Crystal structure of ethyl (1RS,6SR)-4-(2-methyl-1H-imidazol-4-yl)-2-oxo-6-(2,3,5-tri-chloro-phen-yl)cyclo-hex-3-ene-1-carboxyl-ate

Billava J Mohan; Balladka K Sarojini; Hemmige S Yathirajan; Ravindranath Rathore; Christopher Glidewell

doi:10.1107/S2056989015023245

Crystal structure of ethyl (1RS,6SR)-4-(2-methyl-1H-imidazol-4-yl)-2-oxo-6-(2,3,5-tri-chloro-phen-yl)cyclo-hex-3-ene-1-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2016 Jan 1;72(Pt 1):31-4. doi: 10.1107/S2056989015023245.

Authors

Billava J Mohan¹, Balladka K Sarojini², Hemmige S Yathirajan³, Ravindranath Rathore⁴, Christopher Glidewell⁵

Affiliations

¹ Department of Chemistry, P.A. College of Engineering, Mangaluru 574 153, India.
² Department of Studies in Industrial Chemistry, Mangalore University, Mangalagangothri 574 199, India.
³ Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.
⁴ Department of Biotechnology, Dayananda Sagar College of Engineering, Bengaluru 560 078, India.
⁵ School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.

Abstract

The title compound, C19H17Cl3N2O3, has been prepared in a cyclo-condensation reaction between 2,3,5-tri-chloro-benzaldehye and 4-acetyl-2-methyl-1H-imidazole. The cyclo-hexenone ring adopts an envelope conformation with the C atom substituted by the tri-chloro-phenyl ring as the flap. The mutually trans ester and aryl substituents both occupy equatorial sites. In the crystal, a combination of N-H⋯O and C-H⋯N hydrogen bonds links the mol-ecules into ribbons of edge-fused centrosymmetric rings, which enclose R 2 (2)(14) and R 4 (4)(16) alternate ring motifs, propagating along the b-axis direction.

Keywords: crystal structure; cyclocondensation reaction; hydrogen bonding; molecular conformation; molecular stereochemistry.