fund for Doctoral Research of Guangdong Pharmaceutical University.
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Compounds containing thiazole are found to exhibit a wide spectrum of biological activities and many of them are well known antiviral, antifungal agents and some are used as pesticides (Kazzouli et al., 2002; Holla et al., 2003; Hu et al., 2008). The structure of 2-amino-4-arylthiazoles was reported before (He et al., 2006). Herein we report the synthesis and crystal structure of the title compound.
The molecular structure of (I) is illustrated in Fig. 1. The molecules are linked by intermolecular hydrogen bonds (N–H···O) and intramolecular hydrogen bonds (O–H···N) (Table 1). The dihedral angle between the planes of thiazole and the benzene ring is 2.1 (2)°.