Multicomponent Cascade Reactions of Unprotected Ketoses and Amino Acids - Access to a Defined Configured Quaternary Stereogenic Center.
Richter, Celin; Nguyen Trung, Minh; Mahrwald, Rainer; The Journal of organic chemistry 80 (2015) 10849–10865; doi:10.1021/acs.joc.5b02003

data_4031716
_publ_section_title
;
 Multicomponent Cascade Reactions of Unprotected Ketoses and Amino Acids -
 Access to a Defined Configured Quaternary Stereogenic Center.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10849
_journal_page_last               10865
_journal_paper_doi               10.1021/acs.joc.5b02003
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H24 N2 O3 S'
_chemical_formula_sum            'C13 H24 N2 O3 S'
_chemical_formula_weight         288.40
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0282(3)
_cell_length_b                   14.1182(6)
_cell_length_c                   18.3287(13)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.65
_cell_volume                     1559.91(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20192
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.446
_diffrn_reflns_theta_min         2.650
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.5262
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'PLATON, 1990'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2869
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0257
_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^)+(0.0259P)^2^+0.4212P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0664
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2840
_reflns_number_total             2869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02003_si_002.cif
_cod_data_source_block           20d15
_cod_depositor_comments
'Adding full bibliography for 4031716--4031718.cif.'
_cod_database_code               4031716
_shelx_estimated_absorpt_t_min   0.903
_shelx_estimated_absorpt_t_max   0.947
_shelxl_version_number           2013-4
_shelx_res_checksum              60916
_shelx_hkl_checksum              59606