#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:15:31 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178427 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/48/4024828.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_4024828
loop_
_publ_author_name
'Na Fu'
'Jeffrey M. Baumes'
'Easwaran Arunkumar'
'Bruce C. Noll'
'Bradley D. Smith'
_publ_section_title
;
Squaraine Rotaxanes with Boat Conformation Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6462
_journal_page_last               6468
_journal_paper_doi               10.1021/jo901298n
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C38 H32 N2 O2, C32 H28 N4 O4'
_chemical_formula_sum            'C70 H60 N6 O6'
_chemical_formula_weight         1081.24
_chemical_name_common            rotaxane500nm
_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                104.095(2)
_cell_angle_beta                 100.631(2)
_cell_angle_gamma                103.265(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5354(4)
_cell_length_b                   15.9438(6)
_cell_length_c                   18.2433(7)
_cell_measurement_reflns_used    9953
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.608
_cell_measurement_theta_min      2.367
_cell_volume                     2797.50(18)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8-Apex II CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            87679
_diffrn_reflns_theta_full        26.89
_diffrn_reflns_theta_max         26.89
_diffrn_reflns_theta_min         1.38
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'SIEMENS KFF MO2 K90'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick,G.M. (2008) TWINABS. University of Göttingen, Germany.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1140
_exptl_crystal_recrystallization_method
'hexanes vaper difussion into chloroform'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         11876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²+1.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1220
_reflns_number_gt                9582
_reflns_number_total             11876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901298n_si_005.cif
_cod_data_source_block           nfu01_1t5
_cod_database_code               4024828
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
N1 N 0.82849(15) 0.47366(10) 0.14132(9) 0.0274(3) Uani 1 1 d . . .
H1A H 0.8760 0.5242 0.1364 0.033 Uiso 1 1 calc R . .
N2 N 0.89172(15) 0.82557(9) 0.47070(8) 0.0241(3) Uani 1 1 d . . .
H2A H 0.9263 0.8464 0.4361 0.029 Uiso 1 1 calc R . .
N3 N 1.22979(16) 1.01712(10) 0.38335(9) 0.0273(3) Uani 1 1 d . . .
H3A H 1.1545 0.9750 0.3767 0.033 Uiso 1 1 calc R . .
N4 N 1.20093(15) 0.65991(10) 0.06754(9) 0.0256(3) Uani 1 1 d . . .
H4A H 1.1207 0.6473 0.0768 0.031 Uiso 1 1 calc R . .
O1 O 0.81928(15) 0.32847(8) 0.13463(8) 0.0338(3) Uani 1 1 d . . .
O2 O 0.92699(14) 0.83217(9) 0.59904(8) 0.0346(3) Uani 1 1 d . . .
O3 O 1.42466(13) 1.10856(9) 0.46960(8) 0.0335(3) Uani 1 1 d . . .
O4 O 1.37990(14) 0.60825(10) 0.05025(9) 0.0414(4) Uani 1 1 d . . .
C1 C 0.87882(18) 0.40217(11) 0.13011(10) 0.0248(4) Uani 1 1 d . . .
C2 C 0.70004(19) 0.47197(13) 0.16103(12) 0.0328(4) Uani 1 1 d . . .
H2B H 0.6626 0.4137 0.1703 0.039 Uiso 1 1 calc R . .
H2C H 0.6353 0.4768 0.1166 0.039 Uiso 1 1 calc R . .
C3 C 0.71715(17) 0.54894(11) 0.23335(11) 0.0249(4) Uani 1 1 d . . .
C4 C 0.64328(18) 0.61064(12) 0.23185(11) 0.0247(4) Uani 1 1 d . . .
H4B H 0.5826 0.6059 0.1845 0.030 Uiso 1 1 calc R . .
C5 C 0.65788(18) 0.67955(11) 0.29953(11) 0.0246(4) Uani 1 1 d . . .
H5A H 0.6068 0.7213 0.2975 0.029 Uiso 1 1 calc R . .
C6 C 0.74523(17) 0.68836(11) 0.36951(10) 0.0237(4) Uani 1 1 d . . .
C7 C 0.82089(19) 0.62693(12) 0.37048(11) 0.0294(4) Uani 1 1 d . . .
H7A H 0.8826 0.6323 0.4176 0.035 Uiso 1 1 calc R . .
C8 C 0.80676(19) 0.55838(12) 0.30344(12) 0.0310(4) Uani 1 1 d . . .
H8A H 0.8589 0.5172 0.3053 0.037 Uiso 1 1 calc R . .
C9 C 0.75720(19) 0.76141(12) 0.44373(11) 0.0298(4) Uani 1 1 d . . .
H9A H 0.6891 0.7937 0.4336 0.036 Uiso 1 1 calc R . .
H9B H 0.7390 0.7334 0.4849 0.036 Uiso 1 1 calc R . .
C10 C 0.96655(19) 0.85497(11) 0.54568(10) 0.0245(4) Uani 1 1 d . . .
C11 C 1.10643(18) 0.91574(11) 0.55931(10) 0.0224(4) Uani 1 1 d . . .
C12 C 1.14058(17) 0.96223(11) 0.50726(10) 0.0203(3) Uani 1 1 d . . .
H12A H 1.0720 0.9612 0.4649 0.024 Uiso 1 1 calc R . .
C13 C 1.27382(17) 1.01039(11) 0.51596(10) 0.0226(4) Uani 1 1 d . . .
C14 C 1.37160(19) 1.01597(13) 0.58082(11) 0.0309(4) Uani 1 1 d . . .
H14A H 1.4623 1.0500 0.5885 0.037 Uiso 1 1 calc R . .
C15 C 1.3377(2) 0.97228(15) 0.63445(11) 0.0362(5) Uani 1 1 d . . .
H15A H 1.4052 0.9771 0.6789 0.043 Uiso 1 1 calc R . .
C16 C 1.2062(2) 0.92163(13) 0.62381(11) 0.0300(4) Uani 1 1 d . . .
H16A H 1.1840 0.8910 0.6604 0.036 Uiso 1 1 calc R . .
C17 C 1.31583(18) 1.05098(11) 0.45493(10) 0.0242(4) Uani 1 1 d . . .
C18 C 1.2543(2) 1.04621(12) 0.31657(11) 0.0305(4) Uani 1 1 d . . .
H18A H 1.3433 1.0921 0.3322 0.037 Uiso 1 1 calc R . .
H18B H 1.1848 1.0748 0.2995 0.037 Uiso 1 1 calc R . .
C19 C 1.25162(17) 0.96780(11) 0.24873(10) 0.0236(4) Uani 1 1 d . . .
C20 C 1.18988(19) 0.96010(12) 0.17238(11) 0.0277(4) Uani 1 1 d . . .
H20A H 1.1465 1.0037 0.1623 0.033 Uiso 1 1 calc R . .
C21 C 1.19068(19) 0.88937(12) 0.11040(11) 0.0280(4) Uani 1 1 d . . .
H21A H 1.1486 0.8856 0.0585 0.034 Uiso 1 1 calc R . .
C22 C 1.25226(17) 0.82426(12) 0.12347(10) 0.0242(4) Uani 1 1 d . . .
C23 C 1.31236(18) 0.83127(12) 0.20018(11) 0.0262(4) Uani 1 1 d . . .
H23A H 1.3542 0.7870 0.2104 0.031 Uiso 1 1 calc R . .
C24 C 1.31206(17) 0.90170(12) 0.26177(10) 0.0249(4) Uani 1 1 d . . .
H24A H 1.3536 0.9051 0.3137 0.030 Uiso 1 1 calc R . .
C25 C 1.2542(2) 0.74756(12) 0.05645(11) 0.0321(4) Uani 1 1 d . . .
H25A H 1.1996 0.7502 0.0071 0.039 Uiso 1 1 calc R . .
H25B H 1.3479 0.7546 0.0518 0.039 Uiso 1 1 calc R . .
C26 C 1.26809(18) 0.59714(12) 0.06439(10) 0.0269(4) Uani 1 1 d . . .
C27 C 1.20195(17) 0.51254(12) 0.08160(10) 0.0239(4) Uani 1 1 d . . .
C28 C 1.07014(17) 0.49269(11) 0.08937(9) 0.0214(3) Uani 1 1 d . . .
H28A H 1.0158 0.5300 0.0774 0.026 Uiso 1 1 calc R . .
C29 C 1.01623(18) 0.41974(11) 0.11414(10) 0.0234(4) Uani 1 1 d . . .
C30 C 1.0938(2) 0.36217(12) 0.12746(11) 0.0295(4) Uani 1 1 d . . .
H30A H 1.0579 0.3114 0.1437 0.035 Uiso 1 1 calc R . .
C31 C 1.2233(2) 0.37919(14) 0.11702(11) 0.0339(5) Uani 1 1 d . . .
H31A H 1.2751 0.3391 0.1250 0.041 Uiso 1 1 calc R . .
C32 C 1.27782(19) 0.45398(13) 0.09504(11) 0.0297(4) Uani 1 1 d . . .
H32A H 1.3673 0.4656 0.0891 0.036 Uiso 1 1 calc R . .
N5 N 0.75927(13) 0.79040(9) 0.15226(8) 0.0185(3) Uani 1 1 d . . .
N6 N 1.38458(14) 0.63922(10) 0.45537(8) 0.0233(3) Uani 1 1 d . . .
O5 O 0.94497(12) 0.65527(8) 0.11876(7) 0.0220(3) Uani 1 1 d . . .
O6 O 0.95487(12) 0.88058(8) 0.33023(7) 0.0218(3) Uani 1 1 d . . .
C33 C 0.94763(16) 0.71546(10) 0.17739(9) 0.0176(3) Uani 1 1 d . . .
C34 C 0.86738(16) 0.77930(10) 0.19231(9) 0.0170(3) Uani 1 1 d . . .
C35 C 0.95139(16) 0.81773(10) 0.27364(9) 0.0175(3) Uani 1 1 d . . .
C36 C 1.02336(16) 0.75070(10) 0.25834(9) 0.0177(3) Uani 1 1 d . . .
C37 C 1.12068(16) 0.72471(11) 0.30637(9) 0.0182(3) Uani 1 1 d . . .
C38 C 1.16910(17) 0.77081(11) 0.38663(10) 0.0232(4) Uani 1 1 d . . .
H38A H 1.1396 0.8214 0.4077 0.028 Uiso 1 1 calc R . .
C39 C 1.25774(18) 0.74503(11) 0.43556(10) 0.0243(4) Uani 1 1 d . . .
H39A H 1.2893 0.7782 0.4895 0.029 Uiso 1 1 calc R . .
C40 C 1.30238(16) 0.66938(11) 0.40624(10) 0.0216(3) Uani 1 1 d . . .
C41 C 1.25812(17) 0.62460(11) 0.32486(10) 0.0219(3) Uani 1 1 d . . .
H41A H 1.2900 0.5754 0.3032 0.026 Uiso 1 1 calc R . .
C42 C 1.16946(17) 0.65162(11) 0.27683(10) 0.0210(3) Uani 1 1 d . . .
H42A H 1.1405 0.6203 0.2225 0.025 Uiso 1 1 calc R . .
C43 C 1.42780(17) 0.68649(12) 0.53935(10) 0.0252(4) Uani 1 1 d . . .
H43A H 1.4694 0.7513 0.5469 0.030 Uiso 1 1 calc R . .
H43B H 1.4984 0.6629 0.5638 0.030 Uiso 1 1 calc R . .
C44 C 1.31697(18) 0.67819(12) 0.58195(10) 0.0250(4) Uani 1 1 d . . .
C45 C 1.1877(2) 0.61991(13) 0.54869(12) 0.0345(4) Uani 1 1 d . . .
H45A H 1.1647 0.5837 0.4957 0.041 Uiso 1 1 calc R . .
C46 C 1.0915(2) 0.61353(16) 0.59127(14) 0.0436(5) Uani 1 1 d . . .
H46A H 1.0033 0.5738 0.5672 0.052 Uiso 1 1 calc R . .
C47 C 1.1235(2) 0.66482(18) 0.66875(14) 0.0460(6) Uani 1 1 d . . .
H47A H 1.0584 0.6593 0.6984 0.055 Uiso 1 1 calc R . .
C48 C 1.2497(2) 0.72354(19) 0.70220(12) 0.0506(7) Uani 1 1 d . . .
H48A H 1.2720 0.7596 0.7552 0.061 Uiso 1 1 calc R . .
C49 C 1.3460(2) 0.73088(16) 0.65915(12) 0.0395(5) Uani 1 1 d . . .
H49A H 1.4329 0.7726 0.6830 0.047 Uiso 1 1 calc R . .
C50 C 1.46407(17) 0.58297(12) 0.42252(11) 0.0241(4) Uani 1 1 d . . .
H50A H 1.5427 0.5891 0.4648 0.029 Uiso 1 1 calc R . .
H50B H 1.4993 0.6072 0.3829 0.029 Uiso 1 1 calc R . .
C51 C 1.39186(17) 0.48360(12) 0.38504(10) 0.0243(4) Uani 1 1 d . . .
C52 C 1.28825(19) 0.43854(13) 0.41070(14) 0.0356(5) Uani 1 1 d . . .
H52A H 1.2597 0.4706 0.4526 0.043 Uiso 1 1 calc R . .
C53 C 1.2262(2) 0.34731(15) 0.37581(19) 0.0567(8) Uani 1 1 d . . .
H53A H 1.1550 0.3170 0.3936 0.068 Uiso 1 1 calc R . .
C54 C 1.2675(3) 0.30001(16) 0.31506(18) 0.0654(9) Uani 1 1 d . . .
H54A H 1.2247 0.2373 0.2910 0.078 Uiso 1 1 calc R . .
C55 C 1.3710(3) 0.34408(17) 0.28941(13) 0.0600(8) Uani 1 1 d . . .
H55A H 1.3998 0.3115 0.2478 0.072 Uiso 1 1 calc R . .
C56 C 1.4335(2) 0.43588(15) 0.32412(12) 0.0397(5) Uani 1 1 d . . .
H56A H 1.5047 0.4660 0.3062 0.048 Uiso 1 1 calc R . .
C57 C 0.69072(17) 0.72767(11) 0.07309(10) 0.0223(4) Uani 1 1 d . . .
H57A H 0.5996 0.6937 0.0733 0.027 Uiso 1 1 calc R . .
H57B H 0.7418 0.6836 0.0599 0.027 Uiso 1 1 calc R . .
C58 C 0.67778(17) 0.77470(11) 0.01066(9) 0.0198(3) Uani 1 1 d . . .
C59 C 0.55294(17) 0.75354(11) -0.04207(10) 0.0215(3) Uani 1 1 d . . .
H59A H 0.4770 0.7117 -0.0373 0.026 Uiso 1 1 calc R . .
C60 C 0.5394(2) 0.79351(13) -0.10160(11) 0.0304(4) Uani 1 1 d . . .
H60A H 0.4544 0.7786 -0.1378 0.036 Uiso 1 1 calc R . .
C61 C 0.6492(2) 0.85466(14) -0.10819(11) 0.0369(5) Uani 1 1 d . . .
H61A H 0.6394 0.8825 -0.1485 0.044 Uiso 1 1 calc R . .
C62 C 0.7743(2) 0.87581(14) -0.05599(12) 0.0350(5) Uani 1 1 d . . .
H62A H 0.8500 0.9178 -0.0608 0.042 Uiso 1 1 calc R . .
C63 C 0.78834(18) 0.83560(12) 0.00287(11) 0.0264(4) Uani 1 1 d . . .
H63A H 0.8740 0.8497 0.0382 0.032 Uiso 1 1 calc R . .
C64 C 0.69508(17) 0.85799(12) 0.18848(10) 0.0236(4) Uani 1 1 d . . .
H64A H 0.7246 0.8727 0.2460 0.028 Uiso 1 1 calc R . .
H64B H 0.5960 0.8309 0.1726 0.028 Uiso 1 1 calc R . .
C65 C 0.72855(18) 0.94429(12) 0.16617(10) 0.0235(4) Uani 1 1 d . . .
C66 C 0.6308(2) 0.96594(13) 0.11732(11) 0.0308(4) Uani 1 1 d . . .
H66A H 0.5418 0.9262 0.0978 0.037 Uiso 1 1 calc R . .
C67 C 0.6633(2) 1.04528(13) 0.09724(12) 0.0379(5) Uani 1 1 d . . .
H67A H 0.5968 1.0591 0.0632 0.046 Uiso 1 1 calc R . .
C68 C 0.7917(2) 1.10430(13) 0.12645(12) 0.0385(5) Uani 1 1 d . . .
H68A H 0.8135 1.1587 0.1128 0.046 Uiso 1 1 calc R . .
C69 C 0.8889(2) 1.08372(13) 0.17600(13) 0.0374(5) Uani 1 1 d . . .
H69A H 0.9773 1.1242 0.1964 0.045 Uiso 1 1 calc R . .
C70 C 0.85703(19) 1.00423(12) 0.19571(11) 0.0298(4) Uani 1 1 d . . .
H70A H 0.9238 0.9907 0.2298 0.036 Uiso 1 1 calc R . .
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'
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
C1 N1 C2 123.87(16) . . ?
C1 N1 H1A 118.1 . . ?
C2 N1 H1A 118.1 . . ?
C10 N2 C9 124.06(15) . . ?
C10 N2 H2A 118.0 . . ?
C9 N2 H2A 118.0 . . ?
C17 N3 C18 123.60(15) . . ?
C17 N3 H3A 118.2 . . ?
C18 N3 H3A 118.2 . . ?
C26 N4 C25 123.51(16) . . ?
C26 N4 H4A 118.2 . . ?
C25 N4 H4A 118.2 . . ?
O1 C1 N1 122.89(17) . . ?
O1 C1 C29 121.81(16) . . ?
N1 C1 C29 115.27(15) . . ?
N1 C2 C3 111.14(14) . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
N1 C2 H2C 109.4 . . ?
C3 C2 H2C 109.4 . . ?
H2B C2 H2C 108.0 . . ?
C4 C3 C8 118.51(16) . . ?
C4 C3 C2 121.19(17) . . ?
C8 C3 C2 120.30(17) . . ?
C3 C4 C5 120.31(17) . . ?
C3 C4 H4B 119.8 . . ?
C5 C4 H4B 119.8 . . ?
C6 C5 C4 121.37(16) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C5 C6 C7 118.13(16) . . ?
C5 C6 C9 121.22(16) . . ?
C7 C6 C9 120.64(16) . . ?
C8 C7 C6 120.72(17) . . ?
C8 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C7 C8 C3 120.96(17) . . ?
C7 C8 H8A 119.5 . . ?
C3 C8 H8A 119.5 . . ?
N2 C9 C6 110.76(15) . . ?
N2 C9 H9A 109.5 . . ?
C6 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 N2 123.49(17) . . ?
O2 C10 C11 121.40(16) . . ?
N2 C10 C11 115.07(15) . . ?
C12 C11 C16 119.10(16) . . ?
C12 C11 C10 121.86(15) . . ?
C16 C11 C10 118.95(16) . . ?
C11 C12 C13 121.26(16) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C12 118.71(17) . . ?
C14 C13 C17 119.09(16) . . ?
C12 C13 C17 122.08(15) . . ?
C15 C14 C13 120.37(18) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 120.59(18) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C15 C16 C11 119.86(18) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
O3 C17 N3 123.04(17) . . ?
O3 C17 C13 121.33(16) . . ?
N3 C17 C13 115.56(15) . . ?
N3 C18 C19 111.81(15) . . ?
N3 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N3 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C24 118.17(16) . . ?
C20 C19 C18 121.16(17) . . ?
C24 C19 C18 120.67(16) . . ?
C19 C20 C21 120.84(17) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C22 C21 C20 120.85(17) . . ?
C22 C21 H21A 119.6 . . ?
C20 C21 H21A 119.6 . . ?
C21 C22 C23 118.26(16) . . ?
C21 C22 C25 121.14(16) . . ?
C23 C22 C25 120.60(17) . . ?
C24 C23 C22 120.94(17) . . ?
C24 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?
C23 C24 C19 120.93(16) . . ?
C23 C24 H24A 119.5 . . ?
C19 C24 H24A 119.5 . . ?
N4 C25 C22 111.74(15) . . ?
N4 C25 H25A 109.3 . . ?
C22 C25 H25A 109.3 . . ?
N4 C25 H25B 109.3 . . ?
C22 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
O4 C26 N4 122.67(18) . . ?
O4 C26 C27 120.71(17) . . ?
N4 C26 C27 116.60(16) . . ?
C28 C27 C32 118.41(17) . . ?
C28 C27 C26 122.59(16) . . ?
C32 C27 C26 118.89(16) . . ?
C29 C28 C27 121.64(16) . . ?
C29 C28 H28A 119.2 . . ?
C27 C28 H28A 119.2 . . ?
C28 C29 C30 118.99(17) . . ?
C28 C29 C1 122.43(15) . . ?
C30 C29 C1 118.54(16) . . ?
C31 C30 C29 119.90(18) . . ?
C31 C30 H30A 120.1 . . ?
C29 C30 H30A 120.1 . . ?
C32 C31 C30 120.60(17) . . ?
C32 C31 H31A 119.7 . . ?
C30 C31 H31A 119.7 . . ?
C31 C32 C27 120.36(18) . . ?
C31 C32 H32A 119.8 . . ?
C27 C32 H32A 119.8 . . ?
C34 N5 C57 119.48(14) . . ?
C34 N5 C64 120.91(14) . . ?
C57 N5 C64 119.21(13) . . ?
C40 N6 C50 118.91(14) . . ?
C40 N6 C43 119.71(14) . . ?
C50 N6 C43 118.04(13) . . ?
O5 C33 C36 136.65(15) . . ?
O5 C33 C34 133.55(14) . . ?
C36 C33 C34 89.76(13) . . ?
N5 C34 C33 134.78(15) . . ?
N5 C34 C35 135.70(15) . . ?
C33 C34 C35 89.21(12) . . ?
O6 C35 C36 136.48(15) . . ?
O6 C35 C34 134.09(15) . . ?
C36 C35 C34 89.42(12) . . ?
C37 C36 C33 134.50(15) . . ?
C37 C36 C35 133.80(15) . . ?
C33 C36 C35 91.45(13) . . ?
C38 C37 C42 117.38(14) . . ?
C38 C37 C36 120.26(15) . . ?
C42 C37 C36 122.34(15) . . ?
C39 C38 C37 122.02(16) . . ?
C39 C38 H38A 119.0 . . ?
C37 C38 H38A 119.0 . . ?
C38 C39 C40 120.43(16) . . ?
C38 C39 H39A 119.8 . . ?
C40 C39 H39A 119.8 . . ?
N6 C40 C39 121.13(15) . . ?
N6 C40 C41 120.96(15) . . ?
C39 C40 C41 117.90(15) . . ?
C42 C41 C40 120.68(15) . . ?
C42 C41 H41A 119.7 . . ?
C40 C41 H41A 119.7 . . ?
C41 C42 C37 121.49(15) . . ?
C41 C42 H42A 119.3 . . ?
C37 C42 H42A 119.3 . . ?
N6 C43 C44 115.23(14) . . ?
N6 C43 H43A 108.5 . . ?
C44 C43 H43A 108.5 . . ?
N6 C43 H43B 108.5 . . ?
C44 C43 H43B 108.5 . . ?
H43A C43 H43B 107.5 . . ?
C45 C44 C49 117.59(19) . . ?
C45 C44 C43 123.85(17) . . ?
C49 C44 C43 118.56(17) . . ?
C46 C45 C44 121.2(2) . . ?
C46 C45 H45A 119.4 . . ?
C44 C45 H45A 119.4 . . ?
C47 C46 C45 120.3(2) . . ?
C47 C46 H46A 119.9 . . ?
C45 C46 H46A 119.9 . . ?
C48 C47 C46 119.3(2) . . ?
C48 C47 H47A 120.3 . . ?
C46 C47 H47A 120.3 . . ?
C47 C48 C49 120.4(2) . . ?
C47 C48 H48A 119.8 . . ?
C49 C48 H48A 119.8 . . ?
C44 C49 C48 121.1(2) . . ?
C44 C49 H49A 119.4 . . ?
C48 C49 H49A 119.4 . . ?
N6 C50 C51 116.43(14) . . ?
N6 C50 H50A 108.2 . . ?
C51 C50 H50A 108.2 . . ?
N6 C50 H50B 108.2 . . ?
C51 C50 H50B 108.2 . . ?
H50A C50 H50B 107.3 . . ?
C52 C51 C56 119.25(19) . . ?
C52 C51 C50 122.19(18) . . ?
C56 C51 C50 118.54(18) . . ?
C53 C52 C51 120.5(2) . . ?
C53 C52 H52A 119.8 . . ?
C51 C52 H52A 119.8 . . ?
C52 C53 C54 120.2(3) . . ?
C52 C53 H53A 119.9 . . ?
C54 C53 H53A 119.9 . . ?
C55 C54 C53 119.8(2) . . ?
C55 C54 H54A 120.1 . . ?
C53 C54 H54A 120.1 . . ?
C54 C55 C56 120.3(3) . . ?
C54 C55 H55A 119.9 . . ?
C56 C55 H55A 119.9 . . ?
C51 C56 C55 120.0(2) . . ?
C51 C56 H56A 120.0 . . ?
C55 C56 H56A 120.0 . . ?
N5 C57 C58 113.31(13) . . ?
N5 C57 H57A 108.9 . . ?
C58 C57 H57A 108.9 . . ?
N5 C57 H57B 108.9 . . ?
C58 C57 H57B 108.9 . . ?
H57A C57 H57B 107.7 . . ?
C63 C58 C59 119.47(16) . . ?
C63 C58 C57 121.53(15) . . ?
C59 C58 C57 118.96(15) . . ?
C60 C59 C58 120.09(17) . . ?
C60 C59 H59A 120.0 . . ?
C58 C59 H59A 120.0 . . ?
C61 C60 C59 120.00(17) . . ?
C61 C60 H60A 120.0 . . ?
C59 C60 H60A 120.0 . . ?
C60 C61 C62 120.25(18) . . ?
C60 C61 H61A 119.9 . . ?
C62 C61 H61A 119.9 . . ?
C63 C62 C61 119.89(19) . . ?
C63 C62 H62A 120.1 . . ?
C61 C62 H62A 120.1 . . ?
C62 C63 C58 120.30(17) . . ?
C62 C63 H63A 119.9 . . ?
C58 C63 H63A 119.9 . . ?
N5 C64 C65 113.43(14) . . ?
N5 C64 H64A 108.9 . . ?
C65 C64 H64A 108.9 . . ?
N5 C64 H64B 108.9 . . ?
C65 C64 H64B 108.9 . . ?
H64A C64 H64B 107.7 . . ?
C70 C65 C66 119.01(17) . . ?
C70 C65 C64 120.02(15) . . ?
C66 C65 C64 120.95(16) . . ?
C67 C66 C65 120.22(18) . . ?
C67 C66 H66A 119.9 . . ?
C65 C66 H66A 119.9 . . ?
C68 C67 C66 120.40(18) . . ?
C68 C67 H67A 119.8 . . ?
C66 C67 H67A 119.8 . . ?
C67 C68 C69 119.64(18) . . ?
C67 C68 H68A 120.2 . . ?
C69 C68 H68A 120.2 . . ?
C70 C69 C68 120.09(19) . . ?
C70 C69 H69A 120.0 . . ?
C68 C69 H69A 120.0 . . ?
C69 C70 C65 120.62(18) . . ?
C69 C70 H70A 119.7 . . ?
C65 C70 H70A 119.7 . . ?
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
N1 C1 1.351(2) . ?
N1 C2 1.459(2) . ?
N1 H1A 0.8800 . ?
N2 C10 1.354(2) . ?
N2 C9 1.459(2) . ?
N2 H2A 0.8800 . ?
N3 C17 1.347(2) . ?
N3 C18 1.450(2) . ?
N3 H3A 0.8800 . ?
N4 C26 1.348(2) . ?
N4 C25 1.459(2) . ?
N4 H4A 0.8800 . ?
O1 C1 1.229(2) . ?
O2 C10 1.227(2) . ?
O3 C17 1.230(2) . ?
O4 C26 1.235(2) . ?
C1 C29 1.506(3) . ?
C2 C3 1.517(2) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.390(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.395(2) . ?
C4 H4B 0.9500 . ?
C5 C6 1.384(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.399(3) . ?
C6 C9 1.519(2) . ?
C7 C8 1.385(3) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.505(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.396(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(2) . ?
C13 C17 1.502(3) . ?
C14 C15 1.384(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 C19 1.521(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.387(3) . ?
C19 C24 1.395(3) . ?
C20 C21 1.392(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.391(3) . ?
C22 C25 1.511(3) . ?
C23 C24 1.383(3) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.503(3) . ?
C27 C28 1.393(2) . ?
C27 C32 1.397(2) . ?
C28 C29 1.388(2) . ?
C28 H28A 0.9500 . ?
C29 C30 1.396(2) . ?
C30 C31 1.387(3) . ?
C30 H30A 0.9500 . ?
C31 C32 1.384(3) . ?
C31 H31A 0.9500 . ?
C32 H32A 0.9500 . ?
N5 C34 1.308(2) . ?
N5 C57 1.479(2) . ?
N5 C64 1.486(2) . ?
N6 C40 1.378(2) . ?
N6 C50 1.460(2) . ?
N6 C43 1.465(2) . ?
O5 C33 1.242(2) . ?
O6 C35 1.2396(19) . ?
C33 C36 1.445(2) . ?
C33 C34 1.473(2) . ?
C34 C35 1.478(2) . ?
C35 C36 1.449(2) . ?
C36 C37 1.425(2) . ?
C37 C38 1.404(2) . ?
C37 C42 1.408(2) . ?
C38 C39 1.373(2) . ?
C38 H38A 0.9500 . ?
C39 C40 1.414(2) . ?
C39 H39A 0.9500 . ?
C40 C41 1.417(2) . ?
C41 C42 1.376(2) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C43 C44 1.516(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.388(3) . ?
C44 C49 1.389(3) . ?
C45 C46 1.387(3) . ?
C45 H45A 0.9500 . ?
C46 C47 1.384(3) . ?
C46 H46A 0.9500 . ?
C47 C48 1.367(4) . ?
C47 H47A 0.9500 . ?
C48 C49 1.394(3) . ?
C48 H48A 0.9500 . ?
C49 H49A 0.9500 . ?
C50 C51 1.511(2) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.385(3) . ?
C51 C56 1.388(3) . ?
C52 C53 1.381(3) . ?
C52 H52A 0.9500 . ?
C53 C54 1.381(4) . ?
C53 H53A 0.9500 . ?
C54 C55 1.378(4) . ?
C54 H54A 0.9500 . ?
C55 C56 1.389(3) . ?
C55 H55A 0.9500 . ?
C56 H56A 0.9500 . ?
C57 C58 1.511(2) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C63 1.389(2) . ?
C58 C59 1.393(2) . ?
C59 C60 1.388(3) . ?
C59 H59A 0.9500 . ?
C60 C61 1.376(3) . ?
C60 H60A 0.9500 . ?
C61 C62 1.391(3) . ?
C61 H61A 0.9500 . ?
C62 C63 1.381(3) . ?
C62 H62A 0.9500 . ?
C63 H63A 0.9500 . ?
C64 C65 1.512(2) . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C65 C70 1.386(3) . ?
C65 C66 1.396(2) . ?
C66 C67 1.387(3) . ?
C66 H66A 0.9500 . ?
C67 C68 1.380(3) . ?
C67 H67A 0.9500 . ?
C68 C69 1.390(3) . ?
C68 H68A 0.9500 . ?
C69 C70 1.386(3) . ?
C69 H69A 0.9500 . ?
C70 H70A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_distance_DA
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A 0.880 2.172 165.81 3.032(2) O5 1_555 y
N2 H2A 0.880 2.183 164.03 3.0389(19) O6 1_555 y
N3 H3A 0.880 2.163 163.90 3.018(2) O6 1_555 y
N4 H4A 0.880 2.148 164.04 3.004(2) O5 1_555 y
