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_1549802
_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         '2(C31 H25 Br Fe N5), Br4 Fe, C2 H3 N'
_chemical_formula_sum            'C64 H53 Br6 Fe3 N11'
_chemical_formula_weight         1623.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-23 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.0269(4)
_cell_length_b                   18.8487(4)
_cell_length_c                   35.2474(6)
_cell_measurement_reflns_used    37636
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.9950
_cell_measurement_theta_min      2.0260
_cell_volume                     12640.9(4)
_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
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_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    -89.00   7.00   0.50    8.00    --  -20.00 -72.00  36.00  192
  2  \w    -70.00   9.00   0.50    8.00    --  -20.00 -72.00-180.00  158
  3  \w      0.00  37.50   0.50    8.00    --  -20.00  72.00-108.00   75
  4  \w    -59.00  70.00   0.50    8.00    --  -20.00  72.00-180.00  258
  5  \w    -89.00 -37.50   0.50    8.00    --  -20.00 -72.00 108.00  103
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011655000
_diffrn_orient_matrix_UB_12      -0.0086663000
_diffrn_orient_matrix_UB_13      0.0195615000
_diffrn_orient_matrix_UB_21      -0.0372161000
_diffrn_orient_matrix_UB_22      0.0023295000
_diffrn_orient_matrix_UB_23      -0.0003527000
_diffrn_orient_matrix_UB_31      -0.0020801000
_diffrn_orient_matrix_UB_32      -0.0365444000
_diffrn_orient_matrix_UB_33      -0.0046805000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            89263
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40246
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6416
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     758
_refine_ls_number_reflns         11121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+13.1213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0760
_reflns_number_gt                9027
_reflns_number_total             11121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc02053a2.cif
_cod_data_source_block           dm-sr5-192-1_mo
_cod_depositor_comments
'Adding full bibliography for 1549798--1549802.cif.'
_cod_database_code               1549802
_chemical_oxdiff_formula         C31H25Br2Fe1N5
_reflns_odcompleteness_completeness 93.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.15
_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:
 C00R(H00R), C01P(H01P)
2.b Secondary CH2 refined with riding coordinates:
 C019(H01A,H01B), C01C(H01D,H01E), C01O(H01I,H01M), C021(H02A,H02B)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00O(H00O), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C014(H014),
 C015(H015), C016(H016), C01A(H01C), C01D(H01F), C01F(H01G), C01G(H01H),
 C01J(H01J), C01K(H01K), C01L(H01L), C01N(H01N), C01Q(H01Q), C01R(H01R),
 C01S(H01S), C01T(H01T), C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y),
 C01Z(H01Z), C020(H020), C022(H022), C023(H023), C024(H024), C025(H025),
 C026(H026), C027(H027), C028(H028), C029(H029)
2.d Idealised Me refined as rotating group:
 C02C(H02C,H02D,H02E)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.595