#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:58:22 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230330 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/76/7057659.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7057659
loop_
_publ_author_name
'Intrieri, Daniela'
'Damiano, Caterina'
'Rizzato, Silvia'
'Paolesse, Roberto'
'Venanzi, Mariano'
'Monti, Donato'
'Savioli, Marco'
'Stefanelli, Manuela'
'Gallo, Emma'
_publ_section_title
;
 Sensing of diclofenac by a porphyrin-based artificial receptor
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15778
_journal_paper_doi               10.1039/C8NJ02737D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C53 H35 F15 N5 O, I ,0.5(C6 H14)'
_chemical_formula_sum            'C56 H42 F15 I N5 O'
_chemical_formula_weight         1212.85
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_update_record
;
2018-05-15 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                103.382(3)
_cell_angle_beta                 90.662(3)
_cell_angle_gamma                106.684(3)
_cell_formula_units_Z            2
_cell_length_a                   11.465(3)
_cell_length_b                   15.353(4)
_cell_length_c                   16.170(5)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.6
_cell_measurement_theta_min      2.2
_cell_measurement_wavelength     0.71073
_cell_volume                     2643.1(13)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CCD_plate
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker ApexII ccd diffractometer'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23475
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5646
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs (Bruker AXS, 2012)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1218
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.432
_refine_diff_density_min         -0.775
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     775
_refine_ls_number_reflns         9334
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.058
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0778P)²+11.1947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         1
_reflns_number_gt                7082
_reflns_number_total             9334
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj02737d2.cif
_cod_data_source_block           3
_cod_depositor_comments          'Adding full bibliography for 7057659.cif.'
_cod_original_cell_volume        2643.2(13)
_cod_database_code               7057659
_restr_u_iso_atom_site_label     F2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I I -0.58171(4) 0.31489(3) 0.41806(2) 0.03842(14) Uani 1 1 d . . . . .
N1 N -0.0912(4) 0.2712(3) 0.7310(3) 0.0253(9) Uani 1 1 d . . . . .
N2 N 0.0829(4) 0.3830(3) 0.8759(3) 0.0253(9) Uani 1 1 d . . . . .
N3 N 0.0086(4) 0.5441(3) 0.8605(2) 0.0227(8) Uani 1 1 d . . . . .
N4 N -0.1566(4) 0.4343(3) 0.7111(3) 0.0246(9) Uani 1 1 d . . . . .
C1 C -0.1736(5) 0.2288(4) 0.6615(3) 0.0284(11) Uani 1 1 d . . . . .
C2 C -0.1801(6) 0.1311(4) 0.6323(4) 0.0378(13) Uani 1 1 d . . . . .
C3 C -0.1017(6) 0.1157(4) 0.6844(4) 0.0394(14) Uani 1 1 d . . . . .
C4 C -0.0462(5) 0.2029(4) 0.7469(4) 0.0318(12) Uani 1 1 d . . . . .
C5 C 0.0428(5) 0.2152(4) 0.8106(4) 0.0346(12) Uani 1 1 d . . . . .
C6 C 0.1041(5) 0.2990(4) 0.8693(3) 0.0311(12) Uani 1 1 d . . . . .
C7 C 0.2028(5) 0.3136(4) 0.9300(4) 0.0368(13) Uani 1 1 d . . . . .
C8 C 0.2411(5) 0.4055(4) 0.9699(4) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.1647(4) 0.4503(4) 0.9364(3) 0.0264(11) Uani 1 1 d . . . . .
C10 C 0.1735(4) 0.5455(4) 0.9607(3) 0.0253(11) Uani 1 1 d . . . . .
C11 C 0.0954(4) 0.5868(4) 0.9279(3) 0.0258(11) Uani 1 1 d . . . . .
C12 C 0.0998(5) 0.6838(4) 0.9582(3) 0.0301(11) Uani 1 1 d . . . . .
C13 C 0.0187(5) 0.6998(4) 0.9078(3) 0.0305(11) Uani 1 1 d . . . . .
C14 C -0.0370(4) 0.6123(3) 0.8455(3) 0.0256(10) Uani 1 1 d . . . . .
C15 C -0.1218(4) 0.6008(4) 0.7781(3) 0.0260(11) Uani 1 1 d . . . . .
C16 C -0.1771(4) 0.5185(4) 0.7163(3) 0.0258(11) Uani 1 1 d . . . . .
C17 C -0.2666(5) 0.5063(4) 0.6489(3) 0.0289(11) Uani 1 1 d . . . . .
C18 C -0.2997(5) 0.4155(4) 0.6059(3) 0.0284(11) Uani 1 1 d . . . . .
C19 C -0.2309(4) 0.3686(3) 0.6447(3) 0.0239(10) Uani 1 1 d . . . . .
C20 C -0.2388(5) 0.2739(4) 0.6211(3) 0.0288(11) Uani 1 1 d . . . . .
C21 C 0.0859(5) 0.1323(4) 0.8139(4) 0.0379(13) Uani 1 1 d . . . . .
C22 C 0.0362(6) 0.0731(4) 0.8658(4) 0.0438(15) Uani 1 1 d . . . . .
C23 C 0.0743(7) -0.0040(4) 0.8677(4) 0.0549(19) Uani 1 1 d . . . . .
C24 C 0.1627(8) -0.0241(5) 0.8173(6) 0.064(2) Uani 1 1 d . . . . .
C25 C 0.2139(7) 0.0333(6) 0.7668(6) 0.073(2) Uani 1 1 d . . . . .
C26 C 0.1748(6) 0.1094(5) 0.7652(5) 0.059(2) Uani 1 1 d . . . . .
C27 C 0.2798(5) 0.6088(4) 1.0202(3) 0.0283(11) Uani 1 1 d . . . . .
C28 C 0.2749(6) 0.6322(5) 1.1068(4) 0.0400(14) Uani 1 1 d . . . . .
C29 C 0.3748(6) 0.6915(5) 1.1604(4) 0.0502(17) Uani 1 1 d . . . . .
C30 C 0.4813(6) 0.7274(5) 1.1267(4) 0.0493(16) Uani 1 1 d . . . . .
C31 C 0.4895(6) 0.7049(5) 1.0400(4) 0.0482(16) Uani 1 1 d . . . . .
C32 C 0.3895(5) 0.6454(4) 0.9870(4) 0.0367(13) Uani 1 1 d . . . . .
C33 C -0.1526(5) 0.6869(3) 0.7693(3) 0.0270(11) Uani 1 1 d . . . . .
C34 C -0.2360(5) 0.7212(4) 0.8174(4) 0.0355(12) Uani 1 1 d . . . . .
C35 C -0.2586(5) 0.8023(4) 0.8122(4) 0.0428(14) Uani 1 1 d . . . . .
C36 C -0.1984(6) 0.8517(4) 0.7569(4) 0.0462(15) Uani 1 1 d . . . . .
C37 C -0.1184(6) 0.8194(4) 0.7074(4) 0.0466(15) Uani 1 1 d . . . . .
C38 C -0.0953(5) 0.7383(4) 0.7138(4) 0.0382(13) Uani 1 1 d . . . . .
C39 C -0.3276(5) 0.2144(4) 0.5469(3) 0.0314(12) Uani 1 1 d . . . . .
C40 C -0.3007(6) 0.2114(4) 0.4644(4) 0.0428(14) Uani 1 1 d . . . . .
C41 C -0.3873(9) 0.1544(5) 0.3956(4) 0.059(2) Uani 1 1 d . . . . .
C42 C -0.4960(8) 0.1025(5) 0.4127(5) 0.058(2) Uani 1 1 d . . . . .
C43 C -0.5256(6) 0.1049(5) 0.4927(5) 0.0516(17) Uani 1 1 d . . . . .
C44 C -0.4426(5) 0.1602(4) 0.5588(4) 0.0416(14) Uani 1 1 d . . . . .
N1S N 0.2667(4) 0.4594(3) 0.6594(3) 0.0371(11) Uani 1 1 d . . . . .
O1 O 0.4001(4) 0.6178(3) 0.9009(2) 0.0461(11) Uani 1 1 d . . . . .
C1B C 0.3721(7) 0.6748(5) 0.8501(4) 0.0501(17) Uani 1 1 d . . . . .
C2B C 0.3664(7) 0.6221(5) 0.7574(4) 0.0545(19) Uani 1 1 d . . . . .
C3B C 0.2654(6) 0.5292(5) 0.7416(4) 0.0462(16) Uani 1 1 d . . . . .
C4B C 0.3869(6) 0.4376(5) 0.6531(4) 0.0433(15) Uani 1 1 d . . . . .
C5B C 0.4253(7) 0.4051(6) 0.7283(5) 0.070(2) Uani 1 1 d . . . . .
H5B3 H 0.502266 0.392769 0.719533 0.105 Uiso 1 1 calc R U . . .
H5B1 H 0.43327 0.45323 0.77979 0.105 Uiso 1 1 calc R U . . .
H5B2 H 0.364602 0.348936 0.733017 0.105 Uiso 1 1 calc R U . . .
C6B C 0.2513(6) 0.4992(5) 0.5835(4) 0.0419(14) Uani 1 1 d . . . . .
C7B C 0.1315(7) 0.5198(6) 0.5757(5) 0.069(2) Uani 1 1 d . . . . .
H7B3 H 0.128307 0.54456 0.526636 0.103 Uiso 1 1 calc R U . . .
H7B2 H 0.065477 0.463028 0.569374 0.103 Uiso 1 1 calc R U . . .
H7B1 H 0.124449 0.564914 0.625984 0.103 Uiso 1 1 calc R U . . .
C8B C 0.1618(6) 0.3730(5) 0.6579(4) 0.0478(16) Uani 1 1 d . . . . .
C9B C 0.1396(7) 0.2951(5) 0.5763(5) 0.067(2) Uani 1 1 d . . . . .
H9B3 H 0.071539 0.243281 0.581129 0.101 Uiso 1 1 calc R U . . .
H9B2 H 0.122145 0.318248 0.528758 0.101 Uiso 1 1 calc R U . . .
H9B1 H 0.211196 0.274647 0.567614 0.101 Uiso 1 1 calc R U . . .
F1 F 0.2266(4) 0.1640(3) 0.7140(4) 0.0909(18) Uani 1 1 d . . . . .
F2 F 0.3007(6) 0.0153(4) 0.7190(5) 0.117(2) Uani 1 1 d . U . . .
F3 F 0.1960(5) -0.0998(3) 0.8190(4) 0.0947(17) Uani 1 1 d . . . . .
F4 F 0.0209(5) -0.0604(3) 0.9178(3) 0.0806(15) Uani 1 1 d . . . . .
F5 F -0.0507(5) 0.0908(3) 0.9150(3) 0.0680(12) Uani 1 1 d . . . . .
F6 F -0.2958(3) 0.6740(3) 0.8723(2) 0.0534(10) Uani 1 1 d . . . . .
F7 F -0.3388(4) 0.8337(3) 0.8611(3) 0.0703(12) Uani 1 1 d . . . . .
F8 F -0.2214(4) 0.9311(3) 0.7515(3) 0.0671(12) Uani 1 1 d . . . . .
F9 F -0.0603(5) 0.8675(3) 0.6525(3) 0.0747(13) Uani 1 1 d . . . . .
F10 F -0.0148(4) 0.7083(3) 0.6645(3) 0.0609(11) Uani 1 1 d . . . . .
F11 F -0.1915(4) 0.2631(3) 0.4491(3) 0.0697(12) Uani 1 1 d . . . . .
F12 F -0.3561(6) 0.1581(4) 0.3169(3) 0.0932(18) Uani 1 1 d . . . . .
F13 F -0.5771(5) 0.0498(3) 0.3456(3) 0.0906(17) Uani 1 1 d . . . . .
F14 F -0.6362(4) 0.0544(3) 0.5079(3) 0.0857(15) Uani 1 1 d . . . . .
F15 F -0.4749(3) 0.1613(3) 0.6384(3) 0.0613(11) Uani 1 1 d . . . . .
H2N H 0.040(8) 0.392(6) 0.851(5) 0.074 Uiso 1 1 d . U . . .
H4N H -0.110(8) 0.431(6) 0.742(5) 0.074 Uiso 1 1 d . U . . .
H2 H -0.225(7) 0.094(6) 0.591(5) 0.074 Uiso 1 1 d . U . . .
H3 H -0.085(7) 0.064(6) 0.682(5) 0.074 Uiso 1 1 d . U . . .
H7 H 0.232(7) 0.270(6) 0.940(5) 0.074 Uiso 1 1 d . U . . .
H8 H 0.304(7) 0.437(6) 1.013(5) 0.074 Uiso 1 1 d . U . . .
H12 H 0.148(7) 0.726(6) 1.005(5) 0.074 Uiso 1 1 d . U . . .
H13 H 0.003(7) 0.752(6) 0.910(5) 0.074 Uiso 1 1 d . U . . .
H17 H -0.290(7) 0.552(6) 0.644(5) 0.074 Uiso 1 1 d . U . . .
H18 H -0.356(7) 0.386(6) 0.559(5) 0.074 Uiso 1 1 d . U . . .
H28 H 0.207(8) 0.608(6) 1.126(5) 0.074 Uiso 1 1 d . U . . .
H29 H 0.368(7) 0.708(6) 1.214(5) 0.074 Uiso 1 1 d . U . . .
H30 H 0.552(8) 0.766(6) 1.156(5) 0.074 Uiso 1 1 d . U . . .
H31 H 0.558(8) 0.732(6) 1.015(5) 0.074 Uiso 1 1 d . U . . .
H1B1 H 0.294(8) 0.686(6) 0.870(5) 0.074 Uiso 1 1 d . U . . .
H1B2 H 0.441(8) 0.734(6) 0.860(5) 0.074 Uiso 1 1 d . U . . .
H2B1 H 0.358(7) 0.664(6) 0.727(5) 0.074 Uiso 1 1 d . U . . .
H2B2 H 0.449(8) 0.609(6) 0.750(5) 0.074 Uiso 1 1 d . U . . .
H3B1 H 0.188(8) 0.534(6) 0.745(5) 0.074 Uiso 1 1 d . U . . .
H3B2 H 0.274(7) 0.498(6) 0.783(5) 0.074 Uiso 1 1 d . U . . .
H4B1 H 0.383(7) 0.396(6) 0.604(5) 0.074 Uiso 1 1 d . U . . .
H4B2 H 0.447(7) 0.499(6) 0.649(5) 0.074 Uiso 1 1 d . U . . .
H6B1 H 0.264(7) 0.455(6) 0.530(5) 0.074 Uiso 1 1 d . U . . .
H6B2 H 0.324(7) 0.561(6) 0.598(5) 0.074 Uiso 1 1 d . U . . .
H8B1 H 0.177(7) 0.345(6) 0.704(5) 0.074 Uiso 1 1 d . U . . .
H8B2 H 0.085(7) 0.400(5) 0.676(5) 0.074 Uiso 1 1 d . U . . .
C1E C -0.3493(13) 1.0873(10) 0.8632(9) 0.133(5) Uiso 1 1 d D . . . .
H1E1 H -0.267975 1.12844 0.865196 0.199 Uiso 1 1 calc R U . A 1
H1E2 H -0.357189 1.028671 0.82309 0.199 Uiso 1 1 calc R U . A 1
H1E3 H -0.407032 1.115575 0.845876 0.199 Uiso 1 1 calc R U . A 1
C2F C -0.373(2) 1.0709(19) 0.9480(13) 0.120(10) Uiso 0.50(2) 1 d D . P B 1
H2F1 H -0.362149 1.131127 0.987862 0.144 Uiso 0.50(2) 1 calc R U P B 1
H2F2 H -0.312462 1.044495 0.965147 0.144 Uiso 0.50(2) 1 calc R U P B 1
C3F C -0.497(3) 1.008(2) 0.9564(11) 0.150(14) Uiso 0.50(2) 1 d D . P B 1
H3F1 H -0.559328 1.036226 0.94554 0.18 Uiso 0.50(2) 1 calc R U P B 1
H3F2 H -0.512534 0.948296 0.914669 0.18 Uiso 0.50(2) 1 calc R U P B 1
C2G C -0.4627(15) 1.0320(13) 0.8917(11) 0.083(7) Uiso 0.50(2) 1 d D . P B 2
H2G1 H -0.487272 0.968738 0.855488 0.1 Uiso 0.50(2) 1 calc R U P B 2
H2G2 H -0.527373 1.059752 0.885537 0.1 Uiso 0.50(2) 1 calc R U P B 2
C3G C -0.4470(16) 1.0278(16) 0.9827(13) 0.098(8) Uiso 0.50(2) 1 d D . P B 2
H3G1 H -0.379486 1.00273 0.988242 0.118 Uiso 0.50(2) 1 calc R U P B 2
H3G2 H -0.423548 1.091477 1.017974 0.118 Uiso 0.50(2) 1 calc R U P B 2
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
C1 N1 C4 105.8(4) .
C6 N2 C9 109.4(4) .
C6 N2 H2N 126(8) .
C9 N2 H2N 124(8) .
C14 N3 C11 106.0(4) .
C16 N4 C19 108.9(4) .
C16 N4 H4N 119(7) .
C19 N4 H4N 132(7) .
N1 C1 C20 125.2(5) .
N1 C1 C2 110.5(4) .
C20 C1 C2 124.3(5) .
C3 C2 C1 106.5(5) .
C3 C2 H2 128(6) .
C1 C2 H2 125(6) .
C2 C3 C4 107.6(5) .
C2 C3 H3 127(6) .
C4 C3 H3 125(6) .
N1 C4 C5 125.7(5) .
N1 C4 C3 109.6(5) .
C5 C4 C3 124.6(5) .
C4 C5 C6 126.8(5) .
C4 C5 C21 117.4(5) .
C6 C5 C21 115.6(5) .
N2 C6 C5 125.5(5) .
N2 C6 C7 107.5(5) .
C5 C6 C7 126.9(5) .
C8 C7 C6 108.0(5) .
C8 C7 H7 126(5) .
C6 C7 H7 126(6) .
C7 C8 C9 107.8(5) .
C7 C8 H8 128(5) .
C9 C8 H8 124(5) .
N2 C9 C10 126.6(4) .
N2 C9 C8 107.2(5) .
C10 C9 C8 126.2(5) .
C9 C10 C11 124.7(5) .
C9 C10 C27 117.5(4) .
C11 C10 C27 117.5(5) .
N3 C11 C10 126.0(5) .
N3 C11 C12 109.8(4) .
C10 C11 C12 124.1(5) .
C13 C12 C11 107.3(5) .
C13 C12 H12 127(5) .
C11 C12 H12 125(5) .
C12 C13 C14 106.7(5) .
C12 C13 H13 128(6) .
C14 C13 H13 126(6) .
N3 C14 C15 125.2(5) .
N3 C14 C13 110.1(4) .
C15 C14 C13 124.6(5) .
C16 C15 C14 126.9(5) .
C16 C15 C33 116.5(4) .
C14 C15 C33 116.6(5) .
N4 C16 C15 125.3(5) .
N4 C16 C17 108.0(4) .
C15 C16 C17 126.7(5) .
C18 C17 C16 107.6(5) .
C18 C17 H17 133(6) .
C16 C17 H17 120(6) .
C17 C18 C19 108.2(5) .
C17 C18 H18 128(5) .
C19 C18 H18 124(5) .
N4 C19 C20 125.8(4) .
N4 C19 C18 107.3(4) .
C20 C19 C18 126.9(5) .
C19 C20 C1 126.1(5) .
C19 C20 C39 116.8(4) .
C1 C20 C39 117.1(5) .
C26 C21 C22 115.8(5) .
C26 C21 C5 122.5(5) .
C22 C21 C5 121.7(6) .
F5 C22 C23 119.1(6) .
F5 C22 C21 119.2(5) .
C23 C22 C21 121.7(6) .
F4 C23 C24 120.6(6) .
F4 C23 C22 119.2(7) .
C24 C23 C22 120.2(6) .
F3 C24 C25 121.6(8) .
F3 C24 C23 119.0(7) .
C25 C24 C23 119.3(6) .
F2 C25 C24 119.8(7) .
F2 C25 C26 120.3(7) .
C24 C25 C26 119.9(7) .
F1 C26 C21 118.7(6) .
F1 C26 C25 118.3(7) .
C21 C26 C25 123.1(7) .
C28 C27 C32 118.2(5) .
C28 C27 C10 122.8(5) .
C32 C27 C10 119.0(5) .
C27 C28 C29 121.5(6) .
C27 C28 H28 116(6) .
C29 C28 H28 122(6) .
C30 C29 C28 119.5(6) .
C30 C29 H29 120(6) .
C28 C29 H29 120(6) .
C29 C30 C31 120.4(6) .
C29 C30 H30 126(5) .
C31 C30 H30 113(5) .
C30 C31 C32 119.7(6) .
C30 C31 H31 122(5) .
C32 C31 H31 118(5) .
O1 C32 C31 119.7(5) .
O1 C32 C27 119.6(5) .
C31 C32 C27 120.6(5) .
C38 C33 C34 116.2(5) .
C38 C33 C15 121.0(5) .
C34 C33 C15 122.7(5) .
F6 C34 C35 118.6(5) .
F6 C34 C33 119.2(5) .
C35 C34 C33 122.2(5) .
F7 C35 C34 120.1(6) .
F7 C35 C36 120.3(6) .
C34 C35 C36 119.5(6) .
F8 C36 C37 120.5(6) .
F8 C36 C35 119.4(6) .
C37 C36 C35 120.1(6) .
F9 C37 C36 120.0(6) .
F9 C37 C38 120.1(6) .
C36 C37 C38 120.0(6) .
F10 C38 C37 118.7(5) .
F10 C38 C33 119.3(5) .
C37 C38 C33 122.0(6) .
C40 C39 C44 116.6(5) .
C40 C39 C20 122.2(5) .
C44 C39 C20 121.2(5) .
F11 C40 C39 119.2(5) .
F11 C40 C41 120.2(6) .
C39 C40 C41 120.6(6) .
F12 C41 C42 123.8(7) .
F12 C41 C40 117.1(8) .
C42 C41 C40 119.0(6) .
C43 C42 C41 121.7(6) .
C43 C42 F13 120.7(8) .
C41 C42 F13 117.5(8) .
C42 C43 F14 120.5(6) .
C42 C43 C44 119.2(7) .
F14 C43 C44 120.3(7) .
F15 C44 C43 117.9(6) .
F15 C44 C39 119.3(5) .
C43 C44 C39 122.8(6) .
C3B N1S C4B 111.5(5) .
C3B N1S C8B 106.3(4) .
C4B N1S C8B 111.6(5) .
C3B N1S C6B 110.3(5) .
C4B N1S C6B 106.3(4) .
C8B N1S C6B 110.8(5) .
C32 O1 C1B 116.0(5) .
O1 C1B C2B 106.9(6) .
O1 C1B H1B1 105(5) .
C2B C1B H1B1 116(5) .
O1 C1B H1B2 108(5) .
C2B C1B H1B2 108(5) .
H1B1 C1B H1B2 112(7) .
C1B C2B C3B 109.0(5) .
C1B C2B H2B1 105(5) .
C3B C2B H2B1 117(5) .
C1B C2B H2B2 105(5) .
C3B C2B H2B2 109(5) .
H2B1 C2B H2B2 111(7) .
N1S C3B C2B 115.3(5) .
N1S C3B H3B1 107(5) .
C2B C3B H3B1 115(5) .
N1S C3B H3B2 104(5) .
C2B C3B H3B2 110(5) .
H3B1 C3B H3B2 104(7) .
N1S C4B C5B 114.5(5) .
N1S C4B H4B1 108(5) .
C5B C4B H4B1 112(5) .
N1S C4B H4B2 103(5) .
C5B C4B H4B2 111(5) .
H4B1 C4B H4B2 107(7) .
C4B C5B H5B3 109.5 .
C4B C5B H5B1 109.5 .
H5B3 C5B H5B1 109.5 .
C4B C5B H5B2 109.5 .
H5B3 C5B H5B2 109.5 .
H5B1 C5B H5B2 109.5 .
C7B C6B N1S 114.2(5) .
C7B C6B H6B1 112(5) .
N1S C6B H6B1 109(5) .
C7B C6B H6B2 111(4) .
N1S C6B H6B2 100(4) .
H6B1 C6B H6B2 110(6) .
C6B C7B H7B3 109.5 .
C6B C7B H7B2 109.5 .
H7B3 C7B H7B2 109.5 .
C6B C7B H7B1 109.5 .
H7B3 C7B H7B1 109.5 .
H7B2 C7B H7B1 109.5 .
N1S C8B C9B 115.3(5) .
N1S C8B H8B1 110(5) .
C9B C8B H8B1 106(5) .
N1S C8B H8B2 104(4) .
C9B C8B H8B2 116(4) .
H8B1 C8B H8B2 105(6) .
C8B C9B H9B3 109.5 .
C8B C9B H9B2 109.5 .
H9B3 C9B H9B2 109.5 .
C8B C9B H9B1 109.5 .
H9B3 C9B H9B1 109.5 .
H9B2 C9B H9B1 109.5 .
C2F C1E H1E1 109.5 .
C2F C1E H1E2 109.5 .
H1E1 C1E H1E2 109.5 .
C2F C1E H1E3 109.5 .
H1E1 C1E H1E3 109.5 .
H1E2 C1E H1E3 109.5 .
C1E C2F C3F 116.5(16) .
C1E C2F H2F1 108.2 .
C3F C2F H2F1 108.2 .
C1E C2F H2F2 108.2 .
C3F C2F H2F2 108.2 .
H2F1 C2F H2F2 107.3 .
C3F C3F C2F 110(3) 2_477
C3F C3F H3F1 109.7 2_477
C2F C3F H3F1 109.7 .
C3F C3F H3F2 109.7 2_477
C2F C3F H3F2 109.7 .
H3F1 C3F H3F2 108.2 .
C1E C2G C3G 112.1(13) .
C1E C2G H2G1 109.2 .
C3G C2G H2G1 109.2 .
C1E C2G H2G2 109.2 .
C3G C2G H2G2 109.2 .
H2G1 C2G H2G2 107.9 .
C3G C3G C2G 117(2) 2_477
C3G C3G H3G1 108 2_477
C2G C3G H3G1 108 .
C3G C3G H3G2 108 2_477
C2G C3G H3G2 108 .
H3G1 C3G H3G2 107.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.365(6) .
N1 C4 1.365(7) .
N2 C6 1.362(7) .
N2 C9 1.363(7) .
N2 H2N 0.69(8) .
N3 C14 1.364(6) .
N3 C11 1.370(6) .
N4 C16 1.364(7) .
N4 C19 1.372(6) .
N4 H4N 0.74(8) .
C1 C20 1.401(7) .
C1 C2 1.443(8) .
C2 C3 1.330(8) .
C2 H2 0.83(8) .
C3 C4 1.445(8) .
C3 H3 0.86(8) .
C4 C5 1.383(8) .
C5 C6 1.396(8) .
C5 C21 1.504(7) .
C6 C7 1.421(8) .
C7 C8 1.349(8) .
C7 H7 0.87(8) .
C8 C9 1.428(7) .
C8 H8 0.93(8) .
C9 C10 1.396(7) .
C10 C11 1.398(7) .
C10 C27 1.489(7) .
C11 C12 1.442(8) .
C12 C13 1.340(8) .
C12 H12 0.92(8) .
C13 C14 1.446(7) .
C13 H13 0.86(8) .
C14 C15 1.398(7) .
C15 C16 1.392(7) .
C15 C33 1.499(7) .
C16 C17 1.430(7) .
C17 C18 1.347(8) .
C17 H17 0.85(8) .
C18 C19 1.433(7) .
C18 H18 0.93(8) .
C19 C20 1.391(7) .
C20 C39 1.497(7) .
C21 C26 1.371(9) .
C21 C22 1.386(8) .
C22 F5 1.332(8) .
C22 C23 1.380(9) .
C23 F4 1.347(8) .
C23 C24 1.367(11) .
C24 F3 1.330(8) .
C24 C25 1.354(11) .
C25 F2 1.320(9) .
C25 C26 1.372(10) .
C26 F1 1.336(8) .
C27 C28 1.368(8) .
C27 C32 1.391(8) .
C28 C29 1.380(9) .
C28 H28 0.86(8) .
C29 C30 1.364(10) .
C29 H29 0.86(8) .
C30 C31 1.375(9) .
C30 H30 0.90(8) .
C31 C32 1.377(8) .
C31 H31 0.92(8) .
C32 O1 1.377(7) .
C33 C38 1.380(8) .
C33 C34 1.383(8) .
C34 F6 1.345(7) .
C34 C35 1.364(8) .
C35 F7 1.341(7) .
C35 C36 1.369(9) .
C36 F8 1.340(7) .
C36 C37 1.350(10) .
C37 F9 1.346(7) .
C37 C38 1.371(9) .
C38 F10 1.338(7) .
C39 C40 1.365(8) .
C39 C44 1.385(8) .
C40 F11 1.336(8) .
C40 C41 1.420(10) .
C41 F12 1.336(8) .
C41 C42 1.343(11) .
C42 C43 1.336(11) .
C42 F13 1.355(8) .
C43 F14 1.342(8) .
C43 C44 1.365(9) .
C44 F15 1.341(7) .
N1S C3B 1.505(8) .
N1S C4B 1.507(8) .
N1S C8B 1.508(7) .
N1S C6B 1.522(7) .
O1 C1B 1.425(9) .
C1B C2B 1.521(9) .
C1B H1B1 1.01(8) .
C1B H1B2 0.99(8) .
C2B C3B 1.522(9) .
C2B H2B1 0.92(8) .
C2B H2B2 1.03(8) .
C3B H3B1 0.91(9) .
C3B H3B2 0.93(8) .
C4B C5B 1.521(9) .
C4B H4B1 0.89(8) .
C4B H4B2 1.01(8) .
C5B H5B3 0.96 .
C5B H5B1 0.96 .
C5B H5B2 0.96 .
C6B C7B 1.505(10) .
C6B H6B1 1.00(8) .
C6B H6B2 1.04(8) .
C7B H7B3 0.96 .
C7B H7B2 0.96 .
C7B H7B1 0.96 .
C8B C9B 1.525(9) .
C8B H8B1 0.98(8) .
C8B H8B2 1.09(8) .
C9B H9B3 0.96 .
C9B H9B2 0.96 .
C9B H9B1 0.96 .
C1E C2F 1.465(15) .
C1E C2G 1.478(15) .
C1E H1E1 0.96 .
C1E H1E2 0.96 .
C1E H1E3 0.96 .
C2F C3F 1.498(17) .
C2F H2F1 0.97 .
C2F H2F2 0.97 .
C3F C3F 1.484(18) 2_477
C3F H3F1 0.97 .
C3F H3F2 0.97 .
C2G C3G 1.498(16) .
C2G H2G1 0.97 .
C2G H2G2 0.97 .
C3G C3G 1.471(17) 2_477
C3G H3G1 0.97 .
C3G H3G2 0.97 .
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_4
C4 N1 C1 C20 -177.5(5) .
C4 N1 C1 C2 -0.5(6) .
N1 C1 C2 C3 0.1(7) .
C20 C1 C2 C3 177.1(5) .
C1 C2 C3 C4 0.4(7) .
C1 N1 C4 C5 178.2(5) .
C1 N1 C4 C3 0.7(6) .
C2 C3 C4 N1 -0.7(7) .
C2 C3 C4 C5 -178.2(6) .
N1 C4 C5 C6 -1.0(9) .
C3 C4 C5 C6 176.1(6) .
N1 C4 C5 C21 -176.0(5) .
C3 C4 C5 C21 1.0(8) .
C9 N2 C6 C5 -176.2(5) .
C9 N2 C6 C7 1.2(6) .
C4 C5 C6 N2 2.7(9) .
C21 C5 C6 N2 177.9(5) .
C4 C5 C6 C7 -174.1(6) .
C21 C5 C6 C7 1.1(9) .
N2 C6 C7 C8 -1.6(7) .
C5 C6 C7 C8 175.7(6) .
C6 C7 C8 C9 1.4(7) .
C6 N2 C9 C10 179.1(5) .
C6 N2 C9 C8 -0.3(6) .
C7 C8 C9 N2 -0.8(6) .
C7 C8 C9 C10 179.9(5) .
N2 C9 C10 C11 2.2(8) .
C8 C9 C10 C11 -178.5(5) .
N2 C9 C10 C27 -172.3(5) .
C8 C9 C10 C27 7.0(8) .
C14 N3 C11 C10 -174.2(5) .
C14 N3 C11 C12 2.7(5) .
C9 C10 C11 N3 -8.4(8) .
C27 C10 C11 N3 166.1(4) .
C9 C10 C11 C12 175.2(5) .
C27 C10 C11 C12 -10.4(7) .
N3 C11 C12 C13 -1.7(6) .
C10 C11 C12 C13 175.3(5) .
C11 C12 C13 C14 0.0(6) .
C11 N3 C14 C15 175.1(5) .
C11 N3 C14 C13 -2.7(5) .
C12 C13 C14 N3 1.7(6) .
C12 C13 C14 C15 -176.2(5) .
N3 C14 C15 C16 1.9(8) .
C13 C14 C15 C16 179.4(5) .
N3 C14 C15 C33 -175.4(4) .
C13 C14 C15 C33 2.2(7) .
C19 N4 C16 C15 177.3(5) .
C19 N4 C16 C17 -1.3(5) .
C14 C15 C16 N4 -0.3(8) .
C33 C15 C16 N4 176.9(5) .
C14 C15 C16 C17 178.0(5) .
C33 C15 C16 C17 -4.8(7) .
N4 C16 C17 C18 1.1(6) .
C15 C16 C17 C18 -177.4(5) .
C16 C17 C18 C19 -0.6(6) .
C16 N4 C19 C20 -177.9(5) .
C16 N4 C19 C18 0.9(5) .
C17 C18 C19 N4 -0.2(6) .
C17 C18 C19 C20 178.6(5) .
N4 C19 C20 C1 0.8(8) .
C18 C19 C20 C1 -177.7(5) .
N4 C19 C20 C39 179.2(5) .
C18 C19 C20 C39 0.6(8) .
N1 C1 C20 C19 -0.1(9) .
C2 C1 C20 C19 -176.8(5) .
N1 C1 C20 C39 -178.5(5) .
C2 C1 C20 C39 4.9(8) .
C4 C5 C21 C26 84.2(8) .
C6 C5 C21 C26 -91.5(8) .
C4 C5 C21 C22 -94.8(7) .
C6 C5 C21 C22 89.6(7) .
C26 C21 C22 F5 -180.0(6) .
C5 C21 C22 F5 -0.9(9) .
C26 C21 C22 C23 -0.2(9) .
C5 C21 C22 C23 178.8(6) .
F5 C22 C23 F4 1.3(10) .
C21 C22 C23 F4 -178.4(6) .
F5 C22 C23 C24 179.5(7) .
C21 C22 C23 C24 -0.2(10) .
F4 C23 C24 F3 -0.5(11) .
C22 C23 C24 F3 -178.7(7) .
F4 C23 C24 C25 179.3(8) .
C22 C23 C24 C25 1.1(12) .
F3 C24 C25 F2 -1.3(14) .
C23 C24 C25 F2 178.9(8) .
F3 C24 C25 C26 178.3(8) .
C23 C24 C25 C26 -1.5(14) .
C22 C21 C26 F1 -179.7(7) .
C5 C21 C26 F1 1.2(11) .
C22 C21 C26 C25 -0.2(11) .
C5 C21 C26 C25 -179.2(8) .
F2 C25 C26 F1 0.2(14) .
C24 C25 C26 F1 -179.4(8) .
F2 C25 C26 C21 -179.4(8) .
C24 C25 C26 C21 1.0(14) .
C9 C10 C27 C28 -93.9(7) .
C11 C10 C27 C28 91.2(7) .
C9 C10 C27 C32 85.6(6) .
C11 C10 C27 C32 -89.3(6) .
C32 C27 C28 C29 0.9(9) .
C10 C27 C28 C29 -179.7(6) .
C27 C28 C29 C30 -0.3(11) .
C28 C29 C30 C31 0.0(11) .
C29 C30 C31 C32 -0.2(11) .
C30 C31 C32 O1 -175.5(6) .
C30 C31 C32 C27 0.8(10) .
C28 C27 C32 O1 175.2(5) .
C10 C27 C32 O1 -4.3(8) .
C28 C27 C32 C31 -1.1(9) .
C10 C27 C32 C31 179.4(6) .
C16 C15 C33 C38 -81.0(6) .
C14 C15 C33 C38 96.6(6) .
C16 C15 C33 C34 101.1(6) .
C14 C15 C33 C34 -81.4(6) .
C38 C33 C34 F6 179.5(5) .
C15 C33 C34 F6 -2.5(8) .
C38 C33 C34 C35 -1.6(8) .
C15 C33 C34 C35 176.5(5) .
F6 C34 C35 F7 0.1(9) .
C33 C34 C35 F7 -178.9(5) .
F6 C34 C35 C36 179.8(5) .
C33 C34 C35 C36 0.8(9) .
F7 C35 C36 F8 -0.7(9) .
C34 C35 C36 F8 179.6(6) .
F7 C35 C36 C37 -179.6(6) .
C34 C35 C36 C37 0.8(10) .
F8 C36 C37 F9 0.5(10) .
C35 C36 C37 F9 179.3(6) .
F8 C36 C37 C38 179.7(6) .
C35 C36 C37 C38 -1.5(10) .
F9 C37 C38 F10 -0.2(9) .
C36 C37 C38 F10 -179.4(6) .
F9 C37 C38 C33 179.9(6) .
C36 C37 C38 C33 0.7(10) .
C34 C33 C38 F10 -179.1(5) .
C15 C33 C38 F10 2.9(8) .
C34 C33 C38 C37 0.8(8) .
C15 C33 C38 C37 -177.2(5) .
C19 C20 C39 C40 80.7(7) .
C1 C20 C39 C40 -100.8(6) .
C19 C20 C39 C44 -98.6(6) .
C1 C20 C39 C44 79.9(7) .
C44 C39 C40 F11 179.4(5) .
C20 C39 C40 F11 0.1(8) .
C44 C39 C40 C41 -0.5(8) .
C20 C39 C40 C41 -179.8(5) .
F11 C40 C41 F12 -2.5(9) .
C39 C40 C41 F12 177.4(5) .
F11 C40 C41 C42 179.4(6) .
C39 C40 C41 C42 -0.8(9) .
F12 C41 C42 C43 -176.3(6) .
C40 C41 C42 C43 1.7(10) .
F12 C41 C42 F13 1.2(10) .
C40 C41 C42 F13 179.2(6) .
C41 C42 C43 F14 178.0(6) .
F13 C42 C43 F14 0.6(10) .
C41 C42 C43 C44 -1.2(11) .
F13 C42 C43 C44 -178.7(6) .
C42 C43 C44 F15 179.9(6) .
F14 C43 C44 F15 0.7(10) .
C42 C43 C44 C39 -0.1(10) .
F14 C43 C44 C39 -179.4(6) .
C40 C39 C44 F15 -179.1(5) .
C20 C39 C44 F15 0.2(8) .
C40 C39 C44 C43 1.0(9) .
C20 C39 C44 C43 -179.7(6) .
C31 C32 O1 C1B -91.4(7) .
C27 C32 O1 C1B 92.3(7) .
C32 O1 C1B C2B -169.6(5) .
O1 C1B C2B C3B 61.3(8) .
C4B N1S C3B C2B 57.0(8) .
C8B N1S C3B C2B 178.9(7) .
C6B N1S C3B C2B -60.9(8) .
C1B C2B C3B N1S -166.4(7) .
C3B N1S C4B C5B 54.3(8) .
C8B N1S C4B C5B -64.5(8) .
C6B N1S C4B C5B 174.6(6) .
C3B N1S C6B C7B -62.5(7) .
C4B N1S C6B C7B 176.4(6) .
C8B N1S C6B C7B 54.9(8) .
C3B N1S C8B C9B 175.4(7) .
C4B N1S C8B C9B -62.7(8) .
C6B N1S C8B C9B 55.5(8) .
C1E C2F C3F C3F 175(3) 2_477
C1E C2G C3G C3G -178(3) 2_477
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
_restr_equal_distance_details
C1E 1_555 C2F 1_555 1
;
 C1E-C2F,C2F-C3F,C3F-C3F, C1E-C2G, C2G-C3G, C3G-C3G are restrained
 to be equal
;
C2F 1_555 C3F 1_555 1 .
C1E 1_555 C2G 1_555 1 .
C2G 1_555 C3G 1_555 1 .
C3F 1_555 C3F 2_555 1 .
C3G 1_555 C3G 2_555 1 .
