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#$Date: 2026-04-08 02:54:24 +0200 (Wed, 08 Apr 2026) $
#$Revision: 305478 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/18/7251854.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_7251854
loop_
_publ_author_name
'Kufel, Lukasz Jan'
'Debono, Julia'
'Barrutia, Elene Sasieta'
'O'Dell, Luke Austin'
'Wieczorek, Wladyslaw'
'Forsyth, Craig M.'
'Forsyth, Maria'
'Pringle, Jennifer M.'
_publ_section_title
;
 The Impact of Anion Structure on the Physicochemical and Transport
 Properties of Hexamethylguanidinium-Based Sodium-Ion Electrolytes
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D6CP00614K
_journal_year                    2026
_chemical_formula_moiety         'C7 H18 N3, C6 F3 N4'
_chemical_formula_sum            'C13 H18 F3 N7'
_chemical_formula_weight         329.34
_chemical_melting_point          386.15
_chemical_name_common            '[HMG][TDI]'
_chemical_name_systematic
'hexamethyl guanidinium 4,5-dicyano-2-(trifluoromethyl)imidazolide'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2026-02-19 deposited with the CCDC.	2026-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.8658(3)
_cell_length_b                   15.6883(3)
_cell_length_c                   12.6267(3)
_cell_measurement_reflns_used    10613
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      78.0710
_cell_measurement_theta_min      5.1510
_cell_volume                     3340.97(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17720
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.938
_diffrn_reflns_theta_min         5.206
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.104
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00048(10)
_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    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0399
_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/[σ²(Fo²)+(0.0556P)²+1.8565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1127
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1714
_reflns_number_total             1881
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cp00614k2.cif
_cod_data_source_block           MX32_25_auto_a
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7251854
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x, -y, -z'
'-x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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
F1 F 0.500000 0.57713(9) 0.92564(9) 0.0642(4) Uani 1 2 d S T P . .
F2 F 0.43632(6) 0.69177(8) 0.90712(7) 0.0683(4) Uani 1 1 d . . . . .
N1 N 0.43213(5) 0.63203(6) 0.70149(7) 0.0308(3) Uani 1 1 d . . . . .
N2 N 0.36573(7) 0.60363(8) 0.44073(9) 0.0454(3) Uani 1 1 d . . . . .
N3 N 0.250000 0.51172(12) 0.250000 0.0307(4) Uani 0.7 2 d S T P A 1
N3' N 0.250000 0.6787(3) 0.250000 0.0424(12) Uani 0.3 2 d S T P A 2
N4 N 0.30356(8) 0.63919(10) 0.19269(12) 0.0362(4) Uani 0.7 1 d . . P A 1
N4' N 0.19564(19) 0.5508(2) 0.3051(3) 0.0343(7) Uani 0.3 1 d . . P A 2
C1 C 0.500000 0.63881(10) 0.75561(12) 0.0282(3) Uani 1 2 d S T P . .
C2 C 0.45866(6) 0.61989(7) 0.60090(8) 0.0271(3) Uani 1 1 d . . . . .
C3 C 0.40685(6) 0.61087(8) 0.51242(9) 0.0330(3) Uani 1 1 d . . . . .
C4 C 0.2695(3) 0.4617(4) 0.1567(5) 0.0433(11) Uani 0.7 1 d . . P A 1
H4A H 0.273152 0.499379 0.094990 0.065 Uiso 0.7 1 calc R U P A 1
H4B H 0.228057 0.419022 0.144661 0.065 Uiso 0.7 1 calc R U P A 1
H4C H 0.320470 0.433004 0.167570 0.065 Uiso 0.7 1 calc R U P A 1
C7 C 0.500000 0.65105(12) 0.87282(13) 0.0364(4) Uani 1 2 d S T P . .
C4' C 0.2687(10) 0.7332(12) 0.1629(14) 0.055(3) Uani 0.3 1 d . . P A 2
H4'1 H 0.280729 0.698466 0.100434 0.083 Uiso 0.3 1 calc R U P A 2
H4'2 H 0.314917 0.768210 0.180865 0.083 Uiso 0.3 1 calc R U P A 2
H4'3 H 0.223353 0.770249 0.147717 0.083 Uiso 0.3 1 calc R U P A 2
C5 C 0.3841(6) 0.6053(9) 0.1788(10) 0.0569(16) Uani 0.7 1 d . . P A 1
H5A H 0.391190 0.555180 0.224164 0.085 Uiso 0.7 1 calc R U P A 1
H5B H 0.422885 0.649068 0.198412 0.085 Uiso 0.7 1 calc R U P A 1
H5C H 0.391979 0.589046 0.104616 0.085 Uiso 0.7 1 calc R U P A 1
C8 C 0.250000 0.59579(10) 0.250000 0.0265(3) Uani 1 2 d S T P . .
C5' C 0.2100(8) 0.4702(10) 0.3558(12) 0.055(4) Uani 0.3 1 d . . P A 2
H5'1 H 0.183919 0.469470 0.425204 0.082 Uiso 0.3 1 calc R U P A 2
H5'2 H 0.267148 0.462037 0.365044 0.082 Uiso 0.3 1 calc R U P A 2
H5'3 H 0.188563 0.424205 0.311793 0.082 Uiso 0.3 1 calc R U P A 2
C6 C 0.2861(5) 0.7176(5) 0.1389(6) 0.0533(13) Uani 0.7 1 d . . P A 1
H6A H 0.229070 0.729088 0.143010 0.080 Uiso 0.7 1 calc R U P A 1
H6B H 0.302033 0.712985 0.064493 0.080 Uiso 0.7 1 calc R U P A 1
H6C H 0.315312 0.764375 0.172530 0.080 Uiso 0.7 1 calc R U P A 1
C6' C 0.1128(15) 0.588(2) 0.312(3) 0.071(7) Uani 0.3 1 d . . P A 2
H6'1 H 0.111118 0.642262 0.273671 0.107 Uiso 0.3 1 calc R U P A 2
H6'2 H 0.098665 0.597120 0.386103 0.107 Uiso 0.3 1 calc R U P A 2
H6'3 H 0.074963 0.548069 0.279581 0.107 Uiso 0.3 1 calc R U P A 2
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'
F F 0.0727 0.0534 '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
C1 N1 C2 101.93(9) . . ?
C8 N3 C4 122.7(3) . . ?
C8 N3 C4 122.7(3) . 8_545 ?
C4 N3 C4 114.6(5) . 8_545 ?
C8 N3' C4' 126.7(7) . 8_545 ?
C8 N3' C4' 126.7(7) . . ?
C4' N3' C4' 106.5(14) 8_545 . ?
C8 N4 C6 123.5(3) . . ?
C8 N4 C5 120.2(5) . . ?
C6 N4 C5 116.3(6) . . ?
C8 N4' C5' 125.1(6) . . ?
C8 N4' C6' 117.0(14) . . ?
C5' N4' C6' 117.9(15) . . ?
N1 C1 N1 117.72(14) . 11_655 ?
N1 C1 C7 121.13(7) . . ?
N1 C1 C7 121.13(7) 11_655 . ?
N1 C2 C2 109.21(6) . 11_655 ?
N1 C2 C3 122.96(10) . . ?
C2 C2 C3 127.81(6) 11_655 . ?
N2 C3 C2 179.43(13) . . ?
F2 C7 F2 108.59(16) . 11_655 ?
F2 C7 F1 104.81(11) . . ?
F2 C7 F1 104.81(11) 11_655 . ?
F2 C7 C1 112.76(10) . . ?
F2 C7 C1 112.76(10) 11_655 . ?
F1 C7 C1 112.51(15) . . ?
N3 C8 N4 120.46(9) . . ?
N3 C8 N4 120.46(9) . 8_545 ?
N4 C8 N4 119.07(18) . 8_545 ?
N3 C8 N4' 58.49(17) . 8_545 ?
N4 C8 N4' 61.99(17) . 8_545 ?
N4 C8 N4' 178.35(18) 8_545 8_545 ?
N3' C8 N4' 121.51(17) . . ?
N4' C8 N4' 117.0(3) 8_545 . ?
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
F1 C7 1.338(2) . ?
F2 C7 1.3225(14) . ?
N1 C1 1.3374(12) . ?
N1 C2 1.3600(14) . ?
N2 C3 1.1460(16) . ?
N3 C8 1.319(2) . ?
N3 C4 1.453(6) . ?
N3 C4 1.453(6) 8_545 ?
N3' C8 1.301(5) . ?
N3' C4' 1.427(18) 8_545 ?
N3' C4' 1.428(18) . ?
N4 C8 1.3429(16) . ?
N4 C6 1.436(8) . ?
N4 C5 1.469(12) . ?
N4' C8 1.350(3) . ?
N4' C5' 1.438(15) . ?
N4' C6' 1.52(3) . ?
C1 C7 1.492(2) . ?
C2 C2 1.394(2) 11_655 ?
C2 C3 1.4254(15) . ?
