3-Dialkylamino-1,2,4-triazoles via Zn<sup>II</sup>-Catalyzed Acyl Hydrazide-Dialkylcyanamide Coupling.
Yunusova, Sevilya N.; Bolotin, Dmitrii S.; Suslonov, Vitalii V.; Vovk, Mikhail A.; Tolstoy, Peter M.; Kukushkin, Vadim Yu; ACS omega 3 (2018) 7224–7234; doi:10.1021/acsomega.8b01047

data_4516078
_publ_section_title
;
 3-Dialkylamino-1,2,4-triazoles via Zn<sup>II</sup>-Catalyzed Acyl
 Hydrazide-Dialkylcyanamide Coupling.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              7224
_journal_page_last               7234
_journal_paper_doi               10.1021/acsomega.8b01047
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C10 H12 N4'
_chemical_formula_sum            'C10 H12 N4'
_chemical_formula_weight         188.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                100.240(5)
_cell_angle_beta                 103.121(5)
_cell_angle_gamma                103.246(6)
_cell_formula_units_Z            4
_cell_length_a                   8.4665(6)
_cell_length_b                   10.3120(7)
_cell_length_c                   11.9037(6)
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.7290
_cell_measurement_theta_min      3.8800
_cell_volume                     955.83(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -93.00 -33.00   0.50    5.64    --  -41.22 -23.00 -88.00  120
  2  \w    -20.00  16.00   0.50    5.64    --  -41.22  23.00  77.00   72
  3  \w     34.00  60.00   0.50    5.64    --   41.22  23.00  77.00   52
  4  \w     79.00 109.00   0.50   14.00    --  101.00 -23.00 -88.00   60
  5  \w     95.00 122.00   0.50   14.00    --  101.00  23.00  77.00   54
  6  \w     39.00  73.00   0.50   14.00    --  101.00 -23.00 -88.00   68
  7  \w   -103.00 -74.00   0.50    5.64    --  -41.22 -54.00 -30.00   58
  8  \w    -73.00 -28.00   0.50    5.64    --  -41.22 104.00  30.00   90
  9  \w    -36.00  13.00   0.50    5.64    --  -41.22  65.00  90.00   98
 10  \w    -48.00 -13.00   0.50    5.64    --  -41.22 138.00  90.00   70
 11  \w    -44.00  19.00   0.50    5.64    --  -41.22  32.00-120.00  126
 12  \w    -99.00 -54.00   0.50    5.64    --  -41.22 -54.00 -90.00   90
 13  \w    -80.00 -52.00   0.50    5.64    --  -41.22 138.00  90.00   56
 14  \w    -63.00 -31.00   0.50    5.64    --  -41.22 -54.00 -30.00   64
 15  \w    -10.00  15.00   0.50    5.64    --  -41.22 104.00  30.00   50
 16  \w     30.00  61.00   0.50    5.64    --   41.22  43.00 150.00   62
 17  \w     25.00  65.00   0.50    5.64    --   41.22 -77.00-120.00   80
 18  \w    -16.00  10.00   0.50    5.64    --   41.22-104.00-120.00   52
 19  \w     23.00  48.00   0.50    5.64    --   41.22 -43.00  60.00   50
 20  \w      5.00  46.00   0.50    5.64    --   41.22 -23.00 -88.00   82
 21  \w     72.00 101.00   0.50    5.64    --   41.22  23.00  77.00   58
 22  \w     24.00  72.00   0.50    5.64    --   41.22-104.00-120.00   96
 23  \w    -16.00   9.00   0.50    5.64    --   41.22 -77.00-120.00   50
 24  \w      6.00  65.00   0.50    5.64    --   41.22 -77.00 -30.00  118
 25  \w     38.00 122.00   0.50   14.00    --  101.00-133.00 -60.00  168
 26  \w     95.00 120.00   0.50   14.00    --  101.00  42.00-180.00   50
 27  \w     41.00 109.00   0.50   14.00    --  101.00 -25.00  30.00  136
 28  \w     70.00  96.00   0.50   14.00    --  101.00-111.00-120.00   52
 29  \w     88.00 115.00   0.50   14.00    --  101.00-111.00  90.00   54
 30  \w     93.00 138.00   0.50   14.00    --  101.00  33.00 -90.00   90
 31  \w     53.00  79.00   0.50   14.00    --  101.00-111.00 150.00   52
 32  \w     55.00 114.00   0.50   14.00    --  101.00-111.00 -30.00  118
 33  \w     53.00 101.00   0.50   14.00    --  101.00 -68.00  90.00   96
 34  \w     49.00  80.00   0.50   14.00    --  101.00 -33.00 120.00   62
 35  \w    125.00 155.00   0.50   14.00    --  101.00  42.00-180.00   60
 36  \w     36.00  81.00   0.50   14.00    --  101.00 -93.00 150.00   90
 37  \w     38.00 116.00   0.50   14.00    --  101.00 -50.00 120.00  156
 38  \w     90.00 115.00   0.50   14.00    --  101.00-111.00 120.00   50
 39  \w    121.00 157.00   0.50   14.00    --  101.00   8.00   0.00   72
 40  \w     46.00  76.00   0.50   14.00    --  101.00-111.00 120.00   60
 41  \w     62.00 127.00   0.50   14.00    --  101.00 -87.00   0.00  130
 42  \w     72.00 106.00   0.50   14.00    --  101.00   8.00   0.00   68
 43  \w     58.00 109.00   0.50   14.00    --  101.00 -93.00 -30.00  102
 44  \w     71.00 119.00   0.50   14.00    --  101.00 -87.00 120.00   96
 45  \w     36.00  62.00   0.50   14.00    --  101.00 -87.00 120.00   52
 46  \w    101.00 142.00   0.50   14.00    --  101.00  25.00 150.00   82
 47  \w     88.00 148.00   0.50   14.00    --  101.00  42.00  90.00  120
 48  \w     83.00 109.00   0.50   14.00    --  101.00-133.00 -30.00   52
 49  \w     92.00 156.00   0.50   14.00    --  101.00  33.00-120.00  128
 50  \w     38.00 109.00   0.50   14.00    --  101.00 -33.00-150.00  142
 51  \w    107.00 133.00   0.50   14.00    --  101.00 111.00 -60.00   52
 52  \w    132.00 157.00   0.50   14.00    --  101.00  33.00-150.00   50
 53  \w     64.00  90.00   0.50   14.00    --  101.00 -42.00-180.00   52
 54  \w     54.00  80.00   0.50   14.00    --  101.00-111.00  90.00   52
 55  \w     38.00 112.00   0.50   14.00    --  101.00 -42.00 -60.00  148
 56  \w     92.00 117.00   0.50   14.00    --  101.00  42.00  60.00   50
 57  \w     83.00 120.00   0.50   14.00    --  101.00 -68.00-120.00   74
 58  \w     56.00 118.00   0.50   14.00    --  101.00 -59.00 -30.00  124
 59  \w     46.00 116.00   0.50   14.00    --  101.00 -59.00-150.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1528993000
_diffrn_orient_matrix_UB_12      0.0542360000
_diffrn_orient_matrix_UB_13      -0.0416416000
_diffrn_orient_matrix_UB_21      -0.1199650000
_diffrn_orient_matrix_UB_22      -0.1353785000
_diffrn_orient_matrix_UB_23      0.0035782000
_diffrn_orient_matrix_UB_31      0.0116214000
_diffrn_orient_matrix_UB_32      0.0612932000
_diffrn_orient_matrix_UB_33      0.1304401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8855
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.989
_diffrn_reflns_theta_min         3.930
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0951P)^2^+0.2828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             3618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01047_si_002.cif
_cod_data_source_block           4_triclinic
_cod_original_cell_volume        955.83(11)
_cod_database_code               4516078
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Zn Cl2 N8 C20'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 98.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), C10A(H10A), C6A(H6A), C9A(H9A), C7A(H7A), C8A(H8A), C8(H8),
 C9(H9), C10(H10), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C4(H4A,H4B,H4C), C5A(H5AA,H5AB,H5AC), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              8669
_shelx_hkl_checksum              57288
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.048
_oxdiff_exptl_absorpt_empirical_full_min 0.195