# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_sh4111
_database_code_depnum_ccdc_archive 'CCDC 2157463'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Saarland University
Germany
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2023-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '[C5HTMG][PF6]'
_chemical_name_common            '[C5HTMG][PF6]'
_chemical_melting_point          352
_chemical_formula_moiety         'C10 H24 N3, F6 P'
_chemical_formula_sum            'C10 H24 F6 N3 P'
_chemical_formula_weight         331.29

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'
N N 0.0061 0.0033 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   8.4524(6)
_cell_length_b                   16.1240(12)
_cell_length_c                   12.1441(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.641(4)
_cell_angle_gamma                90
_cell_volume                     1593.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    152(2)
_cell_measurement_reflns_used    4561
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7208
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      152(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10614
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         28.222
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.909
_reflns_number_total             3424
_reflns_number_gt                3101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.756
_reflns_Friedel_fraction_full    0.816

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2015),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.2657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3424
_refine_ls_number_parameters     237
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
P1 P 0.22965(7) 0.65722(3) 0.53736(5) 0.03074(13) Uani 1 1 d . . . . .
F1 F 0.13801(19) 0.60223(12) 0.60964(14) 0.0579(5) Uani 1 1 d . . . . .
F2 F 0.3925(2) 0.65249(12) 0.63893(14) 0.0604(5) Uani 1 1 d . . . . .
F3 F 0.32289(18) 0.71147(10) 0.46473(12) 0.0484(4) Uani 1 1 d . . . . .
F4 F 0.06704(19) 0.66222(10) 0.43454(14) 0.0501(4) Uani 1 1 d . . . . .
F5 F 0.2833(2) 0.57542(9) 0.48251(15) 0.0604(5) Uani 1 1 d . . . . .
F6 F 0.1754(3) 0.73849(11) 0.59104(14) 0.0710(6) Uani 1 1 d . . . . .
N1 N 0.3473(3) 0.39678(11) 0.48632(17) 0.0376(4) Uani 1 1 d D . . . .
H1N H 0.330(4) 0.4473(10) 0.503(2) 0.048(8) Uiso 1 1 d D . . . .
N2 N 0.2437(2) 0.26404(11) 0.48834(16) 0.0338(4) Uani 1 1 d . . . . .
N3 N 0.2542(2) 0.35456(11) 0.63869(16) 0.0337(4) Uani 1 1 d . . . . .
C1 C 0.2816(3) 0.33850(13) 0.53664(19) 0.0307(5) Uani 1 1 d . . . . .
C2A C 0.4418(8) 0.3807(5) 0.4063(5) 0.0327(13) Uani 0.633(5) 1 d D U P A 1
H2A H 0.378118 0.396237 0.328032 0.039 Uiso 0.633(5) 1 calc R U P A 1
H2B H 0.469739 0.321095 0.406776 0.039 Uiso 0.633(5) 1 calc R U P A 1
C3A C 0.5962(6) 0.4322(3) 0.4427(4) 0.0337(9) Uani 0.633(5) 1 d D U P A 1
H3A H 0.661202 0.414365 0.519621 0.040 Uiso 0.633(5) 1 calc R U P A 1
H3B H 0.566603 0.491217 0.447289 0.040 Uiso 0.633(5) 1 calc R U P A 1
C4A C 0.6994(4) 0.4228(2) 0.3584(3) 0.0318(9) Uani 0.633(5) 1 d D U P A 1
H4A H 0.732278 0.363912 0.357149 0.038 Uiso 0.633(5) 1 calc R U P A 1
H4B H 0.630627 0.436967 0.280947 0.038 Uiso 0.633(5) 1 calc R U P A 1
C5A C 0.8514(6) 0.4758(3) 0.3849(4) 0.0460(11) Uani 0.633(5) 1 d D U P A 1
H5A H 0.819161 0.534440 0.389506 0.055 Uiso 0.633(5) 1 calc R U P A 1
H5B H 0.922786 0.459831 0.460848 0.055 Uiso 0.633(5) 1 calc R U P A 1
C6A C 0.9480(11) 0.4687(9) 0.2985(8) 0.0434(18) Uani 0.633(5) 1 d D U P A 1
H6A H 0.983709 0.411132 0.295155 0.065 Uiso 0.633(5) 1 calc R U P A 1
H6B H 1.044376 0.504957 0.320457 0.065 Uiso 0.633(5) 1 calc R U P A 1
H6C H 0.878928 0.485296 0.223170 0.065 Uiso 0.633(5) 1 calc R U P A 1
C2B C 0.4912(13) 0.3914(8) 0.4316(10) 0.032(2) Uani 0.367(5) 1 d D U P A 2
H2C H 0.518793 0.332219 0.425759 0.038 Uiso 0.367(5) 1 calc R U P A 2
H2D H 0.453941 0.413660 0.352865 0.038 Uiso 0.367(5) 1 calc R U P A 2
C3B C 0.6470(11) 0.4372(5) 0.4942(8) 0.0398(17) Uani 0.367(5) 1 d . U P A 2
H3C H 0.685214 0.414917 0.572917 0.048 Uiso 0.367(5) 1 calc R U P A 2
H3D H 0.620203 0.496481 0.500029 0.048 Uiso 0.367(5) 1 calc R U P A 2
C4B C 0.7901(9) 0.4304(4) 0.4363(6) 0.0401(17) Uani 0.367(5) 1 d . U P A 2
H4C H 0.890580 0.454163 0.488533 0.048 Uiso 0.367(5) 1 calc R U P A 2
H4D H 0.811644 0.371030 0.425511 0.048 Uiso 0.367(5) 1 calc R U P A 2
C5B C 0.7589(9) 0.4729(4) 0.3241(7) 0.0402(17) Uani 0.367(5) 1 d . U P A 2
H5C H 0.730483 0.531591 0.333543 0.048 Uiso 0.367(5) 1 calc R U P A 2
H5D H 0.663120 0.446704 0.269930 0.048 Uiso 0.367(5) 1 calc R U P A 2
C6B C 0.9049(19) 0.4701(17) 0.2731(17) 0.049(4) Uani 0.367(5) 1 d . U P A 2
H6D H 0.927475 0.412451 0.256838 0.073 Uiso 0.367(5) 1 calc R U P A 2
H6E H 1.001620 0.493786 0.327621 0.073 Uiso 0.367(5) 1 calc R U P A 2
H6F H 0.879523 0.502312 0.202042 0.073 Uiso 0.367(5) 1 calc R U P A 2
C7 C 0.1916(4) 0.25224(18) 0.3648(2) 0.0546(7) Uani 1 1 d . . . . .
H7A H 0.176824 0.306401 0.326749 0.082 Uiso 1 1 calc R U . . .
H7B H 0.087384 0.221776 0.343845 0.082 Uiso 1 1 calc R U . . .
H7C H 0.275416 0.220599 0.340649 0.082 Uiso 1 1 calc R U . . .
C8 C 0.2546(3) 0.18864(14) 0.5557(2) 0.0400(6) Uani 1 1 d . . . . .
H8A H 0.308188 0.200969 0.636161 0.060 Uiso 1 1 calc R U . . .
H8B H 0.318976 0.147084 0.527755 0.060 Uiso 1 1 calc R U . . .
H8C H 0.143881 0.167066 0.548654 0.060 Uiso 1 1 calc R U . . .
C9 C 0.1118(3) 0.32147(17) 0.6703(2) 0.0453(6) Uani 1 1 d . . . . .
H9A H 0.041560 0.291219 0.605323 0.068 Uiso 1 1 calc R U . . .
H9B H 0.049394 0.367234 0.691362 0.068 Uiso 1 1 calc R U . . .
H9C H 0.148718 0.283754 0.735472 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3440(4) 0.41965(16) 0.7125(2) 0.0447(6) Uani 1 1 d . . . . .
H10A H 0.453114 0.425790 0.699978 0.067 Uiso 1 1 calc R U . . .
H10B H 0.355451 0.404966 0.792631 0.067 Uiso 1 1 calc R U . . .
H10C H 0.283773 0.472072 0.694804 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
P1 F2 1.5831(16) . ?
P1 F6 1.5852(18) . ?
P1 F1 1.5885(16) . ?
P1 F4 1.5904(16) . ?
P1 F3 1.5934(15) . ?
P1 F5 1.5976(16) . ?
N1 C1 1.322(3) . ?
N1 C2A 1.438(7) . ?
N1 C2B 1.538(12) . ?
N1 H1N 0.863(13) . ?
N2 C1 1.337(3) . ?
N2 C8 1.454(3) . ?
N2 C7 1.458(3) . ?
N3 C1 1.346(3) . ?
N3 C10 1.454(3) . ?
N3 C9 1.460(3) . ?
C2A C3A 1.508(6) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A C4A 1.521(6) . ?
C3A H3A 0.9900 . ?
C3A H3B 0.9900 . ?
C4A C5A 1.505(5) . ?
C4A H4A 0.9900 . ?
C4A H4B 0.9900 . ?
C5A C6A 1.498(12) . ?
C5A H5A 0.9900 . ?
C5A H5B 0.9900 . ?
C6A H6A 0.9800 . ?
C6A H6B 0.9800 . ?
C6A H6C 0.9800 . ?
C2B C3B 1.522(12) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B C4B 1.559(11) . ?
C3B H3C 0.9900 . ?
C3B H3D 0.9900 . ?
C4B C5B 1.483(10) . ?
C4B H4C 0.9900 . ?
C4B H4D 0.9900 . ?
C5B C6B 1.52(2) . ?
C5B H5C 0.9900 . ?
C5B H5D 0.9900 . ?
C6B H6D 0.9800 . ?
C6B H6E 0.9800 . ?
C6B H6F 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
F2 P1 F6 90.37(11) . . ?
F2 P1 F1 89.64(9) . . ?
F6 P1 F1 89.78(12) . . ?
F2 P1 F4 179.47(11) . . ?
F6 P1 F4 89.80(10) . . ?
F1 P1 F4 90.87(9) . . ?
F2 P1 F3 90.11(9) . . ?
F6 P1 F3 90.85(11) . . ?
F1 P1 F3 179.32(11) . . ?
F4 P1 F3 89.39(8) . . ?
F2 P1 F5 90.01(11) . . ?
F6 P1 F5 179.61(11) . . ?
F1 P1 F5 90.29(11) . . ?
F4 P1 F5 89.82(10) . . ?
F3 P1 F5 89.08(9) . . ?
C1 N1 C2A 124.3(4) . . ?
C1 N1 C2B 129.8(5) . . ?
C1 N1 H1N 116(2) . . ?
C2A N1 H1N 119(2) . . ?
C2B N1 H1N 111(2) . . ?
C1 N2 C8 122.18(19) . . ?
C1 N2 C7 122.6(2) . . ?
C8 N2 C7 115.19(19) . . ?
C1 N3 C10 121.1(2) . . ?
C1 N3 C9 122.1(2) . . ?
C10 N3 C9 115.57(19) . . ?
N1 C1 N2 121.1(2) . . ?
N1 C1 N3 119.13(19) . . ?
N2 C1 N3 119.8(2) . . ?
N1 C2A C3A 107.3(4) . . ?
N1 C2A H2A 110.2 . . ?
C3A C2A H2A 110.2 . . ?
N1 C2A H2B 110.2 . . ?
C3A C2A H2B 110.2 . . ?
H2A C2A H2B 108.5 . . ?
C2A C3A C4A 110.9(4) . . ?
C2A C3A H3A 109.5 . . ?
C4A C3A H3A 109.5 . . ?
C2A C3A H3B 109.5 . . ?
C4A C3A H3B 109.5 . . ?
H3A C3A H3B 108.1 . . ?
C5A C4A C3A 114.3(3) . . ?
C5A C4A H4A 108.7 . . ?
C3A C4A H4A 108.7 . . ?
C5A C4A H4B 108.7 . . ?
C3A C4A H4B 108.7 . . ?
H4A C4A H4B 107.6 . . ?
C6A C5A C4A 113.7(5) . . ?
C6A C5A H5A 108.8 . . ?
C4A C5A H5A 108.8 . . ?
C6A C5A H5B 108.8 . . ?
C4A C5A H5B 108.8 . . ?
H5A C5A H5B 107.7 . . ?
C5A C6A H6A 109.5 . . ?
C5A C6A H6B 109.5 . . ?
H6A C6A H6B 109.5 . . ?
C5A C6A H6C 109.5 . . ?
H6A C6A H6C 109.5 . . ?
H6B C6A H6C 109.5 . . ?
C3B C2B N1 115.9(8) . . ?
C3B C2B H2C 108.3 . . ?
N1 C2B H2C 108.3 . . ?
C3B C2B H2D 108.3 . . ?
N1 C2B H2D 108.3 . . ?
H2C C2B H2D 107.4 . . ?
C2B C3B C4B 114.4(7) . . ?
C2B C3B H3C 108.7 . . ?
C4B C3B H3C 108.7 . . ?
C2B C3B H3D 108.7 . . ?
C4B C3B H3D 108.7 . . ?
H3C C3B H3D 107.6 . . ?
C5B C4B C3B 114.5(6) . . ?
C5B C4B H4C 108.6 . . ?
C3B C4B H4C 108.6 . . ?
C5B C4B H4D 108.6 . . ?
C3B C4B H4D 108.6 . . ?
H4C C4B H4D 107.6 . . ?
C4B C5B C6B 113.4(9) . . ?
C4B C5B H5C 108.9 . . ?
C6B C5B H5C 108.9 . . ?
C4B C5B H5D 108.9 . . ?
C6B C5B H5D 108.9 . . ?
H5C C5B H5D 107.7 . . ?
C5B C6B H6D 109.5 . . ?
C5B C6B H6E 109.5 . . ?
H6D C6B H6E 109.5 . . ?
C5B C6B H6F 109.5 . . ?
H6D C6B H6F 109.5 . . ?
H6E C6B H6F 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C2A N1 C1 N2 -25.6(4) . . . . ?
C2B N1 C1 N2 -47.3(6) . . . . ?
C2A N1 C1 N3 153.8(4) . . . . ?
C2B N1 C1 N3 132.1(6) . . . . ?
C8 N2 C1 N1 147.1(2) . . . . ?
C7 N2 C1 N1 -31.7(4) . . . . ?
C8 N2 C1 N3 -32.3(3) . . . . ?
C7 N2 C1 N3 148.9(3) . . . . ?
C10 N3 C1 N1 -22.0(3) . . . . ?
C9 N3 C1 N1 144.4(2) . . . . ?
C10 N3 C1 N2 157.3(2) . . . . ?
C9 N3 C1 N2 -36.2(3) . . . . ?
C1 N1 C2A C3A -131.8(4) . . . . ?
N1 C2A C3A C4A -176.7(4) . . . . ?
C2A C3A C4A C5A 176.8(5) . . . . ?
C3A C4A C5A C6A -177.5(6) . . . . ?
C1 N1 C2B C3B -111.1(8) . . . . ?
N1 C2B C3B C4B -179.9(8) . . . . ?
C2B C3B C4B C5B 67.1(10) . . . . ?
C3B C4B C5B C6B 176.3(12) . . . . ?

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
_geom_hbond_publ_flag
N1 H1N F5 0.863(13) 2.106(16) 2.929(2) 159(3) . yes

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.031


_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sh4811_a
_database_code_depnum_ccdc_archive 'CCDC 2157466'
loop_
_audit_author_name
_audit_author_address
'Bernd Morgenstern'
;Saarland University
Germany
;
_audit_update_record             
;
2022-03-09 deposited with the CCDC.	2023-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '[2O2HTMG][PF6]'
_chemical_name_common            '[2O2HTMG][PF6]'
_chemical_melting_point          322
_chemical_formula_moiety         'C9 H22 N3 O, (P F6)'
_chemical_formula_sum            'C9 H22 F6 N3 O P'
_chemical_formula_weight         333.26

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'
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'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   8.2155(7)
_cell_length_b                   15.5131(14)
_cell_length_c                   12.1578(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.340(3)
_cell_angle_gamma                90
_cell_volume                     1494.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2716
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.83

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC I\^A?S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 Venture, Photon II'
_diffrn_measurement_method       'φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10697
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3056
_reflns_number_gt                2222
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX 3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT  (Bruker, 2019)'
_computing_data_reduction        'SAINT  (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2018/3 (Sheldrick, 2015),                                              
SHELXLe Rev 1000 (Huebschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+0.6596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     244
_refine_ls_number_restraints     124
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
P1 P -0.04231(7) 0.28755(4) 0.10574(4) 0.02865(16) Uani 1 1 d . . . . .
F1A F -0.0466(4) 0.38916(12) 0.1215(2) 0.0592(8) Uani 0.822(7) 1 d D U P A 1
F2A F -0.0315(6) 0.2978(3) -0.0198(3) 0.0618(11) Uani 0.822(7) 1 d D U P A 1
F3A F 0.1571(5) 0.2874(3) 0.1521(5) 0.0520(9) Uani 0.822(7) 1 d D U P A 1
F4A F -0.0415(5) 0.18584(14) 0.0924(2) 0.0535(7) Uani 0.822(7) 1 d D U P A 1
F5A F -0.0576(4) 0.2762(2) 0.2334(2) 0.0502(7) Uani 0.822(7) 1 d D U P A 1
F6A F -0.2445(4) 0.2886(3) 0.0613(3) 0.0515(8) Uani 0.822(7) 1 d D U P A 1
F1B F 0.0295(16) 0.3829(6) 0.0781(12) 0.061(4) Uani 0.178(7) 1 d D U P A 2
F2B F -0.030(2) 0.2668(12) -0.0230(13) 0.057(4) Uani 0.178(7) 1 d D U P A 2
F3B F 0.146(2) 0.2562(11) 0.1507(19) 0.051(4) Uani 0.178(7) 1 d D U P A 2
F4B F -0.1147(17) 0.1987(8) 0.1168(12) 0.058(3) Uani 0.178(7) 1 d D U P A 2
F5B F -0.0516(18) 0.3205(13) 0.2219(11) 0.068(4) Uani 0.178(7) 1 d D U P A 2
F6B F -0.2287(17) 0.3261(9) 0.0507(14) 0.043(3) Uani 0.178(7) 1 d D U P A 2
O1 O 0.66217(19) 0.48741(9) 0.39764(12) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.4274(2) 0.56527(11) 0.17021(14) 0.0282(4) Uani 1 1 d . . . . .
N2 N 0.6946(2) 0.59601(11) 0.15099(14) 0.0280(4) Uani 1 1 d . . . . .
N3 N 0.6147(2) 0.45407(11) 0.16239(14) 0.0280(4) Uani 1 1 d D . . . .
H3N H 0.7036(19) 0.4408(14) 0.1395(17) 0.034 Uiso 1 1 d D U . . .
C1 C 0.5796(2) 0.53887(13) 0.16288(15) 0.0245(4) Uani 1 1 d . . . . .
C2 C 0.4069(3) 0.64452(14) 0.23020(19) 0.0387(5) Uani 1 1 d . . . . .
H2A H 0.342050 0.686407 0.175565 0.058 Uiso 1 1 calc R U . . .
H2B H 0.518241 0.668574 0.267275 0.058 Uiso 1 1 calc R U . . .
H2C H 0.346832 0.631701 0.287974 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2765(3) 0.51298(15) 0.1315(2) 0.0378(5) Uani 1 1 d . . . . .
H3A H 0.184176 0.548715 0.086745 0.057 Uiso 1 1 calc R U . . .
H3B H 0.244881 0.489190 0.197561 0.057 Uiso 1 1 calc R U . . .
H3C H 0.298719 0.465735 0.083898 0.057 Uiso 1 1 calc R U . . .
C4 C 0.6497(3) 0.67872(14) 0.09246(19) 0.0353(5) Uani 1 1 d . . . . .
H4A H 0.712250 0.685778 0.034683 0.053 Uiso 1 1 calc R U . . .
H4B H 0.678593 0.725772 0.148003 0.053 Uiso 1 1 calc R U . . .
H4C H 0.528242 0.679888 0.055558 0.053 Uiso 1 1 calc R U . . .
C5 C 0.8743(3) 0.57523(15) 0.18318(19) 0.0366(5) Uani 1 1 d . . . . .
H5A H 0.905090 0.549131 0.118064 0.055 Uiso 1 1 calc R U . . .
H5B H 0.898523 0.534554 0.247129 0.055 Uiso 1 1 calc R U . . .
H5C H 0.940011 0.628057 0.205954 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5761(3) 0.39174(13) 0.24260(18) 0.0322(5) Uani 1 1 d . . . . .
H6A H 0.589749 0.332613 0.215734 0.039 Uiso 1 1 calc R U . . .
H6B H 0.456875 0.398763 0.244036 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6887(3) 0.40282(14) 0.36192(17) 0.0345(5) Uani 1 1 d . . . . .
H7A H 0.659823 0.359781 0.413861 0.041 Uiso 1 1 calc R U . . .
H7B H 0.808448 0.394875 0.362372 0.041 Uiso 1 1 calc R U . . .
C8 C 0.7520(3) 0.50387(16) 0.51285(18) 0.0450(6) Uani 1 1 d . . . . .
H8A H 0.872830 0.489544 0.524518 0.054 Uiso 1 1 calc R U . . .
H8B H 0.706542 0.467518 0.564735 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7336(3) 0.59712(17) 0.5388(2) 0.0490(6) Uani 1 1 d . . . . .
H9A H 0.779476 0.632718 0.487483 0.073 Uiso 1 1 calc R U . . .
H9B H 0.795404 0.608964 0.618002 0.073 Uiso 1 1 calc R U . . .
H9C H 0.613891 0.610724 0.527848 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
P1 F4B 1.522(10) . ?
P1 F5B 1.522(12) . ?
P1 F2A 1.561(3) . ?
P1 F3B 1.579(16) . ?
P1 F3A 1.585(4) . ?
P1 F4A 1.586(2) . ?
P1 F1A 1.5893(19) . ?
P1 F5A 1.600(3) . ?
P1 F6A 1.605(3) . ?
P1 F6B 1.615(13) . ?
P1 F2B 1.628(15) . ?
P1 F1B 1.659(8) . ?
O1 C7 1.417(2) . ?
O1 C8 1.423(3) . ?
N1 C1 1.340(2) . ?
N1 C3 1.452(3) . ?
N1 C2 1.462(3) . ?
N2 C1 1.331(2) . ?
N2 C5 1.460(3) . ?
N2 C4 1.466(3) . ?
N3 C1 1.347(2) . ?
N3 C6 1.466(3) . ?
N3 H3N 0.873(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.510(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.497(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
F4B P1 F5B 96.1(7) . . ?
F4B P1 F3B 93.5(7) . . ?
F5B P1 F3B 93.9(9) . . ?
F2A P1 F3A 91.5(2) . . ?
F2A P1 F4A 89.88(16) . . ?
F3A P1 F4A 90.19(15) . . ?
F2A P1 F1A 91.47(16) . . ?
F3A P1 F1A 90.70(15) . . ?
F4A P1 F1A 178.36(13) . . ?
F2A P1 F5A 178.7(2) . . ?
F3A P1 F5A 89.7(2) . . ?
F4A P1 F5A 89.64(13) . . ?
F1A P1 F5A 89.00(12) . . ?
F2A P1 F6A 89.5(2) . . ?
F3A P1 F6A 178.8(2) . . ?
F4A P1 F6A 90.45(14) . . ?
F1A P1 F6A 88.63(13) . . ?
F5A P1 F6A 89.27(17) . . ?
F4B P1 F6B 91.2(5) . . ?
F5B P1 F6B 89.2(8) . . ?
F3B P1 F6B 174.0(9) . . ?
F4B P1 F2B 91.8(8) . . ?
F5B P1 F2B 171.8(9) . . ?
F3B P1 F2B 88.0(10) . . ?
F6B P1 F2B 88.2(8) . . ?
F4B P1 F1B 173.6(6) . . ?
F5B P1 F1B 89.8(7) . . ?
F3B P1 F1B 88.6(7) . . ?
F6B P1 F1B 86.3(5) . . ?
F2B P1 F1B 82.2(7) . . ?
C7 O1 C8 112.70(16) . . ?
C1 N1 C3 122.61(18) . . ?
C1 N1 C2 121.50(18) . . ?
C3 N1 C2 115.52(18) . . ?
C1 N2 C5 121.38(17) . . ?
C1 N2 C4 122.73(17) . . ?
C5 N2 C4 115.47(17) . . ?
C1 N3 C6 123.83(17) . . ?
C1 N3 H3N 115.5(15) . . ?
C6 N3 H3N 113.7(15) . . ?
N2 C1 N1 120.34(18) . . ?
N2 C1 N3 119.38(18) . . ?
N1 C1 N3 120.21(18) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 112.24(18) . . ?
N3 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O1 C7 C6 107.16(16) . . ?
O1 C7 H7A 110.3 . . ?
C6 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C6 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
O1 C8 C9 109.0(2) . . ?
O1 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O1 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C5 N2 C1 N1 157.62(18) . . . . ?
C4 N2 C1 N1 -30.2(3) . . . . ?
C5 N2 C1 N3 -25.3(3) . . . . ?
C4 N2 C1 N3 146.86(19) . . . . ?
C3 N1 C1 N2 150.76(19) . . . . ?
C2 N1 C1 N2 -36.6(3) . . . . ?
C3 N1 C1 N3 -26.3(3) . . . . ?
C2 N1 C1 N3 146.39(19) . . . . ?
C6 N3 C1 N2 136.2(2) . . . . ?
C6 N3 C1 N1 -46.7(3) . . . . ?
C1 N3 C6 C7 -71.1(3) . . . . ?
C8 O1 C7 C6 175.47(18) . . . . ?
N3 C6 C7 O1 60.1(2) . . . . ?
C7 O1 C8 C9 173.24(19) . . . . ?

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
_geom_hbond_publ_flag
N3 H3N F1A^a 0.873(10) 2.267(11) 3.120(4) 166.0(19) 1_655 yes
N3 H3N F6B^b 0.873(10) 2.23(2) 2.893(15) 133.0(19) 1_655 yes

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'From the Melt'
