TLC ( ethyl acetate / n - hexane = 1 : 1 ) Rf = 0 . 41 , mp : 242 - 244 ℃, HPLC purity : 98 . 7 %; 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 . 81 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 53 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 22 ( d , J = 7 . 48 Hz , 2 H , 2 - phenyl H - 2 , H - 4 ) , 7 . 80 ( s , 1 H , indenopyridine H - 3 ) , 7 . 71 ( d , J = 8 . 5 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 53 ( d , J = 8 . 08 Hz , 1 H , indenopyridine H - 9 ) , 7 . 51 - 7 . 42 ( m , 4 H , indenopyridine H - 6 , 2 - phenyl H - 3 , H - 4 , H - 5 ) , 6 . 93 ( d , J = 8 . 53 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 87 ( dd , J = 8 . 12 , 2 . 45 Hz , 1 H , indenopyridine H - 7 ) , 3 . 99 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 61 , 158 . 37 , 157 . 15 , 155 . 78 , 145 . 96 , 142 . 00 , 139 . 42 , 135 . 01 , 133 . 66 , 130 . 09 ( 2 C ) , 128 . 94 ( 2 C ) , 128 . 70 , 127 . 02 ( 2 C ) , 126 . 25 , 117 . 18 , 116 . 83 , 115 . 88 ( 3 C ) , 106 . 82 , 33 . 81 .