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_7250522
_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           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 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                 118.2924(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7423(2)
_cell_length_b                   5.11409(7)
_cell_length_c                   18.4872(3)
_cell_measurement_reflns_used    9204
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.4310
_cell_measurement_theta_min      5.4240
_cell_volume                     1393.81(4)
_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      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_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    -48.00 -20.00   0.50    0.05    --  -91.75  45.00 150.00   56
  2  \w    -67.00 -20.00   0.50    0.05    --  -91.75  61.00 120.00   94
  3  \w    -46.00 -20.00   0.50    0.05    --  -91.75  45.00-150.00   52
  4  \w    -25.00  28.00   0.50    0.05    --  -47.37  15.00-119.00  106
  5  \w     25.00 120.00   0.50    0.05    --   47.37  77.00 -60.00  190
  6  \w     25.00 120.00   0.50    0.05    --   47.37  77.00 -60.00  190
  7  \w     35.00 120.00   0.50    0.05    --   47.37  38.00 -60.00  170
  8  \w     34.00 123.00   0.50    0.05    --   47.37  15.00-119.00  178
  9  \w    -27.00  27.00   0.50    0.05    --   47.37 -19.00 -60.00  108
 10  \w    -27.00  24.00   0.50    0.05    --   47.37 -15.00  70.00  102
 11  \w     92.00 128.00   0.50    0.05    --  105.82  15.00-119.00   72
 12  \w     92.00 178.00   0.50    0.05    --  105.82  15.00-119.00  172
 13  \w     40.00  66.00   0.50    0.05    --  105.82 -61.00 -60.00   52
 14  \w     38.00  69.00   0.50    0.05    --  105.82 -61.00 -90.00   62
 15  \w     34.00  66.00   0.50    0.05    --  105.82 -61.00-180.00   64
 16  \w     35.00  70.00   0.50    0.05    --  105.82 -61.00 -30.00   70
 17  \w     33.00  68.00   0.50    0.05    --  105.82 -61.00 120.00   70
 18  \w     33.00  71.00   0.50    0.05    --  105.82 -61.00   0.00   76
 19  \w     34.00  60.00   0.50    0.05    --  105.82 -95.00 -60.00   52
 20  \w     38.00  64.00   0.50    0.05    --  105.82-125.00 -60.00   52
 21  \w     79.00 112.00   0.50    0.05    --  105.82-125.00 -60.00   66
 22  \w     80.00 105.00   0.50    0.05    --  105.82 -95.00 -60.00   50
 23  \w     34.00  80.00   0.50    0.05    --  105.82 -95.00 -90.00   92
 24  \w     34.00  93.00   0.50    0.05    --   47.37-125.00-120.00  118
 25  \w   -120.00 -25.00   0.50    0.05    --  -47.37 -77.00   0.00  190
 26  \w   -120.00 -25.00   0.50    0.05    --  -47.37 -77.00   0.00  190
 27  \w   -122.00 -34.00   0.50    0.05    --  -47.37 -15.00  70.00  176
 28  \w    -94.00 -69.00   0.50    0.05    --  -91.75 -77.00  30.00   50
 29  \w    -97.00 -70.00   0.50    0.05    --  -91.75 -77.00  60.00   54
 30  \w   -104.00 -70.00   0.50    0.05    --  -91.75 -77.00   0.00   68
 31  \w    -96.00 -70.00   0.50    0.05    --  -91.75 -77.00 -60.00   52
 32  \w    -99.00 -69.00   0.50    0.05    --  -91.75 -77.00 -30.00   60
 33  \w   -101.00 -69.00   0.50    0.05    --  -91.75 -76.00  13.07   64
 34  \w   -163.00 -74.00   0.50    0.05    --  -91.75 -65.00  34.48  178
 35  \w   -163.00-114.00   0.50    0.05    --  -91.75 -77.00  30.00   98
 36  \w   -158.00-133.00   0.50    0.05    --  -91.75 -76.00  13.07   50
 37  \w   -112.00 -76.00   0.50    0.05    --  -91.75 -63.00  20.88   72
 38  \w   -101.00 -75.00   0.50    0.05    --  -91.75 -62.00  23.96   52
 39  \w   -101.00 -74.00   0.50    0.05    --  -91.75 -63.00 -34.41   54
 40  \w   -112.00 -76.00   0.50    0.05    --  -91.75 -63.00 -95.33   72
 41  \w   -124.00 -74.00   0.50    0.05    --  -91.75 -64.00 -58.18  100
 42  \w   -101.00 -75.00   0.50    0.05    --  -91.75 -62.00 -28.51   52
 43  \w   -162.00-125.00   0.50    0.05    --  -91.75 -60.00  10.00   74
 44  \w   -159.00-133.00   0.50    0.05    --  -91.75 -63.00  20.88   52
 45  \w   -119.00 -76.00   0.50    0.05    --  -91.75 -60.00  10.00   86
 46  \w   -162.00 -76.00   0.50    0.05    --  -91.75 -58.00 -48.88  172
 47  \w   -161.00 -75.00   0.50    0.05    --  -91.75 -61.00 -93.30  172
 48  \w   -125.00 -76.00   0.50    0.05    --  -91.75 -60.00 -70.90   98
 49  \w   -163.00-115.00   0.50    0.05    --  -91.75 -62.00 -28.51   96
 50  \w   -143.00-117.00   0.50    0.05    --  -91.75 -45.00  30.00   52
 51  \w   -114.00 -79.00   0.50    0.05    --  -91.75 -45.00  30.00   70
 52  \w   -166.00 -78.00   0.50    0.05    --  -91.75 -15.00  70.00  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      0.0988943000
_diffrn_orient_matrix_UB_12      0.0530410000
_diffrn_orient_matrix_UB_13      0.0649921000
_diffrn_orient_matrix_UB_21      0.0300732000
_diffrn_orient_matrix_UB_22      -0.0248325000
_diffrn_orient_matrix_UB_23      -0.0666075000
_diffrn_orient_matrix_UB_31      -0.0152659000
_diffrn_orient_matrix_UB_32      0.2954905000
_diffrn_orient_matrix_UB_33      -0.0172678000
_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  0.0321
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11468
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.549
_diffrn_reflns_theta_min         5.435
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36711
_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    2.126
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.00048(4)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0190
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0288P)^2^+2.5499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1367
_reflns_number_total             1393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01211b2.cif
_cod_data_source_block           rb444e_lt_auto
_cod_database_code               7250522
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C10 H10 N2 Se O4'
_shelx_estimated_absorpt_t_max   0.718
_shelx_estimated_absorpt_t_min   0.332
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C1(H1A), C5(H5), C4(H4)
;
_shelx_res_checksum              10482
_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 2.338
_oxdiff_exptl_absorpt_empirical_full_min 0.694