sp-9-(o-Methylphenyl)fluorene.
While the barriers of rotation of the sp and ap rotamers of 9-(o-methylphenyl)fluorene, C(20)H(16), are sufficiently similar to permit them to equilibrate, both being observed (NMR) in solution, crystallization provides the sp rotamer, (I), exclusively. Although in the sp conformation the intramolecular distance between adjacent C atoms of the phenyl and fluorene rings is small [3.382 (4) A, within 0.02 A of the sum of the van der Waals radii], in the ap conformation the distance between the adjacent o-CH(3) group on the phenyl ring and C atom of the fluorene ring would be much closer, based on that exhibited in the crystalline ap progenitor 9-(o-methylphenyl)-9-fluorenol. The angle between the fluorene and 9-aryl planes of (I) is 75.82 (10) degrees.
Meyers
Cal Y
CY
Meyers Institute for Interdisciplinary Research in Organic and Medicinal Chemistry, and the Department of Chemistry and Biochemistry, Southern Illinois University-4409, Carbondale, IL 62901, USA.
Robinson
Paul D
PD
McLean
Aaron W
AW