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Royal Society of Chemistry, New Journal of Chemistry, 3(36), p. 749

DOI: 10.1039/c2nj20820b

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The chiral structure of 1H-indazoles in the solid state: A crystallographic, vibrational circular dichroism and computational study

This paper is available in a repository.
This paper is available in a repository.

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Abstract

A survey of the Cambridge Crystallographic Database reveals that there are 17 1H-indazoles forming dimers (7), trimers (4) and catemers or chains (6). Amongst the catemers there is one centrosymmetric compound and five non-centrosymmetric ones that crystallize in chiral helices, either M or P, including indazole itself, whose structure has been determined anew. An explanation will be provided for how an achiral molecule crystallizes in a chiral space group. The second part of the paper is devoted to the use of Vibrational Circular Dichroism (VCD) for determining the absolute configuration of a crystal of indazole. This previously needs the complete assignment of its IR and Raman spectra in solution and in the solid-state based on B3LYP/6-31G(d) calculations of indazole dimers and trimers, which are already chiral.