#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/47/7234704.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_7234704
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        4,4'-BPy3
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.267(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7736(2)
_cell_length_b                   18.7721(13)
_cell_length_c                   20.9421(15)
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    93
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.9
_cell_volume                     1477.24(17)
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18887
_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         27.494
_diffrn_reflns_theta_min         3.125
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       Prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3364
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0439
_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)+(0.0585P)²+0.8907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3073
_reflns_number_total             3364
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-3699.cif
_cod_data_source_block           crystalclear
_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      'P 21/c'
_cod_database_code               7234704
_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   0.983
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.5714(3) 0.06624(7) 0.20212(6) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.5958(4) 0.00138(7) 0.23512(6) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.6510 -0.0409 0.2132 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5397(3) -0.00161(7) 0.30017(6) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.4496(4) 0.06085(7) 0.33126(6) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.4042 0.0587 0.3751 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4246(3) 0.12630(7) 0.29948(6) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.4899(4) 0.12832(7) 0.23482(6) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.4787 0.1726 0.2127 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6317(3) 0.07119(7) 0.13306(6) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.7908(4) 0.13158(7) 0.10920(6) 0.0172(3) Uani 1 1 d . . . . .
H8 H 0.8702 0.1694 0.1371 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8309(4) 0.13539(7) 0.04391(6) 0.0187(3) Uani 1 1 d . . . . .
H9 H 0.9430 0.1764 0.0285 0.022 Uiso 1 1 calc R U . . .
N1 N 0.7216(3) 0.08501(6) 0.00153(5) 0.0172(2) Uani 1 1 d . . . . .
C10 C 0.5652(3) 0.02711(6) 0.02431(6) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.5212(3) 0.01767(7) 0.08936(6) 0.0163(3) Uani 1 1 d . . . . .
H11 H 0.4169 -0.0248 0.1037 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5765(4) -0.06935(7) 0.33667(6) 0.0186(3) Uani 1 1 d . . . . .
C13 C 0.4551(4) -0.13385(7) 0.30963(7) 0.0225(3) Uani 1 1 d D . . . .
H13 H 0.3519 -0.1332 0.2665 0.027 Uiso 1 1 calc R U . . .
N2 N 0.4737(4) -0.19678(7) 0.34020(6) 0.0264(3) Uani 1 1 d D . . . .
C14 C 0.6215(4) -0.19656(8) 0.40073(7) 0.0272(3) Uani 1 1 d D . . . .
H14 H 0.6365 -0.2405 0.4234 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7538(4) -0.13607(8) 0.43226(7) 0.0268(3) Uani 1 1 d D . . . .
H15 H 0.8577 -0.1387 0.4753 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7317(4) -0.07138(8) 0.39974(7) 0.0226(3) Uani 1 1 d D . . . .
H16 H 0.8212 -0.0291 0.4202 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3380(4) 0.19256(7) 0.33344(6) 0.0172(3) Uani 1 1 d . . . . .
C18A C 0.157(9) 0.2478(10) 0.2997(5) 0.0182(10) Uani 0.5 1 d D . P A 1
H18A H 0.0768 0.2401 0.2559 0.022 Uiso 0.5 1 calc R U P A 1
N3A N 0.089(4) 0.3112(6) 0.3259(3) 0.0197(8) Uani 0.5 1 d D . P A 1
C19A C 0.177(3) 0.3198(5) 0.3883(3) 0.0195(13) Uani 0.5 1 d D . P A 1
H19A H 0.1208 0.3637 0.4075 0.023 Uiso 0.5 1 calc R U P A 1
C20A C 0.347(5) 0.2680(7) 0.4267(5) 0.0205(11) Uani 0.5 1 d D . P A 1
H20A H 0.4112 0.2767 0.4709 0.025 Uiso 0.5 1 calc R U P A 1
C21A C 0.423(9) 0.2029(9) 0.3994(8) 0.0197(7) Uani 0.5 1 d D . P A 1
H21A H 0.5311 0.1657 0.4251 0.024 Uiso 0.5 1 calc R U P A 1
C18B C 0.443(9) 0.1989(9) 0.3989(7) 0.0197(7) Uani 0.5 1 d D . P A 2
H18B H 0.5739 0.1607 0.4191 0.024 Uiso 0.5 1 calc R U P A 2
N3B N 0.371(4) 0.2550(5) 0.4353(4) 0.0205(11) Uani 0.5 1 d D . P A 2
C19B C 0.211(3) 0.3107(4) 0.4050(3) 0.0183(14) Uani 0.5 1 d D . P A 2
H19B H 0.1676 0.3518 0.4295 0.022 Uiso 0.5 1 calc R U P A 2
C20B C 0.105(5) 0.3117(7) 0.3400(4) 0.0197(8) Uani 0.5 1 d D . P A 2
H20B H -0.0128 0.3521 0.3208 0.024 Uiso 0.5 1 calc R U P A 2
C21B C 0.174(9) 0.2524(10) 0.3033(5) 0.0182(10) Uani 0.5 1 d D . P A 2
H21B H 0.1110 0.2524 0.2584 0.022 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
C2 C1 C6 119.35(12) . .
C2 C1 C7 121.70(11) . .
C6 C1 C7 118.94(11) . .
C1 C2 C3 120.46(12) . .
C1 C2 H2 119.8 . .
C3 C2 H2 119.8 . .
C4 C3 C2 119.00(12) . .
C4 C3 C12 119.61(11) . .
C2 C3 C12 121.38(12) . .
C5 C4 C3 121.64(12) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C4 C5 C6 118.36(12) . .
C4 C5 C17 121.15(11) . .
C6 C5 C17 120.48(12) . .
C5 C6 C1 121.14(12) . .
C5 C6 H6 119.4 . .
C1 C6 H6 119.4 . .
C8 C7 C11 117.50(11) . .
C8 C7 C1 120.51(11) . .
C11 C7 C1 121.94(11) . .
C9 C8 C7 118.85(12) . .
C9 C8 H8 120.6 . .
C7 C8 H8 120.6 . .
N1 C9 C8 124.18(12) . .
N1 C9 H9 117.9 . .
C8 C9 H9 117.9 . .
C9 N1 C10 117.07(11) . .
N1 C10 C11 122.88(11) . .
N1 C10 C10 115.94(14) . 3_655
C11 C10 C10 121.17(14) . 3_655
C7 C11 C10 119.48(12) . .
C7 C11 H11 120.3 . .
C10 C11 H11 120.3 . .
C16 C12 C13 116.99(12) . .
C16 C12 C3 121.50(12) . .
C13 C12 C3 121.51(12) . .
N2 C13 C12 124.67(13) . .
N2 C13 H13 117.7 . .
C12 C13 H13 117.7 . .
C14 N2 C13 116.64(13) . .
N2 C14 C15 123.77(13) . .
N2 C14 H14 118.1 . .
C15 C14 H14 118.1 . .
C14 C15 C16 118.69(13) . .
C14 C15 H15 120.7 . .
C16 C15 H15 120.7 . .
C15 C16 C12 119.23(13) . .
C15 C16 H16 120.4 . .
C12 C16 H16 120.4 . .
C18A C17 C21A 117.0(7) . .
C18B C17 C21B 116.5(6) . .
C18B C17 C5 119.2(4) . .
C18A C17 C5 119.9(4) . .
C21A C17 C5 123.2(4) . .
C21B C17 C5 124.2(4) . .
N3A C18A C17 123.6(6) . .
N3A C18A H18A 118.2 . .
C17 C18A H18A 118.2 . .
C19A N3A C18A 117.9(4) . .
N3A C19A C20A 123.2(4) . .
N3A C19A H19A 118.4 . .
C20A C19A H19A 118.4 . .
C19A C20A C21A 118.9(4) . .
C19A C20A H20A 120.6 . .
C21A C20A H20A 120.6 . .
C20A C21A C17 119.2(6) . .
C20A C21A H21A 120.4 . .
C17 C21A H21A 120.4 . .
N3B C18B C17 124.9(6) . .
N3B C18B H18B 117.6 . .
C17 C18B H18B 117.6 . .
C19B N3B C18B 116.7(2) . .
N3B C19B C20B 123.73(19) . .
N3B C19B H19B 118.1 . .
C20B C19B H19B 118.1 . .
C19B C20B C21B 118.7(2) . .
C19B C20B H20B 120.7 . .
C21B C20B H20B 120.7 . .
C20B C21B C17 119.3(5) . .
C20B C21B H21B 120.3 . .
C17 C21B H21B 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3990(18) .
C1 C6 1.4001(17) .
C1 C7 1.4874(17) .
C2 C3 1.3990(17) .
C2 H2 0.9500 .
C3 C4 1.3982(18) .
C3 C12 1.4835(18) .
C4 C5 1.3963(18) .
C4 H4 0.9500 .
C5 C6 1.3989(17) .
C5 C17 1.4841(17) .
C6 H6 0.9500 .
C7 C8 1.3965(18) .
C7 C11 1.3967(18) .
C8 C9 1.3911(18) .
C8 H8 0.9500 .
C9 N1 1.3360(17) .
C9 H9 0.9500 .
N1 C10 1.3452(17) .
C10 C11 1.3985(17) .
C10 C10 1.491(2) 3_655
C11 H11 0.9500 .
C12 C16 1.3954(19) .
C12 C13 1.3961(19) .
C13 N2 1.3425(18) .
C13 H13 0.9500 .
N2 C14 1.337(2) .
C14 C15 1.383(2) .
C14 H14 0.9500 .
C15 C16 1.391(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18B 1.396(15) .
C17 C18A 1.398(17) .
C17 C21A 1.402(15) .
C17 C21B 1.403(16) .
C18A N3A 1.347(6) .
C18A H18A 0.9500 .
N3A C19A 1.329(6) .
C19A C20A 1.381(7) .
C19A H19A 0.9500 .
C20A C21A 1.391(6) .
C20A H20A 0.9500 .
C21A H21A 0.9500 .
C18B N3B 1.342(2) .
C18B H18B 0.9500 .
N3B C19B 1.337(2) .
C19B C20B 1.384(2) .
C19B H19B 0.9500 .
C20B C21B 1.391(2) .
C20B H20B 0.9500 .
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
C6 C1 C2 C3 0.0(2) . . . .
C7 C1 C2 C3 179.64(12) . . . .
C1 C2 C3 C4 1.67(19) . . . .
C1 C2 C3 C12 -177.86(12) . . . .
C2 C3 C4 C5 -1.9(2) . . . .
C12 C3 C4 C5 177.64(12) . . . .
C3 C4 C5 C6 0.4(2) . . . .
C3 C4 C5 C17 -178.38(12) . . . .
C4 C5 C6 C1 1.3(2) . . . .
C17 C5 C6 C1 -179.91(12) . . . .
C2 C1 C6 C5 -1.5(2) . . . .
C7 C1 C6 C5 178.86(12) . . . .
C2 C1 C7 C8 -145.70(13) . . . .
C6 C1 C7 C8 33.97(19) . . . .
C2 C1 C7 C11 36.78(19) . . . .
C6 C1 C7 C11 -143.55(13) . . . .
C11 C7 C8 C9 -0.02(19) . . . .
C1 C7 C8 C9 -177.65(12) . . . .
C7 C8 C9 N1 1.0(2) . . . .
C8 C9 N1 C10 -0.4(2) . . . .
C9 N1 C10 C11 -1.30(19) . . . .
C9 N1 C10 C10 177.99(14) . . . 3_655
C8 C7 C11 C10 -1.51(19) . . . .
C1 C7 C11 C10 176.08(12) . . . .
N1 C10 C11 C7 2.3(2) . . . .
C10 C10 C11 C7 -176.98(14) 3_655 . . .
C4 C3 C12 C16 -38.87(19) . . . .
C2 C3 C12 C16 140.66(14) . . . .
C4 C3 C12 C13 140.64(14) . . . .
C2 C3 C12 C13 -39.83(19) . . . .
C16 C12 C13 N2 0.8(2) . . . .
C3 C12 C13 N2 -178.71(13) . . . .
C12 C13 N2 C14 -0.3(2) . . . .
C13 N2 C14 C15 -0.3(2) . . . .
N2 C14 C15 C16 0.3(2) . . . .
C14 C15 C16 C12 0.2(2) . . . .
C13 C12 C16 C15 -0.7(2) . . . .
C3 C12 C16 C15 178.80(13) . . . .
C4 C5 C17 C18B 30.3(18) . . . .
C6 C5 C17 C18B -148.5(18) . . . .
C4 C5 C17 C18A -150.2(17) . . . .
C6 C5 C17 C18A 31.0(17) . . . .
C4 C5 C17 C21A 28.4(19) . . . .
C6 C5 C17 C21A -150.4(19) . . . .
C4 C5 C17 C21B -153.8(18) . . . .
C6 C5 C17 C21B 27.4(18) . . . .
C21A C17 C18A N3A 6(4) . . . .
C5 C17 C18A N3A -175(2) . . . .
C17 C18A N3A C19A -5(4) . . . .
C18A N3A C19A C20A 3(3) . . . .
N3A C19A C20A C21A -2(3) . . . .
C19A C20A C21A C17 3(4) . . . .
C18A C17 C21A C20A -4(4) . . . .
C5 C17 C21A C20A 176.9(19) . . . .
C21B C17 C18B N3B 6(4) . . . .
C5 C17 C18B N3B -178(2) . . . .
C17 C18B N3B C19B -5(4) . . . .
C18B N3B C19B C20B 3(3) . . . .
N3B C19B C20B C21B -1(3) . . . .
C19B C20B C21B C17 2(4) . . . .
C18B C17 C21B C20B -4(4) . . . .
C5 C17 C21B C20B 179.9(18) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132564862
