data_2012295 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2001 _journal_volume 57 _journal_page_first 1319 _journal_page_last 1323 _publ_section_title ; Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone ; loop_ _publ_author_name 'Gales, Luis' 'Sousa, Maria Emilia de' 'Pinto, Madalena M. M.' 'Kijjoa, Anake' 'Damas, Ana M.' _chemical_formula_moiety 'C16 H14 O5' _chemical_formula_sum 'C16 H14 O5' _chemical_formula_weight 286.27 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.2730(10) _cell_length_b 15.443(4) _cell_length_c 16.550(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1347.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.411 _diffrn_ambient_temperature 293(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O10 .1263(4) .98200(11) .76476(10) .0659(5) Uani d . 1 . . O O11 -.1765(4) 1.02405(12) .49169(9) .0650(5) Uani d . 1 . . O O12 -.4768(4) .88684(14) .50771(12) .0889(7) Uani d . 1 . . O O13 .4716(4) 1.23093(12) .63195(11) .0751(6) Uani d . 1 . . O O14 .0708(4) 1.15012(12) .57548(11) .0767(6) Uani d . 1 . . O C1 -.1870(5) .98420(16) .56569(14) .0578(6) Uani d . 1 . . C C2 -.3372(5) .91028(18) .57463(16) .0656(7) Uani d . 1 . . C C3 -.3319(6) .8639(2) .64644(18) .0732(8) Uani d . 1 . . C H3 -.450(7) .811(2) .651(2) .100(11) Uiso d . 1 . . H C4 -.1762(7) .88916(18) .70914(19) .0707(7) Uani d . 1 . . C H4 -.170(7) .857(2) .7581(18) .086(9) Uiso d . 1 . . H C5 .4639(6) 1.05602(18) .82292(16) .0665(7) Uani d . 1 . . C H5 .455(6) 1.015(2) .8658(18) .083(9) Uiso d . 1 . . H C6 .6424(6) 1.12058(19) .82110(18) .0703(8) Uani d . 1 . . C H6 .767(6) 1.1247(18) .8633(18) .079(9) Uiso d . 1 . . H C7 .6530(6) 1.17989(19) .75761(16) .0665(7) Uani d . 1 . . C H7 .773(6) 1.2248(18) .7577(16) .070(8) Uiso d . 1 . . H C8 .4804(6) 1.17423(15) .69478(14) .0591(6) Uani d . 1 . . C C9 .1117(5) 1.09513(16) .62757(14) .0573(6) Uani d . 1 . . C C11 -.3865(6) 1.0794(2) .47141(19) .0817(9) Uani d . 1 . . C H11A -.3601 1.1037 .4187 .123 Uiso calc . 1 . . H H11B -.3991 1.1251 .5105 .123 Uiso calc . 1 . . H H11C -.5404 1.0462 .4715 .123 Uiso calc . 1 . . H C12 -.6838(6) .8298(2) .5180(2) .0866(9) Uani d . 1 . . C H12A -.7649 .8203 .4669 .130 Uiso calc . 1 . . H H12B -.8032 .8548 .5551 .130 Uiso calc . 1 . . H H12C -.6240 .7756 .5391 .130 Uiso calc . 1 . . H C13 .6603(7) 1.29780(18) .62707(19) .0792(8) Uani d . 1 . . C H13A .6317 1.3321 .5795 .119 Uiso calc . 1 . . H H13B .8257 1.2720 .6243 .119 Uiso calc . 1 . . H H13C .6497 1.3340 .6741 .119 Uiso calc . 1 . . H C4a -.0259(5) .96225(15) .69987(14) .0581(6) Uani d . 1 . . C C8a .2966(5) 1.10672(15) .69314(14) .0536(6) Uani d . 1 . . C C9a -.0338(5) 1.01263(15) .62985(13) .0536(6) Uani d . 1 . . C C10a .2972(6) 1.04926(16) .75881(14) .0586(6) Uani d . 1 . . C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O10 .0733(12) .0665(10) .0580(9) -.0065(9) -.0047(9) .0109(8) O11 .0660(11) .0795(11) .0495(9) .0052(10) .0019(9) .0011(8) O12 .0872(15) .1058(15) .0738(13) -.0327(13) -.0056(12) -.0122(11) O13 .0863(14) .0677(11) .0712(11) -.0177(11) -.0085(11) .0100(9) O14 .0875(14) .0716(11) .0710(11) -.0105(10) -.0148(11) .0216(9) C1 .0582(14) .0638(14) .0515(13) .0020(13) .0025(11) -.0015(11) C2 .0640(16) .0696(16) .0632(15) -.0068(14) .0046(14) -.0106(12) C3 .076(2) .0709(18) .0730(18) -.0128(16) .0078(16) .0005(14) C4 .0772(19) .0676(16) .0672(16) -.0063(16) .0039(16) .0091(13) C5 .0768(19) .0679(15) .0548(14) .0044(15) -.0082(14) .0050(13) C6 .073(2) .0738(17) .0641(16) .0087(15) -.0126(15) -.0097(14) C7 .0680(18) .0666(16) .0648(16) -.0032(14) -.0056(14) -.0091(13) C8 .0685(16) .0548(13) .0542(13) -.0002(13) .0021(12) -.0013(11) C9 .0615(15) .0580(13) .0523(13) .0056(11) .0031(12) .0048(11) C11 .075(2) .094(2) .0765(18) .0180(17) -.0089(16) .0082(16) C12 .0642(19) .087(2) .109(2) -.0118(17) -.0058(18) -.0153(19) C13 .084(2) .0636(16) .090(2) -.0209(15) .0031(19) .0065(14) C4a .0590(15) .0597(13) .0554(14) .0006(12) .0013(12) .0004(11) C8a .0602(15) .0504(12) .0502(12) .0031(11) .0004(11) .0015(9) C9a .0553(14) .0553(12) .0503(12) .0015(11) .0039(11) .0018(10) C10a .0662(17) .0576(13) .0521(13) .0037(12) .0023(12) .0001(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O10 C4a . 1.375(3) yes O10 C10a . 1.379(3) yes O11 C1 . 1.372(3) yes O11 C11 . 1.438(3) yes O12 C2 . 1.378(3) yes O12 C12 . 1.413(4) yes O13 C8 . 1.360(3) yes O13 C13 . 1.436(3) yes O14 C9 . 1.229(3) yes C8a C10a . 1.403(3) yes C8a C8 . 1.424(4) yes C8a C9 . 1.470(3) yes C5 C6 . 1.371(4) yes C5 C10a . 1.382(4) yes C5 H5 . .95(3) no C8 C7 . 1.385(4) yes C4a C4 . 1.388(4) yes C4a C9a . 1.396(3) yes C7 C6 . 1.395(4) yes C7 H7 . .94(3) no C9a C1 . 1.404(3) yes C9a C9 . 1.488(3) yes C4 C3 . 1.379(4) yes C4 H4 . .95(3) no C13 H13A . .9600 no C13 H13B . .9600 no C13 H13C . .9600 no C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no C1 C2 . 1.398(4) yes C2 C3 . 1.387(4) yes C6 H6 . .96(3) no C3 H3 . 1.03(4) no C11 H11A . .9600 no C11 H11B . .9600 no C11 H11C . .9600 no