Catalytic Asymmetric Synthesis of Chiral γ-Amino Ketones via Umpolung Reactions of Imines
Hu, Lin; Wu, Yongwei; Li, Zhe; Deng, Li; Journal of the American Chemical Society  (2016) –; doi:10.1021/jacs.6b09754

data_4125317
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral \g-Amino Ketones via Umpolung
 Reactions of Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.6b09754
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H15 F3 N2 O3'
_chemical_formula_sum            'C15 H15 F3 N2 O3'
_chemical_formula_weight         328.29
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2016-09-08
_audit_creation_method           CRYSTALS_ver_14.61_build_00000
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.11790(10)
_cell_length_b                   11.3464(2)
_cell_length_c                   32.4270(4)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    100
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     2986.82(7)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            32783
_diffrn_reflns_theta_full        66.695
_diffrn_reflns_theta_max         66.695
_diffrn_reflns_theta_min         2.725
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 2249 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.0009833
_refine_ls_shift/su_mean         0.0000753
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.87P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0663
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0663
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                5266
_reflns_number_total             5277
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.79
_oxford_diffrn_Wilson_scale      2.27
_oxford_refine_ls_r_factor_ref   0.0266
_oxford_refine_ls_scale          0.076985(12)
_oxford_reflns_number_all        5277
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title ZHE_6_126_0M
_cod_data_source_file            ja6b09754_si_002.cif
_cod_data_source_block           ZHE_6_126
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/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 4268 2015-11-12 08:31:59Z antanas 

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_moiety     'C30 H30 F6 N4 O6'
_cod_original_formula_sum        'C30 H30 F6 N4 O6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     656.58
_cod_database_code               4125317