TLC ( ethyl acetate / n - hexane = 1 : 3 ) Rf = 0 . 27 , mp : 224 - 226 ℃, HPLC purity : 95 . 5 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 15 ( 100 %), [ MH + 2 ] : 388 . 22 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 92 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 49 ( s , 1 H , 4 - phenyl 4 - OH ) , 7 . 80 - 7 . 76 ( m , 1 H , 2 - phenyl H - 6 ) , 7 . 73 ( d , J = 8 . 52 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 64 - 7 . 61 ( m , 1 H , 2 - phenyl H - 3 ) , 7 . 58 ( s , 1 H , indenopyridine H - 3 ) , 7 . 51 - 7 . 48 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 33 ( t , J = 7 . 8 Hz , 1 H , indenopyridine H - 7 ) , 7 . 16 ( d , J = 7 . 42 Hz , 1 H , indenopyridine H - 6 ) , 6 . 94 ( d , J = 8 . 5 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 87 ( d , J = 8 . 02 Hz , 1 H , indenopyridine H - 8 ) , 4 . 19 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 161 . 02 , 158 . 74 , 154 . 64 , 154 . 07 , 145 . 49 , 138 . 55 , 132 . 05 , 131 . 84 , 131 . 68 , 130 . 86 ( 2 C ) , 130 . 48 ( 2 C ) , 130 . 17 ( 2 C ) , 127 . 95 , 127 . 84 , 124 . 83 , 120 . 51 , 116 . 89 , 116 . 08 ( 2 C ) , 113 . 31 , 35 . 12 .