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Cocrystals of 2,6‐dichloroaniline and 2,6‐dichlorophenol plus three new pseudopolymorphs of their coformers
Author(s) -
Gerhardt Valeska,
Bolte Michael
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/s2053229615015119
Subject(s) - cocrystal , synthon , chemistry , dimethylacetamide , triazine , molecule , stereochemistry , crystal structure , crystallography , solvent , medicinal chemistry , hydrogen bond , organic chemistry
The structures of cocrystals of 2,6‐dichlorophenol with 2,4‐diamino‐6‐methyl‐1,3,5‐triazine, C 6 H 4 Cl 2 O·C 4 H 7 N 5 , (III), and 2,6‐dichloroaniline with 2,6‐diaminopyrimidin‐4(3 H )‐one and N , N ‐dimethylacetamide, C 6 H 5 Cl 2 N·C 4 H 6 N 4 O·C 4 H 9 NO, (V), plus three new pseudopolymorphs of their coformers, namely 2,4‐diamino‐6‐methyl‐1,3,5‐triazine– N , N ‐dimethylacetamide (1/1), C 4 H 7 N 5 ·C 4 H 9 NO, (I), 2,4‐diamino‐6‐methyl‐1,3,5‐triazine– N ‐methylpyrrolidin‐2‐one (1/1), C 4 H 7 N 5 ·C 5 H 9 NO, (II), and 6‐aminoisocytosine– N ‐methylpyrrolidin‐2‐one (1/1), C 4 H 6 N 4 O·C 5 H 9 NO, (IV), are reported. Both 2,6‐dichlorophenol and 2,6‐dichloroaniline are capable of forming definite synthon motifs, which usually lead to either two‐ or three‐dimensional crystal‐packing arrangements. Thus, the two isomorphous pseudopolymorphs of 2,4‐diamino‐6‐methyl‐1,3,5‐triazine, i.e. (I) and (II), form a three‐dimensional network, while the N ‐methylpyrrolidin‐2‐one solvate of 6‐aminoisocytosine, i.e. (IV), displays two‐dimensional layers. On the basis of these results, attempts to cocrystallize 2,6‐dichlorophenol with 2,4‐diamino‐6‐methyl‐1,3,5‐triazine, (III), and 2,6‐dichloroaniline with 6‐aminoisocytosine, (V), yielded two‐dimensional networks, whereby in cocrystal (III) the overall structure is a consequence of the interaction between the two compounds. By comparison, cocrystal–solvate (V) is mainly built by 6‐aminoisocytosine forming layers, with 2,6‐dichloroaniline and the solvent molecules arranged between the layers.