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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/75/1557567.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_1557567
loop_
_publ_author_name
'Mahmood, Zafar'
'Taddei, Maria'
'Rehmat, Noreen'
'Bussotti, Laura'
'Doria, Sandra'
'Guan, Qinglin'
'Ji, Shaomin'
'Zhao, Jianzhang'
'Di Donato, Mariangela'
'Huo, Yanping'
'Xing, Yong Heng'
_publ_section_title
;
 Color-Tunable Delayed Fluorescence and Efficient Spin--Orbit Charge
 Transfer Intersystem Crossing in Compact Carbazole-Anthracene-Bodipy
 Triads Employing the Sequential Electron Transfer Approach
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.9b11687
_journal_year                    2020
_chemical_formula_sum            'C45 H34 B F2 N3'
_chemical_formula_weight         665.56
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                106.387(6)
_cell_angle_beta                 109.432(6)
_cell_angle_gamma                104.590(6)
_cell_formula_units_Z            2
_cell_length_a                   12.309(4)
_cell_length_b                   12.652(4)
_cell_length_c                   12.944(5)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.68
_cell_measurement_theta_min      2.69
_cell_volume                     1685.3(10)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8649
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.816
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_correction_T_min  0.9561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.330
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0028(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         5901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0737
_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)+(0.1329P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2111
_refine_ls_wR_factor_ref         0.2341
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3376
_reflns_number_total             5901
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp9b11687_si_004.cif
_cod_data_source_block           1
_cod_database_code               1557567
_shelx_shelxl_version_number     2017/1
_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   0.956
_shelx_estimated_absorpt_t_max   0.973
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
C1 C 0.7583(3) 0.1345(3) -0.3575(3) 0.0480(9) Uani 1 1 d . . . . .
C2 C 0.6884(4) 0.0147(4) -0.3931(3) 0.0583(10) Uani 1 1 d . . . . .
H2 H 0.635150 -0.009287 -0.360054 0.070 Uiso 1 1 calc R U . . .
C3 C 0.7017(4) -0.0669(4) -0.4797(4) 0.0707(13) Uani 1 1 d . . . . .
H3 H 0.656112 -0.147573 -0.504617 0.085 Uiso 1 1 calc R U . . .
C4 C 0.7797(5) -0.0343(5) -0.5312(4) 0.0736(13) Uani 1 1 d . . . . .
H4 H 0.784732 -0.092305 -0.590302 0.088 Uiso 1 1 calc R U . . .
C5 C 0.8498(4) 0.0844(5) -0.4944(4) 0.0672(12) Uani 1 1 d . . . . .
H5 H 0.902751 0.107012 -0.528283 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8409(4) 0.1708(4) -0.4060(3) 0.0506(10) Uani 1 1 d . . . . .
C7 C 0.9018(4) 0.2982(4) -0.3468(3) 0.0508(10) Uani 1 1 d . . . . .
C8 C 0.9901(4) 0.3821(4) -0.3586(4) 0.0650(12) Uani 1 1 d . . . . .
H8 H 1.022925 0.357860 -0.412033 0.078 Uiso 1 1 calc R U . . .
C9 C 1.0277(4) 0.5010(4) -0.2899(4) 0.0680(12) Uani 1 1 d . . . . .
H9 H 1.086984 0.557864 -0.296255 0.082 Uiso 1 1 calc R U . . .
C10 C 0.9779(4) 0.5363(4) -0.2116(4) 0.0638(11) Uani 1 1 d . . . . .
H10 H 1.003818 0.617415 -0.167140 0.077 Uiso 1 1 calc R U . . .
C11 C 0.8916(4) 0.4571(4) -0.1961(3) 0.0541(10) Uani 1 1 d . . . . .
H11 H 0.859361 0.482999 -0.142583 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8547(3) 0.3366(4) -0.2640(3) 0.0494(9) Uani 1 1 d . . . . .
C13 C 0.7006(3) 0.2385(3) -0.1990(3) 0.0457(9) Uani 1 1 d . . . . .
C14 C 0.7605(3) 0.3107(3) -0.0783(3) 0.0506(10) Uani 1 1 d . . . . .
H14 H 0.845456 0.356331 -0.042902 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5745(3) 0.1682(3) -0.2508(3) 0.0512(10) Uani 1 1 d . . . . .
H15 H 0.533098 0.119183 -0.331949 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6953(3) 0.3156(3) -0.0097(3) 0.0491(10) Uani 1 1 d . . . . .
H16 H 0.736605 0.366274 0.071021 0.059 Uiso 1 1 calc R U . . .
C17 C 0.5116(4) 0.1719(3) -0.1809(3) 0.0522(10) Uani 1 1 d . . . . .
H17 H 0.427550 0.123089 -0.215871 0.063 Uiso 1 1 calc R U . . .
C18 C 0.5688(3) 0.2462(3) -0.0591(3) 0.0459(9) Uani 1 1 d . . . . .
C19 C 0.3644(4) 0.3298(3) -0.1094(3) 0.0553(10) Uani 1 1 d . . . . .
H19 H 0.412074 0.333544 -0.151875 0.066 Uiso 1 1 calc R U . . .
C20 C 0.4985(3) 0.2515(3) 0.0141(3) 0.0433(9) Uani 1 1 d . . . . .
C21 C 0.6309(4) 0.1791(3) 0.1474(4) 0.0566(10) Uani 1 1 d . . . . .
H21 H 0.677246 0.174446 0.103444 0.068 Uiso 1 1 calc R U . . .
C22 C 0.2674(4) 0.3639(4) -0.1379(4) 0.0621(11) Uani 1 1 d . . . . .
H22 H 0.249952 0.391509 -0.198575 0.074 Uiso 1 1 calc R U . . .
C23 C 0.3970(3) 0.2877(3) -0.0160(3) 0.0439(9) Uani 1 1 d . . . . .
C24 C 0.5296(3) 0.2170(3) 0.1120(3) 0.0434(9) Uani 1 1 d . . . . .
C25 C 0.6615(4) 0.1496(4) 0.2432(4) 0.0620(11) Uani 1 1 d . . . . .
H25 H 0.727537 0.124458 0.263386 0.074 Uiso 1 1 calc R U . . .
C26 C 0.1914(4) 0.3583(3) -0.0763(3) 0.0545(10) Uani 1 1 d . . . . .
H26 H 0.122813 0.379692 -0.098028 0.065 Uiso 1 1 calc R U . . .
C27 C 0.3232(3) 0.2867(3) 0.0502(3) 0.0402(8) Uani 1 1 d . . . . .
C28 C 0.4592(3) 0.2217(3) 0.1814(3) 0.0374(8) Uani 1 1 d . . . . .
C29 C 0.5941(4) 0.1567(4) 0.3127(4) 0.0559(10) Uani 1 1 d . . . . .
H29 H 0.617030 0.138590 0.379607 0.067 Uiso 1 1 calc R U . . .
C30 C 0.2197(3) 0.3216(3) 0.0142(3) 0.0463(9) Uani 1 1 d . . . . .
H30 H 0.169877 0.319063 0.054694 0.056 Uiso 1 1 calc R U . . .
C31 C 0.3553(3) 0.2532(3) 0.1473(3) 0.0381(8) Uani 1 1 d . . . . .
C32 C 0.4967(3) 0.1899(3) 0.2815(3) 0.0462(9) Uani 1 1 d . . . . .
H32 H 0.451878 0.192314 0.326891 0.055 Uiso 1 1 calc R U . . .
C33 C 0.4741(4) 0.5272(4) 0.3012(4) 0.0641(12) Uani 1 1 d . . . . .
H33A H 0.431768 0.528388 0.224663 0.096 Uiso 1 1 calc R U . . .
H33B H 0.521253 0.477834 0.294470 0.096 Uiso 1 1 calc R U . . .
H33C H 0.529306 0.606880 0.357915 0.096 Uiso 1 1 calc R U . . .
C34 C 0.2096(4) -0.0227(3) 0.0282(3) 0.0566(10) Uani 1 1 d . . . . .
H34A H 0.290482 -0.021428 0.071621 0.085 Uiso 1 1 calc R U . . .
H34B H 0.216441 0.027191 -0.014993 0.085 Uiso 1 1 calc R U . . .
H34C H 0.154614 -0.102888 -0.027010 0.085 Uiso 1 1 calc R U . . .
C35 C 0.3802(3) 0.4783(3) 0.3427(3) 0.0459(9) Uani 1 1 d . . . . .
C36 C 0.2969(3) 0.3584(3) 0.3022(3) 0.0421(8) Uani 1 1 d . . . . .
C37 C 0.2790(3) 0.2518(3) 0.2163(3) 0.0393(8) Uani 1 1 d . . . . .
C38 C 0.1915(3) 0.1420(3) 0.1937(3) 0.0407(8) Uani 1 1 d . . . . .
C39 C 0.1587(3) 0.0226(3) 0.1139(3) 0.0437(9) Uani 1 1 d . . . . .
C40 C 0.3586(3) 0.5451(3) 0.4324(3) 0.0528(10) Uani 1 1 d . . . . .
H40 H 0.399785 0.627065 0.475987 0.063 Uiso 1 1 calc R U . . .
C41 C 0.0673(3) -0.0479(3) 0.1310(3) 0.0509(10) Uani 1 1 d . . . . .
H41 H 0.027930 -0.130372 0.091186 0.061 Uiso 1 1 calc R U . . .
C42 C 0.2652(4) 0.4710(3) 0.4477(3) 0.0493(9) Uani 1 1 d . . . . .
C43 C 0.0422(3) 0.0231(3) 0.2173(3) 0.0451(9) Uani 1 1 d . . . . .
C44 C 0.2138(4) 0.5046(4) 0.5355(4) 0.0660(12) Uani 1 1 d . . . . .
H44A H 0.124698 0.476355 0.494208 0.099 Uiso 1 1 calc R U . . .
H44B H 0.247690 0.589785 0.576891 0.099 Uiso 1 1 calc R U . . .
H44C H 0.235947 0.469358 0.592060 0.099 Uiso 1 1 calc R U . . .
C45 C -0.0512(4) -0.0147(4) 0.2626(4) 0.0618(11) Uani 1 1 d . . . . .
H45A H -0.009298 0.006918 0.347034 0.093 Uiso 1 1 calc R U . . .
H45B H -0.095705 -0.099532 0.222434 0.093 Uiso 1 1 calc R U . . .
H45C H -0.108900 0.024160 0.247309 0.093 Uiso 1 1 calc R U . . .
N1 N 0.7672(3) 0.2360(3) -0.2705(3) 0.0487(8) Uani 1 1 d . . . . .
N2 N 0.2264(3) 0.3580(2) 0.3685(2) 0.0440(7) Uani 1 1 d . . . . .
N3 N 0.1185(3) 0.1383(2) 0.2562(2) 0.0420(7) Uani 1 1 d . . . . .
B1 B 0.1202(4) 0.2473(4) 0.3507(4) 0.0510(11) Uani 1 1 d . . . . .
F1 F 0.0060(2) 0.2576(2) 0.3084(3) 0.0791(8) Uani 1 1 d . . . . .
F2 F 0.1442(3) 0.2353(2) 0.4576(2) 0.0834(9) 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
_geom_angle_publ_flag
C2 C1 N1 130.0(3) . . ?
C2 C1 C6 121.5(3) . . ?
N1 C1 C6 108.4(3) . . ?
C3 C2 C1 117.0(4) . . ?
C2 C3 C4 123.0(5) . . ?
C5 C4 C3 119.7(4) . . ?
C4 C5 C6 119.6(4) . . ?
C5 C6 C1 119.2(4) . . ?
C5 C6 C7 133.4(4) . . ?
C1 C6 C7 107.4(3) . . ?
C8 C7 C12 119.6(4) . . ?
C8 C7 C6 133.1(4) . . ?
C12 C7 C6 107.3(3) . . ?
C9 C8 C7 119.0(4) . . ?
C8 C9 C10 120.2(4) . . ?
C11 C10 C9 123.0(4) . . ?
C10 C11 C12 117.0(4) . . ?
C11 C12 N1 130.3(3) . . ?
C11 C12 C7 121.2(4) . . ?
N1 C12 C7 108.4(3) . . ?
C14 C13 C15 119.5(3) . . ?
C14 C13 N1 120.5(3) . . ?
C15 C13 N1 119.9(3) . . ?
C16 C14 C13 120.6(3) . . ?
C17 C15 C13 119.2(3) . . ?
C14 C16 C18 121.2(3) . . ?
C15 C17 C18 122.6(4) . . ?
C16 C18 C17 116.9(3) . . ?
C16 C18 C20 121.3(3) . . ?
C17 C18 C20 121.8(3) . . ?
C22 C19 C23 122.5(4) . . ?
C23 C20 C24 119.7(3) . . ?
C23 C20 C18 119.5(3) . . ?
C24 C20 C18 120.7(3) . . ?
C25 C21 C24 121.8(4) . . ?
C19 C22 C26 120.6(4) . . ?
C20 C23 C19 122.8(3) . . ?
C20 C23 C27 120.1(3) . . ?
C19 C23 C27 117.1(3) . . ?
C20 C24 C21 122.7(3) . . ?
C20 C24 C28 119.9(3) . . ?
C21 C24 C28 117.5(3) . . ?
C21 C25 C29 120.6(4) . . ?
C30 C26 C22 119.3(3) . . ?
C31 C27 C30 122.4(3) . . ?
C31 C27 C23 119.7(3) . . ?
C30 C27 C23 117.9(3) . . ?
C31 C28 C32 122.4(3) . . ?
C31 C28 C24 119.8(3) . . ?
C32 C28 C24 117.8(3) . . ?
C32 C29 C25 119.6(4) . . ?
C26 C30 C27 122.5(3) . . ?
C28 C31 C27 120.7(3) . . ?
C28 C31 C37 119.4(3) . . ?
C27 C31 C37 119.9(3) . . ?
C29 C32 C28 122.6(3) . . ?
C40 C35 C36 105.7(3) . . ?
C40 C35 C33 124.8(3) . . ?
C36 C35 C33 129.5(3) . . ?
C37 C36 N2 120.1(3) . . ?
C37 C36 C35 131.9(3) . . ?
N2 C36 C35 108.0(3) . . ?
C36 C37 C38 121.5(3) . . ?
C36 C37 C31 119.6(3) . . ?
C38 C37 C31 118.9(3) . . ?
N3 C38 C37 120.0(3) . . ?
N3 C38 C39 108.0(3) . . ?
C37 C38 C39 131.9(3) . . ?
C41 C39 C38 105.7(3) . . ?
C41 C39 C34 124.6(3) . . ?
C38 C39 C34 129.7(3) . . ?
C35 C40 C42 109.6(3) . . ?
C39 C41 C43 109.6(3) . . ?
N2 C42 C40 108.8(3) . . ?
N2 C42 C44 123.2(3) . . ?
C40 C42 C44 128.0(3) . . ?
N3 C43 C41 108.4(3) . . ?
N3 C43 C45 123.3(3) . . ?
C41 C43 C45 128.3(3) . . ?
C1 N1 C12 108.4(3) . . ?
C1 N1 C13 126.4(3) . . ?
C12 N1 C13 125.1(3) . . ?
C42 N2 C36 107.9(3) . . ?
C42 N2 B1 126.3(3) . . ?
C36 N2 B1 125.8(3) . . ?
C43 N3 C38 108.2(3) . . ?
C43 N3 B1 125.6(3) . . ?
C38 N3 B1 126.2(3) . . ?
F2 B1 F1 109.3(3) . . ?
F2 B1 N3 111.1(3) . . ?
F1 B1 N3 109.4(3) . . ?
F2 B1 N2 109.7(4) . . ?
F1 B1 N2 111.1(3) . . ?
N3 B1 N2 106.2(3) . . ?
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
C1 C2 1.391(5) . ?
C1 N1 1.400(4) . ?
C1 C6 1.410(5) . ?
C2 C3 1.379(5) . ?
C3 C4 1.385(6) . ?
C4 C5 1.378(6) . ?
C5 C6 1.398(5) . ?
C6 C7 1.435(6) . ?
C7 C8 1.397(5) . ?
C7 C12 1.408(5) . ?
C8 C9 1.375(6) . ?
C9 C10 1.378(6) . ?
C10 C11 1.375(5) . ?
C11 C12 1.390(5) . ?
C12 N1 1.405(5) . ?
C13 C14 1.382(5) . ?
C13 C15 1.388(5) . ?
C13 N1 1.425(4) . ?
C14 C16 1.380(5) . ?
C15 C17 1.371(5) . ?
C16 C18 1.391(5) . ?
C17 C18 1.399(5) . ?
C18 C20 1.481(5) . ?
C19 C22 1.343(5) . ?
C19 C23 1.433(5) . ?
C20 C23 1.409(5) . ?
C20 C24 1.420(5) . ?
C21 C25 1.357(5) . ?
C21 C24 1.428(5) . ?
C22 C26 1.417(5) . ?
C23 C27 1.443(5) . ?
C24 C28 1.440(4) . ?
C25 C29 1.412(5) . ?
C26 C30 1.352(5) . ?
C27 C31 1.404(4) . ?
C27 C30 1.428(5) . ?
C28 C31 1.403(4) . ?
C28 C32 1.430(5) . ?
C29 C32 1.343(5) . ?
C31 C37 1.497(4) . ?
C33 C35 1.500(5) . ?
C34 C39 1.496(5) . ?
C35 C40 1.377(5) . ?
C35 C36 1.427(5) . ?
C36 C37 1.395(5) . ?
C36 N2 1.408(4) . ?
C37 C38 1.408(5) . ?
C38 N3 1.396(4) . ?
C38 C39 1.430(5) . ?
C39 C41 1.372(5) . ?
C40 C42 1.398(5) . ?
C41 C43 1.398(5) . ?
C42 N2 1.351(4) . ?
C42 C44 1.488(5) . ?
C43 N3 1.357(4) . ?
C43 C45 1.491(5) . ?
N2 B1 1.555(5) . ?
N3 B1 1.554(5) . ?
B1 F2 1.377(5) . ?
B1 F1 1.384(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306203
