Room temperature dithiocarbamation of 2-tetralones with elemental sulfur and isothiocyanates S<sub>8</sub>/R-NCS: atom-efficient access to 4-hydroxythiazolidine-2-thiones.
Nguyen, Le Anh; Ngo, Quoc Anh; Retailleau, Pascal; Nguyen, Thanh Binh; Chemical communications (Cambridge, England) 60 (2024) 13586–13589; doi:10.1039/d4cc05053c

data_7133900
_publ_section_title
;
 Room temperature dithiocarbamation of 2-tetralones with elemental sulfur
 and isothiocyanates S<sub>8</sub>/R-N&#xe001;C&#xe001;S: atom-efficient
 access to 4-hydroxythiazolidine-2-thiones.
;
_journal_issue                   92
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13586
_journal_page_last               13589
_journal_paper_doi               10.1039/d4cc05053c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C17 H15 N O S2'
_chemical_formula_sum            'C17 H15 N O S2'
_chemical_formula_weight         313.42
_chemical_name_systematic
rac-(3aR,9bR)-3a-hydroxy-3-phenyl-3a,4,5,9b-tetrahydronaphtho[2,1-d]thiazole-2(3H)-thione
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-08-06 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.99(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2278(8)
_cell_length_b                   22.429(6)
_cell_length_c                   9.660(7)
_cell_measurement_reflns_used    1291
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6990
_cell_measurement_theta_min      2.7940
_cell_volume                     1546.8(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro system (CCD 43.98a 64-bit)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19727
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.803
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
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    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         6347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.856
_reflns_number_gt                5327
_reflns_number_total             6347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05053c2.cif
_cod_data_source_block           B19955
_cod_depositor_comments
'Adding full bibliography for 7133900--7133901.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7133900
_shelx_estimated_absorpt_t_min   0.808
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              20250
_shelx_hkl_checksum              42603