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_7715437
_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         'C84 H58 B2 F20 N4, 4(C3 H6 O)'
_chemical_formula_sum            'C96 H82 B2 F20 N4 O4'
_chemical_formula_weight         1757.27
_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     iterative
_audit_creation_date             2023-04-07
_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                71.475(4)
_cell_angle_beta                 77.749(4)
_cell_angle_gamma                70.273(4)
_cell_formula_units_Z            1
_cell_length_a                   10.9839(7)
_cell_length_b                   13.2502(10)
_cell_length_c                   17.5105(12)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      66.805
_cell_measurement_theta_min      2.680
_cell_volume                     2258.8(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0918
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27687
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        66.824
_diffrn_reflns_theta_max         66.824
_diffrn_reflns_theta_min         2.680
_diffrn_source_current           0.64
_diffrn_source_power             0.028608000000000005
_diffrn_source_voltage           44.7
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.7237
_exptl_absorpt_correction_T_min  0.5753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1428 before and 0.1073 after correction.
The Ratio of minimum to maximum transmission is 0.7949.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     715
_refine_ls_number_reflns         7665
_refine_ls_number_restraints     348
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0982
_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^)+(0.1896P)^2^+0.5388P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2629
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6483
_reflns_number_total             7665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           tn02203_sq
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_database_code               7715437
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.782
_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
O2 \\sim C4 \\sim C5 \\sim C6 \\sim O2A \\sim C4A \\sim C5A \\sim C6A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim C1 \\sim C2 \\sim C3 \\sim O1A \\sim C1A \\sim C2A \\sim C3A \\sim O2
\\sim C4 \\sim C5 \\sim C6 \\sim O2A \\sim C4A \\sim C5A \\sim C6A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
F2A \\sim F2B \\sim F3A \\sim F3B \\sim C39 \\sim C40: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(O2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(O2A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C5A) \\sim Ueq,
Uanis(C6A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(O1A) \\sim Ueq, Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq,
Uanis(C3A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2B) \\sim Ueq, Uanis(F3B) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
3. Others
 Sof(O2A)=Sof(C4A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C6A)=Sof(H6AA)=
 Sof(H6AB)=Sof(H6AC)=1-FVAR(1)
 Sof(O2)=Sof(C4)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=Sof(C6)=Sof(H6A)=Sof(H6B)=
 Sof(H6C)=FVAR(1)
 Sof(C7A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(2)
 Sof(C7)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
 Sof(O1A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(H3AC)=1-FVAR(3)
 Sof(O1)=Sof(C1)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=FVAR(3)
 Sof(F2B)=Sof(F3B)=1-FVAR(4)
 Sof(F2A)=Sof(F3A)=FVAR(4)
4.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C19(H19), C22(H22), C24(H24), C25(H25), C28(H28),
 C30(H30), C31(H31), C34(H34), C35(H35)
4.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C9(H9A,H9B,H9C), C9A(H9AA,H9AB,H9AC),
 C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C2A(H2AA,H2AB,
 H2AC), C3A(H3AA,H3AB,H3AC), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C5A(H5AA,H5AB,
 H5AC), C6A(H6AA,H6AB,H6AC)
;
_shelx_res_checksum              20169
_shelx_fab_checksum              79995
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'