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Mesomorphism and crystal packing of dichotomous compounds; X-ray crystal structure of N-(4-hexyloxybenzylidene)-p-toluidine

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Abstract

The crystal structure of N-(4-hexyloxybenzylidene)-p-toluidine (1) was determined at 150, 273, 295, and 320 K. Compound 1 was studied by differential scanning calorimetry (DSC). According to the DSC analysis, compound 1 exhibits monotropic mesomorphism associated with Cr-Iso-N-S-Cr phase transitions. The crystal packing is built up from alternating loosely packed aliphatic and closely packed aromatic regions, which is typical of enantiotropic mesomorphic compounds. In the closely packed regions, there are two types of weak directional interactions, such as π⋯π stacking interactions and weak C-H O hydrogen bonds, which link the molecules into centrosymmetric dimers. The thermal behavior of compound 1 and its relation to the crystal packing are discussed.

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Authors and Affiliations

  1. N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    L. G. Kuz’mina, P. Kalle & A. V. Churakov

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  1. L. G. Kuz’mina
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  2. P. Kalle
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  3. A. V. Churakov
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Correspondence to L. G. Kuz’mina.

Additional information

Dedicated to Academician of the Russian Academy of Sciences I. L. Eremenko on the occasion of his 70th birthday.

The X-ray diffraction study was performed using equipment of the Shared Facility Center of the N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences. The commercial powdered sample for investigation was supplied by N. S. Kucherepa.

This work was financially supported by the Russian Science Foundation (Project No. 16-13-10273).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1054–1060, June, 2020.

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Kuz’mina, L.G., Kalle, P. & Churakov, A.V. Mesomorphism and crystal packing of dichotomous compounds; X-ray crystal structure of N-(4-hexyloxybenzylidene)-p-toluidine. Russ Chem Bull 69, 1054–1060 (2020). https://doi.org/10.1007/s11172-020-2866-8

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  • DOI: https://doi.org/10.1007/s11172-020-2866-8

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