Electrochemical one-pot cascade synthesis of thio(seleno)cyanato-substituted thiazolidine-2-imines without external electrolyte
Yu, Xiao; Hao, Liqiang; Liu, xian; Jin, Shengkui; Li, Yangchen; Liu, Yiping; Ji, Yafei; Organic & Biomolecular Chemistry  (2024) –; doi:10.1039/D4OB01626B

data_7160192
_publ_section_title
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 Electrochemical one-pot cascade synthesis of
 thio(seleno)cyanato-substituted thiazolidine-2-imines without external
 electrolyte
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D4OB01626B
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H13 N3 O S Se'
_chemical_formula_sum            'C13 H13 N3 O S Se'
_chemical_formula_weight         338.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-23 deposited with the CCDC.	2024-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.722(3)
_cell_length_b                   7.1939(8)
_cell_length_c                   8.2904(8)
_cell_measurement_reflns_used    860
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      50.783
_cell_measurement_theta_min      3.731
_cell_volume                     1414.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            28958
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.727
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    4.939
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1741 before and 0.1027 after correction.
The Ratio of minimum to maximum transmission is 0.6421.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.201(12)
_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     173
_refine_ls_number_reflns         2492
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0515P)^2^+0.2714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0810
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2421
_reflns_number_total             2492
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01626b2.cif
_cod_data_source_block           yx_1_0ma_a
_cod_database_code               7160192
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.470
_shelx_estimated_absorpt_t_min   0.237
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00B(H00E), C00E(H00G), C00H(H00K), C00I(H00L)
2.d Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J)
;
_olex2_submission_special_instructions 'No special instructions were received'