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_4026456
_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         'C19 H14 I N'
_chemical_formula_sum            'C19 H14 I N'
_chemical_formula_weight         383.21
_chemical_melting_point          399
_chemical_name_common            quinoline
_chemical_name_systematic
; 
 Pyrroloquinoline 
;
_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                110.441(8)
_cell_angle_beta                 114.906(8)
_cell_angle_gamma                93.239(7)
_cell_formula_units_Z            2
_cell_length_a                   9.4359(8)
_cell_length_b                   9.7924(8)
_cell_length_c                   9.9841(8)
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0535
_cell_measurement_theta_min      3.6804
_cell_volume                     761.22(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5055
_diffrn_reflns_theta_full        26.25
_diffrn_reflns_theta_max         26.25
_diffrn_reflns_theta_min         3.69
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.096
_exptl_absorpt_correction_T_max  0.7041
_exptl_absorpt_correction_T_min  0.5360
_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            BROWN
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.172
_refine_diff_density_min         -1.796
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0550P)^2^+1.6101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0928
_reflns_number_gt                2880
_reflns_number_total             3058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200638k_si_001.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        761.22(11)
_cod_database_code               4026456