TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 21 , mp : 285 - 287 ℃, HPLC purity : 98 . 9 %; 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 . 82 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 55 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 27 ( d , J = 8 . 47 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 83 ( s , 1 H , indenopyridine H - 3 ) , 7 . 71 ( d , J = 8 . 47 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 56 ( d , J = 8 . 42 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 7 . 45 - 7 . 41 ( m , 2 H , indenopyridine H - 9 , H - 6 ) , 6 . 94 ( d , J = 8 . 35 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 88 ( d , J = 8 . 15 Hz , 1 H , indenopyridine H - 7 ) , 3 . 97 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 63 , 158 . 38 , 157 . 14 , 154 . 37 , 146 . 00 , 141 . 81 , 138 . 17 , 135 . 00 , 133 . 92 , 133 . 77 , 130 . 20 , 129 . 95 , 128 . 98 , 128 . 88 , 128 . 75 ( 2 C ) 128 . 54 , 117 . 24 , 116 . 94 , 115 . 90 ( 2 C ) , 115 . 79 , 106 . 94 , 33 . 80 .