Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivatives via iodocyclization reaction and a DFT mechanistic study.
Sonawane, Amol D.; Garud, Dinesh R.; Udagawa, Taro; Koketsu, Mamoru; Organic & biomolecular chemistry 16 (2018) 245–255; doi:10.1039/c7ob02523h

data_7156008
_publ_section_title
;
 Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline
 derivatives via iodocyclization reaction and a DFT mechanistic study.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              245
_journal_page_last               255
_journal_paper_doi               10.1039/c7ob02523h
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C12 H8 I N S'
_chemical_formula_weight         325.15
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-31 deposited with the CCDC.
2017-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.170(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.189(14)
_cell_length_b                   4.122(4)
_cell_length_c                   19.078(19)
_cell_measurement_reflns_used    3336
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.8064
_cell_measurement_theta_min      1.7040
_cell_volume                     1109.4(19)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CRYSTALCLEAR
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 14.6199
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4593
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    3.038
_exptl_absorpt_correction_T_max  0.5817
_exptl_absorpt_correction_T_min  0.5817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.827
_refine_diff_density_min         -1.479
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.809
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.809
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0470
_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          0.1189
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                1837
_reflns_number_total             2461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02523h3.cif
_cod_data_source_block           amol
_cod_depositor_comments          'Adding full bibliography for 7156008.cif.'
_cod_original_cell_volume        1109.3(19)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7156008