Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles.
Yan, Wuming; Wang, Qiaoyi; Chen, Yunfeng; Petersen, Jeffrey L.; Shi, Xiaodong; Organic letters 12 (2010) 3308–3311; doi:10.1021/ol101082v

data_1503049
_publ_section_title
;
 Iron-catalyzed C-O bond activation for the synthesis of
 propargyl-1,2,3-triazoles and 1,1-bis-triazoles.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3308
_journal_page_last               3311
_journal_paper_doi               10.1021/ol101082v
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H24 N6 O3'
_chemical_formula_weight         420.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 96.776(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0218(8)
_cell_length_b                   14.6605(14)
_cell_length_c                   18.8312(18)
_cell_measurement_reflns_used    3998
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.58
_cell_volume                     2199.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0578
_diffrn_reflns_av_sigmaI/netI    0.1207
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15997
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     567
_refine_ls_number_reflns         9836
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                5216
_reflns_number_total             9836
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101082v_si_002.cif
_cod_data_source_block           xs13ccd
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1503049