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_7160006
_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         'C25 H15 F6 N3 O5 S'
_chemical_formula_sum            'C25 H15 F6 N3 O5 S'
_chemical_formula_weight         583.471
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2k2fjm
_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                106.334(3)
_cell_angle_beta                 92.084(3)
_cell_angle_gamma                95.137(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2215(2)
_cell_length_b                   10.8817(3)
_cell_length_c                   16.0374(6)
_cell_measurement_reflns_used    11366
_cell_measurement_temperature    298.0(7)
_cell_measurement_theta_max      77.6110
_cell_measurement_theta_min      4.1910
_cell_volume                     1202.03(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.0(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9641
_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    -74.00  15.00   0.50    2.40    --  -38.50 101.00 -13.00  178
  2  \w      7.00  86.00   0.50    2.40    --   49.56-101.00-117.00  158
  3  \w    104.00 175.00   0.50    9.52    --  107.46 101.00 -13.00  142
  4  \w     40.00 107.00   0.50    9.52    --  107.46-101.00-117.00  134
  5  \w   -101.00 -26.00   0.50    2.40    --  -38.50 -59.00 163.80  150
  6  \w   -101.00 -27.00   0.50    2.40    --  -38.50 -58.00-163.32  148
  7  \w    -44.00  31.00   0.50    2.40    --  -38.50  19.00 150.00  150
  8  \w    -86.00  -6.00   0.50    2.40    --  -38.50 125.00  60.00  160
  9  \w   -101.00 -27.00   0.50    2.40    --  -38.50 -57.00-120.00  148
 10  \w    -13.00  61.00   0.50    2.40    --   49.56 -57.00 -90.00  148
 11  \w     38.00 113.00   0.50    2.40    --   49.56  57.00   0.00  150
 12  \w     39.00 107.00   0.50    9.52    --  107.46 -94.00-180.00  136
 13  \w     45.00 113.00   0.50    9.52    --  107.46-125.00  30.00  136
 14  \w    103.00 172.00   0.50    9.52    --  107.46  77.00-120.00  138
 15  \w     99.00 176.00   0.50    9.52    --  107.46  15.00 150.00  154
 16  \w     43.00 131.00   0.50    9.52    --  107.46 -77.00-120.00  176
 17  \w     39.00 116.00   0.50    9.52    --  107.46 -15.00-120.00  154
 18  \w     95.00 170.00   0.50    9.52    --  107.46  60.00  36.09  150
 19  \w     45.00 113.00   0.50    9.52    --  107.46-125.00  60.00  136
 20  \w     43.00 112.00   0.50    9.52    --  107.46 -45.00  90.00  138
 21  \w     43.00 112.00   0.50    9.52    --  107.46 -45.00  30.00  138
 22  \w     43.00 112.00   0.50    9.52    --  107.46 -45.00 150.00  138
 23  \w    103.00 172.00   0.50    9.52    --  107.46  77.00-180.00  138
 24  \w     39.00 107.00   0.50    9.52    --  107.46 -94.00  60.00  136
 25  \w     39.00 107.00   0.50    9.52    --  107.46 -94.00 120.00  136
 26  \w     39.00 107.00   0.50    9.52    --  107.46 -94.00 -30.00  136
 27  \w    103.00 172.00   0.50    9.52    --  107.46  77.00 -30.00  138
 28  \w     45.00 121.00   0.50    9.52    --  107.46 -61.00-120.00  152
 29  \w     43.00 112.00   0.50    9.52    --  107.46 -45.00 -60.00  138
 30  \w     45.00 121.00   0.50    9.52    --  107.46 -61.00  30.00  152
 31  \w     39.00 107.00   0.50    9.52    --  107.46 -94.00 150.00  136
 32  \w     99.00 176.00   0.50    9.52    --  107.46  15.00  90.00  154
 33  \w     38.00 113.00   0.50    2.40    --   49.56  57.00  60.00  150
;
_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      -0.0191005000
_diffrn_orient_matrix_UB_12      -0.1103875000
_diffrn_orient_matrix_UB_13      0.0427786000
_diffrn_orient_matrix_UB_21      -0.0936897000
_diffrn_orient_matrix_UB_22      -0.0913824000
_diffrn_orient_matrix_UB_23      -0.0855414000
_diffrn_orient_matrix_UB_31      0.1921622000
_diffrn_orient_matrix_UB_32      -0.0382920000
_diffrn_orient_matrix_UB_33      -0.0302401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.9984
_diffrn_reflns_Laue_measured_fraction_max 0.9641
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17841
_diffrn_reflns_point_group_measured_fraction_full 0.9984
_diffrn_reflns_point_group_measured_fraction_max 0.9641
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         79.47
_diffrn_reflns_theta_min         4.26
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.039
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_description       needle
_exptl_crystal_F_000             595.276
_exptl_crystal_recrystallization_method 'slow diffusion method'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.9574
_refine_diff_density_min         -1.1371
_refine_diff_density_rms         0.4443
_refine_ls_d_res_high            0.7841
_refine_ls_d_res_low             10.3858
_refine_ls_goodness_of_fit_ref   1.0094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     362
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0094
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          -0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1240P)^2^+0.4801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4417
_reflns_number_total             5026
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00812j2.cif
_cod_data_source_block           SP_VS_968_auto
_cod_depositor_comments
'Adding full bibliography for 7160006--7160007.cif.'
_cod_database_code               7160006
_chemical_oxdiff_formula         'C H N O S F'
_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 Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C13(H13), C11(H11), C2(H2), C24(H24), C12(H12), C23(H23),
 C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C25(H25a,H25b,H25c)
;
_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 3.828
_oxdiff_exptl_absorpt_empirical_full_min 0.345