Rearrangement of Quinoxalin-2-ones When Exposed to Enamines Generated in Situ from Ketones and Ammonium Acetate: Method for the Synthesis of 1-(Pyrrolyl)benzimidazolones.
Mamedov, Vakhid A.; Zhukova, Nataliya A.; Beschastnova, Tat'yana N.; Syakaev, Victor V.; Krivolapov, Dmitry B.; Mironova, Ekaterina V.; Zamaletdinova, Anastasiya I.; Rizvanov, Il'dar Kh; Latypov, Shamil K.; The Journal of organic chemistry 80 (2015) 1375–1386; doi:10.1021/jo502135d

data_4030452
_publ_section_title
;
 Rearrangement of Quinoxalin-2-ones When Exposed to Enamines Generated in
 Situ from Ketones and Ammonium Acetate: Method for the Synthesis of
 1-(Pyrrolyl)benzimidazolones.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1375
_journal_page_last               1386
_journal_paper_doi               10.1021/jo502135d
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C31 H31 Br N2 O2'
_chemical_formula_sum            'C31 H31 Br N2 O2'
_chemical_formula_weight         543.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.176(12)
_cell_angle_beta                 76.230(13)
_cell_angle_gamma                65.626(12)
_cell_formula_units_Z            2
_cell_length_a                   11.354(12)
_cell_length_b                   11.372(12)
_cell_length_c                   12.317(13)
_cell_measurement_reflns_used    1327
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.09
_cell_measurement_theta_min      2.31
_cell_volume                     1290(2)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_sigmaI/netI    0.1589
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9987
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.86
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Smart APEX II'
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_correction_T_min  0.7370
_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            colorless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.594
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4986
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1690
_refine_ls_R_factor_gt           0.0950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1573P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.2818
_reflns_number_gt                2672
_reflns_number_total             4986
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502135d_si_006.cif
_cod_data_source_block           v500_fin
_cod_depositor_comments
'Adding full bibliography for 4030450--4030452.cif.'
_cod_database_code               4030452