TLC ( ethyl acetate / n - hexane = 1 : 2 ) Rf = 0 . 21 , mp : 278 - 280 ℃, HPLC purity : 96 . 9 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 15 ( 100 %), [ MH + 2 ] : 388 . 08 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 64 ( s , 2 H , indenopyridine 8 - OH , 4 - phenyl 3 - OH ) , 8 . 27 ( dd , J = 8 . 6 , 2 . 2 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 83 ( s , 1 H , indenopyridine H - 3 ) , 7 . 56 ( dd , J = 8 . 62 , 2 . 27 Hz , 2 H , 2 - phenyl H - 3 , H - 5 ) , 7 . 46 - 7 . 42 ( m , 2 H , indenopyridine H - 6 , H - 9 ) , 7 . 34 ( td , J = 7 . 85 , 2 . 05 Hz , 1 H , 4 - phenyl H - 5 ) , 7 . 24 ( d , J = 7 . 37 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 18 ( s , 1 H , 4 - phenyl H - 2 ) , 6 . 89 ( d , J = 8 . 05 Hz , 1 H , 4 - phenyl H - 4 ) , 6 . 88 ( d , J = 8 . 15 Hz , 1 H , indenopyridine H - 7 ) , 3 . 95 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 83 , 157 . 92 , 157 . 22 , 154 . 57 , 146 . 34 , 141 . 74 , 139 . 38 , 138 . 04 , 135 . 02 , 134 . 41 , 133 . 93 , 130 . 19 , 128 . 96 ( 2 C ) , 128 . 76 ( 2 C ) , 126 . 34 , 119 . 36 , 117 . 43 , 117 . 11 , 116 . 06 , 115 . 41 , 106 . 90 , 33 . 88 .