TLC ( ethyl acetate / n - hexane = 1 : 3 ) Rf = 0 . 3 , mp : 247 - 249 ℃, HPLC purity : 96 . 6 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 14 ( 100 %), [ MH + 2 ] : 388 . 19 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 90 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 53 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 27 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 18 - 8 . 16 ( m , 1 H , 2 - phenyl H - 2 ) , 7 . 91 ( s , 1 H , indenopyridine H - 3 ) , 7 . 89 ( d , J = 8 . 45 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 59 - 7 . 53 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 33 ( t , J = 7 . 82 Hz , 1 H , indenopyridine H - 7 ) , 7 . 15 ( d , J = 7 . 17 Hz , 1 H , indenopyridine H - 6 ) , 6 . 94 ( d , J = 8 . 4 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 89 ( d , J = 8 . 35 Hz , 1 H , indenopyridine H - 8 ) , 4 . 16 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 46 , 158 . 68 , 154 . 04 , 153 . 47 , 146 . 13 , 145 . 71 , 140 . 84 , 134 . 02 , 132 . 36 , 130 . 95 , 130 . 79 , 130 . 33 ( 2 C ) , 129 . 06 , 128 . 11 , 126 . 69 , 125 . 64 , 125 . 02 , 116 . 98 , 116 . 86 , 115 . 92 ( 2 C ) , 113 . 54 , 35 . 08 .