Crystal structure of r-1, c-2-dibenzoyl- t-3, t-4-bis-(2-nitro-phen-yl)cyclo-butane

Acta Crystallogr E Crystallogr Commun. 2017 Nov 17;73(Pt 12):1866-1870. doi: 10.1107/S2056989017015936. eCollection 2017 Dec 1.

Abstract

The condensation reaction of aceto-phenone (1-phenyl-ethan-1-one) with 2-nitro-benzaldehyde in the molten state yielded the expected chalcone, (E)-3-(2-nitro-phen-yl)-1-phenyl-prop-2-en-1-one, and, unexpectedly, the title compound, C30H22N2O6, which results from the syn head-to-head [2 + 2] cyclo-addition of the chalcone. The mol-ecular structure of the dimer shows that the four benzene rings of the substituents are oriented in such a way that potential steric hindrance is minimized, whilst allowing some degree of inter-molecular π-π inter-actions for crystal stabilization. In the mol-ecule, one nitro group is disordered over two positions, with occupancies for each part of 0.876 (7) and 0.127 (7).

Keywords: chalcone; crystal structure; cyclo­butane; truxillic isomer; truxinic isomer.

Grants and funding

This work was funded by VIEP–BUAP grant . Consejo Nacional de Ciencia y Tecnología grants 297948, 277416, and 173585. PRODEP grant UPMP-PTC-007.