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_4027723
_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_moiety         'C28 H31 N O4'
_chemical_formula_sum            'C28 H31 N O4'
_chemical_formula_weight         445.54
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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            8
_cell_length_a                   19.473(3)
_cell_length_b                   33.144(4)
_cell_length_c                   7.8337(10)
_cell_measurement_reflns_used    4612
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.37
_cell_measurement_theta_min      2.43
_cell_volume                     5056.0(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15672
_diffrn_reflns_theta_full        21.41
_diffrn_reflns_theta_max         21.41
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.996
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0694P)^2^+2.3634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                2354
_reflns_number_total             2804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301796r_si_001_4.cif
_cod_data_source_block           dd
_cod_original_cell_volume        5056.1(11)
_cod_database_code               4027723