TLC ( ethyl acetate / n - hexane = 1 : 5 ) Rf = 0 . 23 , mp : 199 - 201 ℃, HPLC purity : 97 . 7 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 12 ( 100 %), [ MH + 2 ] : 388 . 14 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 96 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 45 ( s , 1 H , 4 - phenyl 2 - OH ) , 8 . 19 ( d , J = 8 . 55 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 79 ( s , 1 H , indenopyridine H - 3 ) , 7 . 57 ( d , J = 8 . 52 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 7 . 44 ( dd , J = 7 . 52 , 1 . 4 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 31 ( t , J = 7 . 55 Hz , 2 H , 4 - phenyl H - 4 , indenopyridine H - 7 ) , 7 . 12 ( d , J = 7 . 37 Hz , 1 H , indenopyridine H - 6 ) , 7 . 01 ( t , J = 8 . 02 Hz , 1 H , 4 - phenyl H - 3 ) , 6 . 96 ( t , J = 7 . 42 Hz , 1 H , 4 - phenyl H - 5 ) , 6 . 92 ( d , J = 8 . 02 Hz , 1 H , indenopyridine H - 8 ) , 3 . 93 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 64 , 154 . 56 , 154 . 01 , 153 . 22 , 145 . 56 , 144 . 87 , 137 . 49 , 134 . 45 , 134 . 05 , 130 . 83 , 130 . 37 ( 2 C ) , 129 . 13 ( 2 C ) , 128 . 71 ( 2 C ) , 125 . 18 , 124 . 94 , 119 . 65 , 119 . 08 , 116 . 98 , 116 . 33 , 113 . 56 , 34 . 75 .