#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557902.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_1557902
loop_
_publ_author_name
'Okude, Ryo'
'Mori, Genki'
'Yagi, Akiko'
'Itami, Kenichiro'
_publ_section_title
;
 Programmable synthesis of multiply arylated cubanes through C--H
 metalation and arylation
;
_journal_issue                   29
_journal_name_full               'Chemical Science'
_journal_page_first              7672
_journal_page_last               7675
_journal_paper_doi               10.1039/D0SC01909G
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C34 H42 N2 O2'
_chemical_formula_weight         510.69
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                103.450(3)
_cell_angle_beta                 107.340(3)
_cell_angle_gamma                103.234(3)
_cell_formula_units_Z            4
_cell_length_a                   13.5226(5)
_cell_length_b                   14.1690(5)
_cell_length_c                   17.1029(5)
_cell_measurement_reflns_used    6543
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.0350
_cell_measurement_theta_min      2.5440
_cell_volume                     2881.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31848
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.347
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         10091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0856P)²+2.5830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1775
_refine_ls_wR_factor_ref         0.2124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5906
_reflns_number_total             10091
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01909g2.cif
_cod_data_source_block           2e
_cod_depositor_comments
;

 Adding full bibliography for 1557900--1557907.cif.

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2880.96(18)
_cod_original_formula_sum        'C68 H84 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     1021.39
_cod_database_code               1557902
_shelx_shelxl_version_number     2016/6
_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   0.989
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_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_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 0.3345(2) 0.9958(2) 0.10298(17) 0.0365(7) Uani 1 1 d . . . . .
C1 C 0.3458(3) 1.0880(3) 0.1242(2) 0.0279(9) Uani 1 1 d . . . . .
N1 N 0.4245(2) 1.1558(2) 0.19805(19) 0.0294(7) Uani 1 1 d . . . . .
C2 C 0.5010(3) 1.1193(3) 0.2565(2) 0.0325(9) Uani 1 1 d . . . . .
H10 H 0.551828 1.181297 0.306524 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4439(3) 1.0465(3) 0.2944(3) 0.0449(11) Uani 1 1 d . . . . .
H11 H 0.402018 1.079284 0.323204 0.067 Uiso 1 1 calc R U . . .
H12 H 0.498729 1.030111 0.336450 0.067 Uiso 1 1 calc R U . . .
H13 H 0.394285 0.983366 0.247777 0.067 Uiso 1 1 calc R U . . .
C4 C 0.5719(3) 1.0755(3) 0.2145(3) 0.0467(11) Uani 1 1 d . . . . .
H14 H 0.526770 1.010416 0.168456 0.070 Uiso 1 1 calc R U . . .
H15 H 0.629481 1.063770 0.258073 0.070 Uiso 1 1 calc R U . . .
H16 H 0.605289 1.123907 0.189759 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4380(3) 1.2663(3) 0.2245(2) 0.0295(9) Uani 1 1 d . . . . .
H17 H 0.385607 1.278538 0.175736 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4076(3) 1.2975(3) 0.3027(2) 0.0398(10) Uani 1 1 d . . . . .
H18 H 0.331975 1.256820 0.289497 0.060 Uiso 1 1 calc R U . . .
H19 H 0.414364 1.370366 0.317593 0.060 Uiso 1 1 calc R U . . .
H20 H 0.456776 1.285460 0.351770 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5528(3) 1.3318(3) 0.2396(3) 0.0368(10) Uani 1 1 d . . . . .
H21 H 0.605190 1.329555 0.292374 0.055 Uiso 1 1 calc R U . . .
H22 H 0.554426 1.402810 0.246043 0.055 Uiso 1 1 calc R U . . .
H23 H 0.572423 1.305287 0.190130 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2715(3) 1.1252(3) 0.0629(2) 0.0269(9) Uani 1 1 d . . . . .
C9 C 0.3108(3) 1.1865(3) 0.0043(2) 0.0260(8) Uani 1 1 d . . . . .
C10 C 0.2346(3) 1.2518(3) 0.0161(2) 0.0261(8) Uani 1 1 d . . . . .
H24 H 0.256088 1.327865 0.029722 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1967(3) 1.1926(3) 0.0742(2) 0.0284(9) Uani 1 1 d . . . . .
H25 H 0.190242 1.225130 0.130148 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1007(3) 1.1135(3) -0.0077(2) 0.0278(9) Uani 1 1 d . . . . .
H26 H 0.023371 1.087002 -0.012263 0.033 Uiso 1 1 calc R U . . .
C13 C 0.1755(3) 1.0467(3) -0.0193(2) 0.0283(9) Uani 1 1 d . . . . .
H27 H 0.152948 0.970591 -0.032775 0.034 Uiso 1 1 calc R U . . .
C14 C 0.2136(3) 1.1049(3) -0.0774(2) 0.0268(9) Uani 1 1 d . . . . .
H28 H 0.219540 1.071860 -0.133513 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1393(3) 1.1732(3) -0.0660(2) 0.0257(8) Uani 1 1 d . . . . .
C16 C 0.4244(3) 1.2228(3) 0.0085(2) 0.0243(8) Uani 1 1 d . . . . .
C17 C 0.4838(3) 1.1555(3) 0.0027(2) 0.0299(9) Uani 1 1 d . . . . .
H1 H 0.450692 1.085832 -0.003954 0.036 Uiso 1 1 calc R U . . .
C18 C 0.5902(3) 1.1872(3) 0.0063(2) 0.0299(9) Uani 1 1 d . . . . .
H2 H 0.629019 1.139342 0.002581 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6414(3) 1.2895(3) 0.0153(2) 0.0245(8) Uani 1 1 d . . . . .
C20 C 0.5808(3) 1.3559(3) 0.0196(2) 0.0261(9) Uani 1 1 d . . . . .
H3 H 0.612779 1.425151 0.024481 0.031 Uiso 1 1 calc R U . . .
C21 C 0.4747(3) 1.3238(3) 0.0170(2) 0.0268(9) Uani 1 1 d . . . . .
H4 H 0.435838 1.371546 0.021024 0.032 Uiso 1 1 calc R U . . .
C22 C 0.7564(3) 1.3236(3) 0.0207(2) 0.0266(9) Uani 1 1 d . . . . .
C23 C 0.8017(3) 1.2550(3) -0.0156(2) 0.0311(9) Uani 1 1 d . . . . .
H5 H 0.757864 1.185529 -0.045994 0.037 Uiso 1 1 calc R U . . .
C24 C 0.9103(3) 1.2866(3) -0.0081(2) 0.0341(10) Uani 1 1 d . . . . .
H6 H 0.940207 1.238451 -0.032870 0.041 Uiso 1 1 calc R U . . .
C25 C 0.9748(3) 1.3876(3) 0.0350(3) 0.0368(10) Uani 1 1 d . . . . .
H7 H 1.049108 1.408992 0.040445 0.044 Uiso 1 1 calc R U . . .
C26 C 0.9306(3) 1.4568(3) 0.0700(2) 0.0353(10) Uani 1 1 d . . . . .
H8 H 0.974384 1.526577 0.098951 0.042 Uiso 1 1 calc R U . . .
C27 C 0.8228(3) 1.4258(3) 0.0635(2) 0.0297(9) Uani 1 1 d . . . . .
H9 H 0.793536 1.474554 0.088308 0.036 Uiso 1 1 calc R U . . .
C28 C 0.0713(3) 1.2091(3) -0.1329(2) 0.0261(9) Uani 1 1 d . . . . .
O2 O 0.09029(19) 1.3009(2) -0.12086(16) 0.0311(6) Uani 1 1 d . . . . .
N2 N -0.0079(2) 1.1367(2) -0.20507(18) 0.0277(7) Uani 1 1 d . . . . .
C29 C -0.0297(3) 1.0259(3) -0.2203(2) 0.0350(10) Uani 1 1 d . . . . .
H29 H 0.022749 1.018176 -0.168728 0.042 Uiso 1 1 calc R U . . .
C30 C -0.0059(4) 0.9757(3) -0.2986(3) 0.0502(12) Uani 1 1 d . . . . .
H30 H -0.054515 0.983164 -0.350564 0.075 Uiso 1 1 calc R U . . .
H31 H -0.018403 0.902704 -0.305843 0.075 Uiso 1 1 calc R U . . .
H32 H 0.070360 1.008788 -0.289797 0.075 Uiso 1 1 calc R U . . .
C31 C -0.1444(3) 0.9734(4) -0.2258(3) 0.0555(13) Uani 1 1 d . . . . .
H33 H -0.157822 1.012112 -0.176754 0.083 Uiso 1 1 calc R U . . .
H34 H -0.150987 0.903575 -0.224186 0.083 Uiso 1 1 calc R U . . .
H35 H -0.198294 0.970603 -0.280082 0.083 Uiso 1 1 calc R U . . .
C32 C -0.0775(3) 1.1680(3) -0.2731(2) 0.0319(9) Uani 1 1 d . . . . .
H36 H -0.128836 1.103478 -0.320195 0.038 Uiso 1 1 calc R U . . .
C33 C -0.1477(3) 1.2240(3) -0.2405(3) 0.0400(10) Uani 1 1 d . . . . .
H37 H -0.193724 1.180189 -0.219571 0.060 Uiso 1 1 calc R U . . .
H38 H -0.194187 1.240865 -0.287701 0.060 Uiso 1 1 calc R U . . .
H39 H -0.100479 1.287297 -0.193001 0.060 Uiso 1 1 calc R U . . .
C34 C -0.0100(3) 1.2275(3) -0.3135(3) 0.0402(10) Uani 1 1 d . . . . .
H40 H 0.036727 1.294542 -0.271042 0.060 Uiso 1 1 calc R U . . .
H41 H -0.059021 1.237026 -0.364165 0.060 Uiso 1 1 calc R U . . .
H42 H 0.035748 1.189199 -0.331458 0.060 Uiso 1 1 calc R U . . .
O3 O 0.5017(2) 0.4056(2) 0.64348(17) 0.0397(7) Uani 1 1 d . . . . .
C35 C 0.4190(3) 0.3711(3) 0.6575(2) 0.0318(9) Uani 1 1 d . . . . .
N3 N 0.4224(2) 0.3396(2) 0.72697(18) 0.0307(8) Uani 1 1 d . . . . .
C36 C 0.5289(3) 0.3521(3) 0.7926(2) 0.0368(10) Uani 1 1 d . . . . .
H52 H 0.511983 0.330865 0.840219 0.044 Uiso 1 1 calc R U . . .
C37 C 0.5856(4) 0.2812(4) 0.7589(3) 0.0624(15) Uani 1 1 d . . . . .
H53 H 0.534714 0.210974 0.732646 0.094 Uiso 1 1 calc R U . . .
H54 H 0.649147 0.284108 0.806783 0.094 Uiso 1 1 calc R U . . .
H55 H 0.609797 0.302586 0.715235 0.094 Uiso 1 1 calc R U . . .
C38 C 0.6029(3) 0.4625(3) 0.8335(3) 0.0458(11) Uani 1 1 d . . . . .
H56 H 0.630699 0.484122 0.791513 0.069 Uiso 1 1 calc R U . . .
H57 H 0.664455 0.468643 0.884501 0.069 Uiso 1 1 calc R U . . .
H58 H 0.561431 0.506284 0.850901 0.069 Uiso 1 1 calc R U . . .
C39 C 0.3235(3) 0.2990(3) 0.7444(2) 0.0390(10) Uani 1 1 d . . . . .
H59 H 0.259265 0.286817 0.691169 0.047 Uiso 1 1 calc R U . . .
C40 C 0.3156(4) 0.3773(4) 0.8171(3) 0.0483(12) Uani 1 1 d . . . . .
H60 H 0.378137 0.392581 0.870543 0.073 Uiso 1 1 calc R U . . .
H61 H 0.247535 0.350065 0.825588 0.073 Uiso 1 1 calc R U . . .
H62 H 0.316067 0.440253 0.802418 0.073 Uiso 1 1 calc R U . . .
C41 C 0.3152(4) 0.1964(3) 0.7592(3) 0.0594(14) Uani 1 1 d . . . . .
H63 H 0.327144 0.150545 0.712837 0.089 Uiso 1 1 calc R U . . .
H64 H 0.242361 0.165995 0.759036 0.089 Uiso 1 1 calc R U . . .
H65 H 0.370817 0.206419 0.815110 0.089 Uiso 1 1 calc R U . . .
C42 C 0.3093(3) 0.3600(3) 0.5930(2) 0.0325(9) Uani 1 1 d . . . . .
C43 C 0.2259(3) 0.2524(3) 0.5225(2) 0.0334(9) Uani 1 1 d . . . . .
C44 C 0.2236(3) 0.3027(3) 0.4501(2) 0.0321(9) Uani 1 1 d . . . . .
H66 H 0.230075 0.270660 0.393951 0.039 Uiso 1 1 calc R U . . .
C45 C 0.3028(3) 0.4072(3) 0.5189(2) 0.0379(10) Uani 1 1 d . . . . .
H67 H 0.366874 0.452459 0.512916 0.045 Uiso 1 1 calc R U . . .
C46 C 0.2029(3) 0.4384(3) 0.5288(3) 0.0420(11) Uani 1 1 d . . . . .
H68 H 0.193841 0.506914 0.531018 0.050 Uiso 1 1 calc R U . . .
C47 C 0.2074(4) 0.3904(3) 0.6015(3) 0.0433(11) Uani 1 1 d . . . . .
H69 H 0.200782 0.422962 0.657393 0.052 Uiso 1 1 calc R U . . .
C48 C 0.1275(3) 0.2856(3) 0.5326(2) 0.0371(10) Uani 1 1 d . . . . .
H70 H 0.062495 0.241244 0.538056 0.045 Uiso 1 1 calc R U . . .
C49 C 0.1233(3) 0.3342(3) 0.4591(2) 0.0327(9) Uani 1 1 d . . . . .
C50 C 0.2421(3) 0.1510(3) 0.5173(2) 0.0338(10) Uani 1 1 d . . . . .
C51 C 0.3308(3) 0.1309(3) 0.4989(3) 0.0399(10) Uani 1 1 d . . . . .
H43 H 0.380880 0.182524 0.490074 0.048 Uiso 1 1 calc R U . . .
C52 C 0.3465(3) 0.0379(3) 0.4935(3) 0.0370(10) Uani 1 1 d . . . . .
H44 H 0.406634 0.025914 0.479835 0.044 Uiso 1 1 calc R U . . .
C53 C 0.2764(3) -0.0400(3) 0.5077(2) 0.0355(10) Uani 1 1 d . . . . .
C54 C 0.1889(3) -0.0192(3) 0.5253(2) 0.0362(10) Uani 1 1 d . . . . .
H45 H 0.139192 -0.070773 0.534473 0.043 Uiso 1 1 calc R U . . .
C55 C 0.1710(3) 0.0739(3) 0.5301(2) 0.0358(10) Uani 1 1 d . . . . .
H46 H 0.109723 0.085081 0.542289 0.043 Uiso 1 1 calc R U . . .
C56 C 0.2957(3) -0.1398(3) 0.5034(2) 0.0276(9) Uani 1 1 d . . . . .
C57 C 0.3572(3) -0.1749(3) 0.4584(3) 0.0408(11) Uani 1 1 d . . . . .
H47 H 0.385457 -0.135910 0.426975 0.049 Uiso 1 1 calc R U . . .
C58 C 0.3781(3) -0.2668(3) 0.4588(3) 0.0429(11) Uani 1 1 d . . . . .
H48 H 0.421421 -0.289082 0.428400 0.052 Uiso 1 1 calc R U . . .
C59 C 0.3378(3) -0.3241(3) 0.5017(3) 0.0410(11) Uani 1 1 d . . . . .
H49 H 0.352366 -0.386629 0.501600 0.049 Uiso 1 1 calc R U . . .
C60 C 0.2740(4) -0.2908(3) 0.5465(3) 0.0438(11) Uani 1 1 d . . . . .
H50 H 0.244497 -0.330814 0.576679 0.053 Uiso 1 1 calc R U . . .
C61 C 0.2543(3) -0.1998(3) 0.5465(3) 0.0378(10) Uani 1 1 d . . . . .
H51 H 0.211109 -0.177638 0.577020 0.045 Uiso 1 1 calc R U . . .
C62 C 0.0178(3) 0.3092(3) 0.3849(2) 0.0343(10) Uani 1 1 d . . . . .
O4 O -0.0646(2) 0.2446(3) 0.38009(19) 0.0568(9) Uani 1 1 d . . . . .
N4 N 0.0190(2) 0.3510(2) 0.32130(19) 0.0312(8) Uani 1 1 d . . . . .
C63 C 0.1141(3) 0.4290(3) 0.3263(3) 0.0488(12) Uani 1 1 d . . . . .
H71 H 0.173168 0.443418 0.383359 0.059 Uiso 1 1 calc R U . . .
C64 C 0.1568(4) 0.3913(5) 0.2574(3) 0.083(2) Uani 1 1 d . . . . .
H72 H 0.164385 0.324024 0.256907 0.125 Uiso 1 1 calc R U . . .
H73 H 0.228246 0.439832 0.269466 0.125 Uiso 1 1 calc R U . . .
H74 H 0.105479 0.385360 0.200764 0.125 Uiso 1 1 calc R U . . .
C65 C 0.0886(5) 0.5284(4) 0.3266(4) 0.084(2) Uani 1 1 d . . . . .
H75 H 0.031262 0.517516 0.271289 0.126 Uiso 1 1 calc R U . . .
H76 H 0.154788 0.581877 0.334735 0.126 Uiso 1 1 calc R U . . .
H77 H 0.063466 0.549660 0.373945 0.126 Uiso 1 1 calc R U . . .
C66 C -0.0811(3) 0.3181(3) 0.2419(2) 0.0369(10) Uani 1 1 d . . . . .
H78 H -0.062030 0.355989 0.203130 0.044 Uiso 1 1 calc R U . . .
C67 C -0.1142(4) 0.2036(4) 0.1925(3) 0.0609(14) Uani 1 1 d . . . . .
H79 H -0.052196 0.188527 0.180148 0.091 Uiso 1 1 calc R U . . .
H80 H -0.175973 0.185778 0.137937 0.091 Uiso 1 1 calc R U . . .
H81 H -0.135696 0.163399 0.227698 0.091 Uiso 1 1 calc R U . . .
C68 C -0.1745(4) 0.3456(5) 0.2593(3) 0.0669(16) Uani 1 1 d . . . . .
H82 H -0.198842 0.306649 0.294339 0.100 Uiso 1 1 calc R U . . .
H83 H -0.234969 0.329059 0.204297 0.100 Uiso 1 1 calc R U . . .
H84 H -0.150847 0.419100 0.290673 0.100 Uiso 1 1 calc R U . . .
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
O1 C1 N1 122.3(3) . . ?
O1 C1 C8 117.9(3) . . ?
N1 C1 C8 119.7(3) . . ?
C1 N1 C5 122.7(3) . . ?
C1 N1 C2 119.5(3) . . ?
C5 N1 C2 117.8(3) . . ?
N1 C2 C4 112.2(3) . . ?
N1 C2 C3 113.0(3) . . ?
C4 C2 C3 112.3(3) . . ?
N1 C2 H10 106.2 . . ?
C4 C2 H10 106.2 . . ?
C3 C2 H10 106.2 . . ?
C2 C3 H11 109.5 . . ?
C2 C3 H12 109.5 . . ?
H11 C3 H12 109.5 . . ?
C2 C3 H13 109.5 . . ?
H11 C3 H13 109.5 . . ?
H12 C3 H13 109.5 . . ?
C2 C4 H14 109.5 . . ?
C2 C4 H15 109.5 . . ?
H14 C4 H15 109.5 . . ?
C2 C4 H16 109.5 . . ?
H14 C4 H16 109.5 . . ?
H15 C4 H16 109.5 . . ?
N1 C5 C6 111.1(3) . . ?
N1 C5 C7 112.0(3) . . ?
C6 C5 C7 111.7(3) . . ?
N1 C5 H17 107.3 . . ?
C6 C5 H17 107.3 . . ?
C7 C5 H17 107.3 . . ?
C5 C6 H18 109.5 . . ?
C5 C6 H19 109.5 . . ?
H18 C6 H19 109.5 . . ?
C5 C6 H20 109.5 . . ?
H18 C6 H20 109.5 . . ?
H19 C6 H20 109.5 . . ?
C5 C7 H21 109.5 . . ?
C5 C7 H22 109.5 . . ?
H21 C7 H22 109.5 . . ?
C5 C7 H23 109.5 . . ?
H21 C7 H23 109.5 . . ?
H22 C7 H23 109.5 . . ?
C1 C8 C13 119.9(3) . . ?
C1 C8 C11 133.2(3) . . ?
C13 C8 C11 89.6(3) . . ?
C1 C8 C9 123.1(3) . . ?
C13 C8 C9 89.9(3) . . ?
C11 C8 C9 89.2(3) . . ?
C16 C9 C10 127.6(3) . . ?
C16 C9 C14 123.9(3) . . ?
C10 C9 C14 89.7(3) . . ?
C16 C9 C8 125.6(3) . . ?
C10 C9 C8 89.6(3) . . ?
C14 C9 C8 88.7(2) . . ?
C15 C10 C9 90.6(3) . . ?
C15 C10 C11 90.7(3) . . ?
C9 C10 C11 90.6(3) . . ?
C15 C10 H24 124.8 . . ?
C9 C10 H24 124.8 . . ?
C11 C10 H24 124.8 . . ?
C12 C11 C10 89.7(3) . . ?
C12 C11 C8 90.2(3) . . ?
C10 C11 C8 90.7(3) . . ?
C12 C11 H25 125.1 . . ?
C10 C11 H25 125.1 . . ?
C8 C11 H25 125.1 . . ?
C11 C12 C13 89.8(3) . . ?
C11 C12 C15 90.1(3) . . ?
C13 C12 C15 90.2(3) . . ?
C11 C12 H26 125.2 . . ?
C13 C12 H26 125.2 . . ?
C15 C12 H26 125.2 . . ?
C8 C13 C14 90.7(3) . . ?
C8 C13 C12 90.4(3) . . ?
C14 C13 C12 90.1(3) . . ?
C8 C13 H27 125.0 . . ?
C14 C13 H27 125.0 . . ?
C12 C13 H27 125.0 . . ?
C13 C14 C15 90.5(3) . . ?
C13 C14 C9 90.7(3) . . ?
C15 C14 C9 89.5(3) . . ?
C13 C14 H28 125.1 . . ?
C15 C14 H28 125.1 . . ?
C9 C14 H28 125.1 . . ?
C28 C15 C10 120.5(3) . . ?
C28 C15 C14 128.1(3) . . ?
C10 C15 C14 90.1(3) . . ?
C28 C15 C12 127.9(3) . . ?
C10 C15 C12 89.5(3) . . ?
C14 C15 C12 89.2(3) . . ?
C17 C16 C21 117.7(3) . . ?
C17 C16 C9 120.4(3) . . ?
C21 C16 C9 121.9(3) . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H1 119.2 . . ?
C16 C17 H1 119.2 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H2 119.6 . . ?
C19 C18 H2 119.6 . . ?
C20 C19 C18 117.3(3) . . ?
C20 C19 C22 122.2(3) . . ?
C18 C19 C22 120.5(3) . . ?
C19 C20 C21 121.6(3) . . ?
C19 C20 H3 119.2 . . ?
C21 C20 H3 119.2 . . ?
C20 C21 C16 121.0(3) . . ?
C20 C21 H4 119.5 . . ?
C16 C21 H4 119.5 . . ?
C23 C22 C27 117.9(3) . . ?
C23 C22 C19 121.1(3) . . ?
C27 C22 C19 121.0(3) . . ?
C22 C23 C24 120.9(4) . . ?
C22 C23 H5 119.5 . . ?
C24 C23 H5 119.5 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H6 119.8 . . ?
C23 C24 H6 119.8 . . ?
C26 C25 C24 119.4(4) . . ?
C26 C25 H7 120.3 . . ?
C24 C25 H7 120.3 . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H8 119.7 . . ?
C27 C26 H8 119.7 . . ?
C26 C27 C22 120.8(4) . . ?
C26 C27 H9 119.6 . . ?
C22 C27 H9 119.6 . . ?
O2 C28 N2 122.9(3) . . ?
O2 C28 C15 119.2(3) . . ?
N2 C28 C15 117.8(3) . . ?
C28 N2 C29 123.0(3) . . ?
C28 N2 C32 120.0(3) . . ?
C29 N2 C32 117.0(3) . . ?
N2 C29 C30 111.2(3) . . ?
N2 C29 C31 111.8(3) . . ?
C30 C29 C31 112.8(4) . . ?
N2 C29 H29 106.9 . . ?
C30 C29 H29 106.9 . . ?
C31 C29 H29 106.9 . . ?
C29 C30 H30 109.5 . . ?
C29 C30 H31 109.5 . . ?
H30 C30 H31 109.5 . . ?
C29 C30 H32 109.5 . . ?
H30 C30 H32 109.5 . . ?
H31 C30 H32 109.5 . . ?
C29 C31 H33 109.5 . . ?
C29 C31 H34 109.5 . . ?
H33 C31 H34 109.5 . . ?
C29 C31 H35 109.5 . . ?
H33 C31 H35 109.5 . . ?
H34 C31 H35 109.5 . . ?
N2 C32 C33 112.1(3) . . ?
N2 C32 C34 111.5(3) . . ?
C33 C32 C34 112.9(3) . . ?
N2 C32 H36 106.7 . . ?
C33 C32 H36 106.7 . . ?
C34 C32 H36 106.7 . . ?
C32 C33 H37 109.5 . . ?
C32 C33 H38 109.5 . . ?
H37 C33 H38 109.5 . . ?
C32 C33 H39 109.5 . . ?
H37 C33 H39 109.5 . . ?
H38 C33 H39 109.5 . . ?
C32 C34 H40 109.5 . . ?
C32 C34 H41 109.5 . . ?
H40 C34 H41 109.5 . . ?
C32 C34 H42 109.5 . . ?
H40 C34 H42 109.5 . . ?
H41 C34 H42 109.5 . . ?
O3 C35 N3 122.5(3) . . ?
O3 C35 C42 118.5(3) . . ?
N3 C35 C42 118.9(4) . . ?
C35 N3 C39 122.6(3) . . ?
C35 N3 C36 120.2(3) . . ?
C39 N3 C36 117.0(3) . . ?
N3 C36 C37 112.5(3) . . ?
N3 C36 C38 112.9(3) . . ?
C37 C36 C38 112.3(4) . . ?
N3 C36 H52 106.1 . . ?
C37 C36 H52 106.1 . . ?
C38 C36 H52 106.1 . . ?
C36 C37 H53 109.5 . . ?
C36 C37 H54 109.5 . . ?
H53 C37 H54 109.5 . . ?
C36 C37 H55 109.5 . . ?
H53 C37 H55 109.5 . . ?
H54 C37 H55 109.5 . . ?
C36 C38 H56 109.5 . . ?
C36 C38 H57 109.5 . . ?
H56 C38 H57 109.5 . . ?
C36 C38 H58 109.5 . . ?
H56 C38 H58 109.5 . . ?
H57 C38 H58 109.5 . . ?
N3 C39 C40 110.9(3) . . ?
N3 C39 C41 112.2(4) . . ?
C40 C39 C41 112.9(4) . . ?
N3 C39 H59 106.8 . . ?
C40 C39 H59 106.8 . . ?
C41 C39 H59 106.8 . . ?
C39 C40 H60 109.5 . . ?
C39 C40 H61 109.5 . . ?
H60 C40 H61 109.5 . . ?
C39 C40 H62 109.5 . . ?
H60 C40 H62 109.5 . . ?
H61 C40 H62 109.5 . . ?
C39 C41 H63 109.5 . . ?
C39 C41 H64 109.5 . . ?
H63 C41 H64 109.5 . . ?
C39 C41 H65 109.5 . . ?
H63 C41 H65 109.5 . . ?
H64 C41 H65 109.5 . . ?
C35 C42 C45 120.3(3) . . ?
C35 C42 C47 133.8(3) . . ?
C45 C42 C47 89.3(3) . . ?
C35 C42 C43 123.5(3) . . ?
C45 C42 C43 89.3(3) . . ?
C47 C42 C43 88.3(3) . . ?
C50 C43 C48 128.0(3) . . ?
C50 C43 C44 123.6(3) . . ?
C48 C43 C44 90.0(3) . . ?
C50 C43 C42 124.8(3) . . ?
C48 C43 C42 90.1(3) . . ?
C44 C43 C42 88.8(3) . . ?
C49 C44 C45 90.2(3) . . ?
C49 C44 C43 89.9(3) . . ?
C45 C44 C43 90.9(3) . . ?
C49 C44 H66 125.0 . . ?
C45 C44 H66 125.0 . . ?
C43 C44 H66 125.0 . . ?
C42 C45 C46 90.2(3) . . ?
C42 C45 C44 91.0(3) . . ?
C46 C45 C44 89.9(3) . . ?
C42 C45 H67 125.0 . . ?
C46 C45 H67 125.0 . . ?
C44 C45 H67 125.0 . . ?
C47 C46 C45 90.3(3) . . ?
C47 C46 C49 90.8(3) . . ?
C45 C46 C49 90.2(3) . . ?
C47 C46 H68 125.0 . . ?
C45 C46 H68 125.0 . . ?
C49 C46 H68 125.0 . . ?
C46 C47 C48 89.9(3) . . ?
C46 C47 C42 90.2(3) . . ?
C48 C47 C42 91.1(3) . . ?
C46 C47 H69 125.0 . . ?
C48 C47 H69 125.0 . . ?
C42 C47 H69 125.0 . . ?
C43 C48 C49 90.3(3) . . ?
C43 C48 C47 90.6(3) . . ?
C49 C48 C47 90.0(3) . . ?
C43 C48 H70 125.1 . . ?
C49 C48 H70 125.1 . . ?
C47 C48 H70 125.1 . . ?
C62 C49 C48 120.8(3) . . ?
C62 C49 C44 124.1(3) . . ?
C48 C49 C44 89.8(3) . . ?
C62 C49 C46 131.5(3) . . ?
C48 C49 C46 89.3(3) . . ?
C44 C49 C46 89.7(3) . . ?
C55 C50 C51 117.9(4) . . ?
C55 C50 C43 121.8(4) . . ?
C51 C50 C43 120.3(4) . . ?
C52 C51 C50 121.0(4) . . ?
C52 C51 H43 119.5 . . ?
C50 C51 H43 119.5 . . ?
C51 C52 C53 121.7(4) . . ?
C51 C52 H44 119.1 . . ?
C53 C52 H44 119.1 . . ?
C54 C53 C52 116.6(4) . . ?
C54 C53 C56 122.2(4) . . ?
C52 C53 C56 121.2(4) . . ?
C53 C54 C55 122.5(4) . . ?
C53 C54 H45 118.7 . . ?
C55 C54 H45 118.7 . . ?
C54 C55 C50 120.3(4) . . ?
C54 C55 H46 119.9 . . ?
C50 C55 H46 119.9 . . ?
C61 C56 C57 117.8(4) . . ?
C61 C56 C53 120.2(4) . . ?
C57 C56 C53 122.0(3) . . ?
C56 C57 C58 120.7(4) . . ?
C56 C57 H47 119.7 . . ?
C58 C57 H47 119.7 . . ?
C59 C58 C57 120.9(4) . . ?
C59 C58 H48 119.6 . . ?
C57 C58 H48 119.6 . . ?
C58 C59 C60 119.3(4) . . ?
C58 C59 H49 120.3 . . ?
C60 C59 H49 120.3 . . ?
C61 C60 C59 119.6(4) . . ?
C61 C60 H50 120.2 . . ?
C59 C60 H50 120.2 . . ?
C60 C61 C56 121.8(4) . . ?
C60 C61 H51 119.1 . . ?
C56 C61 H51 119.1 . . ?
O4 C62 N4 122.4(3) . . ?
O4 C62 C49 118.8(3) . . ?
N4 C62 C49 118.6(3) . . ?
C62 N4 C63 123.4(3) . . ?
C62 N4 C66 119.7(3) . . ?
C63 N4 C66 116.9(3) . . ?
N4 C63 C64 111.8(4) . . ?
N4 C63 C65 110.1(4) . . ?
C64 C63 C65 113.7(4) . . ?
N4 C63 H71 107.0 . . ?
C64 C63 H71 107.0 . . ?
C65 C63 H71 107.0 . . ?
C63 C64 H72 109.5 . . ?
C63 C64 H73 109.5 . . ?
H72 C64 H73 109.5 . . ?
C63 C64 H74 109.5 . . ?
H72 C64 H74 109.5 . . ?
H73 C64 H74 109.5 . . ?
C63 C65 H75 109.5 . . ?
C63 C65 H76 109.5 . . ?
H75 C65 H76 109.5 . . ?
C63 C65 H77 109.5 . . ?
H75 C65 H77 109.5 . . ?
H76 C65 H77 109.5 . . ?
N4 C66 C68 113.2(3) . . ?
N4 C66 C67 111.5(3) . . ?
C68 C66 C67 111.4(4) . . ?
N4 C66 H78 106.8 . . ?
C68 C66 H78 106.8 . . ?
C67 C66 H78 106.8 . . ?
C66 C67 H79 109.5 . . ?
C66 C67 H80 109.5 . . ?
H79 C67 H80 109.5 . . ?
C66 C67 H81 109.5 . . ?
H79 C67 H81 109.5 . . ?
H80 C67 H81 109.5 . . ?
C66 C68 H82 109.5 . . ?
C66 C68 H83 109.5 . . ?
H82 C68 H83 109.5 . . ?
C66 C68 H84 109.5 . . ?
H82 C68 H84 109.5 . . ?
H83 C68 H84 109.5 . . ?
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 C1 1.232(4) . ?
C1 N1 1.348(5) . ?
C1 C8 1.503(5) . ?
N1 C5 1.476(5) . ?
N1 C2 1.485(4) . ?
C2 C4 1.515(6) . ?
C2 C3 1.525(5) . ?
C2 H10 1.0000 . ?
C3 H11 0.9800 . ?
C3 H12 0.9800 . ?
C3 H13 0.9800 . ?
C4 H14 0.9800 . ?
C4 H15 0.9800 . ?
C4 H16 0.9800 . ?
C5 C6 1.512(5) . ?
C5 C7 1.526(5) . ?
C5 H17 1.0000 . ?
C6 H18 0.9800 . ?
C6 H19 0.9800 . ?
C6 H20 0.9800 . ?
C7 H21 0.9800 . ?
C7 H22 0.9800 . ?
C7 H23 0.9800 . ?
C8 C13 1.556(5) . ?
C8 C11 1.564(5) . ?
C8 C9 1.597(5) . ?
C9 C16 1.478(5) . ?
C9 C10 1.559(5) . ?
C9 C14 1.573(5) . ?
C10 C15 1.552(5) . ?
C10 C11 1.563(5) . ?
C10 H24 1.0000 . ?
C11 C12 1.557(5) . ?
C11 H25 1.0000 . ?
C12 C13 1.558(5) . ?
C12 C15 1.574(5) . ?
C12 H26 1.0000 . ?
C13 C14 1.558(5) . ?
C13 H27 1.0000 . ?
C14 C15 1.568(5) . ?
C14 H28 1.0000 . ?
C15 C28 1.507(5) . ?
C16 C17 1.385(5) . ?
C16 C21 1.390(5) . ?
C17 C18 1.383(5) . ?
C17 H1 0.9500 . ?
C18 C19 1.406(5) . ?
C18 H2 0.9500 . ?
C19 C20 1.386(5) . ?
C19 C22 1.487(5) . ?
C20 C21 1.386(5) . ?
C20 H3 0.9500 . ?
C21 H4 0.9500 . ?
C22 C23 1.385(5) . ?
C22 C27 1.400(5) . ?
C23 C24 1.391(5) . ?
C23 H5 0.9500 . ?
C24 C25 1.381(6) . ?
C24 H6 0.9500 . ?
C25 C26 1.373(6) . ?
C25 H7 0.9500 . ?
C26 C27 1.385(5) . ?
C26 H8 0.9500 . ?
C27 H9 0.9500 . ?
C28 O2 1.222(4) . ?
C28 N2 1.357(4) . ?
N2 C29 1.474(5) . ?
N2 C32 1.489(4) . ?
C29 C30 1.523(6) . ?
C29 C31 1.524(6) . ?
C29 H29 1.0000 . ?
C30 H30 0.9800 . ?
C30 H31 0.9800 . ?
C30 H32 0.9800 . ?
C31 H33 0.9800 . ?
C31 H34 0.9800 . ?
C31 H35 0.9800 . ?
C32 C33 1.515(5) . ?
C32 C34 1.522(5) . ?
C32 H36 1.0000 . ?
C33 H37 0.9800 . ?
C33 H38 0.9800 . ?
C33 H39 0.9800 . ?
C34 H40 0.9800 . ?
C34 H41 0.9800 . ?
C34 H42 0.9800 . ?
O3 C35 1.229(4) . ?
C35 N3 1.356(5) . ?
C35 C42 1.510(5) . ?
N3 C39 1.475(5) . ?
N3 C36 1.480(5) . ?
C36 C37 1.508(6) . ?
C36 C38 1.516(6) . ?
C36 H52 1.0000 . ?
C37 H53 0.9800 . ?
C37 H54 0.9800 . ?
C37 H55 0.9800 . ?
C38 H56 0.9800 . ?
C38 H57 0.9800 . ?
C38 H58 0.9800 . ?
C39 C40 1.511(6) . ?
C39 C41 1.517(6) . ?
C39 H59 1.0000 . ?
C40 H60 0.9800 . ?
C40 H61 0.9800 . ?
C40 H62 0.9800 . ?
C41 H63 0.9800 . ?
C41 H64 0.9800 . ?
C41 H65 0.9800 . ?
C42 C45 1.554(5) . ?
C42 C47 1.571(6) . ?
C42 C43 1.612(5) . ?
C43 C50 1.489(5) . ?
C43 C48 1.552(5) . ?
C43 C44 1.562(5) . ?
C44 C49 1.561(5) . ?
C44 C45 1.561(6) . ?
C44 H66 1.0000 . ?
C45 C46 1.557(6) . ?
C45 H67 1.0000 . ?
C46 C47 1.541(6) . ?
C46 C49 1.564(6) . ?
C46 H68 1.0000 . ?
C47 C48 1.567(6) . ?
C47 H69 1.0000 . ?
C48 C49 1.560(5) . ?
C48 H70 1.0000 . ?
C49 C62 1.501(5) . ?
C50 C55 1.386(5) . ?
C50 C51 1.399(5) . ?
C51 C52 1.368(6) . ?
C51 H43 0.9500 . ?
C52 C53 1.399(5) . ?
C52 H44 0.9500 . ?
C53 C54 1.381(5) . ?
C53 C56 1.485(5) . ?
C54 C55 1.383(5) . ?
C54 H45 0.9500 . ?
C55 H46 0.9500 . ?
C56 C61 1.378(5) . ?
C56 C57 1.388(5) . ?
C57 C58 1.395(6) . ?
C57 H47 0.9500 . ?
C58 C59 1.345(6) . ?
C58 H48 0.9500 . ?
C59 C60 1.403(6) . ?
C59 H49 0.9500 . ?
C60 C61 1.375(6) . ?
C60 H50 0.9500 . ?
C61 H51 0.9500 . ?
C62 O4 1.237(5) . ?
C62 N4 1.356(5) . ?
N4 C63 1.457(5) . ?
N4 C66 1.487(5) . ?
C63 C64 1.504(7) . ?
C63 C65 1.524(7) . ?
C63 H71 1.0000 . ?
C64 H72 0.9800 . ?
C64 H73 0.9800 . ?
C64 H74 0.9800 . ?
C65 H75 0.9800 . ?
C65 H76 0.9800 . ?
C65 H77 0.9800 . ?
C66 C68 1.493(6) . ?
C66 C67 1.533(6) . ?
C66 H78 1.0000 . ?
C67 H79 0.9800 . ?
C67 H80 0.9800 . ?
C67 H81 0.9800 . ?
C68 H82 0.9800 . ?
C68 H83 0.9800 . ?
C68 H84 0.9800 . ?
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
O1 C1 N1 C5 -179.3(3) . . . . ?
C8 C1 N1 C5 3.5(5) . . . . ?
O1 C1 N1 C2 0.1(5) . . . . ?
C8 C1 N1 C2 -177.2(3) . . . . ?
C1 N1 C2 C4 64.4(4) . . . . ?
C5 N1 C2 C4 -116.3(4) . . . . ?
C1 N1 C2 C3 -63.8(5) . . . . ?
C5 N1 C2 C3 115.5(4) . . . . ?
C1 N1 C5 C6 110.6(4) . . . . ?
C2 N1 C5 C6 -68.7(4) . . . . ?
C1 N1 C5 C7 -123.7(4) . . . . ?
C2 N1 C5 C7 56.9(4) . . . . ?
O1 C1 C8 C13 6.8(5) . . . . ?
N1 C1 C8 C13 -175.8(3) . . . . ?
O1 C1 C8 C11 128.8(4) . . . . ?
N1 C1 C8 C11 -53.9(5) . . . . ?
O1 C1 C8 C9 -105.1(4) . . . . ?
N1 C1 C8 C9 72.2(5) . . . . ?
C1 C8 C9 C16 -6.2(5) . . . . ?
C13 C8 C9 C16 -132.7(4) . . . . ?
C11 C8 C9 C16 137.8(3) . . . . ?
C1 C8 C9 C10 -144.4(3) . . . . ?
C13 C8 C9 C10 89.1(3) . . . . ?
C11 C8 C9 C10 -0.5(2) . . . . ?
C1 C8 C9 C14 125.9(3) . . . . ?
C13 C8 C9 C14 -0.6(3) . . . . ?
C11 C8 C9 C14 -90.2(3) . . . . ?
C16 C9 C10 C15 133.0(4) . . . . ?
C14 C9 C10 C15 -1.5(3) . . . . ?
C8 C9 C10 C15 -90.2(3) . . . . ?
C16 C9 C10 C11 -136.4(4) . . . . ?
C14 C9 C10 C11 89.1(3) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 C12 -90.7(3) . . . . ?
C15 C10 C11 C8 90.1(3) . . . . ?
C9 C10 C11 C8 -0.5(3) . . . . ?
C1 C8 C11 C12 -132.3(4) . . . . ?
C13 C8 C11 C12 0.3(3) . . . . ?
C9 C8 C11 C12 90.2(3) . . . . ?
C1 C8 C11 C10 137.9(4) . . . . ?
C13 C8 C11 C10 -89.4(3) . . . . ?
C9 C8 C11 C10 0.5(2) . . . . ?
C10 C11 C12 C13 90.3(3) . . . . ?
C8 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C15 0.1(3) . . . . ?
C8 C11 C12 C15 -90.6(3) . . . . ?
C1 C8 C13 C14 -128.4(3) . . . . ?
C11 C8 C13 C14 89.8(3) . . . . ?
C9 C8 C13 C14 0.6(3) . . . . ?
C1 C8 C13 C12 141.5(3) . . . . ?
C11 C8 C13 C12 -0.3(3) . . . . ?
C9 C8 C13 C12 -89.5(3) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C15 C12 C13 C8 90.4(3) . . . . ?
C11 C12 C13 C14 -90.4(3) . . . . ?
C15 C12 C13 C14 -0.3(3) . . . . ?
C8 C13 C14 C15 -90.2(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C8 C13 C14 C9 -0.6(3) . . . . ?
C12 C13 C14 C9 89.8(3) . . . . ?
C16 C9 C14 C13 134.0(3) . . . . ?
C10 C9 C14 C13 -89.0(3) . . . . ?
C8 C9 C14 C13 0.6(3) . . . . ?
C16 C9 C14 C15 -135.6(3) . . . . ?
C10 C9 C14 C15 1.5(3) . . . . ?
C8 C9 C14 C15 91.1(3) . . . . ?
C9 C10 C15 C28 -134.3(3) . . . . ?
C11 C10 C15 C28 135.1(3) . . . . ?
C9 C10 C15 C14 1.5(3) . . . . ?
C11 C10 C15 C14 -89.1(3) . . . . ?
C9 C10 C15 C12 90.7(3) . . . . ?
C11 C10 C15 C12 0.1(3) . . . . ?
C13 C14 C15 C28 -140.5(4) . . . . ?
C9 C14 C15 C28 128.7(4) . . . . ?
C13 C14 C15 C10 89.2(3) . . . . ?
C9 C14 C15 C10 -1.5(3) . . . . ?
C13 C14 C15 C12 -0.3(3) . . . . ?
C9 C14 C15 C12 -91.0(3) . . . . ?
C11 C12 C15 C28 -129.6(4) . . . . ?
C13 C12 C15 C28 140.6(4) . . . . ?
C11 C12 C15 C10 -0.1(3) . . . . ?
C13 C12 C15 C10 -89.9(3) . . . . ?
C11 C12 C15 C14 90.1(3) . . . . ?
C13 C12 C15 C14 0.3(3) . . . . ?
C10 C9 C16 C17 175.3(3) . . . . ?
C14 C9 C16 C17 -64.0(5) . . . . ?
C8 C9 C16 C17 52.6(5) . . . . ?
C10 C9 C16 C21 -5.6(5) . . . . ?
C14 C9 C16 C21 115.1(4) . . . . ?
C8 C9 C16 C21 -128.4(4) . . . . ?
C21 C16 C17 C18 0.8(5) . . . . ?
C9 C16 C17 C18 179.9(3) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C17 C18 C19 C22 178.9(3) . . . . ?
C18 C19 C20 C21 1.3(5) . . . . ?
C22 C19 C20 C21 -178.1(3) . . . . ?
C19 C20 C21 C16 -1.0(5) . . . . ?
C17 C16 C21 C20 -0.1(5) . . . . ?
C9 C16 C21 C20 -179.1(3) . . . . ?
C20 C19 C22 C23 -154.8(3) . . . . ?
C18 C19 C22 C23 25.8(5) . . . . ?
C20 C19 C22 C27 25.8(5) . . . . ?
C18 C19 C22 C27 -153.6(3) . . . . ?
C27 C22 C23 C24 1.3(5) . . . . ?
C19 C22 C23 C24 -178.1(3) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 -0.5(6) . . . . ?
C24 C25 C26 C27 1.0(6) . . . . ?
C25 C26 C27 C22 -0.4(5) . . . . ?
C23 C22 C27 C26 -0.8(5) . . . . ?
C19 C22 C27 C26 178.6(3) . . . . ?
C10 C15 C28 O2 -1.8(5) . . . . ?
C14 C15 C28 O2 -119.5(4) . . . . ?
C12 C15 C28 O2 114.6(4) . . . . ?
C10 C15 C28 N2 177.2(3) . . . . ?
C14 C15 C28 N2 59.6(5) . . . . ?
C12 C15 C28 N2 -66.3(5) . . . . ?
O2 C28 N2 C29 179.0(3) . . . . ?
C15 C28 N2 C29 0.0(5) . . . . ?
O2 C28 N2 C32 -1.1(5) . . . . ?
C15 C28 N2 C32 179.8(3) . . . . ?
C28 N2 C29 C30 -115.6(4) . . . . ?
C32 N2 C29 C30 64.5(4) . . . . ?
C28 N2 C29 C31 117.3(4) . . . . ?
C32 N2 C29 C31 -62.5(4) . . . . ?
C28 N2 C32 C33 -64.5(4) . . . . ?
C29 N2 C32 C33 115.4(4) . . . . ?
C28 N2 C32 C34 63.1(4) . . . . ?
C29 N2 C32 C34 -117.0(4) . . . . ?
O3 C35 N3 C39 179.4(4) . . . . ?
C42 C35 N3 C39 -2.8(5) . . . . ?
O3 C35 N3 C36 3.9(5) . . . . ?
C42 C35 N3 C36 -178.3(3) . . . . ?
C35 N3 C36 C37 -70.2(5) . . . . ?
C39 N3 C36 C37 114.0(4) . . . . ?
C35 N3 C36 C38 58.2(5) . . . . ?
C39 N3 C36 C38 -117.6(4) . . . . ?
C35 N3 C39 C40 -104.5(4) . . . . ?
C36 N3 C39 C40 71.2(4) . . . . ?
C35 N3 C39 C41 128.2(4) . . . . ?
C36 N3 C39 C41 -56.1(4) . . . . ?
O3 C35 C42 C45 -9.6(5) . . . . ?
N3 C35 C42 C45 172.6(3) . . . . ?
O3 C35 C42 C47 -132.1(4) . . . . ?
N3 C35 C42 C47 50.0(6) . . . . ?
O3 C35 C42 C43 102.1(4) . . . . ?
N3 C35 C42 C43 -75.7(5) . . . . ?
C35 C42 C43 C50 5.6(6) . . . . ?
C45 C42 C43 C50 132.2(4) . . . . ?
C47 C42 C43 C50 -138.5(4) . . . . ?
C35 C42 C43 C48 144.3(4) . . . . ?
C45 C42 C43 C48 -89.1(3) . . . . ?
C47 C42 C43 C48 0.2(3) . . . . ?
C35 C42 C43 C44 -125.7(4) . . . . ?
C45 C42 C43 C44 0.9(3) . . . . ?
C47 C42 C43 C44 90.2(3) . . . . ?
C50 C43 C44 C49 136.7(4) . . . . ?
C48 C43 C44 C49 -1.0(3) . . . . ?
C42 C43 C44 C49 -91.1(3) . . . . ?
C50 C43 C44 C45 -133.1(4) . . . . ?
C48 C43 C44 C45 89.2(3) . . . . ?
C42 C43 C44 C45 -0.9(3) . . . . ?
C35 C42 C45 C46 -141.7(4) . . . . ?
C47 C42 C45 C46 0.8(3) . . . . ?
C43 C42 C45 C46 89.1(3) . . . . ?
C35 C42 C45 C44 128.3(3) . . . . ?
C47 C42 C45 C44 -89.2(3) . . . . ?
C43 C42 C45 C44 -0.9(3) . . . . ?
C49 C44 C45 C42 90.8(3) . . . . ?
C43 C44 C45 C42 0.9(3) . . . . ?
C49 C44 C45 C46 0.6(3) . . . . ?
C43 C44 C45 C46 -89.3(3) . . . . ?
C42 C45 C46 C47 -0.8(3) . . . . ?
C44 C45 C46 C47 90.2(3) . . . . ?
C42 C45 C46 C49 -91.6(3) . . . . ?
C44 C45 C46 C49 -0.6(3) . . . . ?
C45 C46 C47 C48 -90.3(3) . . . . ?
C49 C46 C47 C48 -0.1(3) . . . . ?
C45 C46 C47 C42 0.8(3) . . . . ?
C49 C46 C47 C42 91.0(3) . . . . ?
C35 C42 C47 C46 132.5(4) . . . . ?
C45 C42 C47 C46 -0.8(3) . . . . ?
C43 C42 C47 C46 -90.1(3) . . . . ?
C35 C42 C47 C48 -137.6(4) . . . . ?
C45 C42 C47 C48 89.1(3) . . . . ?
C43 C42 C47 C48 -0.2(3) . . . . ?
C50 C43 C48 C49 -133.6(4) . . . . ?
C44 C43 C48 C49 1.0(3) . . . . ?
C42 C43 C48 C49 89.8(3) . . . . ?
C50 C43 C48 C47 136.4(4) . . . . ?
C44 C43 C48 C47 -89.0(3) . . . . ?
C42 C43 C48 C47 -0.2(3) . . . . ?
C46 C47 C48 C43 90.4(3) . . . . ?
C42 C47 C48 C43 0.2(3) . . . . ?
C46 C47 C48 C49 0.1(3) . . . . ?
C42 C47 C48 C49 -90.1(3) . . . . ?
C43 C48 C49 C62 129.5(4) . . . . ?
C47 C48 C49 C62 -139.9(4) . . . . ?
C43 C48 C49 C44 -1.0(3) . . . . ?
C47 C48 C49 C44 89.6(3) . . . . ?
C43 C48 C49 C46 -90.7(3) . . . . ?
C47 C48 C49 C46 -0.1(3) . . . . ?
C45 C44 C49 C62 142.1(4) . . . . ?
C43 C44 C49 C62 -126.9(4) . . . . ?
C45 C44 C49 C48 -89.9(3) . . . . ?
C43 C44 C49 C48 1.0(3) . . . . ?
C45 C44 C49 C46 -0.6(3) . . . . ?
C43 C44 C49 C46 90.3(3) . . . . ?
C47 C46 C49 C62 132.3(4) . . . . ?
C45 C46 C49 C62 -137.4(4) . . . . ?
C47 C46 C49 C48 0.1(3) . . . . ?
C45 C46 C49 C48 90.4(3) . . . . ?
C47 C46 C49 C44 -89.6(3) . . . . ?
C45 C46 C49 C44 0.6(3) . . . . ?
C48 C43 C50 C55 -6.7(6) . . . . ?
C44 C43 C50 C55 -128.0(4) . . . . ?
C42 C43 C50 C55 116.4(4) . . . . ?
C48 C43 C50 C51 173.2(4) . . . . ?
C44 C43 C50 C51 51.9(5) . . . . ?
C42 C43 C50 C51 -63.7(5) . . . . ?
C55 C50 C51 C52 0.2(6) . . . . ?
C43 C50 C51 C52 -179.7(4) . . . . ?
C50 C51 C52 C53 -1.2(6) . . . . ?
C51 C52 C53 C54 1.5(6) . . . . ?
C51 C52 C53 C56 -178.7(4) . . . . ?
C52 C53 C54 C55 -0.8(6) . . . . ?
C56 C53 C54 C55 179.4(3) . . . . ?
C53 C54 C55 C50 -0.2(6) . . . . ?
C51 C50 C55 C54 0.5(6) . . . . ?
C43 C50 C55 C54 -179.7(4) . . . . ?
C54 C53 C56 C61 -24.0(5) . . . . ?
C52 C53 C56 C61 156.2(4) . . . . ?
C54 C53 C56 C57 157.6(4) . . . . ?
C52 C53 C56 C57 -22.2(5) . . . . ?
C61 C56 C57 C58 -1.4(5) . . . . ?
C53 C56 C57 C58 177.1(4) . . . . ?
C56 C57 C58 C59 1.0(6) . . . . ?
C57 C58 C59 C60 0.0(6) . . . . ?
C58 C59 C60 C61 -0.5(6) . . . . ?
C59 C60 C61 C56 0.1(6) . . . . ?
C57 C56 C61 C60 0.9(6) . . . . ?
C53 C56 C61 C60 -177.6(4) . . . . ?
C48 C49 C62 O4 -4.3(6) . . . . ?
C44 C49 C62 O4 109.1(4) . . . . ?
C46 C49 C62 O4 -124.8(5) . . . . ?
C48 C49 C62 N4 -178.1(3) . . . . ?
C44 C49 C62 N4 -64.7(5) . . . . ?
C46 C49 C62 N4 61.4(6) . . . . ?
O4 C62 N4 C63 178.5(4) . . . . ?
C49 C62 N4 C63 -7.9(6) . . . . ?
O4 C62 N4 C66 -0.8(6) . . . . ?
C49 C62 N4 C66 172.7(3) . . . . ?
C62 N4 C63 C64 116.3(4) . . . . ?
C66 N4 C63 C64 -64.4(5) . . . . ?
C62 N4 C63 C65 -116.3(4) . . . . ?
C66 N4 C63 C65 63.0(5) . . . . ?
C62 N4 C66 C68 64.8(5) . . . . ?
C63 N4 C66 C68 -114.6(4) . . . . ?
C62 N4 C66 C67 -61.8(5) . . . . ?
C63 N4 C66 C67 118.8(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306324
