# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_FACEs
_database_code_depnum_ccdc_archive 'CCDC 1884116'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_vrf_PLAT214_I                   
;
PROBLEM: Atom F3A       (Anion/Solvent) ADP max/min Ratio        6.4 prolat
RESPONSE: partially disordered PF6 anion accounts for the poor ADP
 max/min parameter
;
_vrf_PLAT971_I                   
;
PROBLEM: Check Calcd Resid. Dens.  0.86A   From Au2             3.57 eA-3  
RESPONSE: high residual electron density position near Au cations
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C48 H44 Au2 N4 P2, C36 H44 O10, C4 H10 O, 2(F6 P)'
_chemical_formula_sum            'C88 H98 Au2 F12 N4 O11 P4'
_chemical_formula_weight         2133.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Au Au -4.4197 7.2980 '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'

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

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

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

_cell_length_a                   8.8880(3)
_cell_length_b                   12.0830(5)
_cell_length_c                   21.1375(7)
_cell_angle_alpha                77.868(2)
_cell_angle_beta                 84.721(2)
_cell_angle_gamma                75.319(2)
_cell_volume                     2145.08(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7680
_cell_measurement_theta_min      3.815
_cell_measurement_theta_max      68.988

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    7.800
_shelx_estimated_absorpt_T_min   0.130
_shelx_estimated_absorpt_T_max   0.430
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1303
_exptl_absorpt_correction_T_max  0.4304
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   'SADABS v2.05(Bruker, 2010)'


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and amega scans'
_diffrn_detector_area_resol_mean .83
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42232
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.140
_diffrn_reflns_theta_max         67.621
_diffrn_reflns_theta_full        67.621
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             7522
_reflns_number_gt                6986
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
 All non-hydrogen atoms were located in Fourier electron density maps and 
 refined using anisotropic displacement parameters.  Both the PF6 and 
 diethyl ether fragments are disordered.  The Et2O molecule is positioned
 close to an inversion center and and refined with 50% occupancy.  The PF6
 was modeled with 2-component disorder with 70:30 occupancy.

 All hydrogen atoms were positioned in calculated sites using Ueq = 1.2 x Uiso
 of the attached C atom (1.5 x Uiso for methyl groups). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+8.1933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7522
_refine_ls_number_parameters     628
_refine_ls_number_restraints     99
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.095
_refine_ls_shift/su_mean         0.002

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
Au2 Au 1.00128(2) 0.76797(2) 0.24420(2) 0.03142(5) Uani 1 1 d . . . . .
P2 P 1.01686(14) 0.66483(11) 0.34856(5) 0.0313(3) Uani 1 1 d . . . . .
P3 P 0.14518(17) 0.78248(15) 0.71140(7) 0.0475(4) Uani 1 1 d . . . . .
F1 F 0.2896(6) 0.7693(5) 0.7517(3) 0.0523(16) Uani 0.7 1 d D U P A 1
F2 F -0.0057(6) 0.8120(6) 0.6676(2) 0.0654(16) Uani 0.7 1 d D U P A 1
F3 F 0.0726(7) 0.9128(5) 0.7233(4) 0.079(2) Uani 0.7 1 d D U P A 1
F4 F 0.2341(8) 0.8326(10) 0.6465(3) 0.118(3) Uani 0.7 1 d D U P A 1
F5 F 0.2044(9) 0.6621(7) 0.6941(5) 0.122(3) Uani 0.7 1 d D U P A 1
F6 F 0.0487(8) 0.7389(6) 0.7724(3) 0.082(2) Uani 0.7 1 d D U P A 1
O1 O 0.9315(4) 1.3464(3) 0.01837(16) 0.0338(7) Uani 1 1 d . . . . .
O2 O 0.6225(4) 1.3231(3) 0.06484(15) 0.0339(7) Uani 1 1 d . . . . .
O3 O 0.3934(4) 1.2172(3) 0.15602(16) 0.0362(8) Uani 1 1 d . . . . .
O4 O 0.4279(4) 0.9772(3) 0.23156(16) 0.0358(8) Uani 1 1 d . . . . .
O5 O 0.5545(4) 0.7799(3) 0.17451(17) 0.0394(8) Uani 1 1 d . . . . .
O11 O 0.417(3) 1.034(2) 0.5114(12) 0.201(10) Uani 0.5 1 d . . P B -1
N3 N 1.1072(4) 0.8311(3) 0.10366(16) 0.0253(8) Uani 1 1 d . . . . .
N4 N 0.8927(4) 0.9529(3) 0.12481(16) 0.0266(8) Uani 1 1 d . . . . .
C6 C 0.8540(5) 1.0819(4) 0.0142(2) 0.0261(9) Uani 1 1 d . . . . .
H6 H 0.7592 1.1347 0.0232 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9308(5) 0.9894(4) 0.0603(2) 0.0256(9) Uani 1 1 d . . . . .
C8 C 1.0698(5) 0.9111(4) 0.0461(2) 0.0261(9) Uani 1 1 d . . . . .
C10 C 0.9996(5) 0.8584(3) 0.15031(18) 0.0223(8) Uani 1 1 d . . . . .
C11 C 1.2441(6) 0.7332(4) 0.1094(2) 0.0325(10) Uani 1 1 d . . . . .
H11A H 1.3375 0.7617 0.1105 0.049 Uiso 1 1 calc R U . . .
H11B H 1.2531 0.6951 0.0721 0.049 Uiso 1 1 calc R U . . .
H11C H 1.2336 0.6770 0.1494 0.049 Uiso 1 1 calc R U . . .
C12 C 0.7506(5) 1.0087(4) 0.1587(2) 0.0324(10) Uani 1 1 d . . . . .
H12A H 0.7379 1.0934 0.1491 0.049 Uiso 1 1 calc R U . . .
H12B H 0.7591 0.9799 0.2055 0.049 Uiso 1 1 calc R U . . .
H12C H 0.6601 0.9898 0.1442 0.049 Uiso 1 1 calc R U . . .
C31 C 0.8350(6) 0.6293(5) 0.3826(2) 0.0378(12) Uani 1 1 d . . . . .
C32 C 0.7908(7) 0.5376(5) 0.3679(3) 0.0483(14) Uani 1 1 d . . . . .
H32 H 0.8604 0.4879 0.3431 0.058 Uiso 1 1 calc R U . . .
C33 C 0.6474(8) 0.5158(6) 0.3883(3) 0.0617(17) Uani 1 1 d . . . . .
H33 H 0.6182 0.4521 0.3771 0.074 Uiso 1 1 calc R U . . .
C34 C 0.5488(8) 0.5853(7) 0.4241(3) 0.068(2) Uani 1 1 d . . . . .
H34 H 0.4499 0.5705 0.4381 0.081 Uiso 1 1 calc R U . . .
C35 C 0.5900(9) 0.6770(9) 0.4405(4) 0.084(3) Uani 1 1 d . . . . .
H35 H 0.5201 0.7254 0.4659 0.100 Uiso 1 1 calc R U . . .
C36 C 0.7358(8) 0.6993(7) 0.4197(4) 0.0684(19) Uani 1 1 d . . . . .
H36 H 0.7656 0.7624 0.4313 0.082 Uiso 1 1 calc R U . . .
C37 C 1.0721(6) 0.7417(4) 0.4046(2) 0.0341(11) Uani 1 1 d . . . . .
C38 C 1.1213(6) 0.6833(5) 0.4663(2) 0.0398(12) Uani 1 1 d . . . . .
H38 H 1.1314 0.6016 0.4789 0.048 Uiso 1 1 calc R U . . .
C39 C 1.1551(7) 0.7454(5) 0.5088(3) 0.0465(14) Uani 1 1 d . . . . .
H39 H 1.1868 0.7063 0.5510 0.056 Uiso 1 1 calc R U . . .
C40 C 1.1430(8) 0.8637(5) 0.4903(3) 0.0514(15) Uani 1 1 d . . . . .
H40 H 1.1648 0.9061 0.5200 0.062 Uiso 1 1 calc R U . . .
C41 C 1.0991(8) 0.9210(5) 0.4281(3) 0.0531(16) Uani 1 1 d . . . . .
H41 H 1.0936 1.0020 0.4148 0.064 Uiso 1 1 calc R U . . .
C42 C 1.0633(7) 0.8588(4) 0.3857(2) 0.0404(13) Uani 1 1 d . . . . .
H42 H 1.0324 0.8977 0.3433 0.049 Uiso 1 1 calc R U . . .
C43 C 1.1603(6) 0.5263(5) 0.3533(2) 0.0372(11) Uani 1 1 d . . . . .
C44 C 1.2805(7) 0.5191(5) 0.3068(3) 0.0453(13) Uani 1 1 d . . . . .
H44 H 1.2841 0.5843 0.2731 0.054 Uiso 1 1 calc R U . . .
C45 C 1.3958(8) 0.4166(6) 0.3094(3) 0.0594(17) Uani 1 1 d . . . . .
H45 H 1.4788 0.4117 0.2776 0.071 Uiso 1 1 calc R U . . .
C46 C 1.3897(9) 0.3220(6) 0.3581(3) 0.0679(19) Uani 1 1 d . . . . .
H46 H 1.4698 0.2523 0.3604 0.082 Uiso 1 1 calc R U . . .
C47 C 1.2671(9) 0.3281(6) 0.4037(3) 0.0648(19) Uani 1 1 d . . . . .
H47 H 1.2612 0.2619 0.4363 0.078 Uiso 1 1 calc R U . . .
C48 C 1.1538(7) 0.4302(5) 0.4017(3) 0.0465(14) Uani 1 1 d . . . . .
H48 H 1.0710 0.4349 0.4336 0.056 Uiso 1 1 calc R U . . .
C61 C 0.8805(6) 1.3215(4) 0.0853(2) 0.0356(11) Uani 1 1 d . . . . .
H61A H 0.9434 1.3488 0.1124 0.043 Uiso 1 1 calc R U . . .
H61B H 0.8936 1.2364 0.1002 0.043 Uiso 1 1 calc R U . . .
C62 C 0.7120(6) 1.3832(4) 0.0916(2) 0.0374(11) Uani 1 1 d . . . . .
H62A H 0.6806 1.3834 0.1377 0.045 Uiso 1 1 calc R U . . .
H62B H 0.6949 1.4651 0.0680 0.045 Uiso 1 1 calc R U . . .
C63 C 0.4594(6) 1.3684(5) 0.0727(2) 0.0394(12) Uani 1 1 d . . . . .
H63A H 0.4056 1.3394 0.0430 0.047 Uiso 1 1 calc R U . . .
H63B H 0.4361 1.4545 0.0600 0.047 Uiso 1 1 calc R U . . .
C64 C 0.3945(6) 1.3365(5) 0.1405(3) 0.0411(13) Uani 1 1 d . . . . .
H64A H 0.4584 1.3537 0.1715 0.049 Uiso 1 1 calc R U . . .
H64B H 0.2870 1.3844 0.1445 0.049 Uiso 1 1 calc R U . . .
C65 C 0.3483(6) 1.1846(5) 0.2220(2) 0.0400(12) Uani 1 1 d . . . . .
H65A H 0.2616 1.2471 0.2342 0.048 Uiso 1 1 calc R U . . .
H65B H 0.4369 1.1760 0.2493 0.048 Uiso 1 1 calc R U . . .
C66 C 0.2975(6) 1.0720(5) 0.2350(2) 0.0388(12) Uani 1 1 d . . . . .
H66A H 0.2455 1.0608 0.2786 0.047 Uiso 1 1 calc R U . . .
H66B H 0.2218 1.0752 0.2027 0.047 Uiso 1 1 calc R U . . .
C67 C 0.3864(6) 0.8692(5) 0.2522(3) 0.0430(12) Uani 1 1 d . . . . .
H67A H 0.2992 0.8671 0.2268 0.052 Uiso 1 1 calc R U . . .
H67B H 0.3520 0.8597 0.2985 0.052 Uiso 1 1 calc R U . . .
C68 C 0.5249(6) 0.7720(5) 0.2425(2) 0.0418(12) Uani 1 1 d . . . . .
H68A H 0.6166 0.7799 0.2629 0.050 Uiso 1 1 calc R U . . .
H68B H 0.5030 0.6956 0.2625 0.050 Uiso 1 1 calc R U . . .
C69 C 0.6910(6) 0.7106(4) 0.1545(2) 0.0357(11) Uani 1 1 d . . . . .
C70 C 0.7825(6) 0.6184(4) 0.1943(2) 0.0375(11) Uani 1 1 d . . . . .
H70 H 0.7511 0.5978 0.2385 0.045 Uiso 1 1 calc R U . . .
C71 C 0.9223(6) 0.5545(4) 0.1698(2) 0.0395(12) Uani 1 1 d . . . . .
H71 H 0.9840 0.4899 0.1975 0.047 Uiso 1 1 calc R U . . .
C72 C 0.9709(6) 0.5840(4) 0.1065(2) 0.0342(11) Uani 1 1 d . . . . .
H72 H 1.0671 0.5417 0.0907 0.041 Uiso 1 1 calc R U . . .
C73 C 0.8758(5) 0.6789(4) 0.0645(2) 0.0311(10) Uani 1 1 d . . . . .
C74 C 0.9230(6) 0.7132(4) -0.0020(2) 0.0328(10) Uani 1 1 d . . . . .
C75 C 0.8259(6) 0.7983(4) -0.0431(2) 0.0350(11) Uani 1 1 d . . . . .
H75 H 0.8556 0.8171 -0.0876 0.042 Uiso 1 1 calc R U . . .
C76 C 0.6818(6) 0.8581(5) -0.0191(3) 0.0399(12) Uani 1 1 d . . . . .
H76 H 0.6146 0.9169 -0.0480 0.048 Uiso 1 1 calc R U . . .
C77 C 0.6371(6) 0.8332(4) 0.0445(3) 0.0372(11) Uani 1 1 d . . . . .
H77 H 0.5415 0.8768 0.0601 0.045 Uiso 1 1 calc R U . . .
C78 C 0.7329(6) 0.7424(4) 0.0876(2) 0.0330(10) Uani 1 1 d . . . . .
C87 C 0.4724(19) 1.0155(13) 0.3979(8) 0.067(4) Uani 0.5 1 d . . P B -1
H87A H 0.4854 0.9357 0.3912 0.101 Uiso 0.5 1 calc R U P B -1
H87B H 0.5243 1.0592 0.3620 0.101 Uiso 0.5 1 calc R U P B -1
H87C H 0.3612 1.0538 0.3999 0.101 Uiso 0.5 1 calc R U P B -1
C88 C 0.501(3) 1.0201(17) 0.5654(10) 0.101(7) Uani 0.5 1 d . . P B -1
H88A H 0.5475 1.0873 0.5621 0.121 Uiso 0.5 1 calc R U P B -1
H88B H 0.5857 0.9483 0.5685 0.121 Uiso 0.5 1 calc R U P B -1
C89 C 0.391(2) 1.0113(14) 0.6255(9) 0.079(5) Uani 0.5 1 d . . P B -1
H89A H 0.3078 1.0829 0.6222 0.118 Uiso 0.5 1 calc R U P B -1
H89B H 0.4497 1.0012 0.6642 0.118 Uiso 0.5 1 calc R U P B -1
H89C H 0.3458 0.9443 0.6286 0.118 Uiso 0.5 1 calc R U P B -1
C90 C 0.5505(17) 1.0119(15) 0.4671(9) 0.099(4) Uani 0.5 1 d . . P B -1
H90A H 0.6209 0.9347 0.4823 0.119 Uiso 0.5 1 calc R U P B -1
H90B H 0.6096 1.0728 0.4620 0.119 Uiso 0.5 1 calc R U P B -1
F1A F 0.2958(13) 0.7921(11) 0.7465(6) 0.048(3) Uani 0.3 1 d D U P A 2
F2A F 0.0163(12) 0.7370(11) 0.6822(6) 0.058(3) Uani 0.3 1 d D U P A 2
F3A F 0.086(2) 0.9016(10) 0.6896(6) 0.147(7) Uani 0.3 1 d D U P A 2
F4A F 0.2523(11) 0.7609(7) 0.6507(4) 0.029(2) Uani 0.3 1 d D U P A 2
F5A F 0.2186(13) 0.6336(7) 0.7387(4) 0.046(3) Uani 0.3 1 d D U P A 2
F6A F 0.0507(12) 0.7853(17) 0.7779(5) 0.107(7) Uani 0.3 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
Au2 C10 2.054(4) . ?
Au2 P2 2.2916(11) . ?
P2 C37 1.819(5) . ?
P2 C43 1.819(5) . ?
P2 C31 1.823(5) . ?
P3 F3A 1.394(11) . ?
P3 F5 1.525(7) . ?
P3 F4A 1.552(8) . ?
P3 F6 1.554(6) . ?
P3 F1 1.561(6) . ?
P3 F6A 1.572(9) . ?
P3 F4 1.601(7) . ?
P3 F3 1.607(6) . ?
P3 F2A 1.608(11) . ?
P3 F2 1.622(5) . ?
P3 F1A 1.629(12) . ?
P3 F5A 1.741(9) . ?
O1 C74 1.364(6) 2_775 ?
O1 C61 1.438(6) . ?
O2 C63 1.421(6) . ?
O2 C62 1.424(6) . ?
O3 C64 1.412(7) . ?
O3 C65 1.418(6) . ?
O4 C67 1.416(6) . ?
O4 C66 1.417(6) . ?
O5 C69 1.376(6) . ?
O5 C68 1.425(6) . ?
O11 C88 1.38(3) . ?
O11 C90 1.45(3) . ?
N3 C10 1.341(5) . ?
N3 C8 1.393(5) . ?
N3 C11 1.460(6) . ?
N4 C10 1.335(5) . ?
N4 C7 1.381(5) . ?
N4 C12 1.473(6) . ?
C6 C8 1.385(6) 2_775 ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(6) . ?
C8 C6 1.385(6) 2_775 ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C31 C32 1.365(9) . ?
C31 C36 1.373(9) . ?
C32 C33 1.380(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.349(11) . ?
C33 H33 0.9500 . ?
C34 C35 1.369(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.402(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C42 1.371(7) . ?
C37 C38 1.397(7) . ?
C38 C39 1.380(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.380(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.390(8) . ?
C40 H40 0.9500 . ?
C41 C42 1.388(9) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.381(7) . ?
C43 C48 1.386(8) . ?
C44 C45 1.388(8) . ?
C44 H44 0.9500 . ?
C45 C46 1.377(10) . ?
C45 H45 0.9500 . ?
C46 C47 1.385(11) . ?
C46 H46 0.9500 . ?
C47 C48 1.376(9) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C61 C62 1.502(7) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.504(7) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 C66 1.503(8) . ?
C65 H65A 0.9900 . ?
C65 H65B 0.9900 . ?
C66 H66A 0.9900 . ?
C66 H66B 0.9900 . ?
C67 C68 1.503(7) . ?
C67 H67A 0.9900 . ?
C67 H67B 0.9900 . ?
C68 H68A 0.9900 . ?
C68 H68B 0.9900 . ?
C69 C70 1.372(7) . ?
C69 C78 1.427(7) . ?
C70 C71 1.404(7) . ?
C70 H70 0.9500 . ?
C71 C72 1.369(7) . ?
C71 H71 0.9500 . ?
C72 C73 1.428(6) . ?
C72 H72 0.9500 . ?
C73 C78 1.410(7) . ?
C73 C74 1.435(7) . ?
C74 O1 1.364(6) 2_775 ?
C74 C75 1.366(7) . ?
C75 C76 1.409(7) . ?
C75 H75 0.9500 . ?
C76 C77 1.361(7) . ?
C76 H76 0.9500 . ?
C77 C78 1.416(7) . ?
C77 H77 0.9500 . ?
C87 C90 1.66(2) . ?
C87 H87A 0.9800 . ?
C87 H87B 0.9800 . ?
C87 H87C 0.9800 . ?
C88 C89 1.53(3) . ?
C88 H88A 0.9900 . ?
C88 H88B 0.9900 . ?
C89 H89A 0.9800 . ?
C89 H89B 0.9800 . ?
C89 H89C 0.9800 . ?
C90 H90A 0.9900 . ?
C90 H90B 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
C10 Au2 P2 177.05(12) . . ?
C37 P2 C43 107.1(2) . . ?
C37 P2 C31 105.5(2) . . ?
C43 P2 C31 106.0(2) . . ?
C37 P2 Au2 113.10(16) . . ?
C43 P2 Au2 110.78(16) . . ?
C31 P2 Au2 113.85(16) . . ?
F3A P3 F4A 96.6(6) . . ?
F5 P3 F6 94.2(5) . . ?
F5 P3 F1 93.6(4) . . ?
F6 P3 F1 92.6(3) . . ?
F3A P3 F6A 92.0(8) . . ?
F4A P3 F6A 171.3(7) . . ?
F5 P3 F4 87.5(5) . . ?
F6 P3 F4 176.2(4) . . ?
F1 P3 F4 90.7(3) . . ?
F5 P3 F3 174.3(4) . . ?
F6 P3 F3 87.8(4) . . ?
F1 P3 F3 91.7(3) . . ?
F4 P3 F3 90.2(5) . . ?
F3A P3 F2A 97.7(9) . . ?
F4A P3 F2A 88.8(5) . . ?
F6A P3 F2A 91.9(7) . . ?
F5 P3 F2 92.0(4) . . ?
F6 P3 F2 90.4(3) . . ?
F1 P3 F2 173.4(4) . . ?
F4 P3 F2 86.2(3) . . ?
F3 P3 F2 82.6(3) . . ?
F3A P3 F1A 97.3(9) . . ?
F4A P3 F1A 88.5(5) . . ?
F6A P3 F1A 88.6(6) . . ?
F2A P3 F1A 165.0(6) . . ?
F3A P3 F5A 179.7(9) . . ?
F4A P3 F5A 83.6(4) . . ?
F6A P3 F5A 87.9(7) . . ?
F2A P3 F5A 82.1(6) . . ?
F1A P3 F5A 82.9(5) . . ?
C74 O1 C61 116.7(4) 2_775 . ?
C63 O2 C62 113.0(4) . . ?
C64 O3 C65 110.9(4) . . ?
C67 O4 C66 111.1(4) . . ?
C69 O5 C68 117.1(4) . . ?
C88 O11 C90 96.0(19) . . ?
C10 N3 C8 109.7(3) . . ?
C10 N3 C11 127.2(3) . . ?
C8 N3 C11 123.1(4) . . ?
C10 N4 C7 110.1(3) . . ?
C10 N4 C12 125.8(4) . . ?
C7 N4 C12 124.0(4) . . ?
C8 C6 C7 113.0(4) 2_775 . ?
C8 C6 H6 123.5 2_775 . ?
C7 C6 H6 123.5 . . ?
N4 C7 C6 130.7(4) . . ?
N4 C7 C8 106.3(4) . . ?
C6 C7 C8 123.0(4) . . ?
C6 C8 N3 130.3(4) 2_775 . ?
C6 C8 C7 124.0(4) 2_775 . ?
N3 C8 C7 105.7(4) . . ?
N4 C10 N3 108.2(3) . . ?
N4 C10 Au2 126.7(3) . . ?
N3 C10 Au2 125.1(3) . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C32 C31 C36 119.1(6) . . ?
C32 C31 P2 120.5(4) . . ?
C36 C31 P2 120.2(5) . . ?
C31 C32 C33 121.4(6) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C34 C33 C32 119.6(7) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 120.6(6) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 119.8(7) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 119.5(8) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C42 C37 C38 120.1(5) . . ?
C42 C37 P2 119.0(4) . . ?
C38 C37 P2 120.9(4) . . ?
C39 C38 C37 119.4(5) . . ?
C39 C38 H38 120.3 . . ?
C37 C38 H38 120.3 . . ?
C40 C39 C38 120.5(5) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 120.0(6) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C42 C41 C40 119.5(5) . . ?
C42 C41 H41 120.3 . . ?
C40 C41 H41 120.3 . . ?
C37 C42 C41 120.4(5) . . ?
C37 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C44 C43 C48 119.8(5) . . ?
C44 C43 P2 117.7(4) . . ?
C48 C43 P2 122.5(4) . . ?
C43 C44 C45 120.0(6) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 119.9(6) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 120.1(6) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C48 C47 C46 120.0(6) . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
C47 C48 C43 120.1(6) . . ?
C47 C48 H48 119.9 . . ?
C43 C48 H48 119.9 . . ?
O1 C61 C62 108.4(4) . . ?
O1 C61 H61A 110.0 . . ?
C62 C61 H61A 110.0 . . ?
O1 C61 H61B 110.0 . . ?
C62 C61 H61B 110.0 . . ?
H61A C61 H61B 108.4 . . ?
O2 C62 C61 108.0(4) . . ?
O2 C62 H62A 110.1 . . ?
C61 C62 H62A 110.1 . . ?
O2 C62 H62B 110.1 . . ?
C61 C62 H62B 110.1 . . ?
H62A C62 H62B 108.4 . . ?
O2 C63 C64 114.2(4) . . ?
O2 C63 H63A 108.7 . . ?
C64 C63 H63A 108.7 . . ?
O2 C63 H63B 108.7 . . ?
C64 C63 H63B 108.7 . . ?
H63A C63 H63B 107.6 . . ?
O3 C64 C63 111.0(4) . . ?
O3 C64 H64A 109.4 . . ?
C63 C64 H64A 109.4 . . ?
O3 C64 H64B 109.4 . . ?
C63 C64 H64B 109.4 . . ?
H64A C64 H64B 108.0 . . ?
O3 C65 C66 111.9(4) . . ?
O3 C65 H65A 109.2 . . ?
C66 C65 H65A 109.2 . . ?
O3 C65 H65B 109.2 . . ?
C66 C65 H65B 109.2 . . ?
H65A C65 H65B 107.9 . . ?
O4 C66 C65 110.1(4) . . ?
O4 C66 H66A 109.6 . . ?
C65 C66 H66A 109.6 . . ?
O4 C66 H66B 109.6 . . ?
C65 C66 H66B 109.6 . . ?
H66A C66 H66B 108.2 . . ?
O4 C67 C68 109.1(4) . . ?
O4 C67 H67A 109.9 . . ?
C68 C67 H67A 109.9 . . ?
O4 C67 H67B 109.9 . . ?
C68 C67 H67B 109.9 . . ?
H67A C67 H67B 108.3 . . ?
O5 C68 C67 107.3(4) . . ?
O5 C68 H68A 110.2 . . ?
C67 C68 H68A 110.2 . . ?
O5 C68 H68B 110.2 . . ?
C67 C68 H68B 110.2 . . ?
H68A C68 H68B 108.5 . . ?
C70 C69 O5 124.2(5) . . ?
C70 C69 C78 121.4(5) . . ?
O5 C69 C78 114.4(4) . . ?
C69 C70 C71 120.2(5) . . ?
C69 C70 H70 119.9 . . ?
C71 C70 H70 119.9 . . ?
C72 C71 C70 120.8(5) . . ?
C72 C71 H71 119.6 . . ?
C70 C71 H71 119.6 . . ?
C71 C72 C73 119.5(5) . . ?
C71 C72 H72 120.2 . . ?
C73 C72 H72 120.2 . . ?
C78 C73 C72 120.6(4) . . ?
C78 C73 C74 118.1(4) . . ?
C72 C73 C74 121.2(4) . . ?
O1 C74 C75 125.5(4) 2_775 . ?
O1 C74 C73 113.8(4) 2_775 . ?
C75 C74 C73 120.7(4) . . ?
C74 C75 C76 119.9(5) . . ?
C74 C75 H75 120.1 . . ?
C76 C75 H75 120.1 . . ?
C77 C76 C75 121.2(5) . . ?
C77 C76 H76 119.4 . . ?
C75 C76 H76 119.4 . . ?
C76 C77 C78 120.1(5) . . ?
C76 C77 H77 120.0 . . ?
C78 C77 H77 120.0 . . ?
C73 C78 C77 119.9(4) . . ?
C73 C78 C69 117.4(4) . . ?
C77 C78 C69 122.7(4) . . ?
C90 C87 H87A 109.5 . . ?
C90 C87 H87B 109.5 . . ?
H87A C87 H87B 109.5 . . ?
C90 C87 H87C 109.5 . . ?
H87A C87 H87C 109.5 . . ?
H87B C87 H87C 109.5 . . ?
O11 C88 C89 109(2) . . ?
O11 C88 H88A 109.9 . . ?
C89 C88 H88A 109.9 . . ?
O11 C88 H88B 110.0 . . ?
C89 C88 H88B 109.9 . . ?
H88A C88 H88B 108.3 . . ?
C88 C89 H89A 109.5 . . ?
C88 C89 H89B 109.5 . . ?
H89A C89 H89B 109.5 . . ?
C88 C89 H89C 109.5 . . ?
H89A C89 H89C 109.5 . . ?
H89B C89 H89C 109.5 . . ?
O11 C90 C87 103.6(13) . . ?
O11 C90 H90A 111.1 . . ?
C87 C90 H90A 111.1 . . ?
O11 C90 H90B 111.0 . . ?
C87 C90 H90B 111.0 . . ?
H90A C90 H90B 109.0 . . ?

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
C10 N4 C7 C6 179.1(5) . . . . ?
C12 N4 C7 C6 1.4(7) . . . . ?
C10 N4 C7 C8 0.2(5) . . . . ?
C12 N4 C7 C8 -177.4(4) . . . . ?
C8 C6 C7 N4 -179.5(4) 2_775 . . . ?
C8 C6 C7 C8 -0.8(7) 2_775 . . . ?
C10 N3 C8 C6 179.9(5) . . . 2_775 ?
C11 N3 C8 C6 -0.5(7) . . . 2_775 ?
C10 N3 C8 C7 -0.5(5) . . . . ?
C11 N3 C8 C7 179.1(4) . . . . ?
N4 C7 C8 C6 179.8(4) . . . 2_775 ?
C6 C7 C8 C6 0.9(8) . . . 2_775 ?
N4 C7 C8 N3 0.1(5) . . . . ?
C6 C7 C8 N3 -178.8(4) . . . . ?
C7 N4 C10 N3 -0.5(5) . . . . ?
C12 N4 C10 N3 177.1(4) . . . . ?
C7 N4 C10 Au2 180.0(3) . . . . ?
C12 N4 C10 Au2 -2.4(6) . . . . ?
C8 N3 C10 N4 0.6(5) . . . . ?
C11 N3 C10 N4 -178.9(4) . . . . ?
C8 N3 C10 Au2 -179.9(3) . . . . ?
C11 N3 C10 Au2 0.6(6) . . . . ?
C37 P2 C31 C32 -155.6(4) . . . . ?
C43 P2 C31 C32 -42.2(5) . . . . ?
Au2 P2 C31 C32 79.9(4) . . . . ?
C37 P2 C31 C36 29.0(5) . . . . ?
C43 P2 C31 C36 142.4(5) . . . . ?
Au2 P2 C31 C36 -95.5(5) . . . . ?
C36 C31 C32 C33 1.5(9) . . . . ?
P2 C31 C32 C33 -174.0(5) . . . . ?
C31 C32 C33 C34 -0.7(9) . . . . ?
C32 C33 C34 C35 -0.1(10) . . . . ?
C33 C34 C35 C36 0.2(12) . . . . ?
C32 C31 C36 C35 -1.4(10) . . . . ?
P2 C31 C36 C35 174.1(6) . . . . ?
C34 C35 C36 C31 0.6(12) . . . . ?
C43 P2 C37 C42 137.6(4) . . . . ?
C31 P2 C37 C42 -109.8(4) . . . . ?
Au2 P2 C37 C42 15.3(5) . . . . ?
C43 P2 C37 C38 -43.1(5) . . . . ?
C31 P2 C37 C38 69.5(5) . . . . ?
Au2 P2 C37 C38 -165.4(4) . . . . ?
C42 C37 C38 C39 2.4(8) . . . . ?
P2 C37 C38 C39 -176.8(4) . . . . ?
C37 C38 C39 C40 -1.1(9) . . . . ?
C38 C39 C40 C41 -1.1(10) . . . . ?
C39 C40 C41 C42 1.8(10) . . . . ?
C38 C37 C42 C41 -1.7(8) . . . . ?
P2 C37 C42 C41 177.6(5) . . . . ?
C40 C41 C42 C37 -0.5(9) . . . . ?
C37 P2 C43 C44 -97.5(4) . . . . ?
C31 P2 C43 C44 150.2(4) . . . . ?
Au2 P2 C43 C44 26.3(5) . . . . ?
C37 P2 C43 C48 81.6(5) . . . . ?
C31 P2 C43 C48 -30.6(5) . . . . ?
Au2 P2 C43 C48 -154.6(4) . . . . ?
C48 C43 C44 C45 -1.2(9) . . . . ?
P2 C43 C44 C45 177.9(5) . . . . ?
C43 C44 C45 C46 0.4(10) . . . . ?
C44 C45 C46 C47 1.3(11) . . . . ?
C45 C46 C47 C48 -2.2(11) . . . . ?
C46 C47 C48 C43 1.4(11) . . . . ?
C44 C43 C48 C47 0.3(9) . . . . ?
P2 C43 C48 C47 -178.8(5) . . . . ?
C74 O1 C61 C62 -172.6(4) 2_775 . . . ?
C63 O2 C62 C61 175.3(4) . . . . ?
O1 C61 C62 O2 73.1(5) . . . . ?
C62 O2 C63 C64 -74.6(6) . . . . ?
C65 O3 C64 C63 173.7(4) . . . . ?
O2 C63 C64 O3 -71.4(6) . . . . ?
C64 O3 C65 C66 162.0(4) . . . . ?
C67 O4 C66 C65 172.1(4) . . . . ?
O3 C65 C66 O4 71.7(5) . . . . ?
C66 O4 C67 C68 175.5(4) . . . . ?
C69 O5 C68 C67 170.1(4) . . . . ?
O4 C67 C68 O5 -68.2(5) . . . . ?
C68 O5 C69 C70 14.6(7) . . . . ?
C68 O5 C69 C78 -165.1(4) . . . . ?
O5 C69 C70 C71 -178.3(5) . . . . ?
C78 C69 C70 C71 1.4(8) . . . . ?
C69 C70 C71 C72 1.1(8) . . . . ?
C70 C71 C72 C73 -1.9(8) . . . . ?
C71 C72 C73 C78 0.1(7) . . . . ?
C71 C72 C73 C74 179.6(5) . . . . ?
C78 C73 C74 O1 174.5(4) . . . 2_775 ?
C72 C73 C74 O1 -4.9(6) . . . 2_775 ?
C78 C73 C74 C75 -5.5(7) . . . . ?
C72 C73 C74 C75 175.1(5) . . . . ?
O1 C74 C75 C76 -176.2(5) 2_775 . . . ?
C73 C74 C75 C76 3.8(7) . . . . ?
C74 C75 C76 C77 0.4(8) . . . . ?
C75 C76 C77 C78 -2.8(8) . . . . ?
C72 C73 C78 C77 -177.4(5) . . . . ?
C74 C73 C78 C77 3.1(7) . . . . ?
C72 C73 C78 C69 2.2(7) . . . . ?
C74 C73 C78 C69 -177.2(4) . . . . ?
C76 C77 C78 C73 0.9(7) . . . . ?
C76 C77 C78 C69 -178.7(5) . . . . ?
C70 C69 C78 C73 -3.0(7) . . . . ?
O5 C69 C78 C73 176.7(4) . . . . ?
C70 C69 C78 C77 176.7(5) . . . . ?
O5 C69 C78 C77 -3.6(7) . . . . ?
C90 O11 C88 C89 -167.3(15) . . . . ?
C88 O11 C90 C87 176.0(16) . . . . ?

_refine_diff_density_max         3.897
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_11rfs05
_database_code_depnum_ccdc_archive 'CCDC 1884122'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H72 F12 N4 O14 P2'
_chemical_formula_weight         1315.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.2760(4)
_cell_length_b                   12.8324(4)
_cell_length_c                   21.9878(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.158(2)
_cell_angle_gamma                90
_cell_volume                     3181.58(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7427
_cell_measurement_theta_min      3.99
_cell_measurement_theta_max      66.43

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             1372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.304
_exptl_absorpt_coefficient_mu    1.494
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42964
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.988
_diffrn_reflns_theta_max         67.713
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5712
_reflns_number_gt                4279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2009)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All non-hydrogen atoms were located in a sequence of difference density maps
 and refined using anisotropic displacement parameters.  The C-C and C-O bonds
 of the ether fragment were restrained with similar distances (esd 0.2 ang). All
 H atoms were placed in calculated positions with Ueq = 1.2 x Uiso (1.5 x 
 Uiso for methyl H atoms).
 
 Refinement with this model resulted in a final R value of near 19%.  
 Significant whole molecule disorder exists for the macrocycle.  
 Additionally, the OH groups were disordered and no H atoms located
 in diff maps.  These H atoms were not included in the model
 since they were ill-defined. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5712
_refine_ls_number_parameters     614
_refine_ls_number_restraints     620
_refine_ls_R_factor_all          0.2134
_refine_ls_R_factor_gt           0.1906
_refine_ls_wR_factor_ref         0.5478
_refine_ls_wR_factor_gt          0.5201
_refine_ls_goodness_of_fit_ref   2.553
_refine_ls_restrained_S_all      2.482
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.6180(3) 0.8646(2) 0.14469(14) 0.1024(10) Uani 1 1 d . U . . .
F1 F 0.5019(7) 0.8162(6) 0.1106(4) 0.134(2) Uani 1 1 d . U . . .
F2 F 0.5325(6) 0.9491(5) 0.1684(3) 0.1092(18) Uani 1 1 d . U . . .
F3 F 0.6342(9) 0.9453(7) 0.0874(3) 0.148(3) Uani 1 1 d . U . . .
F4 F 0.6846(7) 0.7846(6) 0.1064(3) 0.127(2) Uani 1 1 d . U . . .
F5 F 0.7248(8) 0.9083(6) 0.1745(4) 0.142(3) Uani 1 1 d . U . . .
F6 F 0.5876(8) 0.7848(6) 0.1980(3) 0.130(2) Uani 1 1 d . U . . .
O1 O 0.3958(6) 0.5657(6) 0.3022(3) 0.0941(19) Uani 1 1 d . U . . .
O2 O 0.283(3) -0.0299(18) 0.1166(11) 0.163(11) Uani 0.45(2) 1 d . U P A 2
N1 N 0.4587(5) 0.4661(4) 0.1200(2) 0.0558(13) Uani 1 1 d . U . . .
N2 N 0.4294(4) 0.3284(4) 0.0627(2) 0.0470(11) Uani 1 1 d . U . . .
C1 C 0.4805(5) 0.4076(4) -0.0382(2) 0.0444(12) Uani 1 1 d . U . . .
H1 H 0.4686 0.3477 -0.0628 0.053 Uiso 1 1 calc R U . . .
C2 C 0.4643(4) 0.4085(4) 0.0235(2) 0.0426(12) Uani 1 1 d . U . . .
C3 C 0.4839(5) 0.4961(4) 0.0610(2) 0.0446(12) Uani 1 1 d . U . . .
C4 C 0.4267(6) 0.3651(5) 0.1194(3) 0.0564(15) Uani 1 1 d . U . . .
H4 H 0.4054 0.3257 0.1542 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4616(7) 0.5342(5) 0.1742(3) 0.0656(17) Uani 1 1 d . U . . .
H5A H 0.3794 0.5541 0.1850 0.079 Uiso 1 1 calc R U . . .
H5B H 0.5055 0.5988 0.1643 0.079 Uiso 1 1 calc R U . . .
C6 C 0.5211(8) 0.4809(7) 0.2301(3) 0.074(2) Uani 1 1 d . U . . .
H6A H 0.4803 0.4145 0.2393 0.089 Uiso 1 1 calc R U . . .
H6B H 0.6052 0.4655 0.2210 0.089 Uiso 1 1 calc R U . . .
C7 C 0.5134(8) 0.5525(8) 0.2837(3) 0.078(2) Uani 1 1 d . U . . .
H7A H 0.5604 0.5233 0.3178 0.094 Uiso 1 1 calc R U . . .
H7B H 0.5476 0.6211 0.2729 0.094 Uiso 1 1 calc R U . . .
C8 C 0.3995(6) 0.2202(5) 0.0423(3) 0.0537(14) Uani 1 1 d . U . . .
H8A H 0.3364 0.2241 0.0110 0.064 Uiso 1 1 calc R U . . .
H8B H 0.4703 0.1890 0.0231 0.064 Uiso 1 1 calc R U . . .
C9 C 0.3591(6) 0.1507(5) 0.0920(3) 0.0564(15) Uani 1 1 d . U . . .
H9A H 0.2862 0.1795 0.1106 0.068 Uiso 1 1 calc R U . . .
H9B H 0.4210 0.1465 0.1239 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3337(9) 0.0409(6) 0.0665(4) 0.082(2) Uani 1 1 d . U . . .
H10A H 0.2973 -0.0037 0.0981 0.099 Uiso 1 1 calc R U . A 1
H10B H 0.2790 0.0450 0.0313 0.099 Uiso 1 1 calc R U . A 1
O2A O 0.4537(19) -0.0034(14) 0.0470(10) 0.153(8) Uani 0.55(2) 1 d . U P A 1
O3A O 0.7015(9) 0.2695(10) 0.1425(6) 0.060(3) Uani 0.5 1 d D U P B 1
O4A O 0.5622(10) 0.2159(11) 0.2523(8) 0.093(4) Uani 0.5 1 d D U P B 1
O5A O 0.3178(12) 0.2632(10) 0.2405(6) 0.054(3) Uani 0.5 1 d D U P B 1
O6A O 0.8617(8) 0.5244(8) -0.0698(5) 0.067(2) Uani 0.5 1 d D U P B 1
O7A O 0.8079(8) 0.5957(8) -0.1846(4) 0.066(2) Uani 0.5 1 d D U P B 1
C11A C 0.7662(12) 0.3855(12) 0.0679(6) 0.054(3) Uani 0.5 1 d D U P B 1
C12A C 0.780(3) 0.4626(15) 0.1134(11) 0.077(7) Uani 0.5 1 d D U P B 1
H12A H 0.7627 0.4494 0.1549 0.092 Uiso 0.5 1 calc R U P B 1
C13A C 0.822(2) 0.5593(16) 0.0934(9) 0.068(5) Uani 0.5 1 d D U P B 1
H13A H 0.8330 0.6124 0.1230 0.082 Uiso 0.5 1 calc R U P B 1
C14A C 0.8494(14) 0.5837(12) 0.0326(8) 0.068(4) Uani 0.5 1 d D U P B 1
H14A H 0.8761 0.6513 0.0215 0.082 Uiso 0.5 1 calc R U P B 1
C15A C 0.8358(11) 0.5047(11) -0.0113(7) 0.054(3) Uani 0.5 1 d D U P B 1
C16A C 0.7919(10) 0.4059(9) 0.0060(5) 0.055(2) Uani 0.5 1 d D U P B 1
C17A C 0.7833(15) 0.3316(11) -0.0408(7) 0.058(3) Uani 0.5 1 d D U P B 1
H17A H 0.8036 0.3471 -0.0818 0.069 Uiso 0.5 1 calc R U P B 1
C18A C 0.7427(13) 0.2327(10) -0.0228(6) 0.059(3) Uani 0.5 1 d D U P B 1
H18A H 0.7335 0.1800 -0.0528 0.071 Uiso 0.5 1 calc R U P B 1
C19A C 0.7151(11) 0.2087(10) 0.0384(5) 0.055(2) Uani 0.5 1 d D U P B 1
H19A H 0.6882 0.1408 0.0487 0.066 Uiso 0.5 1 calc R U P B 1
C20A C 0.7272(12) 0.2844(10) 0.0839(9) 0.052(3) Uani 0.5 1 d D U P B 1
C21A C 0.6876(13) 0.1681(11) 0.1655(9) 0.066(4) Uani 0.5 1 d D U P B 1
H21A H 0.7596 0.1267 0.1567 0.080 Uiso 0.5 1 calc R U P B 1
H21B H 0.6195 0.1340 0.1451 0.080 Uiso 0.5 1 calc R U P B 1
C22A C 0.6671(16) 0.1703(16) 0.2321(9) 0.083(5) Uani 0.5 1 d D U P B 1
H22A H 0.6692 0.0976 0.2472 0.100 Uiso 0.5 1 calc R U P B 1
H22B H 0.7342 0.2077 0.2513 0.100 Uiso 0.5 1 calc R U P B 1
C23A C 0.4693(17) 0.1513(17) 0.2675(9) 0.075(4) Uani 0.5 1 d D U P B 1
H23A H 0.4961 0.1035 0.3001 0.090 Uiso 0.5 1 calc R U P B 1
H23B H 0.4487 0.1083 0.2317 0.090 Uiso 0.5 1 calc R U P B 1
C24A C 0.3613(16) 0.2053(17) 0.2883(8) 0.074(4) Uani 0.5 1 d D U P B 1
H24A H 0.3013 0.1539 0.3017 0.089 Uiso 0.5 1 calc R U P B 1
H24B H 0.3803 0.2514 0.3231 0.089 Uiso 0.5 1 calc R U P B 1
C25A C 0.9041(17) 0.6249(12) -0.0905(9) 0.076(4) Uani 0.5 1 d D U P B 1
H25A H 0.9810 0.6412 -0.0708 0.091 Uiso 0.5 1 calc R U P B 1
H25B H 0.8466 0.6799 -0.0793 0.091 Uiso 0.5 1 calc R U P B 1
C26A C 0.9185(12) 0.6215(12) -0.1573(7) 0.079(3) Uani 0.5 1 d D U P B 1
H26A H 0.9457 0.6902 -0.1723 0.094 Uiso 0.5 1 calc R U P B 1
H26B H 0.9788 0.5687 -0.1683 0.094 Uiso 0.5 1 calc R U P B 1
C27A C 0.8101(16) 0.6036(12) -0.2495(7) 0.074(4) Uani 0.5 1 d D U P B 1
H27A H 0.7595 0.5479 -0.2668 0.089 Uiso 0.5 1 calc R U P B 1
H27B H 0.8922 0.5913 -0.2636 0.089 Uiso 0.5 1 calc R U P B 1
C28A C 0.768(2) 0.7069(15) -0.2736(12) 0.077(6) Uani 0.5 1 d D U P B 1
H28A H 0.8336 0.7585 -0.2719 0.092 Uiso 0.5 1 calc R U P B 1
H28B H 0.7423 0.6996 -0.3164 0.092 Uiso 0.5 1 calc R U P B 1
O3B O 0.7065(12) 0.2922(9) 0.1171(7) 0.064(3) Uani 0.5 1 d D U P C 2
O4B O 0.5514(8) 0.1922(7) 0.2091(4) 0.061(2) Uani 0.5 1 d D U P C 2
O5B O 0.3482(17) 0.2764(11) 0.2588(8) 0.071(4) Uani 0.5 1 d D U P C 2
O6B O 0.8866(11) 0.6027(11) -0.0653(6) 0.075(3) Uani 0.5 1 d D U P C 2
O7B O 0.8989(9) 0.7312(8) -0.1745(5) 0.078(3) Uani 0.5 1 d D U P C 2
C11B C 0.7765(13) 0.4223(11) 0.0543(6) 0.054(3) Uani 0.5 1 d D U P C 2
C12B C 0.781(2) 0.4881(15) 0.1055(8) 0.057(4) Uani 0.5 1 d D U P C 2
H12B H 0.7610 0.4622 0.1446 0.069 Uiso 0.5 1 calc R U P C 2
C13B C 0.816(2) 0.5912(15) 0.0984(9) 0.071(5) Uani 0.5 1 d D U P C 2
H13B H 0.8153 0.6356 0.1330 0.085 Uiso 0.5 1 calc R U P C 2
C14B C 0.8518(13) 0.6322(15) 0.0424(7) 0.070(3) Uani 0.5 1 d D U P C 2
H14B H 0.8772 0.7026 0.0390 0.084 Uiso 0.5 1 calc R U P C 2
C15B C 0.8490(12) 0.5669(13) -0.0079(7) 0.066(3) Uani 0.5 1 d D U P C 2
C16B C 0.8127(13) 0.4616(14) -0.0030(5) 0.062(3) Uani 0.5 1 d D U P C 2
C17B C 0.8116(12) 0.3971(11) -0.0550(6) 0.065(3) Uani 0.5 1 d D U P C 2
H17B H 0.8358 0.4218 -0.0938 0.078 Uiso 0.5 1 calc R U P C 2
C18B C 0.7725(19) 0.2942(14) -0.0460(8) 0.070(4) Uani 0.5 1 d D U P C 2
H18B H 0.7670 0.2503 -0.0807 0.083 Uiso 0.5 1 calc R U P C 2
C19B C 0.7410(15) 0.2517(13) 0.0105(7) 0.071(4) Uani 0.5 1 d D U P C 2
H19B H 0.7212 0.1801 0.0146 0.086 Uiso 0.5 1 calc R U P C 2
C20B C 0.7400(13) 0.3190(12) 0.0608(7) 0.059(3) Uani 0.5 1 d D U P C 2
C21B C 0.7034(17) 0.1856(12) 0.1324(8) 0.076(4) Uani 0.5 1 d D U P C 2
H21C H 0.7812 0.1533 0.1235 0.092 Uiso 0.5 1 calc R U P C 2
H21D H 0.6424 0.1498 0.1076 0.092 Uiso 0.5 1 calc R U P C 2
C22B C 0.6752(13) 0.1730(12) 0.1990(9) 0.067(4) Uani 0.5 1 d D U P C 2
H22C H 0.6954 0.1014 0.2123 0.081 Uiso 0.5 1 calc R U P C 2
H22D H 0.7232 0.2225 0.2232 0.081 Uiso 0.5 1 calc R U P C 2
C23B C 0.518(2) 0.167(2) 0.2682(8) 0.083(5) Uani 0.5 1 d D U P C 2
H23C H 0.5551 0.2159 0.2974 0.099 Uiso 0.5 1 calc R U P C 2
H23D H 0.5445 0.0954 0.2783 0.099 Uiso 0.5 1 calc R U P C 2
C24B C 0.386(2) 0.1739(12) 0.2721(9) 0.072(4) Uani 0.5 1 d D U P C 2
H24C H 0.3496 0.1246 0.2429 0.087 Uiso 0.5 1 calc R U P C 2
H24D H 0.3600 0.1544 0.3135 0.087 Uiso 0.5 1 calc R U P C 2
C25B C 0.9494(14) 0.6998(12) -0.0665(8) 0.080(3) Uani 0.5 1 d D U P C 2
H25C H 1.0175 0.6982 -0.0380 0.096 Uiso 0.5 1 calc R U P C 2
H25D H 0.8964 0.7581 -0.0551 0.096 Uiso 0.5 1 calc R U P C 2
C26B C 0.9912(14) 0.7117(14) -0.1307(7) 0.082(4) Uani 0.5 1 d D U P C 2
H26C H 1.0487 0.7699 -0.1322 0.099 Uiso 0.5 1 calc R U P C 2
H26D H 1.0337 0.6474 -0.1426 0.099 Uiso 0.5 1 calc R U P C 2
C27B C 0.8534(14) 0.6396(12) -0.2041(8) 0.074(4) Uani 0.5 1 d D U P C 2
H27C H 0.7976 0.6027 -0.1770 0.088 Uiso 0.5 1 calc R U P C 2
H27D H 0.9191 0.5917 -0.2145 0.088 Uiso 0.5 1 calc R U P C 2
C28B C 0.7906(19) 0.675(2) -0.2611(9) 0.080(6) Uani 0.5 1 d D U P C 2
H28C H 0.7888 0.6143 -0.2891 0.096 Uiso 0.5 1 calc R U P C 2
H28D H 0.8414 0.7282 -0.2803 0.096 Uiso 0.5 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 F5 1.481(9) . ?
P1 F4 1.528(7) . ?
P1 F2 1.542(7) . ?
P1 F6 1.595(8) . ?
P1 F1 1.630(8) . ?
P1 F3 1.642(9) . ?
O1 C7 1.399(10) . ?
O2 C10 1.54(2) . ?
N1 C4 1.346(8) . ?
N1 C3 1.384(7) . ?
N1 C5 1.478(8) . ?
N2 C4 1.331(8) . ?
N2 C2 1.400(7) . ?
N2 C8 1.498(8) . ?
C1 C2 1.367(7) . ?
C1 C3 1.393(8) 3_665 ?
C1 H1 0.9500 . ?
C2 C3 1.411(8) . ?
C3 C1 1.393(8) 3_665 ?
C4 H4 0.9500 . ?
C5 C6 1.556(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.497(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.483(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.543(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O2A 1.53(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O3A C20A 1.33(2) . ?
O3A C21A 1.406(15) . ?
O4A C23A 1.378(16) . ?
O4A C22A 1.394(15) . ?
O5A C28A 1.28(3) 3_665 ?
O5A C24A 1.377(16) . ?
O6A C15A 1.344(17) . ?
O6A C25A 1.449(15) . ?
O7A C26A 1.421(15) . ?
O7A C27A 1.431(15) . ?
C11A C16A 1.415(12) . ?
C11A C20A 1.416(13) . ?
C11A C12A 1.416(14) . ?
C12A C13A 1.399(14) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.408(13) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.408(13) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.414(13) . ?
C16A C17A 1.407(13) . ?
C17A C18A 1.407(13) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.416(13) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.400(13) . ?
C19A H19A 0.9500 . ?
C21A C22A 1.483(17) . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C23A C24A 1.475(18) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.480(17) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A C28A 1.502(15) . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C28A O5A 1.28(3) 3_665 ?
C28A C24A 1.87(3) 3_665 ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
O3B C20B 1.34(2) . ?
O3B C21B 1.409(15) . ?
O4B C23B 1.392(16) . ?
O4B C22B 1.435(15) . ?
O5B C24B 1.412(15) . ?
O5B C28B 1.69(3) 3_665 ?
O6B C15B 1.41(2) . ?
O6B C25B 1.434(16) . ?
O7B C27B 1.437(15) . ?
O7B C26B 1.438(15) . ?
C11B C20B 1.396(13) . ?
C11B C12B 1.409(12) . ?
C11B C16B 1.417(13) . ?
C12B C13B 1.388(14) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.400(14) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.390(13) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.416(13) . ?
C16B C17B 1.412(13) . ?
C17B C18B 1.407(13) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.404(14) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.403(13) . ?
C19B H19B 0.9500 . ?
C21B C22B 1.508(18) . ?
C21B H21C 0.9900 . ?
C21B H21D 0.9900 . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23B C24B 1.494(19) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.497(18) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B C28B 1.505(19) . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
C28B O5B 1.69(3) 3_665 ?
C28B H28C 0.9900 . ?
C28B H28D 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
F5 P1 F4 95.6(4) . . ?
F5 P1 F2 95.3(4) . . ?
F4 P1 F2 165.5(5) . . ?
F5 P1 F6 95.4(5) . . ?
F4 P1 F6 94.6(5) . . ?
F2 P1 F6 93.9(4) . . ?
F5 P1 F1 178.8(5) . . ?
F4 P1 F1 83.4(4) . . ?
F2 P1 F1 85.5(4) . . ?
F6 P1 F1 85.4(4) . . ?
F5 P1 F3 90.5(5) . . ?
F4 P1 F3 86.8(5) . . ?
F2 P1 F3 83.5(4) . . ?
F6 P1 F3 173.8(5) . . ?
F1 P1 F3 88.8(5) . . ?
C4 N1 C3 108.3(5) . . ?
C4 N1 C5 125.7(5) . . ?
C3 N1 C5 126.0(5) . . ?
C4 N2 C2 108.9(5) . . ?
C4 N2 C8 127.1(5) . . ?
C2 N2 C8 124.0(5) . . ?
C2 C1 C3 112.9(5) . 3_665 ?
C2 C1 H1 123.6 . . ?
C3 C1 H1 123.6 3_665 . ?
C1 C2 N2 130.1(5) . . ?
C1 C2 C3 124.4(5) . . ?
N2 C2 C3 105.5(5) . . ?
N1 C3 C1 130.1(5) . 3_665 ?
N1 C3 C2 107.1(5) . . ?
C1 C3 C2 122.7(5) 3_665 . ?
N2 C4 N1 110.1(5) . . ?
N2 C4 H4 124.9 . . ?
N1 C4 H4 124.9 . . ?
N1 C5 C6 112.6(6) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 109.1(6) . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O1 C7 C6 111.2(7) . . ?
O1 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 N2 114.0(5) . . ?
C9 C8 H8A 108.8 . . ?
N2 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N2 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 109.8(6) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2A C10 C9 106.2(9) . . ?
O2 C10 C9 110.3(11) . . ?
O2A C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O2A C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C20A O3A C21A 120.4(13) . . ?
C23A O4A C22A 118.1(17) . . ?
C28A O5A C24A 89.8(14) 3_665 . ?
C15A O6A C25A 122.7(13) . . ?
C26A O7A C27A 112.7(12) . . ?
C16A C11A C20A 118.2(14) . . ?
C16A C11A C12A 121.8(14) . . ?
C20A C11A C12A 119.9(14) . . ?
C13A C12A C11A 115.7(19) . . ?
C13A C12A H12A 122.1 . . ?
C11A C12A H12A 122.1 . . ?
C12A C13A C14A 124.8(18) . . ?
C12A C13A H13A 117.6 . . ?
C14A C13A H13A 117.6 . . ?
C15A C14A C13A 117.9(15) . . ?
C15A C14A H14A 121.1 . . ?
C13A C14A H14A 121.1 . . ?
O6A C15A C14A 119.8(14) . . ?
O6A C15A C16A 120.3(12) . . ?
C14A C15A C16A 119.9(13) . . ?
C17A C16A C15A 115.7(12) . . ?
C17A C16A C11A 124.4(12) . . ?
C15A C16A C11A 119.8(11) . . ?
C16A C17A C18A 115.3(14) . . ?
C16A C17A H17A 122.4 . . ?
C18A C17A H17A 122.4 . . ?
C17A C18A C19A 122.4(13) . . ?
C17A C18A H18A 118.8 . . ?
C19A C18A H18A 118.8 . . ?
C20A C19A C18A 120.5(13) . . ?
C20A C19A H19A 119.8 . . ?
C18A C19A H19A 119.8 . . ?
O3A C20A C19A 124.7(13) . . ?
O3A C20A C11A 116.1(12) . . ?
C19A C20A C11A 119.2(15) . . ?
O3A C21A C22A 110.9(15) . . ?
O3A C21A H21A 109.5 . . ?
C22A C21A H21A 109.5 . . ?
O3A C21A H21B 109.5 . . ?
C22A C21A H21B 109.5 . . ?
H21A C21A H21B 108.1 . . ?
O4A C22A C21A 117.1(16) . . ?
O4A C22A H22A 108.0 . . ?
C21A C22A H22A 108.0 . . ?
O4A C22A H22B 108.0 . . ?
C21A C22A H22B 108.0 . . ?
H22A C22A H22B 107.3 . . ?
O4A C23A C24A 114.9(18) . . ?
O4A C23A H23A 108.5 . . ?
C24A C23A H23A 108.5 . . ?
O4A C23A H23B 108.5 . . ?
C24A C23A H23B 108.5 . . ?
H23A C23A H23B 107.5 . . ?
O5A C24A C23A 108.0(14) . . ?
O5A C24A H24A 110.1 . . ?
C23A C24A H24A 110.1 . . ?
O5A C24A H24B 110.1 . . ?
C23A C24A H24B 110.1 . . ?
H24A C24A H24B 108.4 . . ?
O6A C25A C26A 108.8(14) . . ?
O6A C25A H25A 109.9 . . ?
C26A C25A H25A 109.9 . . ?
O6A C25A H25B 109.9 . . ?
C26A C25A H25B 109.9 . . ?
H25A C25A H25B 108.3 . . ?
O7A C26A C25A 109.1(13) . . ?
O7A C26A H26A 109.9 . . ?
C25A C26A H26A 109.9 . . ?
O7A C26A H26B 109.9 . . ?
C25A C26A H26B 109.9 . . ?
H26A C26A H26B 108.3 . . ?
O7A C27A C28A 114.1(15) . . ?
O7A C27A H27A 108.7 . . ?
C28A C27A H27A 108.7 . . ?
O7A C27A H27B 108.7 . . ?
C28A C27A H27B 108.7 . . ?
H27A C27A H27B 107.6 . . ?
O5A C28A C27A 107.6(18) 3_665 . ?
O5A C28A C24A 47.3(9) 3_665 3_665 ?
C27A C28A C24A 147(2) . 3_665 ?
O5A C28A H28A 110.2 3_665 . ?
C27A C28A H28A 110.2 . . ?
C24A C28A H28A 100.6 3_665 . ?
O5A C28A H28B 110.2 3_665 . ?
C27A C28A H28B 110.2 . . ?
C24A C28A H28B 70.2 3_665 . ?
H28A C28A H28B 108.5 . . ?
C20B O3B C21B 118.6(14) . . ?
C23B O4B C22B 111.7(13) . . ?
C24B O5B C28B 128.3(19) . 3_665 ?
C15B O6B C25B 116.8(13) . . ?
C27B O7B C26B 114.7(12) . . ?
C20B C11B C12B 119.9(13) . . ?
C20B C11B C16B 120.9(13) . . ?
C12B C11B C16B 119.1(14) . . ?
C13B C12B C11B 119.5(17) . . ?
C13B C12B H12B 120.3 . . ?
C11B C12B H12B 120.3 . . ?
C12B C13B C14B 122.6(18) . . ?
C12B C13B H13B 118.7 . . ?
C14B C13B H13B 118.7 . . ?
C15B C14B C13B 117.9(17) . . ?
C15B C14B H14B 121.0 . . ?
C13B C14B H14B 121.0 . . ?
C14B C15B O6B 120.7(14) . . ?
C14B C15B C16B 121.3(15) . . ?
O6B C15B C16B 117.9(13) . . ?
C17B C16B C15B 119.9(13) . . ?
C17B C16B C11B 120.7(14) . . ?
C15B C16B C11B 119.5(12) . . ?
C18B C17B C16B 116.0(14) . . ?
C18B C17B H17B 122.0 . . ?
C16B C17B H17B 122.0 . . ?
C19B C18B C17B 124.7(15) . . ?
C19B C18B H18B 117.6 . . ?
C17B C18B H18B 117.6 . . ?
C20B C19B C18B 117.5(15) . . ?
C20B C19B H19B 121.3 . . ?
C18B C19B H19B 121.3 . . ?
O3B C20B C11B 115.0(11) . . ?
O3B C20B C19B 124.9(15) . . ?
C11B C20B C19B 120.1(14) . . ?
O3B C21B C22B 110.0(14) . . ?
O3B C21B H21C 109.7 . . ?
C22B C21B H21C 109.7 . . ?
O3B C21B H21D 109.7 . . ?
C22B C21B H21D 109.7 . . ?
H21C C21B H21D 108.2 . . ?
O4B C22B C21B 109.9(13) . . ?
O4B C22B H22C 109.7 . . ?
C21B C22B H22C 109.7 . . ?
O4B C22B H22D 109.7 . . ?
C21B C22B H22D 109.7 . . ?
H22C C22B H22D 108.2 . . ?
O4B C23B C24B 108.2(14) . . ?
O4B C23B H23C 110.1 . . ?
C24B C23B H23C 110.1 . . ?
O4B C23B H23D 110.1 . . ?
C24B C23B H23D 110.1 . . ?
H23C C23B H23D 108.4 . . ?
O5B C24B C23B 110.2(16) . . ?
O5B C24B H24C 109.6 . . ?
C23B C24B H24C 109.6 . . ?
O5B C24B H24D 109.6 . . ?
C23B C24B H24D 109.6 . . ?
H24C C24B H24D 108.1 . . ?
O6B C25B C26B 105.3(14) . . ?
O6B C25B H25C 110.7 . . ?
C26B C25B H25C 110.7 . . ?
O6B C25B H25D 110.7 . . ?
C26B C25B H25D 110.7 . . ?
H25C C25B H25D 108.8 . . ?
O7B C26B C25B 114.9(13) . . ?
O7B C26B H26C 108.5 . . ?
C25B C26B H26C 108.5 . . ?
O7B C26B H26D 108.5 . . ?
C25B C26B H26D 108.5 . . ?
H26C C26B H26D 107.5 . . ?
O7B C27B C28B 107.4(16) . . ?
O7B C27B H27C 110.2 . . ?
C28B C27B H27C 110.2 . . ?
O7B C27B H27D 110.2 . . ?
C28B C27B H27D 110.2 . . ?
H27C C27B H27D 108.5 . . ?
C27B C28B O5B 121.4(16) . 3_665 ?
C27B C28B H28C 107.0 . . ?
O5B C28B H28C 107.0 3_665 . ?
C27B C28B H28D 107.0 . . ?
O5B C28B H28D 107.0 3_665 . ?
H28C C28B H28D 106.7 . . ?

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
C3 C1 C2 N2 -179.9(5) 3_665 . . . ?
C3 C1 C2 C3 -1.4(8) 3_665 . . . ?
C4 N2 C2 C1 179.4(6) . . . . ?
C8 N2 C2 C1 -1.2(8) . . . . ?
C4 N2 C2 C3 0.7(6) . . . . ?
C8 N2 C2 C3 -179.9(5) . . . . ?
C4 N1 C3 C1 179.4(6) . . . 3_665 ?
C5 N1 C3 C1 1.8(10) . . . 3_665 ?
C4 N1 C3 C2 0.7(6) . . . . ?
C5 N1 C3 C2 -176.9(6) . . . . ?
C1 C2 C3 N1 -179.6(5) . . . . ?
N2 C2 C3 N1 -0.8(5) . . . . ?
C1 C2 C3 C1 1.5(9) . . . 3_665 ?
N2 C2 C3 C1 -179.7(5) . . . 3_665 ?
C2 N2 C4 N1 -0.2(7) . . . . ?
C8 N2 C4 N1 -179.7(5) . . . . ?
C3 N1 C4 N2 -0.3(7) . . . . ?
C5 N1 C4 N2 177.3(6) . . . . ?
C4 N1 C5 C6 45.6(10) . . . . ?
C3 N1 C5 C6 -137.1(7) . . . . ?
N1 C5 C6 C7 -176.5(6) . . . . ?
C5 C6 C7 O1 66.7(9) . . . . ?
C4 N2 C8 C9 2.3(8) . . . . ?
C2 N2 C8 C9 -177.1(5) . . . . ?
N2 C8 C9 C10 -178.6(6) . . . . ?
C8 C9 C10 O2A 67.2(10) . . . . ?
C8 C9 C10 O2 -175.8(14) . . . . ?
C16A C11A C12A C13A -1(3) . . . . ?
C20A C11A C12A C13A 178.4(19) . . . . ?
C11A C12A C13A C14A 0(4) . . . . ?
C12A C13A C14A C15A -1(3) . . . . ?
C25A O6A C15A C14A 0.1(19) . . . . ?
C25A O6A C15A C16A 178.4(12) . . . . ?
C13A C14A C15A O6A -179.4(16) . . . . ?
C13A C14A C15A C16A 2(2) . . . . ?
O6A C15A C16A C17A 2.8(18) . . . . ?
C14A C15A C16A C17A -178.9(13) . . . . ?
O6A C15A C16A C11A 179.2(11) . . . . ?
C14A C15A C16A C11A -2.5(18) . . . . ?
C20A C11A C16A C17A -1(2) . . . . ?
C12A C11A C16A C17A 178(2) . . . . ?
C20A C11A C16A C15A -177.3(12) . . . . ?
C12A C11A C16A C15A 2(2) . . . . ?
C15A C16A C17A C18A 178.3(12) . . . . ?
C11A C16A C17A C18A 2(2) . . . . ?
C16A C17A C18A C19A -1(2) . . . . ?
C17A C18A C19A C20A 0(2) . . . . ?
C21A O3A C20A C19A 16(2) . . . . ?
C21A O3A C20A C11A -166.0(12) . . . . ?
C18A C19A C20A O3A 178.8(12) . . . . ?
C18A C19A C20A C11A 0.7(19) . . . . ?
C16A C11A C20A O3A -178.5(11) . . . . ?
C12A C11A C20A O3A 3(2) . . . . ?
C16A C11A C20A C19A -0.2(19) . . . . ?
C12A C11A C20A C19A -179(2) . . . . ?
C20A O3A C21A C22A 176.4(12) . . . . ?
C23A O4A C22A C21A 100(2) . . . . ?
O3A C21A C22A O4A 66(2) . . . . ?
C22A O4A C23A C24A -179.9(16) . . . . ?
C28A O5A C24A C23A 179(2) 3_665 . . . ?
O4A C23A C24A O5A 64(3) . . . . ?
C15A O6A C25A C26A -177.4(11) . . . . ?
C27A O7A C26A C25A 172.6(11) . . . . ?
O6A C25A C26A O7A 58.2(16) . . . . ?
C26A O7A C27A C28A -94.0(19) . . . . ?
O7A C27A C28A O5A -38(3) . . . 3_665 ?
O7A C27A C28A C24A -74(4) . . . 3_665 ?
C20B C11B C12B C13B -179.0(17) . . . . ?
C16B C11B C12B C13B 3(3) . . . . ?
C11B C12B C13B C14B -3(3) . . . . ?
C12B C13B C14B C15B 2(3) . . . . ?
C13B C14B C15B O6B -178.5(17) . . . . ?
C13B C14B C15B C16B -1(2) . . . . ?
C25B O6B C15B C14B 12.5(19) . . . . ?
C25B O6B C15B C16B -165.2(13) . . . . ?
C14B C15B C16B C17B -179.6(13) . . . . ?
O6B C15B C16B C17B -2(2) . . . . ?
C14B C15B C16B C11B 1(2) . . . . ?
O6B C15B C16B C11B 178.8(12) . . . . ?
C20B C11B C16B C17B 1(2) . . . . ?
C12B C11B C16B C17B 178.6(16) . . . . ?
C20B C11B C16B C15B 179.9(13) . . . . ?
C12B C11B C16B C15B -2(2) . . . . ?
C15B C16B C17B C18B -179.0(15) . . . . ?
C11B C16B C17B C18B 0(2) . . . . ?
C16B C17B C18B C19B -3(3) . . . . ?
C17B C18B C19B C20B 5(3) . . . . ?
C21B O3B C20B C11B -160.8(14) . . . . ?
C21B O3B C20B C19B 19(2) . . . . ?
C12B C11B C20B O3B 3(2) . . . . ?
C16B C11B C20B O3B -179.1(13) . . . . ?
C12B C11B C20B C19B -176.7(16) . . . . ?
C16B C11B C20B C19B 1(2) . . . . ?
C18B C19B C20B O3B 176.6(15) . . . . ?
C18B C19B C20B C11B -4(2) . . . . ?
C20B O3B C21B C22B 174.6(13) . . . . ?
C23B O4B C22B C21B 171.4(17) . . . . ?
O3B C21B C22B O4B 75.5(17) . . . . ?
C22B O4B C23B C24B -171.7(15) . . . . ?
C28B O5B C24B C23B -176.2(16) 3_665 . . . ?
O4B C23B C24B O5B -61(3) . . . . ?
C15B O6B C25B C26B 173.1(12) . . . . ?
C27B O7B C26B C25B -93.8(18) . . . . ?
O6B C25B C26B O7B 69.7(17) . . . . ?
C26B O7B C27B C28B -161.5(15) . . . . ?
O7B C27B C28B O5B -80(2) . . . 3_665 ?

_refine_diff_density_max         2.035
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.191

####################################################################### 
# 
# 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_11rfs03
_database_code_depnum_ccdc_archive 'CCDC 1884120'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_vrf_PLAT029_I                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.869 Why?  
RESPONSE: poorly diffracting crystal
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H40 O10, C12 H16 N4, 2(F6 P)'
_chemical_formula_sum            'C40 H56 F12 N4 O10 P2'
_chemical_formula_weight         1042.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.4853(13)
_cell_length_b                   11.6056(17)
_cell_length_c                   12.1927(18)
_cell_angle_alpha                84.209(7)
_cell_angle_beta                 73.935(6)
_cell_angle_gamma                83.516(7)
_cell_volume                     1143.4(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8127
_cell_measurement_theta_min      4.881
_cell_measurement_theta_max      68.936

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             542
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    1.845
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11844
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.783
_diffrn_reflns_theta_max         66.304
_diffrn_reflns_theta_full        66.304
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.869
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             3476
_reflns_number_gt                2007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2010) and XPREP (Bruker, 2010)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.

All nonhydrogen atoms were located in succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.4608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3476
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.40386(16) 0.74866(13) 0.60164(12) 0.0315(4) Uani 1 1 d . . . . .
F1 F 0.3533(4) 0.8660(3) 0.6606(3) 0.0645(11) Uani 1 1 d . . . . .
F2 F 0.2815(4) 0.6843(3) 0.7085(3) 0.0599(10) Uani 1 1 d . . . . .
F3 F 0.4545(4) 0.6293(3) 0.5445(3) 0.0671(11) Uani 1 1 d . . . . .
F4 F 0.5271(4) 0.8110(3) 0.4966(3) 0.0692(12) Uani 1 1 d . . . . .
F5 F 0.2579(3) 0.7763(3) 0.5407(2) 0.0447(8) Uani 1 1 d . . . . .
F6 F 0.5499(3) 0.7201(3) 0.6633(2) 0.0394(8) Uani 1 1 d . . . . .
O1 O 0.3988(4) 0.0797(3) 0.8744(3) 0.0344(9) Uani 1 1 d . . . . .
O2 O 0.7199(4) 0.0618(3) 0.7258(3) 0.0323(9) Uani 1 1 d . . . . .
O3 O 1.0215(4) 0.1551(3) 0.7054(3) 0.0314(9) Uani 1 1 d . . . . .
O4 O -0.0018(4) 0.5974(3) 1.3416(3) 0.0331(9) Uani 1 1 d . . . . .
O5 O 0.0858(4) 0.4290(3) 1.1565(3) 0.0335(9) Uani 1 1 d . . . . .
N1 N 0.3019(5) 0.7003(4) 1.0470(3) 0.0308(10) Uani 1 1 d . . . . .
N2 N 0.3817(5) 0.6147(4) 1.1942(3) 0.0293(10) Uani 1 1 d . . . . .
C1 C 0.3997(6) 0.6002(4) 1.0093(4) 0.0271(12) Uani 1 1 d . . . . .
C2 C 0.2270(6) 0.7882(5) 0.9783(5) 0.0397(14) Uani 1 1 d . . . . .
H2A H 0.1514 0.8432 1.0285 0.059 Uiso 1 1 calc R U . . .
H2B H 0.1658 0.7506 0.9366 0.059 Uiso 1 1 calc R U . . .
H2C H 0.3132 0.8301 0.9237 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2950(6) 0.7051(5) 1.1578(4) 0.0310(13) Uani 1 1 d . . . . .
H3 H 0.2357 0.7654 1.2039 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4037(6) 0.5924(5) 1.3096(4) 0.0348(13) Uani 1 1 d . . . . .
H4A H 0.3388 0.6528 1.3581 0.052 Uiso 1 1 calc R U . . .
H4B H 0.5204 0.5933 1.3061 0.052 Uiso 1 1 calc R U . . .
H4C H 0.3667 0.5162 1.3420 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4521(6) 0.5449(4) 1.1033(4) 0.0282(12) Uani 1 1 d . . . . .
C6 C 0.5540(6) 0.4434(4) 1.0982(4) 0.0305(13) Uani 1 1 d . . . . .
H6 H 0.5892 0.4068 1.1617 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3178(6) 0.1697(4) 0.9401(4) 0.0277(12) Uani 1 1 d . . . . .
C8 C 0.2219(6) 0.2626(5) 0.9041(4) 0.0336(13) Uani 1 1 d . . . . .
H8 H 0.2077 0.2675 0.8291 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1468(6) 0.3483(5) 0.9776(4) 0.0335(13) Uani 1 1 d . . . . .
H9 H 0.0828 0.4126 0.9523 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1644(6) 0.3408(5) 1.0887(4) 0.0302(13) Uani 1 1 d . . . . .
C11 C 0.2607(6) 0.2456(4) 1.1239(4) 0.0303(12) Uani 1 1 d . . . . .
H11 H 0.2752 0.2394 1.1988 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3339(6) 0.1615(4) 1.0504(4) 0.0305(13) Uani 1 1 d . . . . .
H12 H 0.3968 0.0964 1.0756 0.037 Uiso 1 1 calc R U . . .
C13 C 0.4319(6) 0.1010(5) 0.7518(4) 0.0305(13) Uani 1 1 d . . . . .
H13A H 0.4509 0.1837 0.7289 0.037 Uiso 1 1 calc R U . . .
H13B H 0.3372 0.0829 0.7261 0.037 Uiso 1 1 calc R U . . .
C14 C 0.5817(6) 0.0245(5) 0.6994(4) 0.0293(12) Uani 1 1 d . . . . .
H14A H 0.5668 -0.0571 0.7296 0.035 Uiso 1 1 calc R U . . .
H14B H 0.5998 0.0286 0.6154 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8704(6) 0.0040(5) 0.6624(4) 0.0329(13) Uani 1 1 d . . . . .
H15A H 0.8912 0.0295 0.5800 0.039 Uiso 1 1 calc R U . . .
H15B H 0.8634 -0.0812 0.6714 0.039 Uiso 1 1 calc R U . . .
C16 C 1.0081(6) 0.0340(5) 0.7073(5) 0.0370(14) Uani 1 1 d . . . . .
H16A H 0.9914 0.0001 0.7871 0.044 Uiso 1 1 calc R U . . .
H16B H 1.1134 -0.0026 0.6612 0.044 Uiso 1 1 calc R U . . .
C17 C 1.0629(6) 0.2110(5) 0.5923(4) 0.0358(14) Uani 1 1 d . . . . .
H17A H 0.9641 0.2235 0.5629 0.043 Uiso 1 1 calc R U . . .
H17B H 1.1476 0.1611 0.5405 0.043 Uiso 1 1 calc R U . . .
C18 C -0.1265(6) 0.6756(5) 1.4050(4) 0.0350(13) Uani 1 1 d . . . . .
H18A H -0.1676 0.6413 1.4842 0.042 Uiso 1 1 calc R U . . .
H18B H -0.2198 0.6880 1.3699 0.042 Uiso 1 1 calc R U . . .
C19 C -0.0637(6) 0.4891(5) 1.3414(4) 0.0350(13) Uani 1 1 d . . . . .
H19A H -0.1570 0.5013 1.3064 0.042 Uiso 1 1 calc R U . . .
H19B H -0.1058 0.4572 1.4214 0.042 Uiso 1 1 calc R U . . .
C20 C 0.0625(6) 0.4034(5) 1.2780(4) 0.0346(13) Uani 1 1 d . . . . .
H20A H 0.1678 0.4066 1.2972 0.041 Uiso 1 1 calc R U . . .
H20B H 0.0270 0.3241 1.3003 0.041 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 F1 1.565(3) . ?
P1 F3 1.576(3) . ?
P1 F4 1.581(3) . ?
P1 F5 1.600(3) . ?
P1 F2 1.601(3) . ?
P1 F6 1.607(3) . ?
O1 C7 1.380(5) . ?
O1 C13 1.444(5) . ?
O2 C14 1.421(5) . ?
O2 C15 1.430(5) . ?
O3 C16 1.419(6) . ?
O3 C17 1.433(6) . ?
O4 C19 1.417(6) . ?
O4 C18 1.418(5) . ?
O5 C10 1.374(6) . ?
O5 C20 1.443(5) . ?
N1 C3 1.341(6) . ?
N1 C1 1.389(6) . ?
N1 C2 1.458(6) . ?
N2 C3 1.323(6) . ?
N2 C5 1.395(6) . ?
N2 C4 1.465(6) . ?
C1 C6 1.389(6) 2_667 ?
C1 C5 1.411(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3 0.9500 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.377(7) . ?
C6 C1 1.389(6) 2_667 ?
C6 H6 0.9500 . ?
C7 C12 1.381(6) . ?
C7 C8 1.387(7) . ?
C8 C9 1.385(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.402(7) . ?
C11 C12 1.368(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.491(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.507(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.484(7) 2_667 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C17 1.484(7) 2_667 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.479(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 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
F1 P1 F3 179.0(2) . . ?
F1 P1 F4 90.5(2) . . ?
F3 P1 F4 90.3(2) . . ?
F1 P1 F5 90.20(17) . . ?
F3 P1 F5 90.40(17) . . ?
F4 P1 F5 91.09(17) . . ?
F1 P1 F2 89.9(2) . . ?
F3 P1 F2 89.3(2) . . ?
F4 P1 F2 179.1(2) . . ?
F5 P1 F2 89.75(17) . . ?
F1 P1 F6 89.99(17) . . ?
F3 P1 F6 89.40(17) . . ?
F4 P1 F6 89.26(17) . . ?
F5 P1 F6 179.6(2) . . ?
F2 P1 F6 89.90(16) . . ?
C7 O1 C13 117.2(4) . . ?
C14 O2 C15 111.3(3) . . ?
C16 O3 C17 113.3(4) . . ?
C19 O4 C18 110.4(4) . . ?
C10 O5 C20 115.8(4) . . ?
C3 N1 C1 107.7(4) . . ?
C3 N1 C2 125.5(4) . . ?
C1 N1 C2 126.7(4) . . ?
C3 N2 C5 108.6(4) . . ?
C3 N2 C4 126.0(4) . . ?
C5 N2 C4 125.4(4) . . ?
N1 C1 C6 130.1(5) . 2_667 ?
N1 C1 C5 106.9(4) . . ?
C6 C1 C5 123.0(4) 2_667 . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 N1 111.0(4) . . ?
N2 C3 H3 124.5 . . ?
N1 C3 H3 124.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 130.3(5) . . ?
C6 C5 C1 123.8(4) . . ?
N2 C5 C1 105.8(4) . . ?
C5 C6 C1 113.2(5) . 2_667 ?
C5 C6 H6 123.4 . . ?
C1 C6 H6 123.4 2_667 . ?
O1 C7 C12 115.3(4) . . ?
O1 C7 C8 125.0(4) . . ?
C12 C7 C8 119.7(5) . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.5(5) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O5 C10 C9 117.0(5) . . ?
O5 C10 C11 124.3(5) . . ?
C9 C10 C11 118.7(5) . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 121.1(5) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
O1 C13 C14 107.4(4) . . ?
O1 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O1 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O2 C14 C13 109.1(4) . . ?
O2 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
O2 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O2 C15 C16 108.3(4) . . ?
O2 C15 H15A 110.0 . . ?
C16 C15 H15A 110.0 . . ?
O2 C15 H15B 110.0 . . ?
C16 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
O3 C16 C15 114.5(4) . . ?
O3 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
O3 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
O3 C17 C18 109.4(4) . 2_667 ?
O3 C17 H17A 109.8 . . ?
C18 C17 H17A 109.8 2_667 . ?
O3 C17 H17B 109.8 . . ?
C18 C17 H17B 109.8 2_667 . ?
H17A C17 H17B 108.2 . . ?
O4 C18 C17 111.1(4) . 2_667 ?
O4 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 2_667 . ?
O4 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 2_667 . ?
H18A C18 H18B 108.0 . . ?
O4 C19 C20 112.6(4) . . ?
O4 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
O4 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
O5 C20 C19 109.7(4) . . ?
O5 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
O5 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?

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
C3 N1 C1 C6 -179.3(5) . . . 2_667 ?
C2 N1 C1 C6 -2.4(8) . . . 2_667 ?
C3 N1 C1 C5 -0.2(5) . . . . ?
C2 N1 C1 C5 176.7(5) . . . . ?
C5 N2 C3 N1 0.3(6) . . . . ?
C4 N2 C3 N1 179.0(4) . . . . ?
C1 N1 C3 N2 -0.1(6) . . . . ?
C2 N1 C3 N2 -177.0(5) . . . . ?
C3 N2 C5 C6 178.8(5) . . . . ?
C4 N2 C5 C6 0.0(8) . . . . ?
C3 N2 C5 C1 -0.4(5) . . . . ?
C4 N2 C5 C1 -179.2(4) . . . . ?
N1 C1 C5 C6 -178.9(4) . . . . ?
C6 C1 C5 C6 0.3(8) 2_667 . . . ?
N1 C1 C5 N2 0.4(5) . . . . ?
C6 C1 C5 N2 179.6(4) 2_667 . . . ?
N2 C5 C6 C1 -179.4(5) . . . 2_667 ?
C1 C5 C6 C1 -0.3(8) . . . 2_667 ?
C13 O1 C7 C12 -160.2(4) . . . . ?
C13 O1 C7 C8 21.3(7) . . . . ?
O1 C7 C8 C9 -179.7(4) . . . . ?
C12 C7 C8 C9 1.8(8) . . . . ?
C7 C8 C9 C10 -1.2(8) . . . . ?
C20 O5 C10 C9 161.7(4) . . . . ?
C20 O5 C10 C11 -18.7(7) . . . . ?
C8 C9 C10 O5 -179.8(4) . . . . ?
C8 C9 C10 C11 0.6(7) . . . . ?
O5 C10 C11 C12 179.7(4) . . . . ?
C9 C10 C11 C12 -0.7(7) . . . . ?
C10 C11 C12 C7 1.4(7) . . . . ?
O1 C7 C12 C11 179.4(4) . . . . ?
C8 C7 C12 C11 -2.0(8) . . . . ?
C7 O1 C13 C14 152.4(4) . . . . ?
C15 O2 C14 C13 -170.4(4) . . . . ?
O1 C13 C14 O2 -67.2(5) . . . . ?
C14 O2 C15 C16 -171.7(4) . . . . ?
C17 O3 C16 C15 -64.4(5) . . . . ?
O2 C15 C16 O3 -55.6(6) . . . . ?
C16 O3 C17 C18 -161.8(4) . . . 2_667 ?
C19 O4 C18 C17 179.0(4) . . . 2_667 ?
C18 O4 C19 C20 -179.0(4) . . . . ?
C10 O5 C20 C19 -163.2(4) . . . . ?
O4 C19 C20 O5 -77.6(5) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_11rfs06
_database_code_depnum_ccdc_archive 'CCDC 1884117'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H52 Br4 N4, C36 H44 O10, 2(F6 P)'
_chemical_formula_sum            'C68 H96 Br4 F12 N4 O10 P2'
_chemical_formula_weight         1739.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9879(4)
_cell_length_b                   13.5898(4)
_cell_length_c                   13.7145(4)
_cell_angle_alpha                78.086(2)
_cell_angle_beta                 79.356(2)
_cell_angle_gamma                67.925(2)
_cell_volume                     1843.89(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7838
_cell_measurement_theta_min      3.316
_cell_measurement_theta_max      76.894

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             890
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.522
_exptl_crystal_size_mid          0.477
_exptl_crystal_size_min          0.276
_exptl_absorpt_coefficient_mu    3.842
_shelx_estimated_absorpt_T_min   0.239
_shelx_estimated_absorpt_T_max   0.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2390
_exptl_absorpt_correction_T_max  0.4169
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37174
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.317
_diffrn_reflns_theta_max         67.652
_diffrn_reflns_theta_full        67.652
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             6432
_reflns_number_gt                5811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All non hydrogen atoms were located in successive diff Fourier maps
 and refined using anisotropic displacement parameters.  O3 of the 
 macrocycle component was found to be disordered over two positions
 with occupancy factors refined to 80:20. Residual electron density
 is located near the Br atoms.

 Residual electron density (about 1 e3) reside near the PF6 anion and 
 suggests dissorder.  Attempts were made to model this disorder, however, 
 refinement of the occupancy of this two-component disorder resulted 
 in 90:10 ratio.  Due to the poor refinement of the 10% component, this
 approach was disbanded for the single component model.
 
 The H atoms were placed in calculated positions and refined with
 Uiso=1.2Ueq of the corresponding C atom. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+5.6489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6432
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58564(4) -0.19307(3) -0.56753(3) 0.03191(12) Uani 1 1 d . . . . .
Br2 Br -0.18902(5) 0.72169(3) -0.36401(3) 0.04045(14) Uani 1 1 d . . . . .
P1 P 0.24088(10) 0.67193(8) -0.26927(7) 0.0296(2) Uani 1 1 d . . . . .
F1 F 0.3609(3) 0.6772(3) -0.3520(2) 0.0649(9) Uani 1 1 d . . . . .
F2 F 0.3440(3) 0.5885(2) -0.1942(2) 0.0561(7) Uani 1 1 d . . . . .
F3 F 0.2361(3) 0.5732(2) -0.3118(2) 0.0542(7) Uani 1 1 d . . . . .
F4 F 0.1258(3) 0.6612(3) -0.1826(2) 0.0616(8) Uani 1 1 d . . . . .
F5 F 0.1422(4) 0.7519(3) -0.3412(3) 0.0847(11) Uani 1 1 d . . . . .
F6 F 0.2563(3) 0.7648(2) -0.2228(2) 0.0643(8) Uani 1 1 d . . . . .
O1 O 0.1775(3) 0.25741(19) -0.14186(18) 0.0275(5) Uani 1 1 d . . . . .
O2 O 0.0194(2) 0.3642(2) -0.29160(17) 0.0261(5) Uani 1 1 d . . . . .
O3 O -0.2004(3) 0.3798(3) -0.3776(2) 0.0275(12) Uani 0.802(11) 1 d . . P A 1
O4 O -0.4046(3) 0.3161(2) -0.27649(19) 0.0383(7) Uani 1 1 d . . . . .
O5 O -0.4213(2) 0.15541(19) -0.11899(17) 0.0250(5) Uani 1 1 d . . . . .
N1 N -0.0608(3) 0.0941(2) -0.18900(19) 0.0199(6) Uani 1 1 d . . . . .
N2 N -0.1409(3) 0.2042(2) -0.0781(2) 0.0193(6) Uani 1 1 d . . . . .
C1 C -0.1316(3) 0.1941(3) -0.1743(2) 0.0209(7) Uani 1 1 d . . . . .
H1 H -0.1705 0.2508 -0.2252 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0544(3) -0.0741(3) -0.0744(2) 0.0188(6) Uani 1 1 d . . . . .
H2 H 0.0895 -0.1222 -0.1223 0.023 Uiso 1 1 calc R U . . .
C3 C -0.0197(3) 0.0330(3) -0.0978(2) 0.0182(6) Uani 1 1 d . . . . .
C4 C -0.0725(3) 0.1043(3) -0.0262(2) 0.0187(6) Uani 1 1 d . . . . .
C5 C -0.0282(3) 0.0545(3) -0.2865(2) 0.0213(7) Uani 1 1 d . . . . .
H5A H -0.0874 0.1073 -0.3343 0.026 Uiso 1 1 calc R U . . .
H5B H -0.0445 -0.0138 -0.2775 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1148(3) 0.0364(3) -0.3304(2) 0.0227(7) Uani 1 1 d . . . . .
H6A H 0.1745 -0.0205 -0.2854 0.027 Uiso 1 1 calc R U . . .
H6B H 0.1333 0.1032 -0.3352 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1416(4) 0.0034(3) -0.4346(2) 0.0238(7) Uani 1 1 d . . . . .
H7A H 0.1128 -0.0582 -0.4308 0.029 Uiso 1 1 calc R U . . .
H7B H 0.0887 0.0638 -0.4811 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2868(4) -0.0274(3) -0.4762(2) 0.0254(7) Uani 1 1 d . . . . .
H8A H 0.3393 -0.0898 -0.4312 0.030 Uiso 1 1 calc R U . . .
H8B H 0.3165 0.0331 -0.4773 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3128(4) -0.0559(3) -0.5820(3) 0.0280(8) Uani 1 1 d . . . . .
H9A H 0.2957 -0.1231 -0.5784 0.034 Uiso 1 1 calc R U . . .
H9B H 0.2489 0.0016 -0.6236 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4502(4) -0.0703(3) -0.6337(3) 0.0324(8) Uani 1 1 d . . . . .
H10A H 0.4693 -0.0043 -0.6353 0.039 Uiso 1 1 calc R U . . .
H10B H 0.4546 -0.0803 -0.7039 0.039 Uiso 1 1 calc R U . . .
C11 C -0.2080(3) 0.3029(3) -0.0317(2) 0.0221(7) Uani 1 1 d . . . . .
H11A H -0.1476 0.3102 0.0094 0.027 Uiso 1 1 calc R U . . .
H11B H -0.2870 0.2966 0.0134 0.027 Uiso 1 1 calc R U . . .
C12 C -0.2500(3) 0.4027(3) -0.1092(2) 0.0213(7) Uani 1 1 d . . . . .
H12A H -0.3228 0.4021 -0.1419 0.026 Uiso 1 1 calc R U . . .
H12B H -0.1746 0.4026 -0.1616 0.026 Uiso 1 1 calc R U . . .
C13 C -0.2960(4) 0.5045(3) -0.0606(3) 0.0262(7) Uani 1 1 d . . . . .
H13A H -0.3892 0.5202 -0.0306 0.031 Uiso 1 1 calc R U . . .
H13B H -0.2420 0.4919 -0.0059 0.031 Uiso 1 1 calc R U . . .
C14 C -0.2849(4) 0.6019(3) -0.1360(3) 0.0279(8) Uani 1 1 d . . . . .
H14A H -0.3139 0.6646 -0.1001 0.033 Uiso 1 1 calc R U . . .
H14B H -0.1907 0.5872 -0.1629 0.033 Uiso 1 1 calc R U . . .
C15 C -0.3653(4) 0.6313(3) -0.2236(3) 0.0367(9) Uani 1 1 d . . . . .
H15A H -0.3300 0.5718 -0.2639 0.044 Uiso 1 1 calc R U . . .
H15B H -0.4579 0.6388 -0.1969 0.044 Uiso 1 1 calc R U . . .
C16 C -0.3642(4) 0.7333(3) -0.2909(3) 0.0387(9) Uani 1 1 d . . . . .
H16A H -0.3934 0.7920 -0.2500 0.046 Uiso 1 1 calc R U . . .
H16B H -0.4283 0.7525 -0.3399 0.046 Uiso 1 1 calc R U . . .
C17 C 0.2754(3) 0.0863(3) -0.0552(2) 0.0206(7) Uani 1 1 d . . . . .
C18 C 0.3138(3) 0.0463(3) -0.1483(3) 0.0239(7) Uani 1 1 d . . . . .
H18 H 0.2907 0.0935 -0.2089 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3836(3) -0.0595(3) -0.1500(3) 0.0258(7) Uani 1 1 d . . . . .
H19 H 0.4063 -0.0864 -0.2121 0.031 Uiso 1 1 calc R U . . .
C20 C 0.4235(3) -0.1307(3) -0.0614(2) 0.0230(7) Uani 1 1 d . . . . .
H20 H 0.4745 -0.2042 -0.0644 0.028 Uiso 1 1 calc R U . . .
C21 C 0.3883(3) -0.0932(3) 0.0291(2) 0.0216(7) Uani 1 1 d . . . . .
C22 C 0.3103(3) 0.0164(3) 0.0351(2) 0.0207(7) Uani 1 1 d . . . . .
C23 C 0.2658(3) 0.0567(3) 0.1281(2) 0.0235(7) Uani 1 1 d . . . . .
H23 H 0.2899 0.0103 0.1890 0.028 Uiso 1 1 calc R U . . .
C24 C 0.1886(4) 0.1620(3) 0.1300(3) 0.0258(7) Uani 1 1 d . . . . .
H24 H 0.1567 0.1874 0.1927 0.031 Uiso 1 1 calc R U . . .
C25 C 0.1552(3) 0.2339(3) 0.0407(3) 0.0244(7) Uani 1 1 d . . . . .
H25 H 0.1025 0.3072 0.0433 0.029 Uiso 1 1 calc R U . . .
C26 C 0.1996(3) 0.1967(3) -0.0499(3) 0.0224(7) Uani 1 1 d . . . . .
C27 C 0.1068(3) 0.3699(3) -0.1475(3) 0.0264(7) Uani 1 1 d . . . . .
H27A H 0.1559 0.4045 -0.1208 0.032 Uiso 1 1 calc R U . . .
H27B H 0.0186 0.3838 -0.1078 0.032 Uiso 1 1 calc R U . . .
C28 C 0.0929(4) 0.4134(3) -0.2562(3) 0.0287(8) Uani 1 1 d . . . . .
H28A H 0.0467 0.4922 -0.2645 0.034 Uiso 1 1 calc R U . . .
H28B H 0.1814 0.3981 -0.2954 0.034 Uiso 1 1 calc R U . . .
C29 C 0.0020(4) 0.4056(3) -0.3942(3) 0.0295(8) Uani 1 1 d . . . . .
H29A H 0.0894 0.3954 -0.4342 0.035 Uiso 1 1 calc R U . . .
H29B H -0.0496 0.4836 -0.4009 0.035 Uiso 1 1 calc R U . . .
C30 C -0.0676(4) 0.3509(4) -0.4330(3) 0.0382(10) Uani 1 1 d . . . . .
H30A H -0.0724 0.3751 -0.5059 0.046 Uiso 1 1 calc R U . A 1
H30B H -0.0213 0.2721 -0.4217 0.046 Uiso 1 1 calc R U . A 1
C31 C -0.2889(5) 0.3673(4) -0.4291(3) 0.0511(12) Uani 1 1 d . . . . .
H31A H -0.2534 0.2940 -0.4471 0.061 Uiso 1 1 calc R U . A 1
H31B H -0.2995 0.4192 -0.4920 0.061 Uiso 1 1 calc R U . A 1
C32 C -0.4172(4) 0.3843(3) -0.3695(3) 0.0271(7) Uani 1 1 d . . . . .
H32A H -0.4574 0.4601 -0.3580 0.032 Uiso 1 1 calc R U . . .
H32B H -0.4764 0.3701 -0.4068 0.032 Uiso 1 1 calc R U . . .
C33 C -0.5275(3) 0.3183(3) -0.2217(3) 0.0259(7) Uani 1 1 d . . . . .
H33A H -0.5677 0.2803 -0.2530 0.031 Uiso 1 1 calc R U . . .
H33B H -0.5887 0.3935 -0.2216 0.031 Uiso 1 1 calc R U . . .
C34 C -0.5047(3) 0.2645(3) -0.1165(3) 0.0241(7) Uani 1 1 d . . . . .
H34A H -0.4623 0.3014 -0.0858 0.029 Uiso 1 1 calc R U . . .
H34B H -0.5901 0.2680 -0.0757 0.029 Uiso 1 1 calc R U . . .
O3A O -0.1717(10) 0.3142(11) -0.3899(8) 0.012(4) Uiso 0.198(11) 1 d . . 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
Br1 C10 1.956(4) . ?
Br2 C16 1.964(4) . ?
P1 F5 1.548(3) . ?
P1 F1 1.586(3) . ?
P1 F3 1.591(3) . ?
P1 F4 1.595(3) . ?
P1 F6 1.600(3) . ?
P1 F2 1.616(3) . ?
O1 C26 1.365(4) . ?
O1 C27 1.424(4) . ?
O2 C28 1.420(4) . ?
O2 C29 1.423(4) . ?
O3 C31 1.377(6) . ?
O3 C30 1.464(5) . ?
O4 C32 1.410(4) . ?
O4 C33 1.412(4) . ?
O5 C21 1.368(4) 2 ?
O5 C34 1.424(4) . ?
N1 C1 1.324(4) . ?
N1 C3 1.399(4) . ?
N1 C5 1.476(4) . ?
N2 C1 1.336(4) . ?
N2 C4 1.395(4) . ?
N2 C11 1.478(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(5) . ?
C2 C4 1.384(4) 2 ?
C2 H2 0.9500 . ?
C3 C4 1.415(4) . ?
C4 C2 1.384(4) 2 ?
C5 C6 1.521(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.530(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.518(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.504(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.516(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.532(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.532(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.501(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C22 1.413(5) . ?
C17 C18 1.421(5) . ?
C17 C26 1.426(5) . ?
C18 C19 1.354(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.414(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.373(5) . ?
C20 H20 0.9500 . ?
C21 O5 1.368(4) 2 ?
C21 C22 1.423(5) . ?
C22 C23 1.422(5) . ?
C23 C24 1.365(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.410(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(5) . ?
C25 H25 0.9500 . ?
C27 C28 1.500(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.470(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O3A 1.401(11) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 O3A 1.366(12) . ?
C31 C32 1.454(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.496(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9900 . ?
C34 H34B 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
F5 P1 F1 90.1(2) . . ?
F5 P1 F3 90.7(2) . . ?
F1 P1 F3 89.91(15) . . ?
F5 P1 F4 93.0(2) . . ?
F1 P1 F4 176.9(2) . . ?
F3 P1 F4 89.48(16) . . ?
F5 P1 F6 93.7(2) . . ?
F1 P1 F6 88.73(15) . . ?
F3 P1 F6 175.41(19) . . ?
F4 P1 F6 91.64(17) . . ?
F5 P1 F2 179.9(2) . . ?
F1 P1 F2 89.83(18) . . ?
F3 P1 F2 89.33(16) . . ?
F4 P1 F2 87.09(17) . . ?
F6 P1 F2 86.28(17) . . ?
C26 O1 C27 118.9(3) . . ?
C28 O2 C29 110.4(3) . . ?
C31 O3 C30 111.4(3) . . ?
C32 O4 C33 113.1(3) . . ?
C21 O5 C34 117.0(3) 2 . ?
C1 N1 C3 109.0(3) . . ?
C1 N1 C5 125.3(3) . . ?
C3 N1 C5 125.7(3) . . ?
C1 N2 C4 108.4(3) . . ?
C1 N2 C11 127.4(3) . . ?
C4 N2 C11 124.1(3) . . ?
N1 C1 N2 110.5(3) . . ?
N1 C1 H1 124.7 . . ?
N2 C1 H1 124.7 . . ?
C3 C2 C4 113.0(3) . 2 ?
C3 C2 H2 123.5 . . ?
C4 C2 H2 123.5 2 . ?
C2 C3 N1 130.9(3) . . ?
C2 C3 C4 123.4(3) . . ?
N1 C3 C4 105.7(3) . . ?
C2 C4 N2 130.1(3) 2 . ?
C2 C4 C3 123.6(3) 2 . ?
N2 C4 C3 106.3(3) . . ?
N1 C5 C6 112.4(3) . . ?
N1 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N1 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 110.7(3) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 112.3(3) . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.4(3) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 115.0(3) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C9 C10 Br1 112.8(3) . . ?
C9 C10 H10A 109.0 . . ?
Br1 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
Br1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 112.3(3) . . ?
N2 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N2 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 110.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 112.3(3) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 114.6(3) . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.8(3) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 Br2 112.8(3) . . ?
C15 C16 H16A 109.0 . . ?
Br2 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
Br2 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C22 C17 C18 120.4(3) . . ?
C22 C17 C26 118.4(3) . . ?
C18 C17 C26 121.3(3) . . ?
C19 C18 C17 119.5(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 121.4(3) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O5 C21 C20 124.3(3) 2 . ?
O5 C21 C22 114.9(3) 2 . ?
C20 C21 C22 120.8(3) . . ?
C17 C22 C23 119.7(3) . . ?
C17 C22 C21 118.0(3) . . ?
C23 C22 C21 122.3(3) . . ?
C24 C23 C22 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 119.3(3) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
O1 C26 C25 125.6(3) . . ?
O1 C26 C17 113.2(3) . . ?
C25 C26 C17 121.2(3) . . ?
O1 C27 C28 106.6(3) . . ?
O1 C27 H27A 110.4 . . ?
C28 C27 H27A 110.4 . . ?
O1 C27 H27B 110.4 . . ?
C28 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
O2 C28 C27 109.0(3) . . ?
O2 C28 H28A 109.9 . . ?
C27 C28 H28A 109.9 . . ?
O2 C28 H28B 109.9 . . ?
C27 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
O2 C29 C30 110.8(3) . . ?
O2 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O2 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
O3A C30 C29 132.3(6) . . ?
O3 C30 C29 105.9(3) . . ?
O3 C30 H30A 110.6 . . ?
C29 C30 H30A 110.6 . . ?
O3 C30 H30B 110.6 . . ?
C29 C30 H30B 110.6 . . ?
H30A C30 H30B 108.7 . . ?
O3A C31 C32 123.3(5) . . ?
O3 C31 C32 111.5(4) . . ?
O3 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
O3 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
O4 C32 C31 110.8(3) . . ?
O4 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
O4 C33 C34 108.4(3) . . ?
O4 C33 H33A 110.0 . . ?
C34 C33 H33A 110.0 . . ?
O4 C33 H33B 110.0 . . ?
C34 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
O5 C34 C33 108.6(3) . . ?
O5 C34 H34A 110.0 . . ?
C33 C34 H34A 110.0 . . ?
O5 C34 H34B 110.0 . . ?
C33 C34 H34B 110.0 . . ?
H34A C34 H34B 108.4 . . ?
C31 O3A C30 116.1(8) . . ?

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
C3 N1 C1 N2 0.0(4) . . . . ?
C5 N1 C1 N2 -178.8(3) . . . . ?
C4 N2 C1 N1 -0.4(4) . . . . ?
C11 N2 C1 N1 178.2(3) . . . . ?
C4 C2 C3 N1 -179.4(3) 2 . . . ?
C4 C2 C3 C4 -0.4(5) 2 . . . ?
C1 N1 C3 C2 179.5(3) . . . . ?
C5 N1 C3 C2 -1.7(5) . . . . ?
C1 N1 C3 C4 0.4(3) . . . . ?
C5 N1 C3 C4 179.1(3) . . . . ?
C1 N2 C4 C2 -179.6(3) . . . 2 ?
C11 N2 C4 C2 1.7(5) . . . 2 ?
C1 N2 C4 C3 0.6(3) . . . . ?
C11 N2 C4 C3 -178.0(3) . . . . ?
C2 C3 C4 C2 0.4(5) . . . 2 ?
N1 C3 C4 C2 179.6(3) . . . 2 ?
C2 C3 C4 N2 -179.8(3) . . . . ?
N1 C3 C4 N2 -0.6(3) . . . . ?
C1 N1 C5 C6 105.1(4) . . . . ?
C3 N1 C5 C6 -73.5(4) . . . . ?
N1 C5 C6 C7 -175.8(3) . . . . ?
C5 C6 C7 C8 -173.6(3) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
C7 C8 C9 C10 170.9(3) . . . . ?
C8 C9 C10 Br1 65.0(4) . . . . ?
C1 N2 C11 C12 -9.9(5) . . . . ?
C4 N2 C11 C12 168.5(3) . . . . ?
N2 C11 C12 C13 -169.7(3) . . . . ?
C11 C12 C13 C14 156.5(3) . . . . ?
C12 C13 C14 C15 59.7(4) . . . . ?
C13 C14 C15 C16 174.1(3) . . . . ?
C14 C15 C16 Br2 66.8(4) . . . . ?
C22 C17 C18 C19 0.3(5) . . . . ?
C26 C17 C18 C19 -178.7(3) . . . . ?
C17 C18 C19 C20 -2.4(5) . . . . ?
C18 C19 C20 C21 1.7(5) . . . . ?
C19 C20 C21 O5 179.7(3) . . . 2 ?
C19 C20 C21 C22 0.9(5) . . . . ?
C18 C17 C22 C23 -177.1(3) . . . . ?
C26 C17 C22 C23 2.0(5) . . . . ?
C18 C17 C22 C21 2.2(5) . . . . ?
C26 C17 C22 C21 -178.7(3) . . . . ?
O5 C21 C22 C17 178.3(3) 2 . . . ?
C20 C21 C22 C17 -2.8(5) . . . . ?
O5 C21 C22 C23 -2.5(4) 2 . . . ?
C20 C21 C22 C23 176.5(3) . . . . ?
C17 C22 C23 C24 0.8(5) . . . . ?
C21 C22 C23 C24 -178.5(3) . . . . ?
C22 C23 C24 C25 -2.4(5) . . . . ?
C23 C24 C25 C26 1.0(5) . . . . ?
C27 O1 C26 C25 2.5(5) . . . . ?
C27 O1 C26 C17 -177.9(3) . . . . ?
C24 C25 C26 O1 -178.4(3) . . . . ?
C24 C25 C26 C17 1.9(5) . . . . ?
C22 C17 C26 O1 176.9(3) . . . . ?
C18 C17 C26 O1 -4.0(4) . . . . ?
C22 C17 C26 C25 -3.4(5) . . . . ?
C18 C17 C26 C25 175.7(3) . . . . ?
C26 O1 C27 C28 -177.5(3) . . . . ?
C29 O2 C28 C27 178.7(3) . . . . ?
O1 C27 C28 O2 61.4(3) . . . . ?
C28 O2 C29 C30 176.9(3) . . . . ?
C31 O3 C30 C29 158.3(4) . . . . ?
O2 C29 C30 O3A 38.1(9) . . . . ?
O2 C29 C30 O3 65.4(4) . . . . ?
C30 O3 C31 C32 173.6(4) . . . . ?
C33 O4 C32 C31 -171.6(4) . . . . ?
O3A C31 C32 O4 -15.8(9) . . . . ?
O3 C31 C32 O4 -55.4(5) . . . . ?
C32 O4 C33 C34 -167.0(3) . . . . ?
C21 O5 C34 C33 179.4(3) 2 . . . ?
O4 C33 C34 O5 -62.2(4) . . . . ?
C32 C31 O3A C30 -146.1(7) . . . . ?
C29 C30 O3A C31 111.9(9) . . . . ?

_refine_diff_density_max         1.716
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.090

####################################################################### 
# 
# 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_11rfs02
_database_code_depnum_ccdc_archive 'CCDC 1884119'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H44 O10, C24 H39 N4, 2(F6 P)'
_chemical_formula_sum            'C60 H83 F12 N4 O10 P2'
_chemical_formula_weight         1310.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.8478(2)
_cell_length_b                   12.9719(2)
_cell_length_c                   12.9821(2)
_cell_angle_alpha                75.025(1)
_cell_angle_beta                 67.442(1)
_cell_angle_gamma                69.602(1)
_cell_volume                     1564.75(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7694
_cell_measurement_theta_min      3.711
_cell_measurement_theta_max      68.803

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             689
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    1.465
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5268
_exptl_absorpt_correction_T_max  0.8146
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31447
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.674
_diffrn_reflns_theta_max         67.768
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5501
_reflns_number_gt                4033
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
 All non-hydrogen atoms were located in a series of difference Fourier maps and 
 refined using anisotropic displacement parameters.  The hydrogen atoms
 were placed in fixed positions with Ueq = 1.2xUiso (Ueq = 1.5xUiso for methyl
 groups) of the carbon atom to which they are attached.  Methyl Carbon C12 of
 one of the pendant butyl groups is disorded over two sites and labeled C12 and
 C12a.  Refinement of the occupancy factors resulted in a near 1:1 ratio of
 disordered components.  The model was then refinedwith fixed SOF of 50:50.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5501
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.20799(7) 0.87793(6) 0.23656(6) 0.0268(2) Uani 1 1 d . . . . .
O1 O 0.1207(2) 0.35150(15) 0.15415(15) 0.0280(4) Uani 1 1 d . . . . .
F2 F 0.36536(18) 0.80343(14) 0.19006(16) 0.0429(5) Uani 1 1 d . . . . .
F5 F 0.05070(17) 0.95044(14) 0.28351(16) 0.0406(5) Uani 1 1 d . . . . .
F1 F 0.1578(2) 0.76744(14) 0.28753(16) 0.0466(5) Uani 1 1 d . . . . .
O2 O 0.14137(19) 0.22591(16) 0.36202(15) 0.0291(5) Uani 1 1 d . . . . .
F3 F 0.1842(2) 0.87688(18) 0.12265(15) 0.0518(5) Uani 1 1 d . . . . .
O4 O 0.2266(2) 0.72208(17) -0.21907(18) 0.0389(5) Uani 1 1 d . . . . .
F6 F 0.2288(2) 0.8764(2) 0.35066(17) 0.0640(7) Uani 1 1 d . . . . .
F4 F 0.2574(2) 0.98642(16) 0.1817(2) 0.0607(6) Uani 1 1 d . . . . .
C18 C 0.1508(3) 0.5097(2) 0.0238(2) 0.0259(6) Uani 1 1 d . . . . .
C26 C 0.1334(3) 0.2350(2) 0.1786(2) 0.0280(6) Uani 1 1 d . . . . .
H26A H 0.2327 0.1920 0.1558 0.034 Uiso 1 1 calc R U . . .
H26B H 0.0868 0.2159 0.1367 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1758(3) 0.3928(2) 0.0435(2) 0.0258(6) Uani 1 1 d . . . . .
C17 C 0.2033(3) 0.5615(2) -0.0884(2) 0.0263(6) Uani 1 1 d . . . . .
C22 C 0.1775(3) 0.6791(2) -0.1079(2) 0.0305(6) Uani 1 1 d . . . . .
O3 O 0.3112(2) 0.1716(2) 0.49723(19) 0.0546(7) Uani 1 1 d . . . . .
C19 C 0.0770(3) 0.5761(2) 0.1127(2) 0.0264(6) Uani 1 1 d . . . . .
H19 H 0.0397 0.5425 0.1877 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1093(3) 0.7408(2) -0.0205(3) 0.0330(7) Uani 1 1 d . . . . .
H21 H 0.0954 0.8190 -0.0348 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0602(3) 0.6878(2) 0.0901(3) 0.0316(6) Uani 1 1 d . . . . .
H20 H 0.0144 0.7308 0.1503 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3017(3) 0.3832(3) -0.1532(2) 0.0354(7) Uani 1 1 d . . . . .
H15 H 0.3533 0.3395 -0.2126 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2503(3) 0.3307(2) -0.0428(2) 0.0296(6) Uani 1 1 d . . . . .
H14 H 0.2672 0.2522 -0.0282 0.036 Uiso 1 1 calc R U . . .
O5 O 0.4114(3) 0.8208(2) -0.4040(2) 0.0573(8) Uani 1 1 d . . . . .
C27 C 0.0664(3) 0.2079(2) 0.3026(2) 0.0287(6) Uani 1 1 d . . . . .
H27A H -0.0308 0.2554 0.3256 0.034 Uiso 1 1 calc R U . . .
H27B H 0.0647 0.1293 0.3214 0.034 Uiso 1 1 calc R U . . .
C23 C 0.2069(4) 0.8396(3) -0.2439(3) 0.0460(9) Uani 1 1 d . . . . .
H23A H 0.2545 0.8616 -0.2049 0.055 Uiso 1 1 calc R U . . .
H23B H 0.1066 0.8791 -0.2175 0.055 Uiso 1 1 calc R U . . .
C16 C 0.2787(3) 0.4963(3) -0.1766(2) 0.0336(7) Uani 1 1 d . . . . .
H16 H 0.3132 0.5306 -0.2518 0.040 Uiso 1 1 calc R U . . .
C28 C 0.1041(3) 0.1724(3) 0.4747(2) 0.0351(7) Uani 1 1 d . . . . .
H28A H 0.1407 0.0908 0.4766 0.042 Uiso 1 1 calc R U . . .
H28B H 0.0016 0.1913 0.5085 0.042 Uiso 1 1 calc R U . . .
C24 C 0.2664(4) 0.8697(3) -0.3691(3) 0.0609(12) Uani 1 1 d . . . . .
H24A H 0.2233 0.8428 -0.4079 0.073 Uiso 1 1 calc R U . . .
H24B H 0.2460 0.9515 -0.3891 0.073 Uiso 1 1 calc R U . . .
C29 C 0.1633(4) 0.2097(3) 0.5402(3) 0.0491(9) Uani 1 1 d . . . . .
H29A H 0.1328 0.2918 0.5333 0.059 Uiso 1 1 calc R U . . .
H29B H 0.1301 0.1791 0.6209 0.059 Uiso 1 1 calc R U . . .
C25 C 0.4709(4) 0.8575(5) -0.5200(3) 0.090(2) Uani 1 1 d . . . . .
H25A H 0.4584 0.9386 -0.5327 0.108 Uiso 1 1 calc R U . . .
H25B H 0.4252 0.8419 -0.5650 0.108 Uiso 1 1 calc R U . . .
C30 C 0.3764(5) 0.2041(5) 0.5547(3) 0.0805(17) Uani 1 1 d . . . . .
H30A H 0.3334 0.1865 0.6372 0.097 Uiso 1 1 calc R U . . .
H30B H 0.3643 0.2852 0.5357 0.097 Uiso 1 1 calc R U . . .
N2 N 0.3570(2) 0.43353(17) 0.21719(18) 0.0217(5) Uani 1 1 d . . . . .
N1 N 0.4807(2) 0.29660(16) 0.11920(17) 0.0196(5) Uani 1 1 d . . . . .
C2 C 0.5026(2) 0.3930(2) 0.0470(2) 0.0189(5) Uani 1 1 d . . . . .
C3 C 0.4236(2) 0.4819(2) 0.1095(2) 0.0189(5) Uani 1 1 d . . . . .
C4 C 0.3947(3) 0.3241(2) 0.2192(2) 0.0226(6) Uani 1 1 d . . . . .
H4 H 0.3643 0.2727 0.2834 0.027 Uiso 1 1 calc R U . . .
C1 C 0.5816(2) 0.4081(2) -0.0661(2) 0.0195(5) Uani 1 1 d . . . . .
H1 H 0.6339 0.3488 -0.1093 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5437(3) 0.1830(2) 0.0876(2) 0.0227(6) Uani 1 1 d . . . . .
H5A H 0.6458 0.1695 0.0546 0.027 Uiso 1 1 calc R U . . .
H5B H 0.5092 0.1787 0.0289 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7447(3) -0.0568(2) 0.1260(3) 0.0345(7) Uani 1 1 d . . . . .
H8A H 0.7871 -0.0070 0.0617 0.052 Uiso 1 1 calc R U . . .
H8B H 0.7849 -0.1334 0.1092 0.052 Uiso 1 1 calc R U . . .
H8C H 0.7626 -0.0522 0.1929 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5118(3) 0.0922(2) 0.1860(2) 0.0243(6) Uani 1 1 d . . . . .
H6A H 0.4104 0.1014 0.2160 0.029 Uiso 1 1 calc R U . . .
H6B H 0.5412 0.0982 0.2471 0.029 Uiso 1 1 calc R U . . .
C7 C 0.5881(3) -0.0225(2) 0.1481(2) 0.0284(6) Uani 1 1 d . . . . .
H7A H 0.5481 -0.0786 0.2069 0.034 Uiso 1 1 calc R U . . .
H7B H 0.5714 -0.0226 0.0784 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2655(3) 0.4918(2) 0.3151(2) 0.0268(6) Uani 1 1 d . . . . .
H9A H 0.2062 0.4454 0.3699 0.032 Uiso 1 1 calc R U . . .
H9B H 0.2040 0.5625 0.2899 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2594(4) 0.5702(3) 0.4780(2) 0.0422(8) Uani 1 1 d . . . . .
H11A H 0.3226 0.5795 0.5111 0.051 Uiso 0.5 1 calc R U P A 1
H11B H 0.2050 0.6456 0.4544 0.051 Uiso 1 1 calc R U . A 1
C10 C 0.3492(3) 0.5156(3) 0.3718(3) 0.0378(7) Uani 1 1 d . . . . .
H10A H 0.4046 0.5651 0.3176 0.045 Uiso 1 1 calc R U . . .
H10B H 0.4149 0.4451 0.3922 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1592(8) 0.5127(6) 0.5704(6) 0.055(2) Uani 0.5 1 d . . P B 1
H12A H 0.2108 0.4386 0.5972 0.082 Uiso 0.5 1 calc R U P B 1
H12B H 0.0922 0.5058 0.5409 0.082 Uiso 0.5 1 calc R U P B 1
H12C H 0.1097 0.5564 0.6329 0.082 Uiso 0.5 1 calc R U P B 1
C12A C 0.3467(9) 0.6191(7) 0.5108(6) 0.062(2) Uani 0.5 1 d . . P B 2
H12D H 0.2911 0.6502 0.5812 0.093 Uiso 0.5 1 calc R U P B 2
H12E H 0.3759 0.6780 0.4509 0.093 Uiso 0.5 1 calc R U P B 2
H12F H 0.4291 0.5605 0.5212 0.093 Uiso 0.5 1 calc R 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
P1 F6 1.576(2) . ?
P1 F4 1.578(2) . ?
P1 F5 1.5960(17) . ?
P1 F3 1.6001(19) . ?
P1 F1 1.6019(19) . ?
P1 F2 1.6041(17) . ?
O1 C13 1.369(3) . ?
O1 C26 1.430(3) . ?
O2 C28 1.415(3) . ?
O2 C27 1.420(3) . ?
O4 C22 1.371(3) . ?
O4 C23 1.431(4) . ?
C18 C13 1.416(4) . ?
C18 C17 1.423(4) . ?
C18 C19 1.428(4) . ?
C26 C27 1.495(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C13 C14 1.370(4) . ?
C17 C16 1.412(4) . ?
C17 C22 1.424(4) . ?
C22 C21 1.374(4) . ?
O3 C30 1.417(4) . ?
O3 C29 1.426(4) . ?
C19 C20 1.362(4) . ?
C19 H19 0.9500 . ?
C21 C20 1.406(4) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C15 C16 1.371(4) . ?
C15 C14 1.405(4) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
O5 C24 1.410(4) . ?
O5 C25 1.417(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C23 C24 1.501(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C16 H16 0.9500 . ?
C28 C29 1.488(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C25 C30 1.509(7) 2_665 ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C30 C25 1.509(7) 2_665 ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
N2 C4 1.329(3) . ?
N2 C3 1.399(3) . ?
N2 C9 1.475(3) . ?
N1 C4 1.327(3) . ?
N1 C2 1.389(3) . ?
N1 C5 1.484(3) . ?
C2 C1 1.390(3) . ?
C2 C3 1.409(3) . ?
C3 C1 1.381(3) 2_665 ?
C4 H4 0.9500 . ?
C1 C3 1.381(3) 2_665 ?
C1 H1 0.9500 . ?
C5 C6 1.520(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C8 C7 1.526(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 C7 1.532(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.513(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 C12 1.508(8) . ?
C11 C10 1.531(4) . ?
C11 C12A 1.533(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F6 P1 F4 91.60(14) . . ?
F6 P1 F5 89.42(11) . . ?
F4 P1 F5 91.03(10) . . ?
F6 P1 F3 178.28(13) . . ?
F4 P1 F3 90.05(13) . . ?
F5 P1 F3 90.08(11) . . ?
F6 P1 F1 90.64(13) . . ?
F4 P1 F1 177.74(13) . . ?
F5 P1 F1 89.26(10) . . ?
F3 P1 F1 87.71(11) . . ?
F6 P1 F2 90.62(11) . . ?
F4 P1 F2 89.80(10) . . ?
F5 P1 F2 179.17(11) . . ?
F3 P1 F2 89.86(10) . . ?
F1 P1 F2 89.91(10) . . ?
C13 O1 C26 116.4(2) . . ?
C28 O2 C27 110.2(2) . . ?
C22 O4 C23 116.7(3) . . ?
C13 C18 C17 118.3(2) . . ?
C13 C18 C19 122.2(3) . . ?
C17 C18 C19 119.5(2) . . ?
O1 C26 C27 107.6(2) . . ?
O1 C26 H26A 110.2 . . ?
C27 C26 H26A 110.2 . . ?
O1 C26 H26B 110.2 . . ?
C27 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
O1 C13 C14 125.4(3) . . ?
O1 C13 C18 113.6(2) . . ?
C14 C13 C18 121.0(3) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 C22 122.0(3) . . ?
C18 C17 C22 118.1(3) . . ?
O4 C22 C21 124.8(3) . . ?
O4 C22 C17 114.0(3) . . ?
C21 C22 C17 121.3(3) . . ?
C30 O3 C29 112.6(3) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C22 C21 C20 119.7(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C24 O5 C25 110.0(3) . . ?
O2 C27 C26 110.0(2) . . ?
O2 C27 H27A 109.7 . . ?
C26 C27 H27A 109.7 . . ?
O2 C27 H27B 109.7 . . ?
C26 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
O4 C23 C24 108.3(3) . . ?
O4 C23 H23A 110.0 . . ?
C24 C23 H23A 110.0 . . ?
O4 C23 H23B 110.0 . . ?
C24 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O2 C28 C29 109.0(2) . . ?
O2 C28 H28A 109.9 . . ?
C29 C28 H28A 109.9 . . ?
O2 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
O5 C24 C23 109.4(3) . . ?
O5 C24 H24A 109.8 . . ?
C23 C24 H24A 109.8 . . ?
O5 C24 H24B 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
O3 C29 C28 108.8(3) . . ?
O3 C29 H29A 109.9 . . ?
C28 C29 H29A 109.9 . . ?
O3 C29 H29B 109.9 . . ?
C28 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
O5 C25 C30 107.7(3) . 2_665 ?
O5 C25 H25A 110.2 . . ?
C30 C25 H25A 110.2 2_665 . ?
O5 C25 H25B 110.2 . . ?
C30 C25 H25B 110.2 2_665 . ?
H25A C25 H25B 108.5 . . ?
O3 C30 C25 108.9(4) . 2_665 ?
O3 C30 H30A 109.9 . . ?
C25 C30 H30A 109.9 2_665 . ?
O3 C30 H30B 109.9 . . ?
C25 C30 H30B 109.9 2_665 . ?
H30A C30 H30B 108.3 . . ?
C4 N2 C3 108.7(2) . . ?
C4 N2 C9 124.7(2) . . ?
C3 N2 C9 126.5(2) . . ?
C4 N1 C2 108.4(2) . . ?
C4 N1 C5 126.7(2) . . ?
C2 N1 C5 124.9(2) . . ?
N1 C2 C1 130.4(2) . . ?
N1 C2 C3 106.8(2) . . ?
C1 C2 C3 122.8(2) . . ?
C1 C3 N2 130.6(2) 2_665 . ?
C1 C3 C2 123.9(2) 2_665 . ?
N2 C3 C2 105.5(2) . . ?
N2 C4 N1 110.6(2) . . ?
N2 C4 H4 124.7 . . ?
N1 C4 H4 124.7 . . ?
C3 C1 C2 113.3(2) 2_665 . ?
C3 C1 H1 123.4 2_665 . ?
C2 C1 H1 123.4 . . ?
N1 C5 C6 113.6(2) . . ?
N1 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N1 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 C7 110.3(2) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 C6 114.2(2) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C9 C10 111.3(2) . . ?
N2 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C12 C11 C10 118.4(4) . . ?
C10 C11 C12A 109.3(4) . . ?
C12 C11 H11A 107.7 . . ?
C10 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
C10 C11 H11B 107.7 . . ?
H11A C11 H11B 107.1 . . ?
C9 C10 C11 113.4(3) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12A H12D 109.5 . . ?
C11 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

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
C13 O1 C26 C27 -179.7(2) . . . . ?
C26 O1 C13 C14 -5.3(4) . . . . ?
C26 O1 C13 C18 175.6(2) . . . . ?
C17 C18 C13 O1 -179.8(2) . . . . ?
C19 C18 C13 O1 1.1(4) . . . . ?
C17 C18 C13 C14 1.0(4) . . . . ?
C19 C18 C13 C14 -178.1(3) . . . . ?
C13 C18 C17 C16 -0.3(4) . . . . ?
C19 C18 C17 C16 178.8(2) . . . . ?
C13 C18 C17 C22 179.8(2) . . . . ?
C19 C18 C17 C22 -1.1(4) . . . . ?
C23 O4 C22 C21 1.3(4) . . . . ?
C23 O4 C22 C17 -178.5(2) . . . . ?
C16 C17 C22 O4 2.8(4) . . . . ?
C18 C17 C22 O4 -177.3(2) . . . . ?
C16 C17 C22 C21 -177.1(3) . . . . ?
C18 C17 C22 C21 2.8(4) . . . . ?
C13 C18 C19 C20 177.5(3) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
O4 C22 C21 C20 178.3(2) . . . . ?
C17 C22 C21 C20 -1.8(4) . . . . ?
C18 C19 C20 C21 2.6(4) . . . . ?
C22 C21 C20 C19 -0.9(4) . . . . ?
O1 C13 C14 C15 -179.9(2) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C28 O2 C27 C26 -163.7(2) . . . . ?
O1 C26 C27 O2 -65.1(3) . . . . ?
C22 O4 C23 C24 -179.5(2) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C18 C17 C16 C15 -0.5(4) . . . . ?
C22 C17 C16 C15 179.4(3) . . . . ?
C27 O2 C28 C29 -169.5(2) . . . . ?
C25 O5 C24 C23 -174.1(4) . . . . ?
O4 C23 C24 O5 -64.9(4) . . . . ?
C30 O3 C29 C28 179.7(3) . . . . ?
O2 C28 C29 O3 -65.4(3) . . . . ?
C24 O5 C25 C30 -175.6(4) . . . 2_665 ?
C29 O3 C30 C25 169.1(3) . . . 2_665 ?
C4 N1 C2 C1 -178.7(3) . . . . ?
C5 N1 C2 C1 1.0(4) . . . . ?
C4 N1 C2 C3 -0.1(3) . . . . ?
C5 N1 C2 C3 179.6(2) . . . . ?
C4 N2 C3 C1 -179.8(3) . . . 2_665 ?
C9 N2 C3 C1 -2.7(4) . . . 2_665 ?
C4 N2 C3 C2 0.8(3) . . . . ?
C9 N2 C3 C2 177.9(2) . . . . ?
N1 C2 C3 C1 -179.9(2) . . . 2_665 ?
C1 C2 C3 C1 -1.2(4) . . . 2_665 ?
N1 C2 C3 N2 -0.4(3) . . . . ?
C1 C2 C3 N2 178.3(2) . . . . ?
C3 N2 C4 N1 -0.9(3) . . . . ?
C9 N2 C4 N1 -178.0(2) . . . . ?
C2 N1 C4 N2 0.7(3) . . . . ?
C5 N1 C4 N2 -179.1(2) . . . . ?
N1 C2 C1 C3 179.4(2) . . . 2_665 ?
C3 C2 C1 C3 1.0(4) . . . 2_665 ?
C4 N1 C5 C6 -5.4(4) . . . . ?
C2 N1 C5 C6 175.0(2) . . . . ?
N1 C5 C6 C7 -176.3(2) . . . . ?
C5 C6 C7 C8 72.7(3) . . . . ?
C4 N2 C9 C10 96.8(3) . . . . ?
C3 N2 C9 C10 -79.8(3) . . . . ?
N2 C9 C10 C11 -176.7(2) . . . . ?
C12 C11 C10 C9 55.1(5) . . . . ?
C12A C11 C10 C9 -164.9(4) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_10rfs09_squeezed
_database_code_depnum_ccdc_archive 'CCDC 1884121'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_vrf_PLAT410_I                   
;
PROBLEM: Short Intra H...H Contact  H19A   ..  H20A    ..       1.76 Ang. 
RESPONSE: The macrocylic ether component of the Rotaxane structures are
often probematic and exhibit disorder.  Though this structure is relatively 
well behaved, some minor structural perturbations exist.  Several
restraints were applied with the ether macrocycle was largely allowed to 
refine freely. 
;
_vrf_PLAT601_I                   
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        557 A**3 
RESPONSE: Significant unidentifiable residual electron density was
 observed at 1.5 e/A3 suggesting the possible presence of disorded solvent.
 Processing the data with Platon/Squeeze produced a solventless data set that
 gave satisfactory convergence of the refinement model.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H44 O10, C12 H16 N4, 2(F6 P)'
_chemical_formula_sum            'C48 H60 F12 N4 O10 P2'
_chemical_formula_weight         1142.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           122
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'y, -x, -z'
'-x, -y, z'
'-y, x, -z'
'x, -y+1/2, -z+1/4'
'-x, y+1/2, -z+1/4'
'-y, -x+1/2, z+1/4'
'y, x+1/2, z+1/4'
'x+1/2, y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1, -z+3/4'
'-x+1/2, y+1, -z+3/4'
'-y+1/2, -x+1, z+3/4'
'y+1/2, x+1, z+3/4'

_cell_length_a                   22.7748(2)
_cell_length_b                   22.7748(2)
_cell_length_c                   22.9902(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     11924.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8167
_cell_measurement_theta_min      2.731
_cell_measurement_theta_max      67.417

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             4752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.208
_exptl_absorpt_coefficient_mu    1.464
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_T_max  0.737
_exptl_absorpt_process_details   'SADABS (Bruker, 2009)'
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64801
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.1089
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.731
_diffrn_reflns_theta_max         67.961
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5414
_reflns_number_gt                4530
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2009) and XPREP (Bruker, 2009)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All non-hydrogen atoms were located in a sequence of difference density maps
 and refined using anisotropic displacement parameters.  The C-C and C-O bonds
 of the ether fragment were restrained with similar distances (esd 0.2 ang). All
 H atoms were placed in calculated positions with Ueq = 1.2 x Uiso (1.5 x Uiso for
 methyl H atoms).
 
 Refinement with this model resulted in a final R value of 10%.  Significant
 unidentifiable residual electron density was observed at 1.5 e/A3 suggesting
 the possible presence of disorded solvent.  Processing the data with
 Platon/Squeeze produced a solventless data set that gave satisfactory
 convergence.  The number of electrons (585 e's) determined for this
 void space (2278 A3) corresponds to roughly 15 solvent molecules (Et2O, 42 e's; 
 Acetone, 32 e's). Recrystallization method: vapor diffusion of Et2O in acetone. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1382P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.511(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5414
_refine_ls_number_parameters     348
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37414(8) 0.2500 0.1250 0.0352(4) Uani 1 2 d S T P . .
P2 P 0.2500 0.38648(10) 0.3750 0.0662(7) Uani 1 2 d S T P . .
F1 F 0.42359(14) 0.29355(13) 0.10073(13) 0.0448(7) Uani 1 1 d . . . . .
F2 F 0.37418(15) 0.21544(13) 0.06442(12) 0.0465(7) Uani 1 1 d . . . . .
F3 F 0.32458(14) 0.29333(15) 0.10072(13) 0.0479(7) Uani 1 1 d . . . . .
F4 F 0.2077(3) 0.3374(2) 0.3484(3) 0.121(2) Uani 1 1 d . . . . .
F5 F 0.2891(3) 0.3837(4) 0.3192(3) 0.132(2) Uani 1 1 d . . . . .
F6 F 0.2103(3) 0.4351(2) 0.3460(2) 0.1052(19) Uani 1 1 d . . . . .
O1 O 0.42074(19) 0.1680(2) 0.46398(19) 0.0595(11) Uani 1 1 d D . . . .
O2 O 0.4065(4) 0.1802(3) 0.5874(3) 0.122(3) Uani 1 1 d D . . . .
O3 O 0.13411(16) 0.08484(13) 0.52549(16) 0.0408(8) Uani 1 1 d . . . . .
O4 O 0.20741(17) 0.06378(17) 0.62809(17) 0.0504(9) Uani 1 1 d D . . . .
O5 O 0.3222(2) 0.1074(3) 0.6441(2) 0.0920(19) Uani 1 1 d D . . . .
N1 N 0.26719(19) 0.1769(2) 0.48238(19) 0.0443(10) Uani 1 1 d . . . . .
N2 N 0.26860(18) 0.0816(2) 0.48182(19) 0.0438(10) Uani 1 1 d . . . . .
C1 C 0.2500 0.0649(3) 0.3750 0.0391(15) Uani 1 2 d S T P . .
H1 H 0.2500 0.0232 0.3750 0.047 Uiso 1 2 calc R U P . .
C2 C 0.25847(19) 0.0980(2) 0.4238(2) 0.0358(10) Uani 1 1 d . . . . .
C3 C 0.2582(2) 0.1597(2) 0.4248(2) 0.0339(10) Uani 1 1 d . . . . .
C4 C 0.2500 0.1945(3) 0.3750 0.0363(14) Uani 1 2 d S T P . .
H4 H 0.2500 0.2362 0.3750 0.044 Uiso 1 2 calc R U P . .
C5 C 0.2667(3) 0.2383(3) 0.5028(3) 0.0592(16) Uani 1 1 d . . . . .
H5A H 0.2267 0.2540 0.5003 0.089 Uiso 1 1 calc R U . . .
H5B H 0.2930 0.2619 0.4785 0.089 Uiso 1 1 calc R U . . .
H5C H 0.2801 0.2398 0.5433 0.089 Uiso 1 1 calc R U . . .
C6 C 0.2730(2) 0.1295(3) 0.5139(2) 0.0497(13) Uani 1 1 d . . . . .
H6 H 0.2796 0.1295 0.5547 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2739(3) 0.0212(3) 0.5017(3) 0.0568(15) Uani 1 1 d . . . . .
H7A H 0.3127 0.0059 0.4912 0.085 Uiso 1 1 calc R U . . .
H7B H 0.2435 -0.0029 0.4832 0.085 Uiso 1 1 calc R U . . .
H7C H 0.2691 0.0197 0.5440 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3798(2) 0.0750(2) 0.2821(3) 0.0409(12) Uani 1 1 d . . . . .
C9 C 0.3878(2) 0.0212(2) 0.3070(3) 0.0465(13) Uani 1 1 d . . . . .
H9 H 0.3846 -0.0136 0.2844 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4008(2) 0.0185(2) 0.3659(3) 0.0571(16) Uani 1 1 d . . . . .
H10 H 0.4060 -0.0189 0.3834 0.069 Uiso 1 1 calc R U . . .
C11 C 0.4064(2) 0.0670(3) 0.3998(3) 0.0528(15) Uani 1 1 d . . . . .
H11 H 0.4147 0.0630 0.4401 0.063 Uiso 1 1 calc R U . . .
C12 C 0.39983(18) 0.1237(2) 0.3750(3) 0.0417(11) Uani 1 1 d . . . . .
C13 C 0.38572(18) 0.1280(2) 0.3149(2) 0.0356(10) Uani 1 1 d . . . . .
C14 C 0.3799(2) 0.1840(2) 0.2881(2) 0.0369(10) Uani 1 1 d . . . . .
H14 H 0.3717 0.1869 0.2476 0.044 Uiso 1 1 calc R U . . .
C15 C 0.3861(2) 0.2336(2) 0.3214(3) 0.0443(12) Uani 1 1 d . . . . .
H15 H 0.3805 0.2711 0.3040 0.053 Uiso 1 1 calc R U . . .
C16 C 0.4008(2) 0.2300(2) 0.3808(3) 0.0490(13) Uani 1 1 d . . . . .
H16 H 0.4066 0.2648 0.4029 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4067(2) 0.1761(3) 0.4066(2) 0.0441(12) Uani 1 1 d . . . . .
C18 C 0.4336(4) 0.2188(4) 0.4975(3) 0.088(3) Uani 1 1 d D . . . .
H18A H 0.3978 0.2434 0.5006 0.105 Uiso 1 1 calc R U . . .
H18B H 0.4641 0.2422 0.4774 0.105 Uiso 1 1 calc R U . . .
C19 C 0.4543(5) 0.2038(6) 0.5562(4) 0.114(4) Uani 1 1 d D . . . .
H19A H 0.4865 0.1746 0.5539 0.136 Uiso 1 1 calc R U . . .
H19B H 0.4694 0.2393 0.5761 0.136 Uiso 1 1 calc R U . . .
C20 C 0.4184(6) 0.1213(6) 0.5910(6) 0.151(6) Uani 1 1 d D . . . .
H20A H 0.4612 0.1143 0.5947 0.181 Uiso 1 1 calc R U . . .
H20B H 0.4036 0.1002 0.5564 0.181 Uiso 1 1 calc R U . . .
C25 C 0.1292(3) 0.0363(2) 0.5658(3) 0.0501(13) Uani 1 1 d D . . . .
H25A H 0.1558 0.0040 0.5541 0.060 Uiso 1 1 calc R U . . .
H25B H 0.0885 0.0212 0.5663 0.060 Uiso 1 1 calc R U . . .
C24 C 0.1459(2) 0.0591(2) 0.6244(3) 0.0490(13) Uani 1 1 d D . . . .
H24A H 0.1277 0.0980 0.6308 0.059 Uiso 1 1 calc R U . . .
H24B H 0.1313 0.0320 0.6549 0.059 Uiso 1 1 calc R U . . .
C23 C 0.2253(3) 0.0931(4) 0.6807(2) 0.072(2) Uani 1 1 d D . . . .
H23A H 0.2031 0.0776 0.7144 0.086 Uiso 1 1 calc R U . . .
H23B H 0.2179 0.1358 0.6777 0.086 Uiso 1 1 calc R U . . .
C22 C 0.2888(3) 0.0819(5) 0.6882(3) 0.104(4) Uani 1 1 d D . . . .
H22A H 0.3016 0.0977 0.7262 0.124 Uiso 1 1 calc R U . . .
H22B H 0.2957 0.0390 0.6885 0.124 Uiso 1 1 calc R U . . .
C21 C 0.3860(4) 0.1021(6) 0.6458(5) 0.113(4) Uani 1 1 d D . . . .
H21A H 0.3961 0.0606 0.6537 0.136 Uiso 1 1 calc R U . . .
H21B H 0.4008 0.1257 0.6788 0.136 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 F3 1.600(3) 5 ?
P1 F2 1.600(3) 5 ?
P1 F3 1.600(3) . ?
P1 F2 1.600(3) . ?
P1 F1 1.601(3) 5 ?
P1 F1 1.601(3) . ?
P2 F5 1.563(6) 14_545 ?
P2 F5 1.563(6) . ?
P2 F6 1.577(5) 14_545 ?
P2 F6 1.577(5) . ?
P2 F4 1.597(6) . ?
P2 F4 1.597(6) 14_545 ?
O1 C17 1.370(7) . ?
O1 C18 1.422(9) . ?
O2 C20 1.370(14) . ?
O2 C19 1.411(12) . ?
O3 C8 1.381(7) 14_545 ?
O3 C25 1.446(6) . ?
O4 C24 1.408(7) . ?
O4 C23 1.442(8) . ?
O5 C22 1.394(9) . ?
O5 C21 1.460(11) . ?
N1 C6 1.308(8) . ?
N1 C3 1.397(7) . ?
N1 C5 1.475(8) . ?
N2 C6 1.320(8) . ?
N2 C2 1.404(7) . ?
N2 C7 1.456(7) . ?
C1 C2 1.366(6) 14_545 ?
C1 C2 1.366(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.405(7) . ?
C3 C4 1.404(6) . ?
C4 C3 1.404(6) 14_545 ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.364(7) . ?
C8 O3 1.381(7) 14_545 ?
C8 C13 1.429(7) . ?
C9 C10 1.389(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.357(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(7) . ?
C11 H11 0.9500 . ?
C12 C17 1.407(8) . ?
C12 C13 1.420(8) . ?
C13 C14 1.422(7) . ?
C14 C15 1.374(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.409(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(8) . ?
C16 H16 0.9500 . ?
C18 C19 1.471(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.523(13) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C25 C24 1.494(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C23 C22 1.478(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 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
F3 P1 F2 90.02(17) 5 5 ?
F3 P1 F3 90.3(3) 5 . ?
F2 P1 F3 90.04(16) 5 . ?
F3 P1 F2 90.04(16) 5 . ?
F2 P1 F2 179.9(3) 5 . ?
F3 P1 F2 90.02(17) . . ?
F3 P1 F1 89.58(16) 5 5 ?
F2 P1 F1 90.05(16) 5 5 ?
F3 P1 F1 179.8(2) . 5 ?
F2 P1 F1 89.89(17) . 5 ?
F3 P1 F1 179.8(2) 5 . ?
F2 P1 F1 89.90(17) 5 . ?
F3 P1 F1 89.58(16) . . ?
F2 P1 F1 90.05(16) . . ?
F1 P1 F1 90.6(2) 5 . ?
F5 P2 F5 175.4(6) 14_545 . ?
F5 P2 F6 90.5(4) 14_545 14_545 ?
F5 P2 F6 92.7(4) . 14_545 ?
F5 P2 F6 92.7(4) 14_545 . ?
F5 P2 F6 90.5(4) . . ?
F6 P2 F6 90.8(4) 14_545 . ?
F5 P2 F4 86.6(4) 14_545 . ?
F5 P2 F4 90.1(4) . . ?
F6 P2 F4 177.2(4) 14_545 . ?
F6 P2 F4 89.1(3) . . ?
F5 P2 F4 90.1(4) 14_545 14_545 ?
F5 P2 F4 86.7(4) . 14_545 ?
F6 P2 F4 89.1(3) 14_545 14_545 ?
F6 P2 F4 177.2(4) . 14_545 ?
F4 P2 F4 91.2(5) . 14_545 ?
C17 O1 C18 117.3(5) . . ?
C20 O2 C19 104.5(10) . . ?
C8 O3 C25 118.3(4) 14_545 . ?
C24 O4 C23 111.5(5) . . ?
C22 O5 C21 119.4(6) . . ?
C6 N1 C3 108.0(5) . . ?
C6 N1 C5 127.4(5) . . ?
C3 N1 C5 124.6(5) . . ?
C6 N2 C2 108.9(5) . . ?
C6 N2 C7 126.8(5) . . ?
C2 N2 C7 124.3(5) . . ?
C2 C1 C2 112.9(6) 14_545 . ?
C2 C1 H1 123.5 14_545 . ?
C2 C1 H1 123.5 . . ?
C1 C2 N2 131.0(5) . . ?
C1 C2 C3 124.4(5) . . ?
N2 C2 C3 104.6(4) . . ?
N1 C3 C4 129.3(5) . . ?
N1 C3 C2 107.2(4) . . ?
C4 C3 C2 123.5(5) . . ?
C3 C4 C3 111.3(6) 14_545 . ?
C3 C4 H4 124.4 14_545 . ?
C3 C4 H4 124.4 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 N2 111.4(5) . . ?
N1 C6 H6 124.3 . . ?
N2 C6 H6 124.3 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 O3 125.2(5) . 14_545 ?
C9 C8 C13 121.7(5) . . ?
O3 C8 C13 113.0(4) 14_545 . ?
C8 C9 C10 118.4(5) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 123.0(5) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 C12 119.9(6) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C17 C12 C11 123.5(5) . . ?
C17 C12 C13 117.9(4) . . ?
C11 C12 C13 118.6(5) . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 C8 118.3(4) . . ?
C14 C13 C8 121.2(5) . . ?
C15 C14 C13 119.1(5) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 119.7(5) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 O1 124.1(5) . . ?
C16 C17 C12 121.8(5) . . ?
O1 C17 C12 114.1(5) . . ?
O1 C18 C19 111.9(9) . . ?
O1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
O1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
O2 C19 C18 107.9(8) . . ?
O2 C19 H19A 110.1 . . ?
C18 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
C18 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
O2 C20 C21 103.6(10) . . ?
O2 C20 H20A 111.0 . . ?
C21 C20 H20A 111.0 . . ?
O2 C20 H20B 111.0 . . ?
C21 C20 H20B 111.0 . . ?
H20A C20 H20B 109.0 . . ?
O3 C25 C24 107.1(4) . . ?
O3 C25 H25A 110.3 . . ?
C24 C25 H25A 110.3 . . ?
O3 C25 H25B 110.3 . . ?
C24 C25 H25B 110.3 . . ?
H25A C25 H25B 108.5 . . ?
O4 C24 C25 109.5(4) . . ?
O4 C24 H24A 109.8 . . ?
C25 C24 H24A 109.8 . . ?
O4 C24 H24B 109.8 . . ?
C25 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
O4 C23 C22 107.1(6) . . ?
O4 C23 H23A 110.3 . . ?
C22 C23 H23A 110.3 . . ?
O4 C23 H23B 110.3 . . ?
C22 C23 H23B 110.3 . . ?
H23A C23 H23B 108.5 . . ?
O5 C22 C23 112.1(6) . . ?
O5 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
O5 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O5 C21 C20 115.9(9) . . ?
O5 C21 H21A 108.3 . . ?
C20 C21 H21A 108.3 . . ?
O5 C21 H21B 108.3 . . ?
C20 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?

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
C2 C1 C2 N2 -179.9(6) 14_545 . . . ?
C2 C1 C2 C3 0.4(3) 14_545 . . . ?
C6 N2 C2 C1 -178.8(4) . . . . ?
C7 N2 C2 C1 1.9(8) . . . . ?
C6 N2 C2 C3 0.9(5) . . . . ?
C7 N2 C2 C3 -178.4(5) . . . . ?
C6 N1 C3 C4 -179.7(4) . . . . ?
C5 N1 C3 C4 3.3(8) . . . . ?
C6 N1 C3 C2 0.6(6) . . . . ?
C5 N1 C3 C2 -176.5(5) . . . . ?
C1 C2 C3 N1 178.8(4) . . . . ?
N2 C2 C3 N1 -0.9(5) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
N2 C2 C3 C4 179.4(3) . . . . ?
N1 C3 C4 C3 -179.3(6) . . . 14_545 ?
C2 C3 C4 C3 0.4(3) . . . 14_545 ?
C3 N1 C6 N2 0.0(6) . . . . ?
C5 N1 C6 N2 176.9(5) . . . . ?
C2 N2 C6 N1 -0.5(6) . . . . ?
C7 N2 C6 N1 178.7(5) . . . . ?
O3 C8 C9 C10 -179.0(4) 14_545 . . . ?
C13 C8 C9 C10 1.3(7) . . . . ?
C8 C9 C10 C11 -0.6(8) . . . . ?
C9 C10 C11 C12 -1.0(9) . . . . ?
C10 C11 C12 C17 -178.0(5) . . . . ?
C10 C11 C12 C13 1.9(7) . . . . ?
C17 C12 C13 C14 1.1(6) . . . . ?
C11 C12 C13 C14 -178.8(4) . . . . ?
C17 C12 C13 C8 178.7(4) . . . . ?
C11 C12 C13 C8 -1.1(6) . . . . ?
C9 C8 C13 C12 -0.5(6) . . . . ?
O3 C8 C13 C12 179.8(4) 14_545 . . . ?
C9 C8 C13 C14 177.2(5) . . . . ?
O3 C8 C13 C14 -2.6(6) 14_545 . . . ?
C12 C13 C14 C15 -2.1(6) . . . . ?
C8 C13 C14 C15 -179.7(4) . . . . ?
C13 C14 C15 C16 2.9(7) . . . . ?
C14 C15 C16 C17 -2.6(8) . . . . ?
C15 C16 C17 O1 -179.9(5) . . . . ?
C15 C16 C17 C12 1.5(8) . . . . ?
C18 O1 C17 C16 -4.2(8) . . . . ?
C18 O1 C17 C12 174.5(6) . . . . ?
C11 C12 C17 C16 179.1(5) . . . . ?
C13 C12 C17 C16 -0.8(7) . . . . ?
C11 C12 C17 O1 0.4(7) . . . . ?
C13 C12 C17 O1 -179.5(4) . . . . ?
C17 O1 C18 C19 -173.6(7) . . . . ?
C20 O2 C19 C18 107.1(12) . . . . ?
O1 C18 C19 O2 -69.5(12) . . . . ?
C19 O2 C20 C21 153.8(9) . . . . ?
C8 O3 C25 C24 -179.2(4) 14_545 . . . ?
C23 O4 C24 C25 172.0(5) . . . . ?
O3 C25 C24 O4 -77.5(5) . . . . ?
C24 O4 C23 C22 165.1(6) . . . . ?
C21 O5 C22 C23 178.1(9) . . . . ?
O4 C23 C22 O5 65.0(11) . . . . ?
C22 O5 C21 C20 169.4(11) . . . . ?
O2 C20 C21 O5 64.0(14) . . . . ?

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
C6 H6 O5 0.95 2.33 3.235(7) 159.6 .

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_11rfs04
_database_code_depnum_ccdc_archive 'CCDC 1884118'
_audit_update_record             
;
2018-12-07 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H40 O10, C24 H40 N4, 2(F6 P), C3 H6 O'
_chemical_formula_sum            'C55 H86 F12 N4 O11 P2'
_chemical_formula_weight         1269.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.0528(4)
_cell_length_b                   16.2715(6)
_cell_length_c                   17.9174(6)
_cell_angle_alpha                92.546(2)
_cell_angle_beta                 97.823(2)
_cell_angle_gamma                107.791(2)
_cell_volume                     3027.05(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3716
_cell_measurement_theta_min      2.500
_cell_measurement_theta_max      58.353

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.505
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5429
_exptl_absorpt_correction_T_max  0.8809
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_special_details           
; 
 ? 
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            62977
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.499
_diffrn_reflns_theta_max         67.946
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             10685
_reflns_number_gt                7142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_refine_special_details          
;
All nonhydrogen atoms were located in succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. 
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0487P)²+1.2108P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10685
_refine_ls_number_parameters     763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.41061(7) 0.64853(5) 0.79506(4) 0.02331(17) Uani 1 1 d . . . . .
P2 P 0.45230(8) 0.13562(6) 0.74472(5) 0.0342(2) Uani 1 1 d . . . . .
F1 F 0.50648(17) 0.69358(13) 0.73896(10) 0.0427(5) Uani 1 1 d . . . . .
F2 F 0.50656(16) 0.70947(12) 0.86465(10) 0.0393(5) Uani 1 1 d . . . . .
F3 F 0.33773(18) 0.71863(12) 0.78307(12) 0.0472(5) Uani 1 1 d . . . . .
F4 F 0.31469(16) 0.60379(13) 0.85136(10) 0.0421(5) Uani 1 1 d . . . . .
F5 F 0.31314(17) 0.58808(12) 0.72580(10) 0.0406(5) Uani 1 1 d . . . . .
F6 F 0.48259(18) 0.57816(12) 0.80771(12) 0.0496(5) Uani 1 1 d . . . . .
F7 F 0.32668(19) 0.16318(14) 0.74945(13) 0.0533(6) Uani 1 1 d . . . . .
F8 F 0.4923(2) 0.20319(13) 0.68336(12) 0.0492(5) Uani 1 1 d . . . . .
F9 F 0.57760(17) 0.10719(12) 0.73814(12) 0.0473(5) Uani 1 1 d . . . . .
F10 F 0.37262(19) 0.06248(14) 0.67759(13) 0.0558(6) Uani 1 1 d . . . . .
F11 F 0.4116(2) 0.06732(14) 0.80471(12) 0.0573(6) Uani 1 1 d . . . . .
F24 F 0.5322(2) 0.20863(14) 0.81018(12) 0.0602(6) Uani 1 1 d . . . . .
O1 O 0.05019(18) 0.67001(12) 0.22740(11) 0.0239(4) Uani 1 1 d . . . . .
O2 O 0.09689(18) 0.34325(12) 0.18936(11) 0.0243(4) Uani 1 1 d . . . . .
O3 O 0.08363(18) 0.19135(12) 0.10519(10) 0.0246(4) Uani 1 1 d . . . . .
O4 O 0.08293(19) 0.11592(13) -0.04429(10) 0.0274(5) Uani 1 1 d . . . . .
O5 O 0.00327(18) 0.18509(12) -0.17165(10) 0.0253(4) Uani 1 1 d . . . . .
O6 O -0.29995(19) 0.21335(12) 0.50475(11) 0.0278(5) Uani 1 1 d . . . . .
O7 O -0.32516(19) 0.54540(13) 0.55572(11) 0.0271(5) Uani 1 1 d . . . . .
O8 O -0.23482(18) 0.72431(12) 0.55022(10) 0.0242(4) Uani 1 1 d . . . . .
O9 O -0.09859(18) 0.86481(12) 0.47218(10) 0.0249(4) Uani 1 1 d . . . . .
O10 O 0.14335(19) 0.88124(12) 0.42703(11) 0.0273(5) Uani 1 1 d . . . . .
O11 O 0.2595(2) 0.06243(16) 0.27607(14) 0.0479(6) Uani 1 1 d . . . . .
N1 N 0.0516(2) 0.35972(14) 0.55641(12) 0.0192(5) Uani 1 1 d . . . . .
N2 N -0.0600(2) 0.33174(14) 0.44288(12) 0.0190(5) Uani 1 1 d . . . . .
N3 N -0.0630(2) 0.32585(15) 0.01085(13) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.1001(2) 0.37782(15) -0.04929(12) 0.0209(5) Uani 1 1 d . . . . .
C1 C 0.0768(2) 0.51912(17) 0.57579(15) 0.0192(6) Uani 1 1 d . . . . .
H1 H 0.1268 0.5314 0.6248 0.023 Uiso 1 1 calc R U . . .
C2 C 0.0351(2) 0.43751(18) 0.53584(15) 0.0195(6) Uani 1 1 d . . . . .
C3 C -0.0379(2) 0.41934(17) 0.46336(15) 0.0186(6) Uani 1 1 d . . . . .
C4 C -0.1273(3) 0.28435(18) 0.36928(15) 0.0247(6) Uani 1 1 d . . . . .
H4A H -0.1020 0.3220 0.3284 0.030 Uiso 1 1 calc R U . . .
H4B H -0.2212 0.2710 0.3678 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0973(3) 0.20086(18) 0.35488(16) 0.0252(6) Uani 1 1 d . . . . .
H5A H -0.1412 0.1579 0.3878 0.030 Uiso 1 1 calc R U . . .
H5B H -0.0035 0.2119 0.3684 0.030 Uiso 1 1 calc R U . . .
C6 C -0.1398(3) 0.16357(19) 0.27294(16) 0.0291(7) Uani 1 1 d . . . . .
H6A H -0.1003 0.2079 0.2398 0.035 Uiso 1 1 calc R U . . .
H6B H -0.2344 0.1492 0.2603 0.035 Uiso 1 1 calc R U . . .
C7 C -0.1025(3) 0.0827(2) 0.25723(18) 0.0337(7) Uani 1 1 d . . . . .
H7A H -0.0094 0.0960 0.2716 0.051 Uiso 1 1 calc R U . . .
H7B H -0.1269 0.0631 0.2032 0.051 Uiso 1 1 calc R U . . .
H7C H -0.1473 0.0369 0.2867 0.051 Uiso 1 1 calc R U . . .
C8 C -0.0054(2) 0.29892(18) 0.49996(14) 0.0198(6) Uani 1 1 d . . . . .
H8 H -0.0071 0.2402 0.5002 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1254(3) 0.34574(18) 0.62685(14) 0.0207(6) Uani 1 1 d . . . . .
H9A H 0.1083 0.2827 0.6300 0.025 Uiso 1 1 calc R U . . .
H9B H 0.0958 0.3687 0.6706 0.025 Uiso 1 1 calc R U . . .
C10 C 0.2688(3) 0.38923(18) 0.63150(15) 0.0226(6) Uani 1 1 d . . . . .
H10A H 0.2870 0.4526 0.6301 0.027 Uiso 1 1 calc R U . . .
H10B H 0.2989 0.3674 0.5874 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3411(3) 0.3709(2) 0.70417(15) 0.0264(7) Uani 1 1 d . . . . .
H11A H 0.3186 0.3991 0.7480 0.032 Uiso 1 1 calc R U . . .
H11B H 0.3136 0.3077 0.7086 0.032 Uiso 1 1 calc R U . . .
C12 C 0.4855(3) 0.4037(2) 0.70629(18) 0.0344(7) Uani 1 1 d . . . . .
H12A H 0.5081 0.3757 0.6631 0.052 Uiso 1 1 calc R U . . .
H12B H 0.5283 0.3899 0.7534 0.052 Uiso 1 1 calc R U . . .
H12C H 0.5134 0.4666 0.7037 0.052 Uiso 1 1 calc R U . . .
C13 C 0.1102(2) 0.53502(18) -0.03928(14) 0.0202(6) Uani 1 1 d . . . . .
H13 H 0.1820 0.5577 -0.0645 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0617(2) 0.44804(18) -0.02784(14) 0.0199(6) Uani 1 1 d . . . . .
C15 C -0.0438(3) 0.41435(17) 0.01029(15) 0.0207(6) Uani 1 1 d . . . . .
C16 C -0.1632(3) 0.26219(18) 0.04402(16) 0.0246(6) Uani 1 1 d . . . . .
H16A H -0.2024 0.2934 0.0774 0.030 Uiso 1 1 calc R U . . .
H16B H -0.1230 0.2260 0.0754 0.030 Uiso 1 1 calc R U . . .
C17 C -0.2657(3) 0.2051(2) -0.0155(2) 0.0466(9) Uani 1 1 d . . . . .
H17A H -0.2277 0.1693 -0.0453 0.056 Uiso 1 1 calc R U . . .
H17B H -0.2985 0.2417 -0.0504 0.056 Uiso 1 1 calc R U . . .
C18 C -0.3808(4) 0.1439(2) 0.0176(2) 0.0537(10) Uani 1 1 d . . . . .
H18A H -0.4111 0.1778 0.0540 0.064 Uiso 1 1 calc R U . . .
H18B H -0.4532 0.1157 -0.0235 0.064 Uiso 1 1 calc R U . . .
C19 C -0.3366(4) 0.0787(3) 0.0556(3) 0.0783(14) Uani 1 1 d . . . . .
H19A H -0.2997 0.0491 0.0204 0.117 Uiso 1 1 calc R U . . .
H19B H -0.4094 0.0365 0.0725 0.117 Uiso 1 1 calc R U . . .
H19C H -0.2710 0.1067 0.0994 0.117 Uiso 1 1 calc R U . . .
C20 C 0.2061(3) 0.37983(19) -0.09169(15) 0.0221(6) Uani 1 1 d . . . . .
H20A H 0.2299 0.4346 -0.1163 0.027 Uiso 1 1 calc R U . . .
H20B H 0.1764 0.3312 -0.1320 0.027 Uiso 1 1 calc R U . . .
C21 C 0.3247(3) 0.37295(19) -0.04078(15) 0.0244(6) Uani 1 1 d . . . . .
H21A H 0.3531 0.4202 0.0007 0.029 Uiso 1 1 calc R U . . .
H21B H 0.3026 0.3170 -0.0180 0.029 Uiso 1 1 calc R U . . .
C22 C 0.4335(3) 0.3791(2) -0.08644(16) 0.0275(7) Uani 1 1 d . . . . .
H22A H 0.4044 0.3318 -0.1278 0.033 Uiso 1 1 calc R U . . .
H22B H 0.4544 0.4349 -0.1096 0.033 Uiso 1 1 calc R U . . .
C23 C 0.5542(3) 0.3730(2) -0.03790(18) 0.0389(8) Uani 1 1 d . . . . .
H23A H 0.5807 0.4178 0.0048 0.058 Uiso 1 1 calc R U . . .
H23B H 0.6235 0.3817 -0.0685 0.058 Uiso 1 1 calc R U . . .
H23C H 0.5362 0.3157 -0.0188 0.058 Uiso 1 1 calc R U . . .
C24 C 0.0244(3) 0.30662(19) -0.02491(15) 0.0233(6) Uani 1 1 d . . . . .
H24 H 0.0318 0.2503 -0.0321 0.028 Uiso 1 1 calc R U . . .
C25 C 0.1498(3) 0.74665(18) 0.21671(16) 0.0236(6) Uani 1 1 d . . . . .
H25A H 0.1700 0.7435 0.1647 0.028 Uiso 1 1 calc R U . . .
H25B H 0.2289 0.7529 0.2529 0.028 Uiso 1 1 calc R U . . .
C26 C 0.0716(3) 0.59192(18) 0.21554(14) 0.0209(6) Uani 1 1 d . . . . .
C27 C 0.1833(3) 0.58234(18) 0.19498(15) 0.0217(6) Uani 1 1 d . . . . .
H27 H 0.2517 0.6318 0.1876 0.026 Uiso 1 1 calc R U . . .
C28 C 0.1946(3) 0.49964(18) 0.18525(15) 0.0221(6) Uani 1 1 d . . . . .
H28 H 0.2711 0.4929 0.1711 0.027 Uiso 1 1 calc R U . . .
C29 C 0.0952(3) 0.42729(17) 0.19602(14) 0.0208(6) Uani 1 1 d . . . . .
C30 C -0.0176(3) 0.43769(18) 0.21525(14) 0.0200(6) Uani 1 1 d . . . . .
H30 H -0.0868 0.3883 0.2217 0.024 Uiso 1 1 calc R U . . .
C31 C -0.0291(3) 0.51891(18) 0.22487(14) 0.0204(6) Uani 1 1 d . . . . .
H31 H -0.1063 0.5254 0.2380 0.024 Uiso 1 1 calc R U . . .
C32 C 0.2085(3) 0.32944(18) 0.16646(16) 0.0246(6) Uani 1 1 d . . . . .
H32A H 0.2858 0.3608 0.2035 0.029 Uiso 1 1 calc R U . . .
H32B H 0.2208 0.3513 0.1164 0.029 Uiso 1 1 calc R U . . .
C33 C 0.1895(3) 0.23461(18) 0.16221(16) 0.0256(6) Uani 1 1 d . . . . .
H33A H 0.2682 0.2235 0.1502 0.031 Uiso 1 1 calc R U . . .
H33B H 0.1728 0.2125 0.2116 0.031 Uiso 1 1 calc R U . . .
C34 C 0.0801(3) 0.10480(18) 0.08627(15) 0.0260(6) Uani 1 1 d . . . . .
H34A H -0.0104 0.0678 0.0713 0.031 Uiso 1 1 calc R U . . .
H34B H 0.1174 0.0824 0.1313 0.031 Uiso 1 1 calc R U . . .
C35 C 0.1540(3) 0.09947(19) 0.02256(16) 0.0276(7) Uani 1 1 d . . . . .
H35A H 0.2407 0.1430 0.0332 0.033 Uiso 1 1 calc R U . . .
H35B H 0.1638 0.0412 0.0165 0.033 Uiso 1 1 calc R U . . .
C36 C 0.1476(3) 0.11962(19) -0.10842(16) 0.0262(6) Uani 1 1 d . . . . .
H36A H 0.1831 0.0708 -0.1114 0.031 Uiso 1 1 calc R U . . .
H36B H 0.2195 0.1746 -0.1042 0.031 Uiso 1 1 calc R U . . .
C37 C 0.0515(3) 0.11415(19) -0.17764(16) 0.0252(6) Uani 1 1 d . . . . .
H37A H 0.0929 0.1160 -0.2234 0.030 Uiso 1 1 calc R U . . .
H37B H -0.0200 0.0589 -0.1819 0.030 Uiso 1 1 calc R U . . .
C38 C -0.1028(3) 0.17812(18) -0.22966(16) 0.0256(6) Uani 1 1 d . . . . .
H38A H -0.1726 0.1232 -0.2281 0.031 Uiso 1 1 calc R U . . .
H38B H -0.0751 0.1782 -0.2800 0.031 Uiso 1 1 calc R U . . .
C39 C -0.3405(3) 0.15177(19) 0.55865(18) 0.0312(7) Uani 1 1 d . . . . .
H39A H -0.4354 0.1259 0.5492 0.037 Uiso 1 1 calc R U . . .
H39B H -0.3147 0.1810 0.6106 0.037 Uiso 1 1 calc R U . . .
C40 C -0.3078(3) 0.29557(18) 0.52263(16) 0.0243(6) Uani 1 1 d . . . . .
C41 C -0.3750(3) 0.33039(19) 0.46806(16) 0.0249(6) Uani 1 1 d . . . . .
H41 H -0.4179 0.2968 0.4219 0.030 Uiso 1 1 calc R U . . .
C42 C -0.3796(3) 0.41391(18) 0.48092(15) 0.0242(6) Uani 1 1 d . . . . .
H42 H -0.4266 0.4373 0.4440 0.029 Uiso 1 1 calc R U . . .
C43 C -0.3152(3) 0.46349(18) 0.54807(16) 0.0228(6) Uani 1 1 d . . . . .
C44 C -0.2469(3) 0.42885(19) 0.60228(16) 0.0245(6) Uani 1 1 d . . . . .
H44 H -0.2025 0.4625 0.6482 0.029 Uiso 1 1 calc R U . . .
C45 C -0.2440(3) 0.34493(19) 0.58891(16) 0.0247(6) Uani 1 1 d . . . . .
H45 H -0.1975 0.3213 0.6259 0.030 Uiso 1 1 calc R U . . .
C46 C -0.2512(3) 0.60156(18) 0.62032(15) 0.0245(6) Uani 1 1 d . . . . .
H46A H -0.1584 0.6103 0.6208 0.029 Uiso 1 1 calc R U . . .
H46B H -0.2757 0.5759 0.6673 0.029 Uiso 1 1 calc R U . . .
C47 C -0.2774(3) 0.68576(18) 0.61583(16) 0.0249(6) Uani 1 1 d . . . . .
H47A H -0.3708 0.6762 0.6132 0.030 Uiso 1 1 calc R U . . .
H47B H -0.2318 0.7250 0.6617 0.030 Uiso 1 1 calc R U . . .
C48 C -0.2702(3) 0.80057(18) 0.53947(16) 0.0267(7) Uani 1 1 d . . . . .
H48A H -0.2250 0.8453 0.5818 0.032 Uiso 1 1 calc R U . . .
H48B H -0.3640 0.7872 0.5388 0.032 Uiso 1 1 calc R U . . .
C49 C -0.2351(3) 0.83398(19) 0.46616(17) 0.0273(7) Uani 1 1 d . . . . .
H49A H -0.2717 0.7870 0.4246 0.033 Uiso 1 1 calc R U . . .
H49B H -0.2710 0.8816 0.4546 0.033 Uiso 1 1 calc R U . . .
C50 C -0.0591(3) 0.9072(2) 0.40737(16) 0.0288(7) Uani 1 1 d . . . . .
H50A H -0.1009 0.9523 0.3979 0.035 Uiso 1 1 calc R U . . .
H50B H -0.0850 0.8647 0.3622 0.035 Uiso 1 1 calc R U . . .
C51 C 0.0841(3) 0.94755(19) 0.42153(17) 0.0301(7) Uani 1 1 d . . . . .
H51A H 0.1120 0.9827 0.3796 0.036 Uiso 1 1 calc R U . . .
H51B H 0.1104 0.9863 0.4691 0.036 Uiso 1 1 calc R U . . .
C52 C 0.2788(3) 0.91731(19) 0.44933(18) 0.0314(7) Uani 1 1 d . . . . .
H52A H 0.2981 0.9425 0.5026 0.038 Uiso 1 1 calc R U . . .
H52B H 0.3138 0.9641 0.4173 0.038 Uiso 1 1 calc R U . . .
C53 C 0.4814(3) 0.1067(2) 0.32604(19) 0.0396(8) Uani 1 1 d . . . . .
H53A H 0.4515 0.1151 0.3740 0.059 Uiso 1 1 calc R U . . .
H53B H 0.5411 0.1615 0.3151 0.059 Uiso 1 1 calc R U . . .
H53C H 0.5253 0.0627 0.3298 0.059 Uiso 1 1 calc R U . . .
C54 C 0.3690(3) 0.0774(2) 0.26401(19) 0.0338(7) Uani 1 1 d . . . . .
C55 C 0.3993(3) 0.0674(2) 0.18572(19) 0.0422(8) Uani 1 1 d . . . . .
H55A H 0.3195 0.0385 0.1508 0.063 Uiso 1 1 calc R U . . .
H55B H 0.4575 0.0326 0.1855 0.063 Uiso 1 1 calc R U . . .
H55C H 0.4406 0.1248 0.1696 0.063 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 F6 1.5894(19) . ?
P1 F3 1.5912(19) . ?
P1 F5 1.5964(19) . ?
P1 F2 1.5969(18) . ?
P1 F1 1.5973(18) . ?
P1 F4 1.5989(18) . ?
P2 F24 1.587(2) . ?
P2 F11 1.589(2) . ?
P2 F7 1.5953(19) . ?
P2 F8 1.599(2) . ?
P2 F9 1.6054(19) . ?
P2 F10 1.607(2) . ?
O1 C26 1.375(3) . ?
O1 C25 1.430(3) . ?
O2 C29 1.373(3) . ?
O2 C32 1.428(3) . ?
O3 C33 1.420(3) . ?
O3 C34 1.422(3) . ?
O4 C35 1.423(3) . ?
O4 C36 1.427(3) . ?
O5 C37 1.417(3) . ?
O5 C38 1.429(3) . ?
O6 C40 1.393(3) . ?
O6 C39 1.438(3) . ?
O7 C43 1.373(3) . ?
O7 C46 1.427(3) . ?
O8 C48 1.424(3) . ?
O8 C47 1.426(3) . ?
O9 C49 1.425(3) . ?
O9 C50 1.428(3) . ?
O10 C52 1.423(3) . ?
O10 C51 1.423(3) . ?
O11 C54 1.211(4) . ?
N1 C8 1.325(3) . ?
N1 C2 1.391(3) . ?
N1 C9 1.473(3) . ?
N2 C8 1.331(3) . ?
N2 C3 1.394(3) . ?
N2 C4 1.476(3) . ?
N3 C24 1.333(4) . ?
N3 C15 1.391(3) . ?
N3 C16 1.478(3) . ?
N4 C24 1.336(3) . ?
N4 C14 1.391(3) . ?
N4 C20 1.474(3) . ?
C1 C3 1.387(4) 2_566 ?
C1 C2 1.393(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.400(4) . ?
C3 C1 1.387(4) 2_566 ?
C4 C5 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.520(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.523(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.387(4) 2_565 ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.410(4) . ?
C15 C13 1.387(4) 2_565 ?
C16 C17 1.492(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.565(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.454(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.528(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.526(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 0.9500 . ?
C25 C38 1.490(4) 2_565 ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.385(4) . ?
C26 C31 1.392(4) . ?
C27 C28 1.395(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(4) . ?
C30 C31 1.371(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.489(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.505(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.499(4) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C25 1.490(4) 2_565 ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C52 1.493(4) 2_566 ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C45 1.376(4) . ?
C40 C41 1.392(4) . ?
C41 C42 1.386(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.391(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.393(4) . ?
C44 C45 1.387(4) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 C47 1.488(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.498(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.498(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C39 1.493(4) 2_566 ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.490(5) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 C55 1.499(4) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F6 P1 F3 179.41(12) . . ?
F6 P1 F5 90.80(11) . . ?
F3 P1 F5 89.29(11) . . ?
F6 P1 F2 89.85(11) . . ?
F3 P1 F2 90.06(11) . . ?
F5 P1 F2 179.22(11) . . ?
F6 P1 F1 90.32(11) . . ?
F3 P1 F1 90.26(11) . . ?
F5 P1 F1 90.61(10) . . ?
F2 P1 F1 89.83(10) . . ?
F6 P1 F4 89.84(11) . . ?
F3 P1 F4 89.58(11) . . ?
F5 P1 F4 89.53(10) . . ?
F2 P1 F4 90.02(10) . . ?
F1 P1 F4 179.78(12) . . ?
F24 P2 F11 91.13(13) . . ?
F24 P2 F7 90.61(13) . . ?
F11 P2 F7 90.04(11) . . ?
F24 P2 F8 89.73(13) . . ?
F11 P2 F8 179.13(14) . . ?
F7 P2 F8 90.06(11) . . ?
F24 P2 F9 90.44(12) . . ?
F11 P2 F9 90.49(11) . . ?
F7 P2 F9 178.81(13) . . ?
F8 P2 F9 89.39(11) . . ?
F24 P2 F10 179.17(14) . . ?
F11 P2 F10 89.64(13) . . ?
F7 P2 F10 89.69(12) . . ?
F8 P2 F10 89.50(12) . . ?
F9 P2 F10 89.25(11) . . ?
C26 O1 C25 117.5(2) . . ?
C29 O2 C32 117.0(2) . . ?
C33 O3 C34 111.4(2) . . ?
C35 O4 C36 113.1(2) . . ?
C37 O5 C38 112.4(2) . . ?
C40 O6 C39 115.0(2) . . ?
C43 O7 C46 117.7(2) . . ?
C48 O8 C47 111.3(2) . . ?
C49 O9 C50 111.6(2) . . ?
C52 O10 C51 110.9(2) . . ?
C8 N1 C2 108.7(2) . . ?
C8 N1 C9 124.2(2) . . ?
C2 N1 C9 127.0(2) . . ?
C8 N2 C3 108.3(2) . . ?
C8 N2 C4 125.8(2) . . ?
C3 N2 C4 125.9(2) . . ?
C24 N3 C15 108.3(2) . . ?
C24 N3 C16 124.7(2) . . ?
C15 N3 C16 126.9(2) . . ?
C24 N4 C14 108.6(2) . . ?
C24 N4 C20 124.8(2) . . ?
C14 N4 C20 126.6(2) . . ?
C3 C1 C2 113.1(2) 2_566 . ?
C3 C1 H1 123.4 2_566 . ?
C2 C1 H1 123.4 . . ?
N1 C2 C1 130.2(2) . . ?
N1 C2 C3 106.2(2) . . ?
C1 C2 C3 123.6(2) . . ?
C1 C3 N2 130.3(2) 2_566 . ?
C1 C3 C2 123.3(2) 2_566 . ?
N2 C3 C2 106.4(2) . . ?
N2 C4 C5 112.5(2) . . ?
N2 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N2 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 112.2(2) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 112.3(2) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 N2 110.4(2) . . ?
N1 C8 H8 124.8 . . ?
N2 C8 H8 124.8 . . ?
N1 C9 C10 112.4(2) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 110.4(2) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 112.0(2) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C14 113.4(2) 2_565 . ?
C15 C13 H13 123.3 2_565 . ?
C14 C13 H13 123.3 . . ?
C13 C14 N4 130.5(2) . . ?
C13 C14 C15 123.4(2) . . ?
N4 C14 C15 106.0(2) . . ?
C13 C15 N3 130.3(3) 2_565 . ?
C13 C15 C14 123.1(2) 2_565 . ?
N3 C15 C14 106.6(2) . . ?
N3 C16 C17 111.7(2) . . ?
N3 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 112.9(3) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 108.2(4) . . ?
C19 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
C19 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C21 112.2(2) . . ?
N4 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
N4 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C22 C21 C20 110.3(2) . . ?
C22 C21 H21A 109.6 . . ?
C20 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
C20 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C23 C22 C21 112.2(2) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 N4 110.4(3) . . ?
N3 C24 H24 124.8 . . ?
N4 C24 H24 124.8 . . ?
O1 C25 C38 107.6(2) . 2_565 ?
O1 C25 H25A 110.2 . . ?
C38 C25 H25A 110.2 2_565 . ?
O1 C25 H25B 110.2 . . ?
C38 C25 H25B 110.2 2_565 . ?
H25A C25 H25B 108.5 . . ?
O1 C26 C27 124.7(3) . . ?
O1 C26 C31 115.5(2) . . ?
C27 C26 C31 119.8(3) . . ?
C26 C27 C28 119.6(3) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
O2 C29 C28 125.4(3) . . ?
O2 C29 C30 115.3(2) . . ?
C28 C29 C30 119.4(3) . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C26 120.5(3) . . ?
C30 C31 H31 119.8 . . ?
C26 C31 H31 119.8 . . ?
O2 C32 C33 108.0(2) . . ?
O2 C32 H32A 110.1 . . ?
C33 C32 H32A 110.1 . . ?
O2 C32 H32B 110.1 . . ?
C33 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
O3 C33 C32 109.3(2) . . ?
O3 C33 H33A 109.8 . . ?
C32 C33 H33A 109.8 . . ?
O3 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.3 . . ?
O3 C34 C35 111.6(2) . . ?
O3 C34 H34A 109.3 . . ?
C35 C34 H34A 109.3 . . ?
O3 C34 H34B 109.3 . . ?
C35 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
O4 C35 C34 107.3(2) . . ?
O4 C35 H35A 110.3 . . ?
C34 C35 H35A 110.3 . . ?
O4 C35 H35B 110.3 . . ?
C34 C35 H35B 110.3 . . ?
H35A C35 H35B 108.5 . . ?
O4 C36 C37 107.8(2) . . ?
O4 C36 H36A 110.2 . . ?
C37 C36 H36A 110.2 . . ?
O4 C36 H36B 110.2 . . ?
C37 C36 H36B 110.2 . . ?
H36A C36 H36B 108.5 . . ?
O5 C37 C36 108.7(2) . . ?
O5 C37 H37A 110.0 . . ?
C36 C37 H37A 110.0 . . ?
O5 C37 H37B 110.0 . . ?
C36 C37 H37B 110.0 . . ?
H37A C37 H37B 108.3 . . ?
O5 C38 C25 108.4(2) . 2_565 ?
O5 C38 H38A 110.0 . . ?
C25 C38 H38A 110.0 2_565 . ?
O5 C38 H38B 110.0 . . ?
C25 C38 H38B 110.0 2_565 . ?
H38A C38 H38B 108.4 . . ?
O6 C39 C52 108.5(2) . 2_566 ?
O6 C39 H39A 110.0 . . ?
C52 C39 H39A 110.0 2_566 . ?
O6 C39 H39B 110.0 . . ?
C52 C39 H39B 110.0 2_566 . ?
H39A C39 H39B 108.4 . . ?
C45 C40 C41 119.8(3) . . ?
C45 C40 O6 122.4(3) . . ?
C41 C40 O6 117.6(3) . . ?
C42 C41 C40 120.2(3) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C43 119.9(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
O7 C43 C42 115.7(2) . . ?
O7 C43 C44 124.4(3) . . ?
C42 C43 C44 119.9(3) . . ?
C45 C44 C43 119.6(3) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C40 C45 C44 120.7(3) . . ?
C40 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
O7 C46 C47 107.8(2) . . ?
O7 C46 H46A 110.2 . . ?
C47 C46 H46A 110.2 . . ?
O7 C46 H46B 110.2 . . ?
C47 C46 H46B 110.2 . . ?
H46A C46 H46B 108.5 . . ?
O8 C47 C46 109.5(2) . . ?
O8 C47 H47A 109.8 . . ?
C46 C47 H47A 109.8 . . ?
O8 C47 H47B 109.8 . . ?
C46 C47 H47B 109.8 . . ?
H47A C47 H47B 108.2 . . ?
O8 C48 C49 109.5(2) . . ?
O8 C48 H48A 109.8 . . ?
C49 C48 H48A 109.8 . . ?
O8 C48 H48B 109.8 . . ?
C49 C48 H48B 109.8 . . ?
H48A C48 H48B 108.2 . . ?
O9 C49 C48 109.1(2) . . ?
O9 C49 H49A 109.9 . . ?
C48 C49 H49A 109.9 . . ?
O9 C49 H49B 109.9 . . ?
C48 C49 H49B 109.9 . . ?
H49A C49 H49B 108.3 . . ?
O9 C50 C51 108.8(2) . . ?
O9 C50 H50A 109.9 . . ?
C51 C50 H50A 109.9 . . ?
O9 C50 H50B 109.9 . . ?
C51 C50 H50B 109.9 . . ?
H50A C50 H50B 108.3 . . ?
O10 C51 C50 109.4(2) . . ?
O10 C51 H51A 109.8 . . ?
C50 C51 H51A 109.8 . . ?
O10 C51 H51B 109.8 . . ?
C50 C51 H51B 109.8 . . ?
H51A C51 H51B 108.2 . . ?
O10 C52 C39 109.6(2) . 2_566 ?
O10 C52 H52A 109.8 . . ?
C39 C52 H52A 109.8 2_566 . ?
O10 C52 H52B 109.8 . . ?
C39 C52 H52B 109.8 2_566 . ?
H52A C52 H52B 108.2 . . ?
C54 C53 H53A 109.5 . . ?
C54 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C54 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O11 C54 C53 122.0(3) . . ?
O11 C54 C55 121.9(3) . . ?
C53 C54 C55 116.1(3) . . ?
C54 C55 H55A 109.5 . . ?
C54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?

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
C8 N1 C2 C1 179.9(3) . . . . ?
C9 N1 C2 C1 -3.3(4) . . . . ?
C8 N1 C2 C3 1.0(3) . . . . ?
C9 N1 C2 C3 177.9(2) . . . . ?
C3 C1 C2 N1 -178.3(3) 2_566 . . . ?
C3 C1 C2 C3 0.4(4) 2_566 . . . ?
C8 N2 C3 C1 -178.7(3) . . . 2_566 ?
C4 N2 C3 C1 3.8(4) . . . 2_566 ?
C8 N2 C3 C2 0.9(3) . . . . ?
C4 N2 C3 C2 -176.6(2) . . . . ?
N1 C2 C3 C1 178.5(2) . . . 2_566 ?
C1 C2 C3 C1 -0.5(5) . . . 2_566 ?
N1 C2 C3 N2 -1.1(3) . . . . ?
C1 C2 C3 N2 179.9(2) . . . . ?
C8 N2 C4 C5 -16.4(4) . . . . ?
C3 N2 C4 C5 160.7(2) . . . . ?
N2 C4 C5 C6 -166.3(2) . . . . ?
C4 C5 C6 C7 176.5(3) . . . . ?
C2 N1 C8 N2 -0.5(3) . . . . ?
C9 N1 C8 N2 -177.4(2) . . . . ?
C3 N2 C8 N1 -0.3(3) . . . . ?
C4 N2 C8 N1 177.2(2) . . . . ?
C8 N1 C9 C10 108.1(3) . . . . ?
C2 N1 C9 C10 -68.3(3) . . . . ?
N1 C9 C10 C11 -178.5(2) . . . . ?
C9 C10 C11 C12 172.8(2) . . . . ?
C15 C13 C14 N4 178.9(3) 2_565 . . . ?
C15 C13 C14 C15 -0.7(4) 2_565 . . . ?
C24 N4 C14 C13 179.5(3) . . . . ?
C20 N4 C14 C13 -0.4(4) . . . . ?
C24 N4 C14 C15 -0.9(3) . . . . ?
C20 N4 C14 C15 179.2(2) . . . . ?
C24 N3 C15 C13 179.2(3) . . . 2_565 ?
C16 N3 C15 C13 0.0(4) . . . 2_565 ?
C24 N3 C15 C14 -0.3(3) . . . . ?
C16 N3 C15 C14 -179.6(2) . . . . ?
C13 C14 C15 C13 0.8(4) . . . 2_565 ?
N4 C14 C15 C13 -178.9(2) . . . 2_565 ?
C13 C14 C15 N3 -179.6(2) . . . . ?
N4 C14 C15 N3 0.7(3) . . . . ?
C24 N3 C16 C17 -72.1(4) . . . . ?
C15 N3 C16 C17 107.0(3) . . . . ?
N3 C16 C17 C18 -173.6(3) . . . . ?
C16 C17 C18 C19 -70.5(4) . . . . ?
C24 N4 C20 C21 -75.8(3) . . . . ?
C14 N4 C20 C21 104.2(3) . . . . ?
N4 C20 C21 C22 -177.6(2) . . . . ?
C20 C21 C22 C23 179.7(3) . . . . ?
C15 N3 C24 N4 -0.2(3) . . . . ?
C16 N3 C24 N4 179.1(2) . . . . ?
C14 N4 C24 N3 0.7(3) . . . . ?
C20 N4 C24 N3 -179.4(2) . . . . ?
C26 O1 C25 C38 177.8(2) . . . 2_565 ?
C25 O1 C26 C27 0.9(4) . . . . ?
C25 O1 C26 C31 -178.6(2) . . . . ?
O1 C26 C27 C28 179.4(2) . . . . ?
C31 C26 C27 C28 -1.2(4) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C32 O2 C29 C28 -2.7(4) . . . . ?
C32 O2 C29 C30 177.3(2) . . . . ?
C27 C28 C29 O2 -178.7(2) . . . . ?
C27 C28 C29 C30 1.3(4) . . . . ?
O2 C29 C30 C31 178.7(2) . . . . ?
C28 C29 C30 C31 -1.3(4) . . . . ?
C29 C30 C31 C26 0.0(4) . . . . ?
O1 C26 C31 C30 -179.3(2) . . . . ?
C27 C26 C31 C30 1.2(4) . . . . ?
C29 O2 C32 C33 -179.5(2) . . . . ?
C34 O3 C33 C32 166.0(2) . . . . ?
O2 C32 C33 O3 63.7(3) . . . . ?
C33 O3 C34 C35 -90.7(3) . . . . ?
C36 O4 C35 C34 175.3(2) . . . . ?
O3 C34 C35 O4 -70.2(3) . . . . ?
C35 O4 C36 C37 165.7(2) . . . . ?
C38 O5 C37 C36 -171.3(2) . . . . ?
O4 C36 C37 O5 60.1(3) . . . . ?
C37 O5 C38 C25 177.7(2) . . . 2_565 ?
C40 O6 C39 C52 -157.0(2) . . . 2_566 ?
C39 O6 C40 C45 58.1(3) . . . . ?
C39 O6 C40 C41 -126.9(3) . . . . ?
C45 C40 C41 C42 -1.1(4) . . . . ?
O6 C40 C41 C42 -176.2(2) . . . . ?
C40 C41 C42 C43 1.0(4) . . . . ?
C46 O7 C43 C42 -174.3(2) . . . . ?
C46 O7 C43 C44 6.0(4) . . . . ?
C41 C42 C43 O7 180.0(2) . . . . ?
C41 C42 C43 C44 -0.3(4) . . . . ?
O7 C43 C44 C45 179.5(3) . . . . ?
C42 C43 C44 C45 -0.2(4) . . . . ?
C41 C40 C45 C44 0.6(4) . . . . ?
O6 C40 C45 C44 175.4(2) . . . . ?
C43 C44 C45 C40 0.1(4) . . . . ?
C43 O7 C46 C47 179.7(2) . . . . ?
C48 O8 C47 C46 173.9(2) . . . . ?
O7 C46 C47 O8 -63.1(3) . . . . ?
C47 O8 C48 C49 -174.5(2) . . . . ?
C50 O9 C49 C48 -172.9(2) . . . . ?
O8 C48 C49 O9 -68.0(3) . . . . ?
C49 O9 C50 C51 172.9(2) . . . . ?
C52 O10 C51 C50 -173.1(2) . . . . ?
O9 C50 C51 O10 65.8(3) . . . . ?
C51 O10 C52 C39 -170.0(2) . . . 2_566 ?

_refine_diff_density_max         0.716
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.056

