# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_sv752a
_database_code_depnum_ccdc_archive 'CCDC 2061883'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2021-02-08 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C20 H15 F4 O P)'
_chemical_formula_sum            'C20 H15 F4 O P'
_chemical_formula_weight         378.29
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.0201(6)
_cell_length_b                   9.3245(4)
_cell_length_c                   25.3352(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.9180(10)
_cell_angle_gamma                90
_cell_volume                     3428.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.476
_cell_measurement_theta_min      2.337
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0596 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.9383. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            74625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.580
_diffrn_reflns_theta_min         1.664
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7197
_reflns_number_total             10542
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         10542
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+3.8533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1B-C1B \\sim F1B-C1B \\sim F2B-C1B
 with sigma of 0.02
 P1A-C14A \\sim P1A-C8B
 with sigma of 0.02
 F4B-C20B \\sim F3B-C20B \\sim F2A-C1A \\sim F1A-C1A
 with sigma of 0.02
 P1A-C8C \\sim P1A-C3A \\sim P1A-C3B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C4B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1C) \\sim Ueq, Uanis(O1B) \\sim Ueq: with sigma of 0.015 and sigma for
terminal atoms of 0.03
Uanis(C20A) = Uanis(C1B)
Uanis(F1B) = Uanis(F4A)
Uanis(F3A) = Uanis(F2B)
Uanis(C14A) = Uanis(C8B)
Uanis(C19A) = Uanis(C13B)
Uanis(C18A) = Uanis(C12B)
Uanis(C17A) = Uanis(C11B)
Uanis(C16A) = Uanis(C10B)
Uanis(C15A) = Uanis(C9B)
Uanis(F3B) = Uanis(F2A)
Uanis(F4B) = Uanis(F1A)
Uanis(C20B) = Uanis(C1A)
Uanis(F2C) = Uanis(F1A) = Uanis(F4B)
Uanis(F3B) = Uanis(F2A) = Uanis(F1C)
Uanis(C3C) = Uanis(C8A)
Uanis(C13A) = Uanis(C4C)
Uanis(C12A) = Uanis(C5C)
Uanis(C11A) = Uanis(C6C)
Uanis(C7C) = Uanis(C10A)
Uanis(C2C) = Uanis(C9A)
Uanis(C11C) = Uanis(C6A)
Uanis(C10C) = Uanis(C7A)
Uanis(C2A) = Uanis(C9C)
Uanis(C4A) = Uanis(C13C)
Uanis(C5A) = Uanis(C12C)
Uanis(C8C) = Uanis(C3A)
Uanis(C5B) = Uanis(C5A)
Uanis(C3B) = Uanis(C3A)
4. Others
 Fixed Sof: F1A(0.7) F1B(0.18) F1C(0.12) F2A(0.7) F2B(0.18) F2C(0.12)
 F3A(0.82) F3B(0.18) F4A(0.82) F4B(0.18) O1A(0.7) O1B(0.18) O1C(0.12) C1A(0.7)
 C1B(0.18) C1C(0.12) C3A(0.7) C2A(0.7) C7A(0.7) H7A(0.7) C6A(0.7) H6A(0.7)
 C5A(0.7) H5A(0.7) C4A(0.7) H4A(0.7) C3B(0.18) C4B(0.18) H4B(0.18) C5B(0.18)
 H5B(0.18) C6B(0.18) H6B(0.18) C7B(0.18) H7B(0.18) C2B(0.18) C4C(0.12)
 H4C(0.12) C5C(0.12) H5C(0.12) C6C(0.12) H6C(0.12) C7C(0.12) H7C(0.12)
 C2C(0.12) C3C(0.12) C8A(0.88) C8B(0.18) C13B(0.18) H13B(0.18) C12B(0.18)
 H12B(0.18) C11B(0.18) H11B(0.18) C10B(0.18) H10B(0.18) C9B(0.18) H9B(0.18)
 C9A(0.88) H9A(0.88) C10A(0.88) H10A(0.88) C10C(0.12) H10C(0.12) C11C(0.12)
 H11C(0.12) C12C(0.12) H12C(0.12) C13C(0.12) H13C(0.12) C8C(0.12) C9C(0.12)
 H9C(0.12) C11A(0.88) H11A(0.88) C12A(0.88) H12A(0.88) C13A(0.88) H13A(0.88)
 C14A(0.82) C15A(0.82) H15A(0.82) C16A(0.82) H16A(0.82) C17A(0.82) H17A(0.82)
 C18A(0.82) H18A(0.82) C19A(0.82) H19A(0.82) C20A(0.82) H20A(0.82) C20B(0.18)
 H20B(0.18)
5.a Ternary CH refined with riding coordinates:
 C20(H20), C20A(H20A), C20B(H20B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C7A(H7A), C6A(H6A),
  C5A(H5A), C4A(H4A), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C4C(H4C),
 C5C(H5C), C6C(H6C), C7C(H7C), C13B(H13B), C12B(H12B), C11B(H11B), C10B(H10B),
 C9B(H9B), C9A(H9A), C10A(H10A), C10C(H10C), C11C(H11C), C12C(H12C), C13C(H13C),
  C9C(H9C), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A)
5.c Fitted hexagon refined as free rotating group:
 C3A(C2A,C7A,C6A,C5A,C4A), C3B(C4B,C5B,C6B,C7B,C2B), C4C(C5C,C6C,C7C,C2C,C3C),
 C8B(C13B,C12B,C11B,C10B,C9B), C10C(C11C,C12C,C13C,C8C,C9C)
;
_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 0.53630(4) 0.31499(6) 0.37703(2) 0.01985(11) Uani 1 1 d . . . . .
F1 F 0.51523(9) 0.23819(15) 0.26324(5) 0.0325(3) Uani 1 1 d . . . . .
F2 F 0.65427(9) 0.20922(15) 0.31405(5) 0.0318(3) Uani 1 1 d . . . . .
F3 F 0.43899(9) 0.34720(15) 0.45531(5) 0.0335(3) Uani 1 1 d . . . . .
F4 F 0.48095(10) 0.55000(14) 0.42495(5) 0.0329(3) Uani 1 1 d . . . . .
O1 O 0.54353(12) 0.05909(17) 0.32112(7) 0.0326(4) Uani 1 1 d . . . . .
C1 C 0.56263(15) 0.2036(2) 0.31469(9) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.56394(16) 0.0305(3) 0.37657(10) 0.0305(5) Uani 1 1 d . . . . .
C3 C 0.56680(14) 0.1454(2) 0.41199(9) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.58920(16) 0.1166(3) 0.46802(10) 0.0317(5) Uani 1 1 d . . . . .
H4 H 0.5915 0.1926 0.4933 0.038 Uiso 1 1 calc R U . . .
C5 C 0.60802(17) -0.0226(3) 0.48687(11) 0.0403(6) Uani 1 1 d . . . . .
H5 H 0.6250 -0.0412 0.5250 0.048 Uiso 1 1 calc R U . . .
C6 C 0.60213(18) -0.1345(3) 0.45028(12) 0.0421(6) Uani 1 1 d . . . . .
H6 H 0.6135 -0.2299 0.4635 0.051 Uiso 1 1 calc R U . . .
C7 C 0.58004(18) -0.1095(3) 0.39493(12) 0.0391(6) Uani 1 1 d . . . . .
H7 H 0.5759 -0.1864 0.3698 0.047 Uiso 1 1 calc R U . . .
C8 C 0.41588(14) 0.3350(2) 0.33913(8) 0.0217(4) Uani 1 1 d . . . . .
C9 C 0.35509(15) 0.2227(2) 0.34039(9) 0.0281(5) Uani 1 1 d . . . . .
H9 H 0.3770 0.1377 0.3601 0.034 Uiso 1 1 calc R U . . .
C10 C 0.26273(16) 0.2350(3) 0.31286(11) 0.0364(6) Uani 1 1 d . . . . .
H10 H 0.2213 0.1589 0.3141 0.044 Uiso 1 1 calc R U . . .
C11 C 0.23089(17) 0.3583(3) 0.28351(12) 0.0427(7) Uani 1 1 d . . . . .
H11 H 0.1678 0.3661 0.2643 0.051 Uiso 1 1 calc R U . . .
C12 C 0.29068(17) 0.4695(3) 0.28222(11) 0.0402(6) Uani 1 1 d . . . . .
H12 H 0.2685 0.5540 0.2622 0.048 Uiso 1 1 calc R U . . .
C13 C 0.38293(16) 0.4590(3) 0.30990(9) 0.0306(5) Uani 1 1 d . . . . .
H13 H 0.4237 0.5363 0.3089 0.037 Uiso 1 1 calc R U . . .
C14 C 0.62064(14) 0.4511(2) 0.37189(8) 0.0228(4) Uani 1 1 d . . . . .
C15 C 0.61399(15) 0.5234(2) 0.32274(9) 0.0253(4) Uani 1 1 d . . . . .
H15 H 0.5655 0.5008 0.2915 0.030 Uiso 1 1 calc R U . . .
C16 C 0.67780(16) 0.6281(3) 0.31927(10) 0.0321(5) Uani 1 1 d . . . . .
H16 H 0.6724 0.6782 0.2859 0.039 Uiso 1 1 calc R U . . .
C17 C 0.74941(16) 0.6597(3) 0.36436(11) 0.0371(6) Uani 1 1 d . . . . .
H17 H 0.7928 0.7319 0.3619 0.045 Uiso 1 1 calc R U . . .
C18 C 0.75793(16) 0.5870(3) 0.41267(11) 0.0378(6) Uani 1 1 d . . . . .
H18 H 0.8078 0.6081 0.4433 0.045 Uiso 1 1 calc R U . . .
C19 C 0.69353(15) 0.4824(3) 0.41693(9) 0.0298(5) Uani 1 1 d . . . . .
H19 H 0.6994 0.4329 0.4504 0.036 Uiso 1 1 calc R U . . .
C20 C 0.51102(15) 0.4123(2) 0.44001(9) 0.0262(4) Uani 1 1 d . . . . .
H20 H 0.5674 0.4143 0.4713 0.031 Uiso 1 1 calc R U . . .
P1A P 0.92207(4) 0.26128(6) 0.62960(2) 0.02274(12) Uani 1 1 d D . . . .
F1A F 0.8317(4) 0.2694(14) 0.5144(3) 0.0371(9) Uani 0.7 1 d D . P A 1
F1B F 1.0818(19) 0.385(4) 0.6873(11) 0.0370(8) Uani 0.18 1 d D . P A 2
F1C F 0.837(3) 0.067(4) 0.5396(10) 0.0256(7) Uani 0.12 1 d . . P A 3
F2A F 0.8300(2) 0.0574(4) 0.55217(9) 0.0256(7) Uani 0.7 1 d D . P A 1
F2B F 0.9770(6) 0.4949(10) 0.7023(3) 0.0382(4) Uani 0.18 1 d D . P A 2
F2C F 0.814(2) 0.267(9) 0.5125(19) 0.0371(9) Uani 0.12 1 d . . P A 3
F3A F 0.96320(13) 0.4292(2) 0.72215(7) 0.0382(4) Uani 0.82 1 d . . P B 1
F3B F 0.8169(10) 0.0452(16) 0.5695(4) 0.0256(7) Uani 0.18 1 d D . P C 2
F4A F 1.0881(4) 0.3642(7) 0.69664(19) 0.0370(8) Uani 0.82 1 d . . P B 1
F4B F 0.8388(16) 0.2227(15) 0.5185(7) 0.0371(9) Uani 0.18 1 d D . P C 2
O1A O 0.74239(14) 0.2285(3) 0.56906(9) 0.0294(5) Uani 0.7 1 d . . P A 1
O1B O 1.0015(7) 0.2733(10) 0.7385(3) 0.032(2) Uani 0.18 1 d D U P A 2
O1C O 0.9427(8) 0.1610(13) 0.5291(4) 0.022(2) Uani 0.12 1 d . . P A 3
C1A C 0.8311(7) 0.2015(6) 0.5617(3) 0.0250(14) Uani 0.7 1 d D . P A 1
C1B C 0.9968(18) 0.3549(19) 0.6933(12) 0.0303(7) Uani 0.18 1 d D . P A 2
C1C C 0.8724(16) 0.189(2) 0.5540(9) 0.029(5) Uani 0.12 1 d . U P A 3
C3A C 0.83051(15) 0.2042(3) 0.66124(10) 0.0210(7) Uani 0.7 1 d DG . P A 1
C2A C 0.74556(19) 0.2062(2) 0.62295(8) 0.0234(7) Uani 0.7 1 d G . P A 1
C7A C 0.66561(15) 0.1774(3) 0.63903(12) 0.0302(8) Uani 0.7 1 d G . P A 1
H7A H 0.6076 0.1787 0.6129 0.036 Uiso 0.7 1 calc R U P A 1
C6A C 0.67061(17) 0.1465(3) 0.69339(13) 0.0326(7) Uani 0.7 1 d G . P A 1
H6A H 0.6160 0.1269 0.7044 0.039 Uiso 0.7 1 calc R U P A 1
C5A C 0.7556(2) 0.1445(3) 0.73168(9) 0.0277(7) Uani 0.7 1 d G . P A 1
H5A H 0.7590 0.1235 0.7688 0.033 Uiso 0.7 1 calc R U P A 1
C4A C 0.83551(16) 0.1734(3) 0.71560(9) 0.0263(7) Uani 0.7 1 d G . P A 1
H4A H 0.8936 0.1720 0.7418 0.032 Uiso 0.7 1 calc R U P A 1
C3B C 0.8519(6) 0.2221(11) 0.6762(3) 0.0210(7) Uani 0.18 1 d DG . P A 2
C4B C 0.7626(6) 0.1711(13) 0.6688(3) 0.055(4) Uani 0.18 1 d G U P A 2
H4B H 0.7218 0.1689 0.6333 0.067 Uiso 0.18 1 calc R U P A 2
C5B C 0.7331(6) 0.1232(13) 0.7134(5) 0.0277(7) Uani 0.18 1 d G . P A 2
H5B H 0.6720 0.0883 0.7084 0.033 Uiso 0.18 1 calc R U P A 2
C6B C 0.7928(8) 0.1263(13) 0.7654(4) 0.063(5) Uani 0.18 1 d G U P A 2
H6B H 0.7726 0.0936 0.7959 0.076 Uiso 0.18 1 calc R U P A 2
C7B C 0.8821(7) 0.1774(12) 0.7728(3) 0.056(5) Uani 0.18 1 d G . P A 2
H7B H 0.9230 0.1795 0.8083 0.068 Uiso 0.18 1 calc R U P A 2
C2B C 0.9117(5) 0.2253(10) 0.7282(4) 0.038(3) Uani 0.18 1 d G . P A 2
C4C C 1.0863(14) 0.075(2) 0.6644(6) 0.0366(7) Uani 0.12 1 d G . P A 3
H4C H 1.0875 0.0901 0.7016 0.044 Uiso 0.12 1 calc R U P A 3
C5C C 1.1548(13) -0.007(2) 0.6509(7) 0.0468(8) Uani 0.12 1 d G . P A 3
H5C H 1.2027 -0.0472 0.6790 0.056 Uiso 0.12 1 calc R U P A 3
C6C C 1.1531(16) -0.029(3) 0.5965(9) 0.0439(9) Uani 0.12 1 d G . P A 3
H6C H 1.1999 -0.0851 0.5873 0.053 Uiso 0.12 1 calc R U P A 3
C7C C 1.0830(16) 0.030(3) 0.5554(6) 0.0374(8) Uani 0.12 1 d G . P A 3
H7C H 1.0818 0.0145 0.5181 0.045 Uiso 0.12 1 calc R U P A 3
C2C C 1.0145(13) 0.111(3) 0.5688(7) 0.0302(7) Uani 0.12 1 d G . P A 3
C3C C 1.0162(14) 0.134(3) 0.6233(9) 0.0240(5) Uani 0.12 1 d G . P A 3
C8A C 1.0071(2) 0.1365(4) 0.61713(13) 0.0240(5) Uani 0.88 1 d . . P A 1
C8B C 0.8996(9) 0.4416(12) 0.5966(7) 0.0259(6) Uani 0.18 1 d DG . P A 2
C13B C 0.9731(7) 0.5060(15) 0.5818(7) 0.0331(7) Uani 0.18 1 d G . P A 2
H13B H 1.0293 0.4551 0.5858 0.040 Uiso 0.18 1 calc R U P A 2
C12B C 0.9645(7) 0.6450(15) 0.5612(6) 0.0421(8) Uani 0.18 1 d G . P A 2
H12B H 1.0147 0.6890 0.5511 0.051 Uiso 0.18 1 calc R U P A 2
C11B C 0.8824(9) 0.7195(11) 0.5554(6) 0.0450(9) Uani 0.18 1 d G . P A 2
H11B H 0.8765 0.8144 0.5413 0.054 Uiso 0.18 1 calc R U P A 2
C10B C 0.8089(7) 0.6550(13) 0.5702(6) 0.0481(9) Uani 0.18 1 d G . P A 2
H10B H 0.7528 0.7060 0.5662 0.058 Uiso 0.18 1 calc R U P A 2
C9B C 0.8175(7) 0.5161(14) 0.5908(6) 0.0380(8) Uani 0.18 1 d G . P A 2
H9B H 0.7673 0.4721 0.6009 0.046 Uiso 0.18 1 calc R U P A 2
C9A C 1.03741(19) 0.1432(4) 0.56970(12) 0.0302(7) Uani 0.88 1 d . . P A 1
H9A H 1.0106 0.2106 0.5421 0.036 Uiso 0.88 1 calc R U P A 1
C10A C 1.1064(2) 0.0524(4) 0.56236(13) 0.0374(8) Uani 0.88 1 d . . P A 1
H10A H 1.1271 0.0592 0.5301 0.045 Uiso 0.88 1 calc R U P A 1
C10C C 0.6599(10) 0.214(2) 0.6411(9) 0.0302(8) Uani 0.12 1 d G . P A 3
H10C H 0.5999 0.2395 0.6203 0.036 Uiso 0.12 1 calc R U P A 3
C11C C 0.6711(11) 0.138(2) 0.6896(9) 0.0326(7) Uani 0.12 1 d G . P A 3
H11C H 0.6187 0.1113 0.7018 0.039 Uiso 0.12 1 calc R U P A 3
C12C C 0.7588(14) 0.1007(17) 0.7201(7) 0.0277(7) Uani 0.12 1 d G . P A 3
H12C H 0.7665 0.0487 0.7532 0.033 Uiso 0.12 1 calc R U P A 3
C13C C 0.8355(10) 0.1397(19) 0.7022(7) 0.0263(7) Uani 0.12 1 d G . P A 3
H13C H 0.8955 0.1142 0.7230 0.032 Uiso 0.12 1 calc R U P A 3
C8C C 0.8244(11) 0.2158(19) 0.6537(8) 0.0210(7) Uani 0.12 1 d DG . P A 3
C9C C 0.7366(14) 0.2530(17) 0.6232(7) 0.0234(7) Uani 0.12 1 d G . P A 3
H9C H 0.7290 0.3051 0.5901 0.028 Uiso 0.12 1 calc R U P A 3
C11A C 1.1447(3) -0.0470(5) 0.60147(16) 0.0439(9) Uani 0.88 1 d . . P A 1
H11A H 1.1930 -0.1075 0.5968 0.053 Uiso 0.88 1 calc R U P A 1
C12A C 1.1126(2) -0.0588(4) 0.64792(13) 0.0468(8) Uani 0.88 1 d . . P A 1
H12A H 1.1372 -0.1301 0.6745 0.056 Uiso 0.88 1 calc R U P A 1
C13A C 1.0447(2) 0.0332(3) 0.65568(11) 0.0366(7) Uani 0.88 1 d . . P A 1
H13A H 1.0237 0.0253 0.6879 0.044 Uiso 0.88 1 calc R U P A 1
C14A C 0.92515(19) 0.4439(3) 0.60398(15) 0.0259(6) Uani 0.82 1 d D . P A 1
C15A C 0.8510(2) 0.5340(4) 0.60099(15) 0.0380(8) Uani 0.82 1 d . . P A 1
H15A H 0.7983 0.5005 0.6115 0.046 Uiso 0.82 1 calc R U P A 1
C16A C 0.8539(3) 0.6744(4) 0.58251(15) 0.0481(9) Uani 0.82 1 d . . P A 1
H16A H 0.8030 0.7367 0.5804 0.058 Uiso 0.82 1 calc R U P A 1
C17A C 0.9304(3) 0.7231(4) 0.56726(14) 0.0450(9) Uani 0.82 1 d . . P A 1
H17A H 0.9325 0.8191 0.5552 0.054 Uiso 0.82 1 calc R U P A 1
C18A C 1.0033(2) 0.6329(4) 0.56958(15) 0.0421(8) Uani 0.82 1 d . . P A 1
H18A H 1.0553 0.6661 0.5583 0.051 Uiso 0.82 1 calc R U P A 1
C19A C 1.0015(2) 0.4939(4) 0.58825(16) 0.0331(7) Uani 0.82 1 d . . P A 1
H19A H 1.0527 0.4324 0.5903 0.040 Uiso 0.82 1 calc R U P A 1
C20A C 1.0041(3) 0.3173(4) 0.7010(2) 0.0303(7) Uani 0.82 1 d . . P B 1
H20A H 1.0128 0.2338 0.7265 0.036 Uiso 0.82 1 calc R U P B 1
C20B C 0.816(4) 0.191(2) 0.5657(14) 0.0250(14) Uani 0.18 1 d D . P C 2
H20B H 0.7556 0.2326 0.5669 0.030 Uiso 0.18 1 calc R U P C 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 C1 2.013(2) . ?
P1 C3 1.813(2) . ?
P1 C8 1.826(2) . ?
P1 C14 1.821(2) . ?
P1 C20 1.956(2) . ?
F1 C1 1.354(2) . ?
F2 C1 1.382(2) . ?
F3 C20 1.380(2) . ?
F4 C20 1.382(3) . ?
O1 C1 1.396(3) . ?
O1 C2 1.384(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.386(3) . ?
C3 C4 1.398(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(3) . ?
C14 C19 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(3) . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?
P1A C1A 1.982(10) . ?
P1A C1B 1.92(3) . ?
P1A C1C 1.99(2) . ?
P1A C3A 1.8396(19) . ?
P1A C3B 1.810(7) . ?
P1A C3C 1.884(16) . ?
P1A C8A 1.815(3) . ?
P1A C8B 1.870(9) . ?
P1A C8C 1.780(11) . ?
P1A C14A 1.827(3) . ?
P1A C20A 1.978(6) . ?
P1A C20B 2.06(5) . ?
F1A C1A 1.357(10) . ?
F1B C1B 1.36(2) . ?
F1C C1C 1.27(4) . ?
F2A C1A 1.364(7) . ?
F2B C1B 1.371(19) . ?
F2C C1C 1.39(6) . ?
F3A C20A 1.387(5) . ?
F3B C20B 1.360(16) . ?
F4A C20A 1.366(5) . ?
F4B C20B 1.356(16) . ?
O1A C1A 1.415(8) . ?
O1A C2A 1.370(3) . ?
O1B C1B 1.361(18) . ?
O1B C2B 1.381(12) . ?
O1C C1C 1.39(3) . ?
O1C C2C 1.353(19) . ?
C3A C2A 1.3900 . ?
C3A C4A 1.3900 . ?
C2A C7A 1.3900 . ?
C7A H7A 0.9500 . ?
C7A C6A 1.3900 . ?
C6A H6A 0.9500 . ?
C6A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C3B C4B 1.3900 . ?
C3B C2B 1.3900 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.3900 . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3900 . ?
C6B H6B 0.9500 . ?
C6B C7B 1.3900 . ?
C7B H7B 0.9500 . ?
C7B C2B 1.3900 . ?
C4C H4C 0.9500 . ?
C4C C5C 1.3900 . ?
C4C C3C 1.3900 . ?
C5C H5C 0.9500 . ?
C5C C6C 1.3900 . ?
C6C H6C 0.9500 . ?
C6C C7C 1.3900 . ?
C7C H7C 0.9500 . ?
C7C C2C 1.3900 . ?
C2C C3C 1.3900 . ?
C8A C9A 1.391(4) . ?
C8A C13A 1.385(4) . ?
C8B C13B 1.3900 . ?
C8B C9B 1.3900 . ?
C13B H13B 0.9500 . ?
C13B C12B 1.3900 . ?
C12B H12B 0.9500 . ?
C12B C11B 1.3900 . ?
C11B H11B 0.9500 . ?
C11B C10B 1.3900 . ?
C10B H10B 0.9500 . ?
C10B C9B 1.3900 . ?
C9B H9B 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C10A 1.386(4) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.371(4) . ?
C10C H10C 0.9500 . ?
C10C C11C 1.3900 . ?
C10C C9C 1.3900 . ?
C11C H11C 0.9500 . ?
C11C C12C 1.3900 . ?
C12C H12C 0.9500 . ?
C12C C13C 1.3900 . ?
C13C H13C 0.9500 . ?
C13C C8C 1.3900 . ?
C8C C9C 1.3900 . ?
C9C H9C 0.9500 . ?
C11A H11A 0.9500 . ?
C11A C12A 1.387(5) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.384(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.381(4) . ?
C14A C19A 1.388(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.395(5) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.380(5) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.369(5) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.383(4) . ?
C19A H19A 0.9500 . ?
C20A H20A 1.0000 . ?
C20B H20B 1.0000 . ?

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
C3 P1 C1 81.78(10) . . ?
C3 P1 C8 115.94(10) . . ?
C3 P1 C14 123.35(10) . . ?
C3 P1 C20 94.82(10) . . ?
C8 P1 C1 90.47(9) . . ?
C8 P1 C20 90.44(9) . . ?
C14 P1 C1 91.30(9) . . ?
C14 P1 C8 120.30(10) . . ?
C14 P1 C20 91.13(9) . . ?
C20 P1 C1 176.54(10) . . ?
C2 O1 C1 107.80(17) . . ?
F1 C1 P1 118.14(15) . . ?
F1 C1 F2 104.96(16) . . ?
F1 C1 O1 105.64(17) . . ?
F2 C1 P1 112.78(14) . . ?
F2 C1 O1 105.87(17) . . ?
O1 C1 P1 108.59(14) . . ?
O1 C2 C3 117.9(2) . . ?
O1 C2 C7 119.7(2) . . ?
C7 C2 C3 122.3(2) . . ?
C2 C3 P1 113.24(16) . . ?
C2 C3 C4 117.8(2) . . ?
C4 C3 P1 128.92(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 120.7 . . ?
C6 C7 C2 118.5(2) . . ?
C6 C7 H7 120.7 . . ?
C9 C8 P1 118.50(17) . . ?
C13 C8 P1 122.16(16) . . ?
C13 C8 C9 119.3(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C15 C14 P1 120.58(16) . . ?
C19 C14 P1 120.13(17) . . ?
C19 C14 C15 119.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
P1 C20 H20 110.6 . . ?
F3 C20 P1 110.84(14) . . ?
F3 C20 F4 105.20(17) . . ?
F3 C20 H20 110.6 . . ?
F4 C20 P1 108.91(13) . . ?
F4 C20 H20 110.6 . . ?
C1B P1A C20B 165.8(11) . . ?
C3A P1A C1A 82.58(17) . . ?
C3A P1A C20A 92.17(16) . . ?
C3B P1A C1B 81.7(7) . . ?
C3B P1A C8B 113.9(6) . . ?
C3B P1A C20B 89.3(8) . . ?
C3C P1A C1C 78.9(10) . . ?
C8A P1A C1A 91.6(2) . . ?
C8A P1A C3A 121.94(16) . . ?
C8A P1A C14A 116.88(17) . . ?
C8A P1A C20A 91.59(16) . . ?
C8B P1A C1B 88.0(6) . . ?
C8B P1A C20B 85.5(8) . . ?
C8C P1A C1C 96.4(9) . . ?
C8C P1A C3C 125.6(10) . . ?
C14A P1A C1A 91.65(19) . . ?
C14A P1A C3A 120.98(14) . . ?
C14A P1A C20A 90.67(15) . . ?
C20A P1A C1A 174.7(2) . . ?
C2A O1A C1A 108.2(4) . . ?
C1B O1B C2B 100.6(14) . . ?
C2C O1C C1C 106.3(15) . . ?
F1A C1A P1A 118.4(6) . . ?
F1A C1A F2A 107.8(7) . . ?
F1A C1A O1A 104.7(7) . . ?
F2A C1A P1A 113.9(6) . . ?
F2A C1A O1A 103.3(4) . . ?
O1A C1A P1A 107.3(3) . . ?
F1B C1B P1A 111(2) . . ?
F1B C1B F2B 94(2) . . ?
F1B C1B O1B 111(2) . . ?
F2B C1B P1A 117.9(16) . . ?
O1B C1B P1A 110.2(14) . . ?
O1B C1B F2B 111(2) . . ?
F1C C1C P1A 127.4(16) . . ?
F1C C1C F2C 97(4) . . ?
F1C C1C O1C 91(2) . . ?
F2C C1C P1A 124(3) . . ?
O1C C1C P1A 111.2(14) . . ?
O1C C1C F2C 99(2) . . ?
C2A C3A P1A 110.30(15) . . ?
C2A C3A C4A 120.0 . . ?
C4A C3A P1A 129.48(15) . . ?
O1A C2A C3A 119.2(2) . . ?
O1A C2A C7A 120.7(2) . . ?
C3A C2A C7A 120.0 . . ?
C2A C7A H7A 120.0 . . ?
C6A C7A C2A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C7A C6A C5A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4B C3B P1A 133.2(5) . . ?
C4B C3B C2B 120.0 . . ?
C2B C3B P1A 105.7(5) . . ?
C3B C4B H4B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C5B C6B C7B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C2B C7B C6B 120.0 . . ?
C2B C7B H7B 120.0 . . ?
O1B C2B C3B 123.2(7) . . ?
O1B C2B C7B 116.8(7) . . ?
C7B C2B C3B 120.0 . . ?
C5C C4C H4C 120.0 . . ?
C5C C4C C3C 120.0 . . ?
C3C C4C H4C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C6C C5C C4C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C7C C6C C5C 120.0 . . ?
C7C C6C H6C 120.0 . . ?
C6C C7C H7C 120.0 . . ?
C2C C7C C6C 120.0 . . ?
C2C C7C H7C 120.0 . . ?
O1C C2C C7C 120.2(17) . . ?
O1C C2C C3C 119.6(17) . . ?
C7C C2C C3C 120.0 . . ?
C4C C3C P1A 128.8(12) . . ?
C2C C3C P1A 110.9(12) . . ?
C2C C3C C4C 120.0 . . ?
C9A C8A P1A 121.5(2) . . ?
C13A C8A P1A 120.1(2) . . ?
C13A C8A C9A 118.4(3) . . ?
C13B C8B P1A 116.4(8) . . ?
C13B C8B C9B 120.0 . . ?
C9B C8B P1A 123.3(8) . . ?
C8B C13B H13B 120.0 . . ?
C8B C13B C12B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B C12B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B C8B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C8A C9A H9A 119.7 . . ?
C10A C9A C8A 120.7(3) . . ?
C10A C9A H9A 119.7 . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A C9A 120.3(3) . . ?
C11A C10A H10A 119.8 . . ?
C11C C10C H10C 120.0 . . ?
C11C C10C C9C 120.0 . . ?
C9C C10C H10C 120.0 . . ?
C10C C11C H11C 120.0 . . ?
C10C C11C C12C 120.0 . . ?
C12C C11C H11C 120.0 . . ?
C11C C12C H12C 120.0 . . ?
C13C C12C C11C 120.0 . . ?
C13C C12C H12C 120.0 . . ?
C12C C13C H13C 120.0 . . ?
C12C C13C C8C 120.0 . . ?
C8C C13C H13C 120.0 . . ?
C13C C8C P1A 120.2(12) . . ?
C13C C8C C9C 120.0 . . ?
C9C C8C P1A 119.8(12) . . ?
C10C C9C H9C 120.0 . . ?
C8C C9C C10C 120.0 . . ?
C8C C9C H9C 120.0 . . ?
C10A C11A H11A 120.2 . . ?
C10A C11A C12A 119.6(3) . . ?
C12A C11A H11A 120.2 . . ?
C11A C12A H12A 119.9 . . ?
C13A C12A C11A 120.1(3) . . ?
C13A C12A H12A 119.9 . . ?
C8A C13A H13A 119.6 . . ?
C12A C13A C8A 120.8(3) . . ?
C12A C13A H13A 119.6 . . ?
C15A C14A P1A 119.5(2) . . ?
C15A C14A C19A 119.6(3) . . ?
C19A C14A P1A 120.9(2) . . ?
C14A C15A H15A 120.2 . . ?
C14A C15A C16A 119.7(3) . . ?
C16A C15A H15A 120.2 . . ?
C15A C16A H16A 119.9 . . ?
C17A C16A C15A 120.1(3) . . ?
C17A C16A H16A 119.9 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0(3) . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 119.8 . . ?
C17A C18A C19A 120.3(3) . . ?
C19A C18A H18A 119.8 . . ?
C14A C19A H19A 119.9 . . ?
C18A C19A C14A 120.2(3) . . ?
C18A C19A H19A 119.9 . . ?
P1A C20A H20A 109.4 . . ?
F3A C20A P1A 108.6(3) . . ?
F3A C20A H20A 109.4 . . ?
F4A C20A P1A 112.5(4) . . ?
F4A C20A F3A 107.5(5) . . ?
F4A C20A H20A 109.4 . . ?
P1A C20B H20B 112.1 . . ?
F3B C20B P1A 106(3) . . ?
F3B C20B H20B 112.1 . . ?
F4B C20B P1A 108(3) . . ?
F4B C20B F3B 106.4(18) . . ?
F4B C20B H20B 112.1 . . ?

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
P1 C3 C4 C5 178.00(18) . . . . ?
P1 C8 C9 C10 178.89(17) . . . . ?
P1 C8 C13 C12 -179.38(19) . . . . ?
P1 C14 C15 C16 179.23(17) . . . . ?
P1 C14 C19 C18 -179.96(18) . . . . ?
O1 C2 C3 P1 3.1(3) . . . . ?
O1 C2 C3 C4 -178.78(19) . . . . ?
O1 C2 C7 C6 178.6(2) . . . . ?
C1 P1 C3 C2 -17.44(17) . . . . ?
C1 P1 C3 C4 164.7(2) . . . . ?
C1 P1 C8 C9 82.73(17) . . . . ?
C1 P1 C8 C13 -98.26(19) . . . . ?
C1 P1 C14 C15 56.24(18) . . . . ?
C1 P1 C14 C19 -122.74(19) . . . . ?
C1 O1 C2 C3 21.2(3) . . . . ?
C1 O1 C2 C7 -159.3(2) . . . . ?
C2 O1 C1 P1 -32.9(2) . . . . ?
C2 O1 C1 F1 -160.59(16) . . . . ?
C2 O1 C1 F2 88.41(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 P1 C8 C9 1.6(2) . . . . ?
C3 P1 C8 C13 -179.35(17) . . . . ?
C3 P1 C14 C15 137.26(17) . . . . ?
C3 P1 C14 C19 -41.7(2) . . . . ?
C3 C2 C7 C6 -1.8(4) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
C5 C6 C7 C2 0.1(4) . . . . ?
C7 C2 C3 P1 -176.45(19) . . . . ?
C7 C2 C3 C4 1.7(3) . . . . ?
C8 P1 C3 C2 69.06(19) . . . . ?
C8 P1 C3 C4 -108.8(2) . . . . ?
C8 P1 C14 C15 -35.1(2) . . . . ?
C8 P1 C14 C19 145.95(17) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C14 P1 C3 C2 -103.57(18) . . . . ?
C14 P1 C3 C4 78.6(2) . . . . ?
C14 P1 C8 C9 174.51(15) . . . . ?
C14 P1 C8 C13 -6.5(2) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C14 0.4(4) . . . . ?
C19 C14 C15 C16 -1.8(3) . . . . ?
C20 P1 C3 C2 161.90(17) . . . . ?
C20 P1 C3 C4 -16.0(2) . . . . ?
C20 P1 C8 C9 -93.93(17) . . . . ?
C20 P1 C8 C13 85.08(19) . . . . ?
C20 P1 C14 C15 -126.23(18) . . . . ?
C20 P1 C14 C19 54.79(19) . . . . ?
P1A C3A C2A O1A 8.7(2) . . . . ?
P1A C3A C2A C7A -175.08(19) . . . . ?
P1A C3A C4A C5A 174.0(2) . . . . ?
P1A C3B C4B C5B 166.6(9) . . . . ?
P1A C3B C2B O1B 9.5(9) . . . . ?
P1A C3B C2B C7B -169.9(7) . . . . ?
P1A C8A C9A C10A 176.2(3) . . . . ?
P1A C8A C13A C12A -177.2(2) . . . . ?
P1A C8B C13B C12B -174.7(12) . . . . ?
P1A C8B C9B C10B 174.3(13) . . . . ?
P1A C8C C9C C10C 178.1(14) . . . . ?
P1A C14A C15A C16A 178.7(3) . . . . ?
P1A C14A C19A C18A -179.2(3) . . . . ?
O1A C2A C7A C6A 176.2(2) . . . . ?
O1C C2C C3C P1A -9.7(17) . . . . ?
O1C C2C C3C C4C 175(2) . . . . ?
C1A P1A C3A C2A -22.2(2) . . . . ?
C1A P1A C3A C4A 163.3(3) . . . . ?
C1A P1A C8A C9A 58.4(3) . . . . ?
C1A P1A C8A C13A -122.7(4) . . . . ?
C1A P1A C14A C15A 72.8(3) . . . . ?
C1A P1A C14A C19A -108.1(3) . . . . ?
C1A O1A C2A C3A 17.9(3) . . . . ?
C1A O1A C2A C7A -158.3(3) . . . . ?
C1B P1A C3B C4B 166.7(8) . . . . ?
C1B P1A C3B C2B -25.3(6) . . . . ?
C1B P1A C8B C13B 71.3(10) . . . . ?
C1B P1A C8B C9B -103.2(11) . . . . ?
C1B O1B C2B C3B 21.1(14) . . . . ?
C1B O1B C2B C7B -159.5(12) . . . . ?
C1C P1A C3C C4C -163.2(18) . . . . ?
C1C P1A C3C C2C 22.6(11) . . . . ?
C1C P1A C8C C13C 129.9(10) . . . . ?
C1C P1A C8C C9C -48.2(12) . . . . ?
C1C O1C C2C C7C 158.3(18) . . . . ?
C1C O1C C2C C3C -17(2) . . . . ?
C3A P1A C8A C9A 140.7(3) . . . . ?
C3A P1A C8A C13A -40.5(4) . . . . ?
C3A P1A C14A C15A -9.5(3) . . . . ?
C3A P1A C14A C19A 169.5(2) . . . . ?
C3A C2A C7A C6A 0.0 . . . . ?
C2A O1A C1A P1A -33.7(3) . . . . ?
C2A O1A C1A F1A -160.3(7) . . . . ?
C2A O1A C1A F2A 87.0(5) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C2A C7A C6A C5A 0.0 . . . . ?
C7A C6A C5A C4A 0.0 . . . . ?
C6A C5A C4A C3A 0.0 . . . . ?
C4A C3A C2A O1A -176.2(2) . . . . ?
C4A C3A C2A C7A 0.0 . . . . ?
C3B P1A C8B C13B 151.3(7) . . . . ?
C3B P1A C8B C9B -23.2(11) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C3B C2B O1B 179.4(10) . . . . ?
C4B C3B C2B C7B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C5B C6B C7B C2B 0.0 . . . . ?
C6B C7B C2B O1B -179.4(9) . . . . ?
C6B C7B C2B C3B 0.0 . . . . ?
C2B O1B C1B P1A -40.5(13) . . . . ?
C2B O1B C1B F1B -165(2) . . . . ?
C2B O1B C1B F2B 91.9(19) . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C4C C5C C6C C7C 0.0 . . . . ?
C5C C4C C3C P1A -174(2) . . . . ?
C5C C4C C3C C2C 0.0 . . . . ?
C5C C6C C7C C2C 0.0 . . . . ?
C6C C7C C2C O1C -175(2) . . . . ?
C6C C7C C2C C3C 0.0 . . . . ?
C7C C2C C3C P1A 175(2) . . . . ?
C7C C2C C3C C4C 0.0 . . . . ?
C2C O1C C1C P1A 35.1(19) . . . . ?
C2C O1C C1C F1C -96(2) . . . . ?
C2C O1C C1C F2C 167(3) . . . . ?
C3C P1A C8C C13C 49.0(14) . . . . ?
C3C P1A C8C C9C -129.2(12) . . . . ?
C3C C4C C5C C6C 0.0 . . . . ?
C8A P1A C3A C2A -109.41(17) . . . . ?
C8A P1A C3A C4A 76.1(2) . . . . ?
C8A P1A C14A C15A 165.5(3) . . . . ?
C8A P1A C14A C19A -15.5(3) . . . . ?
C8A C9A C10A C11A 1.1(5) . . . . ?
C8B P1A C3B C4B 82.6(9) . . . . ?
C8B P1A C3B C2B -109.4(7) . . . . ?
C8B C13B C12B C11B 0.0 . . . . ?
C13B C8B C9B C10B 0.0 . . . . ?
C13B C12B C11B C10B 0.0 . . . . ?
C12B C11B C10B C9B 0.0 . . . . ?
C11B C10B C9B C8B 0.0 . . . . ?
C9B C8B C13B C12B 0.0 . . . . ?
C9A C8A C13A C12A 1.7(6) . . . . ?
C9A C10A C11A C12A 1.6(6) . . . . ?
C10A C11A C12A C13A -2.5(6) . . . . ?
C10C C11C C12C C13C 0.0 . . . . ?
C11C C10C C9C C8C 0.0 . . . . ?
C11C C12C C13C C8C 0.0 . . . . ?
C12C C13C C8C P1A -178.1(14) . . . . ?
C12C C13C C8C C9C 0.0 . . . . ?
C13C C8C C9C C10C 0.0 . . . . ?
C8C P1A C3C C4C -73(2) . . . . ?
C8C P1A C3C C2C 112.6(13) . . . . ?
C9C C10C C11C C12C 0.0 . . . . ?
C11A C12A C13A C8A 0.9(6) . . . . ?
C13A C8A C9A C10A -2.7(5) . . . . ?
C14A P1A C3A C2A 65.28(18) . . . . ?
C14A P1A C3A C4A -109.21(19) . . . . ?
C14A P1A C8A C9A -34.2(4) . . . . ?
C14A P1A C8A C13A 144.7(3) . . . . ?
C14A C15A C16A C17A 0.0(5) . . . . ?
C15A C14A C19A C18A -0.2(4) . . . . ?
C15A C16A C17A C18A 0.8(5) . . . . ?
C16A C17A C18A C19A -1.4(5) . . . . ?
C17A C18A C19A C14A 1.0(5) . . . . ?
C19A C14A C15A C16A -0.4(5) . . . . ?
C20A P1A C3A C2A 157.36(15) . . . . ?
C20A P1A C3A C4A -17.12(19) . . . . ?
C20A P1A C8A C9A -125.8(3) . . . . ?
C20A P1A C8A C13A 53.1(4) . . . . ?
C20A P1A C14A C15A -102.4(3) . . . . ?
C20A P1A C14A C19A 76.6(3) . . . . ?
C20B P1A C3B C4B -2.2(10) . . . . ?
C20B P1A C3B C2B 165.8(9) . . . . ?
C20B P1A C8B C13B -121.4(12) . . . . ?
C20B P1A C8B C9B 64.1(13) . . . . ?

_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_sv1033
_database_code_depnum_ccdc_archive 'CCDC 2061885'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2021-02-08 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F2 O2 P'
_chemical_formula_sum            'C20 H15 F2 O2 P'
_chemical_formula_weight         356.29
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1354(6)
_cell_length_b                   12.5827(8)
_cell_length_c                   14.7085(9)
_cell_angle_alpha                89.257(2)
_cell_angle_beta                 74.417(2)
_cell_angle_gamma                75.991(2)
_cell_volume                     1750.37(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9629
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.514
_cell_measurement_theta_min      3.025
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1376 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.8520.
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    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28652
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_min         2.144
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_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                7989
_reflns_number_total             10683
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_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     451
_refine_ls_number_reflns         10683
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0800P)²+0.1970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C10(H10), C4(H4), C16A(H16A), C7A(H7A), C17A(H17A), C7(H7),
 C16(H16), C6A(H6A), C20A(H20A), C4A(H4A), C12A(H12A), C14A(H14A), C20(H20),
 C13A(H13A), C11A(H11A), C6(H6), C12(H12), C5(H5), C17(H17), C11(H11), C14(H14),
  C13(H13), C5A(H5A), C18A(H18A), C19A(H19A), C18(H18), C19(H19)
;
_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 0.53495(3) 0.54357(3) 0.29336(2) 0.03964(9) Uani 1 1 d . . . . .
P1A P 0.45980(3) 0.90850(2) 0.20910(2) 0.03598(9) Uani 1 1 d . . . . .
O1A O 0.45881(10) 0.80604(7) 0.16202(7) 0.0458(2) Uani 1 1 d . . . . .
F2A F 0.57636(11) 0.96890(8) 0.33538(8) 0.0705(3) Uani 1 1 d . . . . .
O2A O 0.31198(10) 1.10979(7) 0.26756(6) 0.0444(2) Uani 1 1 d . . . . .
O1 O 0.53069(10) 0.64569(8) 0.34309(7) 0.0495(2) Uani 1 1 d . . . . .
F1A F 0.71012(9) 0.83647(9) 0.23330(8) 0.0717(3) Uani 1 1 d . . . . .
O2 O 0.68573(10) 0.34659(7) 0.22586(7) 0.0490(2) Uani 1 1 d . . . . .
F2 F 0.41979(12) 0.48020(8) 0.16814(9) 0.0781(3) Uani 1 1 d . . . . .
F1 F 0.28324(9) 0.61199(10) 0.27043(9) 0.0799(3) Uani 1 1 d . . . . .
C9A C 0.24520(12) 0.97995(11) 0.38124(8) 0.0399(2) Uani 1 1 d . . . . .
C3A C 0.41800(14) 1.11593(10) 0.18771(9) 0.0412(3) Uani 1 1 d . . . . .
C8A C 0.28778(11) 1.00104(9) 0.27682(8) 0.0359(2) Uani 1 1 d . . . . .
C8 C 0.70843(13) 0.45588(10) 0.22209(9) 0.0403(2) Uani 1 1 d . . . . .
C9 C 0.75102(13) 0.48359(11) 0.11927(9) 0.0443(3) Uani 1 1 d . . . . .
C3 C 0.58362(14) 0.33447(11) 0.30591(10) 0.0447(3) Uani 1 1 d . . . . .
C15A C 0.17416(12) 0.99347(11) 0.22798(8) 0.0413(3) Uani 1 1 d . . . . .
C10A C 0.26083(15) 0.87359(12) 0.41073(10) 0.0501(3) Uani 1 1 d . . . . .
H10A H 0.3000 0.8145 0.3665 0.060 Uiso 1 1 calc R U . . .
C1A C 0.57572(13) 0.87671(11) 0.28953(10) 0.0462(3) Uani 1 1 d . . . . .
H1A H 0.5470 0.8229 0.3344 0.055 Uiso 1 1 calc R U . . .
C10 C 0.73283(16) 0.59198(13) 0.09496(11) 0.0555(3) Uani 1 1 d . . . . .
H10 H 0.6909 0.6482 0.1418 0.067 Uiso 1 1 calc R U . . .
C2A C 0.50919(13) 1.01839(11) 0.14437(9) 0.0411(3) Uani 1 1 d . . . . .
C15 C 0.82173(13) 0.46003(11) 0.27209(9) 0.0440(3) Uani 1 1 d . . . . .
C1 C 0.41728(14) 0.57331(12) 0.21412(11) 0.0500(3) Uani 1 1 d . . . . .
H1 H 0.4441 0.6276 0.1691 0.060 Uiso 1 1 calc R U . . .
C4 C 0.57141(17) 0.23154(12) 0.33447(11) 0.0538(3) Uani 1 1 d . . . . .
H4 H 0.6323 0.1685 0.3007 0.065 Uiso 1 1 calc R U . . .
C2 C 0.49276(14) 0.42924(11) 0.35538(10) 0.0451(3) Uani 1 1 d . . . . .
C16A C 0.12940(14) 0.89788(13) 0.22738(10) 0.0505(3) Uani 1 1 d . . . . .
H16A H 0.1706 0.8368 0.2554 0.061 Uiso 1 1 calc R U . . .
C7A C 0.62028(15) 1.02103(14) 0.06440(10) 0.0516(3) Uani 1 1 d . . . . .
H7A H 0.6824 0.9563 0.0346 0.062 Uiso 1 1 calc R U . . .
C17A C 0.02382(17) 0.89241(18) 0.18533(13) 0.0684(5) Uani 1 1 d . . . . .
H17A H -0.0053 0.8277 0.1855 0.082 Uiso 1 1 calc R U . . .
C7 C 0.38704(17) 0.42144(14) 0.43641(11) 0.0561(3) Uani 1 1 d . . . . .
H7 H 0.3258 0.4842 0.4704 0.067 Uiso 1 1 calc R U . . .
C16 C 0.85802(15) 0.55786(14) 0.28334(12) 0.0578(4) Uani 1 1 d . . . . .
H16 H 0.8115 0.6219 0.2616 0.069 Uiso 1 1 calc R U . . .
C6A C 0.63601(18) 1.12090(16) 0.03062(11) 0.0623(4) Uani 1 1 d . . . . .
H6A H 0.7098 1.1239 -0.0222 0.075 Uiso 1 1 calc R U . . .
C20A C 0.11215(17) 1.08348(15) 0.18480(12) 0.0602(4) Uani 1 1 d . . . . .
H20A H 0.1415 1.1481 0.1837 0.072 Uiso 1 1 calc R U . . .
C4A C 0.43258(18) 1.21684(12) 0.15364(11) 0.0543(3) Uani 1 1 d . . . . .
H4A H 0.3703 1.2818 0.1830 0.065 Uiso 1 1 calc R U . . .
C12A C 0.16059(18) 0.94120(19) 0.57209(11) 0.0717(5) Uani 1 1 d . . . . .
H12A H 0.1314 0.9284 0.6359 0.086 Uiso 1 1 calc R U . . .
C14A C 0.18807(15) 1.06701(13) 0.44843(10) 0.0526(3) Uani 1 1 d . . . . .
H14A H 0.1779 1.1388 0.4298 0.063 Uiso 1 1 calc R U . . .
C20 C 0.89337(19) 0.36565(16) 0.30421(14) 0.0712(5) Uani 1 1 d . . . . .
H20 H 0.8706 0.2994 0.2975 0.085 Uiso 1 1 calc R U . . .
C13A C 0.14610(18) 1.04678(17) 0.54366(11) 0.0681(5) Uani 1 1 d . . . . .
H13A H 0.1079 1.1053 0.5885 0.082 Uiso 1 1 calc R U . . .
C11A C 0.21789(17) 0.85516(16) 0.50655(11) 0.0644(4) Uani 1 1 d . . . . .
H11A H 0.2284 0.7837 0.5260 0.077 Uiso 1 1 calc R U . . .
C6 C 0.37520(19) 0.31833(16) 0.46513(12) 0.0645(4) Uani 1 1 d . . . . .
H6 H 0.3053 0.3116 0.5191 0.077 Uiso 1 1 calc R U . . .
C12 C 0.8380(2) 0.5358(2) -0.06838(12) 0.0765(5) Uani 1 1 d . . . . .
H12 H 0.8681 0.5529 -0.1311 0.092 Uiso 1 1 calc R U . . .
C5 C 0.46608(19) 0.22522(14) 0.41454(12) 0.0613(4) Uani 1 1 d . . . . .
H5 H 0.4559 0.1567 0.4350 0.074 Uiso 1 1 calc R U . . .
C17 C 0.96272(18) 0.56058(19) 0.32660(14) 0.0740(5) Uani 1 1 d . . . . .
H17 H 0.9854 0.6266 0.3346 0.089 Uiso 1 1 calc R U . . .
C11 C 0.77676(19) 0.61727(16) 0.00108(12) 0.0675(4) Uani 1 1 d . . . . .
H11 H 0.7643 0.6902 -0.0144 0.081 Uiso 1 1 calc R U . . .
C14 C 0.81196(19) 0.40146(15) 0.04821(11) 0.0646(4) Uani 1 1 d . . . . .
H14 H 0.8242 0.3282 0.0628 0.077 Uiso 1 1 calc R U . . .
C13 C 0.8548(2) 0.42896(19) -0.04523(13) 0.0824(6) Uani 1 1 d . . . . .
H13 H 0.8956 0.3735 -0.0928 0.099 Uiso 1 1 calc R U . . .
C5A C 0.5424(2) 1.21752(15) 0.07495(12) 0.0633(4) Uani 1 1 d . . . . .
H5A H 0.5543 1.2843 0.0508 0.076 Uiso 1 1 calc R U . . .
C18A C -0.03769(19) 0.9815(2) 0.14370(14) 0.0820(6) Uani 1 1 d . . . . .
H18A H -0.1088 0.9776 0.1159 0.098 Uiso 1 1 calc R U . . .
C19A C 0.0059(2) 1.0766(2) 0.14317(15) 0.0826(6) Uani 1 1 d . . . . .
H19A H -0.0359 1.1371 0.1148 0.099 Uiso 1 1 calc R U . . .
C18 C 1.0334(2) 0.4659(2) 0.35778(16) 0.0910(7) Uani 1 1 d . . . . .
H18 H 1.1043 0.4675 0.3865 0.109 Uiso 1 1 calc R U . . .
C19 C 0.9989(2) 0.3699(2) 0.34626(19) 0.0995(8) Uani 1 1 d . . . . .
H19 H 1.0472 0.3059 0.3671 0.119 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 O1 1.4726(9) . ?
P1 C8 1.8731(12) . ?
P1 C1 1.8547(14) . ?
P1 C2 1.7716(14) . ?
P1A O1A 1.4747(9) . ?
P1A C8A 1.8714(11) . ?
P1A C1A 1.8565(14) . ?
P1A C2A 1.7645(13) . ?
F2A C1A 1.3516(16) . ?
O2A C3A 1.3783(15) . ?
O2A C8A 1.4460(14) . ?
F1A C1A 1.3666(16) . ?
O2 C8 1.4462(15) . ?
O2 C3 1.3775(16) . ?
F2 C1 1.3519(16) . ?
F1 C1 1.3617(17) . ?
C9A C8A 1.5180(16) . ?
C9A C10A 1.3869(19) . ?
C9A C14A 1.3876(18) . ?
C3A C2A 1.3862(18) . ?
C3A C4A 1.3856(18) . ?
C8A C15A 1.5332(17) . ?
C8 C9 1.5177(18) . ?
C8 C15 1.5316(18) . ?
C9 C10 1.387(2) . ?
C9 C14 1.3835(19) . ?
C3 C4 1.3802(19) . ?
C3 C2 1.3894(19) . ?
C15A C16A 1.385(2) . ?
C15A C20A 1.390(2) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.393(2) . ?
C1A H1A 0.9800 . ?
C10 H10 0.9300 . ?
C10 C11 1.390(2) . ?
C2A C7A 1.3993(17) . ?
C15 C16 1.391(2) . ?
C15 C20 1.383(2) . ?
C1 H1 0.9800 . ?
C4 H4 0.9300 . ?
C4 C5 1.377(2) . ?
C2 C7 1.393(2) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.387(2) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.375(2) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.367(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.382(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(2) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.391(3) . ?
C20A H20A 0.9300 . ?
C20A C19A 1.394(2) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.375(2) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.373(3) . ?
C12A C11A 1.364(3) . ?
C14A H14A 0.9300 . ?
C14A C13A 1.389(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.383(3) . ?
C13A H13A 0.9300 . ?
C11A H11A 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.381(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.363(3) . ?
C12 C13 1.364(3) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.392(2) . ?
C13 H13 0.9300 . ?
C5A H5A 0.9300 . ?
C18A H18A 0.9300 . ?
C18A C19A 1.372(3) . ?
C19A H19A 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.361(3) . ?
C19 H19 0.9300 . ?

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
O1 P1 C8 119.83(6) . . ?
O1 P1 C1 109.95(6) . . ?
O1 P1 C2 121.77(6) . . ?
C1 P1 C8 106.96(6) . . ?
C2 P1 C8 91.05(6) . . ?
C2 P1 C1 104.94(6) . . ?
O1A P1A C8A 118.99(5) . . ?
O1A P1A C1A 109.61(6) . . ?
O1A P1A C2A 121.90(6) . . ?
C1A P1A C8A 107.81(6) . . ?
C2A P1A C8A 91.22(6) . . ?
C2A P1A C1A 105.25(6) . . ?
C3A O2A C8A 112.17(9) . . ?
C3 O2 C8 112.33(9) . . ?
C10A C9A C8A 120.53(11) . . ?
C10A C9A C14A 119.10(12) . . ?
C14A C9A C8A 120.36(12) . . ?
O2A C3A C2A 117.68(11) . . ?
O2A C3A C4A 120.43(12) . . ?
C4A C3A C2A 121.88(13) . . ?
O2A C8A P1A 104.26(7) . . ?
O2A C8A C9A 108.38(10) . . ?
O2A C8A C15A 108.95(10) . . ?
C9A C8A P1A 113.85(8) . . ?
C9A C8A C15A 112.44(9) . . ?
C15A C8A P1A 108.56(8) . . ?
O2 C8 P1 103.66(8) . . ?
O2 C8 C9 108.56(10) . . ?
O2 C8 C15 109.02(10) . . ?
C9 C8 P1 114.38(8) . . ?
C9 C8 C15 112.11(10) . . ?
C15 C8 P1 108.68(8) . . ?
C10 C9 C8 120.52(12) . . ?
C14 C9 C8 120.78(13) . . ?
C14 C9 C10 118.68(14) . . ?
O2 C3 C4 120.77(13) . . ?
O2 C3 C2 117.59(12) . . ?
C4 C3 C2 121.63(13) . . ?
C16A C15A C8A 120.89(12) . . ?
C16A C15A C20A 118.68(13) . . ?
C20A C15A C8A 120.42(13) . . ?
C9A C10A H10A 120.0 . . ?
C9A C10A C11A 120.08(15) . . ?
C11A C10A H10A 120.0 . . ?
P1A C1A H1A 110.9 . . ?
F2A C1A P1A 111.02(9) . . ?
F2A C1A F1A 106.55(11) . . ?
F2A C1A H1A 110.9 . . ?
F1A C1A P1A 106.42(10) . . ?
F1A C1A H1A 110.9 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.49(15) . . ?
C11 C10 H10 119.8 . . ?
C3A C2A P1A 108.72(9) . . ?
C3A C2A C7A 119.53(12) . . ?
C7A C2A P1A 131.71(11) . . ?
C16 C15 C8 120.79(12) . . ?
C20 C15 C8 120.54(14) . . ?
C20 C15 C16 118.63(14) . . ?
P1 C1 H1 110.7 . . ?
F2 C1 P1 110.63(9) . . ?
F2 C1 F1 107.09(12) . . ?
F2 C1 H1 110.7 . . ?
F1 C1 P1 106.81(10) . . ?
F1 C1 H1 110.7 . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.82(15) . . ?
C5 C4 H4 121.1 . . ?
C3 C2 P1 108.21(10) . . ?
C3 C2 C7 119.83(13) . . ?
C7 C2 P1 131.87(12) . . ?
C15A C16A H16A 119.7 . . ?
C15A C16A C17A 120.67(15) . . ?
C17A C16A H16A 119.7 . . ?
C2A C7A H7A 120.6 . . ?
C6A C7A C2A 118.90(15) . . ?
C6A C7A H7A 120.6 . . ?
C16A C17A H17A 119.8 . . ?
C18A C17A C16A 120.41(18) . . ?
C18A C17A H17A 119.8 . . ?
C2 C7 H7 120.8 . . ?
C6 C7 C2 118.49(15) . . ?
C6 C7 H7 120.8 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.53(16) . . ?
C17 C16 H16 119.7 . . ?
C7A C6A H6A 119.8 . . ?
C7A C6A C5A 120.43(14) . . ?
C5A C6A H6A 119.8 . . ?
C15A C20A H20A 120.1 . . ?
C15A C20A C19A 119.86(18) . . ?
C19A C20A H20A 120.1 . . ?
C3A C4A H4A 121.2 . . ?
C5A C4A C3A 117.61(15) . . ?
C5A C4A H4A 121.2 . . ?
C13A C12A H12A 120.1 . . ?
C11A C12A H12A 120.1 . . ?
C11A C12A C13A 119.88(15) . . ?
C9A C14A H14A 120.1 . . ?
C9A C14A C13A 119.88(15) . . ?
C13A C14A H14A 120.1 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 119.94(19) . . ?
C19 C20 H20 120.0 . . ?
C12A C13A C14A 120.59(16) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A C10A 120.46(16) . . ?
C12A C11A H11A 119.8 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.71(15) . . ?
C5 C6 H6 119.6 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.48(17) . . ?
C13 C12 H12 120.3 . . ?
C4 C5 C6 121.52(15) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.42(18) . . ?
C12 C11 H11 119.8 . . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.70(17) . . ?
C13 C14 H14 120.1 . . ?
C12 C13 C14 121.22(17) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A C6A 121.65(14) . . ?
C4A C5A H5A 119.2 . . ?
C17A C18A H18A 120.1 . . ?
C17A C18A C19A 119.70(16) . . ?
C19A C18A H18A 120.1 . . ?
C20A C19A H19A 119.7 . . ?
C18A C19A C20A 120.68(18) . . ?
C18A C19A H19A 119.7 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.51(18) . . ?
C19 C18 H18 120.2 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.27(19) . . ?
C18 C19 H19 119.4 . . ?

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
P1 C8 C9 C10 42.63(16) . . . . ?
P1 C8 C9 C14 -139.03(13) . . . . ?
P1 C8 C15 C16 -63.96(15) . . . . ?
P1 C8 C15 C20 118.20(14) . . . . ?
P1 C2 C7 C6 175.96(12) . . . . ?
P1A C8A C15A C16A 67.85(13) . . . . ?
P1A C8A C15A C20A -113.32(12) . . . . ?
P1A C2A C7A C6A -177.68(11) . . . . ?
O1A P1A C8A O2A -149.20(7) . . . . ?
O1A P1A C8A C9A 92.88(10) . . . . ?
O1A P1A C8A C15A -33.18(10) . . . . ?
O1A P1A C1A F2A -178.64(9) . . . . ?
O1A P1A C1A F1A 65.81(10) . . . . ?
O1A P1A C2A C3A 138.64(9) . . . . ?
O1A P1A C2A C7A -43.59(15) . . . . ?
O2A C3A C2A P1A -0.44(14) . . . . ?
O2A C3A C2A C7A -178.53(12) . . . . ?
O2A C3A C4A C5A 178.58(13) . . . . ?
O2A C8A C15A C16A -179.20(11) . . . . ?
O2A C8A C15A C20A -0.37(16) . . . . ?
O1 P1 C8 O2 151.76(8) . . . . ?
O1 P1 C8 C9 -90.22(10) . . . . ?
O1 P1 C8 C15 35.90(11) . . . . ?
O1 P1 C1 F2 -179.83(10) . . . . ?
O1 P1 C1 F1 -63.62(11) . . . . ?
O1 P1 C2 C3 -142.04(9) . . . . ?
O1 P1 C2 C7 41.33(17) . . . . ?
O2 C8 C9 C10 157.82(12) . . . . ?
O2 C8 C9 C14 -23.83(17) . . . . ?
O2 C8 C15 C16 -176.30(12) . . . . ?
O2 C8 C15 C20 5.86(18) . . . . ?
O2 C3 C4 C5 -179.30(13) . . . . ?
O2 C3 C2 P1 2.43(15) . . . . ?
O2 C3 C2 C7 179.54(13) . . . . ?
C9A C8A C15A C16A -59.03(15) . . . . ?
C9A C8A C15A C20A 119.80(13) . . . . ?
C9A C10A C11A C12A -0.2(2) . . . . ?
C9A C14A C13A C12A 0.0(3) . . . . ?
C3A O2A C8A P1A 24.77(11) . . . . ?
C3A O2A C8A C9A 146.37(10) . . . . ?
C3A O2A C8A C15A -90.98(11) . . . . ?
C3A C2A C7A C6A -0.1(2) . . . . ?
C3A C4A C5A C6A 0.0(2) . . . . ?
C8A P1A C1A F2A -47.73(11) . . . . ?
C8A P1A C1A F1A -163.28(8) . . . . ?
C8A P1A C2A C3A 12.89(10) . . . . ?
C8A P1A C2A C7A -169.34(14) . . . . ?
C8A O2A C3A C2A -17.36(15) . . . . ?
C8A O2A C3A C4A 163.50(12) . . . . ?
C8A C9A C10A C11A -178.26(13) . . . . ?
C8A C9A C14A C13A 178.35(13) . . . . ?
C8A C15A C16A C17A 178.23(12) . . . . ?
C8A C15A C20A C19A -178.02(15) . . . . ?
C8 P1 C1 F2 48.56(12) . . . . ?
C8 P1 C1 F1 164.78(9) . . . . ?
C8 P1 C2 C3 -15.41(10) . . . . ?
C8 P1 C2 C7 167.96(15) . . . . ?
C8 O2 C3 C4 -163.62(12) . . . . ?
C8 O2 C3 C2 17.41(16) . . . . ?
C8 C9 C10 C11 177.56(14) . . . . ?
C8 C9 C14 C13 -177.67(16) . . . . ?
C8 C15 C16 C17 -178.49(14) . . . . ?
C8 C15 C20 C19 177.72(18) . . . . ?
C9 C8 C15 C16 63.47(16) . . . . ?
C9 C8 C15 C20 -114.37(15) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C14 C13 C12 0.1(3) . . . . ?
C3 O2 C8 P1 -26.65(12) . . . . ?
C3 O2 C8 C9 -148.64(10) . . . . ?
C3 O2 C8 C15 88.96(12) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C2 C7 C6 -0.3(2) . . . . ?
C15A C16A C17A C18A 0.0(2) . . . . ?
C15A C20A C19A C18A -0.5(3) . . . . ?
C10A C9A C8A P1A -42.91(14) . . . . ?
C10A C9A C8A O2A -158.42(11) . . . . ?
C10A C9A C8A C15A 81.08(14) . . . . ?
C10A C9A C14A C13A -0.7(2) . . . . ?
C1A P1A C8A O2A 85.28(8) . . . . ?
C1A P1A C8A C9A -32.64(10) . . . . ?
C1A P1A C8A C15A -158.70(8) . . . . ?
C1A P1A C2A C3A -95.95(10) . . . . ?
C1A P1A C2A C7A 81.82(14) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C2A P1A C8A O2A -21.17(8) . . . . ?
C2A P1A C8A C9A -139.09(9) . . . . ?
C2A P1A C8A C15A 94.85(9) . . . . ?
C2A P1A C1A F2A 48.63(11) . . . . ?
C2A P1A C1A F1A -66.92(10) . . . . ?
C2A C3A C4A C5A -0.5(2) . . . . ?
C2A C7A C6A C5A -0.4(2) . . . . ?
C15 C8 C9 C10 -81.68(15) . . . . ?
C15 C8 C9 C14 96.66(16) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C15 C20 C19 C18 0.7(4) . . . . ?
C1 P1 C8 O2 -82.36(9) . . . . ?
C1 P1 C8 C9 35.66(11) . . . . ?
C1 P1 C8 C15 161.78(9) . . . . ?
C1 P1 C2 C3 92.47(10) . . . . ?
C1 P1 C2 C7 -84.16(15) . . . . ?
C4 C3 C2 P1 -176.52(11) . . . . ?
C4 C3 C2 C7 0.6(2) . . . . ?
C2 P1 C8 O2 23.62(9) . . . . ?
C2 P1 C8 C9 141.64(10) . . . . ?
C2 P1 C8 C15 -92.24(9) . . . . ?
C2 P1 C1 F2 -47.25(12) . . . . ?
C2 P1 C1 F1 68.96(11) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C7 C6 C5 -0.1(2) . . . . ?
C16A C15A C20A C19A 0.8(2) . . . . ?
C16A C17A C18A C19A 0.3(3) . . . . ?
C7A C6A C5A C4A 0.5(3) . . . . ?
C17A C18A C19A C20A -0.1(3) . . . . ?
C7 C6 C5 C4 0.3(3) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C20A C15A C16A C17A -0.6(2) . . . . ?
C4A C3A C2A P1A 178.69(11) . . . . ?
C4A C3A C2A C7A 0.6(2) . . . . ?
C14A C9A C8A P1A 138.07(11) . . . . ?
C14A C9A C8A O2A 22.56(15) . . . . ?
C14A C9A C8A C15A -97.94(14) . . . . ?
C14A C9A C10A C11A 0.8(2) . . . . ?
C20 C15 C16 C17 -0.6(2) . . . . ?
C13A C12A C11A C10A -0.5(3) . . . . ?
C11A C12A C13A C14A 0.6(3) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C13 C12 C11 C10 0.6(3) . . . . ?

_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_sv948
_database_code_depnum_ccdc_archive 'CCDC 2061884'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2021-02-08 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F4 P S'
_chemical_formula_sum            'C20 H15 F4 P S'
_chemical_formula_weight         394.35
_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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   9.0837(10)
_cell_length_b                   22.765(2)
_cell_length_c                   9.4866(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.427(3)
_cell_angle_gamma                90
_cell_volume                     1741.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1588
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.546
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0630 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.8658.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16693
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         1.789
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3822
_reflns_number_total             5301
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.5679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_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
S1 S 0.52669(7) 0.57312(2) 0.06289(5) 0.01860(12) Uani 1 1 d . . . . .
P1 P 0.62773(6) 0.63578(2) 0.39154(5) 0.01222(11) Uani 1 1 d . . . . .
F1 F 0.52488(16) 0.51645(5) 0.29918(14) 0.0229(3) Uani 1 1 d . . . . .
F2 F 0.77021(15) 0.53541(5) 0.32414(13) 0.0217(3) Uani 1 1 d . . . . .
F3 F 0.52486(17) 0.74968(5) 0.40951(14) 0.0246(3) Uani 1 1 d . . . . .
F4 F 0.60063(17) 0.69725(5) 0.62683(14) 0.0255(3) Uani 1 1 d . . . . .
C1 C 0.6156(3) 0.56009(8) 0.2745(2) 0.0155(4) Uani 1 1 d . . . . .
C2 C 0.6136(2) 0.64402(8) 0.0923(2) 0.0148(4) Uani 1 1 d . . . . .
C3 C 0.6660(2) 0.67257(8) 0.2394(2) 0.0134(4) Uani 1 1 d . . . . .
C4 C 0.7426(3) 0.72753(9) 0.2593(2) 0.0166(4) Uani 1 1 d . . . . .
H4 H 0.7818 0.7472 0.3584 0.020 Uiso 1 1 calc R U . . .
C5 C 0.7624(3) 0.75389(9) 0.1367(2) 0.0206(4) Uani 1 1 d . . . . .
H5 H 0.8159 0.7909 0.1531 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7038(3) 0.72602(9) -0.0098(2) 0.0213(4) Uani 1 1 d . . . . .
H6 H 0.7133 0.7447 -0.0948 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6315(3) 0.67102(9) -0.0317(2) 0.0200(4) Uani 1 1 d . . . . .
H7 H 0.5941 0.6515 -0.1309 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4116(2) 0.62705(8) 0.3512(2) 0.0142(4) Uani 1 1 d . . . . .
C9 C 0.2851(3) 0.64751(9) 0.2072(2) 0.0184(4) Uani 1 1 d . . . . .
H9 H 0.3124 0.6644 0.1306 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1200(3) 0.64336(9) 0.1750(3) 0.0234(4) Uani 1 1 d . . . . .
H10 H 0.0351 0.6578 0.0774 0.028 Uiso 1 1 calc R U . . .
C11 C 0.0787(3) 0.61806(10) 0.2855(3) 0.0253(5) Uani 1 1 d . . . . .
H11 H -0.0342 0.6150 0.2633 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2038(3) 0.59724(10) 0.4292(3) 0.0237(5) Uani 1 1 d . . . . .
H12 H 0.1757 0.5797 0.5045 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3688(3) 0.60205(9) 0.4627(2) 0.0187(4) Uani 1 1 d . . . . .
H13 H 0.4533 0.5884 0.5615 0.022 Uiso 1 1 calc R U . . .
C14 C 0.7984(2) 0.60569(8) 0.5718(2) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.7791(3) 0.55573(9) 0.6475(2) 0.0192(4) Uani 1 1 d . . . . .
H15 H 0.6747 0.5365 0.6057 0.023 Uiso 1 1 calc R U . . .
C16 C 0.9119(3) 0.53416(9) 0.7836(2) 0.0233(5) Uani 1 1 d . . . . .
H16 H 0.8972 0.5009 0.8362 0.028 Uiso 1 1 calc R U . . .
C17 C 1.0660(3) 0.56104(10) 0.8430(2) 0.0244(5) Uani 1 1 d . . . . .
H17 H 1.1572 0.5458 0.9351 0.029 Uiso 1 1 calc R U . . .
C18 C 1.0866(3) 0.61024(10) 0.7677(2) 0.0241(5) Uani 1 1 d . . . . .
H18 H 1.1922 0.6285 0.8080 0.029 Uiso 1 1 calc R U . . .
C19 C 0.9537(3) 0.63298(9) 0.6335(2) 0.0194(4) Uani 1 1 d . . . . .
H19 H 0.9682 0.6671 0.5836 0.023 Uiso 1 1 calc R U . . .
C20 C 0.6415(3) 0.70915(9) 0.5057(2) 0.0173(4) Uani 1 1 d . . . . .
H20 H 0.7556 0.7261 0.5499 0.021 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
S1 C1 1.8098(19) . ?
S1 C2 1.762(2) . ?
P1 C1 2.025(2) . ?
P1 C3 1.8354(18) . ?
P1 C8 1.830(2) . ?
P1 C14 1.8318(19) . ?
P1 C20 1.963(2) . ?
F1 C1 1.378(2) . ?
F2 C1 1.378(2) . ?
F3 C20 1.384(2) . ?
F4 C20 1.387(2) . ?
C2 C3 1.408(2) . ?
C2 C7 1.402(3) . ?
C3 C4 1.402(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 C13 1.404(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(3) . ?
C14 C19 1.399(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(3) . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 92.06(9) . . ?
C3 P1 C1 86.50(8) . . ?
C3 P1 C20 93.37(8) . . ?
C8 P1 C1 90.64(8) . . ?
C8 P1 C3 117.32(9) . . ?
C8 P1 C14 121.31(9) . . ?
C8 P1 C20 89.82(9) . . ?
C14 P1 C1 90.16(8) . . ?
C14 P1 C3 121.30(9) . . ?
C14 P1 C20 89.52(9) . . ?
C20 P1 C1 179.53(9) . . ?
S1 C1 P1 110.64(10) . . ?
F1 C1 S1 108.08(13) . . ?
F1 C1 P1 113.92(12) . . ?
F2 C1 S1 108.07(12) . . ?
F2 C1 P1 111.71(13) . . ?
F2 C1 F1 104.07(15) . . ?
C3 C2 S1 120.13(14) . . ?
C7 C2 S1 119.07(15) . . ?
C7 C2 C3 120.79(18) . . ?
C2 C3 P1 117.94(14) . . ?
C4 C3 P1 124.29(14) . . ?
C4 C3 C2 117.77(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.28(18) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(19) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.92(18) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.09(18) . . ?
C6 C7 H7 120.0 . . ?
C9 C8 P1 119.13(14) . . ?
C9 C8 C13 118.89(18) . . ?
C13 C8 P1 121.95(15) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.60(19) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.34(19) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.31(19) . . ?
C12 C13 H13 119.8 . . ?
C15 C14 P1 122.06(16) . . ?
C15 C14 C19 119.16(18) . . ?
C19 C14 P1 118.76(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.26(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.06(19) . . ?
C18 C19 H19 120.0 . . ?
P1 C20 H20 110.5 . . ?
F3 C20 P1 111.62(13) . . ?
F3 C20 F4 105.14(15) . . ?
F3 C20 H20 110.5 . . ?
F4 C20 P1 108.52(13) . . ?
F4 C20 H20 110.5 . . ?

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
S1 C2 C3 P1 -4.1(2) . . . . ?
S1 C2 C3 C4 176.54(15) . . . . ?
S1 C2 C7 C6 -178.19(16) . . . . ?
P1 C3 C4 C5 -177.62(16) . . . . ?
P1 C8 C9 C10 -177.84(16) . . . . ?
P1 C8 C13 C12 178.70(16) . . . . ?
P1 C14 C15 C16 179.69(16) . . . . ?
P1 C14 C19 C18 -178.28(16) . . . . ?
C1 S1 C2 C3 -19.33(17) . . . . ?
C1 S1 C2 C7 159.83(17) . . . . ?
C1 P1 C3 C2 22.38(16) . . . . ?
C1 P1 C3 C4 -158.26(18) . . . . ?
C1 P1 C8 C9 -85.36(16) . . . . ?
C1 P1 C8 C13 96.65(17) . . . . ?
C1 P1 C14 C15 -61.86(17) . . . . ?
C1 P1 C14 C19 116.82(16) . . . . ?
C2 S1 C1 P1 32.80(11) . . . . ?
C2 S1 C1 F1 158.15(13) . . . . ?
C2 S1 C1 F2 -89.79(13) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 P1 C8 C9 1.03(19) . . . . ?
C3 P1 C8 C13 -176.96(15) . . . . ?
C3 P1 C14 C15 -147.86(15) . . . . ?
C3 P1 C14 C19 30.82(19) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -2.5(3) . . . . ?
C5 C6 C7 C2 1.6(3) . . . . ?
C7 C2 C3 P1 176.79(15) . . . . ?
C7 C2 C3 C4 -2.6(3) . . . . ?
C8 P1 C3 C2 -66.53(18) . . . . ?
C8 P1 C3 C4 112.83(18) . . . . ?
C8 P1 C14 C15 29.0(2) . . . . ?
C8 P1 C14 C19 -152.33(15) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
C11 C12 C13 C8 -1.1(3) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C14 P1 C3 C2 110.44(16) . . . . ?
C14 P1 C3 C4 -70.2(2) . . . . ?
C14 P1 C8 C9 -175.93(14) . . . . ?
C14 P1 C8 C13 6.1(2) . . . . ?
C14 C15 C16 C17 -1.8(3) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C14 -1.1(3) . . . . ?
C19 C14 C15 C16 1.0(3) . . . . ?
C20 P1 C3 C2 -158.08(16) . . . . ?
C20 P1 C3 C4 21.28(18) . . . . ?
C20 P1 C8 C9 94.74(16) . . . . ?
C20 P1 C8 C13 -83.25(17) . . . . ?
C20 P1 C14 C15 118.48(17) . . . . ?
C20 P1 C14 C19 -62.83(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
