# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_2F_173K
_database_code_depnum_ccdc_archive 'CCDC 2527440'
loop_
_audit_author_name
_audit_author_address
'Liu Junchao'
;Anhui Ploytechnic University
China
;
_audit_update_record             
;
2026-05-25 deposited with the CCDC.	2026-06-10 downloaded from the CCDC.
;
_audit_creation_date             2026-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.05.15 svn.rea2f22b2 for OlexSys, GUI svn.r7569)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C12 H24 O6, C8 H11 F N'
_chemical_formula_sum            'C20 H35 F7 N O6 P'
_chemical_formula_weight         549.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOFP
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                   12.3530(11)
_cell_length_b                   15.1662(17)
_cell_length_c                   13.4368(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.638(10)
_cell_angle_gamma                90
_cell_volume                     2514.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5378
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      72.8110
_cell_measurement_theta_min      4.5770
_cell_oxdiff_angle_alpha         89.932(7)
_cell_oxdiff_angle_beta          92.732(7)
_cell_oxdiff_angle_gamma         90.036(8)
_cell_oxdiff_length_a            12.3362(12)
_cell_oxdiff_length_b            15.1916(16)
_cell_oxdiff_length_c            13.4336(9)
_cell_oxdiff_measurement_reflns_used 5381
_cell_oxdiff_volume              2514.7(4)
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.696
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1515
_diffrn_reflns_av_unetI/netI     0.0998
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21638
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.431
_diffrn_reflns_theta_min         4.399
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  58.00   0.50    0.30    --   60.10-125.00 -90.00   82
  2  ω     33.00  99.00   0.50    0.30    --   75.12-125.00 -30.00  132
  3  ω     34.00  88.00   0.50    0.30    --   75.12-105.00  25.00  108
  4  ω     19.00  73.00   0.50    0.30    --   60.10-105.00  25.00  108
  5  ω     56.00  83.00   0.50    0.30    --   38.00  52.00 179.49   54
  6  ω   -120.00 -94.00   0.50    0.30    --  -78.00 -59.00 107.51   52
  7  ω    -98.00 -72.00   0.50    0.30    --  -54.00 -52.00 106.45   52
  8  ω   -110.00 -83.00   0.50    0.30    --  -66.00 -54.00  74.17   54
  9  ω   -111.00 -84.00   0.50    0.30    --  -66.00 -51.00  21.54   54
 10  ω   -123.00 -96.00   0.50    0.30    --  -78.89 -54.00 -39.86   54
 11  ω   -123.00 -97.00   0.50    0.30    --  -78.89 -52.00 -46.55   52
 12  ω   -122.00 -96.00   0.50    0.30    --  -78.89 -56.00 -99.94   52
 13  ω   -111.00 -84.00   0.50    0.30    --  -66.00 -48.00-172.04   54
 14  ω   -106.00 -79.00   0.50    0.30    --  -62.00 -53.00-140.21   54
 15  ω   -115.00 -88.00   0.50    0.30    --  -70.00 -48.00 -92.68   54
 16  ω   -120.00 -91.00   0.50    0.30    --  -74.00 -46.00 -23.18   58
 17  ω   -125.00 -96.00   0.50    0.30    --  -78.89 -45.00  47.56   58
 18  ω   -116.00 -87.00   0.50    0.30    --  -70.00 -46.00  61.54   58
 19  ω   -125.00 -95.00   0.50    0.30    --  -78.89 -44.00 157.67   60
 20  ω   -103.00 -76.00   0.50    0.30    --  -58.00 -49.00 151.94   54
 21  ω   -125.00 -95.00   0.50    0.30    --  -78.89 -42.00 165.36   60
 22  ω   -116.00 -86.00   0.50    0.30    --  -70.00 -43.00  92.97   60
 23  ω   -125.00 -95.00   0.50    0.30    --  -78.89 -43.00   8.77   60
 24  ω   -120.00 -90.00   0.50    0.30    --  -74.00 -43.00 -33.58   60
 25  ω   -125.00 -95.00   0.50    0.30    --  -78.89 -42.00-164.10   60
 26  ω     -7.00  19.00   0.50    0.30    --  -10.00  84.00-150.33   52
 27  ω   -108.00 -32.00   0.50    0.30    --  -74.00 139.00  34.53  152
 28  ω    -98.00 -37.00   0.50    0.30    --  -78.89 118.00  -0.65  122
 29  ω    -96.00 -37.00   0.50    0.30    --  -78.89 115.00  45.56  118
 30  ω    -96.00 -37.00   0.50    0.30    --  -78.89 115.00  75.15  118
 31  ω    -86.00 -33.00   0.50    0.30    --  -73.82 105.00 125.00  106
 32  ω    -88.00 -34.00   0.50    0.30    --  -75.26 105.00 125.00  108
 33  ω    -73.00 -19.00   0.50    0.30    --  -60.46 105.00 125.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1059837000
_diffrn_orient_matrix_UB_12      0.0265237000
_diffrn_orient_matrix_UB_13      -0.0575697000
_diffrn_orient_matrix_UB_21      0.0428112000
_diffrn_orient_matrix_UB_22      0.0947689000
_diffrn_orient_matrix_UB_23      -0.0096063000
_diffrn_orient_matrix_UB_31      0.0506673000
_diffrn_orient_matrix_UB_32      -0.0244258000
_diffrn_orient_matrix_UB_33      -0.0988809000
_diffrn_oxdiff_digest_hkl        
;
43c7b5018f9113582802be2c94637f5c07cb82
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2096
_reflns_number_total             4818
_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 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.2253
_refine_ls_R_factor_gt           0.1387
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+13.6491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2602
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C20-C19 = C9-C10 = C18-C17 = C16-C15 = C14-C13 = C12-C11
 1.54 with sigma of 0.005
 C2-C1 = C3-C2
 1.54 with sigma of 0.005
 F1-C4
 1.42 with sigma of 0.005
 O2-C11 = O2-C10 = O1-C9 = O1-C20 = O6-C19 = O6-C18 = O5-C17 = O5-C16 = O4-C15
 = O4-C14 = O3-C13 = O3-C12
 1.43 with sigma of 0.01
 C18-C17
 1.54 with sigma of 0.01
 C2-C1
 1.54 with sigma of 0.01
 P1-F2 = P1-F7 = P1-F3 = P1-F5 = P1-F4 = P1-F6
 1.58 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C1(H1D,H1E), C2(H2A,H2B), C19(H19A,H19B), C12(H12A,H12B),
 C9(H9A,H9B), C13(H13A,H13B), C15(H15A,H15B), C20(H20A,H20B), C18(H18A,H18B),
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8)
3.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C3,C4)
3.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.24981(17) 0.40128(17) 0.69315(16) 0.0659(6) Uani 1 1 d D . . . .
F4 F 0.2475(4) 0.2991(3) 0.7194(4) 0.0792(14) Uani 1 1 d D . . . .
F2 F 0.1489(4) 0.3910(4) 0.6189(4) 0.1002(18) Uani 1 1 d D . . . .
O2 O 0.5396(4) 0.1981(4) 0.5763(4) 0.0716(16) Uani 1 1 d D . . . .
O6 O 0.9316(4) 0.2012(4) 0.5826(4) 0.0664(15) Uani 1 1 d D . . . .
O1 O 0.7329(4) 0.2745(4) 0.5129(4) 0.0679(16) Uani 1 1 d D . . . .
F5 F 0.3494(4) 0.4109(4) 0.7705(4) 0.109(2) Uani 1 1 d D . . . .
O5 O 0.9367(4) 0.1107(4) 0.7721(4) 0.0729(16) Uani 1 1 d D . . . .
F7 F 0.2524(4) 0.5024(3) 0.6672(5) 0.109(2) Uani 1 1 d D . . . .
O3 O 0.5435(5) 0.1137(4) 0.7670(4) 0.0767(17) Uani 1 1 d D . . . .
O4 O 0.7394(5) 0.0291(4) 0.8280(4) 0.0751(17) Uani 1 1 d D . . . .
F1 F 0.9268(4) 0.3711(4) 0.8671(4) 0.107(2) Uani 1 1 d D . . . .
F6 F 0.3306(5) 0.3840(4) 0.6085(4) 0.117(2) Uani 1 1 d D . . . .
F3 F 0.1696(5) 0.4171(4) 0.7791(4) 0.105(2) Uani 1 1 d D . . . .
N1 N 0.7377(5) 0.1876(4) 0.7008(4) 0.0605(18) Uani 1 1 d . . . . .
H1A H 0.743442 0.191405 0.633665 0.073 Uiso 1 1 calc R U . . .
H1B H 0.675229 0.159102 0.714309 0.073 Uiso 1 1 calc R U . . .
H1C H 0.795274 0.157081 0.727859 0.073 Uiso 1 1 calc R U . . .
C17 C 1.0249(6) 0.1132(6) 0.7053(6) 0.077(3) Uani 1 1 d D . . . .
H17A H 1.017099 0.064978 0.655867 0.093 Uiso 1 1 calc R U . . .
H17B H 1.094967 0.105715 0.743209 0.093 Uiso 1 1 calc R U . . .
C1 C 0.7364(7) 0.2769(6) 0.7438(5) 0.067(2) Uani 1 1 d D . . . .
H1D H 0.670292 0.308375 0.719041 0.081 Uiso 1 1 calc R U . . .
H1E H 0.800163 0.310369 0.722660 0.081 Uiso 1 1 calc R U . . .
C2 C 0.7384(7) 0.2720(4) 0.8580(5) 0.073(3) Uani 1 1 d D . . . .
H2A H 0.803361 0.238898 0.882589 0.088 Uiso 1 1 calc R U . . .
H2B H 0.673507 0.240045 0.879142 0.088 Uiso 1 1 calc R U . . .
C19 C 0.9265(6) 0.2812(5) 0.5286(6) 0.075(3) Uani 1 1 d D . . . .
H19A H 0.993593 0.289397 0.492033 0.090 Uiso 1 1 calc R U . . .
H19B H 0.919174 0.331582 0.574637 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4489(6) 0.1155(6) 0.7008(6) 0.078(3) Uani 1 1 d D . . . .
H12A H 0.382668 0.112492 0.739473 0.094 Uiso 1 1 calc R U . . .
H12B H 0.449176 0.064277 0.655150 0.094 Uiso 1 1 calc R U . . .
C9 C 0.6357(5) 0.2718(6) 0.4507(5) 0.072(3) Uani 1 1 d D . . . .
H9A H 0.632952 0.216675 0.411142 0.087 Uiso 1 1 calc R U . . .
H9B H 0.633449 0.322439 0.404181 0.087 Uiso 1 1 calc R U . . .
C13 C 0.5484(7) 0.0335(6) 0.8220(7) 0.083(3) Uani 1 1 d D . . . .
H13A H 0.550151 -0.017082 0.775629 0.099 Uiso 1 1 calc R U . . .
H13B H 0.483110 0.027859 0.861563 0.099 Uiso 1 1 calc R U . . .
C15 C 0.8381(6) 0.0245(7) 0.8880(5) 0.082(3) Uani 1 1 d D . . . .
H15A H 0.840113 -0.030338 0.927944 0.099 Uiso 1 1 calc R U . . .
H15B H 0.843551 0.075459 0.934056 0.099 Uiso 1 1 calc R U . . .
C20 C 0.8278(5) 0.2767(6) 0.4550(5) 0.076(3) Uani 1 1 d D . . . .
H20A H 0.825935 0.328919 0.410744 0.091 Uiso 1 1 calc R U . . .
H20B H 0.831391 0.223055 0.413240 0.091 Uiso 1 1 calc R U . . .
C5 C 0.8449(4) 0.4934(4) 0.9529(4) 0.080(3) Uani 1 1 d G . . . .
H5 H 0.912016 0.524087 0.956862 0.096 Uiso 1 1 calc R U . . .
C6 C 0.7531(5) 0.5315(3) 0.9906(4) 0.078(3) Uani 1 1 d G . . . .
H6 H 0.757340 0.588328 1.020260 0.093 Uiso 1 1 calc R U . . .
C7 C 0.6549(4) 0.4866(4) 0.9847(4) 0.077(3) Uani 1 1 d G . . . .
H7 H 0.592123 0.512642 1.010481 0.093 Uiso 1 1 calc R U . . .
C8 C 0.6487(4) 0.4034(4) 0.9413(4) 0.080(3) Uani 1 1 d G . . . .
H8 H 0.581581 0.372715 0.937305 0.096 Uiso 1 1 calc R U . . .
C3 C 0.7405(5) 0.3653(3) 0.9036(4) 0.067(2) Uani 1 1 d DG . . . .
C4 C 0.8387(4) 0.4102(4) 0.9094(4) 0.072(2) Uani 1 1 d DG . . . .
C18 C 1.0216(6) 0.2028(5) 0.6524(6) 0.077(3) Uani 1 1 d D . . . .
H18A H 1.013189 0.250878 0.701304 0.093 Uiso 1 1 calc R U . . .
H18B H 1.089600 0.212652 0.617791 0.093 Uiso 1 1 calc R U . . .
C10 C 0.5395(6) 0.2758(6) 0.5189(6) 0.077(3) Uani 1 1 d D . . . .
H10A H 0.546234 0.327992 0.563051 0.092 Uiso 1 1 calc R U . . .
H10B H 0.470723 0.280735 0.478426 0.092 Uiso 1 1 calc R U . . .
C11 C 0.4503(6) 0.2016(6) 0.6411(6) 0.086(3) Uani 1 1 d D . . . .
H11A H 0.381290 0.208483 0.601356 0.103 Uiso 1 1 calc R U . . .
H11B H 0.458707 0.252505 0.686851 0.103 Uiso 1 1 calc R U . . .
C16 C 0.9320(7) 0.0258(6) 0.8171(6) 0.080(3) Uani 1 1 d D . . . .
H16A H 1.001179 0.013124 0.854517 0.097 Uiso 1 1 calc R U . . .
H16B H 0.920558 -0.019899 0.765076 0.097 Uiso 1 1 calc R U . . .
C14 C 0.6501(6) 0.0326(7) 0.8917(6) 0.085(3) Uani 1 1 d D . . . .
H14A H 0.653710 0.086436 0.933327 0.102 Uiso 1 1 calc R U . . .
H14B H 0.650045 -0.019617 0.935955 0.102 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 F4 1.589(5) . ?
P1 F2 1.568(5) . ?
P1 F5 1.580(5) . ?
P1 F7 1.573(5) . ?
P1 F6 1.570(5) . ?
P1 F3 1.574(5) . ?
O2 C10 1.409(7) . ?
O2 C11 1.437(7) . ?
O6 C19 1.414(7) . ?
O6 C18 1.422(7) . ?
O1 C9 1.431(7) . ?
O1 C20 1.437(7) . ?
O5 C17 1.445(7) . ?
O5 C16 1.423(7) . ?
O3 C12 1.436(7) . ?
O3 C13 1.423(7) . ?
O4 C15 1.432(7) . ?
O4 C14 1.429(7) . ?
F1 C4 1.384(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.473(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.533(4) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C1 C2 1.535(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.541(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.536(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.533(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.536(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.531(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.536(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C5 H5 0.9500 . ?
C5 C6 1.3900 . ?
C5 C4 1.3900 . ?
C6 H6 0.9500 . ?
C6 C7 1.3900 . ?
C7 H7 0.9500 . ?
C7 C8 1.3900 . ?
C8 H8 0.9500 . ?
C8 C3 1.3900 . ?
C3 C4 1.3900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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 P1 F4 91.3(3) . . ?
F2 P1 F5 178.4(4) . . ?
F2 P1 F7 88.9(3) . . ?
F2 P1 F6 92.0(4) . . ?
F2 P1 F3 88.5(3) . . ?
F5 P1 F4 88.0(3) . . ?
F7 P1 F4 179.9(4) . . ?
F7 P1 F5 91.8(3) . . ?
F7 P1 F3 91.9(4) . . ?
F6 P1 F4 91.0(3) . . ?
F6 P1 F5 89.4(4) . . ?
F6 P1 F7 88.9(3) . . ?
F6 P1 F3 179.0(4) . . ?
F3 P1 F4 88.1(3) . . ?
F3 P1 F5 90.1(3) . . ?
C10 O2 C11 108.6(6) . . ?
C19 O6 C18 109.8(6) . . ?
C9 O1 C20 111.6(5) . . ?
C16 O5 C17 109.5(6) . . ?
C13 O3 C12 110.6(6) . . ?
C14 O4 C15 109.0(6) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
O5 C17 H17A 110.1 . . ?
O5 C17 H17B 110.1 . . ?
O5 C17 C18 107.9(7) . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 H17A 110.1 . . ?
C18 C17 H17B 110.1 . . ?
N1 C1 H1D 109.6 . . ?
N1 C1 H1E 109.6 . . ?
N1 C1 C2 110.4(6) . . ?
H1D C1 H1E 108.1 . . ?
C2 C1 H1D 109.6 . . ?
C2 C1 H1E 109.6 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.6(6) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
O6 C19 H19A 110.1 . . ?
O6 C19 H19B 110.1 . . ?
O6 C19 C20 107.9(6) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
O3 C12 H12A 110.1 . . ?
O3 C12 H12B 110.1 . . ?
O3 C12 C11 108.2(7) . . ?
H12A C12 H12B 108.4 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
O1 C9 H9A 110.2 . . ?
O1 C9 H9B 110.2 . . ?
O1 C9 C10 107.6(6) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
O3 C13 H13A 109.7 . . ?
O3 C13 H13B 109.7 . . ?
O3 C13 C14 109.9(7) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
O4 C15 H15A 110.2 . . ?
O4 C15 H15B 110.2 . . ?
O4 C15 C16 107.3(6) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
O1 C20 C19 107.2(6) . . ?
O1 C20 H20A 110.3 . . ?
O1 C20 H20B 110.3 . . ?
C19 C20 H20A 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C3 C8 C7 120.0 . . ?
C3 C8 H8 120.0 . . ?
C8 C3 C2 121.9(5) . . ?
C8 C3 C4 120.0 . . ?
C4 C3 C2 118.1(5) . . ?
F1 C4 C5 122.1(5) . . ?
F1 C4 C3 117.8(5) . . ?
C3 C4 C5 120.0 . . ?
O6 C18 C17 107.1(6) . . ?
O6 C18 H18A 110.3 . . ?
O6 C18 H18B 110.3 . . ?
C17 C18 H18A 110.3 . . ?
C17 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
O2 C10 C9 108.2(7) . . ?
O2 C10 H10A 110.1 . . ?
O2 C10 H10B 110.1 . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
O2 C11 C12 108.2(7) . . ?
O2 C11 H11A 110.1 . . ?
O2 C11 H11B 110.0 . . ?
C12 C11 H11A 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
O5 C16 C15 108.7(7) . . ?
O5 C16 H16A 109.9 . . ?
O5 C16 H16B 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O4 C14 C13 105.6(7) . . ?
O4 C14 H14A 110.6 . . ?
O4 C14 H14B 110.6 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
H14A C14 H14B 108.8 . . ?

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 H1A O1 0.91 2.05 2.847(8) 144.8 . yes
N1 H1B O3 0.91 1.93 2.828(8) 168.3 . yes
N1 H1C O5 0.91 1.95 2.847(8) 167.9 . 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
O6 C19 C20 O1 65.9(9) . . . . ?
O1 C9 C10 O2 -65.9(9) . . . . ?
O5 C17 C18 O6 -72.7(8) . . . . ?
O3 C12 C11 O2 67.2(9) . . . . ?
O3 C13 C14 O4 -66.9(10) . . . . ?
O4 C15 C16 O5 68.7(9) . . . . ?
N1 C1 C2 C3 178.3(6) . . . . ?
C17 O5 C16 C15 179.8(7) . . . . ?
C1 C2 C3 C8 103.2(6) . . . . ?
C1 C2 C3 C4 -78.9(7) . . . . ?
C2 C3 C4 F1 4.7(6) . . . . ?
C2 C3 C4 C5 -178.0(5) . . . . ?
C19 O6 C18 C17 -177.8(7) . . . . ?
C12 O3 C13 C14 179.7(7) . . . . ?
C9 O1 C20 C19 179.0(7) . . . . ?
C13 O3 C12 C11 -178.0(7) . . . . ?
C15 O4 C14 C13 -177.8(7) . . . . ?
C20 O1 C9 C10 -176.3(7) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C5 C4 F1 177.2(6) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C8 C3 0.0 . . . . ?
C7 C8 C3 C2 177.9(6) . . . . ?
C7 C8 C3 C4 0.0 . . . . ?
C8 C3 C4 F1 -177.3(6) . . . . ?
C8 C3 C4 C5 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C18 O6 C19 C20 -179.5(7) . . . . ?
C10 O2 C11 C12 178.2(7) . . . . ?
C11 O2 C10 C9 179.5(7) . . . . ?
C16 O5 C17 C18 175.6(7) . . . . ?
C14 O4 C15 C16 -177.1(7) . . . . ?

_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 1.746
_oxdiff_exptl_absorpt_empirical_full_min 0.589
####################################################################### 
# 
# 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_3F_298K
_database_code_depnum_ccdc_archive 'CCDC 2545079'
loop_
_audit_author_name
_audit_author_address
Liujunchao
;Anhui Ploytechnic University
China
;
_audit_update_record             
;
2026-05-23 deposited with the CCDC.	2026-06-10 downloaded from the CCDC.
;
_audit_creation_date             2026-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.10 svn.r48fbca5a for OlexSys, GUI svn.r7537)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C8 H11 F N, C12 H24 O6'
_chemical_formula_sum            'C20 H35 F7 N O6 P'
_chemical_formula_weight         549.46
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        Pbca
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.2491(4)
_cell_length_b                   16.5906(4)
_cell_length_c                   18.5124(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5297.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      16.78
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0736 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.9549.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            151722
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3285
_reflns_number_total             4927
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         4927
_refine_ls_number_restraints     1931
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.1529
_refine_ls_restrained_S_all      2.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0214P)²+11.1711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C20-C9
 2.2 with sigma of 0.02
 C11-C10
 2.2 with sigma of 0.02
 C10-C9
 1.54 with sigma of 0.01
 C10-C11
 2.2 with sigma of 0.02
 O1-C9 = O1-C20 = O2-C10 = O2-C11 = O3-C13 = O3-C12 = O4-C15 = O4-C14 = O5-C16
 = O5-C17 = O6-C18 = O6-C19
 1.42 with sigma of 0.01
 C9-C10 = C12-C11 = C14-C13 = C16-C15 = C18-C17 = C20-C19
 1.54 with sigma of 0.01
 O1-C19
 2.2 with sigma of 0.02
 C2-C1 = C3-C2
 1.54 with sigma of 0.02
 C2-C1
 1.63 with sigma of 0.02
 O6-C18 = O5A-C17A = O5A-C16A = O4A-C15A = O4A-C14A = O3A-C13A = O2A-C11A =
 O2A-C10A = O1A-C9A = O1A-C20A = O6A-C19A = O6A-C18A = O1-C20
 1.42 with sigma of 0.02
 C14A-C13A = C16A-C15A = C18A-C17A = C20A-C19A = C9A-C10A = C12A-C11A
 1.54 with sigma of 0.01
 F003-F005 \\sim F003-F009 \\sim F003-F00B \\sim F003-F \\sim F005-F009 \\sim
F005-F00A \\sim F005-
 F00B \\sim F009-F00A \\sim F009-F00B \\sim F009-F \\sim F00A-F00B \\sim F00A-F
\\sim F00B-F \\sim F0-F2 \\sim
 F0-F00C \\sim F0-FA \\sim F2-F3 \\sim F2-F4 \\sim F2-F00C \\sim F3-F4 \\sim
F3-F00C \\sim F3-FA \\sim F4-F00C
 \\sim F4-FA \\sim F00C-FA
 with sigma of 0.04
 P001-F003 \\sim P001-F005 \\sim P001-F009 \\sim P001-F00A \\sim P001-F00B
\\sim P001-F \\sim P001-F0
 \\sim P001-F2 \\sim P001-F3 \\sim P001-F4 \\sim P001-F00C \\sim P001-FA
 with sigma of 0.02
 C1-C2 \\sim C1-C2A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C6-F6 \\sim C6A-F6A
 with sigma of 0.02
3. Rigid bond restraints
 C2, C3, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, H1A, H1B, H1C, C1, C2, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim C10 \\sim C11 \\sim C9 \\sim C12 \\sim O3 \\sim C20 \\sim C13
\\sim C19 \\sim C14 \\sim O6 \\sim O4 \\sim C18 \\sim C15 \\sim C17 \\sim C16
\\sim O5 \\sim C20A \\sim O1A \\sim C19A \\sim C9A \\sim O6A \\sim C10A \\sim
C18A \\sim O2A \\sim C17A \\sim C11A \\sim O5A \\sim C12A \\sim C16A \\sim O3A
\\sim C15A \\sim C13A \\sim O4A \\sim C14A: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
F4 \\sim P001 \\sim F \\sim FA \\sim F009 \\sim F3 \\sim F00A \\sim F005 \\sim
F2 \\sim F003 \\sim F0 \\sim F00B \\sim F00C: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
C2 \\sim C3 \\sim C1: within 2A with sigma of 0.02 and sigma for terminal atoms
of 0.04 within 2A
C7 \\sim N1 \\sim H1A \\sim H1B \\sim H1C \\sim C1 \\sim C2 \\sim C3 \\sim C4
\\sim C5 \\sim C6 \\sim F6 \\sim C8: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
C3A \\sim N1 \\sim H1A \\sim H1B \\sim H1C \\sim C1 \\sim C2 \\sim C2A \\sim C3
\\sim C7 \\sim C4 \\sim C4A \\sim C7A \\sim C6 \\sim C5 \\sim C5A \\sim C6A
\\sim C8 \\sim F6 \\sim C8A \\sim F6A: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
5. Rigid body (RIGU) restrains
 O1, O2, C10, C11, C9, C12, O3, C20, C13, C19, C14, O6, O4, C18, C15, C17, C16,
  O5, C20A, O1A, C19A, C9A, O6A, C10A, C18A, O2A, C17A, C11A, O5A, C12A, C16A,
 O3A, C15A, C13A, O4A, C14A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 F4, P001, F, FA, F009, F3, F00A, F005, F2, F003, F0, F00B, F00C
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C4A, N1, H1A, H1B, H1C, C1, C2, C2A, C3, C3A, C7, C4, C7A, C6, C5, C5A, C6A,
 C8, F6, C8A, F6A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
6. Others
 Sof(F0)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F00C)=Sof(FA)=1-FVAR(1)
 Sof(F003)=Sof(F005)=Sof(F009)=Sof(F00A)=Sof(F00B)=Sof(F)=FVAR(1)
 Sof(H1BC)=Sof(H1BD)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C7A)=Sof(H7A)=Sof(C6A)=
 Sof(C8A)=Sof(H8A)=Sof(C5A)=Sof(H5A)=Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(F6A)=1-
 FVAR(2)
 Sof(H1AA)=Sof(H1AB)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C7)=Sof(H7)=Sof(C6)=Sof(C8)=
 Sof(H8)=Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(F6)=FVAR(2)
 Fixed Sof: O2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5) O1(0.5) C10(0.5) H10A(0.5)
 H10B(0.5) C15(0.5) H15A(0.5) H15B(0.5) C17(0.5) H17A(0.5) H17B(0.5) C18(0.5)
 H18A(0.5) H18B(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5)
 C19(0.5) H19A(0.5) H19B(0.5) C13(0.5) H13A(0.5) H13B(0.5) C14(0.5) H14A(0.5)
 H14B(0.5) C20(0.5) H20A(0.5) H20B(0.5) C16(0.5) H16A(0.5) H16B(0.5) C9(0.5)
 H9A(0.5) H9B(0.5) C20A(0.5) H20C(0.5) H20D(0.5) O2A(0.5) C10A(0.5) H10C(0.5)
 H10D(0.5) C11A(0.5) H11C(0.5) H11D(0.5) C9A(0.5) H9AA(0.5) H9AB(0.5) C12A(0.5)
 H12C(0.5) H12D(0.5) O1A(0.5) O3A(0.5) C13A(0.5) H13C(0.5) H13D(0.5) C19A(0.5)
 H19C(0.5) H19D(0.5) C14A(0.5) H14C(0.5) H14D(0.5) O6A(0.5) O4A(0.5) C18A(0.5)
 H18C(0.5) H18D(0.5) C15A(0.5) H15C(0.5) H15D(0.5) C17A(0.5) H17C(0.5)
 H17D(0.5) C16A(0.5) H16C(0.5) H16D(0.5) O5A(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C10(H10A,H10B), C15(H15A,H15B), C2(H2A,H2B),
 C17(H17A,H17B), C18(H18A,H18B), C11(H11A,H11B), C12(H12A,H12B), C19(H19A,H19B),
  C13(H13A,H13B), C14(H14A,H14B), C20(H20A,H20B), C16(H16A,H16B), C9(H9A,H9B),
 C20A(H20C,H20D), C10A(H10C,H10D), C11A(H11C,H11D), C9A(H9AA,H9AB), C12A(H12C,
 H12D), C13A(H13C,H13D), C19A(H19C,H19D), C14A(H14C,H14D), C18A(H18C,H18D),
 C15A(H15C,H15D), C17A(H17C,H17D), C16A(H16C,H16D), C2A(H2AA,H2AB)
7.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C5(H5), C4(H4), C7A(H7A), C8A(H8A), C5A(H5A), C4A(H4A)
7.c Fitted hexagon refined as free rotating group:
 C7(C6,C8,C5,C4,C3), C7A(C6A,C8A,C5A,C4A,C3A)
7.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P001 P 0.31463(13) 0.35900(11) 0.95646(12) 0.1148(7) Uani 1 1 d D U . . .
N1 N 0.4868(2) 0.1718(3) 0.7629(2) 0.0929(13) Uani 1 1 d . U . . .
H1A H 0.499197 0.145810 0.722475 0.111 Uiso 1 1 calc R U . . .
H1B H 0.465741 0.137438 0.794137 0.111 Uiso 1 1 calc R U . . .
H1C H 0.529289 0.193380 0.782139 0.111 Uiso 1 1 calc R U . . .
F003 F 0.3175(4) 0.4522(3) 0.9750(3) 0.166(2) Uani 0.900(6) 1 d D U P A 1
F005 F 0.2235(3) 0.3589(4) 0.9541(3) 0.178(2) Uani 0.900(6) 1 d D U P A 1
F009 F 0.3094(4) 0.3791(4) 0.8766(3) 0.185(3) Uani 0.900(6) 1 d D U P A 1
F00A F 0.3149(4) 0.2663(3) 0.9424(4) 0.196(3) Uani 0.900(6) 1 d D U P A 1
F00B F 0.3077(5) 0.3444(4) 1.0389(3) 0.202(3) Uani 0.900(6) 1 d D U P A 1
F F 0.4033(3) 0.3593(5) 0.9598(5) 0.236(4) Uani 0.900(6) 1 d D U P A 1
C1 C 0.4293(4) 0.2379(4) 0.7458(4) 0.127(2) Uani 1 1 d D U . . .
H1AA H 0.377388 0.215370 0.744441 0.152 Uiso 0.479(8) 1 calc R U P B 1
H1AB H 0.430732 0.278239 0.783688 0.152 Uiso 0.479(8) 1 calc R U P B 1
H1BC H 0.387222 0.215947 0.717063 0.152 Uiso 0.521(8) 1 calc R U P B 2
H1BD H 0.407455 0.258636 0.790359 0.152 Uiso 0.521(8) 1 calc R U P B 2
O2 O 0.4750(10) 0.0473(9) 0.6625(8) 0.161(4) Uani 0.5 1 d D U P C 1
O3 O 0.6229(12) 0.1753(11) 0.6292(9) 0.191(5) Uani 0.5 1 d D U P C 1
O4 O 0.6256(8) 0.2690(10) 0.7705(8) 0.160(4) Uani 0.5 1 d D U P C 1
O5 O 0.5773(10) 0.1950(11) 0.8918(8) 0.159(4) Uani 0.5 1 d D U P C 1
O6 O 0.4433(9) 0.0971(9) 0.8985(8) 0.151(4) Uani 0.5 1 d D U P C 1
O1 O 0.3825(9) 0.0452(9) 0.7737(8) 0.191(4) Uani 0.5 1 d D U P C 1
C10 C 0.4154(10) -0.0061(12) 0.6477(10) 0.164(5) Uani 0.5 1 d D U P C 1
H10A H 0.435770 -0.059202 0.636588 0.197 Uiso 0.5 1 calc R U P C 1
H10B H 0.384777 0.012554 0.607108 0.197 Uiso 0.5 1 calc R U P C 1
C15 C 0.6830(9) 0.2554(14) 0.8247(9) 0.155(5) Uani 0.5 1 d D U P C 1
H15A H 0.722818 0.296654 0.825605 0.186 Uiso 0.5 1 calc R U P C 1
H15B H 0.706217 0.202247 0.821856 0.186 Uiso 0.5 1 calc R U P C 1
C2 C 0.4467(9) 0.2769(8) 0.6751(7) 0.112(4) Uani 0.479(8) 1 d D U P B 1
H2A H 0.438482 0.237840 0.636853 0.135 Uiso 0.479(8) 1 calc R U P B 1
H2B H 0.500922 0.292201 0.674280 0.135 Uiso 0.479(8) 1 calc R U P B 1
C17 C 0.5392(13) 0.1837(12) 0.9591(9) 0.157(5) Uani 0.5 1 d D U P C 1
H17A H 0.501868 0.226396 0.967587 0.188 Uiso 0.5 1 calc R U P C 1
H17B H 0.576393 0.183415 0.998380 0.188 Uiso 0.5 1 calc R U P C 1
C18 C 0.4984(11) 0.1024(12) 0.9536(10) 0.156(5) Uani 0.5 1 d D U P C 1
H18A H 0.537216 0.060952 0.946082 0.188 Uiso 0.5 1 calc R U P C 1
H18B H 0.473074 0.091263 0.999349 0.188 Uiso 0.5 1 calc R U P C 1
C11 C 0.5197(11) 0.0506(14) 0.5991(10) 0.162(5) Uani 0.5 1 d D U P C 1
H11A H 0.489297 0.075580 0.561143 0.194 Uiso 0.5 1 calc R U P C 1
H11B H 0.531948 -0.003886 0.583856 0.194 Uiso 0.5 1 calc R U P C 1
C12 C 0.5952(13) 0.0977(13) 0.6085(15) 0.159(5) Uani 0.5 1 d D U P C 1
H12A H 0.624197 0.062685 0.640600 0.191 Uiso 0.5 1 calc R U P C 1
H12B H 0.619378 0.090746 0.561674 0.191 Uiso 0.5 1 calc R U P C 1
C19 C 0.3946(12) 0.0283(12) 0.8947(10) 0.166(5) Uani 0.5 1 d D U P C 1
H19A H 0.365478 0.025363 0.939448 0.200 Uiso 0.5 1 calc R U P C 1
H19B H 0.427556 -0.018990 0.892721 0.200 Uiso 0.5 1 calc R U P C 1
C13 C 0.6679(15) 0.1870(10) 0.6933(11) 0.166(5) Uani 0.5 1 d D U P C 1
H13A H 0.719210 0.164204 0.686667 0.199 Uiso 0.5 1 calc R U P C 1
H13B H 0.643390 0.159627 0.733572 0.199 Uiso 0.5 1 calc R U P C 1
C14 C 0.6744(11) 0.2760(10) 0.7093(10) 0.151(5) Uani 0.5 1 d D U P C 1
H14A H 0.726672 0.292910 0.721201 0.182 Uiso 0.5 1 calc R U P C 1
H14B H 0.652816 0.309841 0.671598 0.182 Uiso 0.5 1 calc R U P C 1
C20 C 0.3370(10) 0.0230(14) 0.8323(9) 0.184(5) Uani 0.5 1 d D U P C 1
H20A H 0.317045 -0.031317 0.826834 0.221 Uiso 0.5 1 calc R U P C 1
H20B H 0.294023 0.059964 0.839012 0.221 Uiso 0.5 1 calc R U P C 1
C16 C 0.6240(12) 0.2635(13) 0.8869(12) 0.162(5) Uani 0.5 1 d D U P C 1
H16A H 0.651459 0.271170 0.932140 0.195 Uiso 0.5 1 calc R U P C 1
H16B H 0.591674 0.310534 0.878809 0.195 Uiso 0.5 1 calc R U P C 1
C9 C 0.3662(11) -0.0085(14) 0.7170(9) 0.168(5) Uani 0.5 1 d D U P C 1
H9A H 0.312679 0.000001 0.702949 0.202 Uiso 0.5 1 calc R U P C 1
H9B H 0.369642 -0.062691 0.736356 0.202 Uiso 0.5 1 calc R U P C 1
C20A C 0.3469(11) 0.0162(16) 0.7702(12) 0.180(5) Uani 0.5 1 d D U P D 2
H20C H 0.303403 -0.018632 0.758898 0.216 Uiso 0.5 1 calc R U P D 2
H20D H 0.330949 0.072017 0.765230 0.216 Uiso 0.5 1 calc R U P D 2
O2A O 0.5142(10) 0.0730(11) 0.6401(9) 0.173(5) Uani 0.5 1 d D U P D 2
C10A C 0.4641(12) 0.0163(13) 0.6140(12) 0.168(5) Uani 0.5 1 d D U P D 2
H10C H 0.485897 -0.037385 0.618014 0.202 Uiso 0.5 1 calc R U P D 2
H10D H 0.451250 0.026791 0.563840 0.202 Uiso 0.5 1 calc R U P D 2
C11A C 0.5590(13) 0.0899(16) 0.5862(12) 0.170(5) Uani 0.5 1 d D U P D 2
H11C H 0.537751 0.134353 0.558475 0.205 Uiso 0.5 1 calc R U P D 2
H11D H 0.564272 0.043570 0.554713 0.205 Uiso 0.5 1 calc R U P D 2
C9A C 0.3933(12) 0.0258(13) 0.6622(11) 0.173(5) Uani 0.5 1 d D U P D 2
H9AA H 0.378356 0.082042 0.664656 0.208 Uiso 0.5 1 calc R U P D 2
H9AB H 0.350248 -0.004650 0.642471 0.208 Uiso 0.5 1 calc R U P D 2
C12A C 0.6369(12) 0.1129(17) 0.6179(14) 0.176(5) Uani 0.5 1 d D U P D 2
H12C H 0.661471 0.069437 0.644412 0.211 Uiso 0.5 1 calc R U P D 2
H12D H 0.672294 0.135700 0.582734 0.211 Uiso 0.5 1 calc R U P D 2
O1A O 0.4101(9) -0.0008(10) 0.7271(9) 0.183(4) Uani 0.5 1 d D U P D 2
O3A O 0.6044(9) 0.1674(10) 0.6600(8) 0.169(4) Uani 0.5 1 d D U P D 2
C13A C 0.6778(13) 0.2114(14) 0.6713(10) 0.167(5) Uani 0.5 1 d D U P D 2
H13C H 0.679753 0.258768 0.640593 0.200 Uiso 0.5 1 calc R U P D 2
H13D H 0.721655 0.177153 0.659792 0.200 Uiso 0.5 1 calc R U P D 2
C19A C 0.3785(13) -0.0008(13) 0.8460(12) 0.176(5) Uani 0.5 1 d D U P D 2
H19C H 0.337711 -0.019388 0.877926 0.211 Uiso 0.5 1 calc R U P D 2
H19D H 0.419334 -0.040948 0.844447 0.211 Uiso 0.5 1 calc R U P D 2
C14A C 0.6798(13) 0.2358(14) 0.7509(10) 0.167(5) Uani 0.5 1 d D U P D 2
H14C H 0.709770 0.191634 0.770760 0.200 Uiso 0.5 1 calc R U P D 2
H14D H 0.716196 0.280350 0.748740 0.200 Uiso 0.5 1 calc R U P D 2
O6A O 0.4068(10) 0.0722(11) 0.8681(10) 0.176(4) Uani 0.5 1 d D U P D 2
O4A O 0.6343(10) 0.2592(11) 0.8148(9) 0.173(4) Uani 0.5 1 d D U P D 2
C18A C 0.4505(14) 0.0655(11) 0.9309(11) 0.160(5) Uani 0.5 1 d D U P D 2
H18C H 0.493569 0.029055 0.922653 0.192 Uiso 0.5 1 calc R U P D 2
H18D H 0.418645 0.043210 0.969143 0.192 Uiso 0.5 1 calc R U P D 2
C15A C 0.6552(11) 0.2440(14) 0.8852(11) 0.165(5) Uani 0.5 1 d D U P D 2
H15C H 0.687998 0.286622 0.904004 0.198 Uiso 0.5 1 calc R U P D 2
H15D H 0.682480 0.193031 0.889200 0.198 Uiso 0.5 1 calc R U P D 2
C17A C 0.4815(12) 0.1481(11) 0.9540(12) 0.158(5) Uani 0.5 1 d D U P D 2
H17C H 0.441628 0.188813 0.948393 0.190 Uiso 0.5 1 calc R U P D 2
H17D H 0.497201 0.146710 1.004334 0.190 Uiso 0.5 1 calc R U P D 2
C16A C 0.5778(11) 0.2410(12) 0.9252(12) 0.163(5) Uani 0.5 1 d D U P D 2
H16C H 0.586171 0.248090 0.976638 0.195 Uiso 0.5 1 calc R U P D 2
H16D H 0.544323 0.284129 0.908410 0.195 Uiso 0.5 1 calc R U P D 2
O5A O 0.5423(12) 0.1651(10) 0.9119(10) 0.174(5) Uani 0.5 1 d D U P D 2
F0 F 0.286(2) 0.4337(17) 0.997(3) 0.167(10) Uani 0.100(6) 1 d D U P A 2
F2 F 0.249(2) 0.302(2) 0.985(2) 0.161(10) Uani 0.100(6) 1 d D U P A 2
F3 F 0.268(2) 0.4293(16) 0.955(3) 0.171(10) Uani 0.100(6) 1 d D U P A 2
F4 F 0.323(2) 0.304(2) 0.8926(16) 0.148(11) Uani 0.100(6) 1 d D U P A 2
F00C F 0.368(2) 0.329(2) 1.014(2) 0.153(10) Uani 0.100(6) 1 d D U P A 2
FA F 0.3876(19) 0.405(2) 0.923(3) 0.184(11) Uani 0.100(6) 1 d D U P A 2
C7 C 0.3428(8) 0.3517(7) 0.6039(9) 0.088(4) Uani 0.479(8) 1 d G U P B 1
H7 H 0.333849 0.304822 0.577765 0.105 Uiso 0.479(8) 1 calc R U P B 1
C6 C 0.3022(7) 0.4217(8) 0.5874(7) 0.080(3) Uani 0.479(8) 1 d DG U P B 1
C8 C 0.3156(8) 0.4918(7) 0.6265(9) 0.086(4) Uani 0.479(8) 1 d G U P B 1
H8 H 0.288389 0.538620 0.615454 0.103 Uiso 0.479(8) 1 calc R U P B 1
C5 C 0.3697(8) 0.4920(8) 0.6822(9) 0.101(4) Uani 0.479(8) 1 d G U P B 1
H5 H 0.378640 0.538941 0.708371 0.121 Uiso 0.479(8) 1 calc R U P B 1
C4 C 0.4103(8) 0.4221(10) 0.6987(8) 0.101(4) Uani 0.479(8) 1 d G U P B 1
H4 H 0.446497 0.422203 0.735987 0.121 Uiso 0.479(8) 1 calc R U P B 1
C3 C 0.3969(9) 0.3519(8) 0.6596(9) 0.094(3) Uani 0.479(8) 1 d DG U P B 1
F6 F 0.2548(6) 0.4015(6) 0.5363(5) 0.164(4) Uani 0.479(8) 1 d D U P B 1
C2A C 0.4649(8) 0.3009(8) 0.7078(9) 0.121(4) Uani 0.521(8) 1 d D U P B 2
H2AA H 0.494914 0.279056 0.668015 0.145 Uiso 0.521(8) 1 calc R U P B 2
H2AB H 0.499985 0.329702 0.739559 0.145 Uiso 0.521(8) 1 calc R U P B 2
C7A C 0.3922(8) 0.4349(9) 0.7092(7) 0.100(4) Uani 0.521(8) 1 d G U P B 2
H7A H 0.416156 0.447645 0.752685 0.120 Uiso 0.521(8) 1 calc R U P B 2
C6A C 0.3452(8) 0.4913(7) 0.6750(8) 0.101(4) Uani 0.521(8) 1 d DG U P B 2
C8A C 0.3093(8) 0.4722(7) 0.6100(7) 0.085(4) Uani 0.521(8) 1 d G U P B 2
H8A H 0.277870 0.509889 0.587149 0.102 Uiso 0.521(8) 1 calc R U P B 2
C5A C 0.3204(7) 0.3967(8) 0.5791(6) 0.092(4) Uani 0.521(8) 1 d G U P B 2
H5A H 0.296417 0.383876 0.535640 0.110 Uiso 0.521(8) 1 calc R U P B 2
C4A C 0.3674(8) 0.3403(6) 0.6133(8) 0.090(4) Uani 0.521(8) 1 d G U P B 2
H4A H 0.374834 0.289746 0.592654 0.109 Uiso 0.521(8) 1 calc R U P B 2
C3A C 0.4033(8) 0.3594(8) 0.6783(8) 0.096(3) Uani 0.521(8) 1 d DG U P B 2
F6A F 0.3479(6) 0.5553(5) 0.7125(5) 0.183(4) Uani 0.521(8) 1 d D U P B 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
P001 F003 1.586(5) . ?
P001 F005 1.573(5) . ?
P001 F009 1.518(5) . ?
P001 F00A 1.560(5) . ?
P001 F00B 1.549(5) . ?
P001 F 1.531(5) . ?
P001 F0 1.527(14) . ?
P001 F2 1.575(14) . ?
P001 F3 1.414(13) . ?
P001 F4 1.503(13) . ?
P001 F00C 1.493(13) . ?
P001 FA 1.597(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.512(7) . ?
C1 H1AA 0.9700 . ?
C1 H1AB 0.9700 . ?
C1 H1BC 0.9700 . ?
C1 H1BD 0.9700 . ?
C1 C2 1.489(10) . ?
C1 C2A 1.402(12) . ?
O2 C10 1.385(10) . ?
O2 C11 1.406(10) . ?
O3 C12 1.426(10) . ?
O3 C13 1.430(10) . ?
O4 C15 1.428(9) . ?
O4 C14 1.415(10) . ?
O5 C17 1.422(10) . ?
O5 C16 1.396(10) . ?
O6 C18 1.397(9) . ?
O6 C19 1.418(10) . ?
O1 C20 1.389(9) . ?
O1 C9 1.405(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.538(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.544(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.540(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.524(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.528(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.526(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.511(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C20A O1A 1.381(16) . ?
C20A C19A 1.531(10) . ?
O2A C10A 1.366(15) . ?
O2A C11A 1.292(16) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A C9A 1.521(10) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.515(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A O1A 1.311(16) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A O3A 1.32(3) . ?
O3A C13A 1.476(17) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C13A C14A 1.529(10) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A O6A 1.368(16) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C14A O4A 1.473(16) . ?
O6A C18A 1.390(16) . ?
O4A C15A 1.376(16) . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C18A C17A 1.531(10) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C16A 1.528(10) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C17A O5A 1.337(16) . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C16A O5A 1.423(16) . ?
C7 H7 0.9300 . ?
C7 C6 1.3900 . ?
C7 C3 1.3900 . ?
C6 C8 1.3900 . ?
C6 F6 1.294(11) . ?
C8 H8 0.9300 . ?
C8 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.538(12) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.3900 . ?
C7A C3A 1.3900 . ?
C6A C8A 1.3900 . ?
C6A F6A 1.270(11) . ?
C8A H8A 0.9300 . ?
C8A C5A 1.3900 . ?
C5A H5A 0.9300 . ?
C5A C4A 1.3900 . ?
C4A H4A 0.9300 . ?
C4A C3A 1.3900 . ?

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
F005 P001 F003 92.2(3) . . ?
F009 P001 F003 89.9(4) . . ?
F009 P001 F005 85.0(3) . . ?
F009 P001 F00A 93.1(4) . . ?
F009 P001 F00B 171.3(5) . . ?
F009 P001 F 95.6(5) . . ?
F00A P001 F003 176.5(4) . . ?
F00A P001 F005 89.9(3) . . ?
F00B P001 F003 86.6(3) . . ?
F00B P001 F005 87.1(4) . . ?
F00B P001 F00A 90.6(4) . . ?
F P001 F003 87.5(4) . . ?
F P001 F005 179.2(5) . . ?
F P001 F00A 90.4(4) . . ?
F P001 F00B 92.2(4) . . ?
F0 P001 F2 95.2(14) . . ?
F0 P001 FA 93.4(14) . . ?
F2 P001 FA 171.2(15) . . ?
F3 P001 F0 33(2) . . ?
F3 P001 F2 95.6(14) . . ?
F3 P001 F4 122.8(18) . . ?
F3 P001 F00C 129.5(19) . . ?
F3 P001 FA 92.6(14) . . ?
F4 P001 F0 155(2) . . ?
F4 P001 F2 88.0(13) . . ?
F4 P001 FA 84.9(13) . . ?
F00C P001 F0 97.0(17) . . ?
F00C P001 F2 90.3(14) . . ?
F00C P001 F4 107.4(16) . . ?
F00C P001 FA 86.9(14) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1AA 109.3 . . ?
N1 C1 H1AB 109.3 . . ?
N1 C1 H1BC 109.4 . . ?
N1 C1 H1BD 109.4 . . ?
H1AA C1 H1AB 108.0 . . ?
H1BC C1 H1BD 108.0 . . ?
C2 C1 N1 111.5(7) . . ?
C2 C1 H1AA 109.3 . . ?
C2 C1 H1AB 109.3 . . ?
C2A C1 N1 111.0(7) . . ?
C2A C1 H1BC 109.4 . . ?
C2A C1 H1BD 109.4 . . ?
C10 O2 C11 105.5(10) . . ?
C12 O3 C13 121.8(18) . . ?
C14 O4 C15 99.4(15) . . ?
C16 O5 C17 115.5(17) . . ?
C18 O6 C19 119.4(14) . . ?
C20 O1 C9 107.7(12) . . ?
O2 C10 H10A 110.7 . . ?
O2 C10 H10B 110.7 . . ?
O2 C10 C9 105.1(15) . . ?
H10A C10 H10B 108.8 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
O4 C15 H15A 113.1 . . ?
O4 C15 H15B 113.1 . . ?
O4 C15 C16 93.1(16) . . ?
H15A C15 H15B 110.5 . . ?
C16 C15 H15A 113.1 . . ?
C16 C15 H15B 113.1 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.7(11) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
O5 C17 H17A 110.6 . . ?
O5 C17 H17B 110.6 . . ?
O5 C17 C18 105.8(16) . . ?
H17A C17 H17B 108.7 . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
O6 C18 C17 114.7(16) . . ?
O6 C18 H18A 108.6 . . ?
O6 C18 H18B 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
O2 C11 H11A 109.0 . . ?
O2 C11 H11B 109.0 . . ?
O2 C11 C12 113.0(18) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
O3 C12 C11 141(2) . . ?
O3 C12 H12A 101.7 . . ?
O3 C12 H12B 101.7 . . ?
C11 C12 H12A 101.7 . . ?
C11 C12 H12B 101.7 . . ?
H12A C12 H12B 104.7 . . ?
O6 C19 H19A 107.8 . . ?
O6 C19 H19B 107.8 . . ?
O6 C19 C20 118.1(16) . . ?
H19A C19 H19B 107.1 . . ?
C20 C19 H19A 107.8 . . ?
C20 C19 H19B 107.8 . . ?
O3 C13 H13A 109.8 . . ?
O3 C13 H13B 109.8 . . ?
O3 C13 C14 109.6(17) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
O4 C14 C13 91.9(16) . . ?
O4 C14 H14A 113.3 . . ?
O4 C14 H14B 113.3 . . ?
C13 C14 H14A 113.3 . . ?
C13 C14 H14B 113.3 . . ?
H14A C14 H14B 110.6 . . ?
O1 C20 C19 102.0(11) . . ?
O1 C20 H20A 111.4 . . ?
O1 C20 H20B 111.4 . . ?
C19 C20 H20A 111.4 . . ?
C19 C20 H20B 111.4 . . ?
H20A C20 H20B 109.2 . . ?
O5 C16 C15 110.9(17) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
O1 C9 C10 119.8(16) . . ?
O1 C9 H9A 107.4 . . ?
O1 C9 H9B 107.4 . . ?
C10 C9 H9A 107.4 . . ?
C10 C9 H9B 107.4 . . ?
H9A C9 H9B 106.9 . . ?
H20C C20A H20D 109.2 . . ?
O1A C20A H20C 111.3 . . ?
O1A C20A H20D 111.3 . . ?
O1A C20A C19A 102.1(17) . . ?
C19A C20A H20C 111.3 . . ?
C19A C20A H20D 111.3 . . ?
C11A O2A C10A 104.7(18) . . ?
O2A C10A H10C 111.1 . . ?
O2A C10A H10D 111.1 . . ?
O2A C10A C9A 103.3(17) . . ?
H10C C10A H10D 109.1 . . ?
C9A C10A H10C 111.1 . . ?
C9A C10A H10D 111.1 . . ?
O2A C11A H11C 110.4 . . ?
O2A C11A H11D 110.4 . . ?
O2A C11A C12A 106.6(19) . . ?
H11C C11A H11D 108.6 . . ?
C12A C11A H11C 110.4 . . ?
C12A C11A H11D 110.4 . . ?
C10A C9A H9AA 109.9 . . ?
C10A C9A H9AB 109.9 . . ?
H9AA C9A H9AB 108.3 . . ?
O1A C9A C10A 109.0(19) . . ?
O1A C9A H9AA 109.9 . . ?
O1A C9A H9AB 109.9 . . ?
C11A C12A H12C 113.4 . . ?
C11A C12A H12D 113.4 . . ?
H12C C12A H12D 110.7 . . ?
O3A C12A C11A 91.4(17) . . ?
O3A C12A H12C 113.4 . . ?
O3A C12A H12D 113.4 . . ?
C9A O1A C20A 106.6(18) . . ?
C12A O3A C13A 93.4(16) . . ?
O3A C13A H13C 110.4 . . ?
O3A C13A H13D 110.4 . . ?
O3A C13A C14A 106.7(18) . . ?
H13C C13A H13D 108.6 . . ?
C14A C13A H13C 110.4 . . ?
C14A C13A H13D 110.4 . . ?
C20A C19A H19C 111.0 . . ?
C20A C19A H19D 111.0 . . ?
H19C C19A H19D 109.0 . . ?
O6A C19A C20A 103.8(17) . . ?
O6A C19A H19C 111.0 . . ?
O6A C19A H19D 111.0 . . ?
C13A C14A H14C 100.2 . . ?
C13A C14A H14D 100.2 . . ?
H14C C14A H14D 104.2 . . ?
O4A C14A C13A 146(2) . . ?
O4A C14A H14C 100.2 . . ?
O4A C14A H14D 100.2 . . ?
C19A O6A C18A 111.9(17) . . ?
C15A O4A C14A 125.0(17) . . ?
O6A C18A H18C 109.5 . . ?
O6A C18A H18D 109.5 . . ?
O6A C18A C17A 110.6(18) . . ?
H18C C18A H18D 108.1 . . ?
C17A C18A H18C 109.5 . . ?
C17A C18A H18D 109.5 . . ?
O4A C15A H15C 111.0 . . ?
O4A C15A H15D 111.0 . . ?
O4A C15A C16A 103.6(17) . . ?
H15C C15A H15D 109.0 . . ?
C16A C15A H15C 111.0 . . ?
C16A C15A H15D 111.0 . . ?
C18A C17A H17C 110.2 . . ?
C18A C17A H17D 110.2 . . ?
H17C C17A H17D 108.5 . . ?
O5A C17A C18A 107.4(17) . . ?
O5A C17A H17C 110.2 . . ?
O5A C17A H17D 110.2 . . ?
C15A C16A H16C 110.0 . . ?
C15A C16A H16D 110.0 . . ?
H16C C16A H16D 108.3 . . ?
O5A C16A C15A 108.7(19) . . ?
O5A C16A H16C 110.0 . . ?
O5A C16A H16D 110.0 . . ?
C17A O5A C16A 115.0(17) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C3 120.0 . . ?
C3 C7 H7 120.0 . . ?
C8 C6 C7 120.0 . . ?
F6 C6 C7 105.3(10) . . ?
F6 C6 C8 134.6(10) . . ?
C6 C8 H8 120.0 . . ?
C5 C8 C6 120.0 . . ?
C5 C8 H8 120.0 . . ?
C8 C5 H5 120.0 . . ?
C4 C5 C8 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C7 C3 C2 120.7(11) . . ?
C4 C3 C2 119.2(11) . . ?
C4 C3 C7 120.0 . . ?
C1 C2A H2AA 109.6 . . ?
C1 C2A H2AB 109.6 . . ?
C1 C2A C3A 110.2(12) . . ?
H2AA C2A H2AB 108.1 . . ?
C3A C2A H2AA 109.6 . . ?
C3A C2A H2AB 109.6 . . ?
C6A C7A H7A 120.0 . . ?
C6A C7A C3A 120.0 . . ?
C3A C7A H7A 120.0 . . ?
C8A C6A C7A 120.0 . . ?
F6A C6A C7A 107.0(11) . . ?
F6A C6A C8A 132.9(11) . . ?
C6A C8A H8A 120.0 . . ?
C5A C8A C6A 120.0 . . ?
C5A C8A H8A 120.0 . . ?
C8A C5A H5A 120.0 . . ?
C8A C5A C4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C7A C3A C2A 121.2(10) . . ?
C4A C3A C2A 118.1(10) . . ?
C4A C3A C7A 120.0 . . ?

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 H1A O2 0.89 2.02 2.786(14) 143.6 . yes
N1 H1B O1 0.89 2.13 2.773(12) 128.3 . yes
N1 H1C O4 0.89 2.09 2.889(15) 148.6 . yes
N1 H1C O5 0.89 2.19 2.877(17) 133.4 . 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 C1 C2 C3 -172.2(10) . . . . ?
N1 C1 C2A C3A 169.2(9) . . . . ?
C1 C2 C3 C7 -113.1(13) . . . . ?
C1 C2 C3 C4 71.3(16) . . . . ?
C1 C2A C3A C7A 106.4(12) . . . . ?
C1 C2A C3A C4A -83.6(14) . . . . ?
O2 C10 C9 O1 7(3) . . . . ?
O2 C11 C12 O3 -58(4) . . . . ?
O3 C13 C14 O4 110(2) . . . . ?
O4 C15 C16 O5 75(2) . . . . ?
O5 C17 C18 O6 -60(2) . . . . ?
O6 C19 C20 O1 45(3) . . . . ?
C10 O2 C11 C12 -171.9(19) . . . . ?
C15 O4 C14 C13 91.7(17) . . . . ?
C17 O5 C16 C15 160.4(17) . . . . ?
C18 O6 C19 C20 -177.9(17) . . . . ?
C11 O2 C10 C9 -179.2(19) . . . . ?
C12 O3 C13 C14 -168(2) . . . . ?
C19 O6 C18 C17 -171.5(17) . . . . ?
C13 O3 C12 C11 114(4) . . . . ?
C14 O4 C15 C16 171.1(15) . . . . ?
C20 O1 C9 C10 -172(2) . . . . ?
C16 O5 C17 C18 -175.0(17) . . . . ?
C9 O1 C20 C19 136(2) . . . . ?
C20A C19A O6A C18A -169.2(18) . . . . ?
O2A C10A C9A O1A -70(2) . . . . ?
O2A C11A C12A O3A -54(3) . . . . ?
C10A O2A C11A C12A -149.5(19) . . . . ?
C10A C9A O1A C20A 174.3(18) . . . . ?
C11A O2A C10A C9A -154.9(19) . . . . ?
C11A C12A O3A C13A -160.1(18) . . . . ?
C12A O3A C13A C14A -139(2) . . . . ?
O1A C20A C19A O6A 91(2) . . . . ?
O3A C13A C14A O4A -31(5) . . . . ?
C13A C14A O4A C15A 150(3) . . . . ?
C19A C20A O1A C9A -168.9(18) . . . . ?
C19A O6A C18A C17A 179.8(18) . . . . ?
C14A O4A C15A C16A -153(2) . . . . ?
O6A C18A C17A O5A -78(2) . . . . ?
O4A C15A C16A O5A 78(2) . . . . ?
C18A C17A O5A C16A 178.9(17) . . . . ?
C15A C16A O5A C17A 168.0(19) . . . . ?
C7 C6 C8 C5 0.0 . . . . ?
C6 C7 C3 C2 -175.6(15) . . . . ?
C6 C7 C3 C4 0.0 . . . . ?
C6 C8 C5 C4 0.0 . . . . ?
C8 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 175.6(15) . . . . ?
C5 C4 C3 C7 0.0 . . . . ?
C3 C7 C6 C8 0.0 . . . . ?
C3 C7 C6 F6 -177.3(13) . . . . ?
F6 C6 C8 C5 176.3(18) . . . . ?
C7A C6A C8A C5A 0.0 . . . . ?
C6A C7A C3A C2A 169.8(14) . . . . ?
C6A C7A C3A C4A 0.0 . . . . ?
C6A C8A C5A C4A 0.0 . . . . ?
C8A C5A C4A C3A 0.0 . . . . ?
C5A C4A C3A C2A -170.2(14) . . . . ?
C5A C4A C3A C7A 0.0 . . . . ?
C3A C7A C6A C8A 0.0 . . . . ?
C3A C7A C6A F6A -177.1(14) . . . . ?
F6A C6A C8A C5A 176.2(18) . . . . ?

_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_4F_298K
_database_code_depnum_ccdc_archive 'CCDC 2545078'
loop_
_audit_author_name
_audit_author_address
Liujunchao
;Anhui Ploytechnic University
China
;
_audit_update_record             
;
2026-05-23 deposited with the CCDC.	2026-06-10 downloaded from the CCDC.
;
_audit_creation_date             2026-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.10 svn.r48fbca5a for OlexSys, GUI svn.r7537)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, C12 H24 O6, 0.5(C16 H22 F2 N2)'
_chemical_formula_sum            'C20 H35 F7 N O6 P'
_chemical_formula_weight         549.46
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   11.231(4)
_cell_length_b                   18.764(6)
_cell_length_c                   12.639(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2663.5(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6248
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      18.45
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0983 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.8494.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45761
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.664
_diffrn_reflns_theta_min         2.113
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_oxdiff_ac3_digest_hkl    41564ff55fe99444a83e5c1c55cb25e4870f14
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1150
_reflns_number_total             1680
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     518
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.1421
_refine_ls_restrained_S_all      1.252
_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)+10.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1877
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C8-C2 = C7-C8
 1.54 with sigma of 0.02
 N1-C7
 1.48 with sigma of 0.2
 C1-O9 = C1-C11
 1.42 with sigma of 0.02
 C11-O12
 1.54 with sigma of 0.02
 C12-C8
 1.54 with sigma of 0.01
 F1-C4
 1.38 with sigma of 0.1
 C11-C1 = C10-C13 = C15-C16 = C1A-C19 = C18-C17 = C14-C9
 1.54 with sigma of 0.01
 O9-C14 = O9-C1 = O12-C11 = O12-C10 = O1-C13 = O3-C16 = O1-C15 = O4-C1A = O4-
 C18 = O2-C17 = O2-C9
 1.42 with sigma of 0.01
 C19-O3
 1.42 with sigma of 0.01
 C11-C10
 2.28 with sigma of 0.02
 O12-C1
 2.28 with sigma of 0.02
 O9-C11
 2.28 with sigma of 0.02
 C1A-O3
 2.28 with sigma of 0.02
 C2-C8 \\sim C6-C8
 with sigma of 0.02
 C5-F1 \\sim C3-F1
 with sigma of 0.02
 P1-F3 \\sim P1-F3A
 with sigma of 0.02
 P1-F2 \\sim P1-F2A
 with sigma of 0.02
 P1-F4 \\sim P1-F4A
 with sigma of 0.02
 F3-F2 \\sim F3A-F2A
 with sigma of 0.04
 F3-F4 \\sim F3A-F4A
 with sigma of 0.04
 F2-F4 \\sim F2A-F4A
 with sigma of 0.04
3. Restrained planarity
 C6, C2, C12, C8, C4, F1
 with sigma of 0.02
4. Rigid bond restraints
 P1, F3, F2, F4
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
5. Uiso/Uaniso restraints and constraints
C8 \\sim C3 \\sim C2 \\sim C4 \\sim C12 \\sim C5 \\sim C7 \\sim C6 \\sim N1:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
O12 \\sim C11 \\sim C1 \\sim O9: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
C11 \\sim O12 \\sim C10 \\sim C1 \\sim C13 \\sim O9 \\sim O1 \\sim C14 \\sim
C15 \\sim C9 \\sim C16 \\sim O2 \\sim O3 \\sim C17 \\sim C19 \\sim C18 \\sim
C1A \\sim O4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
F1 \\sim C4: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.02
within 2A
F3 \\sim P1 \\sim F2 \\sim F4: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
P1 \\sim F2 \\sim F2A \\sim F4 \\sim F4A \\sim F3 \\sim F3A: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
6. Rigid body (RIGU) restrains
 C12, C3, C2, C4, C8, C5, C7, C6, N1
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C1, O12, C11, C10, C13, O9, O1, C14, C15, C9, C16, O2, O3, C17, C19, C18, C1A,
  O4
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.01
 P1, F2, F2A, F4, F4A, F3, F3A
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
7. Others
 Sof(F2A)=Sof(F4A)=0.5*(1-FVAR(2))
 Sof(F2)=Sof(F4)=0.5*FVAR(2)
 Fixed Sof: F3(0.25) O12(0.25) C11(0.25) H11B(0.25) H11A(0.25) C1(0.25)
 H1A(0.25) H1B(0.25) N1(0.25) H1D(0.25) H1C(0.25) H1E(0.25) O9(0.25) C8(0.25)
 H8B(0.25) H8A(0.25) C7(0.25) H7B(0.25) H7A(0.25) C12(0.25) C6(0.25) H6(0.25)
 C5(0.25) H5(0.25) C4(0.25) C3(0.25) H3(0.25) C2(0.25) H2(0.25) F1(0.25)
 C9(0.25) H9B(0.25) H9A(0.25) C10(0.25) H10B(0.25) H10A(0.25) C13(0.25)
 H13B(0.25) H13A(0.25) C14(0.25) H14B(0.25) H14A(0.25) O1(0.25) C15(0.25)
 H15A(0.25) H15B(0.25) O2(0.25) C16(0.25) H16A(0.25) H16B(0.25) C17(0.25)
 H17B(0.25) H17A(0.25) O3(0.25) C18(0.25) H18B(0.25) H18A(0.25) C19(0.25)
 H19B(0.25) H19A(0.25) O4(0.25) C1A(0.25) H1AB(0.25) H1AA(0.25) F3A(0.25)
8.a Secondary CH2 refined with riding coordinates:
 C11(H11B,H11A), C1(H1A,H1B), C8(H8B,H8A), C7(H7B,H7A), C9(H9B,H9A), C10(H10B,
 H10A), C13(H13B,H13A), C14(H14B,H14A), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17B,H17A), C18(H18B,H18A), C19(H19B,H19A), C1A(H1AB,H1AA)
8.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C2(H2)
8.c Fitted hexagon refined as free rotating group:
 C12(C6,C5,C4,C3,C2)
8.d Idealised Me refined as rotating group:
 N1(H1D,H1C,H1E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.63202(18) 0.750000 0.1178(10) Uani 1 4 d DS TU P . .
F3 F 0.582(2) 0.6996(9) 0.750000 0.138(6) Uani 0.5 2 d DS TU P A 1
F2 F 0.500000 0.6306(8) 0.8746(7) 0.145(5) Uani 0.63(3) 2 d DS TU P A 1
F4 F 0.3862(15) 0.5819(10) 0.750000 0.167(6) Uani 0.63(3) 2 d DS TU P A 1
O12 O 0.9784(18) 0.3656(7) 0.5609(14) 0.130(5) Uani 0.25 1 d D U P B -1
C11 C 0.8739(16) 0.3223(10) 0.545(3) 0.126(5) Uani 0.25 1 d D U P B -1
H11B H 0.877402 0.277901 0.584695 0.151 Uiso 0.25 1 calc R U P B -1
H11A H 0.858642 0.312571 0.471232 0.151 Uiso 0.25 1 calc R U P B -1
C1 C 0.785(2) 0.3746(14) 0.592(2) 0.128(5) Uani 0.25 1 d D U P B -1
H1A H 0.706299 0.353634 0.599691 0.154 Uiso 0.25 1 calc R U P B -1
H1B H 0.811104 0.392994 0.660090 0.154 Uiso 0.25 1 calc R U P B -1
N1 N 1.012(6) 0.5089(6) 0.5878(8) 0.081(8) Uani 0.25 1 d D U P C -1
H1D H 0.951104 0.506230 0.542379 0.098 Uiso 0.25 1 calc R U P C -1
H1C H 1.061275 0.472748 0.576551 0.098 Uiso 0.25 1 calc R U P C -1
H1E H 1.049978 0.549897 0.578441 0.098 Uiso 0.25 1 calc R U P C -1
O9 O 0.7876(18) 0.4272(11) 0.5129(18) 0.127(4) Uani 0.25 1 d D U P B -1
C8 C 1.0410(17) 0.5565(6) 0.7681(19) 0.120(7) Uani 0.25 1 d D U P C -1
H8B H 1.031043 0.542973 0.841607 0.144 Uiso 0.25 1 calc R U P C -1
H8A H 1.124481 0.550683 0.750268 0.144 Uiso 0.25 1 calc R U P C -1
C7 C 0.965(2) 0.5053(10) 0.6974(13) 0.127(8) Uani 0.25 1 d D U P C -1
H7B H 0.971191 0.456856 0.723879 0.153 Uiso 0.25 1 calc R U P C -1
H7A H 0.882357 0.519465 0.698930 0.153 Uiso 0.25 1 calc R U P C -1
C12 C 1.0098(15) 0.6289(4) 0.7563(16) 0.100(4) Uani 0.25 1 d DG U P C -1
C6 C 0.9075(13) 0.6689(6) 0.739(2) 0.092(6) Uani 0.25 1 d DG U P C -1
H6 H 0.834034 0.646362 0.733044 0.111 Uiso 0.25 1 calc R U P C -1
C5 C 0.9149(11) 0.7427(6) 0.731(2) 0.090(6) Uani 0.25 1 d DG U P C -1
H5 H 0.846407 0.769447 0.719609 0.108 Uiso 0.25 1 calc R U P C -1
C4 C 1.0246(12) 0.7764(4) 0.7402(19) 0.098(6) Uani 0.25 1 d DG U P C -1
C3 C 1.1269(11) 0.7363(6) 0.757(2) 0.101(6) Uani 0.25 1 d DG U P C -1
H3 H 1.200338 0.758871 0.763419 0.121 Uiso 0.25 1 calc R U P C -1
C2 C 1.1195(13) 0.6626(5) 0.765(2) 0.110(7) Uani 0.25 1 d DG U P C -1
H2 H 1.187967 0.635785 0.776853 0.131 Uiso 0.25 1 calc R U P C -1
F1 F 1.0351(13) 0.8485(5) 0.732(2) 0.146(8) Uani 0.25 1 d D U P C -1
C9 C 0.6748(17) 0.4908(19) 0.4818(19) 0.128(4) Uani 0.25 1 d D U P B -1
H9B H 0.686862 0.462448 0.418496 0.153 Uiso 0.25 1 calc R U P B -1
H9A H 0.601167 0.517727 0.479557 0.153 Uiso 0.25 1 calc R U P B -1
C10 C 1.0721(16) 0.3151(11) 0.558(3) 0.117(5) Uani 0.25 1 d D U P B -1
H10B H 1.056048 0.280200 0.503262 0.141 Uiso 0.25 1 calc R U P B -1
H10A H 1.076111 0.290348 0.625230 0.141 Uiso 0.25 1 calc R U P B -1
C13 C 1.191(2) 0.3510(12) 0.536(3) 0.122(5) Uani 0.25 1 d D U P B -1
H13B H 1.248956 0.313031 0.545186 0.147 Uiso 0.25 1 calc R U P B -1
H13A H 1.189386 0.360280 0.460424 0.147 Uiso 0.25 1 calc R U P B -1
C14 C 0.700(2) 0.4521(18) 0.5872(17) 0.132(4) Uani 0.25 1 d D U P B -1
H14B H 0.729742 0.481484 0.644652 0.159 Uiso 0.25 1 calc R U P B -1
H14A H 0.641255 0.417525 0.609754 0.159 Uiso 0.25 1 calc R U P B -1
O1 O 1.2486(19) 0.4111(7) 0.5779(16) 0.130(5) Uani 0.25 1 d D U P B -1
C15 C 1.286(3) 0.4796(10) 0.535(3) 0.135(6) Uani 0.25 1 d D U P B -1
H15A H 1.324685 0.464448 0.469964 0.162 Uiso 0.25 1 calc R U P B -1
H15B H 1.350701 0.491469 0.582063 0.162 Uiso 0.25 1 calc R U P B -1
O2 O 0.7755(14) 0.5289(10) 0.5172(19) 0.132(4) Uani 0.25 1 d D U P B -1
C16 C 1.242(3) 0.5551(15) 0.502(3) 0.135(6) Uani 0.25 1 d D U P B -1
H16A H 1.259602 0.578447 0.569245 0.162 Uiso 0.25 1 calc R U P B -1
H16B H 1.310145 0.567440 0.458566 0.162 Uiso 0.25 1 calc R U P B -1
C17 C 0.6814(18) 0.5651(14) 0.467(2) 0.132(5) Uani 0.25 1 d D U P B -1
H17B H 0.613371 0.574679 0.512455 0.158 Uiso 0.25 1 calc R U P B -1
H17A H 0.657663 0.545485 0.399603 0.158 Uiso 0.25 1 calc R U P B -1
O3 O 1.1634(17) 0.6077(11) 0.4625(19) 0.137(5) Uani 0.25 1 d D U P B -1
C18 C 0.772(2) 0.6259(18) 0.461(4) 0.131(5) Uani 0.25 1 d D U P B -1
H18B H 0.734978 0.658749 0.411840 0.157 Uiso 0.25 1 calc R U P B -1
H18A H 0.764921 0.648400 0.529667 0.157 Uiso 0.25 1 calc R U P B -1
C19 C 1.120(2) 0.6667(13) 0.406(2) 0.142(5) Uani 0.25 1 d D U P B -1
H19B H 1.116765 0.656633 0.330898 0.170 Uiso 0.25 1 calc R U P B -1
H19A H 1.169358 0.708220 0.417724 0.170 Uiso 0.25 1 calc R U P B -1
O4 O 0.8953(18) 0.6341(12) 0.438(2) 0.136(5) Uani 0.25 1 d D U P B -1
C1A C 0.9949(19) 0.6788(11) 0.450(2) 0.143(5) Uani 0.25 1 d D U P B -1
H1AB H 1.005018 0.684711 0.525615 0.172 Uiso 0.25 1 calc R U P B -1
H1AA H 0.970339 0.724946 0.423018 0.172 Uiso 0.25 1 calc R U P B -1
F2A F 0.431(3) 0.6333(14) 0.8570(19) 0.148(7) Uani 0.186(15) 1 d D U P A 2
F4A F 0.448(3) 0.5573(10) 0.717(2) 0.158(11) Uani 0.186(15) 1 d D U P A 2
F3A F 0.6040(19) 0.6797(13) 0.792(2) 0.158(8) Uani 0.25 1 d D 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 F3 1.571(11) 3_656 ?
P1 F3 1.571(11) . ?
P1 F2 1.575(8) 10_557 ?
P1 F2 1.575(8) . ?
P1 F4 1.587(10) 3_656 ?
P1 F4 1.587(10) . ?
P1 F2A 1.561(15) 10_557 ?
P1 F2A 1.561(15) . ?
P1 F2A 1.561(15) 12_655 ?
P1 F2A 1.561(15) 3_656 ?
P1 F4A 1.576(14) 3_656 ?
P1 F4A 1.576(14) 10_557 ?
P1 F4A 1.576(14) 12_655 ?
P1 F4A 1.576(14) . ?
P1 F3A 1.564(12) 12_655 ?
P1 F3A 1.564(13) 10_557 ?
P1 F3A 1.564(12) 3_656 ?
P1 F3A 1.564(13) . ?
O12 C11 1.441(9) . ?
O12 C10 1.416(10) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 C1 1.522(10) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 O9 1.408(9) . ?
N1 H1D 0.8900 . ?
N1 H1C 0.8900 . ?
N1 H1E 0.8900 . ?
N1 C7 1.48(3) . ?
O9 C14 1.436(11) . ?
C8 H8B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 C7 1.563(17) . ?
C8 C12 1.411(9) . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C12 C6 1.3900 . ?
C12 C2 1.3900 . ?
C6 H6 0.9300 . ?
C6 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C4 C3 1.3900 . ?
C4 F1 1.363(11) . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 C14 1.544(11) . ?
C9 O2 1.411(10) . ?
C10 H10B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 C13 1.524(11) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 O1 1.401(10) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
O1 C15 1.458(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.554(10) . ?
O2 C17 1.404(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 O3 1.420(10) . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 C18 1.532(11) . ?
O3 C19 1.405(10) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 O4 1.420(11) . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 C1A 1.523(11) . ?
O4 C1A 1.407(11) . ?
C1A H1AB 0.9700 . ?
C1A H1AA 0.9700 . ?
F2A F4A 1.72(3) 10_557 ?
F2A F3A 1.26(3) 12_655 ?

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
F3 P1 F3 72.3(19) 3_656 . ?
F3 P1 F2 90.8(4) . 10_557 ?
F3 P1 F2 90.8(4) 3_656 . ?
F3 P1 F2 90.8(4) 3_656 10_557 ?
F3 P1 F2 90.8(4) . . ?
F3 P1 F4 90.2(12) . 3_656 ?
F3 P1 F4 90.2(12) 3_656 . ?
F3 P1 F4 162.5(13) . . ?
F3 P1 F4 162.5(13) 3_656 3_656 ?
F3 P1 F4A 159.7(16) . 10_557 ?
F3 P1 F4A 120.0(15) 3_656 10_557 ?
F3 P1 F4A 120.0(15) . 3_656 ?
F3 P1 F4A 159.7(16) 3_656 3_656 ?
F3 P1 F4A 159.7(16) 3_656 12_655 ?
F3 P1 F4A 120.0(15) . 12_655 ?
F3 P1 F3A 25.6(11) . 10_557 ?
F3 P1 F3A 25.6(11) 3_656 12_655 ?
F3 P1 F3A 88.8(8) . 3_656 ?
F3 P1 F3A 25.6(11) 3_656 3_656 ?
F3 P1 F3A 88.8(8) 3_656 10_557 ?
F3 P1 F3A 88.8(8) . 12_655 ?
F2 P1 F2 178.1(11) 10_557 . ?
F2 P1 F4 89.4(3) . . ?
F2 P1 F4 89.4(3) 10_557 3_656 ?
F2 P1 F4 89.4(3) 10_557 . ?
F2 P1 F4 89.4(3) . 3_656 ?
F2 P1 F4A 104.5(14) 10_557 10_557 ?
F2 P1 F4A 73.8(12) . 3_656 ?
F2 P1 F4A 73.8(12) . 10_557 ?
F2 P1 F4A 73.8(12) 10_557 12_655 ?
F2 P1 F4A 104.5(13) . 12_655 ?
F2 P1 F4A 104.5(13) 10_557 3_656 ?
F4 P1 F4 107.3(17) 3_656 . ?
F2A P1 F2A 60(3) 12_655 . ?
F2A P1 F2A 120(3) 10_557 . ?
F2A P1 F4A 88.3(15) 3_656 . ?
F2A P1 F4A 115.3(14) 12_655 . ?
F2A P1 F4A 66.3(15) 10_557 . ?
F2A P1 F4A 93.3(13) . . ?
F2A P1 F3A 131.2(15) 10_557 . ?
F2A P1 F3A 85.0(16) . 3_656 ?
F2A P1 F3A 94.1(14) 3_656 3_656 ?
F2A P1 F3A 47.5(13) 12_655 . ?
F2A P1 F3A 131.2(15) 12_655 3_656 ?
F2A P1 F3A 94.1(14) . . ?
F2A P1 F3A 85.0(16) 3_656 . ?
F2A P1 F3A 47.5(13) 10_557 3_656 ?
F3A P1 F4A 98.2(15) 3_656 . ?
F3A P1 F4A 108.8(19) 12_655 . ?
F3A P1 F4A 151.1(15) . . ?
F3A P1 F4A 134.1(16) 10_557 . ?
F3A P1 F3A 110(2) 3_656 . ?
C10 O12 C11 103.0(12) . . ?
O12 C11 H11B 112.4 . . ?
O12 C11 H11A 112.4 . . ?
O12 C11 C1 96.8(12) . . ?
H11B C11 H11A 110.0 . . ?
C1 C11 H11B 112.4 . . ?
C1 C11 H11A 112.4 . . ?
C11 C1 H1A 111.9 . . ?
C11 C1 H1B 111.9 . . ?
H1A C1 H1B 109.6 . . ?
O9 C1 C11 99.2(12) . . ?
O9 C1 H1A 111.9 . . ?
O9 C1 H1B 111.9 . . ?
H1D N1 H1C 109.5 . . ?
H1D N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
C7 N1 H1D 109.5 . . ?
C7 N1 H1C 109.5 . . ?
C7 N1 H1E 109.5 . . ?
C1 O9 C14 75.3(19) . . ?
H8B C8 H8A 107.7 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C12 C8 H8B 108.9 . . ?
C12 C8 H8A 108.9 . . ?
C12 C8 C7 113.4(11) . . ?
N1 C7 C8 108(3) . . ?
N1 C7 H7B 110.0 . . ?
N1 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C8 C7 H7A 110.0 . . ?
H7B C7 H7A 108.4 . . ?
C6 C12 C8 138.0(7) . . ?
C6 C12 C2 120.0 . . ?
C2 C12 C8 102.0(7) . . ?
C12 C6 H6 120.0 . . ?
C12 C6 C5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 120.0 . . ?
F1 C4 C5 121.5(7) . . ?
F1 C4 C3 118.5(7) . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C12 C2 H2 120.0 . . ?
C3 C2 C12 120.0 . . ?
C3 C2 H2 120.0 . . ?
H9B C9 H9A 112.4 . . ?
C14 C9 H9B 115.3 . . ?
C14 C9 H9A 115.3 . . ?
O2 C9 H9B 115.3 . . ?
O2 C9 H9A 115.3 . . ?
O2 C9 C14 79.5(17) . . ?
O12 C10 H10B 109.4 . . ?
O12 C10 H10A 109.4 . . ?
O12 C10 C13 111.3(19) . . ?
H10B C10 H10A 108.0 . . ?
C13 C10 H10B 109.4 . . ?
C13 C10 H10A 109.4 . . ?
C10 C13 H13B 103.8 . . ?
C10 C13 H13A 103.8 . . ?
H13B C13 H13A 105.4 . . ?
O1 C13 C10 134(2) . . ?
O1 C13 H13B 103.8 . . ?
O1 C13 H13A 103.8 . . ?
O9 C14 C9 73.4(18) . . ?
O9 C14 H14B 116.2 . . ?
O9 C14 H14A 116.2 . . ?
C9 C14 H14B 116.2 . . ?
C9 C14 H14A 116.2 . . ?
H14B C14 H14A 113.2 . . ?
C13 O1 C15 134(3) . . ?
O1 C15 H15A 100.8 . . ?
O1 C15 H15B 100.8 . . ?
O1 C15 C16 144(3) . . ?
H15A C15 H15B 104.4 . . ?
C16 C15 H15A 100.8 . . ?
C16 C15 H15B 100.8 . . ?
C17 O2 C9 60(2) . . ?
C15 C16 H16A 97.0 . . ?
C15 C16 H16B 97.0 . . ?
H16A C16 H16B 103.5 . . ?
O3 C16 C15 157(4) . . ?
O3 C16 H16A 97.0 . . ?
O3 C16 H16B 97.0 . . ?
O2 C17 H17B 114.8 . . ?
O2 C17 H17A 114.8 . . ?
O2 C17 C18 83(2) . . ?
H17B C17 H17A 111.8 . . ?
C18 C17 H17B 114.8 . . ?
C18 C17 H17A 114.8 . . ?
C19 O3 C16 161(2) . . ?
C17 C18 H18B 102.7 . . ?
C17 C18 H18A 102.7 . . ?
H18B C18 H18A 105.0 . . ?
O4 C18 C17 138(3) . . ?
O4 C18 H18B 102.7 . . ?
O4 C18 H18A 102.7 . . ?
O3 C19 H19B 110.8 . . ?
O3 C19 H19A 110.8 . . ?
O3 C19 C1A 104.8(14) . . ?
H19B C19 H19A 108.9 . . ?
C1A C19 H19B 110.8 . . ?
C1A C19 H19A 110.8 . . ?
C1A O4 C18 145(2) . . ?
C19 C1A H1AB 105.5 . . ?
C19 C1A H1AA 105.5 . . ?
O4 C1A C19 127(2) . . ?
O4 C1A H1AB 105.5 . . ?
O4 C1A H1AA 105.5 . . ?
H1AB C1A H1AA 106.1 . . ?
P1 F2A F4A 57.2(10) . 10_557 ?
F3A F2A P1 66.4(11) 12_655 . ?

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
O12 C11 C1 O9 70(2) . . . . ?
O12 C10 C13 O1 48(5) . . . . ?
C11 O12 C10 C13 161(3) . . . . ?
C11 C1 O9 C14 178(2) . . . . ?
C1 O9 C14 C9 -159(2) . . . . ?
C8 C12 C6 C5 -179.4(8) . . . . ?
C8 C12 C2 C3 179.6(5) . . . . ?
C7 C8 C12 C6 35.5(17) . . . . ?
C7 C8 C12 C2 -144.0(15) . . . . ?
C12 C8 C7 N1 78(2) . . . . ?
C12 C6 C5 C4 0.0 . . . . ?
C6 C12 C2 C3 0.0 . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C5 C4 F1 179.5(6) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C12 0.0 . . . . ?
C2 C12 C6 C5 0.0 . . . . ?
F1 C4 C3 C2 -179.5(6) . . . . ?
C9 O2 C17 C18 -166(3) . . . . ?
C10 O12 C11 C1 159(2) . . . . ?
C10 C13 O1 C15 -116(4) . . . . ?
C13 O1 C15 C16 79(7) . . . . ?
C14 C9 O2 C17 -141(2) . . . . ?
O1 C15 C16 O3 -35(14) . . . . ?
C15 C16 O3 C19 -135(8) . . . . ?
O2 C9 C14 O9 -76.1(17) . . . . ?
O2 C17 C18 O4 42(5) . . . . ?
C16 O3 C19 C1A -170(9) . . . . ?
C17 C18 O4 C1A -159(3) . . . . ?
O3 C19 C1A O4 -68(3) . . . . ?
C18 O4 C1A C19 -178(4) . . . . ?
F2A P1 F2A F4A -102(2) 12_655 . . 10_557 ?
F2A P1 F2A F4A 80(3) 10_557 . . 10_557 ?
F2A P1 F2A F3A 130(2) 12_655 . . 12_655 ?
F2A P1 F2A F3A -48(3) 10_557 . . 12_655 ?
F4A P1 F2A F4A -39(3) 3_656 . . 10_557 ?
F4A P1 F2A F4A -24(4) 12_655 . . 10_557 ?
F4A P1 F2A F4A 15.1(16) . . . 10_557 ?
F4A P1 F2A F3A -152(2) 12_655 . . 12_655 ?
F4A P1 F2A F3A -167(2) 3_656 . . 12_655 ?
F4A P1 F2A F3A -113(3) . . . 12_655 ?
F4A P1 F2A F3A -128(4) 10_557 . . 12_655 ?
F3A P1 F2A F4A -153(2) 10_557 . . 10_557 ?
F3A P1 F2A F4A 113(2) 3_656 . . 10_557 ?
F3A P1 F2A F4A -137(2) . . . 10_557 ?
F3A P1 F2A F4A 128(4) 12_655 . . 10_557 ?
F3A P1 F2A F3A 95(3) . . . 12_655 ?
F3A P1 F2A F3A -14.7(15) 3_656 . . 12_655 ?
F3A P1 F2A F3A 80(4) 10_557 . . 12_655 ?

_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_2F_298K
_database_code_depnum_ccdc_archive 'CCDC 2527441'
loop_
_audit_author_name
_audit_author_address
'Liu Junchao'
;Anhui Ploytechnic University
China
;
_audit_update_record             
;
2026-05-23 deposited with the CCDC.	2026-06-10 downloaded from the CCDC.
;
_audit_creation_date             2026-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2026.04.10 svn.r48fbca5a for OlexSys, GUI svn.r7537)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 P, 1(C12 H24 O6), C8 H11 F N'
_chemical_formula_sum            'C20 H35 F7 N O6 P'
_chemical_formula_weight         549.46
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.249(4)
_cell_length_b                   15.792(6)
_cell_length_c                   13.564(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.780(13)
_cell_angle_gamma                90
_cell_volume                     2618.3(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4498
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      18.17
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1437 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.8562.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31398
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_min         1.982
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_oxdiff_ac3_digest_hkl    4196a51a3b3fcbe0672677d737533b302e203a
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2815
_reflns_number_total             4798
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         4798
_refine_ls_number_restraints     1556
_refine_ls_R_factor_all          0.2201
_refine_ls_R_factor_gt           0.1476
_refine_ls_restrained_S_all      0.918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.2161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2194
_refine_ls_wR_factor_ref         0.2391
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H,H,H,H) groups
2. Restrained distances
 N1-C20A = N1-C20
 1.48 with sigma of 0.02
 C19-C13 = C19A-C13A = C20-C19 = C20A-C19A
 1.56 with sigma of 0.02
 C19-C13 \\sim C19A-C13A \\sim C20-C19 \\sim C20A-C19A
 with sigma of 0.02
3. Restrained planarity
 C13A, C14A, C15A, F1A
 with sigma of 0.1
 C19A, C13A, C18A, C14A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
F1A \\sim F1 \\sim C14 \\sim C18: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
F2A \\sim P1 \\sim F4A \\sim F5A \\sim F6A \\sim F2 \\sim F7 \\sim F7A \\sim
F3A \\sim F4 \\sim F5 \\sim F3 \\sim F6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.04 within 2A
C17 \\sim N1 \\sim C20 \\sim C20A \\sim C19 \\sim C19A \\sim C13 \\sim C13A
\\sim C14 \\sim C18 \\sim C18A \\sim C14A \\sim C15 \\sim F1 \\sim C17A \\sim
C15A \\sim F1A \\sim C16 \\sim C16A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.04 within 2A
C7 \\sim O5 \\sim C8 \\sim C9 \\sim C10 \\sim O4 \\sim O6 \\sim C6 \\sim C11
\\sim C5 \\sim C12 \\sim O3 \\sim O1 \\sim C4 \\sim C1 \\sim C3 \\sim C2 \\sim
O2 \\sim O4A \\sim C5A \\sim C6A \\sim O3A \\sim C4A \\sim C7A \\sim C3A \\sim
C8A \\sim O2A \\sim O5A \\sim C2A \\sim C9A \\sim C1A \\sim C10A \\sim O1A
\\sim O6A \\sim C12A \\sim C11A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.04 within 2A
Uanis(C12) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C6)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
5. Rigid body (RIGU) restrains
 C19, N1, C20, C20A, C19A, C13, C13A, C14, C18, C14A, C18A, C15, F1, C17, C15A,
  F1A, C17A, C16, C16A
 with sigma for 1-2 distances of 0.04 and sigma for 1-3 distances of 0.01
 P1, F7, F7A, F2, F2A, F5, F5A, F4, F4A, F3, F3A, F6, F6A
 with sigma for 1-2 distances of 0.04 and sigma for 1-3 distances of 0.01
 O4A, C5A, C6A, O3A, C4A, C7A, C3A, C8A, O2A, O5A, C2A, C9A, C1A, C10A, O1A,
 O6A, C12A, C11A, O5, C8, C9, C7, C10, O4, O6, C6, C11, C5, C12, O3, O1, C4, C1,
  C3, C2, O2
 with sigma for 1-2 distances of 0.04 and sigma for 1-3 distances of 0.04
6. Others
 Sof(H1BF)=Sof(H1BG)=Sof(H1BH)=1-FVAR(1)
 Sof(H1AC)=Sof(H1AD)=Sof(H1AE)=FVAR(1)
 Sof(F7A)=Sof(F2A)=Sof(F5A)=Sof(F4A)=Sof(F3A)=Sof(F6A)=1-FVAR(2)
 Sof(F6)=Sof(F3)=Sof(F5)=Sof(F4)=Sof(F2)=Sof(F7)=FVAR(2)
 Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(O5A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=
 Sof(H9AA)=Sof(H9AB)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C10A)=Sof(H10C)=Sof(H10D)=
 Sof(O4A)=Sof(O6A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C11A)=Sof(H11C)=Sof(H11D)=
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(O3A)=Sof(O1A)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(O2A)=1-FVAR(3)
 Sof(O5)=Sof(O2)=Sof(O4)=Sof(O3)=Sof(O1)=Sof(O6)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C1)=Sof(H1A)=Sof(H1B)=
 Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=
 Sof(H5A)=Sof(H5B)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C9)=Sof(H9A)=Sof(H9B)=FVAR(3)
 Fixed Sof: C15(0.5) H15(0.5) C14(0.5) C13(0.5) C18(0.5) H18(0.5) C17(0.5)
 H17(0.5) C16(0.5) H16(0.5) C20(0.5) H20A(0.5) H20B(0.5) F1(0.7) C19(0.5)
 H19A(0.5) H19B(0.5) C20A(0.5) H20C(0.5) H20D(0.5) C19A(0.5) H19C(0.5)
 H19D(0.5) C15A(0.5) H15A(0.5) C16A(0.5) H16A(0.5) C17A(0.5) H17A(0.5)
 C18A(0.5) H18A(0.5) C13A(0.5) C14A(0.5) F1A(0.3)
7.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B), C2(H2A,H2B), C1(H1A,H1B), C7(H7A,H7B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B),
 C9(H9A,H9B), C20(H20A,H20B), C19(H19A,H19B), C20A(H20C,H20D), C19A(H19C,H19D),
 C5A(H5AA,H5AB), C8A(H8AA,H8AB), C9A(H9AA,H9AB), C7A(H7AA,H7AB), C10A(H10C,
 H10D), C6A(H6AA,H6AB), C11A(H11C,H11D), C12A(H12C,H12D), C4A(H4AA,H4AB),
 C1A(H1AA,H1AB), C3A(H3AA,H3AB), C2A(H2AA,H2AB)
7.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C18(H18), C17(H17), C16(H16), C15A(H15A), C16A(H16A), C17A(H17A),
 C18A(H18A)
7.c Fitted hexagon refined as free rotating group:
 C15(C14,C13,C18,C17,C16), C15A(C16A,C17A,C18A,C13A,C14A)
7.d Idealised Me refined as rotating group:
 N1(H1AC,H1AD,H1AE), N1(H1BF,H1BG,H1BH)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.74839(17) 0.38618(14) 0.30255(16) 0.0811(6) Uani 1 1 d . U . . .
O5 O 0.055(3) 0.186(3) 0.383(3) 0.087(6) Uani 0.51(3) 1 d . U P A 1
O2 O 0.456(4) 0.112(2) 0.226(3) 0.084(6) Uani 0.51(3) 1 d . U P A 1
N1 N 0.2612(4) 0.1714(3) 0.2827(4) 0.0740(15) Uani 1 1 d D U . . .
H1AC H 0.256278 0.117526 0.263816 0.089 Uiso 0.60(7) 1 calc R U P B 1
H1AD H 0.208065 0.183122 0.322269 0.089 Uiso 0.60(7) 1 calc R U P B 1
H1AE H 0.325846 0.180308 0.314947 0.089 Uiso 0.60(7) 1 calc R U P B 1
H1BF H 0.202228 0.146953 0.253357 0.089 Uiso 0.40(7) 1 calc R U P B 2
H1BG H 0.256452 0.170603 0.347879 0.089 Uiso 0.40(7) 1 calc R U P B 2
H1BH H 0.320794 0.143396 0.267358 0.089 Uiso 0.40(7) 1 calc R U P B 2
O4 O 0.067(3) 0.094(2) 0.200(2) 0.074(6) Uani 0.51(3) 1 d . U P A 1
F6 F 0.7473(16) 0.2869(10) 0.2748(10) 0.119(4) Uani 0.705(10) 1 d . U P C 1
O3 O 0.271(2) 0.027(3) 0.156(3) 0.078(6) Uani 0.51(3) 1 d . U P A 1
O1 O 0.4470(16) 0.1906(14) 0.4161(17) 0.070(4) Uani 0.51(3) 1 d . U P A 1
O6 O 0.254(2) 0.259(3) 0.462(3) 0.080(6) Uani 0.51(3) 1 d . U P A 1
F3 F 0.7508(13) 0.4763(7) 0.3503(7) 0.107(3) Uani 0.705(10) 1 d . U P C 1
F5 F 0.8528(8) 0.3767(6) 0.3756(7) 0.121(3) Uani 0.705(10) 1 d . U P C 1
F4 F 0.8297(9) 0.4048(6) 0.2193(7) 0.127(3) Uani 0.705(10) 1 d . U P C 1
F2 F 0.6477(8) 0.3981(7) 0.2271(9) 0.133(4) Uani 0.705(10) 1 d . U P C 1
F7 F 0.6716(12) 0.3681(8) 0.3861(9) 0.149(5) Uani 0.705(10) 1 d . U P C 1
C8 C -0.029(4) 0.178(3) 0.315(3) 0.084(7) Uani 0.51(3) 1 d . U P A 1
H8A H -0.027783 0.223720 0.267533 0.100 Uiso 0.51(3) 1 calc R U P A 1
H8B H -0.097517 0.180459 0.346664 0.100 Uiso 0.51(3) 1 calc R U P A 1
C6 C 0.078(3) 0.015(2) 0.158(3) 0.082(6) Uani 0.51(3) 1 d . U P A 1
H6A H 0.011919 0.001292 0.117615 0.099 Uiso 0.51(3) 1 calc R U P A 1
H6B H 0.089580 -0.027389 0.208506 0.099 Uiso 0.51(3) 1 calc R U P A 1
C2 C 0.5527(18) 0.1177(17) 0.2994(16) 0.081(5) Uani 0.51(3) 1 d . U P A 1
H2A H 0.552692 0.070203 0.344699 0.097 Uiso 0.51(3) 1 calc R U P A 1
H2B H 0.619526 0.115450 0.264934 0.097 Uiso 0.51(3) 1 calc R U P A 1
C1 C 0.549(3) 0.197(2) 0.354(3) 0.089(7) Uani 0.51(3) 1 d . U P A 1
H1A H 0.542065 0.244494 0.309540 0.106 Uiso 0.51(3) 1 calc R U P A 1
H1B H 0.614630 0.203602 0.397279 0.106 Uiso 0.51(3) 1 calc R U P A 1
C7 C -0.020(4) 0.094(3) 0.262(3) 0.092(8) Uani 0.51(3) 1 d . U P A 1
H7A H -0.009991 0.049004 0.310529 0.111 Uiso 0.51(3) 1 calc R U P A 1
H7B H -0.088136 0.083090 0.223057 0.111 Uiso 0.51(3) 1 calc R U P A 1
C10 C 0.155(2) 0.258(2) 0.519(2) 0.076(6) Uani 0.51(3) 1 d . U P A 1
H10A H 0.152612 0.307089 0.561522 0.091 Uiso 0.51(3) 1 calc R U P A 1
H10B H 0.153589 0.207261 0.559431 0.091 Uiso 0.51(3) 1 calc R U P A 1
C11 C 0.351(2) 0.255(2) 0.541(2) 0.082(7) Uani 0.51(3) 1 d . U P A 1
H11A H 0.351055 0.302960 0.585606 0.099 Uiso 0.51(3) 1 calc R U P A 1
H11B H 0.350351 0.202980 0.578388 0.099 Uiso 0.51(3) 1 calc R U P A 1
C12 C 0.447(2) 0.2583(18) 0.479(2) 0.074(6) Uani 0.51(3) 1 d . U P A 1
H12A H 0.444575 0.310327 0.440440 0.089 Uiso 0.51(3) 1 calc R U P A 1
H12B H 0.514068 0.258406 0.520866 0.089 Uiso 0.51(3) 1 calc R U P A 1
C4 C 0.368(2) 0.0362(18) 0.103(2) 0.082(6) Uani 0.51(3) 1 d . U P A 1
H4A H 0.372412 -0.010628 0.056952 0.098 Uiso 0.51(3) 1 calc R U P A 1
H4B H 0.363654 0.088323 0.064717 0.098 Uiso 0.51(3) 1 calc R U P A 1
C5 C 0.175(2) 0.018(3) 0.094(3) 0.091(7) Uani 0.51(3) 1 d . U P A 1
H5A H 0.177932 -0.034036 0.056088 0.110 Uiso 0.51(3) 1 calc R U P A 1
H5B H 0.166962 0.064998 0.047973 0.110 Uiso 0.51(3) 1 calc R U P A 1
C3 C 0.463(3) 0.038(2) 0.169(3) 0.096(7) Uani 0.51(3) 1 d . U P A 1
H3A H 0.465262 -0.012295 0.210651 0.115 Uiso 0.51(3) 1 calc R U P A 1
H3B H 0.528335 0.038735 0.132324 0.115 Uiso 0.51(3) 1 calc R U P A 1
C9 C 0.057(3) 0.258(2) 0.441(2) 0.089(6) Uani 0.51(3) 1 d . U P A 1
H9A H -0.010563 0.262102 0.474352 0.107 Uiso 0.51(3) 1 calc R U P A 1
H9B H 0.061758 0.307964 0.399390 0.107 Uiso 0.51(3) 1 calc R U P A 1
C15 C 0.1793(12) 0.4834(9) 0.0357(12) 0.105(6) Uani 0.5 1 d G U P D 1
H15 H 0.116586 0.512111 0.012207 0.126 Uiso 0.5 1 calc R U P D 1
C14 C 0.1735(11) 0.4238(8) 0.1106(11) 0.079(5) Uani 0.5 1 d G U P D 1
C13 C 0.2672(15) 0.3808(6) 0.1457(8) 0.074(4) Uani 0.5 1 d DG U P D 1
C18 C 0.3667(12) 0.3974(11) 0.1059(11) 0.120(6) Uani 0.5 1 d G U P D 1
H18 H 0.429336 0.368676 0.129347 0.144 Uiso 0.5 1 calc R U P D 1
C17 C 0.3724(12) 0.4570(13) 0.0310(12) 0.149(8) Uani 0.5 1 d G U P D 1
H17 H 0.439012 0.468160 0.004375 0.178 Uiso 0.5 1 calc R U P D 1
C16 C 0.2788(15) 0.5000(10) -0.0041(11) 0.106(7) Uani 0.5 1 d G U P D 1
H16 H 0.282639 0.539878 -0.054196 0.127 Uiso 0.5 1 calc R U P D 1
C20 C 0.2503(14) 0.2269(7) 0.1947(10) 0.070(4) Uani 0.5 1 d D U P D 1
H20A H 0.175470 0.226174 0.166528 0.084 Uiso 0.5 1 calc R U P D 1
H20B H 0.297719 0.207073 0.145004 0.084 Uiso 0.5 1 calc R U P D 1
F1 F 0.0820(8) 0.3854(7) 0.1491(9) 0.187(4) Uani 0.7 1 d . U P D 1
C19 C 0.2822(17) 0.3157(8) 0.2266(10) 0.102(5) Uani 0.5 1 d D U P D 1
H19A H 0.238739 0.332201 0.280688 0.122 Uiso 0.5 1 calc R U P D 1
H19B H 0.358358 0.315595 0.251268 0.122 Uiso 0.5 1 calc R U P D 1
C20A C 0.2682(18) 0.2614(10) 0.2481(12) 0.106(5) Uani 0.5 1 d D U P D 2
H20C H 0.339917 0.284527 0.267217 0.127 Uiso 0.5 1 calc R U P D 2
H20D H 0.213655 0.295705 0.278073 0.127 Uiso 0.5 1 calc R U P D 2
C19A C 0.2489(17) 0.2627(9) 0.1377(11) 0.113(5) Uani 0.5 1 d D U P D 2
H19C H 0.176966 0.239986 0.118740 0.136 Uiso 0.5 1 calc R U P D 2
H19D H 0.303086 0.228025 0.107884 0.136 Uiso 0.5 1 calc R U P D 2
C15A C 0.3274(11) 0.4754(9) 0.0177(13) 0.106(6) Uani 0.5 1 d G U P D 2
H15A H 0.384918 0.502567 -0.010632 0.127 Uiso 0.5 1 calc R U P D 2
C16A C 0.2258(13) 0.5145(7) 0.0183(12) 0.093(6) Uani 0.5 1 d G U P D 2
H16A H 0.215404 0.567965 -0.009585 0.111 Uiso 0.5 1 calc R U P D 2
C17A C 0.1398(10) 0.4739(10) 0.0607(13) 0.110(6) Uani 0.5 1 d G U P D 2
H17A H 0.071850 0.500109 0.061107 0.132 Uiso 0.5 1 calc R U P D 2
C18A C 0.1554(13) 0.3941(9) 0.1024(11) 0.104(6) Uani 0.5 1 d G U P D 2
H18A H 0.097807 0.366853 0.130752 0.125 Uiso 0.5 1 calc R U P D 2
C13A C 0.2569(15) 0.3549(6) 0.1018(9) 0.087(5) Uani 0.5 1 d DG U P D 2
C14A C 0.3429(11) 0.3955(9) 0.0594(11) 0.115(6) Uani 0.5 1 d G U P D 2
F1A F 0.427(2) 0.3561(17) 0.084(2) 0.195(9) Uani 0.3 1 d . U P D 2
F7A F 0.759(2) 0.3335(12) 0.3990(13) 0.106(6) Uani 0.295(10) 1 d . U P C 2
F2A F 0.6209(18) 0.3820(15) 0.317(3) 0.129(7) Uani 0.295(10) 1 d . U P C 2
F5A F 0.8748(17) 0.3816(14) 0.292(3) 0.129(7) Uani 0.295(10) 1 d . U P C 2
F4A F 0.728(3) 0.4316(16) 0.2075(14) 0.133(7) Uani 0.295(10) 1 d . U P C 2
F3A F 0.749(3) 0.4909(18) 0.303(2) 0.110(7) Uani 0.295(10) 1 d . U P C 2
F6A F 0.753(4) 0.300(2) 0.2534(15) 0.088(7) Uani 0.295(10) 1 d . U P C 2
C5A C 0.132(2) 0.023(3) 0.099(3) 0.086(7) Uani 0.49(3) 1 d . U P A 2
H5AA H 0.124859 -0.028124 0.059475 0.103 Uiso 0.49(3) 1 calc R U P A 2
H5AB H 0.125767 0.071389 0.055274 0.103 Uiso 0.49(3) 1 calc R U P A 2
O5A O 0.082(2) 0.194(3) 0.403(2) 0.076(5) Uani 0.49(3) 1 d . U P A 2
C8A C -0.025(4) 0.194(3) 0.340(3) 0.094(8) Uani 0.49(3) 1 d . U P A 2
H8AA H -0.085695 0.201102 0.380794 0.113 Uiso 0.49(3) 1 calc R U P A 2
H8AB H -0.025101 0.241074 0.293299 0.113 Uiso 0.49(3) 1 calc R U P A 2
C9A C 0.094(2) 0.268(2) 0.464(2) 0.081(6) Uani 0.49(3) 1 d . U P A 2
H9AA H 0.032585 0.272157 0.505339 0.097 Uiso 0.49(3) 1 calc R U P A 2
H9AB H 0.093332 0.318030 0.421894 0.097 Uiso 0.49(3) 1 calc R U P A 2
C7A C -0.035(3) 0.113(3) 0.285(3) 0.082(7) Uani 0.49(3) 1 d . U P A 2
H7AA H -0.028707 0.066799 0.332127 0.098 Uiso 0.49(3) 1 calc R U P A 2
H7AB H -0.105971 0.110312 0.250218 0.098 Uiso 0.49(3) 1 calc R U P A 2
C10A C 0.198(2) 0.264(3) 0.525(3) 0.088(7) Uani 0.49(3) 1 d . U P A 2
H10C H 0.200988 0.311652 0.570197 0.105 Uiso 0.49(3) 1 calc R U P A 2
H10D H 0.197112 0.212671 0.565259 0.105 Uiso 0.49(3) 1 calc R U P A 2
O4A O 0.046(3) 0.106(3) 0.219(3) 0.088(7) Uani 0.49(3) 1 d . U P A 2
O6A O 0.286(2) 0.264(3) 0.476(3) 0.082(6) Uani 0.49(3) 1 d . U P A 2
C6A C 0.046(3) 0.026(3) 0.169(3) 0.099(8) Uani 0.49(3) 1 d . U P A 2
H6AA H -0.025014 0.016907 0.133889 0.119 Uiso 0.49(3) 1 calc R U P A 2
H6AB H 0.056915 -0.019429 0.217239 0.119 Uiso 0.49(3) 1 calc R U P A 2
C11A C 0.385(3) 0.253(3) 0.519(2) 0.085(7) Uani 0.49(3) 1 d . U P A 2
H11C H 0.384200 0.200689 0.557036 0.102 Uiso 0.49(3) 1 calc R U P A 2
H11D H 0.397918 0.298713 0.566223 0.102 Uiso 0.49(3) 1 calc R U P A 2
C12A C 0.482(3) 0.249(2) 0.453(2) 0.093(7) Uani 0.49(3) 1 d . U P A 2
H12C H 0.480928 0.298941 0.411084 0.112 Uiso 0.49(3) 1 calc R U P A 2
H12D H 0.549824 0.249562 0.494175 0.112 Uiso 0.49(3) 1 calc R U P A 2
O3A O 0.238(3) 0.024(3) 0.154(3) 0.086(7) Uani 0.49(3) 1 d . U P A 2
O1A O 0.4768(18) 0.1753(15) 0.3938(16) 0.072(4) Uani 0.49(3) 1 d . U P A 2
C4A C 0.327(2) 0.0181(19) 0.091(3) 0.085(6) Uani 0.49(3) 1 d . U P A 2
H4AA H 0.325103 0.066477 0.047195 0.102 Uiso 0.49(3) 1 calc R U P A 2
H4AB H 0.318635 -0.032675 0.051304 0.102 Uiso 0.49(3) 1 calc R U P A 2
C1A C 0.553(3) 0.1684(17) 0.336(2) 0.075(6) Uani 0.49(3) 1 d . U P A 2
H1AA H 0.622521 0.169896 0.374907 0.090 Uiso 0.49(3) 1 calc R U P A 2
H1AB H 0.551237 0.217644 0.292824 0.090 Uiso 0.49(3) 1 calc R U P A 2
C3A C 0.440(3) 0.015(2) 0.152(3) 0.089(7) Uani 0.49(3) 1 d . U P A 2
H3AA H 0.441829 -0.032786 0.196546 0.107 Uiso 0.49(3) 1 calc R U P A 2
H3AB H 0.497921 0.008118 0.107419 0.107 Uiso 0.49(3) 1 calc R U P A 2
C2A C 0.552(2) 0.0887(14) 0.2705(18) 0.075(5) Uani 0.49(3) 1 d . U P A 2
H2AA H 0.616296 0.087291 0.232567 0.090 Uiso 0.49(3) 1 calc R U P A 2
H2AB H 0.551580 0.038271 0.311232 0.090 Uiso 0.49(3) 1 calc R U P A 2
O2A O 0.460(4) 0.092(2) 0.209(3) 0.086(6) Uani 0.49(3) 1 d . 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 F6 1.612(17) . ?
P1 F3 1.563(12) . ?
P1 F5 1.572(7) . ?
P1 F4 1.581(8) . ?
P1 F2 1.562(8) . ?
P1 F7 1.546(9) . ?
P1 F7A 1.549(17) . ?
P1 F2A 1.59(2) . ?
P1 F5A 1.57(2) . ?
P1 F4A 1.482(17) . ?
P1 F3A 1.65(3) . ?
P1 F6A 1.52(4) . ?
O5 C8 1.34(4) . ?
O5 C9 1.39(5) . ?
O2 C2 1.50(4) . ?
O2 C3 1.41(3) . ?
N1 H1AC 0.8900 . ?
N1 H1AD 0.8900 . ?
N1 H1AE 0.8900 . ?
N1 H1BF 0.8900 . ?
N1 H1BG 0.8900 . ?
N1 H1BH 0.8900 . ?
N1 C20 1.479(12) . ?
N1 C20A 1.501(14) . ?
O4 C6 1.38(4) . ?
O4 C7 1.41(4) . ?
O3 C4 1.43(4) . ?
O3 C5 1.42(4) . ?
O1 C1 1.55(4) . ?
O1 C12 1.36(3) . ?
O6 C10 1.49(4) . ?
O6 C11 1.55(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.51(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.51(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.46(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.54(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.49(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.42(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C15 C16 1.3900 . ?
C14 C13 1.3900 . ?
C14 F1 1.404(14) . ?
C13 C18 1.3900 . ?
C13 C19 1.506(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C16 H16 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.512(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C20A C19A 1.501(12) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C13A 1.540(11) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.3900 . ?
C15A C14A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C13A 1.3900 . ?
C13A C14A 1.3900 . ?
C14A F1A 1.23(3) . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A C6A 1.47(4) . ?
C5A O3A 1.45(4) . ?
O5A C8A 1.52(5) . ?
O5A C9A 1.43(4) . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C7A 1.47(4) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.48(3) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A O4A 1.38(4) . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C10A O6A 1.31(4) . ?
O4A C6A 1.43(5) . ?
O6A C11A 1.32(4) . ?
C6A H6AA 0.9700 . ?
C6A H6AB 0.9700 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.54(3) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C12A O1A 1.42(3) . ?
O3A C4A 1.43(4) . ?
O1A C1A 1.27(4) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C3A 1.57(4) . ?
C1A H1AA 0.9700 . ?
C1A H1AB 0.9700 . ?
C1A C2A 1.54(2) . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?
C3A O2A 1.44(4) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A O2A 1.35(5) . ?

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
F3 P1 F6 169.0(7) . . ?
F3 P1 F5 80.4(6) . . ?
F3 P1 F4 97.5(6) . . ?
F3 P1 F2 98.9(6) . . ?
F5 P1 F6 92.8(7) . . ?
F5 P1 F4 86.8(5) . . ?
F4 P1 F6 90.6(7) . . ?
F2 P1 F6 88.3(7) . . ?
F2 P1 F5 177.5(7) . . ?
F2 P1 F4 91.0(6) . . ?
F7 P1 F6 89.7(7) . . ?
F7 P1 F3 82.0(6) . . ?
F7 P1 F5 91.7(7) . . ?
F7 P1 F4 178.4(7) . . ?
F7 P1 F2 90.6(7) . . ?
F7A P1 F2A 84.2(12) . . ?
F7A P1 F5A 91.6(13) . . ?
F7A P1 F3A 122.3(13) . . ?
F2A P1 F3A 92.7(15) . . ?
F5A P1 F2A 174.6(12) . . ?
F5A P1 F3A 92.3(14) . . ?
F4A P1 F7A 174.0(14) . . ?
F4A P1 F2A 91.0(14) . . ?
F4A P1 F5A 93.1(15) . . ?
F4A P1 F3A 61.3(13) . . ?
F4A P1 F6A 93.5(14) . . ?
F6A P1 F7A 83.5(12) . . ?
F6A P1 F2A 95(2) . . ?
F6A P1 F5A 81.3(19) . . ?
F6A P1 F3A 153.7(15) . . ?
C8 O5 C9 117(3) . . ?
C3 O2 C2 110(3) . . ?
H1AC N1 H1AD 109.5 . . ?
H1AC N1 H1AE 109.5 . . ?
H1AD N1 H1AE 109.5 . . ?
H1BF N1 H1BG 109.5 . . ?
H1BF N1 H1BH 109.5 . . ?
H1BG N1 H1BH 109.5 . . ?
C20 N1 H1AC 109.5 . . ?
C20 N1 H1AD 109.5 . . ?
C20 N1 H1AE 109.5 . . ?
C20A N1 H1BF 109.5 . . ?
C20A N1 H1BG 109.5 . . ?
C20A N1 H1BH 109.5 . . ?
C6 O4 C7 110(3) . . ?
C5 O3 C4 113(3) . . ?
C12 O1 C1 108.7(18) . . ?
C10 O6 C11 105(2) . . ?
O5 C8 H8A 109.7 . . ?
O5 C8 H8B 109.7 . . ?
O5 C8 C7 110(3) . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
O4 C6 H6A 110.0 . . ?
O4 C6 H6B 110.0 . . ?
O4 C6 C5 108(3) . . ?
H6A C6 H6B 108.4 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
O2 C2 H2A 109.6 . . ?
O2 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 O2 110(2) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
O1 C1 H1A 110.5 . . ?
O1 C1 H1B 110.5 . . ?
C2 C1 O1 106(2) . . ?
C2 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O4 C7 C8 111(3) . . ?
O4 C7 H7A 109.4 . . ?
O4 C7 H7B 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
O6 C10 H10A 110.6 . . ?
O6 C10 H10B 110.6 . . ?
O6 C10 C9 106(2) . . ?
H10A C10 H10B 108.7 . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
O6 C11 H11A 111.4 . . ?
O6 C11 H11B 111.4 . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 O6 102(2) . . ?
C12 C11 H11A 111.4 . . ?
C12 C11 H11B 111.4 . . ?
O1 C12 C11 111(2) . . ?
O1 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 O3 111(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
O3 C5 C6 109(3) . . ?
O3 C5 H5A 110.0 . . ?
O3 C5 H5B 110.0 . . ?
C6 C5 H5A 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.3 . . ?
O2 C3 C4 106(3) . . ?
O2 C3 H3A 110.5 . . ?
O2 C3 H3B 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.6 . . ?
O5 C9 C10 112(3) . . ?
O5 C9 H9A 109.3 . . ?
O5 C9 H9B 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 F1 130.1(12) . . ?
C13 C14 F1 108.9(12) . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C19 129.9(14) . . ?
C18 C13 C19 110.1(14) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
N1 C20 H20A 110.1 . . ?
N1 C20 H20B 110.1 . . ?
N1 C20 C19 108.1(9) . . ?
H20A C20 H20B 108.4 . . ?
C19 C20 H20A 110.1 . . ?
C19 C20 H20B 110.1 . . ?
C13 C19 C20 114.0(10) . . ?
C13 C19 H19A 108.7 . . ?
C13 C19 H19B 108.7 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
N1 C20A H20C 110.0 . . ?
N1 C20A H20D 110.0 . . ?
N1 C20A C19A 108.4(13) . . ?
H20C C20A H20D 108.4 . . ?
C19A C20A H20C 110.0 . . ?
C19A C20A H20D 110.0 . . ?
C20A C19A H19C 110.0 . . ?
C20A C19A H19D 110.0 . . ?
C20A C19A C13A 108.6(11) . . ?
H19C C19A H19D 108.3 . . ?
C13A C19A H19C 110.0 . . ?
C13A C19A H19D 110.0 . . ?
C16A C15A H15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C13A 120.0 . . ?
C13A C18A H18A 120.0 . . ?
C18A C13A C19A 110.0(14) . . ?
C18A C13A C14A 120.0 . . ?
C14A C13A C19A 129.3(14) . . ?
C13A C14A C15A 120.0 . . ?
F1A C14A C15A 131.2(18) . . ?
F1A C14A C13A 107.4(18) . . ?
H5AA C5A H5AB 108.3 . . ?
C6A C5A H5AA 109.9 . . ?
C6A C5A H5AB 109.9 . . ?
O3A C5A H5AA 109.9 . . ?
O3A C5A H5AB 109.9 . . ?
O3A C5A C6A 109(3) . . ?
C9A O5A C8A 112(3) . . ?
O5A C8A H8AA 110.0 . . ?
O5A C8A H8AB 110.0 . . ?
H8AA C8A H8AB 108.3 . . ?
C7A C8A O5A 109(4) . . ?
C7A C8A H8AA 110.0 . . ?
C7A C8A H8AB 110.0 . . ?
O5A C9A H9AA 109.8 . . ?
O5A C9A H9AB 109.8 . . ?
O5A C9A C10A 109(3) . . ?
H9AA C9A H9AB 108.2 . . ?
C10A C9A H9AA 109.8 . . ?
C10A C9A H9AB 109.8 . . ?
C8A C7A H7AA 109.4 . . ?
C8A C7A H7AB 109.4 . . ?
H7AA C7A H7AB 108.0 . . ?
O4A C7A C8A 111(3) . . ?
O4A C7A H7AA 109.4 . . ?
O4A C7A H7AB 109.4 . . ?
C9A C10A H10C 108.6 . . ?
C9A C10A H10D 108.6 . . ?
H10C C10A H10D 107.6 . . ?
O6A C10A C9A 115(3) . . ?
O6A C10A H10C 108.6 . . ?
O6A C10A H10D 108.6 . . ?
C7A O4A C6A 114(3) . . ?
C10A O6A C11A 122(3) . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
O4A C6A C5A 111(3) . . ?
O4A C6A H6AA 109.5 . . ?
O4A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 108.1 . . ?
O6A C11A H11C 107.9 . . ?
O6A C11A H11D 107.9 . . ?
O6A C11A C12A 118(3) . . ?
H11C C11A H11D 107.2 . . ?
C12A C11A H11C 107.9 . . ?
C12A C11A H11D 107.9 . . ?
C11A C12A H12C 109.5 . . ?
C11A C12A H12D 109.5 . . ?
H12C C12A H12D 108.1 . . ?
O1A C12A C11A 111(3) . . ?
O1A C12A H12C 109.5 . . ?
O1A C12A H12D 109.5 . . ?
C4A O3A C5A 112(3) . . ?
C1A O1A C12A 115(2) . . ?
O3A C4A H4AA 109.3 . . ?
O3A C4A H4AB 109.3 . . ?
O3A C4A C3A 112(3) . . ?
H4AA C4A H4AB 107.9 . . ?
C3A C4A H4AA 109.3 . . ?
C3A C4A H4AB 109.3 . . ?
O1A C1A H1AA 108.2 . . ?
O1A C1A H1AB 108.2 . . ?
O1A C1A C2A 116(3) . . ?
H1AA C1A H1AB 107.3 . . ?
C2A C1A H1AA 108.2 . . ?
C2A C1A H1AB 108.2 . . ?
C4A C3A H3AA 109.2 . . ?
C4A C3A H3AB 109.2 . . ?
H3AA C3A H3AB 107.9 . . ?
O2A C3A C4A 112(3) . . ?
O2A C3A H3AA 109.2 . . ?
O2A C3A H3AB 109.2 . . ?
C1A C2A H2AA 110.2 . . ?
C1A C2A H2AB 110.2 . . ?
H2AA C2A H2AB 108.5 . . ?
O2A C2A C1A 108(2) . . ?
O2A C2A H2AA 110.2 . . ?
O2A C2A H2AB 110.2 . . ?
C2A O2A C3A 114(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 H1AC O3 0.89 2.06 2.86(5) 149.1 . yes
N1 H1AD O5 0.89 2.10 2.95(4) 161.8 . yes
N1 H1AE O1 0.89 1.96 2.83(2) 164.8 . 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
O5 C8 C7 O4 -71(4) . . . . ?
O2 C2 C1 O1 66(3) . . . . ?
N1 C20 C19 C13 -175.8(14) . . . . ?
N1 C20A C19A C13A -179.5(14) . . . . ?
O4 C6 C5 O3 67(4) . . . . ?
O3 C4 C3 O2 -65(4) . . . . ?
O6 C10 C9 O5 64(3) . . . . ?
O6 C11 C12 O1 -61(3) . . . . ?
C8 O5 C9 C10 177(3) . . . . ?
C6 O4 C7 C8 176(3) . . . . ?
C2 O2 C3 C4 179(3) . . . . ?
C1 O1 C12 C11 -179(2) . . . . ?
C7 O4 C6 C5 -179(3) . . . . ?
C10 O6 C11 C12 -179(3) . . . . ?
C11 O6 C10 C9 -178(3) . . . . ?
C12 O1 C1 C2 172(2) . . . . ?
C4 O3 C5 C6 -176(3) . . . . ?
C5 O3 C4 C3 -175(3) . . . . ?
C3 O2 C2 C1 176(3) . . . . ?
C9 O5 C8 C7 -177(3) . . . . ?
C15 C14 C13 C18 0.0 . . . . ?
C15 C14 C13 C19 178.5(13) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C14 C13 C19 C20 81.9(19) . . . . ?
C13 C18 C17 C16 0.0 . . . . ?
C18 C13 C19 C20 -99.4(16) . . . . ?
C18 C17 C16 C15 0.0 . . . . ?
C16 C15 C14 C13 0.0 . . . . ?
C16 C15 C14 F1 -167.0(15) . . . . ?
F1 C14 C13 C18 169.5(12) . . . . ?
F1 C14 C13 C19 -12.0(15) . . . . ?
C19 C13 C18 C17 -178.8(11) . . . . ?
C20A C19A C13A C18A -88.3(16) . . . . ?
C20A C19A C13A C14A 101.2(17) . . . . ?
C19A C13A C14A C15A 169.8(13) . . . . ?
C19A C13A C14A F1A -22.4(19) . . . . ?
C15A C16A C17A C18A 0.0 . . . . ?
C16A C15A C14A C13A 0.0 . . . . ?
C16A C15A C14A F1A -164(2) . . . . ?
C16A C17A C18A C13A 0.0 . . . . ?
C17A C18A C13A C19A -171.6(10) . . . . ?
C17A C18A C13A C14A 0.0 . . . . ?
C18A C13A C14A C15A 0.0 . . . . ?
C18A C13A C14A F1A 167.8(17) . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C5A O3A C4A C3A -178(3) . . . . ?
O5A C8A C7A O4A -65(4) . . . . ?
O5A C9A C10A O6A 64(4) . . . . ?
C8A O5A C9A C10A 179(3) . . . . ?
C8A C7A O4A C6A 176(3) . . . . ?
C9A O5A C8A C7A -176(3) . . . . ?
C9A C10A O6A C11A -174(4) . . . . ?
C7A O4A C6A C5A 179(3) . . . . ?
C10A O6A C11A C12A 177(4) . . . . ?
O6A C11A C12A O1A -67(4) . . . . ?
C6A C5A O3A C4A 178(3) . . . . ?
C11A C12A O1A C1A 179(3) . . . . ?
C12A O1A C1A C2A 179(2) . . . . ?
O3A C5A C6A O4A 67(4) . . . . ?
O3A C4A C3A O2A -62(4) . . . . ?
O1A C1A C2A O2A 64(3) . . . . ?
C4A C3A O2A C2A 174(3) . . . . ?
C1A C2A O2A C3A -172(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
