TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 17 , mp : 254 - 256 ℃, HPLC purity : 95 . 6 %; 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 . 73 ( br , 1 H , indenopyridine 6 - OH ) , 7 . 96 ( s , 1 H , 4 - phenyl H - 2 ) , 7 . 87 - 7 . 82 ( m , 2 H , 4 - phenyl H - 6 , indenopyridine H - 3 ) , 7 . 69 - 7 . 54 ( m , 5 H , 2 - phenyl H - 2 , H - 6 , 4 - phenyl H - 4 , H - 5 , indenopyridine H - 9 ) , 7 . 34 ( t , J = 7 . 23 Hz , 1 H , 2 - phenyl H - 5 ) , 7 . 30 ( t , J = 7 . 62 Hz , 1 H , indenopyridine H - 8 ) , 6 . 90 ( d , J = 7 . 92 Hz , 1 H , 2 - phenyl H - 4 ) , 6 . 84 ( dd , J = 7 . 12 , 2 . 25 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 . 01 , 158 . 03 , 156 . 23 , 154 . 33 , 144 . 77 , 142 . 32 , 140 . 55 , 140 . 45 , 134 . 00 , 133 . 26 , 131 . 08 , 130 . 24 , 130 . 06 , 129 . 11 , 129 . 01 , 128 . 51 , 127 . 62 , 118 . 08 , 117 . 78 , 116 . 33 , 115 . 88 , 113 . 96 , 112 . 09 , 31 . 68 .