#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012295.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012295 loop_ _publ_author_name 'Gales, Luis' 'Sousa, Maria Emilia de' 'Pinto, Madalena M. M.' 'Kijjoa, Anake' 'Damas, Ana M.' _publ_section_title ; Naturally occurring 1,2,8-trimethoxyxanthone and biphenyl ether intermediates leading to 1,2-dimethoxyxanthone ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1319 _journal_page_last 1323 _journal_paper_doi 10.1107/S010827010101349X _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C16 H14 O5' _chemical_formula_sum 'C16 H14 O5' _chemical_formula_weight 286.27 _chemical_name_systematic ; 1,2,8-Trimethoxy-9H-xanthen-9-one ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2730(10) _cell_length_b 15.443(4) _cell_length_c 16.550(6) _cell_measurement_reflns_used 1345 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.15 _cell_measurement_theta_min 4.06 _cell_volume 1347.7(7) _computing_cell_refinement IPDS _computing_data_collection 'IPDS (Stoe & Cie, 1994)' _computing_data_reduction IPDS _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 and ORTEP-3' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .961 _diffrn_measured_fraction_theta_max .961 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_measurement_method 'Image Plate' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .039 _diffrn_reflns_av_sigmaI/netI .023 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8453 _diffrn_reflns_theta_full 24.15 _diffrn_reflns_theta_max 24.15 _diffrn_reflns_theta_min 4.06 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .105 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 600 _exptl_crystal_size_max .8 _exptl_crystal_size_mid .5 _exptl_crystal_size_min .3 _refine_diff_density_max .14 _refine_diff_density_min -.11 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 'not reliably determined' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2068 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all .049 _refine_ls_R_factor_gt .042 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.046P)^2^+0.426P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .108 _reflns_number_gt 1887 _reflns_number_total 2068 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1457.cif _cod_data_source_block IV _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2012295 _cod_database_fobs_code 2012295 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' 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_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C4a O10 C10a 119.53(19) no C1 O11 C11 116.4(2) no C8 O13 C13 118.8(2) no C10a C8a C8 116.5(2) no C10a C8a C9 119.8(2) no C8 C8a C9 123.7(2) no C6 C5 C10a 118.3(3) no C6 C5 H5 122.3(19) no C10a C5 H5 119.3(19) no O13 C8 C7 123.8(2) no O13 C8 C8a 115.7(2) no C7 C8 C8a 120.5(2) no O10 C10a C5 114.7(2) no O10 C10a C8a 122.0(2) no C5 C10a C8a 123.3(3) no O10 C4a C4 115.3(2) no O10 C4a C9a 122.8(2) no C4 C4a C9a 121.9(2) no C8 C7 C6 119.9(3) no C8 C7 H7 119.4(17) no C6 C7 H7 120.7(17) no C4a C9a C1 118.1(2) no C4a C9a C9 118.9(2) no C1 C9a C9 123.0(2) no C2 O12 C12 118.6(2) no O14 C9 C8a 123.4(2) no O14 C9 C9a 121.3(2) no C8a C9 C9a 115.3(2) no C3 C4 C4a 119.1(3) no C3 C4 H4 121(2) no C4a C4 H4 120(2) no O13 C13 H13A 109.5 no O13 C13 H13B 109.5 no H13A C13 H13B 109.5 no O13 C13 H13C 109.5 no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 no O12 C12 H12A 109.5 no O12 C12 H12B 109.5 no H12A C12 H12B 109.5 no O12 C12 H12C 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no O11 C1 C2 118.9(2) no O11 C1 C9a 120.8(2) no C2 C1 C9a 120.1(2) no O12 C2 C3 124.3(3) no O12 C2 C1 115.6(2) no C3 C2 C1 120.0(3) no C5 C6 C7 121.4(3) no C5 C6 H6 120.0(18) no C7 C6 H6 118.5(18) no C4 C3 C2 120.7(3) no C4 C3 H3 121.5(19) no C2 C3 H3 117.8(19) no O11 C11 H11A 109.5 no O11 C11 H11B 109.5 no H11A C11 H11B 109.5 no O11 C11 H11C 109.5 no H11A C11 H11C 109.5 no H11B C11 H11C 109.5 no 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 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135094 2 PubChem 85931281