Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An Experimental and Computational Study
Kim, Seung Wook; Meyer, Cole C.; Mai, Binh Khanh; Liu, Peng; Krische, Michael J.; ACS Catalysis 9 (2019) 9158–; doi:10.1021/acscatal.9b03695

data_4514612
_publ_section_title
;
 Inversion of Enantioselectivity in Allene Gas versus Allyl Acetate
 Reductive Aldehyde Allylation Guided by Metal-Centered Stereogenicity: An
 Experimental and Computational Study
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9158
_journal_paper_doi               10.1021/acscatal.9b03695
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C48 H40 P2, C7 H2 N2 O6, C3 H5, Ir, 2 C7 H8'
_chemical_formula_sum            'C72 H63 Ir N2 O6 P2'
_chemical_formula_weight         1306.38
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.155(2)
_cell_length_b                   17.531(3)
_cell_length_c                   22.268(3)
_cell_measurement_reflns_used    9707
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.55
_cell_volume                     5916.2(15)
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Nonius Kappa CCD with a Bruker Apex II detector'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            168850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         1.776
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    2.368
_exptl_absorpt_correction_T_max  0.7723
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_description       prism
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 5460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0019(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     819
_refine_ls_number_reflns         14106
_refine_ls_number_restraints     777
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0215
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0057P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0353
_refine_ls_wR_factor_ref         0.0357
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                12928
_reflns_number_total             14106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03695_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               4514612
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.444
_shelx_estimated_absorpt_t_max   0.733
_shelx_res_checksum              57586
_shelx_hkl_checksum              4673