Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN
Lin, Bo; Yao, Yunfei; Huang, Yangjie; Lin, Qi; Weng, Zhiqiang; Chemical Communications  (2022) –; doi:10.1039/D2CC03928A

data_7130837
_publ_section_title
;
 Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via
 photocycloaddition of sydnone with CF3CN
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03928A
_journal_year                    2022
_chemical_formula_moiety         'C9 H5 F3 N2 O'
_chemical_formula_sum            'C9 H5 F3 N2 O'
_chemical_formula_weight         214.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-08 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.245(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.5653(19)
_cell_length_b                   4.4815(5)
_cell_length_c                   24.060(2)
_cell_measurement_reflns_used    3620
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      3.68
_cell_volume                     1890.9(3)
_computing_cell_refinement       lb20201022
_computing_data_reduction        lb20201022
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6581
_diffrn_reflns_theta_full        66.51
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_min         3.68
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.251
_exptl_absorpt_correction_T_max  0.9401
_exptl_absorpt_correction_T_min  0.8851
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1027P)^2^+3.8934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2352
_reflns_number_gt                1206
_reflns_number_total             1610
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03928a2.cif
_cod_data_source_block           11
_cod_database_code               7130837
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E)
;
_olex2_submission_special_instructions 'No special instructions were received'