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_1566897
_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         'C53.425 H58.276 B N3, C6 H12'
_chemical_formula_sum            'C59.42 H70.28 B N3'
_chemical_formula_weight         837.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-19
_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                90
_cell_angle_beta                 90.748(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.747(2)
_cell_length_b                   19.582(2)
_cell_length_c                   23.834(2)
_cell_measurement_reflns_used    5236
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      21.75
_cell_measurement_theta_min      2.20
_cell_volume                     10148.8(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      180.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1663
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47356
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.824
_diffrn_reflns_theta_max         24.824
_diffrn_reflns_theta_min         2.200
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.4123 before and 0.3228 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.096
_exptl_crystal_description       block
_exptl_crystal_F_000             3623
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.105
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         8734
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1731
_refine_ls_R_factor_gt           0.0957
_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          0.2667
_refine_ls_wR_factor_ref         0.3228
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4392
_reflns_number_total             8734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01722a2.cif
_cod_data_source_block           nbnn-3
_cod_database_code               1566897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_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
 C1F-C1E
 1.5 with sigma of 0.02
 C1B-C1C
 1.5 with sigma of 0.02
 C1D-C1C
 1.5 with sigma of 0.02
 C1A-C1F
 1.5 with sigma of 0.02
 C1A-C1B
 1.58 with sigma of 0.01
 C1D-C1E
 1.58 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C1B) \\sim Ueq, Uanis(C1F) \\sim Ueq, Uanis(C1C)
\\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C1D) \\sim Ueq: with sigma of 0.001 and
sigma for terminal atoms of 0.002
Uanis(C56) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C50A) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C49A) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C40) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C54) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C39) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C1(0.557) H1A(0.557) H1B(0.557) H1C(0.557) C38(0.8084)
 H38A(0.8084) H38B(0.8084) H38C(0.8084) C39(0.8084) H39A(0.8084) H39B(0.8084)
 H39C(0.8084) C40(0.8084) H40A(0.8084) H40B(0.8084) H40C(0.8084) C49(0.557)
 H49A(0.557) H49B(0.557) H49C(0.557) C50(0.557) H50A(0.557) H50B(0.557)
 H50C(0.557) C49A(0.443) H49D(0.443) H49E(0.443) H49F(0.443) C50A(0.443)
 H50D(0.443) H50E(0.443) H50F(0.443) C56(0.443) H56A(0.443) H56B(0.443)
 H56C(0.443)
5.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C1B(H1BA,H1BB), C1C(H1CA,H1CB), C1D(H1DA,H1DB), C1E(H1EA,
 H1EB), C1F(H1FA,H1FB)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
 C28(H28), C31(H31), C36(H36), C41(H41), C43(H43), C44(H44), C47(H47)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C27(H27A,H27B,
 H27C), C30(H30A,H30B,H30C), C33(H33A,H33B,H33C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C), C40(H40A,H40B,H40C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C),
 C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C49A(H49D,H49E,H49F), C50A(H50D,H50E,H50F), C56(H56A,H56B,H56C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85851
_shelx_hkl_checksum              2443
_shelx_fab_checksum              44085
_olex2_submission_special_instructions 'No special instructions were received'