Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons with delayed fluorescence and aggregation-induced emission under mild conditions
Jiang, Long; Wang, Yu; Tan, Dehui; Chen, Xiaobin; Ma, Tinghao; Zhang, Baoliang; Yang, Deng-Tao; Chemical Science  (2022) –; doi:10.1039/D2SC01722A

data_1566898
_publ_section_title
;
 Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons
 with delayed fluorescence and aggregation-induced emission under mild
 conditions
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01722A
_journal_year                    2022
_chemical_formula_moiety         'C51 H52 B N3, C5 H10'
_chemical_formula_sum            'C56 H62 B N3'
_chemical_formula_weight         787.89
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-17
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-03-25 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                83.621(2)
_cell_angle_beta                 78.486(2)
_cell_angle_gamma                77.897(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0795(12)
_cell_length_b                   14.2380(16)
_cell_length_c                   15.3074(17)
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.62
_cell_volume                     2307.5(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.660
_diffrn_reflns_theta_min         1.361
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.160
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       0.016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         10109
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.1719
_refine_ls_R_factor_gt           0.1046
_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/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2972
_refine_ls_wR_factor_ref         0.3532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5314
_reflns_number_total             10109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01722a2.cif
_cod_data_source_block           NBNN-1f
_cod_database_code               1566898
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C4
 1.5 with sigma of 0.02
 C5-C4
 1.5 with sigma of 0.02
 C1-C5
 1.5 with sigma of 0.02
 C2-C3
 1.5 with sigma of 0.02
 C3-C1
 1.5 with sigma of 0.02
 C1-C2
 2.5 with sigma of 0.02
 C3-C4
 2.5 with sigma of 0.02
 C3-C5
 2.5 with sigma of 0.02
 C5-C2
 2.5 with sigma of 0.02
 C4-C2
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C01J) \\sim Ueq, Uanis(C01I) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C01J) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
4.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00H(H00H), C00I(H00I), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C011(H011),
 C012(H012), C015(H015), C017(H017), C01B(H01M)
4.c Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C018(H01D,H01E,H01F), C019(H01G,H01H,H01I), C01A(H01J,
 H01K,H01L), C01C(H01N,H01O,H01P), C01D(H01Q,H01R,H01S), C01E(H01T,H01U,H01V),
 C01F(H01W,H01X,H01Y), C01G(H01Z,H,HA), C01H(H01,HB,HC), C01I(H1,HD,HE),
 C01J(H2,HF,HG)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              28245
_shelx_hkl_checksum              19203
_shelx_fab_checksum              87485
_olex2_submission_special_instructions 'No special instructions were received'