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_7715433
_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 H57.03 B2 F20 N4, 2(C3 H5 O), 2.813(C3 H6 O), 1.187(C3 H3 O)'
_chemical_formula_sum            'C102 H87.47 B2 F20 N4 O6'
_chemical_formula_weight         1866.84
_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
_atom_sites_solution_primary     iterative
_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                 95.306(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.2106(9)
_cell_length_b                   10.7119(7)
_cell_length_c                   32.530(2)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      72.37
_cell_measurement_theta_min      2.73
_cell_volume                     4583.6(5)
_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      173.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            26188
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.703
_diffrn_reflns_theta_min         3.360
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.7053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0882 before and 0.0557 after correction.
The Ratio of minimum to maximum transmission is 0.9359.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       Block
_exptl_crystal_F_000             1931
_exptl_crystal_size_max          0.535
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     682
_refine_ls_number_reflns         8811
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0681
_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^)+(0.1441P)^2^+2.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6845
_reflns_number_total             8811
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           cu_20230703tn232_0m_a
_cod_depositor_comments
'Adding full bibliography for 7715430--7715439.cif.'
_cod_database_code               7715433
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.828
_shelx_estimated_absorpt_t_min   0.630
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C44-C45
 1.5 with sigma of 0.02
 C44-O2
 1.15 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C45 \\sim C44 \\sim C53 \\sim C43 \\sim C46 \\sim C57: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
O1 \\sim O2: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C45) \\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C43)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=
 Sof(C39)=Sof(H39A)=Sof(H39B)=Sof(H39C)=1-FVAR(1)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C40)=
 Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
 Sof(O1)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C43)=Sof(C57)=1-FVAR(2)
 Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(H45D)=Sof(H45E)=Sof(H45F)=0.5*FVAR(3)
 Sof(O2)=Sof(C53)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(C45)=Sof(C44)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C27(H27), C28(H28), C30(H30),
 C31(H31), C33(H33), C34(H34)
5.b X=CH2 refined with riding coordinates:
 C54(H54A,H54B), C49(H49A,H49B)
5.c Disordered Me refined with riding coordinates:
 C45(H45A,H45B,H45C,H45D,H45E,H45F)
5.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C), C55(H55A,H55B,
 H55C), C56(H56A,H56B,H56C), C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C42(H42A,
 H42B,H42C), C53(H53A,H53B,H53C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C),
 C50(H50A,H50B,H50C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              94973
_olex2_submission_special_instructions 'No special instructions were received'