##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
data_1
_audit_creation_method     'SHELXL-2018/3'
_journal_date_recd_electronic     2023-11-23
_journal_date_accepted     2023-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2024
_journal_volume     80
_journal_issue      1
_journal_page_first     88
_journal_page_last     93
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023010848
_journal_coeditor_code     WM5706
_publ_contact_author_name     'Peter W. R. Corfield'
_publ_contact_author_address
;
Department of Chemistry
Fordham University
441 East Fordham Road
Bronx, NY 10458
USA
;
_publ_contact_author_email     'pcorfield@fordham.edu'
_publ_contact_author_fax     '01(718)8174432'
_publ_contact_author_phone     '01(718)8174454'
_publ_section_title
;
Crystal structures of two formamidinium hexafluoridophosphate salts, one with
batch-dependent disorder
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_address
    'Neary, Michelle C. '
;
Department of Chemistry
 Hunter College
The City University of New York
New York, 10065 NY
USA
;
    'Corfield, Peter W. R.'
;
Department of Chemistry
Fordham University
441 East Fordham Road
Bronx, NY 10458
USA
;
    'Parkin, Sean R.'
;
Department of Chemistry
University of Kentucky
Lexington, KY, 40506-0055
USA
;
    'Saba, Shahrokh'
;
Department of Chemistry
Fordham University
441 East Fordham Road
Bronx, NY 10458
USA
;
_publ_section_synopsis
;
The crystal structures of two nitrogen heterocycle hexafluoridophosphate salts
with terminal animinium groups are described. Unexpectedly, there is cation
disorder in crystals of the morpholinoformamidinium compound obtained from
ethanol recrystallization, which is not found in the original crystals.
;
_chemical_name_systematic
;
Morpholinoformamidinium hexafluorophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H11 N2 O +, F6 P -'
_chemical_formula_sum     'C5 H11 F6 N2 O P'
_chemical_formula_iupac     'C5 H11 N2 O +, P F6 -'
_chemical_formula_weight     260.13
_chemical_melting_point     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P b c a'
_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, -y, -z'
    'x-1/2, y, -z-1/2'
    'x, -y-1/2, z-1/2'
    '-x-1/2, y-1/2, z'
_cell_length_a     10.4638(3)
_cell_length_b     13.4495(4)
_cell_length_c     13.7340(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1932.83(10)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9781
_cell_measurement_theta_min     4.23
_cell_measurement_theta_max     74.6
_cell_measurement_temperature     130(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.09
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.788
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1056
_exptl_absorpt_coefficient_mu     3.301
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.570
_exptl_absorpt_correction_T_max     0.754
_diffrn_ambient_temperature     130(2)
_diffrn_source     'microfocus'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type
;Bruker D8 with PHOTON III area detector
;
_diffrn_measurement_method     'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     36889
_diffrn_reflns_av_R_equivalents     0.0338
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_theta_min     6.253
_diffrn_reflns_theta_max     74.590
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     15
_refine_special_details     ?
_reflns_number_total     1969
_reflns_number_gt     1923
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0265
_refine_ls_R_factor_gt     0.0251
_refine_ls_wR_factor_gt     0.0702
_refine_ls_wR_factor_ref     0.0705
_refine_ls_goodness_of_fit_ref     1.116
_refine_ls_restrained_S_all     1.116
_refine_ls_number_reflns     1969
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0373P)²+0.5170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     ?
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.291
_refine_diff_density_min     -0.281
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015b)
;
_refine_ls_extinction_coef     0.00052(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'P' 'P' 0.2955 0.4335
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX4 (Bruker, 2022)
;
_computing_cell_refinement
;
SAINT (Bruker, 2022)
;
_computing_data_reduction
;
SAINT (Bruker, 2022)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and WinGX (Farrugia,
2012)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.17230(9) 0.55859(6) 0.73256(6) 0.01938(19) Uani d 1 . .
    C C2 0.20187(10) 0.51175(7) 0.82640(7) 0.0203(2) Uani d 1 . .
    H H2A 0.152903 0.449208 0.833665 0.030 Uiso calc 1 . .
    H H2B 0.178416 0.556828 0.880516 0.030 Uiso calc 1 . .
    C C3 0.34450(10) 0.49023(8) 0.82874(8) 0.0220(2) Uani d 1 . .
    H H3A 0.392565 0.553533 0.825341 0.033 Uiso calc 1 . .
    H H3B 0.366643 0.456964 0.890787 0.033 Uiso calc 1 . .
    O O4 0.38048(9) 0.42787(6) 0.74877(5) 0.02532(19) Uani d 1 . .
    C C5 0.34896(11) 0.47236(9) 0.65681(8) 0.0279(3) Uani d 1 . .
    H H5A 0.373554 0.426656 0.603505 0.042 Uiso calc 1 . .
    H H5B 0.398048 0.534754 0.648785 0.042 Uiso calc 1 . .
    C C6 0.20684(12) 0.49485(8) 0.64996(8) 0.0266(2) Uani d 1 . .
    H H6A 0.157068 0.432289 0.652136 0.040 Uiso calc 1 . .
    H H6B 0.187731 0.529177 0.587877 0.040 Uiso calc 1 . .
    C C7 0.14903(9) 0.65374(8) 0.71986(8) 0.0198(2) Uani d 1 . .
    H H7 0.1387(12) 0.6771(10) 0.6554(10) 0.023(3) Uiso d 1 . .
    N N8 0.13576(10) 0.71972(7) 0.78845(7) 0.0252(2) Uani d 1 . .
    H H8A 0.1442(14) 0.7058(12) 0.8468(13) 0.035(3) Uiso d 1 . .
    H H8B 0.1207(16) 0.7800(13) 0.7735(12) 0.035(3) Uiso d 1 . .
    P P1A 0.39982(2) 0.74360(2) 0.49827(2) 0.01852(12) Uani d 0.870(8) A 1
    F F1A 0.36762(8) 0.75062(5) 0.61181(5) 0.03015(19) Uani d 0.870(8) A 1
    F F2A 0.43172(8) 0.73592(6) 0.38461(5) 0.0350(2) Uani d 0.870(8) A 1
    F F3A 0.2971(3) 0.82864(17) 0.47542(12) 0.0382(4) Uani d 0.870(8) A 1
    F F4A 0.2907(2) 0.66066(17) 0.48512(12) 0.0372(4) Uani d 0.870(8) A 1
    F F5A 0.5015(2) 0.65703(19) 0.52252(9) 0.0372(5) Uani d 0.870(8) A 1
    F F6A 0.5081(2) 0.82470(19) 0.51297(13) 0.0418(5) Uani d 0.870(8) A 1
    P P1B 0.39982(2) 0.74360(2) 0.49827(2) 0.01852(12) Uani d 0.130(8) A 2
    F F1B 0.36762(8) 0.75062(5) 0.61181(5) 0.03015(19) Uani d 0.130(8) A 2
    F F2B 0.43172(8) 0.73592(6) 0.38461(5) 0.0350(2) Uani d 0.130(8) A 2
    F F3B 0.2743(11) 0.8078(9) 0.4866(8) 0.028(2) Uiso d 0.130(8) A 2
    F F4B 0.3249(11) 0.6487(8) 0.4898(7) 0.024(2) Uiso d 0.130(8) A 2
    F F5B 0.5314(7) 0.6899(8) 0.5077(6) 0.0209(18) Uiso d 0.130(8) A 2
    F F6B 0.4809(8) 0.8509(7) 0.4946(6) 0.0246(19) Uiso d 0.130(8) 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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C7 . 1.3142(13) ?
    N1 C2 . 1.4675(12) ?
    N1 C6 . 1.4672(13) ?
    C2 C3 . 1.5206(14) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 O4 . 1.4322(12) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    O4 C5 . 1.4360(13) ?
    C5 C6 . 1.5204(16) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 N8 . 1.3016(15) ?
    C7 H7 . 0.946(14) ?
    N8 H8A . 0.827(18) ?
    N8 H8B . 0.850(18) ?
    P1A F6A . 1.5856(10) ?
    P1A F3A . 1.6003(14) ?
    P1A F4A . 1.6063(14) ?
    P1A F5A . 1.6120(11) ?
    P1A F1A . 1.5982(7) ?
    P1A F2A . 1.5997(7) ?
    P1B F4B . 1.502(12) ?
    P1B F3B . 1.581(13) ?
    P1B F5B . 1.560(6) ?
    P1B F1B . 1.5982(7) ?
    P1B F2B . 1.5997(7) ?
    P1B F6B . 1.674(8) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 N1 C2 . . 125.00(9) ?
    C7 N1 C6 . . 120.79(9) ?
    C2 N1 C6 . . 112.10(8) ?
    N1 C2 C3 . . 107.89(8) ?
    N1 C2 H2A . . 110.1 ?
    C3 C2 H2A . . 110.1 ?
    N1 C2 H2B . . 110.1 ?
    C3 C2 H2B . . 110.1 ?
    H2A C2 H2B . . 108.4 ?
    O4 C3 C2 . . 110.69(8) ?
    O4 C3 H3A . . 109.5 ?
    C2 C3 H3A . . 109.5 ?
    O4 C3 H3B . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C5 O4 C3 . . 111.72(8) ?
    O4 C5 C6 . . 111.22(9) ?
    O4 C5 H5A . . 109.4 ?
    C6 C5 H5A . . 109.4 ?
    O4 C5 H5B . . 109.4 ?
    C6 C5 H5B . . 109.4 ?
    H5A C5 H5B . . 108.0 ?
    C5 C6 N1 . . 108.02(9) ?
    C5 C6 H6A . . 110.1 ?
    N1 C6 H6A . . 110.1 ?
    C5 C6 H6B . . 110.1 ?
    N1 C6 H6B . . 110.1 ?
    H6A C6 H6B . . 108.4 ?
    N1 C7 N8 . . 125.98(10) ?
    N1 C7 H7 . . 118.0(8) ?
    N8 C7 H7 . . 116.0(8) ?
    C7 N8 H8A . . 122.4(11) ?
    C7 N8 H8B . . 119.6(11) ?
    H8A N8 H8B . . 118.0(15) ?
    F6A P1A F3A . . 90.75(9) ?
    F6A P1A F4A . . 179.05(8) ?
    F3A P1A F4A . . 89.83(10) ?
    F6A P1A F5A . . 89.94(9) ?
    F3A P1A F5A . . 179.02(8) ?
    F4A P1A F5A . . 89.47(8) ?
    F6A P1A F1A . . 89.19(6) ?
    F3A P1A F1A . . 90.44(7) ?
    F4A P1A F1A . . 90.05(6) ?
    F5A P1A F1A . . 88.87(6) ?
    F6A P1A F2A . . 91.12(6) ?
    F3A P1A F2A . . 89.70(7) ?
    F4A P1A F2A . . 89.64(6) ?
    F5A P1A F2A . . 90.99(6) ?
    F1A P1A F2A . . 179.66(4) ?
    F4B P1B F3B . . 91.3(5) ?
    F4B P1B F5B . . 94.2(4) ?
    F3B P1B F5B . . 174.3(4) ?
    F4B P1B F1B . . 90.9(4) ?
    F3B P1B F1B . . 83.8(4) ?
    F5B P1B F1B . . 97.6(3) ?
    F4B P1B F2B . . 88.8(4) ?
    F3B P1B F2B . . 96.3(4) ?
    F5B P1B F2B . . 82.4(3) ?
    F1B P1B F2B . . 179.66(4) ?
    F4B P1B F6B . . 173.7(5) ?
    F3B P1B F6B . . 87.0(4) ?
    F5B P1B F6B . . 87.4(4) ?
    F1B P1B F6B . . 94.9(3) ?
    F2B P1B F6B . . 85.4(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C2 H2A F4A 2_565 0.99 2.62 3.183(2) 116.3 yes
    C2 H2A F4B 2_565 0.99 2.53 3.126(11) 118.7 yes
    C2 H2B F3A 7_576 0.99 2.37 3.1290(19) 132.9 yes
    C7 H7 F2A 4_466 0.946(14) 2.522(13) 3.0711(12) 117.1(9) yes
    N8 H8A F3A 7_576 0.827(18) 2.428(17) 3.141(2) 144.9(13) yes
    N8 H8A F5A 6_557 0.827(18) 2.425(16) 3.0699(16) 135.4(13) yes
    N8 H8A F3B 7_576 0.827(18) 2.36(2) 3.105(12) 150.1(14) yes
    N8 H8A F5B 6_557 0.827(18) 2.331(18) 3.031(6) 142.8(13) yes
    N8 H8B O4 8_665 0.850(18) 2.018(18) 2.8572(13) 168.8(16) yes
_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.
;
_shelx_estimated_absorpt_T_min     0.448
_shelx_estimated_absorpt_T_max     0.827
data_1recryst
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
Morpholinoformamidinium hexafluorophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H11 N2 O +, F6 P -'
_chemical_formula_sum     'C5 H11 F6 N2 O P'
_chemical_formula_iupac     'C5 H11 N2 O +, P F6 -'
_chemical_formula_weight     260.13
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P c a 21'
_space_group_name_Hall     'P 2c -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     10.4504(14)
_cell_length_b     13.7170(16)
_cell_length_c     13.4157(14)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     1923.1(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9865
_cell_measurement_theta_min     3.38
_cell_measurement_theta_max     33.15
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.240
_exptl_crystal_size_mid     0.230
_exptl_crystal_size_min     0.140
_exptl_crystal_density_diffrn     1.797
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1056
_exptl_absorpt_coefficient_mu     0.356
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.8559
_exptl_absorpt_correction_T_max     0.9705
_diffrn_ambient_temperature     100(2)
_diffrn_source     'microsource'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Venture dual source'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     7.41
_diffrn_reflns_number     42268
_diffrn_reflns_av_R_equivalents     0.0395
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_theta_min     1.949
_diffrn_reflns_theta_max     33.130
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     20
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     7300
_reflns_number_gt     5163
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0537
_refine_ls_R_factor_gt     0.0322
_refine_ls_wR_factor_gt     0.0769
_refine_ls_wR_factor_ref     0.0881
_refine_ls_goodness_of_fit_ref     1.016
_refine_ls_restrained_S_all     1.008
_refine_ls_number_reflns     7300
_refine_ls_number_parameters     364
_refine_ls_number_restraints     154
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0390P)²+0.2600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.016
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.275
_refine_diff_density_min     -0.404
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack     0.5
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'
    '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'
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2022)
;
_computing_data_reduction
;
SAINT (Bruker, 2022)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and WinGX (Farrugia,
2012)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1A 0.8290(2) 0.48239(16) 0.57523(16) 0.0129(4) Uani d 1 . .
    C C2A 0.8000(2) 0.57601(18) 0.6226(2) 0.0140(5) Uani d 1 . .
    H H2A1 0.824879 0.630306 0.578020 0.017 Uiso calc 1 . .
    H H2A2 0.848505 0.582406 0.685693 0.017 Uiso calc 1 . .
    C C3A 0.6569(2) 0.57971(19) 0.6434(2) 0.0151(5) Uani d 1 . .
    H H3A1 0.635556 0.641635 0.677442 0.018 Uiso calc 1 . .
    H H3A2 0.609306 0.577543 0.579648 0.018 Uiso calc 1 . .
    O O4A 0.6192(2) 0.49898(12) 0.70486(17) 0.0177(4) Uani d 1 . .
    C C5A 0.6500(2) 0.40691(18) 0.6598(2) 0.0193(5) Uani d 1 . .
    H H5A1 0.601492 0.399677 0.596823 0.023 Uiso calc 1 . .
    H H5A2 0.624178 0.353401 0.705039 0.023 Uiso calc 1 . .
    C C6A 0.7926(3) 0.39933(17) 0.63826(19) 0.0193(5) Uani d 1 . .
    H H6A1 0.841621 0.400702 0.701372 0.023 Uiso calc 1 . .
    H H6A2 0.811463 0.337321 0.603486 0.023 Uiso calc 1 . .
    C C7A 0.85190(19) 0.47015(19) 0.47963(18) 0.0129(4) Uani d 1 . .
    H H7A 0.858586 0.405015 0.456128 0.016 Uiso calc 1 . .
    N N8A 0.8664(2) 0.54034(17) 0.41380(18) 0.0172(4) Uani d 1 . .
    H H8A1 0.8612(2) 0.5984(15) 0.4316(5) 0.021 Uiso calc 1 . .
    H H8A2 0.8807(4) 0.5267(3) 0.3543(14) 0.021 Uiso calc 1 . .
    N N1B 0.3318(4) 0.0173(3) 0.5727(3) 0.0140(6) Uani d 0.639(4) A 1
    C C2B 0.2939(4) 0.1008(2) 0.6349(3) 0.0194(7) Uani d 0.639(4) A 1
    H H2B1 0.311558 0.162540 0.599144 0.023 Uiso calc 0.639(4) A 1
    H H2B2 0.343451 0.100825 0.697733 0.023 Uiso calc 0.639(4) A 1
    C C3B 0.1518(4) 0.0928(3) 0.6575(3) 0.0215(7) Uani d 0.639(4) A 1
    H H3B1 0.126171 0.146548 0.702529 0.026 Uiso calc 0.639(4) A 1
    H H3B2 0.102490 0.099394 0.594845 0.026 Uiso calc 0.639(4) A 1
    O O4B 0.1222(3) 0.0012(2) 0.7034(2) 0.0191(6) Uani d 0.639(4) A 1
    C C5B 0.1604(5) -0.0796(6) 0.6432(6) 0.0179(10) Uani d 0.639(4) A 1
    H H5B1 0.112518 -0.078428 0.579499 0.022 Uiso calc 0.639(4) A 1
    H H5B2 0.139565 -0.141230 0.678005 0.022 Uiso calc 0.639(4) A 1
    C C6B 0.3031(4) -0.0758(5) 0.6219(5) 0.0143(9) Uani d 0.639(4) A 1
    H H6B1 0.351804 -0.081037 0.684996 0.017 Uiso calc 0.639(4) A 1
    H H6B2 0.327946 -0.130785 0.578259 0.017 Uiso calc 0.639(4) A 1
    C C7B 0.3530(3) 0.0287(2) 0.4776(2) 0.0149(6) Uani d 0.639(4) A 1
    H H7B 0.359065 0.093865 0.454013 0.018 Uiso calc 0.639(4) A 1
    N N8B 0.3668(3) -0.0406(2) 0.4117(3) 0.0192(6) Uani d 0.639(4) A 1
    H H8B1 0.3622(3) -0.099(3) 0.4294(8) 0.023 Uiso calc 0.639(4) A 1
    H H8B2 0.3804(7) -0.0264(6) 0.352(3) 0.023 Uiso calc 0.639(4) A 1
    N N1B' 0.1687(8) 0.0176(6) 0.6935(6) 0.0199(15) Uani d 0.361(4) A 2
    C C2B' 0.1990(10) -0.0769(9) 0.6440(12) 0.021(2) Uani d 0.361(4) A 2
    H H2C3 0.154138 -0.081905 0.579227 0.025 Uiso calc 0.361(4) A 2
    H H2C4 0.172359 -0.132281 0.686577 0.025 Uiso calc 0.361(4) A 2
    C C3B' 0.3421(9) -0.0779(10) 0.6288(11) 0.022(2) Uani d 0.361(4) A 2
    H H3C3 0.385858 -0.070707 0.693820 0.027 Uiso calc 0.361(4) A 2
    H H3C4 0.368428 -0.140949 0.599215 0.027 Uiso calc 0.361(4) A 2
    O O4B' 0.3787(8) 0.0008(5) 0.5636(6) 0.0240(15) Uani d 0.361(4) A 2
    C C5B' 0.3445(8) 0.0923(6) 0.6060(7) 0.0241(17) Uani d 0.361(4) A 2
    H H5C3 0.367287 0.144961 0.558796 0.029 Uiso calc 0.361(4) A 2
    H H5C4 0.394545 0.102477 0.667809 0.029 Uiso calc 0.361(4) A 2
    C C6B' 0.2036(8) 0.0993(5) 0.6303(6) 0.0214(16) Uani d 0.361(4) A 2
    H H6C3 0.185643 0.161482 0.665102 0.026 Uiso calc 0.361(4) A 2
    H H6C4 0.152664 0.097779 0.568073 0.026 Uiso calc 0.361(4) A 2
    C C7B' 0.1453(6) 0.0285(6) 0.7905(5) 0.0185(14) Uani d 0.361(4) A 2
    H H7B' 0.133998 0.093460 0.813339 0.022 Uiso calc 0.361(4) A 2
    N N8B' 0.1362(7) -0.0380(5) 0.8561(6) 0.0237(14) Uani d 0.361(4) A 2
    H H8C3 0.145814 -0.099558 0.839021 0.028 Uiso calc 0.361(4) A 2
    H H8C4 0.120303 -0.022593 0.918522 0.028 Uiso calc 0.361(4) A 2
    P P1 1.10174(10) 0.25140(7) 0.38095(4) 0.0133(2) Uani d 1 . .
    F F1 1.1345(2) 0.13771(15) 0.38914(11) 0.0236(5) Uani d 1 . .
    F F2 1.0694(2) 0.36564(14) 0.37324(14) 0.0266(4) Uani d 1 . .
    F F3 1.2054(2) 0.26335(12) 0.29446(17) 0.0293(5) Uani d 1 . .
    F F4 1.2093(2) 0.27439(14) 0.46292(18) 0.0319(5) Uani d 1 . .
    F F5 0.9982(2) 0.24007(13) 0.46808(17) 0.0344(5) Uani d 1 . .
    F F6 0.9944(2) 0.22733(15) 0.29994(19) 0.0364(5) Uani d 1 . .
    P P1A 0.60169(10) 0.24864(7) 0.38572(4) 0.0148(2) Uani d 0.876(19) B 3
    F F1A 0.5698(2) 0.13505(16) 0.38354(13) 0.0355(6) Uani d 0.876(19) B 3
    F F2A 0.6341(2) 0.36245(16) 0.38891(11) 0.0230(5) Uani d 0.876(19) B 3
    F F3A 0.7033(5) 0.2329(2) 0.2977(4) 0.0302(8) Uani d 0.876(19) B 3
    F F4A 0.7122(4) 0.2274(3) 0.4658(4) 0.0308(7) Uani d 0.876(19) B 3
    F F5A 0.5008(5) 0.2645(2) 0.4755(4) 0.0295(8) Uani d 0.876(19) B 3
    F F6A 0.4912(5) 0.2708(3) 0.3067(4) 0.0333(8) Uani d 0.876(19) B 3
    P P1B 0.60169(10) 0.24864(7) 0.38572(4) 0.0148(2) Uani d 0.124(19) B 4
    F F1B 0.5698(2) 0.13505(16) 0.38354(13) 0.0355(6) Uani d 0.124(19) B 4
    F F2B 0.6341(2) 0.36245(16) 0.38891(11) 0.0230(5) Uani d 0.124(19) B 4
    F F3B 0.723(2) 0.2384(16) 0.3217(19) 0.022(4) Uiso d 0.124(19) B 4
    F F4B 0.690(2) 0.2428(18) 0.4841(18) 0.022(4) Uiso d 0.124(19) B 4
    F F5B 0.4767(16) 0.2571(11) 0.4483(16) 0.013(3) Uiso d 0.124(19) B 4
    F F6B 0.517(2) 0.2531(16) 0.2880(14) 0.018(4) Uiso d 0.124(19) B 4
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1A C7A . 1.315(3) ?
    N1A C2A . 1.465(3) ?
    N1A C6A . 1.469(3) ?
    C2A C3A . 1.522(3) ?
    C2A H2A1 . 0.9900 ?
    C2A H2A2 . 0.9900 ?
    C3A O4A . 1.436(3) ?
    C3A H3A1 . 0.9900 ?
    C3A H3A2 . 0.9900 ?
    O4A C5A . 1.437(3) ?
    C5A C6A . 1.521(3) ?
    C5A H5A1 . 0.9900 ?
    C5A H5A2 . 0.9900 ?
    C6A H6A1 . 0.9900 ?
    C6A H6A2 . 0.9900 ?
    C7A N8A . 1.315(3) ?
    C7A H7A . 0.9500 ?
    N8A H8A1 . 0.83(2) ?
    N8A H8A2 . 0.83(2) ?
    N1B C7B . 1.304(5) ?
    N1B C6B . 1.468(7) ?
    N1B C2B . 1.472(5) ?
    C2B C3B . 1.519(6) ?
    C2B H2B1 . 0.9900 ?
    C2B H2B2 . 0.9900 ?
    C3B O4B . 1.433(5) ?
    C3B H3B1 . 0.9900 ?
    C3B H3B2 . 0.9900 ?
    O4B C5B . 1.428(8) ?
    C5B C6B . 1.519(7) ?
    C5B H5B1 . 0.9900 ?
    C5B H5B2 . 0.9900 ?
    C6B H6B1 . 0.9900 ?
    C6B H6B2 . 0.9900 ?
    C7B N8B . 1.306(4) ?
    C7B H7B . 0.9500 ?
    N8B H8B1 . 0.84(4) ?
    N8B H8B2 . 0.84(4) ?
    N1B' C7B' . 1.333(10) ?
    N1B' C6B' . 1.452(10) ?
    N1B' C2B' . 1.492(14) ?
    C2B' C3B' . 1.509(12) ?
    C2B' H2C3 . 0.9900 ?
    C2B' H2C4 . 0.9900 ?
    C3B' O4B' . 1.442(13) ?
    C3B' H3C3 . 0.9900 ?
    C3B' H3C4 . 0.9900 ?
    O4B' C5B' . 1.424(10) ?
    C5B' C6B' . 1.511(10) ?
    C5B' H5C3 . 0.9900 ?
    C5B' H5C4 . 0.9900 ?
    C6B' H6C3 . 0.9900 ?
    C6B' H6C4 . 0.9900 ?
    C7B' N8B' . 1.271(10) ?
    C7B' H7B' . 0.9500 ?
    N8B' H8C3 . 0.8800 ?
    N8B' H8C4 . 0.8800 ?
    P1 F3 . 1.596(2) ?
    P1 F6 . 1.596(2) ?
    P1 F1 . 1.600(2) ?
    P1 F5 . 1.601(2) ?
    P1 F4 . 1.604(2) ?
    P1 F2 . 1.606(2) ?
    P1A F6A . 1.597(3) ?
    P1A F1A . 1.594(2) ?
    P1A F3A . 1.602(3) ?
    P1A F2A . 1.598(2) ?
    P1A F4A . 1.604(3) ?
    P1A F5A . 1.615(3) ?
    P1B F4B . 1.61(2) ?
    P1B F3B . 1.54(2) ?
    P1B F5B . 1.558(15) ?
    P1B F6B . 1.583(18) ?
    P1B F1B . 1.594(2) ?
    P1B F2B . 1.598(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7A N1A C2A . . 124.9(2) ?
    C7A N1A C6A . . 120.6(2) ?
    C2A N1A C6A . . 112.1(2) ?
    N1A C2A C3A . . 108.1(2) ?
    N1A C2A H2A1 . . 110.1 ?
    C3A C2A H2A1 . . 110.1 ?
    N1A C2A H2A2 . . 110.1 ?
    C3A C2A H2A2 . . 110.1 ?
    H2A1 C2A H2A2 . . 108.4 ?
    O4A C3A C2A . . 110.4(2) ?
    O4A C3A H3A1 . . 109.6 ?
    C2A C3A H3A1 . . 109.6 ?
    O4A C3A H3A2 . . 109.6 ?
    C2A C3A H3A2 . . 109.6 ?
    H3A1 C3A H3A2 . . 108.1 ?
    C3A O4A C5A . . 112.0(2) ?
    O4A C5A C6A . . 111.1(2) ?
    O4A C5A H5A1 . . 109.4 ?
    C6A C5A H5A1 . . 109.4 ?
    O4A C5A H5A2 . . 109.4 ?
    C6A C5A H5A2 . . 109.4 ?
    H5A1 C5A H5A2 . . 108.0 ?
    N1A C6A C5A . . 108.1(2) ?
    N1A C6A H6A1 . . 110.1 ?
    C5A C6A H6A1 . . 110.1 ?
    N1A C6A H6A2 . . 110.1 ?
    C5A C6A H6A2 . . 110.1 ?
    H6A1 C6A H6A2 . . 108.4 ?
    N8A C7A N1A . . 125.6(2) ?
    N8A C7A H7A . . 117.2 ?
    N1A C7A H7A . . 117.2 ?
    C7A N8A H8A1 . . 120.0 ?
    C7A N8A H8A2 . . 120.0 ?
    H8A1 N8A H8A2 . . 120.0 ?
    C7B N1B C6B . . 125.4(4) ?
    C7B N1B C2B . . 120.4(3) ?
    C6B N1B C2B . . 111.5(4) ?
    N1B C2B C3B . . 108.7(3) ?
    N1B C2B H2B1 . . 110.0 ?
    C3B C2B H2B1 . . 110.0 ?
    N1B C2B H2B2 . . 110.0 ?
    C3B C2B H2B2 . . 110.0 ?
    H2B1 C2B H2B2 . . 108.3 ?
    O4B C3B C2B . . 111.1(3) ?
    O4B C3B H3B1 . . 109.4 ?
    C2B C3B H3B1 . . 109.4 ?
    O4B C3B H3B2 . . 109.4 ?
    C2B C3B H3B2 . . 109.4 ?
    H3B1 C3B H3B2 . . 108.0 ?
    C5B O4B C3B . . 112.2(4) ?
    O4B C5B C6B . . 110.7(5) ?
    O4B C5B H5B1 . . 109.5 ?
    C6B C5B H5B1 . . 109.5 ?
    O4B C5B H5B2 . . 109.5 ?
    C6B C5B H5B2 . . 109.5 ?
    H5B1 C5B H5B2 . . 108.1 ?
    N1B C6B C5B . . 108.4(4) ?
    N1B C6B H6B1 . . 110.0 ?
    C5B C6B H6B1 . . 110.0 ?
    N1B C6B H6B2 . . 110.0 ?
    C5B C6B H6B2 . . 110.0 ?
    H6B1 C6B H6B2 . . 108.4 ?
    N1B C7B N8B . . 126.4(3) ?
    N1B C7B H7B . . 116.8 ?
    N8B C7B H7B . . 116.8 ?
    C7B N8B H8B1 . . 120.0 ?
    C7B N8B H8B2 . . 120.0 ?
    H8B1 N8B H8B2 . . 120.0 ?
    C7B' N1B' C6B' . . 122.1(8) ?
    C7B' N1B' C2B' . . 124.8(10) ?
    C6B' N1B' C2B' . . 111.0(8) ?
    N1B' C2B' C3B' . . 106.2(9) ?
    N1B' C2B' H2C3 . . 110.5 ?
    C3B' C2B' H2C3 . . 110.5 ?
    N1B' C2B' H2C4 . . 110.5 ?
    C3B' C2B' H2C4 . . 110.5 ?
    H2C3 C2B' H2C4 . . 108.7 ?
    O4B' C3B' C2B' . . 109.8(9) ?
    O4B' C3B' H3C3 . . 109.7 ?
    C2B' C3B' H3C3 . . 109.7 ?
    O4B' C3B' H3C4 . . 109.7 ?
    C2B' C3B' H3C4 . . 109.7 ?
    H3C3 C3B' H3C4 . . 108.2 ?
    C5B' O4B' C3B' . . 110.5(9) ?
    O4B' C5B' C6B' . . 112.8(7) ?
    O4B' C5B' H5C3 . . 109.0 ?
    C6B' C5B' H5C3 . . 109.0 ?
    O4B' C5B' H5C4 . . 109.0 ?
    C6B' C5B' H5C4 . . 109.0 ?
    H5C3 C5B' H5C4 . . 107.8 ?
    N1B' C6B' C5B' . . 108.7(7) ?
    N1B' C6B' H6C3 . . 109.9 ?
    C5B' C6B' H6C3 . . 109.9 ?
    N1B' C6B' H6C4 . . 109.9 ?
    C5B' C6B' H6C4 . . 109.9 ?
    H6C3 C6B' H6C4 . . 108.3 ?
    N8B' C7B' N1B' . . 127.6(8) ?
    N8B' C7B' H7B' . . 116.2 ?
    N1B' C7B' H7B' . . 116.2 ?
    C7B' N8B' H8C3 . . 120.0 ?
    C7B' N8B' H8C4 . . 120.0 ?
    H8C3 N8B' H8C4 . . 120.0 ?
    F3 P1 F6 . . 90.19(14) ?
    F3 P1 F1 . . 90.29(10) ?
    F6 P1 F1 . . 89.73(11) ?
    F3 P1 F5 . . 179.60(14) ?
    F6 P1 F5 . . 90.11(17) ?
    F1 P1 F5 . . 89.99(11) ?
    F3 P1 F4 . . 90.14(15) ?
    F6 P1 F4 . . 179.35(13) ?
    F1 P1 F4 . . 89.70(11) ?
    F5 P1 F4 . . 89.57(13) ?
    F3 P1 F2 . . 89.75(10) ?
    F6 P1 F2 . . 90.58(12) ?
    F1 P1 F2 . . 179.68(14) ?
    F5 P1 F2 . . 89.97(10) ?
    F4 P1 F2 . . 89.99(12) ?
    F6A P1A F1A . . 91.31(16) ?
    F6A P1A F3A . . 90.92(18) ?
    F1A P1A F3A . . 89.64(15) ?
    F6A P1A F2A . . 89.14(15) ?
    F1A P1A F2A . . 179.49(12) ?
    F3A P1A F2A . . 90.60(15) ?
    F6A P1A F4A . . 179.36(17) ?
    F1A P1A F4A . . 89.15(16) ?
    F3A P1A F4A . . 89.5(2) ?
    F2A P1A F4A . . 90.40(16) ?
    F6A P1A F5A . . 89.85(18) ?
    F1A P1A F5A . . 90.47(15) ?
    F3A P1A F5A . . 179.22(18) ?
    F2A P1A F5A . . 89.28(15) ?
    F4A P1A F5A . . 89.69(16) ?
    F4B P1B F3B . . 88.9(10) ?
    F4B P1B F5B . . 92.3(9) ?
    F3B P1B F5B . . 178.4(8) ?
    F4B P1B F6B . . 178.9(9) ?
    F3B P1B F6B . . 90.2(9) ?
    F5B P1B F6B . . 88.6(7) ?
    F4B P1B F1B . . 94.9(9) ?
    F3B P1B F1B . . 94.2(8) ?
    F5B P1B F1B . . 84.7(6) ?
    F6B P1B F1B . . 84.6(7) ?
    F4B P1B F2B . . 84.6(8) ?
    F3B P1B F2B . . 85.9(8) ?
    F5B P1B F2B . . 95.2(6) ?
    F6B P1B F2B . . 95.9(7) ?
    F1B P1B F2B . . 179.49(12) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7A N1A C2A C3A . . . . 103.6(3) ?
    C6A N1A C2A C3A . . . . -59.2(3) ?
    N1A C2A C3A O4A . . . . 57.4(3) ?
    C2A C3A O4A C5A . . . . -58.2(3) ?
    C3A O4A C5A C6A . . . . 57.9(3) ?
    C7A N1A C6A C5A . . . . -105.2(3) ?
    C2A N1A C6A C5A . . . . 58.4(3) ?
    O4A C5A C6A N1A . . . . -56.3(3) ?
    C2A N1A C7A N8A . . . . 7.9(4) ?
    C6A N1A C7A N8A . . . . 169.3(2) ?
    C7B N1B C2B C3B . . . . 104.8(4) ?
    C6B N1B C2B C3B . . . . -57.8(4) ?
    N1B C2B C3B O4B . . . . 55.8(4) ?
    C2B C3B O4B C5B . . . . -57.4(5) ?
    C3B O4B C5B C6B . . . . 58.3(7) ?
    C7B N1B C6B C5B . . . . -102.8(6) ?
    C2B N1B C6B C5B . . . . 58.6(6) ?
    O4B C5B C6B N1B . . . . -57.7(7) ?
    C6B N1B C7B N8B . . . . -8.3(6) ?
    C2B N1B C7B N8B . . . . -168.2(3) ?
    C7B' N1B' C2B' C3B' . . . . -101.5(12) ?
    C6B' N1B' C2B' C3B' . . . . 62.1(13) ?
    N1B' C2B' C3B' O4B' . . . . -62.4(14) ?
    C2B' C3B' O4B' C5B' . . . . 60.8(13) ?
    C3B' O4B' C5B' C6B' . . . . -56.5(10) ?
    C7B' N1B' C6B' C5B' . . . . 106.4(9) ?
    C2B' N1B' C6B' C5B' . . . . -57.7(10) ?
    O4B' C5B' C6B' N1B' . . . . 54.5(10) ?
    C6B' N1B' C7B' N8B' . . . . -166.6(8) ?
    C2B' N1B' C7B' N8B' . . . . -4.9(14) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C2A H2A1 F4 3_465 0.99 2.36 3.115(3) 132.8 yes
    C2A H2A2 F3 2_765 0.99 2.63 3.189(3) 115.8 yes
    C6A H6A2 F4B . 0.99 2.42 3.17(2) 131.8 yes
    C7A H7A F2 . 0.95 2.53 3.043(3) 114.3 yes
    N8A H8A1 F4 3_465 0.83 2.40 3.096(3) 142.2 yes
    N8A H8A1 F5A 3_565 0.83 2.45 3.135(4) 139.7 yes
    N8A H8A1 F5B 3_565 0.83 2.33 3.043(15) 143.7 yes
    N8A H8A2 O4A 4_654 0.83 2.04 2.864(3) 169.4 yes
    N8B H8B1 F5 3_455 0.84 2.45 3.153(4) 141.3 yes
    N8B H8B2 O4B 4_554 0.84 2.02 2.855(5) 169.2 yes
    N8B' H8C3 F6 2_655 0.88 2.34 3.028(8) 134.7 yes
    N8B' H8C4 O4B' 4 0.88 1.97 2.839(12) 167.8 yes
_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.
;
_shelx_estimated_absorpt_T_min     0.919
_shelx_estimated_absorpt_T_max     0.952
data_2
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
Pyrrolidinoformamidinium hexafluorophosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C5 H11 N2 +, F6 P -'
_chemical_formula_sum     'C5 H11 F6 N2 P'
_chemical_formula_iupac     'C5 H11 N2 +, P F6 -'
_chemical_formula_weight     244.13
_chemical_melting_point     ?
_chemical_absolute_configuration     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'C c'
_space_group_name_Hall     'C -2yc'
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     12.3588(3)
_cell_length_b     12.7942(3)
_cell_length_c     12.2759(3)
_cell_angle_alpha     90
_cell_angle_beta     105.4000(10)
_cell_angle_gamma     90
_cell_volume     1871.38(8)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9886
_cell_measurement_theta_min     3.73
_cell_measurement_theta_max     74.50
_cell_measurement_temperature     130(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.21
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.11
_exptl_crystal_density_diffrn     1.733
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     992
_exptl_absorpt_coefficient_mu     3.279
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_absorpt_correction_T_min     0.639
_exptl_absorpt_correction_T_max     0.754
_diffrn_ambient_temperature     130(2)
_diffrn_source     'microfocus'
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type
;Bruker D8 with PHOTON III area detector
;
_diffrn_measurement_method     'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     17935
_diffrn_reflns_av_R_equivalents     0.0345
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_theta_min     5.072
_diffrn_reflns_theta_max     74.581
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     3467
_reflns_number_gt     3450
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0492
_refine_ls_R_factor_gt     0.0488
_refine_ls_wR_factor_gt     0.1343
_refine_ls_wR_factor_ref     0.1345
_refine_ls_goodness_of_fit_ref     1.074
_refine_ls_restrained_S_all     1.074
_refine_ls_number_reflns     3467
_refine_ls_number_parameters     257
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0850P)²+2.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.004
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.366
_refine_diff_density_min     -0.346
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2015b)
;
_refine_ls_extinction_coef     0.0014(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack     0.49(4)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'P' 'P' 0.2955 0.4335
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX4 (Bruker, 2022)
;
_computing_cell_refinement
;
SAINT (Bruker, 2022)
;
_computing_data_reduction
;
SAINT (Bruker, 2022)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008) and WinGX (Farrugia,
2012)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.3206(4) 0.7280(3) 0.7550(3) 0.0306(9) Uani d 1 . .
    C C2 0.3205(5) 0.8419(4) 0.7666(5) 0.0359(11) Uani d 1 . .
    H H2A 0.291759 0.876189 0.692152 0.054 Uiso calc 1 . .
    H H2B 0.396755 0.868571 0.802754 0.054 Uiso calc 1 . .
    C C3 0.2414(5) 0.8601(4) 0.8420(4) 0.0397(11) Uani d 1 . .
    H H3A 0.283785 0.863514 0.922572 0.059 Uiso calc 1 . .
    H H3B 0.198412 0.925707 0.821178 0.059 Uiso calc 1 . .
    C C4 0.1646(4) 0.7661(4) 0.8193(4) 0.0358(9) Uani d 1 . .
    H H4A 0.105798 0.773984 0.747162 0.054 Uiso calc 1 . .
    H H4B 0.128245 0.755416 0.881246 0.054 Uiso calc 1 . .
    C C5 0.2435(4) 0.6762(4) 0.8132(4) 0.0337(10) Uani d 1 . .
    H H5A 0.284091 0.651192 0.889404 0.050 Uiso calc 1 . .
    H H5B 0.202882 0.617023 0.768457 0.050 Uiso calc 1 . .
    C C6 0.3770(4) 0.6777(4) 0.6965(4) 0.0347(10) Uani d 1 . .
    H H6 0.370295 0.603790 0.691284 0.042 Uiso calc 1 . .
    N N7 0.4439(4) 0.7258(3) 0.6435(4) 0.0409(10) Uani d 1 . .
    H H7A 0.4509(6) 0.792(4) 0.6473(4) 0.049 Uiso calc 1 . .
    H H7B 0.480(2) 0.690(2) 0.606(2) 0.049 Uiso calc 1 . .
    N N11 0.7698(3) 0.2303(3) 0.3159(3) 0.0252(7) Uani d 1 . .
    C C12 0.7633(4) 0.3449(4) 0.2985(4) 0.0321(10) Uani d 1 . .
    H H12A 0.793006 0.382648 0.370603 0.048 Uiso calc 1 . .
    H H12B 0.684995 0.367475 0.264147 0.048 Uiso calc 1 . .
    C C13 0.8362(4) 0.3633(4) 0.2184(4) 0.0374(11) Uani d 1 . .
    H H13A 0.805789 0.420775 0.165124 0.056 Uiso calc 1 . .
    H H13B 0.914031 0.380689 0.260727 0.056 Uiso calc 1 . .
    C C14 0.8322(4) 0.2588(4) 0.1552(4) 0.0349(9) Uani d 1 . .
    H H14A 0.761520 0.251673 0.094543 0.052 Uiso calc 1 . .
    H H14B 0.896670 0.251823 0.122180 0.052 Uiso calc 1 . .
    C C15 0.8383(4) 0.1797(4) 0.2476(4) 0.0340(10) Uani d 1 . .
    H H15A 0.805607 0.111878 0.216390 0.051 Uiso calc 1 . .
    H H15B 0.916660 0.168610 0.292739 0.051 Uiso calc 1 . .
    C C16 0.7173(4) 0.1803(4) 0.3774(4) 0.0314(10) Uani d 1 . .
    H H16 0.722967 0.106294 0.380722 0.038 Uiso calc 1 . .
    N N17 0.6562(4) 0.2270(3) 0.4358(4) 0.0385(9) Uani d 1 . .
    H H17A 0.6505(5) 0.289(4) 0.4342(4) 0.046 Uiso calc 1 . .
    H H17B 0.6253(18) 0.194(2) 0.473(2) 0.046 Uiso calc 1 . .
    P P1 0.52748(8) 0.48090(9) 0.50675(8) 0.0281(3) Uani d 1 . .
    F F1 0.5597(3) 0.6020(2) 0.5039(3) 0.0491(8) Uani d 1 . .
    F F2 0.4952(3) 0.3602(2) 0.5089(3) 0.0473(8) Uani d 1 . .
    F F3 0.5479(6) 0.4896(4) 0.6384(4) 0.0758(15) Uani d 1 . .
    F F4 0.6561(3) 0.4490(3) 0.5209(4) 0.0666(11) Uani d 1 . .
    F F5 0.5090(5) 0.4728(3) 0.3746(4) 0.0730(14) Uani d 1 . .
    F F6 0.4008(3) 0.5132(3) 0.4886(5) 0.0678(13) Uani d 1 . .
    P P2 0.55335(8) 0.97931(9) 0.55060(8) 0.0294(3) Uani d 1 . .
    F F1A 0.5774(4) 0.9564(4) 0.6830(3) 0.0566(9) Uani d 1 . .
    F F2A 0.5294(5) 1.0049(3) 0.4195(3) 0.0607(11) Uani d 1 . .
    F F3A 0.4242(3) 0.9567(3) 0.5382(3) 0.0530(9) Uani d 1 . .
    F F4A 0.5735(4) 0.8594(3) 0.5287(4) 0.0611(11) Uani d 1 . .
    F F5A 0.6830(3) 1.0047(3) 0.5650(4) 0.0552(10) Uani d 1 . .
    F F6A 0.5350(3) 1.1002(2) 0.5742(3) 0.0440(7) Uani d 1 . .
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C6 . 1.296(7) ?
    N1 C5 . 1.490(7) ?
    N1 C2 . 1.465(5) ?
    C2 C3 . 1.531(7) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.512(7) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.523(6) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 N7 . 1.331(7) ?
    C6 H6 . 0.9500 ?
    N7 H7A . 0.86(5) ?
    N7 H7B . 0.86(5) ?
    N11 C16 . 1.289(6) ?
    N11 C12 . 1.481(5) ?
    N11 C15 . 1.489(6) ?
    C12 C13 . 1.517(7) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.540(7) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.506(7) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 N17 . 1.315(6) ?
    C16 H16 . 0.9500 ?
    N17 H17A . 0.79(5) ?
    N17 H17B . 0.79(5) ?
    P1 F5 . 1.580(4) ?
    P1 F3 . 1.572(4) ?
    P1 F6 . 1.576(4) ?
    P1 F2 . 1.597(3) ?
    P1 F4 . 1.606(4) ?
    P1 F1 . 1.602(3) ?
    P2 F3A . 1.589(3) ?
    P2 F2A . 1.591(4) ?
    P2 F5A . 1.598(4) ?
    P2 F1A . 1.600(3) ?
    P2 F4A . 1.588(3) ?
    P2 F6A . 1.601(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 N1 C5 . . 123.5(4) ?
    C6 N1 C2 . . 124.2(5) ?
    C5 N1 C2 . . 112.2(4) ?
    N1 C2 C3 . . 103.1(4) ?
    N1 C2 H2A . . 111.1 ?
    C3 C2 H2A . . 111.1 ?
    N1 C2 H2B . . 111.1 ?
    C3 C2 H2B . . 111.1 ?
    H2A C2 H2B . . 109.1 ?
    C4 C3 C2 . . 103.8(4) ?
    C4 C3 H3A . . 111.0 ?
    C2 C3 H3A . . 111.0 ?
    C4 C3 H3B . . 111.0 ?
    C2 C3 H3B . . 111.0 ?
    H3A C3 H3B . . 109.0 ?
    C3 C4 C5 . . 103.3(4) ?
    C3 C4 H4A . . 111.1 ?
    C5 C4 H4A . . 111.1 ?
    C3 C4 H4B . . 111.1 ?
    C5 C4 H4B . . 111.1 ?
    H4A C4 H4B . . 109.1 ?
    N1 C5 C4 . . 100.8(4) ?
    N1 C5 H5A . . 111.6 ?
    C4 C5 H5A . . 111.6 ?
    N1 C5 H5B . . 111.6 ?
    C4 C5 H5B . . 111.6 ?
    H5A C5 H5B . . 109.4 ?
    N1 C6 N7 . . 122.4(5) ?
    N1 C6 H6 . . 118.8 ?
    N7 C6 H6 . . 118.8 ?
    C6 N7 H7A . . 120.0 ?
    C6 N7 H7B . . 120.0 ?
    H7A N7 H7B . . 120.0 ?
    C16 N11 C12 . . 124.0(4) ?
    C16 N11 C15 . . 124.4(4) ?
    C12 N11 C15 . . 111.5(4) ?
    N11 C12 C13 . . 103.2(4) ?
    N11 C12 H12A . . 111.1 ?
    C13 C12 H12A . . 111.1 ?
    N11 C12 H12B . . 111.1 ?
    C13 C12 H12B . . 111.1 ?
    H12A C12 H12B . . 109.1 ?
    C14 C13 C12 . . 104.3(4) ?
    C14 C13 H13A . . 110.9 ?
    C12 C13 H13A . . 110.9 ?
    C14 C13 H13B . . 110.9 ?
    C12 C13 H13B . . 110.9 ?
    H13A C13 H13B . . 108.9 ?
    C15 C14 C13 . . 102.5(4) ?
    C15 C14 H14A . . 111.3 ?
    C13 C14 H14A . . 111.3 ?
    C15 C14 H14B . . 111.3 ?
    C13 C14 H14B . . 111.3 ?
    H14A C14 H14B . . 109.2 ?
    N11 C15 C14 . . 102.1(4) ?
    N11 C15 H15A . . 111.4 ?
    C14 C15 H15A . . 111.4 ?
    N11 C15 H15B . . 111.4 ?
    C14 C15 H15B . . 111.4 ?
    H15A C15 H15B . . 109.2 ?
    N11 C16 N17 . . 123.1(5) ?
    N11 C16 H16 . . 118.5 ?
    N17 C16 H16 . . 118.5 ?
    C16 N17 H17A . . 120.0 ?
    C16 N17 H17B . . 120.0 ?
    H17A N17 H17B . . 120.0 ?
    F5 P1 F3 . . 179.1(4) ?
    F5 P1 F6 . . 90.3(3) ?
    F3 P1 F6 . . 90.5(3) ?
    F5 P1 F2 . . 89.2(2) ?
    F3 P1 F2 . . 91.4(2) ?
    F6 P1 F2 . . 90.73(19) ?
    F5 P1 F4 . . 87.9(3) ?
    F3 P1 F4 . . 91.3(3) ?
    F6 P1 F4 . . 178.1(3) ?
    F2 P1 F4 . . 89.8(2) ?
    F5 P1 F1 . . 90.5(2) ?
    F3 P1 F1 . . 88.9(2) ?
    F6 P1 F1 . . 89.2(2) ?
    F2 P1 F1 . . 179.7(2) ?
    F4 P1 F1 . . 90.2(2) ?
    F3A P2 F2A . . 91.6(3) ?
    F3A P2 F5A . . 178.5(2) ?
    F2A P2 F5A . . 88.9(3) ?
    F3A P2 F1A . . 88.5(2) ?
    F2A P2 F1A . . 178.7(3) ?
    F5A P2 F1A . . 90.8(2) ?
    F3A P2 F4A . . 90.4(2) ?
    F2A P2 F4A . . 91.3(2) ?
    F5A P2 F4A . . 91.0(2) ?
    F1A P2 F4A . . 90.0(2) ?
    F3A P2 F6A . . 90.4(2) ?
    F2A P2 F6A . . 89.3(2) ?
    F5A P2 F6A . . 88.3(2) ?
    F1A P2 F6A . . 89.4(2) ?
    F4A P2 F6A . . 179.1(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N7 H7B F1 . 0.86 2.11 2.966(5) 176.5 yes
    N7 H7A F3A . 0.86 2.47 3.207(6) 145.2 yes
    N7 H7A F4A . 0.86 2.51 2.945(6) 112.0 yes
    C16 H16 F6 3_545 0.95 2.54 3.153(6) 122.2 yes
    N17 H17A F2 . 0.79 2.51 2.935(5) 115.3 yes
    N17 H17A F4 . 0.79 2.30 3.026(6) 152.2 yes
    N17 H17B F6A 1_545 0.79 2.23 3.019(5) 179.0 yes
_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.
;
_shelx_estimated_absorpt_T_min     0.546
_shelx_estimated_absorpt_T_max     0.714
