##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_journal_date_recd_electronic     2011-12-16
_journal_date_accepted     2012-01-23
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2012
_journal_volume     68
_journal_issue      3
_journal_page_first     o104
_journal_page_last     o107
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270112002934
_journal_coeditor_code     GG3269
_publ_contact_author_name     'Filipe A. Almeida Paz'
_publ_contact_author_address
;
Department of Chemistry
University of Aveiro
CICECO
3810-193 Aveiro
Portugal
;
_publ_contact_author_email     filipe.paz@ua.pt
_publ_contact_author_fax     '+351 234 401470'
_publ_contact_author_phone     '+351 234 370200'
_publ_section_title
;\
5-[4-(Diethoxyphosphoryl)-2,3,5,6-tetrafluorophenyl]-10,15,20-\
tris(pentafluorophenyl)porphyrin
;
loop_
    _publ_author_name
    _publ_author_address
    'Pereira, Carla F.'
;
Department of Chemistry
University of Aveiro
QOPNA and CICECO
3810-193 Aveiro
Portugal
;
    'Fernandes, José A.'
;
Department of Chemistry
University of Aveiro
CICECO
3810-193 Aveiro
Portugal
;
    'Rodrigues, João M. M.'
;
Department of Chemistry
University of Aveiro
QOPNA
3810-193 Aveiro
Portugal
;
    'Vilela, Sérgio M. F.'
;
Department of Chemistry
University of Aveiro
CICECO
3810-193 Aveiro
Portugal
;
    'Tomé, João P. C.'
;
Department of Chemistry
University of Aveiro
QOPNA
3810-193 Aveiro
Portugal
;
    'Almeida Paz, Filipe A.'
;
Department of Chemistry
University of Aveiro
CICECO
3810-193 Aveiro
Portugal
;
data_I
_chemical_name_systematic
;
5-[4-(Diethoxyphosphoryl)-2,3,5,6-tetrafluorophenyl]-10,15,20-
tris(pentafluorophenyl)porphyrin
;
_chemical_name_common     ?
_chemical_formula_moiety     'C48 H20 F19 N4 O3 P'
_chemical_formula_sum     'C48 H20 F19 N4 O3 P'
_chemical_formula_iupac     'C48 H20 F19 N4 O3 P'
_chemical_formula_weight     1092.65
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.530(2)
_cell_length_b     11.2539(17)
_cell_length_c     26.375(3)
_cell_angle_alpha     90.00
_cell_angle_beta     100.024(9)
_cell_angle_gamma     90.00
_cell_volume     4539.3(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5493
_cell_measurement_theta_min     2.23
_cell_measurement_theta_max     24.62
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.08
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.599
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2184
_exptl_absorpt_coefficient_mu     0.188
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.9851
_exptl_absorpt_correction_T_max     0.9944
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII X8 Kappa CCD area-detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     32626
_diffrn_reflns_av_R_equivalents     0.1153
_diffrn_reflns_av_sigmaI/netI     0.1283
_diffrn_reflns_theta_min     3.62
_diffrn_reflns_theta_max     25.35
_diffrn_reflns_theta_full     25.35
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     31
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     8275
_reflns_number_gt     3504
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1976
_refine_ls_R_factor_gt     0.0844
_refine_ls_wR_factor_gt     0.1996
_refine_ls_wR_factor_ref     0.2714
_refine_ls_goodness_of_fit_ref     0.990
_refine_ls_restrained_S_all     0.990
_refine_ls_number_reflns     8275
_refine_ls_number_parameters     678
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                    'w = 1/[σ²(Fo²)+(0.1428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.416
_refine_diff_density_min     -0.341
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2005)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2009)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    P P1 0.16439(12) -0.33648(17) 0.46670(6) 0.0652(6) Uani d . 1 1 . .
    O O1 0.1598(3) -0.2804(4) 0.41705(15) 0.0719(13) Uani d . 1 1 . .
    O O2 0.0863(3) -0.4204(4) 0.47212(15) 0.0707(13) Uani d . 1 1 . .
    O O3 0.2468(3) -0.4131(4) 0.48763(17) 0.0868(16) Uani d . 1 1 . .
    F F1 0.1924(2) 0.0838(3) 0.54643(12) 0.0649(10) Uani d . 1 1 . .
    F F2 0.1613(2) -0.0599(3) 0.46667(11) 0.0669(10) Uani d . 1 1 . .
    F F3 0.1806(3) -0.3904(3) 0.57991(13) 0.0807(12) Uani d . 1 1 . .
    F F4 0.2058(3) -0.2426(3) 0.65892(12) 0.0731(11) Uani d . 1 1 . .
    F F5 0.0266(2) 0.5186(3) 0.66925(13) 0.0673(10) Uani d . 1 1 . .
    F F6 -0.1342(3) 0.6132(4) 0.64182(15) 0.0882(12) Uani d . 1 1 . .
    F F7 -0.2752(2) 0.5047(4) 0.66976(14) 0.0885(13) Uani d . 1 1 . .
    F F8 -0.2534(2) 0.3073(4) 0.72954(14) 0.0816(12) Uani d . 1 1 . .
    F F9 -0.0921(2) 0.2125(3) 0.75712(13) 0.0701(10) Uani d . 1 1 . .
    F F10 0.3384(3) 0.6298(3) 0.84165(14) 0.0870(12) Uani d . 1 1 . .
    F F11 0.3764(3) 0.7932(4) 0.91557(16) 0.0953(13) Uani d . 1 1 . .
    F F12 0.3993(3) 0.7278(4) 1.01585(15) 0.0971(14) Uani d . 1 1 . .
    F F13 0.3848(3) 0.4970(4) 1.04133(13) 0.0877(13) Uani d . 1 1 . .
    F F14 0.3393(3) 0.3333(4) 0.96711(12) 0.0749(11) Uani d . 1 1 . .
    F F15 0.6237(3) 0.1375(4) 0.75765(16) 0.0873(12) Uani d . 1 1 . .
    F F16 0.7822(3) 0.0394(4) 0.7903(2) 0.1208(18) Uani d . 1 1 . .
    F F17 0.8006(3) -0.1359(5) 0.8611(2) 0.132(2) Uani d . 1 1 . .
    F F18 0.6577(4) -0.2269(6) 0.8920(3) 0.171(3) Uani d . 1 1 . .
    F F19 0.4985(3) -0.1341(5) 0.8574(2) 0.145(2) Uani d . 1 1 . .
    N N1 0.1609(3) 0.1585(4) 0.70239(15) 0.0414(11) Uani d . 1 1 . .
    N N2 0.1990(3) 0.3254(4) 0.78848(15) 0.0444(11) Uani d . 1 1 . .
    H H2 0.2278 0.2685 0.7758 0.053 Uiso calc R 1 1 . .
    N N3 0.3714(3) 0.2208(4) 0.81267(16) 0.0464(12) Uani d . 1 1 . .
    N N4 0.3350(3) 0.0582(4) 0.72488(16) 0.0460(12) Uani d . 1 1 . .
    H H4 0.3053 0.1129 0.7384 0.055 Uiso calc R 1 1 . .
    C C1 -0.0037(4) -0.3951(7) 0.4477(3) 0.074(2) Uani d . 1 1 . .
    H H1A -0.0372 -0.4704 0.4437 0.089 Uiso calc R 1 1 . .
    H H1B -0.0035 -0.3626 0.4129 0.089 Uiso calc R 1 1 . .
    C C2 -0.0486(5) -0.3094(7) 0.4773(3) 0.095(2) Uani d . 1 1 . .
    H H2A -0.0465 -0.3390 0.5124 0.142 Uiso calc R 1 1 . .
    H H2B -0.1097 -0.3007 0.4605 0.142 Uiso calc R 1 1 . .
    H H2C -0.0193 -0.2321 0.4784 0.142 Uiso calc R 1 1 . .
    C C3 0.2754(5) -0.5152(7) 0.4624(3) 0.090(2) Uani d . 1 1 . .
    H H3A 0.2741 -0.4977 0.4255 0.108 Uiso calc R 1 1 . .
    H H3B 0.2359 -0.5832 0.4650 0.108 Uiso calc R 1 1 . .
    C C4 0.3669(6) -0.5454(8) 0.4880(4) 0.114(3) Uani d . 1 1 . .
    H H4A 0.4035 -0.4741 0.4900 0.171 Uiso calc R 1 1 . .
    H H4B 0.3908 -0.6065 0.4679 0.171 Uiso calc R 1 1 . .
    H H4C 0.3661 -0.5755 0.5228 0.171 Uiso calc R 1 1 . .
    C C5 0.0818(4) 0.2156(5) 0.69625(19) 0.0442(14) Uani d . 1 1 . .
    C C6 0.0604(3) 0.3071(5) 0.72770(19) 0.0424(14) Uani d . 1 1 . .
    C C7 0.1153(4) 0.3562(5) 0.76999(19) 0.0449(14) Uani d . 1 1 . .
    C C8 0.0934(4) 0.4527(6) 0.8017(2) 0.0560(16) Uani d . 1 1 . .
    H H8 0.0389 0.4929 0.7978 0.067 Uiso calc R 1 1 . .
    C C9 0.1640(4) 0.4752(6) 0.8375(2) 0.0560(16) Uani d . 1 1 . .
    H H9 0.1681 0.5340 0.8637 0.067 Uiso calc R 1 1 . .
    C C10 0.2323(4) 0.3948(5) 0.8295(2) 0.0509(15) Uani d . 1 1 . .
    C C11 0.3161(4) 0.3847(5) 0.85936(19) 0.0482(15) Uani d . 1 1 . .
    C C12 0.3793(4) 0.3005(5) 0.8522(2) 0.0453(14) Uani d . 1 1 . .
    C C13 0.4612(4) 0.2863(6) 0.8868(2) 0.0531(16) Uani d . 1 1 . .
    H H13 0.4822 0.3323 0.9166 0.064 Uiso calc R 1 1 . .
    C C14 0.5024(4) 0.1945(5) 0.8682(2) 0.0528(16) Uani d . 1 1 . .
    H H14 0.5576 0.1622 0.8829 0.063 Uiso calc R 1 1 . .
    C C15 0.4466(4) 0.1550(5) 0.8221(2) 0.0455(14) Uani d . 1 1 . .
    C C16 0.4693(4) 0.0632(5) 0.7899(2) 0.0471(14) Uani d . 1 1 . .
    C C17 0.4182(4) 0.0218(5) 0.7452(2) 0.0492(15) Uani d . 1 1 . .
    C C18 0.4415(4) -0.0647(6) 0.7108(2) 0.0592(17) Uani d . 1 1 . .
    H H18 0.4958 -0.1056 0.7147 0.071 Uiso calc R 1 1 . .
    C C19 0.3746(4) -0.0793(6) 0.6718(2) 0.0593(16) Uani d . 1 1 . .
    H H19 0.3734 -0.1312 0.6433 0.071 Uiso calc R 1 1 . .
    C C20 0.3050(4) -0.0027(5) 0.6808(2) 0.0479(14) Uani d . 1 1 . .
    C C21 0.2211(4) 0.0068(5) 0.65156(19) 0.0485(15) Uani d . 1 1 . .
    C C22 0.1532(4) 0.0812(5) 0.66182(19) 0.0439(14) Uani d . 1 1 . .
    C C23 0.0671(4) 0.0888(5) 0.6306(2) 0.0486(15) Uani d . 1 1 . .
    H H23 0.0461 0.0439 0.6005 0.058 Uiso calc R 1 1 . .
    C C24 0.0226(4) 0.1707(5) 0.6520(2) 0.0461(14) Uani d . 1 1 . .
    H H24 -0.0362 0.1947 0.6405 0.055 Uiso calc R 1 1 . .
    C C25 0.2015(4) -0.0746(5) 0.6055(2) 0.0483(14) Uani d . 1 1 . .
    C C26 0.1893(4) -0.0347(5) 0.5558(2) 0.0503(15) Uani d . 1 1 . .
    C C27 0.1738(4) -0.1092(6) 0.5137(2) 0.0514(15) Uani d . 1 1 . .
    C C28 0.1727(4) -0.2326(6) 0.5202(2) 0.0543(16) Uani d . 1 1 . .
    C C29 0.1841(4) -0.2716(6) 0.5702(2) 0.0582(16) Uani d . 1 1 . .
    C C30 0.1964(4) -0.1962(5) 0.6119(2) 0.0516(15) Uani d . 1 1 . .
    C C31 -0.0288(4) 0.3623(5) 0.71366(19) 0.0439(14) Uani d . 1 1 . .
    C C32 -0.0416(4) 0.4645(5) 0.6848(2) 0.0509(15) Uani d . 1 1 . .
    C C33 -0.1236(5) 0.5140(6) 0.6701(2) 0.0599(17) Uani d . 1 1 . .
    C C34 -0.1937(4) 0.4599(7) 0.6847(2) 0.0618(18) Uani d . 1 1 . .
    C C35 -0.1836(4) 0.3604(6) 0.7142(2) 0.0565(17) Uani d . 1 1 . .
    C C36 -0.1015(4) 0.3105(6) 0.7285(2) 0.0520(16) Uani d . 1 1 . .
    C C37 0.3387(4) 0.4742(6) 0.9018(2) 0.0532(16) Uani d . 1 1 . .
    C C38 0.3487(4) 0.5943(6) 0.8903(2) 0.0636(18) Uani d . 1 1 . .
    C C39 0.3683(5) 0.6778(6) 0.9283(3) 0.0703(19) Uani d . 1 1 . .
    C C40 0.3803(4) 0.6445(7) 0.9787(3) 0.0676(19) Uani d . 1 1 . .
    C C41 0.3728(4) 0.5294(7) 0.9919(2) 0.0656(19) Uani d . 1 1 . .
    C C42 0.3503(4) 0.4462(6) 0.9528(2) 0.0577(16) Uani d . 1 1 . .
    C C43 0.5571(4) 0.0040(6) 0.8070(2) 0.0517(15) Uani d . 1 1 . .
    C C44 0.6306(4) 0.0473(7) 0.7901(3) 0.0611(17) Uani d . 1 1 . .
    C C45 0.7121(5) -0.0020(8) 0.8070(3) 0.078(2) Uani d . 1 1 . .
    C C46 0.7202(6) -0.0920(10) 0.8415(4) 0.087(3) Uani d . 1 1 . .
    C C47 0.6500(7) -0.1388(8) 0.8575(3) 0.096(3) Uani d . 1 1 . .
    C C48 0.5673(5) -0.0895(7) 0.8406(3) 0.084(2) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    P1 O1 . 1.444(5) ?
    P1 O3 . 1.562(5) ?
    P1 O2 . 1.564(5) ?
    P1 C28 . 1.821(6) ?
    O2 C1 . 1.461(7) ?
    O3 C3 . 1.436(8) ?
    F1 C26 . 1.359(6) ?
    F2 C27 . 1.342(6) ?
    F3 C29 . 1.365(7) ?
    F4 C30 . 1.329(6) ?
    F5 C32 . 1.346(7) ?
    F6 C33 . 1.337(7) ?
    F7 C34 . 1.356(7) ?
    F8 C35 . 1.360(7) ?
    F9 C36 . 1.330(7) ?
    F10 C38 . 1.327(7) ?
    F11 C39 . 1.353(8) ?
    F12 C40 . 1.351(7) ?
    F13 C41 . 1.335(7) ?
    F14 C42 . 1.345(7) ?
    F15 C44 . 1.320(8) ?
    F16 C45 . 1.328(9) ?
    F17 C46 . 1.358(8) ?
    F18 C47 . 1.336(10) ?
    F19 C48 . 1.324(8) ?
    N1 C22 . 1.368(6) ?
    N1 C5 . 1.371(7) ?
    N2 C7 . 1.352(7) ?
    N2 C10 . 1.362(7) ?
    N2 H2 . 0.8800 ?
    N3 C12 . 1.365(7) ?
    N3 C15 . 1.369(7) ?
    N4 C20 . 1.361(7) ?
    N4 C17 . 1.374(7) ?
    N4 H4 . 0.8800 ?
    C1 C2 . 1.488(10) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2A . 0.9800 ?
    C2 H2B . 0.9800 ?
    C2 H2C . 0.9800 ?
    C3 C4 . 1.503(10) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C5 C6 . 1.398(7) ?
    C5 C24 . 1.446(7) ?
    C6 C7 . 1.395(7) ?
    C6 C31 . 1.504(7) ?
    C7 C8 . 1.446(8) ?
    C8 C9 . 1.341(8) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.437(8) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.404(8) ?
    C11 C12 . 1.399(8) ?
    C11 C37 . 1.502(8) ?
    C12 C13 . 1.440(8) ?
    C13 C14 . 1.351(8) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.436(8) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.419(8) ?
    C16 C17 . 1.382(8) ?
    C16 C43 . 1.513(8) ?
    C17 C18 . 1.421(8) ?
    C18 C19 . 1.338(8) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.434(8) ?
    C19 H19 . 0.9500 ?
    C20 C21 . 1.398(8) ?
    C21 C22 . 1.409(8) ?
    C21 C25 . 1.510(8) ?
    C22 C23 . 1.446(7) ?
    C23 C24 . 1.335(7) ?
    C23 H23 . 0.9500 ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.367(7) ?
    C25 C30 . 1.384(8) ?
    C26 C27 . 1.378(8) ?
    C27 C28 . 1.399(8) ?
    C28 C29 . 1.371(8) ?
    C29 C30 . 1.376(8) ?
    C31 C32 . 1.375(8) ?
    C31 C36 . 1.386(8) ?
    C32 C33 . 1.381(8) ?
    C33 C34 . 1.360(9) ?
    C34 C35 . 1.356(9) ?
    C35 C36 . 1.385(8) ?
    C37 C42 . 1.361(8) ?
    C37 C38 . 1.400(9) ?
    C38 C39 . 1.370(9) ?
    C39 C40 . 1.360(9) ?
    C40 C41 . 1.353(10) ?
    C41 C42 . 1.392(9) ?
    C43 C48 . 1.368(9) ?
    C43 C44 . 1.385(9) ?
    C44 C45 . 1.384(10) ?
    C45 C46 . 1.353(12) ?
    C46 C47 . 1.344(12) ?
    C47 C48 . 1.399(11) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 P1 O3 . . 118.0(3) ?
    O1 P1 O2 . . 115.5(2) ?
    O3 P1 O2 . . 103.6(3) ?
    O1 P1 C28 . . 114.1(3) ?
    O3 P1 C28 . . 97.9(2) ?
    O2 P1 C28 . . 105.6(3) ?
    C1 O2 P1 . . 122.7(4) ?
    C3 O3 P1 . . 125.3(4) ?
    C22 N1 C5 . . 104.5(4) ?
    C7 N2 C10 . . 110.4(5) ?
    C7 N2 H2 . . 124.8 ?
    C10 N2 H2 . . 124.8 ?
    C12 N3 C15 . . 104.9(4) ?
    C20 N4 C17 . . 110.0(5) ?
    C20 N4 H4 . . 125.0 ?
    C17 N4 H4 . . 125.0 ?
    O2 C1 C2 . . 113.3(6) ?
    O2 C1 H1A . . 108.9 ?
    C2 C1 H1A . . 108.9 ?
    O2 C1 H1B . . 108.9 ?
    C2 C1 H1B . . 108.9 ?
    H1A C1 H1B . . 107.7 ?
    C1 C2 H2A . . 109.5 ?
    C1 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C1 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    O3 C3 C4 . . 108.5(6) ?
    O3 C3 H3A . . 110.0 ?
    C4 C3 H3A . . 110.0 ?
    O3 C3 H3B . . 110.0 ?
    C4 C3 H3B . . 110.0 ?
    H3A C3 H3B . . 108.4 ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N1 C5 C6 . . 125.2(5) ?
    N1 C5 C24 . . 111.3(5) ?
    C6 C5 C24 . . 123.5(5) ?
    C7 C6 C5 . . 126.2(5) ?
    C7 C6 C31 . . 116.2(5) ?
    C5 C6 C31 . . 117.5(5) ?
    N2 C7 C6 . . 127.0(5) ?
    N2 C7 C8 . . 107.0(5) ?
    C6 C7 C8 . . 126.0(5) ?
    C9 C8 C7 . . 107.7(5) ?
    C9 C8 H8 . . 126.2 ?
    C7 C8 H8 . . 126.2 ?
    C8 C9 C10 . . 108.2(5) ?
    C8 C9 H9 . . 125.9 ?
    C10 C9 H9 . . 125.9 ?
    N2 C10 C11 . . 125.9(5) ?
    N2 C10 C9 . . 106.8(5) ?
    C11 C10 C9 . . 127.2(5) ?
    C12 C11 C10 . . 125.6(5) ?
    C12 C11 C37 . . 118.4(5) ?
    C10 C11 C37 . . 115.9(5) ?
    N3 C12 C11 . . 125.1(5) ?
    N3 C12 C13 . . 111.3(5) ?
    C11 C12 C13 . . 123.6(5) ?
    C14 C13 C12 . . 106.1(5) ?
    C14 C13 H13 . . 126.9 ?
    C12 C13 H13 . . 126.9 ?
    C13 C14 C15 . . 106.9(5) ?
    C13 C14 H14 . . 126.6 ?
    C15 C14 H14 . . 126.6 ?
    N3 C15 C16 . . 125.4(5) ?
    N3 C15 C14 . . 110.8(5) ?
    C16 C15 C14 . . 123.7(5) ?
    C17 C16 C15 . . 126.1(5) ?
    C17 C16 C43 . . 117.4(5) ?
    C15 C16 C43 . . 116.5(5) ?
    N4 C17 C16 . . 126.5(5) ?
    N4 C17 C18 . . 106.3(5) ?
    C16 C17 C18 . . 127.2(6) ?
    C19 C18 C17 . . 109.0(5) ?
    C19 C18 H18 . . 125.5 ?
    C17 C18 H18 . . 125.5 ?
    C18 C19 C20 . . 107.8(5) ?
    C18 C19 H19 . . 126.1 ?
    C20 C19 H19 . . 126.1 ?
    N4 C20 C21 . . 125.5(5) ?
    N4 C20 C19 . . 106.8(5) ?
    C21 C20 C19 . . 127.7(5) ?
    C20 C21 C22 . . 126.6(5) ?
    C20 C21 C25 . . 115.8(5) ?
    C22 C21 C25 . . 117.6(5) ?
    N1 C22 C21 . . 124.2(5) ?
    N1 C22 C23 . . 110.8(5) ?
    C21 C22 C23 . . 125.1(5) ?
    C24 C23 C22 . . 107.2(5) ?
    C24 C23 H23 . . 126.4 ?
    C22 C23 H23 . . 126.4 ?
    C23 C24 C5 . . 106.2(5) ?
    C23 C24 H24 . . 126.9 ?
    C5 C24 H24 . . 126.9 ?
    C26 C25 C30 . . 116.2(5) ?
    C26 C25 C21 . . 123.2(6) ?
    C30 C25 C21 . . 120.6(5) ?
    F1 C26 C25 . . 119.5(5) ?
    F1 C26 C27 . . 117.3(5) ?
    C25 C26 C27 . . 123.2(6) ?
    F2 C27 C26 . . 118.0(6) ?
    F2 C27 C28 . . 121.4(5) ?
    C26 C27 C28 . . 120.6(5) ?
    C29 C28 C27 . . 115.7(6) ?
    C29 C28 P1 . . 121.3(5) ?
    C27 C28 P1 . . 122.8(4) ?
    F3 C29 C28 . . 119.5(6) ?
    F3 C29 C30 . . 117.3(5) ?
    C28 C29 C30 . . 123.2(6) ?
    F4 C30 C29 . . 118.8(5) ?
    F4 C30 C25 . . 120.2(5) ?
    C29 C30 C25 . . 121.0(5) ?
    C32 C31 C36 . . 117.5(5) ?
    C32 C31 C6 . . 121.3(5) ?
    C36 C31 C6 . . 121.2(5) ?
    F5 C32 C31 . . 120.1(5) ?
    F5 C32 C33 . . 117.9(6) ?
    C31 C32 C33 . . 122.0(6) ?
    F6 C33 C34 . . 120.3(6) ?
    F6 C33 C32 . . 120.8(6) ?
    C34 C33 C32 . . 119.0(6) ?
    F7 C34 C35 . . 118.8(6) ?
    F7 C34 C33 . . 120.3(7) ?
    C35 C34 C33 . . 120.9(6) ?
    C34 C35 F8 . . 121.0(6) ?
    C34 C35 C36 . . 120.0(6) ?
    F8 C35 C36 . . 118.9(6) ?
    F9 C36 C35 . . 119.8(6) ?
    F9 C36 C31 . . 119.6(5) ?
    C35 C36 C31 . . 120.6(6) ?
    C42 C37 C38 . . 115.9(6) ?
    C42 C37 C11 . . 123.7(6) ?
    C38 C37 C11 . . 120.4(5) ?
    F10 C38 C39 . . 118.4(6) ?
    F10 C38 C37 . . 120.1(6) ?
    C39 C38 C37 . . 121.5(6) ?
    F11 C39 C40 . . 120.3(6) ?
    F11 C39 C38 . . 119.7(6) ?
    C40 C39 C38 . . 120.0(7) ?
    F12 C40 C41 . . 119.6(6) ?
    F12 C40 C39 . . 119.5(7) ?
    C41 C40 C39 . . 120.8(6) ?
    F13 C41 C40 . . 120.7(6) ?
    F13 C41 C42 . . 121.0(7) ?
    C40 C41 C42 . . 118.3(6) ?
    F14 C42 C37 . . 119.7(6) ?
    F14 C42 C41 . . 117.0(6) ?
    C37 C42 C41 . . 123.3(7) ?
    C48 C43 C44 . . 118.1(6) ?
    C48 C43 C16 . . 121.9(6) ?
    C44 C43 C16 . . 119.9(6) ?
    F15 C44 C45 . . 118.9(7) ?
    F15 C44 C43 . . 120.1(6) ?
    C45 C44 C43 . . 121.0(8) ?
    F16 C45 C46 . . 120.0(9) ?
    F16 C45 C44 . . 120.7(9) ?
    C46 C45 C44 . . 119.3(8) ?
    C47 C46 C45 . . 121.3(8) ?
    C47 C46 F17 . . 118.7(10) ?
    C45 C46 F17 . . 120.0(10) ?
    F18 C47 C46 . . 121.5(9) ?
    F18 C47 C48 . . 118.7(9) ?
    C46 C47 C48 . . 119.7(8) ?
    F19 C48 C43 . . 119.9(6) ?
    F19 C48 C47 . . 119.5(8) ?
    C43 C48 C47 . . 120.5(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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 P1 O2 C1 . . . . -36.7(5) ?
    O3 P1 O2 C1 . . . . -167.3(4) yes
    C28 P1 O2 C1 . . . . 90.4(5) ?
    O1 P1 O3 C3 . . . . -59.0(7) ?
    O2 P1 O3 C3 . . . . 70.1(6) ?
    C28 P1 O3 C3 . . . . 178.3(6) yes
    P1 O2 C1 C2 . . . . -81.5(7) yes
    P1 O3 C3 C4 . . . . 166.7(6) yes
    C22 N1 C5 C6 . . . . -177.1(5) ?
    C22 N1 C5 C24 . . . . 1.9(6) ?
    N1 C5 C6 C7 . . . . 0.6(9) ?
    C24 C5 C6 C7 . . . . -178.2(5) ?
    N1 C5 C6 C31 . . . . 177.7(5) ?
    C24 C5 C6 C31 . . . . -1.1(8) ?
    C10 N2 C7 C6 . . . . 178.6(5) ?
    C10 N2 C7 C8 . . . . 0.0(6) ?
    C5 C6 C7 N2 . . . . 0.1(9) ?
    C31 C6 C7 N2 . . . . -177.0(5) ?
    C5 C6 C7 C8 . . . . 178.5(5) ?
    C31 C6 C7 C8 . . . . 1.3(8) ?
    N2 C7 C8 C9 . . . . -0.2(7) ?
    C6 C7 C8 C9 . . . . -178.8(5) ?
    C7 C8 C9 C10 . . . . 0.4(7) ?
    C7 N2 C10 C11 . . . . 177.5(5) ?
    C7 N2 C10 C9 . . . . 0.3(6) ?
    C8 C9 C10 N2 . . . . -0.4(7) ?
    C8 C9 C10 C11 . . . . -177.6(6) ?
    N2 C10 C11 C12 . . . . -0.7(9) ?
    C9 C10 C11 C12 . . . . 175.9(6) ?
    N2 C10 C11 C37 . . . . 178.3(5) ?
    C9 C10 C11 C37 . . . . -5.0(8) ?
    C15 N3 C12 C11 . . . . -178.3(5) ?
    C15 N3 C12 C13 . . . . 0.9(6) ?
    C10 C11 C12 N3 . . . . 5.2(9) ?
    C37 C11 C12 N3 . . . . -173.8(5) ?
    C10 C11 C12 C13 . . . . -173.9(5) ?
    C37 C11 C12 C13 . . . . 7.1(8) ?
    N3 C12 C13 C14 . . . . -1.5(6) ?
    C11 C12 C13 C14 . . . . 177.8(5) ?
    C12 C13 C14 C15 . . . . 1.3(6) ?
    C12 N3 C15 C16 . . . . -177.6(5) ?
    C12 N3 C15 C14 . . . . -0.1(6) ?
    C13 C14 C15 N3 . . . . -0.8(6) ?
    C13 C14 C15 C16 . . . . 176.8(5) ?
    N3 C15 C16 C17 . . . . -2.8(9) ?
    C14 C15 C16 C17 . . . . 180.0(5) ?
    N3 C15 C16 C43 . . . . 178.4(5) ?
    C14 C15 C16 C43 . . . . 1.2(8) ?
    C20 N4 C17 C16 . . . . -179.6(5) ?
    C20 N4 C17 C18 . . . . 1.5(6) ?
    C15 C16 C17 N4 . . . . -2.9(9) ?
    C43 C16 C17 N4 . . . . 175.8(5) ?
    C15 C16 C17 C18 . . . . 175.8(6) ?
    C43 C16 C17 C18 . . . . -5.4(9) ?
    N4 C17 C18 C19 . . . . -0.3(7) ?
    C16 C17 C18 C19 . . . . -179.3(6) ?
    C17 C18 C19 C20 . . . . -0.9(7) ?
    C17 N4 C20 C21 . . . . 176.2(5) ?
    C17 N4 C20 C19 . . . . -2.0(6) ?
    C18 C19 C20 N4 . . . . 1.8(7) ?
    C18 C19 C20 C21 . . . . -176.3(6) ?
    N4 C20 C21 C22 . . . . 0.8(9) ?
    C19 C20 C21 C22 . . . . 178.6(6) ?
    N4 C20 C21 C25 . . . . -177.0(5) ?
    C19 C20 C21 C25 . . . . 0.8(9) ?
    C5 N1 C22 C21 . . . . 177.4(5) ?
    C5 N1 C22 C23 . . . . -1.3(6) ?
    C20 C21 C22 N1 . . . . 1.5(9) ?
    C25 C21 C22 N1 . . . . 179.3(5) ?
    C20 C21 C22 C23 . . . . 179.9(5) ?
    C25 C21 C22 C23 . . . . -2.3(8) ?
    N1 C22 C23 C24 . . . . 0.2(6) ?
    C21 C22 C23 C24 . . . . -178.4(5) ?
    C22 C23 C24 C5 . . . . 0.9(6) ?
    N1 C5 C24 C23 . . . . -1.8(6) ?
    C6 C5 C24 C23 . . . . 177.2(5) ?
    C20 C21 C25 C26 . . . . -111.5(6) ?
    C22 C21 C25 C26 . . . . 70.4(7) ?
    C20 C21 C25 C30 . . . . 67.5(7) ?
    C22 C21 C25 C30 . . . . -110.6(6) ?
    C30 C25 C26 F1 . . . . 179.3(5) ?
    C21 C25 C26 F1 . . . . -1.7(9) ?
    C30 C25 C26 C27 . . . . -0.8(9) ?
    C21 C25 C26 C27 . . . . 178.2(5) ?
    F1 C26 C27 F2 . . . . -1.2(8) ?
    C25 C26 C27 F2 . . . . 178.9(5) ?
    F1 C26 C27 C28 . . . . 177.8(5) ?
    C25 C26 C27 C28 . . . . -2.1(9) ?
    F2 C27 C28 C29 . . . . -178.4(5) ?
    C26 C27 C28 C29 . . . . 2.6(9) ?
    F2 C27 C28 P1 . . . . 5.8(8) ?
    C26 C27 C28 P1 . . . . -173.2(4) ?
    O1 P1 C28 C29 . . . . -175.2(5) ?
    O3 P1 C28 C29 . . . . -49.6(6) ?
    O2 P1 C28 C29 . . . . 57.0(6) ?
    O1 P1 C28 C27 . . . . 0.5(6) ?
    O3 P1 C28 C27 . . . . 126.0(5) ?
    O2 P1 C28 C27 . . . . -127.4(5) ?
    C27 C28 C29 F3 . . . . 177.6(5) ?
    P1 C28 C29 F3 . . . . -6.5(8) ?
    C27 C28 C29 C30 . . . . -0.3(9) ?
    P1 C28 C29 C30 . . . . 175.6(5) ?
    F3 C29 C30 F4 . . . . 1.2(9) ?
    C28 C29 C30 F4 . . . . 179.1(5) ?
    F3 C29 C30 C25 . . . . 179.4(5) ?
    C28 C29 C30 C25 . . . . -2.7(10) ?
    C26 C25 C30 F4 . . . . -178.6(5) ?
    C21 C25 C30 F4 . . . . 2.3(9) ?
    C26 C25 C30 C29 . . . . 3.2(9) ?
    C21 C25 C30 C29 . . . . -175.9(6) ?
    C7 C6 C31 C32 . . . . 81.8(6) ?
    C5 C6 C31 C32 . . . . -95.6(6) ?
    C7 C6 C31 C36 . . . . -99.5(6) ?
    C5 C6 C31 C36 . . . . 83.1(6) ?
    C36 C31 C32 F5 . . . . -179.9(5) ?
    C6 C31 C32 F5 . . . . -1.3(7) ?
    C36 C31 C32 C33 . . . . -0.9(8) ?
    C6 C31 C32 C33 . . . . 177.8(5) ?
    F5 C32 C33 F6 . . . . -0.6(8) ?
    C31 C32 C33 F6 . . . . -179.7(5) ?
    F5 C32 C33 C34 . . . . 179.0(5) ?
    C31 C32 C33 C34 . . . . -0.1(9) ?
    F6 C33 C34 F7 . . . . 1.3(9) ?
    C32 C33 C34 F7 . . . . -178.3(5) ?
    F6 C33 C34 C35 . . . . -178.8(5) ?
    C32 C33 C34 C35 . . . . 1.6(9) ?
    F7 C34 C35 F8 . . . . -1.3(8) ?
    C33 C34 C35 F8 . . . . 178.8(5) ?
    F7 C34 C35 C36 . . . . 177.8(5) ?
    C33 C34 C35 C36 . . . . -2.1(9) ?
    C34 C35 C36 F9 . . . . -179.5(5) ?
    F8 C35 C36 F9 . . . . -0.5(8) ?
    C34 C35 C36 C31 . . . . 1.1(8) ?
    F8 C35 C36 C31 . . . . -179.8(5) ?
    C32 C31 C36 F9 . . . . -179.0(5) ?
    C6 C31 C36 F9 . . . . 2.3(8) ?
    C32 C31 C36 C35 . . . . 0.4(8) ?
    C6 C31 C36 C35 . . . . -178.3(5) ?
    C12 C11 C37 C42 . . . . -68.9(8) ?
    C10 C11 C37 C42 . . . . 112.0(6) ?
    C12 C11 C37 C38 . . . . 111.4(6) ?
    C10 C11 C37 C38 . . . . -67.7(7) ?
    C42 C37 C38 F10 . . . . -179.8(6) ?
    C11 C37 C38 F10 . . . . -0.1(9) ?
    C42 C37 C38 C39 . . . . -0.5(9) ?
    C11 C37 C38 C39 . . . . 179.3(6) ?
    F10 C38 C39 F11 . . . . 0.1(10) ?
    C37 C38 C39 F11 . . . . -179.2(6) ?
    F10 C38 C39 C40 . . . . -179.3(6) ?
    C37 C38 C39 C40 . . . . 1.4(11) ?
    F11 C39 C40 F12 . . . . 0.8(10) ?
    C38 C39 C40 F12 . . . . -179.8(6) ?
    F11 C39 C40 C41 . . . . -179.7(6) ?
    C38 C39 C40 C41 . . . . -0.3(11) ?
    F12 C40 C41 F13 . . . . -0.7(10) ?
    C39 C40 C41 F13 . . . . 179.8(6) ?
    F12 C40 C41 C42 . . . . 177.9(6) ?
    C39 C40 C41 C42 . . . . -1.6(10) ?
    C38 C37 C42 F14 . . . . 178.1(5) ?
    C11 C37 C42 F14 . . . . -1.7(9) ?
    C38 C37 C42 C41 . . . . -1.5(9) ?
    C11 C37 C42 C41 . . . . 178.8(6) ?
    F13 C41 C42 F14 . . . . 1.6(9) ?
    C40 C41 C42 F14 . . . . -177.0(6) ?
    F13 C41 C42 C37 . . . . -178.9(6) ?
    C40 C41 C42 C37 . . . . 2.5(10) ?
    C17 C16 C43 C48 . . . . -92.7(7) ?
    C15 C16 C43 C48 . . . . 86.2(8) ?
    C17 C16 C43 C44 . . . . 89.7(7) ?
    C15 C16 C43 C44 . . . . -91.4(6) ?
    C48 C43 C44 F15 . . . . -179.9(6) ?
    C16 C43 C44 F15 . . . . -2.3(9) ?
    C48 C43 C44 C45 . . . . -0.6(9) ?
    C16 C43 C44 C45 . . . . 177.1(6) ?
    F15 C44 C45 F16 . . . . -1.0(9) ?
    C43 C44 C45 F16 . . . . 179.6(6) ?
    F15 C44 C45 C46 . . . . 177.9(6) ?
    C43 C44 C45 C46 . . . . -1.5(10) ?
    F16 C45 C46 C47 . . . . -177.4(7) ?
    C44 C45 C46 C47 . . . . 3.7(11) ?
    F16 C45 C46 F17 . . . . 3.4(10) ?
    C44 C45 C46 F17 . . . . -175.5(6) ?
    C45 C46 C47 F18 . . . . -179.4(7) ?
    F17 C46 C47 F18 . . . . -0.2(12) ?
    C45 C46 C47 C48 . . . . -3.7(13) ?
    F17 C46 C47 C48 . . . . 175.5(7) ?
    C44 C43 C48 F19 . . . . -179.4(7) ?
    C16 C43 C48 F19 . . . . 2.9(11) ?
    C44 C43 C48 C47 . . . . 0.6(11) ?
    C16 C43 C48 C47 . . . . -177.1(7) ?
    F18 C47 C48 F19 . . . . -2.7(13) ?
    C46 C47 C48 F19 . . . . -178.5(8) ?
    F18 C47 C48 C43 . . . . 177.3(8) ?
    C46 C47 C48 C43 . . . . 1.5(13) ?
