# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_map004
_database_code_depnum_ccdc_archive 'CCDC 2314737'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'pent-3-yn-1-yltriphenylphosphonium iodide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 P, I'
_chemical_formula_sum            'C23 H22 I P'
_chemical_formula_weight         456.27

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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                   10.606(10)
_cell_length_b                   18.313(16)
_cell_length_c                   10.750(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.717(12)
_cell_angle_gamma                90
_cell_volume                     2000(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8795
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      28.04

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    1.684
_shelx_estimated_absorpt_T_min   0.710
_shelx_estimated_absorpt_T_max   0.825
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7833
_exptl_absorpt_correction_T_max  0.9000
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa X8-APEX-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            31690
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         28.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4998
_reflns_number_gt                4330
_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-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0184P)²+1.0327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4998
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0486
_refine_ls_wR_factor_gt          0.0460
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.28234(4) 0.36666(3) 0.66369(4) 0.01322(9) Uani 1 1 d . . . . .
C1 C 0.36800(18) 0.44452(10) 0.75019(17) 0.0160(4) Uani 1 1 d . . . . .
H1A H 0.302244 0.479373 0.764622 0.019 Uiso 1 1 calc R U . . .
H1B H 0.423107 0.428128 0.836469 0.019 Uiso 1 1 calc R U . . .
C2 C 0.45605(18) 0.48485(11) 0.68181(18) 0.0189(4) Uani 1 1 d . . . . .
H2A H 0.523931 0.512538 0.747353 0.023 Uiso 1 1 calc R U . . .
H2B H 0.501842 0.448474 0.642177 0.023 Uiso 1 1 calc R U . . .
C3 C 0.38350(19) 0.53530(11) 0.58084(18) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.3244(2) 0.57662(11) 0.50009(19) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.2526(2) 0.62566(13) 0.3971(2) 0.0332(5) Uani 1 1 d . . . . .
H5A H 0.297659 0.672945 0.406506 0.040 Uiso 1 1 calc R U . . .
H5B H 0.162958 0.632518 0.403168 0.040 Uiso 1 1 calc R U . . .
H5C H 0.249051 0.604460 0.312451 0.040 Uiso 1 1 calc R U . . .
C6 C 0.16053(17) 0.33725(10) 0.73952(17) 0.0150(4) Uani 1 1 d . . . . .
C7 C 0.09513(19) 0.27142(11) 0.70033(19) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.115657 0.242760 0.635090 0.025 Uiso 1 1 calc R U . . .
C8 C 0.00039(19) 0.24793(11) 0.7566(2) 0.0248(4) Uani 1 1 d . . . . .
H8 H -0.044412 0.203162 0.729733 0.030 Uiso 1 1 calc R U . . .
C9 C -0.02933(19) 0.28941(12) 0.8518(2) 0.0255(5) Uani 1 1 d . . . . .
H9 H -0.094440 0.273094 0.890352 0.031 Uiso 1 1 calc R U . . .
C10 C 0.03556(19) 0.35460(12) 0.89100(19) 0.0247(4) Uani 1 1 d . . . . .
H10 H 0.014923 0.382889 0.956605 0.030 Uiso 1 1 calc R U . . .
C11 C 0.13061(18) 0.37900(11) 0.83523(17) 0.0194(4) Uani 1 1 d . . . . .
H11 H 0.174914 0.423894 0.862235 0.023 Uiso 1 1 calc R U . . .
C12 C 0.39498(17) 0.29334(10) 0.66953(17) 0.0148(4) Uani 1 1 d . . . . .
C13 C 0.3614(2) 0.23702(11) 0.57883(19) 0.0224(4) Uani 1 1 d . . . . .
H13 H 0.282625 0.239873 0.509078 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4429(2) 0.17708(12) 0.5906(2) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.420013 0.138542 0.529056 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5583(2) 0.17303(12) 0.6923(2) 0.0268(5) Uani 1 1 d . . . . .
H15 H 0.614504 0.131872 0.699938 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5912(2) 0.22863(12) 0.7821(2) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.670079 0.225457 0.851645 0.031 Uiso 1 1 calc R U . . .
C17 C 0.51052(18) 0.28914(11) 0.77185(19) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.533697 0.327392 0.833970 0.024 Uiso 1 1 calc R U . . .
C18 C 0.20370(17) 0.39005(10) 0.49788(16) 0.0149(4) Uani 1 1 d . . . . .
C19 C 0.07437(18) 0.41564(10) 0.46297(18) 0.0186(4) Uani 1 1 d . . . . .
H19 H 0.025014 0.414993 0.524020 0.022 Uiso 1 1 calc R U . . .
C20 C 0.0187(2) 0.44195(11) 0.33878(19) 0.0246(4) Uani 1 1 d . . . . .
H20 H -0.069728 0.458840 0.314058 0.030 Uiso 1 1 calc R U . . .
C21 C 0.0908(2) 0.44383(11) 0.25034(19) 0.0246(4) Uani 1 1 d . . . . .
H21 H 0.052759 0.463392 0.166009 0.030 Uiso 1 1 calc R U . . .
C22 C 0.2186(2) 0.41728(11) 0.28425(19) 0.0227(4) Uani 1 1 d . . . . .
H22 H 0.267143 0.417645 0.222476 0.027 Uiso 1 1 calc R U . . .
C23 C 0.27568(19) 0.39022(11) 0.40793(18) 0.0200(4) Uani 1 1 d . . . . .
H23 H 0.363172 0.371926 0.431305 0.024 Uiso 1 1 calc R U . . .
I1 I 0.73716(2) 0.06240(2) 0.49103(2) 0.01972(4) 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
P1 C12 1.786(2) . ?
P1 C18 1.789(2) . ?
P1 C6 1.797(2) . ?
P1 C1 1.799(2) . ?
C1 C2 1.534(3) . ?
C2 C3 1.464(3) . ?
C3 C4 1.186(3) . ?
C4 C5 1.458(3) . ?
C6 C11 1.390(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.382(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.387(3) . ?
C12 C13 1.393(3) . ?
C12 C17 1.394(3) . ?
C13 C14 1.380(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.385(3) . ?
C18 C23 1.394(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.384(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
C12 P1 C18 109.30(9) . . ?
C12 P1 C6 108.64(10) . . ?
C18 P1 C6 109.49(10) . . ?
C12 P1 C1 110.14(10) . . ?
C18 P1 C1 110.27(9) . . ?
C6 P1 C1 108.97(10) . . ?
C2 C1 P1 114.86(14) . . ?
C3 C2 C1 113.36(16) . . ?
C4 C3 C2 179.3(2) . . ?
C3 C4 C5 177.9(2) . . ?
C11 C6 C7 119.97(18) . . ?
C11 C6 P1 121.20(15) . . ?
C7 C6 P1 118.83(15) . . ?
C8 C7 C6 119.87(19) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C10 120.06(19) . . ?
C9 C10 C11 120.45(19) . . ?
C10 C11 C6 119.47(19) . . ?
C13 C12 C17 120.08(17) . . ?
C13 C12 P1 119.86(14) . . ?
C17 C12 P1 119.78(14) . . ?
C14 C13 C12 119.81(19) . . ?
C13 C14 C15 120.1(2) . . ?
C16 C15 C14 120.05(19) . . ?
C15 C16 C17 120.63(19) . . ?
C16 C17 C12 119.32(19) . . ?
C23 C18 C19 120.34(17) . . ?
C23 C18 P1 120.02(15) . . ?
C19 C18 P1 119.28(14) . . ?
C20 C19 C18 119.40(18) . . ?
C19 C20 C21 120.41(19) . . ?
C20 C21 C22 120.22(19) . . ?
C23 C22 C21 120.15(19) . . ?
C22 C23 C18 119.46(19) . . ?

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
C12 P1 C1 C2 72.28(15) . . . . ?
C18 P1 C1 C2 -48.43(16) . . . . ?
C6 P1 C1 C2 -168.64(13) . . . . ?
P1 C1 C2 C3 81.07(19) . . . . ?
C12 P1 C6 C11 129.42(15) . . . . ?
C18 P1 C6 C11 -111.28(16) . . . . ?
C1 P1 C6 C11 9.41(17) . . . . ?
C12 P1 C6 C7 -50.87(17) . . . . ?
C18 P1 C6 C7 68.43(17) . . . . ?
C1 P1 C6 C7 -170.88(14) . . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
P1 C6 C7 C8 -179.54(14) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
P1 C6 C11 C10 179.71(14) . . . . ?
C18 P1 C12 C13 -38.95(18) . . . . ?
C6 P1 C12 C13 80.47(18) . . . . ?
C1 P1 C12 C13 -160.24(15) . . . . ?
C18 P1 C12 C17 147.06(15) . . . . ?
C6 P1 C12 C17 -93.51(17) . . . . ?
C1 P1 C12 C17 25.77(18) . . . . ?
C17 C12 C13 C14 0.0(3) . . . . ?
P1 C12 C13 C14 -173.98(16) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
P1 C12 C17 C16 174.07(15) . . . . ?
C12 P1 C18 C23 -39.17(18) . . . . ?
C6 P1 C18 C23 -158.07(15) . . . . ?
C1 P1 C18 C23 82.04(17) . . . . ?
C12 P1 C18 C19 147.76(15) . . . . ?
C6 P1 C18 C19 28.87(18) . . . . ?
C1 P1 C18 C19 -91.03(17) . . . . ?
C23 C18 C19 C20 -0.7(3) . . . . ?
P1 C18 C19 C20 172.32(15) . . . . ?
C18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 1.9(3) . . . . ?
C20 C21 C22 C23 -1.5(3) . . . . ?
C21 C22 C23 C18 -0.1(3) . . . . ?
C19 C18 C23 C22 1.2(3) . . . . ?
P1 C18 C23 C22 -171.79(15) . . . . ?

_refine_diff_density_max         0.629
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_map006
_database_code_depnum_ccdc_archive 'CCDC 2314738'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-04-16 downloaded from the CCDC.
;

_vrf_PLAT094_map006              
;
RESPONSE: The large residual density (this alert and PLAT097 below)
are a Fourier peak located near C4/C5 of the pentyl chain. The residual
peak is outside of the linear chain. It is unclear what this residual
electron density arises from. Examination of the data did not reveal
any unusual problems. Attempts to correct this did not alter the presence
of this peak.
;


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'pent-3-yn-1-yltriphenylphosphonium hexafluorophosphate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 P, F6 P'
_chemical_formula_sum            'C23 H22 F6 P2'
_chemical_formula_weight         474.34

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'
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                   11.1886(11)
_cell_length_b                   17.4838(16)
_cell_length_c                   11.8098(11)
_cell_angle_alpha                90
_cell_angle_beta                 107.4620(10)
_cell_angle_gamma                90
_cell_volume                     2203.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9269
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      28.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.255
_shelx_estimated_absorpt_T_min   0.940
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9383
_exptl_absorpt_correction_T_max  0.9919
_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            41837
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.908
_diffrn_reflns_theta_max         28.355
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5489
_reflns_number_gt                4778
_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-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_refine_special_details          
;
The PF6 anion was found to have disorder in the equatorial fluroine atoms.
These were modeled over two sites with occupancies summed to unity, 
yielding an approximately 0.87:0.13 ratio. The minor component was modeled
with isotropic displacement parameters.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+2.0634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5489
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.037
_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
P1 P 0.78079(4) 0.36369(2) 0.64502(4) 0.01922(11) Uani 1 1 d . . . . .
C1 C 0.86261(17) 0.44484(10) 0.72664(15) 0.0234(3) Uani 1 1 d . . . . .
H1A H 0.800241 0.483425 0.733132 0.028 Uiso 1 1 calc R U . . .
H1B H 0.909062 0.428110 0.808043 0.028 Uiso 1 1 calc R U . . .
C2 C 0.95546(17) 0.48290(10) 0.67031(17) 0.0268(4) Uani 1 1 d . . . . .
H2A H 1.022967 0.508091 0.733263 0.032 Uiso 1 1 calc R U . . .
H2B H 0.994344 0.443053 0.633289 0.032 Uiso 1 1 calc R U . . .
C3 C 0.89420(18) 0.53960(10) 0.58049(17) 0.0270(4) Uani 1 1 d . . . . .
C4 C 0.8396(2) 0.58610(11) 0.51080(18) 0.0332(4) Uani 1 1 d . . . . .
C5 C 0.7719(3) 0.64219(15) 0.4245(2) 0.0522(7) Uani 1 1 d . . . . .
H5A H 0.758345 0.622048 0.344167 0.063 Uiso 1 1 calc R U . . .
H5B H 0.820892 0.689506 0.434016 0.063 Uiso 1 1 calc R U . . .
H5C H 0.690845 0.652832 0.437069 0.063 Uiso 1 1 calc R U . . .
C6 C 0.66258(16) 0.33416(10) 0.70986(15) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.64341(18) 0.37392(11) 0.80497(16) 0.0275(4) Uani 1 1 d . . . . .
H7A H 0.692402 0.417847 0.835677 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5525(2) 0.34926(13) 0.85495(18) 0.0344(4) Uani 1 1 d . . . . .
H8A H 0.539069 0.376515 0.919673 0.041 Uiso 1 1 calc R U . . .
C9 C 0.48169(19) 0.28540(13) 0.8109(2) 0.0359(5) Uani 1 1 d . . . . .
H9A H 0.419627 0.268805 0.845438 0.043 Uiso 1 1 calc R U . . .
C10 C 0.50048(19) 0.24523(12) 0.7166(2) 0.0365(5) Uani 1 1 d . . . . .
H10A H 0.451492 0.201167 0.686699 0.044 Uiso 1 1 calc R U . . .
C11 C 0.59079(18) 0.26937(11) 0.66589(19) 0.0308(4) Uani 1 1 d . . . . .
H11A H 0.603806 0.241834 0.601255 0.037 Uiso 1 1 calc R U . . .
C12 C 0.88870(16) 0.28730(10) 0.65423(16) 0.0231(3) Uani 1 1 d . . . . .
C13 C 0.8587(2) 0.22853(11) 0.57066(18) 0.0318(4) Uani 1 1 d . . . . .
H13A H 0.783810 0.230802 0.505978 0.038 Uiso 1 1 calc R U . . .
C14 C 0.9392(2) 0.16675(12) 0.5830(2) 0.0397(5) Uani 1 1 d . . . . .
H14A H 0.919353 0.126295 0.526739 0.048 Uiso 1 1 calc R U . . .
C15 C 1.0483(2) 0.16381(12) 0.6769(2) 0.0404(5) Uani 1 1 d . . . . .
H15A H 1.103592 0.121589 0.684168 0.048 Uiso 1 1 calc R U . . .
C16 C 1.0777(2) 0.22155(13) 0.7599(2) 0.0382(5) Uani 1 1 d . . . . .
H16A H 1.152722 0.218878 0.824318 0.046 Uiso 1 1 calc R U . . .
C17 C 0.99793(18) 0.28359(11) 0.74976(18) 0.0302(4) Uani 1 1 d . . . . .
H17A H 1.017577 0.323229 0.807414 0.036 Uiso 1 1 calc R U . . .
C18 C 0.71035(17) 0.38911(10) 0.49297(15) 0.0237(3) Uani 1 1 d . . . . .
C19 C 0.58845(18) 0.41812(11) 0.45766(17) 0.0298(4) Uani 1 1 d . . . . .
H19A H 0.539829 0.418499 0.511217 0.036 Uiso 1 1 calc R U . . .
C20 C 0.5392(2) 0.44646(13) 0.34294(19) 0.0388(5) Uani 1 1 d . . . . .
H20A H 0.456249 0.466177 0.318004 0.047 Uiso 1 1 calc R U . . .
C21 C 0.6095(2) 0.44618(13) 0.26541(18) 0.0404(5) Uani 1 1 d . . . . .
H21A H 0.575381 0.466559 0.187811 0.049 Uiso 1 1 calc R U . . .
C22 C 0.7296(2) 0.41640(13) 0.29969(18) 0.0369(5) Uani 1 1 d . . . . .
H22A H 0.777044 0.415448 0.245144 0.044 Uiso 1 1 calc R U . . .
C23 C 0.78085(18) 0.38788(12) 0.41388(16) 0.0298(4) Uani 1 1 d . . . . .
H23A H 0.863481 0.367677 0.437795 0.036 Uiso 1 1 calc R U . . .
P2 P 0.25170(4) 0.42899(3) 0.98399(4) 0.02301(12) Uani 1 1 d . . . . .
F1 F 0.27356(11) 0.44078(7) 1.12385(10) 0.0326(3) Uani 1 1 d . . . . .
F2 F 0.22994(13) 0.41747(8) 0.84524(10) 0.0431(3) Uani 1 1 d . . . . .
F3 F 0.39554(16) 0.4114(2) 1.01143(17) 0.0824(10) Uani 0.876(3) 1 d . . P A 1
F4 F 0.2765(3) 0.51686(10) 0.97029(15) 0.0645(7) Uani 0.876(3) 1 d . . P A 1
F5 F 0.10723(14) 0.44577(14) 0.96023(14) 0.0534(6) Uani 0.876(3) 1 d . . P A 1
F6 F 0.2237(2) 0.34083(9) 0.99977(14) 0.0613(7) Uani 0.876(3) 1 d . . P A 1
F3A F 0.3823(10) 0.4689(6) 0.9983(9) 0.034(3) Uiso 0.124(3) 1 d . . P A 2
F4A F 0.1919(13) 0.5113(8) 0.9620(11) 0.049(3) Uiso 0.124(3) 1 d . . P A 2
F5A F 0.1208(11) 0.3932(8) 0.9617(10) 0.044(3) Uiso 0.124(3) 1 d . . P A 2
F6A F 0.3109(10) 0.3493(6) 0.9943(9) 0.034(3) Uiso 0.124(3) 1 d . . P A 2


_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 C12 1.7817(17) . ?
P1 C18 1.7871(17) . ?
P1 C6 1.7916(18) . ?
P1 C1 1.8030(17) . ?
C1 C2 1.542(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.463(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.187(3) . ?
C4 C5 1.453(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.391(2) . ?
C6 C11 1.396(3) . ?
C7 C8 1.389(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.377(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.386(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C17 1.394(3) . ?
C12 C13 1.394(3) . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.377(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 C23 1.392(3) . ?
C18 C19 1.396(3) . ?
C19 C20 1.392(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.384(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
P2 F6A 1.533(10) . ?
P2 F5A 1.541(12) . ?
P2 F3 1.5738(17) . ?
P2 F4A 1.575(13) . ?
P2 F4 1.5781(17) . ?
P2 F3A 1.582(10) . ?
P2 F5 1.5829(16) . ?
P2 F6 1.5948(17) . ?
P2 F2 1.5954(12) . ?
P2 F1 1.6087(11) . ?

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
C12 P1 C18 109.52(8) . . ?
C12 P1 C6 109.36(8) . . ?
C18 P1 C6 109.97(8) . . ?
C12 P1 C1 109.34(8) . . ?
C18 P1 C1 109.97(8) . . ?
C6 P1 C1 108.65(8) . . ?
C2 C1 P1 114.12(13) . . ?
C2 C1 H1A 108.7 . . ?
P1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
P1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 112.04(15) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 176.4(2) . . ?
C3 C4 C5 179.2(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 119.66(17) . . ?
C7 C6 P1 120.90(14) . . ?
C11 C6 P1 119.42(14) . . ?
C8 C7 C6 119.87(18) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 120.39(19) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C11 119.95(19) . . ?
C9 C10 H10A 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C10 C11 C6 119.95(19) . . ?
C10 C11 H11A 120.0 . . ?
C6 C11 H11A 120.0 . . ?
C17 C12 C13 120.35(17) . . ?
C17 C12 P1 119.85(14) . . ?
C13 C12 P1 119.62(14) . . ?
C14 C13 C12 119.26(19) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 120.57(19) . . ?
C16 C15 H15A 119.7 . . ?
C14 C15 H15A 119.7 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C16 C17 C12 119.44(19) . . ?
C16 C17 H17A 120.3 . . ?
C12 C17 H17A 120.3 . . ?
C23 C18 C19 120.31(17) . . ?
C23 C18 P1 120.17(14) . . ?
C19 C18 P1 119.15(14) . . ?
C20 C19 C18 119.09(19) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 120.41(19) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22A 120.0 . . ?
C23 C22 H22A 120.0 . . ?
C22 C23 C18 119.57(19) . . ?
C22 C23 H23A 120.2 . . ?
C18 C23 H23A 120.2 . . ?
F6A P2 F5A 90.6(6) . . ?
F6A P2 F4A 175.0(6) . . ?
F5A P2 F4A 90.4(7) . . ?
F3 P2 F4 90.64(16) . . ?
F6A P2 F3A 91.7(6) . . ?
F5A P2 F3A 175.9(6) . . ?
F4A P2 F3A 87.0(6) . . ?
F3 P2 F5 178.28(11) . . ?
F4 P2 F5 90.18(13) . . ?
F3 P2 F6 90.64(15) . . ?
F4 P2 F6 178.34(12) . . ?
F5 P2 F6 88.52(12) . . ?
F6A P2 F2 84.0(4) . . ?
F5A P2 F2 85.9(4) . . ?
F3 P2 F2 91.04(9) . . ?
F4A P2 F2 91.1(5) . . ?
F4 P2 F2 89.71(8) . . ?
F3A P2 F2 91.0(4) . . ?
F5 P2 F2 90.48(8) . . ?
F6 P2 F2 91.33(8) . . ?
F6A P2 F1 96.1(4) . . ?
F5A P2 F1 94.1(4) . . ?
F3 P2 F1 89.01(8) . . ?
F4A P2 F1 88.8(5) . . ?
F4 P2 F1 90.19(8) . . ?
F3A P2 F1 89.0(4) . . ?
F5 P2 F1 89.48(8) . . ?
F6 P2 F1 88.77(8) . . ?
F2 P2 F1 179.89(9) . . ?

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
C12 P1 C1 C2 68.38(14) . . . . ?
C18 P1 C1 C2 -51.91(15) . . . . ?
C6 P1 C1 C2 -172.33(12) . . . . ?
P1 C1 C2 C3 85.93(17) . . . . ?
C12 P1 C6 C7 121.32(15) . . . . ?
C18 P1 C6 C7 -118.37(15) . . . . ?
C1 P1 C6 C7 2.04(17) . . . . ?
C12 P1 C6 C11 -57.24(16) . . . . ?
C18 P1 C6 C11 63.07(16) . . . . ?
C1 P1 C6 C11 -176.52(14) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
P1 C6 C7 C8 -179.02(15) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C6 -0.1(3) . . . . ?
C7 C6 C11 C10 0.4(3) . . . . ?
P1 C6 C11 C10 178.93(15) . . . . ?
C18 P1 C12 C17 145.49(15) . . . . ?
C6 P1 C12 C17 -93.93(16) . . . . ?
C1 P1 C12 C17 24.92(18) . . . . ?
C18 P1 C12 C13 -39.40(18) . . . . ?
C6 P1 C12 C13 81.18(17) . . . . ?
C1 P1 C12 C13 -159.96(15) . . . . ?
C17 C12 C13 C14 -0.6(3) . . . . ?
P1 C12 C13 C14 -175.71(16) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C12 -0.6(3) . . . . ?
C13 C12 C17 C16 1.1(3) . . . . ?
P1 C12 C17 C16 176.18(16) . . . . ?
C12 P1 C18 C23 -37.24(17) . . . . ?
C6 P1 C18 C23 -157.45(15) . . . . ?
C1 P1 C18 C23 82.94(17) . . . . ?
C12 P1 C18 C19 149.73(15) . . . . ?
C6 P1 C18 C19 29.53(17) . . . . ?
C1 P1 C18 C19 -90.08(16) . . . . ?
C23 C18 C19 C20 -0.7(3) . . . . ?
P1 C18 C19 C20 172.32(16) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C21 C22 C23 C18 0.4(3) . . . . ?
C19 C18 C23 C22 0.6(3) . . . . ?
P1 C18 C23 C22 -172.34(15) . . . . ?

_refine_diff_density_max         1.631
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.056



