#------------------------------------------------------------------------------ #$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201979 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/23/62/2236287.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_2236287 loop_ _publ_author_name 'Ali, Basem F.' 'Al-Far, Rawhi' 'Haddad, Salim F.' _publ_section_title ; Redetermination of 2,2'-bipyridine-1,1'-diium dibromide ; _journal_coeditor_code HB6957 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3033 _journal_paper_doi 10.1107/S1600536812040214 _journal_volume 68 _journal_year 2012 _chemical_formula_iupac 'C10 H10 N2 2+, 2Br -' _chemical_formula_moiety 'C10 H10 N2 2+, 2(Br -)' _chemical_formula_sum 'C10 H10 Br2 N2' _chemical_formula_weight 318.00 _chemical_name_common ; 2-(Pyridin-1-ium-2-yl)pyridin-1-ium dibromide ; _chemical_name_systematic ; 2,2'-Bipyridine-1,1'-diium; dibromide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 95.830(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.5568(6) _cell_length_b 9.7747(7) _cell_length_c 15.3533(12) _cell_measurement_reflns_used 1832 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.1346 _cell_measurement_theta_min 2.9110 _cell_volume 1128.21(15) _computing_cell_refinement 'CrysAlis PRO (Agilent, 2011)' _computing_data_collection 'CrysAlis PRO (Agilent, 2011)' _computing_data_reduction 'CrysAlis PRO (Agilent, 2011)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0534 _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Agilent Xcalibur EOS' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) x-ray source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 5425 _diffrn_reflns_theta_full 29.20 _diffrn_reflns_theta_max 29.20 _diffrn_reflns_theta_min 3.42 _diffrn_standards_decay_% 0.00 _exptl_absorpt_coefficient_mu 7.148 _exptl_absorpt_correction_T_max 0.489 _exptl_absorpt_correction_T_min 0.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2011)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_description chunk _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.498 _refine_diff_density_min -0.566 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 3054 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0369 _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^)+(0.0250P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.0729 _reflns_number_gt 1884 _reflns_number_total 3054 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL I in P21/c #14 CELL 0.71073 7.556806 9.77474 15.353294 90 95.8297 90 ZERR 4 0.000568 0.000659 0.001249 0 0.0068 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N Br UNIT 40 40 8 8 L.S. 20 0 0 511 PLAN 5 REM reset to P21/c #14 FMAP 2 ACTA CONF BOND HTAB BOND $H BOND $Br EQIV $1 x, y+1, z EQIV $2 -x, 1/2+y, 3/2-z EQIV $3 -1+x, y, z HTAB N1 Br2 HTAB N2 Br1_$1 HTAB C1 Br1 HTAB C9 Br2 HTAB C6 Br2_$1 HTAB C4 Br1_$1 HTAB C3 Br1_$2 RTAB BrBr Br1 Br2_$3 MPLA 6 n1 c1 c2 c3 c5 MPLA 6 n2 c6 c7 c8 c9 c10 OMIT 1 1 1 OMIT 0 1 2 OMIT 1 1 6 REM D:/Salim/exp_413/struct/olex2_exp_413/exp_413.hkl WGHT 0.025000 FVAR 2.68401 BR1 4 0.233967 0.034859 0.673260 11.00000 0.03949 0.03782 = 0.05980 -0.00318 0.01032 0.00431 N1 3 0.447963 0.485807 0.631328 11.00000 0.03968 0.03203 = 0.04406 0.00210 0.00682 -0.00037 AFIX 43 H1A 2 0.536554 0.457964 0.605070 11.00000 -1.20000 AFIX 0 C1 1 0.325724 0.394661 0.649072 11.00000 0.05803 0.03539 = 0.05762 0.00564 0.00120 -0.01287 AFIX 43 H1B 2 0.336907 0.303575 0.633009 11.00000 -1.20000 AFIX 0 N2 3 0.539198 0.844948 0.617710 11.00000 0.03093 0.03163 = 0.04834 0.00145 0.00552 -0.00334 AFIX 43 H2A 2 0.437781 0.871438 0.632317 11.00000 -1.20000 AFIX 0 C2 1 0.184055 0.435595 0.690922 11.00000 0.04292 0.05642 = 0.06734 0.01621 0.00818 -0.01893 AFIX 43 H2B 2 0.094956 0.373856 0.701327 11.00000 -1.20000 AFIX 0 BR2 4 0.744047 0.297662 0.559658 11.00000 0.04997 0.03557 = 0.05800 -0.00453 0.01070 0.00351 C3 1 0.174851 0.569536 0.717527 11.00000 0.03626 0.06018 = 0.06678 0.01769 0.02226 0.00424 AFIX 43 H3A 2 0.082229 0.597912 0.748756 11.00000 -1.20000 AFIX 0 C4 1 0.303321 0.661895 0.697817 11.00000 0.03658 0.03605 = 0.05736 0.00306 0.01108 0.00515 AFIX 43 H4A 2 0.296781 0.752641 0.715409 11.00000 -1.20000 AFIX 0 C5 1 0.440217 0.619744 0.652386 11.00000 0.03005 0.02605 = 0.03788 0.00357 0.00224 -0.00068 C6 1 0.647693 0.939491 0.591239 11.00000 0.04482 0.03676 = 0.05162 0.00536 0.00202 -0.00669 AFIX 43 H6A 2 0.614108 1.031060 0.589791 11.00000 -1.20000 AFIX 0 C7 1 0.808299 0.901928 0.566218 11.00000 0.04782 0.05239 = 0.05259 0.00516 0.01129 -0.01514 AFIX 43 H7A 2 0.885123 0.967107 0.546991 11.00000 -1.20000 AFIX 0 C8 1 0.855269 0.765661 0.569837 11.00000 0.03406 0.06463 = 0.05615 -0.00207 0.01569 -0.00489 AFIX 43 H8A 2 0.964135 0.738309 0.552381 11.00000 -1.20000 AFIX 0 C9 1 0.739818 0.668288 0.599672 11.00000 0.03792 0.03811 = 0.05993 0.00263 0.01124 0.00530 AFIX 43 H9A 2 0.772286 0.576549 0.603550 11.00000 -1.20000 AFIX 0 C10 1 0.576713 0.710545 0.623303 11.00000 0.03038 0.03186 = 0.03495 0.00231 0.00326 0.00014 HKLF 4 REM exp_413 in P21/c #14 REM R1 = 0.0369 for 1884 Fo > 4sig(Fo) and 0.0650 for all 2614 data REM 127 parameters refined using 0 restraints END WGHT 0.0250 0.0000 REM Highest difference peak 0.498, deepest hole -0.566, 1-sigma level 0.092 Q1 1 0.0871 0.0340 0.6783 11.00000 0.05 0.50 Q2 1 0.6130 0.2987 0.5595 11.00000 0.05 0.41 Q3 1 0.3588 0.0356 0.6726 11.00000 0.05 0.41 Q4 1 0.7053 0.3108 0.6184 11.00000 0.05 0.40 Q5 1 0.0421 0.2133 0.6275 11.00000 0.05 0.40 ; _cod_data_source_file hb6957.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2236287 _cod_database_fobs_code 2236287 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _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_symmetry_multiplicity Br Br1 0.23397(5) 0.03486(4) 0.67326(2) 0.04534(13) Uani d . 1 1 N N1 0.4480(4) 0.4858(3) 0.63133(16) 0.0384(7) Uani d . 1 1 H H1A 0.5366 0.4580 0.6051 0.046 Uiso calc R 1 1 C C1 0.3257(6) 0.3947(4) 0.6491(2) 0.0507(10) Uani d . 1 1 H H1B 0.3369 0.3036 0.6330 0.061 Uiso calc R 1 1 N N2 0.5392(4) 0.8449(3) 0.61771(15) 0.0369(7) Uani d . 1 1 H H2A 0.4378 0.8714 0.6323 0.044 Uiso calc R 1 1 C C2 0.1841(6) 0.4356(4) 0.6909(2) 0.0554(11) Uani d . 1 1 H H2B 0.0950 0.3739 0.7013 0.066 Uiso calc R 1 1 Br Br2 0.74405(5) 0.29766(4) 0.55966(2) 0.04749(13) Uani d . 1 1 C C3 0.1749(5) 0.5695(4) 0.7175(2) 0.0532(11) Uani d . 1 1 H H3A 0.0822 0.5979 0.7488 0.064 Uiso calc R 1 1 C C4 0.3033(5) 0.6619(4) 0.6978(2) 0.0429(9) Uani d . 1 1 H H4A 0.2968 0.7526 0.7154 0.051 Uiso calc R 1 1 C C5 0.4402(4) 0.6197(3) 0.65239(19) 0.0314(7) Uani d . 1 1 C C6 0.6477(5) 0.9395(4) 0.5912(2) 0.0446(9) Uani d . 1 1 H H6A 0.6141 1.0311 0.5898 0.054 Uiso calc R 1 1 C C7 0.8083(6) 0.9019(4) 0.5662(2) 0.0505(10) Uani d . 1 1 H H7A 0.8851 0.9671 0.5470 0.061 Uiso calc R 1 1 C C8 0.8553(5) 0.7657(4) 0.5698(2) 0.0509(10) Uani d . 1 1 H H8A 0.9641 0.7383 0.5524 0.061 Uiso calc R 1 1 C C9 0.7398(5) 0.6683(4) 0.5997(2) 0.0449(9) Uani d . 1 1 H H9A 0.7723 0.5765 0.6035 0.054 Uiso calc R 1 1 C C10 0.5767(4) 0.7105(3) 0.62330(19) 0.0324(8) Uani d . 1 1 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 0.0395(2) 0.0378(2) 0.0598(2) 0.00431(18) 0.01032(17) -0.00318(18) N1 0.0397(19) 0.0320(17) 0.0441(16) -0.0004(14) 0.0068(13) 0.0021(13) C1 0.058(3) 0.035(2) 0.058(2) -0.013(2) 0.001(2) 0.0056(18) N2 0.0309(17) 0.0316(17) 0.0483(17) -0.0033(14) 0.0055(13) 0.0014(13) C2 0.043(3) 0.056(3) 0.067(3) -0.019(2) 0.008(2) 0.016(2) Br2 0.0500(3) 0.0356(2) 0.0580(2) 0.00351(19) 0.01070(18) -0.00453(16) C3 0.036(2) 0.060(3) 0.067(2) 0.004(2) 0.0223(19) 0.018(2) C4 0.037(2) 0.036(2) 0.057(2) 0.0052(17) 0.0111(18) 0.0031(17) C5 0.0301(19) 0.0260(18) 0.0379(17) -0.0007(16) 0.0022(14) 0.0036(14) C6 0.045(3) 0.037(2) 0.052(2) -0.0067(19) 0.0020(18) 0.0054(17) C7 0.048(3) 0.052(3) 0.053(2) -0.015(2) 0.0113(19) 0.0052(19) C8 0.034(2) 0.065(3) 0.056(2) -0.005(2) 0.0157(17) -0.002(2) C9 0.038(2) 0.038(2) 0.060(2) 0.0053(18) 0.0112(18) 0.0026(17) C10 0.0304(19) 0.0319(19) 0.0349(17) 0.0001(16) 0.0033(14) 0.0023(14) 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' N N 0.0061 0.0033 '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 C1 N1 C5 123.5(3) C1 N1 H1A 118.3 C5 N1 H1A 118.3 N1 C1 C2 119.6(4) N1 C1 H1B 120.2 C2 C1 H1B 120.2 C6 N2 C10 124.6(3) C6 N2 H2A 117.7 C10 N2 H2A 117.7 C1 C2 C3 119.0(4) C1 C2 H2B 120.5 C3 C2 H2B 120.5 C2 C3 C4 119.9(4) C2 C3 H3A 120.0 C4 C3 H3A 120.0 C5 C4 C3 120.0(3) C5 C4 H4A 120.0 C3 C4 H4A 120.0 N1 C5 C4 117.8(3) N1 C5 C10 117.7(3) C4 C5 C10 124.4(3) N2 C6 C7 119.7(4) N2 C6 H6A 120.1 C7 C6 H6A 120.1 C6 C7 C8 118.9(4) C6 C7 H7A 120.6 C8 C7 H7A 120.6 C7 C8 C9 120.3(4) C7 C8 H8A 119.9 C9 C8 H8A 119.9 C10 C9 C8 119.0(3) C10 C9 H9A 120.5 C8 C9 H9A 120.5 N2 C10 C9 117.6(3) N2 C10 C5 117.5(3) C9 C10 C5 125.0(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.331(4) N1 C5 1.351(4) N1 H1A 0.8600 C1 C2 1.363(6) C1 H1B 0.9300 N2 C6 1.326(4) N2 C10 1.345(4) N2 H2A 0.8600 C2 C3 1.375(5) C2 H2B 0.9300 C3 C4 1.382(5) C3 H3A 0.9300 C4 C5 1.369(4) C4 H4A 0.9300 C5 C10 1.464(4) C6 C7 1.360(5) C6 H6A 0.9300 C7 C8 1.378(5) C7 H7A 0.9300 C8 C9 1.399(5) C8 H8A 0.9300 C9 C10 1.383(5) C9 H9A 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1A Br2 . 0.86 2.37 3.178(3) 156 N2 H2A Br1 1_565 0.86 2.35 3.145(3) 154 C1 H1B Br1 . 0.93 2.83 3.611(4) 143 C9 H9A Br2 . 0.93 2.81 3.675(4) 155 C6 H6A Br2 1_565 0.93 2.84 3.619(4) 142 C4 H4A Br1 1_565 0.93 2.86 3.697(4) 150 C3 H3A Br1 2_556 0.93 2.85 3.677(4) 149 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 C5 N1 C1 C2 -0.2(5) N1 C1 C2 C3 -2.9(6) C1 C2 C3 C4 3.3(6) C2 C3 C4 C5 -0.5(5) C1 N1 C5 C4 3.0(5) C1 N1 C5 C10 -175.6(3) C3 C4 C5 N1 -2.6(5) C3 C4 C5 C10 175.9(3) C10 N2 C6 C7 1.0(5) N2 C6 C7 C8 -0.6(5) C6 C7 C8 C9 -0.7(5) C7 C8 C9 C10 1.6(5) C6 N2 C10 C9 -0.1(5) C6 N2 C10 C5 -178.9(3) C8 C9 C10 N2 -1.2(5) C8 C9 C10 C5 177.6(3) N1 C5 C10 N2 158.5(3) C4 C5 C10 N2 -20.1(5) N1 C5 C10 C9 -20.3(5) C4 C5 C10 C9 161.1(4) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10150570