An asymmetric alkynylation/hydrothiolation cascade: an enantioselective synthesis of thiazolidine-2-imines from imines, acetylenes and isothiocyanates
Alok Ranjan; Anupam Mandal; Swapnil G. Yerande; Dattatraya H. Dethe; Chem.Commun. 51 (2015) 14215–; doi:10.1039/C5cc05549K

data_7117759
_publ_section_title
;
 An asymmetric alkynylation/hydrothiolation cascade: an enantioselective
 synthesis of thiazolidine-2-imines from imines, acetylenes and
 isothiocyanates
;
_journal_name_full               Chem.Commun.
_journal_page_first              14215
_journal_paper_doi               10.1039/C5cc05549K
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C30 H23 Br N2 O S'
_chemical_formula_sum            'C30 H23 Br N2 O S'
_chemical_formula_weight         539.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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-2014/7
_audit_update_record
;
2015-05-29 deposited with the CCDC.
2015-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                75.443(5)
_cell_angle_beta                 87.986(5)
_cell_angle_gamma                89.040(5)
_cell_formula_units_Z            2
_cell_length_a                   9.724(5)
_cell_length_b                   11.581(5)
_cell_length_c                   11.774(5)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.10
_cell_volume                     1282.5(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.2088
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13366
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.096
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.710
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.761
_exptl_transmission_factor_min   0.705
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 1648 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.108(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         9327
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0884
_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^)+(0.0533P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1736
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                5260
_reflns_number_total             9327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05549k2.cif
_cod_data_source_block           compound1
_cod_database_code               7117759
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              85414