Conformation of N‐methyl‐4‐piperidyl 2,4‐dinitrobenzoate |
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Authors: | Laura Andrau Jonathan White |
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Abstract: | The crystal structure of N‐methyl‐4‐piperidyl 2,4‐dinitrobenzoate, C13H15N3O6, (I), at 130 (2) K reveals that, in the solid state, the molecule exists in the equatorial conformation, (Ieq). Thus, the through‐bond interaction present in the axial conformation, (Iax), is not strong enough to overcome the syn–diaxial interactions between the axial methyl substituent and the axial H atoms on the two piperidyl ring C atoms either side of the ester‐linked ring C atom. The carboxylate group in (I) is orthogonal to the aromatic ring, in contrast with other 2,4‐dinitrobenzoates, which are coplanar. The piperidyl–ester C—O bond distance is 1.467 (3) Å, which is actually shorter than other equatorial cyclohexyl–ester C—O distances. This shorter piperidyl–ester C—O bond distance is due to the reduced electron demand of the orthogonal ester group. |
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