Stereoselective Alkylation of (S)-N-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones Catalyzed by (Me3P)2NiCl2.
Fernández-Valparís, Javier; Romo, Juan Manuel; Romea, Pedro; Urpí, Fèlix; Kowalski, Hubert; Font-Bardia, Mercè; Organic letters 17 (2015) 3540–3543; doi:10.1021/acs.orglett.5b01626

data_1520729
_publ_section_title
;
 Stereoselective Alkylation of
 (S)-N-Acyl-4-isopropyl-1,3-thiazolidine-2-thiones Catalyzed by
 (Me3P)2NiCl2.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3540
_journal_page_last               3543
_journal_paper_doi               10.1021/acs.orglett.5b01626
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C25 H31 N O3 S2'
_chemical_formula_sum            'C25 H31 N O3 S2'
_chemical_formula_weight         457.63
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 109.220(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.6067(3)
_cell_length_b                   19.7090(10)
_cell_length_c                   9.7407(5)
_cell_measurement_reflns_used    9381
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.44
_cell_volume                     1197.65(10)
_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-97 (Sheldrick 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         2.067
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 3278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.003(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         7323
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0293
_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^)+(0.0439P)^2^+0.1416P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6980
_reflns_number_total             7323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01626_si_002.cif
_cod_data_source_block           mo_O31TB12_0m
_cod_depositor_comments          'Adding full bibliography for 1520729.cif.'
_cod_database_code               1520729