#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/15/2101567.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_2101567 loop_ _publ_author_name 'N\"ather, C.' 'Nagel, N.' 'Bock, H.' 'Seitz, W.' 'Havlas, Z.' _publ_section_title ; Structural, kinetic and thermodynamic aspects of the conformational dimorphism of diethyl 3,6-dibromo-2,5-dihydroxyterephthalate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 697 _journal_page_last 706 _journal_paper_doi 10.1107/S0108768196003187 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C12 H12 Br2 O6 , 2C2 H6 O' _chemical_formula_sum 'C16 H24 Br2 O8' _chemical_formula_weight 504.17 _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 SHELXL _cell_angle_alpha 116.82(3) _cell_angle_beta 96.10(3) _cell_angle_gamma 102.29(3) _cell_formula_units_Z 1 _cell_length_a 8.002(2) _cell_length_b 8.232(2) _cell_length_c 8.966(2) _cell_measurement_reflns_used 68 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 22.5 _cell_measurement_theta_min 19 _cell_volume 500.9(3) _computing_cell_refinement 'STOE DIF-4' _computing_data_collection 'STOE DIF-4' _computing_data_reduction 'STOE REDU-4' _computing_molecular_graphics 'SHELXTL PC' _computing_publication_material 'SHELXL CIFTAB' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_measurement_device 'STOE AED-II' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0527 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 3556 _diffrn_reflns_theta_max 32.52 _diffrn_reflns_theta_min 2.62 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 120 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 4.084 _exptl_absorpt_correction_T_max 0.522 _exptl_absorpt_correction_T_min 0.383 _exptl_absorpt_correction_type '\y scans (Sheldrick, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 254 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max 1.042 _refine_diff_density_min -2.603 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.097 _refine_ls_goodness_of_fit_obs 1.126 _refine_ls_hydrogen_treatment 'H atoms treated using a riding model' _refine_ls_matrix_type full _refine_ls_number_parameters 120 _refine_ls_number_reflns 3327 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.115 _refine_ls_restrained_S_obs 1.126 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_obs 0.0429 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+0.7709P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1311 _refine_ls_wR_factor_obs 0.1257 _reflns_number_observed 3001 _reflns_number_total 3328 _reflns_observed_criterion >2sigma(I) _cod_data_source_file se0188.cif _cod_data_source_block solvate _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.0834P)^2^+0.7709P] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0834P)^2^+0.7709P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 500.9(2) _cod_database_code 2101567 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -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 Br1 0.0170(2) 0.02651(15) 0.01815(14) 0.00141(10) -0.00079(9) 0.01313(11) O1 0.0056(7) 0.0182(7) 0.0199(8) -0.0047(6) -0.0050(6) 0.0122(7) O2 0.0163(8) 0.0176(8) 0.0217(8) 0.0065(6) 0.0094(7) 0.0112(7) O3 0.0143(8) 0.0127(7) 0.0228(8) 0.0045(6) 0.0096(7) 0.0115(6) C1 0.0062(9) 0.0095(8) 0.0119(8) 0.0007(7) 0.0006(7) 0.0060(7) C2 0.0038(9) 0.0103(8) 0.0126(8) -0.0015(7) -0.0017(7) 0.0061(7) C3 0.0069(9) 0.0115(8) 0.0107(8) 0.0014(7) -0.0007(7) 0.0061(7) C7 0.0069(9) 0.0114(8) 0.0117(8) 0.0002(7) -0.0007(7) 0.0065(7) C8 0.0160(11) 0.0142(9) 0.0220(10) 0.0028(8) 0.0079(9) 0.0123(8) C9 0.0232(13) 0.0133(10) 0.0346(14) 0.0045(9) 0.0108(11) 0.0117(10) O4 0.0184(9) 0.0294(10) 0.0202(9) 0.0138(8) -0.0002(7) 0.0101(8) C11 0.0147(12) 0.0300(13) 0.0197(11) 0.0044(10) 0.0007(9) 0.0080(10) C12 0.0171(13) 0.0297(14) 0.034(2) 0.0009(11) -0.0042(12) 0.0101(12) 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_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br1 -0.16378(3) -0.06760(4) -0.37913(3) 0.02093(11) Uani d . 1 Br O1 -0.3406(2) -0.2367(3) -0.1631(2) 0.0155(3) Uani d . 1 O H01 -0.3908(18) -0.205(4) -0.229(4) 0.019 Uiso calc R 1 H O2 -0.2975(3) -0.1279(3) 0.2497(3) 0.0171(3) Uani d . 1 O O3 -0.1928(2) -0.3674(2) 0.0887(3) 0.0149(3) Uani d . 1 O C1 -0.0998(3) -0.0886(3) 0.0740(3) 0.0093(3) Uani d . 1 C C2 -0.1740(3) -0.1190(3) -0.0879(3) 0.0096(3) Uani d . 1 C C3 -0.0708(3) -0.0293(3) -0.1611(3) 0.0099(4) Uani d . 1 C C7 -0.2084(3) -0.1938(3) 0.1488(3) 0.0103(4) Uani d . 1 C C8 -0.2927(3) -0.4910(3) 0.1459(3) 0.0160(4) Uani d . 1 C H8A -0.4181(3) -0.4952(3) 0.1281(3) 0.019 Uiso calc R 1 H H8B -0.2454(3) -0.4437(3) 0.2694(3) 0.019 Uiso calc R 1 H C9 -0.2729(4) -0.6853(4) 0.0389(4) 0.0235(5) Uani d . 1 C H9A -0.3376(4) -0.7742(4) 0.0722(4) 0.035 Uiso calc R 1 H H9B -0.1481(4) -0.6786(4) 0.0577(4) 0.035 Uiso calc R 1 H H9C -0.3199(4) -0.7299(4) -0.0828(4) 0.035 Uiso calc R 1 H O4 -0.4105(3) 0.2023(3) 0.3530(3) 0.0227(4) Uani d . 1 O H04 -0.378(6) 0.103(4) 0.3145(3) 0.027 Uiso calc R 1 H C11 -0.3702(4) 0.2946(5) 0.5366(4) 0.0238(5) Uani d . 1 C H11B -0.4069(4) 0.1988(5) 0.5739(4) 0.029 Uiso d R 1 H H11A -0.4375(4) 0.3877(5) 0.5804(4) 0.029 Uiso d R 1 H C12 -0.1765(4) 0.3963(5) 0.6124(5) 0.0310(7) Uani d . 1 C H12C -0.1538(4) 0.4587(5) 0.7380(5) 0.047 Uiso d R 1 H H12B -0.1400(4) 0.4921(5) 0.5767(5) 0.047 Uiso d R 1 H H12A -0.1098(4) 0.3039(5) 0.5717(5) 0.047 Uiso d R 1 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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_site_symmetry_1 _geom_angle _geom_angle_publ_flag C7 O3 C8 . 117.5(2) yes C3 C1 C2 2 121.2(2) yes C3 C1 C7 2 121.0(2) yes C2 C1 C7 . 117.7(2) yes O1 C2 C1 . 117.0(2) yes O1 C2 C3 . 125.2(2) yes C1 C2 C3 . 117.8(2) yes C1 C3 C2 2 121.0(2) yes C1 C3 Br1 2 119.6(2) yes C2 C3 Br1 . 119.4(2) yes O2 C7 O3 . 125.0(2) yes O2 C7 C1 . 124.8(2) yes O3 C7 C1 . 110.3(2) yes O3 C8 C9 . 106.1(2) yes O4 C11 C12 . 111.7(3) 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 Br1 C3 . 1.874(2) yes O1 C2 . 1.356(3) yes O2 C7 . 1.216(3) yes O3 C7 . 1.321(3) yes O3 C8 . 1.465(3) yes C1 C3 2 1.393(3) yes C1 C2 . 1.396(3) yes C1 C7 . 1.511(3) yes C2 C3 . 1.397(3) yes C3 C1 2 1.393(3) yes C8 C9 . 1.503(4) yes O4 C11 . 1.430(4) yes C11 C12 . 1.509(4) 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 C1 C2 O1 2 . 179.7(2) no C7 C1 C2 O1 . . 2.0(3) no C3 C1 C2 C3 2 . 0.8(4) no C7 C1 C2 C3 . . -176.9(2) no O1 C2 C3 C1 . 2 -179.6(2) no C1 C2 C3 C1 . 2 -0.8(4) no O1 C2 C3 Br1 . . 0.7(3) no C1 C2 C3 Br1 . . 179.4(2) no C8 O3 C7 O2 . . 1.1(4) no C8 O3 C7 C1 . . -178.9(2) no C3 C1 C7 O2 2 . 85.7(3) no C2 C1 C7 O2 . . -96.5(3) no C3 C1 C7 O3 2 . -94.3(2) no C2 C1 C7 O3 . . 83.4(3) no C7 O3 C8 C9 . . 171.6(2) no C1 C2 O1 H01 . . 151.(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139063288