N-(1,3-Thia­zol-2-yl)benzamide

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

doi:10.1107/S1600536809009374

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o817

doi:10.1107/S1600536809009374

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

Afsaneh Zonouzi,^a Roghieh Mirzazadeh,^a Hossein Rahmani ^b and Seik Weng Ng ^c ^*

^aDepartment of Chemistry, College of Science, University of Tehran, PO Box 13145-143, Tehran, Iran, ^bInstitute of Chemical Industries, Iranian Research Organization for Science and Technology, PO Box 15815-358, Tehran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 March 2009; accepted 13 March 2009; online 25 March 2009)

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

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

Crystal data

C₁₀H₈N₂OS
M_r = 204.24
Monoclinic, P 2₁ /c
a = 12.0142 (2) Å
b = 5.0581 (1) Å
c = 15.4090 (3) Å
β = 99.093 (1)°
V = 924.62 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 123 K
0.35 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXdiffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.898, T_max = 0.955
6130 measured reflections
2104 independent reflections
1900 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.087
S = 1.07
2104 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1ⁱ	0.88 (2)	2.04 (2)	2.922 (2)	173 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009374/bt2897sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009374/bt2897Isup2.hkl

checkCIF report

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.

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

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

C₁₀H₈N₂OS	F(000) = 424
M_r = 204.24	D_x = 1.467 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3661 reflections
a = 12.0142 (2) Å	θ = 2.7–28.3°
b = 5.0581 (1) Å	µ = 0.31 mm⁻¹
c = 15.4090 (3) Å	T = 123 K
β = 99.093 (1)°	Prism, colorless
V = 924.62 (3) Å³	0.35 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	2104 independent reflections
Radiation source: fine-focus sealed tube	1900 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
T_min = 0.898, T_max = 0.955	k = −6→6
6130 measured reflections	l = −18→20

Refinement top

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0497P)² + 0.3231P] where P = (F_o² + 2F_c²)/3
2104 reflections	(Δ/σ)_max = 0.001
131 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₈N₂OS	V = 924.62 (3) Å³
M_r = 204.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0142 (2) Å	µ = 0.31 mm⁻¹
b = 5.0581 (1) Å	T = 123 K
c = 15.4090 (3) Å	0.35 × 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)
T_min = 0.898, T_max = 0.955	R_int = 0.016
6130 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.37 e Å⁻³
2104 reflections	Δρ_min = −0.21 e Å⁻³
131 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.31389 (3)	0.14766 (7)	0.64434 (2)	0.02139 (12)
O1	0.17527 (8)	0.5276 (2)	0.56442 (6)	0.0229 (2)
N1	0.49298 (9)	0.2290 (2)	0.57510 (7)	0.0196 (2)
N2	0.34258 (9)	0.4997 (2)	0.51416 (7)	0.0186 (2)
H2	0.3903 (16)	0.574 (4)	0.4833 (13)	0.039 (5)*
C1	0.43025 (12)	−0.0499 (3)	0.67627 (9)	0.0229 (3)
H1	0.4338	−0.1892	0.7180	0.028*
C2	0.51534 (11)	0.0214 (3)	0.63371 (8)	0.0210 (3)
H2A	0.5863	−0.0656	0.6434	0.025*
C3	0.38904 (11)	0.3090 (2)	0.57304 (8)	0.0173 (3)
C4	0.23427 (11)	0.5903 (3)	0.50994 (8)	0.0179 (3)
C5	0.19345 (10)	0.7638 (3)	0.43320 (8)	0.0178 (3)
C6	0.11908 (11)	0.9675 (3)	0.44382 (9)	0.0207 (3)
H6	0.0981	0.9989	0.4998	0.025*
C7	0.07532 (11)	1.1252 (3)	0.37287 (9)	0.0239 (3)
H7	0.0251	1.2655	0.3804	0.029*
C8	0.10522 (11)	1.0769 (3)	0.29083 (9)	0.0235 (3)
H8	0.0754	1.1848	0.2422	0.028*
C9	0.17835 (11)	0.8722 (3)	0.27946 (9)	0.0221 (3)
H9	0.1978	0.8389	0.2231	0.026*
C10	0.22320 (11)	0.7157 (3)	0.35072 (8)	0.0199 (3)
H10	0.2739	0.5765	0.3432	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02421 (19)	0.02313 (19)	0.01715 (19)	−0.00215 (12)	0.00419 (13)	0.00464 (12)
O1	0.0245 (5)	0.0273 (5)	0.0181 (5)	0.0007 (4)	0.0071 (4)	0.0020 (4)
N1	0.0231 (5)	0.0187 (5)	0.0170 (5)	0.0014 (4)	0.0027 (4)	0.0016 (4)
N2	0.0201 (5)	0.0202 (5)	0.0160 (5)	0.0008 (4)	0.0049 (4)	0.0042 (4)
C1	0.0300 (7)	0.0190 (6)	0.0181 (6)	−0.0018 (5)	−0.0012 (5)	0.0027 (5)
C2	0.0260 (6)	0.0174 (6)	0.0182 (6)	0.0013 (5)	−0.0010 (5)	0.0002 (5)
C3	0.0223 (6)	0.0170 (6)	0.0125 (6)	−0.0019 (5)	0.0027 (5)	−0.0008 (4)
C4	0.0210 (6)	0.0184 (6)	0.0143 (6)	−0.0004 (5)	0.0028 (5)	−0.0018 (5)
C5	0.0180 (6)	0.0189 (6)	0.0161 (6)	−0.0021 (5)	0.0015 (5)	0.0008 (5)
C6	0.0181 (6)	0.0242 (6)	0.0201 (6)	−0.0001 (5)	0.0038 (5)	−0.0028 (5)
C7	0.0206 (6)	0.0209 (6)	0.0291 (7)	0.0022 (5)	0.0007 (5)	−0.0006 (5)
C8	0.0213 (6)	0.0241 (6)	0.0231 (7)	−0.0013 (5)	−0.0022 (5)	0.0061 (5)
C9	0.0221 (6)	0.0277 (7)	0.0163 (6)	−0.0026 (5)	0.0028 (5)	0.0017 (5)
C10	0.0200 (6)	0.0217 (6)	0.0180 (6)	0.0015 (5)	0.0032 (5)	0.0001 (5)

Geometric parameters (Å, º) top

S1—C1	1.7255 (14)	C5—C6	1.3903 (18)
S1—C3	1.7327 (13)	C5—C10	1.3949 (18)
O1—C4	1.2231 (16)	C6—C7	1.3877 (19)
N1—C3	1.3084 (17)	C6—H6	0.9500
N1—C2	1.3834 (16)	C7—C8	1.389 (2)
N2—C4	1.3714 (17)	C7—H7	0.9500
N2—C3	1.3801 (16)	C8—C9	1.387 (2)
N2—H2	0.88 (2)	C8—H8	0.9500
C1—C2	1.348 (2)	C9—C10	1.3913 (18)
C1—H1	0.9500	C9—H9	0.9500
C2—H2A	0.9500	C10—H10	0.9500
C4—C5	1.4919 (17)

C1—S1—C3	88.49 (6)	C6—C5—C4	118.65 (11)
C3—N1—C2	109.69 (11)	C10—C5—C4	121.33 (12)
C4—N2—C3	123.16 (11)	C7—C6—C5	120.24 (12)
C4—N2—H2	121.6 (13)	C7—C6—H6	119.9
C3—N2—H2	114.8 (13)	C5—C6—H6	119.9
C2—C1—S1	110.43 (10)	C6—C7—C8	119.71 (13)
C2—C1—H1	124.8	C6—C7—H7	120.1
S1—C1—H1	124.8	C8—C7—H7	120.1
C1—C2—N1	115.88 (12)	C7—C8—C9	120.40 (12)
C1—C2—H2A	122.1	C7—C8—H8	119.8
N1—C2—H2A	122.1	C9—C8—H8	119.8
N1—C3—N2	121.17 (11)	C8—C9—C10	119.95 (13)
N1—C3—S1	115.46 (10)	C8—C9—H9	120.0
N2—C3—S1	123.29 (10)	C10—C9—H9	120.0
O1—C4—N2	121.95 (12)	C5—C10—C9	119.78 (12)
O1—C4—C5	122.90 (12)	C5—C10—H10	120.1
N2—C4—C5	115.14 (11)	C9—C10—H10	120.1
C6—C5—C10	119.91 (12)

C3—S1—C1—C2	1.28 (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—C10	37.46 (17)
C2—N1—C3—N2	−174.45 (11)	C10—C5—C6—C7	−0.75 (19)
C2—N1—C3—S1	2.29 (14)	C4—C5—C6—C7	−177.03 (11)
C4—N2—C3—N1	−179.70 (12)	C5—C6—C7—C8	0.7 (2)
C4—N2—C3—S1	3.83 (17)	C6—C7—C8—C9	0.1 (2)
C1—S1—C3—N1	−2.12 (10)	C7—C8—C9—C10	−0.7 (2)
C1—S1—C3—N2	174.53 (11)	C6—C5—C10—C9	0.09 (19)
C3—N2—C4—O1	7.78 (19)	C4—C5—C10—C9	176.27 (12)
C3—N2—C4—C5	−170.70 (11)	C8—C9—C10—C5	0.6 (2)
O1—C4—C5—C6	35.22 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.88 (2)	2.04 (2)	2.922 (2)	173 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂OS
M_r	204.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	12.0142 (2), 5.0581 (1), 15.4090 (3)
β (°)	99.093 (1)
V (Å³)	924.62 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.35 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.898, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	6130, 2104, 1900
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.087, 1.07
No. of reflections	2104
No. of parameters	131
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1ⁱ	0.88 (2)	2.04 (2)	2.922 (2)	173 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kumar, V., Parmar, V. S. & Malhotra, S. M. (2007). Tetrahedron Lett. 48, 809–812. Web of Science CrossRef CAS Google Scholar
Prasad, A. K., Kumar, V., Malhotra, S., Ravikumar, V. T., Sanghvib, Y. S. & Parmar, V. S. (2005). Bioorg. Med. Chem. 13, 4467–4472. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar