Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones via a sequential Ugi‒Smiles type/nucleophilic substitution/cyclization reaction
Ramezanpour, Sorour; Rezaei, Mohammad Nasim; Vaezghaemi, Aref; Rominger, Frank; New Journal of Chemistry 42 (2018) 17533–; doi:10.1039/C8NJ03949F

data_7057752
_publ_section_title
;
 Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones
 via a sequential Ugi--Smiles type/nucleophilic substitution/cyclization
 reaction
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17533
_journal_paper_doi               10.1039/C8NJ03949F
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C20 H17 N5 O6 S'
_chemical_formula_weight         455.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-11 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_measurement_reflns_used    22792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.39
_cell_measurement_theta_min      4.85
_cell_volume                     3977.87(17)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16394
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.628
_diffrn_reflns_theta_min         4.856
_diffrn_source                   'Genix3D Cu HF'
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_T_max  1.499
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       'little rod'
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.130
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_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     481
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+1.8895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3261
_reflns_number_total             4055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj03949f2.cif
_cod_data_source_block           sba152
_cod_depositor_comments
'Adding full bibliography for 7057752--7057754.cif.'
_cod_original_cell_volume        3977.88(17)
_cod_database_code               7057752
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.790
_shelx_estimated_absorpt_t_max   0.911
_exptl_absorpt_special_details   'STOE X-AREA Laue Analyzer'
_shelx_res_checksum              68443