#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:57:02 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178830 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/84/4108448.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_4108448
loop_
_publ_author_name
'Jeyaraman Sankar'
'Shigeki Mori'
'Shohei Saito'
'Harapriya Rath'
'Masaaki Suzuki'
'Yasuhide Inokuma'
'Hiroshi Shinokubo'
'Kil Suk Kim'
'Zin Seok Yoon'
'Jae-Yoon Shin'
'Jong Min Lim'
'Yoichi Matsuzaki'
'Osamu Matsushita'
'Atsuya Muranaka'
'Nagao Kobayashi'
'Dongho Kim'
'Atsuhiro Osuka'
_publ_section_title
;
 Unambiguous Identification of Möbius Aromaticity for
 meso-Aryl-Substituted [28]Hexaphyrins(1.1.1.1.1.1)
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13568
_journal_page_last               13579
_journal_paper_doi               10.1021/ja801983d
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C69.34 H43.38 Cl0.65 F12 N6 O1.35'
_chemical_formula_weight         1232.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.042(2)
_cell_angle_beta                 113.657(2)
_cell_angle_gamma                105.822(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8770(14)
_cell_length_b                   14.6082(14)
_cell_length_c                   16.7087(17)
_cell_measurement_reflns_used    5886
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.37
_cell_volume                     2783.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17648
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9269
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       prism
_exptl_crystal_F_000             1262
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     878
_refine_ls_number_reflns         12308
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0677
_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)+(0.0812P)²+3.2757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1723
_refine_ls_wR_factor_ref         0.1943
_reflns_number_gt                8765
_reflns_number_total             12308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja801983d_si_006.cif
_cod_data_source_block           71107sankar
_cod_database_code               4108448
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6821(2) -0.35695(19) 0.17441(18) 0.0198(5) Uani 1 1 d . . .
C2 C 0.6704(2) -0.4437(2) 0.10907(18) 0.0220(5) Uani 1 1 d . . .
H2 H 0.6197 -0.5120 0.0911 0.026 Uiso 1 1 calc R . .
C3 C 0.7437(2) -0.4129(2) 0.07655(19) 0.0232(5) Uani 1 1 d . . .
H3 H 0.7532 -0.4560 0.0318 0.028 Uiso 1 1 calc R . .
C4 C 0.8042(2) -0.3050(2) 0.12073(18) 0.0206(5) Uani 1 1 d . . .
C5 C 0.8916(2) -0.2398(2) 0.11432(19) 0.0229(5) Uani 1 1 d . . .
C6 C 0.9402(2) -0.1336(2) 0.1606(2) 0.0248(6) Uani 1 1 d . . .
C7 C 0.8975(3) -0.0683(2) 0.1951(3) 0.0344(7) Uani 1 1 d . . .
H7 H 0.8228 -0.0878 0.1887 0.041 Uiso 1 1 calc R . .
C8 C 0.9804(3) 0.0277(2) 0.2394(2) 0.0317(7) Uani 1 1 d . . .
H8 H 0.9736 0.0869 0.2689 0.038 Uiso 1 1 calc R . .
C9 C 1.0777(2) 0.0245(2) 0.23422(19) 0.0220(5) Uani 1 1 d . . .
C10 C 1.1904(2) 0.0983(2) 0.28132(18) 0.0211(5) Uani 1 1 d . . .
C11 C 1.2202(2) 0.2024(2) 0.32097(19) 0.0223(5) Uani 1 1 d . . .
C12 C 1.3317(2) 0.2786(2) 0.3815(2) 0.0260(6) Uani 1 1 d . . .
H12 H 1.4003 0.2672 0.4058 0.031 Uiso 1 1 calc R . .
C13 C 1.3249(2) 0.3704(2) 0.3992(2) 0.0270(6) Uani 1 1 d . . .
H13 H 1.3877 0.4345 0.4372 0.032 Uiso 1 1 calc R . .
C14 C 1.2082(2) 0.3548(2) 0.35135(19) 0.0230(5) Uani 1 1 d . . .
C15 C 1.1603(2) 0.4262(2) 0.34273(19) 0.0230(5) Uani 1 1 d . . .
C16 C 1.0418(2) 0.4006(2) 0.29487(18) 0.0218(5) Uani 1 1 d . . .
C17 C 0.9883(2) 0.4691(2) 0.27084(19) 0.0233(5) Uani 1 1 d . . .
H17 H 1.0255 0.5406 0.2878 0.028 Uiso 1 1 calc R . .
C18 C 0.8758(2) 0.4126(2) 0.21988(19) 0.0230(5) Uani 1 1 d . . .
H18 H 0.8173 0.4358 0.1918 0.028 Uiso 1 1 calc R . .
C19 C 0.8602(2) 0.3106(2) 0.21572(17) 0.0208(5) Uani 1 1 d . . .
C20 C 0.7553(2) 0.2286(2) 0.17384(18) 0.0218(5) Uani 1 1 d . . .
C21 C 0.7369(2) 0.1403(2) 0.19572(18) 0.0227(5) Uani 1 1 d . A .
C22 C 0.6436(2) 0.0451(2) 0.14277(19) 0.0252(6) Uani 1 1 d . . .
H22 H 0.5836 0.0264 0.0809 0.030 Uiso 1 1 calc R . .
C23 C 0.6531(2) -0.0155(2) 0.19452(18) 0.0237(6) Uani 1 1 d . . .
H23 H 0.6024 -0.0842 0.1749 0.028 Uiso 1 1 calc R . .
C24 C 0.7520(2) 0.0419(2) 0.28279(18) 0.0222(5) Uani 1 1 d . A .
C25 C 0.7835(2) 0.0176(2) 0.36357(19) 0.0247(6) Uani 1 1 d . . .
C26 C 0.7405(3) -0.0832(2) 0.35700(19) 0.0254(6) Uani 1 1 d . A .
C27 C 0.7145(3) -0.1215(2) 0.4217(2) 0.0362(7) Uani 1 1 d . . .
H27 H 0.7327 -0.0823 0.4827 0.043 Uiso 1 1 calc R A .
C28 C 0.6597(3) -0.2232(2) 0.3793(2) 0.0345(7) Uani 1 1 d . A .
H28 H 0.6269 -0.2696 0.4027 0.041 Uiso 1 1 calc R . .
C29 C 0.6601(2) -0.2482(2) 0.29176(19) 0.0238(6) Uani 1 1 d . . .
C30 C 0.6332(2) -0.3457(2) 0.23151(18) 0.0216(5) Uani 1 1 d . A .
C31 C 0.9423(2) -0.2847(2) 0.0627(2) 0.0252(6) Uani 1 1 d . . .
C32 C 0.9220(3) -0.2818(2) -0.0239(2) 0.0352(7) Uani 1 1 d . . .
C33 C 0.9680(3) -0.3243(3) -0.0735(2) 0.0475(10) Uani 1 1 d . . .
H33 H 0.9513 -0.3213 -0.1336 0.057 Uiso 1 1 calc R . .
C34 C 1.0374(3) -0.3702(3) -0.0345(3) 0.0473(9) Uani 1 1 d . . .
H34 H 1.0679 -0.4013 -0.0686 0.057 Uiso 1 1 calc R . .
C35 C 1.0642(3) -0.3725(3) 0.0527(3) 0.0425(8) Uani 1 1 d . . .
H35 H 1.1159 -0.4018 0.0810 0.051 Uiso 1 1 calc R . .
C36 C 1.0149(3) -0.3314(2) 0.0983(2) 0.0324(7) Uani 1 1 d . . .
C37 C 1.2840(2) 0.06365(19) 0.29640(19) 0.0223(5) Uani 1 1 d . . .
C38 C 1.3633(2) 0.0933(2) 0.2669(2) 0.0274(6) Uani 1 1 d . . .
C39 C 1.4493(3) 0.0598(2) 0.2807(3) 0.0380(8) Uani 1 1 d . . .
H39 H 1.5020 0.0831 0.2593 0.046 Uiso 1 1 calc R . .
C40 C 1.4582(3) -0.0081(2) 0.3259(3) 0.0412(8) Uani 1 1 d . . .
H40 H 1.5167 -0.0331 0.3352 0.049 Uiso 1 1 calc R . .
C41 C 1.3833(3) -0.0399(2) 0.3576(2) 0.0357(7) Uani 1 1 d . . .
H41 H 1.3900 -0.0860 0.3902 0.043 Uiso 1 1 calc R . .
C42 C 1.2988(2) -0.0045(2) 0.34168(19) 0.0263(6) Uani 1 1 d . . .
C43 C 1.2394(2) 0.5347(2) 0.3840(2) 0.0243(6) Uani 1 1 d . . .
C44 C 1.2584(2) 0.5906(2) 0.3310(2) 0.0286(6) Uani 1 1 d . . .
C45 C 1.3337(3) 0.6901(2) 0.3678(2) 0.0354(7) Uani 1 1 d . . .
H45 H 1.3458 0.7248 0.3283 0.042 Uiso 1 1 calc R . .
C46 C 1.3912(3) 0.7383(2) 0.4628(2) 0.0368(8) Uani 1 1 d . . .
H46 H 1.4438 0.8076 0.4899 0.044 Uiso 1 1 calc R . .
C47 C 1.3739(3) 0.6878(2) 0.5196(2) 0.0346(7) Uani 1 1 d . . .
H47 H 1.4120 0.7217 0.5856 0.042 Uiso 1 1 calc R . .
C48 C 1.3006(2) 0.5878(2) 0.4789(2) 0.0290(6) Uani 1 1 d . . .
C49 C 0.6529(2) 0.2364(2) 0.10683(19) 0.0241(6) Uani 1 1 d . . .
C50 C 0.6413(3) 0.2565(2) 0.0272(2) 0.0291(6) Uani 1 1 d . . .
C51 C 0.5473(3) 0.2672(2) -0.0331(2) 0.0355(7) Uani 1 1 d . . .
H51 H 0.5438 0.2822 -0.0866 0.043 Uiso 1 1 calc R . .
C52 C 0.4583(3) 0.2557(2) -0.0145(2) 0.0399(8) Uani 1 1 d . . .
H52 H 0.3920 0.2624 -0.0560 0.048 Uiso 1 1 calc R . .
C53 C 0.4627(3) 0.2350(2) 0.0624(2) 0.0365(7) Uani 1 1 d . . .
H53 H 0.4007 0.2270 0.0752 0.044 Uiso 1 1 calc R . .
C54 C 0.5595(3) 0.2260(2) 0.1206(2) 0.0289(6) Uani 1 1 d . . .
C55 C 0.8641(2) 0.1050(2) 0.45717(15) 0.0272(11) Uani 0.774(3) 1 d PGU A 1
C56 C 0.9819(2) 0.1434(3) 0.49125(18) 0.0444(12) Uani 0.774(3) 1 d PGU A 1
C57 C 1.05457(18) 0.2224(3) 0.57758(19) 0.0481(13) Uani 0.774(3) 1 d PGU A 1
H57 H 1.1351 0.2486 0.6009 0.058 Uiso 0.774(3) 1 calc PR A 1
C58 C 1.0094(2) 0.2629(2) 0.62984(16) 0.0312(10) Uani 0.774(3) 1 d PGU A 1
H58 H 1.0590 0.3169 0.6888 0.037 Uiso 0.774(3) 1 calc PR A 1
C59 C 0.8916(2) 0.2245(2) 0.59576(19) 0.0277(9) Uani 0.774(3) 1 d PGU A 1
H59 H 0.8607 0.2522 0.6315 0.033 Uiso 0.774(3) 1 calc PR A 1
C60 C 0.81890(18) 0.1456(2) 0.50943(19) 0.0234(9) Uani 0.774(3) 1 d PGU A 1
C61 C 0.5564(3) -0.4365(2) 0.23263(19) 0.0241(6) Uani 1 1 d . . .
C62 C 0.4427(3) -0.4566(2) 0.2029(2) 0.0316(7) Uani 1 1 d . A .
C63 C 0.3662(3) -0.5414(2) 0.1991(2) 0.0369(7) Uani 1 1 d . . .
H63 H 0.2878 -0.5521 0.1761 0.044 Uiso 1 1 calc R A .
C64 C 0.4060(3) -0.6106(2) 0.2295(2) 0.0362(7) Uani 1 1 d . A .
H64 H 0.3550 -0.6703 0.2280 0.043 Uiso 1 1 calc R . .
C65 C 0.5199(3) -0.5936(2) 0.2623(2) 0.0338(7) Uani 1 1 d . . .
H65 H 0.5485 -0.6404 0.2848 0.041 Uiso 1 1 calc R A .
C66 C 0.5907(3) -0.5089(2) 0.2619(2) 0.0280(6) Uani 1 1 d . A .
C55B C 0.8460(9) 0.0898(8) 0.4546(5) 0.020(3) Uani 0.226(3) 1 d PGU A 2
C56B C 0.9459(9) 0.0847(8) 0.5164(6) 0.040(3) Uani 0.226(3) 1 d PGU A 2
C57B C 1.0119(8) 0.1555(9) 0.6075(6) 0.047(3) Uani 0.226(3) 1 d PGU A 2
H57B H 1.0802 0.1519 0.6497 0.057 Uiso 0.226(3) 1 calc PR A 2
C58B C 0.9782(10) 0.2315(8) 0.6368(6) 0.038(3) Uani 0.226(3) 1 d PGU A 2
H58B H 1.0233 0.2799 0.6990 0.045 Uiso 0.226(3) 1 calc PR A 2
C59B C 0.8784(10) 0.2366(8) 0.5750(8) 0.033(3) Uani 0.226(3) 1 d PGU A 2
H59B H 0.8553 0.2886 0.5950 0.039 Uiso 0.226(3) 1 calc PR A 2
C60B C 0.8123(8) 0.1658(9) 0.4839(7) 0.026(3) Uani 0.226(3) 1 d PGU A 2
F1 F 0.85422(19) -0.23525(17) -0.06083(13) 0.0498(5) Uani 1 1 d . . .
F2 F 1.03953(18) -0.33496(15) 0.18343(14) 0.0425(5) Uani 1 1 d . . .
F3 F 1.35449(16) 0.15830(13) 0.22116(14) 0.0376(4) Uani 1 1 d . . .
F4 F 1.22460(16) -0.03646(13) 0.37234(12) 0.0343(4) Uani 1 1 d . . .
F5 F 1.19940(15) 0.54413(13) 0.23725(12) 0.0340(4) Uani 1 1 d . . .
F6 F 1.28563(16) 0.53722(13) 0.53400(12) 0.0389(4) Uani 1 1 d . . .
F7 F 0.72729(16) 0.26477(16) 0.00758(13) 0.0424(5) Uani 1 1 d . . .
F8 F 0.56594(16) 0.20933(15) 0.19818(13) 0.0374(4) Uani 1 1 d . . .
F9 F 1.0231(2) 0.1072(3) 0.4422(2) 0.0979(18) Uani 0.774(3) 1 d P A 1
F10 F 0.70979(19) 0.10947(19) 0.47658(17) 0.0382(7) Uani 0.774(3) 1 d P A 1
F11 F 0.40216(16) -0.38930(15) 0.17228(16) 0.0444(5) Uani 1 1 d . . .
F12 F 0.70110(16) -0.49396(14) 0.29208(13) 0.0379(4) Uani 1 1 d . . .
F9B F 0.9741(8) 0.0164(7) 0.4891(7) 0.055(3) Uani 0.226(3) 1 d P . 2
F10B F 0.7169(7) 0.1688(7) 0.4309(6) 0.047(3) Uani 0.226(3) 1 d P A 2
N1 N 0.76237(18) -0.27615(16) 0.17762(15) 0.0198(4) Uani 1 1 d . . .
H1N H 0.7845 -0.2125 0.2126 0.024 Uiso 1 1 calc R . .
N2 N 1.04886(19) -0.07371(16) 0.18328(15) 0.0206(5) Uani 1 1 d . . .
H2N H 1.0939 -0.0957 0.1672 0.025 Uiso 1 1 calc R . .
N3 N 1.14787(19) 0.25199(16) 0.30648(16) 0.0225(5) Uani 1 1 d . . .
H3N H 1.0727 0.2218 0.2728 0.027 Uiso 1 1 calc R . .
N4 N 0.96286(19) 0.30450(16) 0.26160(15) 0.0210(5) Uani 1 1 d . . .
N5 N 0.80147(19) 0.13362(17) 0.27896(15) 0.0229(5) Uani 1 1 d . . .
H5N H 0.8667 0.1824 0.3243 0.027 Uiso 1 1 calc R A .
N6 N 0.70723(19) -0.16248(17) 0.27930(15) 0.0215(5) Uani 1 1 d . A .
O1E O 0.1835(2) 0.88632(17) 0.09531(16) 0.0446(6) Uani 1 1 d . . .
H1E H 0.2280 0.8559 0.1028 0.067 Uiso 1 1 calc R . .
C1E C 0.1845(2) 0.93371(17) 0.02878(16) 0.119(3) Uani 1 1 d R . .
H1E1 H 0.2641 0.9814 0.0518 0.143 Uiso 1 1 calc R . .
H1E2 H 0.1602 0.8805 -0.0311 0.143 Uiso 1 1 calc R . .
C2E C 0.1169(6) 0.9847(5) 0.0125(4) 0.0884(18) Uani 1 1 d . . .
H2E1 H 0.0365 0.9365 -0.0206 0.133 Uiso 1 1 calc R . .
H2E2 H 0.1304 1.0233 -0.0261 0.133 Uiso 1 1 calc R . .
H2E3 H 0.1338 1.0319 0.0721 0.133 Uiso 1 1 calc R . .
C1S C 1.0075(7) 0.4586(6) 0.5022(4) 0.063(2) Uani 0.655(4) 1 d P . 3
H1S1 H 1.0428 0.4627 0.5681 0.076 Uiso 0.655(4) 1 calc PR . 3
H1S2 H 1.0594 0.4495 0.4772 0.076 Uiso 0.655(4) 1 calc PR . 3
Cl1S Cl 0.86843(14) 0.35107(9) 0.43288(10) 0.0468(5) Uani 0.655(4) 1 d P . 3
O2E O 1.0200(14) 0.2475(12) 0.4213(11) 0.130(5) Uani 0.345(4) 1 d PU . 4
H2E H 1.0184 0.2692 0.3782 0.195 Uiso 0.345(4) 1 calc PR . 4
C3E C 1.100(3) 0.329(2) 0.512(2) 0.155(10) Uani 0.345(4) 1 d PU . 4
H3E1 H 1.1770 0.3578 0.5170 0.186 Uiso 0.345(4) 1 calc PR . 4
H3E2 H 1.1075 0.3038 0.5634 0.186 Uiso 0.345(4) 1 calc PR . 4
C4E C 1.046(3) 0.415(2) 0.514(2) 0.155(11) Uani 0.345(4) 1 d PU . 4
H4E1 H 0.9728 0.3909 0.4568 0.233 Uiso 0.345(4) 1 calc PR . 4
H4E2 H 1.0993 0.4788 0.5197 0.233 Uiso 0.345(4) 1 calc PR . 4
H4E3 H 1.0331 0.4271 0.5686 0.233 Uiso 0.345(4) 1 calc PR . 4
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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C30 121.8(2) .
N1 C1 C2 105.9(2) .
C30 C1 C2 132.2(2) .
C3 C2 C1 108.3(2) .
C3 C2 H2 125.9 .
C1 C2 H2 125.9 .
C2 C3 C4 108.6(2) .
C2 C3 H3 125.7 .
C4 C3 H3 125.7 .
N1 C4 C5 124.7(2) .
N1 C4 C3 105.2(2) .
C5 C4 C3 130.1(2) .
C4 C5 C6 123.1(2) .
C4 C5 C31 118.2(2) .
C6 C5 C31 118.5(2) .
N2 C6 C7 106.2(2) .
N2 C6 C5 122.6(2) .
C7 C6 C5 131.2(3) .
C8 C7 C6 108.6(3) .
C8 C7 H7 125.7 .
C6 C7 H7 125.7 .
C7 C8 C9 108.2(3) .
C7 C8 H8 125.9 .
C9 C8 H8 125.9 .
N2 C9 C8 106.3(2) .
N2 C9 C10 122.6(2) .
C8 C9 C10 130.3(3) .
C11 C10 C9 124.0(2) .
C11 C10 C37 117.5(2) .
C9 C10 C37 118.3(2) .
N3 C11 C10 127.0(2) .
N3 C11 C12 106.0(2) .
C10 C11 C12 127.0(3) .
C13 C12 C11 108.7(2) .
C13 C12 H12 125.6 .
C11 C12 H12 125.6 .
C12 C13 C14 108.2(2) .
C12 C13 H13 125.9 .
C14 C13 H13 125.9 .
N3 C14 C15 124.4(2) .
N3 C14 C13 106.3(2) .
C15 C14 C13 129.1(2) .
C14 C15 C16 123.5(2) .
C14 C15 C43 117.6(2) .
C16 C15 C43 118.9(2) .
N4 C16 C15 123.1(2) .
N4 C16 C17 111.1(2) .
C15 C16 C17 125.8(2) .
C18 C17 C16 106.4(2) .
C18 C17 H17 126.8 .
C16 C17 H17 126.8 .
C17 C18 C19 106.8(2) .
C17 C18 H18 126.6 .
C19 C18 H18 126.6 .
N4 C19 C20 123.7(2) .
N4 C19 C18 110.7(2) .
C20 C19 C18 125.5(2) .
C19 C20 C21 125.0(2) .
C19 C20 C49 118.7(2) .
C21 C20 C49 116.1(2) .
N5 C21 C20 125.6(2) .
N5 C21 C22 105.9(2) .
C20 C21 C22 128.2(2) .
C23 C22 C21 108.8(2) .
C23 C22 H22 125.6 .
C21 C22 H22 125.6 .
C22 C23 C24 107.7(2) .
C22 C23 H23 126.1 .
C24 C23 H23 126.1 .
N5 C24 C25 125.4(2) .
N5 C24 C23 106.4(2) .
C25 C24 C23 127.4(3) .
C26 C25 C24 120.3(3) .
C26 C25 C55B 115.1(5) .
C24 C25 C55B 124.1(5) .
C26 C25 C55 122.3(2) .
C24 C25 C55 117.4(3) .
C55B C25 C55 9.3(5) .
N6 C26 C25 121.7(3) .
N6 C26 C27 109.5(3) .
C25 C26 C27 128.6(3) .
C28 C27 C26 106.8(3) .
C28 C27 H27 126.6 .
C26 C27 H27 126.6 .
C27 C28 C29 106.5(3) .
C27 C28 H28 126.7 .
C29 C28 H28 126.7 .
N6 C29 C30 121.9(2) .
N6 C29 C28 110.2(2) .
C30 C29 C28 127.3(3) .
C1 C30 C29 120.8(2) .
C1 C30 C61 119.6(2) .
C29 C30 C61 119.6(2) .
C32 C31 C36 114.9(3) .
C32 C31 C5 122.4(3) .
C36 C31 C5 122.7(3) .
F1 C32 C31 117.5(3) .
F1 C32 C33 119.3(3) .
C31 C32 C33 123.2(3) .
C34 C33 C32 118.5(3) .
C34 C33 H33 120.7 .
C32 C33 H33 120.7 .
C33 C34 C35 121.2(3) .
C33 C34 H34 119.4 .
C35 C34 H34 119.4 .
C34 C35 C36 118.2(4) .
C34 C35 H35 120.9 .
C36 C35 H35 120.9 .
F2 C36 C35 118.5(3) .
F2 C36 C31 117.6(3) .
C35 C36 C31 123.9(3) .
C38 C37 C42 113.8(3) .
C38 C37 C10 124.7(2) .
C42 C37 C10 121.5(3) .
F3 C38 C39 118.0(3) .
F3 C38 C37 117.9(2) .
C39 C38 C37 124.1(3) .
C38 C39 C40 118.7(3) .
C38 C39 H39 120.7 .
C40 C39 H39 120.6 .
C41 C40 C39 120.3(3) .
C41 C40 H40 119.9 .
C39 C40 H40 119.9 .
C42 C41 C40 118.6(3) .
C42 C41 H41 120.7 .
C40 C41 H41 120.7 .
F4 C42 C41 118.6(3) .
F4 C42 C37 116.9(3) .
C41 C42 C37 124.5(3) .
C48 C43 C44 114.6(3) .
C48 C43 C15 122.4(3) .
C44 C43 C15 123.0(3) .
F5 C44 C45 118.2(3) .
F5 C44 C43 117.9(2) .
C45 C44 C43 124.0(3) .
C46 C45 C44 118.2(3) .
C46 C45 H45 120.9 .
C44 C45 H45 120.9 .
C45 C46 C47 120.7(3) .
C45 C46 H46 119.6 .
C47 C46 H46 119.6 .
C48 C47 C46 118.3(3) .
C48 C47 H47 120.9 .
C46 C47 H47 120.9 .
F6 C48 C47 118.6(3) .
F6 C48 C43 117.2(2) .
C47 C48 C43 124.1(3) .
C50 C49 C54 114.3(3) .
C50 C49 C20 124.3(3) .
C54 C49 C20 121.5(3) .
F7 C50 C51 118.3(3) .
F7 C50 C49 117.8(3) .
C51 C50 C49 123.9(3) .
C50 C51 C52 118.3(3) .
C50 C51 H51 120.8 .
C52 C51 H51 120.8 .
C53 C52 C51 121.3(3) .
C53 C52 H52 119.3 .
C51 C52 H52 119.3 .
C52 C53 C54 117.7(3) .
C52 C53 H53 121.2 .
C54 C53 H53 121.2 .
F8 C54 C53 117.8(3) .
F8 C54 C49 117.6(2) .
C53 C54 C49 124.5(3) .
C56 C55 C60 120.0 .
C56 C55 C25 120.7(2) .
C60 C55 C25 119.3(2) .
F9 C56 C57 120.2(2) .
F9 C56 C55 119.8(2) .
C57 C56 C55 120.0 .
C58 C57 C56 120.0 .
C58 C57 H57 120.0 .
C56 C57 H57 120.0 .
C59 C58 C57 120.0 .
C59 C58 H58 120.0 .
C57 C58 H58 120.0 .
C60 C59 C58 120.0 .
C60 C59 H59 120.0 .
C58 C59 H59 120.0 .
F10 C60 C59 120.9(2) .
F10 C60 C55 119.1(2) .
C59 C60 C55 120.0 .
C62 C61 C66 114.3(3) .
C62 C61 C30 122.1(2) .
C66 C61 C30 123.6(3) .
F11 C62 C63 117.3(3) .
F11 C62 C61 117.9(3) .
C63 C62 C61 124.8(3) .
C62 C63 C64 118.0(3) .
C62 C63 H63 121.0 .
C64 C63 H63 121.0 .
C63 C64 C65 120.0(3) .
C63 C64 H64 120.0 .
C65 C64 H64 120.0 .
C66 C65 C64 119.0(3) .
C66 C65 H65 120.5 .
C64 C65 H65 120.5 .
F12 C66 C65 118.6(3) .
F12 C66 C61 117.5(3) .
C65 C66 C61 123.9(3) .
C56B C55B C60B 120.0 .
C56B C55B C25 117.7(7) .
C60B C55B C25 122.3(7) .
F9B C56B C57B 121.0(8) .
F9B C56B C55B 119.0(8) .
C57B C56B C55B 120.0 .
C56B C57B C58B 120.0 .
C56B C57B H57B 120.0 .
C58B C57B H57B 120.0 .
C59B C58B C57B 120.0 .
C59B C58B H58B 120.0 .
C57B C58B H58B 120.0 .
C58B C59B C60B 120.0 .
C58B C59B H59B 120.0 .
C60B C59B H59B 120.0 .
F10B C60B C59B 118.2(8) .
F10B C60B C55B 121.6(8) .
C59B C60B C55B 120.0 .
F9B F9B C56B 142.6(15) 2_756
C4 N1 C1 112.1(2) .
C4 N1 H1N 123.9 .
C1 N1 H1N 124.0 .
C9 N2 C6 110.6(2) .
C9 N2 H2N 124.7 .
C6 N2 H2N 124.7 .
C14 N3 C11 110.7(2) .
C14 N3 H3N 124.7 .
C11 N3 H3N 124.7 .
C16 N4 C19 105.0(2) .
C24 N5 C21 111.1(2) .
C24 N5 H5N 124.5 .
C21 N5 H5N 124.5 .
C29 N6 C26 106.8(2) .
C1E O1E H1E 109.5 .
C2E C1E O1E 114.0(2) .
C2E C1E H1E1 108.7 .
O1E C1E H1E1 108.7 .
C2E C1E H1E2 108.7 .
O1E C1E H1E2 108.7 .
H1E1 C1E H1E2 107.6 .
C1E C2E H2E1 109.5 .
C1E C2E H2E2 109.5 .
H2E1 C2E H2E2 109.5 .
C1E C2E H2E3 109.5 .
H2E1 C2E H2E3 109.5 .
H2E2 C2E H2E3 109.5 .
C1S C1S Cl1S 108.5(8) 2_766
C1S C1S H1S1 110.0 2_766
Cl1S C1S H1S1 110.0 .
C1S C1S H1S2 110.0 2_766
Cl1S C1S H1S2 110.0 .
H1S1 C1S H1S2 108.4 .
C3E O2E H2E 109.5 .
O2E C3E C4E 105(2) .
O2E C3E H3E1 110.7 .
C4E C3E H3E1 110.7 .
O2E C3E H3E2 110.7 .
C4E C3E H3E2 110.7 .
H3E1 C3E H3E2 108.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.358(3) .
C1 C30 1.384(4) .
C1 C2 1.412(4) .
C2 C3 1.352(4) .
C2 H2 0.9500 .
C3 C4 1.426(4) .
C3 H3 0.9500 .
C4 N1 1.352(3) .
C4 C5 1.381(4) .
C5 C6 1.404(4) .
C5 C31 1.473(4) .
C6 N2 1.366(3) .
C6 C7 1.396(4) .
C7 C8 1.357(4) .
C7 H7 0.9500 .
C8 C9 1.401(4) .
C8 H8 0.9500 .
C9 N2 1.359(3) .
C9 C10 1.402(4) .
C10 C11 1.392(4) .
C10 C37 1.469(4) .
C11 N3 1.365(3) .
C11 C12 1.412(4) .
C12 C13 1.350(4) .
C12 H12 0.9500 .
C13 C14 1.413(4) .
C13 H13 0.9500 .
C14 N3 1.363(3) .
C14 C15 1.383(4) .
C15 C16 1.403(4) .
C15 C43 1.477(4) .
C16 N4 1.352(3) .
C16 C17 1.431(4) .
C17 C18 1.335(4) .
C17 H17 0.9500 .
C18 C19 1.429(4) .
C18 H18 0.9500 .
C19 N4 1.359(3) .
C19 C20 1.387(4) .
C20 C21 1.398(4) .
C20 C49 1.468(4) .
C21 N5 1.360(3) .
C21 C22 1.406(4) .
C22 C23 1.357(4) .
C22 H22 0.9500 .
C23 C24 1.412(4) .
C23 H23 0.9500 .
C24 N5 1.356(4) .
C24 C25 1.397(4) .
C25 C26 1.391(4) .
C25 C55B 1.398(7) .
C25 C55 1.521(3) .
C26 N6 1.357(3) .
C26 C27 1.437(4) .
C27 C28 1.342(5) .
C27 H27 0.9500 .
C28 C29 1.435(4) .
C28 H28 0.9500 .
C29 N6 1.345(3) .
C29 C30 1.411(4) .
C30 C61 1.466(4) .
C31 C32 1.371(4) .
C31 C36 1.377(4) .
C32 F1 1.337(4) .
C32 C33 1.380(5) .
C33 C34 1.353(6) .
C33 H33 0.9500 .
C34 C35 1.362(6) .
C34 H34 0.9500 .
C35 C36 1.364(4) .
C35 H35 0.9500 .
C36 F2 1.340(4) .
C37 C38 1.380(4) .
C37 C42 1.381(4) .
C38 F3 1.339(3) .
C38 C39 1.365(4) .
C39 C40 1.368(5) .
C39 H39 0.9500 .
C40 C41 1.363(5) .
C40 H40 0.9500 .
C41 C42 1.361(4) .
C41 H41 0.9500 .
C42 F4 1.342(3) .
C43 C48 1.372(4) .
C43 C44 1.376(4) .
C44 F5 1.344(3) .
C44 C45 1.366(4) .
C45 C46 1.366(5) .
C45 H45 0.9500 .
C46 C47 1.371(5) .
C46 H46 0.9500 .
C47 C48 1.361(4) .
C47 H47 0.9500 .
C48 F6 1.337(3) .
C49 C50 1.378(4) .
C49 C54 1.379(4) .
C50 F7 1.340(4) .
C50 C51 1.365(4) .
C51 C52 1.366(5) .
C51 H51 0.9500 .
C52 C53 1.363(5) .
C52 H52 0.9500 .
C53 C54 1.367(4) .
C53 H53 0.9500 .
C54 F8 1.341(3) .
C55 C56 1.3900 .
C55 C60 1.3900 .
C56 F9 1.279(3) .
C56 C57 1.3900 .
C57 C58 1.3900 .
C57 H57 0.9500 .
C58 C59 1.3900 .
C58 H58 0.9500 .
C59 C60 1.3900 .
C59 H59 0.9500 .
C60 F10 1.284(3) .
C61 C62 1.371(4) .
C61 C66 1.374(4) .
C62 F11 1.351(3) .
C62 C63 1.364(4) .
C63 C64 1.370(5) .
C63 H63 0.9500 .
C64 C65 1.376(5) .
C64 H64 0.9500 .
C65 C66 1.357(4) .
C65 H65 0.9500 .
C66 F12 1.342(3) .
C55B C56B 1.3900 .
C55B C60B 1.3900 .
C56B F9B 1.234(11) .
C56B C57B 1.3900 .
C57B C58B 1.3900 .
C57B H57B 0.9500 .
C58B C59B 1.3900 .
C58B H58B 0.9500 .
C59B C60B 1.3900 .
C59B H59B 0.9500 .
C60B F10B 1.282(10) .
F9B F9B 0.963(15) 2_756
N1 H1N 0.8800 .
N2 H2N 0.8800 .
N3 H3N 0.8800 .
N5 H5N 0.8800 .
O1E C1E 1.4296 .
O1E H1E 0.8400 .
C1E C2E 1.331(7) .
C1E H1E1 0.9900 .
C1E H1E2 0.9900 .
C2E H2E1 0.9800 .
C2E H2E2 0.9800 .
C2E H2E3 0.9800 .
C1S C1S 1.293(14) 2_766
C1S Cl1S 1.824(9) .
C1S H1S1 0.9900 .
C1S H1S2 0.9900 .
O2E C3E 1.45(3) .
O2E H2E 0.8400 .
C3E C4E 1.63(4) .
C3E H3E1 0.9900 .
C3E H3E2 0.9900 .
C4E H4E1 0.9800 .
C4E H4E2 0.9800 .
C4E H4E3 0.9800 .
