Cobalt-Catalyzed Asymmetric Markovnikov Hydroboration of Styrenes
Chen, Xu; Cheng, Zhaoyang; Lu, Zhan; ACS Catalysis 9 (2019) 4025–; doi:10.1021/acscatal.8b05135

data_4514707
_publ_section_title
;
 Cobalt-Catalyzed Asymmetric Markovnikov Hydroboration of Styrenes
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              4025
_journal_paper_doi               10.1021/acscatal.8b05135
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C26 H28 Cl2 Co N4 O'
_chemical_formula_sum            'C26 H28 Cl2 Co N4 O'
_chemical_formula_weight         542.35
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5625(5)
_cell_length_b                   11.3203(4)
_cell_length_c                   24.4937(10)
_cell_measurement_reflns_used    4897
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3969
_cell_measurement_theta_min      2.9040
_cell_volume                     2651.5(2)
_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      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00   47.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   77.0000  150.0000 92

  2 omega  -84.00    8.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   30.0000 92

  3 omega   -7.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  -90.0000 97
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0050630000
_diffrn_orient_matrix_UB_12      0.0101112000
_diffrn_orient_matrix_UB_13      -0.0285098000
_diffrn_orient_matrix_UB_21      0.0500019000
_diffrn_orient_matrix_UB_22      0.0450943000
_diffrn_orient_matrix_UB_23      0.0047830000
_diffrn_orient_matrix_UB_31      0.0545403000
_diffrn_orient_matrix_UB_32      -0.0423162000
_diffrn_orient_matrix_UB_33      -0.0017462000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.910
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65840
_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    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0335P)^2^+0.0463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4046
_reflns_number_total             4859
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b05135_si_002.cif
_cod_data_source_block           170620_cx9198_p1
_cod_original_cell_volume        2651.44(19)
_cod_database_code               4514707
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 o1 n2 cl1 Co1'
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.721
_reflns_odcompleteness_completeness 99.68
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C3(H3), C4(H4A), C9(H9), C10(H10), C11(H11), C12(H12),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              90153
_shelx_hkl_checksum              74019
_olex2_submission_special_instructions 'No special instructions were received'