Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of pyridinium 1,4-zwitterionic thiolates with CF3CN
Yao, Yunfei; Lin, Bo; Wu, Minze; Zhang, Yafang; Huang, Yangjie; Han, Xiaoyan; Weng, Zhiqiang; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01749K

data_7158933
_publ_section_title
;
 Synthesis of 2-trifluoromethyl thiazoles via [3 + 2] cycloaddition of
 pyridinium 1,4-zwitterionic thiolates with CF3CN
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01749K
_journal_year                    2022
_chemical_formula_moiety         'C8 H6 F3 N O4 S'
_chemical_formula_sum            'C8 H6 F3 N O4 S'
_chemical_formula_weight         269.20
_chemical_name_systematic        P-1
_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     dual
_audit_creation_date             2021-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-17 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                74.601(3)
_cell_angle_beta                 77.073(3)
_cell_angle_gamma                82.099(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7049(7)
_cell_length_b                   8.0698(6)
_cell_length_c                   9.0862(8)
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.049
_cell_measurement_theta_min      2.371
_cell_volume                     529.03(8)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.371
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0312P)^2^+0.2814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1807
_reflns_number_total             1877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01749k2.cif
_cod_data_source_block           cf3sz
_cod_database_code               7158933
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              92629
_olex2_submission_special_instructions 'No special instructions were received'