Cu(II)-Catalyzed Oxidative Formation of 5,5'-Bistriazoles.
Brassard, Christopher J.; Zhang, Xiaoguang; Brewer, Christopher R.; Liu, Peiye; Clark, Ronald J.; Zhu, Lei; The Journal of organic chemistry 81 (2016) 12091–12105; doi:10.1021/acs.joc.6b01907

data_4037277
_publ_section_title
;
 Cu(II)-Catalyzed Oxidative Formation of 5,5'-Bistriazoles.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12091
_journal_page_last               12105
_journal_paper_doi               10.1021/acs.joc.6b01907
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C22 H22 N6'
_chemical_formula_sum            'C22 H22 N6'
_chemical_formula_weight         370.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.087(13)
_cell_length_b                   10.022(6)
_cell_length_c                   8.828(5)
_cell_measurement_reflns_used    5708
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.24
_cell_volume                     1954(2)
_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 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0342
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.080
_diffrn_reflns_theta_min         2.032
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   empiricl
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       rod
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
; 
 Flack x determined using 1610 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0306P)^2^+0.2974P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3792
_reflns_number_total             4237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01907_si_001.cif
_cod_data_source_block           zhu212b
_cod_database_code               4037277
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014-3
_shelx_res_checksum              71695
_shelx_hkl_checksum              32708