The crystal structure of (1E,2E)‐2,2′‐dipyridylglyoxime

Abstract

1E,2E)-2,2 -dipyridylglyoxime (1) was synthesized by a literature method involving the reaction of 2,2 -pyridyl with an excess of hydroxylammonium chloride and sodium hydroxide in distilled water. 1 was characterized by elemental analysis, melting point, mass spectrometry, and NMR ( 1 H and 13 C) spectroscopy. In addition, the crystal structure of 1 was determined by low temperature X-ray analysis. 1 crystallizes in the monoclinic space group P2 1 /n with four formula units in the unit cell and the following unit cell parameters: a = 6.269(1)Å, b = 10.258(1) A, c = 9.132(1)Å, β = 107.59(1) • , and V = 559.7(1) A 3 . Strong O· · ·N hydrogen bonds link the molecules of 1, forming three-dimensional hydrogen-bonded networks; whereas the unclassical C· · ·O hydrogen bonds result in the formation of C1,1(9) and C2,2(18) infinite chains and dimmer pairs with the graph-set descriptor R2,2(16). Lastly, the structure of 1 was fully optimized using DFT calculations p)) and the NBO and Mulliken charges were calculated at the same level of theory. C 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:59-65, 2012; View this article online at wileyonlinelibrary.com.

2,2′-[(1E,2E)-1,2-Bis(hydroxyimino)ethane-1,2-diyl]dipyridinium hexachloridorhenate(IV)

“…In the studied crystal structure the cations are the E,E isomers where the glyoxime moieties form interplanar angles of about 55° with planes of aromatic rings. Similar values of the geometrical parameters are observed compared to those published by Sabaté & Delalu (2012) ( Table 2) for (1E,2E)-2,2′-dipyridylglyoxime. However slight differences in overall geometries can be distinguished.…”

“…The cation is a protonated form of (1E,2E)-2,2′-dipyridylglyoxime, C 12 H 10 N 4 O 2 [or (1E,2E)-N,N′dihydroxy-1,2-di(pyridin-2-yl)ethane-1,2-diimine or (1E,2E)-1,2-di(pyridin-2-yl)ethanedione dioxime]. The crystal structure of (1E,2E)-2,2′-dipyridylglyoxime was recently reported by Sabaté & Delalu (2012). In the literature there is known one structure which contains a cyclic form of the C 12 H 10 N 4 O 2 dioxime as a di(2-pyridyl)furoxan coordinated to copper(II) (Richardson & Steel, 2000).…”

“…For background tointeractions, see: Janiak (2000). For related structures of the reported cation, see: Richardson & Steel (2000); Sabaté & Delalu (2012).…”