TLC ( ethyl acetate / n - hexane = 1 : 4 ) Rf = 0 . 2 , mp : 270 - 272 ℃. HPLC purity : 97 . 0 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 20 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 85 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 60 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 07 ( d , J = 8 . 57 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 96 ( s , 1 H , 4 - phenyl H - 2 ) , 7 . 87 - 7 . 84 ( m , 1 H , 4 - phenyl H - 6 ) , 7 . 81 ( s , 1 H , indenopyridine H - 3 ) , 7 . 62 - 7 . 57 ( m , 2 H , 4 - phenyl H - 4 , H - 5 ) , 7 . 33 ( t , J = 7 . 62 Hz , 1 H , indenopyridine H - 7 ) , 7 . 15 ( d , J = 7 . 38 Hz , 1 H , indenopyridine H - 6 ) , 6 . 92 ( d , J = 8 . 6 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 6 . 89 ( d , J = 8 . 17 Hz , 1 H , indenopyridine H - 8 ) , 4 . 14 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 31 , 159 . 01 , 155 . 58 , 154 . 06 , 145 . 57 , 144 . 68 , 140 . 16 , 134 . 00 , 131 . 31 , 131 . 00 , 130 . 82 , 129 . 18 , 129 . 08 , 128 . 53 ( 2 C ) , 128 . 43 , 127 . 49 , 125 . 03 , 116 . 97 , 116 . 10 , 115 . 88 ( 2 C ) , 113 . 40 , 34 . 53 .