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#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/66/4516653.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_4516653
loop_
_publ_author_name
'Song, Xiaozeng'
'Zhang, Dongdong'
'Li, Haoyuan'
'Cai, Minghan'
'Huang, Tianyu'
'Duan, Lian'
_publ_section_title
;
 Exciplex System with Increased Donor-Acceptor Distance as the Sensitizing
 Host for Conventional Fluorescent OLEDs with High Efficiency and
 Extremely Low Roll-Off.
;
_journal_issue                   25
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              22595
_journal_page_last               22602
_journal_paper_doi               10.1021/acsami.9b05963
_journal_volume                  11
_journal_year                    2019
_chemical_formula_moiety         'C78 H84 N4'
_chemical_formula_sum            'C78 H84 N4'
_chemical_formula_weight         1077.49
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   23.201(3)
_cell_length_b                   23.201(3)
_cell_length_c                   21.302(4)
_cell_measurement_reflns_used    8581
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.3932
_cell_volume                     9930(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            26895
_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         27.486
_diffrn_reflns_theta_min         1.393
_exptl_absorpt_coefficient_mu    0.062
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       block
_exptl_crystal_F_000             3480
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5053
_refine_ls_number_restraints     636
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.1075
_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)+(0.1477P)²+18.2787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2998
_refine_ls_wR_factor_ref         0.3111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4852
_reflns_number_total             5042
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am9b05963_si_002.cif
_cod_data_source_block           1_sq
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               4516653
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.000000 0.000000 0.40552(18) 0.0336(8) Uani 1 3 d S TU P . .
N2 N 0.18307(11) 0.27607(10) 0.41191(12) 0.0413(6) Uani 1 1 d . U . . .
C1 C 0.04664(12) 0.06922(12) 0.40646(11) 0.0322(5) Uani 1 1 d . U . . .
C2' C 0.10777(11) 0.09443(11) 0.43802(11) 0.0301(5) Uani 1 1 d . U . . .
H2' H 0.118257 0.065310 0.458210 0.036 Uiso 1 1 calc R U . . .
C3' C 0.15245(12) 0.16206(12) 0.43933(12) 0.0335(5) Uani 1 1 d . U . . .
H3' H 0.193213 0.177998 0.459451 0.040 Uiso 1 1 calc R U . . .
C4' C 0.13682(13) 0.20638(12) 0.41076(13) 0.0366(6) Uani 1 1 d . U . . .
C5' C 0.07663(14) 0.18216(14) 0.38008(14) 0.0419(6) Uani 1 1 d . U . . .
H5' H 0.065694 0.211548 0.361145 0.050 Uiso 1 1 calc R U . . .
C6 C 0.03250(13) 0.11431(13) 0.37739(13) 0.0381(6) Uani 1 1 d . U . . .
H6 H -0.007370 0.098641 0.355702 0.046 Uiso 1 1 calc R U . . .
C7 C 0.24796(13) 0.30619(12) 0.38882(13) 0.0379(6) Uani 1 1 d . U . . .
C8 C 0.28078(14) 0.27758(13) 0.35999(15) 0.0448(7) Uani 1 1 d . U . . .
H8 H 0.261889 0.231589 0.357912 0.054 Uiso 1 1 calc R U . . .
C9 C 0.34307(15) 0.31977(14) 0.33411(16) 0.0496(7) Uani 1 1 d . U . . .
H9 H 0.365312 0.301049 0.313877 0.059 Uiso 1 1 calc R U . . .
C10 C 0.37363(14) 0.38906(14) 0.33724(16) 0.0465(7) Uani 1 1 d . U . . .
C11 C 0.34074(14) 0.41637(12) 0.36954(14) 0.0428(6) Uani 1 1 d . U . . .
H11 H 0.361144 0.462289 0.374306 0.051 Uiso 1 1 calc R U . . .
C12 C 0.27753(14) 0.37567(12) 0.39484(13) 0.0391(6) Uani 1 1 d . U . . .
C13 C 0.22758(15) 0.38801(13) 0.42220(13) 0.0427(6) Uani 1 1 d . U . . .
C14 C 0.22690(19) 0.44614(15) 0.43874(15) 0.0539(8) Uani 1 1 d . U . . .
H14 H 0.265174 0.487361 0.433804 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1694(2) 0.44260(18) 0.46248(16) 0.0641(10) Uani 1 1 d . U . . .
C16 C 0.1132(2) 0.37966(19) 0.46914(18) 0.0674(11) Uani 1 1 d . U . . .
H16 H 0.074416 0.376834 0.484592 0.081 Uiso 1 1 calc R U . . .
C17 C 0.11234(18) 0.32141(17) 0.45401(17) 0.0576(9) Uani 1 1 d . U . . .
H17 H 0.074100 0.280290 0.459535 0.069 Uiso 1 1 calc R U . . .
C18 C 0.16998(15) 0.32598(13) 0.43037(13) 0.0427(6) Uani 1 1 d . U . . .
C19 C 0.43977(15) 0.43437(17) 0.30310(18) 0.0570(8) Uani 1 1 d . U . . .
C20 C 0.4628(3) 0.3960(3) 0.2642(3) 0.117(2) Uani 1 1 d . U . . .
H20A H 0.502610 0.426378 0.242046 0.176 Uiso 1 1 calc R U . . .
H20B H 0.428742 0.368800 0.234567 0.176 Uiso 1 1 calc R U . . .
H20C H 0.471795 0.368139 0.290985 0.176 Uiso 1 1 calc R U . . .
C21 C 0.4926(2) 0.4738(3) 0.3503(3) 0.126(2) Uani 1 1 d . U . . .
H21A H 0.532469 0.505534 0.329113 0.190 Uiso 1 1 calc R U . . .
H21B H 0.501458 0.444451 0.374899 0.190 Uiso 1 1 calc R U . . .
H21C H 0.477713 0.496903 0.377401 0.190 Uiso 1 1 calc R U . . .
C22 C 0.4318(3) 0.4836(3) 0.2620(3) 0.1022(16) Uani 1 1 d . U . . .
H22A H 0.472788 0.511742 0.240477 0.153 Uiso 1 1 calc R U . . .
H22B H 0.420431 0.510439 0.287838 0.153 Uiso 1 1 calc R U . . .
H22C H 0.397024 0.459759 0.231923 0.153 Uiso 1 1 calc R U . . .
C2_1 C 0.1858(9) 0.5138(11) 0.4859(10) 0.067(4) Uani 0.264(8) 1 d D U P A 2
C3_1 C 0.2531(9) 0.5769(7) 0.4722(10) 0.093(6) Uani 0.264(8) 1 d D U P A 2
H3A_1 H 0.245990 0.613524 0.463867 0.139 Uiso 0.264(8) 1 calc R U P A 2
H3B_1 H 0.273371 0.569264 0.436205 0.139 Uiso 0.264(8) 1 calc R U P A 2
H3C_1 H 0.281885 0.587102 0.507849 0.139 Uiso 0.264(8) 1 calc R U P A 2
C4_1 C 0.1798(12) 0.5137(12) 0.5569(9) 0.079(5) Uani 0.264(8) 1 d D U P A 2
H4A_1 H 0.166969 0.545518 0.569246 0.118 Uiso 0.264(8) 1 calc R U P A 2
H4B_1 H 0.221827 0.525260 0.575661 0.118 Uiso 0.264(8) 1 calc R U P A 2
H4C_1 H 0.146653 0.470136 0.570811 0.118 Uiso 0.264(8) 1 calc R U P A 2
C5_1 C 0.1309(11) 0.5220(11) 0.4560(12) 0.105(6) Uani 0.264(8) 1 d D U P A 2
H5A_1 H 0.108209 0.532370 0.487887 0.157 Uiso 0.264(8) 1 calc R U P A 2
H5B_1 H 0.099787 0.481331 0.435430 0.157 Uiso 0.264(8) 1 calc R U P A 2
H5C_1 H 0.149827 0.557436 0.425810 0.157 Uiso 0.264(8) 1 calc R U P A 2
C23_1 C 0.1624(4) 0.5036(4) 0.4780(4) 0.0669(17) Uani 0.736(8) 1 d . U P A 1
C24_1 C 0.1923(4) 0.5542(3) 0.4240(3) 0.084(2) Uani 0.736(8) 1 d . U P A 1
H24A_1 H 0.192855 0.594469 0.435455 0.126 Uiso 0.736(8) 1 calc R U P A 1
H24B_1 H 0.165851 0.535911 0.386884 0.126 Uiso 0.736(8) 1 calc R U P A 1
H24C_1 H 0.236984 0.563771 0.415933 0.126 Uiso 0.736(8) 1 calc R U P A 1
C25_1 C 0.0911(4) 0.4882(4) 0.4890(4) 0.090(2) Uani 0.736(8) 1 d . U P A 1
H25A_1 H 0.090584 0.529125 0.493829 0.134 Uiso 0.736(8) 1 calc R U P A 1
H25B_1 H 0.073846 0.461896 0.526340 0.134 Uiso 0.736(8) 1 calc R U P A 1
H25C_1 H 0.063981 0.464050 0.453746 0.134 Uiso 0.736(8) 1 calc R U P A 1
C26_1 C 0.2039(6) 0.5334(5) 0.5357(4) 0.110(3) Uani 0.736(8) 1 d . U P A 1
H26A_1 H 0.201648 0.571969 0.548086 0.165 Uiso 0.736(8) 1 calc R U P A 1
H26B_1 H 0.249274 0.545946 0.526832 0.165 Uiso 0.736(8) 1 calc R U P A 1
H26C_1 H 0.187368 0.501251 0.569051 0.165 Uiso 0.736(8) 1 calc R U P A 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'
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 C1 119.978(10) . 2
C1 N1 C1 119.982(10) . 3
C1 N1 C1 119.980(10) 2 3
C18 N2 C7 108.2(2) . .
C18 N2 C4' 126.5(2) . .
C7 N2 C4' 125.1(2) . .
C6 C1 C2' 118.0(2) . .
C6 C1 N1 120.8(2) . .
C2' C1 N1 121.2(2) . .
C3' C2' C1 120.7(2) . .
C2' C3' C4' 120.4(2) . .
C5' C4' C3' 119.4(2) . .
C5' C4' N2 120.3(2) . .
C3' C4' N2 120.3(2) . .
C4' C5' C6 120.3(2) . .
C5' C6 C1 121.3(2) . .
C8 C7 N2 129.3(2) . .
C8 C7 C12 121.4(2) . .
N2 C7 C12 109.1(2) . .
C7 C8 C9 117.8(2) . .
C8 C9 C10 122.8(3) . .
C11 C10 C9 117.9(3) . .
C11 C10 C19 120.5(3) . .
C9 C10 C19 121.5(3) . .
C10 C11 C12 120.8(2) . .
C11 C12 C7 119.1(2) . .
C11 C12 C13 134.1(2) . .
C7 C12 C13 106.5(2) . .
C18 C13 C14 119.5(3) . .
C18 C13 C12 107.1(2) . .
C14 C13 C12 133.4(3) . .
C15 C14 C13 120.4(3) . .
C14 C15 C16 117.7(3) . .
C14 C15 C23_1 124.3(4) . .
C16 C15 C23_1 117.9(4) . .
C14 C15 C2_1 109.3(7) . .
C16 C15 C2_1 132.3(7) . .
C17 C16 C15 123.4(3) . .
C16 C17 C18 118.0(3) . .
C17 C18 N2 130.1(3) . .
C17 C18 C13 120.9(3) . .
N2 C18 C13 109.0(2) . .
C21 C19 C20 108.1(5) . .
C21 C19 C22 107.3(4) . .
C20 C19 C22 110.0(4) . .
C21 C19 C10 109.4(3) . .
C20 C19 C10 112.6(3) . .
C22 C19 C10 109.2(3) . .
C5_1 C2_1 C4_1 109.6(18) . .
C5_1 C2_1 C3_1 108.5(17) . .
C4_1 C2_1 C3_1 103.9(16) . .
C5_1 C2_1 C15 102.7(14) . .
C4_1 C2_1 C15 109.7(15) . .
C3_1 C2_1 C15 122.2(14) . .
C26_1 C23_1 C25_1 110.7(8) . .
C26_1 C23_1 C15 105.2(6) . .
C25_1 C23_1 C15 114.8(6) . .
C26_1 C23_1 C24_1 108.7(7) . .
C25_1 C23_1 C24_1 108.4(6) . .
C15 C23_1 C24_1 109.0(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.419(2) .
N1 C1 1.419(2) 2
N1 C1 1.419(2) 3
N2 C18 1.393(3) .
N2 C7 1.394(3) .
N2 C4' 1.425(3) .
C1 C6 1.389(3) .
C1 C2' 1.406(3) .
C2' C3' 1.382(3) .
C3' C4' 1.390(3) .
C4' C5' 1.382(4) .
C5' C6 1.385(4) .
C7 C8 1.380(4) .
C7 C12 1.407(3) .
C8 C9 1.391(4) .
C9 C10 1.397(4) .
C10 C11 1.393(4) .
C10 C19 1.541(4) .
C11 C12 1.396(4) .
C12 C13 1.448(4) .
C13 C18 1.401(4) .
C13 C14 1.402(4) .
C14 C15 1.391(5) .
C15 C16 1.395(6) .
C15 C23_1 1.539(8) .
C15 C2_1 1.58(2) .
C16 C17 1.379(5) .
C17 C18 1.383(4) .
C19 C21 1.493(6) .
C19 C20 1.497(6) .
C19 C22 1.522(5) .
C2_1 C5_1 1.519(17) .
C2_1 C4_1 1.520(18) .
C2_1 C3_1 1.543(17) .
C23_1 C26_1 1.499(12) .
C23_1 C25_1 1.526(10) .
C23_1 C24_1 1.540(9) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 153306944
