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_4034768
_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 Br N6 O2, 3(C2 H6 O S)'
_chemical_formula_sum            'C25 H28 Br N6 O5 S3'
_chemical_formula_weight         668.62
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                74.081(15)
_cell_angle_beta                 83.934(18)
_cell_angle_gamma                83.108(19)
_cell_formula_units_Z            1
_cell_length_a                   5.680(3)
_cell_length_b                   8.711(4)
_cell_length_c                   15.304(7)
_cell_measurement_reflns_used    920
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.29
_cell_measurement_theta_min      2.44
_cell_volume                     720.8(6)
_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 0.981
_diffrn_measured_fraction_theta_max 0.600
_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  0.0409
_diffrn_reflns_av_unetI/netI     0.2470
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.600
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5341
_diffrn_reflns_theta_full        25.011
_diffrn_reflns_theta_max         33.912
_diffrn_reflns_theta_min         3.623
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.5613
_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    1.540
_exptl_crystal_description       plate
_exptl_crystal_F_000             343
_exptl_crystal_size_max          0.644
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.015(17)
_refine_ls_extinction_coef       0.021(4)
_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   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4624
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.1783
_refine_ls_R_factor_gt           0.0676
_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^)+(0.0361P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.319
_reflns_Friedel_fraction_full    0.267
_reflns_Friedel_fraction_max     0.191
_reflns_number_gt                2216
_reflns_number_total             4624
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02161_si_006.cif
_cod_data_source_block           vakh-kp635
_cod_database_code               4034768
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.409
_shelx_estimated_absorpt_t_max   0.923
_shelx_res_checksum              65824
_shelx_hkl_checksum              92125