TLC ( ethyl acetate / n - hexane = 1 : 5 ) Rf = 0 . 16 , mp : 261 - 263 ℃, HPLC purity : 96 . 5 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 19 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 83 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 62 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 04 ( d , J = 8 . 65 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 88 ( d , J = 6 . 8 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 78 ( s , 1 H , indenopyridine H - 3 ) , 7 . 60 - 7 . 47 ( m , 1 H , 3 H , 4 - phenyl H - 3 , H - 4 , H - 5 ) , 7 . 32 ( t , J = 7 . 73 Hz , 1 H , indenopyridine H - 7 ) , 7 . 14 ( d , J = 7 . 37 Hz , 1 H , indenopyridine H - 6 ) , 6 . 91 ( d , J = 8 . 65 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 6 . 89 ( d , J = 7 . 82 Hz , 1 H , indenopyridine H - 8 ) , 4 . 10 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 22 , 158 . 92 , 155 . 46 , 154 . 04 , 146 . 14 , 145 . 50 , 137 . 98 , 131 . 14 , 130 . 68 , 129 . 26 , 129 . 15 ( 2 C ) , 128 . 65 ( 2 C ) , 128 . 39 ( 2 C ) , 125 . 05 , 116 . 90 , 116 . 09 , 115 . 88 ( 2 C ) , 113 . 29 , 34 . 67 .