TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 21 , mp : 218 - 220 ℃, HPLC purity : 95 . 5 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 15 ( 100 %), [ MH + 2 ] : 388 . 14 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 72 ( s , 2 H , indenopyridine 7 - OH , 4 - phenyl 2 - OH ) , 8 . 26 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 15 ( d , J = 7 . 05 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 90 ( d , J = 8 . 25 Hz , 1 H , indenopyridine H - 9 ) , 7 . 70 ( s , 1 H , indenopyridine H - 3 ) , 7 . 55 - 7 . 45 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 39 ( d , J = 7 . 52 Hz , 1 H , 4 - phennyl H - 6 ) , 7 . 29 ( t , J = 7 . 45 Hz , 1 H , 4 - phenyl H - 3 ) , 7 . 03 - 6 . 87 ( m , 4 H , 4 - pheynl H - 3 , H - 5 , indenopyridine H - 6 , H - 8 ) , 3 . 81 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 21 , 159 . 01 , 154 . 42 , 153 . 07 , 146 . 64 , 144 . 18 , 141 . 62 , 134 . 64 , 133 . 83 , 131 . 87 , 130 . 71 ( 2 C ) , 129 . 93 , 128 . 51 , 126 . 42 , 125 . 33 ( 2 C ) , 121 . 84 , 119 . 48 , 118 . 32 , 116 . 22 , 114 . 94 , 112 . 27 , 34 . 11 .