#------------------------------------------------------------------------------
#$Date: 2020-08-06 17:42:28 +0300 (Thu, 06 Aug 2020) $
#$Revision: 255085 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157553.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_7157553
loop_
_publ_author_name
'Mori, Daiki'
'Yoneda, Tomoki'
'Suzuki, Masaaki'
'Hoshino, Tyuji'
'Neya, Saburo'
_publ_section_title
;
 Deprotection of a benzyl unit induces a 22π aromatic macrocycle of
 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5334
_journal_page_last               5338
_journal_paper_doi               10.1039/d0ob01213k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C48 H24 Cl6 F15 N5 O'
_chemical_formula_weight         1184.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-04-10 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                105.2410(10)
_cell_angle_beta                 110.6130(10)
_cell_angle_gamma                98.939(2)
_cell_formula_units_Z            2
_cell_length_a                   12.2776(3)
_cell_length_b                   13.0559(3)
_cell_length_c                   16.5083(4)
_cell_measurement_reflns_used    4860
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.240
_cell_measurement_theta_min      3.045
_cell_volume                     2297.85(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rugaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1320
_diffrn_reflns_av_unetI/netI     0.1611
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24539
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.045
_exptl_absorpt_coefficient_mu    4.388
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.803
_exptl_transmission_factor_min   0.620
_refine_diff_density_max         1.550
_refine_diff_density_min         -1.019
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         8211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0965
_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)+(0.1239P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2355
_refine_ls_wR_factor_ref         0.2705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4860
_reflns_number_total             8211
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01213k2.cif
_cod_data_source_block           1117ty_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157552--7157553.cif.
;
_cod_database_code               7157553
_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   0.474
_shelx_estimated_absorpt_t_max   0.810
loop_
_space_group_symop_operation_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
C1 C 0.8939(5) 0.7630(5) 0.9809(4) 0.0239(12) Uani 1 1 d . . . . .
C2 C 0.8605(5) 0.8618(5) 1.0026(4) 0.0254(12) Uani 1 1 d . . . . .
C3 C 0.7379(4) 0.8411(5) 0.9458(4) 0.0237(12) Uani 1 1 d . . . . .
C4 C 0.6958(5) 0.7282(5) 0.8886(3) 0.0223(12) Uani 1 1 d . . . . .
C5 C 0.5776(5) 0.6660(4) 0.8212(4) 0.0216(12) Uani 1 1 d . . . . .
C6 C 0.5408(5) 0.5625(5) 0.7523(4) 0.0222(12) Uani 1 1 d . . . . .
C7 C 0.4187(5) 0.5009(5) 0.6954(4) 0.0255(13) Uani 1 1 d . . . . .
H3 H 0.3495 0.5199 0.7012 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4170(5) 0.4108(5) 0.6318(4) 0.0225(12) Uani 1 1 d . . . . .
H4 H 0.3464 0.3569 0.5845 0.027 Uiso 1 1 calc R U . . .
N1 N 0.6117(4) 0.5036(4) 0.7221(3) 0.0246(11) Uani 1 1 d . . . . .
H5 H 0.6913 0.5232 0.7470 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5397(5) 0.4096(5) 0.6471(4) 0.0247(13) Uani 1 1 d . . . . .
C10 C 0.5714(4) 0.3308(5) 0.5905(4) 0.0211(12) Uani 1 1 d . . . . .
C11 C 0.6845(5) 0.3124(5) 0.6002(4) 0.0239(12) Uani 1 1 d . . . . .
C12 C 0.7073(5) 0.2454(5) 0.5280(4) 0.0232(12) Uani 1 1 d . . . . .
H6 H 0.6501 0.2095 0.4658 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8233(4) 0.2411(5) 0.5620(4) 0.0247(12) Uani 1 1 d . . . . .
H7 H 0.8610 0.2017 0.5278 0.030 Uiso 1 1 calc R U . . .
C14 C 0.8798(4) 0.3057(5) 0.6581(4) 0.0225(12) Uani 1 1 d . . . . .
N2 N 0.7925(4) 0.3505(4) 0.6779(3) 0.0242(10) Uani 1 1 d . . . . .
H8 H 0.8043 0.3962 0.7319 0.029 Uiso 1 1 calc R U . . .
C15 C 0.9999(5) 0.3154(5) 0.7156(4) 0.0250(13) Uani 1 1 d . . . . .
C16 C 1.0735(4) 0.3829(5) 0.8070(4) 0.0226(12) Uani 1 1 d . . . . .
C17 C 1.1951(5) 0.3905(5) 0.8646(4) 0.0247(12) Uani 1 1 d . . . . .
C18 C 1.2265(5) 0.4710(5) 0.9493(4) 0.0234(12) Uani 1 1 d . . . . .
C19 C 1.1258(4) 0.5113(4) 0.9465(4) 0.0221(12) Uani 1 1 d . . . . .
N3 N 1.0364(4) 0.4584(4) 0.8597(3) 0.0229(10) Uani 1 1 d . . . . .
H9 H 0.9649 0.4709 0.8400 0.027 Uiso 1 1 calc R U . . .
C20 C 1.1082(4) 0.6005(4) 1.0084(4) 0.0206(12) Uani 1 1 d . . . . .
C21 C 1.1756(4) 0.6381(5) 1.1074(4) 0.0244(12) Uani 1 1 d . . . . .
C22 C 1.1756(4) 0.7474(4) 1.1554(3) 0.0217(12) Uani 1 1 d . . . . .
H10 H 1.2348 0.7874 1.2163 0.026 Uiso 1 1 calc R U . . .
C23 C 1.0899(5) 0.7930(5) 1.1128(4) 0.0269(13) Uani 1 1 d . . . . .
H11 H 1.0879 0.8644 1.1443 0.032 Uiso 1 1 calc R U . . .
C24 C 1.0031(4) 0.7333(5) 1.0204(4) 0.0226(12) Uani 1 1 d . . . . .
N4 N 1.0179(4) 0.6426(4) 0.9687(3) 0.0246(11) Uani 1 1 d . . . . .
N5 N 0.7943(3) 0.6838(4) 0.9102(3) 0.0228(10) Uani 1 1 d . . . . .
H12 H 0.7930 0.6157 0.8827 0.027 Uiso 1 1 calc R U . . .
C25 C 0.9411(5) 0.9721(5) 1.0738(4) 0.0293(14) Uani 1 1 d . . . . .
H13 H 0.9127 1.0315 1.0546 0.044 Uiso 1 1 calc R U . . .
H14 H 1.0244 0.9792 1.0798 0.044 Uiso 1 1 calc R U . . .
H15 H 0.9384 0.9771 1.1334 0.044 Uiso 1 1 calc R U . . .
C26 C 0.6727(5) 0.9283(5) 0.9431(4) 0.0323(14) Uani 1 1 d . . . . .
H16 H 0.6205 0.9225 0.9759 0.048 Uiso 1 1 calc R U . . .
H17 H 0.6231 0.9185 0.8789 0.048 Uiso 1 1 calc R U . . .
H18 H 0.7316 1.0012 0.9728 0.048 Uiso 1 1 calc R U . . .
C27 C 0.4766(4) 0.7146(5) 0.8233(4) 0.0238(12) Uani 1 1 d . . . . .
C28 C 0.4365(5) 0.7250(5) 0.8932(4) 0.0281(13) Uani 1 1 d . . . . .
C29 C 0.3434(5) 0.7730(5) 0.8955(4) 0.0331(14) Uani 1 1 d . . . . .
C30 C 0.2865(5) 0.8102(5) 0.8258(4) 0.0299(14) Uani 1 1 d . . . . .
C31 C 0.3224(5) 0.7994(5) 0.7544(4) 0.0310(14) Uani 1 1 d . . . . .
C32 C 0.4157(5) 0.7534(5) 0.7539(4) 0.0257(13) Uani 1 1 d . . . . .
F1 F 0.4915(3) 0.6907(3) 0.9630(2) 0.0368(9) Uani 1 1 d . . . . .
F2 F 0.3088(3) 0.7820(3) 0.9653(2) 0.0426(9) Uani 1 1 d . . . . .
F3 F 0.1987(3) 0.8582(3) 0.8287(2) 0.0441(10) Uani 1 1 d . . . . .
F4 F 0.2674(3) 0.8366(3) 0.6854(2) 0.0436(10) Uani 1 1 d . . . . .
F5 F 0.4479(3) 0.7461(3) 0.6835(2) 0.0366(9) Uani 1 1 d . . . . .
C33 C 0.4697(5) 0.2539(5) 0.5034(4) 0.0238(12) Uani 1 1 d . . . . .
C34 C 0.4268(5) 0.1435(5) 0.4865(4) 0.0262(13) Uani 1 1 d . . . . .
C35 C 0.3324(5) 0.0722(5) 0.4054(4) 0.0280(13) Uani 1 1 d . . . . .
C36 C 0.2784(5) 0.1136(5) 0.3373(4) 0.0286(14) Uani 1 1 d . . . . .
C37 C 0.3172(5) 0.2235(5) 0.3512(4) 0.0259(13) Uani 1 1 d . . . . .
C38 C 0.4100(5) 0.2915(5) 0.4311(4) 0.0239(12) Uani 1 1 d . . . . .
F6 F 0.4764(3) 0.1001(3) 0.5529(2) 0.0340(8) Uani 1 1 d . . . . .
F7 F 0.2928(3) -0.0351(3) 0.3926(2) 0.0366(9) Uani 1 1 d . . . . .
F8 F 0.1879(3) 0.0463(3) 0.2585(2) 0.0400(9) Uani 1 1 d . . . . .
F9 F 0.2655(3) 0.2620(3) 0.2831(2) 0.0369(9) Uani 1 1 d . . . . .
F10 F 0.4498(3) 0.3983(3) 0.4406(2) 0.0327(8) Uani 1 1 d . . . . .
C39 C 1.0547(4) 0.2368(5) 0.6677(4) 0.0260(13) Uani 1 1 d . . . . .
C40 C 1.0513(5) 0.1338(5) 0.6778(4) 0.0311(14) Uani 1 1 d . . . . .
C41 C 1.0952(5) 0.0580(6) 0.6328(5) 0.0377(16) Uani 1 1 d . . . . .
C42 C 1.1413(5) 0.0843(6) 0.5730(5) 0.0378(16) Uani 1 1 d . . . . .
C43 C 1.1421(5) 0.1819(6) 0.5587(4) 0.0351(15) Uani 1 1 d . . . . .
C44 C 1.1021(5) 0.2583(5) 0.6077(4) 0.0268(13) Uani 1 1 d . . . . .
F11 F 1.0050(3) 0.1061(3) 0.7335(2) 0.0440(10) Uani 1 1 d . . . . .
F12 F 1.0911(3) -0.0401(3) 0.6436(3) 0.0535(11) Uani 1 1 d . . . . .
F13 F 1.1837(3) 0.0098(3) 0.5267(3) 0.0551(11) Uani 1 1 d . . . . .
F14 F 1.1811(3) 0.2047(3) 0.4970(3) 0.0506(11) Uani 1 1 d . . . . .
F15 F 1.1083(3) 0.3563(3) 0.5954(2) 0.0404(9) Uani 1 1 d . . . . .
C45 C 1.2817(5) 0.3306(6) 0.8420(4) 0.0411(17) Uani 1 1 d . . . . .
H19 H 1.3614 0.3606 0.8939 0.062 Uiso 1 1 calc R U . . .
H20 H 1.2883 0.3404 0.7869 0.062 Uiso 1 1 calc R U . . .
H21 H 1.2516 0.2518 0.8305 0.062 Uiso 1 1 calc R U . . .
C46 C 1.3512(4) 0.5142(5) 1.0274(4) 0.0259(13) Uani 1 1 d . . . . .
H22 H 1.3630 0.4631 1.0617 0.039 Uiso 1 1 calc R U . . .
H23 H 1.3590 0.5869 1.0687 0.039 Uiso 1 1 calc R U . . .
H24 H 1.4124 0.5207 1.0023 0.039 Uiso 1 1 calc R U . . .
O1 O 1.2243(3) 0.5775(3) 1.1505(2) 0.0248(9) Uani 1 1 d . . . . .
Cl1 Cl 0.48034(14) 0.22573(14) 0.75352(11) 0.0421(4) Uani 1 1 d . . . . .
Cl2 Cl 0.52977(16) 0.01342(15) 0.72995(12) 0.0474(5) Uani 1 1 d . . . . .
Cl3 Cl 0.41035(16) 0.08768(15) 0.84849(12) 0.0499(5) Uani 1 1 d . . . . .
Cl4 Cl -0.19962(17) 0.54213(19) 0.55192(16) 0.0717(7) Uani 1 1 d . . . . .
Cl5 Cl -0.0309(2) 0.63058(19) 0.74400(16) 0.0810(7) Uani 1 1 d . . . . .
Cl6 Cl 0.0559(2) 0.6277(3) 0.60048(19) 0.1132(11) Uani 1 1 d . . . . .
C47 C 0.5170(6) 0.1286(6) 0.8065(4) 0.0382(16) Uani 1 1 d . . . . .
H1 H 0.5975 0.1639 0.8601 0.046 Uiso 1 1 calc R U . . .
C48 C -0.0576(9) 0.5627(9) 0.6273(6) 0.090(3) Uani 1 1 d . . . . .
H2 H -0.0469 0.4875 0.6237 0.108 Uiso 1 1 calc R U . . .
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'
F F 0.0727 0.0534 '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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
N5 C1 C2 107.8(5) . . ?
N5 C1 C24 119.4(5) . . ?
C2 C1 C24 132.7(5) . . ?
C3 C2 C1 108.2(5) . . ?
C3 C2 C25 125.0(5) . . ?
C1 C2 C25 126.9(5) . . ?
C2 C3 C4 107.3(5) . . ?
C2 C3 C26 123.8(5) . . ?
C4 C3 C26 128.7(5) . . ?
N5 C4 C5 123.5(5) . . ?
N5 C4 C3 107.1(4) . . ?
C5 C4 C3 129.4(5) . . ?
C6 C5 C4 129.2(5) . . ?
C6 C5 C27 113.8(4) . . ?
C4 C5 C27 117.0(5) . . ?
N1 C6 C5 128.4(5) . . ?
N1 C6 C7 106.6(5) . . ?
C5 C6 C7 124.9(5) . . ?
C8 C7 C6 108.7(5) . . ?
C8 C7 H3 125.7 . . ?
C6 C7 H3 125.7 . . ?
C7 C8 C9 109.0(5) . . ?
C7 C8 H4 125.5 . . ?
C9 C8 H4 125.5 . . ?
C6 N1 C9 110.4(4) . . ?
C6 N1 H5 124.8 . . ?
C9 N1 H5 124.8 . . ?
N1 C9 C10 130.3(5) . . ?
N1 C9 C8 105.3(5) . . ?
C10 C9 C8 124.2(5) . . ?
C9 C10 C11 131.1(5) . . ?
C9 C10 C33 115.6(4) . . ?
C11 C10 C33 113.3(5) . . ?
N2 C11 C10 129.1(5) . . ?
N2 C11 C12 106.4(5) . . ?
C10 C11 C12 124.5(5) . . ?
C13 C12 C11 109.1(5) . . ?
C13 C12 H6 125.5 . . ?
C11 C12 H6 125.5 . . ?
C12 C13 C14 108.6(5) . . ?
C12 C13 H7 125.7 . . ?
C14 C13 H7 125.7 . . ?
N2 C14 C15 130.6(5) . . ?
N2 C14 C13 106.0(4) . . ?
C15 C14 C13 123.5(5) . . ?
C11 N2 C14 109.9(5) . . ?
C11 N2 H8 125.0 . . ?
C14 N2 H8 125.0 . . ?
C16 C15 C14 131.3(5) . . ?
C16 C15 C39 116.7(5) . . ?
C14 C15 C39 112.0(5) . . ?
N3 C16 C15 123.5(5) . . ?
N3 C16 C17 106.2(4) . . ?
C15 C16 C17 130.3(5) . . ?
C18 C17 C16 107.4(5) . . ?
C18 C17 C45 123.2(5) . . ?
C16 C17 C45 129.3(5) . . ?
C17 C18 C19 108.4(5) . . ?
C17 C18 C46 125.1(5) . . ?
C19 C18 C46 126.2(5) . . ?
N3 C19 C18 107.0(5) . . ?
N3 C19 C20 118.9(4) . . ?
C18 C19 C20 133.4(5) . . ?
C19 N3 C16 110.9(4) . . ?
C19 N3 H9 124.5 . . ?
C16 N3 H9 124.5 . . ?
N4 C20 C19 115.3(5) . . ?
N4 C20 C21 121.7(5) . . ?
C19 C20 C21 122.8(5) . . ?
O1 C21 C22 121.8(5) . . ?
O1 C21 C20 123.5(5) . . ?
C22 C21 C20 114.5(5) . . ?
C23 C22 C21 119.3(5) . . ?
C23 C22 H10 120.3 . . ?
C21 C22 H10 120.3 . . ?
C22 C23 C24 119.9(5) . . ?
C22 C23 H11 120.1 . . ?
C24 C23 H11 120.1 . . ?
N4 C24 C23 120.8(5) . . ?
N4 C24 C1 117.2(5) . . ?
C23 C24 C1 121.9(5) . . ?
C24 N4 C20 119.1(4) . . ?
C1 N5 C4 109.5(4) . . ?
C1 N5 H12 125.2 . . ?
C4 N5 H12 125.2 . . ?
C2 C25 H13 109.5 . . ?
C2 C25 H14 109.5 . . ?
H13 C25 H14 109.5 . . ?
C2 C25 H15 109.5 . . ?
H13 C25 H15 109.5 . . ?
H14 C25 H15 109.5 . . ?
C3 C26 H16 109.5 . . ?
C3 C26 H17 109.5 . . ?
H16 C26 H17 109.5 . . ?
C3 C26 H18 109.5 . . ?
H16 C26 H18 109.5 . . ?
H17 C26 H18 109.5 . . ?
C28 C27 C32 115.6(5) . . ?
C28 C27 C5 123.2(5) . . ?
C32 C27 C5 121.2(5) . . ?
F1 C28 C27 119.1(5) . . ?
F1 C28 C29 118.2(5) . . ?
C27 C28 C29 122.6(5) . . ?
F2 C29 C30 120.2(5) . . ?
F2 C29 C28 120.2(5) . . ?
C30 C29 C28 119.6(5) . . ?
F3 C30 C29 119.7(5) . . ?
F3 C30 C31 120.8(5) . . ?
C29 C30 C31 119.4(5) . . ?
F4 C31 C32 119.8(5) . . ?
F4 C31 C30 119.9(5) . . ?
C32 C31 C30 120.2(5) . . ?
F5 C32 C31 117.8(5) . . ?
F5 C32 C27 119.7(5) . . ?
C31 C32 C27 122.5(5) . . ?
C34 C33 C38 115.1(5) . . ?
C34 C33 C10 123.7(5) . . ?
C38 C33 C10 121.3(5) . . ?
F6 C34 C33 119.4(5) . . ?
F6 C34 C35 117.0(5) . . ?
C33 C34 C35 123.5(5) . . ?
F7 C35 C36 120.0(5) . . ?
F7 C35 C34 121.3(5) . . ?
C36 C35 C34 118.7(5) . . ?
F8 C36 C37 120.4(5) . . ?
F8 C36 C35 119.7(5) . . ?
C37 C36 C35 119.9(5) . . ?
F9 C37 C38 120.5(5) . . ?
F9 C37 C36 119.2(5) . . ?
C38 C37 C36 120.3(5) . . ?
F10 C38 C37 118.6(5) . . ?
F10 C38 C33 118.9(5) . . ?
C37 C38 C33 122.5(5) . . ?
C44 C39 C40 116.4(5) . . ?
C44 C39 C15 123.0(5) . . ?
C40 C39 C15 120.4(5) . . ?
F11 C40 C41 117.5(6) . . ?
F11 C40 C39 120.0(5) . . ?
C41 C40 C39 122.5(6) . . ?
F12 C41 C40 121.4(6) . . ?
F12 C41 C42 120.2(6) . . ?
C40 C41 C42 118.3(6) . . ?
C43 C42 F13 119.7(6) . . ?
C43 C42 C41 121.0(6) . . ?
F13 C42 C41 119.3(6) . . ?
F14 C43 C42 120.8(6) . . ?
F14 C43 C44 119.8(6) . . ?
C42 C43 C44 119.4(6) . . ?
F15 C44 C43 118.5(5) . . ?
F15 C44 C39 119.2(5) . . ?
C43 C44 C39 122.2(6) . . ?
C17 C45 H19 109.5 . . ?
C17 C45 H20 109.5 . . ?
H19 C45 H20 109.5 . . ?
C17 C45 H21 109.5 . . ?
H19 C45 H21 109.5 . . ?
H20 C45 H21 109.5 . . ?
C18 C46 H22 109.5 . . ?
C18 C46 H23 109.5 . . ?
H22 C46 H23 109.5 . . ?
C18 C46 H24 109.5 . . ?
H22 C46 H24 109.5 . . ?
H23 C46 H24 109.5 . . ?
Cl1 C47 Cl3 111.3(3) . . ?
Cl1 C47 Cl2 110.6(3) . . ?
Cl3 C47 Cl2 110.7(4) . . ?
Cl1 C47 H1 108.0 . . ?
Cl3 C47 H1 108.0 . . ?
Cl2 C47 H1 108.0 . . ?
Cl4 C48 Cl6 114.6(5) . . ?
Cl4 C48 Cl5 113.7(7) . . ?
Cl6 C48 Cl5 110.5(5) . . ?
Cl4 C48 H2 105.7 . . ?
Cl6 C48 H2 105.7 . . ?
Cl5 C48 H2 105.7 . . ?
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
C1 N5 1.377(6) . ?
C1 C2 1.408(8) . ?
C1 C24 1.433(7) . ?
C2 C3 1.402(7) . ?
C2 C25 1.511(7) . ?
C3 C4 1.421(7) . ?
C3 C26 1.492(8) . ?
C4 N5 1.396(6) . ?
C4 C5 1.422(7) . ?
C5 C6 1.402(7) . ?
C5 C27 1.485(7) . ?
C6 N1 1.382(7) . ?
C6 C7 1.419(7) . ?
C7 C8 1.346(7) . ?
C7 H3 0.9500 . ?
C8 C9 1.441(7) . ?
C8 H4 0.9500 . ?
N1 C9 1.383(7) . ?
N1 H5 0.8800 . ?
C9 C10 1.400(8) . ?
C10 C11 1.407(7) . ?
C10 C33 1.491(7) . ?
C11 N2 1.383(6) . ?
C11 C12 1.424(7) . ?
C12 C13 1.351(7) . ?
C12 H6 0.9500 . ?
C13 C14 1.432(7) . ?
C13 H7 0.9500 . ?
C14 N2 1.393(6) . ?
C14 C15 1.409(7) . ?
N2 H8 0.8800 . ?
C15 C16 1.401(7) . ?
C15 C39 1.515(8) . ?
C16 N3 1.378(7) . ?
C16 C17 1.431(7) . ?
C17 C18 1.389(7) . ?
C17 C45 1.505(8) . ?
C18 C19 1.408(7) . ?
C18 C46 1.511(7) . ?
C19 N3 1.368(6) . ?
C19 C20 1.434(7) . ?
N3 H9 0.8800 . ?
C20 N4 1.352(6) . ?
C20 C21 1.448(7) . ?
C21 O1 1.278(6) . ?
C21 C22 1.439(8) . ?
C22 C23 1.360(7) . ?
C22 H10 0.9500 . ?
C23 C24 1.428(7) . ?
C23 H11 0.9500 . ?
C24 N4 1.345(7) . ?
N5 H12 0.8800 . ?
C25 H13 0.9800 . ?
C25 H14 0.9800 . ?
C25 H15 0.9800 . ?
C26 H16 0.9800 . ?
C26 H17 0.9800 . ?
C26 H18 0.9800 . ?
C27 C28 1.389(8) . ?
C27 C32 1.396(7) . ?
C28 F1 1.342(6) . ?
C28 C29 1.394(8) . ?
C29 F2 1.344(7) . ?
C29 C30 1.372(8) . ?
C30 F3 1.337(6) . ?
C30 C31 1.379(8) . ?
C31 F4 1.356(6) . ?
C31 C32 1.374(7) . ?
C32 F5 1.340(6) . ?
C33 C34 1.373(8) . ?
C33 C38 1.415(7) . ?
C34 F6 1.362(6) . ?
C34 C35 1.386(7) . ?
C35 F7 1.344(6) . ?
C35 C36 1.378(8) . ?
C36 F8 1.333(6) . ?
C36 C37 1.369(8) . ?
C37 F9 1.347(6) . ?
C37 C38 1.356(7) . ?
C38 F10 1.351(6) . ?
C39 C44 1.378(8) . ?
C39 C40 1.394(8) . ?
C40 F11 1.334(7) . ?
C40 C41 1.373(8) . ?
C41 F12 1.335(7) . ?
C41 C42 1.386(9) . ?
C42 C43 1.355(9) . ?
C42 F13 1.359(7) . ?
C43 F14 1.345(7) . ?
C43 C44 1.380(8) . ?
C44 F15 1.342(6) . ?
C45 H19 0.9800 . ?
C45 H20 0.9800 . ?
C45 H21 0.9800 . ?
C46 H22 0.9800 . ?
C46 H23 0.9800 . ?
C46 H24 0.9800 . ?
Cl1 C47 1.750(7) . ?
Cl2 C47 1.760(7) . ?
Cl3 C47 1.760(7) . ?
Cl4 C48 1.677(9) . ?
Cl5 C48 1.780(10) . ?
Cl6 C48 1.767(10) . ?
C47 H1 1.0000 . ?
C48 H2 1.0000 . ?
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
C8 H4 F14 0.95 2.31 3.237(6) 165.6 1_455
N1 H5 N5 0.88 2.66 3.134(6) 115.1 .
N1 H5 O1 0.88 2.45 2.908(5) 112.5 2_767
C12 H6 F5 0.95 2.60 3.379(6) 139.8 2_666
C13 H7 F13 0.95 2.57 3.190(7) 123.1 2_756
N2 H8 O1 0.88 2.04 2.832(6) 148.6 2_767
N3 H9 N2 0.88 2.62 3.177(6) 121.9 .
N3 H9 O1 0.88 2.38 3.100(5) 139.0 2_767
C23 H11 F8 0.95 2.41 3.273(7) 150.9 1_666
C23 H11 F11 0.95 2.62 3.214(7) 121.1 2_767
N5 H12 N1 0.88 2.63 3.134(6) 117.3 .
N5 H12 O1 0.88 2.39 3.240(6) 161.1 2_767
C47 H1 F2 1.00 2.54 3.372(7) 140.0 2_667
C8 H4 F14 0.95 2.31 3.237(6) 165.6 1_455
N1 H5 N5 0.88 2.66 3.134(6) 115.1 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 C1 C2 C3 1.7(6) . . . . ?
C24 C1 C2 C3 -174.8(6) . . . . ?
N5 C1 C2 C25 -178.0(5) . . . . ?
C24 C1 C2 C25 5.5(11) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C25 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C3 C26 -174.7(5) . . . . ?
C25 C2 C3 C26 5.0(9) . . . . ?
C2 C3 C4 N5 -1.6(6) . . . . ?
C26 C3 C4 N5 172.7(5) . . . . ?
C2 C3 C4 C5 178.1(5) . . . . ?
C26 C3 C4 C5 -7.7(10) . . . . ?
N5 C4 C5 C6 -14.9(9) . . . . ?
C3 C4 C5 C6 165.6(6) . . . . ?
N5 C4 C5 C27 164.0(5) . . . . ?
C3 C4 C5 C27 -15.6(8) . . . . ?
C4 C5 C6 N1 -12.5(9) . . . . ?
C27 C5 C6 N1 168.6(5) . . . . ?
C4 C5 C6 C7 171.8(5) . . . . ?
C27 C5 C6 C7 -7.1(7) . . . . ?
N1 C6 C7 C8 -2.1(6) . . . . ?
C5 C6 C7 C8 174.5(5) . . . . ?
C6 C7 C8 C9 1.5(6) . . . . ?
C5 C6 N1 C9 -174.6(5) . . . . ?
C7 C6 N1 C9 1.8(6) . . . . ?
C6 N1 C9 C10 174.7(5) . . . . ?
C6 N1 C9 C8 -0.9(6) . . . . ?
C7 C8 C9 N1 -0.4(6) . . . . ?
C7 C8 C9 C10 -176.4(5) . . . . ?
N1 C9 C10 C11 11.5(10) . . . . ?
C8 C9 C10 C11 -173.6(5) . . . . ?
N1 C9 C10 C33 -166.7(5) . . . . ?
C8 C9 C10 C33 8.2(8) . . . . ?
C9 C10 C11 N2 16.6(10) . . . . ?
C33 C10 C11 N2 -165.2(5) . . . . ?
C9 C10 C11 C12 -165.2(6) . . . . ?
C33 C10 C11 C12 13.0(8) . . . . ?
N2 C11 C12 C13 1.7(6) . . . . ?
C10 C11 C12 C13 -176.8(5) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C12 C13 C14 N2 -1.7(6) . . . . ?
C12 C13 C14 C15 177.4(5) . . . . ?
C10 C11 N2 C14 175.6(5) . . . . ?
C12 C11 N2 C14 -2.8(6) . . . . ?
C15 C14 N2 C11 -176.2(6) . . . . ?
C13 C14 N2 C11 2.8(6) . . . . ?
N2 C14 C15 C16 -9.0(11) . . . . ?
C13 C14 C15 C16 172.2(6) . . . . ?
N2 C14 C15 C39 170.3(5) . . . . ?
C13 C14 C15 C39 -8.6(8) . . . . ?
C14 C15 C16 N3 -0.7(10) . . . . ?
C39 C15 C16 N3 -179.9(5) . . . . ?
C14 C15 C16 C17 179.2(6) . . . . ?
C39 C15 C16 C17 0.0(9) . . . . ?
N3 C16 C17 C18 -0.5(6) . . . . ?
C15 C16 C17 C18 179.6(6) . . . . ?
N3 C16 C17 C45 -177.3(6) . . . . ?
C15 C16 C17 C45 2.8(10) . . . . ?
C16 C17 C18 C19 1.7(6) . . . . ?
C45 C17 C18 C19 178.8(5) . . . . ?
C16 C17 C18 C46 -173.3(5) . . . . ?
C45 C17 C18 C46 3.7(9) . . . . ?
C17 C18 C19 N3 -2.3(6) . . . . ?
C46 C18 C19 N3 172.7(5) . . . . ?
C17 C18 C19 C20 -172.6(6) . . . . ?
C46 C18 C19 C20 2.4(9) . . . . ?
C18 C19 N3 C16 2.0(6) . . . . ?
C20 C19 N3 C16 174.0(5) . . . . ?
C15 C16 N3 C19 179.0(5) . . . . ?
C17 C16 N3 C19 -0.9(6) . . . . ?
N3 C19 C20 N4 -15.7(7) . . . . ?
C18 C19 C20 N4 153.7(6) . . . . ?
N3 C19 C20 C21 159.8(5) . . . . ?
C18 C19 C20 C21 -30.8(9) . . . . ?
N4 C20 C21 O1 151.1(5) . . . . ?
C19 C20 C21 O1 -24.1(8) . . . . ?
N4 C20 C21 C22 -23.9(7) . . . . ?
C19 C20 C21 C22 160.9(5) . . . . ?
O1 C21 C22 C23 -156.7(5) . . . . ?
C20 C21 C22 C23 18.5(7) . . . . ?
C21 C22 C23 C24 -1.5(8) . . . . ?
C22 C23 C24 N4 -12.8(8) . . . . ?
C22 C23 C24 C1 163.4(5) . . . . ?
N5 C1 C24 N4 21.9(7) . . . . ?
C2 C1 C24 N4 -161.9(6) . . . . ?
N5 C1 C24 C23 -154.5(5) . . . . ?
C2 C1 C24 C23 21.7(10) . . . . ?
C23 C24 N4 C20 7.9(8) . . . . ?
C1 C24 N4 C20 -168.5(5) . . . . ?
C19 C20 N4 C24 -173.5(5) . . . . ?
C21 C20 N4 C24 10.9(8) . . . . ?
C2 C1 N5 C4 -2.7(6) . . . . ?
C24 C1 N5 C4 174.4(5) . . . . ?
C5 C4 N5 C1 -177.0(5) . . . . ?
C3 C4 N5 C1 2.7(6) . . . . ?
C6 C5 C27 C28 109.7(6) . . . . ?
C4 C5 C27 C28 -69.3(7) . . . . ?
C6 C5 C27 C32 -70.6(7) . . . . ?
C4 C5 C27 C32 110.4(6) . . . . ?
C32 C27 C28 F1 -179.2(5) . . . . ?
C5 C27 C28 F1 0.5(8) . . . . ?
C32 C27 C28 C29 -1.2(8) . . . . ?
C5 C27 C28 C29 178.5(5) . . . . ?
F1 C28 C29 F2 -1.4(8) . . . . ?
C27 C28 C29 F2 -179.4(5) . . . . ?
F1 C28 C29 C30 179.2(5) . . . . ?
C27 C28 C29 C30 1.1(9) . . . . ?
F2 C29 C30 F3 1.9(9) . . . . ?
C28 C29 C30 F3 -178.7(5) . . . . ?
F2 C29 C30 C31 -179.4(5) . . . . ?
C28 C29 C30 C31 0.1(9) . . . . ?
F3 C30 C31 F4 -0.7(9) . . . . ?
C29 C30 C31 F4 -179.5(6) . . . . ?
F3 C30 C31 C32 177.7(5) . . . . ?
C29 C30 C31 C32 -1.1(9) . . . . ?
F4 C31 C32 F5 -0.8(8) . . . . ?
C30 C31 C32 F5 -179.2(5) . . . . ?
F4 C31 C32 C27 179.4(5) . . . . ?
C30 C31 C32 C27 1.0(9) . . . . ?
C28 C27 C32 F5 -179.7(5) . . . . ?
C5 C27 C32 F5 0.6(8) . . . . ?
C28 C27 C32 C31 0.2(8) . . . . ?
C5 C27 C32 C31 -179.6(5) . . . . ?
C9 C10 C33 C34 -111.0(6) . . . . ?
C11 C10 C33 C34 70.5(7) . . . . ?
C9 C10 C33 C38 69.0(7) . . . . ?
C11 C10 C33 C38 -109.5(6) . . . . ?
C38 C33 C34 F6 -178.3(5) . . . . ?
C10 C33 C34 F6 1.7(8) . . . . ?
C38 C33 C34 C35 0.1(8) . . . . ?
C10 C33 C34 C35 -179.9(5) . . . . ?
F6 C34 C35 F7 -0.8(8) . . . . ?
C33 C34 C35 F7 -179.2(5) . . . . ?
F6 C34 C35 C36 178.8(5) . . . . ?
C33 C34 C35 C36 0.3(9) . . . . ?
F7 C35 C36 F8 -0.9(8) . . . . ?
C34 C35 C36 F8 179.6(5) . . . . ?
F7 C35 C36 C37 178.6(5) . . . . ?
C34 C35 C36 C37 -0.9(9) . . . . ?
F8 C36 C37 F9 -2.2(8) . . . . ?
C35 C36 C37 F9 178.3(5) . . . . ?
F8 C36 C37 C38 -179.4(5) . . . . ?
C35 C36 C37 C38 1.2(9) . . . . ?
F9 C37 C38 F10 -0.4(8) . . . . ?
C36 C37 C38 F10 176.8(5) . . . . ?
F9 C37 C38 C33 -177.9(5) . . . . ?
C36 C37 C38 C33 -0.7(9) . . . . ?
C34 C33 C38 F10 -177.4(5) . . . . ?
C10 C33 C38 F10 2.6(8) . . . . ?
C34 C33 C38 C37 0.1(8) . . . . ?
C10 C33 C38 C37 -179.9(5) . . . . ?
C16 C15 C39 C44 -99.7(6) . . . . ?
C14 C15 C39 C44 80.9(7) . . . . ?
C16 C15 C39 C40 85.0(7) . . . . ?
C14 C15 C39 C40 -94.4(6) . . . . ?
C44 C39 C40 F11 -179.0(5) . . . . ?
C15 C39 C40 F11 -3.4(8) . . . . ?
C44 C39 C40 C41 1.7(8) . . . . ?
C15 C39 C40 C41 177.3(5) . . . . ?
F11 C40 C41 F12 0.5(9) . . . . ?
C39 C40 C41 F12 179.9(5) . . . . ?
F11 C40 C41 C42 178.6(5) . . . . ?
C39 C40 C41 C42 -2.0(9) . . . . ?
F12 C41 C42 C43 177.6(5) . . . . ?
C40 C41 C42 C43 -0.6(9) . . . . ?
F12 C41 C42 F13 -0.9(9) . . . . ?
C40 C41 C42 F13 -179.1(5) . . . . ?
F13 C42 C43 F14 2.0(8) . . . . ?
C41 C42 C43 F14 -176.5(5) . . . . ?
F13 C42 C43 C44 -178.2(5) . . . . ?
C41 C42 C43 C44 3.3(9) . . . . ?
F14 C43 C44 F15 -3.0(8) . . . . ?
C42 C43 C44 F15 177.3(5) . . . . ?
F14 C43 C44 C39 176.2(5) . . . . ?
C42 C43 C44 C39 -3.6(9) . . . . ?
C40 C39 C44 F15 -179.7(4) . . . . ?
C15 C39 C44 F15 4.8(8) . . . . ?
C40 C39 C44 C43 1.2(8) . . . . ?
C15 C39 C44 C43 -174.3(5) . . . . ?
