Chiral Phosphoric Acid-Catalyzed Enantioselective Reductive Amination of 2-Pyridyl Ketones: Construction of Structurally Chiral Pyridine-Based Ligands.
Abudu Rexit, Abulikemu; Luo, Shiwei; Mailikezati, Maihemuti; The Journal of organic chemistry 81 (2016) 11384–11388; doi:10.1021/acs.joc.6b01772

data_4037227
_publ_section_title
;
 Chiral Phosphoric Acid-Catalyzed Enantioselective Reductive Amination of
 2-Pyridyl Ketones: Construction of Structurally Chiral Pyridine-Based
 Ligands.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11384
_journal_page_last               11388
_journal_paper_doi               10.1021/acs.joc.6b01772
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H12 Br Cl N2'
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_space_group_name_H-M_alt        'P 21 21 21'
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_cell_angle_beta                 90
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_cell_length_b                   8.4967(4)
_cell_length_c                   25.3797(12)
_cell_measurement_reflns_used    2347
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.9559
_cell_measurement_theta_min      3.2031
_cell_volume                     1310.10(10)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra, Oxford Diffraction'
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
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_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
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_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.211
_exptl_absorpt_coefficient_mu    3.320
_exptl_absorpt_correction_T_max  0.4566
_exptl_absorpt_correction_T_min  0.3982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.023(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0286P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                1980
_reflns_number_total             2658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01772_si_001.cif
_cod_data_source_block           shelxl
_cod_database_code               4037227
_shelx_estimated_absorpt_t_min   0.398
_shelx_estimated_absorpt_t_max   0.457
_shelxl_version_number           2013-4
_shelx_res_checksum              17252
_shelx_hkl_checksum              11478