2-Amino-4-tert-butyl-5-(4-chloro­benz­yl)thia­zol-3-ium chloride

Jun-Mei Peng; Lin-Tao Yang; Zhi Qin; Ai-Xi Hu

doi:10.1107/S160053681000721X

. 2010 Mar 3;66(Pt 4):o735. doi: 10.1107/S160053681000721X

2-Amino-4-tert-butyl-5-(4-chlorobenzyl)thiazol-3-ium chloride

Jun-Mei Peng ^a, Lin-Tao Yang ^a, Zhi Qin ^a, Ai-Xi Hu ^a,^*

PMCID: PMC2983809 PMID: 21580581

Abstract

The title compound, C₁₄H₁₈ClN₂S⁺·Cl⁻, crystallizes with two formula units in the asymmetric unit. The dihedral angles between the mean planes of the chlorophenyl and thiazole rings are 87.8 (2) and 88.0 (2)° in the two independent molecules. In the crystal, the anions and cations are connected by N—H⋯Cl hydrogen bonds.

Related literature

For 2-amino-4-arylthiazol compounds, see Marcantonio et al. (2002 ▶) and for their synthesis, see: Hu et al. (2007 ▶). For related structures, see: Cao et al. (2007 ▶); He et al. (2006 ▶); Hu et al. (2007 ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₈ClN₂S⁺·Cl⁻
M _r = 317.26
Monoclinic,
a = 12.0810 (5) Å
b = 17.0208 (8) Å
c = 16.6465 (7) Å
β = 108.587 (1)°
V = 3244.4 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 173 K
0.45 × 0.41 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.801, T _max = 0.840
16212 measured reflections
7029 independent reflections
5252 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.106
S = 1.03
7029 reflections
349 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000721X/bt5189sup1.cif

e-66-0o735-sup1.cif^{(26.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000721X/bt5189Isup2.hkl

e-66-0o735-Isup2.hkl^{(344KB, hkl)}

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
N1—H1⋯Cl3	0.88	2.33	3.0882 (16)	144
N2—H2A⋯Cl3	0.88	2.34	3.1078 (19)	146
N2—H2B⋯Cl4	0.88	2.21	3.0327 (19)	155
N3—H3⋯Cl4	0.88	2.27	3.0289 (17)	145
N4—H4A⋯Cl4	0.88	2.36	3.1131 (19)	143
N4—H4B⋯Cl3ⁱ	0.88	2.22	3.0543 (19)	157

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was funded by the Central University Basic Scientific Research Fund of Hunan University.

supplementary crystallographic information

Comment

Thiazole compounds are important nitrogen-containing heterocyclic compounds, because of their wide range of biological activity. 2-Amino-4-arylthiazol compounds play an important role in the field of organic pharmaceutical chemistry (Marcantonio et al., 2002). The synthesis of 2-amino-4-arylthiazoles was reported before (Cao et al., 2007, He et al., 2006, Hu et al., 2007 b, Xu et al., 2007). The title compound was prepared as part of an ongoing investigation on the synthesis and structural properties of 2-amino-4-arylthiazole derivatives.

Experimental

0.05 mol 2-Chloro-1-(4-chlorophenyl)-4,4-dimethyl-3-pentanone and 0.05 mol thiurea were dissolved in 100 ml EtOH and heated to reflux 12 h. After finishing the reaction, the solution was cooled and the precipitate formed was filtered out, dried, givingthe the title compound, yield 71.3 %. m.p.474–475.1 K.The crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperation.