General Light-Mediated, Highly Diastereoselective Piperidine Epimerization: From Most Accessible to Most Stable Stereoisomer
Shen, Zican; Walker, Morgan M.; Chen, Shuming; Parada, Giovanny A.; Chu, Duc M.; Dongbang, Sun; Mayer, James M.; Houk, K. N.; Ellman, Jonathan A.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c11911

data_4135467
_publ_section_title
;
 General Light-Mediated, Highly Diastereoselective Piperidine
 Epimerization: From Most Accessible to Most Stable Stereoisomer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c11911
_journal_year                    2020
_chemical_formula_moiety         'C6 H2 N3 O9 S, C12 H18 N, C4 H8 O2'
_chemical_formula_sum            'C22 H28 N4 O11 S'
_chemical_formula_weight         556.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.8750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.95300(10)
_cell_length_b                   18.4696(2)
_cell_length_c                   17.1020(3)
_cell_measurement_reflns_used    24863
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.4860
_cell_measurement_theta_min      3.5040
_cell_volume                     2506.35(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2045
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            84093
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.597
_diffrn_reflns_theta_max         66.597
_diffrn_reflns_theta_min         3.527
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       Block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00068(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0687P)^2^+0.1924P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3716
_reflns_number_total             4419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c11911_si_002.cif
_cod_data_source_block           007a-20003
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4135467
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.720
_shelx_estimated_absorpt_t_max   0.817
_shelx_res_checksum              89659
_shelx_hkl_checksum              10347