TLC ( ethyl acetate / n - hexane = 1 : 3 ) Rf = 0 . 17 , mp : 248 - 250 ℃, HPLC purity : 99 . 3 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 31 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 71 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 52 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 09 ( d , J = 8 . 67 Hz , 2 H , 2 - phenyl H - 2 , H - 60 , 7 . 82 ( d , J = 8 . 15 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 73 ( s , 1 H , indenopyridine H - 3 ) , 7 . 58 - 7 . 45 ( m , 4 H , indenopyridine H - 9 , 4 - phenyl H - 3 , H - 4 , H - 5 ) , 7 . 41 ( d , J = 8 . 2 Hz , 1 H , indenopyridine H - 6 ) , 6 . 91 ( d , J = 8 . 56 Hz , 2 H , 2 - phenyl H - 3 , H - 50 , 6 . 85 ( dd , J = 7 . 42 , 2 . 34 Hz , 1 H , indenopyridine H - 7 ) , 3 . 94 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 39 , 158 . 58 , 157 . 11 , 156 . 09 , 145 . 87 , 142 . 05 , 138 . 41 , 134 . 92 , 132 . 93 , 130 . 17 , 129 . 01 ( 2 C ) , 128 . 80 , 128 . 54 ( 2 C ) , 128 . 36 ( 2 C ) , 126 . 17 , 116 . 72 , 116 . 48 , 115 . 66 ( 2 C ) , 106 . 79 , 33 . 39 .