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_1549801
_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         'C31 H25 Cl Fe N5, Cl O4, 2(C H Cl3)'
_chemical_formula_sum            'C33 H27 Cl8 Fe N5 O4'
_chemical_formula_weight         897.04
_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             2016-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2016-11-11 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.2266(14)
_cell_angle_beta                 101.5632(15)
_cell_angle_gamma                98.3455(15)
_cell_formula_units_Z            2
_cell_length_a                   9.68503(17)
_cell_length_b                   9.74597(18)
_cell_length_c                   20.3011(3)
_cell_measurement_reflns_used    22896
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.1810
_cell_measurement_theta_min      2.0590
_cell_volume                     1852.88(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.998
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00-108.00  360
  2  \w    -96.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  230
  3  \w    -71.00  19.00   0.50    8.00    --  -20.00 -72.00 -36.00  180
  4  \w    -45.00  -9.00   0.50    8.00    --  -20.00  72.00-108.00   72
  5  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00 -36.00   61
  6  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  7  \w    -67.50  19.00   0.50    8.00    --  -20.00 -72.00  36.00  173
  8  \w    -65.50   7.00   0.50    8.00    --  -20.00 -72.00-180.00  145
  9  \w    -43.50   3.00   0.50    8.00    --  -20.00 -72.00-108.00   93
 10  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00  36.00   61
 11  \w    -10.00   3.00   0.50    8.00    --  -20.00  72.00 108.00   26
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0158055000
_diffrn_orient_matrix_UB_12      0.0731758000
_diffrn_orient_matrix_UB_13      -0.0009908000
_diffrn_orient_matrix_UB_21      0.0026199000
_diffrn_orient_matrix_UB_22      0.0081018000
_diffrn_orient_matrix_UB_23      0.0351237000
_diffrn_orient_matrix_UB_31      0.0739679000
_diffrn_orient_matrix_UB_32      -0.0041369000
_diffrn_orient_matrix_UB_33      0.0065927000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1263
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            29819
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.053
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_description       needle
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         6522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+1.0027P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1307
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5925
_reflns_number_total             6522
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02053a2.cif
_cod_data_source_block           dm-sr-08-11-2016_mo
_cod_depositor_comments
'Adding full bibliography for 1549798--1549802.cif.'
_cod_database_code               1549801
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         C34H25Cl2Fe1N5O4
_reflns_odcompleteness_completeness 90.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00M(H00M), C01D(H01D), C01F(H01F)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00C), C00O(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C016(H016), C017(H017), C019(H019), C01B(H01B),
 C01C(H01C), C01E(H01E)
;
_shelx_res_checksum              95731
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 4.663
_oxdiff_exptl_absorpt_empirical_full_min 0.279