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_4519063
_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         'C28 H26 N2 O2'
_chemical_formula_sum            'C28 H26 N2 O2'
_chemical_formula_weight         422.51
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8768(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.18927(8)
_cell_length_b                   12.80314(10)
_cell_length_c                   10.83576(9)
_cell_measurement_reflns_used    14926
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8900
_cell_measurement_theta_min      4.0820
_cell_volume                     1125.393(17)
_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 0.993
_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    -83.00   3.00   1.00    1.00    --  -40.91 112.00 -57.00   86
  2  \w     18.00  84.00   1.00    1.00    --   40.91-112.00-150.00   66
  3  \w     72.00  98.00   1.00    4.00    --  112.00-112.00-150.00   26
  4  \w    132.00 158.00   1.00    4.00    --  112.00 112.00 -57.00   26
  5  \w   -114.00 -16.00   1.00    1.00    --  -40.91 -38.00   0.00   98
  6  \w    -54.00 -24.00   1.00    1.00    --  -40.91 -38.00-150.00   30
  7  \w    -48.00 -17.00   1.00    1.00    --  -40.91 -57.00-180.00   31
  8  \w   -112.00 -50.00   1.00    1.00    --  -40.91 -57.00-180.00   62
  9  \w      6.00  31.00   1.00    1.00    --   40.91  85.00 -74.74   25
 10  \w    -20.00  72.00   1.00    1.00    --   40.91 -77.00  60.00   92
 11  \w     10.00  35.00   1.00    1.00    --   42.00  74.00 136.83   25
 12  \w     12.00  38.00   1.00    1.00    --   46.00  82.00 -75.20   26
 13  \w     16.00  41.00   1.00    1.00    --   50.00  81.00 105.70   25
 14  \w     16.00  42.00   1.00    1.00    --   50.00  82.00-120.04   26
 15  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 -15.02   25
 16  \w     16.00  41.00   1.00    1.00    --   50.00  82.00 160.87   25
 17  \w     82.00 109.00   1.00    1.00    --   58.00  64.00-126.38   27
 18  \w     35.00  65.00   1.00    1.00    --   58.00  64.00-126.38   30
 19  \w     95.00 134.00   1.00    1.00    --   62.00  69.00  54.74   39
 20  \w     31.00  58.00   1.00    1.00    --   62.00  69.00  54.74   27
 21  \w     35.00  62.00   1.00    1.00    --   66.00  71.00  82.12   27
 22  \w    101.00 127.00   1.00    1.00    --   66.00  71.00  82.12   26
 23  \w     37.00  62.00   1.00    1.00    --   66.00  70.00-174.39   25
 24  \w     40.00  66.00   1.00    1.00    --   70.00  66.00  59.28   26
 25  \w     39.00  89.00   1.00    1.00    --   70.00  71.00 145.90   50
 26  \w     39.00  70.00   1.00    1.00    --   70.00  70.00 104.12   31
 27  \w     40.00  91.00   1.00    1.00    --   70.00  70.00 -46.41   51
 28  \w     43.00  68.00   1.00    1.00    --   74.00  70.00-104.86   25
 29  \w    115.00 146.00   1.00    1.00    --   74.00  69.00 -75.46   31
 30  \w    112.00 148.00   1.00    1.00    --   74.00  71.00  -6.90   36
 31  \w     43.00  69.00   1.00    1.00    --   74.00  69.00 -75.46   26
 32  \w     43.00  95.00   1.00    1.00    --   74.00  71.00  -6.90   52
 33  \w     52.00  86.00   1.00    4.00    --   82.00  68.00 169.46   34
 34  \w     65.00 102.00   1.00    4.00    --   90.00  52.00-144.19   37
 35  \w     65.00 155.00   1.00    4.00    --   94.00  68.00 -74.97   90
 36  \w     72.00  99.00   1.00    4.00    --  102.00  68.00  16.95   27
 37  \w     48.00 107.00   1.00    4.00    --  112.00 -94.00 -60.00   59
 38  \w     37.00  90.00   1.00    4.00    --  112.00-111.00-120.00   53
 39  \w     36.00 107.00   1.00    4.00    --  112.00-111.00 150.00   71
 40  \w     84.00 175.00   1.00    4.00    --  112.00  61.00  30.00   91
 41  \w     40.00  88.00   1.00    4.00    --  112.00 -61.00-150.00   48
 42  \w     56.00 109.00   1.00    4.00    --  112.00-111.00 -90.00   53
 43  \w     83.00 111.00   1.00    4.00    --  112.00  61.00 150.00   28
 44  \w     86.00 118.00   1.00    4.00    --  112.00  45.00   0.00   32
 45  \w    120.00 176.00   1.00    4.00    --  112.00  61.00 120.00   56
 46  \w    131.00 169.00   1.00    4.00    --  112.00  61.00-150.00   38
 47  \w     83.00 112.00   1.00    4.00    --  112.00  61.00 120.00   29
 48  \w     83.00 109.00   1.00    4.00    --  112.00  61.00-150.00   26
 49  \w     85.00 161.00   1.00    4.00    --  112.00  61.00 -90.00   76
 50  \w    128.00 160.00   1.00    4.00    --  112.00  61.00-120.00   32
 51  \w     84.00 122.00   1.00    4.00    --  112.00  61.00-120.00   38
 52  \w    124.00 176.00   1.00    4.00    --  112.00  61.00 -30.00   52
 53  \w     82.00 176.00   1.00    4.00    --  112.00  67.00 -64.08   94
 54  \w     95.00 134.00   1.00    4.00    --  112.00 -45.00 -30.00   39
 55  \w     83.00 175.00   1.00    4.00    --  112.00  61.00-180.00   92
 56  \w     88.00 118.00   1.00    4.00    --  112.00  45.00-120.00   30
 57  \w     83.00 112.00   1.00    4.00    --  112.00  61.00 -30.00   29
 58  \w     53.00 108.00   1.00    4.00    --  112.00-111.00  30.00   55
 59  \w     43.00  69.00   1.00    4.00    --  112.00 -45.00 -30.00   26
 60  \w     36.00  90.00   1.00    4.00    --  112.00-111.00-180.00   54
 61  \w    111.00 141.00   1.00    4.00    --  112.00 -61.00-150.00   30
 62  \w     84.00 167.00   1.00    4.00    --  112.00  61.00   0.00   83
 63  \w     83.00 177.00   1.00    4.00    --  112.00  61.00  90.00   94
 64  \w     36.00 106.00   1.00    4.00    --  112.00 -94.00  60.00   70
 65  \w     83.00 178.00   1.00    4.00    --  112.00  61.00  60.00   95
 66  \w    116.00 170.00   1.00    4.00    --  112.00  61.00 150.00   54
;
_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      -0.0337195000
_diffrn_orient_matrix_UB_12      -0.0297972000
_diffrn_orient_matrix_UB_13      -0.1389071000
_diffrn_orient_matrix_UB_21      0.0457322000
_diffrn_orient_matrix_UB_22      -0.1142208000
_diffrn_orient_matrix_UB_23      0.0334227000
_diffrn_orient_matrix_UB_31      -0.1812093000
_diffrn_orient_matrix_UB_32      -0.0233073000
_diffrn_orient_matrix_UB_33      0.0137202000
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.038
_diffrn_reflns_theta_min         4.119
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.761
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 2130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0268
_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^)+(0.0343P)^2^+0.1923P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4564
_reflns_number_total             4633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03153_si_002.cif
_cod_data_source_block           agh-r416
_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        1125.392(17)
_cod_database_code               4519063
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C28 H26 N2 O2'
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.808
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_shelx_res_checksum              5617
_shelx_hkl_checksum              86798
_olex2_date_sample_data_collection 2021-04-14
_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 2.133
_oxdiff_exptl_absorpt_empirical_full_min 0.544