Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization.
Su, Yuanting; Huan Do, Dinh Cao; Li, Yongxin; Kinjo, Rei; Journal of the American Chemical Society 141 (2019) 13729–13733; doi:10.1021/jacs.9b06022

data_4128835
_publ_section_title
;
 Metal-Free Selective Borylation of Arenes by a Diazadiborinine via
 C-H/C-F Bond Activation and Dearomatization.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13729
_journal_page_last               13733
_journal_paper_doi               10.1021/jacs.9b06022
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C82.5 H71 B2 Cl N4'
_chemical_formula_weight         1175.50
_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     dual
_cell_angle_alpha                96.263(2)
_cell_angle_beta                 97.224(2)
_cell_angle_gamma                92.9468(19)
_cell_formula_units_Z            2
_cell_length_a                   12.2016(11)
_cell_length_b                   15.2052(14)
_cell_length_c                   17.0465(16)
_cell_measurement_reflns_used    5402
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      23.9793
_cell_measurement_theta_min      2.2288
_cell_volume                     3112.0(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_unetI/netI     0.2177
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10874
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.20
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1075
_refine_ls_number_reflns         10874
_refine_ls_number_restraints     1437
_refine_ls_restrained_S_all      0.938
_refine_ls_R_factor_all          0.2109
_refine_ls_R_factor_gt           0.0932
_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^)+(0.1408P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2249
_refine_ls_wR_factor_ref         0.2743
_reflns_number_gt                4565
_reflns_number_total             10874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b06022_si_016.cif
_cod_data_source_block           rei1236m_0m_4
_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/current/ACS/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C82.50 H71 B2 Cl N4'
_cod_database_code               4128835
_shelx_res_checksum              53795
_shelx_hkl_checksum              46709