Enantioselective Hydrogenation of α-Aryloxy and α-Alkoxy α,β-Unsaturated Carboxylic Acids Catalyzed by Chiral Spiro Iridium/Phosphino-Oxazoline Complexes
Shen Li; Shou-Fei Zhu; Jian-Hua Xie; Song Song; Can-Ming Zhang; Qi-Lin Zhou; Journal of the American Chemical Society 132 (2010) 1172–1179; doi:10.1021/ja909810k

data_4101833
_publ_section_title
;
 Enantioselective Hydrogenation of \a-Aryloxy and \a-Alkoxy
 \a,\b-Unsaturated Carboxylic Acids Catalyzed by Chiral Spiro
 Iridium/Phosphino-Oxazoline Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1172
_journal_page_last               1179
_journal_paper_doi               10.1021/ja909810k
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C95 H90 B F24 Ir N O P'
_chemical_formula_sum            'C95 H90 B F24 Ir N O P'
_chemical_formula_weight         1951.66
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.121(3)
_cell_length_b                   21.195(3)
_cell_length_c                   21.618(3)
_cell_measurement_reflns_used    20578
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      1.4
_cell_volume                     8761(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_sigmaI/netI    0.0919
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            87889
_diffrn_reflns_theta_full        28.72
_diffrn_reflns_theta_max         28.72
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    1.642
_exptl_absorpt_correction_T_max  0.8274
_exptl_absorpt_correction_T_min  0.7140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3952
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.158
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(4)
_refine_ls_extinction_coef       0.00042(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1158
_refine_ls_number_reflns         22653
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0196P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                20204
_reflns_number_total             22653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja909810k_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4101833