# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_boc_pnphe_pnphe
_database_code_depnum_ccdc_archive 'CCDC 2391827'
loop_
_audit_author_name
_audit_author_address
'Alejandro Pedro Ayala'
;Universidade Federal do Ceara
Brazil
;
_audit_update_record             
;
2024-10-18 deposited with the CCDC.	2025-03-06 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V144 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2024-10-17
_diffrn_source_power             0.05500000000000001
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5A), C6(H6), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.d Tetrahedral OH refined with riding coordinates:
 O5(H5)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C23 H26 N4 O9'
_chemical_formula_moiety         'C23 H26 N4 O9'
_chemical_formula_weight         502.48
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_space_group_crystal_system      monoclinic
_space_group_IT_number           3
_space_group_name_H-M_alt        'P 1 2 1'
_space_group_name_Hall           'P 2y'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.4892(3)
_cell_length_b                   5.11310(10)
_cell_length_c                   18.7509(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.4730(10)
_cell_angle_gamma                90
_cell_volume                     1197.36(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.00
_cell_measurement_reflns_used    9883
_cell_measurement_theta_min      3.539
_cell_measurement_theta_max      71.683
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0816 after correction.
The Ratio of minimum to maximum transmission is 0.8149.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.00
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirrors'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms HB'
_diffrn_source_voltage           50
_diffrn_source_current           1.40
_diffrn_detector                 HPAD
_diffrn_detector_type            'Bruker PHOTON II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            52422
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_theta_min         3.539
_diffrn_reflns_theta_max         72.243
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4670
_reflns_number_gt                4218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.987
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
'APEX 4 (2019) Bruker AXS Inc., Madison, WI 53719-1173'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.3854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4670
_refine_ls_number_parameters     328
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_abs_structure_details 
;
 Flack x determined using 1711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;

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'

_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_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.29118(15) 0.5831(3) 0.45292(10) 0.0252(4) Uani 1 1 d . . . . .
O2 O 0.37260(16) 0.8917(4) 0.38431(11) 0.0298(4) Uani 1 1 d . . . . .
O3 O 0.37792(15) 0.2247(3) 0.21525(10) 0.0259(4) Uani 1 1 d . . . . .
O4 O 0.49283(15) 0.7858(5) 0.08697(10) 0.0372(5) Uani 1 1 d . . . . .
O5 O 0.35706(16) 0.7681(6) 0.01009(11) 0.0465(7) Uani 1 1 d . . . . .
H5 H 0.404644 0.816463 -0.018434 0.070 Uiso 1 1 calc R U . . .
O6 O 0.87785(19) 0.7354(6) 0.06213(14) 0.0575(8) Uani 1 1 d . . . . .
O7 O 0.8296(3) 0.3680(6) 0.01567(16) 0.0811(11) Uani 1 1 d . . . . .
O8 O -0.12641(18) 0.0447(5) 0.28441(12) 0.0460(6) Uani 1 1 d . . . . .
O9 O -0.03620(17) 0.1813(5) 0.37528(10) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.39756(17) 0.4582(4) 0.36550(11) 0.0224(5) Uani 1 1 d . . . . .
H1 H 0.384796 0.298442 0.380706 0.027 Uiso 1 1 calc R U . . .
N2 N 0.37257(16) 0.6625(4) 0.19896(11) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.386340 0.816099 0.218140 0.024 Uiso 1 1 calc R U . . .
N3 N 0.8283(2) 0.5295(7) 0.06325(17) 0.0485(8) Uani 1 1 d . . . . .
N4 N -0.05570(18) 0.1776(5) 0.31124(12) 0.0280(5) Uani 1 1 d . . . . .
C1 C 0.7612(2) 0.4733(7) 0.12613(16) 0.0343(7) Uani 1 1 d . . . . .
C2 C 0.7696(2) 0.6325(6) 0.18448(16) 0.0334(7) Uani 1 1 d . . . . .
H2A H 0.817491 0.776765 0.184830 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7065(2) 0.5782(6) 0.24312(16) 0.0289(6) Uani 1 1 d . . . . .
H3 H 0.711642 0.686578 0.284162 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6358(2) 0.3679(5) 0.24298(14) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.6300(2) 0.2087(6) 0.18293(15) 0.0290(6) Uani 1 1 d . . . . .
H5A H 0.582304 0.063891 0.182108 0.035 Uiso 1 1 calc R U . . .
C6 C 0.6935(3) 0.2604(6) 0.12415(16) 0.0368(7) Uani 1 1 d . . . . .
H6 H 0.690462 0.150867 0.083271 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5639(2) 0.3199(5) 0.30610(13) 0.0222(5) Uani 1 1 d . . . . .
H7A H 0.604561 0.352917 0.350753 0.027 Uiso 1 1 calc R U . . .
H7B H 0.540891 0.134667 0.306182 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4646(2) 0.4977(5) 0.30378(13) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.489159 0.683792 0.303593 0.024 Uiso 1 1 calc R U . . .
C9 C 0.40108(19) 0.4471(5) 0.23504(13) 0.0199(5) Uani 1 1 d . . . . .
C10 C 0.32030(19) 0.6543(5) 0.13007(13) 0.0212(5) Uani 1 1 d . . . . .
H10 H 0.305096 0.466103 0.119592 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3976(2) 0.7487(5) 0.07316(14) 0.0232(5) Uani 1 1 d . . . . .
C12 C 0.2116(2) 0.7964(5) 0.12995(14) 0.0230(5) Uani 1 1 d . . . . .
H12A H 0.220658 0.977401 0.147748 0.028 Uiso 1 1 calc R U . . .
H12B H 0.182145 0.804591 0.080809 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1360(2) 0.6480(5) 0.17747(14) 0.0222(5) Uani 1 1 d . . . . .
C14 C 0.0719(2) 0.4507(6) 0.14841(14) 0.0233(5) Uani 1 1 d . . . . .
H14 H 0.072250 0.421599 0.098378 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0076(2) 0.2960(5) 0.19155(14) 0.0246(6) Uani 1 1 d . . . . .
H15 H -0.036594 0.162922 0.171700 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0100(2) 0.3422(5) 0.26448(14) 0.0230(5) Uani 1 1 d . . . . .
C17 C 0.0717(2) 0.5360(5) 0.29483(15) 0.0273(6) Uani 1 1 d . . . . .
H17 H 0.071649 0.562887 0.344964 0.033 Uiso 1 1 calc R U . . .
C18 C 0.1338(2) 0.6912(5) 0.25097(14) 0.0263(6) Uani 1 1 d . . . . .
H18 H 0.175401 0.828491 0.271122 0.032 Uiso 1 1 calc R U . . .
C19 C 0.3544(2) 0.6646(5) 0.39997(13) 0.0224(5) Uani 1 1 d . . . . .
C20 C 0.2418(2) 0.7751(5) 0.50235(13) 0.0244(6) Uani 1 1 d . . . . .
C21 C 0.1658(2) 0.9539(6) 0.46193(15) 0.0293(6) Uani 1 1 d . . . . .
H21A H 0.207106 1.075033 0.432419 0.044 Uiso 1 1 calc R U . . .
H21B H 0.122692 1.053376 0.495894 0.044 Uiso 1 1 calc R U . . .
H21C H 0.118581 0.848750 0.431349 0.044 Uiso 1 1 calc R U . . .
C22 C 0.3291(2) 0.9193(6) 0.54284(16) 0.0312(6) Uani 1 1 d . . . . .
H22A H 0.381301 0.793266 0.561588 0.047 Uiso 1 1 calc R U . . .
H22B H 0.297403 1.016526 0.582465 0.047 Uiso 1 1 calc R U . . .
H22C H 0.365052 1.041553 0.510674 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1790(3) 0.6009(6) 0.55246(16) 0.0322(7) Uani 1 1 d . . . . .
H23A H 0.123051 0.508757 0.525533 0.048 Uiso 1 1 calc R U . . .
H23B H 0.146074 0.708331 0.589592 0.048 Uiso 1 1 calc R U . . .
H23C H 0.227462 0.473278 0.574631 0.048 Uiso 1 1 calc R U . . .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.340(3) . ?
O1 C20 1.487(3) . ?
O2 C19 1.219(3) . ?
O3 C9 1.230(3) . ?
O4 C11 1.230(3) . ?
O5 H5 0.8400 . ?
O5 C11 1.286(3) . ?
O6 N3 1.222(4) . ?
O7 N3 1.216(5) . ?
O8 N4 1.220(3) . ?
O9 N4 1.224(3) . ?
N1 H1 0.8800 . ?
N1 C8 1.448(3) . ?
N1 C19 1.352(3) . ?
N2 H2 0.8800 . ?
N2 C9 1.339(3) . ?
N2 C10 1.443(3) . ?
N3 C1 1.481(4) . ?
N4 C16 1.470(3) . ?
C1 C2 1.367(5) . ?
C1 C6 1.378(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(4) . ?
C4 C5 1.391(4) . ?
C4 C7 1.511(3) . ?
C5 H5A 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.538(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.530(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.523(4) . ?
C10 C12 1.540(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.508(3) . ?
C13 C14 1.395(4) . ?
C13 C18 1.396(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(4) . ?
C16 C17 1.375(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C20 C21 1.516(4) . ?
C20 C22 1.515(4) . ?
C20 C23 1.518(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C20 120.4(2) . . ?
C11 O5 H5 109.5 . . ?
C8 N1 H1 119.7 . . ?
C19 N1 H1 119.7 . . ?
C19 N1 C8 120.6(2) . . ?
C9 N2 H2 118.5 . . ?
C9 N2 C10 123.0(2) . . ?
C10 N2 H2 118.5 . . ?
O6 N3 C1 118.1(3) . . ?
O7 N3 O6 124.3(3) . . ?
O7 N3 C1 117.6(3) . . ?
O8 N4 O9 123.5(2) . . ?
O8 N4 C16 118.6(2) . . ?
O9 N4 C16 118.0(2) . . ?
C2 C1 N3 118.8(3) . . ?
C2 C1 C6 122.3(3) . . ?
C6 C1 N3 118.9(3) . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 120.3(2) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 120.8(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 118.9(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C4 C7 H7A 109.3 . . ?
C4 C7 H7B 109.3 . . ?
C4 C7 C8 111.5(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N1 C8 C7 111.5(2) . . ?
N1 C8 H8 108.4 . . ?
N1 C8 C9 110.5(2) . . ?
C7 C8 H8 108.4 . . ?
C9 C8 C7 109.7(2) . . ?
C9 C8 H8 108.4 . . ?
O3 C9 N2 123.2(2) . . ?
O3 C9 C8 122.0(2) . . ?
N2 C9 C8 114.9(2) . . ?
N2 C10 H10 106.7 . . ?
N2 C10 C11 109.5(2) . . ?
N2 C10 C12 112.3(2) . . ?
C11 C10 H10 106.7 . . ?
C11 C10 C12 114.4(2) . . ?
C12 C10 H10 106.7 . . ?
O4 C11 O5 123.6(2) . . ?
O4 C11 C10 121.2(2) . . ?
O5 C11 C10 115.0(2) . . ?
C10 C12 H12A 110.0 . . ?
C10 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 C10 108.5(2) . . ?
C13 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 C18 118.9(2) . . ?
C18 C13 C12 121.4(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 H15 121.0 . . ?
C15 C16 N4 118.9(2) . . ?
C17 C16 N4 118.6(2) . . ?
C17 C16 C15 122.5(2) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.8(2) . . ?
C18 C17 H17 120.6 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
O1 C19 N1 110.5(2) . . ?
O2 C19 O1 125.9(2) . . ?
O2 C19 N1 123.6(2) . . ?
O1 C20 C21 110.3(2) . . ?
O1 C20 C22 109.5(2) . . ?
O1 C20 C23 102.6(2) . . ?
C21 C20 C23 109.8(2) . . ?
C22 C20 C21 113.7(2) . . ?
C22 C20 C23 110.4(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O4 0.84 1.83 2.625(3) 157.8 2_655 yes
N2 H2 O3 0.88 2.09 2.891(3) 150.5 1_565 yes

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
O6 N3 C1 C2 -9.7(4) . . . . ?
O6 N3 C1 C6 171.2(3) . . . . ?
O7 N3 C1 C2 171.0(3) . . . . ?
O7 N3 C1 C6 -8.1(4) . . . . ?
O8 N4 C16 C15 -15.3(4) . . . . ?
O8 N4 C16 C17 164.9(3) . . . . ?
O9 N4 C16 C15 164.6(2) . . . . ?
O9 N4 C16 C17 -15.2(4) . . . . ?
N1 C8 C9 O3 -74.7(3) . . . . ?
N1 C8 C9 N2 104.9(2) . . . . ?
N2 C10 C11 O4 9.4(4) . . . . ?
N2 C10 C11 O5 -175.1(2) . . . . ?
N2 C10 C12 C13 -66.2(3) . . . . ?
N3 C1 C2 C3 -179.9(3) . . . . ?
N3 C1 C6 C5 -179.5(3) . . . . ?
N4 C16 C17 C18 179.9(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C2 C3 C4 C7 -177.1(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C7 C8 80.7(3) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C7 C8 N1 -178.0(2) . . . . ?
C4 C7 C8 C9 59.2(3) . . . . ?
C5 C4 C7 C8 -97.1(3) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 C4 C5 C6 177.6(3) . . . . ?
C7 C8 C9 O3 48.6(3) . . . . ?
C7 C8 C9 N2 -131.8(2) . . . . ?
C8 N1 C19 O1 176.8(2) . . . . ?
C8 N1 C19 O2 -3.7(4) . . . . ?
C9 N2 C10 C11 -109.6(3) . . . . ?
C9 N2 C10 C12 122.1(2) . . . . ?
C10 N2 C9 O3 -5.8(4) . . . . ?
C10 N2 C9 C8 174.7(2) . . . . ?
C10 C12 C13 C14 -90.4(3) . . . . ?
C10 C12 C13 C18 85.2(3) . . . . ?
C11 C10 C12 C13 168.2(2) . . . . ?
C12 C10 C11 O4 136.5(3) . . . . ?
C12 C10 C11 O5 -48.0(3) . . . . ?
C12 C13 C14 C15 174.9(2) . . . . ?
C12 C13 C18 C17 -173.6(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C13 C18 C17 1.9(4) . . . . ?
C14 C15 C16 N4 -178.8(2) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 -1.6(4) . . . . ?
C18 C13 C14 C15 -0.8(4) . . . . ?
C19 O1 C20 C21 63.3(3) . . . . ?
C19 O1 C20 C22 -62.5(3) . . . . ?
C19 O1 C20 C23 -179.8(2) . . . . ?
C19 N1 C8 C7 137.0(2) . . . . ?
C19 N1 C8 C9 -100.8(3) . . . . ?
C20 O1 C19 O2 -4.5(4) . . . . ?
C20 O1 C19 N1 174.9(2) . . . . ?

