Direct Comparison of C-H Bond Amination Efficacy through Manipulation of Nitrogen-Valence Centered Redox: Imido versus Iminyl.
Wilding, Matthew J. T.; Iovan, Diana A.; Wrobel, Alexandra T.; Lukens, James T.; MacMillan, Samantha N.; Lancaster, Kyle M.; Betley, Theodore A.; Journal of the American Chemical Society 139 (2017) 14757–14766; doi:10.1021/jacs.7b08714

data_4131685
_publ_section_title
;
 Direct Comparison of C-H Bond Amination Efficacy through Manipulation of
 Nitrogen-Valence Centered Redox: Imido versus Iminyl.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14757
_journal_page_last               14766
_journal_paper_doi               10.1021/jacs.7b08714
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C76 H63 Fe N3'
_chemical_formula_sum            'C76 H63 Fe N3'
_chemical_formula_weight         1074.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                68.051(3)
_cell_angle_beta                 84.136(3)
_cell_angle_gamma                79.987(3)
_cell_formula_units_Z            2
_cell_length_a                   14.694(3)
_cell_length_b                   15.145(3)
_cell_length_c                   16.966(4)
_cell_measurement_reflns_used    4573
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.21
_cell_measurement_theta_min      2.28
_cell_volume                     3445.8(13)
_computing_cell_refinement       'SAINT 8.34A (Bruker-AXS,2014)'
_computing_data_collection       'APEX2 v2014.3.0 (Bruker-AXS,2014)'
_computing_data_reduction        'SAINT 8.34A (Bruker-AXS,2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XLMP (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.05
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.1304
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21370
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.753
_diffrn_reflns_theta_min         1.408
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.0577 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.8152.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.202
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         12598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1650
_refine_ls_R_factor_gt           0.0885
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1561P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2473
_refine_ls_wR_factor_ref         0.2798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5860
_reflns_number_total             12598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08714_si_002.cif
_cod_data_source_block           ArLFeNHAr
_cod_depositor_comments
;

2020-10-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '0.5(C76 H63 Fe N3)'
_cod_original_formula_sum        'C40 H0.25 Fe N0.25'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     540.00
_cod_database_code               4131685
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.768
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N004(H004), C00G(H00G), C00J(H00J), C00M(H00M), C00N(H00N), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00U(H00U), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C012(H012), C014(H014), C015(H015), C016(H016), C018(H018),
 C019(H019), C01A(H01A), C01B(H01B), C01C(H01C), C01E(H01E), C01F(H01F),
 C01G(H01G), C01I(H01J), C01J(H01K), C01K(H01L), C01L(H01M), C01M(H01N),
 C01N(H01O), C01O(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T),
 C01U(H01U), C01V(H01V), C01W(H01W), C01Y(H01Z), C01Z(H01), C020(H020),
 C021(H021), C022(H022), C024(H024)
2.b Idealised Me refined as rotating group:
 C01H(H01D,H01H,H01I), C01X(H01X,H01Y,H), C025(H02A,H02B,H02C), C026(H02D,H02E,
 H02F), C027(H02G,H02H,H02I), C028(H02J,H02K,H02L)
;
_shelx_res_checksum              27341
_shelx_hkl_checksum              49966