TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 20 , mp : 321 - 323 ℃, HPLC purity : 96 . 6 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 62 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 69 ( br , 2 H , indenopyridine 7 - OH , 2 - phenyl 4 - OH ) , 8 . 08 ( d , J = 8 . 67 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 88 ( d , J = 8 . 35 Hz , 2 H , 4 - phenyl H - 3 , H - 6 ) , 7 . 84 ( s , 1 H , indenopyridine H - 3 ) , 7 . 62 ( d , J = 8 . 15 Hz , 1 H , indenopyridine H - 9 ) , 7 . 58 ( d , J = 8 . 5 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 7 . 02 ( d , J = 1 . 6 Hz , 1 H , indenopyridine H - 6 ) , 6 . 87 ( d , J = 8 . 62 Hz , 3 H , 2 - phenyl H - 3 , H - 5 , , indenopyridine H - 8 ) , 3 . 97 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 76 , 158 . 90 , 158 . 48 , 155 . 90 , 146 . 64 , 144 . 08 , 137 . 34 , 133 . 54 , 131 . 97 , 130 . 87 , 130 . 35 ( 2 C ) , 130 . 18 , 128 . 94 ( 2 C ) , 128 . 26 ( 2 C ) , 121 . 73 , 115 . 56 ( 2 C ) , 114 . 97 , 114 . 88 , 112 . 15 , 33 . 89 .