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_7134921
_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         'C19 H23 N O2'
_chemical_formula_sum            'C19 H23 N O2'
_chemical_formula_weight         297.38
_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   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-04
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-06-06 deposited with the CCDC.	2025-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.65189(5)
_cell_length_b                   12.52806(7)
_cell_length_c                   12.83597(7)
_cell_measurement_reflns_used    28860
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      80.7730
_cell_measurement_theta_min      4.6070
_cell_volume                     1552.119(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -121.00 -42.00   1.00    0.50    --  -50.90 -55.00 134.00   79
  2  \w     42.00 122.00   1.00    0.50    --   50.90  55.00 -82.00   80
  3  \w    -19.00  60.00   1.00    0.50    --   50.90 -55.00 134.00   79
  4  \w   -160.00 -81.00   1.00    1.80    --  -90.00 -55.00 134.00   79
  5  \w    -63.00 -19.00   1.00    1.80    --  -90.00  55.00 -82.00   44
  6  \w    103.00 178.00   1.00    1.80    --  111.50  55.00 -82.00   75
  7  \w    -26.00  20.00   1.00    0.50    --  -50.90  19.00  30.00   46
  8  \w    -60.00  20.00   1.00    0.50    --  -50.90  55.00 -82.00   80
  9  \w   -119.00 -73.00   1.00    0.50    --  -50.90-125.00 -90.00   46
 10  \w    -26.00  20.00   1.00    0.50    --  -50.90  19.00  60.00   46
 11  \w    -19.00  43.00   1.00    0.50    --   50.90 -38.00  30.00   62
 12  \w    -51.00 -19.00   1.00    1.80    --  -90.00  45.00  30.00   32
 13  \w    -71.00 -19.00   1.00    1.80    --  -90.00  61.00  90.00   52
 14  \w   -160.00 -84.00   1.00    1.80    --  -90.00 -45.00 150.00   76
 15  \w     41.00 105.00   1.00    1.80    --  111.50 -77.00 120.00   64
 16  \w     41.00  71.00   1.00    1.80    --  111.50 -61.00 120.00   30
 17  \w     43.00 112.00   1.00    1.80    --  111.50-125.00  30.00   69
 18  \w     41.00  71.00   1.00    1.80    --  111.50 -61.00  90.00   30
 19  \w    111.00 178.00   1.00    1.80    --  111.50  30.00 150.00   67
 20  \w     41.00  71.00   1.00    1.80    --  111.50 -61.00 -90.00   30
 21  \w     41.00 106.00   1.00    1.80    --  111.50 -94.00 -90.00   65
 22  \w    100.00 178.00   1.00    1.80    --  111.50  61.00 -60.00   78
 23  \w     41.00 106.00   1.00    1.80    --  111.50 -94.00  30.00   65
 24  \w    111.00 178.00   1.00    1.80    --  111.50  30.00-180.00   67
 25  \w     95.00 178.00   1.00    1.80    --  111.50 125.00-150.00   83
 26  \w     43.00 112.00   1.00    1.80    --  111.50-125.00   0.00   69
 27  \w    106.00 178.00   1.00    1.80    --  111.50  45.00   0.00   72
 28  \w     93.00 178.00   1.00    1.80    --  111.50  77.00 150.00   85
 29  \w     41.00  71.00   1.00    1.80    --  111.50 -61.00 -30.00   30
 30  \w    106.00 178.00   1.00    1.80    --  111.50  45.00-120.00   72
 31  \w    100.00 178.00   1.00    1.80    --  111.50  61.00   0.00   78
 32  \w    100.00 178.00   1.00    1.80    --  111.50  61.00  90.00   78
 33  \w    100.00 178.00   1.00    1.80    --  111.50  61.00 -30.00   78
 34  \w    111.00 178.00   1.00    1.80    --  111.50  30.00  60.00   67
 35  \w    100.00 178.00   1.00    1.80    --  111.50  61.00 150.00   78
 36  \w    100.00 178.00   1.00    1.80    --  111.50  61.00-180.00   78
 37  \w    111.00 178.00   1.00    1.80    --  111.50  30.00  90.00   67
 38  \w     95.00 178.00   1.00    1.80    --  111.50 125.00  60.00   83
 39  \w     46.00  72.00   1.00    1.80    --  111.50-125.00  60.00   26
 40  \w     74.00 100.00   1.00    1.80    --  111.50-125.00  60.00   26
 41  \w     69.00 104.00   1.00    1.80    --  111.50 -77.00  30.00   35
 42  \w    119.00 159.00   1.00    1.80    --  111.50 125.00  90.00   40
 43  \w     64.00 107.00   1.00    1.80    --  111.50-125.00-150.00   43
 44  \w    114.00 145.00   1.00    1.80    --  111.50  45.00-150.00   31
 45  \w     44.00  69.00   1.00    1.80    --  111.50 -61.00-150.00   25
 46  \w    143.00 177.00   1.00    1.80    --  111.50  15.00 -60.00   34
 47  \w     43.00  69.00   1.00    1.80    --  111.50 -61.00  30.00   26
 48  \w     43.00  86.00   1.00    1.80    --  111.50 -77.00 -90.00   43
 49  \w    128.00 168.00   1.00    1.80    --  111.50  15.00 120.00   40
 50  \w     47.00  74.00   1.00    1.80    --  111.50-125.00  90.00   27
 51  \w    126.00 177.00   1.00    1.80    --  111.50  45.00 120.00   51
 52  \w    114.00 139.00   1.00    1.80    --  111.50  45.00 150.00   25
 53  \w    113.00 147.00   1.00    1.80    --  111.50  15.00   0.00   34
;
_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      -0.0073471000
_diffrn_orient_matrix_UB_12      0.0989049000
_diffrn_orient_matrix_UB_13      -0.0711284000
_diffrn_orient_matrix_UB_21      0.1504237000
_diffrn_orient_matrix_UB_22      -0.0199399000
_diffrn_orient_matrix_UB_23      -0.0351562000
_diffrn_orient_matrix_UB_31      -0.0529067000
_diffrn_orient_matrix_UB_32      -0.0702405000
_diffrn_orient_matrix_UB_33      -0.0900803000
_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  0.0184
_diffrn_reflns_av_unetI/netI     0.0077
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32973
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.459
_diffrn_reflns_theta_min         4.933
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.1725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3141
_reflns_number_total             3170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04627k2.cif
_cod_data_source_block           L4
_cod_depositor_comments
'Adding full bibliography for 7134921--7134926.cif.'
_cod_original_cell_volume        1552.120(14)
_cod_database_code               7134921
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C76  H92  N4  O8  '
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
;
_shelx_res_checksum              84341
_shelx_hkl_checksum              43346
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.866