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.

SUBMITTER: Caracelli I 

PROVIDER: S-EPMC6690440 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature