3-(Hetero)aryl-4-indolylamino-α-tetralones by Diastereoselective Internal Redox Cyclization: An "Azaenamine" Conjugate Addition
Nugzar Ghavtadze; Rishikesh Narayan; Birgit Wibbeling; Ernst-Ulrich Würthwein; Journal of Organic Chemistry 76 (2011) 5185–5197; doi:10.1021/jo200896y

data_4026447
_publ_section_title
;
 3-(Hetero)aryl-4-indolylamino-\a-tetralones by Diastereoselective
 Internal Redox Cyclization: An "Azaenamine" Conjugate Addition
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5185
_journal_page_last               5197
_journal_paper_doi               10.1021/jo200896y
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C24 H19 Cl N2 O'
_chemical_formula_weight         386.86
_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                74.927(5)
_cell_angle_beta                 88.001(4)
_cell_angle_gamma                77.262(5)
_cell_formula_units_Z            2
_cell_length_a                   6.0519(2)
_cell_length_b                   10.2844(8)
_cell_length_c                   16.9410(8)
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     992.79(10)
_computing_cell_refinement       'Collect (NOnius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SCHAKAL (Keller, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11836
_diffrn_reflns_theta_full        66.81
_diffrn_reflns_theta_max         66.81
_diffrn_reflns_theta_min         4.56
_exptl_absorpt_coefficient_mu    1.825
_exptl_absorpt_correction_T_max  0.9143
_exptl_absorpt_correction_T_min  0.6583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.272
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0714
_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^)+(0.0911P)^2^+1.0295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1862
_refine_ls_wR_factor_ref         0.1945
_reflns_number_gt                2883
_reflns_number_total             3302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200896y_si_003.cif
_cod_data_source_block           wue5756
_cod_database_code               4026447