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_4027342
_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         'C8 H12 Cu N4, Cl O4'
_chemical_formula_sum            'C8 H12 Cl Cu N4 O4'
_chemical_formula_weight         327.21
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   23.9334(9)
_cell_length_b                   8.3486(3)
_cell_length_c                   20.4206(9)
_cell_measurement_reflns_used    3773
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.58
_cell_volume                     4080.2(3)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16180
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    1.813
_exptl_absorpt_correction_T_max  0.8395
_exptl_absorpt_correction_T_min  0.7361
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         7606
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                6314
_reflns_number_total             7606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300841c_si_001_2.cif
_cod_data_source_block           zhu129
_cod_original_sg_symbol_Hall     P2c-2n
_cod_database_code               4027342