#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:13:37 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179236 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/56/4315640.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_4315640
loop_
_publ_author_name
'Yoshimi Oka'
'Nobuyuki Tamaoki'
_publ_contact_author             'Nobuyuki Tamaoki'
_publ_contact_author_email       tamaoki@es.hokudai.ac.jp
_publ_section_title
;
 Structure of Silver(I) Complex Prepared from Azobenzenonaphthalenophane,
 Photochemical Coordination Change of Silver(I) and Silver(I)-Induced
 Acceleration of Z-E Thermal Isomerization of Azobenzene Unit
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4765
_journal_page_last               4767
_journal_paper_doi               10.1021/ic100317p
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C28 H26 N2 O4'
_chemical_formula_weight         454.51
_chemical_name_common            E-[5.5](4,4')azobenzeno(1,5)naphthalenophane
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                112.959(2)
_cell_angle_beta                 107.749(2)
_cell_angle_gamma                103.7260(10)
_cell_formula_units_Z            4
_cell_length_a                   13.8977(10)
_cell_length_b                   14.1796(10)
_cell_length_c                   14.6044(18)
_cell_measurement_reflns_used    5269
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.926
_cell_measurement_theta_min      2.433
_cell_volume                     2306.3(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14165
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         28.42
_diffrn_reflns_theta_min         1.68
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  619
_diffrn_standards_number         61
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         10090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0977P)²+0.4187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                7454
_reflns_number_total             10090
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic100317p_si_002_2.cif
_cod_data_source_block           E-[5.5](4,4')azobenzeno(1,5)naphthalenophane
_cod_database_code               4315640
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
O1 O 0.83484(13) 0.34588(13) -0.23490(13) 0.0570(4) Uani 1 1 d . . .
O2 O 0.91541(11) 0.29119(10) -0.01554(10) 0.0410(3) Uani 1 1 d . . .
O3 O 0.79105(10) 0.28023(11) 0.33905(10) 0.0425(3) Uani 1 1 d . . .
O4 O 0.55192(13) 0.18575(15) 0.35448(13) 0.0680(5) Uani 1 1 d . . .
O5 O 0.25559(13) 0.08572(13) 0.82964(11) 0.0576(4) Uani 1 1 d . . .
O6 O 0.28376(10) 0.29838(11) 0.76627(10) 0.0437(3) Uani 1 1 d . . .
O7 O 0.22530(10) 0.38339(11) 0.38673(10) 0.0419(3) Uani 1 1 d . . .
O8 O 0.18781(11) 0.23103(11) 0.11773(10) 0.0482(3) Uani 1 1 d . . .
N1 N 0.58096(13) 0.29271(15) 0.03626(14) 0.0478(4) Uani 1 1 d . . .
N2 N 0.57925(13) 0.21583(14) -0.04535(13) 0.0464(4) Uani 1 1 d . . .
N3 N 0.15511(12) 0.02342(12) 0.36494(12) 0.0397(3) Uani 1 1 d . . .
N4 N 0.24269(13) 0.03014(13) 0.43138(12) 0.0424(4) Uani 1 1 d . . .
C1 C 0.62880(15) 0.25326(17) -0.10400(15) 0.0447(4) Uani 1 1 d . . .
C2 C 0.68561(17) 0.36555(17) -0.06831(16) 0.0485(5) Uani 1 1 d . . .
H2 H 0.6803 0.4225 -0.0107 0.058 Uiso 1 1 calc R . .
C3 C 0.74984(17) 0.39355(18) -0.11726(17) 0.0499(5) Uani 1 1 d . . .
H3 H 0.7882 0.4701 -0.0937 0.060 Uiso 1 1 calc R . .
C4 C 0.75861(16) 0.31105(18) -0.20006(16) 0.0473(5) Uani 1 1 d . . .
C5 C 0.69442(17) 0.19890(18) -0.24276(17) 0.0510(5) Uani 1 1 d . . .
H5 H 0.6940 0.1422 -0.3053 0.061 Uiso 1 1 calc R . .
C6 C 0.63129(16) 0.17111(18) -0.19287(16) 0.0493(5) Uani 1 1 d . . .
H6 H 0.5890 0.0945 -0.2200 0.059 Uiso 1 1 calc R . .
C7 C 0.90268(18) 0.28584(18) -0.25030(17) 0.0513(5) Uani 1 1 d . . .
H7A H 0.9433 0.3098 -0.2880 0.062 Uiso 1 1 calc R . .
H7B H 0.8544 0.2050 -0.3003 0.062 Uiso 1 1 calc R . .
C8 C 0.98518(18) 0.30107(18) -0.14518(18) 0.0519(5) Uani 1 1 d . . .
H8A H 1.0160 0.3808 -0.0873 0.062 Uiso 1 1 calc R . .
H8B H 1.0468 0.2858 -0.1589 0.062 Uiso 1 1 calc R . .
C9 C 0.94440(18) 0.22983(17) -0.09816(16) 0.0473(4) Uani 1 1 d . . .
H9A H 0.8792 0.1604 -0.1585 0.057 Uiso 1 1 calc R . .
H9B H 1.0032 0.2085 -0.0654 0.057 Uiso 1 1 calc R . .
C10 C 0.87160(14) 0.23695(14) 0.03165(13) 0.0356(4) Uani 1 1 d . . .
C11 C 0.86840(13) 0.30823(14) 0.13015(13) 0.0347(4) Uani 1 1 d . . .
C12 C 0.90715(16) 0.42577(15) 0.17369(16) 0.0431(4) Uani 1 1 d . . .
H12 H 0.9339 0.4586 0.1359 0.052 Uiso 1 1 calc R . .
C13 C 0.90555(17) 0.49082(16) 0.26978(17) 0.0501(5) Uani 1 1 d . . .
H13 H 0.9303 0.5693 0.2978 0.060 Uiso 1 1 calc R . .
C14 C 0.86848(16) 0.44591(16) 0.32919(16) 0.0468(5) Uani 1 1 d . . .
H14 H 0.8704 0.4940 0.3974 0.056 Uiso 1 1 calc R . .
C15 C 0.82956(13) 0.33272(15) 0.28857(14) 0.0373(4) Uani 1 1 d . . .
C16 C 0.82727(13) 0.25989(14) 0.18654(13) 0.0337(4) Uani 1 1 d . . .
C17 C 0.78765(14) 0.14239(15) 0.14211(14) 0.0380(4) Uani 1 1 d . . .
H17 H 0.7597 0.1093 0.1791 0.046 Uiso 1 1 calc R . .
C18 C 0.78978(15) 0.07699(15) 0.04597(15) 0.0408(4) Uani 1 1 d . . .
H18 H 0.7617 -0.0019 0.0159 0.049 Uiso 1 1 calc R . .
C19 C 0.83244(15) 0.12332(14) -0.00991(14) 0.0389(4) Uani 1 1 d . . .
H19 H 0.8341 0.0761 -0.0762 0.047 Uiso 1 1 calc R . .
C20 C 0.80622(16) 0.34988(18) 0.44902(14) 0.0475(5) Uani 1 1 d . . .
H20A H 0.7745 0.4055 0.4495 0.057 Uiso 1 1 calc R . .
H20B H 0.8861 0.3909 0.5005 0.057 Uiso 1 1 calc R . .
C21 C 0.74987(18) 0.2780(2) 0.48674(17) 0.0566(5) Uani 1 1 d . . .
H21A H 0.7507 0.2031 0.4499 0.068 Uiso 1 1 calc R . .
H21B H 0.7944 0.3114 0.5676 0.068 Uiso 1 1 calc R . .
C22 C 0.6323(2) 0.2619(2) 0.4651(2) 0.0696(7) Uani 1 1 d . . .
H22A H 0.6136 0.2358 0.5137 0.084 Uiso 1 1 calc R . .
H22B H 0.6280 0.3357 0.4867 0.084 Uiso 1 1 calc R . .
C23 C 0.54656(15) 0.21452(19) 0.27410(17) 0.0479(5) Uani 1 1 d . . .
C24 C 0.56945(16) 0.32162(19) 0.29157(17) 0.0503(5) Uani 1 1 d . . .
H24 H 0.5828 0.3802 0.3607 0.060 Uiso 1 1 calc R . .
C25 C 0.57299(16) 0.34365(18) 0.20812(17) 0.0478(4) Uani 1 1 d . . .
H25 H 0.5902 0.4179 0.2206 0.057 Uiso 1 1 calc R . .
C26 C 0.55158(15) 0.25828(17) 0.10671(16) 0.0440(4) Uani 1 1 d . . .
C27 C 0.51630(17) 0.14837(18) 0.08594(17) 0.0516(5) Uani 1 1 d . . .
H27 H 0.4945 0.0883 0.0142 0.062 Uiso 1 1 calc R . .
C28 C 0.51296(17) 0.12650(19) 0.16864(18) 0.0525(5) Uani 1 1 d . . .
H28 H 0.4877 0.0514 0.1540 0.063 Uiso 1 1 calc R . .
C29 C 0.23306(15) 0.01672(15) 0.52030(15) 0.0409(4) Uani 1 1 d . . .
C30 C 0.13719(16) -0.00194(16) 0.53433(15) 0.0456(4) Uani 1 1 d . . .
H30 H 0.0683 -0.0264 0.4741 0.055 Uiso 1 1 calc R . .
C31 C 0.14159(17) 0.01479(17) 0.63507(16) 0.0489(5) Uani 1 1 d . . .
H31 H 0.0759 0.0010 0.6444 0.059 Uiso 1 1 calc R . .
C32 C 0.24318(17) 0.05209(16) 0.72339(15) 0.0465(4) Uani 1 1 d . . .
C33 C 0.33594(17) 0.05584(18) 0.70591(17) 0.0528(5) Uani 1 1 d . . .
H33 H 0.4022 0.0692 0.7628 0.063 Uiso 1 1 calc R . .
C34 C 0.33126(17) 0.03990(18) 0.60463(17) 0.0516(5) Uani 1 1 d . . .
H34 H 0.3953 0.0448 0.5927 0.062 Uiso 1 1 calc R . .
C35 C 0.21718(19) 0.1693(2) 0.87070(18) 0.0573(5) Uani 1 1 d . . .
H35A H 0.1893 0.1590 0.9224 0.069 Uiso 1 1 calc R . .
H35B H 0.1546 0.1603 0.8081 0.069 Uiso 1 1 calc R . .
C36 C 0.30732(18) 0.28876(18) 0.93144(16) 0.0514(5) Uani 1 1 d . . .
H36A H 0.2735 0.3424 0.9545 0.062 Uiso 1 1 calc R . .
H36B H 0.3641 0.3002 0.9999 0.062 Uiso 1 1 calc R . .
C37 C 0.36475(16) 0.31796(17) 0.86747(15) 0.0478(5) Uani 1 1 d . . .
H37A H 0.4175 0.3977 0.9124 0.057 Uiso 1 1 calc R . .
H37B H 0.4067 0.2713 0.8509 0.057 Uiso 1 1 calc R . .
C38 C 0.32146(15) 0.32446(15) 0.69943(14) 0.0386(4) Uani 1 1 d . . .
C39 C 0.23744(14) 0.31181(13) 0.60404(14) 0.0347(4) Uani 1 1 d . . .
C40 C 0.12409(14) 0.26636(14) 0.57761(15) 0.0372(4) Uani 1 1 d . . .
H40 H 0.1017 0.2409 0.6221 0.045 Uiso 1 1 calc R . .
C41 C 0.04688(14) 0.25927(14) 0.48777(14) 0.0390(4) Uani 1 1 d . . .
H41 H -0.0293 0.2269 0.4693 0.047 Uiso 1 1 calc R . .
C42 C 0.07796(14) 0.29889(15) 0.42240(14) 0.0383(4) Uani 1 1 d . . .
H42 H 0.0232 0.2959 0.3621 0.046 Uiso 1 1 calc R . .
C43 C 0.18694(14) 0.34185(14) 0.44519(14) 0.0361(4) Uani 1 1 d . . .
C44 C 0.27013(14) 0.34640(14) 0.53536(14) 0.0354(4) Uani 1 1 d . . .
C45 C 0.38294(15) 0.38336(16) 0.55653(15) 0.0429(4) Uani 1 1 d . . .
H45 H 0.4052 0.4048 0.5097 0.051 Uiso 1 1 calc R . .
C46 C 0.45918(15) 0.38779(18) 0.64507(17) 0.0485(5) Uani 1 1 d . . .
H46 H 0.5343 0.4104 0.6578 0.058 Uiso 1 1 calc R . .
C47 C 0.42946(15) 0.35984(17) 0.71758(16) 0.0471(4) Uani 1 1 d . . .
H47 H 0.4845 0.3655 0.7795 0.056 Uiso 1 1 calc R . .
C48 C 0.14341(16) 0.38081(17) 0.29608(15) 0.0437(4) Uani 1 1 d . . .
H48A H 0.1092 0.4321 0.3249 0.052 Uiso 1 1 calc R . .
H48B H 0.0846 0.3041 0.2457 0.052 Uiso 1 1 calc R . .
C49 C 0.19857(18) 0.41660(17) 0.23371(17) 0.0492(5) Uani 1 1 d . . .
H49A H 0.1415 0.4127 0.1704 0.059 Uiso 1 1 calc R . .
H49B H 0.2518 0.4959 0.2835 0.059 Uiso 1 1 calc R . .
C50 C 0.25903(17) 0.34868(17) 0.18995(17) 0.0497(5) Uani 1 1 d . . .
H50A H 0.2901 0.3772 0.1487 0.060 Uiso 1 1 calc R . .
H50B H 0.3213 0.3583 0.2532 0.060 Uiso 1 1 calc R . .
C51 C 0.18310(15) 0.16861(15) 0.17042(14) 0.0394(4) Uani 1 1 d . . .
C52 C 0.08034(15) 0.10440(15) 0.15277(14) 0.0411(4) Uani 1 1 d . . .
H52 H 0.0149 0.0962 0.0988 0.049 Uiso 1 1 calc R . .
C53 C 0.07396(14) 0.05234(15) 0.21465(14) 0.0394(4) Uani 1 1 d . . .
H53 H 0.0036 0.0099 0.2045 0.047 Uiso 1 1 calc R . .
C54 C 0.16889(14) 0.06132(14) 0.29133(14) 0.0368(4) Uani 1 1 d . . .
C55 C 0.27180(15) 0.11818(15) 0.30121(15) 0.0413(4) Uani 1 1 d . . .
H55 H 0.3371 0.1204 0.3497 0.050 Uiso 1 1 calc R . .
C56 C 0.27813(15) 0.17097(16) 0.24042(16) 0.0438(4) Uani 1 1 d . . .
H56 H 0.3479 0.2092 0.2464 0.053 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'
O O 0.0106 0.0060 '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'
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
C4 O1 C7 116.96(15) . . ?
C10 O2 C9 117.37(14) . . ?
C15 O3 C20 117.23(14) . . ?
C23 O4 C22 119.50(18) . . ?
C32 O5 C35 114.62(16) . . ?
C38 O6 C37 117.17(14) . . ?
C43 O7 C48 116.35(14) . . ?
C51 O8 C50 115.00(14) . . ?
N2 N1 C26 114.00(17) . . ?
N1 N2 C1 114.29(17) . . ?
N4 N3 C54 114.48(15) . . ?
N3 N4 C29 113.63(15) . . ?
C6 C1 C2 119.58(19) . . ?
C6 C1 N2 116.04(18) . . ?
C2 C1 N2 123.83(18) . . ?
C3 C2 C1 119.50(19) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 120.35(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 O1 116.80(18) . . ?
C3 C4 C5 120.23(19) . . ?
O1 C4 C5 122.95(19) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.90(19) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 C8 114.86(17) . . ?
O1 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
O1 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 117.59(17) . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
C9 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
O2 C9 C8 109.82(16) . . ?
O2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 C19 124.75(15) . . ?
O2 C10 C11 114.71(15) . . ?
C19 C10 C11 120.54(16) . . ?
C12 C11 C16 119.87(16) . . ?
C12 C11 C10 121.41(16) . . ?
C16 C11 C10 118.71(15) . . ?
C13 C12 C11 119.30(18) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 122.17(18) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 119.79(17) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O3 C15 C14 124.65(16) . . ?
O3 C15 C16 114.89(15) . . ?
C14 C15 C16 120.45(17) . . ?
C17 C16 C11 119.63(15) . . ?
C17 C16 C15 121.97(16) . . ?
C11 C16 C15 118.38(15) . . ?
C18 C17 C16 119.64(16) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 121.69(16) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C10 C19 C18 119.76(16) . . ?
C10 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
O3 C20 C21 109.48(17) . . ?
O3 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
O3 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 C20 116.66(18) . . ?
C22 C21 H21A 108.1 . . ?
C20 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C20 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
O4 C22 C21 115.4(2) . . ?
O4 C22 H22A 108.4 . . ?
C21 C22 H22A 108.4 . . ?
O4 C22 H22B 108.4 . . ?
C21 C22 H22B 108.4 . . ?
H22A C22 H22B 107.5 . . ?
O4 C23 C24 124.4(2) . . ?
O4 C23 C28 115.7(2) . . ?
C24 C23 C28 119.86(19) . . ?
C23 C24 C25 119.73(19) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 120.35(19) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 119.19(19) . . ?
C25 C26 N1 115.68(18) . . ?
C27 C26 N1 124.67(18) . . ?
C28 C27 C26 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C23 119.8(2) . . ?
C27 C28 H28 120.1 . . ?
C23 C28 H28 120.1 . . ?
C30 C29 C34 119.37(18) . . ?
C30 C29 N4 124.20(17) . . ?
C34 C29 N4 115.78(17) . . ?
C31 C30 C29 120.28(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 119.47(19) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
O5 C32 C33 117.56(18) . . ?
O5 C32 C31 122.23(19) . . ?
C33 C32 C31 120.21(18) . . ?
C32 C33 C34 119.31(19) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C29 120.2(2) . . ?
C33 C34 H34 119.9 . . ?
C29 C34 H34 119.9 . . ?
O5 C35 C36 112.82(18) . . ?
O5 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
O5 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
C37 C36 C35 116.68(17) . . ?
C37 C36 H36A 108.1 . . ?
C35 C36 H36A 108.1 . . ?
C37 C36 H36B 108.1 . . ?
C35 C36 H36B 108.1 . . ?
H36A C36 H36B 107.3 . . ?
O6 C37 C36 109.11(16) . . ?
O6 C37 H37A 109.9 . . ?
C36 C37 H37A 109.9 . . ?
O6 C37 H37B 109.9 . . ?
C36 C37 H37B 109.9 . . ?
H37A C37 H37B 108.3 . . ?
O6 C38 C47 125.17(16) . . ?
O6 C38 C39 114.60(15) . . ?
C47 C38 C39 120.23(17) . . ?
C40 C39 C44 119.87(15) . . ?
C40 C39 C38 121.70(16) . . ?
C44 C39 C38 118.43(15) . . ?
C41 C40 C39 119.72(17) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C42 121.29(16) . . ?
C40 C41 H41 119.4 . . ?
C42 C41 H41 119.4 . . ?
C43 C42 C41 120.19(16) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 H42 119.9 . . ?
C42 C43 O7 124.39(15) . . ?
C42 C43 C44 120.45(16) . . ?
O7 C43 C44 115.16(15) . . ?
C39 C44 C45 119.88(15) . . ?
C39 C44 C43 118.31(15) . . ?
C45 C44 C43 121.81(16) . . ?
C46 C45 C44 119.27(17) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 121.71(17) . . ?
C45 C46 H46 119.1 . . ?
C47 C46 H46 119.1 . . ?
C38 C47 C46 120.22(17) . . ?
C38 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
O7 C48 C49 108.82(15) . . ?
O7 C48 H48A 109.9 . . ?
C49 C48 H48A 109.9 . . ?
O7 C48 H48B 109.9 . . ?
C49 C48 H48B 109.9 . . ?
H48A C48 H48B 108.3 . . ?
C50 C49 C48 115.47(16) . . ?
C50 C49 H49A 108.4 . . ?
C48 C49 H49A 108.4 . . ?
C50 C49 H49B 108.4 . . ?
C48 C49 H49B 108.4 . . ?
H49A C49 H49B 107.5 . . ?
O8 C50 C49 112.17(17) . . ?
O8 C50 H50A 109.2 . . ?
C49 C50 H50A 109.2 . . ?
O8 C50 H50B 109.2 . . ?
C49 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C52 C51 O8 118.11(16) . . ?
C52 C51 C56 120.37(17) . . ?
O8 C51 C56 121.51(16) . . ?
C51 C52 C53 119.14(16) . . ?
C51 C52 H52 120.4 . . ?
C53 C52 H52 120.4 . . ?
C52 C53 C54 120.78(16) . . ?
C52 C53 H53 119.6 . . ?
C54 C53 H53 119.6 . . ?
C53 C54 C55 119.39(17) . . ?
C53 C54 N3 116.34(15) . . ?
C55 C54 N3 123.78(16) . . ?
C56 C55 C54 119.65(17) . . ?
C56 C55 H55 120.2 . . ?
C54 C55 H55 120.2 . . ?
C55 C56 C51 120.21(17) . . ?
C55 C56 H56 119.9 . . ?
C51 C56 H56 119.9 . . ?
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 C4 1.379(2) . ?
O1 C7 1.423(3) . ?
O2 C10 1.373(2) . ?
O2 C9 1.421(2) . ?
O3 C15 1.365(2) . ?
O3 C20 1.434(2) . ?
O4 C23 1.373(2) . ?
O4 C22 1.411(3) . ?
O5 C32 1.373(2) . ?
O5 C35 1.411(3) . ?
O6 C38 1.366(2) . ?
O6 C37 1.430(2) . ?
O7 C43 1.371(2) . ?
O7 C48 1.440(2) . ?
O8 C51 1.384(2) . ?
O8 C50 1.443(2) . ?
N1 N2 1.252(2) . ?
N1 C26 1.420(2) . ?
N2 C1 1.425(2) . ?
N3 N4 1.259(2) . ?
N3 C54 1.417(2) . ?
N4 C29 1.424(2) . ?
C1 C6 1.382(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.506(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.523(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C19 1.371(2) . ?
C10 C11 1.421(2) . ?
C11 C12 1.418(2) . ?
C11 C16 1.420(2) . ?
C12 C13 1.356(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.404(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.429(2) . ?
C16 C17 1.416(2) . ?
C17 C18 1.362(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.406(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.509(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.508(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.375(3) . ?
C23 C28 1.390(3) . ?
C24 C25 1.382(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(3) . ?
C27 C28 1.370(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.389(3) . ?
C29 C34 1.391(3) . ?
C30 C31 1.375(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.382(3) . ?
C33 C34 1.384(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.539(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.510(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C47 1.368(3) . ?
C38 C39 1.432(2) . ?
C39 C40 1.414(2) . ?
C39 C44 1.418(2) . ?
C40 C41 1.368(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.403(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.368(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.430(2) . ?
C44 C45 1.420(2) . ?
C45 C46 1.367(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.402(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.509(3) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.508(3) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.382(3) . ?
C51 C56 1.386(3) . ?
C52 C53 1.381(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.385(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.397(2) . ?
C55 C56 1.375(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
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
C26 N1 N2 C1 -168.37(14) . . . . ?
C54 N3 N4 C29 166.33(14) . . . . ?
N1 N2 C1 C6 178.27(16) . . . . ?
N1 N2 C1 C2 6.9(2) . . . . ?
C6 C1 C2 C3 -4.4(3) . . . . ?
N2 C1 C2 C3 166.68(17) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 O1 -172.06(17) . . . . ?
C2 C3 C4 C5 6.5(3) . . . . ?
C7 O1 C4 C3 135.87(18) . . . . ?
C7 O1 C4 C5 -42.6(3) . . . . ?
C3 C4 C5 C6 -7.1(3) . . . . ?
O1 C4 C5 C6 171.32(18) . . . . ?
C4 C5 C6 C1 2.0(3) . . . . ?
C2 C1 C6 C5 3.7(3) . . . . ?
N2 C1 C6 C5 -168.05(17) . . . . ?
C4 O1 C7 C8 -68.5(2) . . . . ?
O1 C7 C8 C9 82.2(2) . . . . ?
C10 O2 C9 C8 176.81(15) . . . . ?
C7 C8 C9 O2 -95.5(2) . . . . ?
C9 O2 C10 C19 -14.4(2) . . . . ?
C9 O2 C10 C11 165.94(15) . . . . ?
O2 C10 C11 C12 0.5(2) . . . . ?
C19 C10 C11 C12 -179.17(16) . . . . ?
O2 C10 C11 C16 -178.26(13) . . . . ?
C19 C10 C11 C16 2.0(2) . . . . ?
C16 C11 C12 C13 0.8(3) . . . . ?
C10 C11 C12 C13 -178.00(17) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 -1.8(3) . . . . ?
C20 O3 C15 C14 -8.7(2) . . . . ?
C20 O3 C15 C16 171.15(15) . . . . ?
C13 C14 C15 O3 -179.63(17) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C12 C11 C16 C17 179.36(15) . . . . ?
C10 C11 C16 C17 -1.8(2) . . . . ?
C12 C11 C16 C15 -2.0(2) . . . . ?
C10 C11 C16 C15 176.85(14) . . . . ?
O3 C15 C16 C17 0.1(2) . . . . ?
C14 C15 C16 C17 179.94(16) . . . . ?
O3 C15 C16 C11 -178.53(13) . . . . ?
C14 C15 C16 C11 1.3(2) . . . . ?
C11 C16 C17 C18 0.2(2) . . . . ?
C15 C16 C17 C18 -178.39(16) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
O2 C10 C19 C18 179.68(15) . . . . ?
C11 C10 C19 C18 -0.6(3) . . . . ?
C17 C18 C19 C10 -1.0(3) . . . . ?
C15 O3 C20 C21 175.05(15) . . . . ?
O3 C20 C21 C22 -92.5(2) . . . . ?
C23 O4 C22 C21 -71.0(3) . . . . ?
C20 C21 C22 O4 76.4(3) . . . . ?
C22 O4 C23 C24 -33.9(3) . . . . ?
C22 O4 C23 C28 147.6(2) . . . . ?
O4 C23 C24 C25 173.16(18) . . . . ?
C28 C23 C24 C25 -8.4(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C24 C25 C26 C27 6.0(3) . . . . ?
C24 C25 C26 N1 -166.54(17) . . . . ?
N2 N1 C26 C25 167.87(16) . . . . ?
N2 N1 C26 C27 -4.2(3) . . . . ?
C25 C26 C27 C28 -6.1(3) . . . . ?
N1 C26 C27 C28 165.71(18) . . . . ?
C26 C27 C28 C23 -1.0(3) . . . . ?
O4 C23 C28 C27 -173.13(18) . . . . ?
C24 C23 C28 C27 8.3(3) . . . . ?
N3 N4 C29 C30 -0.1(3) . . . . ?
N3 N4 C29 C34 -170.79(16) . . . . ?
C34 C29 C30 C31 7.3(3) . . . . ?
N4 C29 C30 C31 -163.06(18) . . . . ?
C29 C30 C31 C32 0.9(3) . . . . ?
C35 O5 C32 C33 126.3(2) . . . . ?
C35 O5 C32 C31 -54.0(3) . . . . ?
C30 C31 C32 O5 170.43(19) . . . . ?
C30 C31 C32 C33 -9.9(3) . . . . ?
O5 C32 C33 C34 -169.84(19) . . . . ?
C31 C32 C33 C34 10.4(3) . . . . ?
C32 C33 C34 C29 -2.1(3) . . . . ?
C30 C29 C34 C33 -6.7(3) . . . . ?
N4 C29 C34 C33 164.44(19) . . . . ?
C32 O5 C35 C36 -90.6(2) . . . . ?
O5 C35 C36 C37 55.2(2) . . . . ?
C38 O6 C37 C36 177.60(16) . . . . ?
C35 C36 C37 O6 56.0(2) . . . . ?
C37 O6 C38 C47 5.1(3) . . . . ?
C37 O6 C38 C39 -175.10(15) . . . . ?
O6 C38 C39 C40 -5.3(2) . . . . ?
C47 C38 C39 C40 174.49(17) . . . . ?
O6 C38 C39 C44 174.50(14) . . . . ?
C47 C38 C39 C44 -5.7(3) . . . . ?
C44 C39 C40 C41 -2.0(2) . . . . ?
C38 C39 C40 C41 177.82(16) . . . . ?
C39 C40 C41 C42 -1.6(3) . . . . ?
C40 C41 C42 C43 2.5(3) . . . . ?
C41 C42 C43 O7 -179.40(15) . . . . ?
C41 C42 C43 C44 0.3(3) . . . . ?
C48 O7 C43 C42 0.2(2) . . . . ?
C48 O7 C43 C44 -179.44(14) . . . . ?
C40 C39 C44 C45 -174.80(16) . . . . ?
C38 C39 C44 C45 5.4(2) . . . . ?
C40 C39 C44 C43 4.6(2) . . . . ?
C38 C39 C44 C43 -175.20(15) . . . . ?
C42 C43 C44 C39 -3.8(2) . . . . ?
O7 C43 C44 C39 175.91(14) . . . . ?
C42 C43 C44 C45 175.64(16) . . . . ?
O7 C43 C44 C45 -4.7(2) . . . . ?
C39 C44 C45 C46 -1.7(3) . . . . ?
C43 C44 C45 C46 178.89(17) . . . . ?
C44 C45 C46 C47 -1.9(3) . . . . ?
O6 C38 C47 C46 -177.92(17) . . . . ?
C39 C38 C47 C46 2.3(3) . . . . ?
C45 C46 C47 C38 1.6(3) . . . . ?
C43 O7 C48 C49 -173.39(14) . . . . ?
O7 C48 C49 C50 56.7(2) . . . . ?
C51 O8 C50 C49 -89.8(2) . . . . ?
C48 C49 C50 O8 57.1(2) . . . . ?
C50 O8 C51 C52 126.51(18) . . . . ?
C50 O8 C51 C56 -52.5(2) . . . . ?
O8 C51 C52 C53 -172.14(15) . . . . ?
C56 C51 C52 C53 6.9(3) . . . . ?
C51 C52 C53 C54 -1.8(3) . . . . ?
C52 C53 C54 C55 -3.8(3) . . . . ?
C52 C53 C54 N3 168.46(15) . . . . ?
N4 N3 C54 C53 178.20(15) . . . . ?
N4 N3 C54 C55 -9.9(2) . . . . ?
C53 C54 C55 C56 4.5(3) . . . . ?
N3 C54 C55 C56 -167.21(17) . . . . ?
C54 C55 C56 C51 0.5(3) . . . . ?
C52 C51 C56 C55 -6.3(3) . . . . ?
O8 C51 C56 C55 172.72(16) . . . . ?
