Table 1.

Co-Crystal Screening Results.

Compound	Charge (kJ/mol)	COO− (cm−1)	C=O (cm−1)	O–H⋯N (cm−1)	Outcome
				*O⋯H–N (cm−1)
3-aminopyridine*	−289	1654	n/a	2615, 2092	salt
2-aminopyridine*	−287	1670	n/a	2524, 1969	salt
2-amino-4,6-dimethylpyrimidine	−287	n/a	1665	2496, 1907	+
2-amino-4-chloro-6-methylpyrimidine	−278	n/a	1686	2529, 1904	+
3-hydroxypyridine	−276	n/a	1693	2533, 1904	+
2-amino-4-hydroxy-6-methylpyrimidine	−273	n/a	1697	2590, 1899	+
2-aminopyrimidine	−272	n/a	1697	2374, 1887	+
4,4′-bipyridine	−268	n/a	1704	2398, 1916	+
2-amino-5-chloropyridine	−267	n/a	1693	2566, 1985	+
4-chloro-2,6-diaminopyrimidine	−263	n/a	1683	2361, 1916	+
3,5-dimethylpyrazole	−256	n/a	1690	n/a	−
2-chloropyrimidine	−256	n/a	1691	n/a	−
Pyrazole	−254	n/a	1691	n/a	−
3,5-dimethyl-4-chloropyrazole	−246	n/a	1691	n/a	−
4-iodo-3,5-dimethylpyrazole	−240	n/a	1691	n/a	−
2-amino-3,5-dibromopyridine	−238	n/a	1696	2378, 1875	+
4-bromopyrazole	−228	n/a	1691	n/a	−
4-iodopyrazole	−227	n/a	1691	n/a	−