One-pot synthesis of 6,11-dihydro-5H-indolizino[8,7-b]indoles via sequential formation of β-enamino ester, Michael addition and Pictet-Spengler reactions
Yan, Chao Guo; Zhu, Dan; Sun, Jing; RSC Adv.  (2014) –; doi:10.1039/C4RA10355F

data_7218721
_publ_section_title
;
 One-pot synthesis of 6,11-dihydro-5H-indolizino[8,7-b]indoles via
 sequential formation of \b-enamino ester, Michael addition and
 Pictet-Spengler reactions
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA10355F
_journal_year                    2014
_chemical_formula_moiety         'C31 H36 F N3 O6'
_chemical_formula_sum            'C31 H36 F N3 O6'
_chemical_formula_weight         565.63
_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                118.534(4)
_cell_angle_beta                 92.439(5)
_cell_angle_gamma                90.153(4)
_cell_formula_units_Z            2
_cell_length_a                   7.7364(12)
_cell_length_b                   14.951(2)
_cell_length_c                   14.954(2)
_cell_measurement_reflns_used    7884
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      2.64
_cell_volume                     1517.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29606
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         6949
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0791
_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^)+(0.0650P)^2^+0.9399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1562
_refine_ls_wR_factor_ref         0.1935
_reflns_number_gt                3564
_reflns_number_total             7002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra10355f2.cif
_cod_data_source_block           b2
_cod_database_code               7218721