Ruthenium-Catalyzed Chemo- and Enantioselective Hydrogenation of Isoquinoline Carbocycles.
Jin, Yushu; Makida, Yusuke; Uchida, Tatsuya; Kuwano, Ryoichi; The Journal of organic chemistry 83 (2018) 3829–3839; doi:10.1021/acs.joc.8b00190

data_4033556
_publ_section_title
;
 Ruthenium-Catalyzed Chemo- and Enantioselective Hydrogenation of
 Isoquinoline Carbocycles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3829
_journal_page_last               3839
_journal_paper_doi               10.1021/acs.joc.8b00190
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.298(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.4860(2)
_cell_length_b                   5.6312(2)
_cell_length_c                   15.5148(4)
_cell_measurement_reflns_used    6124
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      5.82
_cell_volume                     641.35(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6746
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         5.817
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.10
_refine_diff_density_min         -0.11
_refine_ls_abs_structure_details
;
 Flack x determined using 648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.0692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                1856
_reflns_number_total             2198
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b00190_si_001.cif
_cod_data_source_block           sample2
_cod_depositor_comments          'Adding full bibliography for 4033556.cif.'
_cod_database_code               4033556
_shelx_res_checksum              77308
_shelx_hkl_checksum              72848