Experiments and DFT Computations Combine to Decipher Fe-Catalyzed Amidine Synthesis through Nitrene Transfer and Nitrile Insertion
Coin, Guillaume; Dubourdeaux, Patrick; Avenier, Frédéric; Patra, Ranjan; Castro, Ludovic; Lebrun, Colette; Bayle, Pierre-Alain; Pécaut, Jacques; Blondin, Geneviève; Maldivi, Pascale; Latour, Jean-Marc; ACS Catalysis 11 (2021) 2253–2266; doi:10.1021/acscatal.0c03791

data_4518524
_publ_section_title
;
 Experiments and DFT Computations Combine to Decipher Fe-Catalyzed Amidine
 Synthesis through Nitrene Transfer and Nitrile Insertion
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2253
_journal_page_last               2266
_journal_paper_doi               10.1021/acscatal.0c03791
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C15 H22 N2 O2 S'
_chemical_formula_sum            'C15 H22 N2 O2 S'
_chemical_formula_weight         294.40
_chemical_name_common            CHTosMe
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2020-07-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.5640(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.027(2)
_cell_length_b                   10.1457(7)
_cell_length_c                   12.2742(9)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.278
_cell_measurement_theta_min      2.160
_cell_volume                     3174.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9800
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         2.160
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
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_refine_diff_density_rms         0.036
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_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             3670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c03791_si_001.cif
_cod_data_source_block           CHTosMe
_cod_original_cell_volume        3174.4(4)
_cod_database_code               4518524
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'