TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 25 , mp : 271 - 273 ℃, HPLC purity : 95 . 3 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 62 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 78 ( s , 2 H , indenopyridine 6 - OH , 2 - phenyl 4 - OH ) , 8 . 12 ( d , J = 8 . 65 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 91 ( d , J = 8 . 45 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 77 ( s , 1 H , indenopyridine H - 3 ) , 7 . 62 ( d , J = 8 . 42 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 7 . 55 ( d , J = 7 . 4 Hz , 1 H , indenopyridine H - 9 ) , 7 . 31 ( r , J = 7 . 82 Hz , 1 H , indenopyridine H - 8 ) , 6 . 90 - 6 . 87 ( m , 3 H , 2 - phenyl H - 3 , H - 5 , indenopyridine H - 7 ) , 3 . 92 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 72 , 158 . 64 , 156 . 21 , 154 . 14 , 144 . 75 , 142 . 39 , 137 . 21 , 133 . 71 , 131 . 77 , 130 . 49 ( 2 C ) , 130 ( 2 C ) . 03 , 129 . 02 ( 2 C ) , 128 . 84 ( 2 C ) , 128 . 40 ( 2 C ) , 116 . 32 , 115 . 64 ( 2 C ) , 111 . 95 , 31 . 52 .