# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

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

data_4-2-2PF6
_database_code_depnum_ccdc_archive 'CCDC 2160042'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_nottingham_internal_coll_name   OJHALI
_nottingham_internal_coll_number 15784
_nottingham_internal_coll_client JH/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '60.0000, 240.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pcxjh6
_nottingham_internal_coll_date   17/03/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'SN, XDA 017/09'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 21/03/2016
_nottingham_internal_process_user pcxjh6
_nottingham_internal_solution_date 21/03/2016
_nottingham_internal_solution_user pcxjh6
_nottingham_internal_refinement_date 23/11/2021
_nottingham_internal_refinement_user pcxjh6/pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 23/11/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 23/11/2021
_refine_special_details          
;
Rigid bond and similarity restraints were applied to the anisotropic displacement parameters of the phosphorous and fluorine atoms of the hexafluorophosphate residues (SIMU, RIGU). The anisotropic displacement parameters of fluorine atoms F4 and F6 were restrained to have more isotropic character. These restraints on the hexafluorophosphate residues were likely necessary as a result of conformational disorder for which a sensible model could not be developed.
The positions of the water and amide hydrogen atoms were located in the electron difference map and were refined with their O-H and N-H distances restrained to have target values of 0.84 and 0.88 %A respectively (DFIX, esd 0.02). The 1,3 intramolecular hydrogen distances of the water residues are restrianed to target values of 1.32 %A (DFIX). The isotropic displacement parameters of the hydrogen atoms were constrained to be 1.5 times the Ueq of their parent nitrogen and oxygen atoms. All other hydrogen atoms were geometrically placed and refined with a riding model.
;
_audit_creation_date             2021-11-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
"4,4'-(3,6-Dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(1- hexylpyridin-1-ium)"
_chemical_formula_moiety         '2(F6 P), C28 H36 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C28 H40 F12 N4 O4 P2'
_chemical_formula_weight         786.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C28 H36 N4 O2 P2 F12'
_chemical_oxdiff_usercomment     
'OJHALI #15784 JHpyridiniumhexyl IN FOMBLIN FILM ON MICROMOUNT FOR JH/DBA'
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2788(8)
_cell_length_b                   9.8717(7)
_cell_length_c                   19.406(2)
_cell_angle_alpha                94.465(7)
_cell_angle_beta                 99.481(8)
_cell_angle_gamma                97.531(6)
_cell_volume                     1729.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2265
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0120
_cell_measurement_theta_min      4.6470
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_preparation       
'obtained by evaporation from a concentrated water: methyl ethyl ketone solution'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: water, methylethylketone'
_exptl_crystal_size_max          0.1867
_exptl_crystal_size_mid          0.1079
_exptl_crystal_size_min          0.0199
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.1210
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16104
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.398
_diffrn_reflns_theta_max         67.398
_diffrn_reflns_theta_min         4.542
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -109.00  -12.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -57.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   34.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -65.00   32.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   57.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   98.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152 -125.0000  120.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   83.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       43.3152  -99.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega   94.00  178.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  125.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000  -30.0000 63

#__ type_ start__ end____ width___ exp.time_
  9 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
 10 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega   31.00   91.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  150.0000 60

#__ type_ start__ end____ width___ exp.time_
 12 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000   60.0000 63

#__ type_ start__ end____ width___ exp.time_
 14 omega   35.00   98.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -45.0000 -150.0000 63

#__ type_ start__ end____ width___ exp.time_
 15 omega   82.00  177.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   45.0000  -30.0000 95

#__ type_ start__ end____ width___ exp.time_
 16 omega   25.00  109.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -95.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   35.00  121.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322 -125.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
 18 omega   31.00   90.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322  -30.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 19 omega   75.00  175.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1322   77.0000   90.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.0418636000
_diffrn_orient_matrix_UB_12      0.0372576000
_diffrn_orient_matrix_UB_13      -0.0756192000
_diffrn_orient_matrix_UB_21      0.0105648000
_diffrn_orient_matrix_UB_22      -0.1476847000
_diffrn_orient_matrix_UB_23      -0.0286444000
_diffrn_orient_matrix_UB_31      -0.1645918000
_diffrn_orient_matrix_UB_32      -0.0428915000
_diffrn_orient_matrix_UB_33      0.0025919000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3507
_reflns_number_total             6212
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.078
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         6212
_refine_ls_number_restraints     361
_refine_ls_R_factor_all          0.1444
_refine_ls_R_factor_gt           0.0867
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2142
_refine_ls_wR_factor_ref         0.2587
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H,H) groups
2. Restrained distances
 O4-H4A
 0.84 with sigma of 0.02
 N2-H2 = N1-H1
 0.88 with sigma of 0.02
 H4A-H4B
 1.32 with sigma of 0.02
 O4-H4B
 0.84 with sigma of 0.02
 O3-H3A
 0.84 with sigma of 0.02
 H3B-H3A
 1.32 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
P1 \\sim F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim P2 \\sim F7
\\sim F8 \\sim F9 \\sim F10 \\sim F11 \\sim F12: within 3A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 3A
Uanis(F4) \\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 P1, F1, F2, F3, F4, F5, F6, P2, F7, F8, F9, F10, F11, F12
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C22(H22)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.08866(17) 0.23574(15) 0.71815(11) 0.0448(5) Uani 1 1 d . U . . .
F1 F 0.2141(4) 0.3467(4) 0.7023(3) 0.0632(12) Uani 1 1 d . U . . .
F2 F 0.1071(6) 0.3120(6) 0.7948(3) 0.0767(13) Uani 1 1 d . U . . .
F3 F 0.2117(4) 0.1444(4) 0.7468(3) 0.0692(13) Uani 1 1 d . U . . .
F4 F 0.0715(6) 0.1586(7) 0.6424(4) 0.108(2) Uani 1 1 d . U . . .
F5 F -0.0323(4) 0.3284(4) 0.6919(3) 0.0647(12) Uani 1 1 d . U . . .
F6 F -0.0381(5) 0.1261(5) 0.7343(4) 0.0970(19) Uani 1 1 d . U . . .
C1 C 0.1835(6) 0.0697(5) 1.0294(3) 0.0288(11) Uani 1 1 d . . . . .
N1 N 0.2751(5) 0.0657(4) 0.9798(2) 0.0294(10) Uani 1 1 d D . . . .
H1 H 0.308(7) -0.006(5) 0.962(3) 0.044 Uiso 1 1 d D U . . .
O1 O 0.1360(4) -0.0331(4) 1.0568(2) 0.0341(9) Uani 1 1 d . . . . .
O2 O 0.2655(5) 0.5316(4) 0.9747(2) 0.0383(10) Uani 1 1 d . . . . .
N2 N 0.1351(5) 0.4342(4) 1.0553(3) 0.0309(10) Uani 1 1 d D . . . .
H2 H 0.125(8) 0.518(3) 1.072(4) 0.046 Uiso 1 1 d D U . . .
C2 C 0.1611(6) 0.2131(5) 1.0386(3) 0.0282(11) Uani 1 1 d . . . . .
N3 N 0.5852(5) 0.2695(5) 0.8078(3) 0.0335(10) Uani 1 1 d . . . . .
C3 C 0.2396(6) 0.2848(5) 0.9923(3) 0.0277(11) Uani 1 1 d . . . . .
N4 N -0.1019(5) 0.2484(5) 1.2543(3) 0.0322(10) Uani 1 1 d . . . . .
C4 C 0.3106(6) 0.1963(5) 0.9579(3) 0.0284(11) Uani 1 1 d . . . . .
C5 C 0.4078(6) 0.2186(6) 0.9067(3) 0.0297(11) Uani 1 1 d . . . . .
C6 C 0.4287(7) 0.3480(6) 0.8819(3) 0.0395(14) Uani 1 1 d . . . . .
H6 H 0.382297 0.420390 0.899436 0.047 Uiso 1 1 calc R U . . .
C7 C 0.5156(7) 0.3696(6) 0.8327(3) 0.0379(13) Uani 1 1 d . . . . .
H7 H 0.527695 0.457069 0.815447 0.046 Uiso 1 1 calc R U . . .
C8 C 0.5688(6) 0.1451(6) 0.8321(3) 0.0371(13) Uani 1 1 d . . . . .
H8 H 0.618551 0.075060 0.814795 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4817(6) 0.1183(6) 0.8811(3) 0.0359(13) Uani 1 1 d . . . . .
H9 H 0.471984 0.030187 0.897798 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6759(7) 0.2966(6) 0.7530(3) 0.0384(13) Uani 1 1 d . . . . .
H10A H 0.744955 0.228289 0.752343 0.046 Uiso 1 1 calc R U . . .
H10B H 0.735367 0.388857 0.764672 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5818(7) 0.2895(6) 0.6806(3) 0.0398(14) Uani 1 1 d . . . . .
H11A H 0.645558 0.321889 0.647197 0.048 Uiso 1 1 calc R U . . .
H11B H 0.507437 0.352479 0.682383 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5026(7) 0.1459(6) 0.6532(3) 0.0393(13) Uani 1 1 d . . . . .
H12A H 0.436879 0.113961 0.685844 0.047 Uiso 1 1 calc R U . . .
H12B H 0.576484 0.082270 0.651962 0.047 Uiso 1 1 calc R U . . .
C13 C 0.4111(7) 0.1417(6) 0.5796(3) 0.0398(13) Uani 1 1 d . . . . .
H13A H 0.335804 0.203664 0.581190 0.048 Uiso 1 1 calc R U . . .
H13B H 0.476550 0.175818 0.547326 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3345(8) -0.0025(7) 0.5512(4) 0.0505(16) Uani 1 1 d . . . . .
H14A H 0.274488 -0.038834 0.585236 0.061 Uiso 1 1 calc R U . . .
H14B H 0.410344 -0.062935 0.546927 0.061 Uiso 1 1 calc R U . . .
C15 C 0.2344(9) -0.0075(9) 0.4796(5) 0.064(2) Uani 1 1 d . . . . .
H15A H 0.291066 0.035572 0.446642 0.096 Uiso 1 1 calc R U . . .
H15B H 0.151302 0.042084 0.484692 0.096 Uiso 1 1 calc R U . . .
H15C H 0.196839 -0.103341 0.461627 0.096 Uiso 1 1 calc R U . . .
C16 C 0.2213(6) 0.4307(6) 1.0028(3) 0.0311(12) Uani 1 1 d . . . . .
C17 C 0.0993(6) 0.3050(5) 1.0774(3) 0.0292(11) Uani 1 1 d . . . . .
C18 C 0.0196(6) 0.2853(5) 1.1353(3) 0.0301(12) Uani 1 1 d . . . . .
C19 C -0.0316(6) 0.3930(5) 1.1695(3) 0.0316(12) Uani 1 1 d . . . . .
H19 H -0.024897 0.480514 1.152121 0.038 Uiso 1 1 calc R U . . .
C20 C -0.0924(6) 0.3724(6) 1.2291(3) 0.0356(13) Uani 1 1 d . . . . .
H20 H -0.127810 0.446157 1.252389 0.043 Uiso 1 1 calc R U . . .
C21 C -0.0579(7) 0.1418(6) 1.2195(4) 0.0403(14) Uani 1 1 d . . . . .
H21 H -0.068809 0.054292 1.236758 0.048 Uiso 1 1 calc R U . . .
C22 C 0.0015(6) 0.1559(6) 1.1605(3) 0.0356(13) Uani 1 1 d . . . . .
H22 H 0.030378 0.078984 1.136608 0.043 Uiso 1 1 calc R U . . .
C23 C -0.1534(7) 0.2292(6) 1.3222(3) 0.0401(14) Uani 1 1 d . . . . .
H23A H -0.212929 0.137333 1.318988 0.048 Uiso 1 1 calc R U . . .
H23B H -0.217100 0.299037 1.331434 0.048 Uiso 1 1 calc R U . . .
C24 C -0.0232(7) 0.2422(6) 1.3824(3) 0.0410(14) Uani 1 1 d . . . . .
H24A H 0.044928 0.178545 1.370210 0.049 Uiso 1 1 calc R U . . .
H24B H -0.060197 0.212534 1.424673 0.049 Uiso 1 1 calc R U . . .
C25 C 0.0635(7) 0.3860(6) 1.4005(3) 0.0409(14) Uani 1 1 d . . . . .
H25A H 0.114705 0.410203 1.361309 0.049 Uiso 1 1 calc R U . . .
H25B H -0.006199 0.452322 1.405728 0.049 Uiso 1 1 calc R U . . .
C26 C 0.1762(7) 0.3989(7) 1.4673(4) 0.0441(15) Uani 1 1 d . . . . .
H26A H 0.252459 0.340478 1.460072 0.053 Uiso 1 1 calc R U . . .
H26B H 0.126754 0.363732 1.505219 0.053 Uiso 1 1 calc R U . . .
C27 C 0.2515(8) 0.5455(7) 1.4910(4) 0.0500(16) Uani 1 1 d . . . . .
H27A H 0.175304 0.604826 1.496928 0.060 Uiso 1 1 calc R U . . .
H27B H 0.304224 0.579833 1.453960 0.060 Uiso 1 1 calc R U . . .
C28 C 0.3610(8) 0.5562(8) 1.5599(4) 0.0536(17) Uani 1 1 d . . . . .
H28A H 0.440473 0.502776 1.553340 0.080 Uiso 1 1 calc R U . . .
H28B H 0.309903 0.520132 1.596399 0.080 Uiso 1 1 calc R U . . .
H28C H 0.402966 0.652677 1.574063 0.080 Uiso 1 1 calc R U . . .
P2 P 0.44909(16) 0.25528(14) 1.22195(9) 0.0393(4) Uani 1 1 d . U . . .
F7 F 0.5748(4) 0.3800(4) 1.2559(2) 0.0519(10) Uani 1 1 d . U . . .
F8 F 0.5693(4) 0.1609(4) 1.2113(2) 0.0585(11) Uani 1 1 d . U . . .
F9 F 0.4506(5) 0.3078(5) 1.1471(2) 0.0629(11) Uani 1 1 d . U . . .
F10 F 0.4475(5) 0.2067(5) 1.2995(2) 0.0673(12) Uani 1 1 d . U . . .
F11 F 0.3266(4) 0.3529(4) 1.2340(2) 0.0552(10) Uani 1 1 d . U . . .
F12 F 0.3207(4) 0.1341(4) 1.1902(3) 0.0624(12) Uani 1 1 d . U . . .
O3 O 0.3564(5) -0.1951(4) 0.9418(3) 0.0406(10) Uani 1 1 d D . . . .
H3A H 0.384(8) -0.228(7) 0.905(3) 0.061 Uiso 1 1 d D U . . .
H3B H 0.328(8) -0.259(9) 0.961(3) 0.061 Uiso 1 1 d D U . . .
O4 O 0.0837(5) 0.7020(4) 1.1031(2) 0.0368(9) Uani 1 1 d D . . . .
H4A H 0.106(8) 0.781(3) 1.091(3) 0.055 Uiso 1 1 d D U . . .
H4B H 0.052(8) 0.718(6) 1.141(2) 0.055 Uiso 1 1 d D 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 F1 1.577(4) . ?
P1 F2 1.587(6) . ?
P1 F3 1.601(4) . ?
P1 F4 1.575(6) . ?
P1 F5 1.584(4) . ?
P1 F6 1.580(4) . ?
C1 N1 1.388(8) . ?
C1 O1 1.245(7) . ?
C1 C2 1.459(7) . ?
N1 H1 0.88(2) . ?
N1 C4 1.405(7) . ?
O2 C16 1.229(7) . ?
N2 H2 0.88(2) . ?
N2 C16 1.395(8) . ?
N2 C17 1.394(7) . ?
C2 C3 1.421(8) . ?
C2 C17 1.375(8) . ?
N3 C7 1.349(8) . ?
N3 C8 1.348(8) . ?
N3 C10 1.481(8) . ?
C3 C4 1.360(8) . ?
C3 C16 1.474(7) . ?
N4 C20 1.351(7) . ?
N4 C21 1.350(8) . ?
N4 C23 1.490(8) . ?
C4 C5 1.457(8) . ?
C5 C6 1.400(8) . ?
C5 C9 1.382(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.360(9) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.366(9) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.531(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.533(11) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C18 1.455(8) . ?
C18 C19 1.386(8) . ?
C18 C22 1.403(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(9) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.358(9) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.521(9) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.522(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.511(9) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.523(9) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.528(10) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
P2 F7 1.599(4) . ?
P2 F8 1.572(4) . ?
P2 F9 1.582(5) . ?
P2 F10 1.616(5) . ?
P2 F11 1.617(4) . ?
P2 F12 1.581(4) . ?
O3 H3A 0.85(2) . ?
O3 H3B 0.79(7) . ?
O4 H4A 0.85(2) . ?
O4 H4B 0.84(2) . ?

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
F1 P1 F2 89.1(3) . . ?
F1 P1 F3 89.4(2) . . ?
F1 P1 F5 90.5(2) . . ?
F1 P1 F6 179.3(3) . . ?
F2 P1 F3 89.4(3) . . ?
F4 P1 F1 91.1(4) . . ?
F4 P1 F2 179.3(3) . . ?
F4 P1 F3 89.9(3) . . ?
F4 P1 F5 91.7(3) . . ?
F4 P1 F6 89.3(4) . . ?
F5 P1 F2 89.0(3) . . ?
F5 P1 F3 178.4(3) . . ?
F6 P1 F2 90.5(4) . . ?
F6 P1 F3 91.2(2) . . ?
F6 P1 F5 89.0(2) . . ?
N1 C1 C2 104.7(4) . . ?
O1 C1 N1 123.5(5) . . ?
O1 C1 C2 131.8(5) . . ?
C1 N1 H1 128(5) . . ?
C1 N1 C4 111.2(4) . . ?
C4 N1 H1 121(5) . . ?
C16 N2 H2 114(5) . . ?
C17 N2 H2 133(5) . . ?
C17 N2 C16 112.3(4) . . ?
C3 C2 C1 107.2(5) . . ?
C17 C2 C1 143.6(5) . . ?
C17 C2 C3 109.1(5) . . ?
C7 N3 C10 119.6(5) . . ?
C8 N3 C7 119.6(5) . . ?
C8 N3 C10 120.7(5) . . ?
C2 C3 C16 107.5(5) . . ?
C4 C3 C2 109.3(5) . . ?
C4 C3 C16 143.1(5) . . ?
C20 N4 C23 120.8(5) . . ?
C21 N4 C20 119.8(5) . . ?
C21 N4 C23 119.3(5) . . ?
N1 C4 C5 121.4(5) . . ?
C3 C4 N1 107.6(5) . . ?
C3 C4 C5 131.0(5) . . ?
C6 C5 C4 118.9(5) . . ?
C9 C5 C4 123.4(5) . . ?
C9 C5 C6 117.7(5) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.7(5) . . ?
C7 C6 H6 120.1 . . ?
N3 C7 C6 121.5(5) . . ?
N3 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N3 C8 H8 119.5 . . ?
N3 C8 C9 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C5 C9 H9 119.8 . . ?
C8 C9 C5 120.4(5) . . ?
C8 C9 H9 119.8 . . ?
N3 C10 H10A 109.2 . . ?
N3 C10 H10B 109.2 . . ?
N3 C10 C11 112.1(5) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 C12 113.3(5) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C11 C12 C13 112.0(5) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.3(5) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.1(6) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N2 124.2(5) . . ?
O2 C16 C3 132.1(5) . . ?
N2 C16 C3 103.7(4) . . ?
N2 C17 C18 122.1(5) . . ?
C2 C17 N2 107.4(5) . . ?
C2 C17 C18 130.4(5) . . ?
C19 C18 C17 121.9(5) . . ?
C19 C18 C22 118.5(5) . . ?
C22 C18 C17 119.5(5) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(5) . . ?
C20 C19 H19 120.1 . . ?
N4 C20 C19 120.5(5) . . ?
N4 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N4 C21 H21 119.0 . . ?
N4 C21 C22 122.0(5) . . ?
C22 C21 H21 119.0 . . ?
C18 C22 H22 120.4 . . ?
C21 C22 C18 119.2(5) . . ?
C21 C22 H22 120.4 . . ?
N4 C23 H23A 109.4 . . ?
N4 C23 H23B 109.4 . . ?
N4 C23 C24 111.0(5) . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C23 C24 C25 114.8(5) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.8(5) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C25 C26 C27 113.6(5) . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C26 C27 C28 112.4(6) . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
F7 P2 F10 88.8(2) . . ?
F7 P2 F11 88.7(2) . . ?
F8 P2 F7 90.8(2) . . ?
F8 P2 F9 91.6(3) . . ?
F8 P2 F10 89.8(3) . . ?
F8 P2 F11 179.3(3) . . ?
F8 P2 F12 91.1(2) . . ?
F9 P2 F7 89.9(2) . . ?
F9 P2 F10 178.2(3) . . ?
F9 P2 F11 89.0(2) . . ?
F10 P2 F11 89.7(3) . . ?
F12 P2 F7 177.8(3) . . ?
F12 P2 F9 91.2(3) . . ?
F12 P2 F10 90.0(3) . . ?
F12 P2 F11 89.4(2) . . ?
H3A O3 H3B 106(6) . . ?
H4A O4 H4B 103(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88(2) 2.00(3) 2.853(6) 164(7) . yes
N2 H2 O4 0.88(2) 1.98(2) 2.858(6) 175(7) . yes
O3 H3B O2 0.79(7) 2.12(8) 2.871(5) 158(7) 1_545 yes
O4 H4A O1 0.85(2) 2.00(2) 2.839(5) 174(7) 1_565 yes
O4 H4B F2 0.84(2) 2.09(4) 2.866(7) 152(7) 2_567 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C4 C3 -1.2(6) . . . . ?
C1 N1 C4 C5 178.9(5) . . . . ?
C1 C2 C3 C4 -1.8(6) . . . . ?
C1 C2 C3 C16 -178.3(4) . . . . ?
C1 C2 C17 N2 176.4(7) . . . . ?
C1 C2 C17 C18 0.8(12) . . . . ?
N1 C1 C2 C3 1.0(6) . . . . ?
N1 C1 C2 C17 -174.2(7) . . . . ?
N1 C4 C5 C6 174.2(5) . . . . ?
N1 C4 C5 C9 -6.1(8) . . . . ?
O1 C1 N1 C4 179.7(5) . . . . ?
O1 C1 C2 C3 -178.6(6) . . . . ?
O1 C1 C2 C17 6.2(12) . . . . ?
N2 C17 C18 C19 3.2(8) . . . . ?
N2 C17 C18 C22 -172.7(5) . . . . ?
C2 C1 N1 C4 0.0(6) . . . . ?
C2 C3 C4 N1 1.8(6) . . . . ?
C2 C3 C4 C5 -178.3(5) . . . . ?
C2 C3 C16 O2 -178.7(6) . . . . ?
C2 C3 C16 N2 0.9(6) . . . . ?
C2 C17 C18 C19 178.2(6) . . . . ?
C2 C17 C18 C22 2.3(9) . . . . ?
N3 C8 C9 C5 0.3(9) . . . . ?
N3 C10 C11 C12 -67.1(6) . . . . ?
C3 C2 C17 N2 1.2(6) . . . . ?
C3 C2 C17 C18 -174.3(5) . . . . ?
C3 C4 C5 C6 -5.6(9) . . . . ?
C3 C4 C5 C9 174.1(6) . . . . ?
N4 C21 C22 C18 0.8(10) . . . . ?
N4 C23 C24 C25 68.4(7) . . . . ?
C4 C3 C16 O2 6.8(13) . . . . ?
C4 C3 C16 N2 -173.6(7) . . . . ?
C4 C5 C6 C7 -178.2(6) . . . . ?
C4 C5 C9 C8 178.6(6) . . . . ?
C5 C6 C7 N3 -1.3(10) . . . . ?
C6 C5 C9 C8 -1.7(9) . . . . ?
C7 N3 C8 C9 0.6(9) . . . . ?
C7 N3 C10 C11 -78.3(7) . . . . ?
C8 N3 C7 C6 -0.1(9) . . . . ?
C8 N3 C10 C11 100.3(6) . . . . ?
C9 C5 C6 C7 2.1(9) . . . . ?
C10 N3 C7 C6 178.5(6) . . . . ?
C10 N3 C8 C9 -178.0(6) . . . . ?
C10 C11 C12 C13 -178.9(5) . . . . ?
C11 C12 C13 C14 178.6(5) . . . . ?
C12 C13 C14 C15 176.3(6) . . . . ?
C16 N2 C17 C2 -0.6(6) . . . . ?
C16 N2 C17 C18 175.3(5) . . . . ?
C16 C3 C4 N1 176.3(7) . . . . ?
C16 C3 C4 C5 -3.9(12) . . . . ?
C17 N2 C16 O2 179.5(5) . . . . ?
C17 N2 C16 C3 -0.2(6) . . . . ?
C17 C2 C3 C4 175.2(5) . . . . ?
C17 C2 C3 C16 -1.3(6) . . . . ?
C17 C18 C19 C20 -173.0(5) . . . . ?
C17 C18 C22 C21 172.5(6) . . . . ?
C18 C19 C20 N4 0.2(9) . . . . ?
C19 C18 C22 C21 -3.5(9) . . . . ?
C20 N4 C21 C22 2.5(9) . . . . ?
C20 N4 C23 C24 -95.4(6) . . . . ?
C21 N4 C20 C19 -3.0(9) . . . . ?
C21 N4 C23 C24 81.5(7) . . . . ?
C22 C18 C19 C20 3.0(8) . . . . ?
C23 N4 C20 C19 173.9(5) . . . . ?
C23 N4 C21 C22 -174.5(6) . . . . ?
C23 C24 C25 C26 171.1(5) . . . . ?
C24 C25 C26 C27 -173.3(5) . . . . ?
C25 C26 C27 C28 178.1(6) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 5 -3 0.0913 -1.0030 4.9958 -3.0008 0.4550 -0.6624 -0.0570
1 -5 3 0.0913 1.0030 -4.9958 3.0008 -0.4550 0.6624 0.0570
5 1 -2 0.0525 5.0017 1.0018 -2.0000 -0.0208 -0.0378 -0.8714
-5 -1 2 0.0525 -5.0017 -1.0018 2.0000 0.0208 0.0378 0.8714
0 1 5 0.0100 -0.0007 1.0008 5.0019 -0.3409 -0.2911 -0.0298
0 -1 -5 0.0100 0.0007 -1.0008 -5.0019 0.3409 0.2911 0.0298
5 3 -4 0.0597 5.0007 3.0002 -4.0006 0.2050 -0.2757 -0.9621
1 0 0 0.0462 1.0004 0.0006 0.0001 -0.0419 0.0105 -0.1647
1 -1 0 0.0673 1.0010 -0.9989 0.0001 -0.0791 0.1581 -0.1219
2 -3 5 0.0719 2.0023 -2.9958 5.0018 -0.5737 0.3203 -0.1881

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OJHALI
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3-3-2PF6
_database_code_depnum_ccdc_archive 'CCDC 2160044'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_nottingham_internal_coll_name   DPPFMI
_nottingham_internal_coll_number 18960
_nottingham_internal_coll_client FM/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   11/02/2021
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 13/02/2021
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 16/02/2021
_nottingham_internal_solution_user pczspa/pcxfm
_nottingham_internal_refinement_date 16/02/2021
_nottingham_internal_refinement_user pczspa/pcxfm
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 16/02/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 16/02/2021
_refine_special_details          
'Pyrolic lactone hydrogen H1 was refined and its N-H distance restrained to a target value of 0.88 A (DFIX). The isotropic displacement parameter of H1 was constrained to have a value of 1.2 times Ueq of its parent nitrogen atom N1. All other hydogen atoms in the structure were observed in the electron density map before being geometrically placed and refined with a riding model.'
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4 O2, 2(C2 H3 N), 2(F6 P)'
_chemical_formula_sum            'C34 H30 F12 N6 O2 P2'
_chemical_formula_weight         844.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H24N4O2P2F6
_chemical_oxdiff_usercomment     
'DPPFMI #18960 MM-751 FM/DBA fomblin on micromount'
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.56026(5)
_cell_length_b                   13.16435(8)
_cell_length_c                   21.40535(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.7893(6)
_cell_angle_gamma                90
_cell_volume                     1839.17(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    28355
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      75.0510
_cell_measurement_theta_min      3.9240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.007
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             860
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 4 0.0211
0 5 -4 0.0161
0 1 5 0.0307
0 -1 -5 0.0257
-4 -2 5 0.1533
4 2 -5 0.1770

_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0004 -5.0057 3.9737 0.2516 -0.5668 0.2032
0.0004 5.0057 -3.9737 -0.2516 0.5668 -0.2032
0.0018 0.9898 5.0002 0.3665 0.0999 0.0026
-0.0018 -0.9898 -5.0002 -0.3665 -0.0999 -0.0026
-3.9995 -1.9902 4.9765 0.1651 0.0527 0.9877
3.9995 1.9902 -4.9765 -0.1651 -0.0527 -0.9877

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            40002
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.326
_diffrn_reflns_theta_min         3.948
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  25.00   0.50    1.00    --    0.00 -57.00 -30.00  228
  2  ω    -89.00  23.00   0.50    1.00    --    0.00 -38.00  30.00  224
  3  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00-120.00  132
  4  ω     87.00 187.00   0.50    4.00    --   97.70  82.00-120.00  200
  5  ω     74.00 187.00   0.50    4.00    --   97.70  45.00-120.00  226
  6  ω      8.00 135.00   0.50    4.00    --   97.70 -15.00 -90.00  254
  7  ω      8.00 131.00   0.50    4.00    --   97.70 -82.00 150.00  246
  8  ω      8.00 124.00   0.50    4.00    --   97.70 -61.00 -60.00  232
  9  ω      8.00 124.00   0.50    4.00    --   97.70 -61.00 150.00  232
 10  ω     74.00 187.00   0.50    4.00    --   97.70  39.00  -5.29  226
 11  ω      8.00 131.00   0.50    4.00    --   97.70 -82.00  90.00  246
 12  ω      8.00 124.00   0.50    4.00    --   97.70 -61.00 -30.00  232
 13  ω     71.00 187.00   0.50    4.00    --   97.70  61.00  90.00  232
 14  ω      8.00 131.00   0.50    4.00    --   97.70 -82.00 -60.00  246
 15  ω      8.00 131.00   0.50    4.00    --   97.70 -82.00 -30.00  246
 16  ω     79.00 187.00   0.50    4.00    --   97.70  77.00  90.00  216
 17  ω      8.00 131.00   0.50    4.00    --   97.70 -82.00   0.00  246
 18  ω     73.00 187.00   0.50    4.00    --   97.70  30.00   0.00  228
 19  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00-150.00  132
 20  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00  30.00  132
 21  ω    -33.00  33.00   0.50    1.00    --    0.00 -82.00 150.00  132
 22  ω     74.00 187.00   0.50    4.00    --   97.70  45.00 -60.00  226
 23  ω     73.00 187.00   0.50    4.00    --   97.70  30.00-180.00  228
 24  ω     71.00 187.00   0.50    4.00    --   97.70  61.00  60.00  232
 25  ω     74.00 187.00   0.50    4.00    --   97.70  45.00 -90.00  226
 26  ω     74.00 187.00   0.50    4.00    --   97.70  45.00-150.00  226
 27  ω     71.00 151.00   0.50    4.00    --   97.70  61.00 120.00  160
 28  ω     74.00 187.00   0.50    4.00    --   97.70  45.00  30.00  226
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0448139000
_diffrn_orient_matrix_UB_12      0.0068345000
_diffrn_orient_matrix_UB_13      0.0719335000
_diffrn_orient_matrix_UB_21      -0.0712913000
_diffrn_orient_matrix_UB_22      0.1115862000
_diffrn_orient_matrix_UB_23      -0.0020819000
_diffrn_orient_matrix_UB_31      -0.2204356000
_diffrn_orient_matrix_UB_32      -0.0346651000
_diffrn_orient_matrix_UB_33      0.0074582000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3581
_reflns_number_total             3779
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+1.3347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1159
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
3.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7688(2) 0.50689(11) 0.56406(7) 0.0254(3) Uani 1 1 d D . . . .
H1 H 0.884(3) 0.5134(16) 0.5882(9) 0.031 Uiso 1 1 d D U . . .
C2 C 0.7250(2) 0.43239(12) 0.51913(7) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.5376(2) 0.45454(12) 0.48742(7) 0.0240(3) Uani 1 1 d . . . . .
C4 C 0.6136(3) 0.58074(12) 0.56276(8) 0.0251(3) Uani 1 1 d . . . . .
O5 O 0.61890(19) 0.65490(9) 0.59721(6) 0.0308(3) Uani 1 1 d . . . . .
N6 N 0.9317(2) 0.19722(10) 0.45617(6) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.8068(2) 0.27598(12) 0.46550(7) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.677793 0.281429 0.441219 0.029 Uiso 1 1 calc R U . . .
C8 C 0.8658(2) 0.34902(12) 0.51040(7) 0.0236(3) Uani 1 1 d . . . . .
C9 C 1.0571(3) 0.33985(13) 0.54506(8) 0.0280(4) Uani 1 1 d . . . . .
H9 H 1.100167 0.388668 0.576328 0.034 Uiso 1 1 calc R U . . .
C10 C 1.1832(3) 0.25936(14) 0.53360(8) 0.0308(4) Uani 1 1 d . . . . .
H10 H 1.314681 0.253223 0.556345 0.037 Uiso 1 1 calc R U . . .
C11 C 1.1171(3) 0.18791(13) 0.48888(8) 0.0286(4) Uani 1 1 d . . . . .
H11 H 1.202596 0.131994 0.481171 0.034 Uiso 1 1 calc R U . . .
C12 C 0.8555(3) 0.11853(13) 0.40909(8) 0.0286(4) Uani 1 1 d . . . . .
H12A H 0.722877 0.091473 0.420080 0.034 Uiso 1 1 calc R U . . .
H12B H 0.954291 0.061545 0.410463 0.034 Uiso 1 1 calc R U . . .
C13 C 0.8279(3) 0.16189(13) 0.34361(8) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.9912(3) 0.20837(16) 0.31813(9) 0.0401(5) Uani 1 1 d . . . . .
H14 H 1.120456 0.213775 0.342263 0.048 Uiso 1 1 calc R U . . .
C15 C 0.9654(4) 0.24658(18) 0.25786(10) 0.0521(6) Uani 1 1 d . . . . .
H15 H 1.076785 0.278726 0.240653 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7782(4) 0.23824(19) 0.22243(10) 0.0550(6) Uani 1 1 d . . . . .
H16 H 0.761160 0.264587 0.180915 0.066 Uiso 1 1 calc R U . . .
C17 C 0.6158(4) 0.1917(2) 0.24720(11) 0.0522(6) Uani 1 1 d . . . . .
H17 H 0.487372 0.185733 0.222692 0.063 Uiso 1 1 calc R U . . .
C18 C 0.6407(3) 0.15356(16) 0.30818(9) 0.0396(4) Uani 1 1 d . . . . .
H18 H 0.528883 0.121838 0.325402 0.048 Uiso 1 1 calc R U . . .
N21 N 1.1546(3) 0.53670(14) 0.64262(8) 0.0422(4) Uani 1 1 d . . . . .
C22 C 1.2890(4) 0.53723(16) 0.68009(10) 0.0443(5) Uani 1 1 d . . . . .
C23 C 1.4644(4) 0.5382(2) 0.72758(14) 0.0669(8) Uani 1 1 d . . . . .
H23A H 1.556364 0.594029 0.718949 0.100 Uiso 1 1 calc R U . . .
H23B H 1.537921 0.473551 0.726617 0.100 Uiso 1 1 calc R U . . .
H23C H 1.416799 0.547803 0.769135 0.100 Uiso 1 1 calc R U . . .
P31 P 0.65096(7) 0.09358(3) 0.60370(2) 0.02759(14) Uani 1 1 d . . . . .
F32 F 0.64330(17) 0.21379(8) 0.61495(6) 0.0402(3) Uani 1 1 d . . . . .
F33 F 0.88763(19) 0.10179(10) 0.59391(8) 0.0585(4) Uani 1 1 d . . . . .
F34 F 0.7032(2) 0.07494(11) 0.67636(6) 0.0537(4) Uani 1 1 d . . . . .
F35 F 0.65750(18) -0.02641(9) 0.59164(6) 0.0431(3) Uani 1 1 d . . . . .
F36 F 0.41218(17) 0.08570(8) 0.61184(6) 0.0402(3) Uani 1 1 d . . . . .
F37 F 0.5914(2) 0.11361(10) 0.53014(6) 0.0505(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.875(15) . ?
N1 C2 1.383(2) . ?
N1 C4 1.406(2) . ?
C2 C3 1.374(2) . ?
C2 C8 1.459(2) . ?
C3 C3 1.421(3) 3_666 ?
C3 C4 1.462(2) 3_666 ?
C4 O5 1.222(2) . ?
N6 C7 1.349(2) . ?
N6 C11 1.346(2) . ?
N6 C12 1.496(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(2) . ?
C8 C9 1.397(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.507(2) . ?
C13 C14 1.392(3) . ?
C13 C18 1.381(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(3) . ?
C18 H18 0.9500 . ?
N21 C22 1.131(3) . ?
C22 C23 1.456(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
P31 F32 1.6022(12) . ?
P31 F33 1.5912(13) . ?
P31 F34 1.5777(12) . ?
P31 F35 1.6019(12) . ?
P31 F36 1.5969(12) . ?
P31 F37 1.6054(13) . ?

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
C2 N1 H1 125.9(14) . . ?
C2 N1 C4 112.17(13) . . ?
C4 N1 H1 121.6(14) . . ?
N1 C2 C8 122.18(14) . . ?
C3 C2 N1 107.79(14) . . ?
C3 C2 C8 130.02(15) . . ?
C2 C3 C3 108.61(17) . 3_666 ?
C2 C3 C4 143.33(15) . 3_666 ?
C3 C3 C4 108.06(17) 3_666 3_666 ?
N1 C4 C3 103.36(13) . 3_666 ?
O5 C4 N1 124.34(15) . . ?
O5 C4 C3 132.30(15) . 3_666 ?
C7 N6 C12 117.71(14) . . ?
C11 N6 C7 121.57(15) . . ?
C11 N6 C12 120.70(14) . . ?
N6 C7 H7 119.9 . . ?
N6 C7 C8 120.26(15) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C2 118.30(15) . . ?
C7 C8 C9 118.78(15) . . ?
C9 C8 C2 122.93(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.59(16) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.59(16) . . ?
C11 C10 H10 120.2 . . ?
N6 C11 C10 120.19(15) . . ?
N6 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N6 C12 H12A 109.3 . . ?
N6 C12 H12B 109.3 . . ?
N6 C12 C13 111.40(14) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C14 C13 C12 120.39(17) . . ?
C18 C13 C12 119.81(16) . . ?
C18 C13 C14 119.78(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 120.0(2) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
N21 C22 C23 179.1(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F32 P31 F37 88.69(7) . . ?
F33 P31 F32 89.92(7) . . ?
F33 P31 F35 90.19(7) . . ?
F33 P31 F36 178.68(8) . . ?
F33 P31 F37 90.21(8) . . ?
F34 P31 F32 90.71(7) . . ?
F34 P31 F33 91.29(9) . . ?
F34 P31 F35 89.93(7) . . ?
F34 P31 F36 90.02(8) . . ?
F34 P31 F37 178.38(8) . . ?
F35 P31 F32 179.34(7) . . ?
F35 P31 F37 90.67(7) . . ?
F36 P31 F32 90.10(6) . . ?
F36 P31 F35 89.77(6) . . ?
F36 P31 F37 88.47(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N21 0.875(15) 2.046(16) 2.920(2) 177(2) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C3 0.5(2) . . . 3_666 ?
N1 C2 C3 C4 -179.6(2) . . . 3_666 ?
N1 C2 C8 C7 178.08(15) . . . . ?
N1 C2 C8 C9 -2.1(3) . . . . ?
C2 N1 C4 C3 0.74(18) . . . 3_666 ?
C2 N1 C4 O5 -178.76(16) . . . . ?
C2 C8 C9 C10 -179.22(16) . . . . ?
C3 C2 C8 C7 -2.9(3) . . . . ?
C3 C2 C8 C9 176.87(17) . . . . ?
C4 N1 C2 C3 -0.78(19) . . . . ?
C4 N1 C2 C8 178.41(15) . . . . ?
N6 C7 C8 C2 -179.56(14) . . . . ?
N6 C7 C8 C9 0.6(2) . . . . ?
N6 C12 C13 C14 56.5(2) . . . . ?
N6 C12 C13 C18 -124.87(18) . . . . ?
C7 N6 C11 C10 0.5(2) . . . . ?
C7 N6 C12 C13 65.58(19) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C2 C3 C3 -178.63(18) . . . 3_666 ?
C8 C2 C3 C4 1.3(4) . . . 3_666 ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C9 C10 C11 N6 0.7(3) . . . . ?
C11 N6 C7 C8 -1.2(2) . . . . ?
C11 N6 C12 C13 -115.87(17) . . . . ?
C12 N6 C7 C8 177.35(14) . . . . ?
C12 N6 C11 C10 -177.99(16) . . . . ?
C12 C13 C14 C15 179.09(19) . . . . ?
C12 C13 C18 C17 -178.70(19) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C18 C13 C14 C15 0.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.614
_oxdiff_exptl_absorpt_empirical_full_min 0.642

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_3-2-2PF6
_database_code_depnum_ccdc_archive 'CCDC 2160043'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;University of Nottingham
United Kingdom
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2023-01-03 downloaded from the CCDC.
;
_nottingham_internal_coll_name   DPPFMB_C1
_nottingham_internal_coll_number 18572
_nottingham_internal_coll_client FM/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'fine \w scans'
_nottingham_internal_coll_frame_time 0.2
_nottingham_internal_coll_frame_width 0.01
_nottingham_internal_coll_user   pczspa
_nottingham_internal_coll_date   26/01/2020
_nottingham_internal_coll_location DLS
_nottingham_internal_coll_instrument i19-EH1
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 26/01/2020
_nottingham_internal_process_user pczspa
_nottingham_internal_solution_date 26/01/2020
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 10/12/2021
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 10/12/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 10/12/2021
_refine_special_details          
'All hydrogen atoms were observed in the electron density map. The position of amide hydrogen H1 was refined with the N-H distance restrained to a target value of 0.88 %A (DFIX, esd 0.02 %A). All other hydrogen atoms were geometrically placed and refined with a riding model.'
_audit_creation_date             2021-12-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H36 N4 O2, 2(F6 P)'
_chemical_formula_sum            'C28 H36 F12 N4 O2 P2'
_chemical_formula_weight         750.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0167 0.0096 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.0990 0.0908 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

loop_
_symmetry_equiv_pos_as_xyz
-x,y,-z+1/2

_cell_length_a                   34.9289(7)
_cell_length_b                   9.64811(19)
_cell_length_c                   9.32463(17)
_cell_angle_alpha                90.0
_cell_angle_beta                 96.9621(18)
_cell_angle_gamma                90.0
_cell_volume                     3119.21(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5070056337
_cell_measurement_theta_min      2.27018366285
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.9941388463812154
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.078: AIMLESS, version 0.7.4 : 13/12/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         29.477
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3386
_reflns_number_total             4749
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 2.1.1-gcdd629a7b-release'
_computing_data_collection       ?
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 2.1.1-gcdd629a7b-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.6.366-ga657f9d9-dials-2.1 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4749
_refine_ls_number_restraints     175
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+1.0726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1174
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1_$1-H1_$1
 0.88 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11)
4.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.45623(4) 0.56409(13) 0.62453(14) 0.0137(3) Uani 1 1 d . . . . .
H1 H 0.4391(5) 0.5921(18) 0.673(2) 0.016 Uiso 1 1 d . U . . .
C2 C 0.47817(4) 0.65934(16) 0.55413(16) 0.0126(3) Uani 1 1 d . . . . .
O3 O 0.47375(3) 0.78493(11) 0.55659(13) 0.0188(2) Uani 1 1 d . . . . .
C4 C 0.49583(4) 0.42982(15) 0.51639(16) 0.0117(3) Uani 1 1 d . . . . .
C5 C 0.46652(4) 0.42785(15) 0.60267(15) 0.0115(3) Uani 1 1 d . . . . .
N6 N 0.40023(4) 0.22270(13) 0.80281(14) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.41706(4) 0.33056(16) 0.74366(15) 0.0131(3) Uani 1 1 d . . . . .
H7 H 0.407777 0.421761 0.756287 0.016 Uiso 1 1 calc R U . . .
C8 C 0.44778(4) 0.31050(15) 0.66451(15) 0.0117(3) Uani 1 1 d . . . . .
C9 C 0.46015(4) 0.17363(16) 0.64383(16) 0.0142(3) Uani 1 1 d . . . . .
H9 H 0.480456 0.156077 0.587109 0.017 Uiso 1 1 calc R U . . .
C10 C 0.44244(5) 0.06530(16) 0.70688(17) 0.0163(3) Uani 1 1 d . . . . .
H10 H 0.450706 -0.027290 0.694580 0.020 Uiso 1 1 calc R U . . .
C11 C 0.41271(5) 0.09210(16) 0.78779(17) 0.0154(3) Uani 1 1 d . . . . .
H11 H 0.400972 0.017863 0.833199 0.018 Uiso 1 1 calc R U . . .
C12 C 0.36573(5) 0.24957(17) 0.88045(18) 0.0184(3) Uani 1 1 d . . . . .
H12A H 0.368618 0.340677 0.929409 0.022 Uiso 1 1 calc R U . . .
H12B H 0.364217 0.177567 0.955195 0.022 Uiso 1 1 calc R U . . .
C13 C 0.32872(5) 0.24850(17) 0.77590(19) 0.0185(3) Uani 1 1 d . . . . .
H13A H 0.331867 0.311925 0.694684 0.022 Uiso 1 1 calc R U . . .
H13B H 0.307456 0.284854 0.826277 0.022 Uiso 1 1 calc R U . . .
C14 C 0.31742(5) 0.10586(16) 0.71506(18) 0.0173(3) Uani 1 1 d . . . . .
H14A H 0.315719 0.040809 0.796152 0.021 Uiso 1 1 calc R U . . .
H14B H 0.337874 0.071774 0.659187 0.021 Uiso 1 1 calc R U . . .
C15 C 0.27898(5) 0.10606(17) 0.61757(19) 0.0201(3) Uani 1 1 d . . . . .
H15A H 0.258899 0.147012 0.670894 0.024 Uiso 1 1 calc R U . . .
H15B H 0.281319 0.165141 0.532259 0.024 Uiso 1 1 calc R U . . .
C16 C 0.26636(5) -0.03912(17) 0.56660(18) 0.0206(3) Uani 1 1 d . . . . .
H16A H 0.287081 -0.081881 0.517905 0.025 Uiso 1 1 calc R U . . .
H16B H 0.262745 -0.096726 0.651783 0.025 Uiso 1 1 calc R U . . .
C17 C 0.22925(5) -0.0393(2) 0.4636(2) 0.0266(4) Uani 1 1 d . . . . .
H17A H 0.232688 0.016723 0.378394 0.040 Uiso 1 1 calc R U . . .
H17B H 0.208368 -0.000065 0.512184 0.040 Uiso 1 1 calc R U . . .
H17C H 0.222705 -0.134581 0.433596 0.040 Uiso 1 1 calc R U . . .
P1A P 0.36949(2) 0.70957(4) 0.83388(4) 0.01377(11) Uani 1 1 d . . . . .
F2A F 0.41572(3) 0.70005(15) 0.83328(13) 0.0419(3) Uani 1 1 d . . . . .
F3A F 0.37632(3) 0.82708(10) 0.95582(10) 0.0208(2) Uani 1 1 d . . . . .
F4A F 0.32462(3) 0.71890(15) 0.83460(14) 0.0442(3) Uani 1 1 d . . . . .
F5A F 0.36453(3) 0.59195(10) 0.71110(11) 0.0312(3) Uani 1 1 d . . . . .
F6A F 0.36786(4) 0.82454(11) 0.71164(11) 0.0333(3) Uani 1 1 d . . . . .
F7A F 0.37280(4) 0.59373(11) 0.95655(12) 0.0438(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.838(14) . ?
N1 C2 1.409(2) . ?
N1 C5 1.3844(19) . ?
C2 O3 1.2220(18) . ?
C2 C4 1.464(2) 5_666 ?
C4 C4 1.426(3) 5_666 ?
C4 C5 1.377(2) . ?
C5 C8 1.461(2) . ?
N6 C7 1.346(2) . ?
N6 C11 1.346(2) . ?
N6 C12 1.502(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C8 C9 1.410(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.517(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
P1A F2A 1.6182(11) . ?
P1A F3A 1.6030(10) . ?
P1A F4A 1.5707(12) . ?
P1A F5A 1.6063(10) . ?
P1A F6A 1.5866(11) . ?
P1A F7A 1.5934(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 120.4(13) . . ?
C5 N1 H1 126.9(13) . . ?
C5 N1 C2 112.65(12) . . ?
N1 C2 C4 103.19(12) . 5_666 ?
O3 C2 N1 124.12(14) . . ?
O3 C2 C4 132.68(14) . 5_666 ?
C4 C4 C2 107.94(16) 5_666 5_666 ?
C5 C4 C2 143.16(14) . 5_666 ?
C5 C4 C4 108.90(16) . 5_666 ?
N1 C5 C8 122.75(13) . . ?
C4 C5 N1 107.32(13) . . ?
C4 C5 C8 129.93(13) . . ?
C7 N6 C11 121.19(14) . . ?
C7 N6 C12 118.69(13) . . ?
C11 N6 C12 120.05(13) . . ?
N6 C7 H7 119.5 . . ?
N6 C7 C8 120.97(14) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C5 120.94(13) . . ?
C7 C8 C9 118.22(13) . . ?
C9 C8 C5 120.83(13) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.34(14) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.75(14) . . ?
C11 C10 H10 120.1 . . ?
N6 C11 C10 120.46(14) . . ?
N6 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N6 C12 H12A 109.4 . . ?
N6 C12 H12B 109.4 . . ?
N6 C12 C13 111.03(13) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C12 C13 C14 113.99(14) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 112.96(13) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.58(14) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.98(15) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F3A P1A F2A 88.84(6) . . ?
F3A P1A F5A 177.61(6) . . ?
F4A P1A F2A 179.94(8) . . ?
F4A P1A F3A 91.11(6) . . ?
F4A P1A F5A 91.26(7) . . ?
F4A P1A F6A 90.82(7) . . ?
F4A P1A F7A 91.30(8) . . ?
F5A P1A F2A 88.79(6) . . ?
F6A P1A F2A 89.19(7) . . ?
F6A P1A F3A 90.25(6) . . ?
F6A P1A F5A 89.46(6) . . ?
F6A P1A F7A 177.88(8) . . ?
F7A P1A F2A 88.69(8) . . ?
F7A P1A F3A 89.73(6) . . ?
F7A P1A F5A 90.48(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 F2A 0.838(14) 2.069(15) 2.8599(16) 157.3(18) . yes
C7 H7 F5A 0.95 2.24 3.1120(18) 152.8 . yes
C9 H9 O3 0.95 2.28 3.1669(19) 155.1 5_666 yes
C11 H11 F6A 0.95 2.40 3.0581(19) 125.7 1_545 yes
C12 H12B F6A 0.99 2.38 3.162(2) 135.4 6_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C8 C7 3.1(2) . . . . ?
N1 C5 C8 C9 -177.65(14) . . . . ?
C2 N1 C5 C4 0.02(18) . . . . ?
C2 N1 C5 C8 -179.84(13) . . . . ?
C2 C4 C5 N1 179.8(2) 5_666 . . . ?
C2 C4 C5 C8 -0.3(3) 5_666 . . . ?
C4 C4 C5 N1 0.1(2) 5_666 . . . ?
C4 C4 C5 C8 179.94(16) 5_666 . . . ?
C4 C5 C8 C7 -176.69(15) . . . . ?
C4 C5 C8 C9 2.5(2) . . . . ?
C5 N1 C2 O3 178.91(14) . . . . ?
C5 N1 C2 C4 -0.12(17) . . . 5_666 ?
C5 C8 C9 C10 178.36(14) . . . . ?
N6 C7 C8 C5 -178.82(13) . . . . ?
N6 C7 C8 C9 1.9(2) . . . . ?
N6 C12 C13 C14 69.78(17) . . . . ?
C7 N6 C11 C10 -2.1(2) . . . . ?
C7 N6 C12 C13 86.48(16) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 N6 1.6(2) . . . . ?
C11 N6 C7 C8 0.3(2) . . . . ?
C11 N6 C12 C13 -90.57(17) . . . . ?
C12 N6 C7 C8 -176.70(14) . . . . ?
C12 N6 C11 C10 174.84(14) . . . . ?
C12 C13 C14 C15 176.57(13) . . . . ?
C13 C14 C15 C16 -175.51(13) . . . . ?
C14 C15 C16 C17 -177.06(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
