TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 19 , mp : 230 - 232 ℃, HPLC purity : 100 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 24 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 81 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 74 ( s , 1 H , 4 - phenyl 3 - OH ) , 8 . 25 ( d , J = 7 . 1 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 84 ( s , 1 H , indenopyridine H - 3 ) , 7 . 59 - 7 . 44 ( m , 4 H , indenopyridine H - 9 , 2 - phenyl H - 3 , H - 4 , H - 5 ) , 7 . 40 - 7 . 32 ( m , 3 H , indenopyridine H - 8 , 4 - phenyl H - 5 , H - 6 ) , 7 . 22 ( s , 1 H , 4 - phenyl H - 2 ) , 6 . 91 - 6 . 88 ( m , 2 H , 4 - phenyl H - 4 , indenopyridine H - 7 ) , 3 . 93 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 95 , 157 . 96 , 155 . 96 , 154 . 27 , 146 . 35 , 142 . 39 , 139 . 54 , 139 . 23 , 133 . 01 , 130 . 28 , 130 . 15 , 129 . 17 , 129 . 01 ( 3 C ) , 127 . 08 ( 2 C ) , 119 . 44 , 117 . 53 , 115 . 98 , 115 . 76 , 115 . 44 , 112 . 08 , 31 . 90 .