Crystal structure and Hirshfeld surface analysis of 6-amino-8-(2,6-dichlorophenyl)-1,3,4,8-tetrahydro-2H-pyrido[1,2-a]pyrimidine-7,9-dicarbonitrile

In the crystal structure of the title compound, intermolecular N—H⋯N and C—H⋯N hydrogen bonds between the molecules lead to sheets extending parallel to the (110) and (10) planes.

As part of our studies on the chemistry of bridgehead nitrogen heterocycles, as well as taking into account our ongoing structural studies (Mamedov et al., 2013;Naghiyev et al., 2020a,b,c;Naghiyev et al., 2021), we report here the crystal structure and Hirshfeld surface analysis of the title compound, C 16 H 13 Cl 2 N 5 , obtained by an efficient three-component synthetic protocol.

Supramolecular features
In the crystal, intermolecular N-HÁ Á ÁN hydrogen bonds between the amine functions as donor groups and the nitrile N atoms as acceptor groups and intermolecular C-HÁ Á ÁN hydrogen bonds lead to the formation of sheets extending parallel to (110) and (110) (Table 1; Figs. 2, 3 and 4). These hydrogen-bonded sheets cross each other (Fig. 5). C-HÁ Á Á

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Figure 3
A view along [100] showing the intermolecular N-HÁ Á ÁN and C-HÁ Á ÁN hydrogen bonds of the title compound. The dichlorophenyl group and H atoms not involved in hydrogen bonding have been omitted for clarity.
Cg3 is the centroid of the C11-C16 dichlorophenyl ring.

Figure 4
A view along [010] showing the intermolecular N-HÁ Á ÁN and C-HÁ Á ÁN hydrogen bonds of the title compound. The dichlorophenyl group and H atoms not involved in hydrogen bonding have been omitted for clarity.

Database survey
In the crystal of VAMBET, molecules are linked via C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds, forming layers parallel to (101). In the molecule of HECLUZ, the seven-membered pentamethylene ring adopts a twist-boat conformation. In the crystal, hydrogen bonds with 16-membered ring and three chain motifs are generated by N-HÁ Á ÁN and N-HÁ Á ÁO contacts. The amino group is located close to the nitrogen atoms, forming hydrogen bonds with R 1 2 (4) and R 2 2 (12) graphset motifs. This amino group also forms a hydrogen bond with the C O oxygen atom of a molecule translated parallel to [100], which links the molecules into R 4 4 (16) rings. Hydrogenbonded chains are formed along [100] by alternating R 2 2 (12) and R 4 4 (16) rings. These chains are stabilized by intermolecular stacking interactions observed between the pyridine and pyrimidine rings. In LEGLIU, the molecular structure is built up from two fused six-membered rings and one seven-

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.