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_7715439
_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         'C46 H10 B2 F20 N4, 4(C2 H3 N)'
_chemical_formula_sum            'C54 H22 B2 F20 N8'
_chemical_formula_weight         1184.447
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.146(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.4453(13)
_cell_length_b                   20.727(3)
_cell_length_c                   12.4957(19)
_cell_measurement_reflns_used    8483
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.430
_cell_measurement_theta_min      4.179
_cell_volume                     2408.1(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.9915
_diffrn_measured_fraction_theta_max 0.9809
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.9915
_diffrn_reflns_Laue_measured_fraction_max 0.9809
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17519
_diffrn_reflns_point_group_measured_fraction_full 0.9915
_diffrn_reflns_point_group_measured_fraction_max 0.9809
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.47
_diffrn_reflns_theta_min         4.18
_diffrn_source_current           0.64
_diffrn_source_power             0.0285952
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1219 before and 0.0615 after correction.
The Ratio of minimum to maximum transmission is 0.8112.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       plate
_exptl_crystal_F_000             1189.655
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.3925
_refine_diff_density_min         -0.5269
_refine_diff_density_rms         0.0788
_refine_ls_d_res_high            0.8084
_refine_ls_d_res_low             10.5779
_refine_ls_goodness_of_fit_ref   1.0618
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     439
_refine_ls_number_reflns         4682
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.0521
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          -0.0038
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1034P)^2^+1.3367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              -7
_reflns_number_gt                3802
_reflns_number_total             4682
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           TN02221
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_database_code               7715439
_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. Uiso/Uaniso restraints and constraints
N4 \\sim C26 \\sim C27 \\sim N4A \\sim C26A \\sim C27A: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
N3 \\sim C24 \\sim C25 \\sim N3a \\sim C24a \\sim C25a: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
3. Others
 Sof(N4A)=Sof(C26A)=Sof(C27A)=Sof(H27d)=Sof(H27e)=Sof(H27f)=1-FVAR(1)
 Sof(N4)=Sof(C26)=Sof(C27)=Sof(H27a)=Sof(H27b)=Sof(H27c)=FVAR(1)
 Sof(N3a)=Sof(C24a)=Sof(C25a)=Sof(H25d)=Sof(H25e)=Sof(H25f)=1-FVAR(2)
 Sof(N3)=Sof(C24)=Sof(C25)=Sof(H25a)=Sof(H25b)=Sof(H25c)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C5(H5), C4(H4)
4.b Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c), C27(H27a,H27b,H27c), C27A(H27d,H27e,H27f), C25a(H25d,
 H25e,H25f)
;
_olex2_submission_special_instructions 'No special instructions were received'