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_7159760
_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         'C16 H9 Br N2'
_chemical_formula_sum            'C16 H9 Br N2'
_chemical_formula_weight         309.16
_chemical_name_systematic        9-bromobenzo[a]phenazine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.230(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.013(2)
_cell_length_b                   4.6349(7)
_cell_length_c                   16.5622(19)
_cell_measurement_reflns_used    2061
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7910
_cell_measurement_theta_min      3.7200
_cell_volume                     1222.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro system (CCD 43.96a 64-bit)'
_computing_data_reduction        'CrysAlisPro 1.171.43.96a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_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  0.1278
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6207
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        20.807
_diffrn_reflns_theta_max         20.807
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.348
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.96a (Rigaku Oxford Diffraction, 2023)
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            yellow
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: deuterated chloroform'
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.400
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1132P)^2^+1.6583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1009
_reflns_number_total             1276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02028b2.cif
_cod_data_source_block           B19812
_cod_depositor_comments
'Adding full bibliography for 7159759--7159762.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159760
_shelx_res_checksum              12301
_shelx_hkl_checksum              30842