Different packing motifs of isomeric (E)-N'-(halo-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides controlled by C-Hâ¯O inter-actions.
Acta Crystallogr E Crystallogr Commun
; 74(Pt 3): 313-318, 2018 Mar 01.
Article
in En
| MEDLINE
| ID: mdl-29765713
The crystal structures of three isomeric (E)-N'-(chloro-phenyl-methyl-idene)-N-methyl-2-(thio-phen-2-yl)acetohydrazides (C14H13ClN2OS) are described, with the Cl atom in ortho (I), meta (III) and para (IV) positions in the benzene ring. The ortho-bromo derivative (II) (C14H13BrN2OS), which is isostructural with its chloro congener (I), is also reported. Mol-ecules (I)-(III) have similar conformations, which approximate to l-shapes, as indicated by their N-C-C-Ct (t = thio-phene) torsion angles of -90.1â
(3), -91.44â
(18) and -90.7â
(9)°, respectively. The conformation of (IV) is different, with an equivalent torsion angle of -170.75â
(11)° corresponding to a more extended shape for the mol-ecule. The thio-phene ring in each structure features 'flip' rotational disorder. The packing for (I) and (II) features inversion dimers, linked by pairs of C-Hâ¯O inter-actions, which generate R22(14) loops. In the crystal of (III), [010] C(8) chains arise, with adjacent mol-ecules linked by pairs of C-Hâ¯O hydrogen bonds. The packing for (IV) features unusually short C-Hâ¯O inter-actions arising from an H atom attached to the benzene ring (Hâ¯O = 2.18â
Å), which lead to C(9) [301] chains. Hirshfeld fingerprint percentage contact contributions are similar for the four title compounds.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Acta Crystallogr E Crystallogr Commun
Year:
2018
Document type:
Article
Affiliation country:
Brazil
Country of publication:
United kingdom