TLC ( ethyl acetate / n - hexane = 1 : 4 ) Rf = 0 . 27 , mp : 260 - 262 ℃, HPLC purity : 96 . 6 %; 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 . 64 ( br , 2 H , indenopyridine 9 - OH , 2 - phenyl 3 - OH ) , 7 . 94 ( d , J = 8 . 5 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 83 ( s , 1 H , indenopyridine H - 3 ) , 7 . 64 - 7 . 61 ( m , 4 H , 2 - phenyl H - 2 , H - 6 , 4 - phenyl H - 3 , H - 5 ) , 7 . 38 - 7 . 30 ( m , 2 H , 4 - phenyl H - 5 , indenopyridine H - 7 ) , 7 . 16 ( d , J = 7 . 43 Hz , 1 H , indenopyridine H - 6 ) , 6 . 92 ( d , J = 8 . 17 Hz , 1 H , 2 - phenyl H - 4 ) , 6 . 88 ( d , J = 8 . 87 , 2 . 3 Hz , 1 H , indenopyridine H - 8 ) , 4 . 16 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 45 , 158 . 09 , 155 . 35 , 154 . 11 , 145 . 59 , 144 . 87 , 139 . 68 , 136 . 64 , 134 . 13 , 132 . 39 , 130 . 95 ( 2 C ) , 130 . 63 ( 2 C ) , 130 . 18 , 129 . 17 ( 2 C ) , 124 . 90 , 117 . 83 , 117 . 02 , 116 . 52 , 113 . 64 , 113 . 47 , 34 . 65 .