Direct C-H electrophilic borylation with (C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>B-NTf<sub>2</sub> to generate B-N dibenzo[<i>a</i>,<i>h</i>]pyrenes.
Nguyen, Tony; Dutton, Jason L.; Chang, Chia Yun; Zhou, Wen; Piers, Warren E.; Dalton transactions (Cambridge, England : 2003) 53 (2024) 7273–7281; doi:10.1039/d4dt00469h

data_7715431
_publ_section_title
;
 Direct C-H electrophilic borylation with
 (C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>B-NTf<sub>2</sub> to generate B-N
 dibenzo[<i>a</i>,<i>h</i>]pyrenes.
;
_journal_issue                   17
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7273
_journal_page_last               7281
_journal_paper_doi               10.1039/d4dt00469h
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C68 H26 B2 F20 N4'
_chemical_formula_sum            'C68 H26 B2 F20 N4'
_chemical_formula_weight         1300.55
_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             2023-01-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                71.888(4)
_cell_angle_beta                 78.885(4)
_cell_angle_gamma                84.992(4)
_cell_formula_units_Z            1
_cell_length_a                   10.2642(5)
_cell_length_b                   10.8711(6)
_cell_length_c                   12.8590(7)
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.34
_cell_measurement_theta_min      3.67
_cell_volume                     1337.59(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1425
_diffrn_reflns_av_unetI/netI     0.1071
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22874
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        66.943
_diffrn_reflns_theta_max         66.943
_diffrn_reflns_theta_min         3.673
_diffrn_source_current           0.64
_diffrn_source_power             0.028576
_diffrn_source_voltage           44.65
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.261
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6346
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1025 before and 0.0852 after correction.
The Ratio of minimum to maximum transmission is 0.8430.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       rod
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0610
_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^)+(0.0788P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2832
_reflns_number_total             4575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           tn02187
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_original_cell_volume        1337.60(13)
_cod_database_code               7715431
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C21(H21), C9(H9), C7(H7), C20(H20), C18(H18),
 C19(H19), C12(H12), C13(H13), C15(H15), C14(H14)
;
_shelx_res_checksum              50929
_olex2_submission_special_instructions 'No special instructions were received'