2-(4-Chloro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

Hoong-Kun Fun; Ching Kheng Quah; Prakash S Nayak; B Narayana; B K Sarojini

doi:10.1107/S1600536812034629

. 2012 Aug 11;68(Pt 9):o2679. doi: 10.1107/S1600536812034629

2-(4-Chlorophenyl)-N-(1,3-thiazol-2-yl)acetamide

Hoong-Kun Fun ^a,^*,^‡, Ching Kheng Quah ^a,^§, Prakash S Nayak ^b, B Narayana ^b, B K Sarojini ^c

PMCID: PMC3435701 PMID: 22969572

Abstract

In the title compound, C₁₁H₉ClN₂OS, the thiazole ring is nearly planar (r.m.s. deviation = 0.003 Å) and forms a dihedral angle of 64.18 (7)° with the bezene ring. In the crystal, inversion dimers linked by pairs of N—H⋯N_t (t = thiazole) hydrogen bonds generate R ₂ ²(8) loops.

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₉ClN₂OS
M _r = 252.71
Monoclinic,
a = 13.9169 (13) Å
b = 5.5188 (5) Å
c = 15.1836 (14) Å
β = 100.311 (2)°
V = 1147.34 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 296 K
0.35 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.847, T _max = 0.918
11463 measured reflections
3421 independent reflections
2769 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.116
S = 1.02
3421 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034629/hb6927sup1.cif

e-68-o2679-sup1.cif^{(20.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034629/hb6927Isup2.hkl

e-68-o2679-Isup2.hkl^{(167.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034629/hb6927Isup3.cml

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—H1N2⋯N1ⁱ	0.866 (18)	2.096 (18)	2.9606 (16)	176.2 (17)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the thiazol-2-yl ring (S1/N1/C1-C3) is nearly planar (r.m.s. deviation = 0.003 Å) and it forms a dihedral angle of 64.18 (7)° with the bezene ring (C6-C11). Bond lengths and angles are within normal ranges and are comparable to related structures (Fun et al., 2011a, 2011b, 2012a, 2012b).

In the crystal structure, Fig. 2, molecules are linked into an inversion dimer by pairs of N2–H1N2···N1 hydrogen bonds (Table 1), generating R₂²(8) ring motifs (Bernstein et al., 1995).

Experimental

4-Chlorophenylacetic acid (0.170 g, 1 mmol), 2-aminothiazole (0.1 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 ml). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 ml of ice-cold aqueous hydrochloric acid with stirring. The resulting solution was extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound (I). Orange blocks were grown from an acetone and toluene (1:1) solvent mixture by the slow evaporation method (m.p.: 441K).