Design, scope and mechanism of highly active and selective chiral NHC‒iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes
Foster, Daven; Gao, Pengchao; Zhang, Ziyun; Sipos, Gellért; Sobolev, Alexandre N.; Nealon, Gareth; Falivene, Laura; Cavallo, Luigi; Dorta, Reto; Chemical Science 12 (2021) 3751–3767; doi:10.1039/D0SC05884J

data_1560237
_publ_section_title
;
 Design, scope and mechanism of highly active and selective chiral
 NHC--iridium catalysts for the intramolecular hydroamination of a variety
 of unactivated aminoalkenes
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3751
_journal_page_last               3767
_journal_paper_doi               10.1039/D0SC05884J
_journal_volume                  12
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C59 H76 Cl Ir N2'
_chemical_formula_sum            'C59 H76 Cl Ir N2'
_chemical_formula_weight         1040.86
_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   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2020-08-11 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2970(1)
_cell_length_b                   17.0451(1)
_cell_length_c                   17.8125(1)
_cell_measurement_reflns_used    32011
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.213
_cell_measurement_theta_min      3.566
_cell_volume                     4948.03(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0737848
_diffrn_orient_matrix_UB_12      0.0450664
_diffrn_orient_matrix_UB_13      0.0326153
_diffrn_orient_matrix_UB_21      -0.0550386
_diffrn_orient_matrix_UB_22      -0.0721789
_diffrn_orient_matrix_UB_23      -0.0128885
_diffrn_orient_matrix_UB_31      0.0214650
_diffrn_orient_matrix_UB_32      -0.0304232
_diffrn_orient_matrix_UB_33      0.0790823
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.270
_diffrn_reflns_theta_max         67.270
_diffrn_reflns_theta_min         3.589
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.010
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.80552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.575
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 3672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.052(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         8845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                8469
_reflns_number_total             8845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05884j3.cif
_cod_data_source_block           df166
_cod_depositor_comments          'Adding full bibliography for 1560237.cif.'
_cod_database_code               1560237
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.351
_shelx_estimated_absorpt_t_max   0.840
_shelx_res_checksum              367