PyfSeTs as a Novel and Photosensitive Reagent for the Green Light-Induced Arene C-H Selenenylation: A Verstile Strategy for the Synthesis of Aryl Selenides
Shi, Haoliang; Qu, Huorong; Wang, Xinyan; Wei, Jinlian; Wu, Shanchao; Zhang, Yongqiang; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00102E

data_7161066
_publ_section_title
;
 PyfSeTs as a novel and photosensitive reagent for green light-induced
 arene C-H selenenylation: a versatile strategy for the synthesis of aryl
 selenides.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2923
_journal_page_last               2931
_journal_paper_doi               10.1039/d6ob00102e
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C12 H7 F4 N O2 S Se'
_chemical_formula_sum            'C12 H7 F4 N O2 S Se'
_chemical_formula_weight         384.21
_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
_audit_creation_date             2025-06-09
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-07-07 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                102.402(5)
_cell_angle_beta                 98.371(6)
_cell_angle_gamma                103.685(5)
_cell_formula_units_Z            2
_cell_length_a                   6.5644(13)
_cell_length_b                   8.2458(16)
_cell_length_c                   13.659(3)
_cell_measurement_reflns_used    2988
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      64.850
_cell_measurement_theta_min      5.713
_cell_volume                     686.4(2)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15394
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         5.718
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.631
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1489 before and 0.0939 after correction.
The Ratio of minimum to maximum transmission is 0.3620.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.654
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0607
_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^)+(0.1066P)^2^+0.7256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1551
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2416
_reflns_number_total             2444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00102e2.cif
_cod_data_source_block           y20210103_05_6_2nd_0m1_a
_cod_depositor_comments
'Adding full bibliography for 7161064--7161066.cif.'
_cod_database_code               7161066
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.431
_shelx_estimated_absorpt_t_min   0.212
_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. Uiso/Uaniso restraints and constraints
C4 \\sim C6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(N5) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'