Synthesis of 5-Iodopyrrolo[1,2-a]quinolines and Indolo[1,2-a]quinolines via Iodine-Mediated Electrophilic and Regioselective 6-endo-dig Ring Closure
Akhilesh Kumar Verma; Satya Prakash Shukla; Jaspal Singh; Vineeta Rustagi; Journal of Organic Chemistry 76 (2011) 5670–5684; doi:10.1021/jo200638k

data_4026457
_publ_section_title
;
 Synthesis of 5-Iodopyrrolo[1,2-a]quinolines and Indolo[1,2-a]quinolines
 via Iodine-Mediated Electrophilic and Regioselective 6-endo-dig Ring
 Closure
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5670
_journal_page_last               5684
_journal_paper_doi               10.1021/jo200638k
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C24 H18 I N O'
_chemical_formula_sum            'C24 H18 I N O'
_chemical_formula_weight         463.29
_chemical_melting_point          429
_chemical_name_common            HETROCYCLIC
_chemical_name_systematic        INDOLOQUINOLINE
_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                89.215(5)
_cell_angle_beta                 81.700(5)
_cell_angle_gamma                61.836(5)
_cell_formula_units_Z            4
_cell_length_a                   10.733(5)
_cell_length_b                   11.104(5)
_cell_length_c                   18.129(5)
_cell_measurement_reflns_used    16057
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.0054
_cell_measurement_theta_min      3.1745
_cell_volume                     1881.2(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w 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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26052
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.18
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         2.027
_refine_diff_density_min         -1.986
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     487
_refine_ls_number_reflns         8141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+4.3737P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                6980
_reflns_number_total             8141
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200638k_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4026457