#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234705.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7234705
loop_
_publ_author_name
'Yuichiro Watanabe'
'Hisahiro Sasabe'
'Daisuke Yokoyama'
'Teruo Beppu'
'Hiroshi Katagiri'
'Junji Kido'
_publ_section_title
;
 Synthesis, properties, and OLED characteristics of 2,2'-bipyridine-based
 electron-transport materials: the synergistic effect of molecular shape
 anisotropy and a weak hydrogen-bonding network on molecular orientation
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3699
_journal_page_last               3704
_journal_paper_doi               10.1039/C5TC03737A
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C42 H28 N6'
_chemical_formula_sum            'C42 H28 N6'
_chemical_formula_weight         616.70
_chemical_name_systematic        6,6'-BPy3
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.426(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.776(12)
_cell_length_b                   3.8953(14)
_cell_length_c                   23.750(9)
_cell_measurement_reflns_used    3191
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.2
_cell_volume                     3018.6(19)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18153
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         3.447
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0676P)²+1.9894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2946
_reflns_number_total             3437
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3699.cif
_cod_data_source_block           ydkr2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7234705
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20218(3) 0.0801(3) 0.46835(5) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.14909(4) -0.7032(4) 0.19594(5) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.22846(4) 0.2312(4) 0.50737(5) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.21651(4) 0.3518(4) 0.55865(5) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.2357 0.4592 0.5855 0.029 Uiso 1 1 calc R U . . .
C3 C 0.17609(4) 0.3117(4) 0.56954(6) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.1671 0.3931 0.6040 0.033 Uiso 1 1 calc R U . . .
C4 C 0.14880(4) 0.1517(4) 0.52970(6) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.1210 0.1181 0.5367 0.032 Uiso 1 1 calc R U . . .
C5 C 0.16287(4) 0.0409(4) 0.47911(5) 0.0217(3) Uani 1 1 d . . . . .
C6 C 0.18614(5) -0.8476(4) 0.20739(7) 0.0345(4) Uani 1 1 d D . . . .
H6 H 0.1993 -0.9408 0.1768 0.041 Uiso 1 1 calc R U . . .
C7 C 0.20625(5) -0.8685(4) 0.26099(7) 0.0307(3) Uani 1 1 d D . . . .
H7 H 0.2324 -0.9738 0.2671 0.037 Uiso 1 1 calc R U . . .
C8 C 0.18733(4) -0.7323(4) 0.30546(6) 0.0261(3) Uani 1 1 d D . . . .
H8 H 0.2006 -0.7431 0.3428 0.031 Uiso 1 1 calc R U . . .
C9 C 0.14888(4) -0.5790(4) 0.29588(5) 0.0221(3) Uani 1 1 d D . . . .
C10 C 0.13126(5) -0.5723(4) 0.24006(6) 0.0293(3) Uani 1 1 d D . . . .
H10 H 0.1050 -0.4690 0.2327 0.035 Uiso 1 1 calc R U . . .
C11 C 0.12868(4) -0.4193(4) 0.34252(5) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.15268(4) -0.2865(4) 0.38920(5) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.1816 -0.3095 0.3910 0.025 Uiso 1 1 calc R U . . .
C13 C 0.13528(4) -0.1212(4) 0.43316(5) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.09273(4) -0.0967(4) 0.43109(6) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.0805 0.0096 0.4613 0.027 Uiso 1 1 calc R U . . .
C15 C 0.06794(4) -0.2276(4) 0.38481(6) 0.0225(3) Uani 1 1 d . . . . .
C16 C 0.08614(4) -0.3864(4) 0.34083(5) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.0693 -0.4736 0.3093 0.027 Uiso 1 1 calc R U . . .
C17A C 0.0211(3) -0.152(4) 0.3835(5) 0.0192(15) Uani 0.5 1 d D . P A 1
C18A C 0.0009(4) -0.055(4) 0.3324(5) 0.0245(18) Uani 0.5 1 d D . P A 1
H18A H 0.0157 -0.0098 0.3006 0.029 Uiso 0.5 1 calc R U P A 1
C19A C -0.0412(4) -0.025(9) 0.3287(5) 0.0491(17) Uani 0.5 1 d D . P A 1
H19A H -0.0559 0.0397 0.2939 0.059 Uiso 0.5 1 calc R U P A 1
C20A C -0.0622(3) -0.090(8) 0.3760(5) 0.0639(9) Uani 0.5 1 d D . P A 1
H20A H -0.0912 -0.1028 0.3734 0.077 Uiso 0.5 1 calc R U P A 1
N3A N -0.0384(3) -0.135(3) 0.4273(4) 0.046(2) Uani 0.5 1 d D . P A 1
C21A C 0.0009(6) -0.190(5) 0.4308(8) 0.033(2) Uani 0.5 1 d . . P A 1
H21A H 0.0154 -0.2547 0.4657 0.039 Uiso 0.5 1 calc R U P A 1
C17B C 0.0245(3) -0.216(4) 0.3794(5) 0.0192(15) Uani 0.5 1 d D . P A 2
C18B C 0.0009(6) -0.265(5) 0.4257(8) 0.033(2) Uani 0.5 1 d D . P A 2
H18B H 0.0154 -0.3263 0.4608 0.039 Uiso 0.5 1 calc R U P A 2
C19B C -0.0426(4) -0.230(4) 0.4252(5) 0.046(2) Uani 0.5 1 d D . P A 2
H19B H -0.0583 -0.2973 0.4550 0.055 Uiso 0.5 1 calc R U P A 2
C20B C -0.0579(3) -0.085(8) 0.3755(6) 0.0639(9) Uani 0.5 1 d D . P A 2
H20B H -0.0844 0.0126 0.3754 0.077 Uiso 0.5 1 calc R U P A 2
N3B N -0.0405(3) -0.061(7) 0.3261(4) 0.0491(17) Uani 0.5 1 d D . P A 2
C21B C 0.0001(4) -0.127(4) 0.3294(5) 0.0245(18) Uani 0.5 1 d . . P A 2
H21B H 0.0133 -0.1125 0.2955 0.029 Uiso 0.5 1 calc R U P A 2
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C5 118.88(12) . .
C6 N2 C10 116.84(13) . .
N1 C1 C2 122.43(12) . .
N1 C1 C1 116.16(15) . 7_556
C2 C1 C1 121.40(15) . 7_556
C3 C2 C1 118.56(12) . .
C3 C2 H2 120.7 . .
C1 C2 H2 120.7 . .
C2 C3 C4 119.40(13) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C4 C5 118.82(13) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
N1 C5 C4 121.90(12) . .
N1 C5 C13 115.77(12) . .
C4 C5 C13 122.32(12) . .
N2 C6 C7 123.75(14) . .
N2 C6 H6 118.1 . .
C7 C6 H6 118.1 . .
C6 C7 C8 118.27(15) . .
C6 C7 H7 120.9 . .
C8 C7 H7 120.9 . .
C7 C8 C9 120.30(14) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C10 116.73(13) . .
C8 C9 C11 121.29(12) . .
C10 C9 C11 121.93(13) . .
N2 C10 C9 124.12(14) . .
N2 C10 H10 117.9 . .
C9 C10 H10 117.9 . .
C12 C11 C16 118.33(12) . .
C12 C11 C9 119.44(12) . .
C16 C11 C9 122.20(12) . .
C13 C12 C11 121.75(12) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C12 C13 C14 118.95(12) . .
C12 C13 C5 118.79(12) . .
C14 C13 C5 122.17(12) . .
C13 C14 C15 120.48(13) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C16 C15 C14 119.46(12) . .
C16 C15 C17B 116.2(5) . .
C14 C15 C17B 124.3(5) . .
C16 C15 C17A 123.9(5) . .
C14 C15 C17A 116.3(5) . .
C15 C16 C11 121.01(12) . .
C15 C16 H16 119.5 . .
C11 C16 H16 119.5 . .
C21A C17A C18A 121.8(8) . .
C21A C17A C15 121.1(12) . .
C18A C17A C15 117.2(8) . .
C17A C18A C19A 118.1(2) . .
C17A C18A H18A 121.0 . .
C19A C18A H18A 121.0 . .
C18A C19A C20A 120.0(2) . .
C18A C19A H19A 120.0 . .
C20A C19A H19A 120.0 . .
C19A C20A N3A 116.6(2) . .
C19A C20A H20A 121.7 . .
N3A C20A H20A 121.7 . .
C21A N3A C20A 123.1(9) . .
N3A C21A C17A 118.9(15) . .
N3A C21A H21A 120.5 . .
C17A C21A H21A 120.5 . .
C21B C17B C18B 112.3(8) . .
C21B C17B C15 124.6(9) . .
C18B C17B C15 122.9(12) . .
C17B C18B C19B 126.7(15) . .
C17B C18B H18B 116.6 . .
C19B C18B H18B 116.6 . .
C20B C19B C18B 109.4(10) . .
C20B C19B H19B 125.3 . .
C18B C19B H19B 125.3 . .
N3B C20B C19B 129.0(10) . .
N3B C20B H20B 115.5 . .
C19B C20B H20B 115.5 . .
C21B N3B C20B 115.4(4) . .
N3B C21B C17B 124.9(4) . .
N3B C21B H21B 117.6 . .
C17B C21B H21B 117.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3401(17) .
N1 C5 1.3459(18) .
N2 C6 1.343(2) .
N2 C10 1.347(2) .
C1 C2 1.3955(19) .
C1 C1 1.494(3) 7_556
C2 C3 1.383(2) .
C2 H2 0.9500 .
C3 C4 1.387(2) .
C3 H3 0.9500 .
C4 C5 1.3956(19) .
C4 H4 0.9500 .
C5 C13 1.4902(18) .
C6 C7 1.380(2) .
C6 H6 0.9500 .
C7 C8 1.380(2) .
C7 H7 0.9500 .
C8 C9 1.394(2) .
C8 H8 0.9500 .
C9 C10 1.3953(19) .
C9 C11 1.4802(19) .
C10 H10 0.9500 .
C11 C12 1.3966(18) .
C11 C16 1.3970(19) .
C12 C13 1.3935(19) .
C12 H12 0.9500 .
C13 C14 1.3943(19) .
C14 C15 1.3996(18) .
C14 H14 0.9500 .
C15 C16 1.396(2) .
C15 C17B 1.418(10) .
C15 C17A 1.561(9) .
C16 H16 0.9500 .
C17A C21A 1.362(17) .
C17A C18A 1.380(2) .
C18A C19A 1.381(2) .
C18A H18A 0.9500 .
C19A C20A 1.394(2) .
C19A H19A 0.9500 .
C20A N3A 1.395(2) .
C20A H20A 0.9500 .
N3A C21A 1.300(16) .
C21A H21A 0.9500 .
C17B C21B 1.411(5) .
C17B C18B 1.417(17) .
C18B C19B 1.429(16) .
C18B H18B 0.9500 .
C19B C20B 1.361(10) .
C19B H19B 0.9500 .
C20B N3B 1.357(7) .
C20B H20B 0.9500 .
N3B C21B 1.350(6) .
C21B H21B 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 -0.5(2) . . . .
C5 N1 C1 C1 -179.62(14) . . . 7_556
N1 C1 C2 C3 0.4(2) . . . .
C1 C1 C2 C3 179.46(16) 7_556 . . .
C1 C2 C3 C4 0.5(2) . . . .
C2 C3 C4 C5 -1.2(2) . . . .
C1 N1 C5 C4 -0.2(2) . . . .
C1 N1 C5 C13 178.53(12) . . . .
C3 C4 C5 N1 1.1(2) . . . .
C3 C4 C5 C13 -177.63(13) . . . .
C10 N2 C6 C7 0.2(2) . . . .
N2 C6 C7 C8 -0.2(3) . . . .
C6 C7 C8 C9 0.1(2) . . . .
C7 C8 C9 C10 0.0(2) . . . .
C7 C8 C9 C11 -177.62(13) . . . .
C6 N2 C10 C9 0.0(2) . . . .
C8 C9 C10 N2 0.0(2) . . . .
C11 C9 C10 N2 177.57(14) . . . .
C8 C9 C11 C12 27.7(2) . . . .
C10 C9 C11 C12 -149.80(14) . . . .
C8 C9 C11 C16 -154.35(14) . . . .
C10 C9 C11 C16 28.1(2) . . . .
C16 C11 C12 C13 -0.7(2) . . . .
C9 C11 C12 C13 177.35(13) . . . .
C11 C12 C13 C14 1.8(2) . . . .
C11 C12 C13 C5 -174.70(12) . . . .
N1 C5 C13 C12 13.99(19) . . . .
C4 C5 C13 C12 -167.24(14) . . . .
N1 C5 C13 C14 -162.41(13) . . . .
C4 C5 C13 C14 16.4(2) . . . .
C12 C13 C14 C15 -1.8(2) . . . .
C5 C13 C14 C15 174.61(13) . . . .
C13 C14 C15 C16 0.6(2) . . . .
C13 C14 C15 C17B 179.5(8) . . . .
C13 C14 C15 C17A -173.6(7) . . . .
C14 C15 C16 C11 0.5(2) . . . .
C17B C15 C16 C11 -178.4(7) . . . .
C17A C15 C16 C11 174.3(7) . . . .
C12 C11 C16 C15 -0.5(2) . . . .
C9 C11 C16 C15 -178.48(13) . . . .
C16 C15 C17A C21A 141.4(12) . . . .
C14 C15 C17A C21A -44.7(15) . . . .
C16 C15 C17A C18A -37.0(15) . . . .
C14 C15 C17A C18A 137.0(10) . . . .
C21A C17A C18A C19A -6(3) . . . .
C15 C17A C18A C19A 172.7(19) . . . .
C17A C18A C19A C20A 0(3) . . . .
C18A C19A C20A N3A 9(4) . . . .
C19A C20A N3A C21A -15(3) . . . .
C20A N3A C21A C17A 10(3) . . . .
C18A C17A C21A N3A 1(2) . . . .
C15 C17A C21A N3A -177.7(13) . . . .
C16 C15 C17B C21B -44.8(16) . . . .
C14 C15 C17B C21B 136.4(11) . . . .
C16 C15 C17B C18B 141.1(12) . . . .
C14 C15 C17B C18B -37.8(17) . . . .
C21B C17B C18B C19B 0(2) . . . .
C15 C17B C18B C19B 174.5(14) . . . .
C17B C18B C19B C20B -10(2) . . . .
C18B C19B C20B N3B 19(3) . . . .
C19B C20B N3B C21B -14(3) . . . .
C20B N3B C21B C17B 0(3) . . . .
C18B C17B C21B N3B 6(3) . . . .
C15 C17B C21B N3B -168.6(18) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132564863
