#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/85/1518535.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_1518535
loop_
_publ_author_name
'Luo, Jiangshui'
'Jensen, Annemette H.'
'Brooks, Neil R.'
'Sniekers, Jeroen'
'Knipper, Martin'
'Aili, David'
'Li, Qingfeng'
'Vanroy, Bram'
'Wübbenhorst, Michael'
'Yan, Feng'
'Van Meervelt, Luc'
'Shao, Zhigang'
'Fang, Jianhua'
'Luo, Zheng-Hong'
'De Vos, Dirk E.'
'Binnemans, Koen'
'Fransaer, Jan'
_publ_section_title
;
 1,2,4-Triazolium perfluorobutanesulfonate as an archetypal pure protic
 organic ionic plastic crystal electrolyte for all-solid-state fuel cells
;
_journal_issue                   4
_journal_name_full               'Energy Environ. Sci.'
_journal_page_first              1276
_journal_paper_doi               10.1039/C4EE02280G
_journal_volume                  8
_journal_year                    2015
_chemical_formula_moiety         'C2 H4 N3, C4 F9 O3 S'
_chemical_formula_sum            'C6 H4 F9 N3 O3 S'
_chemical_formula_weight         369.18
_chemical_name_common            '1,2,4-Triazolium perfluorobutanesulfonate'
_chemical_name_systematic
;
1,2,4-Triazolium perfluorobutanesulfonate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2014-07-09 deposited with the CCDC.
2015-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.950(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3510(3)
_cell_length_b                   8.2492(5)
_cell_length_c                   30.2383(18)
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.7680
_cell_measurement_theta_min      3.6570
_cell_volume                     1331.59(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0981307000
_diffrn_orient_matrix_UB_12      -0.0195532000
_diffrn_orient_matrix_UB_13      -0.0160859000
_diffrn_orient_matrix_UB_21      0.0690984000
_diffrn_orient_matrix_UB_22      0.0349919000
_diffrn_orient_matrix_UB_23      -0.0167613000
_diffrn_orient_matrix_UB_31      0.0569669000
_diffrn_orient_matrix_UB_32      -0.0761151000
_diffrn_orient_matrix_UB_33      -0.0035815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            6146
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         2.81
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.367
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0906
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0874P)²+4.1767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2334
_refine_ls_wR_factor_ref         0.2404
_reflns_number_gt                2637
_reflns_number_total             3066
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ee02280g3.cif
_cod_data_source_block           kb2022-300
_cod_depositor_comments
'Adding full bibliography for 1518534--1518535.cif.'
_cod_original_cell_volume        1331.59(13)
_cod_database_code               1518535
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'N3 C2 H4 C4 F9 S O3'
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.01
 N4-H4
 0.86 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_refinement_flags_posn
N1 N 0.3138(7) 1.1016(4) 0.19970(14) 0.0379(8) Uani 1 d D
H1 H 0.375(11) 1.198(3) 0.200(2) 0.07(2) Uiso 1 d D
N2 N 0.4562(7) 0.9727(5) 0.19044(16) 0.0477(10) Uani 1 d .
C3 C 0.3043(9) 0.8510(6) 0.19318(19) 0.0475(12) Uani 1 d .
H3 H 0.3486 0.7438 0.1884 0.057 Uiso 1 calc R
N4 N 0.0773(7) 0.8978(5) 0.20367(14) 0.0394(9) Uani 1 d D
H4 H -0.050(8) 0.838(6) 0.208(2) 0.069(19) Uiso 1 d D
C5 C 0.0867(8) 1.0571(5) 0.20792(17) 0.0387(10) Uani 1 d .
H5 H -0.0430 1.1247 0.2153 0.046 Uiso 1 calc R
S6 S 0.84088(17) 0.47481(12) 0.19192(4) 0.0316(3) Uani 1 d .
O7 O 1.1046(6) 0.4460(4) 0.19773(12) 0.0459(8) Uani 1 d .
O8 O 0.6858(5) 0.3416(4) 0.20452(12) 0.0416(8) Uani 1 d .
O9 O 0.7631(6) 0.6291(4) 0.20806(11) 0.0403(8) Uani 1 d .
C10 C 0.7739(9) 0.4947(6) 0.13169(18) 0.0475(11) Uani 1 d .
F11 F 0.5400(7) 0.5517(5) 0.12472(13) 0.0822(13) Uani 1 d .
F12 F 0.9292(9) 0.6078(5) 0.11772(13) 0.0871(13) Uani 1 d .
C13 C 0.7979(13) 0.3389(9) 0.1046(2) 0.0675(16) Uani 1 d .
F14 F 0.5951(12) 0.2452(7) 0.11254(19) 0.130(2) Uani 1 d .
F15 F 0.9968(11) 0.2579(7) 0.11888(16) 0.130(2) Uani 1 d .
C16 C 0.785(2) 0.3578(15) 0.0551(3) 0.109(3) Uani 1 d .
F17 F 0.6444(17) 0.4702(10) 0.04127(18) 0.174(4) Uani 1 d .
F18 F 1.0256(17) 0.4164(12) 0.0471(2) 0.175(3) Uani 1 d .
C19 C 0.784(5) 0.206(3) 0.0276(5) 0.178(7) Uani 1 d .
F20 F 0.536(3) 0.1677(18) 0.0260(4) 0.269(7) Uani 1 d .
F21 F 0.891(3) 0.0900(14) 0.0416(3) 0.246(7) Uani 1 d .
F22 F 0.796(2) 0.2343(14) -0.0138(2) 0.233(5) Uani 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 0.0033 0.0016 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C5 N1 N2 111.3(4)
C3 N2 N1 103.4(3)
N2 C3 N4 112.1(4)
C5 N4 C3 106.4(4)
N1 C5 N4 106.9(4)
O7 S6 O8 114.9(2)
O7 S6 O9 114.4(2)
O7 S6 C10 105.1(2)
O8 S6 C10 104.6(2)
O9 S6 O8 113.56(19)
O9 S6 C10 102.5(2)
F11 C10 S6 107.7(3)
F11 C10 C13 108.8(5)
F12 C10 S6 107.0(4)
F12 C10 F11 107.4(5)
F12 C10 C13 109.8(5)
C13 C10 S6 115.9(4)
F14 C13 C10 106.5(5)
F14 C13 C16 104.5(7)
F15 C13 C10 110.4(5)
F15 C13 F14 107.0(7)
F15 C13 C16 111.4(7)
C16 C13 C10 116.4(7)
F17 C16 C13 113.4(8)
F17 C16 F18 102.9(11)
F17 C16 C19 117.1(12)
F18 C16 C13 103.0(7)
F18 C16 C19 99.0(11)
C19 C16 C13 117.6(12)
F20 C19 C16 100.3(15)
F21 C19 C16 119.7(14)
F21 C19 F20 106(2)
F21 C19 F22 116.2(17)
F22 C19 C16 113.1(17)
F22 C19 F20 97.0(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.348(5)
N1 C5 1.309(5)
N2 C3 1.298(6)
C3 N4 1.333(6)
N4 C5 1.321(5)
S6 O7 1.430(3)
S6 O8 1.444(3)
S6 O9 1.435(3)
S6 C10 1.839(5)
C10 F11 1.340(6)
C10 F12 1.337(6)
C10 C13 1.534(8)
C13 F14 1.367(8)
C13 F15 1.305(8)
C13 C16 1.502(10)
C16 F17 1.247(11)
C16 F18 1.413(12)
C16 C19 1.501(17)
C19 F20 1.36(2)
C19 F21 1.18(2)
C19 F22 1.280(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O7 0.859(10) 2.51(6) 3.053(5) 122(5) 1_465
N1 H1 O8 0.859(10) 2.04(4) 2.805(4) 148(6) 1_565
N4 H4 O9 0.859(10) 1.99(3) 2.791(5) 154(6) 1_455
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
N1 N2 C3 N4 -0.1(6)
N2 N1 C5 N4 -0.6(6)
N2 C3 N4 C5 -0.2(6)
C3 N4 C5 N1 0.5(6)
C5 N1 N2 C3 0.5(6)
S6 C10 C13 F14 73.5(6)
S6 C10 C13 F15 -42.2(7)
S6 C10 C13 C16 -170.5(6)
O7 S6 C10 F11 -168.6(4)
O7 S6 C10 F12 -53.4(4)
O7 S6 C10 C13 69.4(5)
O8 S6 C10 F11 70.0(4)
O8 S6 C10 F12 -174.8(3)
O8 S6 C10 C13 -52.0(5)
O9 S6 C10 F11 -48.8(4)
O9 S6 C10 F12 66.4(4)
O9 S6 C10 C13 -170.8(4)
C10 C13 C16 F17 -32.6(13)
C10 C13 C16 F18 77.8(9)
C10 C13 C16 C19 -174.6(12)
F11 C10 C13 F14 -47.9(7)
F11 C10 C13 F15 -163.6(6)
F11 C10 C13 C16 68.1(8)
F12 C10 C13 F14 -165.2(5)
F12 C10 C13 F15 79.1(7)
F12 C10 C13 C16 -49.2(8)
C13 C16 C19 F20 84.0(17)
C13 C16 C19 F21 -31(3)
C13 C16 C19 F22 -173.7(14)
F14 C13 C16 F17 84.4(11)
F14 C13 C16 F18 -165.1(8)
F14 C13 C16 C19 -57.5(14)
F15 C13 C16 F17 -160.4(9)
F15 C13 C16 F18 -50.0(10)
F15 C13 C16 C19 57.6(15)
F17 C16 C19 F20 -56.6(18)
F17 C16 C19 F21 -171(2)
F17 C16 C19 F22 46(2)
F18 C16 C19 F20 -166.2(13)
F18 C16 C19 F21 79(2)
F18 C16 C19 F22 -63.9(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 129853806
