#------------------------------------------------------------------------------
#$Date: 2025-06-07 03:08:02 +0200 (Sat 07 de Jun de 2025) $
#$Revision: 300009 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/05/7250518.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_7250518
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           '-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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  99.00   0.50    0.05    --  105.25 -95.00 -30.00   90
  2  ω    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-150.00  104
  3  ω    -71.00 -19.00   0.50    0.05    --  -91.75  61.00-120.00  104
  4  ω    -51.00 -20.00   0.50    0.05    --  -91.75  45.00-150.00   62
  5  ω    -51.00 -20.00   0.50    0.05    --  -91.75  45.00-180.00   62
  6  ω    -71.00 -19.00   0.50    0.05    --  -91.75  61.00  30.00  104
  7  ω    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 120.00   62
  8  ω    -51.00 -20.00   0.50    0.05    --  -91.75  45.00 150.00   62
  9  ω    -42.00  26.00   0.50    0.05    --  -47.32  37.00  49.00  136
 10  ω   -120.00 -25.00   0.50    0.05    --  -47.32 -77.00-180.00  190
 11  ω   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00-150.00  188
 12  ω   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00 150.00  188
 13  ω   -163.00 -72.00   0.50    0.05    --  -91.75 -69.00 143.01  182
 14  ω   -163.00 -69.00   0.50    0.05    --  -91.75 -77.00 176.16  188
 15  ω   -163.00 -77.00   0.50    0.05    --  -91.75 -55.00 160.22  172
 16  ω   -163.00 -70.00   0.50    0.05    --  -91.75 -75.00 162.08  186
 17  ω   -163.00 -78.00   0.50    0.05    --  -91.75 -52.00 171.36  170
 18  ω   -163.00 -72.00   0.50    0.05    --  -91.75 -69.00 133.03  182
 19  ω   -163.00 -79.00   0.50    0.05    --  -91.75 -45.00 150.00  168
 20  ω   -163.00 -70.00   0.50    0.05    --  -91.75 -74.00 125.43  186
 21  ω   -163.00 -75.00   0.50    0.05    --  -91.75 -61.00  90.00  176
 22  ω   -165.00 -79.00   0.50    0.05    --  -91.75 -37.00-106.00  172
 23  ω   -166.00 -79.00   0.50    0.05    --  -91.75 -30.00-180.00  174
 24  ω   -120.00 -35.00   0.50    0.05    --  -47.32 -37.00-106.00  170
 25  ω    -27.00  26.00   0.50    0.05    --   47.32 -19.00  90.00  106
 26  ω     33.00 105.00   0.50    0.05    --  105.25 -77.00  60.00  144
 27  ω     33.00  71.00   0.50    0.05    --  105.25 -61.00   0.00   76
 28  ω     42.00  70.00   0.50    0.05    --  105.25 -61.00 -30.00   56
 29  ω     33.00  71.00   0.50    0.05    --  105.25 -61.00 -60.00   76
 30  ω     33.00  71.00   0.50    0.05    --  105.25 -61.00 -90.00   76
 31  ω     33.00  71.00   0.50    0.05    --  105.25 -61.00-120.00   76
 32  ω    -26.00  42.00   0.50    0.05    --   47.32 -37.00-106.00  136
 33  ω     93.00 178.00   0.50    0.05    --  105.25  37.00  49.00  170
 34  ω     35.00 121.00   0.50    0.05    --   47.32  37.00  49.00  172
 35  ω     35.00 120.00   0.50    0.05    --   47.32  38.00-120.00  170
 36  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0327P)²+1.6025P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.545
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.68505(2) 0.09468(4) 0.31090(2) 0.02798(13) Uani 1 1 d . . . . .
O4 O 0.68197(9) 0.1882(3) 0.21835(10) 0.0395(4) Uani 1 1 d . . . . .
O2 O 0.59778(10) 0.1442(3) 0.31349(12) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.68992(11) -0.2374(4) 0.31204(11) 0.0446(4) Uani 1 1 d D . . . .
N1 N 0.56269(12) 0.5289(4) 0.39475(13) 0.0386(4) Uani 1 1 d . . . . .
O1 O 0.76250(10) 0.2034(4) 0.39363(11) 0.0544(5) Uani 1 1 d . . . . .
C3 C 0.51343(12) 0.9004(3) 0.47719(13) 0.0272(4) Uani 1 1 d . . . . .
C2 C 0.59660(13) 0.8511(5) 0.50213(14) 0.0392(5) Uani 1 1 d . . . . .
H2 H 0.636258 0.944776 0.547259 0.047 Uiso 1 1 calc R U . . .
C5 C 0.48382(16) 0.5725(5) 0.36893(17) 0.0468(6) Uani 1 1 d . . . . .
H5 H 0.445869 0.476959 0.322947 0.056 Uiso 1 1 calc R U . . .
C4 C 0.45702(13) 0.7562(5) 0.40882(14) 0.0407(5) Uani 1 1 d . . . . .
H4 H 0.401201 0.784496 0.390217 0.049 Uiso 1 1 calc R U . . .
C1 C 0.61913(14) 0.6634(5) 0.45944(15) 0.0419(5) Uani 1 1 d . . . . .
H1A H 0.674365 0.629819 0.475847 0.050 Uiso 1 1 calc R U . . .
H1 H 0.577(2) 0.400(6) 0.366(2) 0.076(11) Uiso 1 1 d . . . . .
H3 H 0.7240(14) -0.263(6) 0.3023(18) 0.048(8) Uiso 1 1 d 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 106.77(8) . . ?
O2 Se1 O4 110.43(9) . . ?
O2 Se1 O3 101.74(8) . . ?
O1 Se1 O4 113.66(9) . . ?
O1 Se1 O2 114.67(10) . . ?
O1 Se1 O3 108.57(9) . . ?
Se1 O3 H3 103(3) . . ?
C5 N1 C1 121.6(2) . . ?
C5 N1 H1 117(2) . . ?
C1 N1 H1 122(2) . . ?
C2 C3 C3 121.0(2) . 5_676 ?
C4 C3 C3 121.3(2) . 5_676 ?
C4 C3 C2 117.73(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
N1 C5 H5 119.5 . . ?
N1 C5 C4 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C1 C2 120.6(2) . . ?
N1 C1 H1A 119.7 . . ?
C2 C1 H1A 119.7 . . ?
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 1.6220(14) . ?
Se1 O2 1.6154(15) . ?
Se1 O3 1.7145(19) . ?
Se1 O1 1.6018(16) . ?
O3 H3 0.714(17) . ?
N1 C5 1.318(3) . ?
N1 C1 1.331(3) . ?
N1 H1 0.92(4) . ?
C3 C3 1.487(4) 5_676 ?
C3 C2 1.399(3) . ?
C3 C4 1.389(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.371(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C1 H1A 0.9300 . ?
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 0.4(4) . . . . ?
C3 C3 C2 C1 179.1(2) 5_676 . . . ?
C3 C3 C4 C5 -179.3(3) 5_676 . . . ?
C3 C2 C1 N1 0.1(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C5 N1 C1 C2 0.7(4) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
