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_7700476
_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            'C39 H36 N4 P2 Ru'
_chemical_formula_weight         723.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2404(3)
_cell_length_b                   30.6560(11)
_cell_length_c                   11.7644(5)
_cell_measurement_reflns_used    8293
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.57
_cell_volume                     3332.5(2)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13746
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.574
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 2832 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.028(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7510
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0298
_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^)+(0.0151P)^2^+0.8625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0636
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                6702
_reflns_number_total             7510
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt02363a2.cif
_cod_data_source_block           ic19425
_cod_depositor_comments
'Adding full bibliography for 7700474--7700478.cif.'
_cod_database_code               7700476
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.824
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              76940