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_4030451
_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         'C22 H16 N4 O'
_chemical_formula_sum            'C22 H16 N4 O'
_chemical_formula_weight         352.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.676(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.270(4)
_cell_length_b                   20.421(8)
_cell_length_c                   10.817(5)
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.05
_cell_measurement_theta_min      3.35
_cell_volume                     1823.0(14)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22092
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         32.00
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Kappa Apex II CCD'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_correction_T_min  0.9758
_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    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0647
_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^)+(0.1233P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.2252
_reflns_number_gt                3494
_reflns_number_total             6329
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502135d_si_005.cif
_cod_data_source_block           v469_fin
_cod_depositor_comments
'Adding full bibliography for 4030450--4030452.cif.'
_cod_original_cell_volume        1823.2(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030451