# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_uvic1602
_database_code_depnum_ccdc_archive 'CCDC 2214623'
loop_
_audit_author_name
_audit_author_address
'Allen G. Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-10-21 deposited with the CCDC.	2023-06-02 downloaded from the CCDC.
;
_vrf_PLAT242_uvic1602            
;
RESPONSE: The displacement parameters of the P of the PF6 anion are
indeed "smaller" when compared with those of the F in the anion. The F atoms
have extended ADP values, thus the P, that is quite well located, will 
necessarily have smaller ADP values. This alert does not affect the 
conclusions drawn upon this structure.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'dibutyldibut-3-enylammonium hexafluorophosphate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H32 N, F6 P'
_chemical_formula_sum            'C16 H32 F6 N P'
_chemical_formula_weight         383.39

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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   15.2010(18)
_cell_length_b                   9.7668(12)
_cell_length_c                   13.4419(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1995.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5471
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      21.34

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.189
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            33098
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2168
_reflns_number_gt                1582
_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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          
;
The bis-t-Butyl, bis-butylene ammonium cation was found to be located on
the mirror plane within the lattice. This results in heavy disorder
within the butyl arms of the cation. The model was refined as a half
occupancy molecule decoupled from its mirror partner. Due to this
decoupling, C12 and C16 are directly related and refined poorly. Thus 
they were restrained to have the same atomic displacement parameters
and constrained to have similar C---C distances to their respective
bonding methylene carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1374P)²+2.7310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2583
_refine_ls_wR_factor_gt          0.2361
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001

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 0.1904(2) 0.7500 0.4714(3) 0.0341(9) Uani 1 2 d S T P . .
C1 C 0.2816(4) 0.8002(7) 0.4461(5) 0.0429(16) Uani 0.5 1 d . . P A -1
H1A H 0.2907 0.8890 0.4801 0.052 Uiso 0.5 1 calc R U P A -1
H1B H 0.2839 0.8178 0.3736 0.052 Uiso 0.5 1 calc R U P A -1
C2 C 0.3578(4) 0.7074(9) 0.4727(6) 0.064(3) Uani 0.5 1 d . . P A -1
H2A H 0.3621 0.7082 0.5461 0.076 Uiso 0.5 1 calc R U P A -1
H2B H 0.3397 0.6136 0.4537 0.076 Uiso 0.5 1 calc R U P A -1
C3 C 0.4427(5) 0.724(3) 0.4373(7) 0.082(9) Uani 0.5 1 d . . P A -1
H3 H 0.4466 0.7080 0.3677 0.098 Uiso 0.5 1 calc R U P A -1
C4 C 0.5203(6) 0.758(5) 0.4767(7) 0.151(8) Uani 0.5 1 d . . P A -1
H4A H 0.5247 0.7767 0.5459 0.181 Uiso 0.5 1 calc R U P A -1
H4B H 0.5710 0.7631 0.4357 0.181 Uiso 0.5 1 calc R U P A -1
C5 C 0.1845(4) 0.7036(6) 0.5805(5) 0.0403(15) Uani 0.5 1 d . . P A -1
H5A H 0.1233 0.6749 0.5948 0.048 Uiso 0.5 1 calc R U P A -1
H5B H 0.2229 0.6228 0.5900 0.048 Uiso 0.5 1 calc R U P A -1
C6 C 0.2111(6) 0.8142(9) 0.6548(6) 0.0572(19) Uani 0.5 1 d . . P A -1
H6A H 0.1707 0.8934 0.6511 0.069 Uiso 0.5 1 calc R U P A -1
H6B H 0.2719 0.8461 0.6418 0.069 Uiso 0.5 1 calc R U P A -1
C7 C 0.2046(5) 0.741(4) 0.7614(6) 0.081(5) Uani 0.5 1 d . . P A -1
H7 H 0.2116 0.6467 0.7779 0.097 Uiso 0.5 1 calc R U P A -1
C8 C 0.1883(7) 0.8379(13) 0.8159(8) 0.086(3) Uani 0.5 1 d . . P A -1
H8A H 0.1831 0.9273 0.7887 0.103 Uiso 0.5 1 calc R U P A -1
H8B H 0.1807 0.8240 0.8853 0.103 Uiso 0.5 1 calc R U P A -1
C9 C 0.1734(4) 0.6210(6) 0.4059(5) 0.0368(14) Uani 0.5 1 d . . P A -1
H9A H 0.1848 0.6449 0.3355 0.044 Uiso 0.5 1 calc R U P A -1
H9B H 0.2159 0.5489 0.4251 0.044 Uiso 0.5 1 calc R U P A -1
C10 C 0.0804(5) 0.5626(7) 0.4142(6) 0.0480(17) Uani 0.5 1 d . . P A -1
H10A H 0.0767 0.5125 0.4781 0.058 Uiso 0.5 1 calc R U P A -1
H10B H 0.0392 0.6409 0.4187 0.058 Uiso 0.5 1 calc R U P A -1
C11 C 0.0495(9) 0.4757(18) 0.3399(12) 0.054(3) Uani 0.5 1 d D . P A -1
H11A H -0.0144 0.4755 0.3538 0.065 Uiso 0.5 1 calc R U P A -1
H11B H 0.0704 0.3857 0.3641 0.065 Uiso 0.5 1 calc R U P A -1
C12 C 0.0505(13) 0.4550(17) 0.2350(14) 0.098(5) Uani 0.5 1 d D . P A -1
H12A H 0.0357 0.3595 0.2203 0.147 Uiso 0.5 1 calc R U P A -1
H12B H 0.1092 0.4758 0.2090 0.147 Uiso 0.5 1 calc R U P A -1
H12C H 0.0072 0.5155 0.2037 0.147 Uiso 0.5 1 calc R U P A -1
C13 C 0.1237(5) 0.8588(6) 0.4515(5) 0.0398(15) Uani 0.5 1 d . . P A -1
H13A H 0.1399 0.9409 0.4905 0.048 Uiso 0.5 1 calc R U P A -1
H13B H 0.0661 0.8264 0.4764 0.048 Uiso 0.5 1 calc R U P A -1
C14 C 0.1128(5) 0.9006(7) 0.3448(5) 0.0470(16) Uani 0.5 1 d . . P A -1
H14A H 0.0708 0.8385 0.3111 0.056 Uiso 0.5 1 calc R U P A -1
H14B H 0.1700 0.8948 0.3098 0.056 Uiso 0.5 1 calc R U P A -1
C15 C 0.0764(9) 1.0563(17) 0.3411(14) 0.053(4) Uani 0.5 1 d D . P A -1
H15A H 0.0423 1.0779 0.4019 0.064 Uiso 0.5 1 calc R U P A -1
H15B H 0.1255 1.1222 0.3351 0.064 Uiso 0.5 1 calc R U P A -1
C16 C 0.0216(13) 1.0611(18) 0.2555(14) 0.098(5) Uani 0.5 1 d D . P A -1
H16A H 0.0049 1.1562 0.2420 0.147 Uiso 0.5 1 calc R U P A -1
H16B H -0.0315 1.0064 0.2673 0.147 Uiso 0.5 1 calc R U P A -1
H16C H 0.0535 1.0239 0.1983 0.147 Uiso 0.5 1 calc R U P A -1
P1 P 0.19523(8) 0.2500 0.61424(9) 0.0377(4) Uani 1 2 d S T P . .
F1 F 0.2338(2) 0.1395(3) 0.5425(3) 0.1103(13) Uani 1 1 d . . . . .
F2 F 0.1586(3) 0.3587(4) 0.6889(3) 0.1309(15) Uani 1 1 d . . . . .
F3 F 0.2835(3) 0.2500 0.6704(3) 0.137(3) Uani 1 2 d S T P . .
F4 F 0.1079(3) 0.2500 0.5581(4) 0.200(4) Uani 1 2 d S T P . .


_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
N1 C13 1.493(7) . ?
N1 C1 1.510(7) . ?
N1 C5 1.538(7) . ?
N1 C9 1.558(6) . ?
C1 C2 1.514(10) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.385(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.334(19) . ?
C3 H3 0.9500 . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C5 C6 1.525(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.61(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.22(3) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.528(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.392(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.424(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.501(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.619(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.421(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
P1 F4 1.528(4) . ?
P1 F3 1.539(4) . ?
P1 F1 1.562(3) . ?
P1 F1 1.562(3) 7_565 ?
P1 F2 1.563(3) 7_565 ?
P1 F2 1.563(3) . ?

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
C13 N1 C1 110.6(4) . . ?
C13 N1 C5 109.9(4) . . ?
C1 N1 C5 111.3(4) . . ?
C13 N1 C9 111.2(4) . . ?
C1 N1 C9 106.8(4) . . ?
C5 N1 C9 106.9(3) . . ?
N1 C1 C2 117.1(5) . . ?
N1 C1 H1A 108.0 . . ?
C2 C1 H1A 108.0 . . ?
N1 C1 H1B 108.0 . . ?
C2 C1 H1B 108.0 . . ?
H1A C1 H1B 107.3 . . ?
C3 C2 C1 124.1(13) . . ?
C3 C2 H2A 106.3 . . ?
C1 C2 H2A 106.3 . . ?
C3 C2 H2B 106.3 . . ?
C1 C2 H2B 106.3 . . ?
H2A C2 H2B 106.4 . . ?
C4 C3 C2 135.7(10) . . ?
C4 C3 H3 112.1 . . ?
C2 C3 H3 112.1 . . ?
C3 C4 H4A 120.0 . . ?
C3 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
C6 C5 N1 113.6(5) . . ?
C6 C5 H5A 108.9 . . ?
N1 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C7 104.5(13) . . ?
C5 C6 H6A 110.8 . . ?
C7 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
C7 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C8 C7 C6 101(2) . . ?
C8 C7 H7 129.3 . . ?
C6 C7 H7 129.3 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 N1 114.5(5) . . ?
C10 C9 H9A 108.6 . . ?
N1 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N1 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 119.2(8) . . ?
C11 C10 H10A 107.5 . . ?
C9 C10 H10A 107.5 . . ?
C11 C10 H10B 107.5 . . ?
C9 C10 H10B 107.5 . . ?
H10A C10 H10B 107.0 . . ?
C10 C11 C12 142.5(17) . . ?
C10 C11 H11A 101.3 . . ?
C12 C11 H11A 101.3 . . ?
C10 C11 H11B 101.3 . . ?
C12 C11 H11B 101.3 . . ?
H11A C11 H11B 104.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 116.1(5) . . ?
N1 C13 H13A 108.3 . . ?
C14 C13 H13A 108.3 . . ?
N1 C13 H13B 108.3 . . ?
C14 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 108.8(8) . . ?
C13 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
C13 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C16 C15 C14 104.8(13) . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15B 110.8 . . ?
C14 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
F4 P1 F3 179.8(3) . . ?
F4 P1 F1 91.2(2) . . ?
F3 P1 F1 88.6(2) . . ?
F4 P1 F1 91.2(2) . 7_565 ?
F3 P1 F1 88.6(2) . 7_565 ?
F1 P1 F1 87.4(2) . 7_565 ?
F4 P1 F2 90.5(2) . 7_565 ?
F3 P1 F2 89.7(2) . 7_565 ?
F1 P1 F2 93.48(18) . 7_565 ?
F1 P1 F2 178.1(3) 7_565 7_565 ?
F4 P1 F2 90.4(2) . . ?
F3 P1 F2 89.7(2) . . ?
F1 P1 F2 178.1(3) . . ?
F1 P1 F2 93.48(18) 7_565 . ?
F2 P1 F2 85.6(3) 7_565 . ?

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
C13 N1 C1 C2 173.5(6) . . . . ?
C5 N1 C1 C2 51.0(7) . . . . ?
C9 N1 C1 C2 -65.3(7) . . . . ?
N1 C1 C2 C3 166.3(12) . . . . ?
C1 C2 C3 C4 113(4) . . . . ?
C13 N1 C5 C6 -66.6(7) . . . . ?
C1 N1 C5 C6 56.4(7) . . . . ?
C9 N1 C5 C6 172.6(5) . . . . ?
N1 C5 C6 C7 -177.2(6) . . . . ?
C5 C6 C7 C8 -151.8(10) . . . . ?
C13 N1 C9 C10 -53.9(7) . . . . ?
C1 N1 C9 C10 -174.7(5) . . . . ?
C5 N1 C9 C10 66.0(6) . . . . ?
N1 C9 C10 C11 161.1(9) . . . . ?
C9 C10 C11 C12 -39(2) . . . . ?
C1 N1 C13 C14 64.8(7) . . . . ?
C5 N1 C13 C14 -171.8(5) . . . . ?
C9 N1 C13 C14 -53.6(7) . . . . ?
N1 C13 C14 C15 -154.1(6) . . . . ?
C13 C14 C15 C16 -146.7(12) . . . . ?

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.071



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_uvic1601
_database_code_depnum_ccdc_archive 'CCDC 2214624'
loop_
_audit_author_name
_audit_author_address
'Allen G. Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2022-10-21 deposited with the CCDC.	2023-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'dibutyldiallylammonium hexafluorophosphate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H28 N, F6 P'
_chemical_formula_sum            'C14 H28 F6 N P'
_chemical_formula_weight         355.34

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           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                   9.4663(13)
_cell_length_b                   13.2301(18)
_cell_length_c                   14.178(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.998(2)
_cell_angle_gamma                90
_cell_volume                     1771.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            41285
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4431
_reflns_number_gt                3751
_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       'Bruker APEX-3 (Bruker, 2015)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0379P)²+0.8483P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4431
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N1 N 0.74964(10) 0.39789(7) 0.83079(7) 0.01467(19) Uani 1 1 d . . . . .
C1 C 0.61674(12) 0.33267(9) 0.81847(9) 0.0180(2) Uani 1 1 d . . . . .
H1A H 0.5440 0.3696 0.7785 0.022 Uiso 1 1 calc R U . . .
H1B H 0.6398 0.2700 0.7846 0.022 Uiso 1 1 calc R U . . .
C2 C 0.55585(13) 0.30466(10) 0.90948(9) 0.0215(3) Uani 1 1 d . . . . .
H2 H 0.5341 0.3568 0.9522 0.026 Uiso 1 1 calc R U . . .
C3 C 0.53151(16) 0.20992(11) 0.93216(11) 0.0304(3) Uani 1 1 d . . . . .
H3A H 0.5527 0.1570 0.8901 0.036 Uiso 1 1 calc R U . . .
H3B H 0.4927 0.1946 0.9905 0.036 Uiso 1 1 calc R U . . .
C4 C 0.85630(13) 0.35118(9) 0.90363(8) 0.0176(2) Uani 1 1 d . . . . .
H4A H 0.9398 0.3962 0.9121 0.021 Uiso 1 1 calc R U . . .
H4B H 0.8130 0.3469 0.9651 0.021 Uiso 1 1 calc R U . . .
C5 C 0.90463(14) 0.24779(9) 0.87682(9) 0.0205(2) Uani 1 1 d . . . . .
H5 H 0.8369 0.1949 0.8696 0.025 Uiso 1 1 calc R U . . .
C6 C 1.03791(15) 0.22791(11) 0.86299(10) 0.0271(3) Uani 1 1 d . . . . .
H6A H 1.1070 0.2799 0.8699 0.033 Uiso 1 1 calc R U . . .
H6B H 1.0649 0.1615 0.8461 0.033 Uiso 1 1 calc R U . . .
C7 C 0.70738(12) 0.50213(9) 0.86504(8) 0.0165(2) Uani 1 1 d . . . . .
H7A H 0.6300 0.5283 0.8212 0.020 Uiso 1 1 calc R U . . .
H7B H 0.6691 0.4945 0.9279 0.020 Uiso 1 1 calc R U . . .
C8 C 0.82542(13) 0.58030(9) 0.87297(9) 0.0194(2) Uani 1 1 d . . . . .
H8A H 0.8649 0.5890 0.8106 0.023 Uiso 1 1 calc R U . . .
H8B H 0.9024 0.5564 0.9183 0.023 Uiso 1 1 calc R U . . .
C9 C 0.76939(14) 0.68215(10) 0.90648(10) 0.0243(3) Uani 1 1 d . . . . .
H9A H 0.7287 0.6722 0.9683 0.029 Uiso 1 1 calc R U . . .
H9B H 0.8500 0.7296 0.9163 0.029 Uiso 1 1 calc R U . . .
C10 C 0.65807(16) 0.72995(11) 0.83882(11) 0.0303(3) Uani 1 1 d . . . . .
H10A H 0.6411 0.7997 0.8585 0.045 Uiso 1 1 calc R U . . .
H10B H 0.5699 0.6912 0.8393 0.045 Uiso 1 1 calc R U . . .
H10C H 0.6911 0.7299 0.7748 0.045 Uiso 1 1 calc R U . . .
C11 C 0.81733(12) 0.40345(9) 0.73696(8) 0.0165(2) Uani 1 1 d . . . . .
H11A H 0.8330 0.3336 0.7148 0.020 Uiso 1 1 calc R U . . .
H11B H 0.9114 0.4357 0.7479 0.020 Uiso 1 1 calc R U . . .
C12 C 0.73413(13) 0.46065(10) 0.65848(9) 0.0199(2) Uani 1 1 d . . . . .
H12A H 0.7247 0.5325 0.6766 0.024 Uiso 1 1 calc R U . . .
H12B H 0.6380 0.4315 0.6481 0.024 Uiso 1 1 calc R U . . .
C13 C 0.81166(16) 0.45296(11) 0.56784(9) 0.0265(3) Uani 1 1 d . . . . .
H13A H 0.9120 0.4722 0.5817 0.032 Uiso 1 1 calc R U . . .
H13B H 0.8093 0.3819 0.5458 0.032 Uiso 1 1 calc R U . . .
C14 C 0.74688(17) 0.52043(11) 0.48932(10) 0.0309(3) Uani 1 1 d . . . . .
H14A H 0.7952 0.5088 0.4314 0.046 Uiso 1 1 calc R U . . .
H14B H 0.7576 0.5914 0.5082 0.046 Uiso 1 1 calc R U . . .
H14C H 0.6461 0.5045 0.4778 0.046 Uiso 1 1 calc R U . . .
P1 P 0.25852(3) 0.53499(2) 0.82557(2) 0.01711(8) Uani 1 1 d . . . . .
F1 F 0.38800(8) 0.53640(7) 0.90504(5) 0.02801(19) Uani 1 1 d . . . . .
F2 F 0.12929(8) 0.53368(7) 0.74665(6) 0.02955(19) Uani 1 1 d . . . . .
F3 F 0.15485(8) 0.50086(7) 0.90402(6) 0.0307(2) Uani 1 1 d . . . . .
F4 F 0.29096(10) 0.42005(7) 0.80370(7) 0.0389(2) Uani 1 1 d . . . . .
F5 F 0.22639(11) 0.65057(7) 0.84820(7) 0.0429(2) Uani 1 1 d . . . . .
F6 F 0.36346(10) 0.56954(9) 0.74800(6) 0.0436(3) Uani 1 1 d . . . . .


_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
N1 C11 1.5182(14) . ?
N1 C4 1.5240(15) . ?
N1 C7 1.5246(15) . ?
N1 C1 1.5256(15) . ?
C1 C2 1.4961(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3183(19) . ?
C2 H2 0.9500 . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C4 C5 1.4996(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.3168(19) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9500 . ?
C6 H6B 0.9500 . ?
C7 C8 1.5210(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5356(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5131(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.5196(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5271(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.5221(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
P1 F4 1.5862(9) . ?
P1 F5 1.5960(9) . ?
P1 F3 1.5988(8) . ?
P1 F6 1.5993(9) . ?
P1 F2 1.5993(8) . ?
P1 F1 1.6062(8) . ?

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
C11 N1 C4 108.26(9) . . ?
C11 N1 C7 111.81(9) . . ?
C4 N1 C7 109.10(9) . . ?
C11 N1 C1 108.79(9) . . ?
C4 N1 C1 110.51(9) . . ?
C7 N1 C1 108.39(9) . . ?
C2 C1 N1 113.92(10) . . ?
C2 C1 H1A 108.8 . . ?
N1 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
C3 C2 C1 122.02(12) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
C5 C4 N1 113.43(10) . . ?
C5 C4 H4A 108.9 . . ?
N1 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
N1 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 122.17(12) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C8 C7 N1 115.52(9) . . ?
C8 C7 H7A 108.4 . . ?
N1 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
N1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 110.59(10) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C8 114.26(11) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 115.91(10) . . ?
N1 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
N1 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 C13 109.15(10) . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
C13 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 112.56(12) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
F4 P1 F5 179.65(6) . . ?
F4 P1 F3 90.10(5) . . ?
F5 P1 F3 89.77(6) . . ?
F4 P1 F6 90.09(6) . . ?
F5 P1 F6 90.03(6) . . ?
F3 P1 F6 179.37(5) . . ?
F4 P1 F2 90.11(5) . . ?
F5 P1 F2 90.22(5) . . ?
F3 P1 F2 90.41(5) . . ?
F6 P1 F2 90.20(5) . . ?
F4 P1 F1 89.98(5) . . ?
F5 P1 F1 89.69(5) . . ?
F3 P1 F1 89.46(4) . . ?
F6 P1 F1 89.93(5) . . ?
F2 P1 F1 179.84(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
C11 N1 C1 C2 168.74(10) . . . . ?
C4 N1 C1 C2 50.02(13) . . . . ?
C7 N1 C1 C2 -69.48(12) . . . . ?
N1 C1 C2 C3 -125.65(14) . . . . ?
C11 N1 C4 C5 -58.34(13) . . . . ?
C7 N1 C4 C5 179.78(10) . . . . ?
C1 N1 C4 C5 60.71(13) . . . . ?
N1 C4 C5 C6 118.02(13) . . . . ?
C11 N1 C7 C8 -54.96(13) . . . . ?
C4 N1 C7 C8 64.74(12) . . . . ?
C1 N1 C7 C8 -174.87(10) . . . . ?
N1 C7 C8 C9 179.10(10) . . . . ?
C7 C8 C9 C10 -63.35(15) . . . . ?
C4 N1 C11 C12 -172.25(10) . . . . ?
C7 N1 C11 C12 -52.05(13) . . . . ?
C1 N1 C11 C12 67.63(13) . . . . ?
N1 C11 C12 C13 -176.22(10) . . . . ?
C11 C12 C13 C14 -171.86(12) . . . . ?

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
