3,10,14,21-Tetrakis(4-methoxyphenyl)pentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,13,15(20),16,18-decaen-12-one chloroform monosolvate

The asymmetric unit of the title compound, C49H36O6·CHCl3, contains half an organic molecule, the complete molecule being generated by the operation of a crystallographic twofold rotation axis, and half a highly disordered chloroform molecule. The contribution to the diffraction pattern of the latter was removed using the program SQUEEZE in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148–155]; the unit-cell characteristics take into account the presence of CHCl3. The dihedral angles between the planes of the naphthalene ring system and the methoxybenzene rings are 71.05 (7) (syn to the central C=O group) and 57.27 (6)° (anti to the central C=O group). In the crystal, molecules are linked by C—H⋯O interactions, generating C(12) chains running parallel to the b axis.

The asymmetric unit of the title compound, C 49 H 36 O 6 ÁCHCl 3 , contains half an organic molecule, the complete molecule being generated by the operation of a crystallographic twofold rotation axis, and half a highly disordered chloroform molecule. The contribution to the diffraction pattern of the latter was removed using the program SQUEEZE in PLATON [Spek (2009). Acta Cryst. D65,[148][149][150][151][152][153][154][155]; the unitcell characteristics take into account the presence of CHCl 3 . The dihedral angles between the planes of the naphthalene ring system and the methoxybenzene rings are 71.05 (7) (syn to the central C O group) and 57.27 (6) (anti to the central C O group). In the crystal, molecules are linked by C-HÁ Á ÁO interactions, generating C(12) chains running parallel to the b axis.
In the crystal packing, molecules are linked via bifurcated C24-H24c···O3 ii intermolecular hydrogen bonding, which generates C(12) infinite chains running parallel to the b axis. A view of the supramolecular chain is shown in Fig. 2.

S5. Synthesis and crystallization
To a solution of benzo[c]furan (0.20 g, 0.60 mmol) in dry dichloromethane (15 ml), indenone (0.24 g, 0.60 mmol) was added and refluxed till the disappearence of colour due to the benzo[c]furan (10 h). To this, PTSA (0.46 g, 2.42 mmol) was added (9 h). The reaction mixture was poured into saturated solution of NaHCO 3 (40 ml), extracted with CHCl 3 (3 x 15ml) and dried (Na 2 SO 4 ). Removal of solvent followed by coloumn chromatographic purification (silica gel; 10% ethyl acetate in hexane) afforded the fluorenone derivative as a yellow solid. Single crystals suitable for X-ray diffraction were prepared by slow evapouration of a solution of the title compound in chloroform at room temperature.

S6. Refinement
The hydrogen atoms bound to the C atoms are treated as riding atoms, with d(C-H) = 0.93-0.96 Å, and with U iso (H) = 1.2-1.5U eq (C). The void in the crystal contains a highly disordered molecule of chloroform which has beeen removed from the intensity data using the SQUEEZE routine in PLATON [Spek (2009)

Figure 1
The molecular structure of the title compound (chloroform molecule omitted) showing the atom numbering scheme and displacement ellipsoids drawn at 30% probability level. The symmetry code of the unlabelled atoms is -x + 3/2, y, -z + 1/2.