#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2222348.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_2222348 loop_ _publ_author_name 'Khoshtarkib, Zeinab' 'Ebadi, Amin' 'Ahmadi, Roya' 'Alizadeh, Robabeh' _publ_section_title ; 5,5'-Dimethyl-2,2'-bipyridine ; _journal_coeditor_code HK2693 _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1586 _journal_volume 65 _journal_year 2009 _chemical_formula_iupac 'C12 H12 N2' _chemical_formula_moiety 'C12 H12 N2' _chemical_formula_sum 'C12 H12 N2' _chemical_formula_weight 184.24 _chemical_name_systematic ; 5,5'-Dimethyl-2,2'-bipyridine ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 96.04(5) _cell_angle_beta 91.16(4) _cell_angle_gamma 105.03(5) _cell_formula_units_Z 2 _cell_length_a 6.409(4) _cell_length_b 7.312(5) _cell_length_c 11.533(8) _cell_measurement_reflns_used 1133 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.28 _cell_measurement_theta_min 1.78 _cell_volume 518.4(6) _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _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 0.0820 _diffrn_reflns_av_sigmaI/netI 0.0532 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6191 _diffrn_reflns_theta_full 29.28 _diffrn_reflns_theta_max 29.28 _diffrn_reflns_theta_min 1.78 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 196 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.274 _refine_diff_density_min -0.244 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 2739 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0657 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1057P)^2^+0.0566P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1906 _refine_ls_wR_factor_ref 0.2053 _reflns_number_gt 2067 _reflns_number_total 2739 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hk2693.cif _[local]_cod_data_source_block I loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_disorder_assembly _atom_site_disorder_group N N1 0.4778(2) 0.76393(19) 0.53822(13) 0.0604(4) Uani d . 1 . . N N2 0.0741(2) 0.77876(19) 0.99037(14) 0.0656(4) Uani d . 1 . . C C1 0.4223(2) 0.92544(19) 0.52837(12) 0.0486(3) Uani d . 1 . . C C2 0.2280(2) 0.9529(2) 0.56860(14) 0.0579(4) Uani d . 1 . . H H2 0.1916 1.0661 0.5601 0.069 Uiso calc R 1 . . C C3 0.0896(3) 0.8105(3) 0.62124(16) 0.0655(4) Uani d . 1 . . H H3 -0.0407 0.8276 0.6480 0.079 Uiso calc R 1 . . C C4 0.1445(3) 0.6443(2) 0.63387(13) 0.0594(4) Uani d . 1 . . C C5 0.0011(4) 0.4859(3) 0.69263(18) 0.0797(6) Uani d . 1 . . H H5C 0.0475 0.3716 0.6761 0.096 Uiso calc R 1 . . H H5B -0.1459 0.4638 0.6637 0.096 Uiso calc R 1 . . H H5A 0.0105 0.5218 0.7755 0.096 Uiso calc R 1 . . C C6 0.3403(3) 0.6293(2) 0.58998(16) 0.0641(4) Uani d . 1 . . H H6 0.3793 0.5168 0.5971 0.077 Uiso calc R 1 . . C C7 0.0828(2) 0.96057(19) 1.02576(12) 0.0513(4) Uani d . 1 . . C C8 0.2406(3) 1.0695(2) 1.10747(14) 0.0632(4) Uani d . 1 . . H H8 0.2442 1.1958 1.1315 0.076 Uiso calc R 1 . . C C9 0.3905(3) 0.9892(3) 1.15227(15) 0.0679(5) Uani d . 1 . . H H9 0.4973 1.0614 1.2066 0.082 Uiso calc R 1 . . C C10 0.3838(3) 0.8018(2) 1.11714(14) 0.0600(4) Uani d . 1 . . C C11 0.5426(3) 0.7065(3) 1.1636(2) 0.0793(5) Uani d . 1 . . H H11C 0.5070 0.5755 1.1305 0.095 Uiso calc R 1 . . H H11B 0.5374 0.7130 1.2470 0.095 Uiso calc R 1 . . H H11A 0.6856 0.7699 1.1431 0.095 Uiso calc R 1 . . C C12 0.2214(3) 0.7049(2) 1.03580(18) 0.0686(5) Uani d . 1 . . H H12 0.2146 0.5782 1.0109 0.082 Uiso calc R 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 N1 0.0614(8) 0.0537(7) 0.0719(8) 0.0235(6) 0.0113(6) 0.0111(6) N2 0.0615(8) 0.0483(7) 0.0819(9) 0.0103(6) -0.0066(7) -0.0034(6) C1 0.0470(7) 0.0513(7) 0.0491(7) 0.0170(6) -0.0020(5) 0.0031(5) C2 0.0500(8) 0.0626(9) 0.0669(9) 0.0231(6) 0.0037(6) 0.0129(7) C3 0.0508(8) 0.0790(11) 0.0696(9) 0.0200(8) 0.0091(7) 0.0131(8) C4 0.0607(9) 0.0615(9) 0.0513(7) 0.0076(7) 0.0001(6) 0.0067(6) C5 0.0809(13) 0.0784(12) 0.0723(11) 0.0034(10) 0.0095(9) 0.0176(9) C6 0.0734(10) 0.0539(8) 0.0690(9) 0.0212(7) 0.0104(8) 0.0125(7) C7 0.0527(7) 0.0454(7) 0.0523(7) 0.0062(6) 0.0075(6) 0.0052(5) C8 0.0722(10) 0.0521(8) 0.0608(8) 0.0129(7) -0.0068(7) -0.0031(6) C9 0.0727(10) 0.0664(10) 0.0595(9) 0.0131(8) -0.0108(7) 0.0003(7) C10 0.0567(8) 0.0625(9) 0.0620(8) 0.0137(7) 0.0086(7) 0.0158(7) C11 0.0705(11) 0.0809(13) 0.0911(13) 0.0247(10) -0.0004(10) 0.0194(10) C12 0.0640(10) 0.0500(8) 0.0896(12) 0.0137(7) -0.0015(8) 0.0017(8) 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 C1 N1 . 1.334(2) ? C1 C2 . 1.393(2) ? C1 C1 2_676 1.491(3) ? C2 C3 . 1.384(3) ? C2 H2 . 0.9300 ? C3 C4 . 1.371(3) ? C3 H3 . 0.9300 ? C4 C6 . 1.389(3) ? C4 C5 . 1.511(3) ? C5 H5C . 0.9600 ? C5 H5B . 0.9600 ? C5 H5A . 0.9600 ? C6 N1 . 1.340(2) ? C6 H6 . 0.9300 ? C7 N2 . 1.335(2) ? C7 C8 . 1.389(2) ? C7 C7 2_577 1.475(3) ? C8 C9 . 1.368(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.377(3) ? C9 H9 . 0.9300 ? C10 C12 . 1.380(3) ? C10 C11 . 1.494(3) ? C11 H11C . 0.9600 ? C11 H11B . 0.9600 ? C11 H11A . 0.9600 ? C12 N2 . 1.327(2) ? C12 H12 . 0.9300 ? 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 N1 C1 C2 . . 121.57(15) ? N1 C1 C1 . 2_676 116.75(16) ? C2 C1 C1 . 2_676 121.68(16) ? C3 C2 C1 . . 119.51(15) ? C3 C2 H2 . . 120.2 ? C1 C2 H2 . . 120.2 ? C4 C3 C2 . . 119.99(16) ? C4 C3 H3 . . 120.0 ? C2 C3 H3 . . 120.0 ? C3 C4 C6 . . 116.29(16) ? C3 C4 C5 . . 122.09(17) ? C6 C4 C5 . . 121.62(17) ? C4 C5 H5C . . 109.5 ? C4 C5 H5B . . 109.5 ? H5C C5 H5B . . 109.5 ? C4 C5 H5A . . 109.5 ? H5C C5 H5A . . 109.5 ? H5B C5 H5A . . 109.5 ? N1 C6 C4 . . 125.26(16) ? N1 C6 H6 . . 117.4 ? C4 C6 H6 . . 117.4 ? N2 C7 C8 . . 121.30(15) ? N2 C7 C7 . 2_577 116.86(16) ? C8 C7 C7 . 2_577 121.84(17) ? C9 C8 C7 . . 119.40(16) ? C9 C8 H8 . . 120.3 ? C7 C8 H8 . . 120.3 ? C8 C9 C10 . . 120.16(16) ? C8 C9 H9 . . 119.9 ? C10 C9 H9 . . 119.9 ? C9 C10 C12 . . 116.32(17) ? C9 C10 C11 . . 122.45(18) ? C12 C10 C11 . . 121.22(17) ? C10 C11 H11C . . 109.5 ? C10 C11 H11B . . 109.5 ? H11C C11 H11B . . 109.5 ? C10 C11 H11A . . 109.5 ? H11C C11 H11A . . 109.5 ? H11B C11 H11A . . 109.5 ? N2 C12 C10 . . 124.98(16) ? N2 C12 H12 . . 117.5 ? C10 C12 H12 . . 117.5 ? C1 N1 C6 . . 117.36(15) ? C12 N2 C7 . . 117.84(15) ? 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_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N1 C1 C2 C3 . . . . 0.7(2) ? C1 C1 C2 C3 2_676 . . . -179.66(16) ? C1 C2 C3 C4 . . . . 0.3(3) ? C2 C3 C4 C6 . . . . -0.9(3) ? C2 C3 C4 C5 . . . . 178.87(16) ? C3 C4 C6 N1 . . . . 0.7(3) ? C5 C4 C6 N1 . . . . -179.06(16) ? N2 C7 C8 C9 . . . . 0.2(3) ? C7 C7 C8 C9 2_577 . . . -179.88(17) ? C7 C8 C9 C10 . . . . -0.5(3) ? C8 C9 C10 C12 . . . . 0.4(3) ? C8 C9 C10 C11 . . . . -179.67(17) ? C9 C10 C12 N2 . . . . -0.2(3) ? C11 C10 C12 N2 . . . . 179.92(17) ? C2 C1 N1 C6 . . . . -0.9(2) ? C1 C1 N1 C6 2_676 . . . 179.44(15) ? C4 C6 N1 C1 . . . . 0.2(3) ? C10 C12 N2 C7 . . . . -0.1(3) ? C8 C7 N2 C12 . . . . 0.0(3) ? C7 C7 N2 C12 2_577 . . . -179.87(17) ? 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 C9 H9 Cg1 2_677 0.93 2.78 3.669(3) 160 _cod_database_code 2222348