TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 31 , mp : 294 - 296 ℃, HPLC purity : 95 . 2 %; 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 14 . 18 ( s , 1 H , 2 - phenyl 2 - OH ) , 9 . 92 ( s , 1 H , indenopyridine 6 - OH ) , 8 . 21 ( d , J = 7 . 72 Hz , 1 H , 2 - phenyl H - 5 ) , 8 . 13 ( s , 1 H , indenopyridine H - 3 ) , 7 . 90 ( d , J = 7 . 65 Hz , 2 H , 4 - phenyl H - 2 , H - 5 ) , 7 . 63 - 7 . 51 ( m , 3 H , indenopyridine H - 9 , 4 - phenyl H - 3 , H - 5 ) , 7 . 43 ( t , J = 7 . 15 Hz , 1 H , 4 - phenyl H - 4 ) , 7 . 37 - 7 . 29 ( m , 2 H , 2 - phenyl H - 4 , indenopyridine H - 8 ) , 6 . 98 ( d , J = 7 . 5 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 6 . 92 ( d , J = 7 . 1 Hz , 1 H , indenopyridine H - 7 ) , 4 . 01 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 159 . 12 , 157 . 64 , 156 . 40 , 154 . 37 , 147 . 69 , 140 . 54 , 137 . 75 , 133 . 18 , 131 . 35 , 130 . 40 , 129 . 32 ( 2 C ) , 129 . 15 ( 2 C ) , 128 . 83 ( 2 C ) , 127 . 83 , 119 . 67 , 119 . 23 , 118 . 05 , 117 . 15 , 116 . 34 , 111 . 45 , 32 . 06 .