Mechanistic elucidation of C-H oxidation by electron rich non-heme iron(IV)-oxo at room temperature
Sujoy Rana; Aniruddha Dey; Debabrata Maiti; Chem.Commun. 51 (2015) 14469–; doi:10.1039/C5cc04803F

data_7117800
_publ_section_title
;
 Mechanistic elucidation of C-H oxidation by electron rich non-heme
 iron(IV)-oxo at room temperature
;
_journal_name_full               Chem.Commun.
_journal_page_first              14469
_journal_paper_doi               10.1039/C5cc04803F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety
'2(C31 H36 Fe N6 O2), 4(C F3 O3 S), 4(C2 H3 N), N, C'
_chemical_formula_sum            'C75 H84 F12 Fe2 N17 O16 S4'
_chemical_formula_weight         1947.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
2015-03-03 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.910(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.179(9)
_cell_length_b                   15.362(8)
_cell_length_c                   17.899(10)
_cell_measurement_reflns_used    6820
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.9
_cell_measurement_theta_min      3.1
_cell_volume                     4448(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
scan:
    Number of images: 326
               Slice: -110.0000 - 53.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 36.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 116
               Slice: -71.0000 - -13.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -108.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 60
               Slice: -64.0000 - -34.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -36.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 270
               Slice: -110.0000 - 25.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -180.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 231
               Slice: -46.5000 - 69.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -36.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -108.0000
                 XTD: 45.0509
              2theta: -19.9783
scan:
    Number of images: 117
               Slice: -46.5000 - 12.0000
         Image width: 0.5000
            Exp time: 12.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -108.0000
                 XTD: 45.0509
              2theta: -19.9783
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      -0.027847
_diffrn_orient_matrix_UB_12      0.052348
_diffrn_orient_matrix_UB_13      0.017475
_diffrn_orient_matrix_UB_21      0.056192
_diffrn_orient_matrix_UB_22      0.032156
_diffrn_orient_matrix_UB_23      -0.006782
_diffrn_orient_matrix_UB_31      -0.013131
_diffrn_orient_matrix_UB_32      0.011763
_diffrn_orient_matrix_UB_33      -0.053022
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1288
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            46793
_diffrn_reflns_theta_full        29.9492
_diffrn_reflns_theta_max         29.95
_diffrn_reflns_theta_min         3.05
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.517
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       Prism
_exptl_crystal_F_000             2010.0
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         1.0038
_refine_diff_density_min         -0.9089
_refine_diff_density_rms         0.2287
_refine_ls_d_res_high            0.9507
_refine_ls_d_res_low             6.6778
_refine_ls_goodness_of_fit_ref   1.0351
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    64
_refine_ls_number_parameters     585
_refine_ls_number_reflns         5387
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.0193
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.1119
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+71.4366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2804
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -11
_reflns_number_gt                5196
_reflns_number_total             12910
_reflns_shell_number_unique_all  5641
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5cc04803f2.cif
_cod_data_source_block           SHELXL
_cod_database_code               7117800
_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(C23) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C48) \\sim Ueq,
Uanis(C1) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C39) \\sim Ueq, Uanis(C31)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(N10) \\sim Ueq,
Uanis(C35) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(N14) \\sim Ueq,
Uanis(C32) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(N3A)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3. Others
 Fixed Sof: C11(0.5) C7(0.5) N1(0.5) C7(0.5)
4.a Ternary CH refined with riding coordinates:
 C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C32(H32a,H32b)
4.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C20(H20), C22(H22), C26(H26), C27(H27), C31(H31), C34(H34),
 C36(H36), C41(H41), C43(H43)
4.d Idealised Me refined as rotating group:
 C44(H44a,H44b,H44c), C46(H46a,H46b,H46c), C48(H48a,H48b,H48c), C1(H1a,H1b,
 H1c), C3(H3a,H3b,H3c), C4(H4a,H4b,H4c), C9(H9a,H9b,H9c), C10(H10a,H10b,H10c),
 C5(H5a,H5b,H5c)
;
_olex2_submission_special_instructions 'No special instructions were received'