Crystal structure determination and analyses of Hirshfeld surface, crystal voids, intermolecular interaction energies and energy frameworks of 1-benzyl-4-(methylsulfanyl)-3a,7a-dihydro-1H-pyrazolo[3,4-d]pyrimidine

Abstract

The pyrazolopyrimidine moiety in the title molecule, C13H12N4S, is planar with the methylsulfanyl substituent lying essentially in the same plane. The benzyl group is rotated well out of this plane by 73.64 (6)°, giving the molecule an approximate L shape. In the crystal, C—H...π(ring) interactions and C—H...S hydrogen bonds form tubes extending along the a axis. Furthermore, there are π–π interactions 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%) interactions. 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.

Keywords

• crystal structure
• pyrazolopyrimidine
• sulfide
• hydrogen bond
• c—h...π(ring) interaction