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Crystal structure and hydrogen bonding in the hydrated cocrystalline salt tryptaminium–3,5‐dinitrobenzoate–quinoline–water (3/3/2/2)
Author(s) -
Lynch Daniel E.,
Smith Graham,
Keene Tony D.,
Horton Peter N.
Publication year - 2016
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/s2053229616014728
Subject(s) - hydrogen bond , chemistry , crystallography , crystal structure , molecule , quinoline , hydrate , supramolecular chemistry , adduct , ring (chemistry) , stereochemistry , organic chemistry
The study of ternary systems is interesting because it introduces the concept of molecular preference/competition into the system where one molecule may be displaced because the association between the other two is significantly stronger. Current definitions of a tertiary system indicate that solvent molecules are excluded from the molecule count of the system and some of the latest definitions state that any molecule that is not a solid in the parent form at room temperature should also be excluded from the molecule count. In the structure of the quinoline adduct hydrate of tryptaminium 3,5‐dinitrobenzoate, 3C 10 H 13 N 2 + ·3C 7 H 3 N 2 O 6 − ·2C 9 H 7 N·2H 2 O, the asymmetric unit comprises multiple cation and anion species which are conformationally similar among each type set. In the crystal, a one‐dimensional hydrogen‐bonded supramolecular structure is generated through extensive intra‐ and inter‐unit aminium N—H…O and N—H…N, and water O—H…O hydrogen bonds. Within the central‐core hydrogen‐bonding associations, conjoined cyclic R 4 4 (10), R 5 3 (10) and R 4 4 (12) motifs are generated. The unit is expanded into a one‐dimensional column‐like polymer extending along [010]. Present also in the crystal packing of the structure are a total of 19 π–π interactions involving both cation, anion and quinoline species [ring‐centroid separation range = 3.395 (3)–3.797 (3) Å], as well as a number of weak C—H…O hydrogen‐bonding associations. The presence of the two water molecules in the crystal structure is considered to be the principal causative factor in the low symmetry of the asymmetric unit.