Crystal structure determination and analyses of Hirshfeld surface, crystal voids, inter-molecular inter-action energies and energy frameworks of 1-benzyl-4-(methyl-sulfan-yl)-3a,7a-di-hydro-1H-pyrazolo-[3,4-d]pyrimidine.

The pyrazolo-pyrimidine moiety in the title mol-ecule, C13H12N4S, is planar with the methyl-sulfanyl substituent lying essentially in the same plane. The benzyl group is rotated well out of this plane by 73.64 (6)°, giving the mol-ecule an approximate L shape. In the crystal, C-H⋯π(ring) inter-actions and C-H⋯S hydrogen bonds form tubes extending along the a axis. Furthermore, there are π-π inter-actions between parallel phenyl rings with centroid-to-centroid distances of 3.8418 (12) Å. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (47.0%), H⋯N/N⋯H (17.6%) and H⋯C/C⋯H (17.0%) inter-actions. The volume of the crystal voids and the percentage of free space were calculated to be 76.45 Å3 and 6.39%, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the cohesion of the crystal structure is dominated by the dispersion energy contributions.

Crystal structure, Hirshfeld surface analysis, calculations of inter-molecular inter-action energies and energy frameworks and the DFT-optimized mol-ecular structure of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)meth-yl]-3-(prop-1-en-2-yl)-1H-benzimidazol-2-one.

The benzimidazole entity of the title mol-ecule, C17H21N5O, is almost planar (r.m.s. deviation = 0.0262 Å). In the crystal, bifurcated C-H⋯O hydrogen bonds link individual mol-ecules into layers extending parallel to the ac plane. Two weak C-H⋯π(ring) inter-actions may also be effective in the stabilization of the crystal structure. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H⋯H (57.9%), H⋯C/C⋯H (18.1%) and H⋯O/O⋯H (14.9%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the most dominant forces in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization of the title compound is dominated via dispersion energy contributions. The mol-ecular structure optimized by density functional theory (DFT) at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state.

Crystal structure, Hirshfeld surface analysis, calculations of crystal voids, inter-action energy and energy frameworks as well as density functional theory (DFT) calculations of 3-[2-(morpholin-4-yl)eth-yl]-5,5-di-phenyl-imidazolidine-2,4-dione.

In the title mol-ecule, C21H23N3O3, the imidazolidine ring slightly deviates from planarity and the morpholine ring exhibits the chair conformation. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds form helical chains of mol-ecules extending parallel to the c axis that are connected by C-H⋯π(ring) inter-actions. A Hirshfeld surface analysis reveals that the most important contributions for the crystal packing are from H⋯H (55.2%), H⋯C/C⋯H (22.6%) and H⋯O/O⋯H (20.5%) inter-actions. The volume of the crystal voids and the percentage of free space were calculated to be 236.78 Å3 and 12.71%, respectively. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the nearly equal electrostatic and dispersion energy contributions. The DFT-optimized mol-ecular structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state. Moreover, the HOMO-LUMO behaviour was elucidated to determine the energy gap.

Crystal structure and Hirshfeld surface analysis of (Z)-N-{chloro-[(4-ferrocenylphen-yl)imino]-meth-yl}-4-ferrocenylaniline N,N-di-methyl-formamide monosolvate.

The title mol-ecule, [Fe2(C5H5)2(C23H17ClN2)]·C3H7NO, is twisted end to end and the central N/C/N unit is disordered. In the crystal, several C-H⋯π(ring) inter-actions lead to the formation of layers, which are connected by further C-H⋯π(ring) inter-actions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (60.2%) and H⋯C/C⋯H (27.0%) inter-actions. Hydrogen bonding, C-H⋯π(ring) inter-actions and van der Waals inter-actions dominate the crystal packing.

Crystal structure, Hirshfeld surface analysis, crystal voids, inter-action energy calculations and energy frameworks, and DFT calculations of 1-(4-methyl-benz-yl)in-do-line-2,3-dione.

The in-do-line portion of the title mol-ecule, C16H13NO2, is planar. In the crystal, a layer structure is generated by C-H⋯O hydrogen bonds and C-H⋯π(ring), π-stacking and C=O⋯π(ring) inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (43.0%), H⋯C/C⋯H (25.0%) and H⋯O/O⋯H (22.8%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 120.52 Å3 and 9.64%, respectively, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the dispersion energy contributions in the title compound. Moreover, the DFT-optimized structure at the B3LYP/6-311G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state.

Crystal structure, Hirshfeld surface analysis, crystal voids, inter-action energy calculations and energy frameworks and DFT calculations of ethyl 2-cyano-3-(3-hy-droxy-5-methyl-1H-pyrazol-4-yl)-3-phen-yl-propano-ate.

The title compound, C16H17N3O3, is racemic as it crystallizes in a centrosymmetric space group (P ), although the trans disposition of substituents about the central C-C bond is established. The five- and six-membered rings are oriented at a dihedral angle of 75.88 (8)°. In the crystal, N-H⋯N hydrogen bonds form chains of mol-ecules extending along the c-axis direction that are connected by inversion-related pairs of O-H⋯N into ribbons. The ribbons are linked by C-H⋯π(ring) inter-actions, forming layers parallel to the ab plane. A Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (45.9%), H⋯N/N⋯H (23.3%), H⋯C/C⋯H (16.2%) and H⋯O/O⋯H (12.3%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. The volume of the crystal voids and the percentage of free space were calculated to be 100.94 Å3 and 13.20%, showing that there is no large cavity in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the electrostatic energy contributions in the title compound. Moreover, the DFT-optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.

Synthesis, structure and Hirshfeld surface analysis of 1,3-bis-[(1-octyl-1H-1,2,3-triazol-4-yl)meth-yl]-1H-benzo[d]imidazol-2(3H)-one.

The title mol-ecule, C29H44N8O, adopts a conformation resembling a two-bladed fan with the octyl chains largely in fully extended conformations. In the crystal, C-H⋯O hydrogen bonds form chains of mol-ecules extending along the b-axis direction, which are linked by weak C-H⋯N hydrogen bonds and C-H⋯π inter-actions to generate a three-dimensional network. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (68.3%), H⋯N/N⋯H (15.7%) and H⋯C/C⋯H (10.4%) inter-actions.

Crystal structure, Hirshfeld surface analysis, inter-molecular inter-action energies, energy frameworks and DFT calculations of 4-amino-1-(prop-2-yn-1-yl)pyrimidin-2(1H)-one.

In the title mol-ecule, C7H7N3O, the pyrimidine ring is essentially planar, with the propynyl group rotated out of this plane by 15.31 (4)°. In the crystal, a tri-periodic network is formed by N-H⋯O, N-H⋯N and C-H⋯O hydrogen-bonding and slipped π-π stacking inter-actions, leading to narrow channels extending parallel to the c axis. Hirshfeld surface analysis of the crystal structure reveals that the most important contributions for the crystal packing are from H⋯H (36.2%), H⋯C/C⋯H (20.9%), H⋯O/O⋯H (17.8%) and H⋯N/N⋯H (12.2%) inter-actions, showing that hydrogen-bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the stabilization is dominated by the electrostatic energy contributions. The mol-ecular structure optimized by density functional theory (DFT) calculations at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined structure in the solid state. The HOMO-LUMO behaviour was also elucidated to determine the energy gap.