Sodium sulfide-promoted regiodefined redox condensation of o-nitroanilines with aryl ketones to benzo[a]phenazines and quinoxalines
Le, Duc Long; Nguyen, Le Anh; Vo, Ngoc Binh; Nguyen, Thi Thu Tram; Ngo, Quoc Anh; Retailleau, Pascal; Nguyen, Thanh Binh; Organic & Biomolecular Chemistry 22 (2024) 1167–1171; doi:10.1039/D3OB02028B

data_7159762
_publ_section_title
;
 Sodium sulfide-promoted regiodefined redox condensation of
 o-nitroanilines with aryl ketones to benzo[a]phenazines and quinoxalines
;
_journal_issue                   6
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1167
_journal_page_last               1171
_journal_paper_doi               10.1039/D3OB02028B
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C14 H9 Br N2'
_chemical_formula_sum            'C14 H9 Br N2'
_chemical_formula_weight         285.144
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-26
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.633(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6512(5)
_cell_length_b                   4.9125(2)
_cell_length_c                   12.4349(9)
_cell_measurement_reflns_used    4422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6730
_cell_measurement_theta_min      3.3840
_cell_volume                     570.43(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement
'olex2.refine 1.5-ac5-024 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -24.00  90.00   0.50    3.00    --    6.50  37.00  69.00  228
  2  \w      4.00  62.00   0.50    3.00    --   -7.20  37.00  69.00  116
  3  \w     -1.00  25.00   0.50    3.00    --    6.50  57.00 -90.00   52
  4  \w    -22.00  83.00   0.50    3.00    --    6.50  57.00 120.00  210
  5  \w     29.00  95.00   0.50    3.00    --    6.50  57.00 -60.00  132
  6  \w    -21.00   5.00   0.50    3.00    --    6.50  57.00-180.00   52
  7  \w    -24.00  81.00   0.50    3.00    --   -7.20  57.00 -30.00  210
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0221082000
_diffrn_orient_matrix_UB_12      0.0669004000
_diffrn_orient_matrix_UB_13      -0.0521083000
_diffrn_orient_matrix_UB_21      0.0706062000
_diffrn_orient_matrix_UB_22      -0.0100682000
_diffrn_orient_matrix_UB_23      -0.0067661000
_diffrn_orient_matrix_UB_31      -0.0171336000
_diffrn_orient_matrix_UB_32      -0.1275177000
_diffrn_orient_matrix_UB_33      -0.0267934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9965
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10735
_diffrn_reflns_point_group_measured_fraction_full 0.9883
_diffrn_reflns_point_group_measured_fraction_max 0.9375
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         3.39
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_description       stick
_exptl_crystal_F_000             283.744
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: deuterated chloroform'
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.6002
_refine_diff_density_min         -0.4865
_refine_diff_density_rms         0.0565
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.002(5)
_refine_ls_d_res_high            0.7301
_refine_ls_d_res_low             6.0158
_refine_ls_extinction_coef       0.0165(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0575
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.0551
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0240
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0070P)^2^+0.0996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0400
_refine_ls_wR_factor_ref         0.0419
_reflns_Friedel_coverage         0.864
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              6
_reflns_limit_k_min              -6
_reflns_limit_l_max              17
_reflns_limit_l_min              -16
_reflns_number_gt                2440
_reflns_number_total             2878
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob02028b2.cif
_cod_data_source_block           TD55
_cod_depositor_comments
'Adding full bibliography for 7159759--7159762.cif.'
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7159762
_chemical_oxdiff_formula         'C19 H14 Br N2'
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(H2) \\sim Ueq, Uanis(H10) \\sim Ueq: with sigma of 0.03 and sigma for
terminal atoms of 0.02
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.104
_oxdiff_exptl_absorpt_empirical_full_min 0.767