PIFA-mediated intramolecular <i>N</i>-arylation of 2-aminoquinoxalines to afford indolo[2,3-<i>b</i>]quinoxaline derivatives.
Subramaniam, Subhashini V.; Singh, Badal; Pradeep, Natarajan; Peruncheralathan, Saravanan; Organic & biomolecular chemistry 22 (2024) 5803–5808; doi:10.1039/d4ob00812j

data_7160007
_publ_section_title
;
 PIFA-mediated intramolecular <i>N</i>-arylation of 2-aminoquinoxalines to
 afford indolo[2,3-<i>b</i>]quinoxaline derivatives.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5803
_journal_page_last               5808
_journal_paper_doi               10.1039/d4ob00812j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H15 N3 O2 S'
_chemical_formula_sum            'C21 H15 N3 O2 S'
_chemical_formula_weight         373.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2k2fkn
_audit_creation_date             2024-04-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-16 deposited with the CCDC.	2024-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.527(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9867(2)
_cell_length_b                   18.9604(5)
_cell_length_c                   11.5410(3)
_cell_measurement_reflns_used    12739
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      31.9290
_cell_measurement_theta_min      3.6740
_cell_volume                     1728.35(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.837
_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    -21.00  37.00   0.50   25.73    --    7.48 -94.00 150.00  116
  2  \w    -14.00  19.00   0.50   25.73    --   -8.10 -94.00 150.00   66
  3  \w     -3.00  45.00   0.50   25.73    --    7.48  57.00 -30.00   96
  4  \w     -8.00  21.00   0.50   25.73    --    7.48 -99.00 -30.00   58
  5  \w    -43.00  -5.00   0.50   25.73    --   -8.10 -37.00-150.00   76
  6  \w    -74.00 -48.00   0.50   25.73    --   -8.10 -37.00-150.00   52
  7  \w    -73.00  -5.00   0.50   25.73    --   -8.10 -37.00 150.00  136
  8  \w     17.00  43.00   0.50   25.73    --   -8.10  57.00-180.00   52
  9  \w    -31.00   9.00   0.50   25.73    --   -8.10  77.00   0.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0162872000
_diffrn_orient_matrix_UB_12      0.0313248000
_diffrn_orient_matrix_UB_13      0.0333384000
_diffrn_orient_matrix_UB_21      0.0392247000
_diffrn_orient_matrix_UB_22      0.0149916000
_diffrn_orient_matrix_UB_23      -0.0455327000
_diffrn_orient_matrix_UB_31      -0.0790953000
_diffrn_orient_matrix_UB_32      0.0138794000
_diffrn_orient_matrix_UB_33      -0.0260858000
_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  0.0272
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19476
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.922
_diffrn_reflns_theta_min         3.516
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method 'slow diffusion method'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.8341P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4412
_reflns_number_total             4989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00812j2.cif
_cod_data_source_block           vs_900
_cod_depositor_comments
'Adding full bibliography for 7160006--7160007.cif.'
_cod_database_code               7160007
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C84 H60 N12 O8 S4 '
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C19(H19), C2(H2), C17(H17), C3(H3), C5(H5), C4(H4),
 C10(H10), C13(H13), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              43475
_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 1.550
_oxdiff_exptl_absorpt_empirical_full_min 0.375