#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/29/2002939.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_2002939 loop_ _publ_author_name 'Ojala, Charles R.' 'Ojala, William H.' 'Britton, Doyle' 'Gougoutas, J. Z.' _publ_section_title ; Packing similarities of three isosteric molecules: 4,5-dichlorophthalic anhydride, 4,5-dibromophthalic anhydride and 5,6-dichlorobenzfurazan 1-oxide, including three polymorphs of 5,6-dichlorobenzfurazan 1-oxide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 530 _journal_page_last 542 _journal_paper_doi 10.1107/S0108768199000348 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C8 H2 Br2 O3' _chemical_formula_weight 305.92 _chemical_name_common '4,5-dibromophthalic anhydride' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1 (1/2*x+1/2*y,1/2*x-1/2*y,-z)' _symmetry_space_group_name_H-M 'C -1' _audit_creation_method 'SHELXL plus manual additions' _cell_angle_alpha 105.08(3) _cell_angle_beta 99.20(3) _cell_angle_gamma 81.29(3) _cell_formula_units_Z 4 _cell_length_a 12.923(3) _cell_length_b 9.209(2) _cell_length_c 7.6280(15) _cell_measurement_reflns_used 25 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 22 _cell_measurement_theta_min 13 _cell_volume 859.5(4) _diffrn_ambient_temperature 297(2) _diffrn_measurement_device CAD-4 _diffrn_measurement_method \w-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 0.050 _diffrn_reflns_av_sigmaI/netI 0.085 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4009 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_min 2.65 _diffrn_standards_decay_% <1 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 9.40 _exptl_absorpt_correction_T_max 0.52 _exptl_absorpt_correction_T_min 0.23 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North, A. C. T., Phillips, D. C., and Mathews, F. S. (1968). Acta Cryst., A24, 351-359. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 2.364 _exptl_crystal_density_meas ? _exptl_crystal_description plate _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.80 _refine_diff_density_min -0.74 _refine_ls_extinction_coef 0.0047(9) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.028 _refine_ls_goodness_of_fit_obs 1.120 _refine_ls_hydrogen_treatment 'idealized positions' _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2057 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_restrained_S_obs 1.120 _refine_ls_R_factor_all 0.099 _refine_ls_R_factor_obs 0.050 _refine_ls_shift/esd_max 0.01 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.064P)^2^+0.18P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.139 _refine_ls_wR_factor_obs 0.117 _reflns_number_observed 1284 _reflns_number_total 2058 _reflns_observed_criterion >2sigma(I) _cod_data_source_file bk0061.cif _cod_data_source_block BPA _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.064P)^2^+0.18P] 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^)+(0.064P)^2^+0.18P] 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 859.5(3) _cod_original_sg_symbol_H-M C-1 _cod_database_code 2002939 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_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 C1 0.031(3) 0.043(3) 0.038(4) -0.004(3) -0.005(3) 0.013(3) C2 0.036(4) 0.044(3) 0.039(4) -0.002(3) 0.005(3) 0.011(3) C3 0.027(3) 0.045(3) 0.036(3) -0.005(2) -0.004(3) 0.009(3) C4 0.038(4) 0.035(3) 0.040(4) 0.002(3) 0.004(3) 0.013(3) C5 0.039(4) 0.038(3) 0.036(4) -0.008(3) -0.001(3) 0.008(3) C6 0.027(3) 0.038(3) 0.039(4) -0.004(2) -0.002(3) 0.007(3) C7 0.045(4) 0.038(3) 0.047(4) -0.006(3) 0.000(3) 0.010(3) C8 0.035(4) 0.042(3) 0.052(5) -0.004(3) 0.002(3) 0.011(3) O1 0.050(3) 0.050(3) 0.081(4) 0.001(2) -0.020(3) 0.024(3) O2 0.040(3) 0.037(2) 0.068(4) -0.006(2) -0.013(3) 0.012(2) O3 0.045(3) 0.052(3) 0.082(4) -0.018(2) -0.017(3) 0.019(3) Br4 0.0495(5) 0.0434(4) 0.0597(6) 0.0052(3) 0.0031(4) 0.0211(4) Br5 0.0517(5) 0.0473(4) 0.0586(5) -0.0184(3) 0.0002(4) 0.0137(3) 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_disorder_group _atom_site_type_symbol C1 0.5553(5) 0.2655(8) 0.2842(9) 0.0378(14) Uani d . 1 . C C2 0.4529(5) 0.2683(8) 0.1995(10) 0.0399(15) Uani d . 1 . C C3 0.3955(5) 0.3988(8) 0.1619(9) 0.0368(14) Uani d . 1 . C H3 0.3259(5) 0.4010(8) 0.1070(9) 0.044 Uiso calc R 1 . H C4 0.4498(5) 0.5276(7) 0.2125(9) 0.0377(14) Uani d . 1 . C C5 0.5523(5) 0.5250(7) 0.2963(10) 0.0382(14) Uani d . 1 . C C6 0.6090(5) 0.3925(7) 0.3352(9) 0.0356(13) Uani d . 1 . C H6 0.6783(5) 0.3898(7) 0.3918(9) 0.043 Uiso calc R 1 . H C7 0.5912(6) 0.1096(8) 0.3068(11) 0.044(2) Uani d . 1 . C C8 0.4208(6) 0.1150(8) 0.1613(11) 0.044(2) Uani d . 1 . C O1 0.6722(5) 0.0542(6) 0.3695(9) 0.063(2) Uani d . 1 . O O2 0.5069(4) 0.0238(5) 0.2304(8) 0.0509(13) Uani d . 1 . O O3 0.3416(5) 0.0645(6) 0.0907(9) 0.061(2) Uani d . 1 . O Br4 0.37379(6) 0.70771(8) 0.16374(12) 0.0508(3) Uani d . 1 . Br Br5 0.62425(6) 0.69818(9) 0.35590(12) 0.0518(3) Uani d . 1 . Br 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 _geom_angle_publ_flag C2 C1 C6 122.4(6) yes C2 C1 C7 108.0(6) yes C6 C1 C7 129.6(6) yes C1 C2 C3 122.4(7) yes C1 C2 C8 108.5(6) yes C3 C2 C8 129.1(7) yes C2 C3 C4 115.4(6) yes C5 C4 C3 122.3(6) yes C5 C4 Br4 121.1(5) yes C3 C4 Br4 116.6(5) yes C4 C5 C6 121.6(6) yes C4 C5 Br5 121.3(5) yes C6 C5 Br5 117.1(5) yes C1 C6 C5 115.9(6) yes O1 C7 O2 121.2(6) yes O1 C7 C1 132.1(7) yes O2 C7 C1 106.8(6) yes O3 C8 O2 120.9(7) yes O3 C8 C2 132.3(7) yes O2 C8 C2 106.8(6) yes C7 O2 C8 110.0(5) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.376(9) yes C1 C6 1.386(9) yes C1 C7 1.486(9) yes C2 C3 1.385(9) yes C2 C8 1.476(10) yes C3 C4 1.405(9) yes C4 C5 1.376(9) yes C4 Br4 1.888(6) yes C5 C6 1.401(9) yes C5 Br5 1.885(7) yes C7 O1 1.179(9) yes C7 O2 1.403(9) yes C8 O3 1.179(9) yes C8 O2 1.408(8) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21140668 2 PubChem 12658461