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_7715438
_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, C45 H10 B2 F20 N3, 0.5(C2 N2)'
_chemical_formula_sum            'C92 H20 B4 F40 N8'
_chemical_formula_weight         2040.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-08-30
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-15 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.0995(17)
_cell_length_b                   31.488(3)
_cell_length_c                   12.9587(8)
_cell_measurement_reflns_used    8170
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.80
_cell_measurement_theta_min      2.31
_cell_volume                     9833.6(13)
_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 0.993
_diffrn_measured_fraction_theta_max 0.976
_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  0.0885
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26063
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.230
_diffrn_reflns_theta_min         4.120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.210
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1106 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.8055.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       Block
_exptl_crystal_F_000             4032
_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.8(4)
_refine_ls_extinction_coef       0.00019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         9346
_refine_ls_number_restraints     1523
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0834
_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^)+(0.1124P)^2^+5.3036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2053
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                5395
_reflns_number_total             9346
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4dt00469h2.cif
_cod_data_source_block           cu_20230824tn02251_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7715430--7715439.cif.
;
_cod_original_cell_volume        9833.8(12)
_cod_database_code               7715438
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.933
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.2(4)
 0.8(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C43-C58
 1.4 with sigma of 0.02
 B2-C45
 1.6 with sigma of 0.02
 N29-C49
 1.165 with sigma of 0.02
 N29-C48
 2.562 with sigma of 0.02
 N29-C48_$1
 1.318 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
5. Others
 Fixed Sof: H44(0.5) C40(0.5) C39(0.5) C38(0.5) F11(0.5) F13(0.5) F14(0.5)
 C24(0.5) C27(0.5) C29(0.5) C51(0.5) H51(0.5) C45(0.5) C46(0.5) C47(0.5)
 H47(0.5) C48(0.5) C36(0.5) H36(0.5) C37(0.5) H37(0.5) C34(0.5) C33(0.5)
 F23(0.5) F24(0.5) F26(0.5) C41(0.5) C42(0.5) C43(0.5) N28(0.5) C49(0.5)
 N29(0.5) C63(0.5) C62(0.5) H62(0.5) F18(0.5) F17(0.5) F12(0.5) F15(0.5)
 C25(0.5) C28(0.5) C30(0.5) C50(0.5) H50(0.5) C35(0.5) F21(0.5) F22(0.5)
 F27(0.5) B3(0.5) C52(0.5) C53(0.5) C54(0.5) H54(0.5) C55(0.5) H55(0.5)
 C56(0.5) C57(0.5) H57(0.5) N3(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C44(H44), C51(H51), C47(H47),
 C36(H36), C37(H37), C62(H62), C50(H50), C54(H54), C55(H55), C57(H57)
6.b Fitted hexagon refined as free rotating group:
 C60(C40,C39,C38,C58,C59), C52(C53,C54,C55,C56,C57)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              13352
_shelx_fab_checksum              90143
_olex2_submission_special_instructions 'No special instructions were received'