Borane-Catalyzed C(sp3)–F Bond Arylation and Esterification Enabled by Transborylation
Willcox, Dominic R.; Nichol, Gary S.; Thomas, Stephen P.; ACS Catalysis  (2021) 3190–3197; doi:10.1021/acscatal.1c00282

data_4518507
_publ_section_title
;
 Borane-Catalyzed C(sp3)--F Bond Arylation and Esterification Enabled by
 Transborylation
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3190
_journal_page_last               3197
_journal_paper_doi               10.1021/acscatal.1c00282
_journal_year                    2021
_chemical_formula_moiety         'C30 H36 B2 F2 O4'
_chemical_formula_sum            'C30 H36 B2 F2 O4'
_chemical_formula_weight         520.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-15
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.566(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.1379(3)
_cell_length_b                   10.3208(2)
_cell_length_c                   14.2997(2)
_cell_measurement_reflns_used    6218
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      75.5080
_cell_measurement_theta_min      4.9160
_cell_volume                     2639.65(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -82.00  15.00   1.00    5.00    --  -41.79  99.00-111.00   97
  2  \w      6.00  82.00   1.00    5.00    --   41.79 -99.00 141.00   76
  3  \w     32.00 107.00   1.00   15.00    --  111.00 -99.00 141.00   75
  4  \w    104.00 178.00   1.00   15.00    --  111.00  99.00-111.00   74
  5  \w   -114.00 -19.00   1.00    5.00    --  -41.79 -38.00-180.00   95
  6  \w   -114.00 -19.00   1.00    5.00    --  -41.79 -38.00  90.00   95
  7  \w     15.00 112.00   1.00    5.00    --   41.79  57.00  30.00   97
  8  \w     39.00 112.00   1.00   15.00    --  111.00-125.00 -30.00   73
  9  \w     37.00 142.00   1.00   15.00    --  111.00 -77.00 150.00  105
 10  \w     33.00 108.00   1.00   15.00    --  111.00-102.00  31.77   75
 11  \w     97.00 178.00   1.00   15.00    --  111.00 125.00-180.00   81
 12  \w     97.00 178.00   1.00   15.00    --  111.00 125.00 -30.00   81
 13  \w     97.00 178.00   1.00   15.00    --  111.00 125.00-150.00   81
 14  \w     39.00 112.00   1.00   15.00    --  111.00-125.00  30.00   73
 15  \w     30.00 107.00   1.00   15.00    --  111.00 -94.00-120.00   77
 16  \w    103.00 178.00   1.00   15.00    --  111.00  77.00 150.00   75
 17  \w     31.00 156.00   1.00   15.00    --  111.00 -15.00 120.00  125
 18  \w     41.00 139.00   1.00   15.00    --  111.00 -61.00-150.00   98
 19  \w     30.00 107.00   1.00   15.00    --  111.00 -94.00  60.00   77
 20  \w     87.00 178.00   1.00   15.00    --  111.00  45.00 120.00   91
 21  \w    103.00 178.00   1.00   15.00    --  111.00  77.00-150.00   75
 22  \w     87.00 178.00   1.00   15.00    --  111.00  45.00 -60.00   91
 23  \w     87.00 178.00   1.00   15.00    --  111.00  45.00 150.00   91
 24  \w     36.00 135.00   1.00   15.00    --  111.00 -30.00 120.00   99
 25  \w     32.00 107.00   1.00   15.00    --  111.00 -99.00-177.18   75
 26  \w     30.00 107.00   1.00   15.00    --  111.00 -94.00 -30.00   77
 27  \w     39.00 112.00   1.00   15.00    --  111.00-125.00-180.00   73
 28  \w     40.00 135.00   1.00   15.00    --  111.00 -45.00 -90.00   95
 29  \w   -114.00 -19.00   1.00    5.00    --  -41.79 -38.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0788852000
_diffrn_orient_matrix_UB_12      -0.0372898000
_diffrn_orient_matrix_UB_13      0.0505024000
_diffrn_orient_matrix_UB_21      0.0211794000
_diffrn_orient_matrix_UB_22      -0.0406574000
_diffrn_orient_matrix_UB_23      -0.0957738000
_diffrn_orient_matrix_UB_31      0.0273637000
_diffrn_orient_matrix_UB_32      0.1387078000
_diffrn_orient_matrix_UB_33      -0.0144356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21207
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.086
_diffrn_reflns_theta_min         4.945
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  0.4716
_exptl_absorpt_correction_T_min  0.3305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1346 before and 0.0918 after correction.
The Ratio of minimum to maximum transmission is 0.7008.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_recrystallization_method
'The material was recrystallised from toluene by slow cooling'
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0795P)^2^+1.1971P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1325
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2261
_reflns_number_total             2738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00282_si_003.cif
_cod_data_source_block           se20017
_cod_database_code               4518507
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H15 B F O2 '
_chemical_oxdiff_usercomment     '@ 120 K DRW04-029'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
;
_shelx_res_checksum              89054
_shelx_hkl_checksum              59462
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil.'
_olex2_submission_original_sample_id DRW04-029
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 2.270
_oxdiff_exptl_absorpt_empirical_full_min 0.621