Metal-free cascade reactions for one-pot tetrahydroquinoxaline construction through nitroarene reduction and imine hydrogenation with water
Chen, Yanqi; Hao, Subin; Yin, Lingfeng; Song, Xinluo; Liu, Zhiyao; Li, Mingde; Dang, Li; New Journal of Chemistry 48 (2024) 6103–6108; doi:10.1039/D3NJ05093A

data_7063070
_publ_section_title
;
 Metal-free cascade reactions for one-pot tetrahydroquinoxaline
 construction through nitroarene reduction and imine hydrogenation with
 water
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6103
_journal_page_last               6108
_journal_paper_doi               10.1039/D3NJ05093A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_chemical_name_systematic        'CCDC Area Detector'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-08-31 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                109.053(2)
_cell_angle_beta                 93.530(2)
_cell_angle_gamma                92.661(2)
_cell_formula_units_Z            2
_cell_length_a                   5.69230(10)
_cell_length_b                   11.2384(3)
_cell_length_c                   11.8487(3)
_cell_measurement_reflns_used    4819
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      70.8520
_cell_measurement_theta_min      4.7100
_cell_volume                     713.32(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (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      99.99(10)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.962
_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     54.00  79.00   0.50    0.50    --    0.00  38.00-150.00   50
  2  \w    -57.00 -30.00   0.50    0.50    --    0.00 -38.00-150.00   54
  3  \w    -89.00 -56.00   0.50    0.50    --    0.00 -77.00  90.00   66
  4  \w    -15.00  32.00   0.50    0.50    --    0.00  38.00-150.00   94
  5  \w    -16.00  10.00   0.50    0.50    --    0.00 -38.00-150.00   52
  6  \w    -11.00  21.00   0.50    0.50    --    0.00 -77.00  90.00   64
  7  \w      0.00  44.00   0.50    0.50    --   89.30 -77.00   0.00   88
  8  \w     77.00 103.00   0.50    0.50    --   89.30 -82.00 150.00   52
  9  \w     31.00  86.00   0.50    0.50    --   89.30 -61.00  60.00  110
 10  \w      0.00 108.00   0.50    0.50    --   89.30 -61.00 -90.00  216
 11  \w     22.00 108.00   0.50    0.50    --   89.30 -45.00 120.00  172
 12  \w     85.00 112.00   0.50    0.50    --   89.30 -61.00 -60.00   54
 13  \w     41.00  72.00   0.50    0.50    --   89.30 -82.00 150.00   62
 14  \w      0.00 101.00   0.50    0.50    --   89.30 -30.00  30.00  202
 15  \w     23.00  49.00   0.50    0.50    --   89.30 -61.00 -60.00   52
 16  \w     76.00 120.00   0.50    0.50    --   89.30 -82.00 120.00   88
 17  \w     62.00 113.00   0.50    0.50    --   89.30 -77.00   0.00  102
 18  \w     80.00 147.00   0.50    0.50    --   89.30  30.00-120.00  134
 19  \w     19.00 121.00   0.50    0.50    --   89.30 -82.00 -90.00  204
 20  \w     74.00  99.00   0.50    0.50    --   89.30  61.00-120.00   50
 21  \w     72.00 179.00   0.50    0.50    --   89.30  15.00-180.00  214
;
_diffrn_measurement_device       'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0072095000
_diffrn_orient_matrix_UB_12      0.1430742000
_diffrn_orient_matrix_UB_13      0.0221010000
_diffrn_orient_matrix_UB_21      -0.0848140000
_diffrn_orient_matrix_UB_22      0.0217412000
_diffrn_orient_matrix_UB_23      0.1257109000
_diffrn_orient_matrix_UB_31      0.2581582000
_diffrn_orient_matrix_UB_32      0.0139411000
_diffrn_orient_matrix_UB_33      0.0524918000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6217
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.971
_diffrn_reflns_theta_min         3.960
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0661P)^2^+0.5015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2488
_reflns_number_total             2634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05093a2.cif
_cod_data_source_block           20230302b
_cod_depositor_comments
'Adding full bibliography for 7063070--7063071.cif.'
_cod_database_code               7063070
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H O N'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C19(H19), C3(H3), C18(H18), C00C(H00C), C17(H17), C5(H5), C13(H13),
 C16(H16), C15(H15), C11(H11), C12(H12), C1(H1A), C2(H2), C6(H6)
;
_olex2_submission_original_sample_id 'CCDC Area Detector'
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.454