Selective C-H halogenation over hydroxylation by non-heme iron(iv)-oxo.
Rana, Sujoy; Biswas, Jyoti Prasad; Sen, Asmita; Clémancey, Martin; Blondin, Geneviève; Latour, Jean-Marc; Rajaraman, Gopalan; Maiti, Debabrata; Chemical science 9 (2018) 7843–7858; doi:10.1039/c8sc02053a

data_1549798
_publ_section_title
;
 Selective C-H halogenation over hydroxylation by non-heme iron(iv)-oxo.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              7843
_journal_page_last               7858
_journal_paper_doi               10.1039/c8sc02053a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C32 H25 F3 Fe N5 O3 S, C F3 O3 S, C7 H8'
_chemical_formula_sum            'C40 H33 F6 Fe N5 O6 S2'
_chemical_formula_weight         913.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-09-23 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.882(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   42.348(14)
_cell_length_b                   11.696(4)
_cell_length_c                   18.645(6)
_cell_measurement_reflns_used    11855
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      3.0
_cell_volume                     9223(5)
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.913
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -108.0000
                 XTD: 45.0188
              2theta: -19.9819
scan:
    Number of images: 128
               Slice: -59.0000 - 5.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: -180.0000
                 XTD: 45.0188
              2theta: -19.9819
scan:
    Number of images: 62
               Slice: -65.0000 - -34.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -108.0000
                 XTD: 45.0188
              2theta: -19.9819
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: 108.0000
                 XTD: 45.0188
              2theta: -19.9819
scan:
    Number of images: 102
               Slice: -56.5000 - -5.5000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -180.0000
                 XTD: 45.0188
              2theta: -19.9819
scan:
    Number of images: 60
               Slice: -12.5000 - 17.5000
         Image width: 0.5000
            Exp time: 14.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 36.0000
                 XTD: 45.0188
              2theta: -19.9819
;
_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
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_diffrn_orient_matrix_UB_11      0.000101
_diffrn_orient_matrix_UB_12      0.023573
_diffrn_orient_matrix_UB_13      0.001822
_diffrn_orient_matrix_UB_21      0.039073
_diffrn_orient_matrix_UB_22      0.005694
_diffrn_orient_matrix_UB_23      -0.075834
_diffrn_orient_matrix_UB_31      -0.047694
_diffrn_orient_matrix_UB_32      0.004785
_diffrn_orient_matrix_UB_33      -0.024215
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35766
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.097
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Yellowish
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       Prism
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.521
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.00000(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         7845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.1356
_refine_ls_shift/su_max          2.672
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+120.9093P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2786
_refine_ls_wR_factor_ref         0.2892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6759
_reflns_number_total             7845
_reflns_shell_number_unique_all  12932
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02053a2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1549798--1549802.cif.
;
_cod_database_code               1549798
_shelxl_version_number           2012-9
_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 Ternary CH refined with riding coordinates:
 C60(H60)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C0AA(H0AA), C17(H17), C20(H20), C22(H22), C47(H47), C63(H63),
 C66(H66), C83(H83), C91(H91), C98(H98), C104(H104), C106(H106), C111(H111),
 C118(H118), C120(H120), C122(H122), C123(H123), C125(H125), C133(H133),
 C138(H138), C140(H140), C154(H154), C159(H159), C163(H163)
2.d Idealised Me refined as rotating group:
 C149(H14A,H14B,H14C)
;
_shelx_res_checksum              76844
_olex2_submission_special_instructions 'No special instructions were received'