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_7250518
_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 H5 N'
_chemical_formula_sum            'C5 H6 N O4 Se'
_chemical_formula_weight         223.07
_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                 115.2773(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.0562(2)
_cell_length_b                   5.15783(5)
_cell_length_c                   16.9795(2)
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    298.01(10)
_cell_measurement_theta_max      75.0770
_cell_measurement_theta_min      2.8050
_cell_volume                     1429.91(3)
_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 0.964
_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     54.00  99.00   0.50    0.05    --  105.25 -95.00 -30.00   90
  2  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-150.00  104
  3  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-120.00  104
  4  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00-150.00   62
  5  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00-180.00   62
  6  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00  30.00  104
  7  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 120.00   62
  8  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 150.00   62
  9  \w    -42.00  26.00   0.50    0.05    --  -47.32  37.00  49.00  136
 10  \w   -120.00 -25.00   0.50    0.05    --  -47.32 -77.00-180.00  190
 11  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00-150.00  188
 12  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00 150.00  188
 13  \w   -163.00 -72.00   0.50    0.05    --  -91.75 -69.00 143.01  182
 14  \w   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00 176.16  188
 15  \w   -163.00 -77.00   0.50    0.05    --  -91.75 -55.00 160.22  172
 16  \w   -163.00 -70.00   0.50    0.05    --  -91.75 -75.00 162.08  186
 17  \w   -163.00 -78.00   0.50    0.05    --  -91.75 -52.00 171.36  170
 18  \w   -163.00 -72.00   0.50    0.05    --  -91.75 -69.00 133.03  182
 19  \w   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00 150.00  168
 20  \w   -163.00 -70.00   0.50    0.05    --  -91.75 -74.00 125.43  186
 21  \w   -163.00 -75.00   0.50    0.05    --  -91.75 -61.00  90.00  176
 22  \w   -165.00 -79.00   0.50    0.05    --  -91.75 -37.00-106.00  172
 23  \w   -166.00 -79.00   0.50    0.05    --  -91.75 -30.00-180.00  174
 24  \w   -120.00 -35.00   0.50    0.05    --  -47.32 -37.00-106.00  170
 25  \w    -27.00  26.00   0.50    0.05    --   47.32 -19.00  90.00  106
 26  \w     33.00 105.00   0.50    0.05    --  105.25 -77.00  60.00  144
 27  \w     33.00  71.00   0.50    0.05    --  105.25 -61.00   0.00   76
 28  \w     42.00  70.00   0.50    0.05    --  105.25 -61.00 -30.00   56
 29  \w     33.00  71.00   0.50    0.05    --  105.25 -61.00 -60.00   76
 30  \w     33.00  71.00   0.50    0.05    --  105.25 -61.00 -90.00   76
 31  \w     33.00  71.00   0.50    0.05    --  105.25 -61.00-120.00   76
 32  \w    -26.00  42.00   0.50    0.05    --   47.32 -37.00-106.00  136
 33  \w     93.00 178.00   0.50    0.05    --  105.25  37.00  49.00  170
 34  \w     35.00 121.00   0.50    0.05    --   47.32  37.00  49.00  172
 35  \w     35.00 120.00   0.50    0.05    --   47.32  38.00-120.00  170
 36  \w     95.00 178.00   0.50    0.05    --  105.25 125.00 -90.00  166
;
_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      -0.0041620000
_diffrn_orient_matrix_UB_12      0.1234313000
_diffrn_orient_matrix_UB_13      -0.0844097000
_diffrn_orient_matrix_UB_21      0.0908953000
_diffrn_orient_matrix_UB_22      -0.0669537000
_diffrn_orient_matrix_UB_23      0.0278161000
_diffrn_orient_matrix_UB_31      -0.0250013000
_diffrn_orient_matrix_UB_32      -0.2636376000
_diffrn_orient_matrix_UB_33      -0.0465523000
_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12187
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.390
_diffrn_reflns_theta_min         5.419
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30376
_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    2.072
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00149(8)
_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   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0211
_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^)+(0.0327P)^2^+1.6025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1384
_reflns_number_total             1433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01211b2.cif
_cod_data_source_block           rb444_e_auto
_cod_database_code               7250518
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H16 N2 Se O4'
_shelx_estimated_absorpt_t_max   0.545
_shelx_estimated_absorpt_t_min   0.231
_olex2_refinement_description
;
1. Restrained distances
 H3-O3
 0.78 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C1(H1A)
;
_shelx_res_checksum              81419
_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 2.101
_oxdiff_exptl_absorpt_empirical_full_min 0.571