#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/69/4106954.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_4106954
loop_
_publ_author_name
'Michael J. Bojdys'
'Michael E. Briggs'
'James T. A. Jones'
'Dave J. Adams'
'Samantha Y. Chong'
'Marc Schmidtmann'
'Andrew I. Cooper'
_publ_section_title
;
 Supramolecular Engineering of Intrinsic and Extrinsic Porosity in
 Covalent Organic Cages
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16566
_journal_page_last               16571
_journal_paper_doi               10.1021/ja2056374
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C124.5 H89.5 Cl13.5 F12 N12 O0.5'
_chemical_formula_weight         2468.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           146
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   30.587(2)
_cell_length_b                   30.587(2)
_cell_length_c                   21.553(2)
_cell_measurement_reflns_used    7609
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.50
_cell_measurement_theta_min      2.24
_cell_volume                     17463(2)
_computing_cell_refinement       'Bruker AXS SAINT V7.68A'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r6 (Rigaku, 2010)
;
_computing_data_reduction        'Bruker AXS SAINT V7.68A'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            45224
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             7572
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.934
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     980
_refine_ls_number_reflns         11108
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0828
_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)+(0.1000P)²+40.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2298
_reflns_number_gt                7689
_reflns_number_total             11108
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2056374_si_005.cif
_cod_data_source_block           marf
_cod_original_cell_volume        17462(2)
_cod_original_sg_symbol_H-M      'R 3'
_cod_original_formula_sum        'C124.50 H89.50 Cl13.50 F12 N12 O0.50'
_cod_database_code               4106954
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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
N1 N 0.5428(2) 0.2165(2) 0.7717(3) 0.0315(15) Uani 1 1 d . . .
N2 N 0.4715(2) 0.1620(2) 0.6765(3) 0.0308(15) Uani 1 1 d . . .
N3 N 0.6018(3) 0.1529(3) 0.4485(3) 0.0357(16) Uani 1 1 d . . .
N4 N 0.7091(3) 0.2041(3) 0.4315(3) 0.0367(17) Uani 1 1 d . . .
N5 N 0.5535(3) 0.3430(3) -0.1168(3) 0.0457(19) Uani 1 1 d . . .
N6 N 0.4958(3) 0.3485(3) -0.0149(3) 0.0397(17) Uani 1 1 d . . .
N7 N 0.4899(3) 0.2217(3) 0.2280(3) 0.0385(17) Uani 1 1 d . . .
N8 N 0.5361(3) 0.1572(3) 0.2238(3) 0.0438(18) Uani 1 1 d . . .
F1 F 0.4863(3) 0.1358(4) 1.0370(3) 0.119(3) Uani 1 1 d . . .
F2 F 0.25851(19) 0.0138(2) 0.7893(3) 0.0718(18) Uani 1 1 d . . .
F3 F 0.4990(2) -0.0651(2) 0.3400(3) 0.088(2) Uani 1 1 d . . .
F4 F 0.7888(3) 0.1027(3) 0.2514(4) 0.105(3) Uani 1 1 d . . .
F5 F 0.4646(3) 0.3323(3) -0.3778(3) 0.086(2) Uani 1 1 d . . .
F6 F 0.3249(3) 0.3845(3) -0.1205(4) 0.111(3) Uani 1 1 d . . .
F7 F 0.2901(2) 0.1160(3) 0.3837(4) 0.100(3) Uani 1 1 d . . .
F8 F 0.4074(2) -0.0394(2) 0.3798(3) 0.0796(19) Uani 1 1 d . . .
C1 C 0.6499(3) 0.2820(3) 0.7507(3) 0.0318(19) Uani 1 1 d . . .
H1 H 0.6382 0.2468 0.7497 0.038 Uiso 1 1 calc R . .
C2 C 0.6147(3) 0.2989(3) 0.7515(3) 0.0310(19) Uani 1 1 d . . .
C3 C 0.5601(3) 0.2633(3) 0.7598(3) 0.0317(19) Uani 1 1 d . . .
H3A H 0.5371 0.2755 0.7562 0.038 Uiso 1 1 calc R . .
C4 C 0.4883(3) 0.1860(3) 0.7858(4) 0.038(2) Uani 1 1 d . . .
H4A H 0.4724 0.2074 0.7802 0.045 Uiso 1 1 calc R . .
C5 C 0.4643(3) 0.1413(3) 0.7392(3) 0.0309(18) Uani 1 1 d . . .
H5A H 0.4817 0.1211 0.7429 0.037 Uiso 1 1 calc R . .
C6 C 0.5058(3) 0.1628(3) 0.6435(4) 0.037(2) Uani 1 1 d . . .
H6A H 0.5246 0.1483 0.6594 0.044 Uiso 1 1 calc R . .
C7 C 0.5177(3) 0.1854(3) 0.5817(4) 0.0325(19) Uani 1 1 d . . .
C8 C 0.4996(3) 0.2164(3) 0.5625(4) 0.037(2) Uani 1 1 d . . .
H8A H 0.4802 0.2236 0.5907 0.044 Uiso 1 1 calc R . .
C9 C 0.5090(3) 0.2377(3) 0.5030(4) 0.038(2) Uani 1 1 d . . .
C10 C 0.5371(3) 0.2249(3) 0.4616(4) 0.040(2) Uani 1 1 d . . .
H10A H 0.5433 0.2381 0.4206 0.048 Uiso 1 1 calc R . .
C11 C 0.5556(3) 0.1938(3) 0.4791(4) 0.036(2) Uani 1 1 d . . .
C12 C 0.5467(3) 0.1745(3) 0.5401(4) 0.039(2) Uani 1 1 d . . .
H12A H 0.5602 0.1540 0.5532 0.047 Uiso 1 1 calc R . .
C13 C 0.5840(3) 0.1819(3) 0.4357(4) 0.035(2) Uani 1 1 d . . .
H13A H 0.5899 0.1963 0.3953 0.042 Uiso 1 1 calc R . .
C14 C 0.6255(3) 0.1400(3) 0.3993(3) 0.035(2) Uani 1 1 d . . .
H14A H 0.6291 0.1608 0.3619 0.042 Uiso 1 1 calc R . .
C15 C 0.6776(3) 0.1511(3) 0.4201(4) 0.039(2) Uani 1 1 d . . .
H15A H 0.6738 0.1327 0.4599 0.046 Uiso 1 1 calc R . .
C16 C 0.7282(3) 0.2182(3) 0.4856(4) 0.0347(19) Uani 1 1 d . . .
H16 H 0.7198 0.1930 0.5163 0.042 Uiso 1 1 calc R . .
C17 C 0.4826(3) 0.1693(3) 0.8514(4) 0.043(2) Uani 1 1 d . . .
C18 C 0.5045(4) 0.1414(5) 0.8737(5) 0.074(3) Uani 1 1 d . . .
H18A H 0.5218 0.1321 0.8448 0.089 Uiso 1 1 calc R . .
C19 C 0.5027(4) 0.1270(5) 0.9331(6) 0.074(3) Uani 1 1 d . . .
H19A H 0.5144 0.1046 0.9447 0.089 Uiso 1 1 calc R . .
C20 C 0.4847(4) 0.1444(5) 0.9735(5) 0.069(3) Uani 1 1 d . . .
C21 C 0.4626(4) 0.1742(4) 0.9592(5) 0.069(3) Uani 1 1 d . . .
H21A H 0.4500 0.1869 0.9904 0.083 Uiso 1 1 calc R . .
C22 C 0.4605(4) 0.1844(3) 0.8939(4) 0.052(3) Uani 1 1 d . . .
H22A H 0.4435 0.2016 0.8810 0.063 Uiso 1 1 calc R . .
C23 C 0.4094(3) 0.1080(3) 0.7521(3) 0.0318(19) Uani 1 1 d . . .
C24 C 0.3918(4) 0.0582(3) 0.7705(5) 0.055(3) Uani 1 1 d . . .
H24A H 0.4145 0.0458 0.7753 0.065 Uiso 1 1 calc R . .
C25 C 0.3389(4) 0.0258(4) 0.7823(5) 0.054(3) Uani 1 1 d . . .
H25A H 0.3260 -0.0082 0.7948 0.065 Uiso 1 1 calc R . .
C26 C 0.3087(4) 0.0445(5) 0.7754(4) 0.064(3) Uani 1 1 d . . .
C27 C 0.3248(3) 0.0947(4) 0.7569(4) 0.052(3) Uani 1 1 d . . .
H27A H 0.3020 0.1072 0.7531 0.062 Uiso 1 1 calc R . .
C28 C 0.3749(3) 0.1239(3) 0.7447(4) 0.045(2) Uani 1 1 d . . .
H28A H 0.3868 0.1573 0.7303 0.054 Uiso 1 1 calc R . .
C29 C 0.5919(3) 0.0844(3) 0.3834(4) 0.037(2) Uani 1 1 d . . .
C30 C 0.5775(3) 0.0696(3) 0.3220(4) 0.039(2) Uani 1 1 d . . .
H30A H 0.5889 0.0942 0.2900 0.046 Uiso 1 1 calc R . .
C31 C 0.5472(4) 0.0198(4) 0.3077(5) 0.053(3) Uani 1 1 d . . .
H31A H 0.5383 0.0097 0.2657 0.064 Uiso 1 1 calc R . .
C32 C 0.5296(4) -0.0155(3) 0.3537(6) 0.060(3) Uani 1 1 d . . .
C33 C 0.5424(4) -0.0036(4) 0.4145(6) 0.061(3) Uani 1 1 d . . .
H33A H 0.5301 -0.0289 0.4457 0.073 Uiso 1 1 calc R . .
C34 C 0.5752(3) 0.0485(4) 0.4294(4) 0.048(2) Uani 1 1 d . . .
H34A H 0.5854 0.0583 0.4711 0.058 Uiso 1 1 calc R . .
C35 C 0.7034(3) 0.1338(3) 0.3729(4) 0.041(2) Uani 1 1 d . . .
C36 C 0.7159(3) 0.1558(3) 0.3153(4) 0.044(2) Uani 1 1 d . . .
H36A H 0.7057 0.1794 0.3037 0.053 Uiso 1 1 calc R . .
C37 C 0.7437(3) 0.1442(4) 0.2733(4) 0.051(2) Uani 1 1 d . . .
H37A H 0.7518 0.1592 0.2333 0.061 Uiso 1 1 calc R . .
C38 C 0.7583(5) 0.1118(4) 0.2907(5) 0.070(3) Uani 1 1 d . . .
C39 C 0.7456(5) 0.0878(4) 0.3466(6) 0.079(4) Uani 1 1 d . . .
H39A H 0.7559 0.0643 0.3578 0.094 Uiso 1 1 calc R . .
C40 C 0.7166(4) 0.0992(4) 0.3872(5) 0.061(3) Uani 1 1 d . . .
H40A H 0.7061 0.0820 0.4258 0.074 Uiso 1 1 calc R . .
C41 C 0.6566(3) 0.3728(3) -0.0901(4) 0.040(2) Uani 1 1 d . . .
H41 H 0.6494 0.3996 -0.0890 0.049 Uiso 1 1 calc R . .
C42 C 0.6159(3) 0.3223(3) -0.0908(4) 0.036(2) Uani 1 1 d . . .
C43 C 0.5649(3) 0.3113(3) -0.0952(4) 0.038(2) Uani 1 1 d . . .
H43A H 0.5386 0.2794 -0.0815 0.046 Uiso 1 1 calc R . .
C44 C 0.5008(3) 0.3301(3) -0.1228(4) 0.040(2) Uani 1 1 d . . .
H44A H 0.4784 0.2949 -0.1076 0.048 Uiso 1 1 calc R . .
C45 C 0.4965(4) 0.3680(4) -0.0779(4) 0.046(2) Uani 1 1 d . . .
H45A H 0.5268 0.4023 -0.0827 0.056 Uiso 1 1 calc R . .
C46 C 0.5318(4) 0.3742(4) 0.0199(4) 0.048(2) Uani 1 1 d . . .
H46A H 0.5580 0.4059 0.0054 0.058 Uiso 1 1 calc R . .
C47 C 0.5358(4) 0.3579(4) 0.0826(4) 0.050(2) Uani 1 1 d . . .
C48 C 0.5667(3) 0.3943(3) 0.1256(4) 0.046(2) Uani 1 1 d . . .
H48A H 0.5844 0.4290 0.1147 0.055 Uiso 1 1 calc R . .
C49 C 0.5716(3) 0.3785(3) 0.1865(4) 0.040(2) Uani 1 1 d . . .
C50 C 0.5474(3) 0.3290(3) 0.1998(4) 0.040(2) Uani 1 1 d . . .
H50A H 0.5521 0.3188 0.2396 0.047 Uiso 1 1 calc R . .
C51 C 0.5160(3) 0.2921(3) 0.1582(4) 0.039(2) Uani 1 1 d . . .
C52 C 0.5097(3) 0.3068(3) 0.0993(4) 0.041(2) Uani 1 1 d . . .
H52A H 0.4877 0.2821 0.0704 0.050 Uiso 1 1 calc R . .
C53 C 0.4895(3) 0.2373(3) 0.1749(4) 0.042(2) Uani 1 1 d . . .
H53A H 0.4714 0.2133 0.1433 0.051 Uiso 1 1 calc R . .
C54 C 0.4625(3) 0.1666(3) 0.2406(4) 0.041(2) Uani 1 1 d . . .
H54A H 0.4510 0.1482 0.2003 0.049 Uiso 1 1 calc R . .
C55 C 0.5005(3) 0.1536(3) 0.2710(4) 0.039(2) Uani 1 1 d . . .
H55A H 0.5195 0.1792 0.3039 0.047 Uiso 1 1 calc R . .
C56 C 0.5832(3) 0.1871(3) 0.2313(4) 0.036(2) Uani 1 1 d . . .
H56 H 0.5940 0.2068 0.2681 0.043 Uiso 1 1 calc R . .
C57 C 0.4897(3) 0.3333(4) -0.1895(4) 0.044(2) Uani 1 1 d . . .
C58 C 0.4461(4) 0.2940(4) -0.2169(4) 0.050(2) Uani 1 1 d . . .
H58A H 0.4222 0.2669 -0.1920 0.060 Uiso 1 1 calc R . .
C59 C 0.4375(4) 0.2946(4) -0.2826(5) 0.060(3) Uani 1 1 d . . .
H59A H 0.4079 0.2685 -0.3016 0.071 Uiso 1 1 calc R . .
C60 C 0.4729(4) 0.3336(4) -0.3163(4) 0.052(3) Uani 1 1 d . . .
C61 C 0.5155(4) 0.3731(4) -0.2895(5) 0.051(2) Uani 1 1 d . . .
H61A H 0.5396 0.4003 -0.3140 0.061 Uiso 1 1 calc R . .
C62 C 0.5218(4) 0.3717(4) -0.2288(4) 0.048(2) Uani 1 1 d . . .
H62A H 0.5507 0.3995 -0.2108 0.058 Uiso 1 1 calc R . .
C63 C 0.4494(4) 0.3709(4) -0.0898(4) 0.042(2) Uani 1 1 d . . .
C64 C 0.4023(4) 0.3316(4) -0.0769(4) 0.050(2) Uani 1 1 d . . .
H64A H 0.3983 0.3007 -0.0614 0.060 Uiso 1 1 calc R . .
C65 C 0.3607(4) 0.3369(5) -0.0862(5) 0.070(3) Uani 1 1 d . . .
H65A H 0.3277 0.3100 -0.0772 0.083 Uiso 1 1 calc R . .
C66 C 0.3680(5) 0.3821(5) -0.1089(5) 0.065(3) Uani 1 1 d . . .
C67 C 0.4120(5) 0.4199(5) -0.1228(6) 0.074(3) Uani 1 1 d . . .
H67A H 0.4152 0.4502 -0.1390 0.089 Uiso 1 1 calc R . .
C68 C 0.4563(5) 0.4151(4) -0.1132(5) 0.071(3) Uani 1 1 d . . .
H68A H 0.4890 0.4420 -0.1229 0.085 Uiso 1 1 calc R . .
C69 C 0.4172(3) 0.1528(3) 0.2803(4) 0.042(2) Uani 1 1 d . . .
C70 C 0.4211(3) 0.1703(4) 0.3372(5) 0.051(3) Uani 1 1 d . . .
H70A H 0.4537 0.1924 0.3535 0.061 Uiso 1 1 calc R . .
C71 C 0.3784(5) 0.1574(4) 0.3750(5) 0.064(3) Uani 1 1 d . . .
H71A H 0.3822 0.1697 0.4162 0.076 Uiso 1 1 calc R . .
C72 C 0.3324(5) 0.1273(4) 0.3509(8) 0.078(4) Uani 1 1 d . . .
C73 C 0.3272(4) 0.1083(5) 0.2898(7) 0.084(4) Uani 1 1 d . . .
H73A H 0.2948 0.0864 0.2727 0.100 Uiso 1 1 calc R . .
C74 C 0.3692(4) 0.1221(4) 0.2568(6) 0.071(3) Uani 1 1 d . . .
H74A H 0.3659 0.1103 0.2154 0.085 Uiso 1 1 calc R . .
C75 C 0.4750(3) 0.1003(3) 0.3012(4) 0.038(2) Uani 1 1 d . . .
C76 C 0.4528(3) 0.0590(4) 0.2624(5) 0.049(2) Uani 1 1 d . . .
H76A H 0.4540 0.0633 0.2187 0.058 Uiso 1 1 calc R . .
C77 C 0.4284(4) 0.0109(4) 0.2885(5) 0.059(3) Uani 1 1 d . . .
H77A H 0.4128 -0.0183 0.2629 0.071 Uiso 1 1 calc R . .
C78 C 0.4275(4) 0.0064(4) 0.3522(5) 0.061(3) Uani 1 1 d . . .
C79 C 0.4512(4) 0.0484(3) 0.3911(5) 0.051(2) Uani 1 1 d . . .
H79A H 0.4520 0.0447 0.4348 0.062 Uiso 1 1 calc R . .
C80 C 0.4738(3) 0.0962(3) 0.3636(4) 0.046(2) Uani 1 1 d . . .
H80A H 0.4883 0.1257 0.3888 0.055 Uiso 1 1 calc R . .
Cl1 Cl 0.36351(11) 0.35269(12) 0.07968(13) 0.0722(8) Uani 1 1 d . . .
Cl2 Cl 0.43104(13) 0.34790(15) 0.16836(14) 0.0878(10) Uani 1 1 d . . .
Cl3 Cl 0.46665(13) 0.43331(12) 0.0863(2) 0.1121(14) Uani 1 1 d . . .
Cl4 Cl 0.40437(13) 0.09788(13) 0.51034(14) 0.0929(11) Uani 1 1 d . . .
Cl5 Cl 0.33195(12) 0.03958(12) 0.60536(13) 0.0804(9) Uani 1 1 d . . .
Cl6 Cl 0.34988(15) 0.13897(17) 0.5715(2) 0.1153(14) Uani 1 1 d . . .
Cl7 Cl 0.6667 0.3333 0.23999(19) 0.0667(12) Uani 0.33 1 d P A .
Cl8 Cl 0.60795(16) 0.31870(16) 0.35128(19) 0.0717(11) Uani 0.67 1 d P A 1
O1 O 0.5510(6) 0.2814(6) 0.3345(8) 0.043(4) Uiso 0.33 1 d P B 2
Cl9 Cl 0.60959(13) 0.28128(14) 0.08320(15) 0.0919(10) Uani 1 1 d . . .
Cl10 Cl 0.66376(14) 0.27731(14) 0.5752(2) 0.1102(13) Uani 1 1 d . . .
C81 C 0.4251(4) 0.3686(4) 0.0945(6) 0.073(3) Uani 1 1 d . . .
H81 H 0.4348 0.3509 0.0633 0.088 Uiso 1 1 calc R . .
C82 C 0.3750(4) 0.0990(4) 0.5808(5) 0.068(3) Uani 1 1 d . . .
H82 H 0.4020 0.1144 0.6132 0.082 Uiso 1 1 calc R . .
C83 C 0.6667 0.3333 0.3245(8) 0.055(4) Uani 1 3 d S . .
C84 C 0.6667 0.3333 0.0581(8) 0.070(5) Uani 1 3 d S . .
H84 H 0.6667 0.3333 0.0117 0.084 Uiso 1 3 calc SR . .
C85 C 0.6667 0.3333 0.5958(9) 0.071(5) Uani 1 3 d S . .
H85 H 0.6667 0.3333 0.6422 0.085 Uiso 1 3 calc SR . .
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'
Cl Cl 0.1484 0.1585 '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'
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
C3 N1 C4 117.0(7) . .
C6 N2 C5 118.5(7) . .
C13 N3 C14 118.4(7) . .
C16 N4 C15 118.2(7) . .
C43 N5 C44 120.8(8) . .
C46 N6 C45 118.2(8) . .
C53 N7 C54 119.8(7) . .
C56 N8 C55 120.1(7) . .
C2 C1 C2 121.1(8) 2_655 .
C2 C1 H1 119.5 2_655 .
C2 C1 H1 119.5 . .
C1 C2 C1 118.9(8) 3_665 .
C1 C2 C3 119.5(7) 3_665 .
C1 C2 C3 121.3(7) . .
N1 C3 C2 122.2(7) . .
N1 C3 H3A 118.9 . .
C2 C3 H3A 118.9 . .
N1 C4 C17 108.4(7) . .
N1 C4 C5 108.1(6) . .
C17 C4 C5 113.0(7) . .
N1 C4 H4A 109.1 . .
C17 C4 H4A 109.1 . .
C5 C4 H4A 109.1 . .
N2 C5 C23 110.1(6) . .
N2 C5 C4 108.3(6) . .
C23 C5 C4 111.0(6) . .
N2 C5 H5A 109.1 . .
C23 C5 H5A 109.1 . .
C4 C5 H5A 109.1 . .
N2 C6 C7 122.4(8) . .
N2 C6 H6A 118.8 . .
C7 C6 H6A 118.8 . .
C8 C7 C12 119.1(7) . .
C8 C7 C6 120.4(7) . .
C12 C7 C6 120.5(7) . .
C7 C8 C9 122.3(8) . .
C7 C8 H8A 118.8 . .
C9 C8 H8A 118.8 . .
C8 C9 C10 117.1(8) . .
C8 C9 C16 120.2(7) . 3_665
C10 C9 C16 122.7(8) . 3_665
C11 C10 C9 122.1(8) . .
C11 C10 H10A 119.0 . .
C9 C10 H10A 119.0 . .
C10 C11 C12 118.9(7) . .
C10 C11 C13 120.3(7) . .
C12 C11 C13 120.8(7) . .
C11 C12 C7 120.4(8) . .
C11 C12 H12A 119.8 . .
C7 C12 H12A 119.8 . .
N3 C13 C11 123.6(7) . .
N3 C13 H13A 118.2 . .
C11 C13 H13A 118.2 . .
N3 C14 C15 109.7(6) . .
N3 C14 C29 108.6(7) . .
C15 C14 C29 111.3(7) . .
N3 C14 H14A 109.1 . .
C15 C14 H14A 109.1 . .
C29 C14 H14A 109.1 . .
N4 C15 C14 109.8(7) . .
N4 C15 C35 109.4(7) . .
C14 C15 C35 112.9(7) . .
N4 C15 H15A 108.2 . .
C14 C15 H15A 108.2 . .
C35 C15 H15A 108.2 . .
N4 C16 C9 123.9(7) . 2_655
N4 C16 H16 118.0 . .
C9 C16 H16 118.0 2_655 .
C22 C17 C18 116.6(9) . .
C22 C17 C4 121.5(9) . .
C18 C17 C4 121.6(8) . .
C19 C18 C17 124.7(11) . .
C19 C18 H18A 117.6 . .
C17 C18 H18A 117.6 . .
C20 C19 C18 117.7(12) . .
C20 C19 H19A 121.2 . .
C18 C19 H19A 121.2 . .
C19 C20 F1 121.4(13) . .
C19 C20 C21 124.4(10) . .
F1 C20 C21 114.1(12) . .
C20 C21 C22 115.9(9) . .
C20 C21 H21A 122.0 . .
C22 C21 H21A 122.0 . .
C17 C22 C21 120.2(10) . .
C17 C22 H22A 119.9 . .
C21 C22 H22A 119.9 . .
C28 C23 C24 118.2(8) . .
C28 C23 C5 122.5(7) . .
C24 C23 C5 119.3(8) . .
C23 C24 C25 119.5(9) . .
C23 C24 H24A 120.3 . .
C25 C24 H24A 120.3 . .
C26 C25 C24 118.3(9) . .
C26 C25 H25A 120.9 . .
C24 C25 H25A 120.9 . .
C25 C26 F2 117.8(11) . .
C25 C26 C27 124.4(9) . .
F2 C26 C27 117.8(11) . .
C28 C27 C26 115.6(9) . .
C28 C27 H27A 122.2 . .
C26 C27 H27A 122.2 . .
C27 C28 C23 124.0(9) . .
C27 C28 H28A 118.0 . .
C23 C28 H28A 118.0 . .
C34 C29 C30 119.6(8) . .
C34 C29 C14 120.2(8) . .
C30 C29 C14 120.2(7) . .
C31 C30 C29 120.2(9) . .
C31 C30 H30A 119.9 . .
C29 C30 H30A 119.9 . .
C32 C31 C30 119.9(9) . .
C32 C31 H31A 120.0 . .
C30 C31 H31A 120.0 . .
F3 C32 C31 120.3(11) . .
F3 C32 C33 116.9(11) . .
C31 C32 C33 122.8(9) . .
C32 C33 C34 117.4(9) . .
C32 C33 H33A 121.3 . .
C34 C33 H33A 121.3 . .
C29 C34 C33 120.0(9) . .
C29 C34 H34A 120.0 . .
C33 C34 H34A 120.0 . .
C40 C35 C36 118.4(8) . .
C40 C35 C15 121.9(8) . .
C36 C35 C15 119.6(8) . .
C35 C36 C37 120.9(9) . .
C35 C36 H36A 119.6 . .
C37 C36 H36A 119.6 . .
C38 C37 C36 118.7(9) . .
C38 C37 H37A 120.7 . .
C36 C37 H37A 120.7 . .
C37 C38 C39 122.6(9) . .
C37 C38 F4 119.4(10) . .
C39 C38 F4 117.9(11) . .
C38 C39 C40 117.4(10) . .
C38 C39 H39A 121.3 . .
C40 C39 H39A 121.3 . .
C35 C40 C39 121.8(10) . .
C35 C40 H40A 119.1 . .
C39 C40 H40A 119.1 . .
C42 C41 C42 122.0(9) 3_665 .
C42 C41 H41 119.0 3_665 .
C42 C41 H41 119.0 . .
C41 C42 C41 118.0(9) 2_655 .
C41 C42 C43 120.7(8) 2_655 .
C41 C42 C43 121.3(8) . .
N5 C43 C42 121.9(8) . .
N5 C43 H43A 119.0 . .
C42 C43 H43A 119.0 . .
N5 C44 C57 108.8(7) . .
N5 C44 C45 103.7(7) . .
C57 C44 C45 116.1(7) . .
N5 C44 H44A 109.3 . .
C57 C44 H44A 109.3 . .
C45 C44 H44A 109.3 . .
N6 C45 C63 111.0(7) . .
N6 C45 C44 105.0(7) . .
C63 C45 C44 112.0(7) . .
N6 C45 H45A 109.6 . .
C63 C45 H45A 109.6 . .
C44 C45 H45A 109.6 . .
N6 C46 C47 122.8(9) . .
N6 C46 H46A 118.6 . .
C47 C46 H46A 118.6 . .
C48 C47 C52 120.1(8) . .
C48 C47 C46 118.7(9) . .
C52 C47 C46 121.3(9) . .
C47 C48 C49 119.0(8) . .
C47 C48 H48A 120.5 . .
C49 C48 H48A 120.5 . .
C50 C49 C48 118.9(8) . .
C50 C49 C56 122.3(8) . 3_665
C48 C49 C56 118.7(8) . 3_665
C49 C50 C51 123.2(8) . .
C49 C50 H50A 118.4 . .
C51 C50 H50A 118.4 . .
C50 C51 C52 118.7(8) . .
C50 C51 C53 121.6(8) . .
C52 C51 C53 119.7(8) . .
C51 C52 C47 120.0(8) . .
C51 C52 H52A 120.0 . .
C47 C52 H52A 120.0 . .
N7 C53 C51 123.2(8) . .
N7 C53 H53A 118.4 . .
C51 C53 H53A 118.4 . .
N7 C54 C69 110.0(7) . .
N7 C54 C55 107.4(6) . .
C69 C54 C55 113.2(7) . .
N7 C54 H54A 108.7 . .
C69 C54 H54A 108.7 . .
C55 C54 H54A 108.7 . .
N8 C55 C54 108.3(7) . .
N8 C55 C75 109.6(7) . .
C54 C55 C75 113.5(7) . .
N8 C55 H55A 108.4 . .
C54 C55 H55A 108.4 . .
C75 C55 H55A 108.4 . .
N8 C56 C49 123.7(8) . 2_655
N8 C56 H56 118.1 . .
C49 C56 H56 118.1 2_655 .
C62 C57 C58 116.0(8) . .
C62 C57 C44 124.0(8) . .
C58 C57 C44 119.9(8) . .
C57 C58 C59 120.1(9) . .
C57 C58 H58A 119.9 . .
C59 C58 H58A 119.9 . .
C60 C59 C58 117.9(9) . .
C60 C59 H59A 121.0 . .
C58 C59 H59A 121.0 . .
F5 C60 C59 116.6(9) . .
F5 C60 C61 121.1(9) . .
C59 C60 C61 122.3(9) . .
C62 C61 C60 118.2(10) . .
C62 C61 H61A 120.9 . .
C60 C61 H61A 120.9 . .
C61 C62 C57 125.4(10) . .
C61 C62 H62A 117.3 . .
C57 C62 H62A 117.3 . .
C68 C63 C64 121.4(9) . .
C68 C63 C45 116.4(9) . .
C64 C63 C45 122.2(8) . .
C63 C64 C65 119.9(10) . .
C63 C64 H64A 120.1 . .
C65 C64 H64A 120.1 . .
C66 C65 C64 118.4(11) . .
C66 C65 H65A 120.8 . .
C64 C65 H65A 120.8 . .
C67 C66 C65 123.5(10) . .
C67 C66 F6 120.3(11) . .
C65 C66 F6 116.1(11) . .
C66 C67 C68 118.9(11) . .
C66 C67 H67A 120.5 . .
C68 C67 H67A 120.5 . .
C63 C68 C67 117.9(11) . .
C63 C68 H68A 121.0 . .
C67 C68 H68A 121.0 . .
C70 C69 C74 117.8(9) . .
C70 C69 C54 122.2(8) . .
C74 C69 C54 120.0(9) . .
C69 C70 C71 122.5(10) . .
C69 C70 H70A 118.8 . .
C71 C70 H70A 118.8 . .
C72 C71 C70 118.2(11) . .
C72 C71 H71A 120.9 . .
C70 C71 H71A 120.9 . .
C71 C72 F7 120.8(14) . .
C71 C72 C73 120.3(10) . .
F7 C72 C73 118.9(12) . .
C74 C73 C72 118.2(12) . .
C74 C73 H73A 120.9 . .
C72 C73 H73A 120.9 . .
C73 C74 C69 123.0(12) . .
C73 C74 H74A 118.5 . .
C69 C74 H74A 118.5 . .
C80 C75 C76 122.7(8) . .
C80 C75 C55 119.4(8) . .
C76 C75 C55 117.9(8) . .
C75 C76 C77 118.8(9) . .
C75 C76 H76A 120.6 . .
C77 C76 H76A 120.6 . .
C78 C77 C76 118.7(9) . .
C78 C77 H77A 120.6 . .
C76 C77 H77A 120.6 . .
F8 C78 C77 121.1(10) . .
F8 C78 C79 116.6(9) . .
C77 C78 C79 122.1(9) . .
C78 C79 C80 117.7(9) . .
C78 C79 H79A 121.1 . .
C80 C79 H79A 121.1 . .
C75 C80 C79 119.8(9) . .
C75 C80 H80A 120.1 . .
C79 C80 H80A 120.1 . .
Cl1 C81 Cl3 112.1(7) . .
Cl1 C81 Cl2 111.3(6) . .
Cl3 C81 Cl2 110.6(7) . .
Cl1 C81 H81 107.5 . .
Cl3 C81 H81 107.5 . .
Cl2 C81 H81 107.5 . .
Cl5 C82 Cl6 113.8(6) . .
Cl5 C82 Cl4 111.8(6) . .
Cl6 C82 Cl4 108.6(6) . .
Cl5 C82 H82 107.4 . .
Cl6 C82 H82 107.4 . .
Cl4 C82 H82 107.4 . .
Cl8 C83 Cl8 109.3(5) 2_655 3_665
Cl8 C83 Cl8 109.3(5) 2_655 .
Cl8 C83 Cl8 109.3(5) 3_665 .
Cl8 C83 Cl7 109.6(5) 2_655 .
Cl8 C83 Cl7 109.6(5) 3_665 .
Cl8 C83 Cl7 109.6(5) . .
Cl9 C84 Cl9 111.0(5) . 2_655
Cl9 C84 Cl9 111.0(5) . 3_665
Cl9 C84 Cl9 111.0(5) 2_655 3_665
Cl9 C84 H84 107.9 . .
Cl9 C84 H84 107.9 2_655 .
Cl9 C84 H84 107.9 3_665 .
Cl10 C85 Cl10 113.6(5) . 2_655
Cl10 C85 Cl10 113.6(5) . 3_665
Cl10 C85 Cl10 113.6(5) 2_655 3_665
Cl10 C85 H85 104.9 . .
Cl10 C85 H85 104.9 2_655 .
Cl10 C85 H85 104.9 3_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.279(10) .
N1 C4 1.477(11) .
N2 C6 1.256(10) .
N2 C5 1.462(10) .
N3 C13 1.280(10) .
N3 C14 1.447(10) .
N4 C16 1.278(10) .
N4 C15 1.434(11) .
N5 C43 1.270(11) .
N5 C44 1.461(11) .
N6 C46 1.236(11) .
N6 C45 1.480(11) .
N7 C53 1.244(11) .
N7 C54 1.483(11) .
N8 C56 1.274(11) .
N8 C55 1.454(11) .
F1 C20 1.400(12) .
F2 C26 1.373(11) .
F3 C32 1.358(11) .
F4 C38 1.388(11) .
F5 C60 1.346(10) .
F6 C66 1.379(12) .
F7 C72 1.358(13) .
F8 C78 1.355(11) .
C1 C2 1.378(11) 2_655
C1 C2 1.409(11) .
C1 H1 0.9500 .
C2 C1 1.378(11) 3_665
C2 C3 1.479(11) .
C3 H3A 0.9500 .
C4 C17 1.484(12) .
C4 C5 1.553(11) .
C4 H4A 1.0000 .
C5 C23 1.490(11) .
C5 H5A 1.0000 .
C6 C7 1.461(11) .
C6 H6A 0.9500 .
C7 C8 1.380(11) .
C7 C12 1.411(11) .
C8 C9 1.401(12) .
C8 H8A 0.9500 .
C9 C10 1.425(11) .
C9 C16 1.474(12) 3_665
C10 C11 1.379(11) .
C10 H10A 0.9500 .
C11 C12 1.411(12) .
C11 C13 1.444(11) .
C12 H12A 0.9500 .
C13 H13A 0.9500 .
C14 C15 1.520(12) .
C14 C29 1.523(12) .
C14 H14A 1.0000 .
C15 C35 1.535(12) .
C15 H15A 1.0000 .
C16 C9 1.474(12) 2_655
C16 H16 0.9500 .
C17 C22 1.349(13) .
C17 C18 1.407(15) .
C18 C19 1.347(15) .
C18 H18A 0.9500 .
C19 C20 1.281(17) .
C19 H19A 0.9500 .
C20 C21 1.413(17) .
C21 C22 1.449(15) .
C21 H21A 0.9500 .
C22 H22A 0.9500 .
C23 C28 1.375(12) .
C23 C24 1.394(12) .
C24 C25 1.435(14) .
C24 H24A 0.9500 .
C25 C26 1.316(15) .
C25 H25A 0.9500 .
C26 C27 1.416(16) .
C27 C28 1.360(13) .
C27 H27A 0.9500 .
C28 H28A 0.9500 .
C29 C34 1.375(12) .
C29 C30 1.397(12) .
C30 C31 1.363(13) .
C30 H30A 0.9500 .
C31 C32 1.363(15) .
C31 H31A 0.9500 .
C32 C33 1.363(16) .
C33 C34 1.432(14) .
C33 H33A 0.9500 .
C34 H34A 0.9500 .
C35 C40 1.342(13) .
C35 C36 1.373(12) .
C36 C37 1.402(13) .
C36 H36A 0.9500 .
C37 C38 1.327(15) .
C37 H37A 0.9500 .
C38 C39 1.364(16) .
C39 C40 1.407(15) .
C39 H39A 0.9500 .
C40 H40A 0.9500 .
C41 C42 1.385(12) 3_665
C41 C42 1.418(12) .
C41 H41 0.9500 .
C42 C41 1.385(12) 2_655
C42 C43 1.426(12) .
C43 H43A 0.9500 .
C44 C57 1.493(12) .
C44 C45 1.565(12) .
C44 H44A 1.0000 .
C45 C63 1.506(13) .
C45 H45A 1.0000 .
C46 C47 1.467(13) .
C46 H46A 0.9500 .
C47 C48 1.393(13) .
C47 C52 1.402(13) .
C48 C49 1.430(12) .
C48 H48A 0.9500 .
C49 C50 1.344(12) .
C49 C56 1.457(12) 3_665
C50 C51 1.383(12) .
C50 H50A 0.9500 .
C51 C52 1.390(12) .
C51 C53 1.496(12) .
C52 H52A 0.9500 .
C53 H53A 0.9500 .
C54 C69 1.499(13) .
C54 C55 1.549(12) .
C54 H54A 1.0000 .
C55 C75 1.554(12) .
C55 H55A 1.0000 .
C56 C49 1.457(12) 2_655
C56 H56 0.9500 .
C57 C62 1.380(13) .
C57 C58 1.404(13) .
C58 C59 1.443(14) .
C58 H58A 0.9500 .
C59 C60 1.352(14) .
C59 H59A 0.9500 .
C60 C61 1.385(14) .
C61 C62 1.327(12) .
C61 H61A 0.9500 .
C62 H62A 0.9500 .
C63 C68 1.358(14) .
C63 C64 1.365(13) .
C64 C65 1.376(14) .
C64 H64A 0.9500 .
C65 C66 1.375(16) .
C65 H65A 0.9500 .
C66 C67 1.297(16) .
C67 C68 1.446(15) .
C67 H67A 0.9500 .
C68 H68A 0.9500 .
C69 C70 1.319(13) .
C69 C74 1.383(14) .
C70 C71 1.417(14) .
C70 H70A 0.9500 .
C71 C72 1.343(17) .
C71 H71A 0.9500 .
C72 C73 1.416(19) .
C73 C74 1.338(16) .
C73 H73A 0.9500 .
C74 H74A 0.9500 .
C75 C80 1.351(12) .
C75 C76 1.377(13) .
C76 C77 1.394(14) .
C76 H76A 0.9500 .
C77 C78 1.378(15) .
C77 H77A 0.9500 .
C78 C79 1.396(15) .
C79 C80 1.398(13) .
C79 H79A 0.9500 .
C80 H80A 0.9500 .
Cl1 C81 1.722(12) .
Cl2 C81 1.756(12) .
Cl3 C81 1.745(12) .
Cl4 C82 1.775(12) .
Cl5 C82 1.711(12) .
Cl6 C82 1.749(12) .
Cl7 C83 1.821(17) .
Cl8 C83 1.719(7) .
Cl9 C84 1.759(6) .
Cl10 C85 1.729(6) .
C81 H81 1.0000 .
C82 H82 1.0000 .
C83 Cl8 1.719(7) 2_655
C83 Cl8 1.719(7) 3_665
C84 Cl9 1.759(6) 2_655
C84 Cl9 1.759(6) 3_665
C84 H84 1.0000 .
C85 Cl10 1.729(6) 2_655
C85 Cl10 1.729(6) 3_665
C85 H85 1.0000 .
