#------------------------------------------------------------------------------
#$Date: 2026-04-08 02:54:24 +0200 (Wed 08 de Apr de 2026) $
#$Revision: 305478 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/18/7251855.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_7251855
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         'C11 H18 N6'
_chemical_formula_sum            'C11 H18 N6'
_chemical_formula_weight         234.31
_chemical_melting_point          333.15
_chemical_name_common            '[HMG][TCM]'
_chemical_name_systematic        'hexamethylguanidinium tricyanomethanide'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                106.460(2)
_cell_angle_beta                 102.119(2)
_cell_angle_gamma                116.599(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1329(2)
_cell_length_b                   9.4832(2)
_cell_length_c                   9.9233(2)
_cell_measurement_reflns_used    9504
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      78.9180
_cell_measurement_theta_min      5.5790
_cell_volume                     677.76(4)
_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 0.976
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14313
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.780
_diffrn_reflns_theta_min         5.054
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93356
_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    1.148
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0334
_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)+(0.0509P)²+0.0686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2613
_reflns_number_total             2886
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6cp00614k2.cif
_cod_data_source_block           MX33_25_auto
_cod_original_cell_volume        677.76(3)
_cod_database_code               7251855
_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, -z'
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
N1 N 0.84100(17) 0.49031(17) 0.94968(15) 0.0240(3) Uani 0.5 1 d . . P A -1
N2 N 1.02513(17) 0.42682(17) 1.08402(15) 0.0232(3) Uani 0.5 1 d . . P A -1
N3 N 1.13357(17) 0.61197(17) 0.96955(15) 0.0235(3) Uani 0.5 1 d . . P A -1
N4 N 0.13157(17) -0.04826(17) 0.50059(14) 0.0234(3) Uani 0.5 1 d . . P B -1
N5 N -0.02871(17) 0.05913(17) 0.40387(15) 0.0243(3) Uani 0.5 1 d . . P B -1
N6 N -0.07237(17) -0.02718(17) 0.59688(15) 0.0237(3) Uani 0.5 1 d . . P B -1
N7 N 0.31615(11) 0.38213(10) 0.74980(10) 0.0407(2) Uani 1 1 d . . . . .
N8 N 0.72777(12) 0.94799(11) 0.94792(10) 0.0467(2) Uani 1 1 d . . . . .
N9 N 0.36458(14) 0.67229(14) 0.46152(11) 0.0564(3) Uani 1 1 d . . . . .
C1 C 0.47059(11) 0.66529(11) 0.71817(9) 0.02987(19) Uani 1 1 d . . . . .
C2 C 0.38692(11) 0.50892(11) 0.73463(10) 0.03093(19) Uani 1 1 d . . . . .
C3 C 0.61115(12) 0.82093(11) 0.84503(10) 0.0325(2) Uani 1 1 d . . . . .
C4 C 0.41156(12) 0.66828(12) 0.57659(10) 0.0367(2) Uani 1 1 d . . . . .
C10 C 1.000000 0.500000 1.000000 0.0242(2) Uani 1 2 d S . P . .
C11 C 0.8210(10) 0.6302(12) 0.9340(11) 0.0309(11) Uani 0.5 1 d . . P A -1
H11A H 0.938826 0.737672 0.975206 0.046 Uiso 0.5 1 calc R U P A -1
H11B H 0.750951 0.650451 0.990513 0.046 Uiso 0.5 1 calc R U P A -1
H11C H 0.759886 0.596317 0.825757 0.046 Uiso 0.5 1 calc R U P A -1
C12 C 0.6740(5) 0.3249(4) 0.8996(4) 0.0306(6) Uani 0.5 1 d . . P A -1
H12A H 0.698852 0.234711 0.900715 0.046 Uiso 0.5 1 calc R U P A -1
H12B H 0.596935 0.289790 0.795733 0.046 Uiso 0.5 1 calc R U P A -1
H12C H 0.614118 0.339027 0.968871 0.046 Uiso 0.5 1 calc R U P A -1
C13 C 0.9357(9) 0.3950(11) 1.1868(10) 0.0259(11) Uani 0.5 1 d . . P A -1
H13A H 0.875230 0.458314 1.195705 0.039 Uiso 0.5 1 calc R U P A -1
H13B H 1.023458 0.435815 1.287657 0.039 Uiso 0.5 1 calc R U P A -1
H13C H 0.848019 0.269505 1.146375 0.039 Uiso 0.5 1 calc R U P A -1
C14 C 1.1434(9) 0.3622(12) 1.0757(10) 0.0298(10) Uani 0.5 1 d . . P A -1
H14A H 1.184423 0.376509 0.994051 0.045 Uiso 0.5 1 calc R U P A -1
H14B H 1.078537 0.238209 1.054170 0.045 Uiso 0.5 1 calc R U P A -1
H14C H 1.246162 0.428838 1.173461 0.045 Uiso 0.5 1 calc R U P A -1
C15 C 1.3197(5) 0.7138(4) 1.0771(4) 0.0290(6) Uani 0.5 1 d . . P A -1
H15A H 1.324715 0.713062 1.176445 0.043 Uiso 0.5 1 calc R U P A -1
H15B H 1.376323 0.834525 1.088721 0.043 Uiso 0.5 1 calc R U P A -1
H15C H 1.382681 0.662110 1.037938 0.043 Uiso 0.5 1 calc R U P A -1
C16 C 1.1025(10) 0.6302(11) 0.8250(10) 0.0280(12) Uani 0.5 1 d . . P A -1
H16A H 0.977280 0.545593 0.755613 0.042 Uiso 0.5 1 calc R U P A -1
H16B H 1.178591 0.608311 0.777505 0.042 Uiso 0.5 1 calc R U P A -1
H16C H 1.130955 0.748958 0.846100 0.042 Uiso 0.5 1 calc R U P A -1
C20 C 0.000000 0.000000 0.500000 0.0263(2) Uani 1 2 d S . P . .
C21 C 0.2535(4) -0.0216(4) 0.6396(4) 0.0321(6) Uani 0.5 1 d . . P B -1
H21A H 0.219924 -0.134985 0.640335 0.048 Uiso 0.5 1 calc R U P B -1
H21B H 0.247745 0.050590 0.728546 0.048 Uiso 0.5 1 calc R U P B -1
H21C H 0.375080 0.037527 0.643537 0.048 Uiso 0.5 1 calc R U P B -1
C22 C 0.1537(6) -0.1195(5) 0.3613(4) 0.0313(7) Uani 0.5 1 d . . P B -1
H22A H 0.258057 -0.027348 0.357607 0.047 Uiso 0.5 1 calc R U P B -1
H22B H 0.047375 -0.164378 0.272383 0.047 Uiso 0.5 1 calc R U P B -1
H22C H 0.170645 -0.214792 0.360167 0.047 Uiso 0.5 1 calc R U P B -1
C23 C 0.1034(9) 0.1678(10) 0.3609(8) 0.032(2) Uani 0.5 1 d . . P B -1
H23A H 0.221225 0.200974 0.425511 0.048 Uiso 0.5 1 calc R U P B -1
H23B H 0.101450 0.273270 0.374240 0.048 Uiso 0.5 1 calc R U P B -1
H23C H 0.077992 0.103516 0.253659 0.048 Uiso 0.5 1 calc R U P B -1
C24 C -0.2082(4) 0.0201(4) 0.3338(4) 0.0319(6) Uani 0.5 1 d . . P B -1
H24A H -0.293165 -0.076285 0.349687 0.048 Uiso 0.5 1 calc R U P B -1
H5 H -0.240245 -0.013391 0.224013 0.048 Uiso 0.5 1 calc R U P B -1
H24C H -0.211539 0.123982 0.380812 0.048 Uiso 0.5 1 calc R U P B -1
C25 C -0.1330(6) 0.0865(5) 0.6592(5) 0.0318(7) Uani 0.5 1 d . . P B -1
H25A H -0.073439 0.193754 0.645797 0.048 Uiso 0.5 1 calc R U P B -1
H25B H -0.103860 0.116190 0.768284 0.048 Uiso 0.5 1 calc R U P B -1
H25C H -0.262094 0.025422 0.605292 0.048 Uiso 0.5 1 calc R U P B -1
C26 C -0.1112(10) -0.1689(9) 0.6454(9) 0.0312(19) Uani 0.5 1 d . . P B -1
H26A H -0.081421 -0.247215 0.587443 0.047 Uiso 0.5 1 calc R U P B -1
H26B H -0.237943 -0.235014 0.626397 0.047 Uiso 0.5 1 calc R U P B -1
H26C H -0.039870 -0.118671 0.754765 0.047 Uiso 0.5 1 calc R U P B -1
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'
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
C10 N1 C12 118.93(15) . . ?
C10 N1 C11 126.1(3) . . ?
C12 N1 C11 114.9(3) . . ?
C10 N2 C13 123.4(3) . . ?
C10 N2 C14 120.5(4) . . ?
C13 N2 C14 116.1(5) . . ?
C10 N3 C15 121.08(15) . . ?
C10 N3 C16 123.1(3) . . ?
C15 N3 C16 115.7(3) . . ?
C21 N4 C22 115.48(19) . . ?
C21 N4 C20 122.78(14) . . ?
C22 N4 C20 121.69(16) . . ?
C20 N5 C23 125.2(3) . . ?
C20 N5 C24 118.79(16) . . ?
C23 N5 C24 116.0(3) . . ?
C20 N6 C25 117.80(17) . . ?
C20 N6 C26 126.7(4) . . ?
C25 N6 C26 115.3(4) . . ?
C3 C1 C4 119.62(8) . . ?
C3 C1 C2 119.88(8) . . ?
C4 C1 C2 120.48(8) . . ?
N7 C2 C1 178.35(9) . . ?
N8 C3 C1 179.03(10) . . ?
N9 C4 C1 179.38(12) . . ?
N2 C10 N3 122.88(8) . . ?
N2 C10 N1 121.71(8) . . ?
N3 C10 N1 114.88(7) . . ?
N5 C20 N6 129.66(8) . . ?
N5 C20 N4 115.95(8) . . ?
N6 C20 N4 114.38(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
N1 C10 1.3844(12) . ?
N1 C12 1.460(4) . ?
N1 C11 1.463(9) . ?
N2 C10 1.2726(12) . ?
N2 C13 1.449(8) . ?
N2 C14 1.466(7) . ?
N3 C10 1.3724(13) . ?
N3 C15 1.465(4) . ?
N3 C16 1.477(8) . ?
N4 C21 1.453(3) . ?
N4 C22 1.455(4) . ?
N4 C20 1.4643(13) . ?
N5 C20 1.2739(13) . ?
N5 C23 1.432(8) . ?
N5 C24 1.463(3) . ?
N6 C20 1.2970(13) . ?
N6 C25 1.467(4) . ?
N6 C26 1.475(7) . ?
N7 C2 1.1548(12) . ?
N8 C3 1.1514(12) . ?
N9 C4 1.1502(13) . ?
C1 C3 1.4082(12) . ?
C1 C4 1.4083(13) . ?
C1 C2 1.4088(12) . ?
