TY - JOUR
T1 - 2,3,8,12,13-Pentamethoxy-5H-dibenzo[c,n]acridin-7(6H)-one toluene solvate
AU - Lutz, Marlon R
AU - Zeller, Matthias
AU - Becker, Daniel P
PY - 2007/9/1
Y1 - 2007/9/1
N2 - 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.
AB - 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.
KW - Beckmann rearrangement
KW - electrophilic aromatic addition
KW - subsequent demethylation
UR - https://ecommons.luc.edu/chemistry_facpubs/113
U2 - 10.1107/S1600536807040548
DO - 10.1107/S1600536807040548
M3 - Article
VL - E63
JO - Chemistry: Faculty Publications and Other Works
JF - Chemistry: Faculty Publications and Other Works
ER -