Enantioselective C-H amination catalyzed by homoleptic iron salox complexes.
Stroek, Wowa; Rowlinson, Nathalie A. V.; Hudson, Luke A.; Albrecht, Martin; Chemical communications (Cambridge, England) 61 (2025) 15274–15277; doi:10.1039/d5cc04627k

data_7134926
_publ_section_title
;
 Enantioselective C-H amination catalyzed by homoleptic iron salox
 complexes.
;
_journal_issue                   78
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15274
_journal_page_last               15277
_journal_paper_doi               10.1039/d5cc04627k
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H44 Fe N2 O4'
_chemical_formula_sum            'C38 H44 Fe N2 O4'
_chemical_formula_weight         648.6
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-18T11:47:36-00:00
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.7105(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.28670(14)
_cell_length_b                   6.39098(7)
_cell_length_c                   20.0622(2)
_cell_measurement_reflns_used    11445
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.596
_cell_measurement_theta_min      3.801
_cell_volume                     1508.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.101a 64-bit (release 31-08-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_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, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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    -67.00  23.00   0.50    2.00    --  -49.10  72.00  81.00  180
  2  \w   -121.00 -31.00   0.50    2.00    --  -49.10 -72.00 -48.00  180
  3  \w    -22.00  68.00   0.50    2.00    --   49.10 -72.00 -48.00  180
  4  \w     31.00 121.00   0.50    2.00    --   49.10  72.00  81.00  180
  5  \w    -91.00 -18.00   0.50    5.00    --  -90.00  72.00  81.00  146
  6  \w   -161.00 -71.00   0.50    5.00    --  -90.00 -72.00 -48.00  180
  7  \w     93.00 178.00   0.50    5.00    --  111.50  72.00  81.00  170
  8  \w     41.00  91.00   0.50    5.00    --  111.50 -72.00 -48.00  100
  9  \w   -118.00 -73.00   0.50    2.00    --  -49.10-125.00  90.00   90
 10  \w   -118.00 -73.00   0.50    2.00    --  -49.10-125.00-150.00   90
 11  \w    -23.00  26.00   0.50    2.00    --   49.10 -19.00 -30.00   98
 12  \w    -23.00  26.00   0.50    2.00    --   49.10 -19.00-180.00   98
 13  \w    -23.00  26.00   0.50    2.00    --   49.10 -19.00 150.00   98
 14  \w    -71.00 -18.00   0.50    5.00    --  -90.00  61.00-150.00  106
 15  \w   -161.00 -74.00   0.50    5.00    --  -90.00 -65.00 -97.08  174
 16  \w   -161.00 -71.00   0.50    5.00    --  -90.00 -73.00-101.25  180
 17  \w    -51.00 -18.00   0.50    5.00    --  -90.00  45.00 -60.00   66
 18  \w    -51.00 -18.00   0.50    5.00    --  -90.00  45.00 -90.00   66
 19  \w     43.00 111.00   0.50    5.00    --  111.50-125.00  30.00  136
 20  \w     41.00  71.00   0.50    5.00    --  111.50 -61.00  90.00   60
 21  \w    104.00 178.00   0.50    5.00    --  111.50  15.00 -30.00  148
 22  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00-180.00  128
 23  \w     41.00  71.00   0.50    5.00    --  111.50 -61.00   0.00   60
 24  \w     41.00 105.00   0.50    5.00    --  111.50 -77.00  60.00  128
 25  \w     97.00 178.00   0.50    5.00    --  111.50  61.00-180.00  162
 26  \w     43.00 111.00   0.50    5.00    --  111.50-125.00   0.00  136
 27  \w     43.00 111.00   0.50    5.00    --  111.50-125.00-180.00  136
 28  \w     41.00 105.00   0.50    5.00    --  111.50 -94.00-150.00  128
 29  \w     42.00 107.00   0.50    5.00    --  111.50-105.00 -57.56  130
 30  \w     42.00 107.00   0.50    5.00    --  111.50-103.00 162.11  130
 31  \w     43.00 111.00   0.50    5.00    --  111.50-125.00 -60.00  136
 32  \w     91.00 178.00   0.50    5.00    --  111.50  77.00 150.00  174
 33  \w     97.00 178.00   0.50    5.00    --  111.50  61.00  30.00  162
 34  \w     91.00 178.00   0.50    5.00    --  111.50  77.00  60.00  174
 35  \w     41.00 105.00   0.50    5.00    --  111.50 -77.00-150.00  128
 36  \w    109.00 143.00   0.50    5.00    --  111.50  45.00  30.00   68
 37  \w     68.00 111.00   0.50    5.00    --  111.50-125.00-120.00   86
 38  \w     79.00 109.00   0.50    5.00    --  111.50-125.00  60.00   60
 39  \w     98.00 164.00   0.50    5.00    --  111.50  61.00 -90.00  132
 40  \w     67.00 100.00   0.50    5.00    --  111.50 -94.00   0.00   66
 41  \w     53.00  79.00   0.50    5.00    --  111.50 -77.00 -60.00   52
 42  \w     78.00 104.00   0.50    5.00    --  111.50 -94.00 -90.00   52
 43  \w     65.00  91.00   0.50    5.00    --  111.50 -94.00 -30.00   52
 44  \w    125.00 151.00   0.50    5.00    --  111.50  30.00-180.00   52
 45  \w     97.00 156.00   0.50    5.00    --  111.50  61.00  60.00  118
 46  \w     97.00 177.00   0.50    5.00    --  111.50 125.00   0.00  160
 47  \w     94.00 159.00   0.50    5.00    --  111.50  71.00 -66.41  130
 48  \w    100.00 161.00   0.50    5.00    --  111.50  77.00-120.00  122
 49  \w     92.00 125.00   0.50    5.00    --  111.50  77.00 -90.00   66
 50  \w    105.00 172.00   0.50    5.00    --  111.50  30.00  30.00  134
 51  \w    122.00 172.00   0.50    5.00    --  111.50  15.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1091118
_diffrn_orient_matrix_UB_12      0.006979
_diffrn_orient_matrix_UB_13      0.0616146
_diffrn_orient_matrix_UB_21      -0.020394
_diffrn_orient_matrix_UB_22      -0.228001
_diffrn_orient_matrix_UB_23      0.0183031
_diffrn_orient_matrix_UB_31      0.0693946
_diffrn_orient_matrix_UB_32      -0.0777418
_diffrn_orient_matrix_UB_33      -0.0479677
_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  0.0568
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15143
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.96
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.998
_diffrn_reflns_theta_min         6.855
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.375
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.35425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.6643P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                3125
_reflns_number_total             3180
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
        Component 2 rotated by 2.0308\%
        around [-0.43 -0.29 0.85] (reciprocal) or [-0.27 -0.94 0.23] (direct)
;
_cod_data_source_file            d5cc04627k2.cif
_cod_data_source_block           Fe4
_cod_depositor_comments
'Adding full bibliography for 7134921--7134926.cif.'
_cod_database_code               7134926
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.884
_oxdiff_exptl_absorpt_empirical_full_min 0.451
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
        1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
        2.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17), C14(H14), C12(H12)
        2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C11(H11A,H11B), C15(H15A,H15B), C8(H8A,H8B), C18(H18A,H18B),
 C13(H13A,H13B), C19(H19A,H19B)
        2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3), C4(H4)
;
_shelx_res_checksum              24893
_shelx_hkl_checksum              60049