#------------------------------------------------------------------------------
#$Date: 2025-06-07 04:08:02 +0300 (Sat, 07 Jun 2025) $
#$Revision: 300009 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/05/7250522.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7250522
loop_
_publ_author_name
'Beccaria, Roberta'
'Pizzi, Andrea'
'Chakalov, Edem R.'
'Resnati, Giuseppe'
'Tolstoy, Peter'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00 -20.00   0.50    0.05    --  -91.75  45.00 150.00   56
  2  ω    -67.00 -20.00   0.50    0.05    --  -91.75  61.00 120.00   94
  3  ω    -46.00 -20.00   0.50    0.05    --  -91.75  45.00-150.00   52
  4  ω    -25.00  28.00   0.50    0.05    --  -47.37  15.00-119.00  106
  5  ω     25.00 120.00   0.50    0.05    --   47.37  77.00 -60.00  190
  6  ω     25.00 120.00   0.50    0.05    --   47.37  77.00 -60.00  190
  7  ω     35.00 120.00   0.50    0.05    --   47.37  38.00 -60.00  170
  8  ω     34.00 123.00   0.50    0.05    --   47.37  15.00-119.00  178
  9  ω    -27.00  27.00   0.50    0.05    --   47.37 -19.00 -60.00  108
 10  ω    -27.00  24.00   0.50    0.05    --   47.37 -15.00  70.00  102
 11  ω     92.00 128.00   0.50    0.05    --  105.82  15.00-119.00   72
 12  ω     92.00 178.00   0.50    0.05    --  105.82  15.00-119.00  172
 13  ω     40.00  66.00   0.50    0.05    --  105.82 -61.00 -60.00   52
 14  ω     38.00  69.00   0.50    0.05    --  105.82 -61.00 -90.00   62
 15  ω     34.00  66.00   0.50    0.05    --  105.82 -61.00-180.00   64
 16  ω     35.00  70.00   0.50    0.05    --  105.82 -61.00 -30.00   70
 17  ω     33.00  68.00   0.50    0.05    --  105.82 -61.00 120.00   70
 18  ω     33.00  71.00   0.50    0.05    --  105.82 -61.00   0.00   76
 19  ω     34.00  60.00   0.50    0.05    --  105.82 -95.00 -60.00   52
 20  ω     38.00  64.00   0.50    0.05    --  105.82-125.00 -60.00   52
 21  ω     79.00 112.00   0.50    0.05    --  105.82-125.00 -60.00   66
 22  ω     80.00 105.00   0.50    0.05    --  105.82 -95.00 -60.00   50
 23  ω     34.00  80.00   0.50    0.05    --  105.82 -95.00 -90.00   92
 24  ω     34.00  93.00   0.50    0.05    --   47.37-125.00-120.00  118
 25  ω   -120.00 -25.00   0.50    0.05    --  -47.37 -77.00   0.00  190
 26  ω   -120.00 -25.00   0.50    0.05    --  -47.37 -77.00   0.00  190
 27  ω   -122.00 -34.00   0.50    0.05    --  -47.37 -15.00  70.00  176
 28  ω    -94.00 -69.00   0.50    0.05    --  -91.75 -77.00  30.00   50
 29  ω    -97.00 -70.00   0.50    0.05    --  -91.75 -77.00  60.00   54
 30  ω   -104.00 -70.00   0.50    0.05    --  -91.75 -77.00   0.00   68
 31  ω    -96.00 -70.00   0.50    0.05    --  -91.75 -77.00 -60.00   52
 32  ω    -99.00 -69.00   0.50    0.05    --  -91.75 -77.00 -30.00   60
 33  ω   -101.00 -69.00   0.50    0.05    --  -91.75 -76.00  13.07   64
 34  ω   -163.00 -74.00   0.50    0.05    --  -91.75 -65.00  34.48  178
 35  ω   -163.00-114.00   0.50    0.05    --  -91.75 -77.00  30.00   98
 36  ω   -158.00-133.00   0.50    0.05    --  -91.75 -76.00  13.07   50
 37  ω   -112.00 -76.00   0.50    0.05    --  -91.75 -63.00  20.88   72
 38  ω   -101.00 -75.00   0.50    0.05    --  -91.75 -62.00  23.96   52
 39  ω   -101.00 -74.00   0.50    0.05    --  -91.75 -63.00 -34.41   54
 40  ω   -112.00 -76.00   0.50    0.05    --  -91.75 -63.00 -95.33   72
 41  ω   -124.00 -74.00   0.50    0.05    --  -91.75 -64.00 -58.18  100
 42  ω   -101.00 -75.00   0.50    0.05    --  -91.75 -62.00 -28.51   52
 43  ω   -162.00-125.00   0.50    0.05    --  -91.75 -60.00  10.00   74
 44  ω   -159.00-133.00   0.50    0.05    --  -91.75 -63.00  20.88   52
 45  ω   -119.00 -76.00   0.50    0.05    --  -91.75 -60.00  10.00   86
 46  ω   -162.00 -76.00   0.50    0.05    --  -91.75 -58.00 -48.88  172
 47  ω   -161.00 -75.00   0.50    0.05    --  -91.75 -61.00 -93.30  172
 48  ω   -125.00 -76.00   0.50    0.05    --  -91.75 -60.00 -70.90   98
 49  ω   -163.00-115.00   0.50    0.05    --  -91.75 -62.00 -28.51   96
 50  ω   -143.00-117.00   0.50    0.05    --  -91.75 -45.00  30.00   52
 51  ω   -114.00 -79.00   0.50    0.05    --  -91.75 -45.00  30.00   70
 52  ω   -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0288P)²+2.5499P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.37551(2) 0.91771(3) 0.68513(2) 0.00971(10) Uani 1 1 d . . . . .
O4 O 0.46676(8) 0.8268(3) 0.68096(8) 0.0143(3) Uani 1 1 d . . . . .
O1 O 0.36926(9) 0.8065(3) 0.76380(8) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.28609(9) 0.8653(3) 0.59760(8) 0.0154(3) Uani 1 1 d . . . . .
O3 O 0.37783(9) 1.2533(3) 0.69014(9) 0.0157(3) Uani 1 1 d . . . . .
N1 N 0.16916(11) 0.4760(3) 0.56379(10) 0.0143(3) Uani 1 1 d . . . . .
H1 H 0.211388 0.597371 0.579930 0.017 Uiso 1 1 calc R U . . .
C3 C 0.03643(12) 0.1009(3) 0.51365(12) 0.0110(4) Uani 1 1 d . . . . .
C2 C 0.09667(12) 0.1387(4) 0.59719(11) 0.0137(4) Uani 1 1 d . . . . .
H2 H 0.092312 0.033450 0.637526 0.016 Uiso 1 1 calc R U . . .
C1 C 0.16213(12) 0.3293(4) 0.62031(11) 0.0142(4) Uani 1 1 d . . . . .
H1A H 0.202676 0.356973 0.676918 0.017 Uiso 1 1 calc R U . . .
C5 C 0.11389(13) 0.4437(4) 0.48336(12) 0.0161(4) Uani 1 1 d . . . . .
H5 H 0.121225 0.549512 0.444681 0.019 Uiso 1 1 calc R U . . .
C4 C 0.04648(12) 0.2578(4) 0.45645(11) 0.0144(4) Uani 1 1 d . . . . .
H4 H 0.006960 0.236041 0.399341 0.017 Uiso 1 1 calc R U . . .
H1B H 0.4187(18) 1.275(6) 0.7234(17) 0.022(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Se1 O3 106.80(7) . . ?
O4 Se1 H1B 95.1(8) . . ?
O1 Se1 O4 113.88(7) . . ?
O1 Se1 O2 114.70(7) . . ?
O1 Se1 O3 108.27(7) . . ?
O1 Se1 H1B 100.0(8) . . ?
O2 Se1 O4 110.33(7) . . ?
O2 Se1 O3 101.83(7) . . ?
O2 Se1 H1B 121.3(8) . . ?
O3 Se1 H1B 19.7(8) . . ?
Se1 O3 H1B 102(2) . . ?
C1 N1 H1 119.0 . . ?
C1 N1 C5 121.94(17) . . ?
C5 N1 H1 119.0 . . ?
C2 C3 C3 121.0(2) . 5_556 ?
C4 C3 C3 120.9(2) . 5_556 ?
C4 C3 C2 118.18(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 C3 119.46(17) . . ?
C1 C2 H2 120.3 . . ?
N1 C1 C2 120.51(17) . . ?
N1 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
N1 C5 H5 119.9 . . ?
N1 C5 C4 120.26(18) . . ?
C4 C5 H5 119.9 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.65(17) . . ?
C5 C4 H4 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 O4 1.6333(12) . ?
Se1 O1 1.6105(13) . ?
Se1 O2 1.6234(13) . ?
Se1 O3 1.7180(16) . ?
Se1 H1B 1.97(3) . ?
O3 H1B 0.68(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.336(3) . ?
N1 C5 1.338(3) . ?
C3 C3 1.491(3) 5_556 ?
C3 C2 1.401(3) . ?
C3 C4 1.400(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.375(3) . ?
C1 H1A 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.376(3) . ?
C4 H4 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C4 C3 -0.5(3) . . . . ?
C3 C3 C2 C1 -178.9(2) 5_556 . . . ?
C3 C3 C4 C5 179.5(2) 5_556 . . . ?
C3 C2 C1 N1 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C1 N1 C5 C4 0.9(3) . . . . ?
C5 N1 C1 C2 -0.3(3) . . . . ?
C4 C3 C2 C1 1.0(3) . . . . ?
