| Autor: |
Sebbar, Nada Kheira, Hni, Brahim, Hökelek, Tuncer, Jaouhar, Abdelhakim, Taha, Mohamed Labd, Mague, Joel T., Essassi, El Mokhtar |
| Předmět: |
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| Zdroj: |
Acta Crystallographica Section E: Crystallographic Communications; Jun2019, Vol. 75 Issue 6, p721-727, 13p |
| Abstrakt: |
The title compound, C18H12Cl2N2OS, consists of a diÂhydroÂbenzoÂthiaÂzine unit linked by a –CH group to a 2,4-diÂchloroÂphenyl substituent, and to a propaneÂnitrile unit is folded along the S⋯N axis and adopts a flattened-boat conformation. The propaneÂnitrile moiety is nearly perpendicular to the mean plane of the diÂhydroÂbenzoÂthiaÂzine unit. In the crystal, C—HBnz⋯NPrpnit and C—HPrpnit⋯OThz (Bnz = benzene, Prpnit = propaneÂnitrile and Thz = thiaÂzine) hydrogen bonds link the molÂecules into inversion dimers, enclosing R2²(16) and R2²(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O⋯Cl interÂactions. π–π contacts between the benzene and phenyl rings, [centroid–centroid distance = 3.974 (1) Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (23.4%), H⋯Cl/Cl⋯H (19.5%), H⋯C/C⋯H (13.5%), H⋯N/N⋯H (13.3%), C⋯C (10.4%) and H⋯O/O⋯H (5.1%) interÂactions. Hydrogen bonding and van der Waals interÂactions are the dominant interÂactions in the crystal packing. Computational chemistry calculations indicate that the two independent C—HBnz⋯NPrpnit and C—HPrpnit⋯OThz hydrogen bonds in the crystal impart about the same energy (ca 43 kJ mol−1). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molÂecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
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