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_7158934
_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         'C18 H12 F3 N O3 S'
_chemical_formula_sum            'C18 H12 F3 N O3 S'
_chemical_formula_weight         379.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-30 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.951(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8566(2)
_cell_length_b                   35.3036(13)
_cell_length_c                   10.3267(4)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.9680
_cell_measurement_theta_min      2.5000
_cell_volume                     1757.56(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_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    -44.00 -10.00   0.50    2.00    --   42.50 -32.00  90.00   68
  2  \w     14.00  70.00   0.50    2.00    --   42.50 -54.00 -90.00  112
  3  \w     89.00 120.00   0.50    2.00    --   42.50  82.00-150.00   62
  4  \w     28.00  74.00   0.50    2.00    --   42.50 -32.00  90.00   92
  5  \w    -46.00  27.00   0.50    2.00    --   42.50 -77.00  60.00  146
  6  \w     32.00  66.00   0.50    2.00    --   42.50 -77.00  60.00   68
  7  \w     16.00  84.00   0.50    2.00    --   42.50  82.00-150.00  136
  8  \w     19.00  66.00   0.50    2.00    --   42.50 -77.00 -90.00   94
  9  \w     70.00 121.00   0.50    2.00    --   42.50  65.00  30.00  102
 10  \w    -33.00  -8.00   0.50    2.00    --   42.50 -54.00 -90.00   50
 11  \w      5.00  87.00   0.50    2.00    --   93.70 -59.00  90.00  164
 12  \w     38.00  64.00   0.50    2.00    --   93.70 -50.00-120.00   52
 13  \w     52.00 121.00   0.50    2.00    --   93.70 -59.00   0.00  138
 14  \w     45.00  93.00   0.50    2.00    --   93.70 -82.00-150.00   96
 15  \w      6.00  32.00   0.50    2.00    --   93.70 -59.00   0.00   52
 16  \w     62.00 113.00   0.50    2.00    --   93.70 -82.00 -90.00  102
 17  \w      4.00  44.00   0.50    2.00    --   93.70 -82.00 -90.00   80
 18  \w     87.00 183.00   0.50    2.00    --   93.70  33.00-150.00  192
 19  \w     70.00 116.00   0.50    2.00    --   93.70 -50.00-120.00   92
 20  \w     90.00 116.00   0.50    2.00    --   93.70 -82.00-180.00   52
 21  \w     10.00  88.00   0.50    2.00    --   93.70 -42.00   0.00  156
 22  \w     23.00 119.00   0.50    2.00    --   93.70 -59.00 150.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Pro II AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1242100000
_diffrn_orient_matrix_UB_12      0.0060634000
_diffrn_orient_matrix_UB_13      0.1429869000
_diffrn_orient_matrix_UB_21      -0.0561275000
_diffrn_orient_matrix_UB_22      -0.0418648000
_diffrn_orient_matrix_UB_23      0.0297753000
_diffrn_orient_matrix_UB_31      0.2889771000
_diffrn_orient_matrix_UB_32      -0.0107299000
_diffrn_orient_matrix_UB_33      -0.0354856000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8045
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.266
_diffrn_reflns_theta_min         2.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0630
_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^)+(0.1255P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1975
_reflns_number_total             3167
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01749k2.cif
_cod_data_source_block           yyf20220630-1_auto
_cod_database_code               7158934
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.818
_shelx_estimated_absorpt_t_min   0.818
_diffrn_oxdiff_digest_frames
;
014b9febac2010ef93a33cbced70267b3a00026ff68
;
_diffrn_oxdiff_digest_hkl
;
010720270b8c0930370c0c08e546ac027f141e
;
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00D,H00F,H00G)
;
_shelx_res_checksum              32721
_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 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.678