#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/22/2012293.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_2012293 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 H14 O5' _chemical_formula_sum 'C15 H14 O5' _chemical_formula_weight 274.26 _chemical_melting_point .42E-305 _chemical_name_systematic ; 2-(3,4-Dimethoxyphenoxy)benzoic acid ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 76.02(7) _cell_angle_beta 82.46(7) _cell_angle_gamma 64.20(6) _cell_formula_units_Z 2 _cell_length_a 7.920(4) _cell_length_b 8.550(5) _cell_length_c 11.360(7) _cell_measurement_reflns_used 854 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.21 _cell_measurement_theta_min 4.74 _cell_volume 671.8(8) _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 .901 _diffrn_measured_fraction_theta_max .901 _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 .047 _diffrn_reflns_av_sigmaI/netI .039 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 4584 _diffrn_reflns_theta_full 24.14 _diffrn_reflns_theta_max 24.14 _diffrn_reflns_theta_min 4.74 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .102 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 288 _exptl_crystal_size_max .7 _exptl_crystal_size_mid .4 _exptl_crystal_size_min .3 _refine_diff_density_max .14 _refine_diff_density_min -.15 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 189 _refine_ls_number_reflns 1923 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all .058 _refine_ls_R_factor_gt .050 _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^)+(0.098P)^2^+0.065P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .159 _reflns_number_gt 1618 _reflns_number_total 1923 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bm1457.cif _cod_data_source_block II _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_cell_volume 671.8(7) _cod_database_code 2012293 _cod_database_fobs_code 2012293 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 .25935(19) .52786(18) .28297(15) .0871(5) Uani d . 1 . . O O2 .4304(2) .2115(2) .41975(16) .0960(6) Uani d . 1 . . O O3 .2642(2) .05641(19) .49096(16) .0931(6) Uani d . 1 . . O H3 .3679 -.0181 .5146 .140 Uiso calc . 1 . . H O4 .2559(2) .91095(18) -.10998(11) .0805(5) Uani d . 1 . . O O5 .2565(2) 1.14851(18) -.00850(13) .0818(5) Uani d . 1 . . O C1 .0937(3) .5098(2) .31241(16) .0662(5) Uani d . 1 . . C C2 .1019(3) .3482(2) .38412(15) .0633(5) Uani d . 1 . . C C3 -.0656(3) .3280(3) .41072(17) .0736(6) Uani d . 1 . . C H3A -.0624 .2209 .4569 .088 Uiso calc . 1 . . H C4 -.2344(3) .4611(3) .3708(2) .0801(6) Uani d . 1 . . C H4 -.3443 .4449 .3898 .096 Uiso calc . 1 . . H C5 -.2392(3) .6200(3) .3017(2) .0786(6) Uani d . 1 . . C H5 -.354(4) .709(3) .270(2) .089(6) Uiso d . 1 . . H C6 -.0778(3) .6457(3) .27240(18) .0739(6) Uani d . 1 . . C H6 -.082(3) .755(3) .223(2) .079(6) Uiso d . 1 . . H C1' .2517(3) .6894(3) .21153(19) .0718(6) Uani d . 1 . . C C2' .2543(3) .7141(2) .08560(18) .0704(6) Uani d . 1 . . C H2' .2557 .6265 .0498 .085 Uiso calc . 1 . . H C3' .2548(3) .8701(2) .01435(16) .0645(5) Uani d . 1 . . C C4' .2555(3) 1.0000(2) .06998(17) .0644(5) Uani d . 1 . . C C5' .2544(3) .9711(3) .19456(18) .0731(6) Uani d . 1 . . C H5' .2548 1.0572 .2312 .088 Uiso calc . 1 . . H C6' .2527(3) .8147(3) .26675(17) .0757(6) Uani d . 1 . . C H6' .2522 .7958 .3509 .091 Uiso calc . 1 . . H C7 .2768(3) .1981(2) .43362(15) .0662(5) Uani d . 1 . . C C8 .2560(3) .7846(3) -.1720(2) .0867(7) Uani d . 1 . . C H8A .2564 .8300 -.2579 .130 Uiso calc . 1 . . H H8B .1459 .7631 -.1479 .130 Uiso calc . 1 . . H H8C .3659 .6755 -.1518 .130 Uiso calc . 1 . . H C9 .2548(4) 1.2853(3) .0412(2) .0920(7) Uani d . 1 . . C H9A .2560 1.3810 -.0233 .138 Uiso calc . 1 . . H H9B .3636 1.2402 .0892 .138 Uiso calc . 1 . . H H9C .1437 1.3277 .0913 .138 Uiso calc . 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 .0685(8) .0683(9) .1013(10) -.0262(7) -.0054(7) .0201(7) O2 .0748(9) .0744(10) .1130(12) -.0262(7) -.0031(8) .0168(8) O3 .0889(10) .0682(9) .1075(12) -.0331(7) -.0163(8) .0155(8) O4 .1120(11) .0721(8) .0622(8) -.0446(8) .0002(7) -.0121(6) O5 .1122(11) .0623(8) .0762(9) -.0453(7) -.0060(7) -.0049(6) C1 .0688(11) .0651(10) .0585(10) -.0270(9) .0032(8) -.0066(8) C2 .0727(11) .0606(10) .0512(9) -.0260(8) .0031(7) -.0085(7) C3 .0829(13) .0700(12) .0662(11) -.0347(10) .0049(9) -.0098(9) C4 .0702(12) .0863(14) .0822(13) -.0343(10) .0029(10) -.0146(11) C5 .0685(12) .0785(13) .0776(12) -.0235(10) -.0064(9) -.0084(10) C6 .0738(12) .0655(11) .0705(11) -.0242(9) -.0048(9) -.0012(9) C1' .0612(10) .0615(10) .0773(12) -.0229(8) -.0021(8) .0076(9) C2' .0740(11) .0551(10) .0777(12) -.0262(8) .0001(9) -.0085(8) C3' .0680(10) .0577(10) .0615(10) -.0242(8) .0016(8) -.0075(8) C4' .0682(10) .0552(9) .0660(10) -.0256(8) -.0005(8) -.0069(8) C5' .0785(12) .0719(12) .0687(11) -.0310(10) -.0014(9) -.0157(9) C6' .0753(12) .0817(13) .0608(10) -.0300(10) -.0016(9) -.0039(9) C7 .0777(12) .0599(10) .0545(9) -.0278(9) .0041(8) -.0053(8) C8 .0982(15) .0931(15) .0790(13) -.0444(12) .0063(11) -.0323(11) C9 .1114(17) .0695(13) .1067(17) -.0490(12) -.0016(13) -.0180(12) 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 C3' O4 C8 118.16(17) no C7 O3 H3 109.5 no C1 O1 C1' 118.16(15) no C4' O5 C9 117.90(17) no O5 C4' C5' 125.47(19) no O5 C4' C3' 114.88(16) no C5' C4' C3' 119.65(18) no O1 C1 C6 121.75(17) no O1 C1 C2 117.97(16) no C6 C1 C2 120.27(19) no C3 C2 C1 117.91(17) no C3 C2 C7 117.95(17) no C1 C2 C7 124.14(18) no O4 C3' C2' 125.06(19) no O4 C3' C4' 115.35(16) no C2' C3' C4' 119.59(18) no C5 C6 C1 119.70(19) no C5 C6 H6 120.7(13) no C1 C6 H6 119.6(13) no C3' C2' C1' 119.4(2) no C3' C2' H2' 120.3 no C1' C2' H2' 120.3 no C6' C1' C2' 121.58(18) no C6' C1' O1 119.29(19) no C2' C1' O1 119.0(2) no C6 C5 C4 121.1(2) no C6 C5 H5 119.8(15) no C4 C5 H5 119.0(15) no O2 C7 O3 121.77(18) no O2 C7 C2 121.20(17) no O3 C7 C2 117.04(19) no C4' C5' C6' 121.0(2) no C4' C5' H5' 119.5 no C6' C5' H5' 119.5 no C1' C6' C5' 118.81(18) no C1' C6' H6' 120.6 no C5' C6' H6' 120.6 no C4 C3 C2 121.93(19) no C4 C3 H3A 119.0 no C2 C3 H3A 119.0 no C3 C4 C5 119.1(2) no C3 C4 H4 120.5 no C5 C4 H4 120.5 no O4 C8 H8A 109.5 no O4 C8 H8B 109.5 no H8A C8 H8B 109.5 no O4 C8 H8C 109.5 no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no O5 C9 H9A 109.5 no O5 C9 H9B 109.5 no H9A C9 H9B 109.5 no O5 C9 H9C 109.5 no H9A C9 H9C 109.5 no H9B C9 H9C 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 O1 C1 . 1.376(2) yes O1 C1' . 1.403(2) yes O2 C7 . 1.257(3) yes O3 C7 . 1.268(2) yes O3 H3 . .8200 no O4 C3' . 1.370(2) yes O4 C8 . 1.425(3) yes O5 C4' . 1.366(2) yes O5 C9 . 1.410(3) yes C4' C5' . 1.376(3) yes C4' C3' . 1.407(3) yes C1 C6 . 1.391(3) yes C1 C2 . 1.403(3) yes C2 C3 . 1.397(3) yes C2 C7 . 1.480(3) yes C3' C2' . 1.384(3) yes C6 C5 . 1.375(3) yes C6 H6 . .96(2) no C2' C1' . 1.393(3) yes C2' H2' . .9300 no C1' C6' . 1.369(3) yes C5 C4 . 1.382(3) yes C5 H5 . .94(3) no C5' C6' . 1.394(3) yes C5' H5' . .9300 no C6' H6' . .9300 no C3 C4 . 1.369(3) yes C3 H3A . .9300 no C4 H4 . .9300 no C8 H8A . .9600 no C8 H8B . .9600 no C8 H8C . .9600 no C9 H9A . .9600 no C9 H9B . .9600 no C9 H9C . .9600 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O3 H3 O2 2_656 .82 1.81 2.612(3) 168 O3 H3 O3 2_656 .82 2.78 3.449(4) 140 loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135095