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_7250521
_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             2024-12-13
_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                 108.101(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6801(4)
_cell_length_b                   6.20570(10)
_cell_length_c                   13.0059(2)
_cell_measurement_reflns_used    8217
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      76.3580
_cell_measurement_theta_min      4.7060
_cell_volume                     1509.79(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_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      N~2~
_diffrn_ambient_temperature      100.01(11)
_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 0.965
_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    -27.00  27.00   0.50    0.05    --   47.12 -19.00-150.00  108
  2  \w    -27.00  28.00   0.50    0.05    --  -47.12  19.00 -90.00  110
  3  \w    -27.00  28.00   0.50    0.05    --  -47.12  19.00  30.00  110
  4  \w    -27.00  28.00   0.50    0.05    --  -47.12  19.00  90.00  110
  5  \w    -27.00  27.00   0.50    0.05    --   47.12 -19.00  60.00  108
  6  \w    -27.00  27.00   0.50    0.05    --   47.12 -19.00 -30.00  108
  7  \w     33.00 105.00   0.50    0.05    --  105.82 -95.00  60.00  144
  8  \w     48.00 112.00   0.50    0.05    --   47.12-152.00 -97.00  128
  9  \w     36.00 112.00   0.50    0.05    --  105.82-125.00 -90.00  152
 10  \w     74.00 110.00   0.50    0.05    --  105.82-125.00-180.00   72
 11  \w     48.00 130.00   0.50    0.05    --  105.82-152.00 -97.00  164
 12  \w     48.00 130.00   0.50    0.05    --  105.82-152.00 -97.00  164
 13  \w     33.00 105.00   0.50    0.05    --  105.82 -95.00 -60.00  144
 14  \w     55.00  97.00   0.50    0.05    --  105.82 -95.00 -30.00   84
 15  \w     32.00  91.00   0.50    0.05    --   47.12-122.00  62.00  118
 16  \w     36.00 110.00   0.50    0.05    --  105.82-122.00  62.00  148
 17  \w     33.00 105.00   0.50    0.05    --  105.82 -95.00 120.00  144
 18  \w     33.00 105.00   0.50    0.05    --  105.82 -77.00 120.00  144
 19  \w     33.00  71.00   0.50    0.05    --  105.82 -61.00  60.00   76
 20  \w     43.00  85.00   0.50    0.05    --  105.82 -77.00-120.00   84
 21  \w     92.00 125.00   0.50    0.05    --  105.82  15.00 -30.00   66
 22  \w     92.00 178.00   0.50    0.05    --  105.82  15.00 -30.00  172
 23  \w     93.00 125.00   0.50    0.05    --  105.82  45.00  60.00   64
 24  \w    112.00 138.00   0.50    0.05    --  105.82 122.00 144.00   52
 25  \w     77.00 164.00   0.50    0.05    --  105.82 152.00 -55.00  174
 26  \w   -104.00 -27.00   0.50    0.05    --  -47.12 152.00 -55.00  154
 27  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-180.00  104
 28  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-120.00  104
 29  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00-180.00   62
 30  \w    -71.00 -19.00   0.50    0.05    --  -91.75  61.00   0.00  104
 31  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 -60.00   62
 32  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 -90.00   62
 33  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00  90.00   62
 34  \w    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 120.00   62
 35  \w    -84.00 -11.00   0.50    0.05    --  -47.12 122.00 144.00  146
 36  \w    -85.00 -22.00   0.50    0.05    --  -91.75 122.00 144.00  126
 37  \w   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00-120.00  168
 38  \w   -163.00 -76.00   0.50    0.05    --  -91.75 -59.00 -31.53  174
 39  \w   -163.00 -76.00   0.50    0.05    --  -91.75 -59.00 -31.53  174
 40  \w   -163.00 -76.00   0.50    0.05    --  -91.75 -59.00 169.98  174
 41  \w   -161.00 -75.00   0.50    0.05    --  -91.75-122.00  62.00  172
 42  \w   -120.00 -55.00   0.50    0.05    --  -47.12-152.00 -97.00  130
 43  \w   -147.00 -55.00   0.50    0.05    --  -91.75-152.00 -97.00  184
;
_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      -0.0800447000
_diffrn_orient_matrix_UB_12      0.0565340000
_diffrn_orient_matrix_UB_13      -0.0442928000
_diffrn_orient_matrix_UB_21      -0.0191372000
_diffrn_orient_matrix_UB_22      -0.2403253000
_diffrn_orient_matrix_UB_23      0.0022924000
_diffrn_orient_matrix_UB_31      -0.0027025000
_diffrn_orient_matrix_UB_32      0.0261693000
_diffrn_orient_matrix_UB_33      0.1164589000
_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  0.0540
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_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       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12501
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.675
_diffrn_reflns_theta_min         4.728
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.540
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_description       block
_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         0.686
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         1531
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0282
_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^)+(0.0498P)^2^+2.5852P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1453
_reflns_number_total             1531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01211b2.cif
_cod_data_source_block           rb147_3_lt_auto
_cod_database_code               7250521
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C5 H6 N Se O4'
_shelx_estimated_absorpt_t_max   0.736
_shelx_estimated_absorpt_t_min   0.355
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C1(H1A), C3(H3), C5(H5), C4(H4)
;
_shelx_res_checksum              83777
_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 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.478