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_4129747
_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            'C15 H13 Cl'
_chemical_formula_weight         228.70
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   11.6801(4)
_cell_length_b                   16.8701(6)
_cell_length_c                   18.0924(6)
_cell_measurement_reflns_used    9951
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.70
_cell_measurement_theta_min      3.58
_cell_volume                     3565.0(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  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.975
_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  0.0438
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
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_diffrn_reflns_limit_l_min       -21
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_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.221
_diffrn_reflns_theta_min         3.582
_exptl_absorpt_coefficient_mu    2.557
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.4301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 Bruker ASX'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       shard
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.654
_exptl_crystal_size_mid          0.421
_exptl_crystal_size_min          0.221
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.057(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+0.6576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0699
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_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                7326
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b10148_si_001.cif
_cod_data_source_block           mrf58
_cod_database_code               4129747
_shelxl_version_number           2014-3
_shelx_res_checksum              18395
_shelx_hkl_checksum              85537