TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 25 , mp : 208 - 210 ℃, HPLC purity : 96 . 2 %; 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 . 78 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 60 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 12 ( d , J = 8 . 6 Hz , 2 H , 2 - pehnyl H - 2 , H - 6 ) , 7 . 91 ( s , 1 H , 4 - phenyl H - 2 ) , 7 . 81 - 7 . 79 ( m , 1 H , 4 - phenyl H - 6 ) , 7 . 77 ( s , 1 H , indenopyridine H - 3 ) , 7 . 57 - 7 . 55 ( m , 2 H , 4 - phenyl H - 4 , H - 5 ) , 7 . 45 ( s , 1 H , indenopyridine H - 6 ) , 6 . 91 - 6 . 85 ( m , 3 H , 2 - phenyl H - 3 , H - 5 , indenopyridine H - 7 ) , 3 . 95 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 56 , 158 . 74 , 157 . 21 , 156 . 25 , 144 . 54 , 142 . 00 , 140 . 62 , 135 . 05 , 133 . 94 , 133 . 12 , 130 . 97 , 130 . 08 , 128 . 85 , 128 . 56 , 128 . 42 ( 2 C ) , 127 . 49 , 126 . 37 , 116 . 95 , 116 . 58 , 115 . 74 ( 2 C ) , 106 . 85 , 33 . 30 .