Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of o-Alkynylaryl Isocyanides with Iodine
Takenori Mitamura; Akiya Ogawa; Journal of Organic Chemistry 76 (2011) 1163–1166; doi:10.1021/jo1021772

data_4026053
_publ_section_title
;
 Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of
 o-Alkynylaryl Isocyanides with Iodine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1163
_journal_page_last               1166
_journal_paper_doi               10.1021/jo1021772
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H11 I2 N O '
_chemical_formula_sum            'C16 H11 I2 N O'
_chemical_formula_weight         487.08
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.5870(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            16
_cell_length_a                   36.7158(7)
_cell_length_b                   8.06317(15)
_cell_length_c                   20.2857(4)
_cell_measurement_reflns_used    28464
_cell_measurement_temperature    103.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     5999.4(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      103.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            28935
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_exptl_absorpt_coefficient_mu    4.190
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_description       block
_exptl_crystal_F_000             3648.00
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.77
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6889
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.0030
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0380P)^2^+16.9755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0710
_reflns_number_gt                6665
_reflns_number_total             6889
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo1021772_si_003.cif
_cod_data_source_block           '_OME'
_cod_original_cell_volume        5999.36(19)
_cod_original_formula_sum        'C16 H11 I2 N O '
_cod_database_code               4026053