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_7118055
_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_formula_sum            'C17 H16 I2 N2 O3 S'
_chemical_formula_weight         582.18
_chemical_name_systematic        HYC-767-1
_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
_audit_update_record
;
2014-09-26 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                97.897(2)
_cell_angle_beta                 91.846(2)
_cell_angle_gamma                103.895(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2509(8)
_cell_length_b                   11.4870(14)
_cell_length_c                   12.2569(15)
_cell_measurement_reflns_used    2492
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.570
_cell_measurement_theta_min      4.609
_cell_volume                     979.4(2)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5844
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    3.336
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10118
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.117
_refine_diff_density_max         1.706
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0859P)^2^+1.5411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                3029
_reflns_number_total             3789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc05715a2.cif
_cod_data_source_block           cd213594
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118055