Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles.
Liu, Peiye; Clark, Ronald J.; Zhu, Lei; The Journal of organic chemistry 83 (2018) 5092–5103; doi:10.1021/acs.joc.8b00424

data_4035522
_publ_section_title
;
 Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed
 Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5092
_journal_page_last               5103
_journal_paper_doi               10.1021/acs.joc.8b00424
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H13 N5 O3'
_chemical_formula_sum            'C17 H13 N5 O3'
_chemical_formula_weight         335.32
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 108.7114(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4077(5)
_cell_length_b                   16.3992(9)
_cell_length_c                   12.0895(6)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      2.17
_cell_volume                     1578.79(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      103(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19611
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.336
_diffrn_reflns_theta_min         1.778
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.7210
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.464
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
; 
 Flack x determined using 3521 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         8074
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0315
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.3459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0761
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                7779
_reflns_number_total             8074
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00424_si_003.cif
_cod_data_source_block           zhu232
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4035522
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.972
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              67359
_shelx_hkl_checksum              79302