#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/15/2101565.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_2101565 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_sum 'C12 H12 Br2 O6' _chemical_formula_weight 412.04 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 93.110(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.6220(10) _cell_length_b 7.8530(10) _cell_length_c 19.103(3) _cell_measurement_reflns_used 78 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 17 _cell_measurement_theta_min 14 _cell_volume 1441.3(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 'SHELXTL CIFTAB' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(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 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2876 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 2.14 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 120 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu 5.645 _exptl_absorpt_correction_T_max 0.244 _exptl_absorpt_correction_T_min 0.169 _exptl_absorpt_correction_type '\y scans (Sheldrick, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.899 _exptl_crystal_density_meas ? _exptl_crystal_description block _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 1.023 _refine_diff_density_min -0.904 _refine_ls_extinction_coef 0.0017(6) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.144 _refine_ls_hydrogen_treatment 'H atoms treated using a riding model' _refine_ls_matrix_type full _refine_ls_number_parameters 186 _refine_ls_number_reflns 2546 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_restrained_S_obs 1.144 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_obs 0.0490 _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^)+(0.0804P)^2^+3.0422P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1543 _refine_ls_wR_factor_obs 0.1391 _reflns_number_observed 1892 _reflns_number_total 2546 _reflns_observed_criterion >2sigma(I) _cod_data_source_file se0188.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0804P)^2^+3.0422P] 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^)+(0.0804P)^2^+3.0422P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2101565 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 0.0609(5) 0.0617(5) 0.0781(5) 0.0088(3) 0.0059(3) -0.0084(3) O1 0.075(3) 0.042(2) 0.034(2) 0.007(2) 0.001(2) -0.004(2) O2 0.080(3) 0.041(2) 0.068(3) -0.004(2) -0.035(2) -0.004(2) O3 0.068(3) 0.044(2) 0.056(2) 0.004(2) -0.017(2) 0.009(2) C1 0.053(3) 0.028(2) 0.036(3) -0.001(2) -0.008(2) 0.000(2) C2 0.057(3) 0.026(2) 0.039(3) -0.002(2) 0.001(2) 0.001(2) C3 0.041(3) 0.025(2) 0.054(3) 0.002(2) 0.003(2) 0.002(2) C7 0.053(3) 0.041(3) 0.044(3) 0.004(3) -0.009(2) 0.000(2) C8 0.076(4) 0.069(4) 0.059(4) 0.012(4) -0.009(3) 0.004(3) C9 0.069(5) 0.136(8) 0.095(6) 0.021(5) -0.006(4) -0.008(6) Br11 0.0610(5) 0.0629(5) 0.0847(5) 0.0130(3) 0.0249(4) 0.0039(3) O11 0.067(3) 0.040(2) 0.049(2) 0.006(2) 0.006(2) 0.002(2) O12 0.093(3) 0.044(2) 0.045(2) -0.008(2) 0.031(2) 0.002(2) O13 0.099(3) 0.040(2) 0.068(3) -0.013(2) 0.050(3) -0.020(2) C11 0.053(3) 0.024(2) 0.045(3) -0.001(2) 0.020(2) -0.002(2) C12 0.048(3) 0.028(3) 0.041(3) -0.003(2) 0.009(2) -0.002(2) C13 0.045(3) 0.028(2) 0.053(3) 0.001(2) 0.019(2) 0.000(2) C17 0.051(3) 0.042(3) 0.042(3) -0.004(3) 0.017(2) -0.006(2) C18 0.095(6) 0.075(5) 0.082(5) -0.013(4) 0.048(5) -0.038(4) C19 0.074(5) 0.203(11) 0.053(4) 0.036(7) 0.008(4) 0.011(6) 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 0.80829(7) -0.64140(9) 0.46781(4) 0.0668(3) Uani d . 1 Br O1 0.5528(5) -0.5923(5) 0.3642(2) 0.0503(10) Uani d . 1 O H01 0.598(6) -0.681(4) 0.3635(3) 0.055(19) Uiso calc R 1 H O2 0.2292(5) -0.5949(5) 0.3626(2) 0.0645(13) Uani d . 1 O O3 0.2786(4) -0.3167(5) 0.3625(2) 0.0567(11) Uani d . 1 O C1 0.4004(6) -0.4850(6) 0.4455(3) 0.0393(12) Uani d . 1 C C2 0.5289(6) -0.5509(6) 0.4318(3) 0.0404(12) Uani d . 1 C C3 0.6290(5) -0.5640(6) 0.4869(3) 0.0399(11) Uani d . 1 C C7 0.2920(6) -0.4745(7) 0.3856(3) 0.0466(13) Uani d . 1 C C8 0.1760(8) -0.2833(10) 0.3046(4) 0.068(2) Uani d . 1 C H8A 0.2060(8) -0.1879(10) 0.2770(4) 0.082 Uiso calc R 1 H H8B 0.1669(8) -0.3823(10) 0.2744(4) 0.082 Uiso calc R 1 H C9 0.0434(8) -0.2450(13) 0.3334(5) 0.100(3) Uani d . 1 C H9A -0.0246(8) -0.2230(13) 0.2959(5) 0.150 Uiso calc R 1 H H9B 0.0530(8) -0.1464(13) 0.3630(5) 0.150 Uiso calc R 1 H H9C 0.0141(8) -0.3402(13) 0.3604(5) 0.150 Uiso calc R 1 H Br11 0.18413(7) 0.14013(9) 0.51466(4) 0.0688(3) Uani d . 1 Br O11 0.3404(4) 0.0793(5) 0.3795(2) 0.0518(10) Uani d . 1 O H011 0.302(4) 0.172(3) 0.3828(10) 0.034(14) Uiso calc R 1 H O12 0.6417(5) 0.0847(5) 0.3293(2) 0.0597(12) Uani d . 1 O O13 0.6042(5) -0.1941(5) 0.3416(2) 0.0675(13) Uani d . 1 O C11 0.5498(6) -0.0204(6) 0.4342(3) 0.0399(12) Uani d . 1 C C12 0.4174(5) 0.0453(6) 0.4396(3) 0.0391(11) Uani d . 1 C C13 0.3675(5) 0.0639(6) 0.5068(3) 0.0410(12) Uani d . 1 C C17 0.6036(6) -0.0352(7) 0.3617(3) 0.0448(13) Uani d . 1 C C18 0.6559(9) -0.2316(10) 0.2724(4) 0.082(2) Uani d . 1 C H18A 0.7016(9) -0.1318(10) 0.2545(4) 0.099 Uiso calc R 1 H H18B 0.7234(9) -0.3233(10) 0.2763(4) 0.099 Uiso calc R 1 H C19 0.5421(9) -0.2802(16) 0.2247(4) 0.110(4) Uani d . 1 C H19A 0.5767(9) -0.3045(16) 0.1796(4) 0.165 Uiso calc R 1 H H19B 0.4760(9) -0.1888(16) 0.2205(4) 0.165 Uiso calc R 1 H H19C 0.4978(9) -0.3798(16) 0.2422(4) 0.165 Uiso calc 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_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O3 C8 . . 118.0(5) yes C2 C1 C3 . 3_646 120.6(5) yes C2 C1 C7 . . 117.8(5) yes C3 C1 C7 3_646 . 121.5(5) yes O1 C2 C1 . . 117.9(5) yes O1 C2 C3 . . 123.6(5) yes C1 C2 C3 . . 118.4(5) yes C2 C3 C1 . 3_646 120.9(5) yes C2 C3 Br1 . . 118.8(4) yes C1 C3 Br1 3_646 . 120.2(4) yes O2 C7 O3 . . 125.7(5) yes O2 C7 C1 . . 123.5(5) yes O3 C7 C1 . . 110.9(5) yes C9 C8 O3 . . 108.8(6) yes C17 O13 C18 . . 117.7(5) yes C12 C11 C13 . 3_656 121.4(5) yes C12 C11 C17 . . 117.4(5) yes C13 C11 C17 3_656 . 121.1(5) yes O11 C12 C11 . . 118.2(5) yes O11 C12 C13 . . 123.7(5) yes C11 C12 C13 . . 117.9(5) yes C11 C13 C12 3_656 . 120.6(5) yes C11 C13 Br11 3_656 . 120.9(4) yes C12 C13 Br11 . . 118.5(4) yes O12 C17 O13 . . 126.4(5) yes O12 C17 C11 . . 123.0(5) yes O13 C17 C11 . . 110.6(5) yes C19 C18 O13 . . 109.9(6) yes 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 . 1.883(5) yes O1 C2 . 1.363(6) yes O2 C7 . 1.193(7) yes O3 C7 . 1.319(7) yes O3 C8 . 1.465(8) yes C1 C2 . 1.378(8) yes C1 C3 3_646 1.392(7) yes C1 C7 . 1.508(7) yes C2 C3 . 1.392(7) yes C3 C1 3_646 1.392(7) yes C8 C9 . 1.447(11) yes Br11 C13 . 1.877(5) yes O11 C12 . 1.359(7) yes O12 C17 . 1.196(6) yes O13 C17 . 1.306(7) yes O13 C18 . 1.468(7) yes C11 C12 . 1.384(7) yes C11 C13 3_656 1.386(8) yes C11 C17 . 1.509(7) yes C12 C13 . 1.402(7) yes C13 C11 3_656 1.386(8) yes C18 C19 . 1.437(11) 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_1 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C3 C1 C2 O1 3_646 . -178.3(4) no C7 C1 C2 O1 . . 4.1(7) no C3 C1 C2 C3 3_646 . -1.3(8) no C7 C1 C2 C3 . . -178.9(5) no O1 C2 C3 C1 . 3_646 178.1(5) no C1 C2 C3 C1 . 3_646 1.3(8) no O1 C2 C3 Br1 . . 0.5(7) no C1 C2 C3 Br1 . . -176.4(4) no C8 O3 C7 O2 . . 1.5(9) no C8 O3 C7 C1 . . -179.3(5) no C2 C1 C7 O2 . . 75.6(8) no C3 C1 C7 O2 3_646 . -102.0(7) no C2 C1 C7 O3 . . -103.6(6) no C3 C1 C7 O3 3_646 . 78.7(7) no C7 O3 C8 C9 . . 89.2(8) no C13 C11 C12 O11 3_656 . -177.7(4) no C17 C11 C12 O11 . . 5.1(7) no C13 C11 C12 C13 3_656 . -1.2(8) no C17 C11 C12 C13 . . -178.4(5) no O11 C12 C13 C11 . 3_656 177.5(5) no C11 C12 C13 C11 . 3_656 1.2(8) no O11 C12 C13 Br11 . . 0.0(7) no C11 C12 C13 Br11 . . -176.3(4) no C18 O13 C17 O12 . . -0.1(10) no C18 O13 C17 C11 . . -179.0(6) no C12 C11 C17 O12 . . 74.7(8) no C13 C11 C17 O12 3_656 . -102.5(7) no C12 C11 C17 O13 . . -106.4(6) no C13 C11 C17 O13 3_656 . 76.4(6) no C17 O13 C18 C19 . . -108.7(8) no C1 C2 O1 H01 . . -141.(5) no C3 C2 O1 H01 . . 42.(5) no C11 C12 O11 H011 . . -136.(4) no C13 C12 O11 H011 . . 48.(4) no