TLC ( ethyl acetate / n - hexane = 1 : 7 ) Rf = 0 . 19 mp : 222 - 224 ℃, HPLC purity : 95 . 6 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 12 ( 100 %), [ MH + 2 ] : 388 . 11 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 93 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 46 ( s , 1 H , 4 - phenyl 2 - OH ) , 8 . 23 ( s , 1 H , 2 - phenyl H - 2 ) , 8 . 13 ( d , J = 7 . 25 Hz , 1 H , 2 - phenyl H - 6 ) , 7 . 82 ( s , 1 H , indenopyridine H - 3 ) , 7 . 59 - 7 . 55 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 46 ( d , J = 7 . 5 Hz , 1 H , 4 - phenyl H - 6 ) , 7 . 32 ( t , J = 7 . 77 Hz , 2 H , 4 - phenyl H - 4 , indenopyridine H - 7 ) , 7 . 12 ( d , J = 7 . 43 Hz , 1 H , indenopyridine H - 6 ) , 7 . 03 ( d , J = 8 . 2 Hz , 1 H , 4 - phenyl H - 3 ) , 6 . 96 ( t , J = 7 . 52 Hz , 1 H , 4 - phenyl H - 5 ) , 6 . 89 ( d , J = 8 . 02 Hz , 1 H , indenopyridine H - 8 ) , 6 . 94 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 64 , 154 . 55 , 154 . 01 , 152 . 92 , 145 . 62 , 144 . 87 , 140 . 92 , 134 . 80 , 134 . 05 , 131 . 01 , 130 . 88 , 130 . 80 , 130 . 35 , 129 . 00 , 126 . 63 , 125 . 57 , 125 . 25 , 124 . 91 , 119 . 60 , 119 . 35 , 116 . 95 , 116 . 33 , 113 . 69 , 34 . 78 .