TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 23 , mp : 303 - 305 ℃, HPLC purity : 99 . 1 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 15 ( 100 %), [ MH + 2 ] : 388 . 17 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 86 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 69 ( s , 1 H , 4 - phenyl 2 - OH ) , 8 . 25 ( d , J = 8 . 57 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 78 ( s , 1 H , indenopyridine H - 3 ) , 7 . 58 - 7 . 54 ( m , 3 H , indenopyridine H - 9 , 2 - phenyl H - 3 , H - 5 ) , 7 . 42 ( dd , J = 7 . 5 , 1 . 3 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 31 ( t , J = 7 . 62 Hz , 2 H , 4 - phenyl H - 4 , indenopyridine H - 8 ) , 7 . 03 ( d , J = 7 . 92 Hz , 1 H , 4 - phenyl H - 3 ) , 6 . 96 ( t , J = 7 . 42 Hz , 1 H , 4 - phenyl H - 5 ) , 6 . 88 ( d , J = 7 . 83 Hz , 1 H , indenopyridine H - 7 ) , 3 . 75 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 14 , 154 . 57 , 154 . 27 , 153 . 94 , 144 . 98 , 142 . 46 , 138 . 19 , 135 . 27 , 133 . 86 , 130 . 88 , 130 . 25 ( 2 C ) , 130 . 00 , 129 . 05 ( 2 C ) , 128 . 77 ( 2 C ) , 125 . 31 , 119 . 69 , 119 . 49 , 116 . 30 , 115 . 81 , 112 . 12 , 31 . 81 .