O-Transfer-facilitated cyclizations of propargylamides with TMSN3: selective synthesis of tetrazoles and dihydroimidazoles.
Hu, Yancheng; Yi, Ruxia; Yu, Xinzhang; Xin, Xiaoyi; Wang, Chunxiang; Wan, Boshun; Chemical communications (Cambridge, England) 51 (2015) 15398–15401; doi:10.1039/c5cc05715a

data_7118054
_publ_section_title
;
 O-Transfer-facilitated cyclizations of propargylamides with TMSN3:
 selective synthesis of tetrazoles and dihydroimidazoles.
;
_journal_issue                   84
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              15398
_journal_page_last               15401
_journal_paper_doi               10.1039/c5cc05715a
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H15 I N4 O'
_chemical_formula_weight         478.28
_chemical_name_systematic        HYC-Tetrazole
_chemical_properties_physical    Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-09-26 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.3839(14)
_cell_length_b                   36.433(2)
_cell_length_c                   10.0332(7)
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      47.784
_cell_measurement_theta_min      4.472
_cell_volume                     8182.2(9)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24429
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         2.136
_exptl_absorpt_coefficient_mu    1.585
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6038
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate/pentane'
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
; 
 Flack x determined using 2843 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.017(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7958
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0298P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6935
_reflns_number_total             7958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05715a2.cif
_cod_data_source_block           cd214239
_cod_original_cell_volume        8182.3(9)
_cod_original_sg_symbol_H-M      'A b a 2'
_cod_database_code               7118054
_shelxl_version_number           2013-4
_shelx_res_checksum              33681