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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/7/23/51/7235181.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_7235181
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 H31 B F N3'
_chemical_formula_weight         667.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 131.7267(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2980(9)
_cell_length_b                   12.8948(5)
_cell_length_c                   16.2166(6)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.16
_cell_measurement_theta_min      4.34
_cell_volume                     3479.9(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11879
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         4.337
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 2861 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_coef       0.00089(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6539
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0481
_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)+(0.0871P)²+1.9012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                6194
_reflns_number_total             6539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2017-5-1452.cif
_cod_data_source_block           ic17609
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7235181
_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   0.863
_shelx_estimated_absorpt_t_max   0.888
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'
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 0.5289(2) 0.9229(3) 0.3248(3) 0.0283(7) Uani 1 1 d . . . . .
N1 N 0.58550(17) 1.0190(2) 0.3474(2) 0.0364(6) Uani 1 1 d . . . . .
N2 N 0.72707(18) 0.7017(2) 0.7474(2) 0.0369(7) Uani 1 1 d . . . . .
N3 N 0.39699(17) 0.6798(2) -0.0700(2) 0.0349(6) Uani 1 1 d . . . . .
C1 C 0.45557(19) 0.9923(2) 0.2932(2) 0.0262(6) Uani 1 1 d . . . . .
C2 C 0.3824(2) 0.9633(3) 0.2569(3) 0.0381(8) Uani 1 1 d . . . . .
H2 H 0.3706 0.8924 0.2567 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3255(2) 1.0401(5) 0.2202(3) 0.0580(13) Uani 1 1 d . . . . .
C4 C 0.3398(3) 1.1436(4) 0.2192(4) 0.0626(14) Uani 1 1 d . . . . .
H4 H 0.2994 1.1939 0.1930 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4142(3) 1.1731(3) 0.2572(4) 0.0548(11) Uani 1 1 d . . . . .
H5 H 0.4259 1.2440 0.2575 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4709(2) 1.0976(3) 0.2945(3) 0.0376(8) Uani 1 1 d . . . . .
C7 C 0.5515(2) 1.1118(3) 0.3336(3) 0.0386(8) Uani 1 1 d . . . . .
C8 C 0.5937(4) 1.2038(4) 0.3577(4) 0.0648(14) Uani 1 1 d . . . . .
H8 H 0.5700 1.2692 0.3478 0.078 Uiso 1 1 calc R U . . .
C9 C 0.6704(4) 1.1976(5) 0.3961(4) 0.0762(18) Uani 1 1 d . . . . .
H9 H 0.7004 1.2591 0.4144 0.091 Uiso 1 1 calc R U . . .
C10 C 0.7032(3) 1.1032(6) 0.4081(4) 0.0712(17) Uani 1 1 d . . . . .
H10 H 0.7559 1.0992 0.4338 0.085 Uiso 1 1 calc R U . . .
C11 C 0.6605(2) 1.0147(4) 0.3831(3) 0.0526(11) Uani 1 1 d . . . . .
H11 H 0.6834 0.9494 0.3908 0.063 Uiso 1 1 calc R U . . .
C12 C 0.5781(2) 0.8564(3) 0.4376(3) 0.0318(7) Uani 1 1 d . . . . .
C13 C 0.5707(2) 0.8722(3) 0.5138(3) 0.0434(9) Uani 1 1 d . . . . .
H13 H 0.5317 0.9204 0.4972 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6180(3) 0.8206(4) 0.6149(3) 0.0488(10) Uani 1 1 d . . . . .
H14 H 0.6102 0.8328 0.6650 0.059 Uiso 1 1 calc R U . . .
C15 C 0.6761(2) 0.7520(3) 0.6421(3) 0.0350(7) Uani 1 1 d . . . . .
C16 C 0.6861(3) 0.7354(4) 0.5684(4) 0.0686(16) Uani 1 1 d . . . . .
H16 H 0.7263 0.6890 0.5859 0.082 Uiso 1 1 calc R U . . .
C17 C 0.6368(4) 0.7874(5) 0.4677(4) 0.0730(17) Uani 1 1 d . . . . .
H17 H 0.6441 0.7746 0.4171 0.088 Uiso 1 1 calc R U . . .
C18 C 0.8027(2) 0.7372(3) 0.8394(3) 0.0365(7) Uani 1 1 d . . . . .
C19 C 0.8443(3) 0.8228(4) 0.8489(3) 0.0517(11) Uani 1 1 d . . . . .
H19 H 0.8239 0.8646 0.7867 0.062 Uiso 1 1 calc R U . . .
C20 C 0.9168(3) 0.8449(4) 0.9529(4) 0.0670(15) Uani 1 1 d . . . . .
H20 H 0.9464 0.9039 0.9625 0.080 Uiso 1 1 calc R U . . .
C21 C 0.9476(3) 0.7832(4) 1.0442(4) 0.0657(14) Uani 1 1 d . . . . .
H21 H 0.9974 0.8010 1.1147 0.079 Uiso 1 1 calc R U . . .
C22 C 0.9066(2) 0.6966(4) 1.0331(3) 0.0487(10) Uani 1 1 d . . . . .
H22 H 0.9285 0.6536 1.0951 0.058 Uiso 1 1 calc R U . . .
C23 C 0.8326(2) 0.6729(3) 0.9298(3) 0.0332(7) Uani 1 1 d . . . . .
C24 C 0.7723(2) 0.5960(3) 0.8910(2) 0.0312(7) Uani 1 1 d . . . . .
C25 C 0.7651(2) 0.5150(3) 0.9405(3) 0.0400(8) Uani 1 1 d . . . . .
H25 H 0.8080 0.4995 1.0164 0.048 Uiso 1 1 calc R U . . .
C26 C 0.6959(3) 0.4576(3) 0.8793(4) 0.0493(10) Uani 1 1 d . . . . .
H26 H 0.6903 0.4033 0.9133 0.059 Uiso 1 1 calc R U . . .
C27 C 0.6331(3) 0.4787(3) 0.7665(4) 0.0474(9) Uani 1 1 d . . . . .
H27 H 0.5859 0.4372 0.7251 0.057 Uiso 1 1 calc R U . . .
C28 C 0.6382(2) 0.5579(3) 0.7144(3) 0.0396(8) Uani 1 1 d . . . . .
H28 H 0.5956 0.5714 0.6379 0.047 Uiso 1 1 calc R U . . .
C29 C 0.7074(2) 0.6170(3) 0.7774(3) 0.0308(7) Uani 1 1 d . . . . .
C30 C 0.4964(2) 0.8562(3) 0.2171(2) 0.0303(7) Uani 1 1 d . . . . .
C31 C 0.4687(3) 0.7554(3) 0.2038(3) 0.0511(11) Uani 1 1 d . . . . .
H31 H 0.4717 0.7256 0.2599 0.061 Uiso 1 1 calc R U . . .
C32 C 0.4368(3) 0.6973(3) 0.1098(3) 0.0517(11) Uani 1 1 d . . . . .
H32 H 0.4190 0.6283 0.1031 0.062 Uiso 1 1 calc R U . . .
C33 C 0.4310(2) 0.7401(3) 0.0266(3) 0.0322(7) Uani 1 1 d . . . . .
C34 C 0.4561(2) 0.8396(3) 0.0368(3) 0.0364(8) Uani 1 1 d . . . . .
H34 H 0.4517 0.8698 -0.0205 0.044 Uiso 1 1 calc R U . . .
C35 C 0.4881(2) 0.8968(3) 0.1308(3) 0.0353(7) Uani 1 1 d . . . . .
H35 H 0.5049 0.9660 0.1362 0.042 Uiso 1 1 calc R U . . .
C36 C 0.4387(2) 0.6248(3) -0.0911(3) 0.0314(7) Uani 1 1 d . . . . .
C37 C 0.5208(2) 0.6147(3) -0.0266(3) 0.0381(8) Uani 1 1 d . . . . .
H37 H 0.5576 0.6468 0.0439 0.046 Uiso 1 1 calc R U . . .
C38 C 0.5477(2) 0.5558(3) -0.0684(4) 0.0461(9) Uani 1 1 d . . . . .
H38 H 0.6038 0.5473 -0.0258 0.055 Uiso 1 1 calc R U . . .
C39 C 0.4934(3) 0.5092(3) -0.1721(4) 0.0510(10) Uani 1 1 d . . . . .
H39 H 0.5131 0.4697 -0.1992 0.061 Uiso 1 1 calc R U . . .
C40 C 0.4116(2) 0.5195(3) -0.2360(3) 0.0423(8) Uani 1 1 d . . . . .
H40 H 0.3752 0.4876 -0.3067 0.051 Uiso 1 1 calc R U . . .
C41 C 0.3830(2) 0.5773(3) -0.1956(3) 0.0322(7) Uani 1 1 d . . . . .
C42 C 0.3040(2) 0.6046(3) -0.2385(3) 0.0332(7) Uani 1 1 d . . . . .
C43 C 0.2253(2) 0.5839(3) -0.3370(3) 0.0442(9) Uani 1 1 d . . . . .
H43 H 0.2159 0.5404 -0.3919 0.053 Uiso 1 1 calc R U . . .
C44 C 0.1622(2) 0.6274(4) -0.3528(3) 0.0522(10) Uani 1 1 d . . . . .
H44 H 0.1088 0.6131 -0.4190 0.063 Uiso 1 1 calc R U . . .
C45 C 0.1748(3) 0.6922(4) -0.2736(4) 0.0494(10) Uani 1 1 d . . . . .
H45 H 0.1298 0.7225 -0.2878 0.059 Uiso 1 1 calc R U . . .
C46 C 0.2513(2) 0.7133(3) -0.1750(3) 0.0415(8) Uani 1 1 d . . . . .
H46 H 0.2600 0.7567 -0.1206 0.050 Uiso 1 1 calc R U . . .
C47 C 0.3151(2) 0.6681(3) -0.1589(3) 0.0330(7) Uani 1 1 d . . . . .
F1 F 0.2529(2) 1.0187(3) 0.1765(3) 0.0932(11) 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C12 B1 C1 115.6(3) . .
C12 B1 C30 114.7(3) . .
C1 B1 C30 108.6(3) . .
C12 B1 N1 108.0(3) . .
C1 B1 N1 96.8(2) . .
C30 B1 N1 111.8(3) . .
C7 N1 C11 120.1(4) . .
C7 N1 B1 111.9(3) . .
C11 N1 B1 128.0(4) . .
C29 N2 C18 108.9(3) . .
C29 N2 C15 126.4(3) . .
C18 N2 C15 124.5(3) . .
C36 N3 C47 108.9(3) . .
C36 N3 C33 126.6(3) . .
C47 N3 C33 124.5(3) . .
C2 C1 C6 118.9(3) . .
C2 C1 B1 130.5(3) . .
C6 C1 B1 110.2(3) . .
C1 C2 C3 118.3(4) . .
F1 C3 C4 114.6(5) . .
F1 C3 C2 122.2(5) . .
C4 C3 C2 123.0(4) . .
C3 C4 C5 118.7(4) . .
C6 C5 C4 118.7(4) . .
C5 C6 C1 122.4(4) . .
C5 C6 C7 127.2(4) . .
C1 C6 C7 110.2(3) . .
N1 C7 C8 120.4(4) . .
N1 C7 C6 110.5(3) . .
C8 C7 C6 129.1(4) . .
C9 C8 C7 118.6(5) . .
C10 C9 C8 120.2(5) . .
C11 C10 C9 120.0(5) . .
N1 C11 C10 120.7(5) . .
C13 C12 C17 115.8(3) . .
C13 C12 B1 123.0(3) . .
C17 C12 B1 120.9(3) . .
C12 C13 C14 122.6(4) . .
C15 C14 C13 120.0(3) . .
C16 C15 C14 119.0(3) . .
C16 C15 N2 120.6(3) . .
C14 C15 N2 120.4(3) . .
C15 C16 C17 119.2(4) . .
C12 C17 C16 123.3(4) . .
C19 C18 N2 128.8(3) . .
C19 C18 C23 122.5(3) . .
N2 C18 C23 108.7(3) . .
C20 C19 C18 116.9(4) . .
C19 C20 C21 121.9(4) . .
C22 C21 C20 120.6(4) . .
C21 C22 C23 119.1(3) . .
C22 C23 C18 118.9(3) . .
C22 C23 C24 133.9(3) . .
C18 C23 C24 107.1(3) . .
C25 C24 C29 118.9(3) . .
C25 C24 C23 134.5(3) . .
C29 C24 C23 106.6(3) . .
C26 C25 C24 119.7(3) . .
C25 C26 C27 120.4(4) . .
C28 C27 C26 121.6(4) . .
C27 C28 C29 117.6(3) . .
N2 C29 C28 129.5(3) . .
N2 C29 C24 108.7(3) . .
C28 C29 C24 121.8(3) . .
C35 C30 C31 116.6(3) . .
C35 C30 B1 123.4(3) . .
C31 C30 B1 119.8(3) . .
C30 C31 C32 121.5(3) . .
C33 C32 C31 120.0(4) . .
C34 C33 C32 119.5(3) . .
C34 C33 N3 121.2(3) . .
C32 C33 N3 119.2(3) . .
C33 C34 C35 120.0(3) . .
C30 C35 C34 122.3(3) . .
N3 C36 C37 129.2(3) . .
N3 C36 C41 108.7(3) . .
C37 C36 C41 122.1(3) . .
C36 C37 C38 117.7(3) . .
C37 C38 C39 120.8(4) . .
C40 C39 C38 121.2(3) . .
C39 C40 C41 119.2(3) . .
C40 C41 C36 118.9(3) . .
C40 C41 C42 134.2(3) . .
C36 C41 C42 106.8(3) . .
C43 C42 C47 118.6(3) . .
C43 C42 C41 134.6(3) . .
C47 C42 C41 106.7(3) . .
C44 C43 C42 119.0(3) . .
C43 C44 C45 121.4(4) . .
C46 C45 C44 121.3(4) . .
C45 C46 C47 117.1(4) . .
N3 C47 C46 128.5(3) . .
N3 C47 C42 108.8(3) . .
C46 C47 C42 122.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 C12 1.617(5) .
B1 C1 1.620(5) .
B1 C30 1.622(5) .
B1 N1 1.626(5) .
N1 C7 1.353(5) .
N1 C11 1.359(5) .
N2 C29 1.381(4) .
N2 C18 1.389(5) .
N2 C15 1.429(4) .
N3 C36 1.381(4) .
N3 C47 1.390(5) .
N3 C33 1.432(4) .
C1 C2 1.368(5) .
C1 C6 1.397(5) .
C2 C3 1.392(6) .
C3 F1 1.294(6) .
C3 C4 1.374(8) .
C4 C5 1.385(8) .
C5 C6 1.376(6) .
C6 C7 1.466(6) .
C7 C8 1.399(6) .
C8 C9 1.377(9) .
C9 C10 1.367(10) .
C10 C11 1.364(7) .
C12 C13 1.368(5) .
C12 C17 1.376(6) .
C13 C14 1.392(5) .
C14 C15 1.376(6) .
C15 C16 1.371(6) .
C16 C17 1.391(6) .
C18 C19 1.383(6) .
C18 C23 1.407(5) .
C19 C20 1.382(6) .
C20 C21 1.393(7) .
C21 C22 1.377(7) .
C22 C23 1.394(5) .
C23 C24 1.435(5) .
C24 C25 1.391(5) .
C24 C29 1.419(4) .
C25 C26 1.369(6) .
C26 C27 1.404(7) .
C27 C28 1.378(6) .
C28 C29 1.382(5) .
C30 C35 1.386(5) .
C30 C31 1.392(5) .
C31 C32 1.395(5) .
C32 C33 1.382(5) .
C33 C34 1.366(5) .
C34 C35 1.389(5) .
C36 C37 1.383(5) .
C36 C41 1.410(5) .
C37 C38 1.392(5) .
C38 C39 1.395(6) .
C39 C40 1.378(6) .
C40 C41 1.396(5) .
C41 C42 1.442(5) .
C42 C43 1.403(5) .
C42 C47 1.405(5) .
C43 C44 1.372(6) .
C44 C45 1.395(6) .
C45 C46 1.382(6) .
C46 C47 1.391(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339181
