#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/23/2222348.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_paper_doi               10.1107/S1600536809019151
_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       'φ and ω'
_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/[σ²(Fo²)+(0.1057P)²+0.0566P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            hk2693.cif
_cod_data_source_block           I
_cod_database_code               2222348
_cod_database_fobs_code          2222348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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_
_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_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_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
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) ?
