#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008148.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_2008148 loop_ _publ_author_name 'Gerkin, Roger E.' _publ_section_title ; Hydrogen bonding in (2R,3R)-(+)-2,3-dimethoxybutanedioic acid [(+)-tartaric acid dimethyl ether] ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 209 _journal_page_last 211 _journal_paper_doi 10.1107/S0108270198012694 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C6 H10 O6 ' _chemical_formula_sum 'C6 H10 O6' _chemical_formula_weight 178.14 _chemical_name_common '(+)-tartaric acid dimethyl ether' _chemical_name_systematic '(2R,3R)-(+)-2,3-dimethoxybutanedioic acid' _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'I 2y' _symmetry_space_group_name_H-M 'I 1 2 1' _cell_angle_alpha 90 _cell_angle_beta 90.147(5) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.0863(5) _cell_length_b 4.3394(6) _cell_length_c 13.2126(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.5 _cell_measurement_theta_min 14.5 _cell_volume 406.29(7) _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, 1995) ; _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 AFC-5S _diffrn_measurement_method '\w/2\q 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 0.010 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 706 _diffrn_reflns_theta_max 30.03 _diffrn_reflns_theta_min 2.0 _diffrn_standards_decay_% ' +- 0.8 (ave. max. rel. intensity)' _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.456 _exptl_crystal_description 'cut prism' _exptl_crystal_F_000 188 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.21 _refine_diff_density_min -0.16 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_obs 1.90 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 62 _refine_ls_number_reflns 659 _refine_ls_R_factor_gt 0.031 _refine_ls_shift/su_max '< 0.01' _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/\s^2^(F^2^)' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.056 _reflns_number_gt 569 _reflns_number_total 659 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file fr1158.cif _cod_data_source_block 1 _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 6 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/\s^2^(F^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^2^)'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 406.29(6) _cod_original_sg_symbol_H-M 'I 2' _cod_database_code 2008148 loop_ _symmetry_equiv_pos_as_xyz x,y,z '-x, y, -z' '1/2+x, 1/2+y, 1/2+z' '1/2 -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 -0.2195(2) 0.5812 0.87064(9) 0.0493(4) Uani ? ? O2 -0.0661(2) 0.2023(5) 0.79055(8) 0.0489(4) Uani ? ? O3 0.1805(2) 0.1393(5) 0.94821(8) 0.0354(3) Uani ? ? C1 -0.0846(2) 0.3751(5) 0.86120(10) 0.0324(4) Uani ? ? C2 0.0534(2) 0.3872(5) 0.94990(10) 0.0277(4) Uani ? ? C3 0.3411(3) 0.1911(8) 0.8863(2) 0.0614(7) Uani ? ? H1 -0.282(3) 0.604(7) 0.817(2) 0.084(8) Uiso ? ? H2 0.120(2) 0.593(5) 0.9440(10) 0.034(5) Uiso ? ? H3 0.4237 0.0102 0.8888 0.0737 Uiso calc C3 H4 0.3003 0.2268 0.8163 0.0737 Uiso calc C3 H5 0.4099 0.3720 0.9110 0.0737 Uiso calc C3 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 0.0581(8) 0.0550(10) 0.0351(7) 0.0128(8) -0.0234(6) 0.0037(7) O2 0.0495(7) 0.0690(10) 0.0281(5) -0.0056(9) -0.0139(5) -0.0133(7) O3 0.0383(6) 0.0359(7) 0.0320(6) 0.0037(6) -0.0027(4) -0.0019(6) C1 0.0363(9) 0.0381(10) 0.0228(7) -0.0119(9) -0.0082(6) 0.0076(7) C2 0.0355(9) 0.0257(8) 0.0217(7) -0.0019(8) -0.0091(6) -0.0005(7) C3 0.0430(10) 0.081(2) 0.0600(10) 0.0050(10) 0.0093(9) -0.0030(10) 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 .003 .002 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' 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 ? ? 112.0(10) no C2 O3 C3 ? ? 113.7(2) no O1 C1 O2 ? ? 125.20(10) yes O1 C1 C2 ? ? 111.70(10) yes O2 C1 C2 ? ? 123.1(2) yes O3 C2 C1 ? ? 111.80(10) no O3 C2 C2 ? 2_557 109.48(10) no O3 C2 H2 ? ? 112.3(9) no C1 C2 C2 ? 2_557 110.3(2) yes C1 C2 H2 ? ? 105.6(9) no C2 C2 H2 2_557 ? 107.2(10) no O3 C3 H3 ? ? 109.5 no O3 C3 H4 ? ? 109.5 no O3 C3 H5 ? ? 109.5 no H3 C3 H4 ? ? 109.5 no H3 C3 H5 ? ? 109.5 no H4 C3 H5 ? ? 109.5 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 C1 ? ? 1.315(2) yes O1 H1 ? ? 0.84(2) no O2 C1 ? ? 1.205(2) yes O3 C2 ? ? 1.403(2) yes O3 C3 ? ? 1.421(2) yes C1 C2 ? ? 1.525(2) yes C2 C2 ? 2_557 1.527(3) yes C2 H2 ? ? 1.01(2) no C3 H3 ? ? 0.980 no C3 H4 ? ? 0.980 no C3 H5 ? ? 0.980 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 O1 H1 O2 4_456 0.84(2) 1.84(2) 2.665(2) 172(3) yes C2 H2 O3 1_565 1.01(2) 2.41(2) 3.386(2) 162.0(10) yes 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_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C1 C2 C2 C1 . 2_557 2_557 175.8(2) yes C1 C2 O3 C3 . . . 85.0(2) yes O3 C2 C2 C1 . 2_557 2_557 52.30(10) yes C2 C2 O3 C3 2_557 2_557 2_557 -152.40(10) yes O3 C2 C2 O3 . 2_557 2_557 -71.2(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 14092549