Crystal structure of 1,3-bis[(E)-benzylideneamino]propan-2-ol

The molecular and crystal structure of the title Schiff base derivative is reported. The crystal packing depends on O—H⋯N hydrogen-bonds, augmented by C—H⋯π interactions.


Chemical context
During the last decades, interest in Schiff bases and their complexes has been constant due to their extensive use for industrial purposes and also for their broad range of biological activities (Al Zoubi et al. 2016;Sahu et al. 2012;Da Silva et al., 2011;Przybylski et al. 2009). The common structural feature of these compounds is the presence of a azomethine group (-R-C N-), which can act as a hydrogen-bond acceptor or a ligand. To gain more insight into the structural and spectroscopic properties of this potentially polydentate ligand, we report herein the molecular structure of the title compound.

Supramolecular features
As found in related structures (Rivera, Miranda-Carvajal, Ríos-Motta & Bolte, 2016;Moodley & Van Zyl, 2012) in the crystal, molecules are linked by an O1-H1Á Á ÁN1 hydrogen bond, Table 1, forming columnar structures built from C(5) chains along the b-axis direction. In addition, pairs of the chains are linked by weak C24-H24Á Á ÁCg1 interactions (Table 1 and Fig. 2), involving the C11-C16 phenyl ring, together with C15-H15Á Á ÁCg2 and C15-H15Á Á ÁCg3 contacts involving the phenyl rings of the two disorder components; the centroids are defined in Table 1. It is noteworthy that the shortest (and presumably the strongest) of these non-classical contacts is C15-H15Á Á ÁCg3 involving the phenyl ring in the minor disorder component (Table 1).

Synthesis and crystallization
The title compound was prepared as described by . The crude product was recrystallized from diethyl ether solution with slow evaporation of the solvent, giving colorless crystals suitable for X-ray diffraction, m.p. 396.8-398 K, yield, 40%.  Table 1 Hydrogen-bond geometry (Å , ).

Figure 1
The molecular structure of the title compound, Displacement ellipsoids are drawn at the 50% probability level. Only the major occupancy disorder component is shown.

Figure 2
The crystal packing of the title compound showing the extended hydrogen-bonded network.

1,3-Bis[(E)-benzylideneamino]propan-2-ol
Crystal data Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.