<i>Se</i>-Aryl-<i>N</i>-phenylphenoselenazinium salts: aryl radical precursors incorporating a photosensitizer unit.
Kurokawa, Takuma; Takahashi, Shintaro; Kano, Naokazu; Chemical communications (Cambridge, England) 61 (2025) 14454–14457; doi:10.1039/d5cc03637b

data_7134896
_publ_section_title
;
 <i>Se</i>-Aryl-<i>N</i>-phenylphenoselenazinium salts: aryl radical
 precursors incorporating a photosensitizer unit.
;
_journal_issue                   75
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14454
_journal_page_last               14457
_journal_paper_doi               10.1039/d5cc03637b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C19 H16 N Se, C F3 O3 S, C5 H10 O'
_chemical_formula_sum            'C25 H26 F3 N O4 S Se'
_chemical_formula_weight         572.49
_chemical_properties_physical    Light-sensitive
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-06-10 deposited with the CCDC.	2025-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                83.126(2)
_cell_angle_beta                 88.202(2)
_cell_angle_gamma                79.760(2)
_cell_formula_units_Z            2
_cell_length_a                   10.3394(2)
_cell_length_b                   10.4055(3)
_cell_length_c                   11.5682(3)
_cell_measurement_reflns_used    11202
_cell_measurement_temperature    121.0(7)
_cell_measurement_theta_max      30.4980
_cell_measurement_theta_min      2.0350
_cell_volume                     1215.89(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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_environment      N~2~
_diffrn_ambient_temperature      121.0(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.946
_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      3.00  52.00   0.50    4.00    --   20.00  54.00 -60.00   98
  2  \w     80.00 106.00   0.50    4.00    --   20.00  54.00 -60.00   52
  3  \w    -73.00 -28.00   0.50    4.00    --   20.00  54.00  60.00   90
  4  \w    -23.00  73.00   0.50    4.00    --   20.00  54.00  60.00  192
  5  \w    -71.00  12.00   0.50    4.00    --   20.00  54.00 120.00  166
  6  \w    -74.00 107.00   0.50    4.00    --   20.00  54.00 -90.00  362
  7  \w    -74.00  56.00   0.50    4.00    --   20.00  54.00-150.00  260
  8  \w     85.00 110.00   0.50    4.00    --   20.00  54.00-150.00   50
  9  \w    -69.00 -44.00   0.50    4.00    --   20.00  54.00 150.00   50
 10  \w      3.00  96.00   0.50    4.00    --   20.00  54.00 150.00  186
 11  \w    -74.00 -45.00   0.50    4.00    --   20.00  54.00  30.00   58
 12  \w      2.00  29.00   0.50    4.00    --   20.00  54.00  30.00   54
 13  \w     72.00  97.00   0.50    4.00    --   20.00  54.00  30.00   50
 14  \w    -67.00   3.00   0.50    4.00    --   20.00  54.00 -30.00  140
 15  \w     38.00  64.00   0.50    4.00    --   20.00  54.00 -30.00   52
 16  \w     74.00  99.00   0.50    4.00    --   20.00  54.00 -30.00   50
 17  \w    -63.00 -38.00   0.50    4.00    --   20.00  54.00-120.00   50
 18  \w      5.00  30.00   0.50    4.00    --   20.00  54.00-120.00   50
 19  \w     62.00  87.00   0.50    4.00    --   20.00  54.00-120.00   50
 20  \w    -70.00 -42.00   0.50    4.00    --   20.00  54.00  90.00   56
 21  \w     63.00  88.00   0.50    4.00    --   20.00  54.00  90.00   50
 22  \w    -46.00 -21.00   0.50    4.00    --   20.00  54.00 -60.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0296602000
_diffrn_orient_matrix_UB_12      -0.0470529000
_diffrn_orient_matrix_UB_13      -0.0241241000
_diffrn_orient_matrix_UB_21      -0.0579276000
_diffrn_orient_matrix_UB_22      0.0179982000
_diffrn_orient_matrix_UB_23      0.0330780000
_diffrn_orient_matrix_UB_31      -0.0249998000
_diffrn_orient_matrix_UB_32      0.0482265000
_diffrn_orient_matrix_UB_33      -0.0462427000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24085
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.734
_diffrn_reflns_theta_min         2.002
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.564
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.259
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         7149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0433
_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^)+(0.0676P)^2^+0.4912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5977
_reflns_number_total             7149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03637b2.cif
_cod_data_source_block           tkm538
_cod_depositor_comments
'Adding full bibliography for 7134895--7134897.cif.'
_cod_database_code               7134896
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C20H16NSeO3SF3
_shelx_estimated_absorpt_t_max   0.678
_shelx_estimated_absorpt_t_min   0.574
_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. Others
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(C38)=Sof(H38A)=Sof(H38B)=Sof(H38C)=Sof(C37)=
 Sof(H37A)=Sof(H37B)=1-FVAR(1)
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C34)=
 Sof(H34A)=Sof(H34B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C36(H36A,H36B), C37(H37A,H37B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C12(H12), C21(H21), C15(H15), C17(H17), C8(H8), C6(H6),
 C18(H18), C20(H20), C19(H19), C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              95823
_shelx_hkl_checksum              38843
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.867