#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012844.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_2012844 loop_ _publ_author_name 'Tomura, Masaaki' 'Akhtaruzzaman, Md.' 'Suzuki, Kazuharu' 'Yamashita, Yoshiro' _publ_section_title ; 4,7-Diiodo-2,1,3-benzothiadiazole and 7,7'-diiodo-4,4'-bi(2,1,3-benzothiadiazole) ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o373 _journal_page_last o375 _journal_paper_doi 10.1107/S0108270102008296 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C12 H4 I2 N4 S2' _chemical_formula_sum 'C12 H4 I2 N4 S2' _chemical_formula_weight 522.11 _chemical_melting_point 311 _chemical_name_systematic ; 7,7'-diiodo-4,4'-bis(2,1,3-benzothiadiazole) ; _space_group_IT_number 43 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.892(14) _cell_length_b 33.38(2) _cell_length_c 3.942(3) _cell_measurement_reflns_used 3274 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 3.13 _cell_volume 2749(3) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Molecular Structure Corporation & Rigaku Corporation, 2001)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation & Rigaku Corporation, 2000)' _computing_molecular_graphics 'ORTEP-III (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 14.62 _diffrn_measured_fraction_theta_full 0.971 _diffrn_measured_fraction_theta_max 0.971 _diffrn_measurement_device_type 'Rigaku Mercury CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graphite monochromator' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.035 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 6500 _diffrn_reflns_theta_full 27.47 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_min 3.12 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.873 _exptl_absorpt_correction_T_max 0.829 _exptl_absorpt_correction_T_min 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Jacobson, 1998)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 2.523 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1936 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.98 _refine_diff_density_min -1.07 _refine_ls_abs_structure_details 'Flack (1983); 538 Friedel pairs Query' _refine_ls_abs_structure_Flack -0.01(8) _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.212 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1438 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.211 _refine_ls_R_factor_all 0.057 _refine_ls_R_factor_gt 0.055 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0648P)^2^+102.9652P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.151 _refine_ls_wR_factor_ref 0.152 _reflns_number_gt 1394 _reflns_number_total 1438 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ta1368.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 2012844 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol I1 0.17133(4) 0.08701(2) 0.7312(2) 0.0485(4) Uani d . 1 . . I S1 0.07266(13) 0.21576(9) 1.0625(9) 0.0386(9) Uani d . 1 . . S N1 0.0992(4) 0.1722(3) 0.967(4) 0.034(2) Uani d . 1 . . N N2 0.1327(4) 0.2431(2) 0.949(3) 0.0285(19) Uani d . 1 . . N C1 0.1995(5) 0.1463(3) 0.708(3) 0.025(2) Uani d . 1 . . C C2 0.1575(5) 0.1771(3) 0.839(3) 0.025(2) Uani d . 1 . . C C3 0.1774(5) 0.2185(3) 0.824(3) 0.025(2) Uani d . 1 . . C C4 0.2387(4) 0.2293(3) 0.695(3) 0.025(2) Uani d . 1 . . C C5 0.2763(5) 0.1985(3) 0.577(3) 0.026(2) Uani d . 1 . . C H5 0.3163 0.2044 0.4862 0.031 Uiso calc R 1 . . H C6 0.2561(6) 0.1580(3) 0.588(4) 0.039(4) Uani d . 1 . . C H6 0.2840 0.1384 0.5073 0.047 Uiso calc R 1 . . H 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 I1 0.0454(5) 0.0290(4) 0.0710(7) -0.0053(3) 0.0004(5) -0.0047(4) S1 0.0267(13) 0.0337(14) 0.055(3) -0.0008(10) 0.0127(13) -0.0007(13) N1 0.032(4) 0.029(4) 0.041(6) -0.003(3) 0.015(5) -0.006(6) N2 0.025(4) 0.022(4) 0.038(5) -0.004(3) 0.004(4) -0.007(4) C1 0.030(5) 0.020(4) 0.027(6) 0.002(3) 0.001(4) -0.003(4) C2 0.017(4) 0.020(4) 0.038(7) -0.001(3) -0.003(4) -0.002(4) C3 0.025(5) 0.015(4) 0.035(7) 0.002(3) 0.009(4) 0.001(4) C4 0.018(4) 0.022(5) 0.036(6) -0.002(3) -0.009(4) -0.006(5) C5 0.026(5) 0.027(5) 0.025(6) 0.000(4) 0.007(4) -0.002(4) C6 0.026(5) 0.019(5) 0.073(11) 0.000(4) -0.004(5) -0.011(5) 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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_3 _geom_angle _geom_angle_publ_flag N1 S1 N2 . 100.3(4) yes C2 N1 S1 . 107.3(7) yes C3 N2 S1 . 107.2(7) yes C6 C1 C2 . 117.1(9) yes C6 C1 I1 . 123.4(8) no C2 C1 I1 . 119.5(7) no N1 C2 C3 . 113.2(9) yes N1 C2 C1 . 127.3(9) yes C3 C2 C1 . 119.5(9) yes N2 C3 C2 . 111.9(9) yes N2 C3 C4 . 127.1(9) yes C2 C3 C4 . 121.0(9) yes C5 C4 C3 . 116.4(9) yes C5 C4 C4 14 121.5(10) yes C3 C4 C4 14 122.1(10) yes C4 C5 C6 . 122.2(10) yes C4 C5 H5 . 118.9 no C6 C5 H5 . 118.9 no C1 C6 C5 . 123.8(10) no C1 C6 H6 . 118.1 no C5 C6 H6 . 118.1 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 I1 C1 . 2.065(9) yes S1 N1 . 1.599(9) yes S1 N2 . 1.616(9) yes N1 C2 . 1.331(13) yes N2 C3 . 1.337(13) yes C1 C6 . 1.332(16) yes C1 C2 . 1.446(14) yes C2 C3 . 1.445(13) yes C3 C4 . 1.423(13) yes C4 C5 . 1.376(14) yes C4 C4 14 1.462(18) yes C5 C6 . 1.417(15) yes C5 H5 . 0.9300 no C6 H6 . 0.9300 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 N2 S1 N1 C2 . . -0.1(11) no N1 S1 N2 C3 . . 0.6(11) no S1 N1 C2 C3 . . -0.4(14) no S1 N1 C2 C1 . . -178.1(11) no C6 C1 C2 N1 . . 179.5(13) no I1 C1 C2 N1 . . -2.8(18) no C6 C1 C2 C3 . . 2.0(17) no I1 C1 C2 C3 . . 179.6(8) no S1 N2 C3 C2 . . -0.9(13) no S1 N2 C3 C4 . . -179.6(10) no N1 C2 C3 N2 . . 0.8(15) no C1 C2 C3 N2 . . 178.7(11) no N1 C2 C3 C4 . . 179.7(12) no C1 C2 C3 C4 . . -2.4(17) no N2 C3 C4 C5 . . -179.3(11) no C2 C3 C4 C5 . . 2.0(17) no N2 C3 C4 C4 . 14 2.1(17) no C2 C3 C4 C4 . 14 -176.5(8) no C3 C4 C5 C6 . . -1.3(17) no C4 C4 C5 C6 14 . 177.3(9) no C2 C1 C6 C5 . . -1(2) no I1 C1 C6 C5 . . -178.8(10) no C4 C5 C6 C1 . . 1(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 90707239