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_4516081
_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 H16 N4'
_chemical_formula_sum            'C12 H16 N4'
_chemical_formula_weight         216.29
_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     iterative
_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                75.686(4)
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_cell_length_a                   8.6523(4)
_cell_length_b                   11.7604(7)
_cell_length_c                   12.8395(6)
_cell_measurement_reflns_used    7566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.2840
_cell_measurement_theta_min      2.9180
_cell_volume                     1199.33(11)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -20.00   20.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  -90.0000 40

  2 omega  -86.00  -42.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678 -178.0000   30.0000 44

  3 omega  -25.00   12.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000  150.0000 37

  4 omega  -23.00    7.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -      -22.2678  -99.0000   60.0000 30

  5 omega    0.00   94.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000   90.0000 94

  6 omega   42.00   95.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000  -30.0000 53

  7 omega   44.00   92.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000 -150.0000 48

  8 omega  -43.00   49.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -38.0000  -90.0000 92

  9 omega  -25.00   65.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000 -180.0000 90

 10 omega  -24.00   65.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   60.0000 89

 11 omega    3.00   63.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000 -180.0000 60

 12 omega   35.00   64.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -60.0000 29

 13 omega    0.00   91.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   38.0000  -60.0000 91

 14 omega   44.00   92.00   1.0000   21.8000
omega____ theta____ kappa____ phi______ frames
    -       23.3616   57.0000  -30.0000 48
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0018432000
_diffrn_orient_matrix_UB_12      -0.0572164000
_diffrn_orient_matrix_UB_13      -0.0077326000
_diffrn_orient_matrix_UB_21      -0.0347049000
_diffrn_orient_matrix_UB_22      -0.0133194000
_diffrn_orient_matrix_UB_23      0.0530816000
_diffrn_orient_matrix_UB_31      -0.0792444000
_diffrn_orient_matrix_UB_32      0.0281628000
_diffrn_orient_matrix_UB_33      -0.0195783000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20603
_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         27.500
_diffrn_reflns_theta_min         2.632
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0619P)^2^+0.5066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             5506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01047_si_002.cif
_cod_data_source_block           10
_cod_original_cell_volume        1199.32(11)
_cod_database_code               4516081
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 h14 n4 o zn1'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N1A(H1A), C7(H7), C7A(H7A), C8(H8), C11(H11), C10(H10), C11A(H11A),
 C10A(H10A), C8A(H8A)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC), C4A(H4AA,H4AB,H4AC), C4(H4A,H4B,H4C),
 C12(H12D,H12E,H12F), C12A(H12A,H12B,H12C)
;
_shelx_res_checksum              24097
_shelx_hkl_checksum              15757
_olex2_submission_special_instructions 'No special instructions were received'