Enantioselective Synthesis of α-Allyl Amino Esters via Hydrogen-Bond-Donor Catalysis.
Bendelsmith, Andrew J.; Kim, Seohyun Chris; Wasa, Masayuki; Roche, Stéphane P; Jacobsen, Eric N.; Journal of the American Chemical Society 141 (2019) 11414–11419; doi:10.1021/jacs.9b05556

data_4127394
_publ_section_title
;
 Enantioselective Synthesis of \a-Allyl Amino Esters via
 Hydrogen-Bond-Donor Catalysis.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11414
_journal_page_last               11419
_journal_paper_doi               10.1021/jacs.9b05556
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H23 N O4 S'
_chemical_formula_weight         397.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1729(2)
_cell_length_b                   10.5450(4)
_cell_length_c                   35.9696(11)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.6
_cell_measurement_theta_min      2.49
_cell_volume                     1962.08(12)
_computing_cell_refinement       'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT 8.35A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            35289
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.628
_diffrn_reflns_theta_min         2.457
_exptl_absorpt_coefficient_mu    1.703
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1265 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_coef       0.0020(3)
_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   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3382
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0283P)^2^+1.2884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0862
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3263
_reflns_number_total             3382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05556_si_002.cif
_cod_data_source_block           80909535
_cod_database_code               4127394
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.706
_shelx_estimated_absorpt_t_max   0.848
_shelx_res_checksum              83653
_shelx_hkl_checksum              26107