Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones.
Shugrue, Christopher R.; Featherston, Aaron L.; Lackner, Rachel M.; Lin, Angela; Miller, Scott J.; The Journal of organic chemistry 83 (2018) 4491–4504; doi:10.1021/acs.joc.8b00207

data_4034947
_publ_section_title
;
 Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed
 Reductive Aminations of 3-Amidocyclohexanones.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4491
_journal_page_last               4504
_journal_paper_doi               10.1021/acs.joc.8b00207
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H26 N2 O3 S'
_chemical_formula_sum            'C20 H26 N2 O3 S'
_chemical_formula_weight         374.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 98.443(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4315(2)
_cell_length_b                   9.5202(2)
_cell_length_c                   21.4109(6)
_cell_measurement_reflns_used    23867
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.4800
_cell_measurement_theta_min      4.1480
_cell_volume                     1901.64(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0989
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13138
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.178
_diffrn_reflns_theta_max         67.178
_diffrn_reflns_theta_min         2.086
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       Needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
; 
 Flack x determined using 2315 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         13138
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+1.4940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1888
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                10457
_reflns_number_total             13138
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00207_si_003.cif
_cod_data_source_block           007b-17129
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034947
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.728
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              92742
_shelx_hkl_checksum              35537