Work

Different intermolecular interactions in solvated and unsolvated isatin-based dithiocarbazate imine derivatives

Year: 2025

Type: article

Abstract: The syntheses and structures of 2-fluorobenzyl ( Z )-2-(2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate dimethyl sulfoxide monosolvate, C 16 H 12 FN 3 OS 2 ·C 2 H 6 OS ( 1 ) and 2-fluorobenzyl ( Z )-2-(5-bromo-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C 16 H 11 BrFN 3 OS 2 ( 2 ) are reported. Both structures feature a Z -configuration with respect to the C=N bond and the fluorobenzyl ring is approximately orthogonal to the isatin moiety. For 1 , the crystal packing features weak C ar —H...S (ar = aromatic) hydrogen bonds that link adjacent molecules in a C (10) fashion to form pleated chains propagating along [001] and short S...O contacts between dimethyl sulfoxide solvent molecules forming chains along [010]. The N—H hydrogen bond donors in 1 form either intramolecular or discrete N—H...O (DMSO) hydrogen bonds. In 2 , alternating R 2 2 (8)-type pairwise N—H...O hydrogen bonds and short F...Br contacts link the molecules into chains propagating along [2 1 0]. The later unsolvated structure is of notably poorer quality and exhibits disorder in its o -fluorobenzyl group, with a 180° flip and a small twist around the S—C bond. These findings are consistent with the results of Hirshfeld surface analyses.

Source: Acta Crystallographica Section E Crystallographic Communications

DOI: 10.1107/s2056989025011028

Authors: Aidan P. McKay, David B. Cordes, Mohd Abdul Fatah Abdul Manan

Institutions: University of St Andrews, Universiti Teknologi MARA System, Universiti Teknologi MARA

Language: English

Topic: Crystal structures of chemical compounds

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $500

Funder: Universiti Teknologi MARA