Conformational Studies of Substituted Chromans: Crystal Structures of 2,2′-(1E,1′E)-(2,3-Dimethylchroman-2,4-diyl)bis(Azan-1-yl-1-ylidene)bis(Methan-1-yl-1-ylidene)Diphenol (I) and 2,2′-(1E,1′E)-(2-Ethyl-3-Methylchroman-2,4-diyl)bis(Azan-1-yl-1-ylidene)bis(Methan-1-yl-1-ylidene)Diphenol (II)
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The title compounds C25H24N2O3 (I) and C26H26N2O3 (II) crystallize in the triclinic space group P-1 with cell parameters a = 8.981(1), b = 9.933(1), c = 12.369(2) Å, α = 78.537(2), β = 84.515(2), γ = 73.561(2)° Z = 2 (I) and a = 11.4630(9), b = 12.955(1), c = 16.154(1) Å, α = 70.425(1), β = 87.403(1), γ = 71.850(1)°, Z = 4 (II). In both compounds the phenolic groups in the Schiff base substituents form intramolecular hydrogen bonds with the imine nitrogen atoms thereby rendering these substituents nearly planar. A detailed analysis of the amount by which the heterocyclic ring deviates from planarity (extent of puckering) in these and a series of related molecules shows that the extent of the deviation is largely unaffected by the number, size and placement of substituents on this ring.The structures of the title compounds together with an analysis of published structures of related chromans indicate that the amount by which the heterocyclic ring deviates from planarity (extent of puckering) is largely independent of the number and placement of its substituents.