TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 22 , mp : 239 - 241 ℃, HPLC purity : 98 . 7 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 12 ( 100 %), [ MH + 2 ] : 388 . 15 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 63 ( s , 2 H , indenopyridine 8 - OH , 4 - phenyl 3 - OH ) , 8 . 33 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 22 ( dd , J = 6 . 81 , 1 . 6 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 90 ( s , 1 H , indenopyridine H - 3 ) , 7 . 58 - 7 . 48 ( m , 3 H , indenopyridine H - 9 , 2 - phenyl H - 4 , H - 5 ) , 7 . 43 ( d , J = 8 . 2 Hz , 1 H , indenopyridine H - 6 ) , 7 . 35 ( t , J = 7 . 7 Hz , 1 H , 4 - phenyl H - 50 , 7 . 26 ( d , J = 7 . 77 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 20 ( s , 1 H , 4 - phenyl H - 2 ) , 6 . 90 - 6 . 86 ( m , 2 H , 4 - phenyl H - 4 , indenopyridine H - 7 ) , 3 . 97 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 74 , 157 . 90 , 157 . 22 , 154 . 07 , 146 . 35 , 141 . 63 , 141 . 30 , 139 . 27 , 134 . 98 , 134 . 73 , 133 . 93 , 130 . 83 , 130 . 11 , 128 . . 84 , 126 . 61 , 126 . 33 , 125 . 56 , 119 . 38 , 117 . 74 , 117 . 13 , 115 . 96 , 115 . 47 , 106 . 84 , 33 . 67 .