Enantioselective Desymmetrization via Carbonyl-Directed Catalytic Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling.
Hoang, Gia L.; Yang, Zhao-Di; Smith, Sean M.; Pal, Rhitankar; Miska, Judy L.; Pérez, Damaris E; Pelter, Libbie S. W.; Zeng, Xiao Cheng; Takacs, James M.; Organic letters 17 (2015) 940–943; doi:10.1021/ol503764d

data_1518635
_publ_section_title
;
 Enantioselective Desymmetrization via Carbonyl-Directed Catalytic
 Asymmetric Hydroboration and Suzuki-Miyaura Cross-Coupling.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              940
_journal_page_last               943
_journal_paper_doi               10.1021/ol503764d
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C26 H29 B F4 N2 O2'
_chemical_formula_weight         488.32
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXTL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4470(4)
_cell_length_b                   16.3195(8)
_cell_length_c                   17.2927(8)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.56
_cell_measurement_theta_min      2.71
_cell_volume                     2383.8(2)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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  0.0241
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20098
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         69.959
_diffrn_reflns_theta_min         3.724
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
; 
 Flack x determined using 1739 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.16(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         4313
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0568P)^2^+1.4569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1085
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.909
_reflns_number_gt                4273
_reflns_number_total             4313
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol503764d_si_003.cif
_cod_data_source_block           q43e
_cod_depositor_comments
'Adding full bibliography for 1518634--1518635.cif.'
_cod_database_code               1518635
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.932
_shelxl_version_number           2013-4
_shelx_res_checksum              74278
_shelx_hkl_checksum              68205