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_1574377
_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         'C28 H21 F3 O'
_chemical_formula_sum            'C28 H21 F3 O'
_chemical_formula_weight         430.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-17
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-05 deposited with the CCDC.	2025-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.414(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7028(6)
_cell_length_b                   5.5202(2)
_cell_length_c                   33.5271(14)
_cell_measurement_reflns_used    8065
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.403
_cell_measurement_theta_min      2.429
_cell_volume                     2159.49(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      300.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            32058
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.359
_diffrn_reflns_theta_min         2.428
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1168 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.8771.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0061(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0775P)^2^+0.4129P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2919
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01073j2.cif
_cod_data_source_block           mo_wangm250117_1
_cod_depositor_comments
'Adding full bibliography for 1574376--1574377.cif.'
_cod_database_code               1574377
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 F002-C00S \\sim F2-C00S
 with sigma of 0.02
 F003-C00S \\sim F0-C00S
 with sigma of 0.02
 F004-C00S \\sim F1-C00S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F0) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(F1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Others
 Sof(F0)=Sof(F1)=Sof(F2)=1-FVAR(1)
 Sof(F002)=Sof(F003)=Sof(F004)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00F(H00F)
5.b Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00E)
5.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W)
;
_shelx_res_checksum              76078
_olex2_submission_special_instructions 'No special instructions were received'