N-Methyl-1,2-diphenylcyclobuteno[3,4-a]naphthalene-2,3-dicarboximide

✍ Scribed by Liu, Qingjian

• Publisher: International Union of Crystallography
• Year: 2007
• Tongue: English
• Weight: 803 KB
• Volume: 63
• Category: Article
• ISSN: 1600-5368
• DOI: 10.1107/s1600536807022568

✦ Synopsis

The title compound, C 27 H 19 NO 2 , is the product of a photochemical reaction between N-methylnaphthalene-2,3dicarboximide and diphenylacetylene. The cyclobutene ring in the molecule is almost perpendicular to the plane of the dihydronaphthalimide system; the interplanar angle between the cyclobutene ring and the plane through the two sixmembered rings of the naphthalimide system is 70.66 (9) . The interplanar angle between the two phenyl substituents on the cyclobutene ring is 42.47 (8) .

Related literature

For information on the photochemistry of naphthalenedicarboximides with alkynes see Liu et al. (2006) and for related structures see Liu et al. (2003Liu et al. ( , 2006)).

Experimental

Crystal data

C 27 H 19 NO 2 M r = 389.43 Monoclinic, P2 1 =c a = 10.763 (2) A b = 7.9925 (15) A c = 23.438 (5) A = 97.326 (3) V = 1999.8 (7) A ˚3 Z = 4 Mo K radiation = 0.08 mm À1 T = 298 (2) K 0.28 Â 0.22 Â 0.08 mm Data collection Bruker SMART APEX CCD areadetector diffractometer Absorption correction: none 10516 measured reflections 3715 independent reflections 2456 reflections with I > 2(I) R int = 0.062 Refinement R[F 2 > 2(F 2 )] = 0.058 wR(F 2 ) = 0.123 S = 1.01 3715 reflections