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_4034770
_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         'C18 H13 N7 O2 S, 4(H2 O)'
_chemical_formula_sum            'C18 H21 N7 O6 S'
_chemical_formula_weight         463.48
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.623(3)
_cell_length_b                   18.287(9)
_cell_length_c                   33.616(15)
_cell_measurement_reflns_used    1145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      3.33
_cell_volume                     4071(3)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.723
_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  0.2336
_diffrn_reflns_av_unetI/netI     0.2533
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.723
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            14841
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         3.637
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4561
_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    1.512
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0177(14)
_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   0.852
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      0.853
_refine_ls_R_factor_all          0.3980
_refine_ls_R_factor_gt           0.0773
_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^)+(0.0378P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                952
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02161_si_005.cif
_cod_data_source_block           vakh_s632
_cod_database_code               4034770
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              16173
_shelx_hkl_checksum              53054