# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2026

####################################################################### 
# 
# 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_test_a
_database_code_depnum_ccdc_archive 'CCDC 2520839'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 F18 P, C6 H11 N2'
_chemical_formula_sum            'C12 H11 F18 N2 P'
_chemical_formula_weight         556.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'

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

_cell_length_a                   16.9560(2)
_cell_length_b                   8.65060(10)
_cell_length_c                   14.9967(2)
_cell_angle_alpha                90
_cell_angle_beta                 119.598(2)
_cell_angle_gamma                90
_cell_volume                     1912.67(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.99(10)
_cell_measurement_reflns_used    13970
_cell_measurement_theta_min      3.2570
_cell_measurement_theta_max      77.1500

_exptl_crystal_description       capillary
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.987
_exptl_absorpt_correction_T_min  0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.348
_oxdiff_exptl_absorpt_empirical_full_max 6.939
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      99.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            13266
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.931
_diffrn_reflns_theta_max         77.469
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.878
_reflns_number_total             3432
_reflns_number_gt                3413
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_max     0.698
_reflns_Friedel_fraction_full    0.756

_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       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.1156P)²+0.6077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3432
_refine_ls_number_parameters     300
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1_1 P 0.46341(6) 0.80256(11) 0.57863(7) 0.0200(2) Uani 1 1 d . . . . .
F2_1 F 0.37275(17) 0.7269(3) 0.5712(2) 0.0294(5) Uani 1 1 d . . . . .
F3_1 F 0.45623(16) 0.6816(3) 0.49174(19) 0.0224(5) Uani 1 1 d . . . . .
F1_1 F 0.47543(18) 0.9259(3) 0.6664(2) 0.0281(5) Uani 1 1 d . . . . .
C1_2 C 0.3807(3) 0.9483(5) 0.4769(4) 0.0269(8) Uani 1 1 d . . . . .
F1_2 F 0.4218(2) 1.0828(3) 0.4739(2) 0.0351(6) Uani 1 1 d . . . . .
C2_2 C 0.3243(3) 0.8960(6) 0.3636(4) 0.0310(9) Uani 1 1 d . . . . .
F2_2 F 0.3177(2) 0.9915(4) 0.5030(3) 0.0390(7) Uani 1 1 d . . . . .
F3_2 F 0.2678(2) 1.0077(4) 0.3080(3) 0.0414(7) Uani 1 1 d . . . . .
F4_2 F 0.2757(2) 0.7704(4) 0.3550(2) 0.0368(6) Uani 1 1 d . . . . .
F5_2 F 0.37638(19) 0.8644(4) 0.3228(2) 0.0346(6) Uani 1 1 d . . . . .
C1_3 C 0.5723(3) 0.8792(4) 0.5787(3) 0.0210(7) Uani 1 1 d . . . . .
F1_3 F 0.54985(17) 0.9228(3) 0.48098(19) 0.0265(5) Uani 1 1 d . . . . .
C2_3 C 0.6297(3) 1.0160(5) 0.6483(4) 0.0285(9) Uani 1 1 d . . . . .
F2_3 F 0.63235(16) 0.7614(3) 0.6012(2) 0.0242(5) Uani 1 1 d . . . . .
F3_3 F 0.6674(2) 0.9803(3) 0.7473(2) 0.0382(7) Uani 1 1 d . . . . .
F4_3 F 0.6964(2) 1.0476(3) 0.6287(2) 0.0384(7) Uani 1 1 d . . . . .
F5_3 F 0.5807(2) 1.1425(3) 0.6312(3) 0.0386(7) Uani 1 1 d . . . . .
C1_4 C 0.5291(3) 0.6552(5) 0.6889(3) 0.0216(7) Uani 1 1 d . . . . .
F1_4 F 0.61549(17) 0.7018(3) 0.75603(19) 0.0254(5) Uani 1 1 d . . . . .
C2_4 C 0.5366(3) 0.4852(5) 0.6625(4) 0.0254(8) Uani 1 1 d . . . . .
F2_4 F 0.48720(19) 0.6470(3) 0.7471(2) 0.0314(6) Uani 1 1 d . . . . .
F3_4 F 0.58627(18) 0.4705(3) 0.6171(2) 0.0275(5) Uani 1 1 d . . . . .
F4_4 F 0.5757(2) 0.4015(3) 0.7483(2) 0.0324(6) Uani 1 1 d . . . . .
F5_4 F 0.4550(2) 0.4243(3) 0.6014(2) 0.0336(6) Uani 1 1 d . . . . .
N1_5 N 0.6547(3) 0.5037(5) 0.4497(3) 0.0300(8) Uani 1 1 d . . . . .
C1_5 C 0.5673(3) 0.5444(5) 0.3988(3) 0.0256(8) Uani 1 1 d . . . . .
H1_5 H 0.545046 0.646418 0.378231 0.031 Uiso 1 1 calc R U . . .
N2_5 N 0.5172(3) 0.4200(4) 0.3818(3) 0.0230(7) Uani 1 1 d . . . . .
C3_5 C 0.5750(4) 0.2941(5) 0.4239(4) 0.0312(9) Uani 1 1 d . . . . .
H3_5 H 0.557418 0.189510 0.422491 0.037 Uiso 1 1 calc R U . . .
C4_5 C 0.7324(4) 0.6093(8) 0.4831(5) 0.0465(14) Uani 1 1 d . . . . .
H4A_5 H 0.764291 0.586107 0.445104 0.070 Uiso 1 1 calc R U . . .
H4B_5 H 0.774005 0.595763 0.556667 0.070 Uiso 1 1 calc R U . . .
H4C_5 H 0.710663 0.716341 0.469602 0.070 Uiso 1 1 calc R U . . .
C5_5 C 0.4179(3) 0.4140(5) 0.3300(4) 0.0289(9) Uani 1 1 d . . . . .
H5A_5 H 0.392975 0.517520 0.302298 0.035 Uiso 1 1 calc R U . . .
H5AB_5 H 0.398607 0.386082 0.380424 0.035 Uiso 1 1 calc R U . . .
C6_5 C 0.3799(4) 0.2976(6) 0.2437(4) 0.0342(10) Uani 1 1 d . . . . .
H6A_5 H 0.313737 0.293505 0.212730 0.051 Uiso 1 1 calc R U . . .
H6B_5 H 0.405491 0.195339 0.270622 0.051 Uiso 1 1 calc R U . . .
H6C_5 H 0.395778 0.328295 0.191615 0.051 Uiso 1 1 calc R U . . .
C2_5 C 0.6598(4) 0.3474(7) 0.4666(4) 0.0358(10) Uani 1 1 d . . . . .
H2_5 H 0.713751 0.288062 0.502061 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1_1 F2_1 1.623(3) . ?
P1_1 F3_1 1.628(3) . ?
P1_1 F1_1 1.627(3) . ?
P1_1 C1_2 1.942(4) . ?
P1_1 C1_4 1.944(4) . ?
P1_1 C1_3 1.961(4) . ?
C1_2 F2_2 1.360(5) . ?
C1_2 F1_2 1.368(5) . ?
C1_2 C2_2 1.549(7) . ?
C2_2 F3_2 1.325(6) . ?
C2_2 F5_2 1.327(6) . ?
C2_2 F4_2 1.330(6) . ?
C1_3 F2_3 1.360(5) . ?
C1_3 F1_3 1.372(5) . ?
C1_3 C2_3 1.561(6) . ?
C2_3 F5_3 1.320(6) . ?
C2_3 F4_3 1.329(6) . ?
C2_3 F3_3 1.331(6) . ?
C1_4 F1_4 1.366(5) . ?
C1_4 F2_4 1.373(5) . ?
C1_4 C2_4 1.544(6) . ?
C2_4 F3_4 1.325(5) . ?
C2_4 F4_4 1.334(5) . ?
C2_4 F5_4 1.334(5) . ?
N1_5 C1_5 1.335(6) . ?
N1_5 C2_5 1.370(8) . ?
N1_5 C4_5 1.474(7) . ?
C1_5 N2_5 1.315(6) . ?
C1_5 H1_5 0.9500 . ?
N2_5 C3_5 1.391(6) . ?
N2_5 C5_5 1.467(6) . ?
C3_5 C2_5 1.334(8) . ?
C3_5 H3_5 0.9500 . ?
C4_5 H4A_5 0.9800 . ?
C4_5 H4B_5 0.9800 . ?
C4_5 H4C_5 0.9800 . ?
C5_5 C6_5 1.511(7) . ?
C5_5 H5A_5 0.9900 . ?
C5_5 H5AB_5 0.9900 . ?
C6_5 H6A_5 0.9800 . ?
C6_5 H6B_5 0.9800 . ?
C6_5 H6C_5 0.9800 . ?
C2_5 H2_5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2_1 P1_1 F3_1 89.54(14) . . ?
F2_1 P1_1 F1_1 93.21(15) . . ?
F3_1 P1_1 F1_1 177.21(14) . . ?
F2_1 P1_1 C1_2 85.22(17) . . ?
F3_1 P1_1 C1_2 92.78(17) . . ?
F1_1 P1_1 C1_2 87.92(17) . . ?
F2_1 P1_1 C1_4 85.35(16) . . ?
F3_1 P1_1 C1_4 92.54(15) . . ?
F1_1 P1_1 C1_4 87.22(16) . . ?
C1_2 P1_1 C1_4 169.13(19) . . ?
F2_1 P1_1 C1_3 174.69(17) . . ?
F3_1 P1_1 C1_3 85.17(15) . . ?
F1_1 P1_1 C1_3 92.08(16) . . ?
C1_2 P1_1 C1_3 95.43(19) . . ?
C1_4 P1_1 C1_3 94.46(18) . . ?
F2_2 C1_2 F1_2 105.1(4) . . ?
F2_2 C1_2 C2_2 104.4(4) . . ?
F1_2 C1_2 C2_2 105.2(4) . . ?
F2_2 C1_2 P1_1 108.5(3) . . ?
F1_2 C1_2 P1_1 113.4(3) . . ?
C2_2 C1_2 P1_1 119.2(3) . . ?
F3_2 C2_2 F5_2 107.4(4) . . ?
F3_2 C2_2 F4_2 108.3(4) . . ?
F5_2 C2_2 F4_2 107.9(4) . . ?
F3_2 C2_2 C1_2 109.9(4) . . ?
F5_2 C2_2 C1_2 112.0(4) . . ?
F4_2 C2_2 C1_2 111.3(4) . . ?
F2_3 C1_3 F1_3 104.4(3) . . ?
F2_3 C1_3 C2_3 105.0(3) . . ?
F1_3 C1_3 C2_3 104.9(3) . . ?
F2_3 C1_3 P1_1 109.7(2) . . ?
F1_3 C1_3 P1_1 109.2(3) . . ?
C2_3 C1_3 P1_1 122.2(3) . . ?
F5_3 C2_3 F4_3 108.0(4) . . ?
F5_3 C2_3 F3_3 108.6(4) . . ?
F4_3 C2_3 F3_3 107.6(4) . . ?
F5_3 C2_3 C1_3 111.9(4) . . ?
F4_3 C2_3 C1_3 109.0(4) . . ?
F3_3 C2_3 C1_3 111.6(4) . . ?
F1_4 C1_4 F2_4 104.5(3) . . ?
F1_4 C1_4 C2_4 106.0(3) . . ?
F2_4 C1_4 C2_4 104.4(3) . . ?
F1_4 C1_4 P1_1 112.9(3) . . ?
F2_4 C1_4 P1_1 108.4(3) . . ?
C2_4 C1_4 P1_1 119.4(3) . . ?
F3_4 C2_4 F4_4 107.8(3) . . ?
F3_4 C2_4 F5_4 108.4(4) . . ?
F4_4 C2_4 F5_4 107.5(3) . . ?
F3_4 C2_4 C1_4 112.2(3) . . ?
F4_4 C2_4 C1_4 109.5(4) . . ?
F5_4 C2_4 C1_4 111.3(4) . . ?
C1_5 N1_5 C2_5 108.5(4) . . ?
C1_5 N1_5 C4_5 125.7(5) . . ?
C2_5 N1_5 C4_5 125.8(5) . . ?
N2_5 C1_5 N1_5 108.8(4) . . ?
N2_5 C1_5 H1_5 125.6 . . ?
N1_5 C1_5 H1_5 125.6 . . ?
C1_5 N2_5 C3_5 108.0(4) . . ?
C1_5 N2_5 C5_5 126.5(4) . . ?
C3_5 N2_5 C5_5 125.5(4) . . ?
C2_5 C3_5 N2_5 107.3(4) . . ?
C2_5 C3_5 H3_5 126.3 . . ?
N2_5 C3_5 H3_5 126.3 . . ?
N1_5 C4_5 H4A_5 109.5 . . ?
N1_5 C4_5 H4B_5 109.5 . . ?
H4A_5 C4_5 H4B_5 109.5 . . ?
N1_5 C4_5 H4C_5 109.5 . . ?
H4A_5 C4_5 H4C_5 109.5 . . ?
H4B_5 C4_5 H4C_5 109.5 . . ?
N2_5 C5_5 C6_5 111.7(4) . . ?
N2_5 C5_5 H5A_5 109.3 . . ?
C6_5 C5_5 H5A_5 109.3 . . ?
N2_5 C5_5 H5AB_5 109.3 . . ?
C6_5 C5_5 H5AB_5 109.3 . . ?
H5A_5 C5_5 H5AB_5 107.9 . . ?
C5_5 C6_5 H6A_5 109.5 . . ?
C5_5 C6_5 H6B_5 109.5 . . ?
H6A_5 C6_5 H6B_5 109.5 . . ?
C5_5 C6_5 H6C_5 109.5 . . ?
H6A_5 C6_5 H6C_5 109.5 . . ?
H6B_5 C6_5 H6C_5 109.5 . . ?
C3_5 C2_5 N1_5 107.3(4) . . ?
C3_5 C2_5 H2_5 126.4 . . ?
N1_5 C2_5 H2_5 126.4 . . ?

_refine_diff_density_max         0.708
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.106

####################################################################### 
# 
# 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_test_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2520843'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H15 N2, C2 F10 P'
_chemical_formula_sum            'C10 H15 F10 N2 P'
_chemical_formula_weight         384.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.8239(2)
_cell_length_b                   8.38760(10)
_cell_length_c                   14.1448(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.1230(10)
_cell_angle_gamma                90
_cell_volume                     1521.44(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17242
_cell_measurement_theta_min      4.6510
_cell_measurement_theta_max      78.6640

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_exptl_absorpt_coefficient_mu    2.660
_exptl_absorpt_correction_T_min  0.220
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.460
_oxdiff_exptl_absorpt_empirical_full_max 53.980
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            23281
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.649
_diffrn_reflns_theta_max         79.723
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3278
_reflns_number_gt                3176
_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       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0796P)²+1.1152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3278
_refine_ls_number_parameters     248
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1_1 P 0.50537(4) 0.36126(6) 0.69781(4) 0.02895(17) Uani 1 1 d . . . . .
F2_1 F 0.41489(10) 0.48559(19) 0.72408(10) 0.0433(4) Uani 1 1 d . . . . .
F3_1 F 0.56066(10) 0.49336(15) 0.63195(9) 0.0342(3) Uani 1 1 d . . . . .
F4_1 F 0.59734(10) 0.23866(14) 0.67123(9) 0.0333(3) Uani 1 1 d . . . . .
F5_1 F 0.43974(11) 0.30034(19) 0.60833(10) 0.0431(3) Uani 1 1 d . . . . .
F1_1 F 0.45223(12) 0.22655(18) 0.76219(10) 0.0455(4) Uani 1 1 d . . . . .
C1_2 C 0.58139(16) 0.4386(3) 0.80500(14) 0.0304(4) Uani 1 1 d . . . . .
F1_2 F 0.59728(11) 0.59808(16) 0.79788(10) 0.0418(3) Uani 1 1 d . . . . .
C2_2 C 0.68922(19) 0.3681(3) 0.82707(16) 0.0396(5) Uani 1 1 d . . . . .
F2_2 F 0.52527(11) 0.41728(19) 0.88611(9) 0.0427(3) Uani 1 1 d . . . . .
F3_2 F 0.75576(11) 0.3946(2) 0.75692(10) 0.0492(4) Uani 1 1 d . . . . .
F4_2 F 0.68471(15) 0.21354(19) 0.84385(11) 0.0565(4) Uani 1 1 d . . . . .
F5_2 F 0.72870(12) 0.4377(2) 0.90486(11) 0.0537(4) Uani 1 1 d . . . . .
N1_3 N 0.58721(13) 0.1522(2) 0.39653(12) 0.0281(4) Uani 1 1 d . . . . .
C1_3 C 0.47646(18) 0.1317(3) 0.3737(2) 0.0402(5) Uani 1 1 d . . . . .
H1A_3 H 0.462059 0.177452 0.311251 0.060 Uiso 1 1 calc R U . . .
H1B_3 H 0.433987 0.186079 0.421317 0.060 Uiso 1 1 calc R U . . .
H1C_3 H 0.459316 0.017845 0.373188 0.060 Uiso 1 1 calc R U . . .
N2_3 N 0.72628(15) 0.2449(2) 0.46118(13) 0.0348(4) Uani 1 1 d . . . . .
C3_3 C 0.66875(18) 0.0625(3) 0.36280(15) 0.0341(4) Uani 1 1 d . . . . .
H3_3 H 0.664535 -0.023877 0.319514 0.041 Uiso 1 1 calc R U . . .
C4_3 C 0.75598(18) 0.1214(3) 0.40334(17) 0.0399(5) Uani 1 1 d . . . . .
H4_3 H 0.825143 0.084361 0.393677 0.048 Uiso 1 1 calc R U . . .
C5_3 C 0.62461(17) 0.2621(2) 0.45527(14) 0.0314(4) Uani 1 1 d . . . . .
H5_3 H 0.584494 0.340086 0.487594 0.038 Uiso 1 1 calc R U . . .
C1_4 C 0.7888(3) 0.3445(4) 0.5289(2) 0.0315(7) Uani 0.757(6) 1 d . U P A 1
H1A_4 H 0.827722 0.274089 0.572671 0.038 Uiso 0.757(6) 1 calc R U P A 1
H1AB_4 H 0.741293 0.411798 0.566880 0.038 Uiso 0.757(6) 1 calc R U P A 1
C2_4 C 0.8654(3) 0.4506(4) 0.4754(2) 0.0305(6) Uani 0.757(6) 1 d . U P A 1
H2A_4 H 0.911561 0.504544 0.521554 0.037 Uiso 0.757(6) 1 calc R U P A 1
H2AB_4 H 0.909567 0.382800 0.434556 0.037 Uiso 0.757(6) 1 calc R U P A 1
C3_4 C 0.8120(3) 0.5763(5) 0.4145(3) 0.0339(7) Uani 0.757(6) 1 d . U P A 1
H3A_4 H 0.761481 0.636819 0.453278 0.041 Uiso 0.757(6) 1 calc R U P A 1
H3AB_4 H 0.773104 0.523543 0.362637 0.041 Uiso 0.757(6) 1 calc R U P A 1
C4_4 C 0.8926(4) 0.6908(6) 0.3728(3) 0.0480(10) Uani 0.757(6) 1 d . U P A 1
H4A_4 H 0.946226 0.629719 0.339327 0.072 Uiso 0.757(6) 1 calc R U P A 1
H4B_4 H 0.925178 0.752229 0.423896 0.072 Uiso 0.757(6) 1 calc R U P A 1
H4C_4 H 0.858164 0.763723 0.328566 0.072 Uiso 0.757(6) 1 calc R U P A 1
C1_14 C 0.8205(9) 0.3081(14) 0.5090(8) 0.0314(13) Uani 0.243(6) 1 d . U P A 2
H1A_14 H 0.818676 0.282618 0.577287 0.038 Uiso 0.243(6) 1 calc R U P A 2
H1AB_14 H 0.884113 0.260189 0.481412 0.038 Uiso 0.243(6) 1 calc R U P A 2
C2_14 C 0.8208(10) 0.4823(12) 0.4948(7) 0.0328(10) Uani 0.243(6) 1 d . U P A 2
H2A_14 H 0.874613 0.528505 0.536978 0.039 Uiso 0.243(6) 1 calc R U P A 2
H2AB_14 H 0.752507 0.524146 0.515867 0.039 Uiso 0.243(6) 1 calc R U P A 2
C3_14 C 0.8402(10) 0.5421(15) 0.3975(9) 0.0331(12) Uani 0.243(6) 1 d . U P A 2
H3A_14 H 0.782622 0.505315 0.356090 0.040 Uiso 0.243(6) 1 calc R U P A 2
H3AB_14 H 0.905383 0.493385 0.373792 0.040 Uiso 0.243(6) 1 calc R U P A 2
C4_14 C 0.8491(11) 0.7190(15) 0.3885(9) 0.040(2) Uani 0.243(6) 1 d . U P A 2
H4A_14 H 0.858632 0.747522 0.321935 0.059 Uiso 0.243(6) 1 calc R U P A 2
H4B_14 H 0.909045 0.756443 0.425394 0.059 Uiso 0.243(6) 1 calc R U P A 2
H4C_14 H 0.785321 0.769170 0.412446 0.059 Uiso 0.243(6) 1 calc R U 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_1 F5_1 1.6021(13) . ?
P1_1 F1_1 1.6041(14) . ?
P1_1 F2_1 1.6043(14) . ?
P1_1 F4_1 1.6099(13) . ?
P1_1 F3_1 1.6127(13) . ?
P1_1 C1_2 1.914(2) . ?
C1_2 F1_2 1.357(3) . ?
C1_2 F2_2 1.367(2) . ?
C1_2 C2_2 1.535(3) . ?
C2_2 F4_2 1.319(3) . ?
C2_2 F3_2 1.329(3) . ?
C2_2 F5_2 1.344(3) . ?
N1_3 C5_3 1.330(3) . ?
N1_3 C3_3 1.375(3) . ?
N1_3 C1_3 1.466(3) . ?
C1_3 H1A_3 0.9800 . ?
C1_3 H1B_3 0.9800 . ?
C1_3 H1C_3 0.9800 . ?
N2_3 C5_3 1.314(3) . ?
N2_3 C4_3 1.374(3) . ?
N2_3 C1_14 1.482(11) . ?
N2_3 C1_4 1.502(4) . ?
C3_3 C4_3 1.350(3) . ?
C3_3 H3_3 0.9500 . ?
C4_3 H4_3 0.9500 . ?
C5_3 H5_3 0.9500 . ?
C1_4 C2_4 1.526(5) . ?
C1_4 H1A_4 0.9900 . ?
C1_4 H1AB_4 0.9900 . ?
C2_4 C3_4 1.523(5) . ?
C2_4 H2A_4 0.9900 . ?
C2_4 H2AB_4 0.9900 . ?
C3_4 C4_4 1.530(6) . ?
C3_4 H3A_4 0.9900 . ?
C3_4 H3AB_4 0.9900 . ?
C4_4 H4A_4 0.9800 . ?
C4_4 H4B_4 0.9800 . ?
C4_4 H4C_4 0.9800 . ?
C1_14 C2_14 1.474(16) . ?
C1_14 H1A_14 0.9900 . ?
C1_14 H1AB_14 0.9900 . ?
C2_14 C3_14 1.487(17) . ?
C2_14 H2A_14 0.9900 . ?
C2_14 H2AB_14 0.9900 . ?
C3_14 C4_14 1.494(19) . ?
C3_14 H3A_14 0.9900 . ?
C3_14 H3AB_14 0.9900 . ?
C4_14 H4A_14 0.9800 . ?
C4_14 H4B_14 0.9800 . ?
C4_14 H4C_14 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F5_1 P1_1 F1_1 90.04(8) . . ?
F5_1 P1_1 F2_1 90.65(7) . . ?
F1_1 P1_1 F2_1 91.03(9) . . ?
F5_1 P1_1 F4_1 89.76(7) . . ?
F1_1 P1_1 F4_1 89.71(8) . . ?
F2_1 P1_1 F4_1 179.16(8) . . ?
F5_1 P1_1 F3_1 89.64(8) . . ?
F1_1 P1_1 F3_1 178.58(8) . . ?
F2_1 P1_1 F3_1 90.36(8) . . ?
F4_1 P1_1 F3_1 88.90(7) . . ?
F5_1 P1_1 C1_2 178.53(9) . . ?
F1_1 P1_1 C1_2 90.30(9) . . ?
F2_1 P1_1 C1_2 87.91(8) . . ?
F4_1 P1_1 C1_2 91.68(8) . . ?
F3_1 P1_1 C1_2 90.05(8) . . ?
F1_2 C1_2 F2_2 105.70(17) . . ?
F1_2 C1_2 C2_2 105.04(18) . . ?
F2_2 C1_2 C2_2 104.74(17) . . ?
F1_2 C1_2 P1_1 110.59(14) . . ?
F2_2 C1_2 P1_1 110.63(14) . . ?
C2_2 C1_2 P1_1 119.17(15) . . ?
F4_2 C2_2 F3_2 109.1(2) . . ?
F4_2 C2_2 F5_2 107.2(2) . . ?
F3_2 C2_2 F5_2 107.3(2) . . ?
F4_2 C2_2 C1_2 112.0(2) . . ?
F3_2 C2_2 C1_2 111.31(19) . . ?
F5_2 C2_2 C1_2 109.68(18) . . ?
C5_3 N1_3 C3_3 108.83(18) . . ?
C5_3 N1_3 C1_3 124.56(19) . . ?
C3_3 N1_3 C1_3 126.61(18) . . ?
N1_3 C1_3 H1A_3 109.5 . . ?
N1_3 C1_3 H1B_3 109.5 . . ?
H1A_3 C1_3 H1B_3 109.5 . . ?
N1_3 C1_3 H1C_3 109.5 . . ?
H1A_3 C1_3 H1C_3 109.5 . . ?
H1B_3 C1_3 H1C_3 109.5 . . ?
C5_3 N2_3 C4_3 108.72(18) . . ?
C5_3 N2_3 C1_14 142.9(5) . . ?
C4_3 N2_3 C1_14 108.3(5) . . ?
C5_3 N2_3 C1_4 120.5(2) . . ?
C4_3 N2_3 C1_4 130.6(2) . . ?
C4_3 C3_3 N1_3 106.4(2) . . ?
C4_3 C3_3 H3_3 126.8 . . ?
N1_3 C3_3 H3_3 126.8 . . ?
C3_3 C4_3 N2_3 107.4(2) . . ?
C3_3 C4_3 H4_3 126.3 . . ?
N2_3 C4_3 H4_3 126.3 . . ?
N2_3 C5_3 N1_3 108.68(19) . . ?
N2_3 C5_3 H5_3 125.7 . . ?
N1_3 C5_3 H5_3 125.7 . . ?
N2_3 C1_4 C2_4 110.6(3) . . ?
N2_3 C1_4 H1A_4 109.5 . . ?
C2_4 C1_4 H1A_4 109.5 . . ?
N2_3 C1_4 H1AB_4 109.5 . . ?
C2_4 C1_4 H1AB_4 109.5 . . ?
H1A_4 C1_4 H1AB_4 108.1 . . ?
C3_4 C2_4 C1_4 113.3(3) . . ?
C3_4 C2_4 H2A_4 108.9 . . ?
C1_4 C2_4 H2A_4 108.9 . . ?
C3_4 C2_4 H2AB_4 108.9 . . ?
C1_4 C2_4 H2AB_4 108.9 . . ?
H2A_4 C2_4 H2AB_4 107.7 . . ?
C2_4 C3_4 C4_4 110.4(4) . . ?
C2_4 C3_4 H3A_4 109.6 . . ?
C4_4 C3_4 H3A_4 109.6 . . ?
C2_4 C3_4 H3AB_4 109.6 . . ?
C4_4 C3_4 H3AB_4 109.6 . . ?
H3A_4 C3_4 H3AB_4 108.1 . . ?
C3_4 C4_4 H4A_4 109.5 . . ?
C3_4 C4_4 H4B_4 109.5 . . ?
H4A_4 C4_4 H4B_4 109.5 . . ?
C3_4 C4_4 H4C_4 109.5 . . ?
H4A_4 C4_4 H4C_4 109.5 . . ?
H4B_4 C4_4 H4C_4 109.5 . . ?
C2_14 C1_14 N2_3 107.2(9) . . ?
C2_14 C1_14 H1A_14 110.3 . . ?
N2_3 C1_14 H1A_14 110.3 . . ?
C2_14 C1_14 H1AB_14 110.3 . . ?
N2_3 C1_14 H1AB_14 110.3 . . ?
H1A_14 C1_14 H1AB_14 108.5 . . ?
C1_14 C2_14 C3_14 117.4(12) . . ?
C1_14 C2_14 H2A_14 107.9 . . ?
C3_14 C2_14 H2A_14 107.9 . . ?
C1_14 C2_14 H2AB_14 107.9 . . ?
C3_14 C2_14 H2AB_14 107.9 . . ?
H2A_14 C2_14 H2AB_14 107.2 . . ?
C2_14 C3_14 C4_14 115.2(12) . . ?
C2_14 C3_14 H3A_14 108.5 . . ?
C4_14 C3_14 H3A_14 108.5 . . ?
C2_14 C3_14 H3AB_14 108.5 . . ?
C4_14 C3_14 H3AB_14 108.5 . . ?
H3A_14 C3_14 H3AB_14 107.5 . . ?
C3_14 C4_14 H4A_14 109.5 . . ?
C3_14 C4_14 H4B_14 109.5 . . ?
H4A_14 C4_14 H4B_14 109.5 . . ?
C3_14 C4_14 H4C_14 109.5 . . ?
H4A_14 C4_14 H4C_14 109.5 . . ?
H4B_14 C4_14 H4C_14 109.5 . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_test_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2520841'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 F10 P , C6 H11 N2'
_chemical_formula_sum            'C8 H11 F10 N2 P'
_chemical_formula_weight         356.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_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                   9.40700(10)
_cell_length_b                   9.85750(10)
_cell_length_c                   14.6083(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.3740(10)
_cell_angle_gamma                90
_cell_volume                     1346.25(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16161
_cell_measurement_theta_min      4.4850
_cell_measurement_theta_max      79.2850

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    2.951
_exptl_absorpt_correction_T_min  0.151
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_oxdiff_exptl_absorpt_empirical_full_min 0.485
_oxdiff_exptl_absorpt_empirical_full_max 2.124
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            19775
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.730
_diffrn_reflns_theta_max         79.930
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2917
_reflns_number_gt                2887
_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       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.1003P)²+0.6001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2917
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1600
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
N1_1 N 0.67810(18) 0.6947(2) 0.44936(11) 0.0375(4) Uani 1 1 d . . . . .
N2_1 N 0.47561(18) 0.7936(2) 0.45746(11) 0.0370(4) Uani 1 1 d . . . . .
C1_1 C 0.7826(3) 0.4707(3) 0.4281(2) 0.0605(7) Uani 1 1 d . . . . .
H1A_1 H 0.691832 0.437759 0.396445 0.091 Uiso 1 1 calc R U . . .
H1B_1 H 0.785387 0.453149 0.494285 0.091 Uiso 1 1 calc R U . . .
H1C_1 H 0.862195 0.423527 0.403936 0.091 Uiso 1 1 calc R U . . .
C2_1 C 0.7953(2) 0.6200(3) 0.41216(16) 0.0465(5) Uani 1 1 d . . . . .
H2A_1 H 0.888435 0.652745 0.442356 0.056 Uiso 1 1 calc R U . . .
H2AB_1 H 0.792206 0.637795 0.345268 0.056 Uiso 1 1 calc R U . . .
C3_1 C 0.3349(2) 0.8549(3) 0.42963(16) 0.0455(5) Uani 1 1 d . . . . .
H3A_1 H 0.313074 0.848752 0.362587 0.068 Uiso 1 1 calc R U . . .
H3B_1 H 0.336317 0.950381 0.448373 0.068 Uiso 1 1 calc R U . . .
H3C_1 H 0.261569 0.806356 0.459385 0.068 Uiso 1 1 calc R U . . .
C4_1 C 0.5609(2) 0.7403(2) 0.40071(12) 0.0380(4) Uani 1 1 d . . . . .
H4_1 H 0.541063 0.735657 0.335584 0.046 Uiso 1 1 calc R U . . .
C5_1 C 0.5413(2) 0.7809(3) 0.54650(14) 0.0435(5) Uani 1 1 d . . . . .
H5_1 H 0.504198 0.810280 0.601058 0.052 Uiso 1 1 calc R U . . .
C6_1 C 0.6674(2) 0.7193(3) 0.54132(13) 0.0426(5) Uani 1 1 d . . . . .
H6_1 H 0.736342 0.696851 0.591554 0.051 Uiso 1 1 calc R U . . .
P1_2 P 0.30921(5) 0.52622(6) 0.23587(3) 0.0372(2) Uani 1 1 d . . . . .
C1_2 C 0.1103(2) 0.5545(3) 0.24456(15) 0.0435(5) Uani 1 1 d . . . . .
C2_2 C 0.0055(3) 0.5523(3) 0.15616(18) 0.0509(6) Uani 1 1 d . . . . .
F1_2 F 0.33376(14) 0.54693(14) 0.34603(8) 0.0429(3) Uani 1 1 d . . . . .
F2_2 F 0.33002(14) 0.68632(15) 0.22060(9) 0.0451(3) Uani 1 1 d . . . . .
F3_2 F 0.28455(14) 0.50587(16) 0.12589(8) 0.0455(3) Uani 1 1 d . . . . .
F4_2 F 0.28879(14) 0.36569(16) 0.24959(8) 0.0454(3) Uani 1 1 d . . . . .
F5_2 F 0.47793(13) 0.50468(17) 0.23408(9) 0.0492(4) Uani 1 1 d . . . . .
F6_2 F 0.08783(15) 0.67598(19) 0.28437(11) 0.0593(4) Uani 1 1 d . . . . .
F7_2 F 0.06016(15) 0.45864(19) 0.30027(10) 0.0578(4) Uani 1 1 d . . . . .
F8_2 F -0.12839(15) 0.5742(2) 0.17815(12) 0.0643(5) Uani 1 1 d . . . . .
F9_2 F 0.03470(17) 0.65011(19) 0.09841(11) 0.0602(4) Uani 1 1 d . . . . .
F10_2 F 0.00584(16) 0.43376(18) 0.11366(10) 0.0576(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
N1_1 C4_1 1.323(3) . ?
N1_1 C6_1 1.380(2) . ?
N1_1 C2_1 1.478(3) . ?
N2_1 C4_1 1.325(3) . ?
N2_1 C5_1 1.382(3) . ?
N2_1 C3_1 1.470(3) . ?
C1_1 C2_1 1.497(4) . ?
C1_1 H1A_1 0.9800 . ?
C1_1 H1B_1 0.9800 . ?
C1_1 H1C_1 0.9800 . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2AB_1 0.9900 . ?
C3_1 H3A_1 0.9800 . ?
C3_1 H3B_1 0.9800 . ?
C3_1 H3C_1 0.9800 . ?
C4_1 H4_1 0.9500 . ?
C5_1 C6_1 1.342(3) . ?
C5_1 H5_1 0.9500 . ?
C6_1 H6_1 0.9500 . ?
P1_2 F5_2 1.6044(13) . ?
P1_2 F2_2 1.6088(15) . ?
P1_2 F4_2 1.6093(16) . ?
P1_2 F3_2 1.6101(12) . ?
P1_2 F1_2 1.6132(12) . ?
P1_2 C1_2 1.910(2) . ?
C1_2 F6_2 1.358(3) . ?
C1_2 F7_2 1.365(3) . ?
C1_2 C2_2 1.536(3) . ?
C2_2 F10_2 1.324(3) . ?
C2_2 F9_2 1.330(3) . ?
C2_2 F8_2 1.351(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
C4_1 N1_1 C6_1 108.46(17) . . ?
C4_1 N1_1 C2_1 125.67(17) . . ?
C6_1 N1_1 C2_1 125.70(18) . . ?
C4_1 N2_1 C5_1 108.33(18) . . ?
C4_1 N2_1 C3_1 125.37(17) . . ?
C5_1 N2_1 C3_1 126.30(18) . . ?
C2_1 C1_1 H1A_1 109.5 . . ?
C2_1 C1_1 H1B_1 109.5 . . ?
H1A_1 C1_1 H1B_1 109.5 . . ?
C2_1 C1_1 H1C_1 109.5 . . ?
H1A_1 C1_1 H1C_1 109.5 . . ?
H1B_1 C1_1 H1C_1 109.5 . . ?
N1_1 C2_1 C1_1 110.87(18) . . ?
N1_1 C2_1 H2A_1 109.5 . . ?
C1_1 C2_1 H2A_1 109.5 . . ?
N1_1 C2_1 H2AB_1 109.5 . . ?
C1_1 C2_1 H2AB_1 109.5 . . ?
H2A_1 C2_1 H2AB_1 108.1 . . ?
N2_1 C3_1 H3A_1 109.5 . . ?
N2_1 C3_1 H3B_1 109.5 . . ?
H3A_1 C3_1 H3B_1 109.5 . . ?
N2_1 C3_1 H3C_1 109.5 . . ?
H3A_1 C3_1 H3C_1 109.5 . . ?
H3B_1 C3_1 H3C_1 109.5 . . ?
N1_1 C4_1 N2_1 108.98(16) . . ?
N1_1 C4_1 H4_1 125.5 . . ?
N2_1 C4_1 H4_1 125.5 . . ?
C6_1 C5_1 N2_1 107.07(18) . . ?
C6_1 C5_1 H5_1 126.5 . . ?
N2_1 C5_1 H5_1 126.5 . . ?
C5_1 C6_1 N1_1 107.16(18) . . ?
C5_1 C6_1 H6_1 126.4 . . ?
N1_1 C6_1 H6_1 126.4 . . ?
F5_2 P1_2 F2_2 89.53(8) . . ?
F5_2 P1_2 F4_2 90.22(8) . . ?
F2_2 P1_2 F4_2 179.16(7) . . ?
F5_2 P1_2 F3_2 90.03(7) . . ?
F2_2 P1_2 F3_2 89.44(7) . . ?
F4_2 P1_2 F3_2 89.76(7) . . ?
F5_2 P1_2 F1_2 90.04(7) . . ?
F2_2 P1_2 F1_2 90.46(7) . . ?
F4_2 P1_2 F1_2 90.35(7) . . ?
F3_2 P1_2 F1_2 179.88(9) . . ?
F5_2 P1_2 C1_2 177.02(9) . . ?
F2_2 P1_2 C1_2 90.06(10) . . ?
F4_2 P1_2 C1_2 90.23(9) . . ?
F3_2 P1_2 C1_2 92.92(8) . . ?
F1_2 P1_2 C1_2 87.02(8) . . ?
F6_2 C1_2 F7_2 105.94(18) . . ?
F6_2 C1_2 C2_2 104.9(2) . . ?
F7_2 C1_2 C2_2 105.03(19) . . ?
F6_2 C1_2 P1_2 110.95(15) . . ?
F7_2 C1_2 P1_2 110.14(16) . . ?
C2_2 C1_2 P1_2 118.98(16) . . ?
F10_2 C2_2 F9_2 109.3(2) . . ?
F10_2 C2_2 F8_2 107.7(2) . . ?
F9_2 C2_2 F8_2 107.4(2) . . ?
F10_2 C2_2 C1_2 111.8(2) . . ?
F9_2 C2_2 C1_2 111.4(2) . . ?
F8_2 C2_2 C1_2 109.1(2) . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.385
_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_test_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2520840'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT029_test_a              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.934 Why?  
RESPONSE: Capillary was moving out of the beam at some angles. Lead to omission of some data, therefore the completeness lowered up to 93.4%
;

_vrf_PLAT097_test_a              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.51 eA-3
RESPONSE: Capillary was moving out of the beam at some angles.
;

_vrf_PLAT230_test_a              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.51 eA-3
RESPONSE: Capillary was moving out of the beam at some angles.
;

_vrf_PLAT340_test_a              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.51 eA-3
RESPONSE: Capillary was moving out of the beam at some angles.
;

_vrf_PLAT910_test_a              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.51 eA-3
RESPONSE: Capillary was moving out of the beam at some angles.
;

_vrf_PLAT911_test_a              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 1.51 eA-3
RESPONSE: Capillary was moving out of the beam at some angles.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H11 N2 , F14 C4 P'
_chemical_formula_sum            'C10 H11 F14 N2 P'
_chemical_formula_weight         456.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7017(2)
_cell_length_b                   12.7582(4)
_cell_length_c                   15.3820(4)
_cell_angle_alpha                71.555(2)
_cell_angle_beta                 87.074(2)
_cell_angle_gamma                83.244(2)
_cell_volume                     1608.53(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(10)
_cell_measurement_reflns_used    12748
_cell_measurement_theta_min      3.0260
_cell_measurement_theta_max      76.9640

_exptl_crystal_description       capillary
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    3.010
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_oxdiff_exptl_absorpt_empirical_full_min 0.753
_oxdiff_exptl_absorpt_empirical_full_max 2.846
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14126
_diffrn_reflns_av_unetI/netI     0.1160
_diffrn_reflns_av_R_equivalents  0.1784
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         8.976
_diffrn_reflns_theta_max         77.730
_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measured_fraction_theta_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.934
_reflns_number_total             6081
_reflns_number_gt                5645
_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       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0250P)²+21.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6081
_refine_ls_number_parameters     494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.1253
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2596
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_1 P 0.76061(19) 0.48740(13) 0.25755(11) 0.0261(4) Uani 1 1 d . . . . .
F1_1 F 0.5761(4) 0.4988(3) 0.2433(3) 0.0339(9) Uani 1 1 d . . . . .
F2_1 F 0.7715(5) 0.3575(3) 0.2653(3) 0.0332(9) Uani 1 1 d . . . . .
F3_1 F 0.9448(5) 0.4769(3) 0.2726(3) 0.0347(9) Uani 1 1 d . . . . .
F4_1 F 0.7471(5) 0.6168(3) 0.2503(3) 0.0338(9) Uani 1 1 d . . . . .
C1_2 C 0.7359(10) 0.4393(7) 0.3863(6) 0.045(2) Uani 1 1 d . . . . .
F1_2 F 0.6074(5) 0.3860(3) 0.4139(3) 0.0349(9) Uani 1 1 d . . . . .
C2_2 C 0.7406(12) 0.5173(8) 0.4408(6) 0.052(2) Uani 1 1 d . . . . .
F2_2 F 0.8605(6) 0.3573(4) 0.4301(4) 0.0633(16) Uani 1 1 d . . . . .
F3_2 F 0.7283(6) 0.4639(4) 0.5317(3) 0.0432(11) Uani 1 1 d . . . . .
F4_2 F 0.6099(7) 0.5927(5) 0.4141(4) 0.0706(18) Uani 1 1 d . . . . .
F5_2 F 0.8665(6) 0.5693(4) 0.4278(3) 0.0502(13) Uani 1 1 d . . . . .
C1_3 C 0.8090(9) 0.5220(6) 0.1303(6) 0.0379(17) Uani 1 1 d . . . . .
F1_3 F 0.9157(5) 0.4370(4) 0.1122(3) 0.0510(12) Uani 1 1 d . . . . .
C2_3 C 0.6811(9) 0.5341(6) 0.0617(5) 0.0387(17) Uani 1 1 d . . . . .
F2_3 F 0.8795(5) 0.6172(4) 0.0980(3) 0.0393(10) Uani 1 1 d . . . . .
F3_3 F 0.5845(5) 0.6250(4) 0.0613(3) 0.0473(11) Uani 1 1 d . . . . .
F4_3 F 0.7454(5) 0.5504(4) -0.0226(3) 0.0414(10) Uani 1 1 d . . . . .
F5_3 F 0.6088(6) 0.4445(4) 0.0824(3) 0.0512(13) Uani 1 1 d . . . . .
P1_4 P 0.500000 1.000000 0.000000 0.0227(5) Uani 1 2 d S . P . .
F2_4 F 0.5423(5) 0.8982(3) -0.0417(3) 0.0363(9) Uani 1 1 d . . . . .
P2_4 P 1.000000 1.000000 0.500000 0.0225(5) Uani 1 2 d S . P . .
F3_4 F 1.0325(5) 0.8715(3) 0.5619(3) 0.0371(10) Uani 1 1 d . . . . .
F4_4 F 1.0860(5) 0.9678(4) 0.4151(3) 0.0373(10) Uani 1 1 d . . . . .
F1_4 F 0.6210(5) 1.0714(4) -0.0694(3) 0.0440(11) Uani 1 1 d . . . . .
C1_5 C 0.8088(8) 0.9659(6) 0.4668(5) 0.0297(14) Uani 1 1 d . . . . .
F1_5 F 0.7182(5) 0.9250(4) 0.5428(3) 0.0406(10) Uani 1 1 d . . . . .
C2_5 C 0.7016(9) 1.0529(6) 0.3988(6) 0.0385(17) Uani 1 1 d . . . . .
F2_5 F 0.8347(5) 0.8791(4) 0.4291(3) 0.0430(11) Uani 1 1 d . . . . .
F3_5 F 0.6538(5) 1.1389(3) 0.4319(3) 0.0402(10) Uani 1 1 d . . . . .
F4_5 F 0.5774(5) 1.0114(4) 0.3845(4) 0.0509(12) Uani 1 1 d . . . . .
F5_5 F 0.7736(6) 1.0952(4) 0.3191(3) 0.0501(12) Uani 1 1 d . . . . .
C1_6 C 0.6640(10) 0.9332(7) 0.0859(6) 0.046(2) Uani 1 1 d . . . . .
F1_6 F 0.6448(7) 0.8240(4) 0.1283(4) 0.0548(14) Uani 1 1 d . . . . .
C2_6 C 0.6931(11) 0.9811(7) 0.1577(6) 0.048(2) Uani 1 1 d . . . . .
F2_6 F 0.8100(6) 0.9359(5) 0.0392(4) 0.0625(15) Uani 1 1 d . . . . .
F3_6 F 0.7321(6) 1.0834(4) 0.1272(3) 0.0545(14) Uani 1 1 d . . . . .
F4_6 F 0.8046(5) 0.9184(4) 0.2146(3) 0.0444(11) Uani 1 1 d . . . . .
F5_6 F 0.5592(6) 0.9799(5) 0.2094(3) 0.0543(13) Uani 1 1 d . . . . .
C1_7 C 0.8469(8) 0.7348(5) 0.7354(5) 0.0294(14) Uani 1 1 d . . . . .
H1_7 H 0.951427 0.730300 0.714561 0.035 Uiso 1 1 calc R U . . .
N1_7 N 0.7316(6) 0.7037(4) 0.7016(4) 0.0258(11) Uani 1 1 d . . . . .
C2_7 C 0.5971(8) 0.7227(5) 0.7483(5) 0.0307(15) Uani 1 1 d . . . . .
H2_7 H 0.496392 0.707927 0.737782 0.037 Uiso 1 1 calc R U . . .
N2_7 N 0.7954(7) 0.7736(4) 0.8032(4) 0.0286(12) Uani 1 1 d . . . . .
C3_7 C 0.6376(8) 0.7665(5) 0.8122(5) 0.0309(14) Uani 1 1 d . . . . .
H3_7 H 0.570058 0.788375 0.855327 0.037 Uiso 1 1 calc R U . . .
C4_7 C 0.7430(9) 0.6556(6) 0.6260(5) 0.0384(17) Uani 1 1 d . . . . .
H4A_7 H 0.675623 0.702053 0.576133 0.058 Uiso 1 1 calc R U . . .
H4B_7 H 0.710763 0.580447 0.648044 0.058 Uiso 1 1 calc R U . . .
H4C_7 H 0.850313 0.652161 0.603487 0.058 Uiso 1 1 calc R U . . .
C5_7 C 0.8853(8) 0.8190(6) 0.8582(5) 0.0348(16) Uani 1 1 d . . . . .
H5A_7 H 0.994790 0.787156 0.858697 0.042 Uiso 1 1 calc R U . . .
H5AB_7 H 0.845629 0.796881 0.922190 0.042 Uiso 1 1 calc R U . . .
C6_7 C 0.8768(9) 0.9438(6) 0.8214(6) 0.0394(17) Uani 1 1 d . . . . .
H6A_7 H 0.925686 0.965778 0.760398 0.059 Uiso 1 1 calc R U . . .
H6B_7 H 0.931004 0.971400 0.862657 0.059 Uiso 1 1 calc R U . . .
H6C_7 H 0.768201 0.975458 0.817131 0.059 Uiso 1 1 calc R U . . .
C1_8 C 0.3422(8) 0.7170(5) 0.2547(4) 0.0268(13) Uani 1 1 d . . . . .
H1_8 H 0.447594 0.705079 0.237509 0.032 Uiso 1 1 calc R U . . .
N1_8 N 0.2237(6) 0.6851(5) 0.2220(4) 0.0284(12) Uani 1 1 d . . . . .
C2_8 C 0.0891(8) 0.7186(6) 0.2625(6) 0.0362(17) Uani 1 1 d . . . . .
H2_8 H -0.013372 0.707445 0.251668 0.043 Uiso 1 1 calc R U . . .
N2_8 N 0.2902(6) 0.7687(4) 0.3156(4) 0.0266(11) Uani 1 1 d . . . . .
C3_8 C 0.1320(8) 0.7703(6) 0.3204(5) 0.0336(15) Uani 1 1 d . . . . .
H3_8 H 0.064254 0.802137 0.357855 0.040 Uiso 1 1 calc R U . . .
C4_8 C 0.2297(8) 0.6307(6) 0.1513(5) 0.0326(15) Uani 1 1 d . . . . .
H4A_8 H 0.150422 0.577789 0.165071 0.039 Uiso 1 1 calc R U . . .
H4AB_8 H 0.332395 0.588016 0.151601 0.039 Uiso 1 1 calc R U . . .
C5_8 C 0.2017(11) 0.7134(7) 0.0583(6) 0.045(2) Uani 1 1 d . . . . .
H5A_8 H 0.293754 0.752522 0.037415 0.067 Uiso 1 1 calc R U . . .
H5B_8 H 0.112990 0.767168 0.061460 0.067 Uiso 1 1 calc R U . . .
H5C_8 H 0.179921 0.674817 0.015183 0.067 Uiso 1 1 calc R U . . .
C6_8 C 0.3835(9) 0.8138(6) 0.3682(5) 0.0339(15) Uani 1 1 d . . . . .
H6A_8 H 0.490826 0.811528 0.345592 0.051 Uiso 1 1 calc R U . . .
H6B_8 H 0.379891 0.769302 0.432993 0.051 Uiso 1 1 calc R U . . .
H6C_8 H 0.342644 0.890833 0.361326 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1_1 F4_1 1.609(4) . ?
P1_1 F3_1 1.615(4) . ?
P1_1 F1_1 1.615(4) . ?
P1_1 F2_1 1.615(4) . ?
P1_1 C1_2 1.888(8) . ?
P1_1 C1_3 1.901(8) . ?
C1_2 F1_2 1.356(8) . ?
C1_2 F2_2 1.444(10) . ?
C1_2 C2_2 1.496(13) . ?
C2_2 F5_2 1.321(9) . ?
C2_2 F3_2 1.352(9) . ?
C2_2 F4_2 1.389(12) . ?
C1_3 F2_3 1.364(8) . ?
C1_3 F1_3 1.430(10) . ?
C1_3 C2_3 1.533(10) . ?
C2_3 F5_3 1.313(8) . ?
C2_3 F3_3 1.348(10) . ?
C2_3 F4_3 1.350(9) . ?
P1_4 F1_4 1.604(4) 2_675 ?
P1_4 F1_4 1.604(4) . ?
P1_4 F2_4 1.621(4) . ?
P1_4 F2_4 1.621(4) 2_675 ?
P1_4 C1_6 1.924(7) . ?
P1_4 C1_6 1.924(7) 2_675 ?
P2_4 F4_4 1.613(4) 2_776 ?
P2_4 F4_4 1.613(4) . ?
P2_4 F3_4 1.614(4) 2_776 ?
P2_4 F3_4 1.614(4) . ?
P2_4 C1_5 1.902(7) . ?
P2_4 C1_5 1.902(7) 2_776 ?
C1_5 F1_5 1.370(8) . ?
C1_5 F2_5 1.394(8) . ?
C1_5 C2_5 1.523(9) . ?
C2_5 F4_5 1.315(8) . ?
C2_5 F5_5 1.330(9) . ?
C2_5 F3_5 1.363(10) . ?
C1_6 F1_6 1.365(9) . ?
C1_6 F2_6 1.426(11) . ?
C1_6 C2_6 1.466(12) . ?
C2_6 F3_6 1.318(9) . ?
C2_6 F4_6 1.344(9) . ?
C2_6 F5_6 1.375(12) . ?
C1_7 N1_7 1.309(8) . ?
C1_7 N2_7 1.328(10) . ?
C1_7 H1_7 0.9500 . ?
N1_7 C2_7 1.379(9) . ?
N1_7 C4_7 1.471(9) . ?
C2_7 C3_7 1.354(10) . ?
C2_7 H2_7 0.9500 . ?
N2_7 C3_7 1.383(9) . ?
N2_7 C5_7 1.466(9) . ?
C3_7 H3_7 0.9500 . ?
C4_7 H4A_7 0.9800 . ?
C4_7 H4B_7 0.9800 . ?
C4_7 H4C_7 0.9800 . ?
C5_7 C6_7 1.506(10) . ?
C5_7 H5A_7 0.9900 . ?
C5_7 H5AB_7 0.9900 . ?
C6_7 H6A_7 0.9800 . ?
C6_7 H6B_7 0.9800 . ?
C6_7 H6C_7 0.9800 . ?
C1_8 N1_8 1.327(8) . ?
C1_8 N2_8 1.339(9) . ?
C1_8 H1_8 0.9500 . ?
N1_8 C2_8 1.385(9) . ?
N1_8 C4_8 1.461(9) . ?
C2_8 C3_8 1.353(11) . ?
C2_8 H2_8 0.9500 . ?
N2_8 C3_8 1.374(9) . ?
N2_8 C6_8 1.454(9) . ?
C3_8 H3_8 0.9500 . ?
C4_8 C5_8 1.496(10) . ?
C4_8 H4A_8 0.9900 . ?
C4_8 H4AB_8 0.9900 . ?
C5_8 H5A_8 0.9800 . ?
C5_8 H5B_8 0.9800 . ?
C5_8 H5C_8 0.9800 . ?
C6_8 H6A_8 0.9800 . ?
C6_8 H6B_8 0.9800 . ?
C6_8 H6C_8 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F4_1 P1_1 F3_1 90.2(2) . . ?
F4_1 P1_1 F1_1 89.3(2) . . ?
F3_1 P1_1 F1_1 179.3(3) . . ?
F4_1 P1_1 F2_1 179.1(2) . . ?
F3_1 P1_1 F2_1 90.6(2) . . ?
F1_1 P1_1 F2_1 89.9(2) . . ?
F4_1 P1_1 C1_2 93.7(3) . . ?
F3_1 P1_1 C1_2 87.9(3) . . ?
F1_1 P1_1 C1_2 91.7(3) . . ?
F2_1 P1_1 C1_2 86.0(3) . . ?
F4_1 P1_1 C1_3 91.1(3) . . ?
F3_1 P1_1 C1_3 86.3(3) . . ?
F1_1 P1_1 C1_3 94.2(3) . . ?
F2_1 P1_1 C1_3 89.4(3) . . ?
C1_2 P1_1 C1_3 172.5(4) . . ?
F1_2 C1_2 F2_2 103.7(6) . . ?
F1_2 C1_2 C2_2 107.0(8) . . ?
F2_2 C1_2 C2_2 98.7(7) . . ?
F1_2 C1_2 P1_1 112.3(5) . . ?
F2_2 C1_2 P1_1 111.7(6) . . ?
C2_2 C1_2 P1_1 121.4(5) . . ?
F5_2 C2_2 F3_2 107.2(7) . . ?
F5_2 C2_2 F4_2 110.7(8) . . ?
F3_2 C2_2 F4_2 108.4(8) . . ?
F5_2 C2_2 C1_2 114.8(8) . . ?
F3_2 C2_2 C1_2 111.2(7) . . ?
F4_2 C2_2 C1_2 104.3(7) . . ?
F2_3 C1_3 F1_3 105.6(6) . . ?
F2_3 C1_3 C2_3 105.4(6) . . ?
F1_3 C1_3 C2_3 101.4(6) . . ?
F2_3 C1_3 P1_1 111.9(5) . . ?
F1_3 C1_3 P1_1 111.3(5) . . ?
C2_3 C1_3 P1_1 120.0(5) . . ?
F5_3 C2_3 F3_3 112.1(7) . . ?
F5_3 C2_3 F4_3 108.2(6) . . ?
F3_3 C2_3 F4_3 108.8(6) . . ?
F5_3 C2_3 C1_3 111.6(6) . . ?
F3_3 C2_3 C1_3 107.2(6) . . ?
F4_3 C2_3 C1_3 108.9(6) . . ?
F1_4 P1_4 F1_4 180.0(3) 2_675 . ?
F1_4 P1_4 F2_4 89.3(2) 2_675 . ?
F1_4 P1_4 F2_4 90.7(2) . . ?
F1_4 P1_4 F2_4 90.7(2) 2_675 2_675 ?
F1_4 P1_4 F2_4 89.3(2) . 2_675 ?
F2_4 P1_4 F2_4 180.0(2) . 2_675 ?
F1_4 P1_4 C1_6 90.5(3) 2_675 . ?
F1_4 P1_4 C1_6 89.5(3) . . ?
F2_4 P1_4 C1_6 87.5(3) . . ?
F2_4 P1_4 C1_6 92.5(3) 2_675 . ?
F1_4 P1_4 C1_6 89.5(3) 2_675 2_675 ?
F1_4 P1_4 C1_6 90.5(3) . 2_675 ?
F2_4 P1_4 C1_6 92.5(3) . 2_675 ?
F2_4 P1_4 C1_6 87.5(3) 2_675 2_675 ?
C1_6 P1_4 C1_6 180.0 . 2_675 ?
F4_4 P2_4 F4_4 180.0(4) 2_776 . ?
F4_4 P2_4 F3_4 88.8(2) 2_776 2_776 ?
F4_4 P2_4 F3_4 91.2(2) . 2_776 ?
F4_4 P2_4 F3_4 91.2(2) 2_776 . ?
F4_4 P2_4 F3_4 88.8(2) . . ?
F3_4 P2_4 F3_4 180.0 2_776 . ?
F4_4 P2_4 C1_5 89.7(3) 2_776 . ?
F4_4 P2_4 C1_5 90.3(3) . . ?
F3_4 P2_4 C1_5 92.0(2) 2_776 . ?
F3_4 P2_4 C1_5 88.0(2) . . ?
F4_4 P2_4 C1_5 90.3(3) 2_776 2_776 ?
F4_4 P2_4 C1_5 89.7(3) . 2_776 ?
F3_4 P2_4 C1_5 88.0(2) 2_776 2_776 ?
F3_4 P2_4 C1_5 92.0(2) . 2_776 ?
C1_5 P2_4 C1_5 180.0 . 2_776 ?
F1_5 C1_5 F2_5 104.1(5) . . ?
F1_5 C1_5 C2_5 105.0(6) . . ?
F2_5 C1_5 C2_5 103.8(6) . . ?
F1_5 C1_5 P2_4 110.9(4) . . ?
F2_5 C1_5 P2_4 110.1(5) . . ?
C2_5 C1_5 P2_4 121.5(5) . . ?
F4_5 C2_5 F5_5 109.1(6) . . ?
F4_5 C2_5 F3_5 107.6(6) . . ?
F5_5 C2_5 F3_5 107.2(6) . . ?
F4_5 C2_5 C1_5 111.4(6) . . ?
F5_5 C2_5 C1_5 111.3(6) . . ?
F3_5 C2_5 C1_5 110.1(6) . . ?
F1_6 C1_6 F2_6 106.9(7) . . ?
F1_6 C1_6 C2_6 107.1(7) . . ?
F2_6 C1_6 C2_6 101.7(7) . . ?
F1_6 C1_6 P1_4 109.4(5) . . ?
F2_6 C1_6 P1_4 110.3(6) . . ?
C2_6 C1_6 P1_4 120.5(6) . . ?
F3_6 C2_6 F4_6 107.6(6) . . ?
F3_6 C2_6 F5_6 109.2(8) . . ?
F4_6 C2_6 F5_6 106.7(6) . . ?
F3_6 C2_6 C1_6 114.7(7) . . ?
F4_6 C2_6 C1_6 111.6(8) . . ?
F5_6 C2_6 C1_6 106.8(7) . . ?
N1_7 C1_7 N2_7 109.5(6) . . ?
N1_7 C1_7 H1_7 125.2 . . ?
N2_7 C1_7 H1_7 125.2 . . ?
C1_7 N1_7 C2_7 109.2(6) . . ?
C1_7 N1_7 C4_7 125.6(6) . . ?
C2_7 N1_7 C4_7 125.2(6) . . ?
C3_7 C2_7 N1_7 106.1(6) . . ?
C3_7 C2_7 H2_7 126.9 . . ?
N1_7 C2_7 H2_7 126.9 . . ?
C1_7 N2_7 C3_7 107.6(6) . . ?
C1_7 N2_7 C5_7 127.3(6) . . ?
C3_7 N2_7 C5_7 125.1(6) . . ?
C2_7 C3_7 N2_7 107.5(7) . . ?
C2_7 C3_7 H3_7 126.3 . . ?
N2_7 C3_7 H3_7 126.3 . . ?
N1_7 C4_7 H4A_7 109.5 . . ?
N1_7 C4_7 H4B_7 109.5 . . ?
H4A_7 C4_7 H4B_7 109.5 . . ?
N1_7 C4_7 H4C_7 109.5 . . ?
H4A_7 C4_7 H4C_7 109.5 . . ?
H4B_7 C4_7 H4C_7 109.5 . . ?
N2_7 C5_7 C6_7 111.9(6) . . ?
N2_7 C5_7 H5A_7 109.2 . . ?
C6_7 C5_7 H5A_7 109.2 . . ?
N2_7 C5_7 H5AB_7 109.2 . . ?
C6_7 C5_7 H5AB_7 109.2 . . ?
H5A_7 C5_7 H5AB_7 107.9 . . ?
C5_7 C6_7 H6A_7 109.5 . . ?
C5_7 C6_7 H6B_7 109.5 . . ?
H6A_7 C6_7 H6B_7 109.5 . . ?
C5_7 C6_7 H6C_7 109.5 . . ?
H6A_7 C6_7 H6C_7 109.5 . . ?
H6B_7 C6_7 H6C_7 109.5 . . ?
N1_8 C1_8 N2_8 109.5(6) . . ?
N1_8 C1_8 H1_8 125.2 . . ?
N2_8 C1_8 H1_8 125.2 . . ?
C1_8 N1_8 C2_8 108.2(6) . . ?
C1_8 N1_8 C4_8 126.9(6) . . ?
C2_8 N1_8 C4_8 124.7(6) . . ?
C3_8 C2_8 N1_8 106.6(6) . . ?
C3_8 C2_8 H2_8 126.7 . . ?
N1_8 C2_8 H2_8 126.7 . . ?
C1_8 N2_8 C3_8 107.4(6) . . ?
C1_8 N2_8 C6_8 126.6(6) . . ?
C3_8 N2_8 C6_8 126.0(6) . . ?
C2_8 C3_8 N2_8 108.2(7) . . ?
C2_8 C3_8 H3_8 125.9 . . ?
N2_8 C3_8 H3_8 125.9 . . ?
N1_8 C4_8 C5_8 111.4(6) . . ?
N1_8 C4_8 H4A_8 109.3 . . ?
C5_8 C4_8 H4A_8 109.3 . . ?
N1_8 C4_8 H4AB_8 109.3 . . ?
C5_8 C4_8 H4AB_8 109.3 . . ?
H4A_8 C4_8 H4AB_8 108.0 . . ?
C4_8 C5_8 H5A_8 109.5 . . ?
C4_8 C5_8 H5B_8 109.5 . . ?
H5A_8 C5_8 H5B_8 109.5 . . ?
C4_8 C5_8 H5C_8 109.5 . . ?
H5A_8 C5_8 H5C_8 109.5 . . ?
H5B_8 C5_8 H5C_8 109.5 . . ?
N2_8 C6_8 H6A_8 109.5 . . ?
N2_8 C6_8 H6B_8 109.5 . . ?
H6A_8 C6_8 H6B_8 109.5 . . ?
N2_8 C6_8 H6C_8 109.5 . . ?
H6A_8 C6_8 H6C_8 109.5 . . ?
H6B_8 C6_8 H6C_8 109.5 . . ?

_refine_diff_density_max         1.509
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.174

####################################################################### 
# 
# 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_test_a_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2520842'
loop_
_audit_author_name
_audit_author_address
'Maik Finze'
;University of Wuerzburg
Germany
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H11 N2 ,F6 P'
_chemical_formula_sum            'C6 H11 F6 N2 P'
_chemical_formula_weight         256.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.60170(10)
_cell_length_b                   8.98230(10)
_cell_length_c                   13.42880(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.5750(10)
_cell_angle_gamma                90
_cell_volume                     1016.449(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17507
_cell_measurement_theta_min      3.3670
_cell_measurement_theta_max      76.9400

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.064
_exptl_absorpt_correction_T_min  0.208
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.111a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.543
_oxdiff_exptl_absorpt_empirical_full_max 2.116
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            29850
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.249
_diffrn_reflns_theta_max         77.300
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2166
_reflns_number_gt                2062
_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       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0404P)²+0.5229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2166
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C1_1 C 0.19448(16) 0.40584(15) 0.30754(10) 0.0204(3) Uani 1 1 d . . . . .
H1_1 H 0.088057 0.431524 0.278050 0.025 Uiso 1 1 calc R U . . .
N1_1 N 0.32056(14) 0.43347(13) 0.26740(9) 0.0204(2) Uani 1 1 d . . . . .
C2_1 C 0.40437(17) 0.32039(18) 0.41300(12) 0.0268(3) Uani 1 1 d . . . . .
H2_1 H 0.469568 0.275127 0.470512 0.032 Uiso 1 1 calc R U . . .
N2_1 N 0.24171(14) 0.33637(13) 0.39573(9) 0.0200(3) Uani 1 1 d . . . . .
C3_1 C 0.45325(17) 0.38107(18) 0.33293(11) 0.0255(3) Uani 1 1 d . . . . .
H3_1 H 0.559587 0.386700 0.323395 0.031 Uiso 1 1 calc R U . . .
C4_1 C 0.31853(19) 0.51055(18) 0.17076(11) 0.0272(3) Uani 1 1 d . . . . .
H4A_1 H 0.381580 0.454092 0.130546 0.041 Uiso 1 1 calc R U . . .
H4B_1 H 0.363738 0.610404 0.184332 0.041 Uiso 1 1 calc R U . . .
H4C_1 H 0.208930 0.518623 0.132876 0.041 Uiso 1 1 calc R U . . .
C5_1 C 0.13777(17) 0.28958(16) 0.46511(11) 0.0234(3) Uani 1 1 d . . . . .
H5A_1 H 0.147686 0.180770 0.476345 0.028 Uiso 1 1 calc R U . . .
H5AB_1 H 0.025960 0.311675 0.433608 0.028 Uiso 1 1 calc R U . . .
C6_1 C 0.18149(18) 0.36958(18) 0.56633(11) 0.0272(3) Uani 1 1 d . . . . .
H6A_1 H 0.173955 0.477372 0.555103 0.041 Uiso 1 1 calc R U . . .
H6B_1 H 0.290316 0.343493 0.599231 0.041 Uiso 1 1 calc R U . . .
H6C_1 H 0.108447 0.339580 0.610067 0.041 Uiso 1 1 calc R U . . .
P1_2 P 0.22851(4) 0.84213(4) 0.37194(2) 0.01875(13) Uani 1 1 d . . . . .
F2_2 F 0.07304(10) 0.92290(10) 0.39458(7) 0.0284(2) Uani 1 1 d . . . . .
F3_2 F 0.33869(10) 0.95356(11) 0.44700(7) 0.0329(2) Uani 1 1 d . . . . .
F4_2 F 0.38401(10) 0.76075(10) 0.34895(7) 0.0272(2) Uani 1 1 d . . . . .
F5_2 F 0.11760(11) 0.73028(11) 0.29578(8) 0.0358(2) Uani 1 1 d . . . . .
F6_2 F 0.22891(12) 0.95358(12) 0.27911(7) 0.0366(2) Uani 1 1 d . . . . .
F1_2 F 0.22689(11) 0.72968(12) 0.46379(8) 0.0388(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
C1_1 N1_1 1.3278(18) . ?
C1_1 N2_1 1.3281(18) . ?
C1_1 H1_1 0.9500 . ?
N1_1 C3_1 1.3768(19) . ?
N1_1 C4_1 1.4680(18) . ?
C2_1 C3_1 1.346(2) . ?
C2_1 N2_1 1.3791(18) . ?
C2_1 H2_1 0.9500 . ?
N2_1 C5_1 1.4759(18) . ?
C3_1 H3_1 0.9500 . ?
C4_1 H4A_1 0.9800 . ?
C4_1 H4B_1 0.9800 . ?
C4_1 H4C_1 0.9800 . ?
C5_1 C6_1 1.517(2) . ?
C5_1 H5A_1 0.9900 . ?
C5_1 H5AB_1 0.9900 . ?
C6_1 H6A_1 0.9800 . ?
C6_1 H6B_1 0.9800 . ?
C6_1 H6C_1 0.9800 . ?
P1_2 F3_2 1.5914(9) . ?
P1_2 F1_2 1.5964(10) . ?
P1_2 F6_2 1.5993(9) . ?
P1_2 F2_2 1.6032(9) . ?
P1_2 F5_2 1.6044(9) . ?
P1_2 F4_2 1.6076(9) . ?

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
N1_1 C1_1 N2_1 108.73(12) . . ?
N1_1 C1_1 H1_1 125.6 . . ?
N2_1 C1_1 H1_1 125.6 . . ?
C1_1 N1_1 C3_1 108.46(12) . . ?
C1_1 N1_1 C4_1 125.54(12) . . ?
C3_1 N1_1 C4_1 125.98(12) . . ?
C3_1 C2_1 N2_1 107.01(13) . . ?
C3_1 C2_1 H2_1 126.5 . . ?
N2_1 C2_1 H2_1 126.5 . . ?
C1_1 N2_1 C2_1 108.51(12) . . ?
C1_1 N2_1 C5_1 125.52(12) . . ?
C2_1 N2_1 C5_1 125.93(12) . . ?
C2_1 C3_1 N1_1 107.29(12) . . ?
C2_1 C3_1 H3_1 126.4 . . ?
N1_1 C3_1 H3_1 126.4 . . ?
N1_1 C4_1 H4A_1 109.5 . . ?
N1_1 C4_1 H4B_1 109.5 . . ?
H4A_1 C4_1 H4B_1 109.5 . . ?
N1_1 C4_1 H4C_1 109.5 . . ?
H4A_1 C4_1 H4C_1 109.5 . . ?
H4B_1 C4_1 H4C_1 109.5 . . ?
N2_1 C5_1 C6_1 110.99(12) . . ?
N2_1 C5_1 H5A_1 109.4 . . ?
C6_1 C5_1 H5A_1 109.4 . . ?
N2_1 C5_1 H5AB_1 109.4 . . ?
C6_1 C5_1 H5AB_1 109.4 . . ?
H5A_1 C5_1 H5AB_1 108.0 . . ?
C5_1 C6_1 H6A_1 109.5 . . ?
C5_1 C6_1 H6B_1 109.5 . . ?
H6A_1 C6_1 H6B_1 109.5 . . ?
C5_1 C6_1 H6C_1 109.5 . . ?
H6A_1 C6_1 H6C_1 109.5 . . ?
H6B_1 C6_1 H6C_1 109.5 . . ?
F3_2 P1_2 F1_2 90.29(6) . . ?
F3_2 P1_2 F6_2 90.34(6) . . ?
F1_2 P1_2 F6_2 179.38(6) . . ?
F3_2 P1_2 F2_2 90.50(5) . . ?
F1_2 P1_2 F2_2 90.16(5) . . ?
F6_2 P1_2 F2_2 89.83(5) . . ?
F3_2 P1_2 F5_2 179.71(6) . . ?
F1_2 P1_2 F5_2 90.00(6) . . ?
F6_2 P1_2 F5_2 89.38(6) . . ?
F2_2 P1_2 F5_2 89.56(5) . . ?
F3_2 P1_2 F4_2 89.71(5) . . ?
F1_2 P1_2 F4_2 89.84(5) . . ?
F6_2 P1_2 F4_2 90.17(5) . . ?
F2_2 P1_2 F4_2 179.79(6) . . ?
F5_2 P1_2 F4_2 90.23(5) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.061

