TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 21 , mp : 281 - 283 ℃, HPLC purity : 98 . 9 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 09 ( 100 %), [ MH + 2 ] : 388 . 21 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 90 ( s , 1 H , indenopyridine 6 - OH ) , 9 . 83 ( s , 1 H , 4 - phenyl 4 - OH ) , 8 . 31 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 22 ( d , J = 7 . 05 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 90 ( s , 1 H , indenopyridine H - 3 ) , 7 . 76 ( d , J = 8 . 5 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 58 ( d , J = 7 . 42 Hz , 1 H , indenopyridine H - 9 ) , 7 . 54 - 7 . 43 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 31 ( t , J = 7 . 77 Hz , 1 H , indenopyridine H - 8 ) , 6 . 95 ( d , J = 8 . 57 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 89 ( d , J = 7 . 82 Hz , 1 H , indenopyridine H - 7 ) , 3 . 96 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 55 , 159 . 04 , 154 . 77 , 154 . 72 , 146 . 85 , 142 . 81 , 142 . 06 , 134 . 52 , 133 . 79 , 131 . 41 , 130 . 84 ( 2 C ) , 130 . 78 , 129 . 53 , 129 . 41 , 129 . 10 , 127 . 23 , 126 . 23 , 118 . 07 , 116 . 49 ( 2 C ) , 116 . 34 , 112 . 71 , 32 . 69 .