Rearrangement of thiazolidine derivatives - a synthesis of a chiral fused oxathiane-γ-lactam bicyclic system.
Kamińska, Karolina; Iwan, Dominika; Trojnar, Jakub; Daszkiewicz, Marek; Rode, Joanna E.; Wojaczyński, Jacek; Wojaczyńska, Elżbieta; Organic & biomolecular chemistry 21 (2023) 9182–9191; doi:10.1039/d3ob01454a

data_7159645
_publ_section_title
;
 Rearrangement of thiazolidine derivatives - a synthesis of a chiral fused
 oxathiane-&#x3b3;-lactam bicyclic system.
;
_journal_issue                   46
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9182
_journal_page_last               9191
_journal_paper_doi               10.1039/d3ob01454a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C9 H15 N O2 S'
_chemical_formula_sum            'C9 H15 N O2 S'
_chemical_formula_weight         201.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2c6ffg
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-21 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.918(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.872(3)
_cell_length_b                   6.6196(7)
_cell_length_c                   16.260(2)
_cell_measurement_reflns_used    1176
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.7960
_cell_measurement_theta_min      3.6620
_cell_volume                     2023.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.6249
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5194
_diffrn_reflns_point_group_measured_fraction_full 0.780
_diffrn_reflns_point_group_measured_fraction_max 0.747
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.726
_diffrn_reflns_theta_min         2.648
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 430 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0103(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3217
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0752
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0830P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.382
_reflns_Friedel_fraction_full    0.515
_reflns_Friedel_fraction_max     0.454
_reflns_number_gt                1916
_reflns_number_total             3217
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01454a2.cif
_cod_data_source_block           EWKK21-016kr1
_cod_depositor_comments
'Adding full bibliography for 7159641--7159650.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7159645
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.857
_shelx_estimated_absorpt_t_max   0.991
_oxdiff_exptl_absorpt_empirical_full_min 0.475
_oxdiff_exptl_absorpt_empirical_full_max 16.455
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              33336