Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes through Catalytic Regioselective Hydroboration.
Xi, Yumeng; Hartwig, John F.; Journal of the American Chemical Society 138 (2016) 6703–6706; doi:10.1021/jacs.6b02478

data_4130348
_publ_section_title
;
 Diverse Asymmetric Hydrofunctionalization of Aliphatic Internal Alkenes
 through Catalytic Regioselective Hydroboration.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6703
_journal_page_last               6706
_journal_paper_doi               10.1021/jacs.6b02478
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H30 B Cl3 O4'
_chemical_formula_weight         463.61
_chemical_name_common            YX-3-217B
_chemical_name_systematic        hartwig106
_space_group.centring_type       primitive
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.9250(10)
_cell_angle_beta                 109.9040(10)
_cell_angle_gamma                94.5190(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8418(5)
_cell_length_b                   11.2380(6)
_cell_length_c                   12.2846(7)
_cell_measurement_reflns_used    9821
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.27
_cell_volume                     1233.44(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29929
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.354
_diffrn_reflns_theta_min         1.820
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
; 
 Flack x determined using 3823 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.026(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8930
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0506P)^2^+0.4538P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                8351
_reflns_number_total             8930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02478_si_001.cif
_cod_data_source_block           hartwig106
_cod_original_cell_volume        1233.43(12)
_cod_database_code               4130348
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              85896
_shelx_hkl_checksum              71372