Reductive Nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing Indolines and Tetrahydroquinolines
James C. Anderson; Adam Noble; Derek A. Tocher; Journal of Organic Chemistry 77 (2012) 6703–6727; doi:10.1021/jo3010827

data_4027384
_publ_section_title
;
 Reductive Nitro-Mannich Route for the Synthesis of 1,2-Diamine Containing
 Indolines and Tetrahydroquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6703
_journal_page_last               6727
_journal_paper_doi               10.1021/jo3010827
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C22 H29 Br N2 O2'
_chemical_formula_weight         433.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.817(3)
_cell_angle_beta                 74.115(3)
_cell_angle_gamma                62.824(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6156(18)
_cell_length_b                   10.448(2)
_cell_length_c                   12.197(2)
_cell_measurement_temperature    150(2)
_cell_volume                     1045.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8594
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    1.986
_exptl_absorpt_correction_T_max  0.7966
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.732
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.000(2)
_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   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          2.012
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1049P)^2^+1.2112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.1899
_reflns_number_gt                3607
_reflns_number_total             4589
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3010827_si_004.cif
_cod_data_source_block           str0847
_cod_database_code               4027384