#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003695.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_2003695 loop_ _publ_author_name 'Dunne, S. J.' 'von Nagy-Felsobuki, E. I.' 'Mackay, M. F.' _publ_section_title ; 2,2'-Oxybispyridine and 2,2'-Selenobispyridine ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1454 _journal_page_last 1457 _journal_paper_doi 10.1107/S010827019500014X _journal_volume 51 _journal_year 1995 _chemical_formula_moiety 'C10 H8 N2 Se' _chemical_formula_sum 'C10 H8 N2 Se' _chemical_formula_weight 235.2 _chemical_name_systematic ; 2,2'-Selenobispyridine ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _cell_angle_alpha 90.0 _cell_angle_beta 113.10(1) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 12.370(1) _cell_length_b 5.977(1) _cell_length_c 13.909(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 291(1) _cell_measurement_theta_max 38 _cell_measurement_theta_min 20 _cell_volume 945.9(2) _computing_cell_refinement 'Rigaku-AFC Software' _computing_data_collection 'Rigaku-AFC Software (1974)' _computing_data_reduction 'Rigaku-AFC Software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'Xtal3.0 (Hall & Stewart, 1990)' _computing_structure_refinement SHELX76 _computing_structure_solution 'SHELX76 (Sheldrick, 1976)' _diffrn_ambient_temperature 291.0(10) _diffrn_measurement_device 'Rigaku-AFC diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type 'Copper K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .018 _diffrn_reflns_av_sigmaI/netI 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1656 _diffrn_reflns_theta_max 65.0 _diffrn_reflns_theta_min 7.0 _diffrn_standards_decay_% <3.4 _diffrn_standards_interval_count 50 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 5.09 _exptl_absorpt_correction_T_max .404 _exptl_absorpt_correction_T_min .241 _exptl_absorpt_correction_type 'Gaussian (Sheldrick, 1976)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.651 _exptl_crystal_description prismatic _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.26 _refine_diff_density_max .56 _refine_diff_density_min -.58 _refine_ls_abs_structure_Flack 0 _refine_ls_extinction_coef '2.27(7) x 10^-6^' _refine_ls_extinction_method 'SHELX76 (Sheldrick, 1976)' _refine_ls_goodness_of_fit_obs 3.71 _refine_ls_hydrogen_treatment 'H atoms: see text' _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 119 _refine_ls_number_reflns 1313 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs .041 _refine_ls_shift/esd_max .005 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/[\s^2^(F)+0.00015F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs .056 _reflns_number_observed 1313 _reflns_number_total 1585 _reflns_observed_criterion I>3.5\sI _cod_data_source_file kh1016.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value '1/[\s^2^(F)+0.00015F^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)+0.00015F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 945.9(4) _cod_original_sg_symbol_H-M P21/a _cod_database_code 2003695 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,1/2+y,-z 1/2+x,1/2-y,z 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 Se1 0.0904(4) 0.0038(2) 0.0557(3) 0.0341(3) 0.0017(2) 0.0737(4) N1 0.0547(17) -0.0062(13) 0.0227(13) 0.0384(16) -0.0009(13) 0.0484(15) C2 0.0445(18) 0.0014(14) 0.0141(13) 0.0353(19) 0.0030(13) 0.0361(14) C3 0.0512(20) -0.0063(15) 0.0142(15) 0.0391(19) -0.0012(15) 0.0409(16) C4 0.0653(24) 0.0018(17) 0.0151(17) 0.0407(24) -0.0034(15) 0.0437(22) C5 0.0653(25) 0.0107(19) 0.0280(19) 0.0538(23) -0.0018(18) 0.0527(21) C6 0.0534(21) -0.0007(17) 0.0306(18) 0.0575(26) 0.0013(18) 0.05911(21) N1' 0.0479(16) 0.0065(13) 0.0205(13) 0.0444(17) 0.0038(13) 0.0463(17) C2' 0.0483(19) 0.0040(15) 0.0187(14) 0.0400(20) -0.0011(14) 0.0381(15) C3' 0.0463(19) 0.0031(17) 0.0144(15) 0.0609(23) -0.0033(17) 0.0432(17) C4' 0.0385(18) -0.0043(20) 0.0178(16) 0.0818(32) -0.0093(20) 0.0549(20) C5' 0.0644(25) -0.0196(21) 0.0317(20) 0.0667(29) -0.0052(19) 0.0536(20) C6' 0.0686(24) -0.0001(18) 0.0239(18) 0.0493(22) 0.0041(16) 0.0436(17) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv Se1 0.24979(4) 0.16197(7) 0.25696(3) 4.64(2) N1 0.4009(3) 0.0696(5) 0.1652(2) 3.66(7) C2 0.3154(3) -0.0305(5) 0.1832(2) 3.09(7) C3 0.2751(3) -0.2441(6) 0.1488(3) 3.55(8) C4 0.32811(4) -0.3604(6) 0.0947(3) 4.09(9) C5 0.4172(4) -0.2600(7) 0.0740(3) 4.40(10) C6 0.4508(3) -0.0450(7) 0.1113(3) 4.27(10) N1' 0.2435(2) -0.2339(5) 0.3626(2) 3.60(7) C2' 0.1805(3) -0.0520(6) 0.3210(2) 3.28(8) C3' 0.0746(3) -0.0013(7) 0.3251(3) 4.04(8) C4' 0.0296(3) -0.1471(8) 0.3760(3) 4.62(10) C5' 0.0916(4) -0.3413(7) 0.4192(3) 4.65(11) C6' 0.1967(4) -0.3791(7) 0.4095(3) 4.20(9) H3 0.2037 -0.3167 0.1644 3.55 H4 0.3006 -0.5290 0.0684 4.09 H5 0.4595 -0.3404 0.0301 4.40 H6 0.5209 0.0335 0.0958 4.27 H3' 0.0278 0.1493 0.2894 4.04 H4' -0.0530 -0.1117 0.3824 4.62 H5' 0.0581 -0.4595 0.4595 4.65 H6' 0.2437 -0.5322 0.4410 4.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C ? International_Tables_Vol_IV_Table_2.3.1 .017 .009 H ? International_Tables_Vol_IV_Table_2.3. 0 0 N ? International_Tables_Vol_IV_Table_2.3.1 .029 .018 Se ? Internaltional_Tables_Vol_IV_Table_2.3.1 -0.879 1.139 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 -1 -2 1 1 -4 -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 Se1 C2' 101.9(2) yes C2 N1 C6 117.1(2) yes Se1 C2 N1 111.6(2) yes Se1 C2 C3 124.5(2) yes N1 C2 C3 123.9(2) yes C2 C3 C4 118.3(3) yes C3 C4 C5 119.2(3) yes C4 C5 C6 118.1(3) yes N1 C6 C5 123.3(3) yes C2' N1' C6' 116.6(2) yes Se1 C2' N1' 116.7(2) yes Se1 C2' C3' 118.4(3) yes N1' C2' C3' 124.8(3) yes C2' C3' C4' 118.1(3) yes C3' C4' C5' 119.1(3) yes C4' C5' C6' 118.4(3) yes N1' C6' C5' 123.0(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Se1 C2 1.940(4) yes Se1 C2' 1.940(4) yes N1 C2 1.322(5) yes N1 C6 1.332(6) yes C2 C3 1.386(5) yes C3 C4 1.366(7) yes C4 C5 1.381(7) yes C5 C6 1.387(6) yes N1' C2' 1.331(4) yes N1' C6' 1.345(6) yes C2' C3' 1.367(6) yes C3' C4' 1.371(7) yes C4' C5' 1.391(6) yes C5' C6' 1.377(7) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 297304