Cobalt-Catalyzed Regio- and Enantioselective Markovnikov 1,2-Hydrosilylation of Conjugated Dienes
Wen, Huanan; Wang, Kuan; Zhang, Yanlu; Liu, Guixia; Huang, Zheng; ACS Catalysis 9 (2019) 1612–; doi:10.1021/acscatal.8b04481

data_4514760
_publ_section_title
;
 Cobalt-Catalyzed Regio- and Enantioselective Markovnikov
 1,2-Hydrosilylation of Conjugated Dienes
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1612
_journal_paper_doi               10.1021/acscatal.8b04481
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C12 H16 Cl2 Co N2 O'
_chemical_formula_sum            'C12.5 H16 Cl2 Co N1.5 O'
_chemical_formula_weight         333.10
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                76.7230(10)
_cell_angle_beta                 86.7030(10)
_cell_angle_gamma                85.1260(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5586(2)
_cell_length_b                   8.9303(2)
_cell_length_c                   9.6822(2)
_cell_measurement_reflns_used    5347
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.955
_cell_measurement_theta_min      5.314
_cell_volume                     717.08(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7632
_diffrn_reflns_point_group_measured_fraction_full 0.634
_diffrn_reflns_point_group_measured_fraction_max 0.631
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.929
_diffrn_reflns_theta_min         5.312
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.648
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1028 before and 0.0629 after correction. The Ratio of minimum to maximum transmission is 0.6252. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             341
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.313
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         3459
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.809
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0369
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.273
_reflns_Friedel_fraction_full    0.273
_reflns_Friedel_fraction_max     0.271
_reflns_number_gt                3195
_reflns_number_total             3459
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b04481_si_002.cif
_cod_data_source_block           mjl18335_0m
_cod_original_formula_sum        'C12.50 H16 Cl2 Co N1.50 O'
_cod_database_code               4514760
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.672
_shelx_estimated_absorpt_t_min   0.357
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C21(H21), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C23(H23A,H23B,H23C), C24(H24B,H24A,H24C)
;
_shelx_res_checksum              18015
_shelx_hkl_checksum              5124
_olex2_submission_special_instructions 'No special instructions were received'