Chiral phosphoric acid catalyzed enantioselective transfer deuteration of ketimines by use of benzothiazoline as a deuterium donor: synthesis of optically active deuterated amines.
Sakamoto, Tsubasa; Mori, Keiji; Akiyama, Takahiko; Organic letters 14 (2012) 3312–3315; doi:10.1021/ol3012869

data_1507845
_publ_section_title
;
 Chiral phosphoric acid catalyzed enantioselective transfer deuteration of
 ketimines by use of benzothiazoline as a deuterium donor: synthesis of
 optically active deuterated amines.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3312
_journal_page_last               3315
_journal_paper_doi               10.1021/ol3012869
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C22 H21 Br N O3'
_chemical_formula_weight         427.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.897(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.467(7)
_cell_length_b                   5.711(3)
_cell_length_c                   13.534(7)
_cell_measurement_reflns_used    1578
_cell_measurement_temperature    123
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.77
_cell_volume                     951.7(9)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0701
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_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5144
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    2.182
_exptl_absorpt_correction_T_max  0.8113
_exptl_absorpt_correction_T_min  0.7355
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             438
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_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.860
_refine_diff_density_min         -1.547
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.038(19)
_refine_ls_extinction_method     none
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_refine_ls_number_parameters     249
_refine_ls_number_reflns         3835
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0827
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1922
_refine_ls_wR_factor_ref         0.2236
_reflns_number_gt                2729
_reflns_number_total             3835
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3012869_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 1507845.cif.
;
_cod_original_cell_volume        951.6(8)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               1507845