TLC ( ethyl acetate / n - hexane = 2 : 3 ) Rf = 0 . 19 , mp : 314 - 316 ℃, HPLC purity : 95 . 4 %; ESI LC / MS : m / z calcd for C 24 H 17 ClNO 2 [ MH ] + 386 . 09 ; found 386 . 01 ( 100 %), [ MH + 2 ] : 388 . 12 ( 32 . 6 %). 1 H NMR ( 250 MHz , DMSO - d 6 ) δ 9 . 84 ( s , 1 H , indenopyridine 7 - OH ) , 9 . 82 ( s , 1 H , 4 - phenyl 4 - OH ) , 7 . 77 ( d , J = 8 . 25 Hz , 1 H , indenopyridine H - 9 ) , 7 . 71 - 7 . 68 ( m , 1 H , 2 - phenyl H - 6 ) , 7 . 66 ( d , J = 8 . 23 Hz , 2 H , 4 - phenyl H - 2 , H - 6 ) , 7 . 61 - 7 . 57 ( m , 1 H , 2 - phenyl H - 30 , 7 . 48 - 7 . 45 ( m , 2 H , 2 - phenyl H - 4 , H - 5 ) , 7 . 40 ( s , 1 H , indenopyridine H - 3 ) , 7 . 03 ( s , 1 H , indenopyridine H - 6 ) , 6 . 91 ( d , J = 8 . 37 Hz , 2 H , 4 - phenyl H - 3 , H - 5 ) , 6 . 85 ( dd , J = 8 . 67 , 1 . 45 Hz , 1 H , indenopyridine H - 8 ) , 4 . 01 ( s , 2 H , indenopyridine H - 5 ) . 13 C NMR ( 62 . 5 MHz , DMSO - d 6 ) δ 160 . 88 , 159 . 02 , 158 . 38 , 155 . 49 , 146 . 78 , 144 . 58 , 139 . 78 , 132 . 10 , 131 . 84 , 131 . 80 , 131 . 63 , 130 . 11 , 130 . 05 , 130 . 00 ( 2 C ) , 128 . 55 , 127 . 58 , 121 . 94 , 119 . 99 , 115 . 98 ( 2 C ) , 115 . 07 , 112 . 25 , 34 . 51 .