TLC ( ethyl acetate / n - hexane = 1 : 3 ) Rf = 0 . 24 , mp : 290 - 292 ℃, HPLC purity : 98 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 29 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 14 . 33 ( s , 1 H , 2 - phenyl 2 - OH ) , 9 . 95 ( s , 1 H , indenopyridine 7 - OH ) , 8 . 16 ( d , J = 7 . 87 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 99 ( s , 1 H , indenopyridine H - 3 ) , 7 . 86 ( d , J = 7 . 3 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 77 ( d , J = 8 . 27 Hz , 1 H , indenopyridine H - 9 ) , 7 . 60 - 7 . 52 ( m , 3 H , 4 - phenyl H - 3 , H - 4 , H - 5 ) , 7 . 30 ( t , J = 7 . 45 Hz , 1 H , 2 - phenyl H - 4 ) , 7 . 06 ( s , 1 H , indenopyridine H - 6 ) , 6 . 95 ( d , J = 7 . 82 Hz , 2 H , 2 - phenyl H - 3 , H - 50 , 6 . 90 ( d , J = 8 . 7 Hz , 1 H , indenopyridine H - 8 ) , 4 . 07 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 159 . 64 , 159 . 22 , 157 . 74 , 156 . 06 , 147 . 27 , 147 . 02 , 137 . 92 , 132 . 37 , 131 . 22 , 130 . 12 , 129 . 23 , 129 . 12 ( 2 C ) , 128 . 76 ( 2 C ) , 127 . 64 , 121 . 58 , 119 . 67 , 119 . 16 , 118 . 07 , 115 . 58 , 115 . 45 , 112 . 51 , 34 . 41 .