#------------------------------------------------------------------------------
#$Date: 2024-05-05 07:02:31 +0300 (Sun, 05 May 2024) $
#$Revision: 291690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/98/7159851.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_7159851
loop_
_publ_author_name
'Le Roy, Marie M.'
'Claes, Sandra'
'Saffon-Merceron, Nathalie'
'Schols, Dominique'
'Troadec, Thibault'
'Tripier, Raphaël'
_publ_section_title
;
 Selective synthesis of an elusive C-functional bis-cyclam and
 study of its inhibition of the CXCR4 chemokine receptor.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3059
_journal_page_last               3067
_journal_paper_doi               10.1039/d3ob02050a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C36 H54 N8 O4'
_chemical_formula_weight         662.87
_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
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-07 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                63.913(2)
_cell_angle_beta                 89.426(2)
_cell_angle_gamma                73.285(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1829(8)
_cell_length_b                   13.8753(10)
_cell_length_c                   14.2627(10)
_cell_measurement_reflns_used    9248
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      2.82
_cell_volume                     1717.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            53091
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.155
_diffrn_reflns_theta_min         1.604
_diffrn_source                   'Incoatec microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       plate
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         9117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0797
_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)+(0.1294P)²+1.5512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.2686
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5459
_reflns_number_total             9117
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob02050a2.cif
_cod_data_source_block           4
_cod_depositor_comments          'Adding full bibliography for 7159851.cif.'
_cod_database_code               7159851
_shelx_shelxl_version_number     2018/3
_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   0.983
_shelx_estimated_absorpt_t_max   0.991
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 0.8028(3) 0.23388(17) 0.54057(19) 0.0524(6) Uani 1 1 d . . . . .
O2 O 0.5728(3) 0.29111(17) -0.12301(16) 0.0487(6) Uani 1 1 d . . . . .
N1 N 0.8054(2) 0.40026(19) 0.53037(17) 0.0324(5) Uani 1 1 d . . . . .
N2 N 0.8409(3) 0.5278(2) 0.63270(19) 0.0418(6) Uani 1 1 d . . . . .
N3 N 0.6145(2) 0.6268(2) 0.52820(18) 0.0338(5) Uani 1 1 d . . . . .
N4 N 0.7231(2) 0.57343(18) 0.36648(16) 0.0295(5) Uani 1 1 d . . . . .
N5 N 0.7006(2) 0.10609(18) -0.04729(17) 0.0296(5) Uani 1 1 d . . . . .
N6 N 0.8975(2) -0.0732(2) -0.0666(2) 0.0438(6) Uani 1 1 d . . . . .
N7 N 0.7396(2) -0.15635(19) 0.0470(2) 0.0363(6) Uani 1 1 d . . . . .
N8 N 0.7283(2) -0.01152(19) 0.14225(18) 0.0343(5) Uani 1 1 d . . . . .
C1 C 0.7896(3) 0.3347(2) 0.4867(2) 0.0344(6) Uani 1 1 d . . . . .
C2 C 0.8698(3) 0.3448(3) 0.6404(2) 0.0449(7) Uani 1 1 d . . . . .
H2A H 0.971371 0.328067 0.642856 0.054 Uiso 1 1 calc R U . . .
H2B H 0.850324 0.272352 0.679145 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8156(3) 0.4186(3) 0.6920(2) 0.0471(8) Uani 1 1 d . . . . .
H3A H 0.715088 0.431295 0.694041 0.056 Uiso 1 1 calc R U . . .
H3B H 0.862260 0.381183 0.765349 0.056 Uiso 1 1 calc R U . . .
C4 C 0.8095(4) 0.5993(4) 0.6864(3) 0.0579(10) Uani 1 1 d . . . . .
H4A H 0.848596 0.662075 0.651562 0.070 Uiso 1 1 calc R U . . .
H4B H 0.855276 0.553873 0.760222 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6556(4) 0.6482(4) 0.6863(3) 0.0572(9) Uani 1 1 d . . . . .
H5A H 0.618423 0.587121 0.731905 0.069 Uiso 1 1 calc R U . . .
H5B H 0.639797 0.703722 0.714437 0.069 Uiso 1 1 calc R U . . .
C6 C 0.5819(4) 0.7056(3) 0.5747(3) 0.0472(8) Uani 1 1 d . . . . .
H6A H 0.480731 0.731782 0.575177 0.057 Uiso 1 1 calc R U . . .
H6B H 0.610906 0.772434 0.531367 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5408(3) 0.6836(2) 0.4205(2) 0.0374(6) Uani 1 1 d . . . . .
H7A H 0.568117 0.751507 0.377434 0.045 Uiso 1 1 calc R U . . .
H7B H 0.439815 0.708354 0.422273 0.045 Uiso 1 1 calc R U . . .
C8 C 0.5744(3) 0.6052(2) 0.3721(2) 0.0339(6) Uani 1 1 d . . . . .
H8A H 0.548036 0.536829 0.415261 0.041 Uiso 1 1 calc R U . . .
H8B H 0.522217 0.642730 0.300552 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7672(3) 0.5060(2) 0.3108(2) 0.0328(6) Uani 1 1 d . . . . .
H9A H 0.865692 0.497543 0.301442 0.039 Uiso 1 1 calc R U . . .
H9B H 0.712525 0.546618 0.239859 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7504(3) 0.3889(2) 0.3679(2) 0.0342(6) Uani 1 1 d . . . . .
H10 H 0.650360 0.398053 0.354343 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8063(3) 0.5189(2) 0.4668(2) 0.0291(5) Uani 1 1 d . . . . .
H11 H 0.903798 0.515098 0.453433 0.035 Uiso 1 1 calc R U . . .
C12 C 0.7641(3) 0.5886(2) 0.5272(2) 0.0331(6) Uani 1 1 d . . . . .
H12 H 0.792088 0.658083 0.489165 0.040 Uiso 1 1 calc R U . . .
C13 C 0.8333(3) 0.3081(3) 0.3256(3) 0.0424(7) Uani 1 1 d . . . . .
H13A H 0.931830 0.303734 0.331467 0.051 Uiso 1 1 calc R U . . .
H13B H 0.827302 0.231475 0.369999 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7828(3) 0.3442(2) 0.2128(2) 0.0373(6) Uani 1 1 d . . . . .
C15 C 0.8354(3) 0.4140(3) 0.1279(3) 0.0435(7) Uani 1 1 d . . . . .
H15 H 0.906670 0.440107 0.140702 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7857(4) 0.4456(3) 0.0262(3) 0.0479(8) Uani 1 1 d . . . . .
H16 H 0.823200 0.492932 -0.030480 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6807(3) 0.4089(3) 0.0051(3) 0.0446(7) Uani 1 1 d . . . . .
H17 H 0.646850 0.431278 -0.065615 0.053 Uiso 1 1 calc R U . . .
C18 C 0.6258(3) 0.3396(2) 0.0880(2) 0.0381(7) Uani 1 1 d . . . . .
C19 C 0.6768(3) 0.3092(3) 0.1900(2) 0.0383(6) Uani 1 1 d . . . . .
H19 H 0.638320 0.262877 0.246688 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5135(3) 0.2965(3) 0.0682(3) 0.0452(8) Uani 1 1 d . . . . .
H20A H 0.453739 0.355000 0.001699 0.054 Uiso 1 1 calc R U . . .
H20B H 0.455440 0.285874 0.125800 0.054 Uiso 1 1 calc R U . . .
C21 C 0.5665(3) 0.1849(2) 0.0608(2) 0.0354(6) Uani 1 1 d . . . . .
H21 H 0.485373 0.156721 0.065663 0.043 Uiso 1 1 calc R U . . .
C22 C 0.6154(3) 0.1996(2) -0.0436(2) 0.0327(6) Uani 1 1 d . . . . .
C23 C 0.7552(3) 0.1223(3) -0.1461(2) 0.0387(6) Uani 1 1 d . . . . .
H23A H 0.837779 0.147092 -0.149022 0.046 Uiso 1 1 calc R U . . .
H23B H 0.684622 0.182177 -0.205952 0.046 Uiso 1 1 calc R U . . .
C24 C 0.7937(3) 0.0143(3) -0.1554(3) 0.0441(7) Uani 1 1 d . . . . .
H24A H 0.710660 -0.009283 -0.155285 0.053 Uiso 1 1 calc R U . . .
H24B H 0.831281 0.025916 -0.222489 0.053 Uiso 1 1 calc R U . . .
C25 C 0.9574(4) -0.1777(3) -0.0770(4) 0.0638(11) Uani 1 1 d . . . . .
H25A H 1.041626 -0.225854 -0.024964 0.077 Uiso 1 1 calc R U . . .
H25B H 0.985128 -0.157961 -0.148244 0.077 Uiso 1 1 calc R U . . .
C26 C 0.8558(4) -0.2446(3) -0.0599(4) 0.0627(11) Uani 1 1 d . . . . .
H26A H 0.777791 -0.201945 -0.118054 0.075 Uiso 1 1 calc R U . . .
H26B H 0.902924 -0.318065 -0.059280 0.075 Uiso 1 1 calc R U . . .
C27 C 0.8024(3) -0.2640(3) 0.0431(3) 0.0520(9) Uani 1 1 d . . . . .
H27A H 0.732471 -0.303416 0.052598 0.062 Uiso 1 1 calc R U . . .
H27B H 0.879462 -0.313117 0.101476 0.062 Uiso 1 1 calc R U . . .
C28 C 0.6886(3) -0.1775(2) 0.1481(2) 0.0422(7) Uani 1 1 d . . . . .
H28A H 0.766242 -0.226064 0.206159 0.051 Uiso 1 1 calc R U . . .
H28B H 0.619438 -0.217517 0.157764 0.051 Uiso 1 1 calc R U . . .
C29 C 0.6238(3) -0.0677(3) 0.1515(2) 0.0395(7) Uani 1 1 d . . . . .
H29A H 0.546997 -0.018511 0.092960 0.047 Uiso 1 1 calc R U . . .
H29B H 0.585583 -0.081799 0.218743 0.047 Uiso 1 1 calc R U . . .
C30 C 0.6770(3) 0.0921(3) 0.1522(2) 0.0376(6) Uani 1 1 d . . . . .
H30A H 0.755383 0.119872 0.155197 0.045 Uiso 1 1 calc R U . . .
H30B H 0.637501 0.075582 0.219141 0.045 Uiso 1 1 calc R U . . .
C31 C 0.7919(2) 0.0086(2) 0.0481(2) 0.0294(5) Uani 1 1 d . . . . .
H31 H 0.875203 0.029589 0.057180 0.035 Uiso 1 1 calc R U . . .
C32 C 0.8438(3) -0.0981(2) 0.0339(2) 0.0354(6) Uani 1 1 d . . . . .
H32 H 0.923412 -0.151390 0.090594 0.042 Uiso 1 1 calc R U . . .
O3 O 0.3697(3) -0.0539(3) 0.5775(2) 0.0747(8) Uani 1 1 d . . . . .
O4 O 0.1842(3) 0.0914(3) 0.4806(2) 0.0731(8) Uani 1 1 d . . . . .
C33 C 0.2992(4) 0.0080(3) 0.4933(3) 0.0605(10) Uani 1 1 d . . . . .
C34 C 0.3261(6) 0.0033(5) 0.3946(4) 0.0826(14) Uani 1 1 d . . . . .
H34A H 0.410205 0.023350 0.373219 0.124 Uiso 1 1 calc R U . . .
H34B H 0.247652 0.056808 0.339886 0.124 Uiso 1 1 calc R U . . .
H34C H 0.338692 -0.073391 0.404293 0.124 Uiso 1 1 calc R U . . .
C35 C 0.1431(4) 0.1027(3) 0.5784(4) 0.0686(11) Uani 1 1 d . . . . .
H35A H 0.226630 0.086638 0.624604 0.082 Uiso 1 1 calc R U . . .
H35B H 0.083096 0.180807 0.558543 0.082 Uiso 1 1 calc R U . . .
C36 C 0.0681(5) 0.0217(4) 0.6344(4) 0.0771(13) Uani 1 1 d . . . . .
H36A H -0.013617 0.037556 0.587818 0.116 Uiso 1 1 calc R U . . .
H36B H 0.039167 0.029163 0.697286 0.116 Uiso 1 1 calc R U . . .
H36C H 0.129061 -0.055460 0.655405 0.116 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
C1 N1 C2 118.4(2) . . ?
C1 N1 C11 123.0(2) . . ?
C2 N1 C11 115.3(2) . . ?
C12 N2 C4 110.3(3) . . ?
C12 N2 C3 110.7(2) . . ?
C4 N2 C3 113.2(3) . . ?
C12 N3 C7 110.4(2) . . ?
C12 N3 C6 109.4(2) . . ?
C7 N3 C6 109.6(2) . . ?
C11 N4 C9 109.7(2) . . ?
C11 N4 C8 113.5(2) . . ?
C9 N4 C8 114.0(2) . . ?
C22 N5 C23 117.0(2) . . ?
C22 N5 C31 121.9(2) . . ?
C23 N5 C31 114.3(2) . . ?
C32 N6 C24 111.9(2) . . ?
C32 N6 C25 110.7(3) . . ?
C24 N6 C25 113.0(3) . . ?
C28 N7 C27 110.0(2) . . ?
C28 N7 C32 109.4(2) . . ?
C27 N7 C32 109.5(2) . . ?
C31 N8 C30 110.4(2) . . ?
C31 N8 C29 113.1(2) . . ?
C30 N8 C29 113.2(2) . . ?
O1 C1 N1 121.7(3) . . ?
O1 C1 C10 119.7(3) . . ?
N1 C1 C10 118.6(2) . . ?
N1 C2 C3 110.7(2) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C2 109.6(3) . . ?
N2 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N2 C4 C5 113.3(3) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 109.4(3) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N3 C6 C5 110.5(3) . . ?
N3 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N3 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N3 C7 C8 110.1(2) . . ?
N3 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
N4 C8 C7 108.7(2) . . ?
N4 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
N4 C8 H8B 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.3 . . ?
N4 C9 C10 113.1(2) . . ?
N4 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N4 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C1 C10 C9 113.0(2) . . ?
C1 C10 C13 109.4(2) . . ?
C9 C10 C13 112.1(2) . . ?
C1 C10 H10 107.4 . . ?
C9 C10 H10 107.4 . . ?
C13 C10 H10 107.4 . . ?
N4 C11 N1 112.2(2) . . ?
N4 C11 C12 111.1(2) . . ?
N1 C11 C12 111.8(2) . . ?
N4 C11 H11 107.1 . . ?
N1 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
N2 C12 N3 112.2(2) . . ?
N2 C12 C11 110.6(2) . . ?
N3 C12 C11 113.2(2) . . ?
N2 C12 H12 106.8 . . ?
N3 C12 H12 106.8 . . ?
C11 C12 H12 106.8 . . ?
C14 C13 C10 113.2(2) . . ?
C14 C13 H13A 108.9 . . ?
C10 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C10 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C19 117.5(3) . . ?
C15 C14 C13 122.8(3) . . ?
C19 C14 C13 119.7(3) . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 118.7(3) . . ?
C19 C18 C20 120.1(3) . . ?
C17 C18 C20 121.2(3) . . ?
C18 C19 C14 122.5(3) . . ?
C18 C19 H19 118.8 . . ?
C14 C19 H19 118.8 . . ?
C18 C20 C21 114.8(2) . . ?
C18 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C18 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 C30 110.5(2) . . ?
C22 C21 C20 113.2(3) . . ?
C30 C21 C20 113.6(2) . . ?
C22 C21 H21 106.3 . . ?
C30 C21 H21 106.3 . . ?
C20 C21 H21 106.3 . . ?
O2 C22 N5 121.7(3) . . ?
O2 C22 C21 120.9(3) . . ?
N5 C22 C21 117.3(2) . . ?
N5 C23 C24 110.4(2) . . ?
N5 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
N5 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N6 C24 C23 109.0(3) . . ?
N6 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
N6 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
N6 C25 C26 112.3(3) . . ?
N6 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
N6 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C27 C26 C25 109.2(3) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
N7 C27 C26 111.0(3) . . ?
N7 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
N7 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
N7 C28 C29 109.9(2) . . ?
N7 C28 H28A 109.7 . . ?
C29 C28 H28A 109.7 . . ?
N7 C28 H28B 109.7 . . ?
C29 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
N8 C29 C28 109.4(2) . . ?
N8 C29 H29A 109.8 . . ?
C28 C29 H29A 109.8 . . ?
N8 C29 H29B 109.8 . . ?
C28 C29 H29B 109.8 . . ?
H29A C29 H29B 108.3 . . ?
N8 C30 C21 112.7(2) . . ?
N8 C30 H30A 109.0 . . ?
C21 C30 H30A 109.0 . . ?
N8 C30 H30B 109.0 . . ?
C21 C30 H30B 109.0 . . ?
H30A C30 H30B 107.8 . . ?
N8 C31 N5 112.5(2) . . ?
N8 C31 C32 111.7(2) . . ?
N5 C31 C32 112.2(2) . . ?
N8 C31 H31 106.7 . . ?
N5 C31 H31 106.7 . . ?
C32 C31 H31 106.7 . . ?
N6 C32 N7 112.0(2) . . ?
N6 C32 C31 110.6(2) . . ?
N7 C32 C31 113.0(2) . . ?
N6 C32 H32 106.9 . . ?
N7 C32 H32 106.9 . . ?
C31 C32 H32 106.9 . . ?
C33 O4 C35 116.8(3) . . ?
O3 C33 O4 122.3(4) . . ?
O3 C33 C34 125.9(4) . . ?
O4 C33 C34 111.9(4) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 O4 108.5(4) . . ?
C36 C35 H35A 110.0 . . ?
O4 C35 H35A 110.0 . . ?
C36 C35 H35B 110.0 . . ?
O4 C35 H35B 110.0 . . ?
H35A C35 H35B 108.4 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 1.231(3) . ?
O2 C22 1.229(3) . ?
N1 C1 1.352(4) . ?
N1 C2 1.467(3) . ?
N1 C11 1.492(3) . ?
N2 C12 1.454(4) . ?
N2 C4 1.467(4) . ?
N2 C3 1.473(4) . ?
N3 C12 1.464(3) . ?
N3 C7 1.470(4) . ?
N3 C6 1.473(4) . ?
N4 C11 1.429(3) . ?
N4 C9 1.454(4) . ?
N4 C8 1.462(3) . ?
N5 C22 1.361(3) . ?
N5 C23 1.457(4) . ?
N5 C31 1.492(3) . ?
N6 C32 1.459(4) . ?
N6 C24 1.461(4) . ?
N6 C25 1.475(4) . ?
N7 C28 1.462(4) . ?
N7 C27 1.472(4) . ?
N7 C32 1.474(3) . ?
N8 C31 1.435(4) . ?
N8 C30 1.450(4) . ?
N8 C29 1.462(3) . ?
C1 C10 1.521(4) . ?
C2 C3 1.492(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.518(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.515(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.490(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.525(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.541(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.532(4) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.504(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(5) . ?
C14 C19 1.398(4) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(4) . ?
C18 C20 1.514(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.537(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.511(4) . ?
C21 C30 1.531(4) . ?
C21 H21 1.0000 . ?
C23 C24 1.501(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.530(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.499(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.498(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.524(4) . ?
C31 H31 1.0000 . ?
C32 H32 1.0000 . ?
O3 C33 1.205(5) . ?
O4 C33 1.335(5) . ?
O4 C35 1.512(6) . ?
C33 C34 1.457(6) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.476(6) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 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
C2 N1 C1 O1 13.9(4) . . . . ?
C11 N1 C1 O1 172.7(3) . . . . ?
C2 N1 C1 C10 -167.8(2) . . . . ?
C11 N1 C1 C10 -9.1(4) . . . . ?
C1 N1 C2 C3 -150.1(3) . . . . ?
C11 N1 C2 C3 49.5(3) . . . . ?
C12 N2 C3 C2 64.1(3) . . . . ?
C4 N2 C3 C2 -171.5(2) . . . . ?
N1 C2 C3 N2 -57.6(3) . . . . ?
C12 N2 C4 C5 53.0(4) . . . . ?
C3 N2 C4 C5 -71.7(4) . . . . ?
N2 C4 C5 C6 -51.6(4) . . . . ?
C12 N3 C6 C5 -59.5(3) . . . . ?
C7 N3 C6 C5 179.4(2) . . . . ?
C4 C5 C6 N3 54.4(4) . . . . ?
C12 N3 C7 C8 58.7(3) . . . . ?
C6 N3 C7 C8 179.3(2) . . . . ?
C11 N4 C8 C7 59.4(3) . . . . ?
C9 N4 C8 C7 -174.0(2) . . . . ?
N3 C7 C8 N4 -61.6(3) . . . . ?
C11 N4 C9 C10 61.8(3) . . . . ?
C8 N4 C9 C10 -66.8(3) . . . . ?
O1 C1 C10 C9 -168.1(3) . . . . ?
N1 C1 C10 C9 13.6(4) . . . . ?
O1 C1 C10 C13 -42.5(4) . . . . ?
N1 C1 C10 C13 139.2(3) . . . . ?
N4 C9 C10 C1 -39.9(3) . . . . ?
N4 C9 C10 C13 -164.1(2) . . . . ?
C9 N4 C11 N1 -54.9(3) . . . . ?
C8 N4 C11 N1 74.0(3) . . . . ?
C9 N4 C11 C12 179.1(2) . . . . ?
C8 N4 C11 C12 -52.0(3) . . . . ?
C1 N1 C11 N4 30.1(3) . . . . ?
C2 N1 C11 N4 -170.6(2) . . . . ?
C1 N1 C11 C12 155.7(2) . . . . ?
C2 N1 C11 C12 -45.0(3) . . . . ?
C4 N2 C12 N3 -57.7(3) . . . . ?
C3 N2 C12 N3 68.3(3) . . . . ?
C4 N2 C12 C11 174.7(2) . . . . ?
C3 N2 C12 C11 -59.2(3) . . . . ?
C7 N3 C12 N2 -177.7(2) . . . . ?
C6 N3 C12 N2 61.6(3) . . . . ?
C7 N3 C12 C11 -51.6(3) . . . . ?
C6 N3 C12 C11 -172.3(2) . . . . ?
N4 C11 C12 N2 175.0(2) . . . . ?
N1 C11 C12 N2 48.8(3) . . . . ?
N4 C11 C12 N3 48.0(3) . . . . ?
N1 C11 C12 N3 -78.2(3) . . . . ?
C1 C10 C13 C14 169.2(2) . . . . ?
C9 C10 C13 C14 -64.7(3) . . . . ?
C10 C13 C14 C15 90.9(3) . . . . ?
C10 C13 C14 C19 -87.7(3) . . . . ?
C19 C14 C15 C16 -0.8(4) . . . . ?
C13 C14 C15 C16 -179.5(3) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C16 C17 C18 C20 -178.9(3) . . . . ?
C17 C18 C19 C14 -1.0(4) . . . . ?
C20 C18 C19 C14 178.3(3) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C13 C14 C19 C18 180.0(3) . . . . ?
C19 C18 C20 C21 -91.2(3) . . . . ?
C17 C18 C20 C21 88.1(4) . . . . ?
C18 C20 C21 C22 -77.3(3) . . . . ?
C18 C20 C21 C30 49.8(4) . . . . ?
C23 N5 C22 O2 8.5(4) . . . . ?
C31 N5 C22 O2 157.8(2) . . . . ?
C23 N5 C22 C21 -175.8(2) . . . . ?
C31 N5 C22 C21 -26.5(3) . . . . ?
C30 C21 C22 O2 -152.3(3) . . . . ?
C20 C21 C22 O2 -23.6(4) . . . . ?
C30 C21 C22 N5 32.1(3) . . . . ?
C20 C21 C22 N5 160.7(2) . . . . ?
C22 N5 C23 C24 -155.9(2) . . . . ?
C31 N5 C23 C24 52.5(3) . . . . ?
C32 N6 C24 C23 63.0(3) . . . . ?
C25 N6 C24 C23 -171.3(2) . . . . ?
N5 C23 C24 N6 -59.1(3) . . . . ?
C32 N6 C25 C26 53.6(4) . . . . ?
C24 N6 C25 C26 -72.7(4) . . . . ?
N6 C25 C26 C27 -53.0(5) . . . . ?
C28 N7 C27 C26 -179.9(2) . . . . ?
C32 N7 C27 C26 -59.6(3) . . . . ?
C25 C26 C27 N7 55.8(4) . . . . ?
C27 N7 C28 C29 -179.6(2) . . . . ?
C32 N7 C28 C29 60.1(3) . . . . ?
C31 N8 C29 C28 57.6(3) . . . . ?
C30 N8 C29 C28 -176.0(2) . . . . ?
N7 C28 C29 N8 -62.0(3) . . . . ?
C31 N8 C30 C21 61.3(3) . . . . ?
C29 N8 C30 C21 -66.6(3) . . . . ?
C22 C21 C30 N8 -50.0(3) . . . . ?
C20 C21 C30 N8 -178.4(2) . . . . ?
C30 N8 C31 N5 -51.4(3) . . . . ?
C29 N8 C31 N5 76.5(3) . . . . ?
C30 N8 C31 C32 -178.6(2) . . . . ?
C29 N8 C31 C32 -50.7(3) . . . . ?
C22 N5 C31 N8 35.9(3) . . . . ?
C23 N5 C31 N8 -174.0(2) . . . . ?
C22 N5 C31 C32 162.9(2) . . . . ?
C23 N5 C31 C32 -47.1(3) . . . . ?
C24 N6 C32 N7 69.8(3) . . . . ?
C25 N6 C32 N7 -57.2(3) . . . . ?
C24 N6 C32 C31 -57.3(3) . . . . ?
C25 N6 C32 C31 175.8(2) . . . . ?
C28 N7 C32 N6 -179.2(2) . . . . ?
C27 N7 C32 N6 60.1(3) . . . . ?
C28 N7 C32 C31 -53.5(3) . . . . ?
C27 N7 C32 C31 -174.2(3) . . . . ?
N8 C31 C32 N6 175.3(2) . . . . ?
N5 C31 C32 N6 48.0(3) . . . . ?
N8 C31 C32 N7 48.8(3) . . . . ?
N5 C31 C32 N7 -78.5(3) . . . . ?
C35 O4 C33 O3 -2.0(6) . . . . ?
C35 O4 C33 C34 178.4(3) . . . . ?
C33 O4 C35 C36 -82.3(4) . . . . ?
