Document Type

Article

Publication Date

9-2007

Publication Title

Acta Crystallographica Section E: Crystalographic Communications

Volume

E63

Pages

o3857-o3858

Publisher Name

International Union of Crystallography

Abstract

The title compound, C26H25NO6·C7H8, formed by an unexpected tandem reaction of Beckmann rearrangement, electrophilic aromatic addition and subsequent demethyl­ation, was crystallized as its toluene solvate. The crystal under investigation was found to be nonmerohedrally twinned by a rotation around the reciprocal axis [100]; the twin ratio refined to 0.688 (2):0.312 (2). The mol­ecule exhibits an unusual helical arrangement of three six-membered rings that are all connected at one central C atom. The helix effectively performs one full turn around this atom, and the thread pitch, as defined by the distance of the terminal C atoms of the helix, is 4.98 (3) Å. The angles around the central atom are between 104.7 (2) and 115.2 (2)°. The middle ring, a cyclo­hexa-2,4-dienimine ring containing only one saturated C atom, is essentially planar, with an r.m.s. deviation from the mean plane of only 0.035 Å. The other two rings have conformations best described as between envelope and screw-boat, with puckering amplitudes of 0.527 (2) and 0.544 (2) Å, respectively. The packing appears to be dominated by a combination of simple dispersion forces, weak C-HO hydrogen bonds and C-H inter­actions.

Identifier

ISSN: 2056-9890

Comments

Author Posting © International Union of Crystallography, 2007. This is the author's version of the work. It is posted here by permission of International Union of Crystallography for personal use, not for redistribution. The definitive version was published in Acta Crystallographica Section E: Crystalographic Communications, Volume E63, September 2007. https://doi.org/10.1107/S1600536807040548

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