Cobalt-Catalyzed Enantioselective Hydrogenation of Minimally Functionalized Alkenes: Isotopic Labeling Provides Insight into the Origin of Stereoselectivity and Alkene Insertion Preferences.
Friedfeld, Max R.; Shevlin, Michael; Margulieux, Grant W.; Campeau, Louis-Charles; Chirik, Paul J.; Journal of the American Chemical Society 138 (2016) 3314–3324; doi:10.1021/jacs.5b10148

data_4129745
_publ_section_title
;
 Cobalt-Catalyzed Enantioselective Hydrogenation of Minimally
 Functionalized Alkenes: Isotopic Labeling Provides Insight into the
 Origin of Stereoselectivity and Alkene Insertion Preferences.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3314
_journal_page_last               3324
_journal_paper_doi               10.1021/jacs.5b10148
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C16 H16 O'
_chemical_formula_weight         224.29
_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
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.930(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6454(4)
_cell_length_b                   5.5106(3)
_cell_length_c                   14.2743(7)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.01
_cell_measurement_theta_min      3.10
_cell_volume                     601.05(5)
_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-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.000
_diffrn_reflns_theta_min         3.098
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.7535
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (BRUEKR AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0375P)^2^+0.1202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2293
_reflns_number_total             2322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10148_si_001.cif
_cod_data_source_block           mrf55
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129745
_shelxl_version_number           2014-3
_shelx_res_checksum              36718
_shelx_hkl_checksum              62003