Catalytic and stoichiometric flavanone oxidation mediated by nonheme oxoiron(iv) complexes as flavone synthase mimics: kinetic, mechanistic and computational studies.
Turcas, Ramona; Kripli, Balázs; Attia, Amr A. A.; Lakk-Bogáth, Dóra; Speier, Gábor; Giorgi, Michel; Silaghi-Dumitrescu, Radu; Kaizer, József; Dalton transactions (Cambridge, England : 2003) 47 (2018) 14416–14420; doi:10.1039/c8dt03519a

data_7047538
_publ_section_title
;
 Catalytic and stoichiometric flavanone oxidation mediated by nonheme
 oxoiron(iv) complexes as flavone synthase mimics: kinetic, mechanistic
 and computational studies.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14416
_journal_page_last               14420
_journal_paper_doi               10.1039/c8dt03519a
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety
'C32 H27 Cl Fe N5, C4 H8 O2, Cl O4, 0.5(C3 H5 O2), 0.5(C3 H6 O)'
_chemical_formula_sum            'C39 H40.5 Cl2 Fe N5 O7.5'
_chemical_formula_weight         826.01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-05-03 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                68.454(3)
_cell_angle_beta                 75.982(2)
_cell_angle_gamma                61.907(3)
_cell_formula_units_Z            2
_cell_length_a                   12.3536(3)
_cell_length_b                   12.7733(4)
_cell_length_c                   15.3745(3)
_cell_measurement_reflns_used    13091
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      70.0530
_cell_measurement_theta_min      4.0440
_cell_volume                     1983.55(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega    6.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   84.0000  105.3144 26

  2 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000   86.0102 25

  3 omega   33.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   77.8753 25

  4 omega   44.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   77.0000   80.0050 33

  5 omega   67.00  164.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000   30.0000 97

  6 omega  135.00  173.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  111.0000   30.0000 38

  7 omega  108.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   27.7166 43

  8 omega   79.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  157.2452 45

  9 omega   68.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000  150.0000 103

 10 omega   67.00  171.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000  120.0000 104

 11 omega   67.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000   60.0000 83

 12 omega   67.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000  -90.0000 111

 13 omega  109.00  152.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000 -173.7609 43

 14 omega   67.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000 -150.0000 105

 15 omega   67.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000  -60.0000 91

 16 omega   67.00  168.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000  -30.0000 101

 17 omega   67.00  156.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000    0.0000 89

 18 omega   67.00  169.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000 -180.0000 102

 19 omega   67.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000 -120.0000 77

 20 omega   67.00  167.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393   77.0000   90.0000 100

 21 omega   53.00  123.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -61.0000  120.0000 70

 22 omega   44.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5600 -125.0000  177.0000 52

 23 omega   25.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -94.0000  120.0000 83

 24 omega   32.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000  -30.0000 84

 25 omega   86.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393 -111.0000 -150.0000 26

 26 omega   41.00  122.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      103.0393  -77.0000  -30.0000 81

 27 omega   24.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   75.0000   -5.5871 27

 28 omega   32.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   27.7166 74

 29 omega   36.00   75.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -72.4189 39

 30 omega   28.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000   12.2652 27

 31 omega   17.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000   40.9606 29

 32 omega   10.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   85.0000  -37.0867 25

 33 omega   29.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000 -101.8779 27

 34 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   81.0000 -113.7159 25

 35 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000 -168.6355 25

 36 omega   36.00   80.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000 -173.7609 44

 37 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000 -127.6796 25

 38 omega   -3.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   95.0000   13.7704 25

 39 omega   20.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   79.0000  157.8903 25

 40 omega   28.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  157.2452 28

 41 omega  -86.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600   19.0000 -150.0000 133

 42 omega -116.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600  -57.0000   90.0000 110

 43 omega -116.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600  -38.0000 -180.0000 110

 44 omega -121.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5600  178.0000 -150.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0917000000
_diffrn_orient_matrix_UB_12      0.0187753000
_diffrn_orient_matrix_UB_13      0.0869357000
_diffrn_orient_matrix_UB_21      0.0992340000
_diffrn_orient_matrix_UB_22      -0.1088911000
_diffrn_orient_matrix_UB_23      0.0637669000
_diffrn_orient_matrix_UB_31      0.0432448000
_diffrn_orient_matrix_UB_32      0.0909602000
_diffrn_orient_matrix_UB_33      0.0080716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29771
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.315
_diffrn_reflns_theta_min         4.071
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       plate
_exptl_crystal_F_000             859
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         7432
_refine_ls_number_restraints     35
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0556
_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^)+(0.1067P)^2^+1.2469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1656
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6612
_reflns_number_total             7432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt03519a2.cif
_cod_data_source_block           bob32
_cod_depositor_comments          'Adding full bibliography for 7047538.cif.'
_cod_original_cell_volume        1983.54(12)
_cod_original_formula_sum        'C39 H40.50 Cl2 Fe N5 O7.50'
_cod_database_code               7047538
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c18 h18 fe1 n6 o10 s2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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. Shared sites
{O10, C46}
3. Restrained distances
 C39-O7
 1.45 with sigma of 0.02
4. Rigid bond restraints
 O5, O6, C33, C34, C35, C36
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O7, O8, C37, C38, C39, C40
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O11, C44, C45, C46
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O9, O10, C41, C42, C43
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(O10) = Uanis(C46)
6. Others
 Fixed Sof: O7(0.5) O8(0.5) C37(0.5) H37A(0.5) H37B(0.5) H37C(0.5) C38(0.5)
 H38A(0.5) H38B(0.5) C39(0.5) C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5) O5(0.5)
 O6(0.5) C33(0.5) H33A(0.5) H33B(0.5) H33C(0.5) C34(0.5) H34A(0.5) H34B(0.5)
 C35(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) O9(0.5) O10(0.5) C41(0.5)
 H41A(0.5) H41B(0.5) H41C(0.5) C42(0.5) H42A(0.5) H42B(0.5) C43(0.5) O11(0.5)
 C44(0.5) H44A(0.5) H44B(0.5) H44C(0.5) C45(0.5) C46(0.5) H46A(0.5) H46B(0.5)
 H46C(0.5)
7.a Ternary CH refined with riding coordinates:
 C1(H1)
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C13(H13A,H13B), C23(H23A,H23B), C38(H38A,H38B), C34(H34A,H34B),
 C42(H42A,H42B)
7.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21), C25(H25), C26(H26),
  C28(H28), C29(H29), C30(H30), C31(H31)
7.d Idealised Me refined with riding coordinates:
 C37(H37A,H37B,H37C), C40(H40A,H40B,H40C), C33(H33A,H33B,H33C), C36(H36A,H36B,
 H36C), C41(H41A,H41B,H41C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C)
;
_olex2_submission_special_instructions 'No special instructions were received'