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Acta Cryst. (2009). E65, o817    [ doi:10.1107/S1600536809009374 ]

N-(1,3-Thiazol-2-yl)benzamide

A. Zonouzi, R. Mirzazadeh, H. Rahmani and S. W. Ng

Abstract top

The title compound, C10H8N2OS, features a nonplanar molecule [dihedral angle between the two aromatic rings = 43.6 (1)°]. Two molecules are linked by N-H...N hydrogen bonds about a centre of inversion, giving rise to a hydrogen-bonded dimer.

Related literature top

The synthesis uses microwave radiation, which compares with benzoylation by reacting benzoyl cyanide in an ionic liquid: see: Kumar et al. (2007); Prasad et al. (2005).

Experimental top

2-Aminothiazole (1 g, 10 mmol) and benzoyl cyanide (1.31 g, 10 mmol) were stirred together without any solvent for 3 h at 323 K. The oily product was purified by recrystalization from ethanol (yield 1.97 g, 90%); m.p. 383 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

The amino H-atom was located in a difference Fouier map, and was freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellisoid plot (Barbour, 2001) of C10H8N2OS; probability levels are set at 70% and H-atoms are drawn as spheres of arbitrary radius.
N-(1,3-Thiazol-2-yl)benzamide top
Crystal data top
C10H8N2OSF(000) = 424
Mr = 204.24Dx = 1.467 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3661 reflections
a = 12.0142 (2) Åθ = 2.7–28.3°
b = 5.0581 (1) ŵ = 0.31 mm−1
c = 15.4090 (3) ÅT = 123 K
β = 99.093 (1)°Prism, colorless
V = 924.62 (3) Å30.35 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		2104 independent reflections
Radiation source: fine-focus sealed tube1900 reflections with I > 2σ(I)
graphiteRint = 0.016
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −15→15
Tmin = 0.898, Tmax = 0.955k = −6→6
6130 measured reflectionsl = −18→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3231P]
where P = (Fo2 + 2Fc2)/3
2104 reflections(Δ/σ)max = 0.001
131 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C10H8N2OSV = 924.62 (3) Å3
Mr = 204.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.0142 (2) ŵ = 0.31 mm−1
b = 5.0581 (1) ÅT = 123 K
c = 15.4090 (3) Å0.35 × 0.20 × 0.15 mm
β = 99.093 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2104 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1900 reflections with I > 2σ(I)
Tmin = 0.898, Tmax = 0.955Rint = 0.016
6130 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087Δρmax = 0.37 e Å−3
S = 1.07Δρmin = −0.21 e Å−3
2104 reflectionsAbsolute structure: ?
131 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.31389 (3)0.14766 (7)0.64434 (2)0.02139 (12)
O10.17527 (8)0.5276 (2)0.56442 (6)0.0229 (2)
N10.49298 (9)0.2290 (2)0.57510 (7)0.0196 (2)
N20.34258 (9)0.4997 (2)0.51416 (7)0.0186 (2)
H20.3903 (16)0.574 (4)0.4833 (13)0.039 (5)*
C10.43025 (12)−0.0499 (3)0.67627 (9)0.0229 (3)
H10.4338−0.18920.71800.028*
C20.51534 (11)0.0214 (3)0.63371 (8)0.0210 (3)
H2A0.5863−0.06560.64340.025*
C30.38904 (11)0.3090 (2)0.57304 (8)0.0173 (3)
C40.23427 (11)0.5903 (3)0.50994 (8)0.0179 (3)
C50.19345 (10)0.7638 (3)0.43320 (8)0.0178 (3)
C60.11908 (11)0.9675 (3)0.44382 (9)0.0207 (3)
H60.09810.99890.49980.025*
C70.07532 (11)1.1252 (3)0.37287 (9)0.0239 (3)
H70.02511.26550.38040.029*
C80.10522 (11)1.0769 (3)0.29083 (9)0.0235 (3)
H80.07541.18480.24220.028*
C90.17835 (11)0.8722 (3)0.27946 (9)0.0221 (3)
H90.19780.83890.22310.026*
C100.22320 (11)0.7157 (3)0.35072 (8)0.0199 (3)
H100.27390.57650.34320.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02421 (19)0.02313 (19)0.01715 (19)−0.00215 (12)0.00419 (13)0.00464 (12)
O10.0245 (5)0.0273 (5)0.0181 (5)0.0007 (4)0.0071 (4)0.0020 (4)
N10.0231 (5)0.0187 (5)0.0170 (5)0.0014 (4)0.0027 (4)0.0016 (4)
N20.0201 (5)0.0202 (5)0.0160 (5)0.0008 (4)0.0049 (4)0.0042 (4)
C10.0300 (7)0.0190 (6)0.0181 (6)−0.0018 (5)−0.0012 (5)0.0027 (5)
C20.0260 (6)0.0174 (6)0.0182 (6)0.0013 (5)−0.0010 (5)0.0002 (5)
C30.0223 (6)0.0170 (6)0.0125 (6)−0.0019 (5)0.0027 (5)−0.0008 (4)
C40.0210 (6)0.0184 (6)0.0143 (6)−0.0004 (5)0.0028 (5)−0.0018 (5)
C50.0180 (6)0.0189 (6)0.0161 (6)−0.0021 (5)0.0015 (5)0.0008 (5)
C60.0181 (6)0.0242 (6)0.0201 (6)−0.0001 (5)0.0038 (5)−0.0028 (5)
C70.0206 (6)0.0209 (6)0.0291 (7)0.0022 (5)0.0007 (5)−0.0006 (5)
C80.0213 (6)0.0241 (6)0.0231 (7)−0.0013 (5)−0.0022 (5)0.0061 (5)
C90.0221 (6)0.0277 (7)0.0163 (6)−0.0026 (5)0.0028 (5)0.0017 (5)
C100.0200 (6)0.0217 (6)0.0180 (6)0.0015 (5)0.0032 (5)0.0001 (5)
Geometric parameters (Å, °) top
S1—C11.7255 (14)C5—C61.3903 (18)
S1—C31.7327 (13)C5—C101.3949 (18)
O1—C41.2231 (16)C6—C71.3877 (19)
N1—C31.3084 (17)C6—H60.9500
N1—C21.3834 (16)C7—C81.389 (2)
N2—C41.3714 (17)C7—H70.9500
N2—C31.3801 (16)C8—C91.387 (2)
N2—H20.88 (2)C8—H80.9500
C1—C21.348 (2)C9—C101.3913 (18)
C1—H10.9500C9—H90.9500
C2—H2A0.9500C10—H100.9500
C4—C51.4919 (17)
C1—S1—C388.49 (6)C6—C5—C4118.65 (11)
C3—N1—C2109.69 (11)C10—C5—C4121.33 (12)
C4—N2—C3123.16 (11)C7—C6—C5120.24 (12)
C4—N2—H2121.6 (13)C7—C6—H6119.9
C3—N2—H2114.8 (13)C5—C6—H6119.9
C2—C1—S1110.43 (10)C6—C7—C8119.71 (13)
C2—C1—H1124.8C6—C7—H7120.1
S1—C1—H1124.8C8—C7—H7120.1
C1—C2—N1115.88 (12)C7—C8—C9120.40 (12)
C1—C2—H2A122.1C7—C8—H8119.8
N1—C2—H2A122.1C9—C8—H8119.8
N1—C3—N2121.17 (11)C8—C9—C10119.95 (13)
N1—C3—S1115.46 (10)C8—C9—H9120.0
N2—C3—S1123.29 (10)C10—C9—H9120.0
O1—C4—N2121.95 (12)C5—C10—C9119.78 (12)
O1—C4—C5122.90 (12)C5—C10—H10120.1
N2—C4—C5115.14 (11)C9—C10—H10120.1
C6—C5—C10119.91 (12)
C3—S1—C1—C21.28 (10)N2—C4—C5—C6−146.32 (12)
S1—C1—C2—N1−0.31 (15)O1—C4—C5—C10−141.00 (14)
C3—N1—C2—C1−1.25 (16)N2—C4—C5—C1037.46 (17)
C2—N1—C3—N2−174.45 (11)C10—C5—C6—C7−0.75 (19)
C2—N1—C3—S12.29 (14)C4—C5—C6—C7−177.03 (11)
C4—N2—C3—N1−179.70 (12)C5—C6—C7—C80.7 (2)
C4—N2—C3—S13.83 (17)C6—C7—C8—C90.1 (2)
C1—S1—C3—N1−2.12 (10)C7—C8—C9—C10−0.7 (2)
C1—S1—C3—N2174.53 (11)C6—C5—C10—C90.09 (19)
C3—N2—C4—O17.78 (19)C4—C5—C10—C9176.27 (12)
C3—N2—C4—C5−170.70 (11)C8—C9—C10—C50.6 (2)
O1—C4—C5—C635.22 (18)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.88 (2)2.04 (2)2.922 (2)173 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···N1i0.88 (2)2.04 (2)2.922 (2)173 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

The authors thank the Research Council of Tehran University and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Kumar, V., Parmar, V. S. & Malhotra, S. M. (2007). Tetrahedron Lett. 48, 809–812.

Prasad, A. K., Kumar, V., Malhotra, S., Ravikumar, V. T., Sanghvib, Y. S. & Parmar, V. S. (2005). Bioorg. Org. Med. Chem. 13, 4467–4472.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.