TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 22 , mp : 231 - 233 ℃, HPLC purity : 100 %; ESI LC / MS : m / z calcd for C 24 H 18 NO 2 [ MH ] + 352 . 13 ; found 352 . 27 . 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 82 ( s , 1 H , indenopyridine 7 - OH ) , 9 . 57 ( s , 1 H , 2 - phenyl 3 - OH ) , 7 . 87 ( d , J = 8 . 67 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 83 ( d , J = 8 . 07 Hz , 1 H , indenopyridine H - 9 ) , 7 . 66 - 7 . 49 ( m , 6 H , indenopyridine H - 3 , 4 - phenyl H - 2 , H - 3 , H - 4 , H - 5 , H - 6 ) , 7 . 29 ( t , J = 7 . 87 Hz , 1 H , 2 - phenyl H - 5 ) , 7 . 02 ( s , 1 H , indenopyridine H - 6 ) , 6 . 90 ( d , J = 8 . 2 Hz , 1 H , 2 - phenyl H - 4 ) , 6 . 83 ( d , J = 7 . 97 Hz , 1 H , indenopyridine H - 8 ) , 4 . 02 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 84 , 158 . 95 , 157 . 83 , 155 . 70 , 146 . 73 , 145 . 34 , 140 . 73 , 138 . 35 , 132 . 11 , 131 . 87 , 129 . 75 , 128 . 99 ( 2 C ) , 128 . 74 , 128 . 47 ( 2 C ) , 121 . 69 , 117 . 69 , 116 . 19 , 115 . 91 , 115 . 00 , 113 . 72 , 112 . 19 , 34 . 03 .