Difunctionalization of C-C σ-Bonds Enabled by the Reaction of Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction Development, Scope, and Stereochemical Origins.
Bennett, Steven H.; Fawcett, Alexander; Denton, Elliott H.; Biberger, Tobias; Fasano, Valerio; Winter, Nils; Aggarwal, Varinder K.; Journal of the American Chemical Society 142 (2020) 16766–16775; doi:10.1021/jacs.0c07357

data_4135257
_publ_section_title
;
 Difunctionalization of C-C \s-Bonds Enabled by the Reaction of
 Bicyclo[1.1.0]butyl Boronate Complexes with Electrophiles: Reaction
 Development, Scope, and Stereochemical Origins.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16766
_journal_page_last               16775
_journal_paper_doi               10.1021/jacs.0c07357
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H33 B O3'
_chemical_formula_sum            'C26 H33 B O3'
_chemical_formula_weight         404.33
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.0127(3)
_cell_length_b                   11.0765(4)
_cell_length_c                   10.3165(4)
_cell_measurement_reflns_used    3064
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.70
_cell_volume                     1143.98(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10464
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_min         1.974
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0638 before and 0.0448 after correction. The Ratio of minimum to maximum transmission is 0.8205. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.574
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         5128
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0338P)^2^+0.1767P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0868
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.913
_reflns_Friedel_fraction_max     0.876
_reflns_number_gt                4414
_reflns_number_total             5128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c07357_si_006.cif
_cod_data_source_block           testm1
_cod_depositor_comments
'Adding full bibliography for 4135252--4135257.cif.'
_cod_database_code               4135257
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              64564
_shelx_hkl_checksum              38589
_olex2_submission_special_instructions 'No special instructions were received'