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_4128402
_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_absolute_configuration rmad
_chemical_formula_moiety         'C34 H31 Co I2 O3'
_chemical_formula_sum            'C34 H31 Co I2 O3'
_chemical_formula_weight         800.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9249(2)
_cell_length_b                   12.0314(3)
_cell_length_c                   25.6817(6)
_cell_measurement_reflns_used    28089
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      31.3120
_cell_measurement_theta_min      3.0810
_cell_volume                     3066.66(12)
_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 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_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    -13.00  96.00   1.00    4.76    --   19.91  77.00-120.00  109
  2  \w     34.00 107.00   1.00    4.76    --   19.91-178.00 150.00   73
  3  \w    -51.00  48.00   1.00    4.76    --   19.91 -57.00 120.00   99
  4  \w      5.00  93.00   1.00    4.76    --   19.91  57.00 120.00   88
  5  \w     -8.00  78.00   1.00    4.76    --   19.91  57.00  30.00   86
  6  \w    -54.00  43.00   1.00    4.76    --   19.91 -38.00-150.00   97
  7  \w    -89.00 -60.00   1.00    4.76    --  -20.22 145.00 -53.33   29
  8  \w    -39.00  54.00   1.00    4.76    --  -20.22  38.00   0.00   93
  9  \w    -97.00 -66.00   1.00    4.76    --  -20.22 155.00 171.32   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462383000
_diffrn_orient_matrix_UB_12      0.0445513000
_diffrn_orient_matrix_UB_13      0.0029348000
_diffrn_orient_matrix_UB_21      -0.0509546000
_diffrn_orient_matrix_UB_22      -0.0323837000
_diffrn_orient_matrix_UB_23      -0.0119929000
_diffrn_orient_matrix_UB_31      -0.0193685000
_diffrn_orient_matrix_UB_32      -0.0210132000
_diffrn_orient_matrix_UB_33      0.0247024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            66536
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.998
_diffrn_reflns_theta_min         2.594
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.606
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.238
_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            'dark brown'
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.154
_refine_diff_density_max         1.173
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details
;
 Flack x determined using 3663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         10868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0277P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                9555
_reflns_number_total             10868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02569_si_005.cif
_cod_data_source_block           koz-01-451
_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        3066.65(12)
_cod_database_code               4128402
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H31 O3 Co1 I2'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C23(H23),
 C24(H24), C25(H25), C26(H26), C28(H28)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C)
;
_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 1.544
_oxdiff_exptl_absorpt_empirical_full_min 0.612