Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation of 1,3-Disubstituted Isoquinolines
Kim, Alexia N.; Ngamnithiporn, Aurapat; Welin, Eric R.; Daiger, Martin T.; Grünanger, Christian U.; Bartberger, Michael D.; Virgil, Scott C.; Stoltz, Brian M.; ACS Catalysis  (2020) 3241–3248; doi:10.1021/acscatal.0c00211

data_4517437
_publ_section_title
;
 Iridium-Catalyzed Enantioselective and Diastereoselective Hydrogenation
 of 1,3-Disubstituted Isoquinolines
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              3241
_journal_page_last               3248
_journal_paper_doi               10.1021/acscatal.0c00211
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H15 N O S'
_chemical_formula_sum            'C14 H15 N O S'
_chemical_formula_weight         245.33
_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'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2019-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506),
 SHELXL-2018/3, and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 96.337(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3309(19)
_cell_length_b                   6.6556(18)
_cell_length_c                   10.916(3)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.61
_cell_measurement_theta_min      2.46
_cell_volume                     601.6(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_collection
'BIS 2018.9.0.2/05-Oct-2018 & APEX3_2018.7-2 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Kappa'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Triumph focusing graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25734
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.613
_diffrn_reflns_theta_min         1.877
_diffrn_source                   'sealed tube'
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_type              'XRD C-TECH Long Fine Focus'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0498 before and 0.0444 after correction. 
The Ratio of minimum to maximum transmission is 0.9299. 
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5228
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                4632
_reflns_number_total             5228
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00211_si_002.cif
_cod_data_source_block           d19110
_cod_depositor_comments          'Adding full bibliography for 4517437.cif.'
_cod_database_code               4517437
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.911
_refine_ls_abs_structure_hooft   0.03(2)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Shared sites
{H12, H12A}
{H14, H14A}
3. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(S1)
Uanis(S1A) = Uanis(C13A)
4. Others
 Sof(S1A)=Sof(C13A)=Sof(H13A)=Sof(H12A)=Sof(H14A)=1-FVAR(1)
 Sof(S1)=Sof(C13)=Sof(H13)=Sof(H12)=Sof(H14)=FVAR(1)
;
_shelx_res_checksum              30227
_shelx_hkl_checksum              51053
_olex2_submission_special_instructions 'No special instructions were received'