Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation.
Labelle, Anthony; Arndtsen, Bruce A.; Chemical communications (Cambridge, England) 59 (2023) 728–731; doi:10.1039/d2cc05924j

data_7131085
_publ_section_title
;
 Chiral BINOL-based borate counterions: from cautionary tale on anion
 stability to enantioselective Cu-catalyzed cyclopropanation.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              728
_journal_page_last               731
_journal_paper_doi               10.1039/d2cc05924j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C36 H26 B Cu F2 N2 O2'
_chemical_formula_sum            'C36 H26 B Cu F2 N2 O2'
_chemical_formula_weight         630.94
_chemical_name_common            'Compound 3b'
_chemical_name_systematic
'Bis(acetonitrile)copper(I) 4,4-difluoro-2,6-diphenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaborepin-4-uide'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-27 deposited with the CCDC.	2022-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0757(3)
_cell_length_b                   14.0725(3)
_cell_length_c                   19.5245(5)
_cell_measurement_reflns_used    6817
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      135.461
_cell_measurement_theta_min      7.743
_cell_volume                     3043.14(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ShelXle (J. Appl. Cryst. 2011, 44, 1281-1284)'
_computing_publication_material  'ShelXle (J. Appl. Cryst. 2011, 44, 1281-1284)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Photon 200'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1495
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            52720
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.492
_diffrn_reflns_theta_min         3.872
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_transmission_factor_max   0.7536
_exptl_transmission_factor_min   0.4505
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.972
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details
;
 Flack x determined using 1599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0737
_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^)+(0.1343P)^2^+0.3513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.2277
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4358
_reflns_number_total             6032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05924j2.cif
_cod_data_source_block           AL1_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7131085.cif.
;
_cod_database_code               7131085
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.838
_shelx_res_checksum              46327
_shelx_hkl_checksum              798