Premium
The interplay of solvation, molecular conformation and supramolecular assembly in 1,1′‐({[(ethane‐1,2‐diyl)dioxy](1,2‐phenylene)}bis(methanylylidene))bis(thiosemicarbazide) and its N , N ‐dimethylformamide disolvate
Author(s) -
Mohamed Shaaban K.,
Younes Sabry H. H.,
AbdelRaheem Eman M. M.,
Mague Joel T.,
Akkurt Mehmet,
Glidewell Christopher
Publication year - 2015
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229615018744
Subject(s) - chemistry , molecule , crystallography , aryl , supramolecular chemistry , ring (chemistry) , hydrogen bond , solvent , stereochemistry , dihedral angle , crystal structure , alkyl , organic chemistry
The wide diversity of applications of thiosemicarbazones and bis(thiosemicarbazones) has seen them used as anticancer and antitubercular agents, and as ligands in metal complexes designed to act as site‐specific radiopharmaceuticals. Molecules of 1,1′‐({[(ethane‐1,2‐diyl)dioxy](1,2‐phenylene)}bis(methanylylidene))bis(thiosemicarbazide) {alternative name: 2,2′‐[ethane‐1,2‐diylbis(oxy)]dibenzaldehyde bis(thiosemicarbazide)}, C 18 H 20 N 6 O 2 S 2 , (I), lie across twofold rotation axes in the space group C 2/ c , with an O—C—C—O torsion angle of −59.62 (13)° and a trans ‐planar arrangement of the thiosemicarbazide fragments relative to the adjacent aryl rings. The molecules of (I) are linked by N—H...S hydrogen bonds to form sheets containing R 2 4 (38) rings and two types of R 2 2 (8) ring. In the N , N ‐dimethylformamide disolvate, C 18 H 20 N 6 O 2 S 2 ·2C 3 H 7 NO, (II), the independent molecular components all lie in general positions, but one of the solvent molecules is disordered over two sets of atomic sites having occupancies of 0.839 (3) and 0.161 (3). The O—C—C—O torsion angle in the ArOCH 2 CH 2 OAr component is −75.91 (14)° and the independent thiosemicarbazide fragments both adopt a cis ‐planar arrangement relative to the adjacent aryl rings. The ArOCH 2 CH 2 OAr components in (II) are linked by N—H...S hydrogen bonds to form deeply puckered sheets containing R 2 2 (8), R 2 4 (8) and two types of R 2 2 (38) rings, and which contain cavities which accommodate all of the solvent molecules in the interior of the sheets. Comparisons are made with some related compounds.