2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive Couplings with Ketones.
Li, Kangnan; Shao, Xinxin; Tseng, Luke; Malcolmson, Steven J.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b12213

data_4126976
_publ_section_title
;
 2-Azadienes as Reagents for Preparing Chiral Amines: Synthesis of
 1,2-Amino Tertiary Alcohols by Cu-Catalyzed Enantioselective Reductive
 Couplings with Ketones.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12213
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H22 Br N O3'
_chemical_formula_sum            'C15 H22 Br N O3'
_chemical_formula_weight         344.24
_chemical_name_common            sxx-2-29
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 100.8244(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2460(5)
_cell_length_b                   10.5505(5)
_cell_length_c                   13.9596(7)
_cell_measurement_reflns_used    2044
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      35.2404
_cell_measurement_theta_min      2.1730
_cell_volume                     1626.85(13)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47150
_diffrn_reflns_theta_full        35.06
_diffrn_reflns_theta_max         35.06
_diffrn_reflns_theta_min         1.84
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Friedel opposites not treated as equivalent in abs. corr.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.254
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.250
_refine_ls_abs_structure_details
;

Flack x determined using 5418 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0080(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     377
_refine_ls_number_reflns         14341
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                12708
_reflns_number_total             14341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b12213_si_003.cif
_cod_data_source_block           rds692
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126976
_shelx_res_checksum              60640
_shelx_hkl_checksum              67491