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_7134924
_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         'C26 H32 Fe N2 O4'
_chemical_formula_sum            'C26 H32 Fe N2 O4'
_chemical_formula_weight         492.38
_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             2023-11-02T18:20:01-00:00
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.7213(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.23289(15)
_cell_length_b                   5.80595(8)
_cell_length_c                   17.0105(2)
_cell_measurement_reflns_used    12315
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      80.201
_cell_measurement_theta_min      7.318
_cell_volume                     1190.80(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (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      173.01(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 0.994
_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    -84.00  -9.00   0.50    1.00    --  -49.99 120.00-110.00  150
  2  \w   -106.00 -28.00   0.50    1.00    --  -49.99 154.00  47.00  156
  3  \w   -121.00 -53.00   0.50    1.00    --  -49.99-154.00   7.00  136
  4  \w     31.00  90.00   0.50    1.00    --   49.99-120.00 165.00  118
  5  \w     49.00 112.00   0.50    1.00    --   49.99-154.00   7.00  126
  6  \w     75.00 122.00   0.50    1.00    --   49.99 154.00  47.00   94
  7  \w    -84.00 -21.00   0.50   10.00    --  -90.00 120.00-110.00  126
  8  \w   -159.00 -77.00   0.50   10.00    --  -90.00-120.00 165.00  164
  9  \w   -146.00 -53.00   0.50   10.00    --  -90.00-154.00   7.00  186
 10  \w     49.00 131.00   0.50   10.00    --  111.50-154.00   7.00  164
 11  \w     98.00 178.00   0.50   10.00    --  111.50 120.00-110.00  160
 12  \w     43.00 110.00   0.50   10.00    --  111.50-120.00 165.00  134
 13  \w    -62.00 -29.00   0.50    1.00    --    2.00 157.00 113.28   66
 14  \w    -42.00 -13.00   0.50    1.00    --    2.00 126.00 -94.80   58
 15  \w    -13.00  14.00   0.50    1.00    --   18.00 102.00-124.35   54
 16  \w     16.00  42.00   0.50    1.00    --   42.00  91.00-164.94   52
 17  \w   -122.00 -45.00   0.50    1.00    --  -49.99 -19.00  90.00  154
 18  \w     39.00 130.00   0.50    1.00    --   58.00  75.00 175.38  182
 19  \w    -91.00 -44.00   0.50    1.00    --  -62.00 -72.00  19.95   94
 20  \w     44.00  72.00   0.50    1.00    --   62.00  75.00-164.93   56
 21  \w     75.00 104.00   0.50    1.00    --   62.00  76.00 151.37   58
 22  \w     44.00  69.00   0.50    1.00    --   62.00  76.00 151.37   50
 23  \w     44.00  71.00   0.50    1.00    --   62.00  75.00-175.86   54
 24  \w    -78.00 -51.00   0.50    1.00    --  -66.00 -65.00  -5.19   54
 25  \w   -122.00 -94.00   0.50    1.00    --  -66.00 -76.00 -53.06   56
 26  \w    -86.00 -54.00   0.50    1.00    --  -66.00 -60.00  88.15   64
 27  \w    -84.00 -57.00   0.50    1.00    --  -70.00 -59.00  81.80   54
 28  \w    -94.00 -56.00   0.50    1.00    --  -70.00 -62.00 -89.16   76
 29  \w    -92.00 -61.00   0.50    1.00    --  -70.00 -59.00 -21.80   62
 30  \w    -89.00 -61.00   0.50    1.00    --  -74.00 -60.00  82.71   56
 31  \w    -90.00 -63.00   0.50    1.00    --  -78.00 -65.00 -51.95   54
 32  \w    -91.00 -64.00   0.50   10.00    --  -82.00 -72.00  24.93   54
 33  \w   -108.00 -72.00   0.50   10.00    --  -90.00 -73.00  79.44   72
 34  \w   -100.00 -75.00   0.50   10.00    --  -90.00 -66.00  62.05   50
 35  \w    -98.00 -70.00   0.50   10.00    --  -90.00 -77.00  30.00   56
 36  \w    -97.00 -70.00   0.50   10.00    --  -90.00 -77.00 -30.00   54
 37  \w    -99.00 -72.00   0.50   10.00    --  -90.00 -72.00 -24.98   54
 38  \w    -98.00 -71.00   0.50   10.00    --  -90.00 -76.00  17.25   54
 39  \w   -160.00-133.00   0.50   10.00    --  -90.00 -77.00 -90.00   54
 40  \w   -120.00 -71.00   0.50   10.00    --  -90.00 -77.00   0.00   98
 41  \w   -145.00-118.00   0.50   10.00    --  -90.00 -77.00-150.00   54
 42  \w    -95.00 -70.00   0.50   10.00    --  -90.00 -77.00  60.00   50
 43  \w     46.00 126.00   0.50   10.00    --  102.00-144.00 163.61  160
 44  \w    112.00 177.00   0.50   10.00    --  111.50  45.00-150.00  130
 45  \w     64.00 111.00   0.50   10.00    --  111.50-125.00 -90.00   94
 46  \w    145.00 172.00   0.50   10.00    --  111.50  61.00 -30.00   54
 47  \w     78.00 105.00   0.50   10.00    --  111.50 -94.00  30.00   54
 48  \w    143.00 175.00   0.50   10.00    --  111.50  61.00 150.00   64
 49  \w     93.00 153.00   0.50   10.00    --  111.50  77.00  30.00  120
 50  \w     95.00 141.00   0.50   10.00    --  111.50  77.00-150.00   92
 51  \w    112.00 159.00   0.50   10.00    --  111.50 125.00 -60.00   94
 52  \w     98.00 139.00   0.50   10.00    --  111.50  61.00 150.00   82
 53  \w    104.00 139.00   0.50   10.00    --  111.50  61.00 -30.00   70
 54  \w    126.00 161.00   0.50   10.00    --  111.50 125.00  90.00   70
 55  \w     98.00 149.00   0.50   10.00    --  111.50  61.00-120.00  102
 56  \w     99.00 178.00   0.50   10.00    --  111.50  61.00-180.00  158
 57  \w    105.00 165.00   0.50   10.00    --  111.50  45.00   0.00  120
 58  \w     93.00 177.00   0.50   10.00    --  111.50  77.00  90.00  168
 59  \w     75.00 102.00   0.50   10.00    --  111.50 -94.00 -30.00   54
 60  \w    100.00 176.00   0.50   10.00    --  111.50  61.00 -60.00  152
 61  \w     42.00  73.00   0.50   10.00    --  111.50 -94.00 -30.00   62
 62  \w     75.00 105.00   0.50   10.00    --  111.50-125.00 150.00   60
 63  \w     45.00 110.00   0.50   10.00    --  111.50-125.00 120.00  130
 64  \w     44.00  71.00   0.50   10.00    --  111.50 -61.00  30.00   54
 65  \w     93.00 144.00   0.50   10.00    --  111.50  77.00 150.00  102
 66  \w    107.00 150.00   0.50   10.00    --  111.50  45.00  30.00   86
 67  \w     45.00  86.00   0.50   10.00    --  111.50 -77.00  30.00   82
 68  \w     78.00 105.00   0.50   10.00    --  111.50 -94.00 -60.00   54
 69  \w    100.00 150.00   0.50   10.00    --  111.50  61.00  90.00  100
 70  \w    104.00 175.00   0.50   10.00    --  111.50  61.00  60.00  142
 71  \w    102.00 167.00   0.50   10.00    --  111.50  61.00 120.00  130
 72  \w     94.00 119.00   0.50   10.00    --  111.50  77.00 -60.00   50
 73  \w    138.00 173.00   0.50   10.00    --  111.50  77.00  60.00   70
 74  \w    139.00 177.00   0.50   10.00    --  111.50  77.00-120.00   76
 75  \w     96.00 134.00   0.50   10.00    --  111.50  77.00  60.00   76
 76  \w    100.00 173.00   0.50   10.00    --  111.50  61.00   0.00  146
 77  \w     81.00 109.00   0.50   10.00    --  111.50-125.00  60.00   56
 78  \w     45.00  78.00   0.50   10.00    --  111.50-125.00  60.00   66
 79  \w    141.00 175.00   0.50   10.00    --  111.50  61.00-150.00   68
 80  \w     41.00  78.00   0.50   10.00    --  111.50 -77.00 -90.00   74
 81  \w    101.00 129.00   0.50   10.00    --  111.50  61.00-150.00   56
 82  \w     44.00  92.00   0.50   10.00    --  111.50 -94.00   0.00   96
 83  \w    112.00 158.00   0.50   10.00    --  111.50 125.00 -30.00   92
 84  \w     42.00  69.00   0.50   10.00    --  111.50 -61.00-150.00   54
 85  \w    118.00 156.00   0.50   10.00    --  111.50 125.00 -90.00   76
 86  \w     42.00 102.00   0.50   10.00    --  111.50 -94.00 150.00  120
 87  \w    148.00 176.00   0.50   10.00    --  111.50  77.00 120.00   56
 88  \w     98.00 139.00   0.50   10.00    --  111.50  77.00 120.00   82
 89  \w    113.00 143.00   0.50   10.00    --  111.50 125.00-150.00   60
 90  \w    101.00 178.00   0.50   10.00    --  111.50  61.00  30.00  154
 91  \w     96.00 149.00   0.50   10.00    --  111.50  77.00 -90.00  106
;
_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      0.0402475
_diffrn_orient_matrix_UB_12      0.0141363
_diffrn_orient_matrix_UB_13      -0.0809658
_diffrn_orient_matrix_UB_21      -0.1133431
_diffrn_orient_matrix_UB_22      -0.0898283
_diffrn_orient_matrix_UB_23      -0.0421658
_diffrn_orient_matrix_UB_31      -0.0430385
_diffrn_orient_matrix_UB_32      0.249274
_diffrn_orient_matrix_UB_33      -0.0105074
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16934
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.376
_diffrn_reflns_theta_min         4.866
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.361
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
        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,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.37
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0867P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                2287
_reflns_number_total             2329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04627k2.cif
_cod_data_source_block           Fe2+
_cod_depositor_comments
'Adding full bibliography for 7134921--7134926.cif.'
_cod_database_code               7134924
_shelx_estimated_absorpt_t_min   0.286
_shelx_estimated_absorpt_t_max   0.689
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.535
_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
 At 1.5 times of:
  All C(H,H,H) groups
        2.a Ternary CH refined with riding coordinates:
 C9(H9)
        2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
        2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C2(H2)
        2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              4907
_shelx_hkl_checksum              39838