#------------------------------------------------------------------------------
#$Date: 2020-05-07 17:54:20 +0300 (Thu, 07 May 2020) $
#$Revision: 251847 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/76/4517646.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_4517646
loop_
_publ_author_name
'Hsieh, Chia-Min'
'Wu, Tien-Lin'
'Jayakumar, Jayachandran'
'Wang, Ying-Chun'
'Ko, Chang-Lun'
'Hung, Wen-Yi'
'Lin, Tzu-Chieh'
'Wu, Hsin-Hui'
'Lin, Kuan-Heng'
'Lin, Cheng-Hung'
'Hsieh, Shuchen'
'Cheng, Chien-Hong'
_publ_section_title
;
 Diboron-based Delayed Fluorescent Emitters with Orange-to-red Emission
 and Superior OLEDs Efficiency.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.0c03711
_journal_year                    2020
_chemical_formula_sum            'C52 H44 B2 N2'
_chemical_formula_weight         718.51
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 106.920(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   21.1057(12)
_cell_length_b                   7.7008(5)
_cell_length_c                   12.7349(7)
_cell_measurement_reflns_used    3019
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.8422
_cell_measurement_theta_min      2.8309
_cell_volume                     1980.2(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15044
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.017
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lamellar
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0864P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2679
_reflns_number_total             3964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am0c03711_si_002.cif
_cod_data_source_block           190402LT
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4517646
_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.
;
_shelxl_version_number           2014/6
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
N1 N 0.18210(7) 0.44103(19) 0.43627(12) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.17222(10) 0.8423(3) 0.6570(2) 0.0449(6) Uani 1 1 d . . . . .
H1 H 0.1692 0.9317 0.7067 0.054 Uiso 1 1 calc R U . . .
C2 C 0.13977(9) 0.8588(2) 0.54630(19) 0.0397(5) Uani 1 1 d . . . . .
H6 H 0.1146 0.9605 0.5200 0.048 Uiso 1 1 calc R U . . .
C3 C 0.14364(9) 0.7277(2) 0.47310(18) 0.0352(5) Uani 1 1 d . . . . .
H7 H 0.1214 0.7402 0.3971 0.042 Uiso 1 1 calc R U . . .
C4 C 0.18019(9) 0.5784(2) 0.51177(16) 0.0300(4) Uani 1 1 d . . . . .
C5 C 0.24502(8) 0.3580(2) 0.45181(15) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.25679(9) 0.1904(2) 0.49263(16) 0.0310(4) Uani 1 1 d . . . . .
H8 H 0.2225 0.1285 0.5110 0.037 Uiso 1 1 calc R U . . .
C7 C 0.31778(9) 0.1120(2) 0.50700(15) 0.0296(4) Uani 1 1 d . . . . .
C8 C 0.36972(8) 0.2002(2) 0.48112(14) 0.0237(4) Uani 1 1 d . . . . .
C9 C 0.44511(8) -0.0048(2) 0.39272(14) 0.0240(4) Uani 1 1 d . . . . .
C10 C 0.49565(8) 0.0997(2) 0.60072(14) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.21289(9) 0.5629(3) 0.62277(17) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.2381 0.4616 0.6496 0.043 Uiso 1 1 calc R U . . .
C12 C 0.20906(10) 0.6948(3) 0.69486(18) 0.0441(5) Uani 1 1 d . . . . .
H5 H 0.2319 0.6837 0.7707 0.053 Uiso 1 1 calc R U . . .
C13 C 0.01330(11) 0.1266(3) 0.3132(2) 0.0501(6) Uani 1 1 d . . . . .
H2 H -0.0245 0.0552 0.2850 0.060 Uiso 1 1 calc R U . . .
C14 C 0.06499(11) 0.1205(3) 0.26793(19) 0.0478(6) Uani 1 1 d . . . . .
H22 H 0.0631 0.0432 0.2089 0.057 Uiso 1 1 calc R U . . .
C15 C 0.11974(10) 0.2260(3) 0.30768(17) 0.0384(5) Uani 1 1 d . . . . .
H3 H 0.1547 0.2225 0.2745 0.046 Uiso 1 1 calc R U . . .
C16 C 0.12432(9) 0.3375(2) 0.39594(16) 0.0300(4) Uani 1 1 d . . . . .
C17 C 0.32857(10) -0.0700(2) 0.55233(19) 0.0411(5) Uani 1 1 d . . . . .
H9 H 0.3557 -0.0661 0.6292 0.062 Uiso 1 1 calc R U . . .
H10 H 0.3513 -0.1388 0.5095 0.062 Uiso 1 1 calc R U . . .
H11 H 0.2857 -0.1233 0.5478 0.062 Uiso 1 1 calc R U . . .
C18 C 0.35707(8) 0.3708(2) 0.44020(14) 0.0248(4) Uani 1 1 d . . . . .
C19 C 0.29538(8) 0.4463(2) 0.42572(14) 0.0255(4) Uani 1 1 d . . . . .
H12 H 0.2877 0.5610 0.3973 0.031 Uiso 1 1 calc R U . . .
C20 C 0.40987(9) 0.4712(2) 0.40872(17) 0.0359(5) Uani 1 1 d . . . . .
H14 H 0.4117 0.4331 0.3362 0.054 Uiso 1 1 calc R U . . .
H15 H 0.4528 0.4504 0.4630 0.054 Uiso 1 1 calc R U . . .
H13 H 0.3995 0.5954 0.4064 0.054 Uiso 1 1 calc R U . . .
C21 C 0.39442(9) -0.0054(2) 0.29385(14) 0.0265(4) Uani 1 1 d . . . . .
H19 H 0.3546 0.0558 0.2893 0.032 Uiso 1 1 calc R U . . .
C22 C 0.40047(9) -0.0923(2) 0.20230(15) 0.0286(4) Uani 1 1 d . . . . .
H16 H 0.3653 -0.0902 0.1357 0.034 Uiso 1 1 calc R U . . .
C23 C 0.54168(9) 0.1827(2) 0.79152(15) 0.0292(4) Uani 1 1 d . . . . .
H17 H 0.5370 0.2420 0.8542 0.035 Uiso 1 1 calc R U . . .
C24 C 0.49075(9) 0.1866(2) 0.69404(15) 0.0273(4) Uani 1 1 d . . . . .
H18 H 0.4516 0.2499 0.6908 0.033 Uiso 1 1 calc R U . . .
C25 C 0.01689(10) 0.2379(3) 0.4001(2) 0.0461(6) Uani 1 1 d . . . . .
H21 H -0.0186 0.2421 0.4320 0.055 Uiso 1 1 calc R U . . .
C26 C 0.07209(9) 0.3438(3) 0.44131(17) 0.0363(5) Uani 1 1 d . . . . .
H20 H 0.0739 0.4205 0.5006 0.044 Uiso 1 1 calc R U . . .
B1 B 0.43716(10) 0.1011(2) 0.49258(17) 0.0242(4) Uani 1 1 d . . . . .
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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
C16 N1 C5 117.54(14) . . ?
C16 N1 C4 117.76(15) . . ?
C5 N1 C4 116.13(14) . . ?
C12 C1 C2 119.6(2) . . ?
C12 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 120.50(19) . . ?
C1 C2 H6 119.7 . . ?
C3 C2 H6 119.7 . . ?
C2 C3 C4 119.76(19) . . ?
C2 C3 H7 120.1 . . ?
C4 C3 H7 120.1 . . ?
C11 C4 C3 119.45(18) . . ?
C11 C4 N1 121.09(16) . . ?
C3 C4 N1 119.44(17) . . ?
C19 C5 C6 118.81(16) . . ?
C19 C5 N1 119.58(15) . . ?
C6 C5 N1 121.61(16) . . ?
C7 C6 C5 120.90(17) . . ?
C7 C6 H8 119.5 . . ?
C5 C6 H8 119.5 . . ?
C6 C7 C8 121.06(16) . . ?
C6 C7 C17 119.14(17) . . ?
C8 C7 C17 119.80(16) . . ?
C7 C8 C18 117.35(15) . . ?
C7 C8 B1 119.10(15) . . ?
C18 C8 B1 123.45(16) . . ?
C21 C9 C10 118.64(16) . 3_656 ?
C21 C9 B1 120.06(15) . . ?
C10 C9 B1 121.28(15) 3_656 . ?
C24 C10 C9 118.44(16) . 3_656 ?
C24 C10 B1 120.90(16) . . ?
C9 C10 B1 120.64(15) 3_656 . ?
C4 C11 C12 120.30(18) . . ?
C4 C11 H4 119.8 . . ?
C12 C11 H4 119.8 . . ?
C1 C12 C11 120.4(2) . . ?
C1 C12 H5 119.8 . . ?
C11 C12 H5 119.8 . . ?
C14 C13 C25 119.4(2) . . ?
C14 C13 H2 120.3 . . ?
C25 C13 H2 120.3 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H22 119.8 . . ?
C15 C14 H22 119.8 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H3 119.6 . . ?
C16 C15 H3 119.6 . . ?
C26 C16 C15 118.70(18) . . ?
C26 C16 N1 122.16(17) . . ?
C15 C16 N1 119.14(18) . . ?
C7 C17 H9 109.5 . . ?
C7 C17 H10 109.5 . . ?
H9 C17 H10 109.5 . . ?
C7 C17 H11 109.5 . . ?
H9 C17 H11 109.5 . . ?
H10 C17 H11 109.5 . . ?
C19 C18 C8 120.58(16) . . ?
C19 C18 C20 119.25(16) . . ?
C8 C18 C20 120.15(16) . . ?
C5 C19 C18 121.30(16) . . ?
C5 C19 H12 119.4 . . ?
C18 C19 H12 119.4 . . ?
C18 C20 H14 109.5 . . ?
C18 C20 H15 109.5 . . ?
H14 C20 H15 109.5 . . ?
C18 C20 H13 109.5 . . ?
H14 C20 H13 109.5 . . ?
H15 C20 H13 109.5 . . ?
C22 C21 C9 121.86(17) . . ?
C22 C21 H19 119.1 . . ?
C9 C21 H19 119.1 . . ?
C21 C22 C23 119.40(16) . 3_656 ?
C21 C22 H16 120.3 . . ?
C23 C22 H16 120.3 3_656 . ?
C24 C23 C22 120.13(17) . 3_656 ?
C24 C23 H17 119.9 . . ?
C22 C23 H17 119.9 3_656 . ?
C23 C24 C10 121.52(16) . . ?
C23 C24 H18 119.2 . . ?
C10 C24 H18 119.2 . . ?
C13 C25 C26 120.6(2) . . ?
C13 C25 H21 119.7 . . ?
C26 C25 H21 119.7 . . ?
C16 C26 C25 120.1(2) . . ?
C16 C26 H20 120.0 . . ?
C25 C26 H20 120.0 . . ?
C10 B1 C9 118.08(15) . . ?
C10 B1 C8 122.97(16) . . ?
C9 B1 C8 118.92(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.422(2) . ?
N1 C5 1.435(2) . ?
N1 C4 1.438(2) . ?
C1 C12 1.381(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(3) . ?
C2 H6 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H7 0.9500 . ?
C4 C11 1.386(3) . ?
C5 C19 1.381(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.385(2) . ?
C6 H8 0.9500 . ?
C7 C8 1.408(2) . ?
C7 C17 1.507(2) . ?
C8 C18 1.410(2) . ?
C8 B1 1.584(3) . ?
C9 C21 1.395(2) . ?
C9 C10 1.429(2) 3_656 ?
C9 B1 1.561(3) . ?
C10 C24 1.394(3) . ?
C10 C9 1.429(2) 3_656 ?
C10 B1 1.559(2) . ?
C11 C12 1.387(3) . ?
C11 H4 0.9500 . ?
C12 H5 0.9500 . ?
C13 C14 1.375(3) . ?
C13 C25 1.385(3) . ?
C13 H2 0.9500 . ?
C14 C15 1.382(3) . ?
C14 H22 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H3 0.9500 . ?
C16 C26 1.386(3) . ?
C17 H9 0.9800 . ?
C17 H10 0.9800 . ?
C17 H11 0.9800 . ?
C18 C19 1.388(2) . ?
C18 C20 1.503(3) . ?
C19 H12 0.9500 . ?
C20 H14 0.9800 . ?
C20 H15 0.9800 . ?
C20 H13 0.9800 . ?
C21 C22 1.382(3) . ?
C21 H19 0.9500 . ?
C22 C23 1.388(2) 3_656 ?
C22 H16 0.9500 . ?
C23 C24 1.386(2) . ?
C23 C22 1.388(2) 3_656 ?
C23 H17 0.9500 . ?
C24 H18 0.9500 . ?
C25 C26 1.394(3) . ?
C25 H21 0.9500 . ?
C26 H20 0.9500 . ?
