#------------------------------------------------------------------------------
#$Date: 2022-10-03 17:40:12 +0300 (Mon, 03 Oct 2022) $
#$Revision: 278324 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/45/2004595.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_2004595
loop_
_publ_author_name
'Wang, W.'
'Baba, A.'
'Schmehl, R. H.'
'Mague, J. T.'
_publ_section_title
;
 A Rigid Bis-Bidentate Bridging Ligand:
 1,4-Bis(2,2'-bipyrid-4-yl)benzene
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              658
_journal_page_last               660
_journal_paper_doi               10.1107/S010827019501242X
_journal_volume                  52
_journal_year                    1996
_chemical_formula_structural     'C26 H18 N4'
_chemical_formula_sum            'C26 H18 N4'
_chemical_formula_weight         386.46
_chemical_name_systematic
;
1,4-bis(2,2'-bipyrid-4-yl)benzene
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.000(9)
_cell_angle_beta                 114.01(1)
_cell_angle_gamma                90.00(1)
_cell_formula_units_Z            2
_cell_length_a                   10.025(1)
_cell_length_b                   8.689(1)
_cell_length_c                   12.063(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      19
_cell_measurement_theta_min      11
_cell_volume                     959.86(18)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN PROCESS (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'MolEN CIF VAX (Fair, 1990)'
_computing_structure_refinement  'MolEN LSFM'
_computing_structure_solution    'SIR88 (Burla et al., 1989)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1922
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        <1.0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.494
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fₒ²/[σ²(Fₒ²) + 0.0016Fₒ⁴]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.047
_reflns_number_observed          1091
_reflns_number_total             1685
_reflns_observed_criterion       >2.0\s(I)
_cod_data_source_file            cr1205.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 4F~o~^2^/[\s^2^(F~o~^2^) +
0.0016F~o~^4^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 4F~o~^2^/[\s^2^(F~o~^2^) + 0.0016F~o~^4^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        959.9(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2004595
_cod_database_fobs_code          2004595
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
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 0.0572(8) 0.0770(10) 0.0395(7) 0.0115(8) 0.0124(6) -0.0109(7)
N2 0.0526(7) 0.0557(9) 0.0418(6) 0.0034(7) 0.0169(5) 0.0025(7)
C1 0.0452(8) 0.0450(10) 0.0342(7) -0.0056(8) 0.0149(6) -0.0006(7)
C2 0.0590(10) 0.0590(10) 0.0370(8) 0.0011(9) 0.0138(7) 0.0007(8)
C3 0.0740(10) 0.0680(10) 0.0324(7) -0.0060(10) 0.0169(7) -0.0085(9)
C4 0.0670(10) 0.0680(10) 0.0494(8) -0.0030(10) 0.0293(6) -0.0163(9)
C5 0.0620(10) 0.089(2) 0.0549(9) 0.0180(10) 0.0174(8) -0.0170(10)
C6 0.0454(8) 0.0425(9) 0.0373(7) -0.0046(8) 0.0168(6) 0.0008(7)
C7 0.0484(8) 0.0431(9) 0.0367(7) -0.0004(8) 0.0179(5) 0.0003(7)
C8 0.0528(8) 0.0420(9) 0.0391(7) -0.0057(8) 0.0213(5) -0.0023(7)
C9 0.0609(9) 0.0490(10) 0.0486(8) 0.0065(9) 0.0261(6) -0.0014(8)
C10 0.0568(9) 0.0580(10) 0.0503(9) 0.0121(9) 0.0207(7) 0.0038(9)
C11 0.0522(8) 0.0386(9) 0.0390(7) -0.0060(8) 0.0202(6) -0.0050(7)
C12 0.0481(8) 0.0530(10) 0.0406(7) 0.0008(8) 0.0188(6) -0.0042(8)
C13 0.0545(8) 0.0540(10) 0.0422(7) -0.0006(8) 0.0254(5) -0.0075(8)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
N1 0.5122(2) 0.2379(2) 0.9877(1) 0.0603(5) Uani ?
N2 0.8044(1) -0.0197(2) 1.0165(1) 0.0508(4) Uani ?
C1 0.6380(2) 0.1625(2) 1.0420(1) 0.0419(5) Uani ?
C2 0.7197(2) 0.1731(2) 1.1656(2) 0.0536(6) Uani ?
C3 0.6710(2) 0.2621(2) 1.2352(1) 0.0598(6) Uani ?
C4 0.5410(2) 0.3368(3) 1.1810(2) 0.0600(6) Uani ?
C5 0.4669(2) 0.3219(3) 1.0582(2) 0.0710(7) Uani ?
C6 0.6850(2) 0.0679(2) 0.9618(1) 0.0418(5) Uani ?
C7 0.6076(2) 0.0716(2) 0.8369(1) 0.0425(5) Uani ?
C8 0.6526(2) -0.0160(2) 0.7620(1) 0.0438(5) Uani ?
C9 0.7753(2) -0.1081(2) 0.8197(1) 0.0517(5) Uani ?
C10 0.8454(2) -0.1051(2) 0.9440(2) 0.0555(6) Uani ?
C11 0.5735(2) -0.0102(2) 0.6276(1) 0.0427(5) Uani ?
C12 0.6433(2) -0.0453(2) 0.5518(1) 0.0472(5) Uani ?
C13 0.4281(2) 0.0351(2) 0.5725(1) 0.0485(5) Uani ?
H2 0.8094 0.1188 1.2022 0.0643 Uiso calc
H3 0.7270 0.2715 1.3201 0.0718 Uiso calc
H4 0.5031 0.3974 1.2271 0.0720 Uiso calc
H5 0.3768 0.3751 1.0204 0.0852 Uiso calc
H7 0.5232 0.1346 0.8022 0.0510 Uiso calc
H9 0.8101 -0.1724 0.7735 0.0620 Uiso calc
H10 0.9291 -0.1685 0.9810 0.0666 Uiso calc
H12 0.7434 -0.0738 0.5857 0.0566 Uiso calc
H13 0.3772 0.0631 0.6208 0.0582 Uiso calc
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
C1 N1 C5 117.1(2) yes
C6 N2 C10 116.4(2) yes
N1 C1 C2 121.6(2) yes
N1 C1 C6 116.1(2) yes
C2 C1 C6 122.3(2) yes
C1 C2 C3 119.8(2) yes
C2 C3 C4 119.0(2) yes
C3 C4 C5 117.9(2) yes
N1 C5 C4 124.6(2) yes
N2 C6 C1 116.7(2) yes
N2 C6 C7 122.6(2) yes
C1 C6 C7 120.7(2) yes
C6 C7 C8 120.5(2) yes
C7 C8 C9 116.4(2) yes
C7 C8 C11 121.3(2) yes
C9 C8 C11 122.3(2) yes
C8 C9 C10 119.3(2) yes
N2 C10 C9 124.7(2) yes
C8 C11 C12 121.4(2) yes
C8 C11 C13 121.4(2) yes
C12 C11 C13 117.2(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 1.333(2) yes
N1 C5 1.333(3) yes
N2 C6 1.344(2) yes
N2 C10 1.333(3) yes
C1 C2 1.382(2) yes
C1 C6 1.484(3) yes
C2 C3 1.369(3) yes
C3 C4 1.361(3) yes
C4 C5 1.367(3) yes
C6 C7 1.387(2) yes
C7 C8 1.389(3) yes
C8 C9 1.394(3) yes
C8 C11 1.487(2) yes
C9 C10 1.373(3) yes
C11 C12 1.392(3) yes
C11 C13 1.390(3) yes
