Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

The title compound consists of a substituted 2-[(E)-2-arylethenyl]-3-arylquinazolin-4(3H)-one skeleton. The substituents at the ethylene fragment are located in trans positions. In the crystal, molecules are connected via O—H⋯O hydrogen bonds forming a 21 helix propagating along the a-axis direction.


Supramolecular features
In the crystal of 1, molecules are connected via O-HÁ Á ÁO hydrogen bonds forming a 2 1 helix, with graph set C(3), propagating along the a-axis direction (Table 1 and Fig. 2). This is similar to the crystal packing reported for the structure of diltiazem acetylsalicilate hydrate (Stepanovs et al., 2016). In 1, the helices are linked via C-HÁ Á Á interactions, forming slabs lying parallel to the ab plane (Table 1 and Fig. 3).

Database survey
A search of the Cambridge Structural Database (Version 5.37; Groom & Allen, 2014) for substructure S1 (Fig. 4) gave 137 hits, while a search for substructure S2 (2-arylvinyl 3-aryl quinazolin-4(3H)-one skeleton, Fig. 4) gave only three hits: Nosova et al. (2012); Trashakhova et al. (2011);Ovchinnikova et al. (2014). However, none of the characterized single crystals contains a hydrogen-bond donor/acceptor in the aryl substituent at position 3 of the quinazolinone unit and information on intermolecular interactions of such structures is still missing. The only example containing a carboxylic functionality at the 3-aryl substituent of quinazolin-4(3H)-one was analysed as a complex with Staphylococcus aureus at the PBP2a binding site (Bouley et al., 2015). The molecular structure of compound 1, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Table 1 Hydrogen-bond geometry (Å , ).

Figure 3
A view along the a axis of the crystal packing of compound 1. The hydrogen bonds are shown as dashed lines and the C-HÁ Á Á interactions (see Table 1) are represented as thin black lines.

Figure 2
A fragment of the crystal structure of compound 1, showing the helix-like hydrogen-bonded chain propagating along the a-axis direction.
Single crystals suitable for X-ray analysis were obtained by slow evaporation from ethanol at room temperature (m.p. > 523 K).

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 Synthesis of the title compound, 1.

Figure 4
Substructures used for the Database survey.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.