TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 18 , mp : 251 - 253 ℃, HPLC purity : 95 . 9 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 62 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 55 ( s , 2 H , indenopyridine 8 - OH , 2 - phenyl 3 - OH ) , 7 . 88 ( d , J = 8 . 4 Hz , 2 H , 4 - phenyl H - 2 m H - 6 ) , 7 . 77 ( s , 1 H , indenopyridine H - 3 ) , 7 . 68 - 7 . 65 ( m , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 61 ( d , J = 8 . 35 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 7 . 46 - 7 . 42 ( m , 2 H , indenopyridine H - 6 , H - 9 ) , 7 . 30 ( t , J = 7 . 85 Hz , 1 H , 2 - phenyl H - 5 ) , 6 . 87 ( td , J = 8 . 15 , 2 . 22 Hz , 2 H , 2 - phenyl H - 4 , indenopyridine H - 7 ) , 3 . 97 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 64 , 157 . 92 , 157 . 16 , 156 . 03 , 144 . 63 , 141 . 75 , 140 . 51 , 137 . 01 , 134 . 92 , 134 . 04 , 133 . 77 , 130 . 48 ( 2 C ) , 129 . 87 , 129 . 01 ( 2 C ) , 126 . 22 , 117 . 81 , 117 . 42 , 117 . 00 , 116 . 14 , 113 . 81 , 106 . 77 , 33 . 34 .