#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006080.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_2006080 loop_ _publ_author_name 'Kanno, H.' 'Iijima, K.' _publ_contact_author ; Dr Kinya Iijima Department of Chemistry Faculty of Science Shizuoka University 836 Oya, Shizuoka 422 Japan ; _publ_section_title ; 4,4'-Dimethyl-2,2'-bipyridine 1,1'-Dioxide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 498 _journal_page_last 499 _journal_paper_doi 10.1107/S010827019601548X _journal_volume 53 _journal_year 1997 _chemical_formula_sum 'C12 H12 N2 O2' _chemical_formula_weight 216.24 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_type_scat_source 'International Tables (1974)' _cell_angle_alpha 90.00(0) _cell_angle_beta 107.09(3) _cell_angle_gamma 90.00(0) _cell_formula_units_Z 4 _cell_length_a 11.232(4) _cell_length_b 9.175(3) _cell_length_c 10.444(4) _cell_measurement_reflns_used 23 _cell_measurement_temperature 298 _cell_measurement_theta_max 17.5 _cell_measurement_theta_min 14.3 _cell_volume 1028.8(7) _computing_cell_refinement 'MXC Software' _computing_data_collection 'MXC Software (MAC Science, 1989)' _computing_data_reduction 'Crystan (Gilmore & Brown, 1988)' _computing_molecular_graphics 'ORTEP (Johnson, 1965), Crystan' _computing_publication_material Crystan _computing_structure_refinement Crystan _computing_structure_solution Crystan _diffrn_measurement_device 'Mac Science MXC3' _diffrn_measurement_method '2\q/\w ' _diffrn_radiation_type 'Mo K\a ' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1328 _diffrn_reflns_theta_max 26.43 _diffrn_standards_decay_% ' < 2 ' _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_meas 1.38 _exptl_crystal_density_method ' flotation in a mixture of benzene and carbon tetrachloride' _exptl_crystal_description Needle _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.26 _refine_diff_density_min -0.29 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_obs 1.590 _refine_ls_hydrogen_treatment 'H atoms not refined ' _refine_ls_number_parameters 73 _refine_ls_number_reflns 948 _refine_ls_R_factor_obs 0.0572 _refine_ls_shift/esd_max 0.0025 _refine_ls_shift/esd_mean 0.0004 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F~o~)+0.0005F~o~^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0585 _reflns_number_observed 948 _reflns_number_total 1087 _reflns_observed_criterion 'refl observed if I > 1.25 \s(I) ' _cod_data_source_file oh1103.cif _cod_data_source_block dm-bpdo _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: '_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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1/[\s^2^(F~o~)+0.0005F~o~^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~o~)+0.0005F~o~^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_original_formula_sum 'C12 H12 O2 N2' _cod_database_code 2006080 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z -X+0.5,-Y+0.5,-Z +X+0.5,+Y+0.5,+Z -X,+Y,-Z+0.5 +X,-Y,+Z+0.5 +X+0.5,-Y+0.5,+Z+0.5 -X+0.5,+Y+0.5,-Z+0.5 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O1 0.0434(7) -0.0164(5) 0.0052(5) 0.0441(7) -0.0017(5) 0.0305(6) N1 0.0332(7) -0.0011(5) 0.0079(5) 0.0320(7) 0.0000(5) 0.0232(6) C1 0.0317(8) 0.0040(6) 0.0089(6) 0.0307(7) 0.0024(6) 0.0226(7) C2 0.0355(8) 0.0010(6) 0.0096(6) 0.0323(8) 0.0021(6) 0.0248(7) C3 0.0284(7) 0.0025(6) 0.0074(6) 0.0325(8) -0.0025(6) 0.0247(7) C4 0.0331(8) 0.0041(6) 0.0063(6) 0.0364(8) -0.0007(6) 0.0201(6) C5 0.0381(8) -0.0002(7) 0.0099(6) 0.0350(8) 0.0037(6) 0.0228(7) C6 0.0425(9) -0.0042(7) 0.0042(7) 0.0383(9) -0.0014(7) 0.0314(8) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type O1 1.000 0.07679(9) 0.37492(12) 0.15658(9) 0.0411(6) Ueq N1 1.000 -0.00741(10) 0.27788(13) 0.10241(11) 0.0304(6) Ueq C1 1.000 -0.03299(13) 0.16608(15) 0.17728(12) 0.0291(7) Ueq C2 1.000 -0.11315(13) 0.05656(15) 0.11614(13) 0.0317(7) Ueq C3 1.000 -0.17504(12) 0.05802(15) -0.02047(13) 0.0294(7) Ueq C4 1.000 -0.15232(13) 0.17816(16) -0.09051(13) 0.0309(7) Ueq C5 1.000 -0.07021(13) 0.28429(15) -0.03061(13) 0.0328(7) Ueq C6 1.000 -0.26282(14) -0.06115(17) -0.08518(14) 0.0393(8) Ueq H2 1.000 -0.12525 -0.02222 0.17152 0.050 Uiso H4 1.000 -0.19672 0.18756 -0.18390 0.050 Uiso H5 1.000 -0.05573 0.37339 -0.07186 0.050 Uiso H6A 1.000 -0.33090 -0.02816 -0.15876 0.050 Uiso H6B 1.000 -0.22593 -0.14503 -0.11327 0.050 Uiso H6C 1.000 -0.30023 -0.10066 -0.02107 0.050 Uiso 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 O1 N1 C1 . . 120.8(2) yes O1 N1 C5 . . 120.4(2) yes C1 N1 C5 . . 118.8(2) yes N1 C1 C1 . 5_555 117.3(2) yes N1 C1 C2 . . 120.0(2) yes C1 C1 C2 5_555 . 122.6(2) yes C1 C2 C3 . . 122.1(2) yes C2 C3 C4 . . 115.7(2) yes C2 C3 C6 . . 121.4(2) yes C4 C3 C6 . . 122.8(2) yes C3 C4 C5 . . 122.1(2) yes N1 C5 C4 . . 121.1(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . N1 . 1.301(2) yes N1 . C1 . 1.370(2) yes N1 . C5 . 1.362(2) yes C1 . C1 5_555 1.482(2) yes C1 . C2 . 1.375(2) yes C2 . C3 . 1.391(2) yes C3 . C4 . 1.387(2) yes C3 . C6 . 1.494(3) yes C4 . C5 . 1.361(2) 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_2 _geom_torsion _geom_torsion_publ_flag O1 N1 C1 C2 . . -173.6(2) no O1 N1 C5 C4 . . 175.5(2) no C5 N1 C1 C2 . . 5.3(2) no C1 N1 C5 C4 . . -3.4(2) no C1 C1 N1 O1 5_555 . 3.8(2) no C1 C1 N1 C5 5_555 . -177.4(2) no N1 C1 C1 N1 5_555 5_555 65.1(2) no N1 C1 C1 C2 5_555 5_555 -117.6(2) no C2 C1 C1 N1 5_555 5_555 -117.6(2) no C2 C1 C1 C2 5_555 5_555 59.7(2) no N1 C1 C2 C3 . . -3.1(2) no C1 C1 C2 C3 . . 179.7(3) no C1 C2 C3 C4 . . -1.1(2) no C1 C2 C3 C6 . . -179.4(3) no C2 C3 C4 C5 . . 3.0(2) no C6 C3 C4 C5 . . -178.7(3) no C3 C4 C5 N1 . . -0.9(2) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 54480914