N-(1,3-Thia­zol-2-yl)benzamide

Abstract

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,

• a = 12.0142 (2) Å

• b = 5.0581 (1) Å

• c = 15.4090 (3) Å

• β = 99.093 (1)°

• V = 924.62 (3) ų

• 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[F ² > 2σ(F ²)] = 0.029

• wR(F ²) = 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

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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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) .

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

C10H8N2OS	F(000) = 424
Mr = 204.24	Dx = 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

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

Refinement

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(Fo2) + (0.0497P)2 + 0.3231P] where P = (Fo2 + 2Fc2)/3
2104 reflections	(Δ/σ)max = 0.001
131 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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 codes: (i) −x+1, −y+1, −z+1.