Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and 3-Iodo-1,2-dihydropyridines
Xiaoyi Xin; Dongping Wang; Fan Wu; Xincheng Li; Boshun Wan; Journal of Organic Chemistry 78 (2013) 4065–4074; doi:10.1021/jo400387b

data_4028178
_publ_section_title
;
 Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization
 of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and
 3-Iodo-1,2-dihydropyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4065
_journal_page_last               4074
_journal_paper_doi               10.1021/jo400387b
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C28 H24 I N O6 S'
_chemical_formula_weight         629.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_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                89.194(3)
_cell_angle_beta                 83.704(3)
_cell_angle_gamma                73.888(3)
_cell_formula_units_Z            2
_cell_length_a                   9.6086(4)
_cell_length_b                   11.3986(5)
_cell_length_c                   14.7124(6)
_cell_measurement_reflns_used    2569
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.34
_cell_volume                     1538.51(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Smart Apex II CCD'
_diffrn_measurement_method       'omega 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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8436
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.146
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_correction_T_min  0.9535
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.616
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         6432
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          1.819
_refine_ls_shift/su_mean         0.186
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1227P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1811
_reflns_number_gt                4919
_reflns_number_total             6432
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400387b_si_002.cif
_cod_data_source_block           9
_cod_original_cell_volume        1538.51(11)
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4028178