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_4128400
_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         'C30 H23 Co I2 O3, [C7H8]'
_chemical_formula_sum            'C30 H23 Co I2 O3'
_chemical_formula_weight         744.21
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-02-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.255(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.8651(5)
_cell_length_b                   7.3449(3)
_cell_length_c                   15.0607(6)
_cell_measurement_reflns_used    4524
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      27.4430
_cell_measurement_theta_min      3.8810
_cell_volume                     1627.33(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 0.880
_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    -20.00   5.00   1.00    9.15    --   -9.84 -99.00 -30.00   25
  2  \w    -90.00   9.00   1.00    9.15    --   -9.84 -19.00 150.00   99
  3  \w    -71.00  13.00   1.00    9.15    --   -9.84 -37.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0285207000
_diffrn_orient_matrix_UB_12      0.0007038000
_diffrn_orient_matrix_UB_13      -0.0339229000
_diffrn_orient_matrix_UB_21      -0.0383108000
_diffrn_orient_matrix_UB_22      -0.0152864000
_diffrn_orient_matrix_UB_23      -0.0330325000
_diffrn_orient_matrix_UB_31      -0.0063373000
_diffrn_orient_matrix_UB_32      0.0953655000
_diffrn_orient_matrix_UB_33      -0.0050619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9713
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.719
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.429
_diffrn_reflns_theta_min         3.307
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015).
 Analytical numeric absorption correction using a multifaceted crystal
 model based on expressions derived by R.C. Clark & J.S. Reid.
 (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897).
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            'metallic intense black'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.113
_platon_squeeze_details
;
TITL shelx            P 21         R = 0.06
CELL   14.8651    7.3449   15.0607     90.00     98.25     90.00
SPGR P21
C101 0.973 0.120 0.520 !       7.59 eA-3
C102 0.033 0.560 0.402 !       6.37 eA-3
C103 0.156 0.444 0.432 !       6.06 eA-3
C104 0.904 0.122 0.430 !       5.85 eA-3
C105 0.107 0.476 0.383 !       5.26 eA-3
C106 0.829 1.003 0.459 !       4.71 eA-3
C107 0.969 0.574 0.318 !       3.83 eA-3
C108 0.066 1.016 0.643 !       1.75 eA-3
C109 0.086 0.574 0.503 !       1.63 eA-3
C110 0.074 0.185 0.649 !       1.54 eA-3
C111 0.069 0.618 0.636 !       1.47 eA-3
C112 0.892 0.190 0.375 !       1.45 eA-3
C113 0.017 0.683 0.542 !       1.43 eA-3
Q114 0.152 0.322 0.410 !       1.42 eA-3
C115 0.013 0.932 0.708 !       1.42 eA-3
C116 0.018 0.175 0.720 !       1.40 eA-3
C117 0.047 0.396 0.426 !       1.36 eA-3
Q118 0.086 0.724 0.496 !       1.36 eA-3
C119 0.182 0.575 0.658 !       1.35 eA-3
C120 0.975 0.601 0.443 !       1.31 eA-3
Q121 0.089 0.660 0.448 !       1.31 eA-3
C122 0.980 0.754 0.492 !       1.28 eA-3
C123 0.128 0.736 0.602 !       1.24 eA-3
C124 0.967 0.527 0.481 !       1.24 eA-3
Q125 0.215 0.435 0.660 !       1.23 eA-3
C126 0.060 0.299 0.746 !       1.20 eA-3
C127 0.998 0.690 0.400 !       1.17 eA-3
Q128 0.873 0.704 0.281 !       1.16 eA-3
Q129 0.060 0.166 0.796 !       1.15 eA-3
Q130 0.140 0.558 0.424 !       1.14 eA-3
C131 0.860 0.103 0.361 !       1.13 eA-3
Q132 0.752 0.927 0.561 !       1.11 eA-3
Q133 0.958 0.282 0.667 !       1.11 eA-3
C134 0.937 0.914 0.674 !       1.11 eA-3
C135 0.857 0.670 0.439 !       1.11 eA-3
C136 0.867 0.852 0.510 !       1.11 eA-3
C137 0.935 0.514 0.287 !       1.11 eA-3
C138 0.921 0.723 0.409 !       1.10 eA-3
C139 0.079 0.458 0.556 !       1.09 eA-3
Q140 0.202 0.265 0.501 !       1.06 eA-3
C141 0.857 0.499 0.362 !       1.05 eA-3
Q142 0.069 0.779 0.436 !       1.02 eA-3
C143 0.969 0.731 0.356 !       1.01 eA-3
Q144 0.795 0.016 0.545 !       0.99 eA-3
Q145 0.926 0.248 0.308 !       0.98 eA-3
C146 0.839 0.187 0.434 !       0.98 eA-3
Q147 0.280 0.650 0.606 !       0.97 eA-3
Q148 0.300 0.493 0.622 !       0.97 eA-3
C149 0.063 0.868 0.610 !       0.96 eA-3
C150 0.187 0.302 0.549 !       0.95 eA-3
Q151 0.120 0.955 0.801 !       0.93 eA-3
C152 0.902 0.280 0.420 !       0.93 eA-3
Q153 0.969 0.213 0.341 !       0.93 eA-3
C154 0.981 0.596 0.172 !       0.92 eA-3
Q155 0.937 0.333 0.823 !       0.92 eA-3
Q156 0.887 0.690 0.534 !       0.92 eA-3
C157 0.078 0.761 0.560 !       0.91 eA-3
C158 0.874 0.662 0.375 !       0.90 eA-3
Q159 0.172 0.653 0.463 !       0.90 eA-3
C160 0.921 0.838 0.433 !       0.89 eA-3
C161 0.060 0.710 0.607 !       0.89 eA-3
Q162 0.910 0.766 0.594 !       0.88 eA-3
Q163 0.123 0.309 0.346 !       0.88 eA-3
Q164 0.209 0.635 0.531 !       0.88 eA-3
C165 0.124 0.963 0.702 !       0.88 eA-3
Q166 0.859 0.019 0.668 !       0.88 eA-3
Q167 0.703 0.915 0.420 !       0.87 eA-3
C168 0.954 0.630 0.505 !       0.87 eA-3
Q169 0.043 0.153 0.432 !       0.86 eA-3
C170 0.225 0.657 0.716 !       0.86 eA-3
Q171 0.141 0.053 0.754 !       0.86 eA-3
C172 0.076 0.541 0.311 !       0.85 eA-3
Q173 0.781 0.570 0.330 !       0.85 eA-3
Q174 0.279 0.189 0.449 !       0.84 eA-3
Q175 0.063 0.962 0.833 !       0.84 eA-3
Q176 0.208 0.778 0.689 !       0.84 eA-3
C177 0.878 0.862 0.331 !       0.84 eA-3
Q178 0.922 0.110 0.618 !       0.84 eA-3
Q179 0.093 0.264 0.345 !       0.83 eA-3
Q180 0.967 0.091 0.859 !       0.83 eA-3
Q181 0.799 0.282 0.400 !       0.82 eA-3
C182 0.029 0.028 0.765 !       0.82 eA-3
Q183 0.310 0.491 0.705 !       0.81 eA-3
Q184 0.043 0.714 0.378 !       0.81 eA-3
C185 0.081 0.797 0.659 !       0.80 eA-3
C186 0.029 0.517 0.577 !       0.80 eA-3
Q187 0.917 0.633 0.253 !       0.80 eA-3
C188 0.905 0.569 0.426 !       0.79 eA-3
Q189 0.942 0.414 0.233 !       0.79 eA-3
Q190 0.233 0.431 0.359 !       0.79 eA-3
C191 0.124 0.911 0.675 !       0.79 eA-3
Q192 0.104 0.204 0.765 !       0.79 eA-3
C193 0.956 0.864 0.347 !       0.79 eA-3
Q194 0.211 0.381 0.404 !       0.78 eA-3
Q195 0.767 0.945 0.640 !       0.78 eA-3
Q196 0.818 0.886 0.657 !       0.77 eA-3
Q197 0.163 0.748 0.500 !       0.77 eA-3
Q198 0.036 0.780 0.392 !       0.77 eA-3
Q199 0.999 0.410 0.578 !       0.77 eA-3
;
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 1787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6465
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.984
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0196P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0602
_reflns_Friedel_coverage         0.521
_reflns_Friedel_fraction_full    0.745
_reflns_Friedel_fraction_max     0.532
_reflns_number_gt                5659
_reflns_number_total             6465
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02569_si_003.cif
_cod_data_source_block           XSJ-174_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Analytical' was
changed to 'analytical' 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_database_code               4128400
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C30 H23 O3 Co1 I2'
_reflns_odcompleteness_completeness 99.64
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C19(H19), C20(H20), C21(H21), C22(H22), C24(H24)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_platon_squeeze_void_probe_radius 1.20
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.737