Site-Selective Electrophilic Cyclization and Subsequent Ring-Opening: A Synthetic Route to Pyrrolo[1,2-a]quinolines and Indolizines
Trapti Aggarwal; Sonu Kumar; Devendra K. Dhaked; Rakesh K. Tiwari; Prasad V. Bharatam; Akhilesh K. Verma; Journal of Organic Chemistry 77 (2012) 8562–8573; doi:10.1021/jo3015374

data_4027563
_publ_section_title
;
 Site-Selective Electrophilic Cyclization and Subsequent Ring-Opening: A
 Synthetic Route to Pyrrolo[1,2-a]quinolines and Indolizines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8562
_journal_page_last               8573
_journal_paper_doi               10.1021/jo3015374
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C24 H18 I N O3'
_chemical_formula_sum            'C24 H18 I N O3'
_chemical_formula_weight         495.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.341(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.5692(16)
_cell_length_b                   7.5130(3)
_cell_length_c                   17.2889(8)
_cell_measurement_reflns_used    3575
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.03
_cell_volume                     3970.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25981
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.8533
_exptl_absorpt_correction_T_min  0.8152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0195
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0267P)^2^+4.7152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0505
_reflns_number_gt                3575
_reflns_number_total             3902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3015374_si_002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4027563