TLC ( ethyl acetate / n - hexane = 1 : 1 ) Rf = 0 . 43 , mp : 286 - 288 ℃, HPLC purity : 98 . 43 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + found 386 . 10 ( 100 %), [ MH + 2 ] : 388 . 20 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 73 ( s , 2 H , indenopyridine 7 - OH , 4 - phenyl 3 - OH ) , 8 . 26 ( d , J = 8 . 5 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 88 ( d , J = 8 . 27 Hz , 1 H , indenopyridine H - 9 ) , 7 . 73 ( s , 1 H , indenopyridine H - 3 ) , 7 . 55 ( d , J = 8 . 5 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 7 . 34 ( t , J = 7 . 75 Hz , 1 H , 4 - phenyl H - 5 ) , 7 . 23 ( d , J = 7 . 77 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 16 9 s , 1 H , 4 - phenyl H - 2 ) , 7 . 03 ( s , 1 H , indenopyridine H - 6 ) , 6 . 89 ( d , J = 8 . 15 Hz , 2 H , 4 - phenyl H - 4 , indenopyridine H - 8 ) , 3 . 98 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 89 , 158 . 95 , 157 . 71 , 154 . 13 , 146 . 62 , 145 . 62 , 139 . 34 , 137 . 98 , 133 . 58 , 132 . 29 , 131 . 60 , 129 . 97 , 128 . 69 ( 2 C ) , 128 . 49 ( 2 C ) , 121 . 75 , 119 . 11 , 115 . 94 , 115 . 71 , 115 . 16 , 114 . 96 , 112 . 10 , 34 . 06 .