Enantioselective C-H Bond Oxidation using Bio-Inspired Chiral Fe-TAML Catalyst
Dey Biswas, Doyel; Das, Soumadip; Pal, Debraj; Sen Gupta, Sayam; Chemical Communications  (2026) –; doi:10.1039/D5CC06607G

data_7135322
_publ_section_title
;
 Enantioselective C-H Bond Oxidation using Bio-Inspired Chiral Fe-TAML
 Catalyst
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06607G
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H23 Cl Fe N5 O4, 2(C8 H20 N)'
_chemical_formula_sum            'C43 H63 Cl Fe N7 O4'
_chemical_formula_weight         833.30
_chemical_name_common            (R,R)-1
_chemical_name_systematic        (R,R)-[(Ph,Me)-FebTAML][Cl]
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-03-26
_audit_creation_method
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_audit_update_record
;
2025-09-25 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                88.500(2)
_cell_angle_beta                 81.057(2)
_cell_angle_gamma                88.7800(10)
_cell_formula_units_Z            2
_cell_length_a                   9.0356(2)
_cell_length_b                   13.1688(2)
_cell_length_c                   17.9549(3)
_cell_measurement_reflns_used    25744
_cell_measurement_temperature    99.98(18)
_cell_measurement_theta_max      67.9850
_cell_measurement_theta_min      2.4880
_cell_volume                     2109.40(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_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   -102.00 -23.00   0.50    0.32    --  -40.58 146.00 -79.00  158
  2  \w    -87.00 -12.00   0.50    0.32    --  -40.58 125.00 114.00  150
  3  \w   -109.00 -58.00   0.50    0.32    --  -40.58-146.00-129.00  102
  4  \w     34.00  89.00   0.50    0.32    --   40.58-125.00  36.00  110
  5  \w     45.00 105.00   0.50    0.32    --   40.58-146.00-129.00  120
  6  \w   -147.00 -73.00   0.50    1.29    --  -82.50-125.00  36.00  148
  7  \w   -151.00 -58.00   0.50    1.29    --  -82.50-146.00-129.00  186
  8  \w    -87.00 -18.00   0.50    1.29    --  -82.50 125.00 114.00  138
  9  \w     80.00 165.00   0.50    1.29    --   96.35 146.00 -79.00  170
 10  \w     94.00 161.00   0.50    1.29    --   96.35 125.00 114.00  134
 11  \w     34.00 112.00   0.50    1.29    --   96.35-125.00  36.00  156
 12  \w     45.00 128.00   0.50    1.29    --   96.35-146.00-129.00  166
 13  \w    -31.00  30.00   0.50    0.32    --  -40.58  25.00-150.00  122
 14  \w   -107.00 -21.00   0.50    0.32    --  -40.58 -50.00-150.00  172
 15  \w   -111.00 -26.00   0.50    0.32    --  -40.58 -25.00  90.00  170
 16  \w   -107.00 -25.00   0.50    0.32    --  -40.58 -38.00-120.00  164
 17  \w    -67.00  28.00   0.50    0.32    --  -40.58  77.00  60.00  190
 18  \w    -26.00  57.00   0.50    0.32    --   40.58 -50.00 150.00  166
 19  \w    -25.00  43.00   0.50    0.32    --   40.58 -38.00  30.00  136
 20  \w     25.00 107.00   0.50    0.32    --   40.58  38.00  90.00  164
 21  \w      8.00  42.00   0.50    0.32    --   40.58  92.00 -89.22   68
 22  \w    -29.00  31.00   0.50    0.32    --   40.58 -25.00 -90.00  120
 23  \w     10.00  43.00   0.50    0.32    --   40.58  88.00-166.75   66
 24  \w   -150.00 -69.00   0.50    1.29    --  -82.50 -33.00-150.00  162
 25  \w    -47.00 -15.00   0.50    1.29    --  -82.50  42.00-120.00   64
 26  \w    -47.00 -15.00   0.50    1.29    --  -82.50  42.00   0.00   64
 27  \w    -47.00 -15.00   0.50    1.29    --  -82.50  42.00-180.00   64
 28  \w    -47.00 -15.00   0.50    1.29    --  -82.50  42.00 -30.00   64
 29  \w   -151.00 -61.00   0.50    1.29    --  -82.50 -59.00 -90.00  180
 30  \w   -102.00 -23.00   0.50    1.29    --  -82.50 146.00 -79.00  158
 31  \w    -57.00 -16.00   0.50    1.29    --  -82.50  50.00 150.00   82
 32  \w   -150.00 -69.00   0.50    1.29    --  -82.50 -33.00 -30.00  162
 33  \w     83.00 164.00   0.50    1.29    --   96.35  33.00  90.00  162
 34  \w     23.00 106.00   0.50    1.29    --   96.35 -96.00 150.00  166
 35  \w     83.00 164.00   0.50    1.29    --   96.35  33.00 120.00  162
 36  \w     23.00 106.00   0.50    1.29    --   96.35 -96.00  30.00  166
 37  \w     33.00 110.00   0.50    1.29    --   96.35-117.00 -30.00  154
 38  \w     33.00 110.00   0.50    1.29    --   96.35-117.00  90.00  154
 39  \w     44.00 127.00   0.50    1.29    --   96.35-145.00 -30.00  166
 40  \w     72.00 164.00   0.50    1.29    --   96.35  68.00  30.00  184
 41  \w     30.00  57.00   0.50    1.29    --   96.35 -50.00 150.00   54
 42  \w     99.00 160.00   0.50    1.29    --   96.35 117.00 150.00  122
 43  \w     83.00 164.00   0.50    1.29    --   96.35  33.00-180.00  162
 44  \w     28.00  68.00   0.50    1.29    --   96.35 -59.00 -90.00   80
 45  \w    105.00 170.00   0.50    1.29    --   96.35  96.00   0.00  130
 46  \w     44.00 127.00   0.50    1.29    --   96.35-145.00  30.00  166
 47  \w     29.00  83.00   0.50    1.29    --   96.35 -68.00 150.00  108
 48  \w     83.00 164.00   0.50    1.29    --   96.35  33.00-120.00  162
 49  \w     28.00  68.00   0.50    1.29    --   96.35 -59.00  90.00   80
 50  \w     28.00 105.00   0.50    1.29    --   96.35 -77.00-150.00  154
 51  \w     23.00 106.00   0.50    1.29    --   96.35 -96.00-150.00  166
 52  \w     28.00  68.00   0.50    1.29    --   96.35 -59.00  60.00   80
 53  \w     33.00 110.00   0.50    1.29    --   96.35-117.00  30.00  154
 54  \w     28.00 105.00   0.50    1.29    --   96.35 -77.00  60.00  154
 55  \w     83.00 164.00   0.50    1.29    --   96.35  33.00 -30.00  162
 56  \w     33.00 110.00   0.50    1.29    --   96.35-117.00 120.00  154
 57  \w     29.00  83.00   0.50    1.29    --   96.35 -68.00-120.00  108
 58  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00 -60.00  190
 59  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00  30.00  190
 60  \w    -78.00   4.00   0.50    0.32    --  -40.58 104.00-150.00  164
 61  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00 120.00  190
 62  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00 -30.00  190
 63  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00  60.00  190
 64  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00 -90.00  190
 65  \w   -109.00 -14.00   0.50    0.32    --  -40.58 -77.00-180.00  190
 66  \w     10.00  43.00   0.50    0.32    --   40.58  87.00 -97.24   66
 67  \w     14.00 109.00   0.50    0.32    --   40.58  77.00   0.00  190
 68  \w    -29.00  31.00   0.50    0.32    --   40.58 -25.00-180.00  120
 69  \w     12.00  43.00   0.50    0.32    --   40.58  83.00-155.58   62
 70  \w     11.00  43.00   0.50    0.32    --   40.58  86.00 159.19   64
 71  \w     25.00 107.00   0.50    0.32    --   40.58  38.00-120.00  164
 72  \w     18.00 108.00   0.50    0.32    --   40.58  64.00 120.00  180
 73  \w      9.00  42.00   0.50    0.32    --   40.58  91.00 124.55   66
 74  \w     10.00  43.00   0.50    0.32    --   40.58  87.00  45.43   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1268883000
_diffrn_orient_matrix_UB_12      -0.0766859000
_diffrn_orient_matrix_UB_13      0.0213023000
_diffrn_orient_matrix_UB_21      -0.0045224000
_diffrn_orient_matrix_UB_22      0.0232349000
_diffrn_orient_matrix_UB_23      0.0839790000
_diffrn_orient_matrix_UB_31      -0.1169533000
_diffrn_orient_matrix_UB_32      0.0853148000
_diffrn_orient_matrix_UB_33      -0.0064839000
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38828
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         2.492
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.847
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            deep
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    not
_exptl_crystal_description       block
_exptl_crystal_F_000             890
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.912
_exptl_transmission_factor_min   0.725
_refine_diff_density_max         1.701
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details
;
 Flack x determined using 3851 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1031
_refine_ls_number_reflns         12102
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0622
_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^)+(0.1224P)^2^+8.0509P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.580
_reflns_Friedel_fraction_full    0.581
_reflns_Friedel_fraction_max     0.575
_reflns_number_gt                11549
_reflns_number_total             12102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06607g2.cif
_cod_data_source_block           ddb_cat2_reduced
_cod_database_code               7135322
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'H N O C Fe Cl'
_chemical_oxdiff_usercomment     '100 K'
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.365
_diffrn_oxdiff_ac3_digest_hkl    418fd467e7a25680b57a73ba6d2b6399f1f0c9
_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 Secondary CH2 refined with riding coordinates:
 C79(H79A,H79B), C87(H87A,H87B), C81(H81A,H81B), C96(H96A,H96B), C93(H93A,
 H93B), C83(H83A,H83B), C109(H10K,H10L), C84(H84A,H84B), C102(H10D,H10E),
 C100(H10F,H10G), C107(H10M,H10N), C91(H91A,H91B), C98(H98A,H98B), C89(H89A,
 H89B), C105(H10R,H10S), C111(H11M,H11N)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C4(H4), C24(H24), C6(H6), C51(H51), C5(H5), C55(H55), C28(H28),
 C25(H25), C33(H33), C13(H13), C40(H40), C27(H27), C32(H32), C26(H26), C52(H52),
  C53(H53), C7(H7), C42(H42), C14(H14), C41(H41), C54(H54), C17(H17), C44(H44),
 C15(H15), C43(H43), C34(H34), C16(H16)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C46(H46A,H46B,H46C), C22(H22A,H22B,H22C), C82(H82A,H82B,
 H82C), C97(H97A,H97B,H97C), C110(H11G,H11H,H11I), C103(H10A,H10B,H10C),
 C19(H19A,H19B,H19C), C80(H80A,H80B,H80C), C49(H49A,H49B,H49C), C90(H90A,H90B,
 H90C), C101(H10H,H10I,H10J), C108(H10O,H10P,H10Q), C99(H99A,H99B,H99C),
 C85(H85A,H85B,H85C), C88(H88A,H88B,H88C), C94(H94A,H94B,H94C), C113(H11D,H11E,
 H11F), C38(H38A,H38B,H38C), C112(H11J,H11K,H11L), C92(H92A,H92B,H92C),
 C106(H10T,H10U,H10V)
;
_shelx_res_checksum              32614
_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 2.061
_oxdiff_exptl_absorpt_empirical_full_min 0.625