Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts.
Touge, Taichiro; Sakaguchi, Kazuhiko; Tamaki, Nao; Nara, Hideki; Yokozawa, Tohru; Matsumura, Kazuhiko; Kayaki, Yoshihito; Journal of the American Chemical Society 141 (2019) 16354–16361; doi:10.1021/jacs.9b07297

data_4127675
_publ_section_title
;
 Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic
 Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of
 Keto Acids with Oxo-Tethered Ruthenium Catalysts.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16354
_journal_page_last               16361
_journal_paper_doi               10.1021/jacs.9b07297
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C72 H48 N24 Zn6 I12 2(C13 H12 O2) (C6 H12)'
_chemical_formula_sum            'C104 H84 I12 N24 O4 Zn6'
_chemical_formula_weight         3648.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 109.1430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   36.2700(3)
_cell_length_b                   14.50280(10)
_cell_length_c                   34.6393(3)
_cell_measurement_reflns_used    57240
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.2350
_cell_measurement_theta_min      2.5780
_cell_volume                     17213.3(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'shelXle (Hubschele et al., 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  "'XtaLAB Synergy, Dualflex, HyPix"
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            171259
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.501
_diffrn_reflns_theta_min         2.488
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    18.147
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_correction_T_min  0.043
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             6896
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.099
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.546
_refine_diff_density_rms         0.274
_refine_ls_abs_structure_details
;
 Flack x determined using 13084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1425
_refine_ls_number_reflns         35636
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0798
_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^)+(0.1863P)^2^+6.2521P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2224
_refine_ls_wR_factor_ref         0.2317
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                31979
_reflns_number_total             35636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07297_si_012.cif
_cod_data_source_block           exp_78
_cod_database_code               4127675
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              99411
_shelx_hkl_checksum              11253