Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols: Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of Phthalimido-Allene via Hydrogen Auto-Transfer.
Spielmann, Kim; Xiang, Ming; Schwartz, Leyah A.; Krische, Michael J.; Journal of the American Chemical Society 141 (2019) 14136–14141; doi:10.1021/jacs.9b08715

data_4128809
_publ_section_title
;
 Direct Conversion of Primary Alcohols to 1,2-Amino Alcohols:
 Enantioselective Iridium-Catalyzed Carbonyl Reductive Coupling of
 Phthalimido-Allene via Hydrogen Auto-Transfer.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14136
_journal_page_last               14141
_journal_paper_doi               10.1021/jacs.9b08715
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C44 H40 P2, C7 H2 N2 O6, C3 H5, Ir, C4 H8 O'
_chemical_formula_sum            'C58 H55 Ir N2 O7 P2'
_chemical_formula_weight         1146.18
_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
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.339(2)
_cell_length_b                   17.764(2)
_cell_length_c                   18.920(3)
_cell_measurement_reflns_used    7998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.23
_cell_measurement_theta_min      2.29
_cell_volume                     4819.3(12)
_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 0.994
_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  0.0906
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            67534
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.413
_diffrn_reflns_theta_min         2.293
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    2.896
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS. G. M. Sheldrick
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       prism
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.197
_refine_diff_density_min         -0.918
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details
;
 Flack x determined using 4223 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         12021
_refine_ls_number_restraints     420
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0318P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                10460
_reflns_number_total             12021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b08715_si_004.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        4819.4(11)
_cod_database_code               4128809
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.568
_shelx_estimated_absorpt_t_max   0.761
_shelx_res_checksum              6316
_shelx_hkl_checksum              35639