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_4516082
_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         'C12 H14 N4'
_chemical_formula_sum            'C12 H14 N4'
_chemical_formula_weight         214.27
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-12-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_cell_angle_alpha                90
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_cell_length_c                   20.4674(4)
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_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3430
_cell_measurement_theta_min      3.2320
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
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_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -38.00  -11.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -      -10.9969  -38.0000 -120.0000 27

  2 omega  -15.00   30.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -      -10.9969  -99.0000  -90.0000 45

  3 omega  -33.00   -6.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -      -10.9969  -57.0000   90.0000 27

  4 omega   48.00  101.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  178.0000  150.0000 53

  5 omega   10.00   51.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157   57.0000   30.0000 41

  6 omega  -53.00  -21.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -19.0000  120.0000 32

  7 omega  -63.00   45.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -77.0000 -180.0000 108

  8 omega   57.00   84.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  178.0000  -90.0000 27

  9 omega   19.00   44.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -99.0000  150.0000 25

 10 omega  -11.00   15.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157   38.0000 -180.0000 26

 11 omega  -16.00    9.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -19.0000  120.0000 25

 12 omega   60.00   95.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157 -178.0000  -30.0000 35

 13 omega    7.00   32.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157  -57.0000   90.0000 25

 14 omega  -71.00   25.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157    0.0000 -150.0000 96

 15 omega   -7.00   87.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157   38.0000 -150.0000 94

 16 omega  -12.00   87.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       12.7157   38.0000  -60.0000 99

 17 omega    4.00   35.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       14.0000 -128.0000    0.3621 31

 18 omega   42.00   72.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       14.0000 -128.0000    0.3621 30

 19 omega   43.00   68.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       14.0000 -121.0000 -102.2200 25

 20 omega   14.00   73.00   1.0000   21.6800
omega____ theta____ kappa____ phi______ frames
    -       14.0000 -129.0000   60.0855 59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0188539000
_diffrn_orient_matrix_UB_12      0.0307538000
_diffrn_orient_matrix_UB_13      -0.0227751000
_diffrn_orient_matrix_UB_21      -0.0026405000
_diffrn_orient_matrix_UB_22      -0.0349594000
_diffrn_orient_matrix_UB_23      -0.0235935000
_diffrn_orient_matrix_UB_31      -0.0439168000
_diffrn_orient_matrix_UB_32      -0.0110992000
_diffrn_orient_matrix_UB_33      0.0112002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            54658
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.231
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+3.9940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2273
_reflns_number_total             2572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01047_si_002.cif
_cod_data_source_block           13
_cod_original_cell_volume        4494.73(13)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4516082
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'N4 C12'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C12(H12), C9(H9), C10(H10), C11(H11)
;
_shelx_res_checksum              27077
_shelx_hkl_checksum              59575
_olex2_date_sample_data_collection 2017-11-16
_olex2_submission_special_instructions 'No special instructions were received'