TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 27 , mp : 218 - 220 ℃, HPLC purity : 95 . 0 %; 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 . 82 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 60 ( s , 1 H , 2 - phenyl 3 - OH ) , 7 . 93 ( d , J = 8 . 32 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 80 ( s , 1 H , indenopyridine H - 3 ) , 7 . 67 - 7 . 62 ( m , 3 H , 2 - phenyl H - 2 , H - 6 , indenopyridine H - 9 ) , 7 . 56 ( d , J = 7 . 43 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 7 . 36 - 7 . 27 ( m , 2 H , 2 - phenyl H - 5 , indenopyridine H - 8 ) , 6 . 89 ( d , J = 7 . 95 Hz , 1 H , 2 - phenyl H - 7 ) , 6 . 85 ( d , J = 8 . 1 Hz , 1 H , indenopyridine H - 7 ) , 3 . 95 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 97 , 158 . 00 , 156 . 16 , 154 . 29 , 144 . 89 , 142 . 30 , 140 . 55 , 137 . 09 , 133 . 91 , 133 . 09 , 130 . 66 ( 2 C ) , 130 . 19 , 130 . 01 , 129 . 17 ( 2 C ) , 129 . 04 , 117 . 96 , 117 . 59 , 116 . 25 , 115 . 78 , 113 . 89 , 112 . 01 , 31 . 84 .