6,6'-Dihydr-oxy-2,2'-[(pentane-1,5-diyl-dioxy)bis-(nitrilo-methyl-idyne)]diphenol

Abstract

The mol-ecule of the title compound, C(19)H(22)N(2)O(6), assumes a W-shaped configuration with the dihedral angle between the two halves of the mol-ecule being 82.48 (5)°. There is one half-mol-ecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the five methylene groups in the [-CH=N-O-(CH(2))(5)-O-N=CH-] bridge. The dihedral angle formed by the two benzene rings in each mol-ecule of the title compound is 84.18 (4)°. There are strong intra-molecular O-H⋯N and O-H⋯O hydrogen bonds and weak inter-molecular π-π stacking inter-actions between neighbouring benzene rings, and the inter-molecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Å along the b and c axes, respectively. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link each mol-ecule to two others, forming an infinite three-dimensional supra-molecular structure.

Fig. 1.

The molecular structure of the title compound with atom numbering scheme [Symmetry codes: -x + 1, y, -z + 3/2]. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

Fig. 2.

The W shape configuration of the title compound.

Fig. 3.

Part of the supramolecular structure of the title compound along b axis. Intra- and intermolecular hydrogen bonds are shown as dashed lines.