Issue 6, 2022

C–H⋯N[triple bond, length as m-dash]C hydrogen bonding in cyanobenzene-ethylenedithio-tetrathiafulvalene compounds

Abstract

The importance of C–H⋯N[triple bond, length as m-dash]C interactions in the crystal engineering of conducting materials was recently evidenced by a new type of two-dimensional conducting material with the composition of (5-CNB-EDT-TTF)4A with a variety of anions A, where CNB-EDT-TTF denotes the electron donor cyanobenzene-ethylenedithio-tetrathiafulvalene, which has been described in the last few years, presenting a new type of bilayer structure. The unique bilayer donor structure of these compounds is due to the network of C–H⋯N[triple bond, length as m-dash]C interactions, which although generally considered weak, are effective in the self-assembly of the crystal structure. The role of these weak interactions is made clear by a comparison of the salts of this donor and the related isomer 4-CNB-EDT-TTF, where no bilayer structure is obtained but a variety of related interactions are observed instead. This comparison allows different patterns of weak C–H⋯N[triple bond, length as m-dash]C interactions to be identified in these compounds, which can be described as combinations of several different synthons of type R22(10), R22(24), R22(26), R23(10), R24(8), R24(10), R48(20), and R34(30) or C(5) and C(6) infinite chains. The different patterns of interactions are comparable with those observed in other cyano compounds, as well as the magnitude of the interaction enthalpy associated with the different synthons, as estimated by means of density functional theory (DFT) calculations.

Graphical abstract: C–H⋯N [[triple bond, length as m-dash]] C hydrogen bonding in cyanobenzene-ethylenedithio-tetrathiafulvalene compounds

Article information

Article type
Highlight
Submitted
20 Xim 2021
Accepted
06 Qun 2022
First published
07 Qun 2022

CrystEngComm, 2022,24, 1145-1155

C–H⋯N[triple bond, length as m-dash]C hydrogen bonding in cyanobenzene-ethylenedithio-tetrathiafulvalene compounds

S. Rabaça, I. C. Santos, G. Lopes, V. da Gama, L. F. Veiros and M. Almeida, CrystEngComm, 2022, 24, 1145 DOI: 10.1039/D1CE01551F

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