TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 18 , mp : 245 - 247 ℃, HPLC purity : 100 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 26 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 74 ( s , 2 H , indenopyridine 6 - OH , 2 - phenyl 4 - OH ) , 8 . 11 ( d , J = 7 . 27 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 85 ( d , J = 6 . 88 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 76 ( s , 1 H , indenopyridine H - 3 ) , 7 . 60 - 7 . 50 ( m , 4 H , 4 - phenyl H - 3 , H - 4 , H - 5 , indenopyridine H - 9 ) , 7 . 31 ( t , J = 7 . 89 Hz , 1 H , indenopyridine H - 8 ) , 6 . 90 - 6 . 87 ( m , 3 H , 2 - phenyl H - 3 , H - 5 , indenopyridine H - 7 ) , 3 . 96 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 63 , 158 . 60 , 156 . 15 , 154 . 16 , 146 . 04 , 142 . 52 , 138 . 42 , 131 . 85 , 130 . 14 , 130 . 07 , 129 . 07 , 128 . 86 ( 2 C ) , 128 . 84 , 128 . 61 ( 2 C ) , 128 . 40 ( 2 C ) , 116 . 50 , 115 . 67 ( 2 C ) , 115 . 57 , 111 . 97 , 31 . 84 .