Cis-selective and highly enantioselective hydrogenation of 2,3,4-trisubstituted quinolines.
Zhang, Zhenhua; Du, Haifeng; Organic letters 17 (2015) 2816–2819; doi:10.1021/acs.orglett.5b01240

data_1519496
_publ_section_title
;
 Cis-selective and highly enantioselective hydrogenation of
 2,3,4-trisubstituted quinolines.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2816
_journal_page_last               2819
_journal_paper_doi               10.1021/acs.orglett.5b01240
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 Br N'
_chemical_formula_sum            'C22 H20 Br N'
_chemical_formula_weight         378.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                102.328(8)
_cell_angle_beta                 106.299(8)
_cell_angle_gamma                90.659(7)
_cell_formula_units_Z            1
_cell_length_a                   6.134(3)
_cell_length_b                   7.123(4)
_cell_length_c                   10.777(6)
_cell_measurement_reflns_used    2086
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      32.7919
_cell_measurement_theta_min      2.9360
_cell_volume                     440.2(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.1708
              2theta: -21.1662
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.1708
              2theta: -21.1662
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 180.0000
                 XTD: 40.1708
              2theta: -21.1662
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 10.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 40.1708
              2theta: -21.1662
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0195
_diffrn_orient_matrix_UB_12      0.0318
_diffrn_orient_matrix_UB_13      0.1662
_diffrn_orient_matrix_UB_21      -0.1176
_diffrn_orient_matrix_UB_22      -0.0735
_diffrn_orient_matrix_UB_23      0.0392
_diffrn_orient_matrix_UB_31      0.0375
_diffrn_orient_matrix_UB_32      -0.0823
_diffrn_orient_matrix_UB_33      0.0408
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7216
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_min         2.936
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       Plate
_exptl_crystal_F_000             194
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.018(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0402P)^2^+0.0109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                3777
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01240_si_001.cif
_cod_data_source_block           sa4001
_cod_depositor_comments          'Adding full bibliography for 1519496.cif.'
_cod_database_code               1519496
_diffrn_number_total             1984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              85577
_shelx_hkl_checksum              48269
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'