One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine Derivatives via H<sub>2</sub>SO<sub>4</sub>-Catalyzed Rearrangement of Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and 2,5,6-Triaminopyrimidin-4-ols.
Mamedov, Vakhid A.; Zhukova, Nataliya A.; Gubaidullin, Aidar T.; Syakaev, Victor V.; Kadyrova, Milyausha S.; Beschastnova, Tat'yana N.; Bazanova, Olga B.; Rizvanov, Il Dar Kh; Latypov, Shamil K.; The Journal of organic chemistry 83 (2018) 14942–14953; doi:10.1021/acs.joc.8b02161

data_4034769
_publ_section_title
;
 One-Pot Synthesis of 7-(Benzimidazol-2-yl)thioxolumazine and -lumazine
 Derivatives via H<sub>2</sub>SO<sub>4</sub>-Catalyzed Rearrangement of
 Quinoxalinones When Exposed to 5,6-Diamino-2-mercapto- and
 2,5,6-Triaminopyrimidin-4-ols.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14942
_journal_page_last               14953
_journal_paper_doi               10.1021/acs.joc.8b02161
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C19 H10 Cl2 N6 O S, C3 H7 N O, H2 O'
_chemical_formula_sum            'C22 H19 Cl2 N7 O3 S'
_chemical_formula_weight         532.40
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.015(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5695(18)
_cell_length_b                   10.9440(12)
_cell_length_c                   14.1194(18)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      21.25
_cell_measurement_theta_min      2.36
_cell_volume                     2396.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0923
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22724
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         31.740
_diffrn_reflns_theta_min         3.444
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
 Siemens Area Detector Absorption Correction Program.
 Bruker AXS. Madison. Wisconsin. USA
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       plate
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.675
_exptl_crystal_size_mid          0.539
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       0.0025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7514
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.0693
_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^)+(0.0665P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1707
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3403
_reflns_number_total             7514
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02161_si_004.cif
_cod_data_source_block           vakh-s686_1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034769
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.775
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              72369
_shelx_hkl_checksum              74397