O-Trifluoromethylation of ketones: an alternative straightforward route to alkenyl trifluoromethyl ethers
Gao, Chi; Liu, Yang; Li, Cheng-Sheng; Guo, He; Wang, Sheng-Han; Xu, Cong; Wang, Mang; Chemical Science 16 (2025) 8561–8568; doi:10.1039/D5SC01073J

data_1574376
_publ_section_title
;
 O-Trifluoromethylation of ketones: an alternative straightforward route
 to alkenyl trifluoromethyl ethers
;
_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              8561
_journal_page_last               8568
_journal_paper_doi               10.1039/D5SC01073J
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C17 H14 F N3'
_chemical_formula_sum            'C17 H14 F N3'
_chemical_formula_weight         279.31
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2ktcwn
_audit_creation_date             2024-08-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-08-16 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.936(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1473(13)
_cell_length_b                   6.2052(5)
_cell_length_c                   18.1878(17)
_cell_measurement_reflns_used    1451
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9790
_cell_measurement_theta_min      4.5830
_cell_volume                     1419.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.845
_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      1.00  85.00   1.00   17.50    --   10.85  38.00-180.00   84
  2  \w    -15.00  76.00   1.00   17.50    --   10.85  57.00  90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0113412000
_diffrn_orient_matrix_UB_12      -0.0034868000
_diffrn_orient_matrix_UB_13      0.0405540000
_diffrn_orient_matrix_UB_21      -0.0552458000
_diffrn_orient_matrix_UB_22      0.0023969000
_diffrn_orient_matrix_UB_23      -0.0038190000
_diffrn_orient_matrix_UB_31      -0.0015351000
_diffrn_orient_matrix_UB_32      -0.1142645000
_diffrn_orient_matrix_UB_33      -0.0013395000
_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  0.0246
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6716
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.370
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0601
_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^)+(0.0663P)^2^+0.2899P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1725
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1861
_reflns_number_total             3308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01073j2.cif
_cod_data_source_block           220307-wm01-pwy_auto
_cod_depositor_comments
'Adding full bibliography for 1574376--1574377.cif.'
_cod_database_code               1574376
_shelx_shelxl_version_number     2019/2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00C(H00C), C00F(H00F), C00H(H00H), C00I(H00I),
 C00K(H00L), C00L(H00M)
2.b Idealised Me refined as rotating group:
 C00G(H00B,H00D,H00E), C00J(H00G,H00J,H00K)
;
_shelx_res_checksum              17534
_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 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.819