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#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/51/7235182.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_7235182
loop_
_publ_author_name
'Yi-Jiun Shiu'
'Yi-Ting Chen'
'Wei-Kai Lee'
'Chung-Chih Wu'
'Tzu-Chieh Lin'
'Shih-Hung Liu'
'Pi-Tai Chou'
'Chin-Wei Lu'
'I-Chen Cheng'
'Yi-Jyun Lien'
'Yun Chi'
_publ_section_title
;
 Efficient thermally activated delayed fluorescence of functional
 phenylpyridinato boron complexes and high performance organic
 light-emitting diodes
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1452
_journal_page_last               1462
_journal_paper_doi               10.1039/C6TC04994J
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C47 H35 B F N3'
_chemical_formula_weight         671.59
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                101.835(3)
_cell_angle_beta                 95.538(2)
_cell_angle_gamma                110.288(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7399(5)
_cell_length_b                   13.7142(8)
_cell_length_c                   14.6944(8)
_cell_measurement_reflns_used    9533
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.44
_cell_volume                     1771.61(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.243
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0646P)²+0.9962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6320
_reflns_number_total             8134
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2017-5-1452.cif
_cod_data_source_block           ic17607
_cod_database_code               7235182
_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   0.985
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
B1 B 0.03154(19) 0.14436(13) 0.76610(12) 0.0205(3) Uani 1 1 d . . . . .
N1 N 0.16182(15) 0.09842(11) 0.74679(9) 0.0251(3) Uani 1 1 d . . . . .
N2 N 0.30065(15) 0.53241(10) 1.08333(9) 0.0245(3) Uani 1 1 d . . . . .
N3 N -0.23923(15) 0.24381(12) 0.43995(10) 0.0270(3) Uani 1 1 d . . . . .
C1 C -0.07971(17) 0.04002(12) 0.79246(10) 0.0225(3) Uani 1 1 d . . . . .
C2 C -0.22252(19) 0.01574(14) 0.81124(12) 0.0309(4) Uani 1 1 d . . . . .
H2 H -0.2707 0.0653 0.8115 0.037 Uiso 1 1 calc R U . . .
C3 C -0.2929(2) -0.08250(18) 0.82953(14) 0.0449(5) Uani 1 1 d . . . . .
C4 C -0.2290(3) -0.15729(17) 0.83131(17) 0.0543(6) Uani 1 1 d . . . . .
H4 H -0.2820 -0.2237 0.8448 0.065 Uiso 1 1 calc R U . . .
C5 C -0.0873(3) -0.13408(16) 0.81316(15) 0.0469(5) Uani 1 1 d . . . . .
H5 H -0.0401 -0.1841 0.8138 0.056 Uiso 1 1 calc R U . . .
C6 C -0.0141(2) -0.03582(13) 0.79371(12) 0.0305(4) Uani 1 1 d . . . . .
C7 C 0.1330(2) 0.00213(13) 0.76854(11) 0.0295(4) Uani 1 1 d . . . . .
C8 C 0.2382(2) -0.04508(16) 0.76363(14) 0.0447(5) Uani 1 1 d . . . . .
H8 H 0.2210 -0.1106 0.7813 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3679(2) 0.00422(19) 0.73275(15) 0.0500(6) Uani 1 1 d . . . . .
H9 H 0.4399 -0.0280 0.7281 0.060 Uiso 1 1 calc R U . . .
C10 C 0.3932(2) 0.09999(19) 0.70868(14) 0.0453(5) Uani 1 1 d . . . . .
H10 H 0.4813 0.1336 0.6862 0.054 Uiso 1 1 calc R U . . .
C11 C 0.28875(19) 0.14644(15) 0.71771(12) 0.0325(4) Uani 1 1 d . . . . .
H11 H 0.3070 0.2136 0.7031 0.039 Uiso 1 1 calc R U . . .
C12 C 0.10130(16) 0.25047(12) 0.85446(10) 0.0203(3) Uani 1 1 d . . . . .
C13 C 0.10379(17) 0.24661(12) 0.94898(11) 0.0226(3) Uani 1 1 d . . . . .
H13 H 0.0616 0.1787 0.9625 0.027 Uiso 1 1 calc R U . . .
C14 C 0.16537(17) 0.33797(12) 1.02387(11) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.1611 0.3317 1.0868 0.028 Uiso 1 1 calc R U . . .
C15 C 0.23344(16) 0.43880(12) 1.00738(10) 0.0207(3) Uani 1 1 d . . . . .
C16 C 0.23175(17) 0.44488(12) 0.91393(11) 0.0238(3) Uani 1 1 d . . . . .
H16 H 0.2759 0.5127 0.9006 0.029 Uiso 1 1 calc R U . . .
C17 C 0.16630(18) 0.35293(12) 0.84005(11) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.1656 0.3599 0.7770 0.029 Uiso 1 1 calc R U . . .
C18 C 0.38240(16) 0.53172(12) 1.16811(10) 0.0218(3) Uani 1 1 d . . . . .
C19 C 0.45050(18) 0.45826(13) 1.17241(11) 0.0268(3) Uani 1 1 d . . . . .
H19 H 0.4399 0.4038 1.1175 0.032 Uiso 1 1 calc R U . . .
C20 C 0.5337(2) 0.46481(15) 1.25700(13) 0.0355(4) Uani 1 1 d . . . . .
H20 H 0.5800 0.4146 1.2596 0.043 Uiso 1 1 calc R U . . .
C21 C 0.5504(2) 0.54345(16) 1.33784(13) 0.0374(4) Uani 1 1 d . . . . .
H21 H 0.6083 0.5475 1.3954 0.045 Uiso 1 1 calc R U . . .
C22 C 0.4820(2) 0.61606(14) 1.33395(12) 0.0328(4) Uani 1 1 d . . . . .
H22 H 0.4924 0.6701 1.3891 0.039 Uiso 1 1 calc R U . . .
C23 C 0.39851(19) 0.61003(13) 1.24995(11) 0.0278(3) Uani 1 1 d . . . . .
H23 H 0.3515 0.6599 1.2480 0.033 Uiso 1 1 calc R U . . .
C24 C 0.33587(18) 0.63492(12) 1.06173(10) 0.0227(3) Uani 1 1 d . . . . .
C25 C 0.48261(18) 0.69687(13) 1.06071(11) 0.0277(3) Uani 1 1 d . . . . .
H25 H 0.5598 0.6723 1.0759 0.033 Uiso 1 1 calc R U . . .
C26 C 0.5159(2) 0.79435(14) 1.03760(13) 0.0347(4) Uani 1 1 d . . . . .
H26 H 0.6162 0.8368 1.0370 0.042 Uiso 1 1 calc R U . . .
C27 C 0.4038(2) 0.83003(15) 1.01544(14) 0.0383(4) Uani 1 1 d . . . . .
H27 H 0.4266 0.8968 0.9992 0.046 Uiso 1 1 calc R U . . .
C28 C 0.2583(2) 0.76848(15) 1.01695(14) 0.0370(4) Uani 1 1 d . . . . .
H28 H 0.1814 0.7933 1.0017 0.044 Uiso 1 1 calc R U . . .
C29 C 0.22300(19) 0.67086(14) 1.04045(12) 0.0301(4) Uani 1 1 d . . . . .
H29 H 0.1228 0.6292 1.0420 0.036 Uiso 1 1 calc R U . . .
C30 C -0.03796(16) 0.16807(12) 0.67297(10) 0.0208(3) Uani 1 1 d . . . . .
C31 C -0.01590(17) 0.13473(12) 0.58088(11) 0.0242(3) Uani 1 1 d . . . . .
H31 H 0.0464 0.0950 0.5705 0.029 Uiso 1 1 calc R U . . .
C32 C -0.08217(18) 0.15773(14) 0.50369(11) 0.0264(3) Uani 1 1 d . . . . .
H32 H -0.0662 0.1326 0.4419 0.032 Uiso 1 1 calc R U . . .
C33 C -0.17122(17) 0.21724(13) 0.51733(11) 0.0238(3) Uani 1 1 d . . . . .
C34 C -0.19558(19) 0.25130(14) 0.60754(12) 0.0293(4) Uani 1 1 d . . . . .
H34 H -0.2567 0.2920 0.6176 0.035 Uiso 1 1 calc R U . . .
C35 C -0.13120(19) 0.22628(14) 0.68320(11) 0.0287(4) Uani 1 1 d . . . . .
H35 H -0.1510 0.2494 0.7443 0.034 Uiso 1 1 calc R U . . .
C36 C -0.14895(18) 0.30756(13) 0.38777(11) 0.0261(3) Uani 1 1 d . . . . .
C37 C 0.0008(2) 0.37076(16) 0.42441(15) 0.0392(4) Uani 1 1 d . . . . .
H37 H 0.0426 0.3729 0.4863 0.047 Uiso 1 1 calc R U . . .
C38 C 0.0887(2) 0.43035(18) 0.37142(18) 0.0531(6) Uani 1 1 d . . . . .
H38 H 0.1906 0.4726 0.3971 0.064 Uiso 1 1 calc R U . . .
C39 C 0.0302(3) 0.42912(18) 0.28153(17) 0.0520(6) Uani 1 1 d . . . . .
H39 H 0.0912 0.4703 0.2455 0.062 Uiso 1 1 calc R U . . .
C40 C -0.1179(2) 0.36748(16) 0.24466(14) 0.0409(5) Uani 1 1 d . . . . .
H40 H -0.1591 0.3670 0.1832 0.049 Uiso 1 1 calc R U . . .
C41 C -0.2071(2) 0.30618(14) 0.29656(12) 0.0294(4) Uani 1 1 d . . . . .
H41 H -0.3084 0.2630 0.2699 0.035 Uiso 1 1 calc R U . . .
C42 C -0.39231(17) 0.22671(14) 0.43430(11) 0.0263(3) Uani 1 1 d . . . . .
C43 C -0.4895(2) 0.13103(16) 0.44826(13) 0.0361(4) Uani 1 1 d . . . . .
H43 H -0.4529 0.0783 0.4607 0.043 Uiso 1 1 calc R U . . .
C44 C -0.6393(2) 0.1128(2) 0.44401(14) 0.0505(6) Uani 1 1 d . . . . .
H44 H -0.7050 0.0478 0.4540 0.061 Uiso 1 1 calc R U . . .
C45 C -0.6936(2) 0.1885(2) 0.42536(14) 0.0545(6) Uani 1 1 d . . . . .
H45 H -0.7966 0.1753 0.4218 0.065 Uiso 1 1 calc R U . . .
C46 C -0.5984(2) 0.2830(2) 0.41200(13) 0.0471(5) Uani 1 1 d . . . . .
H46 H -0.6361 0.3349 0.3989 0.056 Uiso 1 1 calc R U . . .
C47 C -0.4476(2) 0.30327(16) 0.41741(12) 0.0333(4) Uani 1 1 d . . . . .
H47 H -0.3822 0.3696 0.4095 0.040 Uiso 1 1 calc R U . . .
F1 F -0.43413(15) -0.11043(13) 0.84446(11) 0.0687(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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
C30 B1 C1 113.13(12) . .
C30 B1 C12 112.55(12) . .
C1 B1 C12 113.78(12) . .
C30 B1 N1 111.89(12) . .
C1 B1 N1 96.59(11) . .
C12 B1 N1 107.73(12) . .
C11 N1 C7 120.66(15) . .
C11 N1 B1 127.47(14) . .
C7 N1 B1 111.79(13) . .
C18 N2 C15 121.76(13) . .
C18 N2 C24 116.23(12) . .
C15 N2 C24 117.74(12) . .
C36 N3 C42 121.73(13) . .
C36 N3 C33 119.78(13) . .
C42 N3 C33 116.70(12) . .
C2 C1 C6 118.40(15) . .
C2 C1 B1 130.97(14) . .
C6 C1 B1 110.62(14) . .
C1 C2 C3 118.05(18) . .
F1 C3 C4 116.47(18) . .
F1 C3 C2 119.6(2) . .
C4 C3 C2 123.93(19) . .
C3 C4 C5 118.61(18) . .
C4 C5 C6 118.7(2) . .
C5 C6 C1 122.34(18) . .
C5 C6 C7 127.29(17) . .
C1 C6 C7 110.32(14) . .
N1 C7 C8 119.74(18) . .
N1 C7 C6 110.33(14) . .
C8 C7 C6 129.93(17) . .
C9 C8 C7 119.26(19) . .
C10 C9 C8 120.05(18) . .
C9 C10 C11 119.1(2) . .
N1 C11 C10 121.14(18) . .
C13 C12 C17 115.47(13) . .
C13 C12 B1 123.36(13) . .
C17 C12 B1 121.16(13) . .
C14 C13 C12 122.71(14) . .
C13 C14 C15 120.49(14) . .
C16 C15 C14 117.88(14) . .
C16 C15 N2 121.01(14) . .
C14 C15 N2 121.10(13) . .
C17 C16 C15 120.68(14) . .
C16 C17 C12 122.72(14) . .
C23 C18 C19 118.89(14) . .
C23 C18 N2 118.24(14) . .
C19 C18 N2 122.85(14) . .
C20 C19 C18 119.81(15) . .
C21 C20 C19 121.01(17) . .
C20 C21 C22 119.32(16) . .
C23 C22 C21 120.10(16) . .
C22 C23 C18 120.88(16) . .
C25 C24 C29 120.25(15) . .
C25 C24 N2 119.90(14) . .
C29 C24 N2 119.84(15) . .
C26 C25 C24 119.84(16) . .
C27 C26 C25 120.15(17) . .
C26 C27 C28 119.81(17) . .
C29 C28 C27 120.81(17) . .
C28 C29 C24 119.13(16) . .
C31 C30 C35 115.79(14) . .
C31 C30 B1 126.13(13) . .
C35 C30 B1 118.08(13) . .
C32 C31 C30 122.41(14) . .
C33 C32 C31 119.85(14) . .
C34 C33 C32 119.21(14) . .
C34 C33 N3 119.39(14) . .
C32 C33 N3 121.40(14) . .
C33 C34 C35 120.30(15) . .
C34 C35 C30 122.43(15) . .
C41 C36 C37 118.35(15) . .
C41 C36 N3 120.40(15) . .
C37 C36 N3 121.23(15) . .
C38 C37 C36 120.53(19) . .
C39 C38 C37 120.8(2) . .
C38 C39 C40 119.27(18) . .
C39 C40 C41 120.61(19) . .
C40 C41 C36 120.44(17) . .
C47 C42 C43 119.12(16) . .
C47 C42 N3 121.97(15) . .
C43 C42 N3 118.89(16) . .
C44 C43 C42 120.0(2) . .
C45 C44 C43 120.4(2) . .
C46 C45 C44 119.83(18) . .
C45 C46 C47 120.5(2) . .
C46 C47 C42 120.07(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C30 1.610(2) .
B1 C1 1.614(2) .
B1 C12 1.623(2) .
B1 N1 1.624(2) .
N1 C11 1.341(2) .
N1 C7 1.363(2) .
N2 C18 1.4159(19) .
N2 C15 1.4180(19) .
N2 C24 1.437(2) .
N3 C36 1.413(2) .
N3 C42 1.418(2) .
N3 C33 1.4340(19) .
C1 C2 1.383(2) .
C1 C6 1.399(2) .
C2 C3 1.379(3) .
C3 F1 1.347(2) .
C3 C4 1.375(3) .
C4 C5 1.370(3) .
C5 C6 1.392(3) .
C6 C7 1.457(3) .
C7 C8 1.389(2) .
C8 C9 1.380(3) .
C9 C10 1.376(3) .
C10 C11 1.378(3) .
C12 C13 1.399(2) .
C12 C17 1.397(2) .
C13 C14 1.388(2) .
C14 C15 1.394(2) .
C15 C16 1.392(2) .
C16 C17 1.387(2) .
C18 C23 1.393(2) .
C18 C19 1.393(2) .
C19 C20 1.386(2) .
C20 C21 1.384(3) .
C21 C22 1.384(3) .
C22 C23 1.382(2) .
C24 C25 1.390(2) .
C24 C29 1.386(2) .
C25 C26 1.384(2) .
C26 C27 1.381(3) .
C27 C28 1.380(3) .
C28 C29 1.387(2) .
C30 C31 1.399(2) .
C30 C35 1.402(2) .
C31 C32 1.396(2) .
C32 C33 1.384(2) .
C33 C34 1.384(2) .
C34 C35 1.385(2) .
C36 C41 1.398(2) .
C36 C37 1.396(2) .
C37 C38 1.383(3) .
C38 C39 1.382(3) .
C39 C40 1.380(3) .
C40 C41 1.389(2) .
C42 C47 1.388(2) .
C42 C43 1.395(2) .
C43 C44 1.385(3) .
C44 C45 1.379(4) .
C45 C46 1.372(3) .
C46 C47 1.388(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339182
