TBAI-promoted synthesis of thioenamines <i>via</i> C-S bond formation between enaminones and thiosulfonates.
Chang, Meng-Ran; Wu, Yu-Xi; Li, He-Yi; Li, Yao-Yao; Cui, Jing-Jing; Chi, Ru-An; Guan, Zhi-Peng; Han, Qing-Wen; Dong, Zhi-Bing; Organic & biomolecular chemistry 23 (2025) 10194–10199; doi:10.1039/d5ob01371b

data_7160806
_publ_section_title
;
 TBAI-promoted synthesis of thioenamines <i>via</i> C-S bond formation
 between enaminones and thiosulfonates.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10194
_journal_page_last               10199
_journal_paper_doi               10.1039/d5ob01371b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C19 H21 N O2 S'
_chemical_formula_sum            'C19 H21 N O2 S'
_chemical_formula_weight         327.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-10 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.542(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.752(4)
_cell_length_b                   11.319(2)
_cell_length_c                   8.2409(19)
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.52
_cell_measurement_theta_min      2.83
_cell_volume                     1741.0(6)
_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 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            25738
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.198
_diffrn_reflns_theta_min         2.829
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5778
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0875 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.7754.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0709
_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^)+(0.0411P)^2^+2.2253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1682
_reflns_number_total             3085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01371b2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7160806.cif.'
_cod_original_cell_volume        1741.0(7)
_cod_database_code               7160806
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C15(H15), C10(H10), C14(H14), C4(H4), C2(H2), C5(H5),
 C1(H1)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              78595
_olex2_submission_special_instructions 'No special instructions were received'