#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/65/2006554.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_2006554 loop_ _publ_author_name 'Blackburn, Anthony C.' 'Gerkin, Roger E.' _publ_section_title ; 1,4-Dimethoxy-2-naphthoic Acid ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1425 _journal_page_last 1427 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C13 H12 O4 ' _chemical_formula_sum 'C13 H12 O4' _chemical_formula_weight 232.24 _chemical_name_common '1,4-dimethoxy-2-naphthoic acid' _chemical_name_systematic ' ?' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 92.84(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 3.971(2) _cell_length_b 8.904(2) _cell_length_c 31.417(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 14.6 _cell_measurement_theta_min 13.3 _cell_volume 1109.5(6) _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_type 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 0.020 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_number 3118 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% '+-1.8% (ave. max. rel. intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_meas none _exptl_crystal_description 'cut column' _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.22 _refine_diff_density_min -0.20 _refine_ls_extinction_coef '12(4) \\times 10^-7^' _refine_ls_extinction_method 'Zachariasen (1963,1968)' _refine_ls_goodness_of_fit_ref 1.58 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 1663 _refine_ls_R_factor_gt 0.059 _refine_ls_shift/su_max '< 0.01' _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme w=1/\s~F~^2^ _refine_ls_wR_factor_ref 0.053 _reflns_number_gt 1663 _reflns_number_total 2736 _reflns_threshold_expression 'I > 0.75\s~I~' _[local]_cod_data_source_file bk1333.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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_adp_type' tag value 'Uij' was replaced with 'Uani' value 17 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 ; _cod_database_code 2006554 loop_ _symmetry_equiv_pos_as_xyz x,y,z '-x, 1/2 +y, 1/2 -z' -x,-y,-z 'x, 1/2 -y, 1/2 +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_calc_attached_atom O1 .3266(4) .0670(2) .13339(5) .0466(4) Uani ? ? O2 .1371(6) .0034(2) .05174(6) .0755(7) Uani ? ? O3 -.1344(6) .1773(2) .01404(5) .0728(6) Uani ? ? O4 -.2828(4) .6218(2) .10645(5) .0548(5) Uani ? ? C1 .1559(5) .1992(2) .12513(6) .0377(6) Uani ? ? C2 .0089(5) .2339(2) .08568(6) .0387(6) Uani ? ? C3 -.1433(5) .3776(2) .07900(6) .0404(6) Uani ? ? C4 -.1477(6) .4808(2) .11053(7) .0409(6) Uani ? ? C5 -.0028(6) .5514(2) .18582(7) .0485(7) Uani ? ? C6 .1410(7) .5163(3) .22491(7) .0557(8) Uani ? ? C7 .2953(7) .3763(3) .23160(7) .0558(7) Uani ? ? C8 .3027(6) .2739(3) .19965(7) .0481(7) Uani ? ? C9 .1532(5) .3058(2) .15881(6) .0391(6) Uani ? ? C10 -.0011(5) .4481(2) .15169(6) .0390(6) Uani ? ? C11 .1248(7) -.0563(3) .14611(8) .0595(8) Uani ? ? C12 .0068(6) .1306(3) .04870(7) .0456(7) Uani ? ? C13 -.4235(7) .6646(3) .06583(8) .0592(8) Uani ? ? H1A .110(10) -.052(6) .028(2) .06(2) Uiso ? ? H1B -.18(2) .104(7) -.007(2) .09(2) Uiso ? ? H3 -.2470 .4020 .0509 .0484 Uiso ? ? H5 -.1101 .6495 .1814 .0587 Uiso ? ? H6 .1376 .5895 .2483 .0668 Uiso ? ? H7 .3995 .3515 .2598 .0668 Uiso ? ? H8 .4135 .1770 .2050 .0575 Uiso ? ? H9 .2641 -.1466 .1490 .0712 Uiso ? ? H10 .0267 -.0330 .1733 .0712 Uiso ? ? H11 -.0576 -.0736 .1243 .0712 Uiso ? ? H12 -.5105 .7672 .0671 .0710 Uiso ? ? H13 -.2468 .6604 .0449 .0710 Uiso ? ? H14 -.6053 .5957 .0571 .0710 Uiso ? ? 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 .0475(9) .0369(8) .0552(9) .0083(8) -.0006(8) .0099(7) O2 .125(2) .0490(10) .0500(10) .0350(10) -.0140(10) -.0071(9) O3 .114(2) .0580(10) .0450(10) .0260(10) -.0180(10) -.0044(9) O4 .0720(10) .0343(9) .0572(10) .0146(8) -.0030(9) .0055(7) C1 .0350(10) .0330(10) .0440(10) .0020(10) .0030(10) .0083(10) C2 .0430(10) .0340(10) .0390(10) .0000(10) .0020(10) .0054(9) C3 .0450(10) .0360(10) .0400(10) .0020(10) -.0021(10) .0092(10) C4 .0440(10) .0310(10) .0480(10) .0010(10) .0030(10) .0041(10) C5 .0540(10) .0390(10) .0530(10) -.0060(10) .0070(10) -.0010(10) C6 .062(2) .057(2) .0480(10) -.0100(10) .0040(10) -.0090(10) C7 .060(2) .063(2) .0430(10) -.0080(10) -.0060(10) .0020(10) C8 .0470(10) .0510(10) .0460(10) -.0030(10) -.0040(10) .0070(10) C9 .0370(10) .0380(10) .0420(10) -.0050(10) .0018(10) .0058(10) C10 .0400(10) .0360(10) .0420(10) -.0060(10) .0046(10) .0025(9) C11 .072(2) .0390(10) .068(2) .0050(10) .0080(10) .0140(10) C12 .0540(10) .0390(10) .0440(10) .0080(10) .0030(10) .0040(10) C13 .066(2) .0420(10) .068(2) .0120(10) -.0030(10) .0150(10) 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 C1 ? ? 1.377(2) no O1 C11 ? ? 1.427(3) no C12 O2 ? ? 1.247(3) yes O2 H1A ? ? .89(6) no C12 O3 ? ? 1.270(2) yes O3 H1B ? ? .93(7) no O4 C4 ? ? 1.369(2) no O4 C13 ? ? 1.419(3) no C1 C2 ? ? 1.379(3) no C1 C9 ? ? 1.422(3) no C2 C3 ? ? 1.426(3) no C2 C12 ? ? 1.482(3) no C3 C4 ? ? 1.352(3) no C3 H3 ? ? .9788 no C4 C10 ? ? 1.422(3) no C5 C6 ? ? 1.365(3) no C5 C10 ? ? 1.413(3) no C5 H5 ? ? .9786 no C6 C7 ? ? 1.400(4) no C6 H6 ? ? .9828 no C7 C8 ? ? 1.357(3) no C7 H7 ? ? .9839 no C8 C9 ? ? 1.416(3) no C8 H8 ? ? .9795 no C9 C10 ? ? 1.420(3) no C11 H9 ? ? .9776 no C11 H10 ? ? .9774 no C11 H11 ? ? .9849 no C13 H12 ? ? .9785 no C13 H13 ? ? .9860 no C13 H14 ? ? .9763 no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson and Simpson (1965)' C .002 .002 'Cromer and Waber (1974)' O .008 .006 'Cromer and Waber (1974)' 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 C1 O1 C11 115.6(2) no C12 O2 H1A 113(3) no C12 O3 H1B 115(3) no C4 O4 C13 117.7(2) no C9 C1 O1 116.9(2) yes C2 C1 O1 122.9(2) yes C2 C1 C9 120.1(2) no C1 C2 C3 119.4(2) no C1 C2 C12 123.5(2) no C3 C2 C12 117.1(2) no C2 C3 C4 121.5(2) no C2 C3 H3 119.2015 no C4 C3 H3 119.2913 no C3 C4 O4 125.0(2) yes C10 C4 O4 114.4(2) yes C3 C4 C10 120.5(2) no C6 C5 C10 121.1(2) no C6 C5 H5 119.4313 no C10 C5 H5 119.4778 no C5 C6 C7 120.0(2) no C5 C6 H6 119.9779 no C7 C6 H6 120.0639 no C6 C7 C8 120.8(2) no C6 C7 H7 119.7761 no C8 C7 H7 119.3966 no C7 C8 C9 120.8(2) no C7 C8 H8 119.4465 no C9 C8 H8 119.7449 no C1 C9 C8 121.5(2) no C1 C9 C10 119.8(2) no C8 C9 C10 118.7(2) no C4 C10 C5 122.7(2) no C4 C10 C9 118.7(2) no C5 C10 C9 118.6(2) no O1 C11 H9 109.6169 no O1 C11 H10 109.5655 no O1 C11 H11 109.2067 no H9 C11 H10 109.8885 no H9 C11 H11 109.2618 no H10 C11 H11 109.2849 no C2 C12 O2 121.2(2) yes C2 C12 O3 117.0(2) yes O2 C12 O3 121.8(2) yes O4 C13 H12 109.7032 no O4 C13 H13 109.1911 no O4 C13 H14 109.6376 no H12 C13 H13 109.1035 no H12 C13 H14 109.9057 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 _geom_hbond_publ_flag O2 H1A O3 3_555 0.89(6) 1.74(6) 2.619(2) 167(5) yes O3 H1B O2 3_555 0.93(7) 1.73(7) 2.619(2) 159(6) yes _journal_paper_doi 10.1107/S0108270197008299