Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(III) complexes bearing an amidato ligand.
Dai, Zengjin; Pan, Ying-Min; Wang, Shou-Guo; Zhang, Xumu; Yin, Qin; Organic & biomolecular chemistry 19 (2021) 8934–8939; doi:10.1039/d1ob01710a

data_7158327
_publ_section_title
;
 Direct reductive amination of ketones with ammonium salt catalysed by
 Cp*Ir(III) complexes bearing an amidato ligand.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8934
_journal_page_last               8939
_journal_paper_doi               10.1039/d1ob01710a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H32 Cl Ir N O P, 0.323(H2 O)'
_chemical_formula_sum            'C27 H32.65 Cl Ir N O1.32 P'
_chemical_formula_weight         650.96
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-25 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8894(7)
_cell_length_b                   13.1148(7)
_cell_length_c                   14.7203(8)
_cell_measurement_reflns_used    9604
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      4.52
_cell_volume                     2488.3(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47540
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.330
_diffrn_reflns_theta_min         4.515
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.144
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1469 before and 0.0858 after correction.
The Ratio of minimum to maximum transmission is 0.2258.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_description       needle
_exptl_crystal_F_000             1285
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.788
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.110
_refine_ls_abs_structure_details
;
 Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0510P)^2^+1.1084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0682
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4569
_reflns_number_total             4582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01710a2.cif
_cod_data_source_block           cxy3274
_cod_depositor_comments          'Adding full bibliography for 7158327.cif.'
_cod_database_code               7158327
_shelx_shelxl_version_number     2018/3
_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, All O(H,H) groups
2. Others
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(1)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C2(H2)
3.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C1(H1A,H1B), C4(H4A,H4B)
3.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C17(H17), C8(H8), C7(H7), C11(H11), C16(H16),
 C9(H9), C10(H10)
3.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,
 H23C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              99471
_olex2_submission_special_instructions 'No special instructions were received'