#------------------------------------------------------------------------------
#$Date: 2019-11-23 18:40:53 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234478 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/62/4036264.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_4036264
loop_
_publ_author_name
'Naoda, Koji'
'Mori, Hirotaka'
'Oh, Juwon'
'Park, Kyu Hyung'
'Kim, Dongho'
'Osuka, Atsuhiro'
_publ_section_title
;
 5,20-Di(pyridin-2-yl)-[28]hexaphyrin(1.1.1.1.1.1): A Stable Hückel
 Antiaromatic Hexaphyrin Stabilized by Intramolecular Hydrogen Bonding and
 Protonation-Induced Conformational Twist To Gain Möbius Aromaticity.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11726
_journal_page_last               11733
_journal_paper_doi               10.1021/acs.joc.5b01348
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety
'C32 H22 F20 N8, 0.636(CHCl3), 0.305(C6H14), 0.389(C2H6O)'
_chemical_formula_sum            'C35.25 H18.25 Cl1.91 F10 N4 O0.39'
_chemical_formula_weight         761.66
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.172(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.633(4)
_cell_length_b                   24.880(6)
_cell_length_c                   17.612(5)
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      25.4
_cell_volume                     6670(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            42432
_diffrn_reflns_theta_full        68.96
_diffrn_reflns_theta_max         68.96
_diffrn_reflns_theta_min         6.82
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_T_max  0.9754
_exptl_absorpt_correction_T_min  0.3149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            dark_red
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             3066
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         6074
_refine_ls_number_restraints     62
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1324
_refine_ls_R_factor_gt           0.0935
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2767
_refine_ls_wR_factor_ref         0.3009
_reflns_number_gt                3460
_reflns_number_total             6074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01348_si_004.cif
_cod_data_source_block           50608n
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4036264
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C27 C 0.3257(8) 0.4617(3) 0.0634(7) 0.039(4) Uani 0.59(3) 1 d PG A 1
C28 C 0.2851(8) 0.4761(6) 0.1229(6) 0.068(5) Uani 0.59(3) 1 d PG A 1
C29 C 0.2548(8) 0.5283(6) 0.1269(6) 0.053(4) Uani 0.59(3) 1 d PG A 1
C30 C 0.2651(8) 0.5661(4) 0.0715(10) 0.056(4) Uani 0.59(3) 1 d PG A 1
C31 C 0.3057(9) 0.5516(4) 0.0121(9) 0.051(3) Uani 0.59(3) 1 d PG A 1
C32 C 0.3360(8) 0.4994(4) 0.0080(7) 0.042(3) Uani 0.59(3) 1 d PG A 1
F6 F 0.3715(12) 0.4839(4) -0.0501(9) 0.073(3) Uani 0.59(3) 1 d P A 1
F7 F 0.3185(14) 0.5868(5) -0.0433(10) 0.087(4) Uani 0.59(3) 1 d P A 1
F8 F 0.2417(11) 0.6180(6) 0.0742(8) 0.073(4) Uani 0.59(3) 1 d P A 1
F9 F 0.2167(6) 0.5434(6) 0.1817(6) 0.075(3) Uani 0.59(3) 1 d P A 1
F10 F 0.2697(7) 0.4417(5) 0.1742(6) 0.065(3) Uani 0.59(3) 1 d P A 1
C39 C 0.3144(14) 0.4643(6) 0.0565(9) 0.071(10) Uani 0.41(3) 1 d PG A 2
C40 C 0.3103(14) 0.4968(8) -0.0084(7) 0.065(7) Uani 0.41(3) 1 d PGD A 2
C41 C 0.2911(16) 0.5512(8) -0.0049(11) 0.102(13) Uani 0.41(3) 1 d PGD A 2
C42 C 0.2759(19) 0.5730(6) 0.0634(14) 0.076(9) Uani 0.41(3) 1 d PGD A 2
C43 C 0.280(2) 0.5405(9) 0.1284(10) 0.078(8) Uani 0.41(3) 1 d PGD A 2
C44 C 0.2993(18) 0.4861(8) 0.1249(7) 0.062(6) Uani 0.41(3) 1 d PGD A 2
F11 F 0.3312(17) 0.4799(6) -0.0726(9) 0.076(4) Uani 0.41(3) 1 d PD A 2
F12 F 0.307(2) 0.4573(9) 0.1904(12) 0.097(7) Uani 0.41(3) 1 d PD A 2
F13 F 0.261(3) 0.5598(9) 0.1960(15) 0.141(12) Uani 0.41(3) 1 d PD A 2
F14 F 0.2818(16) 0.5824(9) -0.0657(13) 0.104(6) Uani 0.41(3) 1 d PD A 2
F15 F 0.253(2) 0.6239(10) 0.0693(19) 0.137(13) Uani 0.41(3) 1 d PD A 2
C16 C 0.44497(19) 0.07269(10) 0.12095(19) 0.0574(12) Uani 1 1 d G . .
C17 C 0.39139(17) 0.04281(12) 0.15809(18) 0.0553(12) Uani 1 1 d G . .
C18 C 0.4042(2) -0.01228(12) 0.1678(2) 0.0756(16) Uani 1 1 d G . .
C19 C 0.4706(2) -0.03748(10) 0.1404(2) 0.0759(17) Uani 1 1 d G . .
C20 C 0.5242(2) -0.00760(14) 0.1032(2) 0.0748(17) Uani 1 1 d G . .
C21 C 0.51135(18) 0.04749(14) 0.09352(19) 0.0645(14) Uani 1 1 d G . .
F1 F 0.32700(17) 0.06423(10) 0.18354(17) 0.0631(8) Uani 1 1 d . . .
F2 F 0.3527(2) -0.04105(13) 0.2038(2) 0.0888(11) Uani 1 1 d . . .
F3 F 0.4833(2) -0.09060(13) 0.1517(3) 0.1043(13) Uani 1 1 d . . .
F4 F 0.5878(2) -0.03214(16) 0.0777(2) 0.0995(12) Uani 1 1 d . . .
F5 F 0.56059(18) 0.07418(14) 0.05469(18) 0.0768(9) Uani 1 1 d . . .
N1 N 0.2949(2) 0.10595(15) 0.0245(2) 0.0524(9) Uani 1 1 d . . .
N2 N 0.4905(2) 0.22377(14) 0.1428(2) 0.0500(9) Uani 1 1 d . . .
N3 N 0.4599(2) 0.33762(15) 0.1205(2) 0.0493(9) Uani 1 1 d . . .
H1 H 0.4296 0.3080 0.1064 0.059 Uiso 1 1 calc R . .
N4 N 0.7102(2) 0.30139(17) 0.3135(2) 0.0621(11) Uani 1 1 d . . .
C1 C 0.2159(3) 0.12811(18) -0.0082(3) 0.0507(11) Uani 1 1 d . . .
C2 C 0.2117(3) 0.18304(18) 0.0184(3) 0.0530(11) Uani 1 1 d . . .
H2 H 0.1628 0.2066 0.0056 0.064 Uiso 1 1 calc R . .
C3 C 0.2909(3) 0.19401(18) 0.0650(3) 0.0527(11) Uani 1 1 d . . .
H3 H 0.3092 0.2270 0.0907 0.063 Uiso 1 1 calc R . .
C4 C 0.3423(3) 0.14582(18) 0.0680(3) 0.0501(11) Uani 1 1 d . . .
C5 C 0.4281(3) 0.13283(18) 0.1103(3) 0.0515(11) Uani 1 1 d . . .
C6 C 0.4946(3) 0.16915(18) 0.1464(3) 0.0504(11) Uani 1 1 d . . .
C7 C 0.5805(3) 0.1514(2) 0.1911(3) 0.0541(11) Uani 1 1 d . . .
H4 H 0.5995 0.1154 0.2019 0.065 Uiso 1 1 calc R . .
C8 C 0.6269(3) 0.1962(2) 0.2138(3) 0.0535(12) Uani 1 1 d . . .
H5 H 0.6858 0.1981 0.2435 0.064 Uiso 1 1 calc R . .
C9 C 0.5695(3) 0.24151(18) 0.1840(3) 0.0503(11) Uani 1 1 d . . .
C10 C 0.5959(3) 0.29534(18) 0.1935(3) 0.0500(11) Uani 1 1 d . . .
C11 C 0.5446(2) 0.33941(18) 0.1637(2) 0.0478(10) Uani 1 1 d . . .
C12 C 0.5685(3) 0.39481(18) 0.1730(3) 0.0516(11) Uani 1 1 d . . .
H6 H 0.6239 0.4085 0.1999 0.062 Uiso 1 1 calc R . .
C13 C 0.4987(3) 0.42446(19) 0.1366(3) 0.0526(11) Uani 1 1 d . . .
H7 H 0.4964 0.4626 0.1345 0.063 Uiso 1 1 calc R . .
C14 C 0.4292(3) 0.38912(17) 0.1022(2) 0.0466(10) Uani 1 1 d . A .
C15 C 0.3476(3) 0.40435(18) 0.0571(3) 0.0494(11) Uani 1 1 d . . .
C22 C 0.6895(3) 0.30699(19) 0.2360(3) 0.0575(13) Uani 1 1 d . . .
C23 C 0.7498(3) 0.3233(3) 0.1960(4) 0.105(3) Uani 1 1 d . . .
H8 H 0.7336 0.3277 0.1410 0.126 Uiso 1 1 calc R . .
C24 C 0.8358(4) 0.3334(3) 0.2370(6) 0.109(3) Uani 1 1 d . . .
H9 H 0.8780 0.3464 0.2104 0.131 Uiso 1 1 calc R . .
C25 C 0.8583(3) 0.3248(2) 0.3128(4) 0.0786(18) Uani 1 1 d . . .
H10 H 0.9175 0.3289 0.3410 0.094 Uiso 1 1 calc R . .
C26 C 0.7937(3) 0.3100(2) 0.3498(4) 0.0724(15) Uani 1 1 d . . .
H11 H 0.8095 0.3055 0.4048 0.087 Uiso 1 1 calc R . .
C33 C 0.1096(12) 0.1121(5) 0.1666(8) 0.133(6) Uani 0.636(6) 1 d P . .
H12 H 0.1630 0.1035 0.1466 0.160 Uiso 0.636(6) 1 calc PR . .
Cl1 Cl 0.1239(2) 0.16734(18) 0.2143(3) 0.1441(18) Uani 0.636(6) 1 d P . .
Cl2 Cl 0.0818(5) 0.0569(2) 0.2184(3) 0.220(3) Uani 0.636(6) 1 d P . .
Cl3 Cl 0.01061(18) 0.11739(16) 0.08267(18) 0.1168(14) Uani 0.636(6) 1 d P . .
C34 C -0.0248(17) 0.2710(10) 0.0375(14) 0.128(9) Uani 0.389(16) 1 d PDU B 1
H13 H 0.0198 0.2691 0.0874 0.153 Uiso 0.389(16) 1 calc PR B 1
H14 H 0.0041 0.2722 -0.0070 0.153 Uiso 0.389(16) 1 calc PR B 1
C38 C -0.0918(16) 0.3170(10) 0.0358(13) 0.143(10) Uani 0.389(16) 1 d PDU B 1
H15 H -0.0612 0.3517 0.0398 0.215 Uiso 0.389(16) 1 calc PR B 1
H16 H -0.1201 0.3130 0.0797 0.215 Uiso 0.389(16) 1 calc PR B 1
H17 H -0.1364 0.3156 -0.0133 0.215 Uiso 0.389(16) 1 calc PR B 1
O1 O -0.1031(16) 0.2210(9) 0.0284(12) 0.173(9) Uani 0.389(16) 1 d PDU B 1
H18 H -0.0789 0.1908 0.0283 0.260 Uiso 0.389(16) 1 calc PR B 1
C45 C -0.0285(13) 0.2334(10) 0.0485(15) 0.189(10) Uani 0.611(16) 1 d PDU B 2
H19 H 0.0235 0.2503 0.0365 0.283 Uiso 0.611(16) 1 calc PR B 2
H20 H -0.0353 0.1969 0.0268 0.283 Uiso 0.611(16) 1 calc PR B 2
H21 H -0.0215 0.2316 0.1052 0.283 Uiso 0.611(16) 1 calc PR B 2
C34A C -0.1258(14) 0.2730(11) 0.0059(12) 0.166(8) Uani 0.611(16) 1 d PDU B 2
H22 H -0.1157 0.3099 0.0271 0.199 Uiso 0.611(16) 1 calc PR B 2
H23 H -0.1294 0.2755 -0.0509 0.199 Uiso 0.611(16) 1 calc PR B 2
C37 C -0.2186(15) 0.2543(12) 0.0169(14) 0.195(10) Uani 0.611(16) 1 d PDU . 2
H24 H -0.2039 0.2210 0.0479 0.234 Uiso 0.611(16) 1 calc PR B 2
H25 H -0.2313 0.2812 0.0542 0.234 Uiso 0.611(16) 1 calc PR 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
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
C28 C27 C32 120.0 . .
C28 C27 C15 117.4(8) . .
C32 C27 C15 122.3(8) . .
F10 C28 C29 117.2(11) . .
F10 C28 C27 122.7(11) . .
C29 C28 C27 120.0 . .
F9 C29 C28 121.9(11) . .
F9 C29 C30 118.1(11) . .
C28 C29 C30 120.0 . .
F8 C30 C29 123.2(12) . .
F8 C30 C31 116.7(12) . .
C29 C30 C31 120.0 . .
F7 C31 C32 117.2(10) . .
F7 C31 C30 122.8(10) . .
C32 C31 C30 120.0 . .
F6 C32 C31 121.3(9) . .
F6 C32 C27 118.7(9) . .
C31 C32 C27 120.0 . .
C40 C39 C44 120.0 . .
C40 C39 C15 120.6(11) . .
C44 C39 C15 119.0(11) . .
F11 C40 C39 123.1(16) . .
F11 C40 C41 116.6(16) . .
C39 C40 C41 120.0 . .
F14 C41 C42 118(2) . .
F14 C41 C40 122(2) . .
C42 C41 C40 120.0 . .
F15 C42 C43 117(2) . .
F15 C42 C41 123(2) . .
C43 C42 C41 120.0 . .
F13 C43 C42 122.0(17) . .
F13 C43 C44 118.0(17) . .
C42 C43 C44 120.0 . .
F12 C44 C43 117.4(15) . .
F12 C44 C39 122.5(15) . .
C43 C44 C39 120.0 . .
C17 C16 C21 120.0 . .
C17 C16 C5 118.6(3) . .
C21 C16 C5 121.4(3) . .
F1 C17 C16 122.5(2) . .
F1 C17 C18 117.5(2) . .
C16 C17 C18 120.0 . .
F2 C18 C17 120.0(3) . .
F2 C18 C19 120.0(3) . .
C17 C18 C19 120.0 . .
F3 C19 C18 119.3(3) . .
F3 C19 C20 120.7(3) . .
C18 C19 C20 120.0 . .
F4 C20 C21 120.6(3) . .
F4 C20 C19 119.4(3) . .
C21 C20 C19 120.0 . .
F5 C21 C20 118.4(3) . .
F5 C21 C16 121.5(3) . .
C20 C21 C16 120.0 . .
C1 N1 C4 105.6(4) . .
C9 N2 C6 105.8(3) . .
C11 N3 C14 109.9(4) . .
C11 N3 H1 125.0 . .
C14 N3 H1 125.0 . .
C26 N4 C22 117.2(5) . .
N1 C1 C15 118.2(4) . 7
N1 C1 C2 110.4(4) . .
C15 C1 C2 131.3(4) 7 .
C3 C2 C1 106.5(4) . .
C3 C2 H2 126.7 . .
C1 C2 H2 126.7 . .
C2 C3 C4 106.4(4) . .
C2 C3 H3 126.8 . .
C4 C3 H3 126.8 . .
N1 C4 C5 117.3(4) . .
N1 C4 C3 111.0(3) . .
C5 C4 C3 131.6(4) . .
C6 C5 C4 127.0(4) . .
C6 C5 C16 118.9(3) . .
C4 C5 C16 113.9(4) . .
N2 C6 C5 126.5(4) . .
N2 C6 C7 110.8(4) . .
C5 C6 C7 122.7(4) . .
C8 C7 C6 106.2(4) . .
C8 C7 H4 126.9 . .
C6 C7 H4 126.9 . .
C7 C8 C9 106.7(4) . .
C7 C8 H5 126.6 . .
C9 C8 H5 126.6 . .
N2 C9 C10 125.7(4) . .
N2 C9 C8 110.5(4) . .
C10 C9 C8 123.7(4) . .
C11 C10 C9 125.5(4) . .
C11 C10 C22 116.5(4) . .
C9 C10 C22 117.9(4) . .
N3 C11 C10 125.9(4) . .
N3 C11 C12 106.8(4) . .
C10 C11 C12 127.3(4) . .
C13 C12 C11 108.1(4) . .
C13 C12 H6 126.0 . .
C11 C12 H6 126.0 . .
C12 C13 C14 108.7(4) . .
C12 C13 H7 125.6 . .
C14 C13 H7 125.6 . .
N3 C14 C15 127.6(4) . .
N3 C14 C13 106.4(3) . .
C15 C14 C13 125.9(4) . .
C14 C15 C1 128.1(4) . 7
C14 C15 C27 114.7(6) . .
C1 C15 C27 117.1(6) 7 .
C14 C15 C39 121.2(8) . .
C1 C15 C39 110.7(8) 7 .
C27 C15 C39 6.5(11) . .
N4 C22 C23 121.6(4) . .
N4 C22 C10 117.9(4) . .
C23 C22 C10 120.4(5) . .
C22 C23 C24 118.9(6) . .
C22 C23 H8 120.5 . .
C24 C23 H8 120.5 . .
C25 C24 C23 119.9(6) . .
C25 C24 H9 120.0 . .
C23 C24 H9 120.0 . .
C24 C25 C26 118.0(5) . .
C24 C25 H10 121.0 . .
C26 C25 H10 121.0 . .
N4 C26 C25 124.2(6) . .
N4 C26 H11 117.9 . .
C25 C26 H11 117.9 . .
Cl1 C33 Cl2 114.8(7) . .
Cl1 C33 Cl3 110.1(7) . .
Cl2 C33 Cl3 101.8(9) . .
Cl1 C33 H12 109.9 . .
Cl2 C33 H12 109.9 . .
Cl3 C33 H12 109.9 . .
C38 C34 O1 94.0(17) . .
C38 C34 H13 112.9 . .
O1 C34 H13 112.9 . .
C38 C34 H14 112.9 . .
O1 C34 H14 112.9 . .
H13 C34 H14 110.3 . .
C34 C38 H15 109.5 . .
C34 C38 H16 109.5 . .
H15 C38 H16 109.5 . .
C34 C38 H17 109.5 . .
H15 C38 H17 109.5 . .
H16 C38 H17 109.5 . .
C34 O1 H18 109.5 . .
C34A C45 H19 109.5 . .
C34A C45 H20 109.5 . .
H19 C45 H20 109.5 . .
C34A C45 H21 109.5 . .
H19 C45 H21 109.5 . .
H20 C45 H21 109.5 . .
C37 C34A C45 119.6(17) . .
C37 C34A H22 107.4 . .
C45 C34A H22 107.4 . .
C37 C34A H23 107.4 . .
C45 C34A H23 107.4 . .
H22 C34A H23 107.0 . .
C37 C37 C34A 139(4) 7_455 .
C37 C37 H24 102.2 7_455 .
C34A C37 H24 102.2 . .
C37 C37 H25 102.2 7_455 .
C34A C37 H25 102.2 . .
H24 C37 H25 104.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C27 C28 1.3900 .
C27 C32 1.3900 .
C27 C15 1.477(9) .
C28 F10 1.308(11) .
C28 C29 1.3900 .
C29 F9 1.300(12) .
C29 C30 1.3900 .
C30 F8 1.345(14) .
C30 C31 1.3900 .
C31 F7 1.358(12) .
C31 C32 1.3900 .
C32 F6 1.328(12) .
C39 C40 1.3900 .
C39 C44 1.3900 .
C39 C15 1.578(14) .
C40 F11 1.315(16) .
C40 C41 1.3900 .
C41 F14 1.303(18) .
C41 C42 1.3900 .
C42 F15 1.33(2) .
C42 C43 1.3900 .
C43 F13 1.376(17) .
C43 C44 1.3900 .
C44 F12 1.341(16) .
C16 C17 1.3900 .
C16 C21 1.3900 .
C16 C5 1.523(5) .
C17 F1 1.305(4) .
C17 C18 1.3900 .
C18 F2 1.340(4) .
C18 C19 1.3900 .
C19 F3 1.345(4) .
C19 C20 1.3900 .
C20 F4 1.330(4) .
C20 C21 1.3900 .
C21 F5 1.319(4) .
N1 C1 1.356(5) .
N1 C4 1.364(6) .
N2 C9 1.357(5) .
N2 C6 1.361(6) .
N3 C11 1.370(5) .
N3 C14 1.380(6) .
N3 H1 0.8800 .
N4 C26 1.334(6) .
N4 C22 1.336(6) .
C1 C15 1.410(6) 7
C1 C2 1.451(7) .
C2 C3 1.348(6) .
C2 H2 0.9500 .
C3 C4 1.437(6) .
C3 H3 0.9500 .
C4 C5 1.416(6) .
C5 C6 1.414(6) .
C6 C7 1.462(6) .
C7 C8 1.340(7) .
C7 H4 0.9500 .
C8 C9 1.463(6) .
C8 H5 0.9500 .
C9 C10 1.400(7) .
C10 C11 1.388(6) .
C10 C22 1.512(6) .
C11 C12 1.428(6) .
C12 C13 1.352(6) .
C12 H6 0.9500 .
C13 C14 1.421(6) .
C13 H7 0.9500 .
C14 C15 1.393(6) .
C15 C1 1.410(6) 7
C22 C23 1.362(8) .
C23 C24 1.397(9) .
C23 H8 0.9500 .
C24 C25 1.318(10) .
C24 H9 0.9500 .
C25 C26 1.371(9) .
C25 H10 0.9500 .
C26 H11 0.9500 .
C33 Cl1 1.599(15) .
C33 Cl2 1.757(15) .
C33 Cl3 1.886(18) .
C33 H12 1.0000 .
C34 C38 1.55(2) .
C34 O1 1.73(2) .
C34 H13 0.9900 .
C34 H14 0.9900 .
C38 H15 0.9800 .
C38 H16 0.9800 .
C38 H17 0.9800 .
O1 H18 0.8400 .
C45 C34A 1.82(2) .
C45 H19 0.9800 .
C45 H20 0.9800 .
C45 H21 0.9800 .
C34A C37 1.58(2) .
C34A H22 0.9900 .
C34A H23 0.9900 .
C37 C37 1.05(4) 7_455
C37 H24 0.9900 .
C37 H25 0.9900 .
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
C32 C27 C28 F10 176.5(12) . .
C15 C27 C28 F10 3.0(10) . .
C32 C27 C28 C29 0.0 . .
C15 C27 C28 C29 -173.4(11) . .
F10 C28 C29 F9 3.5(13) . .
C27 C28 C29 F9 -179.8(11) . .
F10 C28 C29 C30 -176.6(12) . .
C27 C28 C29 C30 0.0 . .
F9 C29 C30 F8 3.5(15) . .
C28 C29 C30 F8 -176.3(15) . .
F9 C29 C30 C31 179.8(11) . .
C28 C29 C30 C31 0.0 . .
F8 C30 C31 F7 -2.8(12) . .
C29 C30 C31 F7 -179.3(13) . .
F8 C30 C31 C32 176.6(14) . .
C29 C30 C31 C32 0.0 . .
F7 C31 C32 F6 -3.6(13) . .
C30 C31 C32 F6 177.0(9) . .
F7 C31 C32 C27 179.4(12) . .
C30 C31 C32 C27 0.0 . .
C28 C27 C32 F6 -177.1(9) . .
C15 C27 C32 F6 -4.0(12) . .
C28 C27 C32 C31 0.0 . .
C15 C27 C32 C31 173.1(11) . .
C44 C39 C40 F11 174.0(17) . .
C15 C39 C40 F11 2(2) . .
C44 C39 C40 C41 0.0 . .
C15 C39 C40 C41 -172.4(19) . .
F11 C40 C41 F14 10(2) . .
C39 C40 C41 F14 -176(2) . .
F11 C40 C41 C42 -174.4(16) . .
C39 C40 C41 C42 0.0 . .
F14 C41 C42 F15 0(2) . .
C40 C41 C42 F15 -177(3) . .
F14 C41 C42 C43 176(2) . .
C40 C41 C42 C43 0.0 . .
F15 C42 C43 F13 0(3) . .
C41 C42 C43 F13 -177(2) . .
F15 C42 C43 C44 177(3) . .
C41 C42 C43 C44 0.0 . .
F13 C43 C44 F12 -6(2) . .
C42 C43 C44 F12 177(2) . .
F13 C43 C44 C39 177(2) . .
C42 C43 C44 C39 0.0 . .
C40 C39 C44 F12 -177(2) . .
C15 C39 C44 F12 -4.0(17) . .
C40 C39 C44 C43 0.0 . .
C15 C39 C44 C43 172.5(19) . .
C21 C16 C17 F1 -178.6(3) . .
C5 C16 C17 F1 0.5(4) . .
C21 C16 C17 C18 0.0 . .
C5 C16 C17 C18 179.1(3) . .
F1 C17 C18 F2 -1.5(3) . .
C16 C17 C18 F2 179.8(3) . .
F1 C17 C18 C19 178.6(3) . .
C16 C17 C18 C19 0.0 . .
F2 C18 C19 F3 -1.2(4) . .
C17 C18 C19 F3 178.6(3) . .
F2 C18 C19 C20 -179.8(3) . .
C17 C18 C19 C20 0.0 . .
F3 C19 C20 F4 1.0(4) . .
C18 C19 C20 F4 179.6(3) . .
F3 C19 C20 C21 -178.6(3) . .
C18 C19 C20 C21 0.0 . .
F4 C20 C21 F5 3.7(3) . .
C19 C20 C21 F5 -176.8(3) . .
F4 C20 C21 C16 -179.6(3) . .
C19 C20 C21 C16 0.0 . .
C17 C16 C21 F5 176.7(3) . .
C5 C16 C21 F5 -2.4(4) . .
C17 C16 C21 C20 0.0 . .
C5 C16 C21 C20 -179.1(3) . .
C4 N1 C1 C15 179.9(4) . 7
C4 N1 C1 C2 -2.9(5) . .
N1 C1 C2 C3 2.6(5) . .
C15 C1 C2 C3 179.3(5) 7 .
C1 C2 C3 C4 -1.2(5) . .
C1 N1 C4 C5 178.7(4) . .
C1 N1 C4 C3 2.2(5) . .
C2 C3 C4 N1 -0.6(5) . .
C2 C3 C4 C5 -176.5(5) . .
N1 C4 C5 C6 166.8(4) . .
C3 C4 C5 C6 -17.4(8) . .
N1 C4 C5 C16 -17.7(6) . .
C3 C4 C5 C16 158.0(5) . .
C17 C16 C5 C6 117.8(4) . .
C21 C16 C5 C6 -63.1(5) . .
C17 C16 C5 C4 -58.1(4) . .
C21 C16 C5 C4 121.0(4) . .
C9 N2 C6 C5 -178.3(5) . .
C9 N2 C6 C7 -0.7(5) . .
C4 C5 C6 N2 -4.8(8) . .
C16 C5 C6 N2 179.9(4) . .
C4 C5 C6 C7 177.9(5) . .
C16 C5 C6 C7 2.6(7) . .
N2 C6 C7 C8 0.0(5) . .
C5 C6 C7 C8 177.7(4) . .
C6 C7 C8 C9 0.7(5) . .
C6 N2 C9 C10 177.6(5) . .
C6 N2 C9 C8 1.1(5) . .
C7 C8 C9 N2 -1.2(5) . .
C7 C8 C9 C10 -177.7(5) . .
N2 C9 C10 C11 1.5(8) . .
C8 C9 C10 C11 177.5(4) . .
N2 C9 C10 C22 -175.0(4) . .
C8 C9 C10 C22 1.0(7) . .
C14 N3 C11 C10 178.8(4) . .
C14 N3 C11 C12 -0.2(5) . .
C9 C10 C11 N3 0.3(8) . .
C22 C10 C11 N3 176.9(4) . .
C9 C10 C11 C12 179.1(5) . .
C22 C10 C11 C12 -4.4(7) . .
N3 C11 C12 C13 0.8(5) . .
C10 C11 C12 C13 -178.2(5) . .
C11 C12 C13 C14 -1.0(5) . .
C11 N3 C14 C15 177.7(4) . .
C11 N3 C14 C13 -0.4(5) . .
C12 C13 C14 N3 0.9(5) . .
C12 C13 C14 C15 -177.3(4) . .
N3 C14 C15 C1 -12.8(8) . 7
C13 C14 C15 C1 165.1(5) . 7
N3 C14 C15 C27 166.0(6) . .
C13 C14 C15 C27 -16.1(8) . .
N3 C14 C15 C39 166.6(8) . .
C13 C14 C15 C39 -15.6(10) . .
C28 C27 C15 C14 -87.5(8) . .
C32 C27 C15 C14 99.3(9) . .
C28 C27 C15 C1 91.5(9) . 7
C32 C27 C15 C1 -81.8(9) . 7
C28 C27 C15 C39 97(9) . .
C32 C27 C15 C39 -77(9) . .
C40 C39 C15 C14 108.1(14) . .
C44 C39 C15 C14 -64.4(16) . .
C40 C39 C15 C1 -72.5(15) . 7
C44 C39 C15 C1 115.1(13) . 7
C40 C39 C15 C27 112(9) . .
C44 C39 C15 C27 -60(8) . .
C26 N4 C22 C23 -3.1(8) . .
C26 N4 C22 C10 177.7(4) . .
C11 C10 C22 N4 108.0(5) . .
C9 C10 C22 N4 -75.2(6) . .
C11 C10 C22 C23 -71.2(7) . .
C9 C10 C22 C23 105.6(6) . .
N4 C22 C23 C24 1.2(11) . .
C10 C22 C23 C24 -179.6(6) . .
C22 C23 C24 C25 3.0(12) . .
C23 C24 C25 C26 -4.8(11) . .
C22 N4 C26 C25 1.1(8) . .
C24 C25 C26 N4 2.9(9) . .
C45 C34A C37 C37 -126(6) . 7_455
