Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron "Ate" Complexes and C(sp(2)) Halides or Triflates: NaOTf as a Grignard Activator and Halide Scavenger.
Lovinger, Gabriel J.; Aparece, Mark D.; Morken, James P.; Journal of the American Chemical Society 139 (2017) 3153–3160; doi:10.1021/jacs.6b12663

data_4125640
_publ_section_title
;
 Pd-Catalyzed Conjunctive Cross-Coupling between Grignard-Derived Boron
 &quot;Ate&quot; Complexes and C(sp(2)) Halides or Triflates: NaOTf as a
 Grignard Activator and Halide Scavenger.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3153
_journal_page_last               3160
_journal_paper_doi               10.1021/jacs.6b12663
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H25 B O3 S'
_chemical_formula_sum            'C20 H25 B O3 S'
_chemical_formula_weight         356.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
_cell_angle_beta                 102.765(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.818(2)
_cell_length_b                   14.500(3)
_cell_length_c                   12.569(3)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.18
_cell_volume                     1922.9(7)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44417
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_min         1.661
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2013). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
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_exptl_crystal_description       prism
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_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 3599 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       na
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     539
_refine_ls_number_reflns         9584
_refine_ls_number_restraints     523
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0500
_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^)+(0.0400P)^2^+1.1473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1150
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8680
_reflns_number_total             9584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b12663_si_002.cif
_cod_data_source_block           C20H25BO3S
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1922.8(7)
_cod_database_code               4125640
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.898
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              81354
_shelx_hkl_checksum              51829