Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly Enantioselective 3d-Metal-Catalyzed C-H Functionalizations.
Ozols, Kristers; Jang, Yun-Suk; Cramer, Nicolai; Journal of the American Chemical Society 141 (2019) 5675–5680; doi:10.1021/jacs.9b02569

data_4128396
_publ_section_title
;
 Chiral Cyclopentadienyl Cobalt(III) Complexes Enable Highly
 Enantioselective 3d-Metal-Catalyzed C-H Functionalizations.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5675
_journal_page_last               5680
_journal_paper_doi               10.1021/jacs.9b02569
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C11 H15 Co I2 O'
_chemical_formula_sum            'C11 H15 Co I2 O'
_chemical_formula_weight         475.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 112.29(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0976(12)
_cell_length_b                   12.673(3)
_cell_length_c                   8.5700(15)
_cell_measurement_reflns_used    1695
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.3140
_cell_measurement_theta_min      5.5360
_cell_volume                     713.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -120.00 -89.00   1.00    2.50    --  -42.76 -99.00-180.00   31
  2  \w   -121.00 -87.00   1.00    2.50    --  -42.76 -99.00 120.00   34
  3  \w   -114.00 -17.00   1.00    2.50    --  -42.76 -57.00  30.00   97
  4  \w    -66.00  23.00   1.00    2.50    --  -42.76  57.00-180.00   89
  5  \w     30.00  80.00   1.00    2.50    --   42.76-125.00 -30.00   50
  6  \w     63.00 134.00   1.00   10.00    --  105.68 -30.00  30.00   71
  7  \w     25.00 106.00   1.00   10.00    --  105.68 -94.00 -90.00   81
  8  \w     86.00 113.00   1.00   10.00    --  105.68-125.00-120.00   27
  9  \w     71.00 109.00   1.00   10.00    --  105.68 -94.00   0.00   38
 10  \w     38.00  69.00   1.00   10.00    --  105.68 -94.00   0.00   31
 11  \w     43.00  81.00   1.00   10.00    --  105.68-125.00-150.00   38
 12  \w     78.00 109.00   1.00   10.00    --  105.68-127.00 179.00   31
 13  \w     84.00 164.00   1.00   10.00    --  105.68  30.00  90.00   80
 14  \w    105.00 164.00   1.00   10.00    --  105.68 125.00 -30.00   59
 15  \w     86.00 176.00   1.00   10.00    --  105.68  30.00  30.00   90
 16  \w     38.00 130.00   1.00   10.00    --  105.68 -61.00   0.00   92
 17  \w     57.00 126.00   1.00   10.00    --  105.68 -30.00-150.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0373011000
_diffrn_orient_matrix_UB_12      -0.0967448000
_diffrn_orient_matrix_UB_13      -0.1169672000
_diffrn_orient_matrix_UB_21      0.0696966000
_diffrn_orient_matrix_UB_22      -0.0732102000
_diffrn_orient_matrix_UB_23      0.1547627000
_diffrn_orient_matrix_UB_31      -0.2208102000
_diffrn_orient_matrix_UB_32      -0.0067092000
_diffrn_orient_matrix_UB_33      -0.0091528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3909
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         5.579
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    43.211
_exptl_absorpt_correction_T_max  0.438
_exptl_absorpt_correction_T_min  0.007
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.216
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.048
_refine_diff_density_max         1.970
_refine_diff_density_min         -1.813
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1321
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0758
_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^)+(0.0638P)^2^+12.0436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1863
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1144
_reflns_number_total             1321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02569_si_006.cif
_cod_data_source_block           koz-01-025
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        713.3(2)
_cod_database_code               4128396
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C11 H15 O1 Co I2'
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 O1-C7
 1.15 with sigma of 0.02
 Co1-C7
 1.9 with sigma of 0.02
 H4B-H4A = H4A-H4A_$1
 1.568 with sigma of 0.02
 C4-H4B = C4-H4A
 0.98 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(I2) = Uanis(O1)
Uanis(I2) = Uanis(C7)
4. Others
 Fixed Sof: I2(0.5) O1(0.5) C7(0.5)
5.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.987
_oxdiff_exptl_absorpt_empirical_full_min 0.426