TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 17 , mp : 303 - 305 ℃, HPLC purity : 98 . 2 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 62 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 77 ( s , 1 H , indenopyridine 8 - OH ) , 9 . 58 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 10 ( d , J = 8 . 6 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 88 ( d , J = 8 . 45 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 75 ( s , 1 H , indenopyridine H - 3 ) , 7 . 61 ( d , J = 8 . 4 Hz , 2 H , 4 - pehnyl H - 3 , H - 5 ) , 7 . 44 ( s , 1 H , indenopyridine H - 9 ) , 7 . 42 ( d , J = 8 . 42 Hz , 1 H , indenopyridine H - 6 ) , 6 . 90 ( d , J = 7 . 57 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 6 . 86 ( dd , J = 7 . 52 , 2 . 27 Hz , 1 H , indenopyridine H - 7 ) , 3 . 94 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 53 , 158 . 70 , 157 . 18 , 156 . 19 , 144 . 67 , 141 . 99 , 137 . 26 , 134 . 97 , 133 . 77 , 132 . 96 , 130 . 57 ( 2 C ) , 130 . 08 , 129 . 08 , ( 2 C ) 128 . 48 ( 2 C ) , 126 . 28 , 116 . 88 , 116 . 41 , 115 . 72 ( 2 C ) , 106 . 83 , 33 . 36 .