#------------------------------------------------------------------------------
#$Date: 2025-11-29 19:28:37 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303634 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/58/1575865.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_1575865
loop_
_publ_author_name
'Lin, Yun-Hsien'
'Wang, Xiqu'
'Szczepanik, Dariusz W.'
'Wieczorkiewicz, Paweł A'
'Miljanić, Ognjen Š'
_publ_section_title
;
 Inverted azolophanes: alternant o-heteroarene/p-arene
 macrocycles.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              19967
_journal_page_last               19972
_journal_paper_doi               10.1039/d5sc05981j
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C79 H79.8 N11 O9'
_chemical_formula_weight         1327.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-07 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.757(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.9415(8)
_cell_length_b                   9.5284(3)
_cell_length_c                   32.2718(9)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.08
_cell_measurement_theta_min      3.09
_cell_volume                     8691.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX6'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1168
_diffrn_reflns_av_unetI/netI     0.0972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            74150
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.403
_diffrn_reflns_theta_min         2.663
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.7236
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ('SADABS')
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_description       plate
_exptl_crystal_F_000             2811
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     951
_refine_ls_number_reflns         15437
_refine_ls_number_restraints     262
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.1737
_refine_ls_R_factor_gt           0.0899
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²+9.5484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1930
_refine_ls_wR_factor_ref         0.2290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7634
_reflns_number_total             15437
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc05981j2.cif
_cod_data_source_block           JL641_XW3084
_cod_depositor_comments
'Adding full bibliography for 1575863--1575867.cif.'
_cod_original_cell_volume        8691.8(4)
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_original_formula_sum        'C79 H79.80 N11 O9'
_cod_database_code               1575865
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37218(9) 1.0658(3) 0.12565(10) 0.0474(7) Uani 1 1 d . . . . .
H1 H 0.343599 1.069867 0.119506 0.071 Uiso 1 1 calc R U . . .
O2 O 0.33163(14) 0.2013(4) 0.61021(14) 0.0915(13) Uani 1 1 d . . . . .
H2' H 0.303555 0.217587 0.590224 0.137 Uiso 1 1 calc R U . . .
O3 O 0.92138(16) 0.3272(7) 0.31156(16) 0.147(2) Uani 1 1 d . . . . .
H3' H 0.948910 0.313055 0.333123 0.220 Uiso 1 1 calc R U . . .
O4 O 0.87045(9) -0.5401(3) 0.78297(10) 0.0507(8) Uani 1 1 d . . . . .
H4 H 0.897689 -0.554849 0.786064 0.076 Uiso 1 1 calc R U . . .
O5 O 0.36212(12) 0.4293(4) 0.43115(13) 0.0711(10) Uani 1 1 d . . . . .
O6 O 0.57943(12) 0.7556(4) 0.25043(13) 0.0760(11) Uani 1 1 d . . . . .
O7 O 0.66755(12) -0.2163(5) 0.66700(12) 0.0909(14) Uani 1 1 d . . . . .
N1 N 0.45906(11) 0.6108(4) 0.29591(11) 0.0397(8) Uani 1 1 d . . . . .
N2 N 0.51754(11) 0.6276(4) 0.27783(11) 0.0426(9) Uani 1 1 d . . . . .
H2N H 0.533582 0.653192 0.263109 0.051 Uiso 1 1 calc R U . . .
N3 N 0.45077(11) 0.3062(4) 0.49429(12) 0.0409(8) Uani 1 1 d . . . . .
H3N H 0.426156 0.359014 0.476979 0.049 Uiso 1 1 calc R U . . .
N4 N 0.49818(12) 0.1667(4) 0.55150(11) 0.0423(9) Uani 1 1 d . . . . .
N5 N 0.74373(12) 0.3445(4) 0.35465(12) 0.0536(10) Uani 1 1 d . . . . .
N6 N 0.79457(12) 0.2346(4) 0.41883(13) 0.0544(10) Uani 1 1 d . . . . .
H6N H 0.821002 0.195980 0.439814 0.065 Uiso 1 1 calc R U . . .
N7 N 0.78134(11) -0.0932(3) 0.60969(11) 0.0390(8) Uani 1 1 d . . . . .
N8 N 0.72149(11) -0.1223(4) 0.62514(11) 0.0411(8) Uani 1 1 d . . . . .
H8 H 0.705039 -0.151375 0.639058 0.049 Uiso 1 1 calc R U . . .
C1 C 0.44614(14) 0.7700(4) 0.22979(14) 0.0410(10) Uani 1 1 d . . . . .
C2 C 0.46801(15) 0.8490(5) 0.20875(16) 0.0526(12) Uani 1 1 d . . . . .
H2A H 0.500598 0.834624 0.217964 0.063 Uiso 1 1 calc R U . . .
C3 C 0.44297(14) 0.9473(5) 0.17485(16) 0.0489(11) Uani 1 1 d . . . . .
H3A H 0.458738 1.001910 0.161733 0.059 Uiso 1 1 calc R U . . .
C4 C 0.39486(14) 0.9675(4) 0.15960(14) 0.0411(10) Uani 1 1 d . . . . .
C5 C 0.37236(15) 0.8880(5) 0.17964(14) 0.0436(11) Uani 1 1 d . . . . .
H5 H 0.339508 0.900242 0.169527 0.052 Uiso 1 1 calc R U . . .
C6 C 0.39792(14) 0.7910(5) 0.21434(14) 0.0445(11) Uani 1 1 d . . . . .
H6 H 0.382251 0.737703 0.227878 0.053 Uiso 1 1 calc R U . . .
C7 C 0.47299(13) 0.6708(4) 0.26725(14) 0.0387(10) Uani 1 1 d . . . . .
C8 C 0.49667(13) 0.5281(4) 0.32698(14) 0.0390(10) Uani 1 1 d . . . . .
C9 C 0.53331(14) 0.5369(4) 0.31551(14) 0.0426(10) Uani 1 1 d . . . . .
C10 C 0.49386(13) 0.4596(4) 0.36612(13) 0.0372(10) Uani 1 1 d . . . . .
C11 C 0.46971(13) 0.5252(4) 0.38705(14) 0.0394(10) Uani 1 1 d . . . . .
H11 H 0.454040 0.611585 0.374588 0.047 Uiso 1 1 calc R U . . .
C12 C 0.46783(13) 0.4680(4) 0.42566(14) 0.0401(10) Uani 1 1 d . . . . .
H12 H 0.450508 0.514804 0.438784 0.048 Uiso 1 1 calc R U . . .
C13 C 0.49111(13) 0.3423(4) 0.44551(14) 0.0365(10) Uani 1 1 d . . . . .
C14 C 0.51502(13) 0.2738(4) 0.42403(14) 0.0387(10) Uani 1 1 d . . . . .
H14 H 0.530221 0.186580 0.436149 0.046 Uiso 1 1 calc R U . . .
C15 C 0.51667(14) 0.3317(4) 0.38559(14) 0.0418(10) Uani 1 1 d . . . . .
H15 H 0.533496 0.284432 0.372026 0.050 Uiso 1 1 calc R U . . .
C16 C 0.58093(14) 0.4765(4) 0.33378(15) 0.0411(10) Uani 1 1 d . . . . .
C17 C 0.59874(15) 0.4444(5) 0.30301(15) 0.0486(11) Uani 1 1 d . . . . .
H17 H 0.579494 0.458768 0.270380 0.058 Uiso 1 1 calc R U . . .
C18 C 0.64393(15) 0.3919(5) 0.31903(15) 0.0508(12) Uani 1 1 d . . . . .
H18 H 0.655171 0.370662 0.297192 0.061 Uiso 1 1 calc R U . . .
C19 C 0.67349(14) 0.3693(5) 0.36678(14) 0.0425(10) Uani 1 1 d . . . . .
C20 C 0.65575(14) 0.4035(4) 0.39748(14) 0.0407(10) Uani 1 1 d . . . . .
H20 H 0.675159 0.389915 0.430122 0.049 Uiso 1 1 calc R U . . .
C21 C 0.61054(13) 0.4568(4) 0.38175(14) 0.0410(10) Uani 1 1 d . . . . .
H21 H 0.599529 0.480023 0.403628 0.049 Uiso 1 1 calc R U . . .
C22 C 0.48951(13) 0.2833(4) 0.48665(14) 0.0372(10) Uani 1 1 d . . . . .
C23 C 0.45715(14) 0.2340(5) 0.53260(14) 0.0398(10) Uani 1 1 d . . . . .
C24 C 0.51876(13) 0.1975(4) 0.52269(13) 0.0377(10) Uani 1 1 d . . . . .
C25 C 0.72154(14) 0.3167(5) 0.38187(15) 0.0452(11) Uani 1 1 d . . . . .
C26 C 0.78734(17) 0.2930(6) 0.37794(16) 0.0564(13) Uani 1 1 d . . . . .
C27 C 0.75299(14) 0.2466(5) 0.42176(15) 0.0445(11) Uani 1 1 d . . . . .
C28 C 0.42345(15) 0.2286(5) 0.55154(16) 0.0475(11) Uani 1 1 d . . . . .
C29 C 0.43796(19) 0.1789(6) 0.59627(18) 0.0653(14) Uani 1 1 d . . . . .
H29 H 0.469851 0.149718 0.614447 0.078 Uiso 1 1 calc R U . . .
C30 C 0.4071(2) 0.1705(6) 0.61537(19) 0.0723(16) Uani 1 1 d . . . . .
H30 H 0.418030 0.136948 0.646426 0.087 Uiso 1 1 calc R U . . .
C31 C 0.3607(2) 0.2107(6) 0.5893(2) 0.0691(16) Uani 1 1 d . . . . .
C32 C 0.34552(17) 0.2607(5) 0.5451(2) 0.0625(14) Uani 1 1 d . . . . .
H32 H 0.313564 0.289644 0.527254 0.075 Uiso 1 1 calc R U . . .
C33 C 0.37657(16) 0.2696(5) 0.52590(18) 0.0556(13) Uani 1 1 d . . . . .
H33 H 0.365485 0.304097 0.494934 0.067 Uiso 1 1 calc R U . . .
C34 C 0.56619(13) 0.1392(4) 0.53576(13) 0.0379(10) Uani 1 1 d . . . . .
C35 C 0.60132(14) 0.2136(4) 0.53164(14) 0.0397(10) Uani 1 1 d . . . . .
H35 H 0.594850 0.304843 0.518254 0.048 Uiso 1 1 calc R U . . .
C36 C 0.64598(14) 0.1554(5) 0.54695(14) 0.0419(10) Uani 1 1 d . . . . .
H36 H 0.669697 0.208092 0.543998 0.050 Uiso 1 1 calc R U . . .
C37 C 0.65681(14) 0.0218(4) 0.56652(14) 0.0382(10) Uani 1 1 d . . . . .
C38 C 0.62089(14) -0.0535(4) 0.56982(13) 0.0400(10) Uani 1 1 d . . . . .
H38 H 0.626863 -0.146161 0.582120 0.048 Uiso 1 1 calc R U . . .
C39 C 0.57665(14) 0.0059(5) 0.55528(13) 0.0401(10) Uani 1 1 d . . . . .
H39 H 0.553002 -0.045592 0.558742 0.048 Uiso 1 1 calc R U . . .
C40 C 0.82288(17) 0.2998(6) 0.36142(17) 0.0666(15) Uani 1 1 d . . . . .
C41 C 0.8102(2) 0.3248(9) 0.3159(2) 0.108(3) Uani 1 1 d . . . . .
H41 H 0.777613 0.334747 0.294340 0.130 Uiso 1 1 calc R U . . .
C42 C 0.8432(2) 0.3361(11) 0.3000(2) 0.137(4) Uani 1 1 d . . . . .
H42 H 0.833292 0.357350 0.268012 0.164 Uiso 1 1 calc R U . . .
C43 C 0.8894(2) 0.3172(9) 0.3294(2) 0.108(2) Uani 1 1 d . . . . .
C44 C 0.9034(2) 0.2852(10) 0.3747(3) 0.136(3) Uani 1 1 d . . . . .
H44 H 0.935823 0.268335 0.395480 0.163 Uiso 1 1 calc R U . . .
C45 C 0.8698(2) 0.2770(9) 0.3909(2) 0.111(3) Uani 1 1 d . . . . .
H45 H 0.879666 0.255182 0.422825 0.133 Uiso 1 1 calc R U . . .
C46 C 0.74888(15) 0.1857(4) 0.46161(15) 0.0435(11) Uani 1 1 d . . . . .
C47 C 0.70766(14) 0.1189(4) 0.45579(14) 0.0409(10) Uani 1 1 d . . . . .
H47 H 0.680913 0.116290 0.425649 0.049 Uiso 1 1 calc R U . . .
C48 C 0.70513(14) 0.0565(4) 0.49311(14) 0.0402(10) Uani 1 1 d . . . . .
H48 H 0.676351 0.014035 0.488424 0.048 Uiso 1 1 calc R U . . .
C49 C 0.74457(14) 0.0546(4) 0.53821(15) 0.0388(10) Uani 1 1 d . . . . .
C50 C 0.78546(14) 0.1212(4) 0.54347(15) 0.0431(10) Uani 1 1 d . . . . .
H50 H 0.812456 0.122039 0.573447 0.052 Uiso 1 1 calc R U . . .
C51 C 0.78810(14) 0.1857(5) 0.50687(15) 0.0467(11) Uani 1 1 d . . . . .
H51 H 0.816587 0.230969 0.511931 0.056 Uiso 1 1 calc R U . . .
C52 C 0.70489(13) -0.0371(4) 0.58620(13) 0.0372(10) Uani 1 1 d . . . . .
C53 C 0.74227(14) -0.0199(4) 0.57664(14) 0.0382(10) Uani 1 1 d . . . . .
C54 C 0.76757(14) -0.1541(4) 0.63849(14) 0.0403(10) Uani 1 1 d . . . . .
C55 C 0.79597(13) -0.2498(4) 0.67734(14) 0.0400(10) Uani 1 1 d . . . . .
C56 C 0.83965(14) -0.2972(5) 0.68424(14) 0.0445(11) Uani 1 1 d . . . . .
H56 H 0.852340 -0.263469 0.664722 0.053 Uiso 1 1 calc R U . . .
C57 C 0.86539(14) -0.3940(5) 0.71950(15) 0.0447(11) Uani 1 1 d . . . . .
H57 H 0.895257 -0.425942 0.723583 0.054 Uiso 1 1 calc R U . . .
C58 C 0.84783(14) -0.4434(5) 0.74829(14) 0.0419(10) Uani 1 1 d . . . . .
C59 C 0.80432(15) -0.3952(6) 0.74189(16) 0.0616(14) Uani 1 1 d . . . . .
H59 H 0.791737 -0.428926 0.761516 0.074 Uiso 1 1 calc R U . . .
C60 C 0.77896(16) -0.2983(6) 0.70712(16) 0.0608(14) Uani 1 1 d . . . . .
H60 H 0.749504 -0.264752 0.703661 0.073 Uiso 1 1 calc R U . . .
C61 C 0.2722(4) 0.7151(11) 0.3328(4) 0.101(3) Uani 0.620(8) 1 d . . P A 1
H61A H 0.275386 0.652818 0.310289 0.151 Uiso 0.620(8) 1 calc R U P A 1
H61B H 0.302962 0.757583 0.353314 0.151 Uiso 0.620(8) 1 calc R U P A 1
H61C H 0.249247 0.789175 0.315961 0.151 Uiso 0.620(8) 1 calc R U P A 1
C62 C 0.2546(4) 0.6279(18) 0.3633(4) 0.102(4) Uani 0.620(8) 1 d . U P A 1
H62A H 0.247224 0.692529 0.383029 0.122 Uiso 0.620(8) 1 calc R U P A 1
H62B H 0.225245 0.576917 0.342407 0.122 Uiso 0.620(8) 1 calc R U P A 1
C61' C 0.2424(8) 0.7399(19) 0.3480(7) 0.101(3) Uani 0.380(8) 1 d . . P A 2
H61D H 0.225914 0.786801 0.317546 0.151 Uiso 0.380(8) 1 calc R U P A 2
H61E H 0.268230 0.799717 0.369776 0.151 Uiso 0.380(8) 1 calc R U P A 2
H61F H 0.220064 0.722916 0.360424 0.151 Uiso 0.380(8) 1 calc R U P A 2
C62' C 0.2614(6) 0.608(2) 0.3425(5) 0.102(4) Uani 0.380(8) 1 d . U P A 2
H62C H 0.283034 0.624306 0.328866 0.122 Uiso 0.380(8) 1 calc R U P A 2
H62D H 0.235250 0.546744 0.320694 0.122 Uiso 0.380(8) 1 calc R U P A 2
C64 C 0.33482(19) 0.5021(6) 0.4001(2) 0.0702(15) Uani 1 1 d . . . . .
H64 H 0.345128 0.542710 0.379520 0.084 Uiso 1 1 calc R U . . .
C65 C 0.2709(2) 0.4605(8) 0.4232(3) 0.109(2) Uani 1 1 d . . . . .
H65A H 0.236127 0.449651 0.405515 0.131 Uiso 1 1 calc R U . . .
H65B H 0.285106 0.366046 0.432742 0.131 Uiso 1 1 calc R U . . .
C66 C 0.2828(2) 0.5440(7) 0.4634(3) 0.125(3) Uani 1 1 d . . . . .
H66A H 0.317297 0.548059 0.482147 0.187 Uiso 1 1 calc R U . . .
H66B H 0.269049 0.502684 0.482127 0.187 Uiso 1 1 calc R U . . .
H66C H 0.270324 0.639016 0.453774 0.187 Uiso 1 1 calc R U . . .
C67 C 0.5742(3) 1.0820(9) 0.2863(3) 0.156(3) Uani 1 1 d . . . . .
H67A H 0.553912 1.163524 0.271832 0.234 Uiso 1 1 calc R U . . .
H67B H 0.597557 1.105255 0.318442 0.234 Uiso 1 1 calc R U . . .
H67C H 0.554814 1.002908 0.286723 0.234 Uiso 1 1 calc R U . . .
C68 C 0.6007(3) 1.0405(8) 0.2571(3) 0.142(3) Uani 1 1 d . . . . .
H68A H 0.577486 1.006199 0.225771 0.171 Uiso 1 1 calc R U . . .
H68B H 0.616714 1.123978 0.252797 0.171 Uiso 1 1 calc R U . . .
C70 C 0.6219(2) 0.7919(7) 0.2773(2) 0.0874(19) Uani 1 1 d . . . . .
H70 H 0.644324 0.721552 0.294583 0.105 Uiso 1 1 calc R U . . .
C71 C 0.6859(3) 0.9670(10) 0.3156(3) 0.148(3) Uani 1 1 d . . . . .
H71A H 0.685642 1.045050 0.335685 0.178 Uiso 1 1 calc R U . . .
H71B H 0.701683 0.885704 0.336012 0.178 Uiso 1 1 calc R U . . .
C72 C 0.63117(18) -0.2007(7) 0.66953(17) 0.0750(17) Uani 1 1 d . . . . .
H72 H 0.609183 -0.276028 0.658243 0.090 Uiso 1 1 calc R U . . .
N12 N 0.61869(13) -0.0919(5) 0.68608(15) 0.0700(13) Uani 1 1 d . . . . .
N13 N 0.6363(2) 0.9284(7) 0.2822(2) 0.120(2) Uani 1 1 d . . . . .
N14 N 0.28944(17) 0.5308(5) 0.39218(17) 0.0796(14) Uani 1 1 d . . . . .
C74 C 0.5800(3) -0.1069(10) 0.7003(3) 0.058(2) Uani 0.601(5) 1 d . U P B 1
H74A H 0.566546 -0.202805 0.693250 0.069 Uiso 0.601(5) 1 calc R U P B 1
H74B H 0.592769 -0.089627 0.734268 0.069 Uiso 0.601(5) 1 calc R U P B 1
C75 C 0.5428(3) -0.0008(10) 0.6728(3) 0.065(2) Uani 0.601(5) 1 d . . P B 1
H75A H 0.534589 -0.007985 0.639615 0.097 Uiso 0.601(5) 1 calc R U P B 1
H75B H 0.554766 0.093614 0.684228 0.097 Uiso 0.601(5) 1 calc R U P B 1
H75C H 0.514517 -0.018530 0.676626 0.097 Uiso 0.601(5) 1 calc R U P B 1
C76 C 0.6462(8) 0.042(3) 0.6941(5) 0.096(5) Uani 0.601(5) 1 d . U P B 1
H76 H 0.637023 0.118220 0.672663 0.115 Uiso 0.601(5) 1 calc R U P B 1
C77 C 0.6868(6) 0.0391(15) 0.7369(5) 0.143(5) Uani 0.601(5) 1 d . . P B 1
H77A H 0.693772 -0.040940 0.756600 0.171 Uiso 0.601(5) 1 calc R U P B 1
H77B H 0.707708 0.117271 0.746633 0.171 Uiso 0.601(5) 1 calc R U P B 1
C74' C 0.5664(4) -0.0591(15) 0.6669(5) 0.058(2) Uani 0.399(5) 1 d . . P B 2
H74C H 0.560212 0.041418 0.658565 0.069 Uiso 0.399(5) 1 calc R U P B 2
H74D H 0.547270 -0.116217 0.638728 0.069 Uiso 0.399(5) 1 calc R U P B 2
C75' C 0.5546(5) -0.0952(15) 0.7057(5) 0.065(2) Uani 0.399(5) 1 d . U P B 2
H75D H 0.522932 -0.059751 0.697779 0.097 Uiso 0.399(5) 1 calc R U P B 2
H75E H 0.577849 -0.051944 0.734933 0.097 Uiso 0.399(5) 1 calc R U P B 2
H75F H 0.555224 -0.197296 0.709517 0.097 Uiso 0.399(5) 1 calc R U P B 2
C76' C 0.6516(13) 0.011(4) 0.7147(9) 0.096(5) Uani 0.399(5) 1 d . U P B 2
H76A H 0.683620 -0.030446 0.730851 0.115 Uiso 0.399(5) 1 calc R U P B 2
H76B H 0.642913 0.043786 0.738824 0.115 Uiso 0.399(5) 1 calc R U P B 2
C77' C 0.6520(9) 0.146(2) 0.6828(7) 0.143(5) Uani 0.399(5) 1 d . . P B 2
H77C H 0.662040 0.114623 0.659849 0.214 Uiso 0.399(5) 1 calc R U P B 2
H77D H 0.674125 0.217439 0.703176 0.214 Uiso 0.399(5) 1 calc R U P B 2
H77E H 0.620182 0.186362 0.666368 0.214 Uiso 0.399(5) 1 calc R U P B 2
C87 C 0.7131(3) 1.0099(11) 0.2911(4) 0.192(5) Uani 1 1 d . . . . .
H87A H 0.715068 0.930977 0.272606 0.288 Uiso 1 1 calc R U . . .
H87B H 0.745037 1.038139 0.314151 0.288 Uiso 1 1 calc R U . . .
H87C H 0.697187 1.089076 0.270267 0.288 Uiso 1 1 calc R U . . .
O1_1 O 0.2425(4) 0.269(2) 0.5585(7) 0.114(5) Uani 0.639(10) 1 d D U P C 1
O2_1 O 0.1494(4) 0.3406(13) 0.4947(5) 0.161(5) Uani 0.639(10) 1 d D U P C 1
C1_1 C 0.2170(5) 0.3648(16) 0.5716(5) 0.132(5) Uani 0.639(10) 1 d D U P C 1
H1A_1 H 0.238823 0.435541 0.593463 0.159 Uiso 0.639(10) 1 calc R U P C 1
H1B_1 H 0.201530 0.314582 0.587720 0.159 Uiso 0.639(10) 1 calc R U P C 1
C2_1 C 0.1797(5) 0.4371(13) 0.5278(5) 0.152(6) Uani 0.639(10) 1 d D U P C 1
H2A_1 H 0.160786 0.501328 0.536602 0.183 Uiso 0.639(10) 1 calc R U P C 1
H2B_1 H 0.195590 0.493999 0.513571 0.183 Uiso 0.639(10) 1 calc R U P C 1
C3_1 C 0.1749(5) 0.2369(15) 0.4852(4) 0.139(6) Uani 0.639(10) 1 d D U P C 1
H3A_1 H 0.191078 0.279814 0.468597 0.167 Uiso 0.639(10) 1 calc R U P C 1
H3B_1 H 0.152631 0.165093 0.464318 0.167 Uiso 0.639(10) 1 calc R U P C 1
C4_1 C 0.2108(5) 0.1677(15) 0.5291(5) 0.126(5) Uani 0.639(10) 1 d D U P C 1
H4A_1 H 0.194702 0.121275 0.545208 0.151 Uiso 0.639(10) 1 calc R U P C 1
H4B_1 H 0.228139 0.095281 0.521196 0.151 Uiso 0.639(10) 1 calc R U P C 1
O1_2 O 0.2367(7) 0.287(4) 0.5449(13) 0.114(5) Uani 0.361(10) 1 d D U P C 2
O2_2 O 0.1397(6) 0.286(2) 0.5105(9) 0.161(5) Uani 0.361(10) 1 d D U P C 2
C1_2 C 0.2072(9) 0.200(3) 0.5083(10) 0.126(5) Uani 0.361(10) 1 d D U P C 2
H1A_2 H 0.224524 0.113528 0.508358 0.151 Uiso 0.361(10) 1 calc R U P C 2
H1B_2 H 0.197171 0.248256 0.477984 0.151 Uiso 0.361(10) 1 calc R U P C 2
C2_2 C 0.1639(8) 0.162(2) 0.5143(12) 0.177(8) Uani 0.361(10) 1 d D U P C 2
H2A_2 H 0.143471 0.094651 0.489715 0.212 Uiso 0.361(10) 1 calc R U P C 2
H2B_2 H 0.173677 0.118020 0.545299 0.212 Uiso 0.361(10) 1 calc R U P C 2
C3_2 C 0.1684(8) 0.359(3) 0.5521(9) 0.166(8) Uani 0.361(10) 1 d D U P C 2
H3A_2 H 0.177294 0.296269 0.579463 0.199 Uiso 0.361(10) 1 calc R U P C 2
H3B_2 H 0.151374 0.440843 0.555528 0.199 Uiso 0.361(10) 1 calc R U P C 2
C4_2 C 0.2128(9) 0.406(3) 0.5488(11) 0.132(5) Uani 0.361(10) 1 d D U P C 2
H4A_2 H 0.203630 0.467457 0.521206 0.159 Uiso 0.361(10) 1 calc R U P C 2
H4B_2 H 0.233809 0.460040 0.577178 0.159 Uiso 0.361(10) 1 calc R U P C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 N1 C8 106.7(3) . . ?
C7 N2 C9 108.6(3) . . ?
C23 N3 C22 108.5(3) . . ?
C23 N4 C24 105.2(3) . . ?
C26 N5 C25 106.3(4) . . ?
C26 N6 C27 107.5(4) . . ?
C54 N7 C53 106.5(3) . . ?
C54 N8 C52 108.7(3) . . ?
C6 C1 C2 117.9(4) . . ?
C6 C1 C7 121.0(4) . . ?
C2 C1 C7 121.2(4) . . ?
C3 C2 C1 121.0(4) . . ?
C2 C3 C4 120.8(4) . . ?
O1 C4 C3 117.7(4) . . ?
O1 C4 C5 123.4(4) . . ?
C3 C4 C5 118.9(4) . . ?
C6 C5 C4 120.0(4) . . ?
C5 C6 C1 121.4(4) . . ?
N1 C7 N2 110.2(4) . . ?
N1 C7 C1 126.7(4) . . ?
N2 C7 C1 123.1(4) . . ?
C9 C8 N1 109.0(4) . . ?
C9 C8 C10 131.2(4) . . ?
N1 C8 C10 119.6(3) . . ?
N2 C9 C8 105.4(3) . . ?
N2 C9 C16 118.9(4) . . ?
C8 C9 C16 135.7(4) . . ?
C11 C10 C15 117.5(4) . . ?
C11 C10 C8 119.5(4) . . ?
C15 C10 C8 123.0(4) . . ?
C12 C11 C10 121.8(4) . . ?
C11 C12 C13 120.8(4) . . ?
C12 C13 C14 117.8(4) . . ?
C12 C13 C22 120.6(4) . . ?
C14 C13 C22 121.6(4) . . ?
C15 C14 C13 120.9(4) . . ?
C14 C15 C10 121.2(4) . . ?
C17 C16 C21 118.0(4) . . ?
C17 C16 C9 119.5(4) . . ?
C21 C16 C9 122.4(4) . . ?
C18 C17 C16 121.1(4) . . ?
C17 C18 C19 121.3(4) . . ?
C20 C19 C18 117.3(4) . . ?
C20 C19 C25 123.7(4) . . ?
C18 C19 C25 118.9(4) . . ?
C21 C20 C19 121.8(4) . . ?
C20 C21 C16 120.4(4) . . ?
C24 C22 N3 104.8(3) . . ?
C24 C22 C13 134.4(4) . . ?
N3 C22 C13 120.8(4) . . ?
N4 C23 N3 111.4(3) . . ?
N4 C23 C28 123.5(4) . . ?
N3 C23 C28 125.1(4) . . ?
C22 C24 N4 110.1(3) . . ?
C22 C24 C34 132.0(4) . . ?
N4 C24 C34 117.9(4) . . ?
C27 C25 N5 108.6(4) . . ?
C27 C25 C19 132.0(4) . . ?
N5 C25 C19 119.3(4) . . ?
N5 C26 N6 111.2(4) . . ?
N5 C26 C40 124.3(4) . . ?
N6 C26 C40 124.5(4) . . ?
N6 C27 C25 106.3(4) . . ?
N6 C27 C46 120.5(4) . . ?
C25 C27 C46 133.1(4) . . ?
C29 C28 C33 117.7(4) . . ?
C29 C28 C23 119.7(4) . . ?
C33 C28 C23 122.7(4) . . ?
C28 C29 C30 121.6(5) . . ?
C31 C30 C29 119.9(5) . . ?
C32 C31 C30 119.7(5) . . ?
C32 C31 O2 122.8(5) . . ?
C30 C31 O2 117.5(5) . . ?
C31 C32 C33 120.5(5) . . ?
C28 C33 C32 120.7(5) . . ?
C35 C34 C39 118.5(4) . . ?
C35 C34 C24 123.3(4) . . ?
C39 C34 C24 118.1(4) . . ?
C34 C35 C36 120.4(4) . . ?
C35 C36 C37 121.6(4) . . ?
C36 C37 C38 117.7(4) . . ?
C36 C37 C52 122.2(4) . . ?
C38 C37 C52 120.0(4) . . ?
C39 C38 C37 120.5(4) . . ?
C38 C39 C34 121.3(4) . . ?
C41 C40 C45 117.5(5) . . ?
C41 C40 C26 120.9(5) . . ?
C45 C40 C26 121.6(5) . . ?
C40 C41 C42 121.8(6) . . ?
C43 C42 C41 120.3(6) . . ?
C42 C43 C44 119.8(5) . . ?
C42 C43 O3 118.3(6) . . ?
C44 C43 O3 121.9(6) . . ?
C43 C44 C45 119.5(6) . . ?
C40 C45 C44 121.0(6) . . ?
C47 C46 C51 117.8(4) . . ?
C47 C46 C27 121.7(4) . . ?
C51 C46 C27 120.4(4) . . ?
C48 C47 C46 121.0(4) . . ?
C47 C48 C49 121.2(4) . . ?
C50 C49 C48 117.1(4) . . ?
C50 C49 C53 122.3(4) . . ?
C48 C49 C53 120.5(4) . . ?
C51 C50 C49 122.1(4) . . ?
C50 C51 C46 120.7(4) . . ?
C53 C52 N8 105.6(3) . . ?
C53 C52 C37 134.3(4) . . ?
N8 C52 C37 119.9(3) . . ?
C52 C53 N7 109.3(3) . . ?
C52 C53 C49 129.8(4) . . ?
N7 C53 C49 120.8(3) . . ?
N7 C54 N8 110.0(4) . . ?
N7 C54 C55 126.3(4) . . ?
N8 C54 C55 123.6(4) . . ?
C56 C55 C60 118.1(4) . . ?
C56 C55 C54 121.0(4) . . ?
C60 C55 C54 120.8(4) . . ?
C55 C56 C57 121.0(4) . . ?
C58 C57 C56 120.4(4) . . ?
O4 C58 C57 123.9(4) . . ?
O4 C58 C59 117.1(4) . . ?
C57 C58 C59 118.9(4) . . ?
C58 C59 C60 120.6(4) . . ?
C55 C60 C59 120.9(4) . . ?
N14 C62 C61 110.8(11) . . ?
C61' C62' N14 110.2(14) . . ?
O5 C64 N14 124.3(6) . . ?
C66 C65 N14 109.4(6) . . ?
N13 C68 C67 109.8(7) . . ?
O6 C70 N13 122.3(6) . . ?
C87 C71 N13 112.0(7) . . ?
O7 C72 N12 127.4(6) . . ?
C72 N12 C76' 122.6(18) . . ?
C72 N12 C76 118.5(10) . . ?
C72 N12 C74 119.7(5) . . ?
C76 N12 C74 121.6(10) . . ?
C72 N12 C74' 118.8(7) . . ?
C76' N12 C74' 117.5(19) . . ?
C70 N13 C71 120.6(7) . . ?
C70 N13 C68 119.1(6) . . ?
C71 N13 C68 120.1(7) . . ?
C64 N14 C62 133.6(8) . . ?
C64 N14 C65 119.0(5) . . ?
C62 N14 C65 106.9(7) . . ?
C64 N14 C62' 109.0(9) . . ?
C65 N14 C62' 130.2(9) . . ?
C75 C74 N12 107.0(7) . . ?
C77 C76 N12 110.8(14) . . ?
C75' C74' N12 105.6(10) . . ?
N12 C76' C77' 110.6(18) . . ?
C4_1 O1_1 C1_1 108.2(10) . . ?
C2_1 O2_1 C3_1 111.4(10) . . ?
O1_1 C1_1 C2_1 108.9(12) . . ?
O2_1 C2_1 C1_1 112.0(10) . . ?
O2_1 C3_1 C4_1 111.7(10) . . ?
O1_1 C4_1 C3_1 109.5(13) . . ?
C1_2 O1_2 C4_2 112.2(17) . . ?
C2_2 O2_2 C3_2 104.2(18) . . ?
O1_2 C1_2 C2_2 109.3(18) . . ?
O2_2 C2_2 C1_2 106.6(17) . . ?
O2_2 C3_2 C4_2 107.0(16) . . ?
O1_2 C4_2 C3_2 109.1(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 C4 1.365(5) . ?
O2 C31 1.381(5) . ?
O3 C43 1.392(6) . ?
O4 C58 1.368(5) . ?
O5 C64 1.196(6) . ?
O6 C70 1.271(6) . ?
O7 C72 1.211(5) . ?
N1 C7 1.328(5) . ?
N1 C8 1.395(5) . ?
N2 C7 1.363(5) . ?
N2 C9 1.382(5) . ?
N3 C23 1.345(5) . ?
N3 C22 1.387(5) . ?
N4 C23 1.325(5) . ?
N4 C24 1.397(5) . ?
N5 C26 1.331(5) . ?
N5 C25 1.387(5) . ?
N6 C26 1.349(5) . ?
N6 C27 1.380(5) . ?
N7 C54 1.333(5) . ?
N7 C53 1.394(5) . ?
N8 C54 1.361(5) . ?
N8 C52 1.378(5) . ?
C1 C6 1.395(5) . ?
C1 C2 1.399(6) . ?
C1 C7 1.458(6) . ?
C2 C3 1.378(6) . ?
C3 C4 1.391(5) . ?
C4 C5 1.393(5) . ?
C5 C6 1.387(6) . ?
C8 C9 1.385(5) . ?
C8 C10 1.461(5) . ?
C9 C16 1.469(5) . ?
C10 C11 1.388(5) . ?
C10 C15 1.409(6) . ?
C11 C12 1.387(5) . ?
C12 C13 1.398(5) . ?
C13 C14 1.408(5) . ?
C13 C22 1.465(5) . ?
C14 C15 1.381(5) . ?
C16 C17 1.389(6) . ?
C16 C21 1.401(5) . ?
C17 C18 1.380(6) . ?
C18 C19 1.399(6) . ?
C19 C20 1.390(5) . ?
C19 C25 1.466(5) . ?
C20 C21 1.385(5) . ?
C22 C24 1.372(5) . ?
C23 C28 1.465(5) . ?
C24 C34 1.479(5) . ?
C25 C27 1.381(6) . ?
C26 C40 1.463(6) . ?
C27 C46 1.471(6) . ?
C28 C29 1.378(6) . ?
C28 C33 1.388(6) . ?
C29 C30 1.387(6) . ?
C30 C31 1.375(7) . ?
C31 C32 1.360(7) . ?
C32 C33 1.397(6) . ?
C34 C35 1.385(5) . ?
C34 C39 1.388(6) . ?
C35 C36 1.389(5) . ?
C36 C37 1.391(6) . ?
C37 C38 1.399(5) . ?
C37 C52 1.472(5) . ?
C38 C39 1.386(5) . ?
C40 C41 1.350(7) . ?
C40 C45 1.367(7) . ?
C41 C42 1.375(7) . ?
C42 C43 1.343(8) . ?
C43 C44 1.349(8) . ?
C44 C45 1.396(7) . ?
C46 C47 1.394(5) . ?
C46 C51 1.414(6) . ?
C47 C48 1.379(5) . ?
C48 C49 1.413(5) . ?
C49 C50 1.390(5) . ?
C49 C53 1.461(5) . ?
C50 C51 1.368(6) . ?
C52 C53 1.375(5) . ?
C54 C55 1.472(6) . ?
C55 C56 1.383(5) . ?
C55 C60 1.385(6) . ?
C56 C57 1.396(6) . ?
C57 C58 1.373(5) . ?
C58 C59 1.385(6) . ?
C59 C60 1.386(6) . ?
C61 C62 1.578(17) . ?
C62 N14 1.413(15) . ?
C61' C62' 1.45(3) . ?
C62' N14 1.605(18) . ?
C64 N14 1.377(7) . ?
C65 C66 1.414(9) . ?
C65 N14 1.535(8) . ?
C67 C68 1.582(11) . ?
C68 N13 1.495(9) . ?
C70 N13 1.365(8) . ?
C71 C87 1.478(10) . ?
C71 N13 1.487(8) . ?
C72 N12 1.311(6) . ?
N12 C76' 1.42(3) . ?
N12 C76 1.50(2) . ?
N12 C74 1.511(9) . ?
N12 C74' 1.519(12) . ?
C74 C75 1.497(12) . ?
C76 C77 1.39(2) . ?
C74' C75' 1.504(18) . ?
C76' C77' 1.65(3) . ?
O1_1 C4_1 1.398(11) . ?
O1_1 C1_1 1.416(11) . ?
O2_1 C2_1 1.399(11) . ?
O2_1 C3_1 1.402(11) . ?
C1_1 C2_1 1.525(14) . ?
C3_1 C4_1 1.497(15) . ?
O1_2 C1_2 1.392(14) . ?
O1_2 C4_2 1.404(14) . ?
O2_2 C2_2 1.391(14) . ?
O2_2 C3_2 1.403(14) . ?
C1_2 C2_2 1.530(18) . ?
C3_2 C4_2 1.538(18) . ?
