Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy.
Hu, Bin; Deng, Li; The Journal of organic chemistry 84 (2019) 994–1005; doi:10.1021/acs.joc.8b02893

data_4036003
_publ_section_title
;
 Direct Catalytic Asymmetric Synthesis of Trifluoromethylated \g-Amino
 Esters/Lactones via Umpolung Strategy.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              994
_journal_page_last               1005
_journal_paper_doi               10.1021/acs.joc.8b02893
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H13 F3 N2 O4'
_chemical_formula_sum            'C14 H13 F3 N2 O4'
_chemical_formula_weight         330.26
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2016-12-07
_audit_creation_method           CRYSTALS_ver_14.61_build_00000
_cell_angle_alpha                90
_cell_angle_beta                 117.2428(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9367(2)
_cell_length_b                   6.76280(10)
_cell_length_c                   16.9558(3)
_cell_measurement_reflns_used    9643
_cell_measurement_temperature    100
_cell_measurement_theta_max      67
_cell_measurement_theta_min      3
_cell_volume                     1624.73(4)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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    'USER DEFINED STRUCTURE SOLUTION'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.028
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
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_diffrn_reflns_theta_max         66.687
_diffrn_reflns_theta_min         2.931
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.064
_exptl_absorpt_correction_T_max  0.93
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.247
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_platon_squeeze_details
;
TITL 1 in C:\Users\foxman1\Desktop\bi  At 13:
CELL   15.9370    6.7630   16.9560     90.00    117.24     90.00
SPGR P21
C101 0.122 0.493 0.094 !       2.42 eA-3
C102 0.993 0.291 0.000 !       2.42 eA-3
C103 0.879 0.256 0.939 !       1.96 eA-3
C104 0.021 0.461 0.034 !       1.80 eA-3
C105 0.925 0.925 0.983 !       1.47 eA-3
C106 0.892 0.624 0.939 !       0.74 eA-3
;
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details 'Flack (1983), 2404 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5457
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.0103717
_refine_ls_shift/su_mean         0.0009590
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0623
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0623
_reflns_limit_h_max              16
_reflns_limit_h_min              -18
_reflns_limit_k_max              8
_reflns_limit_k_min              -7
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5295
_reflns_number_total             5457
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0243
_oxford_refine_ls_scale          0.7005(9)
_oxford_reflns_number_all        5457
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '1 in C:\Users\foxman1\Desktop\bi At 13:43 on'
_cod_data_source_file            jo8b02893_si_002.cif
_cod_data_source_block           binh_08_37_QD
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4036003
_platon_squeeze_void_probe_radius 1.20