TLC ( ethyl acetate / n - hexane = 1 : 1 ) Rf = 0 . 41 , mp : 242 - 244 ℃, HPLC purity : 100 %; 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 9 . 54 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 53 ( s , 1 H , 2 - phenyl 3 - OH ) , 7 . 83 ( d , J = 7 . 5 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 76 ( s , 1 H , indenopyridine H - 3 ) , 7 . 67 ( s , 1 H , indenopyridine H - 9 ) , 7 . 65 - 7 . 41 ( m , 6 H , 4 - phenyl H - 2 , H - 3 , H - 4 , H - 4 , H - 5 , H - 6 , indenopyridine H - 6 ) , 7 . 30 ( t , J = 7 . 8 Hz , 1 H , 2 - phenyl H - 50 , 6 . 87 ( td , J = 8 . 02 , 2 . 27 Hz , 2 H , 2 - phenyl H - 4 , indenopyridine H - 7 ) , 3 . 98 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 55 , 157 . 91 , 157 . 13 , 155 . 96 , 145 . 90 , 141 . 85 , 140 . 61 , 138 . 20 , 134 . 95 , 134 . 08 , 129 . 87 , 129 . 03 ( 2 C ) , 128 . 88 , 128 . 55 ( 2 C ) , 126 . 22 , 117 . 78 , 117 . 56 , 116 . 90 , 116 . 08 , 113 . 78 , 106 . 75 , 33 . 43 .