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_1503050
_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            'C23 H17 N3'
_chemical_formula_weight         335.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 96.166(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.3847(12)
_cell_length_b                   5.6909(4)
_cell_length_c                   40.749(3)
_cell_measurement_reflns_used    8760
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.51
_cell_volume                     3547.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            23912
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.4002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1308
_refine_ls_wR_factor_ref         0.1519
_reflns_number_gt                5026
_reflns_number_total             8040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101082v_si_003.cif
_cod_data_source_block           xs8ccd
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1503050