Photoredox-catalyzed allylation of C(sp<sup>3</sup>)-H bonds in <i>N</i>-trifluoroethyl hydroxylamines or hydroxamides <i>via</i> hydrogen atom transfer.
Wang, Jia-Yin; Dai, Jin-Long; Wang, Tao; Zhang, Ming-Xian; Sha, Hong-Kai; Yan, Shenghu; Organic & biomolecular chemistry 23 (2025) 10051–10056; doi:10.1039/d5ob01288k

data_7160747
_publ_section_title
;
 Photoredox-catalyzed allylation of C(sp<sup>3</sup>)-H bonds in
 <i>N</i>-trifluoroethyl hydroxylamines or hydroxamides <i>via</i>
 hydrogen atom transfer.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10051
_journal_page_last               10056
_journal_paper_doi               10.1039/d5ob01288k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H22 F3 N O4'
_chemical_formula_sum            'C18 H22 F3 N O4'
_chemical_formula_weight         373.36
_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_creation_date             2024-07-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-07-30 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.141(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.644(4)
_cell_length_b                   5.2728(9)
_cell_length_c                   18.686(4)
_cell_measurement_reflns_used    2928
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.44
_cell_volume                     1836.9(6)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12437
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.211
_diffrn_reflns_theta_max         25.211
_diffrn_reflns_theta_min         2.180
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8127.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.012(2)
_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   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0750P)^2^+1.1691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1763
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             3305
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01288k2.cif
_cod_data_source_block           a3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7160747.cif.
;
_cod_database_code               7160747
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.591(2)
 0.409(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C3(H3), C7(H7), C1(H1A), C2(H2)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C10(H10A,H10B,H10C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              21429
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU