Proton Delocalization in Short Hydrogen Bonds Assembling HSeO4– Anions into Supramolecular Adducts
Beccaria, Roberta; Pizzi, Andrea; Chakalov, Edem R.; Resnati, Giuseppe; Tolstoy, Peter; Physical Chemistry Chemical Physics  (2025) –; doi:10.1039/D5CP01211B

data_7250517
_publ_section_title
;
 Proton Delocalization in Short Hydrogen Bonds Assembling HSeO4-- Anions
 into Supramolecular Adducts
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP01211B
_journal_year                    2025
_chemical_formula_moiety         'H O4 Se, C5 H6 N'
_chemical_formula_sum            'C5 H7 N O4 Se'
_chemical_formula_weight         224.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-17 deposited with the CCDC.	2025-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.0590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8196(2)
_cell_length_b                   6.26820(10)
_cell_length_c                   13.2167(2)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    298.01(10)
_cell_measurement_theta_max      76.1580
_cell_measurement_theta_min      3.5720
_cell_volume                     1551.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_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     36.00  62.00   0.50    0.05    --  105.25-125.00 -30.00   52
  2  \w     67.00  99.00   0.50    0.05    --  105.25-125.00 -30.00   64
  3  \w     87.00 112.00   0.50    0.05    --  105.25-125.00 -90.00   50
  4  \w     62.00 109.00   0.50    0.05    --  105.25-125.00-120.00   94
  5  \w     40.00  77.00   0.50    0.05    --  105.25-125.00 -90.00   74
  6  \w     36.00  61.00   0.50    0.05    --  105.25 -61.00-120.00   50
  7  \w     41.00  67.00   0.50    0.05    --  105.25 -61.00 -90.00   52
  8  \w     33.00  64.00   0.50    0.05    --  105.25 -61.00-180.00   62
  9  \w    -25.00  43.00   0.50    0.05    --   47.32 -38.00-120.00  136
 10  \w    -27.00  25.00   0.50    0.05    --   47.32 -16.00  -4.00  104
 11  \w     39.00  66.00   0.50    0.05    --  105.25 -61.00 120.00   54
 12  \w     33.00  71.00   0.50    0.05    --  105.25 -61.00 150.00   76
 13  \w     92.00 178.00   0.50    0.05    --  105.25  16.00 165.00  172
 14  \w     33.00 120.00   0.50    0.05    --   47.32  57.00-120.00  174
 15  \w     25.00 120.00   0.50    0.05    --   47.32  77.00-150.00  190
 16  \w     25.00 120.00   0.50    0.05    --   47.32  77.00 -90.00  190
 17  \w     33.00 120.00   0.50    0.05    --   47.32  57.00-150.00  174
 18  \w     35.00 120.00   0.50    0.05    --   47.32  38.00-180.00  170
 19  \w     85.00 124.00   0.50    0.05    --  105.25  77.00-180.00   78
 20  \w    144.00 175.00   0.50    0.05    --  105.25  77.00-180.00   62
 21  \w     34.00 122.00   0.50    0.05    --   47.32  16.00 165.00  176
 22  \w    -25.00  27.00   0.50    0.05    --  -47.32  16.00 165.00  104
 23  \w    -51.00 -23.00   0.50    0.05    --  -91.75  45.00 150.00   56
 24  \w    -72.00 -26.00   0.50    0.05    --  -91.75 125.00-150.00   92
 25  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00-132.03  188
 26  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00-120.00  188
 27  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00 -60.00  188
 28  \w    -96.00 -70.00   0.50    0.05    --  -91.75 -77.00   0.00   52
 29  \w   -159.00-101.00   0.50    0.05    --  -91.75 -77.00   0.00  116
 30  \w   -163.00-112.00   0.50    0.05    --  -91.75 -77.00 -30.00  102
 31  \w    -98.00 -72.00   0.50    0.05    --  -91.75 -77.00 -30.00   52
 32  \w    -97.00 -71.00   0.50    0.05    --  -91.75 -77.00 -90.00   52
 33  \w    -95.00 -70.00   0.50    0.05    --  -91.75 -75.00 -91.74   50
 34  \w    -94.00 -69.00   0.50    0.05    --  -91.75 -77.00-150.00   50
 35  \w   -101.00 -70.00   0.50    0.05    --  -91.75 -75.00-108.62   62
 36  \w   -163.00-113.00   0.50    0.05    --  -91.75 -75.00-108.62  100
 37  \w   -163.00 -75.00   0.50    0.05    --  -91.75 -62.00 -69.42  176
 38  \w   -105.00 -73.00   0.50    0.05    --  -91.75 -66.00 -40.68   64
 39  \w   -100.00 -75.00   0.50    0.05    --  -91.75 -61.00 -66.18   50
 40  \w   -106.00 -76.00   0.50    0.05    --  -91.75 -61.00 -90.00   60
 41  \w   -148.00-122.00   0.50    0.05    --  -91.75 -77.00-150.00   52
 42  \w   -148.00-122.00   0.50    0.05    --  -91.75 -61.00-120.00   52
 43  \w   -117.00 -75.00   0.50    0.05    --  -91.75 -61.00-120.00   84
 44  \w   -103.00 -77.00   0.50    0.05    --  -91.75 -61.00-180.00   52
 45  \w   -114.00 -76.00   0.50    0.05    --  -91.75 -59.00-163.31   76
 46  \w   -151.00-125.00   0.50    0.05    --  -91.75 -59.00-163.31   52
 47  \w   -131.00 -77.00   0.50    0.05    --  -91.75 -55.00-108.43  108
 48  \w   -147.00-114.00   0.50    0.05    --  -91.75 -61.00 -66.18   66
 49  \w   -163.00 -75.00   0.50    0.05    --  -91.75 -61.00 -30.00  176
 50  \w   -166.00 -78.00   0.50    0.05    --  -91.75 -16.00  -4.00  176
 51  \w   -122.00 -34.00   0.50    0.05    --  -47.32 -16.00  -4.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0733073000
_diffrn_orient_matrix_UB_12      -0.0085866000
_diffrn_orient_matrix_UB_13      -0.0167639000
_diffrn_orient_matrix_UB_21      -0.0368828000
_diffrn_orient_matrix_UB_22      -0.0519390000
_diffrn_orient_matrix_UB_23      -0.1192994000
_diffrn_orient_matrix_UB_31      -0.0053717000
_diffrn_orient_matrix_UB_32      0.2400585000
_diffrn_orient_matrix_UB_33      -0.0263971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13252
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.434
_diffrn_reflns_theta_min         4.721
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.00302(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0268
_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^)+(0.0462P)^2^+0.6451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1456
_reflns_number_total             1547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01211b2.cif
_cod_data_source_block           rb147_auto
_cod_database_code               7250517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C8 H12 N Se O5'
_shelx_estimated_absorpt_t_max   0.741
_shelx_estimated_absorpt_t_min   0.363
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C5(H5), C4(H4), C3(H3)
;
_shelx_res_checksum              34202
_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 5.125
_oxdiff_exptl_absorpt_empirical_full_min 0.433