# 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. 
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data_cu_20240117_ys_zbu_b_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2k4wh3
_database_code_depnum_ccdc_archive 'CCDC 2358185'
loop_
_audit_author_name
_audit_author_address
'jiapeng wang'
;North University of China
China
;
_audit_update_record             
;
2024-05-25 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 S, 2(C8 H11 N10 O2), 6(H2 O)'
_chemical_formula_sum            'C16 H34 N20 O14 S'
_chemical_formula_weight         762.69
_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'
S S 0.3331 0.5567 '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        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.3798(6)
_cell_length_b                   6.4900(2)
_cell_length_c                   25.5179(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.008(2)
_cell_angle_gamma                90
_cell_volume                     3227.51(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      78.469
_cell_measurement_theta_min      3.623
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.804
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0945 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.8857.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18012
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.464
_diffrn_reflns_theta_min         3.623
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2807
_reflns_number_total             3449
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.323
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+1.3524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B), O4(H4A,H4B), O7(H7C,H7D)
2.b X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C1(H1C,H1D,H1E), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
S1 S 0.500000 0.70976(8) 0.750000 0.01910(14) Uani 1 2 d S T P . .
O5 O 0.47979(7) 0.8394(2) 0.78968(6) 0.0403(4) Uani 1 1 d . . . . .
O6 O 0.44140(6) 0.5783(2) 0.72145(5) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.42818(7) 0.4243(2) 0.42168(5) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.36437(7) 0.7167(2) 0.41067(5) 0.0322(3) Uani 1 1 d . . . . .
N1 N 0.45528(8) 0.2151(2) 0.66669(6) 0.0261(3) Uani 1 1 d . . . . .
H1A H 0.4757(11) 0.100(4) 0.6811(9) 0.031 Uiso 1 1 d . U . . .
H1B H 0.4500(12) 0.316(4) 0.6873(10) 0.043(6) Uiso 1 1 d . . . . .
N2 N 0.41684(7) 0.4313(2) 0.58808(5) 0.0212(3) Uani 1 1 d . . . . .
H2 H 0.3959(13) 0.533(4) 0.6010(10) 0.051(7) Uiso 1 1 d . . . . .
N3 N 0.45055(7) 0.2465(2) 0.52743(5) 0.0238(3) Uani 1 1 d . . . . .
N4 N 0.46795(7) 0.1507(2) 0.57793(5) 0.0220(3) Uani 1 1 d . . . . .
N5 N 0.33942(7) 0.7718(2) 0.58348(5) 0.0235(3) Uani 1 1 d . . . . .
N6 N 0.30819(7) 0.9131(2) 0.60809(6) 0.0239(3) Uani 1 1 d . . . . .
N7 N 0.24500(9) 1.2240(3) 0.58274(7) 0.0366(4) Uani 1 1 d . . . . .
H7A H 0.227673 1.316202 0.557156 0.044 Uiso 1 1 calc R U . . .
H7B H 0.239093 1.237122 0.615386 0.044 Uiso 1 1 calc R U . . .
N8 N 0.29256(7) 1.0279(2) 0.52409(6) 0.0246(3) Uani 1 1 d . . . . .
N9 N 0.33670(8) 0.8368(2) 0.44279(6) 0.0288(3) Uani 1 1 d . . . . .
N10 N 0.39931(8) 0.5459(2) 0.44350(6) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.50613(9) -0.0419(3) 0.58612(7) 0.0251(4) Uani 1 1 d . . . . .
H1C H 0.504049 -0.102123 0.550449 0.038 Uiso 1 1 calc R U . . .
H1D H 0.485965 -0.137997 0.606715 0.038 Uiso 1 1 calc R U . . .
H1E H 0.554078 -0.015326 0.606700 0.038 Uiso 1 1 calc R U . . .
C2 C 0.44797(8) 0.2617(2) 0.61483(6) 0.0203(3) Uani 1 1 d . . . . .
C3 C 0.41948(8) 0.4149(3) 0.53526(6) 0.0213(3) Uani 1 1 d . . . . .
C4 C 0.39117(8) 0.5666(3) 0.49313(6) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.35203(8) 0.7494(3) 0.49129(6) 0.0222(3) Uani 1 1 d . . . . .
C6 C 0.32819(8) 0.8495(3) 0.53373(7) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.28021(8) 1.0643(3) 0.57205(7) 0.0233(3) Uani 1 1 d . . . . .
C8 C 0.30578(11) 0.8827(3) 0.66394(7) 0.0362(5) Uani 1 1 d . . . . .
H8A H 0.262948 0.812822 0.663359 0.054 Uiso 1 1 calc R U . . .
H8B H 0.307856 1.016715 0.682078 0.054 Uiso 1 1 calc R U . . .
H8C H 0.344896 0.798218 0.684040 0.054 Uiso 1 1 calc R U . . .
O3 O 0.22540(7) 0.2943(2) 0.68952(6) 0.0387(3) Uani 1 1 d G . . . .
H3A H 0.194011 0.383770 0.690423 0.058 Uiso 1 1 d G U . . .
H3B H 0.262461 0.340258 0.713169 0.058 Uiso 1 1 d G U . . .
O4 O 0.33946(7) 0.4687(2) 0.76766(7) 0.0414(4) Uani 1 1 d G . . . .
H4A H 0.373601 0.521897 0.758253 0.062 Uiso 1 1 d G U . . .
H4B H 0.323739 0.569989 0.782760 0.062 Uiso 1 1 d G U . . .
O7 O 0.63102(8) 1.0637(3) 0.69923(7) 0.0464(4) Uani 1 1 d G . . . .
H7C H 0.599946 1.011555 0.712519 0.070 Uiso 1 1 d G U . . .
H7D H 0.634020 1.192058 0.709448 0.070 Uiso 1 1 d G 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
S1 O5 1.4650(13) . ?
S1 O5 1.4650(13) 2_656 ?
S1 O6 1.4751(12) 2_656 ?
S1 O6 1.4751(12) . ?
O1 N10 1.2124(18) . ?
O2 N9 1.3665(18) . ?
O2 N10 1.4454(18) . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.87(3) . ?
N1 C2 1.323(2) . ?
N2 H2 0.90(3) . ?
N2 C2 1.351(2) . ?
N2 C3 1.369(2) . ?
N3 N4 1.3807(18) . ?
N3 C3 1.307(2) . ?
N4 C1 1.455(2) . ?
N4 C2 1.340(2) . ?
N5 N6 1.3695(18) . ?
N5 C6 1.322(2) . ?
N6 C7 1.352(2) . ?
N6 C8 1.454(2) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N7 C7 1.333(2) . ?
N8 C6 1.350(2) . ?
N8 C7 1.341(2) . ?
N9 C5 1.313(2) . ?
N10 C4 1.331(2) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 H1E 0.9800 . ?
C3 C4 1.447(2) . ?
C4 C5 1.423(2) . ?
C5 C6 1.462(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O3 H3A 0.8693 . ?
O3 H3B 0.8701 . ?
O4 H4A 0.8710 . ?
O4 H4B 0.8692 . ?
O7 H7C 0.8695 . ?
O7 H7D 0.8700 . ?

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
O5 S1 O5 109.93(13) . 2_656 ?
O5 S1 O6 109.97(8) 2_656 . ?
O5 S1 O6 108.83(7) 2_656 2_656 ?
O5 S1 O6 108.83(7) . . ?
O5 S1 O6 109.97(8) . 2_656 ?
O6 S1 O6 109.32(11) . 2_656 ?
N9 O2 N10 108.04(11) . . ?
H1A N1 H1B 121(2) . . ?
C2 N1 H1A 120.9(14) . . ?
C2 N1 H1B 115.8(16) . . ?
C2 N2 H2 128.0(16) . . ?
C2 N2 C3 106.65(13) . . ?
C3 N2 H2 125.3(16) . . ?
C3 N3 N4 103.74(13) . . ?
N3 N4 C1 120.11(13) . . ?
C2 N4 N3 111.46(13) . . ?
C2 N4 C1 128.37(14) . . ?
C6 N5 N6 102.21(13) . . ?
N5 N6 C8 120.81(14) . . ?
C7 N6 N5 109.54(13) . . ?
C7 N6 C8 129.57(14) . . ?
H7A N7 H7B 120.0 . . ?
C7 N7 H7A 120.0 . . ?
C7 N7 H7B 120.0 . . ?
C7 N8 C6 102.67(13) . . ?
C5 N9 O2 107.03(14) . . ?
O1 N10 O2 117.13(13) . . ?
O1 N10 C4 135.62(15) . . ?
C4 N10 O2 107.25(13) . . ?
N4 C1 H1C 109.5 . . ?
N4 C1 H1D 109.5 . . ?
N4 C1 H1E 109.5 . . ?
H1C C1 H1D 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
N1 C2 N2 126.19(15) . . ?
N1 C2 N4 127.71(15) . . ?
N4 C2 N2 106.09(14) . . ?
N2 C3 C4 123.84(14) . . ?
N3 C3 N2 112.07(14) . . ?
N3 C3 C4 124.09(14) . . ?
N10 C4 C3 120.30(15) . . ?
N10 C4 C5 106.11(14) . . ?
C5 C4 C3 133.59(15) . . ?
N9 C5 C4 111.57(14) . . ?
N9 C5 C6 117.86(15) . . ?
C4 C5 C6 130.57(15) . . ?
N5 C6 N8 115.78(14) . . ?
N5 C6 C5 122.68(15) . . ?
N8 C6 C5 121.54(14) . . ?
N7 C7 N6 124.75(15) . . ?
N7 C7 N8 125.44(15) . . ?
N8 C7 N6 109.80(14) . . ?
N6 C8 H8A 109.5 . . ?
N6 C8 H8B 109.5 . . ?
N6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H3A O3 H3B 104.4 . . ?
H4A O4 H4B 104.5 . . ?
H7C O7 H7D 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N10 C4 C3 -2.1(3) . . . . ?
O1 N10 C4 C5 178.8(2) . . . . ?
O2 N9 C5 C4 0.3(2) . . . . ?
O2 N9 C5 C6 179.82(14) . . . . ?
O2 N10 C4 C3 178.70(14) . . . . ?
O2 N10 C4 C5 -0.46(18) . . . . ?
N2 C3 C4 N10 176.03(15) . . . . ?
N2 C3 C4 C5 -5.1(3) . . . . ?
N3 N4 C2 N1 178.88(17) . . . . ?
N3 N4 C2 N2 0.34(18) . . . . ?
N3 C3 C4 N10 -4.0(3) . . . . ?
N3 C3 C4 C5 174.93(17) . . . . ?
N4 N3 C3 N2 0.49(18) . . . . ?
N4 N3 C3 C4 -179.52(15) . . . . ?
N5 N6 C7 N7 178.78(17) . . . . ?
N5 N6 C7 N8 -0.5(2) . . . . ?
N6 N5 C6 N8 -0.03(19) . . . . ?
N6 N5 C6 C5 -179.54(15) . . . . ?
N9 O2 N10 O1 -178.74(15) . . . . ?
N9 O2 N10 C4 0.65(18) . . . . ?
N9 C5 C6 N5 178.35(16) . . . . ?
N9 C5 C6 N8 -1.1(2) . . . . ?
N10 O2 N9 C5 -0.56(18) . . . . ?
N10 C4 C5 N9 0.1(2) . . . . ?
N10 C4 C5 C6 -179.33(17) . . . . ?
C1 N4 C2 N1 -4.0(3) . . . . ?
C1 N4 C2 N2 177.44(15) . . . . ?
C2 N2 C3 N3 -0.30(19) . . . . ?
C2 N2 C3 C4 179.71(15) . . . . ?
C3 N2 C2 N1 -178.60(17) . . . . ?
C3 N2 C2 N4 -0.03(18) . . . . ?
C3 N3 N4 C1 -177.88(14) . . . . ?
C3 N3 N4 C2 -0.51(18) . . . . ?
C3 C4 C5 N9 -178.87(18) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
C4 C5 C6 N5 -2.2(3) . . . . ?
C4 C5 C6 N8 178.28(17) . . . . ?
C6 N5 N6 C7 0.32(18) . . . . ?
C6 N5 N6 C8 177.46(17) . . . . ?
C6 N8 C7 N6 0.46(19) . . . . ?
C6 N8 C7 N7 -178.83(18) . . . . ?
C7 N8 C6 N5 -0.3(2) . . . . ?
C7 N8 C6 C5 179.25(15) . . . . ?
C8 N6 C7 N7 2.0(3) . . . . ?
C8 N6 C7 N8 -177.32(18) . . . . ?

_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_cu_20240117_ys_
_audit_block_doi                 10.5517/ccdc.csd.cc2k4wj4
_database_code_depnum_ccdc_archive 'CCDC 2358186'
loop_
_audit_author_name
_audit_author_address
'jiapeng wang'
;North University of China
China
;
_audit_update_record             
;
2024-05-25 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)

;
_audit_creation_date             2024-03-11
_chemical_formula_sum            'C10 H13 N13 O7'
_chemical_formula_weight         427.330
_refine_ls_R_factor_all          0.041
_cell_length_a                   7.2046(2)
_cell_length_b                   12.8063(3)
_cell_length_c                   18.8900(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 100.014(2)
_cell_angle_gamma                90.000
_cell_volume                     1716.3(1)
_cell_formula_units_Z            4
_symmetry_cell_setting           monoclinic
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  -P_2yn

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? ?
N ? ?
H ? ?
C ? ?


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O1 O 0.2874(2) 0.4030(1) 0.2883(1) 1.000 4 e ? d Uani 0.0413(3)
O2 O 0.4863(2) 0.3870(1) 0.3877(1) 1.000 4 e ? d Uani 0.0380(3)
O3 O 1.0661(2) 0.5578(1) 0.6369(1) 1.000 4 e ? d Uani 0.0316(3)
O4 O 1.1887(2) 0.6979(1) 0.7024(1) 1.000 4 e ? d Uani 0.0376(3)
O5 O 0.6002(2) 1.1573(1) 0.4508(1) 1.000 4 e ? d Uani 0.0385(3)
O6 O 0.6245(2) 0.9889(1) 0.4427(1) 1.000 4 e ? d Uani 0.0345(3)
N1 N 0.4025(2) 0.4413(1) 0.3378(1) 1.000 4 e ? d Uani 0.0295(3)
N2 N 0.4280(2) 0.5452(1) 0.3344(1) 1.000 4 e ? d Uani 0.0295(3)
N3 N 0.5598(2) 0.6932(1) 0.3930(1) 1.000 4 e ? d Uani 0.0252(3)
N4 N 0.6795(2) 0.7246(1) 0.4530(1) 1.000 4 e ? d Uani 0.0247(3)
N5 N 0.6570(2) 0.5523(1) 0.4500(1) 1.000 4 e ? d Uani 0.0242(3)
H5 H 0.676(3) 0.488(2) 0.4640(12) 1.000 4 e ? d Uiso 0.050(6)
N6 N 0.9368(2) 0.5417(1) 0.5760(1) 1.000 4 e ? d Uani 0.0288(3)
N7 N 1.0794(2) 0.6687(1) 0.6497(1) 1.000 4 e ? d Uani 0.0276(3)
N8 N 1.0414(2) 0.8870(1) 0.6465(1) 1.000 4 e ? d Uani 0.0308(3)
N9 N 0.9877(2) 0.9856(1) 0.6249(1) 1.000 4 e ? d Uani 0.0300(3)
N10 N 0.8314(2) 0.8850(1) 0.5460(1) 1.000 4 e ? d Uani 0.0242(3)
H10 H 0.760(3) 0.8629(15) 0.5110(11) 1.000 4 e ? d Uiso 0.031(5)
N11 N 0.7944(2) 1.0784(1) 0.5358(1) 1.000 4 e ? d Uani 0.0291(3)
N12 N 0.6696(2) 1.0730(1) 0.4745(1) 1.000 4 e ? d Uani 0.0282(3)
C1 C 0.5431(2) 0.5882(1) 0.3902(1) 1.000 4 e ? d Uani 0.0243(3)
C2 C 0.7367(2) 0.6383(1) 0.4862(1) 1.000 4 e ? d Uani 0.0233(3)
C3 C 0.8736(2) 0.6331(1) 0.5524(1) 1.000 4 e ? d Uani 0.0238(3)
C4 C 0.9594(2) 0.7148(1) 0.5976(1) 1.000 4 e ? d Uani 0.0244(3)
C5 C 0.9438(2) 0.8275(1) 0.5972(1) 1.000 4 e ? d Uani 0.0240(3)
C6 C 1.0698(3) 1.0756(1) 0.6665(1) 1.000 4 e ? d Uani 0.0392(4)
H6A H 0.9804 1.1023 0.6957 1.000 4 e ? calc Uiso 0.05900
H6B H 1.0976 1.1304 0.6336 1.000 4 e ? calc Uiso 0.05900
H6C H 1.1866 1.0545 0.6979 1.000 4 e ? calc Uiso 0.05900
C7 C 0.8611(2) 0.9865(1) 0.5643(1) 1.000 4 e ? d Uani 0.0250(3)
C8 C 0.4630(2) 0.7687(1) 0.3422(1) 1.000 4 e ? d Uani 0.0347(4)
H8A H 0.3751 0.8096 0.3653 1.000 4 e ? d Uiso 0.05200
H8B H 0.3929 0.7320 0.3004 1.000 4 e ? d Uiso 0.05200
H8C H 0.5554 0.8156 0.3265 1.000 4 e ? d Uiso 0.05200
O7 O 0.7481(2) 0.3544(1) 0.5098(1) 1.000 4 e ? d Uani 0.0358(3)
H7A H 0.7124 0.2914 0.4966 1.000 4 e ? d Uiso 0.05400
H7B H 0.8338 0.3457 0.5479 1.000 4 e ? d Uiso 0.05400
N13 N 1.0220(3) 0.3276(1) 0.6519(1) 1.000 4 e ? d Uani 0.0464(4)
C9 C 0.9672(3) 0.3682(2) 0.7810(1) 1.000 4 e ? d Uani 0.0468(5)
H9A H 0.8647 0.4191 0.7786 1.000 4 e ? calc Uiso 0.07000
H9B H 1.0822 0.3971 0.8097 1.000 4 e ? calc Uiso 0.07000
H9C H 0.9325 0.3038 0.8034 1.000 4 e ? calc Uiso 0.07000
C10 C 1.0001(2) 0.3457(1) 0.7090(1) 1.000 4 e ? d Uani 0.0348(4)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 . . 1.2384(18) no
O2 N1 . . 1.2403(18) no
O3 N6 . . 1.3648(17) no
O3 N7 . . 1.4418(17) no
O4 N7 . . 1.2161(17) no
O5 N12 . . 1.2409(18) no
O6 N12 . . 1.2489(17) no
N1 N2 . . 1.347(2) no
N2 C1 . . 1.342(2) no
N3 N4 . . 1.3602(17) no
N3 C1 . . 1.351(2) no
N3 C8 . . 1.453(2) no
N4 C2 . . 1.302(2) no
N5 H5 . . 0.86(2) no
N5 C1 . . 1.355(2) no
N5 C2 . . 1.3682(19) no
N6 C3 . . 1.305(2) no
N7 C4 . . 1.330(2) no
N8 N9 . . 1.361(2) no
N8 C5 . . 1.309(2) no
N9 C6 . . 1.460(2) no
N9 C7 . . 1.335(2) no
N10 H10 . . 0.82(2) no
N10 C5 . . 1.365(2) no
N10 C7 . . 1.352(2) no
N11 N12 . . 1.339(2) no
N11 C7 . . 1.347(2) no
C2 C3 . . 1.454(2) no
C3 C4 . . 1.422(2) no
C4 C5 . . 1.448(2) no
C6 H6A . . 0.9800 no
C6 H6B . . 0.9800 no
C6 H6C . . 0.9800 no
C8 H8A . . 0.9807 no
C8 H8B . . 0.9803 no
C8 H8C . . 0.9795 no
O7 H7A . . 0.8698 no
O7 H7B . . 0.8702 no
N13 C10 . . 1.140(2) no
C9 H9A . . 0.9800 no
C9 H9B . . 0.9800 no
C9 H9C . . 0.9800 no
C9 C10 . . 1.450(3) no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N6 O3 N7 . . . 107.78(10) no
O1 N1 O2 . . . 121.68(14) no
O1 N1 N2 . . . 115.69(14) no
O2 N1 N2 . . . 122.63(13) no
C1 N2 N1 . . . 115.94(13) no
N4 N3 C8 . . . 121.07(13) no
C1 N3 N4 . . . 111.43(12) no
C1 N3 C8 . . . 127.47(13) no
C2 N4 N3 . . . 104.59(12) no
C1 N5 H5 . . . 128.1(16) no
C1 N5 C2 . . . 106.51(13) no
C2 N5 H5 . . . 125.4(16) no
C3 N6 O3 . . . 107.43(12) no
O4 N7 O3 . . . 117.03(12) no
O4 N7 C4 . . . 135.67(14) no
C4 N7 O3 . . . 107.29(12) no
C5 N8 N9 . . . 103.78(13) no
N8 N9 C6 . . . 120.24(14) no
C7 N9 N8 . . . 112.40(13) no
C7 N9 C6 . . . 127.35(14) no
C5 N10 H10 . . . 126.9(14) no
C7 N10 H10 . . . 126.2(14) no
C7 N10 C5 . . . 106.85(13) no
N12 N11 C7 . . . 116.05(13) no
O5 N12 O6 . . . 121.47(14) no
O5 N12 N11 . . . 115.82(13) no
O6 N12 N11 . . . 122.71(13) no
N2 C1 N3 . . . 118.48(14) no
N2 C1 N5 . . . 135.93(15) no
N3 C1 N5 . . . 105.59(13) no
N4 C2 N5 . . . 111.87(13) no
N4 C2 C3 . . . 124.30(14) no
N5 C2 C3 . . . 123.80(14) no
N6 C3 C2 . . . 118.62(13) no
N6 C3 C4 . . . 111.40(13) no
C4 C3 C2 . . . 129.95(14) no
N7 C4 C3 . . . 106.09(13) no
N7 C4 C5 . . . 119.02(14) no
C3 C4 C5 . . . 134.89(14) no
N8 C5 N10 . . . 111.63(14) no
N8 C5 C4 . . . 123.10(14) no
N10 C5 C4 . . . 125.25(14) no
N9 C6 H6A . . . 109.50 no
N9 C6 H6B . . . 109.50 no
N9 C6 H6C . . . 109.50 no
H6A C6 H6B . . . 109.50 no
H6A C6 H6C . . . 109.50 no
H6B C6 H6C . . . 109.50 no
N9 C7 N10 . . . 105.34(14) no
N9 C7 N11 . . . 119.56(14) no
N11 C7 N10 . . . 135.10(15) no
N3 C8 H8A . . . 109.50 no
N3 C8 H8B . . . 109.50 no
N3 C8 H8C . . . 109.50 no
H8A C8 H8B . . . 109.40 no
H8A C8 H8C . . . 109.50 no
H8B C8 H8C . . . 109.50 no
H7A O7 H7B . . . 104.50 no
H9A C9 H9B . . . 109.50 no
H9A C9 H9C . . . 109.50 no
H9B C9 H9C . . . 109.50 no
C10 C9 H9A . . . 109.50 no
C10 C9 H9B . . . 109.50 no
C10 C9 H9C . . . 109.50 no
N13 C10 C9 . . . 178.5(2) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 N2 C1 . . . . 175.79(13) no
O2 N1 N2 C1 . . . . -3.3(2) no
O3 N6 C3 C2 . . . . 178.19(12) no
O3 N6 C3 C4 . . . . -0.18(16) no
O3 N7 C4 C3 . . . . -0.55(15) no
O3 N7 C4 C5 . . . . -179.99(12) no
O4 N7 C4 C3 . . . . -179.70(17) no
O4 N7 C4 C5 . . . . 0.9(3) no
N1 N2 C1 N3 . . . . -173.77(13) no
N1 N2 C1 N5 . . . . 6.1(2) no
N3 N4 C2 N5 . . . . -0.42(16) no
N3 N4 C2 C3 . . . . 177.57(13) no
N4 N3 C1 N2 . . . . 179.40(12) no
N4 N3 C1 N5 . . . . -0.53(16) no
N4 C2 C3 N6 . . . . -171.83(14) no
N4 C2 C3 C4 . . . . 6.2(2) no
N5 C2 C3 N6 . . . . 5.9(2) no
N5 C2 C3 C4 . . . . -176.07(14) no
N6 O3 N7 O4 . . . . 179.80(12) no
N6 O3 N7 C4 . . . . 0.47(15) no
N6 C3 C4 N7 . . . . 0.48(17) no
N6 C3 C4 C5 . . . . 179.78(16) no
N7 O3 N6 C3 . . . . -0.17(15) no
N7 C4 C5 N8 . . . . -0.7(2) no
N7 C4 C5 N10 . . . . 177.81(13) no
N8 N9 C7 N10 . . . . 0.21(17) no
N8 N9 C7 N11 . . . . -179.75(13) no
N9 N8 C5 N10 . . . . -0.10(16) no
N9 N8 C5 C4 . . . . 178.60(14) no
N12 N11 C7 N9 . . . . 179.26(13) no
N12 N11 C7 N10 . . . . -0.7(3) no
C1 N3 N4 C2 . . . . 0.59(16) no
C1 N5 C2 N4 . . . . 0.11(16) no
C1 N5 C2 C3 . . . . -177.89(13) no
C2 N5 C1 N2 . . . . -179.66(16) no
C2 N5 C1 N3 . . . . 0.25(15) no
C2 C3 C4 N7 . . . . -177.65(14) no
C2 C3 C4 C5 . . . . 1.7(3) no
C3 C4 C5 N8 . . . . -179.95(15) no
C3 C4 C5 N10 . . . . -1.4(3) no
C5 N8 N9 C6 . . . . -179.05(15) no
C5 N8 N9 C7 . . . . -0.08(17) no
C5 N10 C7 N9 . . . . -0.26(16) no
C5 N10 C7 N11 . . . . 179.70(17) no
C6 N9 C7 N10 . . . . 179.10(15) no
C6 N9 C7 N11 . . . . -0.9(3) no
C7 N10 C5 N8 . . . . 0.23(17) no
C7 N10 C5 C4 . . . . -178.44(14) no
C7 N11 N12 O5 . . . . 175.88(13) no
C7 N11 N12 O6 . . . . -4.0(2) no
C8 N3 N4 C2 . . . . 178.79(13) no
C8 N3 C1 N2 . . . . 1.3(2) no
C8 N3 C1 N5 . . . . -178.58(14) no
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2k4wk5
_database_code_depnum_ccdc_archive 'CCDC 2358187'
loop_
_audit_author_name
_audit_author_address
'jiapeng wang'
;North University of China
China
;
_audit_update_record             
;
2024-05-25 deposited with the CCDC.	2024-12-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H28 N12 O3'
_chemical_formula_weight         460.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   10.205(2)
_cell_length_b                   10.512(2)
_cell_length_c                   11.184(3)
_cell_angle_alpha                90.850(4)
_cell_angle_beta                 94.688(4)
_cell_angle_gamma                96.027(4)
_cell_volume                     1188.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2171
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      24.50

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6023
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4139
_reflns_number_gt                2760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1076P)²+0.0551P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     332
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1679
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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 0.19860(16) 0.43018(17) 0.15235(19) 0.0657(6) Uani 1 1 d . . . . .
N10 N 0.47741(19) 0.13468(17) 0.2742(2) 0.0475(5) Uani 1 1 d . . . . .
N0AA N 0.59689(18) 0.57955(16) 0.15787(19) 0.0442(5) Uani 1 1 d . . . . .
N5 N 0.74729(18) 0.45095(18) 0.1303(2) 0.0489(6) Uani 1 1 d . . . . .
N4 N 0.63343(18) 0.37237(17) 0.1323(2) 0.0466(5) Uani 1 1 d . . . . .
N9 N 0.41141(19) -0.03255(18) 0.1552(2) 0.0504(6) Uani 1 1 d . . . . .
N8 N 0.34934(19) 0.06578(18) 0.1057(2) 0.0504(6) Uani 1 1 d . . . . .
N1 N 0.8856(2) 0.88668(19) 0.1576(2) 0.0562(6) Uani 1 1 d . . . . .
N2 N 0.82713(19) 0.66989(18) 0.1465(2) 0.0506(6) Uani 1 1 d . . . . .
N7 N 0.21676(19) 0.29754(19) 0.1634(2) 0.0546(6) Uani 1 1 d . . . . .
N6 N 0.32083(19) 0.4976(2) 0.1469(2) 0.0549(6) Uani 1 1 d . . . . .
N11 N 0.5558(2) -0.0739(2) 0.3209(2) 0.0595(6) Uani 1 1 d . . . . .
O2 O 0.11753(19) 0.22593(19) 0.1702(2) 0.0888(8) Uani 1 1 d . . . . .
C6 C 0.5479(2) 0.4548(2) 0.1488(2) 0.0396(6) Uani 1 1 d . . . . .
C4 C 0.7252(2) 0.5750(2) 0.1453(2) 0.0419(6) Uani 1 1 d . . . . .
C9 C 0.3934(2) 0.1616(2) 0.1802(2) 0.0406(6) Uani 1 1 d . . . . .
C7 C 0.4074(2) 0.4125(2) 0.1544(2) 0.0416(6) Uani 1 1 d . . . . .
C10 C 0.4863(2) 0.0097(2) 0.2555(2) 0.0466(6) Uani 1 1 d . . . . .
C8 C 0.3449(2) 0.2872(2) 0.1644(2) 0.0409(6) Uani 1 1 d . . . . .
N12 N 0.7131(3) -0.0967(3) 0.4751(3) 0.0772(8) Uani 1 1 d . . . . .
C0AA C 0.7963(2) 0.7860(2) 0.1528(2) 0.0500(6) Uani 1 1 d . . . . .
H0AA H 0.7076 0.7990 0.1540 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6392(3) -0.0261(3) 0.4062(3) 0.0605(8) Uani 1 1 d . . . . .
H12 H 0.6481 0.0620 0.4201 0.073 Uiso 1 1 calc R U . . .
C5 C 0.8718(3) 0.4007(3) 0.1111(4) 0.0727(9) Uani 1 1 d . . . . .
H5A H 0.8805 0.3266 0.1591 0.109 Uiso 1 1 calc R U . . .
H5B H 0.9439 0.4649 0.1338 0.109 Uiso 1 1 calc R U . . .
H5C H 0.8730 0.3776 0.0279 0.109 Uiso 1 1 calc R U . . .
C11 C 0.3921(3) -0.1604(2) 0.1006(3) 0.0700(9) Uani 1 1 d . . . . .
H11A H 0.3019 -0.1956 0.1048 0.105 Uiso 1 1 calc R U . . .
H11B H 0.4499 -0.2140 0.1429 0.105 Uiso 1 1 calc R U . . .
H11C H 0.4116 -0.1559 0.0182 0.105 Uiso 1 1 calc R U . . .
C1 C 0.8485(3) 1.0166(3) 0.1640(3) 0.0775(10) Uani 1 1 d . . . . .
H1A H 0.7539 1.0141 0.1566 0.116 Uiso 1 1 calc R U . . .
H1B H 0.8843 1.0653 0.1001 0.116 Uiso 1 1 calc R U . . .
H1C H 0.8829 1.0560 0.2397 0.116 Uiso 1 1 calc R U . . .
C2 C 1.0236(3) 0.8704(3) 0.1528(4) 0.0947(12) Uani 1 1 d . . . . .
H2A H 1.0582 0.8412 0.2287 0.142 Uiso 1 1 calc R U . . .
H2B H 1.0714 0.9507 0.1355 0.142 Uiso 1 1 calc R U . . .
H2C H 1.0332 0.8085 0.0910 0.142 Uiso 1 1 calc R U . . .
C14 C 0.8085(4) -0.0397(5) 0.5697(4) 0.1115(15) Uani 1 1 d . . . . .
H14A H 0.8060 0.0514 0.5721 0.167 Uiso 1 1 calc R U . . .
H14B H 0.8956 -0.0586 0.5539 0.167 Uiso 1 1 calc R U . . .
H14C H 0.7869 -0.0742 0.6455 0.167 Uiso 1 1 calc R U . . .
C13 C 0.6977(5) -0.2360(4) 0.4617(4) 0.1175(15) Uani 1 1 d . . . . .
H13A H 0.6672 -0.2730 0.5337 0.176 Uiso 1 1 calc R U . . .
H13B H 0.7812 -0.2651 0.4474 0.176 Uiso 1 1 calc R U . . .
H13C H 0.6344 -0.2615 0.3952 0.176 Uiso 1 1 calc R U . . .
O3 O 0.8622(15) 0.2918(13) 0.5252(10) 0.276(9) Uani 0.656(13) 1 d DG . P A 1
C15 C 0.8022(14) 0.3350(11) 0.4164(6) 0.187(7) Uani 0.656(13) 1 d DG . P A 1
H15A H 0.8671 0.3873 0.3745 0.225 Uiso 0.656(13) 1 calc R U P A 1
H15B H 0.7666 0.2626 0.3647 0.225 Uiso 0.656(13) 1 calc R U P A 1
C16 C 0.6992(14) 0.4080(12) 0.4452(10) 0.206(8) Uani 0.656(13) 1 d DG . P A 1
H16A H 0.6152 0.3698 0.4070 0.248 Uiso 0.656(13) 1 calc R U P A 1
H16B H 0.7156 0.4945 0.4168 0.248 Uiso 0.656(13) 1 calc R U P A 1
C17 C 0.6955(14) 0.4099(14) 0.5718(11) 0.327(19) Uani 0.656(13) 1 d DG . P A 1
H17A H 0.6097 0.3726 0.5931 0.392 Uiso 0.656(13) 1 calc R U P A 1
H17B H 0.7102 0.4973 0.6029 0.392 Uiso 0.656(13) 1 calc R U P A 1
C18 C 0.7963(18) 0.3381(13) 0.6213(6) 0.249(11) Uani 0.656(13) 1 d DG . P A 1
H18A H 0.8583 0.3918 0.6756 0.299 Uiso 0.656(13) 1 calc R U P A 1
H18B H 0.7578 0.2671 0.6658 0.299 Uiso 0.656(13) 1 calc R U P A 1
O3A O 0.8044(18) 0.2489(9) 0.5321(18) 0.182(10) Uani 0.344(13) 1 d DG . P A 2
C18A C 0.8908(18) 0.3474(16) 0.486(3) 0.48(6) Uani 0.344(13) 1 d DG . P A 2
H18C H 0.9067 0.3261 0.4039 0.570 Uiso 0.344(13) 1 calc R U P A 2
H18D H 0.9749 0.3574 0.5339 0.570 Uiso 0.344(13) 1 calc R U P A 2
C17A C 0.830(2) 0.4627(13) 0.489(3) 0.29(2) Uani 0.344(13) 1 d DG . P A 2
H17C H 0.8172 0.4955 0.4090 0.352 Uiso 0.344(13) 1 calc R U P A 2
H17D H 0.8854 0.5268 0.5390 0.352 Uiso 0.344(13) 1 calc R U P A 2
C16A C 0.706(2) 0.4354(15) 0.538(2) 0.163(13) Uani 0.344(13) 1 d DG . P A 2
H16C H 0.7033 0.4867 0.6102 0.196 Uiso 0.344(13) 1 calc R U P A 2
H16D H 0.6351 0.4554 0.4802 0.196 Uiso 0.344(13) 1 calc R U P A 2
C15A C 0.690(2) 0.3033(17) 0.564(2) 0.215(17) Uani 0.344(13) 1 d DG . P A 2
H15C H 0.6801 0.2925 0.6491 0.258 Uiso 0.344(13) 1 calc R U P A 2
H15D H 0.6119 0.2612 0.5191 0.258 Uiso 0.344(13) 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
O1 N6 1.375(3) . ?
O1 N7 1.432(3) . ?
N10 C10 1.341(3) . ?
N10 C9 1.354(3) . ?
N0AA C4 1.334(3) . ?
N0AA C6 1.352(3) . ?
N5 N4 1.355(3) . ?
N5 C4 1.356(3) . ?
N5 C5 1.456(3) . ?
N4 C6 1.314(3) . ?
N9 C10 1.347(3) . ?
N9 N8 1.368(3) . ?
N9 C11 1.455(3) . ?
N8 C9 1.316(3) . ?
N1 C0AA 1.320(3) . ?
N1 C2 1.442(4) . ?
N1 C1 1.457(3) . ?
N2 C0AA 1.295(3) . ?
N2 C4 1.363(3) . ?
N7 O2 1.205(2) . ?
N7 C8 1.323(3) . ?
N6 C7 1.321(3) . ?
N11 C12 1.285(4) . ?
N11 C10 1.370(3) . ?
C6 C7 1.463(3) . ?
C9 C8 1.466(3) . ?
C7 C8 1.412(3) . ?
N12 C12 1.324(4) . ?
N12 C14 1.456(5) . ?
N12 C13 1.461(5) . ?
C0AA H0AA 0.9300 . ?
C12 H12 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O3 C18 1.4200 . ?
O3 C15 1.4200 . ?
C15 C16 1.4200 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.4200 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.4200 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O3A C18A 1.4200 . ?
O3A C15A 1.4200 . ?
C18A C17A 1.4200 . ?
C18A H18C 0.9700 . ?
C18A H18D 0.9700 . ?
C17A C16A 1.4200 . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C16A C15A 1.4200 . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?

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
N6 O1 N7 108.06(15) . . ?
C10 N10 C9 102.0(2) . . ?
C4 N0AA C6 102.72(18) . . ?
N4 N5 C4 110.84(17) . . ?
N4 N5 C5 121.27(19) . . ?
C4 N5 C5 127.9(2) . . ?
C6 N4 N5 101.45(18) . . ?
C10 N9 N8 109.65(19) . . ?
C10 N9 C11 129.0(2) . . ?
N8 N9 C11 121.4(2) . . ?
C9 N8 N9 101.95(19) . . ?
C0AA N1 C2 120.3(2) . . ?
C0AA N1 C1 121.7(2) . . ?
C2 N1 C1 118.0(2) . . ?
C0AA N2 C4 116.4(2) . . ?
O2 N7 C8 136.5(2) . . ?
O2 N7 O1 115.76(19) . . ?
C8 N7 O1 107.71(18) . . ?
C7 N6 O1 106.24(19) . . ?
C12 N11 C10 117.1(2) . . ?
N4 C6 N0AA 116.3(2) . . ?
N4 C6 C7 121.1(2) . . ?
N0AA C6 C7 122.57(19) . . ?
N0AA C4 N5 108.67(19) . . ?
N0AA C4 N2 131.0(2) . . ?
N5 C4 N2 120.3(2) . . ?
N8 C9 N10 116.32(19) . . ?
N8 C9 C8 120.4(2) . . ?
N10 C9 C8 123.1(2) . . ?
N6 C7 C8 111.6(2) . . ?
N6 C7 C6 119.4(2) . . ?
C8 C7 C6 129.0(2) . . ?
N10 C10 N9 110.1(2) . . ?
N10 C10 N11 130.4(2) . . ?
N9 C10 N11 119.5(2) . . ?
N7 C8 C7 106.39(19) . . ?
N7 C8 C9 119.7(2) . . ?
C7 C8 C9 133.83(19) . . ?
C12 N12 C14 121.7(3) . . ?
C12 N12 C13 120.9(3) . . ?
C14 N12 C13 117.4(3) . . ?
N2 C0AA N1 122.6(2) . . ?
N2 C0AA H0AA 118.7 . . ?
N1 C0AA H0AA 118.7 . . ?
N11 C12 N12 122.8(3) . . ?
N11 C12 H12 118.6 . . ?
N12 C12 H12 118.6 . . ?
N5 C5 H5A 109.5 . . ?
N5 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N5 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N9 C11 H11A 109.5 . . ?
N9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N12 C14 H14A 109.5 . . ?
N12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C18 O3 C15 108.0 . . ?
C16 C15 O3 108.0 . . ?
C16 C15 H15A 110.1 . . ?
O3 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
O3 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
C15 C16 C17 108.0 . . ?
C15 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
C16 C17 C18 108.0 . . ?
C16 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
C16 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
O3 C18 C17 108.0 . . ?
O3 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
O3 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
C18A O3A C15A 108.0 . . ?
O3A C18A C17A 108.0 . . ?
O3A C18A H18C 110.1 . . ?
C17A C18A H18C 110.1 . . ?
O3A C18A H18D 110.1 . . ?
C17A C18A H18D 110.1 . . ?
H18C C18A H18D 108.4 . . ?
C18A C17A C16A 108.0 . . ?
C18A C17A H17C 110.1 . . ?
C16A C17A H17C 110.1 . . ?
C18A C17A H17D 110.1 . . ?
C16A C17A H17D 110.1 . . ?
H17C C17A H17D 108.4 . . ?
C15A C16A C17A 108.0 . . ?
C15A C16A H16C 110.1 . . ?
C17A C16A H16C 110.1 . . ?
C15A C16A H16D 110.1 . . ?
C17A C16A H16D 110.1 . . ?
H16C C16A H16D 108.4 . . ?
O3A C15A C16A 108.0 . . ?
O3A C15A H15C 110.1 . . ?
C16A C15A H15C 110.1 . . ?
O3A C15A H15D 110.1 . . ?
C16A C15A H15D 110.1 . . ?
H15C C15A H15D 108.4 . . ?

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
C4 N5 N4 C6 -0.1(3) . . . . ?
C5 N5 N4 C6 -178.7(3) . . . . ?
C10 N9 N8 C9 0.8(3) . . . . ?
C11 N9 N8 C9 -179.6(2) . . . . ?
N6 O1 N7 O2 179.4(2) . . . . ?
N6 O1 N7 C8 0.0(3) . . . . ?
N7 O1 N6 C7 -0.2(3) . . . . ?
N5 N4 C6 N0AA -0.1(3) . . . . ?
N5 N4 C6 C7 178.6(2) . . . . ?
C4 N0AA C6 N4 0.3(3) . . . . ?
C4 N0AA C6 C7 -178.5(2) . . . . ?
C6 N0AA C4 N5 -0.3(3) . . . . ?
C6 N0AA C4 N2 -179.7(3) . . . . ?
N4 N5 C4 N0AA 0.3(3) . . . . ?
C5 N5 C4 N0AA 178.8(3) . . . . ?
N4 N5 C4 N2 179.7(2) . . . . ?
C5 N5 C4 N2 -1.7(4) . . . . ?
C0AA N2 C4 N0AA -5.3(4) . . . . ?
C0AA N2 C4 N5 175.3(2) . . . . ?
N9 N8 C9 N10 -0.6(3) . . . . ?
N9 N8 C9 C8 -176.5(2) . . . . ?
C10 N10 C9 N8 0.2(3) . . . . ?
C10 N10 C9 C8 175.9(2) . . . . ?
O1 N6 C7 C8 0.3(3) . . . . ?
O1 N6 C7 C6 178.8(2) . . . . ?
N4 C6 C7 N6 -166.5(2) . . . . ?
N0AA C6 C7 N6 12.2(4) . . . . ?
N4 C6 C7 C8 11.8(4) . . . . ?
N0AA C6 C7 C8 -169.5(2) . . . . ?
C9 N10 C10 N9 0.3(3) . . . . ?
C9 N10 C10 N11 -179.2(3) . . . . ?
N8 N9 C10 N10 -0.7(3) . . . . ?
C11 N9 C10 N10 179.6(2) . . . . ?
N8 N9 C10 N11 178.9(2) . . . . ?
C11 N9 C10 N11 -0.7(4) . . . . ?
C12 N11 C10 N10 -9.6(4) . . . . ?
C12 N11 C10 N9 170.8(3) . . . . ?
O2 N7 C8 C7 -179.1(3) . . . . ?
O1 N7 C8 C7 0.1(3) . . . . ?
O2 N7 C8 C9 -1.8(5) . . . . ?
O1 N7 C8 C9 177.3(2) . . . . ?
N6 C7 C8 N7 -0.2(3) . . . . ?
C6 C7 C8 N7 -178.6(2) . . . . ?
N6 C7 C8 C9 -176.9(3) . . . . ?
C6 C7 C8 C9 4.7(5) . . . . ?
N8 C9 C8 N7 57.3(3) . . . . ?
N10 C9 C8 N7 -118.3(3) . . . . ?
N8 C9 C8 C7 -126.4(3) . . . . ?
N10 C9 C8 C7 58.0(4) . . . . ?
C4 N2 C0AA N1 178.3(2) . . . . ?
C2 N1 C0AA N2 1.6(4) . . . . ?
C1 N1 C0AA N2 179.7(3) . . . . ?
C10 N11 C12 N12 -179.4(3) . . . . ?
C14 N12 C12 N11 178.9(3) . . . . ?
C13 N12 C12 N11 -3.6(5) . . . . ?
C18 O3 C15 C16 0.0 . . . . ?
O3 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C15 O3 C18 C17 0.0 . . . . ?
C16 C17 C18 O3 0.0 . . . . ?
C15A O3A C18A C17A 0.0 . . . . ?
O3A C18A C17A C16A 0.0 . . . . ?
C18A C17A C16A C15A 0.0 . . . . ?
C18A O3A C15A C16A 0.0 . . . . ?
C17A C16A C15A O3A 0.0 . . . . ?

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
C14 H14A O3 0.96 2.60 3.519(15) 159.7 .
C12 H12 O3A 0.93 2.63 3.413(12) 142.2 .
C5 H5B O1 0.96 2.65 3.310(3) 126.0 1_655
C14 H14A O3 0.96 2.60 3.519(15) 159.7 .
C14 H14A O3A 0.96 2.13 3.073(10) 166.2 .

_refine_diff_density_max         0.753
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042

