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A whole zoo of hydrogen bonds in one crystal structure: tris(isonicotinium) hydrogensulfate sulfate monohydrate
Author(s) -
Truong Khai-Nghi,
Lothmann Niklas,
Englert Ulli
Publication year - 2017
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/s2053229617008269
Subject(s) - hydrogen bond , chemistry , pyridinium , pyridine , sulfuric acid , protonation , sulfate , crystallography , molecule , medicinal chemistry , inorganic chemistry , organic chemistry , ion
Depending on the reaction partner, the organic ditopic molecule isonicotinic acid (Hina) can act either as a Brønsted acid or base. With sulfuric acid, the pyridine ring is protonated to become a pyridinium cation. Crystallization from ethanol affords the title compound tris(4‐carboxypyridinium) hydrogensulfate sulfate monohydrate, 3C 6 H 6 NO 2 + ·HSO 4 − ·SO 4 2− ·H 2 O or [(H 2 ina) 3 (HSO 4 )(SO 4 )(H 2 O)]. This solid contains 11 classical hydrogen bonds of very different flavour and nonclassical C—H…O contacts. All N—H and O—H donors find at least one acceptor within a suitable distance range, with one of the three pyridinium H atoms engaged in bifurcated N—H…O hydrogen bonds. The shortest hydrogen‐bonding O…O distance is subtended by hydrogensulfate and sulfate anions, viz. 2.4752 (19) Å, and represents one of the shortest hydrogen bonds ever reported between these residues.