Imidazopyridine substituted cyclic selenonium(IV) salts as chalcogen bond catalysts.
Kuczmera, Thomas J.; Puylaert, Pim; Wirth, Thomas; Nachtsheim, Boris J.; Chemical communications (Cambridge, England) 61 (2025) 14169–14172; doi:10.1039/d5cc04027b

data_7134883
_publ_section_title
;
 Imidazopyridine substituted cyclic selenonium(IV) salts as chalcogen bond
 catalysts.
;
_journal_issue                   74
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14169
_journal_page_last               14172
_journal_paper_doi               10.1039/d5cc04027b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C20 H16 N2 Se, 2(C F3 O3 S)'
_chemical_formula_sum            'C22 H16 F6 N2 O6 S2 Se'
_chemical_formula_weight         661.45
_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             2024-12-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-06 deposited with the CCDC.	2025-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                87.959(2)
_cell_angle_beta                 87.081(2)
_cell_angle_gamma                70.209(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6925(4)
_cell_length_b                   8.6622(4)
_cell_length_c                   20.1522(11)
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.33
_cell_volume                     1261.63(11)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            41923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.569
_diffrn_reflns_theta_min         2.499
_diffrn_source                   'microfocus Ims X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    1.741
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1131 before and 0.0592 after correction.
The Ratio of minimum to maximum transmission is 0.8922.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.338
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         7676
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0541P)^2^+2.9912P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6095
_reflns_number_total             7676
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04027b2.cif
_cod_data_source_block           kuczmerat240506
_cod_depositor_comments          'Adding full bibliography for 7134883.cif.'
_cod_database_code               7134883
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.733
_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. Restrained distances
 S2B-O6B \\sim S2A-O6A
 with sigma of 0.02
 S2B-C22B \\sim S2A-C22A
 with sigma of 0.02
 F4B-C22B \\sim F4A-C22A
 with sigma of 0.02
 F6B-C22B \\sim F6A-C22A
 with sigma of 0.02
 C22B-F5B \\sim C22A-F5A
 with sigma of 0.02
 S2B-F4B \\sim S2A-F4A
 with sigma of 0.04
 S2B-F6B \\sim S2A-F6A
 with sigma of 0.04
 S2B-F5B \\sim S2A-F5A
 with sigma of 0.04
 O6B-C22B \\sim O6A-C22A
 with sigma of 0.04
 F4B-F6B \\sim F4A-F6A
 with sigma of 0.04
 F4B-F5B \\sim F4A-F5A
 with sigma of 0.04
 F6B-F5B \\sim F6A-F5A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C22B) \\sim Ueq, Uanis(F5B) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F4B)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 F5B, C22B, F4B, F6B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C22A)=Sof(S2A)=Sof(O6A)=Sof(F4A)=Sof(F6A)=Sof(F5A)=1-FVAR(1)
 Sof(S2B)=Sof(O6B)=Sof(F4B)=Sof(F6B)=Sof(C22B)=Sof(F5B)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C9(H9), C10(H10), C3(H3), C16(H16), C2(H2), C4(H4), C5(H5),
 C12(H12), C19(H19), C17(H17), C11(H11), C18(H18)
6.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              45018
_shelx_hkl_checksum              93989
_olex2_submission_special_instructions 'No special instructions were received'