Highly Diastereoselective Functionalization of Piperidines by Photoredox Catalyzed α-Amino C-H Arylation and Epimerization.
Walker, Morgan M.; Koronkiewicz, Brian; Chen, Shuming; Houk, K. N.; Mayer, James M.; Ellman, Jonathan A.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13165

data_4134796
_publ_section_title
;
 Highly Diastereoselective Functionalization of Piperidines by Photoredox
 Catalyzed \a-Amino C-H Arylation and Epimerization.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13165
_journal_year                    2020
_chemical_formula_moiety         'C20 H23 N2 O, C6 H2 N3 O9 S, 0.5(C7 H8)'
_chemical_formula_sum            'C29.5 H29 N5 O10 S'
_chemical_formula_weight         645.64
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                81.734(2)
_cell_angle_beta                 86.081(2)
_cell_angle_gamma                75.200(3)
_cell_formula_units_Z            2
_cell_length_a                   8.9495(3)
_cell_length_b                   9.6147(3)
_cell_length_c                   18.2756(5)
_cell_measurement_reflns_used    17512
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      35.3810
_cell_measurement_theta_min      3.1480
_cell_volume                     1503.77(8)
_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 5.8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Dectris Pilatus 3R'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35175
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55232
_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    1.426
_exptl_crystal_description       Plate
_exptl_crystal_F_000             674
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         6892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0407P)^2^+0.6746P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0837
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6140
_reflns_number_total             6892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13165_si_006.cif
_cod_data_source_block           007c-20017
_cod_original_formula_sum        'C29.50 H29 N5 O10 S'
_cod_database_code               4134796
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              95810
_shelx_hkl_checksum              69333