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_4027383
_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 H18 Br F3 N2 O4 S'
_chemical_formula_weight         543.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.425(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.066(2)
_cell_length_b                   8.7343(13)
_cell_length_c                   18.513(3)
_cell_measurement_temperature    150(2)
_cell_volume                     2270.4(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.933
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18148
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  0.8282
_exptl_absorpt_correction_T_min  0.4660
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.300
_refine_diff_density_min         -1.361
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0810P)^2^+2.4371P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                4218
_reflns_number_total             5250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3010827_si_003.cif
_cod_data_source_block           str0815
_cod_original_cell_volume        2270.2(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4027383