Selective reduction of formamides to O-silylated hemiaminals or methylamines with HSiMe<sub>2</sub>Ph catalyzed by iridium complexes.
Guzmán, Jefferson; Bernal, Ana M.; García-Orduña, Pilar; Lahoz, Fernando J.; Oro, Luis A.; Fernández-Alvarez, Francisco J; Dalton transactions (Cambridge, England : 2003) 48 (2019) 4255–4262; doi:10.1039/c8dt05070h

data_7049153
_publ_section_title
;
 Selective reduction of formamides to O-silylated hemiaminals or
 methylamines with HSiMe<sub>2</sub>Ph catalyzed by iridium complexes.
;
_journal_issue                   13
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4255
_journal_page_last               4262
_journal_paper_doi               10.1039/c8dt05070h
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C22 H39 Cl Ir N O Si'
_chemical_formula_sum            'C22 H39 Cl Ir N O Si'
_chemical_formula_weight         589.28
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-07-23 deposited with the CCDC.    2019-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                94.4790(10)
_cell_angle_beta                 91.3980(10)
_cell_angle_gamma                94.6700(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8806(4)
_cell_length_b                   10.5584(4)
_cell_length_c                   12.7712(5)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.916
_cell_measurement_theta_min      2.613
_cell_volume                     1189.30(8)
_computing_cell_refinement
'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_data_collection       'SMART in APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction
'SAINT+ in APEX3 v. 2017.3 (Bruker AXS, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker Smart APEX CCD system'
_diffrn_measurement_method       'narrow \w frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17208
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.916
_diffrn_reflns_theta_min         2.302
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    5.788
_exptl_absorpt_correction_T_max  0.5636
_exptl_absorpt_correction_T_min  0.3963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       prism
_exptl_crystal_F_000             588
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.055
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0172
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0174P)^2^+1.0477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5534
_reflns_number_total             5722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt05070h2.cif
_cod_data_source_block           cmpnd_2
_cod_depositor_comments          'Adding full bibliography for 7049153.cif.'
_cod_database_code               7049153
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              75593