Synthesis of 3-(tri/difluoromethyl)-1H-1,2,4-triazol-5(4H)-ones via the cyclization of hydrazinecarboxamides with tri/difluoroacetic anhydride.
You, Yi; Chen, Yueji; You, Chenhui; Wang, Junwen; Weng, Zhiqiang; Organic & biomolecular chemistry 17 (2019) 9343–9347; doi:10.1039/c9ob01865d

data_7157125
_publ_section_title
;
 Synthesis of 3-(tri/difluoromethyl)-1H-1,2,4-triazol-5(4H)-ones via the
 cyclization of hydrazinecarboxamides with tri/difluoroacetic anhydride.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9343
_journal_page_last               9347
_journal_paper_doi               10.1039/c9ob01865d
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C10 H9 F2 N3 O'
_chemical_formula_sum            'C10 H9 F2 N3 O'
_chemical_formula_weight         225.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-17
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.04.16 svn.r3589 for OlexSys, GUI svn.r5734)
;
_audit_update_record
;
2019-04-17 deposited with the CCDC.    2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.544(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8495(17)
_cell_length_b                   10.2381(11)
_cell_length_c                   13.1866(15)
_cell_measurement_reflns_used    2649
_cell_measurement_temperature    295.54(10)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      2.6970
_cell_volume                     2071.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.54(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.825
_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    -48.00  77.00   0.50   13.00    --   -9.70  43.00 -30.00  250
  2  \w    -92.00 -65.00   0.50   13.00    --   -9.70  43.00 -60.00   54
  3  \w    -34.00  66.00   0.50   13.00    --   -9.70  43.00 -60.00  200
  4  \w    -98.00 -58.00   0.50   13.00    --   -9.70  43.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0164707000
_diffrn_orient_matrix_UB_12      0.0637387000
_diffrn_orient_matrix_UB_13      -0.0038361000
_diffrn_orient_matrix_UB_21      -0.0420053000
_diffrn_orient_matrix_UB_22      0.0209169000
_diffrn_orient_matrix_UB_23      -0.0282544000
_diffrn_orient_matrix_UB_31      -0.0099985000
_diffrn_orient_matrix_UB_32      0.0174710000
_diffrn_orient_matrix_UB_33      0.0476997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.471
_diffrn_reflns_theta_min         2.550
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0112(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0527P)^2^+0.5681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1081
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1751
_reflns_number_total             2380
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01865d2.cif
_cod_data_source_block           cyj-2-2f-2a
_cod_depositor_comments
'Adding full bibliography for 7157125--7157126.cif.'
_cod_database_code               7157125
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00A(H00A), C00B(H00B), C00D(H00D), C00F(H00F)
2.c Idealised Me refined as rotating group:
 C00G(H00C,H00G,H00H)
;
_shelx_res_checksum              57687
_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 1.355
_oxdiff_exptl_absorpt_empirical_full_min 0.696