# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
# 
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data_1BCP2
_database_code_depnum_ccdc_archive 'CCDC 2293125'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_refine_special_details          
;Crystals were small and weakly-diffracting and it was necessary to use 
synchrotron radiation to obtain data with reasonable intensity. The asymmetric
unit contains two molecules of the tetra-amidinium cation and four BCP2- 
anions. One of these anions is disordered; this was modelled over two 
positions, with occupancies of 0.5 each.  There is one well-defined water 
molecule located between two carboxylate groups and an amidinium group, 
as well as a large amount of ill-defined electron density that could not be 
modelled and was included in the model using the OLEX2 mask feature. This 
removed a total of 940 e- from a volume of 3120 A3 (30% of the unit cell 
volume). This is consistent with the presence of approx. 94 water molecules, 
or approximately 12 water molecules per formula unit in addition to the one 
well-ordered water molecule in the asymmetric unit (which contains two formula 
units).  It was not necessary to use any crystallographic restraints during 
the refinement.,SQUEEZE
;

# start Validation Reply Forms
_vrf_PLAT098_1BCP2               
;
PROBLEM: Large Reported Min.  (Negative) Residual Density      -0.85 eA-3  
RESPONSE: This relatively small peak is located relatively close to one of
the amidinium NH groups.
;
_vrf_PLAT241_1BCP2               
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C62 Check 
RESPONSE: These alerts are related to the three `belt' carbon atoms of one of 
the BCP2- molecules, which appears to be twirling slightly about its axis.
;
# end Validation Reply Form

_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 N8, 2(C7 H6 O4), 0.5(H2 O)'
_chemical_formula_sum            'C43 H45 N8 O8.5'
_chemical_formula_weight         809.87
_chemical_melting_point          ?

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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.804(3)
_cell_length_b                   30.856(6)
_cell_length_c                   21.944(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.44(3)
_cell_angle_gamma                90
_cell_volume                     10488(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    101.0(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      1.33
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.958

_exptl_absorpt_correction_type   None

_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.026
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3416
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            129151
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.683
_diffrn_reflns_theta_min         1.154
_diffrn_ambient_temperature      101.0(2)
_diffrn_detector_area_resol_mean 13.3
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_detector_type 'Dectris Eiger 16M'
_diffrn_measurement_device_type  'MX2 Beamline Australian Synchrotron'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                16298
_reflns_number_total             19615

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'AS QEGUI'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1102
_refine_ls_number_reflns         19615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0906
_refine_ls_restrained_S_all      1.062
_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)+(0.1531P)²+22.5597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2681
_refine_ls_wR_factor_ref         0.2767

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: C104(0.5) H10C(0.5) H10D(0.5) C102(0.5) H10E(0.5) H10F(0.5)
 C103(0.5) H10G(0.5) H10H(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5) C1B(0.5) H1BA(0.5)
 H1BB(0.5) C1C(0.5) H1CA(0.5) H1CB(0.5)
3.a Free rotating group:
 O100(H10I,H10J)
3.b Secondary CH2 refined with riding coordinates:
 C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C94(H94A,H94B), C92(H92A,
 H92B), C93(H93A,H93B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B),
 C104(H10C,H10D), C102(H10E,H10F), C103(H10G,H10H), C1A(H1AA,H1AB), C1B(H1BA,
 H1BB), C1C(H1CA,H1CB)
3.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C26(H26), C57(H57), C015(H015), C43(H43), C21(H21), C28(H28),
 C4(H4), C12(H12), C6(H6), C33(H33), C18(H18), C44(H44), C29(H29), C55(H55),
 C22(H22), C19(H19), C14(H14), C41(H41), C3(H3), C7(H7), C51(H51), C47(H47),
 C50(H50), C48(H48), C11(H11), C15(H15), C54(H54), C32(H32), C35(H35), C40(H40),
  C36(H36)
3.d X=CH2 refined with riding coordinates:
 N14(H14A,H14B), N8(H8A,H8B), N2(H2A,H2B), N7(H7A,H7B), N16(H16A,H16B), N6(H6A,
 H6B), N1(H1A,H1B), N17(H17A,H17B), N13(H13A,H13B), N5(H5A,H5B), N15(H15A,H15B),
  N12(H12A,H12B), N3(H3A,H3B), N4(H4A,H4B), N11(H11A,H11B), N10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.34397(14) 0.38457(7) 0.93602(10) 0.0211(5) Uani 1 1 d . . . . .
O4 O 0.47796(14) 0.42742(7) 0.70132(10) 0.0216(5) Uani 1 1 d . . . . .
O1 O 0.31213(15) 0.31829(7) 0.89585(10) 0.0256(5) Uani 1 1 d . . . . .
O3 O 0.37917(16) 0.38311(8) 0.64806(10) 0.0283(5) Uani 1 1 d . . . . .
O22 O 0.24729(15) 0.08092(8) 0.64929(10) 0.0257(5) Uani 1 1 d . . . . .
O21 O 0.42047(16) 0.18731(8) 0.45509(11) 0.0271(5) Uani 1 1 d . . . . .
O11 O 0.43144(16) 0.46518(7) 0.19473(11) 0.0285(5) Uani 1 1 d . . . . .
O20 O 0.39586(16) 0.11966(8) 0.42081(11) 0.0295(5) Uani 1 1 d . . . . .
O23 O 0.34090(19) 0.12726(9) 0.70292(12) 0.0404(7) Uani 1 1 d . . . . .
O10 O 0.33695(19) 0.41593(8) 0.14775(12) 0.0362(6) Uani 1 1 d . . . . .
N14 N 0.24901(17) 0.29375(8) 0.00097(12) 0.0203(5) Uani 1 1 d . . . . .
H14A H 0.267498 0.301475 -0.032716 0.024 Uiso 1 1 calc R U . . .
H14B H 0.221300 0.269085 0.001752 0.024 Uiso 1 1 calc R U . . .
N8 N 0.47557(17) 0.32071(9) 0.59216(12) 0.0231(6) Uani 1 1 d . . . . .
H8A H 0.530212 0.325274 0.591071 0.028 Uiso 1 1 calc R U . . .
H8B H 0.448402 0.338290 0.613361 0.028 Uiso 1 1 calc R U . . .
N2 N -0.01944(18) 0.29156(9) 0.84601(13) 0.0245(6) Uani 1 1 d . . . . .
H2A H -0.033745 0.298050 0.881682 0.029 Uiso 1 1 calc R U . . .
H2B H -0.003222 0.265025 0.839098 0.029 Uiso 1 1 calc R U . . .
N7 N 0.47203(17) 0.26045(9) 0.52980(12) 0.0225(6) Uani 1 1 d . . . . .
H7A H 0.526632 0.264124 0.527795 0.027 Uiso 1 1 calc R U . . .
H7B H 0.442752 0.238608 0.510194 0.027 Uiso 1 1 calc R U . . .
N16 N 0.12122(18) 0.05126(9) 0.29951(13) 0.0231(6) Uani 1 1 d . . . . .
H16A H 0.123903 0.023267 0.307358 0.028 Uiso 1 1 calc R U . . .
H16B H 0.078742 0.061774 0.271297 0.028 Uiso 1 1 calc R U . . .
N6 N 0.12785(18) 0.05953(9) 0.54380(12) 0.0240(6) Uani 1 1 d . . . . .
H6A H 0.131924 0.032322 0.532704 0.029 Uiso 1 1 calc R U . . .
H6B H 0.165256 0.070206 0.575326 0.029 Uiso 1 1 calc R U . . .
N1 N -0.04616(19) 0.36133(9) 0.81184(13) 0.0261(6) Uani 1 1 d . . . . .
H1A H -0.060697 0.368428 0.847219 0.031 Uiso 1 1 calc R U . . .
H1B H -0.047670 0.380942 0.782520 0.031 Uiso 1 1 calc R U . . .
N17 N 0.24533(18) 0.06330(9) 0.37246(13) 0.0264(6) Uani 1 1 d . . . . .
H17A H 0.249735 0.035479 0.381316 0.032 Uiso 1 1 calc R U . . .
H17B H 0.284159 0.081570 0.392062 0.032 Uiso 1 1 calc R U . . .
O31 O 0.9635(2) 0.43421(9) 0.74157(13) 0.0452(7) Uani 1 1 d . . . . .
N13 N -0.24443(18) 0.25370(10) 0.32181(13) 0.0270(6) Uani 1 1 d . . . . .
H13A H -0.299182 0.256577 0.323890 0.032 Uiso 1 1 calc R U . . .
H13B H -0.213487 0.232702 0.342344 0.032 Uiso 1 1 calc R U . . .
O13 O 0.59294(19) 0.28916(10) 0.30022(14) 0.0477(8) Uani 1 1 d . . . . .
N5 N 0.00839(18) 0.06918(9) 0.46552(12) 0.0248(6) Uani 1 1 d . . . . .
H5A H 0.011200 0.042079 0.453601 0.030 Uiso 1 1 calc R U . . .
H5B H -0.032548 0.086312 0.445778 0.030 Uiso 1 1 calc R U . . .
N15 N 0.3034(2) 0.35569(9) 0.05063(13) 0.0308(7) Uani 1 1 d . . . . .
H15A H 0.322558 0.364153 0.017534 0.037 Uiso 1 1 calc R U . . .
H15B H 0.311793 0.372045 0.084140 0.037 Uiso 1 1 calc R U . . .
N12 N -0.2543(2) 0.31269(10) 0.25663(13) 0.0324(7) Uani 1 1 d . . . . .
H12A H -0.309115 0.316019 0.258215 0.039 Uiso 1 1 calc R U . . .
H12B H -0.229513 0.330534 0.234225 0.039 Uiso 1 1 calc R U . . .
O12 O 0.5454(2) 0.31279(12) 0.38112(15) 0.0558(9) Uani 1 1 d . . . . .
C65 C 0.41746(19) 0.40027(10) 0.69735(14) 0.0185(6) Uani 1 1 d . . . . .
N3 N -0.24920(19) 0.38345(11) 0.41713(15) 0.0342(7) Uani 1 1 d . . . . .
H3A H -0.287707 0.400599 0.394670 0.041 Uiso 1 1 calc R U . . .
H3B H -0.261606 0.369753 0.449427 0.041 Uiso 1 1 calc R U . . .
N4 N -0.1513(2) 0.39793(11) 0.35473(14) 0.0350(7) Uani 1 1 d . . . . .
H4A H -0.188172 0.415331 0.331215 0.042 Uiso 1 1 calc R U . . .
H4B H -0.099789 0.393686 0.346301 0.042 Uiso 1 1 calc R U . . .
C25 C 0.28171(19) 0.27038(10) 0.51151(14) 0.0188(6) Uani 1 1 d . . . . .
H25 H 0.300143 0.264136 0.473797 0.023 Uiso 1 1 calc R U . . .
C27 C 0.16602(18) 0.27575(9) 0.56923(13) 0.0160(6) Uani 1 1 d . . . . .
C26 C 0.19538(19) 0.26836(10) 0.51402(13) 0.0181(6) Uani 1 1 d . . . . .
H26 H 0.154616 0.261772 0.477205 0.022 Uiso 1 1 calc R U . . .
C23 C 0.4343(2) 0.28749(10) 0.56198(14) 0.0199(6) Uani 1 1 d . . . . .
C57 C 0.13242(19) 0.18341(10) 0.24479(13) 0.0177(6) Uani 1 1 d . . . . .
H57 H 0.105472 0.193368 0.204659 0.021 Uiso 1 1 calc R U . . .
C015 C 0.13809(18) 0.13940(10) 0.25644(13) 0.0171(6) Uani 1 1 d . . . . .
H015 H 0.116990 0.119387 0.224088 0.020 Uiso 1 1 calc R U . . .
C60 C 0.33590(19) 0.35692(10) 0.89200(14) 0.0204(6) Uani 1 1 d . . . . .
N11 N 0.3558(2) 0.39604(12) 0.49169(16) 0.0423(8) Uani 1 1 d . . . . .
H11A H 0.391638 0.411368 0.519273 0.051 Uiso 1 1 calc R U . . .
H11B H 0.299805 0.397978 0.489778 0.051 Uiso 1 1 calc R U . . .
N10 N 0.4686(2) 0.36760(11) 0.45649(15) 0.0360(7) Uani 1 1 d . . . . .
H10A H 0.504840 0.382826 0.483946 0.043 Uiso 1 1 calc R U . . .
H10B H 0.488371 0.350267 0.430667 0.043 Uiso 1 1 calc R U . . .
C53 C 0.17502(19) 0.12427(10) 0.31609(14) 0.0190(6) Uani 1 1 d . . . . .
C43 C 0.0302(2) 0.26412(11) 0.33340(14) 0.0228(7) Uani 1 1 d . . . . .
H43 H 0.072051 0.258408 0.369990 0.027 Uiso 1 1 calc R U . . .
C5 C 0.04461(18) 0.28266(10) 0.63088(14) 0.0171(6) Uani 1 1 d . . . . .
C24 C 0.34211(19) 0.28167(10) 0.56486(14) 0.0185(6) Uani 1 1 d . . . . .
O32 O 0.6902(2) 0.35261(13) 0.51986(15) 0.0663(11) Uani 1 1 d . . . . .
C17 C 0.06231(19) 0.13056(10) 0.52897(14) 0.0184(6) Uani 1 1 d . . . . .
C21 C 0.02676(19) 0.20415(10) 0.49630(14) 0.0195(6) Uani 1 1 d . . . . .
H21 H 0.002565 0.223967 0.464449 0.023 Uiso 1 1 calc R U . . .
C16 C 0.0659(2) 0.08422(10) 0.51327(14) 0.0212(6) Uani 1 1 d . . . . .
C28 C 0.22782(19) 0.28466(10) 0.62263(13) 0.0178(6) Uani 1 1 d . . . . .
H28 H 0.210399 0.287818 0.661416 0.021 Uiso 1 1 calc R U . . .
C52 C 0.1810(2) 0.07752(10) 0.33014(14) 0.0197(6) Uani 1 1 d . . . . .
C4 C 0.06947(19) 0.32344(10) 0.65683(14) 0.0194(6) Uani 1 1 d . . . . .
H4 H 0.101529 0.342422 0.635932 0.023 Uiso 1 1 calc R U . . .
C12 C 0.0368(2) 0.33249(11) 0.49250(15) 0.0221(6) Uani 1 1 d . . . . .
H12 H 0.096482 0.339525 0.500485 0.027 Uiso 1 1 calc R U . . .
C56 C 0.1656(2) 0.21356(10) 0.29086(14) 0.0183(6) Uani 1 1 d . . . . .
C45 C 0.2627(2) 0.31901(10) 0.05001(14) 0.0205(6) Uani 1 1 d . . . . .
C6 C -0.00835(19) 0.25727(10) 0.66024(14) 0.0200(6) Uani 1 1 d . . . . .
H6 H -0.030209 0.230652 0.641789 0.024 Uiso 1 1 calc R U . . .
C2 C 0.00023(19) 0.30933(10) 0.74292(14) 0.0189(6) Uani 1 1 d . . . . .
C1 C -0.02230(19) 0.32165(10) 0.80282(14) 0.0203(6) Uani 1 1 d . . . . .
C20 C 0.05869(18) 0.21960(10) 0.55597(14) 0.0173(6) Uani 1 1 d . . . . .
C33 C 0.2997(2) 0.28073(10) 0.34257(14) 0.0223(6) Uani 1 1 d . . . . .
H33 H 0.321417 0.255678 0.325714 0.027 Uiso 1 1 calc R U . . .
C18 C 0.09371(19) 0.14581(10) 0.58905(14) 0.0196(6) Uani 1 1 d . . . . .
H18 H 0.115717 0.125900 0.621342 0.024 Uiso 1 1 calc R U . . .
C44 C -0.0559(2) 0.26694(11) 0.33749(14) 0.0231(7) Uani 1 1 d . . . . .
H44 H -0.072984 0.262731 0.376210 0.028 Uiso 1 1 calc R U . . .
C29 C 0.3142(2) 0.28897(10) 0.61982(14) 0.0209(6) Uani 1 1 d . . . . .
H29 H 0.354746 0.297018 0.656072 0.025 Uiso 1 1 calc R U . . .
C42 C 0.0572(2) 0.26939(9) 0.27736(13) 0.0184(6) Uani 1 1 d . . . . .
C55 C 0.1995(2) 0.19809(10) 0.35075(14) 0.0221(6) Uani 1 1 d . . . . .
H55 H 0.220009 0.218039 0.383301 0.026 Uiso 1 1 calc R U . . .
C22 C 0.02952(19) 0.16039(10) 0.48236(14) 0.0200(6) Uani 1 1 d . . . . .
H22 H 0.009054 0.150680 0.440978 0.024 Uiso 1 1 calc R U . . .
C19 C 0.09306(19) 0.18959(10) 0.60199(13) 0.0191(6) Uani 1 1 d . . . . .
H19 H 0.116359 0.199495 0.642872 0.023 Uiso 1 1 calc R U . . .
C34 C 0.2120(2) 0.29101(10) 0.32521(13) 0.0197(6) Uani 1 1 d . . . . .
C8 C 0.06921(19) 0.26865(10) 0.56951(14) 0.0177(6) Uani 1 1 d . . . . .
C46 C 0.2329(2) 0.30434(10) 0.10694(14) 0.0200(6) Uani 1 1 d . . . . .
C90 C 0.3996(2) 0.14869(11) 0.46140(15) 0.0224(6) Uani 1 1 d . . . . .
C49 C 0.1791(2) 0.27539(10) 0.21443(13) 0.0195(6) Uani 1 1 d . . . . .
C14 C -0.0792(2) 0.28665(10) 0.50761(14) 0.0208(6) Uani 1 1 d . . . . .
H14 H -0.099124 0.261753 0.525994 0.025 Uiso 1 1 calc R U . . .
C39 C -0.1175(2) 0.27607(10) 0.28378(14) 0.0226(7) Uani 1 1 d . . . . .
C41 C -0.0053(2) 0.27708(10) 0.22391(14) 0.0226(7) Uani 1 1 d . . . . .
H41 H 0.011412 0.279447 0.184760 0.027 Uiso 1 1 calc R U . . .
C3 C 0.04826(19) 0.33649(10) 0.71212(15) 0.0214(6) Uani 1 1 d . . . . .
H3 H 0.066465 0.364044 0.729152 0.026 Uiso 1 1 calc R U . . .
C13 C 0.00948(19) 0.29635(10) 0.52013(13) 0.0179(6) Uani 1 1 d . . . . .
C38 C -0.2089(2) 0.28072(11) 0.28807(14) 0.0247(7) Uani 1 1 d . . . . .
C7 C -0.0296(2) 0.26998(10) 0.71543(15) 0.0214(6) Uani 1 1 d . . . . .
H7 H -0.064870 0.251829 0.734951 0.026 Uiso 1 1 calc R U . . .
C51 C 0.1874(2) 0.33237(10) 0.13948(14) 0.0241(7) Uani 1 1 d . . . . .
H51 H 0.174899 0.361197 0.125305 0.029 Uiso 1 1 calc R U . . .
C47 C 0.2510(2) 0.26258(10) 0.12845(14) 0.0207(6) Uani 1 1 d . . . . .
H47 H 0.280601 0.243318 0.106132 0.025 Uiso 1 1 calc R U . . .
C50 C 0.1611(2) 0.31779(10) 0.19188(15) 0.0248(7) Uani 1 1 d . . . . .
H50 H 0.129948 0.336796 0.213439 0.030 Uiso 1 1 calc R U . . .
C48 C 0.2261(2) 0.24856(10) 0.18279(14) 0.0207(6) Uani 1 1 d . . . . .
H48 H 0.241555 0.220298 0.198271 0.025 Uiso 1 1 calc R U . . .
C95 C 0.3073(2) 0.10812(11) 0.65347(14) 0.0235(7) Uani 1 1 d . . . . .
C75 C 0.4462(2) 0.39224(10) 0.23097(14) 0.0229(7) Uani 1 1 d . . . . .
C37 C 0.1538(2) 0.26237(10) 0.27656(13) 0.0190(6) Uani 1 1 d . . . . .
C11 C -0.0212(2) 0.35879(11) 0.45324(15) 0.0241(7) Uani 1 1 d . . . . .
H11 H -0.000810 0.383419 0.434516 0.029 Uiso 1 1 calc R U . . .
C15 C -0.1382(2) 0.31277(11) 0.46889(15) 0.0244(7) Uani 1 1 d . . . . .
H15 H -0.198012 0.305923 0.461253 0.029 Uiso 1 1 calc R U . . .
C10 C -0.1092(2) 0.34923(11) 0.44117(14) 0.0233(7) Uani 1 1 d . . . . .
C54 C 0.2033(2) 0.15427(10) 0.36292(14) 0.0218(6) Uani 1 1 d . . . . .
H54 H 0.225638 0.144408 0.403969 0.026 Uiso 1 1 calc R U . . .
C32 C 0.3551(2) 0.30657(11) 0.38395(15) 0.0250(7) Uani 1 1 d . . . . .
H32 H 0.414068 0.298573 0.396500 0.030 Uiso 1 1 calc R U . . .
C31 C 0.3249(2) 0.34433(11) 0.40734(15) 0.0259(7) Uani 1 1 d . . . . .
C35 C 0.1827(2) 0.32907(11) 0.34835(15) 0.0242(7) Uani 1 1 d . . . . .
H35 H 0.123657 0.337022 0.336428 0.029 Uiso 1 1 calc R U . . .
C40 C -0.0912(2) 0.28127(11) 0.22749(14) 0.0246(7) Uani 1 1 d . . . . .
H40 H -0.132688 0.287790 0.191042 0.029 Uiso 1 1 calc R U . . .
C61 C 0.35893(19) 0.37140(10) 0.83209(14) 0.0205(6) Uani 1 1 d . . . . .
C02U C 0.3903(2) 0.38752(10) 0.75735(14) 0.0201(6) Uani 1 1 d . . . . .
C76 C 0.4009(2) 0.42679(10) 0.18855(15) 0.0244(7) Uani 1 1 d . . . . .
C70 C 0.5516(2) 0.31535(11) 0.32573(16) 0.0255(7) Uani 1 1 d . . . . .
C9 C -0.1733(2) 0.37828(11) 0.40246(15) 0.0260(7) Uani 1 1 d . . . . .
C66 C 0.3387(2) 0.11953(11) 0.59511(15) 0.0245(7) Uani 1 1 d . . . . .
C91 C 0.3738(2) 0.13580(11) 0.52140(15) 0.0234(7) Uani 1 1 d . . . . .
C71 C 0.5036(2) 0.35050(10) 0.28575(15) 0.0230(7) Uani 1 1 d . . . . .
C36 C 0.2392(2) 0.35547(11) 0.38871(15) 0.0264(7) Uani 1 1 d . . . . .
H36 H 0.218496 0.381510 0.403642 0.032 Uiso 1 1 calc R U . . .
O30 O 0.9639(3) 0.47749(14) 0.66129(18) 0.0786(14) Uani 1 1 d . . . . .
C30 C 0.3855(2) 0.37073(12) 0.45405(16) 0.0311(8) Uani 1 1 d . . . . .
C105 C 0.7667(2) 0.38985(12) 0.60709(17) 0.0295(7) Uani 1 1 d . . . . .
C72 C 0.4540(2) 0.39059(12) 0.30280(16) 0.0308(8) Uani 1 1 d . . . . .
H72A H 0.489466 0.413578 0.326917 0.037 Uiso 1 1 calc R U . . .
H72B H 0.399981 0.384552 0.317698 0.037 Uiso 1 1 calc R U . . .
C106 C 0.6917(2) 0.36343(13) 0.57349(18) 0.0325(8) Uani 1 1 d . . . . .
C73 C 0.5437(2) 0.38083(12) 0.24333(19) 0.0329(8) Uani 1 1 d . . . . .
H73A H 0.564768 0.366758 0.208629 0.039 Uiso 1 1 calc R U . . .
H73B H 0.583495 0.403340 0.264637 0.039 Uiso 1 1 calc R U . . .
C101 C 0.8600(2) 0.42108(12) 0.65030(18) 0.0334(8) Uani 1 1 d . . . . .
O33 O 0.6372(3) 0.3517(2) 0.6034(2) 0.115(2) Uani 1 1 d . . . . .
C74 C 0.4266(3) 0.34400(12) 0.2299(2) 0.0401(10) Uani 1 1 d . . . . .
H74A H 0.439556 0.327641 0.194032 0.048 Uiso 1 1 calc R U . . .
H74B H 0.370905 0.335667 0.240663 0.048 Uiso 1 1 calc R U . . .
C100 C 0.9350(3) 0.44592(13) 0.6868(2) 0.0399(9) Uani 1 1 d . . . . .
C94 C 0.4260(3) 0.1388(2) 0.58776(18) 0.0548(14) Uani 1 1 d . . . . .
H94A H 0.438564 0.168458 0.604309 0.066 Uiso 1 1 calc R U . . .
H94B H 0.476384 0.119166 0.597988 0.066 Uiso 1 1 calc R U . . .
C92 C 0.3454(5) 0.09074(16) 0.5399(2) 0.0639(16) Uani 1 1 d . . . . .
H92A H 0.290025 0.079845 0.515422 0.077 Uiso 1 1 calc R U . . .
H92B H 0.390941 0.068257 0.547548 0.077 Uiso 1 1 calc R U . . .
C93 C 0.2977(3) 0.1537(2) 0.5478(2) 0.0617(16) Uani 1 1 d . . . . .
H93A H 0.303084 0.184114 0.562310 0.074 Uiso 1 1 calc R U . . .
H93B H 0.239361 0.146721 0.523761 0.074 Uiso 1 1 calc R U . . .
C62 C 0.3685(5) 0.41733(15) 0.8074(2) 0.078(2) Uani 1 1 d . . . . .
H62A H 0.314407 0.434192 0.795637 0.093 Uiso 1 1 calc R U . . .
H62B H 0.416919 0.434694 0.830743 0.093 Uiso 1 1 calc R U . . .
C63 C 0.3131(4) 0.3602(3) 0.76601(19) 0.084(2) Uani 1 1 d . . . . .
H63A H 0.255661 0.373664 0.751850 0.101 Uiso 1 1 calc R U . . .
H63B H 0.314604 0.329343 0.754090 0.101 Uiso 1 1 calc R U . . .
C64 C 0.4418(4) 0.3611(2) 0.8104(3) 0.083(2) Uani 1 1 d . . . . .
H64A H 0.450759 0.330248 0.801076 0.099 Uiso 1 1 calc R U . . .
H64B H 0.494569 0.375106 0.834037 0.099 Uiso 1 1 calc R U . . .
C104 C 0.7856(6) 0.4037(4) 0.6773(4) 0.047(2) Uani 0.5 1 d . . P A 1
H10C H 0.746176 0.425630 0.689291 0.057 Uiso 0.5 1 calc R U P A 1
H10D H 0.799684 0.379985 0.708004 0.057 Uiso 0.5 1 calc R U P A 1
C102 C 0.8471(5) 0.4067(3) 0.5831(4) 0.042(2) Uani 0.5 1 d . . P A 2
H10E H 0.887431 0.384284 0.573749 0.050 Uiso 0.5 1 calc R U P A 2
H10F H 0.836222 0.430030 0.551578 0.050 Uiso 0.5 1 calc R U P A 2
C103 C 0.7989(6) 0.4333(3) 0.5890(5) 0.053(3) Uani 0.5 1 d . . P A 1
H10G H 0.760405 0.458308 0.590846 0.063 Uiso 0.5 1 calc R U P A 1
H10H H 0.824789 0.433381 0.551403 0.063 Uiso 0.5 1 calc R U P A 1
O100 O 0.62886(15) 0.27502(8) 0.48644(11) 0.0284(5) Uani 1 1 d G . . . .
H10I H 0.653018 0.298288 0.501665 0.043 Uiso 1 1 d G U . . .
H10J H 0.607293 0.281350 0.448876 0.043 Uiso 1 1 d G U . . .
C1A C 0.8630(5) 0.3749(3) 0.6193(6) 0.061(3) Uani 0.5 1 d . . P A 1
H1AA H 0.890535 0.373501 0.582620 0.074 Uiso 0.5 1 calc R U P A 1
H1AB H 0.878251 0.350165 0.648174 0.074 Uiso 0.5 1 calc R U P A 1
C1B C 0.7631(5) 0.4347(3) 0.6376(5) 0.049(2) Uani 0.5 1 d . . P A 2
H1BA H 0.735408 0.435675 0.674305 0.059 Uiso 0.5 1 calc R U P A 2
H1BB H 0.746989 0.459402 0.608935 0.059 Uiso 0.5 1 calc R U P A 2
C1C C 0.8246(6) 0.3757(3) 0.6666(5) 0.048(2) Uani 0.5 1 d . . P A 2
H1CA H 0.862208 0.350471 0.663627 0.057 Uiso 0.5 1 calc R U P A 2
H1CB H 0.798052 0.374865 0.703850 0.057 Uiso 0.5 1 calc R U P A 2


_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
O2 C60 1.276(4) . ?
O4 C65 1.261(4) . ?
O1 C60 1.258(4) . ?
O3 C65 1.248(4) . ?
O22 C95 1.256(4) . ?
O21 C90 1.251(4) . ?
O11 C76 1.276(4) . ?
O20 C90 1.256(4) . ?
O23 C95 1.257(4) . ?
O10 C76 1.256(4) . ?
N14 H14A 0.8800 . ?
N14 H14B 0.8800 . ?
N14 C45 1.311(4) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C23 1.320(4) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C1 1.321(4) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C23 1.310(4) . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
N16 C52 1.323(4) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C16 1.315(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.308(4) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N17 C52 1.309(4) . ?
O31 C100 1.250(5) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N13 C38 1.313(5) . ?
O13 C70 1.240(5) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C16 1.327(4) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N15 C45 1.300(4) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C38 1.329(4) . ?
O12 C70 1.241(5) . ?
C65 C02U 1.515(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C9 1.313(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C9 1.315(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(4) . ?
C25 C24 1.400(4) . ?
C27 C26 1.400(4) . ?
C27 C28 1.396(4) . ?
C27 C8 1.547(4) . ?
C26 H26 0.9500 . ?
C23 C24 1.482(4) . ?
C57 H57 0.9500 . ?
C57 C015 1.382(4) . ?
C57 C56 1.397(4) . ?
C015 H015 0.9500 . ?
C015 C53 1.403(4) . ?
C60 C61 1.500(4) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C30 1.290(5) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C30 1.309(5) . ?
C53 C52 1.474(4) . ?
C53 C54 1.389(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.384(5) . ?
C43 C42 1.389(5) . ?
C5 C4 1.405(4) . ?
C5 C6 1.394(4) . ?
C5 C8 1.536(4) . ?
C24 C29 1.382(5) . ?
O32 C106 1.219(5) . ?
C17 C16 1.474(4) . ?
C17 C18 1.395(4) . ?
C17 C22 1.397(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.391(4) . ?
C21 C22 1.387(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.381(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(4) . ?
C12 C11 1.388(5) . ?
C56 C55 1.401(4) . ?
C56 C37 1.542(4) . ?
C45 C46 1.490(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.376(5) . ?
C2 C1 1.478(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.395(4) . ?
C20 C19 1.398(4) . ?
C20 C8 1.545(4) . ?
C33 H33 0.9500 . ?
C33 C34 1.399(5) . ?
C33 C32 1.383(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(4) . ?
C44 H44 0.9500 . ?
C44 C39 1.400(4) . ?
C29 H29 0.9500 . ?
C42 C41 1.395(4) . ?
C42 C37 1.546(4) . ?
C55 H55 0.9500 . ?
C55 C54 1.377(4) . ?
C22 H22 0.9500 . ?
C19 H19 0.9500 . ?
C34 C37 1.541(4) . ?
C34 C35 1.394(4) . ?
C8 C13 1.546(4) . ?
C46 C51 1.407(5) . ?
C46 C47 1.383(4) . ?
C90 C91 1.507(4) . ?
C49 C50 1.408(4) . ?
C49 C48 1.387(4) . ?
C49 C37 1.548(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.406(4) . ?
C14 C15 1.388(4) . ?
C39 C38 1.474(5) . ?
C39 C40 1.389(5) . ?
C41 H41 0.9500 . ?
C41 C40 1.381(5) . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C51 H51 0.9500 . ?
C51 C50 1.373(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.397(4) . ?
C50 H50 0.9500 . ?
C48 H48 0.9500 . ?
C95 C66 1.504(5) . ?
C75 C76 1.500(4) . ?
C75 C71 1.870(5) . ?
C75 C72 1.557(4) . ?
C75 C73 1.551(5) . ?
C75 C74 1.519(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.395(5) . ?
C15 H15 0.9500 . ?
C15 C10 1.399(5) . ?
C10 C9 1.486(4) . ?
C54 H54 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.395(5) . ?
C31 C36 1.379(5) . ?
C31 C30 1.497(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.390(5) . ?
C40 H40 0.9500 . ?
C61 C02U 1.873(4) . ?
C61 C62 1.535(5) . ?
C61 C63 1.526(5) . ?
C61 C64 1.513(5) . ?
C02U C62 1.524(6) . ?
C02U C63 1.526(5) . ?
C02U C64 1.518(5) . ?
C70 C71 1.502(5) . ?
C66 C91 1.880(5) . ?
C66 C94 1.540(5) . ?
C66 C92 1.523(5) . ?
C66 C93 1.530(5) . ?
C91 C94 1.527(5) . ?
C91 C92 1.540(5) . ?
C91 C93 1.538(6) . ?
C71 C72 1.550(5) . ?
C71 C73 1.542(5) . ?
C71 C74 1.559(5) . ?
C36 H36 0.9500 . ?
O30 C100 1.254(5) . ?
C105 C106 1.505(5) . ?
C105 C101 1.856(5) . ?
C105 C104 1.569(9) . ?
C105 C102 1.557(8) . ?
C105 C103 1.514(9) . ?
C105 C1A 1.561(9) . ?
C105 C1B 1.543(9) . ?
C105 C1C 1.504(10) . ?
C72 H72A 0.9900 . ?
C72 H72B 0.9900 . ?
C106 O33 1.236(5) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C101 C100 1.502(5) . ?
C101 C104 1.516(9) . ?
C101 C102 1.514(9) . ?
C101 C103 1.539(9) . ?
C101 C1A 1.583(10) . ?
C101 C1B 1.558(9) . ?
C101 C1C 1.574(9) . ?
C74 H74A 0.9900 . ?
C74 H74B 0.9900 . ?
C94 H94A 0.9900 . ?
C94 H94B 0.9900 . ?
C92 H92A 0.9900 . ?
C92 H92B 0.9900 . ?
C93 H93A 0.9900 . ?
C93 H93B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 H64A 0.9900 . ?
C64 H64B 0.9900 . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C102 H10E 0.9900 . ?
C102 H10F 0.9900 . ?
C103 H10G 0.9900 . ?
C103 H10H 0.9900 . ?
O100 H10I 0.8499 . ?
O100 H10J 0.8498 . ?
C1A H1AA 0.9900 . ?
C1A H1AB 0.9900 . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?

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
H14A N14 H14B 120.0 . . ?
C45 N14 H14A 120.0 . . ?
C45 N14 H14B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C23 N8 H8A 120.0 . . ?
C23 N8 H8B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C23 N7 H7A 120.0 . . ?
C23 N7 H7B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
C52 N16 H16A 120.0 . . ?
C52 N16 H16B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C16 N6 H6A 120.0 . . ?
C16 N6 H6B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C52 N17 H17A 120.0 . . ?
C52 N17 H17B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C38 N13 H13A 120.0 . . ?
C38 N13 H13B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C16 N5 H5A 120.0 . . ?
C16 N5 H5B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
C45 N15 H15A 120.0 . . ?
C45 N15 H15B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C38 N12 H12A 120.0 . . ?
C38 N12 H12B 120.0 . . ?
O4 C65 C02U 117.0(3) . . ?
O3 C65 O4 124.9(3) . . ?
O3 C65 C02U 118.1(3) . . ?
H3A N3 H3B 120.0 . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
C26 C25 H25 120.2 . . ?
C26 C25 C24 119.6(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C27 C8 118.6(2) . . ?
C28 C27 C26 117.5(3) . . ?
C28 C27 C8 123.5(3) . . ?
C25 C26 C27 121.9(3) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
N8 C23 C24 117.7(3) . . ?
N7 C23 N8 122.2(3) . . ?
N7 C23 C24 120.1(3) . . ?
C015 C57 H57 119.4 . . ?
C015 C57 C56 121.3(3) . . ?
C56 C57 H57 119.4 . . ?
C57 C015 H015 120.0 . . ?
C57 C015 C53 120.0(3) . . ?
C53 C015 H015 120.0 . . ?
O2 C60 C61 117.3(3) . . ?
O1 C60 O2 124.7(3) . . ?
O1 C60 C61 118.0(3) . . ?
H11A N11 H11B 120.0 . . ?
C30 N11 H11A 120.0 . . ?
C30 N11 H11B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C30 N10 H10A 120.0 . . ?
C30 N10 H10B 120.0 . . ?
C015 C53 C52 121.2(3) . . ?
C54 C53 C015 118.8(3) . . ?
C54 C53 C52 120.0(3) . . ?
C44 C43 H43 119.0 . . ?
C44 C43 C42 121.9(3) . . ?
C42 C43 H43 119.0 . . ?
C4 C5 C8 120.6(3) . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 C8 121.8(3) . . ?
C25 C24 C23 120.5(3) . . ?
C29 C24 C25 119.2(3) . . ?
C29 C24 C23 120.3(3) . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 C22 118.7(3) . . ?
C22 C17 C16 119.6(3) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C22 C21 C20 121.3(3) . . ?
N6 C16 N5 121.6(3) . . ?
N6 C16 C17 120.1(3) . . ?
N5 C16 C17 118.1(3) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.6 . . ?
N16 C52 C53 118.9(3) . . ?
N17 C52 N16 122.1(3) . . ?
N17 C52 C53 119.0(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C13 C12 H12 119.3 . . ?
C13 C12 C11 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C57 C56 C55 118.1(3) . . ?
C57 C56 C37 119.4(3) . . ?
C55 C56 C37 122.1(3) . . ?
N14 C45 C46 118.6(3) . . ?
N15 C45 N14 121.8(3) . . ?
N15 C45 C46 119.6(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 C7 118.9(3) . . ?
C7 C2 C1 119.2(3) . . ?
N2 C1 C2 118.5(3) . . ?
N1 C1 N2 121.3(3) . . ?
N1 C1 C2 120.2(3) . . ?
C21 C20 C19 118.0(3) . . ?
C21 C20 C8 121.5(3) . . ?
C19 C20 C8 119.9(3) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C32 C33 C34 120.8(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C43 C44 H44 120.5 . . ?
C43 C44 C39 119.1(3) . . ?
C39 C44 H44 120.5 . . ?
C24 C29 C28 120.7(3) . . ?
C24 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C43 C42 C41 118.3(3) . . ?
C43 C42 C37 118.1(3) . . ?
C41 C42 C37 123.4(3) . . ?
C56 C55 H55 119.7 . . ?
C54 C55 C56 120.7(3) . . ?
C54 C55 H55 119.7 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C20 C19 H19 119.4 . . ?
C18 C19 C20 121.1(3) . . ?
C18 C19 H19 119.4 . . ?
C33 C34 C37 118.8(3) . . ?
C35 C34 C33 118.3(3) . . ?
C35 C34 C37 122.7(3) . . ?
C5 C8 C27 112.7(2) . . ?
C5 C8 C20 114.1(2) . . ?
C5 C8 C13 103.5(2) . . ?
C20 C8 C27 101.9(2) . . ?
C20 C8 C13 112.3(2) . . ?
C13 C8 C27 112.7(2) . . ?
C51 C46 C45 121.2(3) . . ?
C47 C46 C45 119.4(3) . . ?
C47 C46 C51 119.5(3) . . ?
O21 C90 O20 125.2(3) . . ?
O21 C90 C91 118.1(3) . . ?
O20 C90 C91 116.6(3) . . ?
C50 C49 C37 118.7(3) . . ?
C48 C49 C50 118.0(3) . . ?
C48 C49 C37 122.9(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C15 C14 C13 121.2(3) . . ?
C44 C39 C38 119.5(3) . . ?
C40 C39 C44 119.4(3) . . ?
C40 C39 C38 121.1(3) . . ?
C42 C41 H41 119.8 . . ?
C40 C41 C42 120.5(3) . . ?
C40 C41 H41 119.8 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C12 C13 C8 123.7(3) . . ?
C12 C13 C14 118.2(3) . . ?
C14 C13 C8 117.8(3) . . ?
N13 C38 N12 121.1(3) . . ?
N13 C38 C39 120.6(3) . . ?
N12 C38 C39 118.3(3) . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C46 C51 H51 120.2 . . ?
C50 C51 C46 119.6(3) . . ?
C50 C51 H51 120.2 . . ?
C46 C47 H47 119.8 . . ?
C46 C47 C48 120.4(3) . . ?
C48 C47 H47 119.8 . . ?
C49 C50 H50 119.2 . . ?
C51 C50 C49 121.7(3) . . ?
C51 C50 H50 119.2 . . ?
C49 C48 C47 120.8(3) . . ?
C49 C48 H48 119.6 . . ?
C47 C48 H48 119.6 . . ?
O22 C95 O23 124.1(3) . . ?
O22 C95 C66 117.8(3) . . ?
O23 C95 C66 118.1(3) . . ?
C76 C75 C71 178.2(3) . . ?
C76 C75 C72 125.7(3) . . ?
C76 C75 C73 127.2(3) . . ?
C76 C75 C74 128.0(3) . . ?
C72 C75 C71 52.84(19) . . ?
C73 C75 C71 52.57(19) . . ?
C73 C75 C72 86.5(3) . . ?
C74 C75 C71 53.58(19) . . ?
C74 C75 C72 87.6(3) . . ?
C74 C75 C73 88.4(3) . . ?
C56 C37 C42 102.4(2) . . ?
C56 C37 C34 112.8(2) . . ?
C56 C37 C49 113.0(2) . . ?
C42 C37 C49 113.7(2) . . ?
C34 C37 C42 111.5(2) . . ?
C34 C37 C49 103.8(2) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C10 119.6(3) . . ?
C10 C15 H15 120.2 . . ?
C11 C10 C15 119.2(3) . . ?
C11 C10 C9 121.4(3) . . ?
C15 C10 C9 119.2(3) . . ?
C53 C54 H54 119.5 . . ?
C55 C54 C53 121.0(3) . . ?
C55 C54 H54 119.5 . . ?
C33 C32 H32 119.8 . . ?
C33 C32 C31 120.3(3) . . ?
C31 C32 H32 119.8 . . ?
C32 C31 C30 119.2(3) . . ?
C36 C31 C32 119.1(3) . . ?
C36 C31 C30 121.6(3) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 C34 120.5(3) . . ?
C36 C35 H35 119.7 . . ?
C39 C40 H40 119.6 . . ?
C41 C40 C39 120.7(3) . . ?
C41 C40 H40 119.6 . . ?
C60 C61 C02U 177.8(3) . . ?
C60 C61 C62 130.0(3) . . ?
C60 C61 C63 127.8(3) . . ?
C60 C61 C64 126.1(3) . . ?
C62 C61 C02U 52.0(2) . . ?
C63 C61 C02U 52.1(2) . . ?
C63 C61 C62 86.2(4) . . ?
C64 C61 C02U 51.9(2) . . ?
C64 C61 C62 86.0(4) . . ?
C64 C61 C63 86.0(4) . . ?
C65 C02U C61 178.9(3) . . ?
C65 C02U C62 127.8(3) . . ?
C65 C02U C63 128.5(3) . . ?
C65 C02U C64 127.2(3) . . ?
C62 C02U C61 52.5(2) . . ?
C62 C02U C63 86.7(4) . . ?
C63 C02U C61 52.2(2) . . ?
C64 C02U C61 51.7(2) . . ?
C64 C02U C62 86.3(4) . . ?
C64 C02U C63 85.9(4) . . ?
O11 C76 C75 118.0(3) . . ?
O10 C76 O11 123.9(3) . . ?
O10 C76 C75 118.0(3) . . ?
O13 C70 O12 123.5(3) . . ?
O13 C70 C71 117.2(3) . . ?
O12 C70 C71 119.3(3) . . ?
N3 C9 N4 122.5(3) . . ?
N3 C9 C10 119.0(3) . . ?
N4 C9 C10 118.4(3) . . ?
C95 C66 C91 177.3(3) . . ?
C95 C66 C94 129.3(3) . . ?
C95 C66 C92 128.9(3) . . ?
C95 C66 C93 124.9(3) . . ?
C94 C66 C91 51.90(19) . . ?
C92 C66 C91 52.6(2) . . ?
C92 C66 C94 86.4(3) . . ?
C92 C66 C93 87.1(4) . . ?
C93 C66 C91 52.4(2) . . ?
C93 C66 C94 86.1(3) . . ?
C90 C91 C66 178.5(3) . . ?
C90 C91 C94 129.0(3) . . ?
C90 C91 C92 127.7(3) . . ?
C90 C91 C93 127.0(3) . . ?
C94 C91 C66 52.5(2) . . ?
C94 C91 C92 86.2(3) . . ?
C94 C91 C93 86.2(3) . . ?
C92 C91 C66 51.7(2) . . ?
C93 C91 C66 52.0(2) . . ?
C93 C91 C92 86.2(4) . . ?
C70 C71 C75 175.8(3) . . ?
C70 C71 C72 131.0(3) . . ?
C70 C71 C73 124.8(3) . . ?
C70 C71 C74 126.2(3) . . ?
C72 C71 C75 53.18(18) . . ?
C72 C71 C74 86.5(3) . . ?
C73 C71 C75 53.0(2) . . ?
C73 C71 C72 87.1(3) . . ?
C73 C71 C74 87.3(3) . . ?
C74 C71 C75 51.64(19) . . ?
C31 C36 C35 120.8(3) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
N11 C30 N10 120.5(3) . . ?
N11 C30 C31 120.3(3) . . ?
N10 C30 C31 119.2(3) . . ?
C106 C105 C101 178.2(3) . . ?
C106 C105 C104 127.3(4) . . ?
C106 C105 C102 129.1(4) . . ?
C106 C105 C103 128.6(4) . . ?
C106 C105 C1A 124.7(4) . . ?
C106 C105 C1B 127.2(4) . . ?
C104 C105 C101 51.7(3) . . ?
C102 C105 C101 51.7(3) . . ?
C103 C105 C101 53.2(4) . . ?
C103 C105 C104 90.5(6) . . ?
C103 C105 C1A 86.5(6) . . ?
C1A C105 C101 54.4(4) . . ?
C1A C105 C104 85.6(6) . . ?
C1B C105 C101 53.6(3) . . ?
C1B C105 C102 87.1(6) . . ?
C1C C105 C106 123.6(4) . . ?
C1C C105 C101 54.7(3) . . ?
C1C C105 C102 89.6(5) . . ?
C1C C105 C1B 87.2(6) . . ?
C75 C72 H72A 116.1 . . ?
C75 C72 H72B 116.1 . . ?
C71 C72 C75 74.0(2) . . ?
C71 C72 H72A 116.1 . . ?
C71 C72 H72B 116.1 . . ?
H72A C72 H72B 113.1 . . ?
O32 C106 C105 118.9(3) . . ?
O32 C106 O33 123.3(4) . . ?
O33 C106 C105 117.6(4) . . ?
C75 C73 H73A 116.1 . . ?
C75 C73 H73B 116.1 . . ?
C71 C73 C75 74.4(2) . . ?
C71 C73 H73A 116.1 . . ?
C71 C73 H73B 116.1 . . ?
H73A C73 H73B 113.1 . . ?
C100 C101 C105 178.5(3) . . ?
C100 C101 C104 124.3(4) . . ?
C100 C101 C102 127.5(4) . . ?
C100 C101 C103 129.3(4) . . ?
C100 C101 C1A 126.9(4) . . ?
C100 C101 C1B 126.9(4) . . ?
C100 C101 C1C 127.6(4) . . ?
C104 C101 C105 54.3(4) . . ?
C104 C101 C103 91.6(6) . . ?
C104 C101 C1A 86.6(6) . . ?
C102 C101 C105 53.9(3) . . ?
C102 C101 C1B 88.1(5) . . ?
C102 C101 C1C 88.6(6) . . ?
C103 C101 C105 51.9(4) . . ?
C103 C101 C1A 84.9(7) . . ?
C1A C101 C105 53.3(3) . . ?
C1B C101 C105 52.9(3) . . ?
C1B C101 C1C 84.2(6) . . ?
C1C C101 C105 51.2(4) . . ?
C75 C74 C71 74.8(2) . . ?
C75 C74 H74A 116.0 . . ?
C75 C74 H74B 116.0 . . ?
C71 C74 H74A 116.0 . . ?
C71 C74 H74B 116.0 . . ?
H74A C74 H74B 113.0 . . ?
O31 C100 O30 124.0(4) . . ?
O31 C100 C101 117.5(3) . . ?
O30 C100 C101 118.5(4) . . ?
C66 C94 H94A 115.9 . . ?
C66 C94 H94B 115.9 . . ?
C91 C94 C66 75.6(3) . . ?
C91 C94 H94A 115.9 . . ?
C91 C94 H94B 115.9 . . ?
H94A C94 H94B 112.9 . . ?
C66 C92 C91 75.7(3) . . ?
C66 C92 H92A 115.9 . . ?
C66 C92 H92B 115.9 . . ?
C91 C92 H92A 115.9 . . ?
C91 C92 H92B 115.9 . . ?
H92A C92 H92B 112.9 . . ?
C66 C93 C91 75.5(3) . . ?
C66 C93 H93A 115.9 . . ?
C66 C93 H93B 115.9 . . ?
C91 C93 H93A 115.9 . . ?
C91 C93 H93B 115.9 . . ?
H93A C93 H93B 112.9 . . ?
C61 C62 H62A 115.9 . . ?
C61 C62 H62B 115.9 . . ?
C02U C62 C61 75.5(3) . . ?
C02U C62 H62A 115.9 . . ?
C02U C62 H62B 115.9 . . ?
H62A C62 H62B 112.9 . . ?
C61 C63 C02U 75.7(3) . . ?
C61 C63 H63A 115.9 . . ?
C61 C63 H63B 115.9 . . ?
C02U C63 H63A 115.9 . . ?
C02U C63 H63B 115.9 . . ?
H63A C63 H63B 112.9 . . ?
C61 C64 C02U 76.3(3) . . ?
C61 C64 H64A 115.8 . . ?
C61 C64 H64B 115.8 . . ?
C02U C64 H64A 115.8 . . ?
C02U C64 H64B 115.8 . . ?
H64A C64 H64B 112.8 . . ?
C105 C104 H10C 116.1 . . ?
C105 C104 H10D 116.1 . . ?
C101 C104 C105 74.0(4) . . ?
C101 C104 H10C 116.1 . . ?
C101 C104 H10D 116.1 . . ?
H10C C104 H10D 113.1 . . ?
C105 C102 H10E 116.1 . . ?
C105 C102 H10F 116.1 . . ?
C101 C102 C105 74.4(4) . . ?
C101 C102 H10E 116.1 . . ?
C101 C102 H10F 116.1 . . ?
H10E C102 H10F 113.1 . . ?
C105 C103 C101 74.9(4) . . ?
C105 C103 H10G 116.0 . . ?
C105 C103 H10H 116.0 . . ?
C101 C103 H10G 116.0 . . ?
C101 C103 H10H 116.0 . . ?
H10G C103 H10H 113.0 . . ?
H10I O100 H10J 104.4 . . ?
C105 C1A C101 72.4(4) . . ?
C105 C1A H1AA 116.3 . . ?
C105 C1A H1AB 116.3 . . ?
C101 C1A H1AA 116.3 . . ?
C101 C1A H1AB 116.3 . . ?
H1AA C1A H1AB 113.3 . . ?
C105 C1B C101 73.5(4) . . ?
C105 C1B H1BA 116.2 . . ?
C105 C1B H1BB 116.2 . . ?
C101 C1B H1BA 116.2 . . ?
C101 C1B H1BB 116.2 . . ?
H1BA C1B H1BB 113.2 . . ?
C105 C1C C101 74.2(5) . . ?
C105 C1C H1CA 116.1 . . ?
C105 C1C H1CB 116.1 . . ?
C101 C1C H1CA 116.1 . . ?
C101 C1C H1CB 116.1 . . ?
H1CA C1C H1CB 113.1 . . ?

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
O2 C60 C61 C62 -18.2(6) . . . . ?
O2 C60 C61 C63 -141.1(5) . . . . ?
O2 C60 C61 C64 101.7(5) . . . . ?
O4 C65 C02U C62 50.1(6) . . . . ?
O4 C65 C02U C63 171.7(5) . . . . ?
O4 C65 C02U C64 -69.0(6) . . . . ?
O1 C60 C61 C62 163.5(5) . . . . ?
O1 C60 C61 C63 40.6(6) . . . . ?
O1 C60 C61 C64 -76.6(6) . . . . ?
O3 C65 C02U C62 -130.4(5) . . . . ?
O3 C65 C02U C63 -8.8(6) . . . . ?
O3 C65 C02U C64 110.5(5) . . . . ?
O22 C95 C66 C94 -157.9(4) . . . . ?
O22 C95 C66 C92 -34.2(6) . . . . ?
O22 C95 C66 C93 84.6(5) . . . . ?
O21 C90 C91 C94 -59.1(5) . . . . ?
O21 C90 C91 C92 179.7(4) . . . . ?
O21 C90 C91 C93 61.2(5) . . . . ?
O20 C90 C91 C94 122.9(5) . . . . ?
O20 C90 C91 C92 1.6(6) . . . . ?
O20 C90 C91 C93 -116.9(5) . . . . ?
O23 C95 C66 C94 24.1(6) . . . . ?
O23 C95 C66 C92 147.8(5) . . . . ?
O23 C95 C66 C93 -93.4(5) . . . . ?
N14 C45 C46 C51 -133.4(3) . . . . ?
N14 C45 C46 C47 47.3(4) . . . . ?
N8 C23 C24 C25 137.7(3) . . . . ?
N8 C23 C24 C29 -39.9(4) . . . . ?
N7 C23 C24 C25 -41.7(4) . . . . ?
N7 C23 C24 C29 140.8(3) . . . . ?
O13 C70 C71 C72 -173.1(4) . . . . ?
O13 C70 C71 C73 -51.6(5) . . . . ?
O13 C70 C71 C74 64.5(5) . . . . ?
N15 C45 C46 C51 48.4(5) . . . . ?
N15 C45 C46 C47 -131.0(3) . . . . ?
O12 C70 C71 C72 9.7(5) . . . . ?
O12 C70 C71 C73 131.3(4) . . . . ?
O12 C70 C71 C74 -112.7(4) . . . . ?
C65 C02U C62 C61 -178.7(3) . . . . ?
C65 C02U C63 C61 179.0(3) . . . . ?
C65 C02U C64 C61 179.8(3) . . . . ?
C25 C24 C29 C28 0.8(5) . . . . ?
C27 C28 C29 C24 -4.4(5) . . . . ?
C27 C8 C13 C12 -18.9(4) . . . . ?
C27 C8 C13 C14 167.9(3) . . . . ?
C26 C25 C24 C23 -175.1(3) . . . . ?
C26 C25 C24 C29 2.5(5) . . . . ?
C26 C27 C28 C29 4.4(4) . . . . ?
C26 C27 C8 C5 -173.8(3) . . . . ?
C26 C27 C8 C20 63.5(3) . . . . ?
C26 C27 C8 C13 -57.1(4) . . . . ?
C23 C24 C29 C28 178.4(3) . . . . ?
C57 C015 C53 C52 179.3(3) . . . . ?
C57 C015 C53 C54 1.6(4) . . . . ?
C57 C56 C55 C54 2.8(5) . . . . ?
C57 C56 C37 C42 74.1(3) . . . . ?
C57 C56 C37 C34 -165.9(3) . . . . ?
C57 C56 C37 C49 -48.6(4) . . . . ?
C015 C57 C56 C55 -4.4(5) . . . . ?
C015 C57 C56 C37 -177.1(3) . . . . ?
C015 C53 C52 N16 -30.7(4) . . . . ?
C015 C53 C52 N17 149.3(3) . . . . ?
C015 C53 C54 C55 -3.3(5) . . . . ?
C60 C61 C62 C02U 178.5(3) . . . . ?
C60 C61 C63 C02U -177.2(3) . . . . ?
C60 C61 C64 C02U 178.6(3) . . . . ?
C43 C44 C39 C38 -177.8(3) . . . . ?
C43 C44 C39 C40 1.2(5) . . . . ?
C43 C42 C41 C40 2.9(5) . . . . ?
C43 C42 C37 C56 66.1(3) . . . . ?
C43 C42 C37 C34 -54.8(4) . . . . ?
C43 C42 C37 C49 -171.7(3) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C5 C6 C7 C2 1.3(5) . . . . ?
C5 C8 C13 C12 103.2(3) . . . . ?
C5 C8 C13 C14 -70.1(3) . . . . ?
C24 C25 C26 C27 -2.4(5) . . . . ?
C17 C18 C19 C20 2.0(5) . . . . ?
C21 C20 C19 C18 -1.3(5) . . . . ?
C21 C20 C8 C27 -97.7(3) . . . . ?
C21 C20 C8 C5 140.5(3) . . . . ?
C21 C20 C8 C13 23.2(4) . . . . ?
C16 C17 C18 C19 177.2(3) . . . . ?
C16 C17 C22 C21 -179.2(3) . . . . ?
C28 C27 C26 C25 -1.0(4) . . . . ?
C28 C27 C8 C5 13.3(4) . . . . ?
C28 C27 C8 C20 -109.4(3) . . . . ?
C28 C27 C8 C13 130.0(3) . . . . ?
C52 C53 C54 C55 179.1(3) . . . . ?
C4 C5 C6 C7 -5.3(4) . . . . ?
C4 C5 C8 C27 49.2(4) . . . . ?
C4 C5 C8 C20 164.8(3) . . . . ?
C4 C5 C8 C13 -72.8(3) . . . . ?
C12 C11 C10 C15 -0.2(5) . . . . ?
C12 C11 C10 C9 176.2(3) . . . . ?
C56 C57 C015 C53 2.2(5) . . . . ?
C56 C55 C54 C53 1.0(5) . . . . ?
C45 C46 C51 C50 -179.8(3) . . . . ?
C45 C46 C47 C48 178.0(3) . . . . ?
C6 C5 C4 C3 5.2(4) . . . . ?
C6 C5 C8 C27 -135.9(3) . . . . ?
C6 C5 C8 C20 -20.3(4) . . . . ?
C6 C5 C8 C13 102.1(3) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C7 C6 -178.8(3) . . . . ?
C20 C21 C22 C17 2.0(5) . . . . ?
C20 C8 C13 C12 -133.3(3) . . . . ?
C20 C8 C13 C14 53.4(4) . . . . ?
C33 C34 C37 C56 48.4(4) . . . . ?
C33 C34 C37 C42 163.0(3) . . . . ?
C33 C34 C37 C49 -74.2(3) . . . . ?
C33 C34 C35 C36 -1.4(5) . . . . ?
C33 C32 C31 C36 0.1(5) . . . . ?
C33 C32 C31 C30 177.5(3) . . . . ?
C18 C17 C16 N6 -29.8(5) . . . . ?
C18 C17 C16 N5 154.2(3) . . . . ?
C18 C17 C22 C21 -1.4(5) . . . . ?
C44 C43 C42 C41 -1.0(5) . . . . ?
C44 C43 C42 C37 -175.6(3) . . . . ?
C44 C39 C38 N13 -42.8(5) . . . . ?
C44 C39 C38 N12 137.6(3) . . . . ?
C44 C39 C40 C41 0.7(5) . . . . ?
C42 C43 C44 C39 -1.1(5) . . . . ?
C42 C41 C40 C39 -2.8(5) . . . . ?
C55 C56 C37 C42 -98.2(3) . . . . ?
C55 C56 C37 C34 21.7(4) . . . . ?
C55 C56 C37 C49 139.1(3) . . . . ?
C22 C17 C16 N6 148.0(3) . . . . ?
C22 C17 C16 N5 -28.0(4) . . . . ?
C22 C17 C18 C19 -0.6(5) . . . . ?
C22 C21 C20 C19 -0.7(5) . . . . ?
C22 C21 C20 C8 170.1(3) . . . . ?
C19 C20 C8 C27 72.9(3) . . . . ?
C19 C20 C8 C5 -48.9(4) . . . . ?
C19 C20 C8 C13 -166.2(3) . . . . ?
C34 C33 C32 C31 -2.4(5) . . . . ?
C34 C35 C36 C31 -0.9(5) . . . . ?
C8 C27 C26 C25 -174.3(3) . . . . ?
C8 C27 C28 C29 177.3(3) . . . . ?
C8 C5 C4 C3 -179.7(3) . . . . ?
C8 C5 C6 C7 179.6(3) . . . . ?
C8 C20 C19 C18 -172.3(3) . . . . ?
C46 C51 C50 C49 0.5(5) . . . . ?
C46 C47 C48 C49 3.2(5) . . . . ?
C90 C91 C94 C66 179.7(4) . . . . ?
C90 C91 C92 C66 -178.2(3) . . . . ?
C90 C91 C93 C66 178.6(3) . . . . ?
C14 C15 C10 C11 -0.3(5) . . . . ?
C14 C15 C10 C9 -176.8(3) . . . . ?
C41 C42 C37 C56 -108.3(3) . . . . ?
C41 C42 C37 C34 130.9(3) . . . . ?
C41 C42 C37 C49 13.9(4) . . . . ?
C3 C2 C1 N2 -140.4(3) . . . . ?
C3 C2 C1 N1 41.0(4) . . . . ?
C3 C2 C7 C6 3.1(5) . . . . ?
C13 C12 C11 C10 0.4(5) . . . . ?
C13 C14 C15 C10 0.7(5) . . . . ?
C38 C39 C40 C41 179.7(3) . . . . ?
C7 C2 C1 N2 41.6(4) . . . . ?
C7 C2 C1 N1 -137.0(3) . . . . ?
C7 C2 C3 C4 -3.3(5) . . . . ?
C51 C46 C47 C48 -1.4(5) . . . . ?
C47 C46 C51 C50 -0.4(5) . . . . ?
C50 C49 C48 C47 -3.1(5) . . . . ?
C50 C49 C37 C56 171.9(3) . . . . ?
C50 C49 C37 C42 55.8(4) . . . . ?
C50 C49 C37 C34 -65.6(3) . . . . ?
C48 C49 C50 C51 1.2(5) . . . . ?
C48 C49 C37 C56 -14.3(4) . . . . ?
C48 C49 C37 C42 -130.5(3) . . . . ?
C48 C49 C37 C34 108.2(3) . . . . ?
C95 C66 C94 C91 -176.9(4) . . . . ?
C95 C66 C92 C91 177.1(4) . . . . ?
C95 C66 C93 C91 179.9(3) . . . . ?
C37 C56 C55 C54 175.2(3) . . . . ?
C37 C42 C41 C40 177.3(3) . . . . ?
C37 C34 C35 C36 -175.2(3) . . . . ?
C37 C49 C50 C51 175.3(3) . . . . ?
C37 C49 C48 C47 -176.9(3) . . . . ?
C11 C12 C13 C8 -173.3(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C11 C10 C9 N3 -143.6(3) . . . . ?
C11 C10 C9 N4 36.3(5) . . . . ?
C15 C14 C13 C12 -0.5(5) . . . . ?
C15 C14 C13 C8 173.1(3) . . . . ?
C15 C10 C9 N3 32.8(5) . . . . ?
C15 C10 C9 N4 -147.3(3) . . . . ?
C54 C53 C52 N16 146.9(3) . . . . ?
C54 C53 C52 N17 -33.1(5) . . . . ?
C32 C33 C34 C37 177.1(3) . . . . ?
C32 C33 C34 C35 3.0(5) . . . . ?
C32 C31 C36 C35 1.6(5) . . . . ?
C32 C31 C30 N11 -156.1(4) . . . . ?
C32 C31 C30 N10 23.5(5) . . . . ?
C35 C34 C37 C56 -137.8(3) . . . . ?
C35 C34 C37 C42 -23.2(4) . . . . ?
C35 C34 C37 C49 99.6(3) . . . . ?
C40 C39 C38 N13 138.2(3) . . . . ?
C40 C39 C38 N12 -41.4(5) . . . . ?
C76 C75 C72 C71 -178.7(3) . . . . ?
C76 C75 C73 C71 177.8(3) . . . . ?
C76 C75 C74 C71 -179.1(4) . . . . ?
C70 C71 C72 C75 180.0(4) . . . . ?
C70 C71 C73 C75 175.5(3) . . . . ?
C70 C71 C74 C75 -175.5(3) . . . . ?
C36 C31 C30 N11 21.3(5) . . . . ?
C36 C31 C30 N10 -159.2(3) . . . . ?
C30 C31 C36 C35 -175.8(3) . . . . ?
C72 C75 C76 O11 64.9(5) . . . . ?
C72 C75 C76 O10 -117.4(4) . . . . ?
C72 C75 C71 C73 -119.0(3) . . . . ?
C72 C75 C71 C74 119.6(4) . . . . ?
C72 C75 C73 C71 44.3(2) . . . . ?
C72 C75 C74 C71 -43.9(2) . . . . ?
C72 C71 C73 C75 -44.5(2) . . . . ?
C72 C71 C74 C75 44.2(2) . . . . ?
C106 C105 C104 C101 178.2(4) . . . . ?
C106 C105 C102 C101 -178.0(4) . . . . ?
C106 C105 C103 C101 -179.9(4) . . . . ?
C106 C105 C1A C101 -178.1(4) . . . . ?
C106 C105 C1B C101 178.1(4) . . . . ?
C106 C105 C1C C101 179.9(4) . . . . ?
C73 C75 C76 O11 -51.9(5) . . . . ?
C73 C75 C76 O10 125.8(4) . . . . ?
C73 C75 C71 C72 119.0(3) . . . . ?
C73 C75 C71 C74 -121.4(4) . . . . ?
C73 C75 C72 C71 -44.1(2) . . . . ?
C73 C75 C74 C71 42.7(3) . . . . ?
C73 C71 C72 C75 44.4(2) . . . . ?
C73 C71 C74 C75 -43.1(3) . . . . ?
C74 C75 C76 O11 -175.2(4) . . . . ?
C74 C75 C76 O10 2.5(6) . . . . ?
C74 C75 C71 C72 -119.6(4) . . . . ?
C74 C75 C71 C73 121.4(4) . . . . ?
C74 C75 C72 C71 44.4(3) . . . . ?
C74 C75 C73 C71 -43.4(3) . . . . ?
C74 C71 C72 C75 -43.1(2) . . . . ?
C74 C71 C73 C75 42.1(2) . . . . ?
C100 C101 C104 C105 -179.4(4) . . . . ?
C100 C101 C102 C105 179.3(4) . . . . ?
C100 C101 C103 C105 -178.9(5) . . . . ?
C100 C101 C1A C105 178.2(4) . . . . ?
C100 C101 C1B C105 -178.2(4) . . . . ?
C100 C101 C1C C105 178.9(4) . . . . ?
C94 C66 C91 C92 120.0(5) . . . . ?
C94 C66 C91 C93 -119.6(5) . . . . ?
C94 C66 C92 C91 -43.1(3) . . . . ?
C94 C66 C93 C91 43.3(3) . . . . ?
C94 C91 C92 C66 43.5(3) . . . . ?
C94 C91 C93 C66 -43.8(3) . . . . ?
C92 C66 C91 C94 -120.0(5) . . . . ?
C92 C66 C91 C93 120.5(5) . . . . ?
C92 C66 C94 C91 43.6(3) . . . . ?
C92 C66 C93 C91 -43.3(3) . . . . ?
C92 C91 C94 C66 -43.0(3) . . . . ?
C92 C91 C93 C66 42.7(3) . . . . ?
C93 C66 C91 C94 119.6(5) . . . . ?
C93 C66 C91 C92 -120.5(5) . . . . ?
C93 C66 C94 C91 -43.7(3) . . . . ?
C93 C66 C92 C91 43.1(3) . . . . ?
C93 C91 C94 C66 43.4(3) . . . . ?
C93 C91 C92 C66 -42.9(3) . . . . ?
C62 C61 C02U C63 -120.2(6) . . . . ?
C62 C61 C02U C64 120.0(6) . . . . ?
C62 C61 C63 C02U 43.0(4) . . . . ?
C62 C61 C64 C02U -43.1(4) . . . . ?
C62 C02U C63 C61 -43.4(4) . . . . ?
C62 C02U C64 C61 43.5(4) . . . . ?
C63 C61 C02U C62 120.2(6) . . . . ?
C63 C61 C02U C64 -119.8(6) . . . . ?
C63 C61 C62 C02U -43.2(4) . . . . ?
C63 C61 C64 C02U 43.4(4) . . . . ?
C63 C02U C62 C61 43.2(4) . . . . ?
C63 C02U C64 C61 -43.4(4) . . . . ?
C64 C61 C02U C62 -120.0(6) . . . . ?
C64 C61 C02U C63 119.8(6) . . . . ?
C64 C61 C62 C02U 43.1(4) . . . . ?
C64 C61 C63 C02U -43.2(4) . . . . ?
C64 C02U C62 C61 -42.9(4) . . . . ?
C64 C02U C63 C61 43.1(4) . . . . ?
C104 C105 C106 O32 -174.3(7) . . . . ?
C104 C105 C106 O33 1.5(9) . . . . ?
C104 C105 C101 C103 -127.2(9) . . . . ?
C104 C105 C101 C1A 116.4(9) . . . . ?
C104 C105 C103 C101 38.7(6) . . . . ?
C104 C105 C1A C101 -44.8(6) . . . . ?
C104 C101 C100 O31 38.0(8) . . . . ?
C104 C101 C100 O30 -140.5(7) . . . . ?
C104 C101 C103 C105 -40.3(6) . . . . ?
C104 C101 C1A C105 46.8(6) . . . . ?
C102 C105 C106 O32 0.2(8) . . . . ?
C102 C105 C106 O33 176.0(7) . . . . ?
C102 C105 C101 C1B 120.1(8) . . . . ?
C102 C105 C101 C1C -123.3(8) . . . . ?
C102 C105 C1B C101 -42.8(5) . . . . ?
C102 C105 C1C C101 41.0(5) . . . . ?
C102 C101 C100 O31 -138.1(7) . . . . ?
C102 C101 C100 O30 43.4(8) . . . . ?
C102 C101 C1B C105 44.3(5) . . . . ?
C102 C101 C1C C105 -42.5(5) . . . . ?
C103 C105 C106 O32 57.3(8) . . . . ?
C103 C105 C106 O33 -126.9(8) . . . . ?
C103 C105 C101 C104 127.2(9) . . . . ?
C103 C105 C101 C1A -116.4(10) . . . . ?
C103 C105 C104 C101 -39.6(6) . . . . ?
C103 C105 C1A C101 45.9(6) . . . . ?
C103 C101 C100 O31 164.9(7) . . . . ?
C103 C101 C100 O30 -13.6(9) . . . . ?
C103 C101 C104 C105 38.8(6) . . . . ?
C103 C101 C1A C105 -45.1(6) . . . . ?
C1A C105 C106 O32 -60.1(9) . . . . ?
C1A C105 C106 O33 115.7(8) . . . . ?
C1A C105 C101 C104 -116.4(9) . . . . ?
C1A C105 C101 C103 116.4(10) . . . . ?
C1A C105 C104 C101 46.9(6) . . . . ?
C1A C105 C103 C101 -46.9(6) . . . . ?
C1A C101 C100 O31 -76.9(9) . . . . ?
C1A C101 C100 O30 104.5(8) . . . . ?
C1A C101 C104 C105 -46.0(6) . . . . ?
C1A C101 C103 C105 46.1(6) . . . . ?
C1B C105 C106 O32 122.7(7) . . . . ?
C1B C105 C106 O33 -61.5(8) . . . . ?
C1B C105 C101 C102 -120.1(8) . . . . ?
C1B C105 C101 C1C 116.6(8) . . . . ?
C1B C105 C102 C101 44.2(5) . . . . ?
C1B C105 C1C C101 -46.1(5) . . . . ?
C1B C101 C100 O31 100.3(7) . . . . ?
C1B C101 C100 O30 -78.3(8) . . . . ?
C1B C101 C102 C105 -43.6(5) . . . . ?
C1B C101 C1C C105 45.8(5) . . . . ?
C1C C105 C106 O32 -121.8(7) . . . . ?
C1C C105 C106 O33 54.0(8) . . . . ?
C1C C105 C101 C102 123.3(8) . . . . ?
C1C C105 C101 C1B -116.6(8) . . . . ?
C1C C105 C102 C101 -43.0(6) . . . . ?
C1C C105 C1B C101 46.9(5) . . . . ?
C1C C101 C100 O31 -14.5(9) . . . . ?
C1C C101 C100 O30 166.9(7) . . . . ?
C1C C101 C102 C105 40.7(5) . . . . ?
C1C C101 C1B C105 -44.5(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.234 0.000 -0.707 1559.6 470.5 ?
2 -0.091 0.500 -0.243 1559.6 470.5 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_1CUB2
_database_code_depnum_ccdc_archive 'CCDC 2293126'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_refine_special_details          
;Despite the use of long exposure times, it was only possible to collect 
diffraction data to a maximum resolution of 0.88 %A.  The asymmetric unit 
contains one quarter of a tetra-amidinium molecule and half a molecule of CUB2-. 
There is a large amount of diffuse electron density, believed to arise from 
water solvent molecules, that could not be modelled. This was included in the 
model using the solvent mask feature of OLEX2; this removed a total of 333 e-
 from a volume of 2302 %A3 (55% of the unit cell volume). This is consistent 
with the presence of approx. 33 water molecules, or approximately 17 water 
molecules per formula unit.  Despite the relatively low data resolution, 
the structure solves and refines smoothly. It was necessary to apply DFIX 
restraints to the C-N bond lengths and one of the cubane C-C bond lengths 
(about a symmetry position), as well as RIGU restraints to the ellipsoids of 
the CUB2- ellipsoid parameters in order to achieve a sensible refinement.,SQUEEZE
;


# start Validation Reply Form
_vrf_THETM01_1CUB2               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Despite the use of Cu radiation and long exposure times, it was only
possible to measure diffraction data to a resolution of 0.88 A.
;
# end Validation Reply Form


_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 N8, 2(C10 H6 O4)'
_chemical_formula_sum            'C49 H44 N8 O8'
_chemical_formula_weight         872.92
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           118
_space_group_name_H-M_alt        'P -4 n 2'
_space_group_name_Hall           'P -4 -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'

_cell_length_a                   23.5856(15)
_cell_length_b                   23.5856(15)
_cell_length_c                   7.5250(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4186.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    870
_cell_measurement_temperature    150
_cell_measurement_theta_max      56.9230
_cell_measurement_theta_min      5.3060
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             916
_exptl_crystal_recrystallization_method 
'Crystallized using tetra-amidinium.4Cl with TBA2.cubanedicarboxylate in 80% EtOH in water. Final concentration of tetra-amidinium = 0.50 mM.'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5646
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.820
_diffrn_reflns_theta_full        60.805
_diffrn_reflns_theta_max         60.805
_diffrn_reflns_theta_min         4.191
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -20.00   1.00   40.00    --  -36.03 -57.00  30.00   83
  2  ω     78.00 134.00   1.00  155.00    --   85.03 178.00 150.00   56
  3  ω    115.00 148.00   1.00  155.00    --   85.03 111.00 150.00   33
  4  ω     54.00 149.00   1.00  155.00    --   85.03  15.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          'cold-mounted using a muCHILL device'
_reflns_Friedel_coverage         0.478
_reflns_Friedel_fraction_full    0.607
_reflns_Friedel_fraction_max     0.607
_reflns_number_gt                1888
_reflns_number_total             2614
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 498 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.026
_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)+(0.1513P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2132
_refine_ls_wR_factor_ref         0.2342

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C2-N1
 1.31 with sigma of 0.005
 C2-N2
 1.31 with sigma of 0.005
 C14_$1-C14
 1.55 with sigma of 0.01
3. Rigid body (RIGU) restrains
 C13, C12, C14, C11, C10, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C14(H14)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C7(H7), C8(H8)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
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
N2 N 0.67297(18) 0.3995(2) 0.5963(6) 0.0521(12) Uani 1 1 d D . . . .
H2A H 0.690018 0.385394 0.690499 0.063 Uiso 1 1 calc R U . . .
H2B H 0.687647 0.428840 0.540735 0.063 Uiso 1 1 calc R U . . .
C1 C 0.500000 0.500000 0.000000 0.0234(17) Uani 1 4 d S T P . .
C6 C 0.53449(18) 0.46088(19) 0.1246(5) 0.0284(10) Uani 1 1 d . . . . .
C5 C 0.5073(2) 0.4344(2) 0.2596(5) 0.0356(11) Uani 1 1 d . . . . .
H5 H 0.467172 0.437163 0.266798 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5366(2) 0.4025(2) 0.3907(6) 0.0455(13) Uani 1 1 d . . . . .
H4 H 0.515954 0.383176 0.480537 0.055 Uiso 1 1 calc R U . . .
N1 N 0.6037(2) 0.3329(2) 0.6209(7) 0.0653(15) Uani 1 1 d D . . . .
H1A H 0.620813 0.318949 0.715033 0.078 Uiso 1 1 calc R U . . .
H1B H 0.571948 0.317509 0.582558 0.078 Uiso 1 1 calc R U . . .
C2 C 0.6252(2) 0.3764(2) 0.5381(6) 0.0496(14) Uani 1 1 d D . . . .
C3 C 0.5938(2) 0.3995(2) 0.3884(6) 0.0463(13) Uani 1 1 d . . . . .
C7 C 0.5952(2) 0.4591(2) 0.1190(6) 0.0458(13) Uani 1 1 d . . . . .
H7 H 0.614888 0.479118 0.028604 0.055 Uiso 1 1 calc R U . . .
O2 O 0.7182(2) 0.3573(3) -0.0930(8) 0.122(3) Uani 1 1 d . . . . .
C8 C 0.6261(3) 0.4276(3) 0.2476(7) 0.0637(17) Uani 1 1 d . . . . .
H8 H 0.666282 0.424949 0.242363 0.076 Uiso 1 1 calc R U . . .
O1 O 0.6466(3) 0.2989(3) -0.0614(8) 0.135(3) Uani 1 1 d . . . . .
C11 C 0.7269(3) 0.2845(3) 0.1292(7) 0.0673(18) Uani 1 1 d . . . . .
C10 C 0.6956(4) 0.3158(3) -0.0216(8) 0.081(2) Uani 1 1 d . . . . .
C12 C 0.7644(4) 0.3096(4) 0.2716(9) 0.093(2) Uani 1 1 d . . . . .
H12 H 0.771953 0.351012 0.288722 0.111 Uiso 1 1 calc R U . . .
C13 C 0.7397(3) 0.2709(3) 0.4079(7) 0.082(2) Uani 1 1 d . . . . .
H13 H 0.727368 0.282862 0.529393 0.098 Uiso 1 1 calc R U . . .
C14 C 0.7005(3) 0.2451(3) 0.2670(8) 0.097(3) Uani 1 1 d D . . . .
H14 H 0.659022 0.237800 0.281888 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
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.325(5) . ?
C1 C6 1.547(4) 2_665 ?
C1 C6 1.547(4) 4_655 ?
C1 C6 1.547(4) . ?
C1 C6 1.547(4) 3_565 ?
C6 C5 1.354(6) . ?
C6 C7 1.432(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.421(7) . ?
C4 H4 0.9500 . ?
C4 C3 1.350(7) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.304(5) . ?
C2 C3 1.454(7) . ?
C3 C8 1.463(8) . ?
C7 H7 0.9500 . ?
C7 C8 1.421(8) . ?
O2 C10 1.239(9) . ?
C8 H8 0.9500 . ?
O1 C10 1.259(10) . ?
C11 C10 1.543(8) . ?
C11 C12 1.511(10) . ?
C11 C13 1.505(9) 7_545 ?
C11 C14 1.525(10) . ?
C12 C12 1.543(15) 7_545 ?
C12 H12 1.0000 . ?
C12 C13 1.492(12) . ?
C13 H13 1.0000 . ?
C13 C14 1.533(10) . ?
C14 C14 1.509(10) 7_545 ?
C14 H14 1.0000 . ?

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
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C6 C1 C6 105.4(3) 3_565 4_655 ?
C6 C1 C6 111.57(15) 3_565 . ?
C6 C1 C6 105.4(3) 2_665 . ?
C6 C1 C6 111.57(15) 4_655 . ?
C6 C1 C6 111.57(15) 3_565 2_665 ?
C6 C1 C6 111.57(15) 2_665 4_655 ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 118.8(4) . . ?
C7 C6 C1 121.7(3) . . ?
C6 C5 H5 118.8 . . ?
C6 C5 C4 122.3(4) . . ?
C4 C5 H5 118.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
N2 C2 C3 122.4(5) . . ?
N1 C2 N2 119.8(4) . . ?
N1 C2 C3 117.8(5) . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 C8 120.4(5) . . ?
C2 C3 C8 117.7(5) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 H8 121.3 . . ?
C7 C8 C3 117.5(5) . . ?
C7 C8 H8 121.3 . . ?
C12 C11 C10 127.9(7) . . ?
C12 C11 C14 89.8(5) . . ?
C13 C11 C10 121.9(5) 7_545 . ?
C13 C11 C12 90.3(5) 7_545 . ?
C13 C11 C14 88.9(5) 7_545 . ?
C14 C11 C10 126.5(6) . . ?
O2 C10 O1 122.9(6) . . ?
O2 C10 C11 119.4(7) . . ?
O1 C10 C11 117.6(7) . . ?
C11 C12 C12 89.0(5) . 7_545 ?
C11 C12 H12 125.4 . . ?
C12 C12 H12 125.4 7_545 . ?
C13 C12 C11 91.0(6) . . ?
C13 C12 C12 89.5(5) . 7_545 ?
C13 C12 H12 125.4 . . ?
C11 C13 H13 124.7 7_545 . ?
C11 C13 C14 91.2(5) 7_545 . ?
C12 C13 C11 91.2(6) . 7_545 ?
C12 C13 H13 124.7 . . ?
C12 C13 C14 90.2(5) . . ?
C14 C13 H13 124.7 . . ?
C11 C14 C13 89.0(6) . . ?
C11 C14 H14 125.5 . . ?
C13 C14 H14 125.5 . . ?
C14 C14 C11 91.4(4) 7_545 . ?
C14 C14 C13 88.5(4) 7_545 . ?
C14 C14 H14 125.5 7_545 . ?

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
N2 C2 C3 C4 -139.1(6) . . . . ?
N2 C2 C3 C8 31.4(7) . . . . ?
C1 C6 C5 C4 -173.3(4) . . . . ?
C1 C6 C7 C8 173.0(4) . . . . ?
C6 C1 C6 C5 -72.3(3) 3_565 . . . ?
C6 C1 C6 C5 170.1(4) 4_655 . . . ?
C6 C1 C6 C5 48.9(3) 2_665 . . . ?
C6 C1 C6 C7 0.3(4) 4_655 . . . ?
C6 C1 C6 C7 117.8(5) 3_565 . . . ?
C6 C1 C6 C7 -120.9(5) 2_665 . . . ?
C6 C5 C4 C3 2.6(8) . . . . ?
C6 C7 C8 C3 -2.5(8) . . . . ?
C5 C6 C7 C8 3.2(8) . . . . ?
C5 C4 C3 C2 168.4(5) . . . . ?
C5 C4 C3 C8 -1.9(8) . . . . ?
C4 C3 C8 C7 1.9(8) . . . . ?
N1 C2 C3 C4 37.9(7) . . . . ?
N1 C2 C3 C8 -151.5(5) . . . . ?
C2 C3 C8 C7 -168.7(5) . . . . ?
C7 C6 C5 C4 -3.2(7) . . . . ?
C11 C12 C13 C11 90.4(5) . . . 7_545 ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C11 C13 C14 C11 -90.4(5) 7_545 . . . ?
C11 C13 C14 C14 1.0(5) 7_545 . . 7_545 ?
C10 C11 C12 C12 -131.0(7) . . . 7_545 ?
C10 C11 C12 C13 139.5(7) . . . . ?
C10 C11 C14 C13 -140.4(7) . . . . ?
C10 C11 C14 C14 131.2(7) . . . 7_545 ?
C12 C11 C10 O2 35.9(11) . . . . ?
C12 C11 C10 O1 -141.3(8) . . . . ?
C12 C11 C14 C13 -0.8(5) . . . . ?
C12 C11 C14 C14 -89.2(5) . . . 7_545 ?
C12 C12 C13 C11 1.4(5) 7_545 . . 7_545 ?
C12 C12 C13 C14 -89.8(5) 7_545 . . . ?
C12 C13 C14 C11 0.8(5) . . . . ?
C12 C13 C14 C14 92.2(5) . . . 7_545 ?
C13 C11 C10 O2 -83.5(10) 7_545 . . . ?
C13 C11 C10 O1 99.2(10) 7_545 . . . ?
C13 C11 C12 C12 1.4(5) 7_545 . . 7_545 ?
C13 C11 C12 C13 -88.1(6) 7_545 . . . ?
C13 C11 C14 C13 89.5(5) 7_545 . . . ?
C13 C11 C14 C14 1.0(5) 7_545 . . 7_545 ?
C14 C11 C10 O2 160.7(7) . . . . ?
C14 C11 C10 O1 -16.5(11) . . . . ?
C14 C11 C12 C12 90.3(4) . . . 7_545 ?
C14 C11 C12 C13 0.8(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.887 1151.3 166.6 ?
2 0.500 0.000 -0.161 1151.3 166.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_Gamma_1CUB2
_database_code_depnum_ccdc_archive 'CCDC 2293128'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_refine_special_details          
;The structure of gamma-1CUB2 was obtained by heating a single crystal of 
beta-1CUB2 to 313 K on the X-ray diffractometer, and it was collected at this 
temperature. The crystal appeared to suffer during this process, and crystal 
data quality is poor. Diffraction could only be obtained to a resolution of 
1.1 A and a very high value of Rint was obtained (0.37). Numerous attempts 
were made to improve this by looking for twin laws and/or reprocessing in 
different space groups. However, none of these processes improved the data 
processing. Despite the limitations of the data, refinement proceeded smoothly 
and it was not necessary to use any crystallographic restraints during the 
refinement. The asymmetric unit contains half a tetra-amidinium cation and two 
half molecules of CUB2-. There is an area of diffuse electron density, believed 
to arise from water solvent molecules, that could not be modelled. 
This was included in the model using the solvent mask feature of OLEX2; this 
removed a total of 96 e- from a volume of 886 A3 (19% of the unit cell volume).  
This is consistent with the presence of approx. 9.6 water molecules, or 
approximately 2.4 water molecules per formula unit.,SQUEEZE
;

# start Validation Reply Form
_vrf_RINTA01_Gamma_1CUB2         
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Numerous attempts were made to improve this, by looking for twin 
laws and/or reprocessing in different space groups. However, none of these 
processes improved the data processing. Despite the limitations of the data, 
refinement proceeded smoothly and it was not necessary to use any 
crystallographic restraints during the refinement.
;
_vrf_THETM01_Gamma_1CUB2         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: This crystal was obtained by a single-crystal-to-single-crystal
transformation of beta-1.CUB2 by heating to 313 K. As a result, crystal 
quality is poor and diffraction could only be obtained to a resolution of 
1.1 A.
;
_vrf_PLAT020_Gamma_1CUB2         
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.368 Report
RESPONSE: Numerous attempts were made to improve this, by looking for twin 
laws and/or reprocessing in different space groups. However, none of these 
processes improved the data processing. Despite the limitations of the data, 
refinement proceeded smoothly and it was not necessary to use any 
crystallographic restraints during the refinement.
;
_vrf_PLAT026_Gamma_1CUB2         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: This crystal was obtained by a single-crystal-to-single-crystal
transformation of beta-1.CUB2 by heating to 313 K. As a result, crystal 
quality is poor and diffraction could only be obtained to a resolution of 
1.1 A, and many weak reflections.
;
_vrf_PLAT088_Gamma_1CUB2         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.35 Note  
RESPONSE: This crystal was obtained by a single-crystal-to-single-crystal
transformation of beta-1.CUB2 by heating to 313 K. As a result, crystal 
quality is poor and diffraction could only be obtained to a resolution of 
1.1 A, resulting in a poor data-to-parameter ratio.
;
_vrf_PLAT340_Gamma_1CUB2         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01912 Ang.  
RESPONSE: This crystal was obtained by a single-crystal-to-single-crystal
transformation of beta-1.CUB2 by heating to 313 K. As a result, crystal 
quality is poor and diffraction could only be obtained to a resolution of 
1.1 A.
;
# end Validation Reply Form
_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 N8, 2(C10 H6 O4)'
_chemical_formula_sum            'C49 H44 N8 O8'
_chemical_formula_weight         872.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H50N50O50
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.879(5)
_cell_length_b                   12.595(4)
_cell_length_c                   27.719(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.35(4)
_cell_angle_gamma                90
_cell_volume                     4733(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    417
_cell_measurement_temperature    313.11(10)
_cell_measurement_theta_max      55.6260
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 5 12 0.0585
5 -6 -11 0.0278
1 6 -12 0.1383
-1 -6 13 0.0953
4 6 9 0.0332
-4 -5 -8 0.0338
-7 5 6 0.0741
8 -4 -5 0.0475

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.6943 5.1818 12.0587 0.0511 0.2234 0.9734
4.5859 -5.6833 -10.8877 -0.0306 -0.1379 -0.9900
0.9098 5.9424 -12.3167 -0.2257 -0.9420 0.2483
-1.2237 -5.5894 13.1137 0.2289 0.9561 -0.1828
3.8471 5.6047 8.7327 -0.8039 0.1935 0.5624
-4.4323 -5.2951 -8.3446 0.8430 -0.2027 -0.4983
-7.3541 4.5519 5.8539 0.4435 -0.1037 0.8902
8.0122 -3.7040 -4.5239 -0.5731 0.1349 -0.8083

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3680
_diffrn_reflns_av_unetI/netI     0.2645
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7023
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        44.487
_diffrn_reflns_theta_max         44.486
_diffrn_reflns_theta_min         3.871
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      313.11(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00   25.00    --  -36.03  57.00  60.00   84
  2  ω    -53.00  31.00   1.00   25.00    --  -36.03  57.00 -60.00   84
  3  ω    -53.00  31.00   1.00   25.00    --  -36.03  57.00-180.00   84
  4  ω     20.00 103.00   1.00  100.00    --   85.19 -61.00-120.00   83
  5  ω     21.00 105.00   1.00  100.00    --   85.19-111.00-120.00   84
  6  ω    115.00 150.00   1.00  100.00    --   85.19 111.00 120.00   35
  7  ω     71.00 146.00   1.00  100.00    --   85.19 178.00 120.00   75
  8  ω    103.00 153.00   1.00  100.00    --   85.19  77.00-120.00   50
  9  ω    103.00 149.00   1.00  100.00    --   85.19  77.00  30.00   46
 10  ω    105.00 155.00   1.00  100.00    --   85.19 111.00 -90.00   50
 11  ω    103.00 135.00   1.00  100.00    --   85.19  77.00-150.00   32
 12  ω     69.00 153.00   1.00  100.00    --   85.19  30.00 -30.00   84
 13  ω     17.00 106.00   1.00  100.00    --   85.19 -95.00  90.00   89
 14  ω     68.00 146.00   1.00  100.00    --   85.19  61.00-180.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1029896000
_diffrn_orient_matrix_UB_12      -0.0510588000
_diffrn_orient_matrix_UB_13      -0.0139166000
_diffrn_orient_matrix_UB_21      0.0189435000
_diffrn_orient_matrix_UB_22      -0.0569838000
_diffrn_orient_matrix_UB_23      0.0503902000
_diffrn_orient_matrix_UB_31      -0.0440413000
_diffrn_orient_matrix_UB_32      0.0953623000
_diffrn_orient_matrix_UB_33      0.0225969000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                691
_reflns_number_total             1867

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.1102
_refine_ls_restrained_S_all      0.928
_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)+(0.1038P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2598
_refine_ls_wR_factor_ref         0.3184

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C32(H32), C23(H23), C33(H33), C34(H34), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C3(H3), C13(H13), C6(H6), C10(H10), C7(H7), C11(H11)
2.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N1(H1A,H1B), N2(H2A,H2B), N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O12 O 0.1154(8) 0.4607(8) 0.2923(3) 0.091(3) Uani 1 1 d . . . . .
O1 O 0.1169(8) 0.7638(8) 0.3742(4) 0.091(3) Uani 1 1 d . . . . .
O11 O 0.0296(8) 0.3187(8) 0.2935(4) 0.094(3) Uani 1 1 d . . . . .
C5 C 0.1871(9) 0.1692(9) 0.4594(4) 0.055(3) Uani 1 1 d . . . . .
O2 O 0.2696(9) 0.7106(10) 0.3720(4) 0.122(4) Uani 1 1 d . . . . .
C9 C 0.3100(10) 0.3014(10) 0.4702(4) 0.056(3) Uani 1 1 d . . . . .
N3 N 0.4241(9) 0.5754(9) 0.3578(4) 0.085(3) Uani 1 1 d . . . . .
H3A H 0.454223 0.610556 0.338912 0.102 Uiso 1 1 calc R U . . .
H3B H 0.374615 0.603112 0.367268 0.102 Uiso 1 1 calc R U . . .
N1 N 0.0555(9) -0.0730(10) 0.3115(4) 0.088(4) Uani 1 1 d . . . . .
H1A H 0.026286 -0.097673 0.283274 0.105 Uiso 1 1 calc R U . . .
H1B H 0.087692 -0.114965 0.333715 0.105 Uiso 1 1 calc R U . . .
N2 N 0.0001(9) 0.0912(9) 0.2852(4) 0.091(4) Uani 1 1 d . . . . .
H2A H -0.028639 0.064999 0.257192 0.110 Uiso 1 1 calc R U . . .
H2B H -0.003689 0.158154 0.290641 0.110 Uiso 1 1 calc R U . . .
C8 C 0.250000 0.2346(14) 0.500000 0.074(6) Uani 1 2 d S T P . .
N4 N 0.5303(10) 0.4361(9) 0.3578(4) 0.089(4) Uani 1 1 d . . . . .
H4A H 0.560540 0.471077 0.338856 0.107 Uiso 1 1 calc R U . . .
H4B H 0.549554 0.373112 0.367301 0.107 Uiso 1 1 calc R U . . .
C4 C 0.2258(10) 0.0797(9) 0.4388(4) 0.071(4) Uani 1 1 d . . . . .
H4 H 0.286003 0.052463 0.455493 0.085 Uiso 1 1 calc R U . . .
C20 C 0.2055(17) 0.7388(10) 0.3935(6) 0.089(5) Uani 1 1 d . . . . .
C14 C 0.3995(11) 0.2688(10) 0.4595(5) 0.070(4) Uani 1 1 d . . . . .
H14 H 0.429745 0.207434 0.474091 0.084 Uiso 1 1 calc R U . . .
C3 C 0.1809(11) 0.0324(10) 0.3970(5) 0.069(4) Uani 1 1 d . . . . .
H3 H 0.209556 -0.027760 0.386541 0.083 Uiso 1 1 calc R U . . .
C2 C 0.0927(11) 0.0699(10) 0.3684(4) 0.067(4) Uani 1 1 d . . . . .
C12 C 0.4010(10) 0.4195(10) 0.4065(4) 0.062(4) Uani 1 1 d . . . . .
C30 C 0.1046(13) 0.3661(13) 0.2869(4) 0.074(4) Uani 1 1 d . . . . .
C24 C 0.3019(9) 0.6467(10) 0.5162(5) 0.072(4) Uani 1 1 d . . . . .
H24 H 0.340462 0.583245 0.528360 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4435(11) 0.3259(11) 0.4278(5) 0.074(4) Uani 1 1 d . . . . .
H13 H 0.502140 0.301797 0.420521 0.088 Uiso 1 1 calc R U . . .
C1 C 0.0511(12) 0.0273(12) 0.3207(5) 0.083(4) Uani 1 1 d . . . . .
C32 C 0.2528(11) 0.2203(10) 0.2959(5) 0.080(4) Uani 1 1 d . . . . .
H32 H 0.255656 0.197368 0.329929 0.096 Uiso 1 1 calc R U . . .
C6 C 0.0955(11) 0.2036(10) 0.4309(5) 0.070(4) Uani 1 1 d . . . . .
H6 H 0.064565 0.261656 0.441735 0.084 Uiso 1 1 calc R U . . .
C23 C 0.3324(9) 0.7333(11) 0.4824(5) 0.078(4) Uani 1 1 d . . . . .
H23 H 0.393662 0.732295 0.470256 0.094 Uiso 1 1 calc R U . . .
C33 C 0.2302(10) 0.1457(11) 0.2502(5) 0.080(4) Uani 1 1 d . . . . .
H33 H 0.217217 0.069428 0.251469 0.097 Uiso 1 1 calc R U . . .
C21 C 0.2315(11) 0.7351(10) 0.4502(5) 0.081(4) Uani 1 1 d . . . . .
C15 C 0.4537(12) 0.4793(11) 0.3723(5) 0.070(4) Uani 1 1 d . . . . .
C10 C 0.2664(11) 0.3930(12) 0.4466(6) 0.091(5) Uani 1 1 d . . . . .
H10 H 0.206973 0.416762 0.453102 0.110 Uiso 1 1 calc R U . . .
C31 C 0.1792(11) 0.3037(11) 0.2680(4) 0.076(4) Uani 1 1 d . . . . .
C7 C 0.0503(11) 0.1541(13) 0.3875(5) 0.091(5) Uani 1 1 d . . . . .
H7 H -0.010875 0.178598 0.370681 0.109 Uiso 1 1 calc R U . . .
C34 C 0.1578(11) 0.2266(12) 0.2230(5) 0.093(5) Uani 1 1 d . . . . .
H34 H 0.092532 0.210735 0.202577 0.111 Uiso 1 1 calc R U . . .
C22 C 0.1977(10) 0.8249(12) 0.4834(5) 0.092(5) Uani 1 1 d . . . . .
H22 H 0.158341 0.887790 0.471300 0.110 Uiso 1 1 calc R U . . .
C11 C 0.3096(14) 0.4493(12) 0.4137(6) 0.101(5) Uani 1 1 d . . . . .
H11 H 0.277000 0.506817 0.396522 0.121 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
O12 C30 1.206(16) . ?
O1 C20 1.27(2) . ?
O11 C30 1.247(16) . ?
C5 C8 1.513(16) . ?
C5 C4 1.420(16) . ?
C5 C6 1.413(17) . ?
O2 C20 1.225(19) . ?
C9 C8 1.542(15) . ?
C9 C14 1.399(16) . ?
C9 C10 1.398(18) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C15 1.313(16) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.293(15) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.348(17) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C15 1.331(16) . ?
C4 H4 0.9300 . ?
C4 C3 1.334(17) . ?
C20 C21 1.53(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.376(17) . ?
C3 H3 0.9300 . ?
C3 C2 1.391(19) . ?
C2 C1 1.429(19) . ?
C2 C7 1.372(18) . ?
C12 C13 1.391(17) . ?
C12 C15 1.517(18) . ?
C12 C11 1.376(19) . ?
C30 C31 1.483(19) . ?
C24 C24 1.53(2) 2_556 ?
C24 H24 0.9800 . ?
C24 C23 1.555(18) . ?
C24 C21 1.583(18) 2_556 ?
C13 H13 0.9300 . ?
C32 H32 0.9800 . ?
C32 C33 1.554(19) . ?
C32 C31 1.551(19) . ?
C32 C34 1.593(19) 7 ?
C6 H6 0.9300 . ?
C6 C7 1.380(19) . ?
C23 H23 0.9800 . ?
C23 C21 1.491(19) . ?
C23 C22 1.603(19) 2_556 ?
C33 H33 0.9800 . ?
C33 C31 1.584(19) 7 ?
C33 C34 1.514(19) . ?
C21 C22 1.59(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(19) . ?
C31 C34 1.56(2) . ?
C7 H7 0.9300 . ?
C34 H34 0.9800 . ?
C22 C22 1.54(3) 2_556 ?
C22 H22 0.9800 . ?
C11 H11 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C5 C8 121.6(11) . . ?
C6 C5 C8 123.8(11) . . ?
C6 C5 C4 113.0(10) . . ?
C14 C9 C8 124.0(12) . . ?
C10 C9 C8 118.1(12) . . ?
C10 C9 C14 117.3(11) . . ?
H3A N3 H3B 120.0 . . ?
C15 N3 H3A 120.0 . . ?
C15 N3 H3B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C5 C8 C5 114.0(15) . 2_556 ?
C5 C8 C9 113.8(7) 2_556 . ?
C5 C8 C9 101.0(6) 2_556 2_556 ?
C5 C8 C9 101.0(6) . . ?
C5 C8 C9 113.8(7) . 2_556 ?
C9 C8 C9 113.9(15) . 2_556 ?
H4A N4 H4B 120.0 . . ?
C15 N4 H4A 120.0 . . ?
C15 N4 H4B 120.0 . . ?
C5 C4 H4 118.1 . . ?
C3 C4 C5 123.9(12) . . ?
C3 C4 H4 118.1 . . ?
O1 C20 C21 115.7(16) . . ?
O2 C20 O1 127.1(15) . . ?
O2 C20 C21 117.0(18) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(11) . . ?
C13 C14 H14 119.4 . . ?
C4 C3 H3 118.9 . . ?
C4 C3 C2 122.2(12) . . ?
C2 C3 H3 118.9 . . ?
C3 C2 C1 122.1(14) . . ?
C7 C2 C3 116.1(11) . . ?
C7 C2 C1 121.7(14) . . ?
C13 C12 C15 117.9(14) . . ?
C11 C12 C13 119.4(13) . . ?
C11 C12 C15 122.5(13) . . ?
O12 C30 O11 122.7(14) . . ?
O12 C30 C31 119.3(16) . . ?
O11 C30 C31 117.8(14) . . ?
C24 C24 H24 125.4 2_556 . ?
C24 C24 C23 89.3(9) 2_556 . ?
C24 C24 C21 89.3(10) 2_556 2_556 ?
C23 C24 H24 125.4 . . ?
C23 C24 C21 90.7(10) . 2_556 ?
C21 C24 H24 125.4 2_556 . ?
C14 C13 C12 120.5(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N1 C1 N2 118.6(12) . . ?
N1 C1 C2 121.5(13) . . ?
N2 C1 C2 119.7(13) . . ?
C33 C32 H32 124.5 . . ?
C33 C32 C34 91.3(10) . 7 ?
C31 C32 H32 124.5 . . ?
C31 C32 C33 90.4(10) . . ?
C31 C32 C34 91.6(10) . 7 ?
C34 C32 H32 124.5 7 . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.4(13) . . ?
C7 C6 H6 118.8 . . ?
C24 C23 H23 124.5 . . ?
C24 C23 C22 90.6(11) . 2_556 ?
C21 C23 C24 91.8(10) . . ?
C21 C23 H23 124.5 . . ?
C21 C23 C22 90.8(10) . 2_556 ?
C22 C23 H23 124.5 2_556 . ?
C32 C33 H33 124.8 . . ?
C32 C33 C31 88.9(10) . 7 ?
C31 C33 H33 124.8 7 . ?
C34 C33 C32 89.8(10) . . ?
C34 C33 H33 124.8 . . ?
C34 C33 C31 93.4(11) . 7 ?
C20 C21 C24 126.0(12) . 2_556 ?
C20 C21 C22 122.5(13) . . ?
C24 C21 C22 90.0(11) 2_556 . ?
C23 C21 C20 126.8(15) . . ?
C23 C21 C24 89.6(10) . 2_556 ?
C23 C21 C22 91.1(10) . . ?
N3 C15 N4 120.2(13) . . ?
N3 C15 C12 119.1(14) . . ?
N4 C15 C12 120.6(12) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(13) . . ?
C11 C10 H10 119.2 . . ?
C30 C31 C32 128.1(11) . . ?
C30 C31 C33 124.2(13) . 7 ?
C30 C31 C34 125.8(13) . . ?
C32 C31 C33 87.0(11) . 7 ?
C32 C31 C34 88.2(10) . . ?
C34 C31 C33 91.4(11) . 7 ?
C2 C7 C6 122.2(13) . . ?
C2 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C32 C34 H34 125.7 7 . ?
C33 C34 C32 88.0(10) . 7 ?
C33 C34 C31 91.6(11) . . ?
C33 C34 H34 125.7 . . ?
C31 C34 C32 88.4(11) . 7 ?
C31 C34 H34 125.7 . . ?
C23 C22 H22 126.0 2_556 . ?
C21 C22 C23 88.7(10) . 2_556 ?
C21 C22 H22 126.0 . . ?
C22 C22 C23 88.8(10) 2_556 2_556 ?
C22 C22 C21 89.3(10) 2_556 . ?
C22 C22 H22 126.0 2_556 . ?
C12 C11 C10 119.8(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?

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
O12 C30 C31 C32 111.8(16) . . . . ?
O12 C30 C31 C33 -5.2(18) . . . 7 ?
O12 C30 C31 C34 -127.0(15) . . . . ?
O1 C20 C21 C24 73.2(17) . . . 2_556 ?
O1 C20 C21 C23 -164.7(12) . . . . ?
O1 C20 C21 C22 -44.4(19) . . . . ?
O11 C30 C31 C32 -72.9(19) . . . . ?
O11 C30 C31 C33 170.2(12) . . . 7 ?
O11 C30 C31 C34 48.3(19) . . . . ?
C5 C4 C3 C2 2.7(19) . . . . ?
C5 C6 C7 C2 -2(2) . . . . ?
O2 C20 C21 C24 -102.0(18) . . . 2_556 ?
O2 C20 C21 C23 20(2) . . . . ?
O2 C20 C21 C22 140.4(14) . . . . ?
C9 C14 C13 C12 1.7(19) . . . . ?
C9 C10 C11 C12 -5(2) . . . . ?
C8 C5 C4 C3 -166.0(11) . . . . ?
C8 C5 C6 C7 165.3(11) . . . . ?
C8 C9 C14 C13 172.0(10) . . . . ?
C8 C9 C10 C11 -171.0(13) . . . . ?
C4 C5 C8 C5 -44.6(8) . . . 2_556 ?
C4 C5 C8 C9 -159.7(11) . . . 2_556 ?
C4 C5 C8 C9 77.8(13) . . . . ?
C4 C5 C6 C7 -0.3(17) . . . . ?
C4 C3 C2 C1 172.1(12) . . . . ?
C4 C3 C2 C7 -4.6(19) . . . . ?
C20 C21 C22 C23 135.8(14) . . . 2_556 ?
C20 C21 C22 C22 -135.4(15) . . . 2_556 ?
C14 C9 C8 C5 34.5(16) . . . 2_556 ?
C14 C9 C8 C5 -88.1(12) . . . . ?
C14 C9 C8 C9 149.5(13) . . . 2_556 ?
C14 C9 C10 C11 0(2) . . . . ?
C3 C2 C1 N1 38(2) . . . . ?
C3 C2 C1 N2 -146.8(14) . . . . ?
C3 C2 C7 C6 4(2) . . . . ?
C30 C31 C34 C32 133.9(14) . . . 7 ?
C30 C31 C34 C33 -138.1(14) . . . . ?
C24 C24 C23 C21 0.2(11) 2_556 . . . ?
C24 C24 C23 C22 91.0(10) 2_556 . . 2_556 ?
C24 C23 C21 C20 -136.9(13) . . . . ?
C24 C23 C21 C24 -0.2(10) . . . 2_556 ?
C24 C23 C21 C22 89.8(11) . . . . ?
C24 C21 C22 C23 1.6(10) 2_556 . . 2_556 ?
C24 C21 C22 C22 90.4(10) 2_556 . . 2_556 ?
C13 C12 C15 N3 -169.5(12) . . . . ?
C13 C12 C15 N4 9.2(17) . . . . ?
C13 C12 C11 C10 8(2) . . . . ?
C1 C2 C7 C6 -172.5(13) . . . . ?
C32 C33 C34 C32 88.7(9) . . . 7 ?
C32 C33 C34 C31 0.4(11) . . . . ?
C32 C31 C34 C32 -88.4(10) . . . 7 ?
C32 C31 C34 C33 -0.4(11) . . . . ?
C6 C5 C8 C5 151.0(12) . . . 2_556 ?
C6 C5 C8 C9 35.9(15) . . . 2_556 ?
C6 C5 C8 C9 -86.6(12) . . . . ?
C6 C5 C4 C3 -0.1(16) . . . . ?
C23 C21 C22 C23 -88.0(10) . . . 2_556 ?
C23 C21 C22 C22 0.8(12) . . . 2_556 ?
C33 C32 C31 C30 136.5(16) . . . . ?
C33 C32 C31 C33 -91.1(10) . . . 7 ?
C33 C32 C31 C34 0.4(11) . . . . ?
C33 C31 C34 C32 -1.4(10) 7 . . 7 ?
C33 C31 C34 C33 86.6(11) 7 . . . ?
C21 C24 C23 C21 -89.2(10) 2_556 . . . ?
C21 C24 C23 C22 1.6(10) 2_556 . . 2_556 ?
C15 C12 C13 C14 179.4(11) . . . . ?
C15 C12 C11 C10 -178.2(13) . . . . ?
C10 C9 C8 C5 -154.9(12) . . . 2_556 ?
C10 C9 C8 C5 82.6(15) . . . . ?
C10 C9 C8 C9 -39.8(10) . . . 2_556 ?
C10 C9 C14 C13 1.3(19) . . . . ?
C31 C32 C33 C31 93.0(11) . . . 7 ?
C31 C32 C33 C34 -0.4(11) . . . . ?
C31 C33 C34 C32 -0.2(10) 7 . . 7 ?
C31 C33 C34 C31 -88.5(11) 7 . . . ?
C7 C2 C1 N1 -145.6(15) . . . . ?
C7 C2 C1 N2 30(2) . . . . ?
C34 C32 C33 C31 1.4(10) 7 . . 7 ?
C34 C32 C33 C34 -92.0(10) 7 . . . ?
C34 C32 C31 C30 -132.3(15) 7 . . . ?
C34 C32 C31 C33 0.1(10) 7 . . 7 ?
C34 C32 C31 C34 91.7(11) 7 . . . ?
C22 C23 C21 C20 132.5(13) 2_556 . . . ?
C22 C23 C21 C24 -90.8(11) 2_556 . . 2_556 ?
C22 C23 C21 C22 -0.8(11) 2_556 . . . ?
C11 C12 C13 C14 -6.2(19) . . . . ?
C11 C12 C15 N3 16.3(18) . . . . ?
C11 C12 C15 N4 -165.0(13) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 14.3 0.2 ?
2 -0.582 0.582 -0.082 414.6 47.7 ?
3 -0.802 -0.302 -0.802 414.6 47.7 ?
4 0.000 0.500 0.500 14.3 0.2 ?
5 0.500 0.000 0.000 14.3 0.2 ?
6 0.500 0.500 0.500 14.3 0.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_ins_header                      
;
TITL PMN-C-8-2mM-40C-reprosmart-1 in I2/a 
REM I2/a (#15 in standard setting)
CELL 1.54184  13.878668  12.595229  27.718681  90.0000 102.3506  90.0000
ZERR    2.00   0.005292   0.003543   0.012192   0.0000   0.0433   0.0000
LATT  2
SYMM -x+1/2, y,-z 
SFAC C H N O
UNIT 100.00 100.00 100.00 100.00
REM  CrysAlisPro recorded range (K): Min=313.1; max=313.1; aver:313.1
TEMP 40
SIZE 0.07 0.13 0.25
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 44.395
_oxdiff_exptl_absorpt_empirical_full_min 0.292

####################################################################### 
# 
# 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_Delta_1CUB2
_database_code_depnum_ccdc_archive 'CCDC 2293129'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_refine_special_details          
;The asymmetric unit contains half a tetra-amidinium cation as well as two half 
molecules of CUB2-. One of the phenyl rings of the tetra-amidinium cation is 
disordered. This was modelled over two positions (occupancies 0.5 each) and it 
was necessary to restrain the C-C bond lengths of this disordered group using 
DFIX restraints in order to achieve a sensible refinement.  There is an area of 
diffuse electron density, believed to arise from water solvent molecules, 
that could not be modelled. This was included in the model using the solvent 
mask feature of OLEX2; this removed a total of 266 e- from a volume of 996 A3 
(20% of the unit cell volume).  This is consistent with the presence of approx. 
27 water molecules, or approximately 6.7 water molecules per formula unit.,SQUEEZE
;

_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H32 N8, 2(C10 H6 O4)'
_chemical_formula_sum            'C49 H44 N8 O8'
_chemical_formula_weight         872.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H50N50O50
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   11.6434(3)
_cell_length_b                   16.4405(5)
_cell_length_c                   26.1717(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.002(2)
_cell_angle_gamma                90
_cell_volume                     4982.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7889
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      74.6510
_cell_measurement_theta_min      3.1850
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 16 0.0649
-7 -1 3 0.0893
7 2 -1 0.0914
2 10 -3 0.0392
-7 0 -1 0.0868
1 -10 4 0.0457
0 -3 -16 0.0231

_exptl_crystal_recrystallization_method 
'Crystallized using tetra-amidinium.4Cl with TBA2.cubanedicarboxylate in 90% EtOH in water. Final concentration of tetra-amidinium = 1 mM'
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.092
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1962 2.4274 16.4967 0.2311 0.9665 -0.1116
-7.4805 -1.4107 2.6391 0.0347 0.1542 0.9874
7.4704 1.5977 -1.3766 -0.0170 -0.0802 -0.9966
1.8089 10.1885 -3.3787 -0.9002 0.2141 -0.3793
-7.4882 -0.0772 -0.5354 -0.1605 0.0409 0.9862
0.6895 -10.3528 3.6230 0.9713 -0.2319 0.0529
-0.1336 -2.5003 -16.3953 -0.2291 -0.9609 0.1554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20473
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.253
_diffrn_reflns_theta_min         3.179
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00 -11.00   0.50   20.00    --  -46.45 115.00-160.00  144
  2  ω    -80.00 -45.00   0.50   20.00    --  -46.45-171.00 -32.00   70
  3  ω     30.00  77.00   0.50   20.00    --   46.45-115.00 109.00   94
  4  ω     70.00 108.00   0.50   80.00    --  107.75 171.00 -18.00   76
  5  ω     69.00 103.00   0.50   80.00    --  107.75-115.00 109.00   68
  6  ω    115.00 151.00   0.50   80.00    --  107.75 115.00-160.00   72
  7  ω     98.00 123.00   0.50   80.00    --  107.75-171.00 -32.00   50
  8  ω      0.00  29.00   0.50   20.00    --  -46.45  19.00  90.00   58
  9  ω    -19.00  26.00   0.50   20.00    --  -46.45  38.00 -30.00   90
 10  ω     -7.00  27.00   0.50   20.00    --  -46.45  19.00-150.00   68
 11  ω     -8.00  30.00   0.50   20.00    --  -46.45  19.00 120.00   76
 12  ω     -2.00  24.00   0.50   20.00    --  -46.45  19.00-180.00   52
 13  ω     96.00 174.00   0.50   80.00    --  107.75  30.00  30.00  156
 14  ω     32.00  58.00   0.50   80.00    --  107.75 -30.00  60.00   52
 15  ω     37.00  66.00   0.50   80.00    --  107.75 -45.00 -90.00   58
 16  ω     32.00  58.00   0.50   80.00    --  107.75 -30.00-150.00   52
 17  ω     63.00  94.00   0.50   80.00    --  107.75 -95.00 -60.00   62
 18  ω     45.00 103.00   0.50   80.00    --  107.75 -95.00 120.00  116
 19  ω     33.00  59.00   0.50   80.00    --  107.75 -30.00  30.00   52
 20  ω     86.00 112.00   0.50   80.00    --  107.75 -77.00 -30.00   52
 21  ω     41.00  68.00   0.50   80.00    --  107.75 -45.00 120.00   54
 22  ω     38.00  63.00   0.50   80.00    --  107.75 -77.00  90.00   50
 23  ω     33.00  58.00   0.50   80.00    --  107.75 -30.00   0.00   50
 24  ω     33.00  59.00   0.50   80.00    --  107.75 -30.00 -90.00   52
 25  ω     84.00 121.00   0.50   80.00    --  107.75 -77.00  90.00   74
 26  ω     38.00  64.00   0.50   80.00    --  107.75 -45.00-120.00   52
 27  ω     44.00  90.00   0.50   80.00    --  107.75 -95.00 -90.00   92
 28  ω     34.00  64.00   0.50   80.00    --  107.75 -95.00 150.00   60
 29  ω     81.00 106.00   0.50   80.00    --  107.75 -95.00 150.00   50
 30  ω     34.00  59.00   0.50   80.00    --  107.75 -30.00  90.00   50
 31  ω     45.00 112.00   0.50   80.00    --  107.75-125.00-120.00  134
 32  ω     34.00  59.00   0.50   80.00    --  107.75 -30.00 -30.00   50
 33  ω     42.00  73.00   0.50   80.00    --  107.75 -77.00 -30.00   62
 34  ω     37.00  64.00   0.50   80.00    --  107.75 -45.00 -60.00   54
 35  ω     33.00  59.00   0.50   80.00    --  107.75 -30.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0204001000
_diffrn_orient_matrix_UB_12      -0.0831898000
_diffrn_orient_matrix_UB_13      0.0264944000
_diffrn_orient_matrix_UB_21      -0.0096390000
_diffrn_orient_matrix_UB_22      0.0401523000
_diffrn_orient_matrix_UB_23      0.0525645000
_diffrn_orient_matrix_UB_31      -0.1311066000
_diffrn_orient_matrix_UB_32      -0.0159302000
_diffrn_orient_matrix_UB_33      -0.0059813000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4180
_reflns_number_total             5243

_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0856
_refine_ls_restrained_S_all      1.061
_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)+(0.1529P)²+6.4509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2519
_refine_ls_wR_factor_ref         0.2652

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C10-C11A
 1.4 with sigma of 0.01
 C5-C4
 1.4 with sigma of 0.005
 C3-C8
 1.4 with sigma of 0.005
 C11A-C12A
 1.4 with sigma of 0.01
 C14A-C15A
 1.4 with sigma of 0.01
 C12A-C13
 1.4 with sigma of 0.01
 C7-C6
 1.4 with sigma of 0.005
 C13-C14
 1.4 with sigma of 0.01
 C13-C14A
 1.4 with sigma of 0.01
 C14-C15
 1.4 with sigma of 0.01
 C15A-C10
 1.4 with sigma of 0.01
 C15-C10
 1.4 with sigma of 0.01
 C8-C7
 1.4 with sigma of 0.005
 C10-C11
 1.4 with sigma of 0.01
 C6-C5
 1.4 with sigma of 0.005
 C11-C12
 1.4 with sigma of 0.01
 C4-C3
 1.4 with sigma of 0.005
 C12-C13
 1.4 with sigma of 0.01
3. Others
 Fixed Sof: C12A(0.5) H12A(0.5) C11A(0.5) H11A(0.5) C15(0.5) H15(0.5) C14(0.5)
 H14(0.5) C14A(0.5) H14A(0.5) C15A(0.5) H15A(0.5) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5)
4.a Ternary CH refined with riding coordinates:
 C32(H32), C34(H34), C33(H33), C24(H24), C22(H22), C23(H23)
4.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C5(H5), C4(H4), C12A(H12A), C11A(H11A), C15(H15), C14(H14),
 C14A(H14A), C15A(H15A), C11(H11), C12(H12)
4.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N1(H1A,H1B), N4(H4A,H4B), N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
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
O11 O 0.74379(16) 0.54252(11) 0.20360(8) 0.0510(5) Uani 1 1 d . . . . .
O10 O 0.59282(17) 0.56103(12) 0.24829(8) 0.0532(5) Uani 1 1 d . . . . .
N2 N 0.0270(2) 0.04724(14) 0.32185(9) 0.0474(5) Uani 1 1 d . . . . .
H2A H -0.013503 0.013738 0.300806 0.057 Uiso 1 1 calc R U . . .
H2B H 0.101902 0.051945 0.320616 0.057 Uiso 1 1 calc R U . . .
O2 O 0.7305(2) 0.35415(15) 0.36822(10) 0.0721(7) Uani 1 1 d . . . . .
C6 C 0.17342(19) 0.24606(14) 0.46280(9) 0.0402(5) Uani 1 1 d D . . . .
N1 N -0.1357(2) 0.08353(19) 0.35712(12) 0.0659(8) Uani 1 1 d . . . . .
H1A H -0.176712 0.050153 0.336202 0.079 Uiso 1 1 calc R U . . .
H1B H -0.169537 0.112534 0.379502 0.079 Uiso 1 1 calc R U . . .
C30 C 0.6859(2) 0.58469(16) 0.23148(10) 0.0445(6) Uani 1 1 d . . . . .
C1 C 0.250000 0.3004(2) 0.500000 0.0401(7) Uani 1 2 d S T P A .
N4 N 0.5607(3) 0.46809(18) 0.33290(12) 0.0700(8) Uani 1 1 d . . . . .
H4A H 0.590216 0.494802 0.308215 0.084 Uiso 1 1 calc R U . . .
H4B H 0.594470 0.423511 0.345597 0.084 Uiso 1 1 calc R U . . .
C3 C 0.0440(2) 0.14543(16) 0.39065(10) 0.0454(6) Uani 1 1 d D . . . .
C2 C -0.0243(2) 0.09002(17) 0.35494(11) 0.0473(6) Uani 1 1 d . . . . .
C31 C 0.7229(2) 0.67023(15) 0.24321(10) 0.0429(6) Uani 1 1 d . . . . .
C13 C 0.3150(2) 0.35394(15) 0.46427(10) 0.0430(6) Uani 1 1 d D . . . .
N3 N 0.4189(3) 0.56055(17) 0.33130(12) 0.0700(8) Uani 1 1 d . . . . .
H3A H 0.449064 0.586775 0.306626 0.084 Uiso 1 1 calc R U . . .
H3B H 0.355631 0.578957 0.343007 0.084 Uiso 1 1 calc R U . . .
C32 C 0.6932(3) 0.72327(17) 0.28953(11) 0.0504(7) Uani 1 1 d . . . . .
H32 H 0.652186 0.703598 0.318907 0.060 Uiso 1 1 calc R U . . .
C34 C 0.8484(2) 0.70608(17) 0.24761(12) 0.0495(6) Uani 1 1 d . . . . .
H34 H 0.920741 0.673792 0.246158 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4172(3) 0.44758(18) 0.39107(12) 0.0550(7) Uani 1 1 d D . . . .
C33 C 0.8187(3) 0.75843(16) 0.29403(11) 0.0495(6) Uani 1 1 d . . . . .
H33 H 0.869768 0.765016 0.326938 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4678(3) 0.49437(19) 0.35054(12) 0.0568(7) Uani 1 1 d . . . . .
C21 C 0.7295(3) 0.2649(2) 0.29862(14) 0.0616(8) Uani 1 1 d . . . . .
C24 C 0.6940(3) 0.3217(2) 0.25236(14) 0.0634(8) Uani 1 1 d . . . . .
H24 H 0.652533 0.374688 0.254230 0.076 Uiso 1 1 calc R U . . .
C22 C 0.6842(3) 0.1896(2) 0.26724(15) 0.0651(9) Uani 1 1 d . . . . .
H22 H 0.636009 0.145140 0.279978 0.078 Uiso 1 1 calc R U . . .
C20 C 0.7133(3) 0.2836(2) 0.35303(16) 0.0723(10) Uani 1 1 d . . . . .
C23 C 0.6472(3) 0.2464(2) 0.22119(14) 0.0616(8) Uani 1 1 d . . . . .
H23 H 0.571749 0.243729 0.199190 0.074 Uiso 1 1 calc R U . . .
C8 C 0.1579(3) 0.1293(2) 0.40581(16) 0.0762(11) Uani 1 1 d D . . . .
H8 H 0.194180 0.083892 0.391763 0.091 Uiso 1 1 calc R U . . .
C7 C 0.2202(3) 0.1783(2) 0.44127(18) 0.0856(14) Uani 1 1 d D . . . .
H7 H 0.298709 0.165079 0.451420 0.103 Uiso 1 1 calc R U . . .
C5 C 0.0617(3) 0.2648(2) 0.44425(17) 0.0811(12) Uani 1 1 d D . . . .
H5 H 0.027668 0.313105 0.455632 0.097 Uiso 1 1 calc R U . . .
O1 O 0.6959(5) 0.2241(3) 0.38285(17) 0.152(2) Uani 1 1 d . . . . .
C4 C -0.0023(3) 0.2150(3) 0.40944(19) 0.0912(15) Uani 1 1 d D . . . .
H4 H -0.080015 0.229144 0.398245 0.109 Uiso 1 1 calc R U . . .
C12A C 0.4010(9) 0.3217(5) 0.4396(4) 0.064(3) Uani 0.5 1 d D . P A 2
H12A H 0.428275 0.268023 0.446985 0.077 Uiso 0.5 1 calc R U P A 2
C11A C 0.4479(7) 0.3691(4) 0.4035(3) 0.055(2) Uani 0.5 1 d D . P A 2
H11A H 0.506490 0.345152 0.385771 0.066 Uiso 0.5 1 calc R U P A 2
C15 C 0.3029(5) 0.4520(5) 0.3932(3) 0.0603(19) Uani 0.5 1 d D . P A 1
H15 H 0.256111 0.486260 0.370335 0.072 Uiso 0.5 1 calc R U P A 1
C14 C 0.2550(5) 0.4057(4) 0.4291(3) 0.0514(14) Uani 0.5 1 d D . P A 1
H14 H 0.173821 0.409414 0.430021 0.062 Uiso 0.5 1 calc R U P A 1
C14A C 0.2832(8) 0.4357(4) 0.4576(4) 0.075(3) Uani 0.5 1 d D . P A 2
H14A H 0.228865 0.459886 0.477645 0.090 Uiso 0.5 1 calc R U P A 2
C15A C 0.3340(8) 0.4805(5) 0.4206(4) 0.080(3) Uani 0.5 1 d D . P A 2
H15A H 0.311464 0.535618 0.415062 0.096 Uiso 0.5 1 calc R U P A 2
C11 C 0.4863(8) 0.3915(8) 0.4198(5) 0.104(5) Uani 0.5 1 d D . P A 1
H11 H 0.566028 0.385073 0.415955 0.125 Uiso 0.5 1 calc R U P A 1
C12 C 0.4302(9) 0.3451(8) 0.4546(6) 0.099(5) Uani 0.5 1 d D . P A 1
H12 H 0.474311 0.304235 0.473354 0.119 Uiso 0.5 1 calc R U P A 1


_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
O11 C30 1.253(3) . ?
O10 C30 1.273(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.307(3) . ?
O2 C20 1.236(4) . ?
C6 C1 1.536(3) . ?
C6 C7 1.385(3) . ?
C6 C5 1.374(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.309(4) . ?
C30 C31 1.493(3) . ?
C1 C13 1.540(3) 2_556 ?
C1 C13 1.540(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C9 1.295(4) . ?
C3 C2 1.476(4) . ?
C3 C8 1.370(3) . ?
C3 C4 1.377(3) . ?
C31 C32 1.561(4) . ?
C31 C34 1.568(3) . ?
C31 C33 1.569(4) 7_665 ?
C13 C12A 1.355(7) . ?
C13 C14 1.387(6) . ?
C13 C14A 1.400(6) . ?
C13 C12 1.398(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C9 1.304(4) . ?
C32 H32 1.0000 . ?
C32 C34 1.559(4) 7_665 ?
C32 C33 1.565(4) . ?
C34 H34 1.0000 . ?
C34 C33 1.557(4) . ?
C10 C9 1.482(4) . ?
C10 C11A 1.370(6) . ?
C10 C15 1.339(6) . ?
C10 C15A 1.408(6) . ?
C10 C11 1.391(8) . ?
C33 H33 1.0000 . ?
C21 C24 1.550(5) . ?
C21 C22 1.548(5) . ?
C21 C20 1.488(5) . ?
C21 C23 1.587(4) 7_655 ?
C24 H24 1.0000 . ?
C24 C22 1.569(4) 7_655 ?
C24 C23 1.550(5) . ?
C22 H22 1.0000 . ?
C22 C23 1.549(6) . ?
C20 O1 1.281(6) . ?
C23 H23 1.0000 . ?
C8 H8 0.9500 . ?
C8 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C12A H12A 0.9500 . ?
C12A C11A 1.381(8) . ?
C11A H11A 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.373(7) . ?
C14 H14 0.9500 . ?
C14A H14A 0.9500 . ?
C14A C15A 1.398(7) . ?
C15A H15A 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.402(8) . ?
C12 H12 0.9500 . ?

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
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
C7 C6 C1 119.9(2) . . ?
C5 C6 C1 124.0(2) . . ?
C5 C6 C7 115.7(2) . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
O11 C30 O10 124.2(2) . . ?
O11 C30 C31 118.6(2) . . ?
O10 C30 C31 117.1(2) . . ?
C6 C1 C6 108.9(3) 2_556 . ?
C6 C1 C13 103.73(13) 2_556 2_556 ?
C6 C1 C13 103.72(13) . . ?
C6 C1 C13 115.32(12) 2_556 . ?
C6 C1 C13 115.33(12) . 2_556 ?
C13 C1 C13 110.3(3) 2_556 . ?
H4A N4 H4B 120.0 . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
C8 C3 C2 120.3(2) . . ?
C8 C3 C4 117.5(3) . . ?
C4 C3 C2 122.3(2) . . ?
N2 C2 N1 120.5(3) . . ?
N2 C2 C3 119.9(2) . . ?
N1 C2 C3 119.5(2) . . ?
C30 C31 C32 127.1(2) . . ?
C30 C31 C34 128.0(2) . . ?
C30 C31 C33 120.8(2) . 7_665 ?
C32 C31 C34 90.8(2) . . ?
C32 C31 C33 89.2(2) . 7_665 ?
C34 C31 C33 89.39(19) . 7_665 ?
C12A C13 C1 120.0(4) . . ?
C12A C13 C14A 121.1(5) . . ?
C14 C13 C1 120.5(3) . . ?
C14 C13 C12 111.7(5) . . ?
C14A C13 C1 118.9(3) . . ?
C12 C13 C1 126.3(5) . . ?
H3A N3 H3B 120.0 . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
C31 C32 H32 125.4 . . ?
C31 C32 C33 89.0(2) . . ?
C34 C32 C31 90.7(2) 7_665 . ?
C34 C32 H32 125.4 7_665 . ?
C34 C32 C33 89.89(19) 7_665 . ?
C33 C32 H32 125.4 . . ?
C31 C34 H34 125.4 . . ?
C32 C34 C31 90.5(2) 7_665 . ?
C32 C34 H34 125.4 7_665 . ?
C33 C34 C31 89.1(2) . . ?
C33 C34 C32 89.7(2) . 7_665 ?
C33 C34 H34 125.4 . . ?
C11A C10 C9 123.1(4) . . ?
C11A C10 C15A 114.2(4) . . ?
C15 C10 C9 118.2(4) . . ?
C15 C10 C11 122.4(5) . . ?
C15A C10 C9 122.7(3) . . ?
C11 C10 C9 118.6(5) . . ?
C31 C33 H33 124.8 7_665 . ?
C32 C33 C31 90.2(2) . 7_665 ?
C32 C33 H33 124.8 . . ?
C34 C33 C31 90.4(2) . 7_665 ?
C34 C33 C32 91.1(2) . . ?
C34 C33 H33 124.8 . . ?
N4 C9 N3 119.2(3) . . ?
N4 C9 C10 119.5(3) . . ?
N3 C9 C10 121.3(3) . . ?
C24 C21 C23 89.5(3) . 7_655 ?
C22 C21 C24 91.1(3) . . ?
C22 C21 C23 90.1(2) . 7_655 ?
C20 C21 C24 125.0(3) . . ?
C20 C21 C22 127.0(3) . . ?
C20 C21 C23 123.1(3) . 7_655 ?
C21 C24 H24 125.2 . . ?
C21 C24 C22 90.5(3) . 7_655 ?
C21 C24 C23 88.9(3) . . ?
C22 C24 H24 125.2 7_655 . ?
C23 C24 H24 125.2 . . ?
C23 C24 C22 90.8(2) . 7_655 ?
C21 C22 C24 89.9(2) . 7_655 ?
C21 C22 H22 125.5 . . ?
C21 C22 C23 89.0(3) . . ?
C24 C22 H22 125.5 7_655 . ?
C23 C22 C24 90.2(3) . 7_655 ?
C23 C22 H22 125.5 . . ?
O2 C20 C21 117.9(3) . . ?
O2 C20 O1 123.5(4) . . ?
O1 C20 C21 118.0(3) . . ?
C21 C23 H23 125.3 7_655 . ?
C24 C23 C21 89.2(2) . 7_655 ?
C24 C23 H23 125.3 . . ?
C22 C23 C21 89.8(3) . 7_655 ?
C22 C23 C24 91.0(3) . . ?
C22 C23 H23 125.3 . . ?
C3 C8 H8 119.8 . . ?
C3 C8 C7 120.5(3) . . ?
C7 C8 H8 119.8 . . ?
C6 C7 H7 118.6 . . ?
C8 C7 C6 122.9(3) . . ?
C8 C7 H7 118.6 . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C13 C12A H12A 121.0 . . ?
C13 C12A C11A 118.0(7) . . ?
C11A C12A H12A 121.0 . . ?
C10 C11A C12A 125.7(6) . . ?
C10 C11A H11A 117.2 . . ?
C12A C11A H11A 117.2 . . ?
C10 C15 H15 120.9 . . ?
C10 C15 C14 118.3(5) . . ?
C14 C15 H15 120.9 . . ?
C13 C14 H14 117.2 . . ?
C15 C14 C13 125.6(5) . . ?
C15 C14 H14 117.2 . . ?
C13 C14A H14A 121.1 . . ?
C15A C14A C13 117.8(5) . . ?
C15A C14A H14A 121.1 . . ?
C10 C15A H15A 118.6 . . ?
C14A C15A C10 122.9(6) . . ?
C14A C15A H15A 118.6 . . ?
C10 C11 H11 122.3 . . ?
C10 C11 C12 115.4(8) . . ?
C12 C11 H11 122.3 . . ?
C13 C12 C11 125.6(9) . . ?
C13 C12 H12 117.2 . . ?
C11 C12 H12 117.2 . . ?

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
O11 C30 C31 C32 -157.9(3) . . . . ?
O11 C30 C31 C34 -30.1(4) . . . . ?
O11 C30 C31 C33 86.7(3) . . . 7_665 ?
O10 C30 C31 C32 26.1(4) . . . . ?
O10 C30 C31 C34 153.9(3) . . . . ?
O10 C30 C31 C33 -89.4(3) . . . 7_665 ?
C6 C1 C13 C12A 45.5(7) 2_556 . . . ?
C6 C1 C13 C12A -73.5(7) . . . . ?
C6 C1 C13 C14 -179.8(4) 2_556 . . . ?
C6 C1 C13 C14 61.2(5) . . . . ?
C6 C1 C13 C14A 106.1(6) . . . . ?
C6 C1 C13 C14A -134.9(6) 2_556 . . . ?
C6 C1 C13 C12 14.9(10) 2_556 . . . ?
C6 C1 C13 C12 -104.0(9) . . . . ?
C6 C5 C4 C3 -1.8(8) . . . . ?
C30 C31 C32 C34 -129.0(3) . . . 7_665 ?
C30 C31 C32 C33 141.1(3) . . . . ?
C30 C31 C34 C32 129.8(3) . . . 7_665 ?
C30 C31 C34 C33 -140.5(3) . . . . ?
C1 C6 C7 C8 -176.8(4) . . . . ?
C1 C6 C5 C4 177.8(4) . . . . ?
C1 C13 C12A C11A 172.7(7) . . . . ?
C1 C13 C14 C15 -175.4(7) . . . . ?
C1 C13 C14A C15A -172.7(8) . . . . ?
C1 C13 C12 C11 176.1(12) . . . . ?
C3 C8 C7 C6 -0.9(8) . . . . ?
C2 C3 C8 C7 -176.4(4) . . . . ?
C2 C3 C4 C5 177.7(4) . . . . ?
C31 C32 C33 C31 90.8(2) . . . 7_665 ?
C31 C32 C33 C34 0.4(2) . . . . ?
C31 C34 C33 C31 -90.61(19) . . . 7_665 ?
C31 C34 C33 C32 -0.4(2) . . . . ?
C13 C1 C13 C12A 162.5(7) 2_556 . . . ?
C13 C1 C13 C14 -62.8(4) 2_556 . . . ?
C13 C1 C13 C14A -17.9(6) 2_556 . . . ?
C13 C1 C13 C12 132.0(9) 2_556 . . . ?
C13 C12A C11A C10 1.9(16) . . . . ?
C13 C14A C15A C10 -1.7(17) . . . . ?
C32 C31 C34 C32 -89.3(2) . . . 7_665 ?
C32 C31 C34 C33 0.4(2) . . . . ?
C32 C34 C33 C31 -0.12(19) 7_665 . . 7_665 ?
C32 C34 C33 C32 90.1(2) 7_665 . . . ?
C34 C31 C32 C34 89.5(2) . . . 7_665 ?
C34 C31 C32 C33 -0.4(2) . . . . ?
C34 C32 C33 C31 0.2(2) 7_665 . . 7_665 ?
C34 C32 C33 C34 -90.3(2) 7_665 . . . ?
C10 C15 C14 C13 0.2(13) . . . . ?
C10 C11 C12 C13 -3(2) . . . . ?
C33 C31 C32 C34 0.12(19) 7_665 . . 7_665 ?
C33 C31 C32 C33 -89.8(2) 7_665 . . . ?
C33 C31 C34 C32 -0.2(2) 7_665 . . 7_665 ?
C33 C31 C34 C33 89.5(2) 7_665 . . . ?
C9 C10 C11A C12A -177.7(8) . . . . ?
C9 C10 C15 C14 177.0(6) . . . . ?
C9 C10 C15A C14A 177.8(9) . . . . ?
C9 C10 C11 C12 -175.3(11) . . . . ?
C21 C24 C23 C21 -90.5(3) . . . 7_655 ?
C21 C24 C23 C22 -0.7(2) . . . . ?
C21 C22 C23 C21 89.9(2) . . . 7_655 ?
C21 C22 C23 C24 0.7(2) . . . . ?
C24 C21 C22 C24 89.5(3) . . . 7_655 ?
C24 C21 C22 C23 -0.7(2) . . . . ?
C24 C21 C20 O2 -39.1(5) . . . . ?
C24 C21 C20 O1 149.0(5) . . . . ?
C24 C22 C23 C21 -0.1(2) 7_655 . . 7_655 ?
C24 C22 C23 C24 -89.2(2) 7_655 . . . ?
C22 C21 C24 C22 -90.1(2) . . . 7_655 ?
C22 C21 C24 C23 0.7(2) . . . . ?
C22 C21 C20 O2 -163.0(3) . . . . ?
C22 C21 C20 O1 25.1(6) . . . . ?
C22 C24 C23 C21 0.0(3) 7_655 . . 7_655 ?
C22 C24 C23 C22 89.8(3) 7_655 . . . ?
C20 C21 C24 C22 131.4(3) . . . 7_655 ?
C20 C21 C24 C23 -137.8(3) . . . . ?
C20 C21 C22 C24 -133.3(4) . . . 7_655 ?
C20 C21 C22 C23 136.5(4) . . . . ?
C23 C21 C24 C22 0.1(2) 7_655 . . 7_655 ?
C23 C21 C24 C23 90.8(2) 7_655 . . . ?
C23 C21 C22 C24 0.0(3) 7_655 . . 7_655 ?
C23 C21 C22 C23 -90.2(3) 7_655 . . . ?
C23 C21 C20 O2 77.4(5) 7_655 . . . ?
C23 C21 C20 O1 -94.6(5) 7_655 . . . ?
C8 C3 C2 N2 -28.3(5) . . . . ?
C8 C3 C2 N1 151.0(4) . . . . ?
C8 C3 C4 C5 -3.1(7) . . . . ?
C7 C6 C1 C6 -43.2(3) . . . 2_556 ?
C7 C6 C1 C13 80.1(4) . . . . ?
C7 C6 C1 C13 -159.2(3) . . . 2_556 ?
C7 C6 C5 C4 5.1(7) . . . . ?
C5 C6 C1 C6 144.4(4) . . . 2_556 ?
C5 C6 C1 C13 28.4(4) . . . 2_556 ?
C5 C6 C1 C13 -92.3(3) . . . . ?
C5 C6 C7 C8 -3.8(7) . . . . ?
C4 C3 C2 N2 150.9(4) . . . . ?
C4 C3 C2 N1 -29.9(5) . . . . ?
C4 C3 C8 C7 4.4(7) . . . . ?
C12A C13 C14A C15A 6.9(15) . . . . ?
C11A C10 C9 N4 -14.6(7) . . . . ?
C11A C10 C9 N3 163.6(6) . . . . ?
C11A C10 C15A C14A -2.9(15) . . . . ?
C15 C10 C9 N4 -151.0(5) . . . . ?
C15 C10 C9 N3 27.2(6) . . . . ?
C15 C10 C11 C12 -5.8(19) . . . . ?
C14 C13 C12 C11 9.8(19) . . . . ?
C14A C13 C12A C11A -7.0(14) . . . . ?
C15A C10 C9 N4 164.6(7) . . . . ?
C15A C10 C9 N3 -17.1(8) . . . . ?
C15A C10 C11A C12A 3.0(13) . . . . ?
C11 C10 C9 N4 18.9(9) . . . . ?
C11 C10 C9 N3 -162.9(9) . . . . ?
C11 C10 C15 C14 7.4(13) . . . . ?
C12 C13 C14 C15 -8.2(12) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.343 0.000 0.500 498.3 133.2 ?
2 -0.524 0.500 0.000 498.3 133.2 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_ins_header                      
;
TITL PMN-C-1-CUB-Block-90EtOH_auto_repro in I2/a 
REM I2/a (#15 in standard setting)
CELL 1.54184  11.643430  16.440511  26.171720  90.0000  96.0022  90.0000
ZERR    2.00   0.000253   0.000460   0.000809   0.0000   0.0023   0.0000
LATT  2
SYMM -x+1/2, y,-z 
SFAC C H N O
UNIT 100.00 100.00 100.00 100.00
REM  CrysAlisPro recorded range (K): Min=150.0; max=150.0; aver:150.0
TEMP -123
SIZE 0.09 0.11 0.21
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.489
_oxdiff_exptl_absorpt_empirical_full_min 0.633

####################################################################### 
# 
# 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_Beta_1CUB2
_database_code_depnum_ccdc_archive 'CCDC 2293127'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_refine_special_details          
;The asymmetric unit contains one tetra-amidinium cation as well as one full 
molecule and two half molecules of CUB2-. A number of water molecules could be 
refined sensibly, although it was necessary to add restraints to some of their 
hydrogen atom positions to achieve a sensible refinement. There is an 
additional area of diffuse electron density, believed to arise from water 
solvent molecules, that could not be modelled. This was included in the model 
using the solvent mask feature of OLEX2; this removed a total of 43 e- from a 
volume of 252 %A3 (10% of the unit cell volume). This is consistent with the 
presence of approx. 4.3 water molecules, or approximately 2 water molecules 
per formula unit in addition to the 8 water molecules that could be 
crystallographically modelled.  Refinement proceeded smoothly and it was 
not necessary to use any crystallographic restraints during the refinement 
apart from those on hydrogen atom positions.,SQUEEZE
;

# start Validation Reply Form
_vrf_PLAT097_Beta_1CUB2          
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.00 eA-3  
RESPONSE: This is located close to O3 (a carboxylate oxygen atom).
;
_vrf_PLAT230_Beta_1CUB2          
;
PROBLEM: Hirshfeld Test Diff for    O3       --C49      .        7.1 s.u.  
RESPONSE: This appears to be due to minor `waggling' of a carboxylate group.
;
_vrf_PLAT420_Beta_1CUB2          
;
PROBLEM: D-H Bond Without Acceptor  O110     --H11B     .     Please Check 
RESPONSE: This is a water solvent molecule.
;
# end Validation Reply Form

_audit_creation_date             2023-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C5 H3 O2), 8(H2 O), C29 H32 N8'
_chemical_formula_sum            'C49 H60 N8 O16'
_chemical_formula_weight         1017.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         C39H54N8O12
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.6429(3)
_cell_length_b                   15.3717(3)
_cell_length_c                   16.0809(3)
_cell_angle_alpha                62.706(2)
_cell_angle_beta                 89.940(2)
_cell_angle_gamma                63.745(2)
_cell_volume                     2600.17(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30035
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.6930
_cell_measurement_theta_min      4.2360
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89009
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 2 2 0.0847
-2 -2 -1 0.0396
0 0 -9 0.0981
-4 -6 -9 0.0849
7 8 1 0.0919
3 4 10 0.1034
-6 -6 4 0.0617
8 2 -4 0.0751
-8 -2 4 0.0184
-3 -3 7 0.0699
6 3 -7 0.0733
0 3 -7 0.1104
-1 -9 -6 0.0856
0 8 8 0.0769
1 -5 -10 0.0659

_exptl_crystal_recrystallization_method 
'Crystallised using tetra-amidinium.4Cl with TBA2.cubanedicarboxylate in 50%EtOH in water. Final concentration of tetra-amidinium = 2 mM'
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.094
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9987 2.4980 1.9992 -0.0750 -0.2976 -0.0005
-1.9990 -2.4983 -0.9996 0.0735 0.2522 -0.1012
0.3809 -0.4084 -9.3014 0.0914 0.3918 0.9155
-4.1108 -5.5214 -9.2191 0.2014 0.8478 0.4905
7.3149 8.4644 1.3843 -0.1956 -0.8130 0.5484
3.1509 4.4613 9.5959 -0.1818 -0.7670 -0.6153
-5.8596 -6.3407 3.7437 0.1041 0.4265 -0.8985
8.0411 1.6522 -4.3185 0.5824 -0.5534 0.5955
-8.0135 -1.6911 4.4048 -0.5759 0.5474 -0.6072
-3.2580 -3.1199 7.3131 0.0082 -0.0045 -1.0000
6.1799 2.7246 -6.6219 0.3026 -0.2895 0.9081
-0.0429 2.9499 -6.6942 -0.2979 0.2791 0.9129
-1.2165 -9.4442 -5.9458 0.8693 0.4736 -0.1415
0.0673 8.2908 8.3779 -0.8607 -0.4679 -0.2003
1.3781 -5.4775 -10.0246 0.7074 0.3834 0.5938

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59597
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.895
_diffrn_reflns_theta_min         3.730
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  49.00   1.00    4.56    --   36.95  67.00 111.68   32
  2  ω     20.00  59.00   1.00    4.56    --   36.95  57.00  90.00   39
  3  ω      4.00  29.00   1.00    4.56    --   36.95  89.00 -83.48   25
  4  ω     63.00  92.00   1.00    4.56    --   36.95  67.00 111.68   29
  5  ω     77.00 103.00   1.00    4.56    --   36.95  57.00-150.00   26
  6  ω     78.00 104.00   1.00    4.56    --   36.95  38.00   0.00   26
  7  ω     23.00  49.00   1.00    4.56    --   36.95  38.00-150.00   26
  8  ω      8.00  73.00   1.00    4.56    --   36.95 -99.00   0.00   65
  9  ω     51.00  98.00   1.00    4.56    --   36.95  68.00-121.92   47
 10  ω     73.00 100.00   1.00    4.56    --   36.95  32.00 -12.00   27
 11  ω     64.00 103.00   1.00    4.56    --   36.95  71.00   7.90   39
 12  ω     59.00  86.00   1.00    4.56    --   36.95  19.00 -60.00   27
 13  ω      7.00  32.00   1.00    4.56    --   36.95  83.00  53.11   25
 14  ω    -34.00  59.00   1.00    4.56    --   36.95 -19.00  60.00   93
 15  ω      5.00  30.00   1.00    4.56    --   36.95  87.00  -6.75   25
 16  ω     65.00 102.00   1.00    4.56    --   36.95  38.00-150.00   37
 17  ω    -27.00  56.00   1.00    4.56    --   36.95 -38.00 150.00   83
 18  ω     19.00  61.00   1.00    4.56    --   36.95  38.00   0.00   42
 19  ω     11.00  64.00   1.00    4.56    --   36.95 -77.00-120.00   53
 20  ω     76.00 102.00   1.00    4.56    --   36.95  57.00  90.00   26
 21  ω     22.00  63.00   1.00    4.56    --   36.95  57.00-150.00   41
 22  ω     22.00  49.00   1.00    4.56    --   36.95  57.00 -30.00   27
 23  ω      4.00  29.00   1.00    4.56    --   36.95  89.00-131.39   25
 24  ω    -26.00  50.00   1.00    4.56    --   36.95 -57.00  30.00   76
 25  ω     70.00 102.00   1.00    4.56    --   36.95  38.00-180.00   32
 26  ω     16.00  62.00   1.00    4.56    --   36.95  71.00   7.90   46
 27  ω     16.00  42.00   1.00    4.56    --   36.95  68.00-121.92   26
 28  ω    -31.00  -6.00   1.00    4.56    --   36.95   0.00-150.00   25
 29  ω     37.00  88.00   1.00    4.56    --   36.95-125.00-180.00   51
 30  ω      4.00  29.00   1.00    4.56    --   36.95  89.00 140.72   25
 31  ω      4.00  30.00   1.00    4.56    --   36.95  89.00-164.73   26
 32  ω     30.00  56.00   1.00    4.56    --   36.95  38.00-180.00   26
 33  ω     16.00  43.00   1.00    4.56    --   36.95  32.00 -12.00   27
 34  ω     15.00  42.00   1.00    4.56    --   36.95  19.00 -60.00   27
 35  ω     -3.00 104.00   1.00    4.56    --   36.95   0.00-150.00  107
 36  ω     40.00  95.00   1.00    4.56    --   36.95  38.00  90.00   55
 37  ω     91.00 117.00   1.00   18.25    --  111.00  64.00 -60.00   26
 38  ω     94.00 120.00   1.00   18.25    --  111.00  50.00  60.00   26
 39  ω     94.00 130.00   1.00   18.25    --  111.00  50.00 150.00   36
 40  ω    153.00 178.00   1.00   18.25    --  111.00  64.00 120.00   25
 41  ω     91.00 118.00   1.00   18.25    --  111.00  64.00 120.00   27
 42  ω     43.00 106.00   1.00   18.25    --  111.00 -92.00  30.00   63
 43  ω     41.00  81.00   1.00   18.25    --  111.00 -20.00 148.65   40
 44  ω     94.00 120.00   1.00   18.25    --  111.00  50.00   0.00   26
 45  ω    143.00 169.00   1.00   18.25    --  111.00  64.00-180.00   26
 46  ω     87.00 152.00   1.00   18.25    --  111.00  25.00 120.00   65
 47  ω     57.00 109.00   1.00   18.25    --  111.00-111.00-150.00   52
 48  ω    123.00 177.00   1.00   18.25    --  111.00  64.00   0.00   54
 49  ω     91.00 117.00   1.00   18.25    --  111.00  64.00-180.00   26
 50  ω     91.00 117.00   1.00   18.25    --  111.00  64.00   0.00   26
 51  ω     91.00 117.00   1.00   18.25    --  111.00  64.00  60.00   26
 52  ω    132.00 178.00   1.00   18.25    --  111.00  64.00  60.00   46
 53  ω     91.00 117.00   1.00   18.25    --  111.00  64.00-120.00   26
 54  ω    132.00 171.00   1.00   18.25    --  111.00  64.00-120.00   39
 55  ω     93.00 134.00   1.00   18.25    --  111.00  38.00   0.00   41
 56  ω     94.00 120.00   1.00   18.25    --  111.00  50.00 120.00   26
 57  ω    131.00 176.00   1.00   18.25    --  111.00  50.00 120.00   45
 58  ω     94.00 125.00   1.00   18.25    --  111.00  50.00-150.00   31
 59  ω     94.00 120.00   1.00   18.25    --  111.00  50.00 -60.00   26
 60  ω    130.00 156.00   1.00   18.25    --  111.00  50.00 -60.00   26
 61  ω    122.00 148.00   1.00   18.25    --  111.00  25.00 -60.00   26
 62  ω     95.00 122.00   1.00   18.25    --  111.00  50.00-180.00   27
 63  ω    133.00 169.00   1.00   18.25    --  111.00  64.00  30.00   36
 64  ω     88.00 131.00   1.00   18.25    --  111.00 -64.00-150.00   43
 65  ω     41.00 127.00   1.00   18.25    --  111.00 -15.00  59.01   86
 66  ω     91.00 117.00   1.00   18.25    --  111.00  64.00  30.00   26
 67  ω     77.00 108.00   1.00   18.25    --  111.00-111.00-120.00   31
 68  ω     94.00 120.00   1.00   18.25    --  111.00  50.00-120.00   26
 69  ω     91.00 139.00   1.00   18.25    --  111.00  64.00 150.00   48
 70  ω    143.00 169.00   1.00   18.25    --  111.00  38.00-120.00   26
 71  ω    125.00 178.00   1.00   18.25    --  111.00  64.00  90.00   53
 72  ω     49.00  75.00   1.00   18.25    --  111.00 -64.00-150.00   26
 73  ω     91.00 117.00   1.00   18.25    --  111.00  64.00  90.00   26
 74  ω     86.00 156.00   1.00   18.25    --  111.00  25.00 -30.00   70
 75  ω    133.00 174.00   1.00   18.25    --  111.00  64.00 -90.00   41
 76  ω     91.00 117.00   1.00   18.25    --  111.00  64.00 -90.00   26
 77  ω     93.00 118.00   1.00   18.25    --  111.00  38.00 120.00   25
 78  ω     67.00 109.00   1.00   18.25    --  111.00-111.00 -30.00   42
 79  ω     46.00  71.00   1.00   18.25    --  111.00 -92.00-150.00   25
 80  ω    102.00 137.00   1.00   18.25    --  111.00 178.00  90.00   35
 81  ω     94.00 120.00   1.00   18.25    --  111.00  50.00  30.00   26
 82  ω     92.00 135.00   1.00   18.25    --  111.00  38.00-150.00   43
 83  ω    144.00 169.00   1.00   18.25    --  111.00  50.00 -30.00   25
 84  ω     94.00 121.00   1.00   18.25    --  111.00  50.00 -30.00   27
 85  ω     68.00 129.00   1.00   18.25    --  111.00 -38.00  60.00   61
 86  ω     92.00 126.00   1.00   18.25    --  111.00  38.00-120.00   34
 87  ω    131.00 157.00   1.00   18.25    --  111.00  38.00  60.00   26
 88  ω     92.00 121.00   1.00   18.25    --  111.00  38.00  60.00   29
 89  ω    126.00 152.00   1.00   18.25    --  111.00  64.00 -30.00   26
 90  ω     43.00  73.00   1.00   18.25    --  111.00-111.00-120.00   30
 91  ω     50.00  95.00   1.00   18.25    --  111.00 -50.00-150.00   45
 92  ω     87.00 120.00   1.00   18.25    --  111.00  25.00 -90.00   33
 93  ω    143.00 176.00   1.00   18.25    --  111.00  38.00 150.00   33
 94  ω     93.00 118.00   1.00   18.25    --  111.00  38.00-180.00   25
 95  ω     94.00 131.00   1.00   18.25    --  111.00  38.00 150.00   37
 96  ω    140.00 176.00   1.00   18.25    --  111.00  64.00-150.00   36
 97  ω     86.00 112.00   1.00   18.25    --  111.00  25.00 150.00   26
 98  ω    131.00 157.00   1.00   18.25    --  111.00  25.00 150.00   26
 99  ω     41.00  90.00   1.00   18.25    --  111.00 -25.00 -30.00   49
100  ω    104.00 134.00   1.00   18.25    --  111.00 -25.00 -30.00   30
101  ω     92.00 130.00   1.00   18.25    --  111.00  38.00 -90.00   38
102  ω     92.00 117.00   1.00   18.25    --  111.00  64.00 -30.00   25
103  ω     66.00  96.00   1.00   18.25    --  111.00 178.00  90.00   30
104  ω     89.00 124.00   1.00   18.25    --  111.00  25.00  90.00   35
105  ω     86.00 115.00   1.00   18.25    --  111.00  25.00  30.00   29
106  ω     75.00 105.00   1.00   18.25    --  111.00 -92.00-120.00   30
107  ω     93.00 118.00   1.00   18.25    --  111.00  38.00  30.00   25
108  ω     91.00 117.00   1.00   18.25    --  111.00  64.00-150.00   26
109  ω     94.00 140.00   1.00   18.25    --  111.00  50.00  90.00   46
110  ω     81.00 109.00   1.00   18.25    --  111.00-111.00 150.00   28
111  ω     86.00 121.00   1.00   18.25    --  111.00  25.00  60.00   35
112  ω     60.00 109.00   1.00   18.25    --  111.00-111.00 120.00   49
113  ω     45.00  79.00   1.00   18.25    --  111.00 -38.00 -30.00   34
114  ω     89.00 125.00   1.00   18.25    --  111.00 -38.00 -30.00   36
115  ω     74.00 118.00   1.00   18.25    --  111.00 -64.00 -30.00   44
116  ω     43.00  78.00   1.00   18.25    --  111.00-111.00 150.00   35
117  ω     94.00 145.00   1.00   18.25    --  111.00  50.00 -90.00   51
118  ω     86.00 164.00   1.00   18.25    --  111.00  25.00   0.00   78
119  ω     82.00 109.00   1.00   18.25    --  111.00-111.00  30.00   27
120  ω     88.00 113.00   1.00   18.25    --  111.00  25.00-150.00   25
121  ω    126.00 166.00   1.00   18.25    --  111.00  25.00-150.00   40
122  ω     88.00 118.00   1.00   18.25    --  111.00  25.00 -60.00   30
123  ω    123.00 149.00   1.00   18.25    --  111.00  50.00-180.00   26
124  ω     61.00  97.00   1.00   18.25    --  111.00 -77.00 120.00   36
125  ω    111.00 138.00   1.00   18.25    --  111.00 -77.00 120.00   27
126  ω     43.00  94.00   1.00   18.25    --  111.00 -50.00 -60.00   51
127  ω    143.00 169.00   1.00   18.25    --  111.00  64.00 -60.00   26
128  ω    146.00 172.00   1.00   18.25    --  111.00  50.00 150.00   26
129  ω    100.00 131.00   1.00   18.25    --  111.00 -20.00 148.65   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0927888000
_diffrn_orient_matrix_UB_12      -0.1030494000
_diffrn_orient_matrix_UB_13      -0.0015069000
_diffrn_orient_matrix_UB_21      -0.0912090000
_diffrn_orient_matrix_UB_22      -0.0097964000
_diffrn_orient_matrix_UB_23      -0.0454278000
_diffrn_orient_matrix_UB_31      0.0032546000
_diffrn_orient_matrix_UB_32      0.0786212000
_diffrn_orient_matrix_UB_33      -0.1017442000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9656
_reflns_number_total             10469
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         10469
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.032
_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)+(0.0602P)²+2.3789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1297

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 H17B-H16B
 2.38 with sigma of 0.02
 H17A-H17B
 1.4 with sigma of 0.01
 H10A-H10B
 1.4 with sigma of 0.01
 H10A-O10_$1
 2.12 with sigma of 0.02
 O140-H14B
 0.88 with sigma of 0.01
3.a Free rotating group:
 O130(H13A,H13B), O120(H12A,H12B), O160(H16A,H16B), O100(H10A,H10B), O150(H15A,
 H15B), O110(H11A,H11B), O140(H14A), O170(H17A,H17B)
3.b Ternary CH refined with riding coordinates:
 C64(H64), C62(H62), C54(H54), C52(H52), C53(H53), C11(H11), C43(H43),
 C42(H42), C44(H44), C47(H47), C45(H45), C46(H46)
3.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C27(H27), C23(H23), C3(H3), C31(H31), C22(H22), C12(H12), C7(H7),
 C15(H15), C28(H28), C9(H9), C30(H30), C4(H4), C20(H20), C14(H14), C6(H6)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N5(H5A,H5B), N6(H6A,H6B), N8(H8A,H8B), N3(H3A,H3B), N4(H4A,H4B),
 N7(H7A,H7B), N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O21 O 0.74159(10) 0.52047(10) 0.89991(8) 0.0209(2) Uani 1 1 d . . . . .
O20 O 0.85197(10) 0.53353(10) 0.79815(8) 0.0210(2) Uani 1 1 d . . . . .
O11 O 0.38722(10) 0.42287(10) 0.70982(9) 0.0241(3) Uani 1 1 d . . . . .
O130 O 0.99733(10) 0.57203(11) 0.68220(9) 0.0270(3) Uani 1 1 d G . . . .
H13A H 0.956099 0.624499 0.623663 0.040 Uiso 1 1 d G U . . .
H13B H 0.948777 0.569406 0.717122 0.040 Uiso 1 1 d G U . . .
O1 O 0.32848(12) -0.29664(10) 0.91633(9) 0.0280(3) Uani 1 1 d . . . . .
O10 O 0.45715(12) 0.52614(12) 0.71304(10) 0.0304(3) Uani 1 1 d . . . . .
O2 O 0.33220(16) -0.19746(13) 0.98089(10) 0.0431(4) Uani 1 1 d . . . . .
N1 N 0.37629(12) 0.38631(12) -0.01151(11) 0.0237(3) Uani 1 1 d . . . . .
H1A H 0.398147 0.430537 -0.054300 0.028 Uiso 1 1 calc R U . . .
H1B H 0.356310 0.395533 0.037175 0.028 Uiso 1 1 calc R U . . .
O120 O 0.55626(14) 0.88537(14) 0.13459(13) 0.0438(4) Uani 1 1 d G . . . .
H12A H 0.582053 0.931929 0.109376 0.066 Uiso 1 1 d G U . . .
H12B H 0.591574 0.844074 0.195641 0.066 Uiso 1 1 d G U . . .
O160 O 0.31883(15) 0.29712(14) 0.67766(12) 0.0431(4) Uani 1 1 d G . . . .
H16A H 0.350602 0.332753 0.683732 0.065 Uiso 1 1 d G U . . .
H16B H 0.289504 0.332597 0.615855 0.065 Uiso 1 1 d DG U . . .
N5 N -0.18592(12) 0.40517(12) 0.28604(11) 0.0229(3) Uani 1 1 d . . . . .
H5A H -0.249749 0.457996 0.284509 0.028 Uiso 1 1 calc R U . . .
H5B H -0.120999 0.393771 0.310920 0.028 Uiso 1 1 calc R U . . .
N6 N -0.28322(11) 0.35859(12) 0.21368(11) 0.0219(3) Uani 1 1 d . . . . .
H6A H -0.347800 0.411064 0.211593 0.026 Uiso 1 1 calc R U . . .
H6B H -0.282836 0.316435 0.190640 0.026 Uiso 1 1 calc R U . . .
N8 N 0.57279(12) -0.36829(12) 0.71414(10) 0.0241(3) Uani 1 1 d . . . . .
H8A H 0.621443 -0.407697 0.770668 0.029 Uiso 1 1 calc R U . . .
H8B H 0.517245 -0.381072 0.707650 0.029 Uiso 1 1 calc R U . . .
N3 N 0.25920(13) -0.33893(12) 0.12310(11) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.254715 -0.386819 0.109872 0.029 Uiso 1 1 calc R U . . .
H3B H 0.288264 -0.297632 0.087764 0.029 Uiso 1 1 calc R U . . .
O3 O 0.23987(15) 0.15635(15) 0.47363(11) 0.0438(4) Uani 1 1 d . . . . .
N4 N 0.17863(14) -0.38942(13) 0.24989(11) 0.0260(3) Uani 1 1 d . . . . .
H4A H 0.173219 -0.437884 0.238110 0.031 Uiso 1 1 calc R U . . .
H4B H 0.154642 -0.381300 0.298050 0.031 Uiso 1 1 calc R U . . .
N7 N 0.66558(13) -0.27053(13) 0.64821(11) 0.0260(3) Uani 1 1 d . . . . .
H7A H 0.714568 -0.309588 0.704502 0.031 Uiso 1 1 calc R U . . .
H7B H 0.671913 -0.218203 0.597835 0.031 Uiso 1 1 calc R U . . .
N2 N 0.40280(13) 0.29048(13) -0.09218(11) 0.0265(3) Uani 1 1 d . . . . .
H2A H 0.424925 0.333711 -0.135805 0.032 Uiso 1 1 calc R U . . .
H2B H 0.400274 0.236514 -0.096647 0.032 Uiso 1 1 calc R U . . .
O100 O 0.48321(12) 0.51695(14) 0.08644(12) 0.0478(4) Uani 1 1 d G . . . .
H10A H 0.477538 0.531805 0.132897 0.072 Uiso 1 1 d DG U . . .
H10B H 0.429302 0.578128 0.037125 0.072 Uiso 1 1 d DG U . . .
O150 O 0.96210(15) 0.36047(15) 0.61079(13) 0.0454(4) Uani 1 1 d G . . . .
H15A H 1.013173 0.358006 0.645565 0.068 Uiso 1 1 d G U . . .
H15B H 0.993515 0.329390 0.577251 0.068 Uiso 1 1 d G U . . .
O4 O 0.10041(15) 0.26944(13) 0.50959(11) 0.0467(4) Uani 1 1 d . . . . .
O110 O 0.35987(18) 0.97305(14) 0.97384(14) 0.0532(5) Uani 1 1 d G . . . .
H11A H 0.362035 0.914525 0.976204 0.080 Uiso 1 1 d G U . . .
H11B H 0.290082 1.026569 0.944844 0.080 Uiso 1 1 d G U . . .
O140 O 0.11761(16) 0.34493(14) 0.73691(16) 0.0520(4) Uani 1 1 d DG . . . .
H14A H 0.080700 0.415794 0.719997 0.078 Uiso 1 1 d G U . . .
O170 O 0.19960(15) 0.40765(15) 0.48729(14) 0.0510(4) Uani 1 1 d G . . . .
H17A H 0.148347 0.477365 0.466436 0.076 Uiso 1 1 d DG U . . .
H17B H 0.161429 0.374167 0.489789 0.076 Uiso 1 1 d DG U . . .
C60 C 0.82930(13) 0.52296(12) 0.87774(11) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.23832(13) -0.08474(12) 0.24691(11) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.28052(12) 0.07953(12) 0.19125(11) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.24628(12) -0.00024(12) 0.26895(11) 0.0138(3) Uani 1 1 d . . . . .
C26 C 0.33556(12) -0.07705(12) 0.36703(11) 0.0145(3) Uani 1 1 d . . . . .
C18 C 0.13034(12) 0.08334(12) 0.27026(11) 0.0146(3) Uani 1 1 d . . . . .
C21 C -0.07832(13) 0.25349(13) 0.25649(11) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.03609(13) 0.13732(13) 0.19422(11) 0.0177(3) Uani 1 1 d . . . . .
H19 H 0.043205 0.116121 0.146605 0.021 Uiso 1 1 calc R U . . .
C50 C 0.43967(13) 0.47665(13) 0.67587(11) 0.0184(3) Uani 1 1 d . . . . .
C27 C 0.30749(13) -0.12986(13) 0.45284(11) 0.0184(3) Uani 1 1 d . . . . .
H27 H 0.232396 -0.116726 0.450773 0.022 Uiso 1 1 calc R U . . .
C61 C 0.91417(13) 0.51221(12) 0.94516(11) 0.0158(3) Uani 1 1 d . . . . .
C13 C 0.23067(14) -0.24761(13) 0.21626(11) 0.0176(3) Uani 1 1 d . . . . .
C23 C 0.11869(13) 0.11723(13) 0.33818(11) 0.0184(3) Uani 1 1 d . . . . .
H23 H 0.182006 0.082723 0.389452 0.022 Uiso 1 1 calc R U . . .
C3 C 0.26269(13) 0.10491(13) 0.09589(11) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.230947 0.070364 0.077633 0.021 Uiso 1 1 calc R U . . .
C31 C 0.44834(13) -0.10447(13) 0.37148(12) 0.0184(3) Uani 1 1 d . . . . .
H31 H 0.470424 -0.074535 0.313412 0.022 Uiso 1 1 calc R U . . .
C51 C 0.47597(13) 0.48572(13) 0.58603(11) 0.0173(3) Uani 1 1 d . . . . .
C22 C 0.01521(14) 0.20110(13) 0.33163(12) 0.0195(3) Uani 1 1 d . . . . .
H22 H 0.008243 0.222886 0.378844 0.023 Uiso 1 1 calc R U . . .
C24 C -0.18755(13) 0.34322(13) 0.25113(11) 0.0181(3) Uani 1 1 d . . . . .
C12 C 0.31621(13) -0.22091(13) 0.19432(11) 0.0182(3) Uani 1 1 d . . . . .
H12 H 0.371478 -0.257056 0.167918 0.022 Uiso 1 1 calc R U . . .
C7 C 0.32145(14) 0.13661(13) 0.21477(11) 0.0188(3) Uani 1 1 d . . . . .
H7 H 0.329168 0.124219 0.278551 0.023 Uiso 1 1 calc R U . . .
C5 C 0.33739(13) 0.23179(13) 0.05202(12) 0.0182(3) Uani 1 1 d . . . . .
C29 C 0.49846(13) -0.22132(13) 0.54513(11) 0.0187(3) Uani 1 1 d . . . . .
C15 C 0.15568(14) -0.11539(14) 0.27177(12) 0.0199(3) Uani 1 1 d . . . . .
H15 H 0.101229 -0.080442 0.299367 0.024 Uiso 1 1 calc R U . . .
C28 C 0.38778(14) -0.20115(13) 0.54093(12) 0.0202(3) Uani 1 1 d . . . . .
H28 H 0.367353 -0.236347 0.598564 0.024 Uiso 1 1 calc R U . . .
C16 C 0.22257(14) -0.32910(13) 0.19550(12) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.32078(13) -0.14152(13) 0.21098(11) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.380740 -0.125644 0.197780 0.020 Uiso 1 1 calc R U . . .
C64 C 0.95725(13) 0.59897(13) 0.91522(12) 0.0189(3) Uani 1 1 d . . . . .
H64 H 0.925093 0.672402 0.852659 0.023 Uiso 1 1 calc R U . . .
C62 C 0.91711(13) 0.49891(14) 1.04778(11) 0.0196(3) Uani 1 1 d . . . . .
H62 H 0.856651 0.498157 1.082850 0.023 Uiso 1 1 calc R U . . .
C8 C 0.37350(13) 0.30652(13) -0.02031(12) 0.0203(3) Uani 1 1 d . . . . .
C54 C 0.48745(14) 0.60443(13) 0.44537(12) 0.0197(3) Uani 1 1 d . . . . .
H54 H 0.477821 0.681533 0.405081 0.024 Uiso 1 1 calc R U . . .
C30 C 0.52860(14) -0.17479(14) 0.45950(12) 0.0204(3) Uani 1 1 d . . . . .
H30 H 0.604659 -0.191262 0.461284 0.024 Uiso 1 1 calc R U . . .
C32 C 0.58308(14) -0.29032(14) 0.63938(12) 0.0207(3) Uani 1 1 d . . . . .
C52 C 0.57040(14) 0.51260(14) 0.54779(12) 0.0196(3) Uani 1 1 d . . . . .
H52 H 0.622455 0.521638 0.582777 0.024 Uiso 1 1 calc R U . . .
C53 C 0.60808(14) 0.42116(13) 0.51782(11) 0.0196(3) Uani 1 1 d . . . . .
H53 H 0.687988 0.362931 0.530649 0.024 Uiso 1 1 calc R U . . .
C4 C 0.29073(14) 0.18011(13) 0.02706(11) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.277947 0.196509 -0.037811 0.023 Uiso 1 1 calc R U . . .
C20 C -0.06745(13) 0.22122(13) 0.18729(12) 0.0185(3) Uani 1 1 d . . . . .
H20 H -0.130668 0.256526 0.135630 0.022 Uiso 1 1 calc R U . . .
C11 C 0.95955(13) 0.58589(13) 1.01732(12) 0.0203(3) Uani 1 1 d . . . . .
H11 H 0.930082 0.649686 1.030030 0.024 Uiso 1 1 calc R U . . .
C14 C 0.15157(14) -0.19596(14) 0.25693(12) 0.0215(3) Uani 1 1 d . . . . .
H14 H 0.094827 -0.215855 0.274499 0.026 Uiso 1 1 calc R U . . .
C6 C 0.35083(14) 0.21074(13) 0.14675(12) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.380145 0.247310 0.164424 0.023 Uiso 1 1 calc R U . . .
C40 C 0.31875(17) -0.20786(15) 0.90906(13) 0.0272(4) Uani 1 1 d . . . . .
C41 C 0.28778(19) -0.10911(16) 0.80991(13) 0.0306(4) Uani 1 1 d . . . . .
C49 C 0.18387(19) 0.17576(19) 0.53045(14) 0.0341(4) Uani 1 1 d . . . . .
C43 C 0.22289(18) 0.07530(16) 0.72804(14) 0.0337(4) Uani 1 1 d . . . . .
H43 H 0.199917 0.143148 0.734137 0.040 Uiso 1 1 calc R U . . .
C48 C 0.22072(18) 0.07638(17) 0.63124(14) 0.0322(4) Uani 1 1 d . . . . .
C42 C 0.34180(17) -0.03164(17) 0.77485(14) 0.0332(4) Uani 1 1 d . . . . .
H42 H 0.406963 -0.042597 0.814743 0.040 Uiso 1 1 calc R U . . .
C44 C 0.16761(19) -0.0004(2) 0.76353(15) 0.0440(5) Uani 1 1 d . . . . .
H44 H 0.103478 0.011587 0.795128 0.053 Uiso 1 1 calc R U . . .
C47 C 0.3403(2) -0.03186(19) 0.67854(17) 0.0517(7) Uani 1 1 d . . . . .
H47 H 0.404809 -0.043921 0.647359 0.062 Uiso 1 1 calc R U . . .
C45 C 0.1658(3) -0.0007(3) 0.66704(16) 0.0652(9) Uani 1 1 d . . . . .
H45 H 0.100327 0.010478 0.627296 0.078 Uiso 1 1 calc R U . . .
C46 C 0.2851(4) -0.1076(2) 0.71273(18) 0.0722(11) Uani 1 1 d . . . . .
H46 H 0.308144 -0.175091 0.706136 0.087 Uiso 1 1 calc R U . . .
H14B H 0.179(3) 0.337(5) 0.715(4) 0.15(2) Uiso 1 1 d D . . . .


_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
O21 C60 1.260(2) . ?
O20 C60 1.270(2) . ?
O11 C50 1.266(2) . ?
O130 H13A 0.8698 . ?
O130 H13B 0.8705 . ?
O1 C40 1.260(2) . ?
O10 C50 1.253(2) . ?
O2 C40 1.261(2) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C8 1.314(2) . ?
O120 H12A 0.8699 . ?
O120 H12B 0.8705 . ?
O160 H16A 0.8699 . ?
O160 H16B 0.8695 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C24 1.316(2) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C24 1.312(2) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C32 1.315(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C16 1.312(2) . ?
O3 C49 1.247(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C16 1.316(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C32 1.312(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C8 1.315(2) . ?
O100 H10A 0.8701 . ?
O100 H10B 0.8715 . ?
O150 H15A 0.8704 . ?
O150 H15B 0.8703 . ?
O4 C49 1.261(3) . ?
O110 H11A 0.8700 . ?
O110 H11B 0.8700 . ?
O140 H14A 0.8702 . ?
O140 H14B 0.886(10) . ?
O170 H17A 0.8705 . ?
O170 H17B 0.8695 . ?
C60 C61 1.487(2) . ?
C10 C1 1.5400(19) . ?
C10 C15 1.396(2) . ?
C10 C9 1.398(2) . ?
C2 C1 1.544(2) . ?
C2 C3 1.390(2) . ?
C2 C7 1.401(2) . ?
C1 C26 1.546(2) . ?
C1 C18 1.543(2) . ?
C26 C27 1.399(2) . ?
C26 C31 1.396(2) . ?
C18 C19 1.402(2) . ?
C18 C23 1.392(2) . ?
C21 C22 1.392(2) . ?
C21 C24 1.484(2) . ?
C21 C20 1.395(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(2) . ?
C50 C51 1.492(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(2) . ?
C61 C64 1.568(2) . ?
C61 C62 1.565(2) . ?
C61 C11 1.573(2) 2_767 ?
C13 C12 1.395(2) . ?
C13 C16 1.483(2) . ?
C13 C14 1.393(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(2) . ?
C31 H31 0.9500 . ?
C31 C30 1.387(2) . ?
C51 C54 1.566(2) 2_666 ?
C51 C52 1.564(2) . ?
C51 C53 1.585(2) 2_666 ?
C22 H22 0.9500 . ?
C12 H12 0.9500 . ?
C12 C9 1.390(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.384(2) . ?
C5 C8 1.480(2) . ?
C5 C4 1.392(2) . ?
C5 C6 1.398(2) . ?
C29 C28 1.395(2) . ?
C29 C30 1.390(2) . ?
C29 C32 1.484(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.388(2) . ?
C28 H28 0.9500 . ?
C9 H9 0.9500 . ?
C64 H64 1.0000 . ?
C64 C62 1.567(2) 2_767 ?
C64 C11 1.559(2) . ?
C62 H62 1.0000 . ?
C62 C11 1.564(2) . ?
C54 H54 1.0000 . ?
C54 C52 1.563(2) . ?
C54 C53 1.563(2) 2_666 ?
C30 H30 0.9500 . ?
C52 H52 1.0000 . ?
C52 C53 1.566(2) . ?
C53 H53 1.0000 . ?
C4 H4 0.9500 . ?
C20 H20 0.9500 . ?
C11 H11 1.0000 . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C40 C41 1.496(2) . ?
C41 C42 1.562(3) . ?
C41 C44 1.572(3) . ?
C41 C46 1.552(3) . ?
C49 C48 1.505(3) . ?
C43 H43 1.0000 . ?
C43 C48 1.549(3) . ?
C43 C42 1.552(3) . ?
C43 C44 1.555(3) . ?
C48 C47 1.565(3) . ?
C48 C45 1.567(3) . ?
C42 H42 1.0000 . ?
C42 C47 1.550(3) . ?
C44 H44 1.0000 . ?
C44 C45 1.553(3) . ?
C47 H47 1.0000 . ?
C47 C46 1.553(4) . ?
C45 H45 1.0000 . ?
C45 C46 1.555(5) . ?
C46 H46 1.0000 . ?

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
H13A O130 H13B 104.5 . . ?
H1A N1 H1B 120.0 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H12A O120 H12B 104.4 . . ?
H16A O160 H16B 104.5 . . ?
H5A N5 H5B 120.0 . . ?
C24 N5 H5A 120.0 . . ?
C24 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C24 N6 H6A 120.0 . . ?
C24 N6 H6B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C32 N8 H8A 120.0 . . ?
C32 N8 H8B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C16 N3 H3A 120.0 . . ?
C16 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C16 N4 H4A 120.0 . . ?
C16 N4 H4B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C32 N7 H7A 120.0 . . ?
C32 N7 H7B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C8 N2 H2A 120.0 . . ?
C8 N2 H2B 120.0 . . ?
H10A O100 H10B 104.4 . . ?
H15A O150 H15B 109.5 . . ?
H11A O110 H11B 104.5 . . ?
H14A O140 H14B 104.1 . . ?
H17A O170 H17B 104.5 . . ?
O21 C60 O20 123.07(14) . . ?
O21 C60 C61 121.23(14) . . ?
O20 C60 C61 115.70(14) . . ?
C15 C10 C1 120.84(13) . . ?
C15 C10 C9 118.17(14) . . ?
C9 C10 C1 120.65(13) . . ?
C3 C2 C1 122.19(13) . . ?
C3 C2 C7 118.26(14) . . ?
C7 C2 C1 119.28(13) . . ?
C10 C1 C2 114.43(12) . . ?
C10 C1 C26 103.34(11) . . ?
C10 C1 C18 111.70(12) . . ?
C2 C1 C26 111.38(12) . . ?
C18 C1 C2 102.23(11) . . ?
C18 C1 C26 114.18(12) . . ?
C27 C26 C1 120.52(13) . . ?
C31 C26 C1 121.05(14) . . ?
C31 C26 C27 118.12(14) . . ?
C19 C18 C1 119.11(13) . . ?
C23 C18 C1 121.93(13) . . ?
C23 C18 C19 118.50(14) . . ?
C22 C21 C24 119.35(14) . . ?
C22 C21 C20 119.40(14) . . ?
C20 C21 C24 121.24(14) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.14(14) . . ?
C20 C19 H19 119.4 . . ?
O11 C50 C51 118.45(14) . . ?
O10 C50 O11 121.87(15) . . ?
O10 C50 C51 119.60(14) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 120.93(15) . . ?
C28 C27 H27 119.5 . . ?
C60 C61 C64 123.22(13) . . ?
C60 C61 C62 131.31(14) . . ?
C60 C61 C11 121.05(13) . 2_767 ?
C64 C61 C11 89.15(11) . 2_767 ?
C62 C61 C64 90.42(11) . . ?
C62 C61 C11 90.09(11) . 2_767 ?
C12 C13 C16 120.60(14) . . ?
C14 C13 C12 119.44(14) . . ?
C14 C13 C16 119.96(15) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 C18 120.57(14) . . ?
C22 C23 H23 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.75(14) . . ?
C4 C3 H3 119.6 . . ?
C26 C31 H31 119.5 . . ?
C30 C31 C26 120.93(15) . . ?
C30 C31 H31 119.5 . . ?
C50 C51 C54 126.66(13) . 2_666 ?
C50 C51 C52 128.07(14) . . ?
C50 C51 C53 121.42(13) . 2_666 ?
C54 C51 C53 89.17(12) 2_666 2_666 ?
C52 C51 C54 90.55(12) . 2_666 ?
C52 C51 C53 89.40(12) . 2_666 ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.60(14) . . ?
C23 C22 H22 119.7 . . ?
N5 C24 C21 118.57(14) . . ?
N6 C24 N5 121.14(15) . . ?
N6 C24 C21 120.28(14) . . ?
C13 C12 H12 119.9 . . ?
C9 C12 C13 120.15(14) . . ?
C9 C12 H12 119.9 . . ?
C2 C7 H7 119.4 . . ?
C6 C7 C2 121.18(15) . . ?
C6 C7 H7 119.4 . . ?
C4 C5 C8 120.43(15) . . ?
C4 C5 C6 118.91(15) . . ?
C6 C5 C8 120.66(15) . . ?
C28 C29 C32 120.86(15) . . ?
C30 C29 C28 119.09(14) . . ?
C30 C29 C32 120.05(15) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.26(15) . . ?
C14 C15 H15 119.4 . . ?
C27 C28 C29 120.21(15) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
N3 C16 N4 121.70(15) . . ?
N3 C16 C13 119.06(15) . . ?
N4 C16 C13 119.24(15) . . ?
C10 C9 H9 119.6 . . ?
C12 C9 C10 120.86(14) . . ?
C12 C9 H9 119.6 . . ?
C61 C64 H64 125.1 . . ?
C62 C64 C61 90.70(11) 2_767 . ?
C62 C64 H64 125.1 2_767 . ?
C11 C64 C61 89.43(12) . . ?
C11 C64 H64 125.1 . . ?
C11 C64 C62 90.58(11) . 2_767 ?
C61 C62 C64 89.66(12) . 2_767 ?
C61 C62 H62 125.6 . . ?
C64 C62 H62 125.6 2_767 . ?
C11 C62 C61 89.33(12) . . ?
C11 C62 C64 89.53(12) . 2_767 ?
C11 C62 H62 125.6 . . ?
N1 C8 N2 121.54(16) . . ?
N1 C8 C5 119.94(15) . . ?
N2 C8 C5 118.51(15) . . ?
C51 C54 H54 125.1 2_666 . ?
C52 C54 C51 90.84(12) . 2_666 ?
C52 C54 H54 125.1 . . ?
C53 C54 C51 89.45(12) 2_666 2_666 ?
C53 C54 H54 125.1 2_666 . ?
C53 C54 C52 90.23(12) 2_666 . ?
C31 C30 C29 120.42(15) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
N8 C32 C29 119.77(15) . . ?
N7 C32 N8 120.53(15) . . ?
N7 C32 C29 119.66(15) . . ?
C51 C52 H52 125.3 . . ?
C51 C52 C53 89.41(12) . . ?
C54 C52 C51 90.57(12) . . ?
C54 C52 H52 125.3 . . ?
C54 C52 C53 89.95(12) . . ?
C53 C52 H52 125.3 . . ?
C51 C53 H53 125.2 2_666 . ?
C54 C53 C51 89.80(12) 2_666 2_666 ?
C54 C53 C52 90.58(12) 2_666 . ?
C54 C53 H53 125.2 2_666 . ?
C52 C53 C51 90.04(11) . 2_666 ?
C52 C53 H53 125.2 . . ?
C3 C4 C5 120.72(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.77(14) . . ?
C19 C20 H20 120.1 . . ?
C61 C11 H11 125.0 2_767 . ?
C64 C11 C61 89.67(12) . 2_767 ?
C64 C11 C62 90.82(12) . . ?
C64 C11 H11 125.0 . . ?
C62 C11 C61 90.63(12) . 2_767 ?
C62 C11 H11 125.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.96(15) . . ?
C15 C14 H14 120.0 . . ?
C7 C6 C5 120.01(14) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O1 C40 O2 123.40(17) . . ?
O1 C40 C41 118.20(16) . . ?
O2 C40 C41 118.40(16) . . ?
C40 C41 C42 126.91(17) . . ?
C40 C41 C44 122.58(17) . . ?
C40 C41 C46 127.38(16) . . ?
C42 C41 C44 88.98(15) . . ?
C46 C41 C42 89.75(16) . . ?
C46 C41 C44 89.6(2) . . ?
O3 C49 O4 125.5(2) . . ?
O3 C49 C48 115.4(2) . . ?
O4 C49 C48 119.11(19) . . ?
C48 C43 H43 124.8 . . ?
C48 C43 C42 90.88(16) . . ?
C48 C43 C44 90.92(16) . . ?
C42 C43 H43 124.8 . . ?
C42 C43 C44 89.97(15) . . ?
C44 C43 H43 124.8 . . ?
C49 C48 C43 128.06(17) . . ?
C49 C48 C47 125.15(18) . . ?
C49 C48 C45 124.16(17) . . ?
C43 C48 C47 89.16(16) . . ?
C43 C48 C45 89.23(16) . . ?
C47 C48 C45 89.3(2) . . ?
C41 C42 H42 125.2 . . ?
C43 C42 C41 90.76(15) . . ?
C43 C42 H42 125.2 . . ?
C47 C42 C41 89.92(16) . . ?
C47 C42 C43 89.59(16) . . ?
C47 C42 H42 125.2 . . ?
C41 C44 H44 125.3 . . ?
C43 C44 C41 90.28(15) . . ?
C43 C44 H44 125.3 . . ?
C45 C44 C41 89.8(2) . . ?
C45 C44 C43 89.54(16) . . ?
C45 C44 H44 125.3 . . ?
C48 C47 H47 125.1 . . ?
C42 C47 C48 90.36(16) . . ?
C42 C47 H47 125.1 . . ?
C42 C47 C46 90.14(16) . . ?
C46 C47 C48 90.3(2) . . ?
C46 C47 H47 125.1 . . ?
C48 C45 H45 125.1 . . ?
C44 C45 C48 90.31(17) . . ?
C44 C45 H45 125.1 . . ?
C44 C45 C46 90.13(18) . . ?
C46 C45 C48 90.2(2) . . ?
C46 C45 H45 125.1 . . ?
C41 C46 C47 90.18(18) . . ?
C41 C46 C45 90.5(2) . . ?
C41 C46 H46 125.1 . . ?
C47 C46 C45 90.17(18) . . ?
C47 C46 H46 125.1 . . ?
C45 C46 H46 125.1 . . ?

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
O21 C60 C61 C64 -127.13(16) . . . . ?
O21 C60 C61 C62 -1.2(2) . . . . ?
O21 C60 C61 C11 120.95(16) . . . 2_767 ?
O20 C60 C61 C64 53.5(2) . . . . ?
O20 C60 C61 C62 179.46(14) . . . . ?
O20 C60 C61 C11 -58.42(19) . . . 2_767 ?
O11 C50 C51 C54 -32.6(2) . . . 2_666 ?
O11 C50 C51 C52 -159.36(15) . . . . ?
O11 C50 C51 C53 83.06(19) . . . 2_666 ?
O1 C40 C41 C42 -135.8(2) . . . . ?
O1 C40 C41 C44 107.3(2) . . . . ?
O1 C40 C41 C46 -11.2(4) . . . . ?
O10 C50 C51 C54 150.53(16) . . . 2_666 ?
O10 C50 C51 C52 23.8(2) . . . . ?
O10 C50 C51 C53 -93.79(19) . . . 2_666 ?
O2 C40 C41 C42 45.2(3) . . . . ?
O2 C40 C41 C44 -71.8(3) . . . . ?
O2 C40 C41 C46 169.8(3) . . . . ?
O3 C49 C48 C43 143.1(2) . . . . ?
O3 C49 C48 C47 21.2(3) . . . . ?
O3 C49 C48 C45 -96.2(3) . . . . ?
O4 C49 C48 C43 -37.8(3) . . . . ?
O4 C49 C48 C47 -159.7(2) . . . . ?
O4 C49 C48 C45 82.9(3) . . . . ?
C60 C61 C64 C62 -127.11(15) . . . 2_767 ?
C60 C61 C64 C11 142.32(15) . . . . ?
C60 C61 C62 C64 133.33(16) . . . 2_767 ?
C60 C61 C62 C11 -137.14(16) . . . . ?
C10 C1 C26 C27 -76.28(16) . . . . ?
C10 C1 C26 C31 97.30(16) . . . . ?
C10 C1 C18 C19 -47.83(18) . . . . ?
C10 C1 C18 C23 140.07(15) . . . . ?
C10 C15 C14 C13 -0.2(3) . . . . ?
C2 C1 C26 C27 160.41(13) . . . . ?
C2 C1 C26 C31 -26.01(18) . . . . ?
C2 C1 C18 C19 74.96(16) . . . . ?
C2 C1 C18 C23 -97.14(16) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C7 C6 C5 1.5(2) . . . . ?
C1 C10 C15 C14 -176.51(15) . . . . ?
C1 C10 C9 C12 177.63(14) . . . . ?
C1 C2 C3 C4 177.66(14) . . . . ?
C1 C2 C7 C6 -178.61(14) . . . . ?
C1 C26 C27 C28 178.39(14) . . . . ?
C1 C26 C31 C30 -179.01(14) . . . . ?
C1 C18 C19 C20 -173.63(14) . . . . ?
C1 C18 C23 C22 173.45(14) . . . . ?
C26 C1 C18 C19 -164.63(13) . . . . ?
C26 C1 C18 C23 23.3(2) . . . . ?
C26 C27 C28 C29 0.0(2) . . . . ?
C26 C31 C30 C29 1.3(2) . . . . ?
C18 C1 C26 C27 45.25(18) . . . . ?
C18 C1 C26 C31 -141.17(14) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C18 C23 C22 C21 -0.6(2) . . . . ?
C19 C18 C23 C22 1.3(2) . . . . ?
C50 C51 C52 C54 -130.86(16) . . . . ?
C50 C51 C52 C53 139.20(16) . . . . ?
C27 C26 C31 C30 -5.3(2) . . . . ?
C61 C64 C11 C61 90.85(11) . . . 2_767 ?
C61 C64 C11 C62 0.23(11) . . . . ?
C61 C62 C11 C61 -89.91(11) . . . 2_767 ?
C61 C62 C11 C64 -0.23(11) . . . . ?
C13 C12 C9 C10 -2.0(2) . . . . ?
C23 C18 C19 C20 -1.3(2) . . . . ?
C3 C2 C1 C10 24.02(19) . . . . ?
C3 C2 C1 C26 140.76(14) . . . . ?
C3 C2 C1 C18 -96.90(16) . . . . ?
C3 C2 C7 C6 -4.3(2) . . . . ?
C31 C26 C27 C28 4.6(2) . . . . ?
C51 C54 C52 C51 -89.44(12) 2_666 . . . ?
C51 C54 C52 C53 -0.03(11) 2_666 . . . ?
C51 C52 C53 C51 90.60(12) . . . 2_666 ?
C51 C52 C53 C54 0.79(11) . . . 2_666 ?
C22 C21 C24 N5 29.5(2) . . . . ?
C22 C21 C24 N6 -149.38(16) . . . . ?
C22 C21 C20 C19 0.2(2) . . . . ?
C24 C21 C22 C23 -179.67(15) . . . . ?
C24 C21 C20 C19 179.71(14) . . . . ?
C12 C13 C16 N3 -29.3(2) . . . . ?
C12 C13 C16 N4 150.90(16) . . . . ?
C12 C13 C14 C15 2.5(2) . . . . ?
C7 C2 C1 C10 -161.94(13) . . . . ?
C7 C2 C1 C26 -45.20(18) . . . . ?
C7 C2 C1 C18 77.14(16) . . . . ?
C7 C2 C3 C4 3.6(2) . . . . ?
C15 C10 C1 C2 -143.79(14) . . . . ?
C15 C10 C1 C26 94.93(16) . . . . ?
C15 C10 C1 C18 -28.26(19) . . . . ?
C15 C10 C9 C12 4.3(2) . . . . ?
C28 C29 C30 C31 3.4(2) . . . . ?
C28 C29 C32 N8 27.4(2) . . . . ?
C28 C29 C32 N7 -150.43(16) . . . . ?
C16 C13 C12 C9 177.78(14) . . . . ?
C16 C13 C14 C15 -176.69(15) . . . . ?
C9 C10 C1 C2 43.04(19) . . . . ?
C9 C10 C1 C26 -78.24(16) . . . . ?
C9 C10 C1 C18 158.57(14) . . . . ?
C9 C10 C15 C14 -3.2(2) . . . . ?
C64 C61 C62 C64 -89.30(11) . . . 2_767 ?
C64 C61 C62 C11 0.23(11) . . . . ?
C64 C62 C11 C61 -0.25(11) 2_767 . . 2_767 ?
C64 C62 C11 C64 89.43(11) 2_767 . . . ?
C62 C61 C64 C62 90.34(12) . . . 2_767 ?
C62 C61 C64 C11 -0.23(11) . . . . ?
C62 C64 C11 C61 0.15(11) 2_767 . . 2_767 ?
C62 C64 C11 C62 -90.47(12) 2_767 . . . ?
C8 C5 C4 C3 176.28(14) . . . . ?
C8 C5 C6 C7 -177.05(14) . . . . ?
C54 C51 C52 C54 89.15(12) 2_666 . . . ?
C54 C51 C52 C53 -0.79(11) 2_666 . . . ?
C54 C52 C53 C51 0.03(11) . . . 2_666 ?
C54 C52 C53 C54 -89.77(12) . . . 2_666 ?
C30 C29 C28 C27 -4.0(2) . . . . ?
C30 C29 C32 N8 -153.28(16) . . . . ?
C30 C29 C32 N7 28.9(2) . . . . ?
C32 C29 C28 C27 175.34(15) . . . . ?
C32 C29 C30 C31 -175.99(15) . . . . ?
C53 C51 C52 C54 -0.01(11) 2_666 . . . ?
C53 C51 C52 C53 -89.95(11) 2_666 . . . ?
C53 C54 C52 C51 0.01(11) 2_666 . . . ?
C53 C54 C52 C53 89.42(12) 2_666 . . . ?
C4 C5 C8 N1 154.09(16) . . . . ?
C4 C5 C8 N2 -26.3(2) . . . . ?
C4 C5 C6 C7 2.1(2) . . . . ?
C20 C21 C22 C23 -0.1(2) . . . . ?
C20 C21 C24 N5 -150.02(16) . . . . ?
C20 C21 C24 N6 31.1(2) . . . . ?
C11 C61 C64 C62 0.25(11) 2_767 . . 2_767 ?
C11 C61 C64 C11 -90.32(12) 2_767 . . . ?
C11 C61 C62 C64 -0.15(11) 2_767 . . 2_767 ?
C11 C61 C62 C11 89.38(12) 2_767 . . . ?
C14 C13 C12 C9 -1.4(2) . . . . ?
C14 C13 C16 N3 149.92(16) . . . . ?
C14 C13 C16 N4 -29.9(2) . . . . ?
C6 C5 C8 N1 -26.7(2) . . . . ?
C6 C5 C8 N2 152.91(16) . . . . ?
C6 C5 C4 C3 -2.9(2) . . . . ?
C40 C41 C42 C43 -132.0(2) . . . . ?
C40 C41 C42 C47 138.4(2) . . . . ?
C40 C41 C44 C43 135.24(18) . . . . ?
C40 C41 C44 C45 -135.23(18) . . . . ?
C40 C41 C46 C47 -138.1(2) . . . . ?
C40 C41 C46 C45 131.7(2) . . . . ?
C41 C42 C47 C48 91.07(16) . . . . ?
C41 C42 C47 C46 0.7(2) . . . . ?
C41 C44 C45 C48 -90.64(19) . . . . ?
C41 C44 C45 C46 -0.47(17) . . . . ?
C49 C48 C47 C42 137.75(18) . . . . ?
C49 C48 C47 C46 -132.11(19) . . . . ?
C49 C48 C45 C44 -137.0(2) . . . . ?
C49 C48 C45 C46 132.8(2) . . . . ?
C43 C48 C47 C42 -0.31(16) . . . . ?
C43 C48 C47 C46 89.83(16) . . . . ?
C43 C48 C45 C44 0.4(2) . . . . ?
C43 C48 C45 C46 -89.77(17) . . . . ?
C43 C42 C47 C48 0.31(16) . . . . ?
C43 C42 C47 C46 -90.0(2) . . . . ?
C43 C44 C45 C48 -0.4(2) . . . . ?
C43 C44 C45 C46 89.81(18) . . . . ?
C48 C43 C42 C41 -90.22(15) . . . . ?
C48 C43 C42 C47 -0.31(16) . . . . ?
C48 C43 C44 C41 90.18(16) . . . . ?
C48 C43 C44 C45 0.4(2) . . . . ?
C48 C47 C46 C41 -91.1(2) . . . . ?
C48 C47 C46 C45 -0.60(17) . . . . ?
C48 C45 C46 C41 90.79(18) . . . . ?
C48 C45 C46 C47 0.60(17) . . . . ?
C42 C41 C44 C43 0.69(15) . . . . ?
C42 C41 C44 C45 90.23(16) . . . . ?
C42 C41 C46 C47 0.7(2) . . . . ?
C42 C41 C46 C45 -89.46(17) . . . . ?
C42 C43 C48 C49 -135.7(2) . . . . ?
C42 C43 C48 C47 0.31(16) . . . . ?
C42 C43 C48 C45 89.62(19) . . . . ?
C42 C43 C44 C41 -0.70(16) . . . . ?
C42 C43 C44 C45 -90.5(2) . . . . ?
C42 C47 C46 C41 -0.7(2) . . . . ?
C42 C47 C46 C45 89.76(18) . . . . ?
C44 C41 C42 C43 -0.69(16) . . . . ?
C44 C41 C42 C47 -90.28(17) . . . . ?
C44 C41 C46 C47 89.7(2) . . . . ?
C44 C41 C46 C45 -0.47(17) . . . . ?
C44 C43 C48 C49 134.3(2) . . . . ?
C44 C43 C48 C47 -89.68(17) . . . . ?
C44 C43 C48 C45 -0.4(2) . . . . ?
C44 C43 C42 C41 0.70(16) . . . . ?
C44 C43 C42 C47 90.61(17) . . . . ?
C44 C45 C46 C41 0.48(18) . . . . ?
C44 C45 C46 C47 -89.71(17) . . . . ?
C47 C48 C45 C44 89.5(2) . . . . ?
C47 C48 C45 C46 -0.60(17) . . . . ?
C45 C48 C47 C42 -89.54(17) . . . . ?
C45 C48 C47 C46 0.60(17) . . . . ?
C46 C41 C42 C43 88.9(2) . . . . ?
C46 C41 C42 C47 -0.7(2) . . . . ?
C46 C41 C44 C43 -89.07(17) . . . . ?
C46 C41 C44 C45 0.47(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 150.1 38.7 ?
2 0.000 0.000 0.500 102.2 4.3 ?
3 0.500 0.000 0.500 15.1 1.9 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_ins_header                      
;
TITL PMN-C-8-2mM_repro_1 in P1 
REM P1 (#1 in standard setting)
CELL 1.54184  13.642899  15.371658  16.080858  62.7056  89.9400  63.7451
ZERR    5.00   0.000272   0.000291   0.000277   0.0018   0.0015   0.0019
LATT -1
SFAC C H N O
UNIT 195.00 270.00 40.00 60.00
REM  CrysAlisPro recorded range (K): Min=150.0; max=150.0; aver:150.0
TEMP -123
SIZE 0.09 0.16 0.27
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.262
_oxdiff_exptl_absorpt_empirical_full_min 0.793
