CeCl3.7H2O Catalyzed C-C and C-N Bond-Forming Cascade Cyclization with Subsequent Side-Chain Functionalization and Rearrangement: A Domino Approach to Pentasubstituted Pyrrole Analogues
Dipankar Dhara; Krishnanka S. Gayen; Saikat Khamarui; Palash Pandit; Sukla Ghosh; Dilip K. Maiti; Journal of Organic Chemistry 77 (2012) 10441–10449; doi:10.1021/jo301796r

data_4027720
_publ_section_title
;
 CeCl3.7H2O Catalyzed C-C and C-N Bond-Forming Cascade Cyclization with
 Subsequent Side-Chain Functionalization and Rearrangement: A Domino
 Approach to Pentasubstituted Pyrrole Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10441
_journal_page_last               10449
_journal_paper_doi               10.1021/jo301796r
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C21 H25 N O5'
_chemical_formula_weight         371.42
_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                90.033(2)
_cell_angle_beta                 102.509(2)
_cell_angle_gamma                113.507(2)
_cell_formula_units_Z            2
_cell_length_a                   9.7999(3)
_cell_length_b                   10.1149(3)
_cell_length_c                   11.2907(4)
_cell_measurement_reflns_used    7292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      0.782
_cell_volume                     997.21(6)
_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 0.782
_diffrn_measured_fraction_theta_max 0.782
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4104
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.995
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       cubic
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.044
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1786
_reflns_number_gt                1864
_reflns_number_total             3137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301796r_si_001_1.cif
_cod_data_source_block           dd136_0m
_cod_database_code               4027720