TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 18 , mp : 300 - 302 ℃, HPLC purity : 99 . 9 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 16 ( 100 %), [ MH + 2 ] : 388 . 15 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 83 ( s , 2 H , indenopyridine 7 - OH , 4 - phenyl 2 - OH ) , 8 . 22 ( d , J = 8 . 57 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 87 ( d , J = 8 . 27 Hz , 1 H , indenopyridine H - 9 ) , 7 . 65 ( s , 1 H , indenopyridine H - 3 ) , 7 . 54 ( d , J = 8 . 57 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 7 . 38 ( dd , J = 7 . 55 , 1 . 5 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 29 ( t , J = 8 . 1 Hz , 1 H , 4 - phenyl H - 4 ) , 7 . 03 - 6 . 99 ( m , 2 H , 4 - phenyl H - 3 , indenopyridine H - 6 ) , 6 . 94 ( t , J = 7 . 42 Hz , 1 H , 4 - phenyl H - 50 , 6 . 87 ( dd , J = 8 . 3 , 2 . 0 Hz , 1 H , indenopyridine H - 8 ) , 3 . 79 ( s , 2 H , indenopyridine H - 8 ) , 3 . 79 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 21 , 159 . 01 , 154 . 47 , 153 . 51 , 146 . 68 , 144 . 19 , 138 . 33 , 134 . 33 , 133 . 58 , 131 . 97 , 130 . 66 , 129 . 98 , 128 . 87 ( 2 C ) , 128 . 57 ( 2 C ) , 125 . 42 , 121 . 80 , 119 . 53 , 118 . 06 , 116 . 25 , 114 . 97 , 112 . 34 , 34 . 13 .