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_7063071
_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_absolute_configuration unk
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2023-08-09
_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                90.00
_cell_angle_beta                 105.805(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1113(5)
_cell_length_b                   6.7331(3)
_cell_length_c                   11.6092(7)
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.6540
_cell_measurement_theta_min      6.5350
_cell_volume                     610.06(6)
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_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    -13.00  26.00   0.50    0.50    --    0.00 -77.00-180.00   78
  2  \w    -88.00 -44.00   0.50    0.50    --    0.00 -77.00-180.00   88
  3  \w    -87.00 -39.00   0.50    0.50    --    0.00 -38.00 -60.00   96
  4  \w     27.00 118.00   0.50    0.50    --   89.30 -82.00  30.00  182
  5  \w     16.00 106.00   0.50    0.50    --   89.30 -15.00 -30.00  180
  6  \w     72.00 120.00   0.50    0.50    --   89.30 -82.00 -90.00   96
  7  \w      8.00 110.00   0.50    0.50    --   89.30 -15.00  60.00  204
  8  \w     59.00  84.00   0.50    0.50    --   89.30 -45.00  90.00   50
  9  \w     28.00 101.00   0.50    0.50    --   89.30 -61.00  30.00  146
;
_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      0.1912826000
_diffrn_orient_matrix_UB_12      0.0038543000
_diffrn_orient_matrix_UB_13      0.0696680000
_diffrn_orient_matrix_UB_21      -0.0494012000
_diffrn_orient_matrix_UB_22      -0.0043483000
_diffrn_orient_matrix_UB_23      0.1190161000
_diffrn_orient_matrix_UB_31      0.0046852000
_diffrn_orient_matrix_UB_32      -0.2285274000
_diffrn_orient_matrix_UB_33      -0.0009140000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2450
_diffrn_reflns_theta_full        70.57
_diffrn_reflns_theta_max         70.57
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72842
_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            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_coef       0.0040(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1479
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.4440P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                1398
_reflns_number_total             1479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3nj05093a2.cif
_cod_data_source_block           20230310a
_cod_depositor_comments
'Adding full bibliography for 7063070--7063071.cif.'
_cod_database_code               7063071
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H O N'
_reflns_odcompleteness_completeness 99.48
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7C(H7C)
2.b Aromatic/amide H refined with riding coordinates:
 N2N(H2N), N1N(H1N), C13C(H13C), C14C(H14C), C15C(H15C), C4C(H4C), C6C(H6C),
 C2C(H2C), C3C(H3C), C1C(H1C)
2.c Idealised Me refined as rotating group:
 C11C(H11A,H11B,H11C)
;
_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 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.652