Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of Internal Alkynes.
Guo, Jun; Cheng, Biao; Shen, Xuzhong; Lu, Zhan; Journal of the American Chemical Society 139 (2017) 15316–15319; doi:10.1021/jacs.7b09832

data_4131740
_publ_section_title
;
 Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of
 Internal Alkynes.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15316
_journal_page_last               15319
_journal_paper_doi               10.1021/jacs.7b09832
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H38 Cl2 Co N4, C7 H8'
_chemical_formula_sum            'C38 H46 Cl2 Co N4'
_chemical_formula_weight         688.62
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.706(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5943(5)
_cell_length_b                   16.0090(6)
_cell_length_c                   21.0879(11)
_cell_measurement_reflns_used    5676
_cell_measurement_temperature    183.1
_cell_measurement_theta_max      29.4806
_cell_measurement_theta_min      2.7163
_cell_volume                     3576.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      183.1
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -64.00   36.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871  -38.0000 -180.0000 100

  2 omega  -15.00   73.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -       10.6871   38.0000    0.0000 88

  3 omega  -73.00   21.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5621  -77.0000   60.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0518969000
_diffrn_orient_matrix_UB_12      0.0079243000
_diffrn_orient_matrix_UB_13      0.0207286000
_diffrn_orient_matrix_UB_21      -0.0308955000
_diffrn_orient_matrix_UB_22      -0.0219339000
_diffrn_orient_matrix_UB_23      0.0245484000
_diffrn_orient_matrix_UB_31      0.0289293000
_diffrn_orient_matrix_UB_32      -0.0376478000
_diffrn_orient_matrix_UB_33      -0.0099925000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.1149
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23119
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.722
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       plate
_exptl_crystal_F_000             1452
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 2866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     827
_refine_ls_number_reflns         12617
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0176P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                8871
_reflns_number_total             12617
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09832_si_002.cif
_cod_data_source_block           161229_cb7121_red
_cod_database_code               4131740
_chemical_oxdiff_formula         'c10 h10 n2 o8 Co1'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.863
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C14(H14), C17(H17), C21(H21), C23(H23), C45(H45), C48(H48), C51(H51), C54(H54)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C52(H52A,H52B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C27(H27), C28(H28),
 C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C41(H41), C42(H42),
  C43(H43), C58(H58), C59(H59), C60(H60), C61(H61), C62(H62), C63(H63),
 C64(H64), C65(H65), C66(H66), C67(H67), C70(H70), C71(H71), C72(H72), C73(H73),
  C74(H74)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C38(H38A,
 H38B,H38C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C49(H49A,H49B,H49C),
 C50(H50A,H50B,H50C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C69(H69A,H69B,
 H69C), C76(H76A,H76B,H76C)
;
_shelx_res_checksum              49536
_shelx_hkl_checksum              61889
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'