<i>N</i>-TFA-Gly-Bt-Based Stereoselective Synthesis of Substituted 3-Amino Tetrahydro-2<i>H</i>-pyran-2-ones via an Organocatalyzed Cascade Process.
Han, Liuqing; Li, Ke; Xu, Haitong; Mei, Tao; Sun, Yali; Qu, Jingping; Song, Yuming; The Journal of organic chemistry 84 (2019) 10526–10534; doi:10.1021/acs.joc.9b01488

data_4034049
_publ_section_title
;
 <i>N</i>-TFA-Gly-Bt-Based Stereoselective Synthesis of Substituted
 3-Amino Tetrahydro-2<i>H</i>-pyran-2-ones via an Organocatalyzed Cascade
 Process.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10526
_journal_page_last               10534
_journal_paper_doi               10.1021/acs.joc.9b01488
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C23 H19 F3 Fe N4 O3'
_chemical_formula_weight         512.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   'riding mode'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.437(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.807(5)
_cell_length_b                   10.896(3)
_cell_length_c                   10.885(3)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.3702
_cell_measurement_theta_min      2.4921
_cell_volume                     2426.9(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0724
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16158
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.118
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       stick
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.3812
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.16(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4266
_refine_ls_number_restraints     505
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0842P)^2^+3.7815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3872
_reflns_number_total             4266
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01488_si_002.cif
_cod_data_source_block           1_sq
_cod_original_cell_volume        2427.0(11)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4034049
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.687
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              44454
_shelx_hkl_checksum              25608
_shelx_fab_checksum              91404