Diastereoselective and Catalytic α-Alkylation of Chiral N-Acyl Thiazolidinethiones with Stable Carbocationic Salts.
Kennington, Stuart C. D.; Ferré, Mònica; Romo, Juan M.; Romea, Pedro; Urpí, Fèlix; Font-Bardia, Mercè; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00657

data_4032516
_publ_section_title
;
 Diastereoselective and Catalytic \a-Alkylation of Chiral N-Acyl
 Thiazolidinethiones with Stable Carbocationic Salts.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00657
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H22 N2 O3 S2'
_chemical_formula_sum            'C23 H22 N2 O3 S2'
_chemical_formula_weight         438.54
_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   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6175(2)
_cell_length_b                   12.9014(4)
_cell_length_c                   19.9410(7)
_cell_measurement_reflns_used    5495
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.57
_cell_volume                     2217.00(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16042
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.410
_diffrn_reflns_theta_min         2.575
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0445P)^2^+0.4413P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1202
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3441
_reflns_number_total             4541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00657_si_003.cif
_cod_data_source_block           mo_O31UB144B_0m_a
_cod_database_code               4032516