#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:34:13 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230193 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/70/7057003.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_7057003
loop_
_publ_author_name
'Almeida, José'
'Silva, André M. N.'
'Rebelo, Susana L. H.'
'Cunha-Silva, Luís'
'Rangel, Maria'
'de Castro, Baltazar'
'Leite, Andreia'
'Silva, Ana M. G.'
_publ_section_title
;
 Synthesis and coordination studies of
 5-(4′-carboxyphenyl)-10,15,20-tris(pentafluorophenyl)porphyrin and
 its pyrrolidine-fused chlorin derivative
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              8169
_journal_paper_doi               10.1039/C7NJ05165D
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C45 H15 F15 N4 O2, 0.5(C6), C6 H14'
_chemical_formula_sum            'C54 H36 F15 N4 O2'
_chemical_formula_weight         1057.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             '29 November 2017'
_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_audit_update_record
;
2017-11-29 deposited with the CCDC.
2018-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.737(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.7872(9)
_cell_length_b                   24.9663(13)
_cell_length_c                   26.3075(13)
_cell_measurement_reflns_used    6583
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.25
_cell_measurement_theta_min      3.56
_cell_volume                     11020.8(10)
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            71076
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       prism
_exptl_crystal_F_000             4312
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         9700
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      3.290
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2499
_refine_ls_wR_factor_ref         0.2696
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7884
_reflns_number_total             9700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj05165d2.cif
_cod_data_source_block           LCS16034
_cod_depositor_comments          'Adding full bibliography for 7057003.cif.'
_cod_database_code               7057003
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
F6 F 0.71983(10) 0.77388(7) 0.25863(6) 0.0461(5) Uani 1 1 d . . .
F10 F 0.85888(11) 0.71829(8) 0.40736(7) 0.0570(5) Uani 1 1 d . . .
F5 F 0.35390(12) 0.74590(8) 0.33720(6) 0.0606(6) Uani 1 1 d . . .
F1 F 0.43219(12) 0.72073(9) 0.50824(6) 0.0608(6) Uani 1 1 d . . .
F7 F 0.83181(12) 0.84870(7) 0.24325(7) 0.0576(5) Uani 1 1 d . . .
N1 N 0.48581(12) 0.59436(7) 0.39880(7) 0.0234(4) Uani 1 1 d . . .
F11 F 0.72493(12) 0.48565(9) 0.21951(7) 0.0657(6) Uani 1 1 d . . .
F9 F 0.97001(12) 0.79337(9) 0.39195(8) 0.0690(6) Uani 1 1 d . . .
O1 O 0.33282(14) 0.29037(9) 0.51905(8) 0.0516(6) Uani 1 1 d D . .
O2 O 0.23851(13) 0.29940(9) 0.45882(8) 0.0534(6) Uani 1 1 d . . .
N2 N 0.59099(12) 0.68231(8) 0.37166(7) 0.0246(5) Uani 1 1 d D . .
N4 N 0.60164(12) 0.51572(8) 0.36984(7) 0.0263(5) Uani 1 1 d D . .
F8 F 0.95831(13) 0.85748(8) 0.30902(9) 0.0680(6) Uani 1 1 d . . .
F13 F 0.91767(12) 0.35160(9) 0.23053(10) 0.0758(7) Uani 1 1 d . . .
F15 F 0.83975(14) 0.43891(10) 0.37776(8) 0.0748(7) Uani 1 1 d . . .
N3 N 0.70428(12) 0.60256(8) 0.33928(8) 0.0286(5) Uani 1 1 d . . .
F4 F 0.25003(14) 0.82068(10) 0.36401(9) 0.0836(8) Uani 1 1 d . . .
F3 F 0.23427(15) 0.84576(9) 0.46329(10) 0.0861(8) Uani 1 1 d . . .
F14 F 0.92925(14) 0.36518(10) 0.33300(10) 0.0850(8) Uani 1 1 d . . .
F12 F 0.81317(14) 0.41055(11) 0.17529(9) 0.0881(9) Uani 1 1 d . . .
F2 F 0.32562(15) 0.79571(10) 0.53530(8) 0.0804(7) Uani 1 1 d . . .
C2 C 0.44457(15) 0.54951(9) 0.41162(9) 0.0258(5) Uani 1 1 d . . .
C5 C 0.43674(15) 0.63602(10) 0.40977(9) 0.0265(5) Uani 1 1 d . . .
C1 C 0.47360(15) 0.49656(9) 0.40899(8) 0.0264(5) Uani 1 1 d . . .
C6 C 0.45643(15) 0.69061(9) 0.40554(9) 0.0264(5) Uani 1 1 d . . .
C10 C 0.65229(15) 0.71570(9) 0.35971(9) 0.0263(5) Uani 1 1 d . . .
C7 C 0.52833(15) 0.71140(9) 0.38864(8) 0.0251(5) Uani 1 1 d . . .
C20 C 0.54669(15) 0.48160(9) 0.38963(9) 0.0266(5) Uani 1 1 d . . .
C21 C 0.42454(15) 0.45186(9) 0.42890(9) 0.0278(5) Uani 1 1 d . . .
C34 C 0.78568(15) 0.74288(10) 0.33300(10) 0.0313(6) Uani 1 1 d . . .
C8 C 0.55086(16) 0.76651(10) 0.38684(9) 0.0293(6) Uani 1 1 d . . .
H8 H 0.5190 0.7961 0.3962 0.035 Uiso 1 1 calc R U .
C9 C 0.62587(15) 0.76894(10) 0.36941(9) 0.0285(5) Uani 1 1 d . . .
H9 H 0.6558 0.8007 0.3645 0.034 Uiso 1 1 calc R U .
C27 C 0.29974(17) 0.31504(11) 0.48078(10) 0.0353(6) Uani 1 1 d . . .
C28 C 0.39666(16) 0.73115(10) 0.42133(10) 0.0309(6) Uani 1 1 d . . .
C24 C 0.34173(16) 0.36358(10) 0.46380(9) 0.0322(6) Uani 1 1 d . . .
C15 C 0.74854(16) 0.56087(11) 0.32131(10) 0.0322(6) Uani 1 1 d . . .
C12 C 0.74834(15) 0.64702(10) 0.33060(10) 0.0308(6) Uani 1 1 d . . .
C11 C 0.72567(15) 0.69995(10) 0.34151(9) 0.0277(5) Uani 1 1 d . . .
C3 C 0.36711(16) 0.56323(11) 0.43065(10) 0.0341(6) Uani 1 1 d . . .
H3 H 0.3277 0.5391 0.4421 0.041 Uiso 1 1 calc R U .
C35 C 0.78072(16) 0.77754(10) 0.29177(10) 0.0329(6) Uani 1 1 d . . .
C19 C 0.57372(16) 0.42851(10) 0.38181(10) 0.0329(6) Uani 1 1 d . . .
H19 H 0.5479 0.3968 0.3925 0.040 Uiso 1 1 calc R U .
C17 C 0.66153(15) 0.48595(10) 0.34859(9) 0.0288(5) Uani 1 1 d . . .
C16 C 0.72847(15) 0.50673(10) 0.32477(9) 0.0300(6) Uani 1 1 d . . .
C4 C 0.36211(16) 0.61690(11) 0.42887(11) 0.0350(6) Uani 1 1 d . . .
H4 H 0.3180 0.6382 0.4383 0.042 Uiso 1 1 calc DR U .
C26 C 0.45060(17) 0.42514(11) 0.47223(10) 0.0351(6) Uani 1 1 d . . .
H26 H 0.4971 0.4372 0.4902 0.042 Uiso 1 1 calc R U .
C39 C 0.85121(17) 0.74953(11) 0.36647(10) 0.0378(6) Uani 1 1 d . . .
C25 C 0.41001(17) 0.38105(11) 0.48991(10) 0.0364(6) Uani 1 1 d . . .
H25 H 0.4287 0.3629 0.5197 0.044 Uiso 1 1 calc R U .
C40 C 0.78095(15) 0.46626(10) 0.30077(11) 0.0357(6) Uani 1 1 d . . .
C22 C 0.35526(16) 0.43474(11) 0.40366(10) 0.0336(6) Uani 1 1 d . . .
H22 H 0.3361 0.4532 0.3742 0.040 Uiso 1 1 calc R U .
C23 C 0.31434(17) 0.39112(11) 0.42119(10) 0.0373(6) Uani 1 1 d . . .
H23 H 0.2668 0.3798 0.4039 0.045 Uiso 1 1 calc R U .
C18 C 0.64326(16) 0.43083(10) 0.35635(10) 0.0337(6) Uani 1 1 d . . .
H18 H 0.6739 0.4011 0.3457 0.040 Uiso 1 1 calc R U .
C14 C 0.82261(17) 0.57976(12) 0.30104(11) 0.0407(7) Uani 1 1 d . . .
H14 H 0.8629 0.5586 0.2863 0.049 Uiso 1 1 calc R U .
C13 C 0.82327(17) 0.63304(11) 0.30710(11) 0.0393(7) Uani 1 1 d . . .
H13 H 0.8644 0.6570 0.2979 0.047 Uiso 1 1 calc R U .
C33 C 0.34811(18) 0.75706(12) 0.38625(11) 0.0400(7) Uani 1 1 d . . .
C36 C 0.83830(19) 0.81613(11) 0.28378(11) 0.0426(7) Uani 1 1 d . . .
C37 C 0.90228(18) 0.82082(12) 0.31696(12) 0.0453(7) Uani 1 1 d . . .
C29 C 0.38753(18) 0.74486(11) 0.47196(11) 0.0397(7) Uani 1 1 d . . .
C41 C 0.77576(17) 0.45741(12) 0.24827(11) 0.0418(7) Uani 1 1 d . . .
C38 C 0.90849(18) 0.78771(13) 0.35890(12) 0.0443(7) Uani 1 1 d . . .
C45 C 0.83362(19) 0.43420(13) 0.32769(12) 0.0478(8) Uani 1 1 d . . .
C44 C 0.8800(2) 0.39535(13) 0.30537(15) 0.0553(9) Uani 1 1 d . . .
C30 C 0.3341(2) 0.78327(13) 0.48656(12) 0.0520(8) Uani 1 1 d . . .
C43 C 0.87339(18) 0.38823(13) 0.25346(14) 0.0519(8) Uani 1 1 d . . .
C31 C 0.2871(2) 0.80874(13) 0.44976(14) 0.0550(9) Uani 1 1 d . . .
C42 C 0.82068(18) 0.41915(15) 0.22493(13) 0.0536(9) Uani 1 1 d . . .
C32 C 0.2947(2) 0.79623(13) 0.39996(14) 0.0539(9) Uani 1 1 d . . .
C57 C 0.5000 0.72870(19) 0.2500 0.0590(13) Uani 1 2 d S T P
C55 C 0.5000 0.6281(2) 0.2500 0.082(2) Uani 1 2 d S T P
C52 C 0.5000 0.4733(2) 0.2500 0.0737(17) Uani 1 2 d S T P
C54 C 0.5000 0.5730(2) 0.2500 0.087(2) Uani 1 2 d S T P
C49 C 0.8923(4) 0.6335(3) 0.1613(2) 0.1106(19) Uani 1 1 d . . .
H49A H 0.8440 0.6272 0.1812 0.133 Uiso 1 1 calc R U .
H49B H 0.8754 0.6355 0.1250 0.133 Uiso 1 1 calc R U .
C47 C 0.9143(4) 0.5359(3) 0.1541(3) 0.130(2) Uani 1 1 d . . .
H47A H 0.8965 0.5370 0.1178 0.156 Uiso 1 1 calc R U .
H47B H 0.8669 0.5284 0.1745 0.156 Uiso 1 1 calc R U .
C48 C 0.9460(4) 0.5880(3) 0.1685(3) 0.120(2) Uani 1 1 d . . .
H48A H 0.9941 0.5946 0.1486 0.144 Uiso 1 1 calc R U .
H48B H 0.9630 0.5865 0.2048 0.144 Uiso 1 1 calc R U .
C50 C 0.9300(4) 0.6893(4) 0.1778(3) 0.148(3) Uani 1 1 d . . .
H50A H 0.9467 0.6877 0.2142 0.178 Uiso 1 1 calc R U .
H50B H 0.9780 0.6961 0.1579 0.178 Uiso 1 1 calc R U .
C56 C 0.4581(4) 0.6728(2) 0.2595(2) 0.0411(13) Uani 0.5 1 d . . P
C53 C 0.5386(4) 0.5298(3) 0.2373(2) 0.0525(16) Uani 0.5 1 d . . P
C51 C 0.8731(5) 0.7338(4) 0.1699(3) 0.172(4) Uani 1 1 d . . .
H51A H 0.8589 0.7368 0.1336 0.258 Uiso 1 1 calc R U .
H51B H 0.8976 0.7673 0.1818 0.258 Uiso 1 1 calc R U .
H51C H 0.8250 0.7268 0.1890 0.258 Uiso 1 1 calc R U .
C46 C 0.9729(5) 0.4908(4) 0.1613(4) 0.188(4) Uani 1 1 d . . .
H46A H 1.0225 0.4997 0.1445 0.281 Uiso 1 1 calc R U .
H46B H 0.9504 0.4579 0.1465 0.281 Uiso 1 1 calc R U .
H46C H 0.9840 0.4853 0.1978 0.281 Uiso 1 1 calc R U .
H2 H 0.5953(19) 0.6487(7) 0.3726(12) 0.046(9) Uiso 1 1 d D . .
H5 H 0.6046(17) 0.5548(13) 0.3703(10) 0.037(8) Uiso 1 1 d . . .
H1 H 0.324(3) 0.2568(11) 0.530(2) 0.13(2) Uiso 1 1 d D . .
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'
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
C5 N1 C2 105.0(2) . .
C27 O1 H1 129(4) . .
C7 N2 C10 110.1(2) . .
C7 N2 H2 126(2) . .
C10 N2 H2 123(2) . .
C20 N4 C17 109.0(2) . .
C20 N4 H5 130.6(17) . .
C17 N4 H5 120.3(17) . .
C12 N3 C15 105.0(2) . .
N1 C2 C1 125.3(2) . .
N1 C2 C3 111.0(2) . .
C1 C2 C3 123.6(2) . .
N1 C5 C6 125.3(2) . .
N1 C5 C4 110.9(2) . .
C6 C5 C4 123.7(2) . .
C20 C1 C2 125.3(2) . .
C20 C1 C21 115.4(2) . .
C2 C1 C21 119.2(2) . .
C7 C6 C5 126.3(2) . .
C7 C6 C28 115.5(2) . .
C5 C6 C28 118.2(2) . .
N2 C10 C11 125.9(2) . .
N2 C10 C9 106.6(2) . .
C11 C10 C9 127.4(2) . .
N2 C7 C6 126.0(2) . .
N2 C7 C8 107.1(2) . .
C6 C7 C8 126.9(2) . .
N4 C20 C1 125.7(2) . .
N4 C20 C19 107.7(2) . .
C1 C20 C19 126.3(2) . .
C26 C21 C22 119.1(2) . .
C26 C21 C1 119.1(2) . .
C22 C21 C1 121.7(2) . .
C35 C34 C39 116.5(2) . .
C35 C34 C11 122.7(2) . .
C39 C34 C11 120.8(2) . .
C9 C8 C7 107.7(2) . .
C9 C8 H8 126.1 . .
C7 C8 H8 126.1 . .
C8 C9 C10 108.4(2) . .
C8 C9 H9 125.8 . .
C10 C9 H9 125.8 . .
O2 C27 O1 123.3(2) . .
O2 C27 C24 121.3(2) . .
O1 C27 C24 115.4(2) . .
C33 C28 C29 116.6(2) . .
C33 C28 C6 121.5(2) . .
C29 C28 C6 121.9(2) . .
C23 C24 C25 119.6(2) . .
C23 C24 C27 120.2(2) . .
C25 C24 C27 120.1(2) . .
N3 C15 C16 125.3(2) . .
N3 C15 C14 111.1(2) . .
C16 C15 C14 123.4(2) . .
N3 C12 C11 125.6(2) . .
N3 C12 C13 110.9(2) . .
C11 C12 C13 123.5(2) . .
C10 C11 C12 125.7(2) . .
C10 C11 C34 117.2(2) . .
C12 C11 C34 117.1(2) . .
C4 C3 C2 106.2(2) . .
C4 C3 H3 126.9 . .
C2 C3 H3 126.9 . .
F6 C35 C36 118.4(2) . .
F6 C35 C34 119.8(2) . .
C36 C35 C34 121.8(3) . .
C18 C19 C20 108.3(2) . .
C18 C19 H19 125.9 . .
C20 C19 H19 125.9 . .
N4 C17 C16 125.8(2) . .
N4 C17 C18 107.4(2) . .
C16 C17 C18 126.8(2) . .
C15 C16 C17 125.8(2) . .
C15 C16 C40 118.7(2) . .
C17 C16 C40 115.4(2) . .
C3 C4 C5 106.7(2) . .
C3 C4 H4 126.6 . .
C5 C4 H4 126.6 . .
C21 C26 C25 121.0(2) . .
C21 C26 H26 119.5 . .
C25 C26 H26 119.5 . .
F10 C39 C38 118.2(2) . .
F10 C39 C34 119.6(2) . .
C38 C39 C34 122.2(3) . .
C26 C25 C24 119.4(2) . .
C26 C25 H25 120.3 . .
C24 C25 H25 120.3 . .
C45 C40 C41 115.9(3) . .
C45 C40 C16 123.7(3) . .
C41 C40 C16 120.3(2) . .
C23 C22 C21 120.2(2) . .
C23 C22 H22 119.9 . .
C21 C22 H22 119.9 . .
C22 C23 C24 120.6(2) . .
C22 C23 H23 119.7 . .
C24 C23 H23 119.7 . .
C19 C18 C17 107.6(2) . .
C19 C18 H18 126.2 . .
C17 C18 H18 126.2 . .
C13 C14 C15 106.5(2) . .
C13 C14 H14 126.8 . .
C15 C14 H14 126.8 . .
C14 C13 C12 106.5(2) . .
C14 C13 H13 126.8 . .
C12 C13 H13 126.8 . .
F5 C33 C28 119.7(2) . .
F5 C33 C32 118.0(3) . .
C28 C33 C32 122.3(3) . .
F7 C36 C37 119.9(3) . .
F7 C36 C35 120.1(3) . .
C37 C36 C35 120.0(3) . .
F8 C37 C36 120.2(3) . .
F8 C37 C38 120.0(3) . .
C36 C37 C38 119.8(3) . .
F1 C29 C30 118.1(3) . .
F1 C29 C28 119.8(2) . .
C30 C29 C28 122.1(3) . .
F11 C41 C42 117.9(3) . .
F11 C41 C40 119.9(2) . .
C42 C41 C40 122.2(3) . .
F9 C38 C39 120.6(3) . .
F9 C38 C37 119.7(3) . .
C39 C38 C37 119.7(3) . .
F15 C45 C40 119.4(3) . .
F15 C45 C44 117.1(3) . .
C40 C45 C44 123.4(3) . .
F14 C44 C43 120.2(3) . .
F14 C44 C45 121.1(3) . .
C43 C44 C45 118.7(3) . .
F2 C30 C29 121.4(3) . .
F2 C30 C31 119.5(3) . .
C29 C30 C31 119.2(3) . .
F13 C43 C44 120.5(3) . .
F13 C43 C42 119.7(3) . .
C44 C43 C42 119.9(3) . .
F3 C31 C32 119.9(3) . .
F3 C31 C30 120.0(3) . .
C32 C31 C30 120.1(3) . .
F12 C42 C41 121.1(3) . .
F12 C42 C43 119.1(3) . .
C41 C42 C43 119.9(3) . .
F4 C32 C31 120.7(3) . .
F4 C32 C33 119.6(3) . .
C31 C32 C33 119.7(3) . .
C56 C57 C56 56.7(4) . 2_655
C56 C55 C56 68.1(6) 2_655 .
C56 C55 C54 145.9(3) 2_655 .
C56 C55 C54 145.9(3) . .
C53 C52 C53 55.3(5) 2_655 .
C53 C54 C53 68.7(7) . 2_655
C53 C54 C55 145.7(4) . .
C53 C54 C55 145.7(4) 2_655 .
C48 C49 C50 114.1(6) . .
C48 C49 H49A 108.7 . .
C50 C49 H49A 108.7 . .
C48 C49 H49B 108.7 . .
C50 C49 H49B 108.7 . .
H49A C49 H49B 107.6 . .
C48 C47 C46 113.9(6) . .
C48 C47 H47A 108.8 . .
C46 C47 H47A 108.8 . .
C48 C47 H47B 108.8 . .
C46 C47 H47B 108.8 . .
H47A C47 H47B 107.7 . .
C47 C48 C49 116.4(6) . .
C47 C48 H48A 108.2 . .
C49 C48 H48A 108.2 . .
C47 C48 H48B 108.2 . .
C49 C48 H48B 108.2 . .
H48A C48 H48B 107.3 . .
C51 C50 C49 111.8(7) . .
C51 C50 H50A 109.3 . .
C49 C50 H50A 109.3 . .
C51 C50 H50B 109.3 . .
C49 C50 H50B 109.3 . .
H50A C50 H50B 107.9 . .
C55 C56 C56 55.9(3) . 2_655
C55 C56 C57 117.6(4) . .
C56 C56 C57 61.6(2) 2_655 .
C54 C53 C53 55.7(4) . 2_655
C54 C53 C52 118.0(5) . .
C53 C53 C52 62.4(3) 2_655 .
C50 C51 H51A 109.5 . .
C50 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C50 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C47 C46 H46A 109.5 . .
C47 C46 H46B 109.5 . .
H46A C46 H46B 109.5 . .
C47 C46 H46C 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F6 C35 1.326(3) .
F10 C39 1.332(3) .
F5 C33 1.327(3) .
F1 C29 1.339(3) .
F7 C36 1.343(3) .
N1 C5 1.363(3) .
N1 C2 1.364(3) .
F11 C41 1.326(4) .
F9 C38 1.337(3) .
O1 C27 1.291(3) .
O1 H1 0.91(2) .
O2 C27 1.228(3) .
N2 C7 1.365(3) .
N2 C10 1.368(3) .
N2 H2 0.844(18) .
N4 C20 1.370(3) .
N4 C17 1.382(3) .
N4 H5 0.98(3) .
F8 C37 1.333(3) .
F13 C43 1.334(3) .
F15 C45 1.323(4) .
N3 C12 1.357(3) .
N3 C15 1.371(3) .
F4 C32 1.337(4) .
F3 C31 1.337(3) .
F14 C44 1.320(4) .
F12 C42 1.326(4) .
F2 C30 1.331(4) .
C2 C1 1.411(3) .
C2 C3 1.449(3) .
C5 C6 1.408(3) .
C5 C4 1.445(3) .
C1 C20 1.393(3) .
C1 C21 1.491(3) .
C6 C7 1.399(3) .
C6 C28 1.493(3) .
C10 C11 1.392(4) .
C10 C9 1.427(3) .
C7 C8 1.428(3) .
C20 C19 1.418(4) .
C21 C26 1.380(4) .
C21 C22 1.389(4) .
C34 C35 1.388(4) .
C34 C39 1.398(4) .
C34 C11 1.492(3) .
C8 C9 1.355(4) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C27 C24 1.478(3) .
C28 C33 1.374(4) .
C28 C29 1.388(4) .
C24 C23 1.382(4) .
C24 C25 1.389(4) .
C15 C16 1.397(4) .
C15 C14 1.447(4) .
C12 C11 1.407(4) .
C12 C13 1.461(4) .
C3 C4 1.343(4) .
C3 H3 0.9500 .
C35 C36 1.385(4) .
C19 C18 1.365(4) .
C19 H19 0.9500 .
C17 C16 1.403(4) .
C17 C18 1.426(4) .
C16 C40 1.493(3) .
C4 H4 0.9500 .
C26 C25 1.383(4) .
C26 H26 0.9500 .
C39 C38 1.373(4) .
C25 H25 0.9500 .
C40 C45 1.373(4) .
C40 C41 1.399(4) .
C22 C23 1.375(4) .
C22 H22 0.9500 .
C23 H23 0.9500 .
C18 H18 0.9500 .
C14 C13 1.340(4) .
C14 H14 0.9500 .
C13 H13 0.9500 .
C33 C32 1.382(4) .
C36 C37 1.368(4) .
C37 C38 1.380(4) .
C29 C30 1.376(4) .
C41 C42 1.373(4) .
C45 C44 1.386(4) .
C44 C43 1.378(5) .
C30 C31 1.384(5) .
C43 C42 1.379(5) .
C31 C32 1.357(5) .
C57 C56 1.586(7) .
C57 C56 1.586(7) 2_655
C55 C56 1.345(7) 2_655
C55 C56 1.345(7) .
C55 C54 1.376(7) .
C52 C53 1.590(8) 2_655
C52 C53 1.590(8) .
C54 C53 1.308(7) .
C54 C53 1.308(7) 2_655
C49 C48 1.459(8) .
C49 C50 1.586(10) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C47 C48 1.451(9) .
C47 C46 1.504(9) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C50 C51 1.477(10) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C56 C56 1.507(12) 2_655
C53 C53 1.476(15) 2_655
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
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_4
C5 N1 C2 C1 -176.9(2) . .
C5 N1 C2 C3 0.6(3) . .
C2 N1 C5 C6 175.9(2) . .
C2 N1 C5 C4 -1.3(3) . .
N1 C2 C1 C20 -4.7(4) . .
C3 C2 C1 C20 178.1(2) . .
N1 C2 C1 C21 174.3(2) . .
C3 C2 C1 C21 -3.0(3) . .
N1 C5 C6 C7 1.3(4) . .
C4 C5 C6 C7 178.2(2) . .
N1 C5 C6 C28 -177.4(2) . .
C4 C5 C6 C28 -0.5(4) . .
C7 N2 C10 C11 179.6(2) . .
C7 N2 C10 C9 -0.6(2) . .
C10 N2 C7 C6 -178.2(2) . .
C10 N2 C7 C8 0.6(2) . .
C5 C6 C7 N2 2.4(4) . .
C28 C6 C7 N2 -179.0(2) . .
C5 C6 C7 C8 -176.2(2) . .
C28 C6 C7 C8 2.5(3) . .
C17 N4 C20 C1 -172.3(2) . .
C17 N4 C20 C19 1.5(3) . .
C2 C1 C20 N4 -0.4(4) . .
C21 C1 C20 N4 -179.4(2) . .
C2 C1 C20 C19 -173.1(2) . .
C21 C1 C20 C19 7.9(3) . .
C20 C1 C21 C26 67.8(3) . .
C2 C1 C21 C26 -111.2(3) . .
C20 C1 C21 C22 -109.0(3) . .
C2 C1 C21 C22 71.9(3) . .
N2 C7 C8 C9 -0.5(3) . .
C6 C7 C8 C9 178.3(2) . .
C7 C8 C9 C10 0.1(3) . .
N2 C10 C9 C8 0.2(3) . .
C11 C10 C9 C8 -179.9(2) . .
C7 C6 C28 C33 81.5(3) . .
C5 C6 C28 C33 -99.7(3) . .
C7 C6 C28 C29 -98.0(3) . .
C5 C6 C28 C29 80.8(3) . .
O2 C27 C24 C23 -2.8(4) . .
O1 C27 C24 C23 175.9(3) . .
O2 C27 C24 C25 178.7(3) . .
O1 C27 C24 C25 -2.6(4) . .
C12 N3 C15 C16 176.3(3) . .
C12 N3 C15 C14 0.3(3) . .
C15 N3 C12 C11 178.0(2) . .
C15 N3 C12 C13 -0.8(3) . .
N2 C10 C11 C12 2.4(4) . .
C9 C10 C11 C12 -177.4(2) . .
N2 C10 C11 C34 -177.4(2) . .
C9 C10 C11 C34 2.8(4) . .
N3 C12 C11 C10 -4.7(4) . .
C13 C12 C11 C10 174.1(3) . .
N3 C12 C11 C34 175.1(2) . .
C13 C12 C11 C34 -6.2(4) . .
C35 C34 C11 C10 -75.5(3) . .
C39 C34 C11 C10 105.4(3) . .
C35 C34 C11 C12 104.7(3) . .
C39 C34 C11 C12 -74.3(3) . .
N1 C2 C3 C4 0.3(3) . .
C1 C2 C3 C4 177.9(2) . .
C39 C34 C35 F6 -179.5(2) . .
C11 C34 C35 F6 1.4(4) . .
C39 C34 C35 C36 1.0(4) . .
C11 C34 C35 C36 -178.1(2) . .
N4 C20 C19 C18 -1.6(3) . .
C1 C20 C19 C18 172.2(2) . .
C20 N4 C17 C16 -179.8(2) . .
C20 N4 C17 C18 -0.9(3) . .
N3 C15 C16 C17 -2.3(4) . .
C14 C15 C16 C17 173.2(3) . .
N3 C15 C16 C40 176.7(2) . .
C14 C15 C16 C40 -7.7(4) . .
N4 C17 C16 C15 4.3(4) . .
C18 C17 C16 C15 -174.3(3) . .
N4 C17 C16 C40 -174.8(2) . .
C18 C17 C16 C40 6.6(4) . .
C2 C3 C4 C5 -1.1(3) . .
N1 C5 C4 C3 1.6(3) . .
C6 C5 C4 C3 -175.8(2) . .
C22 C21 C26 C25 1.7(4) . .
C1 C21 C26 C25 -175.3(3) . .
C35 C34 C39 F10 178.7(2) . .
C11 C34 C39 F10 -2.2(4) . .
C35 C34 C39 C38 -0.9(4) . .
C11 C34 C39 C38 178.2(3) . .
C21 C26 C25 C24 -0.4(4) . .
C23 C24 C25 C26 -1.4(4) . .
C27 C24 C25 C26 177.2(3) . .
C15 C16 C40 C45 104.1(3) . .
C17 C16 C40 C45 -76.7(4) . .
C15 C16 C40 C41 -78.9(3) . .
C17 C16 C40 C41 100.3(3) . .
C26 C21 C22 C23 -1.3(4) . .
C1 C21 C22 C23 175.6(2) . .
C21 C22 C23 C24 -0.5(4) . .
C25 C24 C23 C22 1.8(4) . .
C27 C24 C23 C22 -176.7(3) . .
C20 C19 C18 C17 1.0(3) . .
N4 C17 C18 C19 -0.1(3) . .
C16 C17 C18 C19 178.8(2) . .
N3 C15 C14 C13 0.4(3) . .
C16 C15 C14 C13 -175.7(3) . .
C15 C14 C13 C12 -0.9(3) . .
N3 C12 C13 C14 1.1(3) . .
C11 C12 C13 C14 -177.8(3) . .
C29 C28 C33 F5 179.9(3) . .
C6 C28 C33 F5 0.3(4) . .
C29 C28 C33 C32 2.3(4) . .
C6 C28 C33 C32 -177.3(3) . .
F6 C35 C36 F7 -0.1(4) . .
C34 C35 C36 F7 179.5(2) . .
F6 C35 C36 C37 -179.5(3) . .
C34 C35 C36 C37 0.1(4) . .
F7 C36 C37 F8 -0.3(4) . .
C35 C36 C37 F8 179.2(3) . .
F7 C36 C37 C38 179.3(3) . .
C35 C36 C37 C38 -1.2(5) . .
C33 C28 C29 F1 179.2(3) . .
C6 C28 C29 F1 -1.2(4) . .
C33 C28 C29 C30 -1.4(4) . .
C6 C28 C29 C30 178.2(3) . .
C45 C40 C41 F11 178.3(3) . .
C16 C40 C41 F11 1.1(4) . .
C45 C40 C41 C42 -0.2(4) . .
C16 C40 C41 C42 -177.4(3) . .
F10 C39 C38 F9 -0.3(4) . .
C34 C39 C38 F9 179.3(3) . .
F10 C39 C38 C37 -179.9(3) . .
C34 C39 C38 C37 -0.3(5) . .
F8 C37 C38 F9 1.4(5) . .
C36 C37 C38 F9 -178.2(3) . .
F8 C37 C38 C39 -179.1(3) . .
C36 C37 C38 C39 1.3(5) . .
C41 C40 C45 F15 -177.6(3) . .
C16 C40 C45 F15 -0.5(5) . .
C41 C40 C45 C44 0.4(5) . .
C16 C40 C45 C44 177.5(3) . .
F15 C45 C44 F14 -1.3(5) . .
C40 C45 C44 F14 -179.3(3) . .
F15 C45 C44 C43 178.1(3) . .
C40 C45 C44 C43 0.0(5) . .
F1 C29 C30 F2 -1.1(5) . .
C28 C29 C30 F2 179.5(3) . .
F1 C29 C30 C31 -179.9(3) . .
C28 C29 C30 C31 0.7(5) . .
F14 C44 C43 F13 -1.3(5) . .
C45 C44 C43 F13 179.3(3) . .
F14 C44 C43 C42 178.7(3) . .
C45 C44 C43 C42 -0.7(5) . .
F2 C30 C31 F3 0.4(5) . .
C29 C30 C31 F3 179.3(3) . .
F2 C30 C31 C32 -179.6(3) . .
C29 C30 C31 C32 -0.7(5) . .
F11 C41 C42 F12 -0.3(5) . .
C40 C41 C42 F12 178.2(3) . .
F11 C41 C42 C43 -179.0(3) . .
C40 C41 C42 C43 -0.4(5) . .
F13 C43 C42 F12 2.2(5) . .
C44 C43 C42 F12 -177.8(3) . .
F13 C43 C42 C41 -179.1(3) . .
C44 C43 C42 C41 0.9(5) . .
F3 C31 C32 F4 0.3(5) . .
C30 C31 C32 F4 -179.7(3) . .
F3 C31 C32 C33 -178.5(3) . .
C30 C31 C32 C33 1.5(5) . .
F5 C33 C32 F4 1.2(5) . .
C28 C33 C32 F4 178.9(3) . .
F5 C33 C32 C31 180.0(3) . .
C28 C33 C32 C31 -2.4(5) . .
C56 C55 C54 C53 -7.5(6) 2_655 .
C56 C55 C54 C53 172.5(6) . .
C56 C55 C54 C53 172.6(6) 2_655 2_655
C56 C55 C54 C53 -7.5(6) . 2_655
C46 C47 C48 C49 178.9(6) . .
C50 C49 C48 C47 179.8(6) . .
C48 C49 C50 C51 -179.9(6) . .
C54 C55 C56 C56 180.002(2) . 2_655
C56 C55 C56 C57 -0.002(1) 2_655 .
C54 C55 C56 C57 180.000(1) . .
C56 C57 C56 C55 0.002(1) 2_655 .
C55 C54 C53 C53 180.002(2) . 2_655
C53 C54 C53 C52 -0.002(1) 2_655 .
C55 C54 C53 C52 180.000(1) . .
C53 C52 C53 C54 0.001(1) 2_655 .
