#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:57:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179221 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/45/4314573.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_4314573
loop_
_publ_author_name
'Tanya K. Ronson'
'Christopher Carruthers'
'Julie Fisher'
'Thierry Brotin'
'Lindsay P. Harding'
'Pierre J. Rizkallah'
'Michaele J. Hardie'
_publ_section_title
;
 Tripodal 4-Pyridyl-Derived Host Ligands and Their Metallo-Supramolecular
 Chemistry: Stella Octangula and Bowl-Shaped Assemblies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              675
_journal_page_last               685
_journal_paper_doi               10.1021/ic901972h
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C66.67 H55.67 B0 N6.33 O9.33'
_chemical_formula_weight         1094.84
_chemical_name_systematic
; 
 tris{4-(4-pyridyl)phenylester)cyclotriguaiacylene acetonitrile water clathrate
;
_space_group_IT_number           159
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 3 -2c'
_symmetry_space_group_name_H-M   'P 3 1 c'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   19.3666(4)
_cell_length_b                   19.3666(4)
_cell_length_c                   28.7185(16)
_cell_measurement_reflns_used    9576
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      2.43
_cell_volume                     9328.2(6)
_computing_cell_refinement       'Bruker APEX 2'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker APEX 2'
_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      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            165090
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     718
_refine_ls_number_reflns         10939
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0763
_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)+(0.1731P)²+2.8592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2179
_refine_ls_wR_factor_ref         0.2447
_reflns_number_gt                9211
_reflns_number_total             10939
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901972h_si_001_4.cif
_cod_data_source_block           ligand5clathrate
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4314573
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, 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
O1 O 0.83216(19) 1.69924(19) 0.49325(12) 0.0576(8) Uani 1 1 d . . .
O2 O 0.9668(2) 1.8327(2) 0.46424(14) 0.0720(9) Uani 1 1 d . . .
O3 O 0.7646(3) 1.7639(2) 0.48135(19) 0.0908(14) Uani 1 1 d . . .
O4 O 0.91197(19) 1.51907(19) 0.73185(10) 0.0537(7) Uani 1 1 d . . .
O5 O 0.78172(17) 1.49059(16) 0.68353(11) 0.0516(7) Uani 1 1 d . . .
O6 O 0.9804(2) 1.5183(2) 0.66873(13) 0.0703(9) Uani 1 1 d . . .
O7 O 1.28498(19) 1.89602(18) 0.57854(11) 0.0571(8) Uani 1 1 d . . .
O8 O 1.28336(19) 1.8173(2) 0.65617(12) 0.0619(8) Uani 1 1 d . . .
O9 O 1.35672(18) 2.02586(18) 0.60003(11) 0.0520(7) Uani 1 1 d . . .
N1 N 0.4871(4) 1.3296(3) 0.28032(16) 0.0803(14) Uani 1 1 d . . .
N2 N 0.9179(4) 1.0613(4) 0.8190(3) 0.107(2) Uani 1 1 d . . .
N3 N 1.6814(4) 2.0119(4) 0.36239(19) 0.0863(15) Uani 1 1 d . . .
C1 C 1.0517(3) 1.9149(2) 0.62836(19) 0.0582(11) Uani 1 1 d . . .
H1A H 1.0815 1.9696 0.6154 0.070 Uiso 1 1 calc R . .
H1B H 1.0259 1.9173 0.6576 0.070 Uiso 1 1 calc R . .
C2 C 0.9875(3) 1.8607(2) 0.59367(18) 0.0532(10) Uani 1 1 d . . .
C3 C 1.0056(3) 1.8739(3) 0.54548(19) 0.0582(11) Uani 1 1 d . . .
H3 H 1.0546 1.9188 0.5361 0.070 Uiso 1 1 calc R . .
C4 C 0.9546(3) 1.8242(3) 0.51205(19) 0.0585(11) Uani 1 1 d . . .
C5 C 0.8824(3) 1.7573(3) 0.52631(16) 0.0509(10) Uani 1 1 d . . .
C6 C 0.8618(3) 1.7449(2) 0.57260(16) 0.0502(10) Uani 1 1 d . . .
H6 H 0.8117 1.7008 0.5813 0.060 Uiso 1 1 calc R . .
C7 C 0.9135(3) 1.7965(2) 0.60775(17) 0.0496(10) Uani 1 1 d . . .
C8 C 0.8344(2) 1.6348(2) 0.67283(14) 0.0419(8) Uani 1 1 d . . .
H8 H 0.7879 1.6262 0.6568 0.050 Uiso 1 1 calc R . .
C9 C 0.8857(2) 1.7787(2) 0.65843(16) 0.0484(9) Uani 1 1 d . . .
H9A H 0.9158 1.8280 0.6770 0.058 Uiso 1 1 calc R . .
H9B H 0.8286 1.7626 0.6600 0.058 Uiso 1 1 calc R . .
C10 C 0.8972(2) 1.7134(2) 0.67985(14) 0.0447(9) Uani 1 1 d . . .
C11 C 0.8392(2) 1.5698(2) 0.68885(14) 0.0430(8) Uani 1 1 d . . .
C12 C 0.9090(2) 1.5852(3) 0.71336(14) 0.0473(9) Uani 1 1 d . . .
C13 C 0.9700(3) 1.6613(3) 0.72103(14) 0.0488(9) Uani 1 1 d . . .
H13 H 1.0157 1.6697 0.7380 0.059 Uiso 1 1 calc R . .
C14 C 0.9659(2) 1.7278(2) 0.70391(14) 0.0448(9) Uani 1 1 d . . .
C15 C 1.0380(3) 1.8107(3) 0.71385(16) 0.0551(11) Uani 1 1 d . . .
H15A H 1.0195 1.8500 0.7155 0.066 Uiso 1 1 calc R . .
H15B H 1.0603 1.8097 0.7447 0.066 Uiso 1 1 calc R . .
C16 C 1.1038(2) 1.8384(2) 0.67755(16) 0.0519(10) Uani 1 1 d . . .
C17 C 1.1615(2) 1.8148(2) 0.68420(15) 0.0496(9) Uani 1 1 d . . .
H17 H 1.1581 1.7842 0.7109 0.059 Uiso 1 1 calc R . .
C18 C 1.2232(2) 1.8356(2) 0.65232(14) 0.0491(9) Uani 1 1 d . . .
C19 C 1.2263(3) 1.8805(2) 0.61315(16) 0.0521(10) Uani 1 1 d . . .
C20 C 1.1718(3) 1.9053(2) 0.60664(18) 0.0556(11) Uani 1 1 d . . .
H20 H 1.1758 1.9361 0.5800 0.067 Uiso 1 1 calc R . .
C21 C 1.1099(3) 1.8855(2) 0.63906(17) 0.0533(10) Uani 1 1 d . . .
C22 C 0.7743(3) 1.7088(3) 0.47258(19) 0.0590(11) Uani 1 1 d . . .
C23 C 0.7275(3) 1.6420(3) 0.44055(17) 0.0524(10) Uani 1 1 d . . .
C24 C 0.6788(3) 1.6494(3) 0.4064(2) 0.0739(16) Uani 1 1 d . . .
H24 H 0.6767 1.6973 0.4048 0.089 Uiso 1 1 calc R . .
C25 C 0.6348(3) 1.5890(3) 0.3757(2) 0.0702(14) Uani 1 1 d . . .
H25 H 0.6041 1.5965 0.3525 0.084 Uiso 1 1 calc R . .
C26 C 0.6343(3) 1.5166(3) 0.37784(15) 0.0489(9) Uani 1 1 d . . .
C27 C 0.6800(3) 1.5073(3) 0.41260(14) 0.0493(9) Uani 1 1 d . . .
H27 H 0.6791 1.4580 0.4153 0.059 Uiso 1 1 calc R . .
C28 C 0.7261(3) 1.5685(3) 0.44275(16) 0.0526(10) Uani 1 1 d . . .
H28 H 0.7575 1.5612 0.4655 0.063 Uiso 1 1 calc R . .
C29 C 0.5852(3) 1.4504(3) 0.34430(15) 0.0535(10) Uani 1 1 d . . .
C30 C 0.5766(3) 1.4673(4) 0.29795(18) 0.0646(12) Uani 1 1 d . . .
H30 H 0.6038 1.5208 0.2869 0.078 Uiso 1 1 calc R . .
C31 C 0.5282(4) 1.4058(4) 0.26853(19) 0.0733(15) Uani 1 1 d . . .
H31 H 0.5240 1.4191 0.2372 0.088 Uiso 1 1 calc R . .
C32 C 0.4950(5) 1.3123(4) 0.3253(2) 0.0821(17) Uani 1 1 d . . .
H32 H 0.4663 1.2583 0.3353 0.098 Uiso 1 1 calc R . .
C33 C 0.5433(4) 1.3705(3) 0.35699(17) 0.0676(13) Uani 1 1 d . . .
H33 H 0.5479 1.3556 0.3878 0.081 Uiso 1 1 calc R . .
C34 C 0.9487(3) 1.4885(3) 0.70529(15) 0.0508(9) Uani 1 1 d . . .
C35 C 0.9447(2) 1.4167(2) 0.72696(14) 0.0448(8) Uani 1 1 d . . .
C36 C 0.8958(2) 1.3792(3) 0.76575(14) 0.0500(10) Uani 1 1 d . . .
H36 H 0.8660 1.4005 0.7797 0.060 Uiso 1 1 calc R . .
C37 C 0.8917(2) 1.3097(3) 0.78339(14) 0.0478(9) Uani 1 1 d . . .
H37 H 0.8582 1.2836 0.8093 0.057 Uiso 1 1 calc R . .
C38 C 0.9358(2) 1.2779(2) 0.76370(14) 0.0474(9) Uani 1 1 d . . .
C39 C 0.9855(3) 1.3184(3) 0.72614(16) 0.0543(10) Uani 1 1 d . . .
H39 H 1.0176 1.2990 0.7132 0.065 Uiso 1 1 calc R . .
C40 C 0.9895(3) 1.3865(3) 0.70708(15) 0.0515(10) Uani 1 1 d . . .
H40 H 1.0224 1.4118 0.6808 0.062 Uiso 1 1 calc R . .
C41 C 0.9301(3) 1.2047(3) 0.78269(17) 0.0546(10) Uani 1 1 d . . .
C42 C 0.8598(3) 1.1430(3) 0.80255(15) 0.0505(9) Uani 1 1 d . . .
H42 H 0.8142 1.1490 0.8051 0.061 Uiso 1 1 calc R . .
C43 C 0.8563(3) 1.0732(3) 0.81859(19) 0.0625(12) Uani 1 1 d . . .
H43 H 0.8066 1.0318 0.8299 0.075 Uiso 1 1 calc R . .
C44 C 0.9865(6) 1.1215(6) 0.8015(5) 0.171(6) Uani 1 1 d . . .
H44 H 1.0328 1.1165 0.8026 0.205 Uiso 1 1 calc R . .
C45 C 0.9933(5) 1.1904(4) 0.7819(4) 0.129(4) Uani 1 1 d . . .
H45 H 1.0421 1.2282 0.7677 0.154 Uiso 1 1 calc R . .
C46 C 1.3482(2) 1.9720(3) 0.57499(14) 0.0455(9) Uani 1 1 d . . .
C47 C 1.4037(2) 1.9774(3) 0.53698(14) 0.0466(9) Uani 1 1 d . . .
C48 C 1.4743(3) 2.0498(3) 0.53092(15) 0.0500(9) Uani 1 1 d . . .
H48 H 1.4855 2.0942 0.5501 0.060 Uiso 1 1 calc R . .
C49 C 1.5281(3) 2.0568(3) 0.49655(15) 0.0531(10) Uani 1 1 d . . .
H49 H 1.5764 2.1060 0.4927 0.064 Uiso 1 1 calc R . .
C50 C 1.5118(3) 1.9918(3) 0.46748(14) 0.0515(10) Uani 1 1 d . . .
C51 C 1.4409(3) 1.9203(3) 0.47438(17) 0.0641(12) Uani 1 1 d . . .
H51 H 1.4292 1.8758 0.4552 0.077 Uiso 1 1 calc R . .
C52 C 1.3873(3) 1.9126(3) 0.50840(17) 0.0596(11) Uani 1 1 d . . .
H52 H 1.3393 1.8633 0.5124 0.072 Uiso 1 1 calc R . .
C53 C 1.5705(3) 1.9994(3) 0.43135(15) 0.0578(11) Uani 1 1 d . . .
C54 C 1.6535(4) 2.0453(4) 0.43820(19) 0.0719(14) Uani 1 1 d . . .
H54 H 1.6748 2.0745 0.4662 0.086 Uiso 1 1 calc R . .
C55 C 1.7039(4) 2.0469(5) 0.4026(2) 0.0869(19) Uani 1 1 d . . .
H55 H 1.7596 2.0764 0.4085 0.104 Uiso 1 1 calc R . .
C56 C 1.6027(4) 1.9682(4) 0.35563(19) 0.0779(16) Uani 1 1 d . . .
H56 H 1.5849 1.9423 0.3264 0.093 Uiso 1 1 calc R . .
C57 C 1.5442(4) 1.9576(3) 0.38837(17) 0.0658(12) Uani 1 1 d . . .
H57 H 1.4890 1.9239 0.3820 0.079 Uiso 1 1 calc R . .
C58 C 1.0374(5) 1.9013(5) 0.4484(3) 0.097(2) Uani 1 1 d . . .
H58A H 1.0838 1.8958 0.4559 0.145 Uiso 1 1 calc R . .
H58B H 1.0426 1.9489 0.4638 0.145 Uiso 1 1 calc R . .
H58C H 1.0343 1.9065 0.4146 0.145 Uiso 1 1 calc R . .
C59 C 0.7109(2) 1.4755(3) 0.65820(17) 0.0544(10) Uani 1 1 d . . .
H59A H 0.7251 1.4930 0.6259 0.082 Uiso 1 1 calc R . .
H59B H 0.6876 1.5049 0.6728 0.082 Uiso 1 1 calc R . .
H59C H 0.6721 1.4183 0.6588 0.082 Uiso 1 1 calc R . .
C60 C 1.2842(4) 1.7770(5) 0.6973(2) 0.0805(16) Uani 1 1 d . . .
H60A H 1.2359 1.7245 0.6985 0.121 Uiso 1 1 calc R . .
H60B H 1.2862 1.8082 0.7246 0.121 Uiso 1 1 calc R . .
H60C H 1.3312 1.7704 0.6970 0.121 Uiso 1 1 calc R . .
C61 C 0.3333 0.6667 -0.0010(3) 0.0518(16) Uani 1 3 d S . .
C62 C 0.3333 0.6667 0.0490(3) 0.082(3) Uani 1 3 d S . .
H62A H 0.3800 0.7154 0.0604 0.123 Uiso 0.33 1 calc PR . .
H62B H 0.3354 0.6200 0.0604 0.123 Uiso 0.33 1 calc PR . .
H62C H 0.2846 0.6646 0.0604 0.123 Uiso 0.33 1 calc PR . .
C64 C 0.6389(4) 0.9730(4) 0.0827(2) 0.0756(15) Uani 1 1 d . . .
H64A H 0.6939 0.9850 0.0778 0.113 Uiso 1 1 calc R . .
H64B H 0.6306 0.9789 0.1158 0.113 Uiso 1 1 calc R . .
H64C H 0.6292 1.0101 0.0644 0.113 Uiso 1 1 calc R . .
C63 C 0.5835(4) 0.8908(4) 0.06784(18) 0.0662(14) Uani 1 1 d . . .
N60 N 0.3333 0.6667 -0.0407(3) 0.072(2) Uani 1 3 d S . .
N61 N 0.5407(4) 0.8277(4) 0.05461(19) 0.0808(13) Uani 1 1 d . . .
N62 N 0.6172(5) 1.1595(5) 0.1047(3) 0.123(2) Uiso 1 1 d . . .
C66 C 0.7105(9) 1.2013(9) 0.0318(5) 0.159(4) Uiso 1 1 d . . .
H66A H 0.6899 1.1563 0.0100 0.239 Uiso 1 1 calc R . .
H66B H 0.7641 1.2148 0.0419 0.239 Uiso 1 1 calc R . .
H66C H 0.7127 1.2474 0.0162 0.239 Uiso 1 1 calc R . .
C65 C 0.6659(8) 1.1827(8) 0.0660(5) 0.140(3) Uiso 1 1 d . . .
C68 C 0.8259(6) 0.6288(6) -0.0613(4) 0.120(3) Uiso 1 1 d . . .
H68A H 0.8062 0.6652 -0.0535 0.180 Uiso 1 1 calc R . .
H68B H 0.8765 0.6582 -0.0782 0.180 Uiso 1 1 calc R . .
H68C H 0.8342 0.6065 -0.0327 0.180 Uiso 1 1 calc R . .
C67 C 0.7773(9) 0.5752(9) -0.0857(5) 0.150(4) Uiso 1 1 d . . .
N63 N 0.7260(12) 0.5213(12) -0.1049(7) 0.235(7) Uiso 1 1 d . . .
O12 O 0.6667 1.3333 0.7861(10) 0.252(11) Uiso 1 3 d S . .
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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
C22 O1 C5 118.0(3) . . ?
C4 O2 C58 117.0(5) . . ?
C34 O4 C12 116.7(3) . . ?
C11 O5 C59 115.9(3) . . ?
C46 O7 C19 118.0(3) . . ?
C18 O8 C60 116.8(4) . . ?
C31 N1 C32 116.0(5) . . ?
C43 N2 C44 115.4(5) . . ?
C55 N3 C56 115.9(5) . . ?
C21 C1 C2 111.9(3) . . ?
C7 C2 C3 119.3(4) . . ?
C7 C2 C1 122.6(4) . . ?
C3 C2 C1 118.0(4) . . ?
C4 C3 C2 122.1(4) . . ?
C3 C4 O2 126.1(4) . . ?
C3 C4 C5 118.5(5) . . ?
O2 C4 C5 115.3(5) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 O1 118.9(4) . . ?
C4 C5 O1 120.3(4) . . ?
C5 C6 C7 121.5(4) . . ?
C2 C7 C6 117.8(4) . . ?
C2 C7 C9 124.1(4) . . ?
C6 C7 C9 118.2(4) . . ?
C11 C8 C10 121.4(4) . . ?
C10 C9 C7 113.0(3) . . ?
C14 C10 C8 120.5(4) . . ?
C14 C10 C9 123.7(4) . . ?
C8 C10 C9 115.8(4) . . ?
O5 C11 C8 126.1(4) . . ?
O5 C11 C12 116.3(3) . . ?
C8 C11 C12 117.6(4) . . ?
C13 C12 O4 120.7(4) . . ?
C13 C12 C11 121.6(4) . . ?
O4 C12 C11 117.5(4) . . ?
C12 C13 C14 120.8(4) . . ?
C10 C14 C13 118.1(4) . . ?
C10 C14 C15 125.2(4) . . ?
C13 C14 C15 116.7(4) . . ?
C16 C15 C14 113.8(3) . . ?
C21 C16 C17 119.6(4) . . ?
C21 C16 C15 123.6(4) . . ?
C17 C16 C15 116.8(4) . . ?
C18 C17 C16 121.2(4) . . ?
O8 C18 C17 125.7(4) . . ?
O8 C18 C19 116.2(4) . . ?
C17 C18 C19 118.0(4) . . ?
C20 C19 C18 121.5(4) . . ?
C20 C19 O7 120.2(4) . . ?
C18 C19 O7 118.2(4) . . ?
C19 C20 C21 120.9(5) . . ?
C16 C21 C20 118.8(4) . . ?
C16 C21 C1 124.4(4) . . ?
C20 C21 C1 116.8(4) . . ?
O3 C22 O1 122.4(5) . . ?
O3 C22 C23 127.7(4) . . ?
O1 C22 C23 109.8(4) . . ?
C28 C23 C24 117.0(4) . . ?
C28 C23 C22 123.5(4) . . ?
C24 C23 C22 119.5(4) . . ?
C25 C24 C23 121.5(5) . . ?
C24 C25 C26 121.1(5) . . ?
C25 C26 C27 118.1(4) . . ?
C25 C26 C29 120.8(4) . . ?
C27 C26 C29 121.1(4) . . ?
C28 C27 C26 121.0(4) . . ?
C27 C28 C23 121.2(4) . . ?
C33 C29 C30 116.0(5) . . ?
C33 C29 C26 123.4(4) . . ?
C30 C29 C26 120.5(4) . . ?
C31 C30 C29 119.3(5) . . ?
N1 C31 C30 125.3(5) . . ?
N1 C32 C33 122.4(6) . . ?
C32 C33 C29 121.0(5) . . ?
O6 C34 O4 122.1(4) . . ?
O6 C34 C35 125.8(4) . . ?
O4 C34 C35 112.1(4) . . ?
C40 C35 C36 120.6(4) . . ?
C40 C35 C34 118.1(4) . . ?
C36 C35 C34 121.4(4) . . ?
C37 C36 C35 118.8(4) . . ?
C38 C37 C36 121.5(4) . . ?
C39 C38 C37 117.7(4) . . ?
C39 C38 C41 121.9(4) . . ?
C37 C38 C41 120.5(4) . . ?
C40 C39 C38 122.2(4) . . ?
C35 C40 C39 119.1(4) . . ?
C45 C41 C42 114.5(5) . . ?
C45 C41 C38 122.6(4) . . ?
C42 C41 C38 122.9(4) . . ?
C43 C42 C41 120.9(4) . . ?
N2 C43 C42 124.0(5) . . ?
N2 C44 C45 124.0(6) . . ?
C41 C45 C44 121.0(6) . . ?
O9 C46 O7 123.1(4) . . ?
O9 C46 C47 126.1(4) . . ?
O7 C46 C47 110.8(3) . . ?
C48 C47 C52 119.9(4) . . ?
C48 C47 C46 117.9(4) . . ?
C52 C47 C46 122.1(4) . . ?
C49 C48 C47 119.7(4) . . ?
C48 C49 C50 120.7(4) . . ?
C51 C50 C49 118.3(4) . . ?
C51 C50 C53 121.4(4) . . ?
C49 C50 C53 120.4(4) . . ?
C52 C51 C50 121.5(5) . . ?
C51 C52 C47 120.0(4) . . ?
C54 C53 C57 116.8(5) . . ?
C54 C53 C50 122.5(4) . . ?
C57 C53 C50 120.6(5) . . ?
C55 C54 C53 118.3(6) . . ?
N3 C55 C54 126.1(7) . . ?
N3 C56 C57 125.2(6) . . ?
C56 C57 C53 117.6(6) . . ?
N60 C61 C62 180.000(2) . . ?
N61 C63 C64 177.5(6) . . ?
C66 C65 N62 177.4(14) . . ?
N63 C67 C68 172.9(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C22 1.361(6) . ?
O1 C5 1.420(6) . ?
O2 C4 1.389(7) . ?
O2 C58 1.423(8) . ?
O3 C22 1.198(6) . ?
O4 C34 1.363(6) . ?
O4 C12 1.413(5) . ?
O5 C11 1.381(5) . ?
O5 C59 1.447(6) . ?
O6 C34 1.208(6) . ?
O7 C46 1.368(5) . ?
O7 C19 1.424(5) . ?
O8 C18 1.382(6) . ?
O8 C60 1.419(7) . ?
O9 C46 1.209(5) . ?
N1 C31 1.324(8) . ?
N1 C32 1.362(8) . ?
N2 C43 1.324(8) . ?
N2 C44 1.353(10) . ?
N3 C55 1.300(9) . ?
N3 C56 1.337(9) . ?
C1 C21 1.528(7) . ?
C1 C2 1.528(7) . ?
C2 C7 1.408(6) . ?
C2 C3 1.419(7) . ?
C3 C4 1.369(8) . ?
C4 C5 1.410(7) . ?
C5 C6 1.375(7) . ?
C6 C7 1.421(6) . ?
C7 C9 1.530(7) . ?
C8 C11 1.387(6) . ?
C8 C10 1.408(6) . ?
C9 C10 1.520(6) . ?
C10 C14 1.398(6) . ?
C11 C12 1.418(6) . ?
C12 C13 1.370(6) . ?
C13 C14 1.418(6) . ?
C14 C15 1.540(6) . ?
C15 C16 1.522(6) . ?
C16 C21 1.400(7) . ?
C16 C17 1.416(7) . ?
C17 C18 1.396(6) . ?
C18 C19 1.405(7) . ?
C19 C20 1.374(7) . ?
C20 C21 1.411(7) . ?
C22 C23 1.473(7) . ?
C23 C28 1.411(6) . ?
C23 C24 1.415(7) . ?
C24 C25 1.370(8) . ?
C25 C26 1.400(7) . ?
C26 C27 1.405(6) . ?
C26 C29 1.502(7) . ?
C27 C28 1.376(7) . ?
C29 C33 1.388(8) . ?
C29 C30 1.401(7) . ?
C30 C31 1.377(9) . ?
C32 C33 1.387(8) . ?
C34 C35 1.489(6) . ?
C35 C40 1.389(6) . ?
C35 C36 1.407(6) . ?
C36 C37 1.402(7) . ?
C37 C38 1.399(6) . ?
C38 C39 1.396(6) . ?
C38 C41 1.471(6) . ?
C39 C40 1.393(7) . ?
C41 C45 1.382(8) . ?
C41 C42 1.407(6) . ?
C42 C43 1.397(7) . ?
C44 C45 1.393(10) . ?
C46 C47 1.499(6) . ?
C47 C48 1.396(6) . ?
C47 C52 1.396(7) . ?
C48 C49 1.392(7) . ?
C49 C50 1.408(7) . ?
C50 C51 1.394(7) . ?
C50 C53 1.491(6) . ?
C51 C52 1.377(7) . ?
C53 C54 1.409(9) . ?
C53 C57 1.423(7) . ?
C54 C55 1.402(8) . ?
C56 C57 1.407(8) . ?
C61 N60 1.142(11) . ?
C61 C62 1.435(13) . ?
C64 C63 1.469(10) . ?
C63 N61 1.146(8) . ?
N62 C65 1.378(15) . ?
C66 C65 1.238(17) . ?
C68 C67 1.215(16) . ?
C67 N63 1.16(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C7 92.0(5) . . . . ?
C21 C1 C2 C3 -84.9(5) . . . . ?
C7 C2 C3 C4 -2.8(6) . . . . ?
C1 C2 C3 C4 174.2(4) . . . . ?
C2 C3 C4 O2 179.4(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C58 O2 C4 C3 -2.7(7) . . . . ?
C58 O2 C4 C5 177.4(5) . . . . ?
C3 C4 C5 C6 3.6(6) . . . . ?
O2 C4 C5 C6 -176.5(4) . . . . ?
C3 C4 C5 O1 -172.8(4) . . . . ?
O2 C4 C5 O1 7.1(5) . . . . ?
C22 O1 C5 C6 92.3(5) . . . . ?
C22 O1 C5 C4 -91.2(5) . . . . ?
C4 C5 C6 C7 -3.0(6) . . . . ?
O1 C5 C6 C7 173.5(3) . . . . ?
C3 C2 C7 C6 3.4(6) . . . . ?
C1 C2 C7 C6 -173.4(4) . . . . ?
C3 C2 C7 C9 -176.9(4) . . . . ?
C1 C2 C7 C9 6.2(6) . . . . ?
C5 C6 C7 C2 -0.6(6) . . . . ?
C5 C6 C7 C9 179.7(4) . . . . ?
C2 C7 C9 C10 -99.5(4) . . . . ?
C6 C7 C9 C10 80.2(5) . . . . ?
C11 C8 C10 C14 -0.9(6) . . . . ?
C11 C8 C10 C9 177.1(3) . . . . ?
C7 C9 C10 C14 91.2(5) . . . . ?
C7 C9 C10 C8 -86.7(4) . . . . ?
C59 O5 C11 C8 1.0(6) . . . . ?
C59 O5 C11 C12 -179.6(4) . . . . ?
C10 C8 C11 O5 -179.4(4) . . . . ?
C10 C8 C11 C12 1.1(6) . . . . ?
C34 O4 C12 C13 -87.9(5) . . . . ?
C34 O4 C12 C11 95.3(5) . . . . ?
O5 C11 C12 C13 -179.7(4) . . . . ?
C8 C11 C12 C13 -0.2(6) . . . . ?
O5 C11 C12 O4 -2.9(5) . . . . ?
C8 C11 C12 O4 176.6(3) . . . . ?
O4 C12 C13 C14 -177.7(3) . . . . ?
C11 C12 C13 C14 -1.0(6) . . . . ?
C8 C10 C14 C13 -0.3(6) . . . . ?
C9 C10 C14 C13 -178.1(4) . . . . ?
C8 C10 C14 C15 -179.8(4) . . . . ?
C9 C10 C14 C15 2.4(6) . . . . ?
C12 C13 C14 C10 1.3(6) . . . . ?
C12 C13 C14 C15 -179.2(4) . . . . ?
C10 C14 C15 C16 -93.4(5) . . . . ?
C13 C14 C15 C16 87.1(5) . . . . ?
C14 C15 C16 C21 93.5(5) . . . . ?
C14 C15 C16 C17 -86.9(5) . . . . ?
C21 C16 C17 C18 -1.9(6) . . . . ?
C15 C16 C17 C18 178.5(4) . . . . ?
C60 O8 C18 C17 -3.1(7) . . . . ?
C60 O8 C18 C19 175.5(5) . . . . ?
C16 C17 C18 O8 178.3(4) . . . . ?
C16 C17 C18 C19 -0.3(6) . . . . ?
O8 C18 C19 C20 -177.2(4) . . . . ?
C17 C18 C19 C20 1.6(6) . . . . ?
O8 C18 C19 O7 6.6(5) . . . . ?
C17 C18 C19 O7 -174.7(4) . . . . ?
C46 O7 C19 C20 75.6(5) . . . . ?
C46 O7 C19 C18 -108.1(4) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
O7 C19 C20 C21 175.5(4) . . . . ?
C17 C16 C21 C20 2.8(6) . . . . ?
C15 C16 C21 C20 -177.7(4) . . . . ?
C17 C16 C21 C1 -179.7(4) . . . . ?
C15 C16 C21 C1 -0.2(6) . . . . ?
C19 C20 C21 C16 -1.6(6) . . . . ?
C19 C20 C21 C1 -179.3(4) . . . . ?
C2 C1 C21 C16 -96.1(5) . . . . ?
C2 C1 C21 C20 81.4(5) . . . . ?
C5 O1 C22 O3 -0.1(8) . . . . ?
C5 O1 C22 C23 -178.6(4) . . . . ?
O3 C22 C23 C28 -159.5(6) . . . . ?
O1 C22 C23 C28 18.9(6) . . . . ?
O3 C22 C23 C24 18.3(9) . . . . ?
O1 C22 C23 C24 -163.3(5) . . . . ?
C28 C23 C24 C25 -2.5(9) . . . . ?
C22 C23 C24 C25 179.5(6) . . . . ?
C23 C24 C25 C26 2.0(10) . . . . ?
C24 C25 C26 C27 0.3(8) . . . . ?
C24 C25 C26 C29 179.4(5) . . . . ?
C25 C26 C27 C28 -2.1(7) . . . . ?
C29 C26 C27 C28 178.8(4) . . . . ?
C26 C27 C28 C23 1.6(7) . . . . ?
C24 C23 C28 C27 0.7(7) . . . . ?
C22 C23 C28 C27 178.6(4) . . . . ?
C25 C26 C29 C33 -140.6(5) . . . . ?
C27 C26 C29 C33 38.5(7) . . . . ?
C25 C26 C29 C30 36.5(7) . . . . ?
C27 C26 C29 C30 -144.4(5) . . . . ?
C33 C29 C30 C31 0.3(7) . . . . ?
C26 C29 C30 C31 -177.0(5) . . . . ?
C32 N1 C31 C30 -0.6(9) . . . . ?
C29 C30 C31 N1 0.7(9) . . . . ?
C31 N1 C32 C33 -0.4(10) . . . . ?
N1 C32 C33 C29 1.3(10) . . . . ?
C30 C29 C33 C32 -1.2(8) . . . . ?
C26 C29 C33 C32 176.0(5) . . . . ?
C12 O4 C34 O6 3.3(6) . . . . ?
C12 O4 C34 C35 -177.1(3) . . . . ?
O6 C34 C35 C40 8.7(7) . . . . ?
O4 C34 C35 C40 -170.9(4) . . . . ?
O6 C34 C35 C36 -169.7(5) . . . . ?
O4 C34 C35 C36 10.7(6) . . . . ?
C40 C35 C36 C37 -1.3(6) . . . . ?
C34 C35 C36 C37 177.1(4) . . . . ?
C35 C36 C37 C38 0.9(6) . . . . ?
C36 C37 C38 C39 1.0(6) . . . . ?
C36 C37 C38 C41 -179.7(4) . . . . ?
C37 C38 C39 C40 -2.6(6) . . . . ?
C41 C38 C39 C40 178.1(4) . . . . ?
C36 C35 C40 C39 -0.2(6) . . . . ?
C34 C35 C40 C39 -178.7(4) . . . . ?
C38 C39 C40 C35 2.2(7) . . . . ?
C39 C38 C41 C45 30.9(9) . . . . ?
C37 C38 C41 C45 -148.4(8) . . . . ?
C39 C38 C41 C42 -148.2(5) . . . . ?
C37 C38 C41 C42 32.5(7) . . . . ?
C45 C41 C42 C43 -1.6(9) . . . . ?
C38 C41 C42 C43 177.6(4) . . . . ?
C44 N2 C43 C42 -1.6(13) . . . . ?
C41 C42 C43 N2 4.0(9) . . . . ?
C43 N2 C44 C45 -3.1(19) . . . . ?
C42 C41 C45 C44 -2.8(15) . . . . ?
C38 C41 C45 C44 178.0(10) . . . . ?
N2 C44 C45 C41 6(2) . . . . ?
C19 O7 C46 O9 0.6(6) . . . . ?
C19 O7 C46 C47 180.0(4) . . . . ?
O9 C46 C47 C48 3.6(6) . . . . ?
O7 C46 C47 C48 -175.7(4) . . . . ?
O9 C46 C47 C52 -177.2(4) . . . . ?
O7 C46 C47 C52 3.5(6) . . . . ?
C52 C47 C48 C49 -0.4(7) . . . . ?
C46 C47 C48 C49 178.8(4) . . . . ?
C47 C48 C49 C50 0.7(7) . . . . ?
C48 C49 C50 C51 -0.7(7) . . . . ?
C48 C49 C50 C53 -178.9(4) . . . . ?
C49 C50 C51 C52 0.4(7) . . . . ?
C53 C50 C51 C52 178.6(5) . . . . ?
C50 C51 C52 C47 -0.2(8) . . . . ?
C48 C47 C52 C51 0.2(7) . . . . ?
C46 C47 C52 C51 -179.0(4) . . . . ?
C51 C50 C53 C54 -143.0(5) . . . . ?
C49 C50 C53 C54 35.2(7) . . . . ?
C51 C50 C53 C57 35.1(6) . . . . ?
C49 C50 C53 C57 -146.7(5) . . . . ?
C57 C53 C54 C55 0.1(8) . . . . ?
C50 C53 C54 C55 178.3(5) . . . . ?
C56 N3 C55 C54 -2.6(10) . . . . ?
C53 C54 C55 N3 2.7(10) . . . . ?
C55 N3 C56 C57 -0.3(9) . . . . ?
N3 C56 C57 C53 2.9(9) . . . . ?
C54 C53 C57 C56 -2.5(7) . . . . ?
C50 C53 C57 C56 179.3(5) . . . . ?
