Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis of 2-hydrazonoimidazo[4,5-d]thiazolones
Vinogradova, Ekaterina E.; Gazieva, Galina A.; Izmest'ev, Alexei N.; Karnoukhova, Valentina A.; Kravchenko, Angelina N.; RSC Advances 11 (2021) 28395–28400; doi:10.1039/D1RA05568B

data_7243415
_publ_section_title
;
 Dimroth-type N/S-interchange of N-aminothioglycolurils in the synthesis
 of 2-hydrazonoimidazo[4,5-d]thiazolones
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              28395
_journal_page_last               28400
_journal_paper_doi               10.1039/D1RA05568B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C13 H15 N5 O S'
_chemical_formula_sum            'C13 H15 N5 O S'
_chemical_formula_weight         289.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-08-09 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7481(5)
_cell_length_b                   9.6628(4)
_cell_length_c                   30.3545(14)
_cell_measurement_reflns_used    229
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     2859.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST, Photon III detector'
_diffrn_measurement_method       '\f and \w shutterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            41443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_min         2.483
_diffrn_source                   'fine-focus sealed X-Ray tube'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0447P)^2^+2.3493P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2120
_reflns_number_total             2955
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d1ra05568b2.cif
_cod_data_source_block           10a
_cod_database_code               7243415
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              30037