2-Methyl-4-(4-nitro-phen-yl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study.

Abstract

The di-substituted acetyl-ene residue in the title compound, C11H11NO3, is capped at either end by di-methyl-hydroxy and 4-nitro-benzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the mol-ecular packing is the formation, via hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds, of hexa-meric clusters about a site of symmetry . The aggregates are sustained by 12-membered {⋯OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C-H⋯O(nitro) inter-actions, involving both nitro-O atoms. The aforementioned inter-actions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker inter-molecular contacts.