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_7715436
_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         'C56 H36 B2 F20 N2'
_chemical_formula_sum            'C56 H36 B2 F20 N2'
_chemical_formula_weight         1138.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-01-06
_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                90
_cell_angle_beta                 99.2810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.8525(4)
_cell_length_b                   15.3208(5)
_cell_length_c                   9.5674(3)
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      72.43
_cell_measurement_theta_min      2.66
_cell_volume                     2437.91(12)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7899
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.667
_diffrn_reflns_theta_min         2.657
_exptl_absorpt_coefficient_mu    1.267
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 24006 reflections, Rint = 0.0470
 (12253 with I > 3sig(I), Rint = 0.0415)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_description       plank
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         7899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0592
_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^)+(0.0994P)^2^+0.5823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6626
_reflns_number_total             7899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           tn_01_097
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_database_code               7715436
_shelx_shelxl_version_number     2018/3
_publ_section_exptl
;
Any special experimental details
;
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.701
_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.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              53341
_olex2_submission_original_sample_id TN_01_097
_olex2_submission_special_instructions 'No special instructions were received'