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_7134925
_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         'C32 H24 Fe N2 O4'
_chemical_formula_sum            'C32 H24 Fe N2 O4'
_chemical_formula_weight         556.38
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-21T17:32:59-00:00
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.3034(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.66217(17)
_cell_length_b                   5.02730(7)
_cell_length_c                   16.98028(18)
_cell_measurement_reflns_used    12468
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      78.549
_cell_measurement_theta_min      3.851
_cell_volume                     1248.11(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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_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   -119.00 -94.00   0.50    2.00    --  -50.24-130.00 -13.00   50
  2  \w    -88.00 -16.00   0.50    2.00    --  -50.24 130.00  58.00  144
  3  \w    -96.00 -43.00   0.50    2.00    --  -50.24 139.00-127.00  106
  4  \w   -117.00 -92.00   0.50    2.00    --  -50.24-139.00 172.00   50
  5  \w     48.00  73.00   0.50    2.00    --   50.24-139.00 172.00   50
  6  \w     42.00  67.00   0.50    2.00    --   50.24-130.00 -13.00   50
  7  \w    -82.00 -57.00   0.50    6.00    --  -90.00 139.00-127.00   50
  8  \w    -79.00 -54.00   0.50    6.00    --  -90.00 130.00  58.00   50
  9  \w   -135.00-109.00   0.50    6.00    --  -90.00-139.00 172.00   52
 10  \w   -139.00-114.00   0.50    6.00    --  -90.00-130.00 -13.00   50
 11  \w     58.00  95.00   0.50    6.00    --  111.50-130.00 -13.00   74
 12  \w    117.00 143.00   0.50    6.00    --  111.50 139.00-127.00   52
 13  \w     97.00 122.00   0.50    6.00    --  111.50-139.00 172.00   50
 14  \w     93.00 118.00   0.50    6.00    --  111.50 130.00  58.00   50
 15  \w    -63.00 -35.00   0.50    2.00    --    6.00 168.00 -89.82   56
 16  \w    -52.00 -27.00   0.50    2.00    --    6.00 150.00-163.04   50
 17  \w    -54.00 -28.00   0.50    2.00    --    6.00 153.00 100.39   52
 18  \w      1.00  27.00   0.50    2.00    --   26.00  96.00  -4.13   52
 19  \w    -61.00  -9.00   0.50    2.00    --  -30.00 106.00 122.61  104
 20  \w   -123.00 -62.00   0.50    2.00    --  -50.24 -24.00  68.13  122
 21  \w   -117.00 -86.00   0.50    2.00    --  -50.24 -19.00  90.00   62
 22  \w    -81.00 -46.00   0.50    2.00    --  -50.24 -19.00  90.00   70
 23  \w     95.00 121.00   0.50    2.00    --   50.24  77.00-150.00   52
 24  \w     97.00 122.00   0.50    2.00    --   50.24  77.00 -60.00   50
 25  \w     46.00  74.00   0.50    2.00    --   50.24  38.00 120.00   56
 26  \w     31.00  56.00   0.50    2.00    --   50.24  77.00-180.00   50
 27  \w    105.00 130.00   0.50    2.00    --   58.00  76.00  36.01   50
 28  \w     43.00  69.00   0.50    2.00    --   62.00  76.00 153.01   52
 29  \w     45.00  70.00   0.50    2.00    --   62.00  74.00 125.14   50
 30  \w    -82.00 -56.00   0.50    2.00    --  -70.00 -66.00  38.97   52
 31  \w    -82.00 -56.00   0.50    2.00    --  -70.00 -66.00  20.37   52
 32  \w    -82.00 -56.00   0.50    2.00    --  -70.00 -66.00  11.95   52
 33  \w    -83.00 -57.00   0.50    2.00    --  -74.00 -71.00  18.77   52
 34  \w    -84.00 -58.00   0.50    2.00    --  -74.00 -67.00 -20.35   52
 35  \w    -85.00 -59.00   0.50    2.00    --  -74.00 -66.00  -3.43   52
 36  \w    -87.00 -61.00   0.50    2.00    --  -74.00 -65.00  19.29   52
 37  \w    -86.00 -60.00   0.50    2.00    --  -78.00 -74.00 -96.17   52
 38  \w    -88.00 -61.00   0.50    2.00    --  -78.00 -71.00   5.63   54
 39  \w    -90.00 -64.00   0.50    2.00    --  -78.00 -65.00  53.12   52
 40  \w    -89.00 -63.00   0.50    2.00    --  -78.00 -65.00  35.52   52
 41  \w    -90.00 -64.00   0.50    2.00    --  -78.00 -65.00   5.15   52
 42  \w    -88.00 -63.00   0.50    2.00    --  -78.00 -65.00  63.52   50
 43  \w    -86.00 -60.00   0.50    2.00    --  -78.00 -72.00 162.23   52
 44  \w    -94.00 -68.00   0.50    6.00    --  -82.00 -64.00  50.14   52
 45  \w    -95.00 -68.00   0.50    6.00    --  -82.00 -65.00  26.36   54
 46  \w    -95.00 -68.00   0.50    6.00    --  -82.00 -65.00  19.26   54
 47  \w    -93.00 -67.00   0.50    6.00    --  -82.00 -66.00  -9.66   52
 48  \w    -93.00 -67.00   0.50    6.00    --  -86.00 -75.00 178.47   52
 49  \w   -130.00-103.00   0.50    6.00    --  -86.00 -76.00-153.71   54
 50  \w    -93.00 -68.00   0.50    6.00    --  -86.00 -74.00  65.85   50
 51  \w   -145.00-119.00   0.50    6.00    --  -90.00 -75.00   4.18   52
 52  \w    -97.00 -71.00   0.50    6.00    --  -90.00 -77.00  60.00   52
 53  \w    -99.00 -73.00   0.50    6.00    --  -90.00 -74.00-106.14   52
 54  \w   -109.00 -72.00   0.50    6.00    --  -90.00 -73.00  10.29   74
 55  \w   -100.00 -74.00   0.50    6.00    --  -90.00 -72.00  94.40   52
 56  \w   -100.00 -74.00   0.50    6.00    --  -90.00 -71.00  45.69   52
 57  \w   -102.00 -71.00   0.50    6.00    --  -90.00 -75.00-166.75   62
 58  \w   -100.00 -73.00   0.50    6.00    --  -90.00 -74.00  23.34   54
 59  \w    -99.00 -73.00   0.50    6.00    --  -90.00 -71.00  85.40   52
 60  \w   -100.00 -73.00   0.50    6.00    --  -90.00 -77.00  90.00   54
 61  \w   -100.00 -74.00   0.50    6.00    --  -90.00 -71.00  68.34   52
 62  \w     83.00 123.00   0.50    6.00    --   98.00  67.00  94.44   80
 63  \w     37.00 110.00   0.50    6.00    --  102.00-119.00 -12.44  146
 64  \w     95.00 138.00   0.50    6.00    --  111.50  77.00  60.00   86
 65  \w     41.00  85.00   0.50    6.00    --  111.50 -77.00 150.00   88
 66  \w     42.00  81.00   0.50    6.00    --  111.50 -77.00 -30.00   78
 67  \w    108.00 152.00   0.50    6.00    --  111.50  15.00 -90.00   88
 68  \w     43.00  83.00   0.50    6.00    --  111.50 -77.00 -90.00   80
 69  \w     77.00 102.00   0.50    6.00    --  111.50 -94.00  60.00   50
 70  \w     48.00  73.00   0.50    6.00    --  111.50-125.00  60.00   50
 71  \w     75.00 101.00   0.50    6.00    --  111.50   0.00   0.00   52
 72  \w    101.00 126.00   0.50    6.00    --  111.50  61.00  60.00   50
 73  \w     99.00 126.00   0.50    6.00    --  111.50  61.00 -30.00   54
 74  \w     99.00 176.00   0.50    6.00    --  111.50  61.00 -90.00  154
 75  \w     45.00 110.00   0.50    6.00    --  111.50-125.00  90.00  130
 76  \w     92.00 177.00   0.50    6.00    --  111.50  77.00-120.00  170
 77  \w     80.00 106.00   0.50    6.00    --  111.50 -94.00   0.00   52
 78  \w    138.00 174.00   0.50    6.00    --  111.50  77.00 -30.00   72
 79  \w    104.00 139.00   0.50    6.00    --  111.50  45.00  30.00   70
 80  \w     92.00 133.00   0.50    6.00    --  111.50  77.00 -30.00   82
 81  \w    150.00 178.00   0.50    6.00    --  111.50  77.00-180.00   56
 82  \w     99.00 178.00   0.50    6.00    --  111.50  61.00 -60.00  158
 83  \w     98.00 143.00   0.50    6.00    --  111.50  77.00-180.00   90
 84  \w     42.00  79.00   0.50    6.00    --  111.50 -77.00   0.00   74
 85  \w    153.00 178.00   0.50    6.00    --  111.50  77.00  90.00   50
 86  \w     46.00  96.00   0.50    6.00    --  111.50 -77.00  60.00  100
 87  \w    102.00 132.00   0.50    6.00    --  111.50  77.00  90.00   60
 88  \w    144.00 178.00   0.50    6.00    --  111.50  61.00   0.00   68
 89  \w     95.00 148.00   0.50    6.00    --  111.50  77.00 -60.00  106
 90  \w     58.00  84.00   0.50    6.00    --  111.50 -77.00-120.00   52
 91  \w    134.00 169.00   0.50    6.00    --  111.50  61.00-180.00   70
 92  \w     45.00  83.00   0.50    6.00    --  111.50 -77.00-180.00   76
 93  \w     93.00 119.00   0.50    6.00    --  111.50  77.00-150.00   52
 94  \w     98.00 130.00   0.50    6.00    --  111.50  61.00-180.00   64
 95  \w     94.00 176.00   0.50    6.00    --  111.50  77.00 120.00  164
 96  \w    104.00 153.00   0.50    6.00    --  111.50  61.00 150.00   98
 97  \w     92.00 166.00   0.50    6.00    --  111.50  77.00 150.00  148
 98  \w    146.00 177.00   0.50    6.00    --  111.50  15.00   0.00   62
 99  \w    128.00 166.00   0.50    6.00    --  111.50  15.00 120.00   76
100  \w     98.00 127.00   0.50    6.00    --  111.50  61.00   0.00   58
101  \w    108.00 134.00   0.50    6.00    --  111.50  15.00   0.00   52
102  \w     98.00 165.00   0.50    6.00    --  111.50  61.00 120.00  134
103  \w     42.00 103.00   0.50    6.00    --  111.50 -77.00-150.00  122
104  \w     86.00 111.00   0.50    6.00    --  111.50-125.00 120.00   50
105  \w     98.00 177.00   0.50    6.00    --  111.50  61.00-150.00  158
106  \w     44.00  70.00   0.50    6.00    --  111.50-125.00 120.00   52
107  \w    105.00 176.00   0.50    6.00    --  111.50 125.00   0.00  142
108  \w     41.00  95.00   0.50    6.00    --  111.50 -77.00  90.00  108
109  \w    119.00 145.00   0.50    6.00    --  111.50 125.00 -60.00   52
110  \w    107.00 136.00   0.50    6.00    --  111.50  61.00-120.00   58
111  \w     99.00 141.00   0.50    6.00    --  111.50  61.00  30.00   84
112  \w    152.00 178.00   0.50    6.00    --  111.50  30.00  60.00   52
113  \w    111.00 138.00   0.50    6.00    --  111.50  30.00 -60.00   54
114  \w     86.00 111.00   0.50    6.00    --  111.50-125.00  60.00   50
115  \w    144.00 177.00   0.50    6.00    --  111.50  77.00  60.00   66
118  \w     44.00  71.00   0.50    6.00    --  111.50 -61.00  30.00   54
116  \w    131.00 160.00   0.50    6.00    --  111.50  61.00 -30.00   58
117  \w     94.00 178.00   0.50    6.00    --  111.50  77.00  30.00  168
;
_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      -0.0472267
_diffrn_orient_matrix_UB_12      -0.0048147
_diffrn_orient_matrix_UB_13      -0.0841588
_diffrn_orient_matrix_UB_21      0.0940593
_diffrn_orient_matrix_UB_22      -0.0182096
_diffrn_orient_matrix_UB_23      -0.03441
_diffrn_orient_matrix_UB_31      -0.0048633
_diffrn_orient_matrix_UB_32      -0.3058802
_diffrn_orient_matrix_UB_33      0.0033638
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17822
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.472
_diffrn_reflns_theta_min         3.843
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.201
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.35
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.43.95a (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    1.48
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0533P)^2^+0.4884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2327
_reflns_number_total             2388
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
        Component 2 rotated by -169.2782\%
        around [0.01 1.00 -0.00] (reciprocal) or [0.00 1.00 -0.00] (direct)
        Component 3 rotated by -171.1389\%
        around [-0.00 1.00 -0.03] (reciprocal) or [-0.00 1.00 -0.00] (direct)
;
_cod_data_source_file            d5cc04627k2.cif
_cod_data_source_block           Fe5
_cod_depositor_comments
'Adding full bibliography for 7134921--7134926.cif.'
_cod_database_code               7134925
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.863
_oxdiff_exptl_absorpt_empirical_full_min 0.306
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              47212
_shelx_hkl_checksum              21660