Direct transition-metal-free synthesis of 2-heteroaryl-4-quinolones <i>via</i> ANRORC type rearrangement of 3-(2-(2-nitrophenyl)-2-oxoethyl)quinoxalin-2(1<i>H</i>)-ones.
Mamedov, Vakhid A.; Galimullina, Venera R.; Nikolaeva, Dariya V.; Syakaev, Victor V.; Babaeva, Olga B.; Rizvanov, Il'dar Kh; Gubaidullin, Aidar T.; Sinyashin, Oleg G.; Organic & biomolecular chemistry 23 (2025) 9388–9399; doi:10.1039/d5ob01303h

data_7160771
_publ_section_title
;
 Direct transition-metal-free synthesis of 2-heteroaryl-4-quinolones
 <i>via</i> ANRORC type rearrangement of
 3-(2-(2-nitrophenyl)-2-oxoethyl)quinoxalin-2(1<i>H</i>)-ones.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9388
_journal_page_last               9399
_journal_paper_doi               10.1039/d5ob01303h
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C16 H11 N3 O4'
_chemical_formula_sum            'C16 H11 N3 O4'
_chemical_formula_weight         309.28
_chemical_melting_point          274.5(5)
_chemical_name_systematic
(E)-3-(2-(2-nitrophenyl)-2-oxoethylidene)-3,4-dihydroquinoxalin-2(1H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-06-18 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 130.660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.296(11)
_cell_length_b                   12.509(7)
_cell_length_c                   14.318(13)
_cell_measurement_reflns_used    302
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      19.58
_cell_measurement_theta_min      3.26
_cell_volume                     2758(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'area detector PHOTON III'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1742
_diffrn_reflns_av_unetI/netI     0.2318
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6914
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        26.500
_diffrn_reflns_theta_max         27.284
_diffrn_reflns_theta_min         2.098
_diffrn_source                   'microfocus I\mS DIAMOND Mo X-ray tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5842
_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
  Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  SADABS-2016/2, J. Appl. Cryst. 48 (2015) 3-10. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       prism
_exptl_crystal_F_000             1280
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dimethylformamide'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.027(5)
_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   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0992
_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^)+(0.0610P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1200
_reflns_number_total             2457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01303h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '274-275' was changed to
'274.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160771--7160775.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7160771
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              48020