Crystal structure of three solvates of 1,1′-binaphthyl-2,2′-bicarboxylic acid with 2-picoline View Full Text


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Article Info

DATE

2013-03

AUTHORS

L. Yu. Izotova, D. M. Ashurov, S. A. Talipov, B. T. Ibragimov, E. Weber

ABSTRACT

From solutions in 2-picoline (2-methylpyridine), depending on the temperature of crystallization, the universal clathratogen — 1,1′-binaphthyl-2,2′-bicarboxylic acid (BBA) — precipitates as crystals of three types with different composition and structure. Under normal conditions (room temperature), the precipitate is crystals of BBA disolvate with 2-picoline; a temperature reduction of 20°C results in the crystallization of monosolvate dihydrate; and a temperature increase of the same level results in the precipitation of monosolvate. That is, as the temperature of crystallization rises, the number of included guest molecules gradually decreases and the space where they are located becomes more closed. In 1:1:2 BBA/2-picoline/H2O solvate (space group P21/n, a = 11.991(2) Å, b = 9.317(2) Å, c = 22.283(5) Å, β = 99.77(3)○, V = 2453.3(9) Å3, Z = 4), the carboxyl groups of the BBA molecule at the C21 atom are deprotonated and the released proton goes to the nitrogen atom of 2-picoline. BBA molecules interact with those of 2-picoline and water via H bonds to form infinite chains in direction [111], which, in their turn, join together into infinite two-dimensional sheets parallel to plane (−101). 2-Picoline molecules are located in the channels. In BBA/2-picoline disolvate (space group C2/c, a = 11.7523(11) Å, b = 13.8563(13) Å, c = 17.9615(13) Å, β = 108.044(9)○, V = 2781.1(4) Å3, Z = 4), one BBA molecule and two H bond 2-picoline molecules form a 0-dimensional associate of the type G-H-G. The solvent molecules are also located in the channels. In BBA/2-picoline monosolvate (space group P21/c, a = 9.299(5) Å, b = 12.727(5) Å, c = 19.011(5) Å, β = 95.248(5)○, V = 2240.5(16) Å3, Z = 4), each BBA molecule is H-bonded with a 2-picoline molecule to form a 0-dimensional associate of the type H-G. Guest molecules are located in closed cavities. More... »

PAGES

400-407

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s0022476613020194

DOI

http://dx.doi.org/10.1134/s0022476613020194

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1038992330


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