#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/63/2006370.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_2006370 loop_ _publ_author_name 'Blackburn, Anthony C.' 'Gerkin, Roger E.' _publ_section_title ; 5,8-Dimethoxy-1-naphthoic Acid and Methyl 5,8-Dimethoxy-1-naphthoate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1077 _journal_page_last 1080 _journal_paper_doi 10.1107/S0108270197004940 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C14 H14 O4 ' _chemical_formula_sum 'C14 H14 O4' _chemical_formula_weight 246.26 _chemical_name_common 'methyl 5,8-dimethoxy-1-naphthoate' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90 _cell_angle_beta 100.970(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.707(2) _cell_length_b 8.7200(10) _cell_length_c 18.619(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 13.0 _cell_volume 1228.4(4) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device AFC5S _diffrn_measurement_method '\w scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 3241 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% ' +-3.0 (ave. max. rel. intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_meas ? _exptl_crystal_description 'cut plate' _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.21 _refine_diff_density_min -0.21 _refine_ls_extinction_coef '4.7(12) \\times 10^-7^' _refine_ls_extinction_method 'Zachariasen (1963,1968)' _refine_ls_goodness_of_fit_obs 1.66 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 1499 _refine_ls_R_factor_obs .052 _refine_ls_shift/esd_max '< 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = \s~F~^-2^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .034 _reflns_number_observed 1499 _reflns_number_total 3024 _reflns_observed_criterion 'I >1\s~I~' _cod_data_source_file bs1029.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_atom_site_thermal_displace_type' tag value 'Uij' was replaced with 'Uani' value 18 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = \s~F~^-2^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = \s~F~^-2^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/a' _cod_database_code 2006370 loop_ _symmetry_equiv_pos_as_xyz x,y,z '1/2 -x, 1/2 +y, -z' '-x, -y, -z ' '1/2 +x, 1/2-y, z' 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 .0660(10) .0510(10) .0391(10) -.0090(10) .0132(9) .0017(9) O2 .089(2) .0600(10) .0470(10) -.0140(10) .0130(10) .0140(10) O3 .0740(10) .0730(10) .0390(10) .0190(10) .0142(10) -.0090(10) O4 .0610(10) .080(2) .0480(10) .0210(10) -.0011(10) -.0070(10) C1 .053(2) .039(2) .0390(10) .0050(10) .0130(10) .0020(10) C2 .065(2) .071(2) .044(2) .021(2) .020(2) -.002(2) C3 .054(2) .080(2) .052(2) .026(2) .009(2) .001(2) C4 .056(2) .054(2) .037(2) .007(2) .0080(10) .0010(10) C5 .059(2) .045(2) .043(2) .0040(10) .0140(10) .0000(10) C6 .060(2) .070(2) .053(2) .017(2) .020(2) -.009(2) C7 .051(2) .066(2) .058(2) .017(2) .009(2) -.005(2) C8 .053(2) .044(2) .046(2) .0050(10) .0050(10) .0000(10) C9 .048(2) .0320(10) .0400(10) .0010(10) .0120(10) .0010(10) C10 .048(2) .0330(10) .0400(10) .0010(10) .0150(10) .0000(10) C11 .053(2) .045(2) .041(2) .0050(10) .0120(10) .0050(10) C12 .087(3) .094(3) .050(2) .021(3) .017(2) -.019(2) C13 .061(2) .076(3) .061(2) .010(2) -.001(2) .012(2) C14 .068(2) .079(3) .042(2) -.012(2) .000(2) -.002(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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O1 -.1197(2) 1.2135(2) .38978(8) .0516(6) Uani ? ? O2 -.2496(3) .9956(2) .41436(9) .0653(7) Uani ? ? O3 -.2260(2) .9132(2) .04626(9) .0615(6) Uani ? ? O4 .0711(2) .9565(2) .34048(9) .0642(7) Uani ? ? C1 -.2664(3) 1.0719(3) .28940(10) .0431(8) Uani ? ? C2 -.4302(4) 1.1281(4) .2615(2) .0590(10) Uani ? ? C3 -.5024(4) 1.1195(4) .1870(2) .0620(10) Uani ? ? C4 -.4100(4) 1.0519(3) .14050(10) .0492(9) Uani ? ? C5 -.1403(4) .9202(3) .11870(10) .0482(8) Uani ? ? C6 .0229(4) .8637(3) .1445(2) .0600(10) Uani ? ? C7 .0978(4) .8750(3) .2191(2) .0590(10) Uani ? ? C8 .0097(3) .9415(3) .26720(10) .0483(8) Uani ? ? C9 -.1640(3) 1.0028(3) .24240(10) .0395(7) Uani ? ? C10 -.2391(3) .9924(3) .16640(10) .0395(7) Uani ? ? C11 -.2091(3) 1.0842(3) .37110(10) .0455(8) Uani ? ? C12 -.1492(6) .8185(6) -.0014(2) .0770(10) Uani ? ? C13 .2444(5) .9024(5) .3692(2) .0680(10) Uani ? ? C14 -.0559(5) 1.2379(5) .4674(2) .0640(10) Uani ? ? H2 -.495(3) 1.172(3) .2930(10) .057(8) Uiso ? ? H3 -.622(3) 1.156(3) .1670(10) .066(9) Uiso ? ? H4 -.460(3) 1.045(2) .0890(10) .049(7) Uiso ? ? H6 .087(3) .820(3) .1110(10) .065(9) Uiso ? ? H7 .217(3) .836(3) .2370(10) .060(8) Uiso ? ? H12A -.236(4) .823(3) -.050(2) .100(10) Uiso ? ? H12B -.127(4) .716(4) .019(2) .100(10) Uiso ? ? H12C -.037(4) .854(4) -.007(2) .110(10) Uiso ? ? H13A .266(4) .924(3) .4210(10) .090(10) Uiso ? ? H13B .248(4) .790(3) .363(2) .100(10) Uiso ? ? H13C .332(4) .948(4) .342(2) .110(10) Uiso ? ? H14A -.157(4) 1.252(4) .492(2) .110(10) Uiso ? ? H14B .017(4) 1.147(4) .491(2) .110(10) Uiso ? ? H14C .018(4) 1.332(3) .4710(10) .090(10) Uiso ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C .002 .002 'Cromer & Waber (1974)' O .008 .006 'Cromer & Waber (1974)' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 1 2 0 2 4 2 0 5 2 1 7 1 5 -4 2 0 11 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 C11 O1 C14 116.3(2) yes C5 O3 C12 117.1(2) yes C8 O4 C13 117.8(2) yes C2 C1 C9 120.2(2) no C2 C1 C11 115.6(2) yes C9 C1 C11 124.2(2) yes C1 C2 C3 121.7(3) no C1 C2 H2 118.0(10) no C3 C2 H2 119.0(10) no C2 C3 C4 120.0(3) no C2 C3 H3 122.0(10) no C4 C3 H3 117.0(10) no C3 C4 C10 120.7(2) no C3 C4 H4 120.0(10) no C10 C4 H4 119.0(10) no O3 C5 C6 124.7(2) yes O3 C5 C10 114.5(2) yes C6 C5 C10 120.8(2) no C5 C6 C7 120.5(3) no C5 C6 H6 118.0(10) no C7 C6 H6 120.0(10) no C6 C7 C8 121.4(3) no C6 C7 H7 119.0(10) no C8 C7 H7 118.0(10) no O4 C8 C7 125.6(3) yes O4 C8 C9 114.3(2) yes C7 C8 C9 120.1(2) no C1 C9 C8 123.7(2) no C1 C9 C10 118.0(2) no C8 C9 C10 118.3(2) no C4 C10 C5 121.7(2) no C4 C10 C9 119.4(2) no C5 C10 C9 118.9(2) no O1 C11 O2 123.9(2) yes O1 C11 C1 111.1(2) yes O2 C11 C1 124.7(3) yes O3 C12 H12A 104.0(10) no O3 C12 H12B 111.0(10) no O3 C12 H12C 111(2) no H12A C12 H12B 114(2) no H12A C12 H12C 110(2) no H12B C12 H12C 104(2) no O4 C13 H13A 106.0(10) no O4 C13 H13B 109.0(10) no O4 C13 H13C 110.0(10) no H13A C13 H13B 107(2) no H13A C13 H13C 115(2) no H13B C13 H13C 107(2) no O1 C14 H14A 109.0(10) no O1 C14 H14B 111.0(10) no O1 C14 H14C 105.0(10) no H14A C14 H14B 108(2) no H14A C14 H14C 110(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C11 ? ? 1.333(3) yes O1 C14 ? ? 1.450(3) yes O2 C11 ? ? 1.199(3) yes O3 C5 ? ? 1.385(3) yes O3 C12 ? ? 1.422(4) yes O4 C8 ? ? 1.363(3) yes O4 C13 ? ? 1.421(4) yes C1 C2 ? ? 1.361(3) no C1 C9 ? ? 1.419(3) no C1 C11 ? ? 1.506(3) yes C2 C3 ? ? 1.396(4) no C2 H2 ? ? .93(2) no C3 C4 ? ? 1.357(3) no C3 H3 ? ? .98(2) no C4 C10 ? ? 1.412(3) no C4 H4 ? ? .96(2) no C5 C6 ? ? 1.351(3) no C5 C10 ? ? 1.422(3) no C6 C7 ? ? 1.402(4) no C6 H6 ? ? .95(2) no C7 C8 ? ? 1.354(3) no C7 H7 ? ? .97(2) no C8 C9 ? ? 1.434(3) no C9 C10 ? ? 1.427(3) no C12 H12A ? ? 1.02(3) no C12 H12B ? ? .97(3) no C12 H12C ? ? .94(3) no C13 H13A ? ? .97(3) no C13 H13B ? ? .99(3) no C13 H13C ? ? .99(3) no C14 H14A ? ? .98(3) no C14 H14B ? ? 1.02(3) no C14 H14C ? ? 1.00(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 14509265