Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with the Capacity for Stereodivergence.
Ma, Rulin; Young, Jonathon; Promontorio, Rossella; Dannheim, Friederike M.; Pattillo, Christopher C.; White, M. Christina; Journal of the American Chemical Society 141 (2019) 9468–9473; doi:10.1021/jacs.9b02690

data_4127436
_publ_contact_author
; 
M. Christina White 
University of Illinois 
Department of Chemistry 
600 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Synthesis of anti-1,3 Amino Alcohol Motifs via Pd(II)/SOX Catalysis with
 the Capacity for Stereodivergence.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9468
_journal_page_last               9473
_journal_paper_doi               10.1021/jacs.9b02690
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety
; 
C18 H23 N O5 S, 0.288(C5 H12), 0.712(C H2 Cl2) 
;
_chemical_formula_sum            'C20.15 H27.88 Cl1.42 N O5 S'
_chemical_formula_weight         446.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
; 
? 
;
_cell_angle_alpha                80.064(2)
_cell_angle_beta                 89.981(2)
_cell_angle_gamma                75.078(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9675(3)
_cell_length_b                   11.0636(5)
_cell_length_c                   16.9266(8)
_cell_measurement_reflns_used    13712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.45
_cell_volume                     1062.50(9)
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_data_reduction
; 
SAINT V8.34A, XPREP v2014/2, (Bruker, 2014), SADABS V2014/4 
(Krause et al., 2015) 
 
;
_computing_molecular_graphics
; 
SHELXTL v2014-7 (Bruker, 2014), CrystalMaker v9.2.8 (CrystalMaker, 2016) 
;
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2018-3 (Sheldrick, 2015a)'
_computing_structure_solution    'SHELXT-2014-5 (Sheldrick, 2015b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  dm07tsa
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32605
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.184
_diffrn_reflns_theta_min         1.936
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.8700
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS V2014/4 (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             472
_exptl_crystal_id                dm07tsa
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (0 1 0) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.463
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4701
_refine_ls_number_restraints     124
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1094P)^2^+2.6254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.1951
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4301
_reflns_number_total             4701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02690_si_003.cif
_cod_data_source_block           dm07tsa
_cod_database_code               4127436
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              60719
_shelx_hkl_checksum              46468