# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 2225027'
loop_
_audit_author_name
_audit_author_address
'Nathalie Saffon'
;Institut de Chimie de Toulouse
France
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H54 N8 O4'
_chemical_formula_weight         662.87

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1829(8)
_cell_length_b                   13.8753(10)
_cell_length_c                   14.2627(10)
_cell_angle_alpha                63.913(2)
_cell_angle_beta                 89.426(2)
_cell_angle_gamma                73.285(2)
_cell_volume                     1717.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9248
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      23.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53091
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.604
_diffrn_reflns_theta_max         29.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9117
_reflns_number_gt                5459
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1294P)²+1.5512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9117
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2686
_refine_ls_wR_factor_gt          0.2293
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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_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_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) . . . . ?

_refine_diff_density_max         0.780
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.077

