#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003231.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_2003231 loop_ _publ_author_name 'Ferguson, G.' 'Gallagher, J. F.' 'McAlees, A. J.' _publ_section_title ; Ligands for Application in Coordination Chemistry: Three Dicarboxylic Acids ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 454 _journal_page_last 458 _journal_paper_doi 10.1107/S0108270194010000 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'synthesised by authors' _chemical_formula_moiety 'C12 H22 O6 ' _chemical_formula_sum 'C12 H22 O6' _chemical_formula_weight 262.30 _chemical_name_common 'tetramethyl-4,7-dioxadecanedioic acid' _chemical_name_systematic ; 2,2,9,9-tetramethyl-4,7-dioxadecanedioic acid ; _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 90.0 _cell_angle_beta 106.79(2) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 12.457(3) _cell_length_b 9.828(2) _cell_length_c 12.588(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 18.00 _cell_measurement_theta_min 9.00 _cell_volume 1475.4(5) _computing_cell_refinement 'Enraf-Nonius CAD-4 software' _computing_data_collection 'Enraf-Nonius CAD-4 software' _computing_data_reduction 'NRCVAX DATRD2' _computing_molecular_graphics NRCVAX _computing_publication_material 'NRCVAX TABLES Jan 94 Version' _computing_structure_refinement 'NRCVAX LSTSQ' _computing_structure_solution 'NRCVAX SOLVER' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf Nonius CAD-4' _diffrn_measurement_method '\q/2\q scan b/P/b ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'xray tube' _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_wavelength 0.71067 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3347 _diffrn_reflns_theta_max 26.91 _diffrn_reflns_theta_min 2.00 _diffrn_standards_decay_% 2.0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.181 _exptl_crystal_description block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.12 _refine_diff_density_min -0.11 _refine_ls_extinction_coef 4.4E3(15) _refine_ls_extinction_method 'Larson (1970)' _refine_ls_goodness_of_fit_obs 1.35 _refine_ls_hydrogen_treatment ' Hydroxyl H atoms refined isotropically, others riding (C-H 0.95 \%A)' _refine_ls_matrix_type full _refine_ls_number_parameters 172 _refine_ls_number_reflns 1511 _refine_ls_R_factor_all 0.097 _refine_ls_R_factor_obs 0.038 _refine_ls_shift/esd_max 0.006 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F) + 0.0008F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.061 _refine_ls_wR_factor_obs 0.052 _reflns_number_observed 1511 _reflns_number_total 3209 _reflns_observed_criterion 'Inet > 3.0\s(Inet)' _cod_data_source_file ab1215.cif _cod_data_source_block 89-58AMcA _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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F) + 0.0008F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(F) + 0.0008F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1475.4(4) _cod_original_sg_symbol_H-M 'P 21/a' _cod_original_formula_sum 'C12 H22 O6 ' _cod_database_code 2003231 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,1/2+y,-z 1/2+x,1/2-y,z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 _atom_site_aniso_type_symbol O1 0.0559(12) -0.0022(10) 0.0143(10) 0.0666(12) 0.0263(11) 0.0960(14) O O2 0.0607(11) -0.0003(9) 0.0212(10) 0.0679(12) 0.0304(10) 0.0910(13) O C1 0.0548(16) 0.0008(12) 0.0239(12) 0.0499(14) 0.0013(12) 0.0545(14) C C2 0.0566(15) 0.0097(12) 0.0191(12) 0.0500(14) 0.0023(12) 0.0573(14) C C21 0.103(2) 0.0197(15) 0.0308(17) 0.0606(17) -0.0007(14) 0.0751(18) C C22 0.0575(17) 0.0126(15) 0.0208(15) 0.086(2) 0.0089(17) 0.088(2) C C3 0.0707(17) 0.0109(12) 0.0148(13) 0.0497(14) 0.0086(13) 0.0590(15) C O4 0.0838(12) 0.0059(9) 0.0316(9) 0.0514(10) 0.0037(8) 0.0585(10) O C5 0.0653(16) 0.0057(13) 0.0196(13) 0.0692(17) 0.0115(13) 0.0532(14) C C6 0.0642(16) 0.0092(14) 0.0167(12) 0.0768(19) 0.0048(14) 0.0498(14) C O7 0.0637(11) 0.0148(9) 0.0312(9) 0.0745(12) 0.0145(9) 0.0662(11) O C8 0.0741(17) 0.0049(13) 0.0333(14) 0.0591(15) -0.0037(13) 0.0622(15) C C9 0.0628(16) 0.0004(12) 0.0185(12) 0.0514(14) -0.0073(12) 0.0515(14) C C91 0.0777(18) -0.0058(16) 0.0102(14) 0.0710(18) -0.0149(14) 0.0623(16) C C92 0.098(2) 0.0032(15) 0.0362(16) 0.0637(17) -0.0009(14) 0.0672(17) C C10 0.0502(15) 0.0012(12) 0.0138(12) 0.0546(15) -0.0052(12) 0.0536(14) C O10 0.0533(10) -0.0016(9) 0.0226(9) 0.0783(12) -0.0196(9) 0.0702(11) O O11 0.0596(12) -0.0234(12) 0.0319(11) 0.1243(17) -0.0637(14) 0.1027(16) O 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_type_symbol O1 0.00869(16) -0.15882(19) 0.07014(17) 0.0744(13) Uani O O2 0.13893(14) -0.01560(18) 0.05392(16) 0.0734(12) Uani O C1 0.1121(2) -0.1220(2) 0.0900(2) 0.0514(14) Uani C C2 0.1974(2) -0.2201(2) 0.1606(2) 0.0541(14) Uani C C21 0.1905(3) -0.3551(3) 0.0974(2) 0.078(2) Uani C C22 0.3143(2) -0.1604(3) 0.1865(2) 0.0770(19) Uani C C3 0.1655(2) -0.2470(2) 0.2669(2) 0.0606(16) Uani C O4 0.16385(14) -0.12087(15) 0.31971(13) 0.0622(11) Uani O C5 0.1285(2) -0.1305(3) 0.4173(2) 0.0620(16) Uani C C6 0.1362(2) 0.0060(3) 0.4708(2) 0.0636(17) Uani C O7 0.05352(14) 0.09987(17) 0.41246(14) 0.0655(11) Uani O C8 0.0817(2) 0.1699(2) 0.3257(2) 0.0623(16) Uani C C9 -0.0049(2) 0.2824(2) 0.2840(2) 0.0548(14) Uani C C91 -0.1209(2) 0.2233(3) 0.2328(2) 0.0724(17) Uani C C92 0.0337(3) 0.3649(3) 0.1976(2) 0.0737(19) Uani C C10 -0.0043(2) 0.3750(2) 0.3802(2) 0.0530(14) Uani C O10 -0.08870(14) 0.39596(18) 0.40930(14) 0.0663(11) Uani O O11 0.08976(15) 0.4315(2) 0.42822(18) 0.0938(15) Uani O H1 -0.038(3) -0.093(4) 0.031(3) 0.153(16) Uiso H H11 0.088(3) 0.492(4) 0.501(4) 0.186(17) Uiso H H21C 0.210 -0.340 0.031 0.0894 Uiso H H21A 0.241 -0.419 0.142 0.0894 Uiso H H21B 0.116 -0.390 0.080 0.0894 Uiso H H22C 0.332 -0.145 0.119 0.0870 Uiso H H22A 0.317 -0.077 0.225 0.0870 Uiso H H22B 0.367 -0.222 0.231 0.0870 Uiso H H3A 0.219 -0.306 0.314 0.0698 Uiso H H3B 0.093 -0.288 0.249 0.0698 Uiso H H5A 0.053 -0.162 0.398 0.0725 Uiso H H5B 0.175 -0.193 0.467 0.0725 Uiso H H6A 0.208 0.043 0.476 0.0736 Uiso H H6B 0.128 -0.006 0.543 0.0736 Uiso H H8A 0.154 0.208 0.353 0.0751 Uiso H H8B 0.081 0.109 0.267 0.0751 Uiso H H91C -0.173 0.295 0.208 0.0803 Uiso H H91A -0.120 0.167 0.172 0.0803 Uiso H H91B -0.142 0.171 0.287 0.0803 Uiso H H92C -0.018 0.436 0.170 0.0863 Uiso H H92A 0.106 0.402 0.232 0.0863 Uiso H H92B 0.037 0.307 0.138 0.0863 Uiso H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C ? 'International Tables Vol. IV Table 2.2B' 0.002 0.002 H ? 'International Tables Vol. IV Table 2.2B' 0.000 0.000 O ? 'International Tables Vol. IV Table 2.2B' 0.008 0.006 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 0 0 1 1 5 1 5 -2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 O1 H1 . . 111(2) no O1 C1 O2 . . 122.2(2) no O1 C1 C2 . . 115.2(2) no O2 C1 C2 . . 122.6(2) no C1 C2 C21 . . 108.7(2) no C1 C2 C22 . . 110.3(2) no C1 C2 C3 . . 107.9(2) no C21 C2 C22 . . 110.7(2) no C21 C2 C3 . . 108.4(2) no C22 C2 C3 . . 110.8(2) no C2 C3 O4 . . 107.8(2) no C3 O4 C5 . . 113.5(2) no O4 C5 C6 . . 109.5(2) no C5 C6 O7 . . 114.1(2) no C6 O7 C8 . . 114.2(2) no O7 C8 C9 . . 108.0(2) no C8 C9 C91 . . 111.1(2) no C8 C9 C92 . . 106.9(2) no C8 C9 C10 . . 108.7(2) no C91 C9 C92 . . 110.8(2) no C91 C9 C10 . . 110.7(2) no C92 C9 C10 . . 108.6(2) no C9 C10 O10 . . 122.3(2) no C9 C10 O11 . . 115.5(2) no O10 C10 O11 . . 122.2(2) no C10 O11 H11 . . 113(2) no O1 H1 O2 . 2_555 172(4) no O10 H11 O11 2_566 . 167(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 1.291(3) no O1 H1 0.92(4) no O2 C1 1.224(3) no C1 C2 1.518(3) no C2 C21 1.537(4) no C2 C22 1.516(4) no C2 C3 1.525(3) no C3 O4 1.410(3) no O4 C5 1.423(3) no C5 C6 1.492(4) no C6 O7 1.419(3) no O7 C8 1.418(3) no C8 C9 1.528(4) no C9 C91 1.518(4) no C9 C92 1.540(3) no C9 C10 1.513(3) no C10 O10 1.227(3) no C10 O11 1.280(3) no O11 H11 1.10(5) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O2 2.664(4) 2_555 no O2 H1 1.75 2_555 no O10 O11 2.660(3) 2_566 no O10 H11 1.57(5) 2_566 no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C21 63.4(2) no O1 C1 C2 C22 -175.1(3) no O1 C1 C2 C3 -53.9(2) no O2 C1 C2 C21 -116.2(2) no O2 C1 C2 C22 5.30(10) no O2 C1 C2 C3 126.5(3) no C1 C2 C3 O4 -58.1(2) no C21 C2 C3 O4 -175.6(3) no C22 C2 C3 O4 62.8(2) no C2 C3 O4 C5 176.4(2) no C3 O4 C5 C6 176.6(2) no O4 C5 C6 O7 71.9(2) no C5 C6 O7 C8 -84.4(2) no C6 O7 C8 C9 -170.8(3) no O7 C8 C9 C91 -64.1(2) no O7 C8 C9 C92 174.9(3) no O7 C8 C9 C10 57.9(2) no C8 C9 C10 O10 -122.3(3) no C8 C9 C10 O11 58.6(2) no C91 C9 C10 O10 -0.10(10) no C91 C9 C10 O11 -179.2(3) no C92 C9 C10 O10 121.7(3) no C92 C9 C10 O11 -57.3(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 12729069