Syntheses of [1,2,4]triazolo[1,5-a]benzazoles enabled by the transition-metal-free oxidative N-N bond formation
Erchang Shang; Junzhi Zhang; Jinyi Bai; Zhan Wang; Xiang Li; Bing Zhu; Xiaoguang Lei; Chem.Commun. 52 (2016) 7028–; doi:

data_7119142
_publ_section_title
;
 Syntheses of [1,2,4]triazolo[1,5-a]benzazoles enabled by the
 transition-metal-free oxidative N-N bond formation
;
_journal_name_full               Chem.Commun.
_journal_page_first              7028
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C14 H8 F2 N4'
_chemical_formula_sum            'C14 H8 F2 N4'
_chemical_formula_weight         270.24
_chemical_name_systematic        1f
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-12-09 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.317(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3750(2)
_cell_length_b                   20.1126(13)
_cell_length_c                   13.1678(8)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    141(50)
_cell_measurement_theta_max      28.2380
_cell_measurement_theta_min      4.6810
_cell_volume                     1146.48(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      141(50)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   10.00   37.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000    0.0000 27

  2 omega  -52.00   -2.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000    0.0000 50

  3 omega  -16.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000 -180.0000 103

  4 omega   11.00   87.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   38.0000  -90.0000 76

  5 omega  -79.00  100.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017    0.0000   90.0000 179

  6 omega   19.00   78.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -141.0000   24.0000 59

  7 omega  -20.00   30.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000  -60.0000 50

  8 omega  -67.00  -31.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  121.0000   41.0029 36

  9 omega  -72.00  -42.00   1.0000   33.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  129.0000  131.2112 30
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0607669000
_diffrn_orient_matrix_UB_12      0.0210264000
_diffrn_orient_matrix_UB_13      0.0412569000
_diffrn_orient_matrix_UB_21      -0.0368307000
_diffrn_orient_matrix_UB_22      0.0282679000
_diffrn_orient_matrix_UB_23      -0.0316549000
_diffrn_orient_matrix_UB_31      -0.1476188000
_diffrn_orient_matrix_UB_32      0.0016129000
_diffrn_orient_matrix_UB_33      0.0161270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16603
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.127
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0360P)^2^+0.7627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1644
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01976e2.cif
_cod_data_source_block           exp_5375
_cod_original_cell_volume        1146.50(12)
_cod_database_code               7119142
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C14 N4 F2'
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.988
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'