Facile synthesis of 1,5-disubstituted tetrazoles by reacting a ruthenium acetylide complex with trimethylsilyl azide.
Chang, Chao-Wan; Cheng, Ming-Chuan; Lee, Gene-Hsiang; Peng, Shie-Ming; Dalton transactions (Cambridge, England : 2003) 48 (2019) 11732–11742; doi:10.1039/c9dt02363a

data_7700475
_publ_section_title
;
 Facile synthesis of 1,5-disubstituted tetrazoles by reacting a ruthenium
 acetylide complex with trimethylsilyl azide.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11732
_journal_page_last               11742
_journal_paper_doi               10.1039/c9dt02363a
_journal_volume                  48
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H9 F5 N4'
_chemical_formula_weight         340.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.2052(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6879(2)
_cell_length_b                   5.99050(10)
_cell_length_c                   15.1858(4)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.96
_cell_measurement_theta_min      2.91
_cell_volume                     698.28(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5325
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.953
_diffrn_reflns_theta_min         2.914
_exptl_absorpt_coefficient_mu    1.299
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+0.0981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0648
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2768
_reflns_number_total             2818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02363a2.cif
_cod_data_source_block           ic19458
_cod_depositor_comments
'Adding full bibliography for 7700474--7700478.cif.'
_cod_database_code               7700475
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.623
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              66938