9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine

Abstract

The title compound, C26H19ClN2, is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetra­hydro-1H-carbazol-1-one with 2-amino­benzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the mol­ecule is inter­rupted by the saturated ethyl­ene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C—H⋯π inter­actions. No classical hydrogen bonds or stacking inter­actions are observed.

(2RS,5′RS)-3′,4′-Bis(4-chlorophenyl)-3,4-dihydrospiro[acridine-2,5′(4′H)-[1,2]oxazol]-1(2H)-one

“…The chlorine atoms (Cl1 & Cl2) are significantly deviate from the phenyl ring (C16-C21) and (C22-C27) by -0.0113 (19) Å and 0.0666 (8) Å, respectively. The title compound exhibits structural similarities with already reported related structures (Sridharan et al, 2009;Trzybiński et al, 2010).…”

“…For the uses and biological importance of acridines, see: Asthana et al (1991); Di Giorgio et al (2005); Talacki et al (1974). For related structures, see: Sridharan et al (2009); Trzybiń ski et al (2010). For graph-set notation, see: Bernstein et al(1995) Experimental Hydrogen-bond geometry (Å , ).…”

4′-(4-Chlorophenyl)-3′-(4-methoxyphenyl)-3,4-dihydro-1H,4′H-spiro[acridine-2,5′-isoxazol]-1-one

“…The isoxazole ring forms a dihedral angle of 85.75 (7) ° and 81.46 (9) ° with the quinoline bicyclic ring system and the cyclohexane ring, respectively. The title compound exibits structural similarities with already reported related structures (Sridharan et al, 2009;Trzybiński et al, 2010).…”

“…For the uses and biological importance of acridines, see: Asthana et al (1991); Di Giorgio et al (2005); Talacki et al (1974). For related structures, see: Sridharan et al (2009); Trzybiń ski et al (2010). For graph-set notation, see: Bernstein et al (1995).…”