Diastereo- and Enantioselective Synthesis of Structurally Diverse Succinate, Butyrolactone, and Trifluoromethyl Derivatives by Iridium-Catalyzed Hydrogenation of Tetrasubstituted Olefins
Kerdphon, Sutthichat; Ponra, Sudipta; Yang, Jianping; Wu, Haibo; Eriksson, Lars; Andersson, Pher G.; ACS Catalysis 9 (2019) 6169–; doi:10.1021/acscatal.9b01508

data_4514788
_publ_section_title
;
 Diastereo- and Enantioselective Synthesis of Structurally Diverse
 Succinate, Butyrolactone, and Trifluoromethyl Derivatives by
 Iridium-Catalyzed Hydrogenation of Tetrasubstituted Olefins
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              6169
_journal_paper_doi               10.1021/acscatal.9b01508
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H11 F3 O2'
_chemical_formula_sum            'C11 H11 F3 O2'
_chemical_formula_weight         232.20
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2620(2)
_cell_length_b                   7.2620
_cell_length_c                   41.5160(10)
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.6
_cell_measurement_theta_min      4.26
_cell_volume                     2189.41(8)
_computing_cell_refinement       'Apex3 (Bruker AXS)'
_computing_data_collection       'Apex3 (Bruker AXS)'
_computing_data_reduction        'Apex3 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 with Photon 100 CMOS detector'
_diffrn_measurement_method       '\w scans and \f scans to fill Ewald sphere'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            17070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         4.260
_diffrn_source                   'Incotec 1myS'
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0389P)^2^+0.6735P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1996
_reflns_number_total             2017
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01508_si_002.cif
_cod_data_source_block           r
_cod_original_cell_volume        2189.41(13)
_cod_database_code               4514788
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              14022
_shelx_hkl_checksum              1881