Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component C–H Functionalization
Herraiz, Ana G.; Cramer, Nicolai; ACS Catalysis 11 (2021) 11938–11944; doi:10.1021/acscatal.1c03153

data_4519064
_publ_section_title
;
 Cobalt(III)-Catalyzed Diastereo- and Enantioselective Three-Component
 C--H Functionalization
;
_journal_issue                   19
_journal_name_full               'ACS Catalysis'
_journal_page_first              11938
_journal_page_last               11944
_journal_paper_doi               10.1021/acscatal.1c03153
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C72 H70 Co2 I4 O4, C H Cl3'
_chemical_formula_sum            'C73 H71 Cl3 Co2 I4 O4'
_chemical_formula_weight         1744.10
_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             2021-08-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.41118(8)
_cell_length_b                   17.39267(12)
_cell_length_c                   36.5868(2)
_cell_measurement_reflns_used    58521
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      71.7450
_cell_measurement_theta_min      3.6430
_cell_volume                     6625.07(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -76.00  28.00   1.00    5.00    --  -41.16  87.00 -91.00  104
  2  \w     -3.00  63.00   1.00    5.00    --   41.16 -87.00 151.00   66
  3  \w    116.00 141.00   1.00   20.00    --  103.57  87.00 -91.00   25
  4  \w     44.00  74.00   1.00   20.00    --  103.57 -87.00 151.00   30
  5  \w     -4.00  22.00   1.00    5.00    --   34.00  93.00 -51.05   26
  6  \w     -4.00  21.00   1.00    5.00    --   34.00  93.00  53.27   25
  7  \w   -114.00 -19.00   1.00    5.00    --  -41.16 -38.00 -30.00   95
  8  \w    -85.00  -6.00   1.00    5.00    --  -41.16 125.00  30.00   79
  9  \w   -113.00 -13.00   1.00    5.00    --  -41.16 -57.00 -90.00  100
 10  \w   -114.00 -18.00   1.00    5.00    --  -41.16 -38.00 120.00   96
 11  \w      8.00  33.00   1.00    5.00    --   42.00  83.00  96.90   25
 12  \w     14.00  39.00   1.00    5.00    --   46.00  76.00-142.38   25
 13  \w     16.00  41.00   1.00    5.00    --   50.00  82.00 -12.30   25
 14  \w     16.00  41.00   1.00    5.00    --   50.00  81.00 -54.52   25
 15  \w     16.00  41.00   1.00    5.00    --   50.00  82.00 129.57   25
 16  \w     16.00  41.00   1.00    5.00    --   50.00  82.00-117.14   25
 17  \w     16.00  41.00   1.00    5.00    --   50.00  82.00-168.88   25
 18  \w     16.00  42.00   1.00    5.00    --   50.00  82.00  53.90   26
 19  \w     36.00  62.00   1.00    5.00    --   66.00  70.00  15.85   26
 20  \w     35.00  62.00   1.00    5.00    --   66.00  71.00 106.02   27
 21  \w    117.00 143.00   1.00    5.00    --   70.00  70.00 -15.17   26
 22  \w     39.00  66.00   1.00    5.00    --   70.00  71.00 -45.92   27
 23  \w     40.00  66.00   1.00    5.00    --   70.00  69.00 142.71   26
 24  \w     39.00  74.00   1.00    5.00    --   70.00  71.00-125.21   35
 25  \w     39.00  64.00   1.00    5.00    --   70.00  70.00 -15.17   25
 26  \w     40.00  74.00   1.00    5.00    --   70.00  64.00  83.00   34
 27  \w    117.00 143.00   1.00    5.00    --   70.00  69.00 142.71   26
 28  \w     79.00 132.00   1.00    5.00    --   70.00  71.00-169.64   53
 29  \w     39.00  65.00   1.00    5.00    --   70.00  71.00-169.64   26
 30  \w     39.00  65.00   1.00    5.00    --   70.00  69.00  49.96   26
 31  \w    100.00 126.00   1.00   20.00    --   74.00  71.00 -69.72   26
 32  \w     43.00  69.00   1.00   20.00    --   74.00  71.00 -69.72   26
 33  \w     43.00  69.00   1.00   20.00    --   74.00  69.00-103.63   26
 34  \w     47.00  72.00   1.00   20.00    --   78.00  69.00 121.42   25
 35  \w     48.00  74.00   1.00   20.00    --   78.00  71.00 -99.71   26
 36  \w     52.00 108.00   1.00   20.00    --   82.00  66.00-136.69   56
 37  \w     56.00  82.00   1.00   20.00    --   82.00  71.00 173.22   26
 38  \w     55.00  81.00   1.00   20.00    --   86.00  69.00 -30.40   26
 39  \w     55.00  81.00   1.00   20.00    --   86.00  70.00  -1.77   26
 40  \w     56.00  82.00   1.00   20.00    --   86.00  64.00  89.07   26
 41  \w    120.00 146.00   1.00   20.00    --   86.00  69.00 143.43   26
 42  \w     55.00  81.00   1.00   20.00    --   86.00  69.00 143.43   26
 43  \w     61.00  87.00   1.00   20.00    --   90.00  59.00 -57.08   26
 44  \w     59.00  84.00   1.00   20.00    --   90.00  70.00  19.90   25
 45  \w     63.00 120.00   1.00   20.00    --   90.00  63.00 170.41   57
 46  \w     64.00 163.00   1.00   20.00    --   94.00  71.00  45.20   99
 47  \w    132.00 170.00   1.00   20.00    --   98.00  69.00 102.76   38
 48  \w     67.00  93.00   1.00   20.00    --   98.00  69.00 102.76   26
 49  \w    133.00 170.00   1.00   20.00    --  103.57 125.00   0.00   37
 50  \w    124.00 173.00   1.00   20.00    --  103.57  61.00 -60.00   49
 51  \w    111.00 145.00   1.00   20.00    --  103.57  68.00-116.25   34
 52  \w    109.00 176.00   1.00   20.00    --  103.57  61.00-150.00   67
 53  \w     78.00 161.00   1.00   20.00    --  103.57  44.00-170.18   83
 54  \w     74.00 101.00   1.00   20.00    --  103.57  61.00-150.00   27
 55  \w     73.00  99.00   1.00   20.00    --  103.57  68.00-116.25   26
 56  \w     80.00 106.00   1.00   20.00    --  103.57 -97.00  43.17   26
 57  \w     74.00 159.00   1.00   20.00    --  103.57  61.00  90.00   85
 58  \w     74.00 118.00   1.00   20.00    --  103.57  61.00 -60.00   44
 59  \w     22.00 106.00   1.00   20.00    --  103.57 -94.00 120.00   84
 60  \w     23.00  73.00   1.00   20.00    --  103.57 -97.00  43.17   50
 61  \w     73.00 173.00   1.00   20.00    --  103.57  69.00 128.03  100
 62  \w     75.00 174.00   1.00   20.00    --  103.57  61.00 -90.00   99
 63  \w     46.00 111.00   1.00   20.00    --  103.57-125.00-120.00   65
 64  \w     74.00 100.00   1.00   20.00    --  103.57  61.00-120.00   26
 65  \w     35.00 111.00   1.00   20.00    --  103.57-125.00 -30.00   76
 66  \w     46.00 107.00   1.00   20.00    --  103.57-102.00 -27.31   61
 67  \w     74.00 173.00   1.00   20.00    --  103.57  61.00 -30.00   99
 68  \w     30.00  84.00   1.00   20.00    --  103.57 -94.00  60.00   54
 69  \w     74.00 171.00   1.00   20.00    --  103.57  68.00  17.17   97
 70  \w     43.00  69.00   1.00   20.00    --  103.57 -94.00   0.00   26
;
_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      -0.0758343000
_diffrn_orient_matrix_UB_12      0.0324933000
_diffrn_orient_matrix_UB_13      0.0327000000
_diffrn_orient_matrix_UB_21      0.0059747000
_diffrn_orient_matrix_UB_22      -0.0791249000
_diffrn_orient_matrix_UB_23      0.0188746000
_diffrn_orient_matrix_UB_31      0.1269225000
_diffrn_orient_matrix_UB_32      0.0230565000
_diffrn_orient_matrix_UB_33      0.0186240000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            125928
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.506
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.054
_exptl_absorpt_correction_T_max  0.560
_exptl_absorpt_correction_T_min  0.057
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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            'clear dark green'
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_description       prism
_exptl_crystal_F_000             3432
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.908
_refine_diff_density_min         -1.128
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Flack x determined using 4821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     757
_refine_ls_number_reflns         11706
_refine_ls_number_restraints     1343
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0607P)^2^+31.3913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                11465
_reflns_number_total             11706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03153_si_003.cif
_cod_data_source_block           agh-r544
_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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        6625.08(8)
_cod_database_code               4519064
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C73 H71 Cl3 Co2 I4 O4'
_shelx_estimated_absorpt_t_max   0.379
_shelx_estimated_absorpt_t_min   0.102
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C73(H73)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B), C34(H34A,H34B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B),
  C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C70(H70A,H70B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C26(H26),
 C27(H27), C28(H28), C29(H29), C31(H31), C38(H38), C41(H41), C52(H52), C57(H57),
  C56(H56), C55(H55), C54(H54), C62(H62), C63(H63), C64(H64), C65(H65), C67(H67)
4.d Naphthalene refined as free rotating group:
 C59(C50,C51,C52,C53,C58,C57,C56,C55,C54)
4.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C48(H48A,H48B,
 H48C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              85439
_shelx_hkl_checksum              27856
_shelx_fab_checksum              62457
_olex2_date_sample_data_collection 2021-04-22
_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 1.705
_oxdiff_exptl_absorpt_empirical_full_min 0.621