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A series of three bis­[2‐(methyl/tri­fluoro­methyl)‐4H‐3,1‐benzoxazin‐4‐one] compounds
Authors:I. I. Ponomarev  A. Yu. Kovalevsky
Abstract:Each of the three title compounds, namely 6,6′‐methyl­ene­bis­(2‐methyl‐4H‐3,1‐benz­oxazin‐4‐one), C19H14N2O4, 6,6′‐methyl­ene­bis­(2‐tri­fluoro­methyl‐4H‐3,1‐benz­oxazin‐4‐one), C19H8F3N2O4, and 6,6′‐bi­(2‐tri­fluoro­methyl‐4H‐3,1‐benz­oxazin‐4‐one), C18H6F6N2O4, contains two planar benz­ox­azin­one fragments. In the first two compounds, these planes are virtually perpendicular to each other, while the third compound is planar overall. The electronic effects of the substituent groups on the oxazine moiety result in distortion of the bond angles at the C atoms of the C=O and C=N bonds, and in redistribution of electronic density in the oxazine rings. The latter leads to different bond lengths within this ring in the three mol­ecules. All the mol­ecules form stacks in their crystals with distances of 3.2–3.6 Å between adjacent mol­ecules in a stack.
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