TLC ( ethyl acetate / n - hexane = 1 : 1 ) Rf = 0 . 38 , mp : 262 - 264 ℃, HPLC purity : 97 . 2 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 20 ( 100 %), [ MH + 2 ] : 388 . 10 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 77 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 72 ( s , 1 H , 4 - phenyl 3 - OH ) , 7 . 75 - 7 . 71 ( m , 1 H , 2 - phenyl H - 6 ) , 7 . 63 - 7 . 59 ( m , 1 H , 2 - phenyl H - 3 ) , 7 . 54 ( s , 1 H , indenopyridine H - 3 ) , 7 . 50 - 7 . 47 ( m , 3 H , indenopyridine H - 9 , 2 - phenyl H - 4 , H - 5 ) , 7 . 35 ( m , 2 H , indenopyridine H - 8 , 4 - phenyl H - 5 ) , 7 . 27 - 7 . 19 ( m , 2 H , 4 - phenyl H - 2 H - 6 ) , 6 . 90 ( d , J = 7 . 85 Hz , 2 H , 4 - penyl H - 4 , indenopyridine H - 7 ) , 3 . 97 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 82 , 157 . 93 , 155 . 73 , 154 . 17 , 145 . 30 , 142 . 08 , 139 . 35 , 139 . 10 , 133 . 02 , 132 . 05 , 131 . 54 , 130 . 26 , 130 . 15 , 130 . 09 , 129 . 99 , 128 . 91 , 127 . 56 , 121 . 49 , 119 . 23 , 116 . 01 , 115 . 77 , 115 . 26 , 112 . 00 , 32 . 08 .