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_4516079
_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 H11 Cl N4, H2 O'
_chemical_formula_sum            'C10 H13 Cl N4 O'
_chemical_formula_weight         240.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_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                 105.340(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8204(17)
_cell_length_b                   7.1084(7)
_cell_length_c                   24.264(4)
_cell_measurement_reflns_used    3644
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.9080
_cell_measurement_theta_min      3.8700
_cell_volume                     2298.8(5)
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -28.00   5.00   1.00  125.00    --  -14.34 -77.00  60.00   33
  2  \w     -7.00  89.00   1.00  125.00    --   16.06  38.00 150.00   96
  3  \w    -10.00  70.00   1.00  125.00    --   16.06  57.00-120.00   80
  4  \w     -2.00  25.00   1.00  125.00    --  -14.34 -99.00-180.00   27
  5  \w    -53.00 -26.00   1.00  125.00    --  -14.34 -77.00 -60.00   27
  6  \w     51.00  79.00   1.00  125.00    --   16.06   0.00 -30.00   28
  7  \w    -22.00   5.00   1.00  125.00    --   16.06   0.00 -30.00   27
  8  \w     39.00  85.00   1.00  125.00    --   16.06-178.00-150.00   46
  9  \w     62.00 102.00   1.00  125.00    --   16.06-178.00 -60.00   40
 10  \w     35.00  68.00   1.00  125.00    --   16.06-178.00 -30.00   33
 11  \w     63.00  92.00   1.00  125.00    --   16.06-178.00  60.00   29
;
_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      0.0154391000
_diffrn_orient_matrix_UB_12      0.0286012000
_diffrn_orient_matrix_UB_13      0.0290032000
_diffrn_orient_matrix_UB_21      0.0506042000
_diffrn_orient_matrix_UB_22      0.0018299000
_diffrn_orient_matrix_UB_23      -0.0014421000
_diffrn_orient_matrix_UB_31      -0.0056585000
_diffrn_orient_matrix_UB_32      0.0955446000
_diffrn_orient_matrix_UB_33      -0.0086908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12182
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         3.248
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66998
_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    1.391
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0658P)^2^+1.7714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2185
_reflns_number_total             2630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b01047_si_002.cif
_cod_data_source_block           5
_cod_database_code               4516079
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Zn C6 Cl2'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_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, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C6(H6), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              74294
_shelx_hkl_checksum              95053
_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 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.400