Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines.
Zhang, Zhenhua; Du, Haifeng; Organic letters 17 (2015) 6266–6269; doi:10.1021/acs.orglett.5b03307

data_1555480
_publ_section_title
;
 Enantioselective Metal-Free Hydrogenations of Disubstituted Quinolines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6266
_journal_page_last               6269
_journal_paper_doi               10.1021/acs.orglett.5b03307
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H18 Br N'
_chemical_formula_sum            'C21 H18 Br N'
_chemical_formula_weight         364.27
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.952(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.094(3)
_cell_length_b                   14.285(4)
_cell_length_c                   11.689(3)
_cell_measurement_reflns_used    5376
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4774
_cell_measurement_theta_min      1.7424
_cell_volume                     1685.2(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1218
	          2theta: -19.9488
scan:
	Number of images: 354
	           Slice: -108.2500 - 68.7500
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.1218
	          2theta: -19.9488
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1218
	          2theta: -19.9488
;
_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      0.0954
_diffrn_orient_matrix_UB_12      0.0111
_diffrn_orient_matrix_UB_13      -0.0242
_diffrn_orient_matrix_UB_21      -0.0085
_diffrn_orient_matrix_UB_22      -0.0441
_diffrn_orient_matrix_UB_23      -0.0537
_diffrn_orient_matrix_UB_31      -0.0191
_diffrn_orient_matrix_UB_32      0.0659
_diffrn_orient_matrix_UB_33      -0.0511
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19724
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_min         2.018
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.75096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2872 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         7604
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0362
_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^)+(0.0220P)^2^+0.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0708
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                7135
_reflns_number_total             7604
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03307_si_002.cif
_cod_data_source_block           sa4214
_cod_original_cell_volume        1685.3(8)
_cod_database_code               1555480
_diffrn_number_total             4001
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C3(H3), C1A(H1AB), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C5A(H5A), C6A(H6A), C7A(H7A),
  C8A(H8A), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C17A(H17A),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A)
;
_shelx_res_checksum              88771
_shelx_hkl_checksum              87084
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'