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_7134923
_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         'C46 H56 Fe N2 O4'
_chemical_formula_sum            'C46 H56 Fe N2 O4'
_chemical_formula_weight         756.77
_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
_audit_creation_date             2024-01-04T17:42:06-00:00
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.6725(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6453(3)
_cell_length_b                   14.5148(2)
_cell_length_c                   31.1666(5)
_cell_measurement_reflns_used    44955
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      31.177
_cell_measurement_theta_min      2.073
_cell_volume                     8733.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.102a 64-bit (release 15-09-2023))'
_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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1
_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  32.00   0.50   10.00    --   13.07 -40.00 111.00  198
  2  \w     -6.00  93.00   0.50   10.00    --   13.07  40.00 -95.00  198
  3  \w    -64.00  35.00   0.50   10.00    --   13.07 -57.00 -30.00  198
  4  \w    -18.00  54.00   0.50   10.00    --   13.07 -99.00  60.00  144
  5  \w    -19.00  29.00   0.50   10.00    --  -13.38 -99.00  30.00   96
  6  \w    -19.00  29.00   0.50   10.00    --  -13.38 -99.00-120.00   96
  7  \w    -19.00  29.00   0.50   10.00    --  -13.38 -99.00   0.00   96
  8  \w    -18.00  54.00   0.50   10.00    --   13.07 -99.00-180.00  144
  9  \w    -18.00  54.00   0.50   10.00    --   13.07 -99.00 -90.00  144
 10  \w    -19.00  29.00   0.50   10.00    --  -13.38 -99.00  90.00   96
 11  \w    -90.00   8.00   0.50   10.00    --  -13.38 -57.00   0.00  196
 12  \w    -87.00 -42.00   0.50   10.00    --  -13.38-178.00 120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0315171
_diffrn_orient_matrix_UB_12      0.0247748
_diffrn_orient_matrix_UB_13      0.0056474
_diffrn_orient_matrix_UB_21      0.0022618
_diffrn_orient_matrix_UB_22      0.0033149
_diffrn_orient_matrix_UB_23      -0.0223999
_diffrn_orient_matrix_UB_31      -0.0187507
_diffrn_orient_matrix_UB_32      0.0419894
_diffrn_orient_matrix_UB_33      -0.001577
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            131363
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.077
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
        Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       needle
_exptl_crystal_F_000             3232
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 7785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1119
_refine_ls_number_reflns         26650
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0404
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+0.8084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.93
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                20256
_reflns_number_total             26650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04627k2.cif
_cod_data_source_block           Fe7
_cod_depositor_comments
'Adding full bibliography for 7134921--7134926.cif.'
_cod_original_cell_volume        8733.3(2)
_cod_database_code               7134923
_shelx_estimated_absorpt_t_min   0.802
_shelx_estimated_absorpt_t_max   0.971
_oxdiff_exptl_absorpt_empirical_details
;
        Empirical correction (ABSPACK) includes:
        - Absorption correction using spherical harmonics
        - Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.906
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
 At 1.5 times of:
  All C(H,H,H) groups
        2. Uiso/Uaniso restraints and constraints
        Uanis(C86) \\sim Ueq, Uanis(C88A) \\sim Ueq, Uanis(C88) \\sim Ueq, Uanis(C85A)
        \\sim Ueq, Uanis(C86A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
        atoms of 0.01
        Uanis(C92A) \\sim Ueq, Uanis(C92) \\sim Ueq, Uanis(C90A) \\sim Ueq, Uanis(C90)
        \\sim Ueq, Uanis(C91) \\sim Ueq, Uanis(C91A) \\sim Ueq, Uanis(C89) \\sim Ueq:
        with sigma of 0.01 and sigma for terminal atoms of 0.01
        Uanis(C63A) \\sim Ueq, Uanis(C65) \\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C65A)
        \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C64A) \\sim Ueq: with sigma of 0.01 and
        sigma for terminal atoms of 0.01
        3. Others
 Sof(C63A)=Sof(H63D)=Sof(H63E)=Sof(H63F)=Sof(C64A)=Sof(H64D)=Sof(H64E)=
 Sof(H64F)=Sof(C65A)=Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(1)
 Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(H63C)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=
 Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(1)
 Sof(H80A)=Sof(C81A)=Sof(H81A)=Sof(C82A)=Sof(H82A)=Sof(C83A)=Sof(H83A)=
 Sof(C84A)=Sof(H84A)=1-FVAR(2)
 Sof(C84)=Sof(H84)=Sof(C81)=Sof(H81)=Sof(H80)=Sof(C82)=Sof(H82)=Sof(C83)=
 Sof(H83)=FVAR(2)
 Sof(H72A)=Sof(C71A)=Sof(C85A)=Sof(C87A)=Sof(H87D)=Sof(H87E)=Sof(H87F)=
 Sof(C88A)=Sof(H88D)=Sof(H88E)=Sof(H88F)=Sof(C86A)=Sof(H86D)=Sof(H86E)=
 Sof(H86F)=1-FVAR(3)
 Sof(C71)=Sof(H72)=Sof(C85)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(H88C)=Sof(C87)=
 Sof(H87A)=Sof(H87B)=Sof(H87C)=Sof(C86)=Sof(H86A)=Sof(H86B)=Sof(H86C)=FVAR(3)
 Sof(C92A)=Sof(H92D)=Sof(H92E)=Sof(H92F)=Sof(C91A)=Sof(H91D)=Sof(H91E)=
 Sof(H91F)=Sof(C90A)=Sof(H90D)=Sof(H90E)=Sof(H90F)=1-FVAR(4)
 Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(H92C)=Sof(C90)=Sof(H90A)=Sof(H90B)=Sof(H90C)=
 Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(H91C)=FVAR(4)
 Fixed Y: Fe1(0.301101)
        4.a Ternary CH refined with riding coordinates:
 C32(H32), C9(H9), C55(H55), C78(H78)
        4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C77(H77A,H77B), C31(H31A,H31B), C54(H54A,H54B)
        4.c Me refined with riding coordinates:
 C90(H90A,H90B,H90C), C63(H63A,H63B,H63C), C65(H65A,H65B,H65C), C64(H64A,H64B,
 H64C), C63A(H63D,H63E,H63F), C64A(H64D,H64E,H64F), C65A(H65D,H65E,H65F)
        4.d Aromatic/amide H refined with riding coordinates:
 C26(H26), C3(H3), C11(H11), C5(H5), C28(H28), C49(H49), C38(H38), C34(H34),
 C36(H36), C35(H35), C74(H74), C15(H15), C37(H37), C13(H13), C51(H51), C61(H61),
  C59(H59), C12(H12), C14(H14), C57(H57), C60(H60), C84(H84), C72(H72A),
 C72(H72), C58(H58), C81(H81), C80(H80), C80(H80A), C82(H82), C83(H83),
 C81A(H81A), C82A(H82A), C83A(H83A), C84A(H84A)
        4.e Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C42(H42A,H42B,H42C), C67(H67A,H67B,H67C), C69(H69A,H69B,
 H69C), C41(H41A,H41B,H41C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C22(H22A,
 H22B,H22C), C23(H23A,H23B,H23C), C68(H68A,H68B,H68C), C17(H17A,H17B,H17C),
 C45(H45A,H45B,H45C), C21(H21A,H21B,H21C), C46(H46A,H46B,H46C), C44(H44A,H44B,
 H44C), C92(H92A,H92B,H92C), C91(H91A,H91B,H91C), C88(H88A,H88B,H88C), C87(H87A,
 H87B,H87C), C86(H86A,H86B,H86C), C87A(H87D,H87E,H87F), C88A(H88D,H88E,H88F),
 C86A(H86D,H86E,H86F), C92A(H92D,H92E,H92F), C91A(H91D,H91E,H91F), C90A(H90D,
 H90E,H90F)
;
_shelx_res_checksum              88556
_shelx_hkl_checksum              30173
_shelx_fab_checksum              91763