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_4131739
_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         'C27 H30 Br2 Co N4'
_chemical_formula_sum            'C27 H30 Br2 Co N4'
_chemical_formula_weight         629.30
_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     heavy
_audit_creation_date             2017-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.063(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9911(9)
_cell_length_b                   8.7896(6)
_cell_length_c                   12.6256(12)
_cell_measurement_reflns_used    2789
_cell_measurement_temperature    169.9
_cell_measurement_theta_max      29.2936
_cell_measurement_theta_min      2.8833
_cell_volume                     1310.23(19)
_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      169.9
_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  -13.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  150.0000 101

  2 omega  -63.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -38.0000 -150.0000 101

  3 omega  -18.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   77.0000 -150.0000 109
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0155613000
_diffrn_orient_matrix_UB_12      0.0088805000
_diffrn_orient_matrix_UB_13      -0.0565137000
_diffrn_orient_matrix_UB_21      -0.0472403000
_diffrn_orient_matrix_UB_22      -0.0484473000
_diffrn_orient_matrix_UB_23      0.0002415000
_diffrn_orient_matrix_UB_31      -0.0336830000
_diffrn_orient_matrix_UB_32      0.0639126000
_diffrn_orient_matrix_UB_33      0.0079615000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9033
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42100
_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            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_description       plate
_exptl_crystal_F_000             634
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.909
_refine_diff_density_min         -0.862
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 1398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.043(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0593
_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^)+(0.0680P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4058
_reflns_number_total             4769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b09832_si_003.cif
_cod_data_source_block           170629_gj12153
_cod_original_cell_volume        1310.22(18)
_cod_database_code               4131739
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o Co Cl'
_shelx_estimated_absorpt_t_max   0.663
_shelx_estimated_absorpt_t_min   0.317
_reflns_odcompleteness_completeness 99.69
_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:
 C18(H18), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              75666
_shelx_hkl_checksum              13922
_olex2_submission_special_instructions 'No special instructions were received'