Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective C(sp<sup>3</sup>)-H Borylation of Cyclopropanes.
Shi, Yongjia; Gao, Qian; Xu, Senmiao; Journal of the American Chemical Society 141 (2019) 10599–10604; doi:10.1021/jacs.9b04549

data_4127649
_publ_section_title
;
 Chiral Bidentate Boryl Ligand Enabled Iridium-Catalyzed Enantioselective
 C(sp<sup>3</sup>)-H Borylation of Cyclopropanes.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10599
_journal_page_last               10604
_journal_paper_doi               10.1021/jacs.9b04549
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H29 B Br N O3'
_chemical_formula_weight         422.15
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.7240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6867(4)
_cell_length_b                   6.8041(3)
_cell_length_c                   28.1524(11)
_cell_measurement_reflns_used    9761
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.46
_cell_measurement_theta_min      4.14
_cell_volume                     2046.89(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25028
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.735
_diffrn_reflns_theta_min         4.137
_exptl_absorpt_coefficient_mu    2.881
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.156
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         7205
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+3.3017P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                7183
_reflns_number_total             7205
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04549_si_002.cif
_cod_data_source_block           cu_20181231b_0m_a
_cod_original_formula_sum        'C20 H29 B1 Br1 N1 O3'
_cod_database_code               4127649
_shelxl_version_number           2013-2
_shelx_res_checksum              7156
_shelx_hkl_checksum              46992