TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 16 , mp : 251 - 253 ℃, HPLC purity : 97 . 6 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 15 ( 100 %), [ MH + 2 ] : 388 . 19 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 80 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 72 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 29 ( d , J = 8 . 55 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 85 ( s , 1 H , indenopyridine H - 3 ) , 7 . 74 ( d , J = 8 . 55 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 56 ( d , J = 8 . 37 Hz , 3 H , indenopyridine H - 9 , 2 - phenyl H - 3 , H - 5 ) , 7 . 31 ( t , J = 7 . 75 Hz , 1 H , indenopyridine H - 8 ) , 6 . 96 ( d , J = 8 . 74 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 89 ( d , J = 7 . 87 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 . 93 , 158 . 45 , 154 . 49 , 154 . 21 , 146 . 21 , 142 . 31 , 138 . 16 , 133 . 84 , 132 . 88 , 130 . 19 ( 3 C ) , 128 . 92 ( 2 C ) , 128 . 78 ( 2 C ) , 128 . 58 ( 2 C ) , 117 . 18 ( 2 C ) , 115 . 91 ( 2 C ) , 115 . 70 , 112 . 15 , 32 . 00 .