One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions
Kang, Gui-Feng; Zhang, Gang; Beilstein Journal of Organic Chemistry 16 (2020) 1447–1455; doi:10.3762/bjoc.16.120

data_4038522
_publ_section_title
;
 One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via
 three-component reactions
;
_journal_name_full               'Beilstein Journal of Organic Chemistry'
_journal_page_first              1447
_journal_page_last               1455
_journal_paper_doi               10.3762/bjoc.16.120
_journal_volume                  16
_journal_year                    2020
_chemical_formula_moiety         'C10 H11 N3 S2'
_chemical_formula_sum            'C10 H11 N3 S2'
_chemical_formula_weight         237.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.991(9)
_cell_angle_beta                 98.639(8)
_cell_angle_gamma                95.953(8)
_cell_formula_units_Z            2
_cell_length_a                   5.258(4)
_cell_length_b                   8.810(6)
_cell_length_c                   12.257(9)
_cell_measurement_reflns_used    2921
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.465
_cell_measurement_theta_min      2.369
_cell_volume                     547.9(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2311
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         2.369
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1003 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.6931. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.660
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0898
_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^)+4.8484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2067
_reflns_number_total             2311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-16-120-S2.cif
_cod_data_source_block           190128kgf_0m_tw
_cod_depositor_comments          'Adding full bibliography for 4038522.cif.'
_cod_database_code               4038522
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.730(6)
 0.270(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              46277
_shelx_hkl_checksum              79000
_olex2_submission_special_instructions 'No special instructions were received'