#------------------------------------------------------------------------------
#$Date: 2016-03-22 13:01:05 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178969 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/98/4119809.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_4119809
loop_
_publ_author_name
'Masayoshi Takase'
'Tomoyuki Narita'
'Wataru Fujita'
'Motoko S. Asano'
'Tohru Nishinaga'
'Hiroaki Benten'
'Kenji Yoza'
'Klaus Müllen'
_publ_section_title
;
 Pyrrole-Fused Azacoronene Family: The Influence of Replacement with
 Dialkoxybenzenes on the Optical and Electronic Properties in Neutral and
 Oxidized States
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8031
_journal_page_last               8040
_journal_paper_doi               10.1021/ja402371f
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C106 H70 F24 N4 O4'
_chemical_formula_weight         1919.66
_chemical_name_common            3a
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 125.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.648(4)
_cell_length_b                   38.150(8)
_cell_length_c                   15.294(3)
_cell_measurement_temperature    123
_cell_volume                     8817(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker XSHELL'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector system'
_diffrn_measurement_method       'omega scan'
_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  0.1466
_diffrn_reflns_av_sigmaI/netI    0.1578
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19072
_diffrn_reflns_theta_full        23.31
_diffrn_reflns_theta_max         23.31
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       prism
_exptl_crystal_F_000             3928
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     683
_refine_ls_number_reflns         6371
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1743
_refine_ls_R_factor_gt           0.0665
_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)+(0.0948P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1915
_reflns_number_gt                2983
_reflns_number_total             6371
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja402371f_si_001.cif
_cod_data_source_block           3a
_cod_original_cell_volume        8817(3)
_cod_original_sg_symbol_H-M      'C 1 2/c 1 '
_cod_database_code               4119809
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
F1A F 0.2037(8) -0.1948(3) 0.8304(12) 0.079(3) Uani 0.72(3) 1 d PU A 1
F2A F 0.2787(11) -0.2089(3) 0.7714(10) 0.080(4) Uani 0.72(3) 1 d PU A 1
F3A F 0.3376(7) -0.1791(3) 0.9132(8) 0.085(4) Uani 0.72(3) 1 d PU A 1
F1B F 0.232(2) -0.2123(6) 0.7450(18) 0.062(7) Uani 0.28(3) 1 d PU A 2
F2B F 0.3521(14) -0.1890(6) 0.868(3) 0.075(8) Uani 0.28(3) 1 d PU A 2
F3B F 0.239(2) -0.1866(6) 0.870(2) 0.056(7) Uani 0.28(3) 1 d PU A 2
F4 F 0.4772(2) -0.02135(11) 1.1309(3) 0.0577(11) Uani 1 1 d . . .
F5 F 0.3601(2) -0.02318(12) 1.1263(3) 0.0723(13) Uani 1 1 d . . .
F6 F 0.4097(3) -0.06970(12) 1.1060(3) 0.0801(14) Uani 1 1 d . . .
F7A F 0.4227(8) 0.1062(3) 1.1142(5) 0.082(5) Uani 0.74(2) 1 d PU B 1
F8A F 0.3986(5) 0.0538(4) 1.1320(5) 0.073(3) Uani 0.74(2) 1 d PU B 1
F9A F 0.5083(7) 0.0683(4) 1.1243(8) 0.057(3) Uani 0.74(2) 1 d PU B 1
F7B F 0.467(2) 0.1132(7) 1.0992(17) 0.082(9) Uani 0.26(2) 1 d PU B 2
F8B F 0.3943(12) 0.0793(10) 1.1303(13) 0.051(8) Uani 0.26(2) 1 d PU B 2
F9B F 0.489(2) 0.0525(9) 1.127(2) 0.067(10) Uani 0.26(2) 1 d PU B 2
F10 F 0.4859(3) 0.20249(12) 0.8658(4) 0.114(2) Uani 1 1 d . . .
F11 F 0.4080(3) 0.23944(12) 0.7461(4) 0.0979(17) Uani 1 1 d . . .
F12 F 0.3910(3) 0.23133(12) 0.8695(4) 0.0930(16) Uani 1 1 d . . .
C1 C 0.0000 0.09752(18) 0.2500 0.0196(18) Uani 1 2 d S . .
C2 C 0.0446(3) 0.04057(13) 0.3463(4) 0.0189(12) Uani 1 1 d . . .
C3 C 0.0460(3) 0.00459(13) 0.3460(4) 0.0192(12) Uani 1 1 d . . .
C4 C 0.0000 0.05972(17) 0.2500 0.0147(16) Uani 1 2 d S . .
C5 C 0.1035(3) 0.09458(13) 0.4522(4) 0.0215(13) Uani 1 1 d . . .
C6 C 0.1424(3) 0.04158(13) 0.5434(4) 0.0193(13) Uani 1 1 d . . .
C7 C 0.1011(3) -0.04923(13) 0.4515(4) 0.0227(13) Uani 1 1 d . . .
C8 C 0.1430(3) 0.00365(13) 0.5435(4) 0.0204(13) Uani 1 1 d . . .
C9 C 0.0509(4) 0.11558(13) 0.3517(4) 0.0234(13) Uani 1 1 d . . .
C10 C 0.1798(3) -0.02358(13) 0.6189(4) 0.0221(13) Uani 1 1 d . . .
C11 C 0.1542(3) -0.05646(13) 0.5629(4) 0.0216(13) Uani 1 1 d . . .
C12 C 0.1888(3) 0.06829(13) 0.6187(4) 0.0218(13) Uani 1 1 d . . .
C13 C 0.1657(3) 0.10108(13) 0.5613(4) 0.0204(13) Uani 1 1 d . . .
C14 C 0.2701(4) -0.09675(14) 0.7003(4) 0.0285(14) Uani 1 1 d . . .
H14 H 0.3132 -0.0807 0.7101 0.034 Uiso 1 1 calc R . .
C15 C 0.2973(4) -0.12641(15) 0.7643(4) 0.0359(15) Uani 1 1 d . . .
H15 H 0.3583 -0.1302 0.8194 0.043 Uiso 1 1 calc R . .
C16 C 0.1808(3) -0.08992(13) 0.6221(4) 0.0208(13) Uani 1 1 d . . .
C17 C 0.1196(4) -0.11441(14) 0.6073(4) 0.0312(14) Uani 1 1 d . . .
H17 H 0.0584 -0.1104 0.5539 0.037 Uiso 1 1 calc R . .
C18 C 0.1461(4) -0.14442(15) 0.6687(5) 0.0400(16) Uani 1 1 d . . .
H18 H 0.1033 -0.1610 0.6570 0.048 Uiso 1 1 calc R . .
C19 C 0.2353(4) -0.15047(15) 0.7476(5) 0.0358(16) Uani 1 1 d . A .
C20 C 0.2632(6) -0.18307(18) 0.8134(6) 0.0522(19) Uani 1 1 d . . .
C21 C 0.2343(3) -0.02230(13) 0.7379(4) 0.0206(12) Uani 1 1 d . . .
C22 C 0.3399(4) -0.02924(14) 0.9607(4) 0.0278(14) Uani 1 1 d . . .
C23 C 0.3231(4) -0.01287(13) 0.7984(4) 0.0251(14) Uani 1 1 d . . .
H23 H 0.3478 -0.0039 0.7636 0.030 Uiso 1 1 calc R . .
C24 C 0.3756(4) -0.01658(14) 0.9096(4) 0.0303(14) Uani 1 1 d . . .
H24 H 0.4364 -0.0104 0.9508 0.036 Uiso 1 1 calc R . .
C25 C 0.1995(4) -0.03431(14) 0.7915(4) 0.0284(14) Uani 1 1 d . . .
H25 H 0.1385 -0.0401 0.7509 0.034 Uiso 1 1 calc R . .
C26 C 0.2514(4) -0.03801(16) 0.9022(4) 0.0380(16) Uani 1 1 d . . .
H26 H 0.2266 -0.0464 0.9376 0.046 Uiso 1 1 calc R . .
C27 C 0.3963(4) -0.03507(18) 1.0804(5) 0.0423(17) Uani 1 1 d . . .
C28 C 0.2515(4) 0.06627(13) 0.7386(4) 0.0222(13) Uani 1 1 d . . .
C29 C 0.3397(4) 0.07528(14) 0.7893(4) 0.0272(14) Uani 1 1 d . . .
H29 H 0.3612 0.0797 0.7473 0.033 Uiso 1 1 calc R . .
C30 C 0.3959(4) 0.07784(14) 0.8996(4) 0.0328(15) Uani 1 1 d . . .
H30 H 0.4562 0.0840 0.9337 0.039 Uiso 1 1 calc R . .
C31 C 0.3652(4) 0.07150(15) 0.9615(4) 0.0325(15) Uani 1 1 d . B .
C32 C 0.2213(4) 0.05952(14) 0.8005(4) 0.0298(14) Uani 1 1 d . . .
H32 H 0.1612 0.0531 0.7664 0.036 Uiso 1 1 calc R . .
C33 C 0.2780(4) 0.06194(14) 0.9118(4) 0.0339(15) Uani 1 1 d . . .
H33 H 0.2569 0.0570 0.9540 0.041 Uiso 1 1 calc R . .
C34 C 0.4257(5) 0.0755(2) 1.0829(5) 0.051(2) Uani 1 1 d . . .
C35 C 0.2890(4) 0.17216(14) 0.7708(4) 0.0375(16) Uani 1 1 d . . .
H35 H 0.2962 0.1804 0.8342 0.045 Uiso 1 1 calc R . .
C36 C 0.2178(4) 0.13319(12) 0.6175(4) 0.0242(13) Uani 1 1 d . . .
C37 C 0.3380(4) 0.18678(15) 0.7393(5) 0.0373(16) Uani 1 1 d . . .
C38 C 0.2674(4) 0.14893(14) 0.5871(4) 0.0327(15) Uani 1 1 d . . .
H38 H 0.2600 0.1410 0.5234 0.039 Uiso 1 1 calc R . .
C39 C 0.3267(4) 0.17558(15) 0.6454(5) 0.0403(16) Uani 1 1 d . . .
H39 H 0.3591 0.1860 0.6221 0.048 Uiso 1 1 calc R . .
C40 C 0.2292(4) 0.14542(14) 0.7105(4) 0.0301(14) Uani 1 1 d . . .
H40 H 0.1957 0.1354 0.7329 0.036 Uiso 1 1 calc R . .
C41 C 0.4049(5) 0.21456(19) 0.8056(6) 0.061(2) Uani 1 1 d . . .
C42 C 0.0000 -0.01467(17) 0.2500 0.0195(18) Uani 1 2 d S . .
C43 C 0.0000 -0.05181(18) 0.2500 0.0191(18) Uani 1 2 d S . .
C44 C 0.0549(3) -0.06971(13) 0.3509(4) 0.0225(13) Uani 1 1 d . . .
C45 C 0.0629(4) -0.10608(14) 0.3440(4) 0.0264(14) Uani 1 1 d . . .
C46 C 0.1528(4) -0.15773(15) 0.4249(4) 0.0369(16) Uani 1 1 d . . .
H46A H 0.1385 -0.1625 0.3527 0.044 Uiso 1 1 calc R . .
H46B H 0.1164 -0.1734 0.4359 0.044 Uiso 1 1 calc R . .
C47 C 0.2744(4) -0.20240(15) 0.5202(5) 0.0474(18) Uani 1 1 d . . .
H47A H 0.2530 -0.2115 0.4481 0.057 Uiso 1 1 calc R . .
H47B H 0.2449 -0.2159 0.5460 0.057 Uiso 1 1 calc R . .
C48 C 0.2492(4) -0.16423(15) 0.5104(5) 0.0371(16) Uani 1 1 d . . .
H48A H 0.2642 -0.1560 0.5806 0.045 Uiso 1 1 calc R . .
H48B H 0.2845 -0.1504 0.4934 0.045 Uiso 1 1 calc R . .
C49 C 0.3740(5) -0.20792(18) 0.5975(6) 0.066(2) Uani 1 1 d . . .
H49A H 0.4031 -0.1960 0.5695 0.099 Uiso 1 1 calc R . .
H49B H 0.3871 -0.2330 0.6044 0.099 Uiso 1 1 calc R . .
H49C H 0.3957 -0.1983 0.6684 0.099 Uiso 1 1 calc R . .
C50 C 0.0000 0.16903(18) 0.2500 0.0255(19) Uani 1 2 d S . .
H50 H 0.0000 0.1939 0.2500 0.031 Uiso 1 2 calc SR . .
C51 C 0.0438(4) 0.15167(13) 0.3476(4) 0.0239(13) Uani 1 1 d . . .
C52 C 0.0707(4) 0.20691(14) 0.4381(4) 0.0359(15) Uani 1 1 d . . .
H52A H 0.0086 0.2140 0.3833 0.043 Uiso 1 1 calc R . .
H52B H 0.1078 0.2170 0.4175 0.043 Uiso 1 1 calc R . .
C53 C 0.1012(4) 0.22033(14) 0.5469(4) 0.0317(15) Uani 1 1 d . . .
H53A H 0.1010 0.2463 0.5454 0.038 Uiso 1 1 calc R . .
H53B H 0.1629 0.2126 0.6007 0.038 Uiso 1 1 calc R . .
C54 C 0.0735(4) 0.22541(16) 0.6881(5) 0.0452(17) Uani 1 1 d . . .
H54A H 0.1354 0.2194 0.7446 0.068 Uiso 1 1 calc R . .
H54B H 0.0359 0.2170 0.7091 0.068 Uiso 1 1 calc R . .
H54C H 0.0676 0.2509 0.6786 0.068 Uiso 1 1 calc R . .
C55 C 0.0452(4) 0.20822(15) 0.5832(5) 0.0386(16) Uani 1 1 d . . .
H55A H 0.0503 0.1825 0.5927 0.046 Uiso 1 1 calc R . .
H55B H -0.0176 0.2139 0.5266 0.046 Uiso 1 1 calc R . .
C56 C 0.0000 -0.12396(19) 0.2500 0.0262(19) Uani 1 2 d S . .
H56 H 0.0000 -0.1489 0.2500 0.031 Uiso 1 2 calc SR . .
N1 N 0.0909(3) 0.05852(10) 0.4432(3) 0.0195(10) Uani 1 1 d . . .
N2 N 0.0949(3) -0.01306(10) 0.4429(3) 0.0215(11) Uani 1 1 d . . .
O1 O 0.1340(2) -0.12176(9) 0.4320(3) 0.0321(10) Uani 1 1 d . . .
O2 O 0.0777(2) 0.16907(8) 0.4422(3) 0.0285(9) Uani 1 1 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'
F F 0.0171 0.0103 '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'
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
C9 C1 C9 122.7(6) . 2
C9 C1 C4 118.6(3) . .
C9 C1 C4 118.6(3) 2 .
C3 C2 N1 119.8(4) . .
C3 C2 C4 121.3(5) . .
N1 C2 C4 118.8(5) . .
C2 C3 N2 119.2(5) . .
C2 C3 C42 121.8(5) . .
N2 C3 C42 119.0(5) . .
C2 C4 C2 117.1(6) 2 .
C2 C4 C1 121.5(3) 2 .
C2 C4 C1 121.5(3) . .
C13 C5 N1 105.7(4) . .
C13 C5 C9 136.8(5) . .
N1 C5 C9 117.5(4) . .
C12 C6 N1 105.2(4) . .
C12 C6 C8 136.8(5) . .
N1 C6 C8 117.5(4) . .
N2 C7 C11 105.7(4) . .
N2 C7 C44 117.7(4) . .
C11 C7 C44 136.6(5) . .
C10 C8 N2 104.9(4) . .
C10 C8 C6 138.1(5) . .
N2 C8 C6 117.0(4) . .
C51 C9 C1 116.3(5) . .
C51 C9 C5 125.0(5) . .
C1 C9 C5 118.6(5) . .
C8 C10 C11 109.0(4) . .
C8 C10 C21 130.0(5) . .
C11 C10 C21 120.9(4) . .
C7 C11 C10 107.7(4) . .
C7 C11 C16 131.2(4) . .
C10 C11 C16 121.1(4) . .
C6 C12 C13 108.2(4) . .
C6 C12 C28 129.6(5) . .
C13 C12 C28 122.2(4) . .
C5 C13 C12 108.6(4) . .
C5 C13 C36 130.3(5) . .
C12 C13 C36 120.2(4) . .
C15 C14 C16 121.3(5) . .
C15 C14 H14 119.4 . .
C16 C14 H14 119.4 . .
C19 C15 C14 119.6(6) . .
C19 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C17 C16 C14 118.0(5) . .
C17 C16 C11 122.3(5) . .
C14 C16 C11 119.6(5) . .
C18 C17 C16 121.1(6) . .
C18 C17 H17 119.4 . .
C16 C17 H17 119.4 . .
C17 C18 C19 120.0(6) . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C15 C19 C18 119.9(5) . .
C15 C19 C20 120.5(6) . .
C18 C19 C20 119.6(6) . .
F3B C20 F2A 124.2(13) . .
F3B C20 F3A 76.3(14) . .
F2A C20 F3A 105.4(8) . .
F3B C20 F1A 29.1(12) . .
F2A C20 F1A 106.9(9) . .
F3A C20 F1A 103.7(8) . .
F3B C20 F2B 111.8(16) . .
F2A C20 F2B 68.7(12) . .
F3A C20 F2B 41.1(12) . .
F1A C20 F2B 131.5(12) . .
F3B C20 F1B 106.3(16) . .
F2A C20 F1B 31.2(10) . .
F3A C20 F1B 129.9(12) . .
F1A C20 F1B 81.2(12) . .
F2B C20 F1B 98.9(14) . .
F3B C20 C19 117.0(12) . .
F2A C20 C19 112.9(7) . .
F3A C20 C19 113.3(7) . .
F1A C20 C19 113.8(7) . .
F2B C20 C19 111.7(10) . .
F1B C20 C19 109.4(11) . .
C25 C21 C23 118.6(5) . .
C25 C21 C10 119.6(5) . .
C23 C21 C10 121.4(5) . .
C24 C22 C26 120.6(5) . .
C24 C22 C27 121.1(5) . .
C26 C22 C27 118.2(5) . .
C24 C23 C21 120.1(5) . .
C24 C23 H23 120.0 . .
C21 C23 H23 120.0 . .
C22 C24 C23 120.2(5) . .
C22 C24 H24 119.9 . .
C23 C24 H24 119.9 . .
C26 C25 C21 121.7(5) . .
C26 C25 H25 119.2 . .
C21 C25 H25 119.2 . .
C25 C26 C22 118.8(5) . .
C25 C26 H26 120.6 . .
C22 C26 H26 120.6 . .
F5 C27 F4 108.5(5) . .
F5 C27 F6 104.3(5) . .
F4 C27 F6 105.1(5) . .
F5 C27 C22 112.9(5) . .
F4 C27 C22 113.3(5) . .
F6 C27 C22 112.1(5) . .
C32 C28 C29 119.3(5) . .
C32 C28 C12 120.8(5) . .
C29 C28 C12 119.5(5) . .
C30 C29 C28 120.4(5) . .
C30 C29 H29 119.8 . .
C28 C29 H29 119.8 . .
C29 C30 C31 120.2(6) . .
C29 C30 H30 119.9 . .
C31 C30 H30 119.9 . .
C33 C31 C30 119.7(5) . .
C33 C31 C34 119.6(6) . .
C30 C31 C34 120.7(6) . .
C28 C32 C33 120.5(6) . .
C28 C32 H32 119.7 . .
C33 C32 H32 119.7 . .
C31 C33 C32 119.9(5) . .
C31 C33 H33 120.1 . .
C32 C33 H33 120.1 . .
F8B C34 F7A 60.7(14) . .
F8B C34 F9B 113.3(19) . .
F7A C34 F9B 130.7(16) . .
F8B C34 F9A 126.7(11) . .
F7A C34 F9A 107.9(9) . .
F9B C34 F9A 31.8(16) . .
F8B C34 F8A 43.4(15) . .
F7A C34 F8A 103.4(8) . .
F9B C34 F8A 80.2(18) . .
F9A C34 F8A 108.1(7) . .
F8B C34 C31 119.0(10) . .
F7A C34 C31 112.7(6) . .
F9B C34 C31 111.4(15) . .
F9A C34 C31 113.3(7) . .
F8A C34 C31 110.8(7) . .
F8B C34 F7B 99.3(16) . .
F7A C34 F7B 39.7(9) . .
F9B C34 F7B 108.9(18) . .
F9A C34 F7B 77.8(12) . .
F8A C34 F7B 138.6(11) . .
C31 C34 F7B 103.3(9) . .
C37 C35 C40 120.3(5) . .
C37 C35 H35 119.9 . .
C40 C35 H35 119.9 . .
C38 C36 C40 117.7(5) . .
C38 C36 C13 120.0(5) . .
C40 C36 C13 121.6(5) . .
C35 C37 C39 120.5(5) . .
C35 C37 C41 120.7(6) . .
C39 C37 C41 118.8(6) . .
C39 C38 C36 122.8(5) . .
C39 C38 H38 118.6 . .
C36 C38 H38 118.6 . .
C38 C39 C37 118.3(6) . .
C38 C39 H39 120.9 . .
C37 C39 H39 120.9 . .
C35 C40 C36 120.5(6) . .
C35 C40 H40 119.8 . .
C36 C40 H40 119.8 . .
F10 C41 F12 107.4(6) . .
F10 C41 F11 103.5(7) . .
F12 C41 F11 105.4(6) . .
F10 C41 C37 112.9(6) . .
F12 C41 C37 113.7(7) . .
F11 C41 C37 113.1(6) . .
C3 C42 C3 116.6(6) . 2
C3 C42 C43 121.7(3) . .
C3 C42 C43 121.7(3) 2 .
C42 C43 C44 118.5(3) . 2
C42 C43 C44 118.5(3) . .
C44 C43 C44 123.0(7) 2 .
C45 C44 C43 115.5(5) . .
C45 C44 C7 125.4(5) . .
C43 C44 C7 119.0(5) . .
O1 C45 C56 123.5(5) . .
O1 C45 C44 116.5(5) . .
C56 C45 C44 119.9(5) . .
O1 C46 C48 108.2(5) . .
O1 C46 H46A 110.1 . .
C48 C46 H46A 110.1 . .
O1 C46 H46B 110.1 . .
C48 C46 H46B 110.1 . .
H46A C46 H46B 108.4 . .
C48 C47 C49 112.2(5) . .
C48 C47 H47A 109.2 . .
C49 C47 H47A 109.2 . .
C48 C47 H47B 109.2 . .
C49 C47 H47B 109.2 . .
H47A C47 H47B 107.9 . .
C46 C48 C47 113.0(5) . .
C46 C48 H48A 109.0 . .
C47 C48 H48A 109.0 . .
C46 C48 H48B 109.0 . .
C47 C48 H48B 109.0 . .
H48A C48 H48B 107.8 . .
C47 C49 H49A 109.5 . .
C47 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C47 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
C51 C50 C51 122.6(7) 2 .
C51 C50 H50 118.7 2 .
C51 C50 H50 118.7 . .
O2 C51 C50 121.8(5) . .
O2 C51 C9 117.6(4) . .
C50 C51 C9 120.6(5) . .
O2 C52 C53 109.0(4) . .
O2 C52 H52A 109.9 . .
C53 C52 H52A 109.9 . .
O2 C52 H52B 109.9 . .
C53 C52 H52B 109.9 . .
H52A C52 H52B 108.3 . .
C52 C53 C55 114.2(5) . .
C52 C53 H53A 108.7 . .
C55 C53 H53A 108.7 . .
C52 C53 H53B 108.7 . .
C55 C53 H53B 108.7 . .
H53A C53 H53B 107.6 . .
C55 C54 H54A 109.5 . .
C55 C54 H54B 109.5 . .
H54A C54 H54B 109.5 . .
C55 C54 H54C 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
C53 C55 C54 111.7(5) . .
C53 C55 H55A 109.3 . .
C54 C55 H55A 109.3 . .
C53 C55 H55B 109.3 . .
C54 C55 H55B 109.3 . .
H55A C55 H55B 107.9 . .
C45 C56 C45 121.3(7) . 2
C45 C56 H56 119.4 . .
C45 C56 H56 119.4 2 .
C2 N1 C5 124.1(4) . .
C2 N1 C6 122.8(4) . .
C5 N1 C6 112.4(4) . .
C3 N2 C7 123.7(4) . .
C3 N2 C8 123.6(4) . .
C7 N2 C8 112.6(4) . .
C45 O1 C46 119.1(4) . .
C51 O2 C52 117.7(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1A C20 1.355(12) .
F2A C20 1.299(11) .
F3A C20 1.340(11) .
F1B C20 1.40(2) .
F2B C20 1.37(2) .
F3B C20 1.20(3) .
F4 C27 1.333(7) .
F5 C27 1.309(7) .
F6 C27 1.359(7) .
F7A C34 1.281(9) .
F8A C34 1.398(12) .
F9A C34 1.306(12) .
F7B C34 1.58(3) .
F8B C34 1.180(18) .
F9B C34 1.30(3) .
F10 C41 1.309(8) .
F11 C41 1.341(8) .
F12 C41 1.313(8) .
C1 C9 1.437(6) .
C1 C9 1.437(6) 2
C1 C4 1.442(9) .
C2 C3 1.373(7) .
C2 N1 1.382(6) .
C2 C4 1.400(6) .
C3 N2 1.377(6) .
C3 C42 1.399(6) .
C4 C2 1.400(6) 2
C5 C13 1.387(7) .
C5 N1 1.389(6) .
C5 C9 1.482(7) .
C6 C12 1.394(7) .
C6 N1 1.402(6) .
C6 C8 1.447(7) .
C7 N2 1.385(6) .
C7 C11 1.408(7) .
C7 C44 1.471(7) .
C8 C10 1.397(7) .
C8 N2 1.401(6) .
C9 C51 1.381(7) .
C10 C11 1.434(7) .
C10 C21 1.476(7) .
C11 C16 1.473(7) .
C12 C13 1.442(7) .
C12 C28 1.491(7) .
C13 C36 1.485(7) .
C14 C15 1.383(7) .
C14 C16 1.391(7) .
C14 H14 0.9500 .
C15 C19 1.378(8) .
C15 H15 0.9500 .
C16 C17 1.387(7) .
C17 C18 1.376(7) .
C17 H17 0.9500 .
C18 C19 1.386(8) .
C18 H18 0.9500 .
C19 C20 1.489(8) .
C21 C25 1.388(7) .
C21 C23 1.389(7) .
C22 C24 1.377(7) .
C22 C26 1.380(8) .
C22 C27 1.500(8) .
C23 C24 1.385(7) .
C23 H23 0.9500 .
C24 H24 0.9500 .
C25 C26 1.380(7) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C28 C32 1.378(7) .
C28 C29 1.389(7) .
C29 C30 1.372(7) .
C29 H29 0.9500 .
C30 C31 1.386(8) .
C30 H30 0.9500 .
C31 C33 1.380(8) .
C31 C34 1.512(8) .
C32 C33 1.385(7) .
C32 H32 0.9500 .
C33 H33 0.9500 .
C35 C37 1.377(8) .
C35 C40 1.390(8) .
C35 H35 0.9500 .
C36 C38 1.390(7) .
C36 C40 1.390(7) .
C37 C39 1.390(8) .
C37 C41 1.491(9) .
C38 C39 1.378(8) .
C38 H38 0.9500 .
C39 H39 0.9500 .
C40 H40 0.9500 .
C42 C3 1.399(6) 2
C42 C43 1.417(9) .
C43 C44 1.430(6) 2
C43 C44 1.430(6) .
C44 C45 1.406(7) .
C45 O1 1.355(6) .
C45 C56 1.390(6) .
C46 O1 1.436(6) .
C46 C48 1.500(8) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 C48 1.510(8) .
C47 C49 1.522(9) .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
C50 C51 1.380(6) 2
C50 C51 1.380(6) .
C50 H50 0.9500 .
C51 O2 1.365(6) .
C52 O2 1.447(6) .
C52 C53 1.499(7) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C55 1.512(7) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 C55 1.514(7) .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 0.9800 .
C55 H55A 0.9900 .
C55 H55B 0.9900 .
C56 C45 1.390(6) 2
C56 H56 0.9500 .
