TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 21 , mp : 267 - 269 ℃, HPLC purity : 95 . 2 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 21 ( 100 %), [ MH + 2 ] : 388 . 12 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 89 ( s , 1 H , indenopyridine 7 - OH ) , 9 . 87 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 30 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 20 ( d , J = 7 . 17 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 89 ( d , J = 8 . 27 Hz , 1 H , indenopyridine H - 9 ) , 7 . 78 ( s , 1 H , indenopyridine H - 3 ) , 7 . 73 ( d , J = 8 . 45 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 56 - 7 . 46 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 03 ( s , 1 H , indenopyridine H - 6 ) , 6 . 93 ( d , J = 8 . 67 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 91 - 6 . 87 ( m , 1 H , indenopyridine H - 8 ) , 4 . 03 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 14 , 159 . 16 , 158 . 43 , 153 . 89 , 146 . 98 , 145 . 69 , 141 . 72 , 133 . 98 , 132 . 49 , 131 . 88 , 130 . 90 ( 2 C ) , 130 . 26 ( 2 C ) , 128 . 75 , 126 . 66 , 125 . 65 , 122 . 11 , 116 . 29 , 115 . 95 ( 2 C ) , 115 . 18 , 112 . 33 , 34 . 58 .