From nitrobenzenes to substituted tetrahydroquinolines in a single step by a domino reduction/imine formation/aza-diels-alder reaction.
Imrich, Hans-Georg; Conrad, Jürgen; Bubrin, Denis; Beifuss, Uwe; The Journal of organic chemistry 80 (2015) 2319–2332; doi:10.1021/jo502882y

data_4030675
_publ_section_title
;
 From nitrobenzenes to substituted tetrahydroquinolines in a single step
 by a domino reduction/imine formation/aza-diels-alder reaction.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2319
_journal_page_last               2332
_journal_paper_doi               10.1021/jo502882y
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 Br N'
_chemical_formula_sum            'C18 H16 Br N'
_chemical_formula_weight         326.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
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_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90.00
_cell_angle_beta                 95.091(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.666(3)
_cell_length_b                   9.8149(18)
_cell_length_c                   15.315(3)
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_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      4.5
_cell_volume                     1447.2(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
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_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.40
_diffrn_standards_interval_count 298
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
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_refine_diff_density_max         1.223
_refine_diff_density_min         -1.512
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0980P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                2007
_reflns_number_total             2551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502882y_si_001.cif
_cod_data_source_block           im03
_cod_depositor_comments
'Adding full bibliography for 4030673--4030675.cif.'
_cod_original_cell_volume        1447.3(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4030675