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_4027722
_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            'C22 H27 N O5'
_chemical_formula_weight         385.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.623(9)
_cell_length_b                   21.48(2)
_cell_length_c                   10.161(9)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.22
_cell_volume                     2100(3)
_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 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'Fast Fourier Transform'
_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  0.1955
_diffrn_reflns_av_sigmaI/netI    0.1019
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14893
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9304
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3.5(15)
_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     272
_refine_ls_number_reflns         3990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0614
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1738
_reflns_number_gt                3304
_reflns_number_total             3990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301796r_si_001_3.cif
_cod_data_source_block           kg
_cod_database_code               4027722