Peculiarities of supramolecular organization of cyclic ketones with vinylacetylene fragments

Voronova, E.D.; Golovanov, A.A.; Odin, I.S.; Anisimov, M.A.; Dorovatovskii, P.V.; Zubavichus, Y.V.; Vologzhanina, A.V.

Авторы: Voronova Eugenia D., Golovanov Alexander A., Odin Ivan S., Anisimov Maksim A., Dorovatovskii Pavel V., Zubavichus Yan V., Vologzhanina Anna V.
Журнал: ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY
Том: 74
Номер: 12
Год издания: 2018
Издательство: John Wiley & Sons Inc.
Местоположение издательства: United States
Первая страница: 1674
Последняя страница: 1683
DOI: 10.1107/s2053229618015838
Аннотация: 1,5-Diaryl(heteroaryl) pentenynones show a tendency to crystallize in acentric space groups due to their inclination to form C-H center dot center dot center dot O hydrogen-bonded chains instead of dimers and thus exhibit nonlinear optical properties. A series of symmetrical alpha, alpha'-bis(3-arylprop-2-yn-1-ylidene) cycloalkanones and unsymmetrical alpha-(furan-2-ylmethylene)-alpha'-(3-arylprop-2-yn-1-ylidene) cyclohexanones closely related to pentenynones was synthesized, namely 2,5-bis(3-phenylprop-2-yn-1-ylidene) cyclopentanone, C23H16O, 2,5-bis[3-(4-bromophenyl) prop-2-yn-1-ylidene] cyclopentanone, C23H14Br2O, 2,6-bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone, C24H18O, 2,6-bis[3-(4-bromophenyl) prop-2-yn-1-ylidene] cyclohexanone, C24H16Br2O, 4-tert-butyl-2,6-bis(3-phenylprop-2-yn-1-ylidene) cyclohexanone, C28H25O, 4-tert-butyl-2,6-bis[3-(4-methylphenyl) prop-2-yn-1-ylidene]cyclohexanone, C30H30O, 2-(furan-2-ylmethylene)-6-(3-phenylprop-2-yn-1-ylidene) cyclohexanone, C20H16O2, and 6-(3-butylprop-2-yn-1-ylidene)-2-(furan-2-ylmethylene) cyclohexanone, C10H20O2, and investigated by means of X-ray diffraction to understand peculiarities of their supramolecular organization. Four of the eight novel compounds crystallize in acentric space groups. Three of these four compounds contain substituents at the para position of the phenyl ring, which affect the charge density on the H(CPh) atoms and thus stabilize CPh-H center dot center dot center dot O interactions. The fourth compound realizes the C-H center dot center dot center dot O hydrogen bonding via H atoms of the furyl ring. The applicability and shortcomings of the Full Interaction Map tool to predict the likelihood of CH center dot center dot center dot O and C-H center dot center dot center dot Br hydrogen-bonded motifs, and the effect of substituents on the phenyl ring on the supramolecular architecture are discussed.
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Peculiarities of supramolecular organization of cyclic ketones with vinylacetylene fragmentsстатья

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