TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 26 , mp : 194 - 196 ℃. HPLC purity : 97 . 4 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 08 ( 100 %), [ MH + 2 ] : 388 . 20 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 83 ( s , 1 H , indenopyridine 9 - OH ) , 9 . 61 ( s , 1 H , 2 - phenyl 4 - OH ) , 8 . 02 ( d , J = 8 . 70 Hz , 2 H , 2 - phenyl H - 2 , H - 6 ) , 7 . 71 - 7 . 61 ( m , 3 H , 4 - phenyl H - 3 , H - 6 , indenopyridine H - 3 ) , 7 . 55 - 7 . 51 ( m , 3 H , 4 - phenyl H - 4 , H - 5 ) , 7 . 32 ( t , J = 7 . 85 Hz , 1 H , indenopyridine H - 7 ) , 7 . 11 ( d , J = 7 . 57 Hz , 1 H , indenopyridine H - 6 ) , 6 . 95 - 6 . 88 ( 3 H , 2 - phenyl H - 3 , H - 5 , indenopyridine H - 8 ) , 4 . 81 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 39 , 158 . 96 , 155 . 51 , 154 . 02 , 145 . 52 , 144 . 68 , 140 . 16 , 134 . 00 , 131 . 31 , 131 . 00 , 130 . 82 , 129 . 18 , 129 . 08 , 128 . 53 ( 2 C ) , 128 . 43 , 127 . 49 , 125 . 03 , 116 . 97 , 116 . 10 , 115 . 88 ( 2 C ) , 113 . 40 , 34 . 53 .