Hydrogen-bonded salt cocrystals of xenon difluoride and protonated perfluoroamides
Uran, Erik; Lozinšek, Matic; CrystEngComm  (2025) –; doi:10.1039/D5CE00956A

data_7251201
_publ_section_title
;
 Hydrogen-bonded salt cocrystals of xenon difluoride and protonated
 perfluoroamides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00956A
_journal_year                    2025
_chemical_formula_moiety         'C3 H2 F5 N O'
_chemical_formula_sum            'C3 H2 F5 N O'
_chemical_formula_weight         163.06
_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   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2025-10-02
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2025-10-03 deposited with the CCDC.	2025-11-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.140(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7871(5)
_cell_length_b                   5.11704(12)
_cell_length_c                   10.0754(3)
_cell_measurement_reflns_used    9753
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2160
_cell_measurement_theta_min      4.1060
_cell_volume                     1111.94(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger2 R CdTe 1M'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -19.00  33.00   0.50    0.50    --    2.00  76.00 -70.21  104
  2  \w    -42.00  33.00   0.50    0.50    --  -22.00  76.00 175.63  150
  3  \w      2.00  35.00   0.50    0.50    --   22.00  79.00  84.12   66
  4  \w     12.00  56.00   0.50    0.50    --   30.00  75.00   6.73   88
  5  \w     16.00  41.00   0.50    0.50    --   38.00  79.00 110.90   50
  6  \w     16.00  41.00   0.50    0.50    --   38.00  79.00 -99.59   50
  7  \w   -103.00 -73.00   0.50    0.50    --  -48.06 -77.00  30.00   60
  8  \w    -68.00   3.00   0.50    0.50    --  -48.06  77.00 120.00  142
  9  \w    -53.00 -28.00   0.50    0.50    --  -48.06 -77.00  30.00   50
 10  \w    -65.00   4.00   0.50    0.50    --  -48.06  77.00 -30.00  138
 11  \w    -59.00 -27.00   0.50    0.50    --  -48.06 -77.00-120.00   64
 12  \w     27.00  68.00   0.50    0.50    --   48.06  77.00  30.00   82
 13  \w     28.00  54.00   0.50    0.50    --   48.06  77.00 120.00   52
 14  \w     29.00  54.00   0.50    0.50    --   50.00  77.00 -20.15   50
 15  \w     34.00  60.00   0.50    0.50    --   54.00  73.00 -55.20   52
 16  \w     33.00  58.00   0.50    0.50    --   54.00  77.00 176.84   50
 17  \w     80.00 106.00   0.50    0.50    --   58.00  74.00  91.41   52
 18  \w     38.00  67.00   0.50    0.50    --   58.00  75.00 139.37   58
 19  \w     39.00  65.00   0.50    0.50    --   58.00  74.00 -87.67   52
 20  \w     39.00  67.00   0.50    0.50    --   58.00  73.00 -30.05   56
 21  \w     90.00 115.00   0.50    0.50    --   58.00  74.00 -87.67   50
 22  \w     38.00  64.00   0.50    0.50    --   58.00  74.00  91.41   52
 23  \w     39.00  65.00   0.50    0.50    --   58.00  74.00-146.21   52
 24  \w     45.00  71.00   0.50    0.50    --   66.00  76.00 -11.69   52
 25  \w    -82.00 -50.00   0.50    0.50    --  -66.00 -63.00 142.72   64
 26  \w     47.00  73.00   0.50    0.50    --   66.00  74.00-138.01   52
 27  \w     45.00  77.00   0.50    0.50    --   66.00  76.00  11.40   64
 28  \w     46.00  72.00   0.50    0.50    --   66.00  76.00 -90.05   52
 29  \w     97.00 122.00   0.50    0.50    --   66.00  76.00  11.40   50
 30  \w    -77.00 -51.00   0.50    0.50    --  -70.00 -74.00 -73.23   52
 31  \w     50.00  76.00   0.50    0.50    --   70.00  75.00  94.57   52
 32  \w    -75.00 -50.00   0.50    0.50    --  -70.00 -72.00  29.86   50
 33  \w    -88.00 -54.00   0.50    0.50    --  -74.00 -73.00-165.58   68
 34  \w   -102.00 -58.00   0.50    0.50    --  -78.00 -74.00 160.51   88
 35  \w    -88.00 -62.00   0.50    0.50    --  -82.00 -73.00  34.48   52
 36  \w    -90.00 -62.00   0.50    0.50    --  -82.00 -73.00  64.07   56
 37  \w    -87.00 -62.00   0.50    0.50    --  -82.00 -73.00 -80.68   50
 38  \w    -86.00 -61.00   0.50    0.50    --  -82.50 -77.00 -30.00   50
 39  \w    -91.00 -65.00   0.50    0.50    --  -82.50 -66.00   2.50   52
 40  \w    -90.00 -64.00   0.50    0.50    --  -82.50 -73.00   1.22   52
 41  \w    -86.00 -61.00   0.50    0.50    --  -82.50 -77.00 150.00   50
 42  \w    -87.00 -61.00   0.50    0.50    --  -82.50 -76.00-161.93   52
 43  \w    -90.00 -64.00   0.50    0.50    --  -82.50 -71.00 -53.65   52
 44  \w    -91.00 -61.00   0.50    0.50    --  -82.50 -77.00-120.00   60
 45  \w    -51.00 -18.00   0.50    0.50    --  -82.50  45.00  90.00   66
 46  \w    -86.00 -61.00   0.50    0.50    --  -82.50 -77.00  90.00   50
 47  \w    -46.00 -20.00   0.50    0.50    --  -82.50  45.00-180.00   52
 48  \w    -86.00 -61.00   0.50    0.50    --  -82.50 -77.00 120.00   50
 49  \w    -90.00 -65.00   0.50    0.50    --  -82.50 -69.00  37.07   50
 50  \w    -58.00 -30.00   0.50    0.50    --  -82.50  68.00  13.57   56
 51  \w    -88.00 -62.00   0.50    0.50    --  -82.50 -77.00 -90.00   52
 52  \w    -88.00 -62.00   0.50    0.50    --  -82.50 -74.00 129.83   52
 53  \w    -88.00 -62.00   0.50    0.50    --  -82.50 -77.00 -13.13   52
 54  \w    -94.00 -65.00   0.50    0.50    --  -82.50 -72.00 167.32   58
 55  \w     19.00  44.00   0.50    0.50    --   86.00 -43.00-111.74   50
 56  \w     47.00 107.00   0.50    0.50    --  104.00 -80.00 148.10  120
 57  \w     94.00 120.00   0.50    0.50    --  104.00  61.00  90.00   52
 58  \w    139.00 164.00   0.50    0.50    --  104.00  61.00-120.00   50
 59  \w     93.00 126.00   0.50    0.50    --  104.00  61.00-120.00   66
 60  \w    133.00 160.00   0.50    0.50    --  104.00  77.00-180.00   54
 61  \w    122.00 161.00   0.50    0.50    --  104.00  61.00  90.00   78
 62  \w     87.00 126.00   0.50    0.50    --  104.00  77.00   0.00   78
 63  \w     83.00 109.00   0.50    0.50    --  104.00  77.00-180.00   52
 64  \w    133.00 161.00   0.50    0.50    --  104.00  45.00  30.00   56
 65  \w     93.00 160.00   0.50    0.50    --  104.00  61.00 -60.00  134
 66  \w    134.00 160.00   0.50    0.50    --  104.00  77.00  60.00   52
 67  \w     83.00 109.00   0.50    0.50    --  104.00  77.00  60.00   52
 68  \w    122.00 170.00   0.50    0.50    --  104.00  45.00-120.00   96
 69  \w     99.00 132.00   0.50    0.50    --  104.00  45.00 -90.00   66
 70  \w    138.00 164.00   0.50    0.50    --  104.00  61.00  30.00   52
 71  \w     48.00  73.00   0.50    0.50    --  104.00 -77.00  30.00   50
 72  \w    100.00 133.00   0.50    0.50    --  104.00  61.00  30.00   66
 73  \w    127.00 160.00   0.50    0.50    --  104.00  77.00 -30.00   66
 74  \w     85.00 115.00   0.50    0.50    --  104.00  77.00 -30.00   60
 75  \w    125.00 161.00   0.50    0.50    --  104.00  61.00 120.00   72
 76  \w     88.00 114.00   0.50    0.50    --  104.00 -80.00-158.28   52
 77  \w     91.00 123.00   0.50    0.50    --  104.00  61.00 120.00   64
 78  \w     83.00 112.00   0.50    0.50    --  104.00  77.00-150.00   58
 79  \w    133.00 162.00   0.50    0.50    --  104.00  61.00   0.00   58
 80  \w    133.00 160.00   0.50    0.50    --  104.00  77.00 -90.00   54
 81  \w     54.00  80.00   0.50    0.50    --  104.00 -80.00-158.28   52
 82  \w     84.00 110.00   0.50    0.50    --  104.00  77.00 -90.00   52
 83  \w     84.00 116.00   0.50    0.50    --  104.00  77.00 150.00   64
 84  \w    134.00 160.00   0.50    0.50    --  104.00  45.00-180.00   52
 85  \w     48.00  86.00   0.50    0.50    --  104.00 -77.00-150.00   76
 86  \w    127.00 153.00   0.50    0.50    --  104.00  61.00 -30.00   52
 87  \w     90.00 117.00   0.50    0.50    --  104.00  61.00 -30.00   54
 88  \w     47.00  72.00   0.50    0.50    --  104.00 -78.00  60.63   50
 89  \w    133.00 159.00   0.50    0.50    --  104.00  61.00 -90.00   52
 90  \w     48.00  82.00   0.50    0.50    --  104.00 -77.00 120.00   68
 91  \w     91.00 117.00   0.50    0.50    --  104.00  61.00 -90.00   52
 92  \w     80.00 106.00   0.50    0.50    --  104.00 -80.00  45.50   52
 93  \w    125.00 161.00   0.50    0.50    --  104.00  77.00 150.00   72
 94  \w     90.00 130.00   0.50    0.50    --  104.00  61.00   0.00   80
 95  \w    133.00 159.00   0.50    0.50    --  104.00  77.00  30.00   52
 96  \w     83.00 121.00   0.50    0.50    --  104.00  77.00  30.00   76
 97  \w    130.00 158.00   0.50    0.50    --  104.00  77.00-150.00   56
 98  \w     88.00 114.00   0.50    0.50    --  104.00  77.00  90.00   52
 99  \w    131.00 157.00   0.50    0.50    --  104.00  77.00  90.00   52
100  \w     51.00  76.00   0.50    0.50    --  104.00 -80.00  45.50   50
101  \w     50.00  87.00   0.50    0.50    --  104.00 -77.00 150.00   74
102  \w     48.00  74.00   0.50    0.50    --  104.00 -77.00-180.00   52
103  \w     54.00  83.00   0.50    0.50    --  104.00 -77.00   0.00   58
104  \w     47.00  79.00   0.50    0.50    --  104.00 -80.00 -62.67   64
105  \w    122.00 158.00   0.50    0.50    --  104.00  77.00 120.00   72
106  \w     83.00 109.00   0.50    0.50    --  104.00  77.00 120.00   52
107  \w     49.00 105.00   0.50    0.50    --  104.00 -79.00  39.64  112
108  \w    140.00 166.00   0.50    0.50    --  104.00  45.00 -90.00   52
109  \w    136.00 170.00   0.50    0.50    --  104.00  45.00 -30.00   68
110  \w    138.00 168.00   0.50    0.50    --  104.00  45.00 150.00   60
111  \w    122.00 159.00   0.50    0.50    --  104.00  77.00 -60.00   74
112  \w     85.00 111.00   0.50    0.50    --  104.00  77.00 -60.00   52
113  \w     47.00 123.00   0.50    0.50    --  104.00 -80.00 -22.68  152
114  \w    129.00 160.00   0.50    0.50    --  104.00  61.00  60.00   62
115  \w     47.00 100.00   0.50    0.50    --  104.00 -80.00 100.86  106
116  \w     90.00 125.00   0.50    0.50    --  104.00  61.00  60.00   70
117  \w     91.00 122.00   0.50    0.50    --  104.00  61.00-180.00   62
118  \w    139.00 164.00   0.50    0.50    --  104.00  61.00-180.00   50
119  \w     48.00  98.00   0.50    0.50    --  104.00 -77.00 -90.00  100
120  \w     49.00  90.00   0.50    0.50    --  104.00 -80.00  86.53   82
121  \w     48.00  73.00   0.50    0.50    --  104.00 -77.00 -60.00   50
122  \w    136.00 162.00   0.50    0.50    --  104.00  61.00-150.00   52
123  \w     93.00 131.00   0.50    0.50    --  104.00  61.00-150.00   76
124  \w    125.00 151.00   0.50    0.50    --  104.00  45.00-150.00   52
125  \w     99.00 124.00   0.50    0.50    --  104.00 -80.00 -45.44   50
126  \w     52.00  84.00   0.50    0.50    --  104.00 -77.00-120.00   64
127  \w    132.00 161.00   0.50    0.50    --  104.00  77.00-120.00   58
128  \w     48.00  93.00   0.50    0.50    --  104.00 -80.00 -45.44   90
129  \w     86.00 124.00   0.50    0.50    --  104.00  77.00-120.00   76
130  \w    131.00 164.00   0.50    0.50    --  104.00  61.00 150.00   66
131  \w     90.00 125.00   0.50    0.50    --  104.00  61.00 150.00   70
132  \w    136.00 161.00   0.50    0.50    --  104.00  77.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku OD, XtaLAB Synergy-S, Dualflex, Eiger2 R CdTe 1M'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0646913000
_diffrn_orient_matrix_UB_12      0.0920716000
_diffrn_orient_matrix_UB_13      -0.0649865000
_diffrn_orient_matrix_UB_21      -0.0267123000
_diffrn_orient_matrix_UB_22      -0.2713907000
_diffrn_orient_matrix_UB_23      0.0249308000
_diffrn_orient_matrix_UB_31      -0.0142866000
_diffrn_orient_matrix_UB_32      0.0919785000
_diffrn_orient_matrix_UB_33      0.1379381000
_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  0.0470
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.191
_diffrn_reflns_theta_min         4.100
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0976P)^2^+0.5637P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1063
_reflns_number_total             1161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00956a2.cif
_cod_data_source_block           f5c3(o)nh2_1
_cod_database_code               7251201
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'F5 C3 O N H2 '
_chemical_oxdiff_usercomment     '100 K, EU'
_cell_oxdiff_angle_alpha         89.931(2)
_cell_oxdiff_angle_beta          98.164(2)
_cell_oxdiff_angle_gamma         89.953(2)
_cell_oxdiff_length_a            21.7875(6)
_cell_oxdiff_length_b            5.11841(13)
_cell_oxdiff_length_c            10.0731(2)
_cell_oxdiff_measurement_reflns_used 9751
_cell_oxdiff_volume              1111.94(5)
_shelx_estimated_absorpt_t_max   0.873
_shelx_estimated_absorpt_t_min   0.693
_olex2_refinement_description
;
;
_shelx_res_checksum              34221
_olex2_exptl_crystal_mounting_method 'MiTeGen loop'
_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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.717