Journal of Chemical Crystallography p. 113 - 118 (2019)
Update date:2022-08-29
Topics:
Linares Mendez, Iamnica J.
Pleizier, Jeffrey S.
Wang, Hong-Bo
Wisner, James A.
Descriptions of azoheteroaromatic compounds in their cis-isomeric form in the solid state are almost non-existent. Cis-2,2′-azopyridine is a known compound which structure differentiates from the trans-isomer based on spectroscopic evidence (UV–Vis absorption, 1H, and 13C NMR spectroscopy) and with studies regarding its stability, thermal reversion to the trans-isomer, and dipole moment in solution. However, the structure of this compound in the solid state has been unresolved. Herein, we present the crystal structure of cis-2,2′-azopyridine that forms red prismatic crystals in the monoclinic space group C2/c. The unit cell parameters are: a = 23.485 (4), b = 5.9241 (12), c = 21.656 (4) ?, and V = 2717.1 (9) ?3 with 12 molecules per unit cell. Molecules are arranged as two helical conformers (P and M) with C–N=N–C torsion angles and aromatic ring planes’ angles comparable to those reported for cis-azobenzene. Graphical Abstract: The rare structural determination of an azoheteroaromatic cis-isomer of 2-azopyridine that was synthesized, isolated and crystallized is presented. X-ray structure analysis reveals that the molecule forms dimeric complexes containing both M- and P-helical conformers as well as infinite stacked columns in the solid state through a combination of C–H?N hydrogen bonds, C–H?π interactions and lone pair?π contacts. [Figure not available: see fulltext.].
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Doi:10.1021/jo051268h
(2005)Doi:10.1080/07328309808002899
(1998)Doi:10.1007/s10989-019-09998-x
(2020)Doi:10.1021/acs.orglett.8b02168
(2018)Doi:10.1016/0040-4039(93)85116-E
(1993)Doi:10.1080/07391102.2019.1654410
(2020)