Crystal structure of 4-(prop-2-yn-1-yloxy)benzonitrile

Abstract

In the title compound, C10H7NO, the dihedral angle between the aromatic ring and the prop-2-yn-1-yloxy grouping is 9.47 (10)°. The bond lengths indicate electronic conjugation between the cyano group, the benzene ring and the propynyloxy oxygen atom. In the crystal, a hydrogen bond between the acetylenic C—H atom and the cyano nitrogen atom link the molecules into wave-like [30-1] C(11) chains. These chains are connected by Csp2—H...πac(πacis the acetylinic C—C triple bond) close contacts [2.794 (1) Å], resulting in a rolling sheet structure parallel to theacplane and aromatic π–π stacking interactions between the sheets [centroid–centroid distance = 3.593 (2) Å] generate a three-dimensional network.