A synthetically useful catalytic system for aliphatic C-H oxidation with a nonheme cobalt complex and <i>m</i>-CPBA.
Wen, Xiang; Ma, Yidong; Chen, Jie; Wang, Bin; Organic & biomolecular chemistry 22 (2024) 5729–5733; doi:10.1039/d4ob00807c

data_7159993
_publ_section_title
;
 A synthetically useful catalytic system for aliphatic C-H oxidation with
 a nonheme cobalt complex and <i>m</i>-CPBA.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5729
_journal_page_last               5733
_journal_paper_doi               10.1039/d4ob00807c
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H33 Co F3 N5 O3 S, C F3 O3 S'
_chemical_formula_sum            'C32 H33 Co F6 N5 O6 S2'
_chemical_formula_weight         820.68
_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
_audit_creation_date             2021-11-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-08 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7317(2)
_cell_length_b                   20.2300(5)
_cell_length_c                   21.9275(5)
_cell_measurement_reflns_used    12419
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9540
_cell_measurement_theta_min      3.4320
_cell_volume                     3873.32(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0355
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_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     -3.00  86.00   1.00    5.21    --   16.33  37.00  60.00   89
  2  \w    -25.00  55.00   1.00    5.21    --   16.33 -99.00-120.00   80
  3  \w    -51.00  43.00   1.00    5.21    --   16.33 -77.00 120.00   94
  4  \w    -25.00  55.00   1.00    5.21    --   16.33 -99.00 -30.00   80
  5  \w    -25.00  22.00   1.00    5.21    --  -16.79 -99.00  30.00   47
  6  \w      0.00  84.00   1.00    5.21    --   16.33  57.00 150.00   84
  7  \w     35.00  77.00   1.00    5.21    --   16.33 178.00 120.00   42
  8  \w    -84.00  10.00   1.00    5.21    --  -16.79 -77.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0046932000
_diffrn_orient_matrix_UB_12      0.0348286000
_diffrn_orient_matrix_UB_13      -0.0033157000
_diffrn_orient_matrix_UB_21      -0.0492528000
_diffrn_orient_matrix_UB_22      0.0015982000
_diffrn_orient_matrix_UB_23      0.0256993000
_diffrn_orient_matrix_UB_31      0.0644014000
_diffrn_orient_matrix_UB_32      0.0037286000
_diffrn_orient_matrix_UB_33      0.0193732000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47625
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.148
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1684
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.680
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     484
_refine_ls_number_reflns         7891
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0142P)^2^+6.2318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.789
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6781
_reflns_number_total             7891
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00807c2.cif
_cod_data_source_block           20201103_wb_co_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159993.cif.
;
_cod_database_code               7159993
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N'
_shelx_estimated_absorpt_t_max   0.788
_shelx_estimated_absorpt_t_min   0.705
_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. Restrained distances
 S2-C32
 1.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim
Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C32) = Uanis(C32A)
4. Others
 Fixed Sof: S2(0.5) C32(0.5) S2A(0.5) C32A(0.5)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25),
  C26(H26), C28(H28)
5.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              14706
_shelx_fab_checksum              12024
_olex2_date_sample_data_collection 2020-11-03
_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 1.178
_oxdiff_exptl_absorpt_empirical_full_min 0.834