data_2012292 _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 H16 O5' _chemical_formula_sum 'C16 H16 O5' _chemical_formula_weight 288.29 _chemical_melting_point .335E-305 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.306(7) _cell_length_b 7.788(4) _cell_length_c 16.426(7) _cell_angle_alpha 90 _cell_angle_beta 132.31(3) _cell_angle_gamma 90 _cell_volume 1448.0(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.322 _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 O1 .24922(13) .95469(19) .36254(10) .0701(5) Uani d . 1 . . O O2 .52741(18) 1.1418(3) .67270(13) .1062(8) Uani d . 1 . . O O3 .43905(15) .9146(2) .56698(12) .0799(5) Uani d . 1 . . O O4 .08949(12) .7792(2) .00103(11) .0648(4) Uani d . 1 . . O O5 -.10491(12) .6765(2) -.05112(10) .0647(4) Uani d . 1 . . O C1 .27071(16) 1.1278(3) .37561(14) .0511(4) Uani d . 1 . . C C2 .36879(16) 1.1880(3) .48176(15) .0532(4) Uani d . 1 . . C C3 .3895(2) 1.3644(3) .49603(19) .0668(6) Uani d . 1 . . C C4 .3174(2) 1.4790(3) .4103(2) .0730(6) Uani d . 1 . . C C5 .2212(2) 1.4168(3) .30683(19) .0649(5) Uani d . 1 . . C C6 .19786(18) 1.2434(3) .28934(16) .0563(5) Uani d . 1 . . C C1' .15623(18) .8911(3) .25623(14) .0586(5) Uani d . 1 . . C C2' .17351(18) .8712(3) .18365(15) .0575(5) Uani d . 1 . . C C3' .08389(16) .8010(2) .08024(14) .0522(4) Uani d . 1 . . C C4' -.02158(16) .7463(3) .05170(14) .0534(5) Uani d . 1 . . C C5' -.03561(19) .7676(3) .12593(16) .0616(5) Uani d . 1 . . C C6' .0536(2) .8416(3) .22907(16) .0636(5) Uani d . 1 . . C C7 .45267(17) 1.0809(3) .58277(15) .0580(5) Uani d . 1 . . C C8 .1928(3) .8416(4) .0255(3) .0776(7) Uani d . 1 . . C C9 -.2103(2) .6147(4) -.0804(2) .0687(6) Uani d . 1 . . C C10 .5178(3) .8075(5) .6633(2) .0852(8) Uani d . 1 . . C H3 .460(2) 1.401(3) .572(2) .079(7) Uiso d . 1 . . H H4 .336(2) 1.602(4) .424(2) .088(8) Uiso d . 1 . . H H5 .167(2) 1.495(3) .246(2) .075(7) Uiso d . 1 . . H H6 .134(2) 1.201(3) .2192(19) .067(6) Uiso d . 1 . . H H2' .244(2) .902(3) .2046(18) .066(6) Uiso d . 1 . . H H5' -.108(2) .731(3) .105(2) .073(7) Uiso d . 1 . . H H6' .044(2) .854(3) .2804(19) .072(6) Uiso d . 1 . . H H8A -.252(2) .556(3) -.151(2) .086(8) Uiso d . 1 . . H H8B -.254(2) .715(4) -.084(2) .079(7) Uiso d . 1 . . H H8C -.190(2) .531(3) -.025(2) .074(7) Uiso d . 1 . . H H9A .181(3) .818(4) -.040(3) .110(10) Uiso d . 1 . . H H9B .262(3) .777(4) .091(2) .092(9) Uiso d . 1 . . H H9C .205(3) .969(4) .042(2) .096(9) Uiso d . 1 . . H H10A .505(4) .841(6) .710(3) .153(16) Uiso d . 1 . . H H10B .594(4) .830(5) .699(3) .133(13) Uiso d . 1 . . H H10C .494(4) .694(6) .640(3) .156(16) Uiso d . 1 . . H 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 O1 .0700(9) .0592(9) .0393(7) -.0049(7) .0198(7) -.0001(6) O2 .0953(14) .0945(14) .0488(9) .0103(10) .0160(9) -.0106(8) O3 .0726(10) .0693(10) .0459(7) .0002(8) .0188(7) .0077(7) O4 .0586(8) .0822(10) .0578(8) -.0099(7) .0409(7) -.0071(7) O5 .0508(7) .0875(10) .0450(7) -.0137(7) .0279(6) -.0088(7) C1 .0484(9) .0586(11) .0441(9) .0014(8) .0302(8) -.0011(8) C2 .0470(9) .0632(11) .0480(9) .0010(8) .0315(8) -.0019(8) C3 .0608(12) .0680(13) .0596(12) -.0046(10) .0356(10) -.0085(10) C4 .0787(15) .0574(13) .0778(15) -.0022(11) .0505(13) -.0036(11) C5 .0685(13) .0639(13) .0645(12) .0128(10) .0457(11) .0107(10) C6 .0533(10) .0653(12) .0465(10) .0054(9) .0320(9) .0041(8) C1' .0565(11) .0567(11) .0392(9) .0012(8) .0227(8) .0024(7) C2' .0466(10) .0581(11) .0510(10) -.0022(8) .0260(8) .0031(8) C3' .0499(9) .0553(10) .0441(9) .0015(8) .0286(8) .0021(7) C4' .0468(9) .0608(11) .0409(9) -.0004(8) .0248(8) .0015(8) C5' .0514(11) .0782(14) .0503(10) -.0023(10) .0323(9) .0017(9) C6' .0650(12) .0744(14) .0472(10) .0019(10) .0361(10) .0020(9) C7 .0469(9) .0748(13) .0436(9) .0021(9) .0269(8) -.0064(9) C8 .0762(16) .0856(19) .0892(18) -.0148(14) .0630(15) -.0064(15) C9 .0535(11) .0801(16) .0600(13) -.0126(11) .0331(10) -.0059(12) C10 .0695(16) .088(2) .0566(13) .0065(14) .0256(12) .0197(13) 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 O1 C1 . 1.370(3) yes O1 C1' . 1.405(2) yes O4 C3' . 1.371(2) yes O4 C8 . 1.429(3) yes O5 C4' . 1.369(2) yes O5 C9 . 1.422(3) yes O2 C7 . 1.200(2) yes O3 C7 . 1.310(3) yes O3 C10 . 1.444(3) yes C1' C6' . 1.368(3) yes C1' C2' . 1.393(3) yes C2' C3' . 1.389(3) yes C2' H2' . .92(2) no C3' C4' . 1.410(3) yes C4' C5' . 1.383(3) yes C5' C6' . 1.397(3) yes C5' H5' . .96(3) no C6' H6' . .96(3) no C1 C6 . 1.391(3) yes C1 C2 . 1.411(3) yes C2 C3 . 1.394(3) yes C2 C7 . 1.493(3) yes C3 C4 . 1.380(3) yes C3 H3 . 1.00(3) no C4 C5 . 1.387(3) yes C4 H4 . .98(3) no C5 C6 . 1.377(3) yes C5 H5 . .97(3) no C6 H6 . .93(2) no C8 H9A . .98(3) no C8 H9B . 1.00(3) no C8 H9C . 1.02(3) no C9 H8A . .99(3) no C9 H8B . 1.00(3) no C9 H8C . .98(3) no C10 H10A . .94(4) no C10 H10B . .90(4) no C10 H10C . .93(5) no