Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ Generated Copper(I) Catalyst and Electrophilic Triiodide Ion
Wendy S. Brotherton; Ronald J. Clark; Lei Zhu; Journal of Organic Chemistry 77 (2012) 6443–6455; doi:10.1021/jo300841c

data_4027343
_publ_section_title
;
 Synthesis of 5-Iodo-1,4-disubstituted-1,2,3-triazoles Mediated by in Situ
 Generated Copper(I) Catalyst and Electrophilic Triiodide Ion
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6443
_journal_page_last               6455
_journal_paper_doi               10.1021/jo300841c
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H36 N, I3'
_chemical_formula_sum            'C16 H36 I3 N'
_chemical_formula_weight         623.16
_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                83.4610(10)
_cell_angle_beta                 74.2290(10)
_cell_angle_gamma                78.5220(10)
_cell_formula_units_Z            4
_cell_length_a                   9.5161(9)
_cell_length_b                   15.6549(15)
_cell_length_c                   15.8860(15)
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.31
_cell_volume                     2227.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23584
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    4.205
_exptl_absorpt_correction_T_max  0.6818
_exptl_absorpt_correction_T_min  0.5176
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.638
_refine_diff_density_min         -1.240
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         9690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0181P)^2^+5.4577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0728
_reflns_number_gt                8898
_reflns_number_total             9690
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300841c_si_001_3.cif
_cod_data_source_block           zhu130
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4027343