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_1566896
_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 H54 B N3'
_chemical_formula_sum            'C51 H54 B N3'
_chemical_formula_weight         719.78
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-16
_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                 90.452(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.582(3)
_cell_length_b                   33.295(6)
_cell_length_c                   18.241(3)
_cell_measurement_reflns_used    3535
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.68
_cell_measurement_theta_min      2.45
_cell_volume                     9463(3)
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_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  0.1053
_diffrn_reflns_av_unetI/netI     0.1621
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27948
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.881
_diffrn_reflns_theta_min         1.656
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.50 before and 0.4086 after correction.
The Ratio of minimum to maximum transmission is 0.8354.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.010
_exptl_crystal_description       block
_exptl_crystal_F_000             3088
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     570
_refine_ls_number_reflns         10645
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.2659
_refine_ls_R_factor_gt           0.1394
_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          0.3623
_refine_ls_wR_factor_ref         0.4086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3931
_reflns_number_total             10645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01722a2.cif
_cod_data_source_block           nbnn-1
_cod_database_code               1566896
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C51-C38 \\sim C51A-C38
 with sigma of 0.02
 C38-C40 \\sim C38-C40A
 with sigma of 0.02
 C38-C43 \\sim C38-C43A
 with sigma of 0.02
 C42-C53 \\sim C42-C53A
 with sigma of 0.02
 C42-C50 \\sim C42-C50A
 with sigma of 0.02
 C42-C54 \\sim C42-C54A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C51A) \\sim Ueq, Uanis(C43A) \\sim Ueq, Uanis(C40A) \\sim Ueq, Uanis(C51)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C50A) \\sim Ueq,
Uanis(C54A) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C53A) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C54) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
4. Others
 Sof(C43A)=Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C40A)=Sof(H40D)=Sof(H40E)=
 Sof(H40F)=Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=1-FVAR(1)
 Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(H43C)=
 Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
 Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(C54A)=Sof(H54D)=Sof(H54E)=
 Sof(H54F)=Sof(C50A)=Sof(H50D)=Sof(H50E)=Sof(H50F)=1-FVAR(2)
 Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C17(H17), C19(H19), C21(H21), C24(H24), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C37(H37),
  C39(H39), C41(H41), C44(H44)
5.b Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C49(H49A,H49B,H49C), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C48(H48A,H48B,H48C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C53(H53A,
 H53B,H53C), C43(H43A,H43B,H43C), C50(H50A,H50B,H50C), C54(H54A,H54B,H54C),
 C40(H40A,H40B,H40C), C43A(H43D,H43E,H43F), C40A(H40D,H40E,H40F), C51A(H51D,
 H51E,H51F), C53A(H53D,H53E,H53F), C54A(H54D,H54E,H54F), C50A(H50D,H50E,H50F)
;
_shelx_res_checksum              4373
_shelx_hkl_checksum              94765
_shelx_fab_checksum              3719
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'