N-(Thia­zol-2-yl)acetamide

Uzma Yunus; Muhammad Kalim Tahir; Moazzam Hussain Bhatti; Wai-Yeung Wong

doi:10.1107/S1600536808021442

. 2008 Jul 16;64(Pt 8):o1516. doi: 10.1107/S1600536808021442

N-(Thiazol-2-yl)acetamide

Uzma Yunus ^a,^*, Muhammad Kalim Tahir ^a, Moazzam Hussain Bhatti ^a, Wai-Yeung Wong ^b

PMCID: PMC2962142 PMID: 21203224

Abstract

The title compound, C₅H₆N₂OS, was synthesized from acetyl chloride and 2-aminothiazole in dry acetone. The asymmetric unit contains two molecules. The crystal structure is stabilized by N—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Raman et al. (2000 ▶); Wang et al. (2008 ▶); Yunus et al. (2007 ▶ 2008 ▶).

Experimental

Crystal data

C₅H₆N₂OS
M _r = 142.18
Monoclinic,
a = 16.0650 (12) Å
b = 11.3337 (8) Å
c = 7.0670 (5) Å
β = 101.908 (10)°
V = 1259.04 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 173 (2) K
0.30 × 0.26 × 0.22 mm

Data collection

Bruker SMART1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T _min = 0.830, T _max = 1.000 (expected range = 0.757–0.911)
7429 measured reflections
3024 independent reflections
2602 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.104
S = 1.05
3024 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021442/wk2088sup1.cif

e-64-o1516-sup1.cif^{(15.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021442/wk2088Isup2.hkl

e-64-o1516-Isup2.hkl^{(148.4KB, hkl)}

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

Enhanced figure: interactive version of Fig. 1

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3ⁱ	0.88	2.04	2.897 (2)	163
N4—H4A⋯N1ⁱⁱ	0.88	2.07	2.938 (2)	171
C2—H2A⋯O2ⁱⁱⁱ	0.95	2.41	3.350 (2)	171
C7—H7A⋯O1^iv	0.95	2.46	3.382 (2)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

supplementary crystallographic information

Comment

The thiazole ring and its derivatives are of great importance in biological systems due to their vast range of biological activities such as anti-inflammatory, analgesic and antipyretic (Raman et al., 2000). On the other hand amide compounds have extensive applications in the pharmaceutical industry (Wang et al., 2008). As a part of our research the title compound (I) has been synthesized and its crystal structure is reported herein (Yunus et al., 2007; 2008).

The title compound (I) crystallizes in a monoclinic space group with two molecules in asymmetric unit. All the bond lengths and angles are within the normal ranges. The molecules are stabilized by intermolecular hydrogen bonds N—H···N, and C—H···O (Table 1, Fig 2).

Experimental

A mixture of acetyl chloride (26 mmol) and 2-aminothiazole (26 mmol) was refluxed in dry acetone (60 ml) for two hours. After cooling, the mixture was poured into acidified cold water. The resulting yellow solid was filtered and washed with cold acetone. Single crystals of the title compound suitable for single-crystal x-ray analysis were obtained by recrystallization of the yellow solid from ethyl acetate.