methanol monosolvate: single-crystal X-ray diffraction study and Hirshfeld surface analysis

The title compound, C36H37ClN4O7 CH3OH, which crystallizes as a methanol solvate, may possess biological activity, which is inherent for a natural peptide or protein. In the crystal, molecules of the title compound form hydrogen-bonded tetramers with the solvate molecules acting as bridges as a result of the O— H O and N—H O intermolecular hydrogen bonds. Hirshfeld surface analysis was used to study the different types of intermolecular interactions whose contributions are: H H = 53.8%, O H/H O = 19.0%, C H/H C = 14.8%, Cl H/H Cl = 5.3%, N H/H N = 3.2%.


Chemical context
The combined application of Doebner and Ugi-type multicomponent reactions, with the participation of the azoloazine type of carboxylic acid as an acid component in the Ugi reaction to increase the molecular diversity of the target heterocyclic compounds, was reported in our previous publication (Murlykina et al., 2019).

Figure 2
Tetramer of hydrogen-bonded title molecules linked through methanol solvent molecules.

Figure 1
Molecular structure of the title compound (solvent molecule and hydrogen atoms are omitted for clarity). Displacement ellipsoids are shown at the 50% probability level.

Hirshfeld surface analysis
Different types of intra-and intermolecular interactions in a crystal structure can be identified and visualized with Hirshfeld surface analysis (Turner et al., 2017). The molecular Hirshfeld surface of the major compound was generated using a high surface resolution with three-dimensional d norm surfaces. The areas that are coloured red on the d norm surfaces correspond to contacts that are shorter than the van der Waals radii sum of the closest atoms (Fig. 3). These red spots indicate atoms participating in hydrogen bonding or short contacts. The brightest red spots are observed at the hydroxyl groups of both the main and the methanol molecules, indicating a strong O-HÁ Á ÁO intermolecular hydrogen bond. In addition, brightred spots are observed at the carboxyl group and at the hydrogen atom of the amino group, indicating short contacts. It should be mentioned that smaller red areas are found at the nitrogen atom of the partially saturated five-membered heterocycle, at the C31H 3 methyl group and at the C32 O6 carboxyl group, indicating short contacts.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2