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_4027382
_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_moiety         'C24 H20 Br F3 N2 O4'
_chemical_formula_sum            'C24 H20 Br F3 N2 O4'
_chemical_formula_weight         537.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 105.497(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6075(12)
_cell_length_b                   15.5958(11)
_cell_length_c                   9.3671(7)
_cell_measurement_reflns_used    3142
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.3
_cell_measurement_theta_min      2.5
_cell_volume                     2337.9(3)
_computing_cell_refinement       'Bruker SAINT version 6.36A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    ' ?'
_computing_publication_material
'enCIFer (Allen et al., 2004); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14556
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.816
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS version 2007/2; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.91
_refine_diff_density_min         -1.08
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.063P)^2^+3.031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.126
_refine_ls_wR_factor_ref         0.134
_reflns_number_gt                3976
_reflns_number_total             5234
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3010827_si_002.cif
_cod_data_source_block           brnocf
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027382