TLC ( ethyl acetate / n - hexane = 1 : 4 ) Rf = 0 . 2 , mp : 271 - 273 ℃, HPLC purity : 98 . 1 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 10 ( 100 %), [ MH + 2 ] : 388 . 30 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 77 ( s , 1 H , indenopyridine 7 - OH ) , 9 . 65 ( s , 1 H , 4 - phenyl 3 - OH ) , 7 . 78 ( d , J = 8 . 25 Hz , 1 H , indenopyridine H - 9 ) , 7 . 73 - 7 . 69 ( m , 1 H , 2 - phenyl H - 6 ) , 7 . 61 - 7 . 57 ( m , 1 H , 2 - phenyl H - 3 ) , 7 . 51 - 7 . 43 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 41 ( s , 1 H , indenopyridine H - 3 ) , 7 . 34 ( t , J = 7 . 8 Hz , 1 H , 4 - phenyl H - 5 ) , 7 . 20 ( d , J = 7 . 82 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 14 ( s , 1 H , 4 - phenyl H - 2 ) , 7 . 04 ( s , 1 H , indenopyridine H - 6 ) , 6 . 89 - 6 . 86 ( m , 2 H , 4 - phenyl H - 4 , indenopyridine H - 8 ) , 4 . 03 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 95 , 159 . 09 , 157 . 95 , 155 . 49 , 146 . 68 , 144 . 72 , 139 . 55 , 139 . 32 , 132 . 20 , 132 . 04 , 131 . 72 , 131 . 55 , 130 . 24 ( 2 C ) , 130 . 08 , 127 . 55 , 121 . 93 , 120 . 19 , 119 . 19 , 115 . 94 , 115 . 22 , 115 . 14 , 112 . 26 , 34 . 26 .