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_4516077
_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      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)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.7647(3)
_cell_length_b                   13.7647(3)
_cell_length_c                   20.6510(9)
_cell_measurement_reflns_used    2805
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7110
_cell_measurement_theta_min      3.8460
_cell_volume                     3912.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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
;
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'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -116.00 -18.00   1.00    5.00    --  -40.38 -38.00 -30.00   98
  2  \w     70.00 103.00   1.00    5.00    --   40.38 178.00 -30.00   33
  3  \w    127.00 153.00   1.00    5.00    --  113.00 112.00 -60.00   26
  4  \w    149.00 178.00   1.00    5.00    --  113.00 112.00 -90.00   29
  5  \w    143.00 169.00   1.00    5.00    --  113.00  30.00-180.00   26
  6  \w    116.00 142.00   1.00    5.00    --  113.00 112.00 -90.00   26
  7  \w     94.00 142.00   1.00    5.00    --  113.00  45.00   0.00   48
  8  \w     86.00 145.00   1.00    5.00    --  113.00  45.00  90.00   59
  9  \w    129.00 158.00   1.00    5.00    --  113.00  45.00 120.00   29
 10  \w    133.00 174.00   1.00    5.00    --  113.00  30.00 150.00   41
 11  \w    108.00 159.00   1.00    5.00    --  113.00 111.00 156.00   51
 12  \w     83.00 114.00   1.00    5.00    --  113.00  30.00 150.00   31
 13  \w     36.00  86.00   1.00    5.00    --  113.00 -15.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0383389000
_diffrn_orient_matrix_UB_12      0.0681486000
_diffrn_orient_matrix_UB_13      -0.0534492000
_diffrn_orient_matrix_UB_21      -0.1025576000
_diffrn_orient_matrix_UB_22      0.0426886000
_diffrn_orient_matrix_UB_23      -0.0085609000
_diffrn_orient_matrix_UB_31      0.0228834000
_diffrn_orient_matrix_UB_32      0.0778509000
_diffrn_orient_matrix_UB_33      0.0513900000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5946
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_min         3.859
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.278
_exptl_crystal_description       prism
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0463
_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^)+(0.0803P)^2^+1.8547P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1734
_reflns_number_total             1856
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01047_si_002.cif
_cod_data_source_block           4_tetragonal
_cod_original_cell_volume        3912.7(3)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               4516077
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Zn Cl2 C40'
_reflns_odcompleteness_completeness 99.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.663(2)
 0.337(2)
2. 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
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              44128
_shelx_hkl_checksum              29058
_olex2_date_sample_data_collection 1498484000.56
_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 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.611