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_7157126
_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         '3(C10 H8 F3 N3 O)'
_chemical_formula_sum            'C30 H24 F9 N9 O3'
_chemical_formula_weight         729.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-05 deposited with the CCDC.    2019-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                84.402(6)
_cell_angle_beta                 81.612(7)
_cell_angle_gamma                85.682(7)
_cell_formula_units_Z            2
_cell_length_a                   8.042(4)
_cell_length_b                   10.654(5)
_cell_length_c                   20.098(9)
_cell_measurement_reflns_used    1814
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.722
_cell_measurement_theta_min      2.565
_cell_volume                     1692.2(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.1174
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13751
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.745
_diffrn_reflns_theta_min         1.028
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.7122.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.1827
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1092P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.2402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3141
_reflns_number_total             7329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob01865d2.cif
_cod_data_source_block           cyj-2-2a
_cod_depositor_comments
'Adding full bibliography for 7157125--7157126.cif.'
_cod_original_cell_volume        1692.3(13)
_cod_database_code               7157126
_shelx_shelxl_version_number     2018/3
_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 Aromatic/amide H refined with riding coordinates:
 N008(H008), N00A(H00A), N00B(H00B), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012), C013(H013),
 C017(H017), C019(H019), C01A(H01G)
2.b Idealised Me refined as rotating group:
 C01D(H01A,H01B,H01C), C01E(H01D,H01E,H01F), C01F(H01H,H01I,H01J)
;
_shelx_res_checksum              17866
_olex2_submission_special_instructions 'No special instructions were received'