TLC ( ethyl acetate / n - hexane = 1 : 4 ) Rf = 0 . 22 , mp : 212 - 214 ℃, HPLC purity : 95 . 5 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 16 ( 100 %), [ MH + 2 ] : 388 . 14 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 77 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 52 ( s , 1 H , 4 - phenyl 3 - OH ) , 8 . 27 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 17 ( dd , J = 6 . 7 , 1 . 95 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 90 ( s , 1 H , indenopyridine H - 3 ) , 7 . 61 - 7 . 52 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 39 - 7 . 12 ( m , 5 H , 4 - phenyl H - 2 , H - 5 , H - 6 , indenopyridine H - 6 , H - 7 ) , 6 . 92 - 6 . 88 ( m , 2 H , 4 - phenyl H - 4 , indenopyridine H - 8 ) , 4 . 12 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 55 , 158 . 03 , 154 . 12 , 153 . 69 , 146 . 38 , 145 . 81 , 140 . 78 , 139 . 05 , 134 . 10 , 133 . 04 , 131 . 05 , 130 . 98 , 130 . 31 , 129 . 220 , 126 . 77 , 125 . 71 , 125 . 12 , 119 . 55 , 117 . 41 , 116 . 97 , 116 . 26 , 115 . 58 , 113 . 75 , 34 . 90 .