#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012294.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_2012294 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 'C15 H12 O4' _chemical_formula_sum 'C15 H12 O4' _chemical_formula_weight 256.25 _chemical_melting_point .406E-305 _chemical_name_systematic ; 1,2-Dimethoxy-9H-xanthen-9-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 97.23(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.953(2) _cell_length_b 13.930(6) _cell_length_c 17.670(8) _cell_measurement_reflns_used 1542 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.11 _cell_measurement_theta_min 3.74 _cell_volume 1209.5(9) _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 .938 _diffrn_measured_fraction_theta_max .938 _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 .71069 _diffrn_reflns_av_R_equivalents .056 _diffrn_reflns_av_sigmaI/netI .035 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 7542 _diffrn_reflns_theta_full 24.12 _diffrn_reflns_theta_max 24.12 _diffrn_reflns_theta_min 3.74 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .103 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 536 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _refine_diff_density_max .17 _refine_diff_density_min -.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 1807 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.072 _refine_ls_R_factor_all .080 _refine_ls_R_factor_gt .052 _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^)+(0.08P)^2^+0.422P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .168 _reflns_number_gt 1225 _reflns_number_total 1807 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1457.cif _cod_data_source_block III _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_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012294 _cod_database_fobs_code 2012294 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x-1/2, 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 .1782(4) .04584(12) .12661(11) .0671(6) Uani d . 1 . . O O11 .6932(4) .25908(13) .31078(12) .0722(6) Uani d . 1 . . O O12 .9964(5) .11133(14) .36272(12) .0788(7) Uani d . 1 . . O O13 .2837(5) .32503(13) .20306(12) .0824(7) Uani d . 1 . . O C1 .6361(6) .17037(18) .27668(16) .0614(7) Uani d . 1 . . C C2 .8009(6) .0927(2) .30233(16) .0634(7) Uani d . 1 . . C C3 .7572(6) .00285(19) .26745(17) .0661(8) Uani d . 1 . . C H3 .8704 -.0484 .2836 .079 Uiso calc . 1 . . H C4 .5477(6) -.0101(2) .20938(16) .0644(8) Uani d . 1 . . C H4 .502(6) -.076(2) .1884(16) .074(8) Uiso d . 1 . . H C5 -.2023(7) .0912(2) .04099(17) .0735(8) Uani d . 1 . . C H5 -.2205 .0277 .0249 .088 Uiso calc . 1 . . H C6 -.3784(7) .1603(3) .00908(18) .0820(9) Uani d . 1 . . C H6 -.5162 .1432 -.0293 .098 Uiso calc . 1 . . H C7 -.3548(7) .2560(2) .03311(19) .0795(9) Uani d . 1 . . C H7 -.4756 .3021 .0109 .095 Uiso calc . 1 . . H C8 -.1530(7) .2813(2) .08945(18) .0739(9) Uani d . 1 . . C H8 -.131(6) .347(2) .1089(17) .081(9) Uiso d . 1 . . H C9 .2513(6) .23974(19) .18346(16) .0643(8) Uani d . 1 . . C C11 .5135(7) .2855(2) .36529(19) .0802(9) Uani d . 1 . . C H11A .5650 .3473 .3864 .120 Uiso calc . 1 . . H H11B .5259 .2387 .4054 .120 Uiso calc . 1 . . H H11C .3299 .2882 .3404 .120 Uiso calc . 1 . . H C12 1.1668(8) .0336(2) .3915(2) .0874(10) Uani d . 1 . . C H12A 1.2944 .0557 .4333 .131 Uiso calc . 1 . . H H12B 1.2637 .0094 .3518 .131 Uiso calc . 1 . . H H12C 1.0569 -.0166 .4088 .131 Uiso calc . 1 . . H C4a .3821(6) .06718(18) .18490(15) .0595(7) Uani d . 1 . . C C8a .0339(6) .21248(19) .12325(15) .0616(7) Uani d . 1 . . C C9a .4242(6) .15965(17) .21638(15) .0590(7) Uani d . 1 . . C C10a .0032(6) .1177(2) .09776(15) .0637(7) 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 .0663(14) .0570(11) .0760(12) .0006(9) .0010(10) -.0071(9) O11 .0668(15) .0565(11) .0931(14) -.0060(9) .0087(10) -.0137(10) O12 .0740(15) .0685(12) .0886(14) .0055(10) -.0094(11) -.0082(10) O13 .0887(18) .0516(12) .1030(16) .0015(10) -.0036(12) -.0062(10) C1 .0600(19) .0510(15) .0737(17) -.0050(12) .0099(13) -.0052(12) C2 .0582(19) .0609(16) .0698(16) -.0010(12) .0028(13) -.0038(12) C3 .068(2) .0551(16) .0750(17) .0035(12) .0107(14) .0009(13) C4 .068(2) .0502(15) .0755(18) -.0007(13) .0092(14) -.0043(12) C5 .068(2) .0779(19) .0739(19) -.0058(15) .0058(15) -.0072(15) C6 .073(2) .095(2) .0761(19) .0000(18) .0013(16) .0039(17) C7 .072(2) .082(2) .084(2) .0077(16) .0042(17) .0097(17) C8 .073(2) .0691(19) .080(2) .0038(15) .0115(16) .0060(15) C9 .064(2) .0543(16) .0757(17) .0002(13) .0128(14) .0000(13) C11 .081(2) .0732(19) .086(2) .0033(16) .0103(17) -.0193(16) C12 .082(3) .081(2) .094(2) .0100(17) -.0081(18) .0014(17) C4a .0576(19) .0537(15) .0671(16) -.0026(12) .0067(13) -.0025(12) C8a .0592(19) .0591(16) .0668(16) -.0001(12) .0087(13) .0021(12) C9a .0580(19) .0480(14) .0714(16) -.0024(11) .0100(13) -.0029(11) C10a .062(2) .0618(16) .0681(16) .0017(13) .0112(13) .0001(13) 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 C10a O10 C4a 119.1(2) no C1 O11 C11 114.1(2) no C2 O12 C12 117.5(2) no O12 C2 C1 115.6(2) no O12 C2 C3 124.5(3) no C1 C2 C3 119.9(3) no C1 C9a C4a 117.1(2) no C1 C9a C9 123.9(2) no C4a C9a C9 119.0(2) no C10a C8a C8 117.8(3) no C10a C8a C9 121.3(3) no C8 C8a C9 120.9(3) no O10 C4a C4 114.4(2) no O10 C4a C9a 123.3(2) no C4 C4a C9a 122.3(3) no O10 C10a C5 116.3(3) no O10 C10a C8a 121.9(3) no C5 C10a C8a 121.7(3) no O11 C1 C2 118.0(3) no O11 C1 C9a 121.0(2) no C2 C1 C9a 120.9(2) no C6 C5 C10a 118.8(3) no C6 C5 H5 120.6 no C10a C5 H5 120.6 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 C7 C8 C8a 121.0(3) no C7 C8 H8 122.3(18) no C8a C8 H8 116.7(18) no C8 C7 C6 119.5(3) no C8 C7 H7 120.3 no C6 C7 H7 120.3 no C4 C3 C2 120.4(3) no C4 C3 H3 119.8 no C2 C3 H3 119.8 no C3 C4 C4a 119.4(3) no C3 C4 H4 120.7(17) no C4a C4 H4 119.7(17) no O13 C9 C8a 120.5(3) no O13 C9 C9a 124.3(3) no C8a C9 C9a 115.2(2) no C5 C6 C7 121.3(3) no C5 C6 H6 119.4 no C7 C6 H6 119.4 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 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 C10a . 1.379(3) yes O10 C4a . 1.381(3) yes O11 C1 . 1.388(3) yes O11 C11 . 1.439(4) yes O12 C2 . 1.373(3) yes O12 C12 . 1.426(4) yes O13 C9 . 1.242(3) yes C2 C1 . 1.396(4) yes C2 C3 . 1.400(4) yes C9a C1 . 1.406(4) yes C9a C4a . 1.408(4) yes C9a C9 . 1.480(4) yes C8a C10a . 1.397(4) yes C8a C8 . 1.412(4) yes C8a C9 . 1.465(4) yes C4a C4 . 1.389(4) yes C10a C5 . 1.387(4) yes C5 C6 . 1.372(5) yes C5 H5 . .9300 no C11 H11A . .9600 no C11 H11B . .9600 no C11 H11C . .9600 no C8 C7 . 1.365(5) yes C8 H8 . .98(3) no C7 C6 . 1.400(5) yes C7 H7 . .9300 no C3 C4 . 1.376(4) yes C3 H3 . .9300 no C4 H4 . 1.00(3) no C6 H6 . .9300 no C12 H12A . .9600 no C12 H12B . .9600 no C12 H12C . .9600 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10248976 2 PubChem 14189053