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_4035521
_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         'C16 H11 Br N4 O'
_chemical_formula_sum            'C16 H11 Br N4 O'
_chemical_formula_weight         355.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.5591(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3518(5)
_cell_length_b                   10.0455(4)
_cell_length_c                   13.0967(5)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      29.36
_cell_measurement_theta_min      2.66
_cell_volume                     1466.01(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_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 0.951
_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  0.0172
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.445
_diffrn_reflns_theta_min         1.895
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       irregular,
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.349
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.267
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0190
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0222P)^2^+0.8723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3648
_reflns_number_total             3855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00424_si_001.cif
_cod_data_source_block           zhu230
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035521
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.440
_shelx_estimated_absorpt_t_max   0.521
_exptl_absorpt_special_details   SADABS
_shelx_res_checksum              99012
_shelx_hkl_checksum              68323