TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 18 , mp : 248 - 250 ℃, 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 . 20 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 71 ( s , 2 H , indenopyridine 7 - OH , 2 - phenyl 4 - OH ) , 8 . 10 ( d , J = 8 . 35 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 87 - 7 . 84 ( m , 2 H , 4 - phenyl H - 2 , indenopyridine H - 9 ) , 7 . 79 - 7 . 77 ( m , 1 H , 4 - phenyl H - 6 ) , 7 . 65 ( s , 1 H , indenopyridine H - 30 , 7 . 60 - 7 . 54 ( m , 2 H , 4 - phenyl H - 4 , H - 5 ) , 7 . 02 ( s , 1 H , indenopyridine H - 6 ) , 6 . 89 - 6 . 86 ( m , 3 H , 2 - phenyl H - 3 , H - 5 , indenopyridine H - 8 ) , 3 . 98 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 89 , 159 . 04 , 158 . 63 , 155 . 99 , 146 . 88 , 144 . 05 , 140 . 80 , 133 . 94 , 132 . 04 , 131 . 19 , 130 . 97 , 130 . 22 , 128 . 77 , 128 . 49 ( 2 C ) , 128 . 36 , 127 . 46 , 121 . 92 , 115 . 68 ( 2 C ) , 115 . 18 , 115 . 09 , 112 . 34 , 33 . 96 .