# Supplementary Information (SI) for Materials Horizons.
# 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_cu_20230525_zh_nlg_lcc_a_3_y_0
_database_code_depnum_ccdc_archive 'CCDC 2338095'
loop_
_audit_author_name
_audit_author_address
'Frank '
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-08-12 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2024-08-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 N16 O10, C H4 O, H2 O'
_chemical_formula_sum            'C13 H10 N16 O12'
_chemical_formula_weight         582.37
_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      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                   7.0832(19)
_cell_length_b                   11.664(3)
_cell_length_c                   13.430(4)
_cell_angle_alpha                98.143(12)
_cell_angle_beta                 95.040(12)
_cell_angle_gamma                94.764(12)
_cell_volume                     1089.1(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    241
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      49.535
_cell_measurement_theta_min      6.833
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0994 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.8554.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12122
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.678
_diffrn_reflns_theta_min         3.341
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                2311
_reflns_number_total             3915
_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       'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0034(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      0.953
_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)+(0.1008P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5A-N9
 1.2 with sigma of 0.02
 O11-H11B
 0.88 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O5A)=1-FVAR(1)
 Sof(O5)=FVAR(1)
5.a Free rotating group:
 O11(H11A)
5.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N15(H15A,H15B)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
5.d Idealised tetrahedral OH refined as rotating group:
 O12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.6518(6) 1.0164(3) 0.6992(3) 0.0423(9) Uani 1 1 d . . . . .
C2 C 0.5621(5) 0.9070(3) 0.7145(3) 0.0393(9) Uani 1 1 d . . . . .
C3 C 0.8578(5) 0.9069(3) 0.8186(3) 0.0390(9) Uani 1 1 d . . . . .
C4 C 0.9278(6) 0.8271(3) 0.8765(3) 0.0421(9) Uani 1 1 d . . . . .
C5 C 0.7834(5) 0.7348(3) 0.8688(3) 0.0376(8) Uani 1 1 d . . . . .
C6 C 0.7708(6) 0.6304(3) 0.9162(3) 0.0402(9) Uani 1 1 d . . . . .
C7 C 0.6760(5) 0.5184(3) 0.8803(3) 0.0393(9) Uani 1 1 d . . . . .
C8 C 0.5762(5) 0.4691(3) 0.7809(3) 0.0386(9) Uani 1 1 d . . . . .
C9 C 0.6431(5) 0.4665(3) 0.6845(3) 0.0372(8) Uani 1 1 d . . . . .
C10 C 0.5010(5) 0.4019(3) 0.6164(3) 0.0358(8) Uani 1 1 d . . . . .
C11 C 0.1992(5) 0.3028(3) 0.6379(3) 0.0353(8) Uani 1 1 d . . . . .
C12 C 0.1969(5) 0.2708(3) 0.5315(3) 0.0402(9) Uani 1 1 d . . . . .
N1 N 0.5485(5) 1.0888(3) 0.6376(3) 0.0477(9) Uani 1 1 d . . . . .
N2 N 0.8242(5) 1.0625(3) 0.7372(3) 0.0444(8) Uani 1 1 d . . . . .
N3 N 0.9341(5) 1.0096(3) 0.7972(3) 0.0437(8) Uani 1 1 d . . . . .
N4 N 0.3977(5) 0.8541(3) 0.6786(3) 0.0498(9) Uani 1 1 d . . . . .
H4A H 0.360962 0.786375 0.695905 0.060 Uiso 1 1 calc R U . . .
H4B H 0.322263 0.885866 0.636975 0.060 Uiso 1 1 calc R U . . .
N5 N 0.6792(4) 0.8572(3) 0.7794(2) 0.0374(7) Uani 1 1 d . . . . .
N6 N 0.6296(4) 0.7532(3) 0.8100(2) 0.0393(8) Uani 1 1 d . . . . .
N7 N 1.1179(5) 0.8314(4) 0.9220(3) 0.0596(11) Uani 1 1 d . . . . .
N8 N 0.8395(5) 0.6290(3) 1.0117(2) 0.0423(8) Uani 1 1 d . . . . .
N9 N 0.6880(5) 0.4498(3) 0.9503(3) 0.0492(9) Uani 1 1 d D . . . .
N10 N 0.4053(4) 0.4125(3) 0.7762(2) 0.0381(7) Uani 1 1 d . . . . .
N11 N 0.3617(4) 0.3721(3) 0.6755(2) 0.0350(7) Uani 1 1 d . . . . .
N12 N 0.8257(5) 0.5063(3) 0.6626(3) 0.0427(8) Uani 1 1 d . . . . .
N13 N 0.4877(5) 0.3686(3) 0.5153(2) 0.0411(8) Uani 1 1 d . . . . .
N14 N 0.3325(5) 0.3023(3) 0.4754(2) 0.0414(8) Uani 1 1 d . . . . .
N15 N 0.0762(5) 0.2762(3) 0.6994(3) 0.0439(8) Uani 1 1 d . . . . .
H15A H 0.098357 0.302902 0.764389 0.053 Uiso 1 1 calc R U . . .
H15B H -0.029075 0.231553 0.676016 0.053 Uiso 1 1 calc R U . . .
N16 N 0.0396(5) 0.1961(3) 0.4744(3) 0.0519(9) Uani 1 1 d . . . . .
O1 O 0.3983(5) 1.0463(3) 0.5876(3) 0.0616(9) Uani 1 1 d . . . . .
O2 O 0.6160(5) 1.1886(3) 0.6397(3) 0.0615(9) Uani 1 1 d . . . A 4
O3 O 1.2082(6) 0.9284(4) 0.9415(4) 0.1108(19) Uani 1 1 d . . . . .
O4 O 1.1810(5) 0.7414(3) 0.9369(3) 0.0702(10) Uani 1 1 d . . . B 4
O6 O 0.7909(4) 0.5145(2) 1.0344(2) 0.0488(7) Uani 1 1 d . . . . .
O7 O 0.9378(4) 0.5583(3) 0.7331(2) 0.0579(8) Uani 1 1 d . . . . .
O8 O 0.8675(4) 0.4858(3) 0.5752(2) 0.0548(8) Uani 1 1 d . . . . .
O9 O 0.0370(5) 0.1729(4) 0.3833(2) 0.0760(11) Uani 1 1 d . . . . .
O10 O -0.0864(5) 0.1596(4) 0.5211(3) 0.0818(12) Uani 1 1 d . . . C 4
O5 O 0.9276(5) 0.6996(3) 1.0789(2) 0.0488(10) Uani 0.910(8) 1 d . . P D 1
O5A O 0.583(4) 0.376(2) 0.972(2) 0.052(11) Uani 0.090(8) 1 d D U P D 2
C13 C 0.5395(7) 0.8520(5) 1.1044(4) 0.0650(13) Uani 1 1 d . . . . .
H13A H 0.606306 0.810593 1.051563 0.097 Uiso 1 1 calc R U . . .
H13B H 0.498721 0.923644 1.082682 0.097 Uiso 1 1 calc R U . . .
H13C H 0.427737 0.802336 1.116274 0.097 Uiso 1 1 calc R U . . .
O12 O 0.6613(5) 0.8797(3) 1.1933(3) 0.0683(9) Uani 1 1 d . . . . .
H12 H 0.762872 0.915463 1.181486 0.102 Uiso 1 1 calc R U . . .
O11 O 0.2834(5) 0.6212(3) 0.6485(3) 0.0547(8) Uani 1 1 d DG . . . .
H11A H 0.292380 0.616026 0.583857 0.082 Uiso 1 1 d G U . . .
H11B H 0.162(4) 0.597(5) 0.652(5) 0.10(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
C1 C2 1.427(5) . ?
C1 N1 1.459(5) . ?
C1 N2 1.321(5) . ?
C2 N4 1.291(5) . ?
C2 N5 1.371(5) . ?
C3 C4 1.390(5) . ?
C3 N3 1.352(5) . ?
C3 N5 1.375(5) . ?
C4 C5 1.408(5) . ?
C4 N7 1.423(5) . ?
C5 C6 1.451(5) . ?
C5 N6 1.339(5) . ?
C6 C7 1.417(5) . ?
C6 N8 1.334(5) . ?
C7 C8 1.471(5) . ?
C7 N9 1.320(5) . ?
C8 C9 1.414(5) . ?
C8 N10 1.322(5) . ?
C9 C10 1.391(5) . ?
C9 N12 1.408(5) . ?
C10 N11 1.372(5) . ?
C10 N13 1.351(5) . ?
C11 C12 1.423(5) . ?
C11 N11 1.364(5) . ?
C11 N15 1.300(5) . ?
C12 N14 1.332(5) . ?
C12 N16 1.445(5) . ?
N1 O1 1.234(4) . ?
N1 O2 1.216(4) . ?
N2 N3 1.321(5) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 N6 1.365(4) . ?
N7 O3 1.235(5) . ?
N7 O4 1.209(5) . ?
N8 O6 1.433(4) . ?
N8 O5 1.219(4) . ?
N9 O6 1.378(4) . ?
N9 O5A 1.173(17) . ?
N10 N11 1.366(4) . ?
N12 O7 1.233(4) . ?
N12 O8 1.231(4) . ?
N13 N14 1.316(5) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
N16 O9 1.214(5) . ?
N16 O10 1.217(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 O12 1.392(5) . ?
O12 H12 0.8400 . ?
O11 H11A 0.8698 . ?
O11 H11B 0.89(2) . ?

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
C2 C1 N1 119.4(3) . . ?
N2 C1 C2 126.3(3) . . ?
N2 C1 N1 114.3(3) . . ?
N4 C2 C1 130.5(4) . . ?
N4 C2 N5 119.8(3) . . ?
N5 C2 C1 109.6(3) . . ?
N3 C3 C4 132.7(4) . . ?
N3 C3 N5 123.1(3) . . ?
N5 C3 C4 104.2(3) . . ?
C3 C4 C5 106.6(3) . . ?
C3 C4 N7 125.7(4) . . ?
C5 C4 N7 127.1(4) . . ?
C4 C5 C6 131.8(3) . . ?
N6 C5 C4 111.4(3) . . ?
N6 C5 C6 116.8(3) . . ?
C7 C6 C5 130.4(3) . . ?
N8 C6 C5 122.7(3) . . ?
N8 C6 C7 106.6(3) . . ?
C6 C7 C8 131.0(3) . . ?
N9 C7 C6 111.2(3) . . ?
N9 C7 C8 117.8(3) . . ?
C9 C8 C7 128.6(3) . . ?
N10 C8 C7 119.2(3) . . ?
N10 C8 C9 112.1(3) . . ?
C10 C9 C8 105.9(3) . . ?
C10 C9 N12 126.2(3) . . ?
N12 C9 C8 127.3(4) . . ?
N11 C10 C9 104.2(3) . . ?
N13 C10 C9 132.5(3) . . ?
N13 C10 N11 123.3(3) . . ?
N11 C11 C12 110.2(3) . . ?
N15 C11 C12 130.6(4) . . ?
N15 C11 N11 119.2(3) . . ?
C11 C12 N16 120.5(4) . . ?
N14 C12 C11 125.8(4) . . ?
N14 C12 N16 113.7(3) . . ?
O1 N1 C1 118.6(3) . . ?
O2 N1 C1 117.4(4) . . ?
O2 N1 O1 124.0(3) . . ?
C1 N2 N3 121.8(3) . . ?
N2 N3 C3 115.9(3) . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 C3 123.1(3) . . ?
N6 N5 C2 123.0(3) . . ?
N6 N5 C3 113.9(3) . . ?
C5 N6 N5 104.0(3) . . ?
O3 N7 C4 116.5(4) . . ?
O4 N7 C4 118.8(4) . . ?
O4 N7 O3 124.7(4) . . ?
C6 N8 O6 107.3(3) . . ?
O5 N8 C6 135.5(3) . . ?
O5 N8 O6 117.3(3) . . ?
C7 N9 O6 106.7(3) . . ?
O5A N9 C7 133.0(15) . . ?
O5A N9 O6 112.0(16) . . ?
C8 N10 N11 103.8(3) . . ?
C11 N11 C10 123.0(3) . . ?
C11 N11 N10 123.0(3) . . ?
N10 N11 C10 114.0(3) . . ?
O7 N12 C9 117.8(3) . . ?
O8 N12 C9 119.0(3) . . ?
O8 N12 O7 123.2(3) . . ?
N14 N13 C10 115.9(3) . . ?
N13 N14 C12 121.8(3) . . ?
C11 N15 H15A 120.0 . . ?
C11 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
O9 N16 C12 119.6(4) . . ?
O9 N16 O10 122.9(4) . . ?
O10 N16 C12 117.5(4) . . ?
N9 O6 N8 108.2(3) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
C13 O12 H12 109.5 . . ?
H11A O11 H11B 103.5 . . ?

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
C1 C2 N5 C3 -2.3(5) . . . . ?
C1 C2 N5 N6 178.4(3) . . . . ?
C1 N2 N3 C3 -1.3(6) . . . . ?
C2 C1 N1 O1 -11.1(6) . . . . ?
C2 C1 N1 O2 168.3(4) . . . . ?
C2 C1 N2 N3 -1.1(7) . . . . ?
C2 N5 N6 C5 177.9(4) . . . . ?
C3 C4 C5 C6 -176.6(4) . . . . ?
C3 C4 C5 N6 -0.1(5) . . . . ?
C3 C4 N7 O3 25.8(7) . . . . ?
C3 C4 N7 O4 -152.7(5) . . . . ?
C3 N5 N6 C5 -1.4(4) . . . . ?
C4 C3 N3 N2 179.3(4) . . . . ?
C4 C3 N5 C2 -177.9(4) . . . . ?
C4 C3 N5 N6 1.4(4) . . . . ?
C4 C5 C6 C7 -148.7(5) . . . . ?
C4 C5 C6 N8 37.8(7) . . . . ?
C4 C5 N6 N5 0.9(4) . . . . ?
C5 C4 N7 O3 -163.9(5) . . . . ?
C5 C4 N7 O4 17.6(7) . . . . ?
C5 C6 C7 C8 6.7(7) . . . . ?
C5 C6 C7 N9 -175.3(4) . . . . ?
C5 C6 N8 O6 176.2(3) . . . . ?
C5 C6 N8 O5 -3.4(7) . . . . ?
C6 C5 N6 N5 178.0(3) . . . . ?
C6 C7 C8 C9 52.4(6) . . . . ?
C6 C7 C8 N10 -132.1(4) . . . . ?
C6 C7 N9 O6 0.1(5) . . . . ?
C6 C7 N9 O5A 145(3) . . . . ?
C6 N8 O6 N9 -1.4(4) . . . . ?
C7 C6 N8 O6 1.4(4) . . . . ?
C7 C6 N8 O5 -178.2(4) . . . . ?
C7 C8 C9 C10 175.2(4) . . . . ?
C7 C8 C9 N12 3.3(6) . . . . ?
C7 C8 N10 N11 -175.8(3) . . . . ?
C7 N9 O6 N8 0.8(4) . . . . ?
C8 C7 N9 O6 178.4(3) . . . . ?
C8 C7 N9 O5A -37(3) . . . . ?
C8 C9 C10 N11 0.5(4) . . . . ?
C8 C9 C10 N13 -178.2(4) . . . . ?
C8 C9 N12 O7 -6.6(6) . . . . ?
C8 C9 N12 O8 171.9(4) . . . . ?
C8 N10 N11 C10 0.0(4) . . . . ?
C8 N10 N11 C11 176.3(3) . . . . ?
C9 C8 N10 N11 0.4(4) . . . . ?
C9 C10 N11 C11 -176.7(3) . . . . ?
C9 C10 N11 N10 -0.3(4) . . . . ?
C9 C10 N13 N14 177.1(4) . . . . ?
C10 C9 N12 O7 -176.9(4) . . . . ?
C10 C9 N12 O8 1.6(6) . . . . ?
C10 N13 N14 C12 0.3(5) . . . . ?
C11 C12 N14 N13 0.2(6) . . . . ?
C11 C12 N16 O9 177.5(4) . . . . ?
C11 C12 N16 O10 -2.0(6) . . . . ?
C12 C11 N11 C10 -1.5(5) . . . . ?
C12 C11 N11 N10 -177.5(3) . . . . ?
N1 C1 C2 N4 3.0(7) . . . . ?
N1 C1 C2 N5 -176.2(3) . . . . ?
N1 C1 N2 N3 177.9(3) . . . . ?
N2 C1 C2 N4 -178.0(4) . . . . ?
N2 C1 C2 N5 2.8(6) . . . . ?
N2 C1 N1 O1 169.8(4) . . . . ?
N2 C1 N1 O2 -10.8(6) . . . . ?
N3 C3 C4 C5 -178.8(4) . . . . ?
N3 C3 C4 N7 -6.8(8) . . . . ?
N3 C3 N5 C2 0.3(6) . . . . ?
N3 C3 N5 N6 179.6(4) . . . . ?
N4 C2 N5 C3 178.4(4) . . . . ?
N4 C2 N5 N6 -0.9(6) . . . . ?
N5 C3 C4 C5 -0.8(4) . . . . ?
N5 C3 C4 N7 171.1(4) . . . . ?
N5 C3 N3 N2 1.7(6) . . . . ?
N6 C5 C6 C7 34.9(6) . . . . ?
N6 C5 C6 N8 -138.6(4) . . . . ?
N7 C4 C5 C6 11.6(7) . . . . ?
N7 C4 C5 N6 -171.8(4) . . . . ?
N8 C6 C7 C8 -179.0(4) . . . . ?
N8 C6 C7 N9 -0.9(5) . . . . ?
N9 C7 C8 C9 -125.5(4) . . . . ?
N9 C7 C8 N10 50.0(5) . . . . ?
N10 C8 C9 C10 -0.6(4) . . . . ?
N10 C8 C9 N12 -172.5(4) . . . . ?
N11 C10 N13 N14 -1.4(5) . . . . ?
N11 C11 C12 N14 0.4(5) . . . . ?
N11 C11 C12 N16 179.3(3) . . . . ?
N12 C9 C10 N11 172.5(3) . . . . ?
N12 C9 C10 N13 -6.2(7) . . . . ?
N13 C10 N11 C11 2.2(5) . . . . ?
N13 C10 N11 N10 178.5(3) . . . . ?
N14 C12 N16 O9 -3.4(6) . . . . ?
N14 C12 N16 O10 177.0(4) . . . . ?
N15 C11 C12 N14 -179.3(4) . . . . ?
N15 C11 C12 N16 -0.5(6) . . . . ?
N15 C11 N11 C10 178.3(3) . . . . ?
N15 C11 N11 N10 2.2(5) . . . . ?
N16 C12 N14 N13 -178.8(3) . . . . ?
O5 N8 O6 N9 178.3(3) . . . . ?
O5A N9 O6 N8 -152.0(19) . . . . ?

_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_20230427_zm_nlg_a_3_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2372335'
loop_
_audit_author_name
_audit_author_address
'Frank '
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-08-12 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2024-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C12 H4 N16 O10, 1.75(C2 H3 N)'
_chemical_formula_sum            'C15.50 H9.25 N17.75 O10'
_chemical_formula_weight         604.16
_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      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                   6.4781(2)
_cell_length_b                   13.5834(3)
_cell_length_c                   14.1528(4)
_cell_angle_alpha                71.0000(10)
_cell_angle_beta                 81.949(2)
_cell_angle_gamma                88.8700(10)
_cell_volume                     1165.47(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5200
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.978
_cell_measurement_theta_min      3.336
_shelx_estimated_absorpt_T_max   0.871
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0462 after correction.
The Ratio of minimum to maximum transmission is 0.8849.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             613
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15540
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.075
_diffrn_reflns_theta_min         3.336
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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                3319
_reflns_number_total             4229
_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       'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.047
_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)+(0.0592P)²+0.2332P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1104
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N18-C15
 1.14 with sigma of 0.02
 C15-N18
 1.137 with sigma of 0.01
 C15-C16
 1.456 with sigma of 0.01
 C16-N18
 2.593 with sigma of 0.02
 N19-C17
 1.14 with sigma of 0.02
 C17-N19
 1.137 with sigma of 0.01
 C17-C18
 1.456 with sigma of 0.01
 C18-N19
 2.593 with sigma of 0.02
 N18-C16
 2.59 with sigma of 0.04
 N19-C18
 2.59 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
N18 \\sim C15 \\sim C16: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
N19 \\sim C17 \\sim C18: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 N18, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N19, C17, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O7A)=1-FVAR(1)
 Sof(O7)=FVAR(1)
 Fixed Sof: N18(0.25) C15(0.25) C16(0.25) H16A(0.25) H16B(0.25) H16C(0.25)
 N19(0.5) C17(0.5) C18(0.5) H18A(0.5) H18B(0.5) H18C(0.5)
5.a X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N13(H13A,H13B)
5.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.0128(3) 0.28081(15) 0.94173(14) 0.0584(5) Uani 1 1 d . . . . .
C1 C 0.3156(4) 0.19207(17) 0.93424(16) 0.0373(5) Uani 1 1 d . . . . .
N1 N 0.1597(4) 0.24195(17) 0.98611(16) 0.0502(5) Uani 1 1 d . . . . .
O2 O 0.1760(4) 0.2398(2) 1.07197(17) 0.0810(7) Uani 1 1 d . . . . .
C2 C 0.2973(3) 0.19057(15) 0.83696(15) 0.0289(4) Uani 1 1 d . . . . .
N2 N 0.4690(4) 0.15094(17) 0.98637(16) 0.0488(5) Uani 1 1 d . . . . .
C3 C 0.6117(3) 0.09330(15) 0.85983(15) 0.0292(4) Uani 1 1 d . . . . .
N3 N 0.6221(3) 0.10130(16) 0.95205(15) 0.0459(5) Uani 1 1 d . . . . .
O3 O 0.9879(3) -0.01614(17) 0.89943(15) 0.0663(6) Uani 1 1 d . . . . .
O4 O 1.0490(2) -0.00926(12) 0.74272(12) 0.0420(4) Uani 1 1 d . . . A 4
C4 C 0.7391(3) 0.04776(14) 0.79854(15) 0.0277(4) Uani 1 1 d . . . . .
N4 N 0.4556(2) 0.13619(11) 0.80438(12) 0.0249(3) Uani 1 1 d . . . . .
C5 C 0.6473(3) 0.06782(13) 0.71010(13) 0.0235(4) Uani 1 1 d . . . . .
O5 O 0.9900(3) 0.38794(12) 0.53162(13) 0.0460(4) Uani 1 1 d . . . . .
N5 N 0.1596(3) 0.23074(15) 0.77692(14) 0.0401(4) Uani 1 1 d . . . . .
H5A H 0.170329 0.222441 0.717308 0.048 Uiso 1 1 calc R U . . .
H5B H 0.056158 0.266089 0.796069 0.048 Uiso 1 1 calc R U . . .
O6 O 0.9888(2) 0.21906(11) 0.58230(12) 0.0375(4) Uani 1 1 d . . . . .
N6 N 0.4740(2) 0.12202(12) 0.71291(11) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.7079(3) 0.04105(13) 0.61893(14) 0.0238(4) Uani 1 1 d . . . . .
O7 O 0.7996(2) -0.13479(10) 0.67872(11) 0.0315(5) Uani 0.907(5) 1 d . . P B 1
C7 C 0.6964(3) 0.10393(14) 0.51827(14) 0.0231(4) Uani 1 1 d . . . . .
N7 N 0.9374(3) 0.00325(14) 0.81515(14) 0.0372(4) Uani 1 1 d . . . . .
N8 N 0.7643(2) -0.05216(12) 0.61635(12) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.6424(3) 0.21394(13) 0.48059(13) 0.0232(4) Uani 1 1 d . . . . .
O8 O 0.7887(2) -0.04714(10) 0.51141(10) 0.0305(3) Uani 1 1 d . . . . .
N9 N 0.7412(3) 0.05193(12) 0.45501(13) 0.0285(4) Uani 1 1 d . . . . .
O9 O 0.0824(3) 0.55119(12) 0.24939(13) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.7410(3) 0.30225(14) 0.48800(14) 0.0251(4) Uani 1 1 d . . . . .
N10 N 0.9176(3) 0.30369(12) 0.53704(12) 0.0291(4) Uani 1 1 d . . . . .
O10 O 0.2692(3) 0.67789(11) 0.25621(14) 0.0487(4) Uani 1 1 d . . . . .
C10 C 0.6349(3) 0.38832(14) 0.43482(14) 0.0255(4) Uani 1 1 d . . . . .
N11 N 0.4839(2) 0.23966(11) 0.42805(12) 0.0251(3) Uani 1 1 d . . . . .
C11 C 0.3384(3) 0.40279(14) 0.34598(14) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.3708(3) 0.50959(14) 0.33003(15) 0.0294(4) Uani 1 1 d . . . . .
N12 N 0.4805(2) 0.34517(11) 0.40196(12) 0.0244(3) Uani 1 1 d . . . . .
N13 N 0.2016(3) 0.35268(13) 0.31729(13) 0.0329(4) Uani 1 1 d . . . . .
H13A H 0.203713 0.284362 0.334244 0.039 Uiso 1 1 calc R U . . .
H13B H 0.107556 0.387364 0.281073 0.039 Uiso 1 1 calc R U . . .
N14 N 0.6586(3) 0.49242(12) 0.41354(13) 0.0335(4) Uani 1 1 d . . . . .
N15 N 0.5227(3) 0.55049(12) 0.36087(13) 0.0339(4) Uani 1 1 d . . . . .
N16 N 0.2335(3) 0.58486(13) 0.27461(13) 0.0348(4) Uani 1 1 d . . . . .
C13 C -0.2503(4) 0.2858(2) 1.20102(17) 0.0425(5) Uani 1 1 d . . . . .
C14 C -0.3447(4) 0.2140(2) 1.1640(3) 0.0595(7) Uani 1 1 d . . . . .
H14A H -0.291522 0.228581 1.092360 0.089 Uiso 1 1 calc R U . . .
H14B H -0.496381 0.221419 1.172206 0.089 Uiso 1 1 calc R U . . .
H14C H -0.311051 0.142698 1.202128 0.089 Uiso 1 1 calc R U . . .
N17 N -0.1766(4) 0.3433(2) 1.22973(17) 0.0617(6) Uani 1 1 d . . . . .
N18 N 0.527(4) 0.4662(19) 0.8963(13) 0.105(9) Uani 0.25 1 d D U P C -2
C15 C 0.465(3) 0.4842(12) 0.9673(9) 0.072(4) Uani 0.25 1 d D U P C -2
C16 C 0.395(4) 0.5188(15) 1.0535(11) 0.097(6) Uani 0.25 1 d D U P C -2
H16A H 0.343289 0.589637 1.029782 0.145 Uiso 0.25 1 calc R U P C -2
H16B H 0.512146 0.518063 1.090677 0.145 Uiso 0.25 1 calc R U P C -2
H16C H 0.282924 0.471796 1.098107 0.145 Uiso 0.25 1 calc R U P C -2
N19 N 0.4554(18) 0.4372(9) 0.8979(9) 0.089(4) Uani 0.5 1 d D U P D -1
C17 C 0.3157(14) 0.4625(5) 0.9417(6) 0.084(2) Uani 0.5 1 d D U P D -1
C18 C 0.1401(14) 0.4902(6) 1.0030(7) 0.113(4) Uani 0.5 1 d D U P D -1
H18A H 0.040839 0.529394 0.959489 0.169 Uiso 0.5 1 calc R U P D -1
H18B H 0.189927 0.533243 1.039401 0.169 Uiso 0.5 1 calc R U P D -1
H18C H 0.070967 0.426710 1.051660 0.169 Uiso 0.5 1 calc R U P D -1
O7A O 0.706(3) 0.0622(13) 0.3776(13) 0.041(5) Uani 0.093(5) 1 d . . P B 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 N1 1.229(3) . ?
C1 N1 1.452(3) . ?
C1 C2 1.405(3) . ?
C1 N2 1.326(3) . ?
N1 O2 1.225(3) . ?
C2 N4 1.368(3) . ?
C2 N5 1.306(3) . ?
N2 N3 1.314(3) . ?
C3 N3 1.355(3) . ?
C3 C4 1.395(3) . ?
C3 N4 1.371(2) . ?
O3 N7 1.225(2) . ?
O4 N7 1.226(2) . ?
C4 C5 1.405(3) . ?
C4 N7 1.425(3) . ?
N4 N6 1.358(2) . ?
C5 N6 1.333(2) . ?
C5 C6 1.452(3) . ?
O5 N10 1.220(2) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
O6 N10 1.236(2) . ?
C6 C7 1.414(3) . ?
C6 N8 1.321(2) . ?
O7 N8 1.222(2) . ?
C7 C8 1.467(3) . ?
C7 N9 1.310(2) . ?
N8 O8 1.451(2) . ?
C8 C9 1.410(2) . ?
C8 N11 1.327(2) . ?
O8 N9 1.377(2) . ?
N9 O7A 1.114(17) . ?
O9 N16 1.232(2) . ?
C9 N10 1.423(2) . ?
C9 C10 1.395(3) . ?
O10 N16 1.224(2) . ?
C10 N12 1.375(2) . ?
C10 N14 1.354(2) . ?
N11 N12 1.359(2) . ?
C11 C12 1.409(3) . ?
C11 N12 1.364(2) . ?
C11 N13 1.311(2) . ?
C12 N15 1.329(3) . ?
C12 N16 1.445(3) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
N14 N15 1.314(2) . ?
C13 C14 1.430(4) . ?
C13 N17 1.131(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N18 C15 1.130(8) . ?
C15 C16 1.457(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N19 C17 1.136(7) . ?
C17 C18 1.453(7) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 C1 N1 120.4(2) . . ?
N2 C1 N1 114.20(19) . . ?
N2 C1 C2 125.4(2) . . ?
O1 N1 C1 117.12(19) . . ?
O2 N1 O1 123.6(2) . . ?
O2 N1 C1 119.2(2) . . ?
N4 C2 C1 110.51(18) . . ?
N5 C2 C1 131.3(2) . . ?
N5 C2 N4 118.19(18) . . ?
N3 N2 C1 122.69(19) . . ?
N3 C3 C4 133.20(19) . . ?
N3 C3 N4 122.67(19) . . ?
N4 C3 C4 104.11(16) . . ?
N2 N3 C3 115.49(18) . . ?
C3 C4 C5 106.04(17) . . ?
C3 C4 N7 127.08(17) . . ?
C5 C4 N7 126.31(18) . . ?
C2 N4 C3 123.16(17) . . ?
N6 N4 C2 122.65(16) . . ?
N6 N4 C3 114.17(16) . . ?
C4 C5 C6 131.85(17) . . ?
N6 C5 C4 111.96(17) . . ?
N6 C5 C6 116.19(16) . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C5 N6 N4 103.72(14) . . ?
C7 C6 C5 127.52(17) . . ?
N8 C6 C5 125.22(16) . . ?
N8 C6 C7 106.92(16) . . ?
C6 C7 C8 128.37(17) . . ?
N9 C7 C6 111.76(16) . . ?
N9 C7 C8 119.86(16) . . ?
O3 N7 O4 124.47(19) . . ?
O3 N7 C4 118.01(19) . . ?
O4 N7 C4 117.46(17) . . ?
C6 N8 O8 106.89(14) . . ?
O7 N8 C6 135.53(17) . . ?
O7 N8 O8 117.57(15) . . ?
C9 C8 C7 129.41(17) . . ?
N11 C8 C7 118.74(14) . . ?
N11 C8 C9 111.79(16) . . ?
N9 O8 N8 107.79(12) . . ?
C7 N9 O8 106.62(15) . . ?
O7A N9 C7 134.1(9) . . ?
O7A N9 O8 116.4(9) . . ?
C8 C9 N10 126.91(17) . . ?
C10 C9 C8 106.29(16) . . ?
C10 C9 N10 126.76(16) . . ?
O5 N10 O6 124.04(16) . . ?
O5 N10 C9 118.30(16) . . ?
O6 N10 C9 117.65(15) . . ?
N12 C10 C9 103.68(15) . . ?
N14 C10 C9 133.96(17) . . ?
N14 C10 N12 122.35(17) . . ?
C8 N11 N12 103.97(13) . . ?
N12 C11 C12 110.47(16) . . ?
N13 C11 C12 131.99(19) . . ?
N13 C11 N12 117.54(16) . . ?
C11 C12 N16 119.79(17) . . ?
N15 C12 C11 125.65(19) . . ?
N15 C12 N16 114.55(17) . . ?
N11 N12 C10 114.24(15) . . ?
N11 N12 C11 122.45(15) . . ?
C11 N12 C10 123.29(15) . . ?
C11 N13 H13A 120.0 . . ?
C11 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
N15 N14 C10 116.14(16) . . ?
N14 N15 C12 122.05(16) . . ?
O9 N16 C12 117.47(16) . . ?
O10 N16 O9 123.02(18) . . ?
O10 N16 C12 119.50(18) . . ?
N17 C13 C14 179.4(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N18 C15 C16 174(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N19 C17 C18 176.6(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N4 C3 -2.1(2) . . . . ?
C1 C2 N4 N6 179.44(16) . . . . ?
C1 N2 N3 C3 -1.0(3) . . . . ?
N1 C1 C2 N4 -177.54(19) . . . . ?
N1 C1 C2 N5 2.3(4) . . . . ?
N1 C1 N2 N3 178.9(2) . . . . ?
C2 C1 N1 O1 0.8(3) . . . . ?
C2 C1 N1 O2 178.0(2) . . . . ?
C2 C1 N2 N3 -1.4(4) . . . . ?
C2 N4 N6 C5 178.91(16) . . . . ?
N2 C1 N1 O1 -179.5(2) . . . . ?
N2 C1 N1 O2 -2.3(4) . . . . ?
N2 C1 C2 N4 2.8(3) . . . . ?
N2 C1 C2 N5 -177.4(2) . . . . ?
C3 C4 C5 N6 0.0(2) . . . . ?
C3 C4 C5 C6 179.52(18) . . . . ?
C3 C4 N7 O3 15.1(3) . . . . ?
C3 C4 N7 O4 -162.14(19) . . . . ?
C3 N4 N6 C5 0.28(19) . . . . ?
N3 C3 C4 C5 -178.6(2) . . . . ?
N3 C3 C4 N7 -6.8(4) . . . . ?
N3 C3 N4 C2 0.0(3) . . . . ?
N3 C3 N4 N6 178.62(18) . . . . ?
C4 C3 N3 N2 -179.8(2) . . . . ?
C4 C3 N4 C2 -178.92(16) . . . . ?
C4 C3 N4 N6 -0.3(2) . . . . ?
C4 C5 N6 N4 -0.15(18) . . . . ?
C4 C5 C6 C7 -140.0(2) . . . . ?
C4 C5 C6 N8 47.6(3) . . . . ?
N4 C3 N3 N2 1.6(3) . . . . ?
N4 C3 C4 C5 0.17(19) . . . . ?
N4 C3 C4 N7 171.91(18) . . . . ?
C5 C4 N7 O3 -174.7(2) . . . . ?
C5 C4 N7 O4 8.0(3) . . . . ?
C5 C6 C7 C8 7.1(3) . . . . ?
C5 C6 C7 N9 -172.70(16) . . . . ?
C5 C6 N8 O7 -7.2(3) . . . . ?
C5 C6 N8 O8 173.73(16) . . . . ?
N5 C2 N4 C3 178.10(17) . . . . ?
N5 C2 N4 N6 -0.4(3) . . . . ?
N6 C5 C6 C7 39.5(2) . . . . ?
N6 C5 C6 N8 -132.89(18) . . . . ?
C6 C5 N6 N4 -179.77(14) . . . . ?
C6 C7 C8 C9 59.9(3) . . . . ?
C6 C7 C8 N11 -122.9(2) . . . . ?
C6 C7 N9 O8 -1.3(2) . . . . ?
C6 C7 N9 O7A 158.0(11) . . . . ?
C6 N8 O8 N9 -0.82(17) . . . . ?
O7 N8 O8 N9 179.93(15) . . . . ?
C7 C6 N8 O7 179.11(19) . . . . ?
C7 C6 N8 O8 0.05(18) . . . . ?
C7 C8 C9 N10 -1.4(3) . . . . ?
C7 C8 C9 C10 176.69(18) . . . . ?
C7 C8 N11 N12 -177.87(15) . . . . ?
N7 C4 C5 N6 -171.84(17) . . . . ?
N7 C4 C5 C6 7.7(3) . . . . ?
N8 C6 C7 C8 -179.40(16) . . . . ?
N8 C6 C7 N9 0.8(2) . . . . ?
N8 O8 N9 C7 1.28(17) . . . . ?
N8 O8 N9 O7A -162.2(9) . . . . ?
C8 C7 N9 O8 178.88(14) . . . . ?
C8 C7 N9 O7A -21.9(11) . . . . ?
C8 C9 N10 O5 176.13(19) . . . . ?
C8 C9 N10 O6 -3.6(3) . . . . ?
C8 C9 C10 N12 1.2(2) . . . . ?
C8 C9 C10 N14 -178.5(2) . . . . ?
C8 N11 N12 C10 1.1(2) . . . . ?
C8 N11 N12 C11 179.64(17) . . . . ?
N9 C7 C8 C9 -120.3(2) . . . . ?
N9 C7 C8 N11 56.9(2) . . . . ?
C9 C8 N11 N12 -0.2(2) . . . . ?
C9 C10 N12 N11 -1.4(2) . . . . ?
C9 C10 N12 C11 179.99(17) . . . . ?
C9 C10 N14 N15 -179.2(2) . . . . ?
N10 C9 C10 N12 179.31(18) . . . . ?
N10 C9 C10 N14 -0.3(4) . . . . ?
C10 C9 N10 O5 -1.6(3) . . . . ?
C10 C9 N10 O6 178.69(18) . . . . ?
C10 N14 N15 C12 -0.1(3) . . . . ?
N11 C8 C9 N10 -178.75(18) . . . . ?
N11 C8 C9 C10 -0.6(2) . . . . ?
C11 C12 N15 N14 -2.0(3) . . . . ?
C11 C12 N16 O9 5.1(3) . . . . ?
C11 C12 N16 O10 -176.02(18) . . . . ?
C12 C11 N12 C10 -1.5(2) . . . . ?
C12 C11 N12 N11 -179.90(16) . . . . ?
N12 C10 N14 N15 1.2(3) . . . . ?
N12 C11 C12 N15 2.6(3) . . . . ?
N12 C11 C12 N16 -178.31(16) . . . . ?
N13 C11 C12 N15 -177.3(2) . . . . ?
N13 C11 C12 N16 1.7(3) . . . . ?
N13 C11 N12 C10 178.51(17) . . . . ?
N13 C11 N12 N11 0.1(3) . . . . ?
N14 C10 N12 N11 178.25(17) . . . . ?
N14 C10 N12 C11 -0.3(3) . . . . ?
N15 C12 N16 O9 -175.72(18) . . . . ?
N15 C12 N16 O10 3.2(3) . . . . ?
N16 C12 N15 N14 178.92(17) . . . . ?

_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_20230423_ys_nlg_a3_2dmso_0m
_database_code_depnum_ccdc_archive 'CCDC 2372337'
loop_
_audit_author_name
_audit_author_address
'Frank '
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-08-12 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2024-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C2 H6 O S), 2(C6 H2 N8 O5)'
_chemical_formula_sum            'C20 H28 N16 O14 S4'
_chemical_formula_weight         844.82
_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           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   23.6344(6)
_cell_length_b                   8.8105(2)
_cell_length_c                   18.3794(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.3560(10)
_cell_angle_gamma                90
_cell_volume                     3588.15(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.133
_cell_measurement_theta_min      4.817
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    3.202
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.7680.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33356
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.263
_diffrn_reflns_theta_min         4.817
_diffrn_ambient_temperature      193.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                5726
_reflns_number_total             6567
_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       'Bruker APEX4'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     627
_refine_ls_number_reflns         6567
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+2.3927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S4-C20 \\sim S4A-C20 \\sim S4-C19 \\sim S4A-C19A
 with sigma of 0.02
 O15-C18 \\sim O15A-C18A
 with sigma of 0.04
 S4-C20 \\sim S4-C20A
 with sigma of 0.02
 O15-C17 \\sim O15A-C17A
 with sigma of 0.04
 S4A-C20 \\sim S4A-C20A
 with sigma of 0.02
 S4A-C20A \\sim S4-C20 \\sim S4-C19 \\sim S4A-C19A
 with sigma of 0.02
 S4-O16 \\sim S4A-O16A
 with sigma of 0.02
 S3-C18 \\sim S3A-C18A
 with sigma of 0.02
 S3-C17 \\sim S3A-C17A
 with sigma of 0.02
 C18-C17 \\sim C18A-C17A
 with sigma of 0.04
 S3-O15 \\sim S3A-O15A
 with sigma of 0.02
 O8-N9 \\sim O8A-N9
 with sigma of 0.02
 N9-O7 \\sim N9-O7A
 with sigma of 0.02
 O1-N1 \\sim O1A-N1A
 with sigma of 0.02
 N1-C6 \\sim N1A-C6
 with sigma of 0.02
 N1-O2 \\sim N1A-O2A
 with sigma of 0.02
 O1-C6 \\sim O1A-C6
 with sigma of 0.04
 O1-O2 \\sim O1A-O2A
 with sigma of 0.04
 C6-O2 \\sim C6-O2A
 with sigma of 0.04
3. Rigid bond restraints
 O5, N7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
S4 \\sim O16 \\sim C19 \\sim C20: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
S4A \\sim O16A \\sim C19A \\sim C20A: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02 within 2A
S3 \\sim O15 \\sim C17 \\sim C18 \\sim S3A \\sim C17A \\sim C18A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
O7 \\sim O8 \\sim O7A \\sim O8A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
O1 \\sim O2 \\sim N1 \\sim O1A \\sim O2A \\sim N1A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O15A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Sof(O1A)=Sof(O2A)=Sof(N1A)=Sof(O7A)=Sof(O8A)=Sof(S3A)=Sof(O15A)=Sof(C17A)=
 Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(S4A)=
 Sof(O16A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=Sof(C20A)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(O7)=Sof(O8)=Sof(S3)=Sof(O15)=Sof(C17)=Sof(H17C)=
 Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(S4)=Sof(O16)=
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 FVAR(1)
 Fixed Sof: O6(0.5) O11(0.5)
6.a X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N10(H10A,H10B)
6.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17C,H17A,H17B), C18(H18A,H18B,H18C), C17A(H17D,H17E,H17F),
 C18A(H18D,H18E,H18F), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,
 H19F), C20A(H20D,H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.67372(3) 0.36848(8) 0.28094(4) 0.05659(19) Uani 1 1 d . . . . .
O13 O 0.60709(8) 0.3458(2) 0.26273(12) 0.0714(6) Uani 1 1 d . . . . .
C13 C 0.68924(13) 0.5568(4) 0.31469(18) 0.0667(8) Uani 1 1 d . . . . .
H13A H 0.661689 0.626185 0.277206 0.100 Uiso 1 1 calc R U . . .
H13B H 0.730996 0.582292 0.320731 0.100 Uiso 1 1 calc R U . . .
H13C H 0.683664 0.566498 0.364888 0.100 Uiso 1 1 calc R U . . .
C14 C 0.68333(13) 0.3922(4) 0.19042(18) 0.0674(8) Uani 1 1 d . . . . .
H14A H 0.673550 0.297072 0.161089 0.101 Uiso 1 1 calc R U . . .
H14B H 0.725304 0.419997 0.198940 0.101 Uiso 1 1 calc R U . . .
H14C H 0.656456 0.472836 0.161047 0.101 Uiso 1 1 calc R U . . .
S2 S 0.89928(2) 0.14069(7) 0.46519(3) 0.04290(15) Uani 1 1 d . . . . .
O14 O 0.90883(8) 0.3027(2) 0.49117(12) 0.0614(5) Uani 1 1 d . . . . .
C15 C 0.92533(14) 0.0274(3) 0.54977(15) 0.0599(7) Uani 1 1 d . . . . .
H15A H 0.908132 0.064773 0.587806 0.090 Uiso 1 1 calc R U . . .
H15B H 0.969466 0.032652 0.571921 0.090 Uiso 1 1 calc R U . . .
H15C H 0.912845 -0.078103 0.536451 0.090 Uiso 1 1 calc R U . . .
C16 C 0.82041(12) 0.1083(3) 0.4401(2) 0.0633(8) Uani 1 1 d . . . . .
H16A H 0.798179 0.172426 0.395785 0.095 Uiso 1 1 calc R U . . .
H16B H 0.808188 0.133372 0.484438 0.095 Uiso 1 1 calc R U . . .
H16C H 0.811455 0.001353 0.426225 0.095 Uiso 1 1 calc R U . . .
O3 O 0.66704(10) -0.0856(2) 0.34189(18) 0.0913(8) Uani 1 1 d . . . . .
O4 O 0.70419(9) -0.0085(2) 0.46237(17) 0.0824(7) Uani 1 1 d . . . . .
O5 O 0.500000 -0.2989(2) 0.250000 0.0582(6) Uani 1 2 d S TU P B .
N2 N 0.48390(7) 0.46243(19) 0.36611(10) 0.0354(4) Uani 1 1 d . . . . .
H2A H 0.458787 0.401334 0.332116 0.042 Uiso 1 1 calc R U . . .
H2B H 0.471581 0.552288 0.375298 0.042 Uiso 1 1 calc R U . . .
N3 N 0.64500(8) 0.4450(2) 0.48605(11) 0.0429(4) Uani 1 1 d . . . . .
N4 N 0.66045(8) 0.3105(2) 0.46828(11) 0.0434(4) Uani 1 1 d . . . . .
N5 N 0.55705(7) 0.27922(18) 0.38715(10) 0.0336(4) Uani 1 1 d . . . . .
N6 N 0.51927(8) 0.18219(18) 0.33589(11) 0.0367(4) Uani 1 1 d . . . . .
N7 N 0.54006(10) -0.2049(2) 0.30599(15) 0.0519(5) Uani 1 1 d . U . . .
N8 N 0.66507(10) -0.0106(2) 0.39755(19) 0.0634(7) Uani 1 1 d . . . . .
C1 C 0.52509(10) -0.0631(2) 0.28481(15) 0.0434(5) Uani 1 1 d . . . . .
C2 C 0.55416(10) 0.0642(2) 0.33407(14) 0.0401(5) Uani 1 1 d . . . . .
C3 C 0.61357(10) 0.0849(2) 0.38551(15) 0.0425(5) Uani 1 1 d . . . . .
C4 C 0.61517(9) 0.2268(2) 0.41906(13) 0.0374(5) Uani 1 1 d . . . . .
C5 C 0.53914(9) 0.4200(2) 0.40270(12) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.58858(10) 0.4956(2) 0.45755(13) 0.0381(5) Uani 1 1 d D . . . .
O1 O 0.5288(6) 0.676(2) 0.4847(10) 0.047(3) Uani 0.559(3) 1 d D U P A 1
O2 O 0.6228(5) 0.7369(11) 0.5032(5) 0.0493(16) Uani 0.559(3) 1 d D U P A 1
N1 N 0.5799(5) 0.6502(13) 0.4795(11) 0.039(2) Uani 0.559(3) 1 d D U P A 1
O1A O 0.5285(7) 0.693(2) 0.4697(12) 0.041(3) Uani 0.441(3) 1 d D U P A 2
O2A O 0.6273(7) 0.7137(16) 0.5251(7) 0.063(3) Uani 0.441(3) 1 d D U P A 2
N1A N 0.5814(8) 0.6405(18) 0.4921(16) 0.047(4) Uani 0.441(3) 1 d D U P A 2
O6 O 0.57190(14) -0.2669(4) 0.34852(18) 0.0422(7) Uani 0.5 1 d . . P B -1
O9 O 0.78139(8) 0.0985(3) 0.21767(16) 0.0873(8) Uani 1 1 d . . . . .
O10 O 0.83942(9) -0.0275(2) 0.17051(12) 0.0697(6) Uani 1 1 d . . . . .
O12 O 1.000000 -0.2398(3) 0.250000 0.0659(7) Uani 1 2 d S T P C .
N9 N 0.90761(10) 0.6997(3) 0.40640(16) 0.0642(6) Uani 1 1 d D . . . .
N10 N 1.01054(8) 0.5004(2) 0.40216(11) 0.0412(4) Uani 1 1 d . . . . .
H10A H 1.037538 0.436469 0.397106 0.049 Uiso 1 1 calc R U . . .
H10B H 1.022265 0.584590 0.428962 0.049 Uiso 1 1 calc R U . . .
N11 N 0.84488(9) 0.5125(3) 0.33200(14) 0.0544(5) Uani 1 1 d . . . . .
N12 N 0.83067(8) 0.3824(3) 0.29495(13) 0.0524(5) Uani 1 1 d . . . . .
N13 N 0.93668(7) 0.33835(19) 0.32868(10) 0.0345(4) Uani 1 1 d . . . . .
N14 N 0.97707(7) 0.23565(19) 0.32066(10) 0.0341(4) Uani 1 1 d . . . . .
N15 N 0.83073(9) 0.0685(3) 0.21333(13) 0.0548(5) Uani 1 1 d . . . . .
N16 N 0.95777(10) -0.1454(2) 0.26671(13) 0.0521(5) Uani 1 1 d . . . . .
C7 C 0.97366(10) -0.0044(2) 0.25998(12) 0.0382(5) Uani 1 1 d . . . . .
C8 C 0.94268(9) 0.1253(2) 0.27827(12) 0.0349(4) Uani 1 1 d . . . . .
C9 C 0.88113(9) 0.1557(3) 0.26069(13) 0.0403(5) Uani 1 1 d . . . . .
C10 C 0.87751(9) 0.2947(3) 0.29389(13) 0.0401(5) Uani 1 1 d . . . . .
C11 C 0.95358(9) 0.4707(2) 0.37016(13) 0.0371(5) Uani 1 1 d . . . . .
C12 C 0.90154(10) 0.5539(3) 0.36791(15) 0.0470(6) Uani 1 1 d . . . . .
O7 O 0.8605(4) 0.7597(10) 0.4084(5) 0.0719(19) Uani 0.559(3) 1 d D U P A 1
O8 O 0.9580(5) 0.751(3) 0.4435(14) 0.054(3) Uani 0.559(3) 1 d D U P A 1
O7A O 0.8658(4) 0.7955(11) 0.3811(7) 0.074(3) Uani 0.441(3) 1 d D U P A 2
O8A O 0.9591(7) 0.722(3) 0.4526(17) 0.063(5) Uani 0.441(3) 1 d D U P A 2
O11 O 0.91980(19) -0.2080(4) 0.2783(2) 0.0624(10) Uani 0.5 1 d . . P C -1
S3 S 0.6042(2) 0.1805(6) 0.6025(4) 0.0668(13) Uani 0.559(3) 1 d D U P A 1
O15 O 0.5837(2) 0.2684(5) 0.6608(2) 0.0427(10) Uani 0.559(3) 1 d D U P A 1
C17 C 0.5894(5) -0.0059(9) 0.6211(6) 0.107(3) Uani 0.559(3) 1 d D U P A 1
H17C H 0.547481 -0.014416 0.618662 0.161 Uiso 0.559(3) 1 calc R U P A 1
H17A H 0.616564 -0.035410 0.672878 0.161 Uiso 0.559(3) 1 calc R U P A 1
H17B H 0.595925 -0.072951 0.582168 0.161 Uiso 0.559(3) 1 calc R U P A 1
C18 C 0.6859(3) 0.1721(9) 0.6468(6) 0.076(2) Uani 0.559(3) 1 d D U P A 1
H18A H 0.702664 0.274491 0.649313 0.115 Uiso 0.559(3) 1 calc R U P A 1
H18B H 0.702139 0.106732 0.615701 0.115 Uiso 0.559(3) 1 calc R U P A 1
H18C H 0.696862 0.130642 0.699420 0.115 Uiso 0.559(3) 1 calc R U P A 1
S3A S 0.6023(2) 0.1809(5) 0.5941(4) 0.0434(10) Uani 0.441(3) 1 d D U P A 2
O15A O 0.5906(3) 0.2951(8) 0.6413(4) 0.0588(19) Uani 0.441(3) 1 d D U P A 2
C17A C 0.5582(4) 0.0153(10) 0.5874(8) 0.080(3) Uani 0.441(3) 1 d D U P A 2
H17D H 0.566619 -0.057345 0.552062 0.120 Uiso 0.441(3) 1 calc R U P A 2
H17E H 0.515259 0.042243 0.567410 0.120 Uiso 0.441(3) 1 calc R U P A 2
H17F H 0.568215 -0.030677 0.638884 0.120 Uiso 0.441(3) 1 calc R U P A 2
C18A C 0.6735(4) 0.1018(10) 0.6347(8) 0.078(3) Uani 0.441(3) 1 d D U P A 2
H18D H 0.677657 0.056152 0.684888 0.117 Uiso 0.441(3) 1 calc R U P A 2
H18E H 0.704135 0.181082 0.642179 0.117 Uiso 0.441(3) 1 calc R U P A 2
H18F H 0.679110 0.023516 0.599901 0.117 Uiso 0.441(3) 1 calc R U P A 2
S4 S 0.83201(5) 0.55885(13) 0.54809(9) 0.0559(5) Uani 0.559(3) 1 d D U P A 1
O16 O 0.8870(5) 0.641(2) 0.5999(7) 0.088(4) Uani 0.559(3) 1 d D U P A 1
C19 C 0.7736(2) 0.6854(6) 0.5471(5) 0.0752(18) Uani 0.559(3) 1 d D U P A 1
H19A H 0.734376 0.638113 0.519846 0.113 Uiso 0.559(3) 1 calc R U P A 1
H19B H 0.777170 0.779183 0.520370 0.113 Uiso 0.559(3) 1 calc R U P A 1
H19C H 0.776879 0.708917 0.600532 0.113 Uiso 0.559(3) 1 calc R U P A 1
C20 C 0.8197(9) 0.4123(16) 0.6077(12) 0.088(5) Uani 0.559(3) 1 d D U P A 1
H20A H 0.817134 0.456841 0.655334 0.132 Uiso 0.559(3) 1 calc R U P A 1
H20B H 0.853211 0.339939 0.620979 0.132 Uiso 0.559(3) 1 calc R U P A 1
H20C H 0.781847 0.359610 0.579556 0.132 Uiso 0.559(3) 1 calc R U P A 1
S4A S 0.82370(6) 0.60100(19) 0.60371(10) 0.0575(6) Uani 0.441(3) 1 d D U P A 2
O16A O 0.8898(6) 0.629(3) 0.6261(8) 0.069(3) Uani 0.441(3) 1 d D U P A 2
C19A C 0.7898(4) 0.6148(14) 0.5018(5) 0.107(3) Uani 0.441(3) 1 d D U P A 2
H19D H 0.793042 0.719376 0.485571 0.160 Uiso 0.441(3) 1 calc R U P A 2
H19E H 0.747125 0.586363 0.486277 0.160 Uiso 0.441(3) 1 calc R U P A 2
H19F H 0.810362 0.546295 0.477144 0.160 Uiso 0.441(3) 1 calc R U P A 2
C20A C 0.8123(9) 0.4018(16) 0.5971(15) 0.071(5) Uani 0.441(3) 1 d D U P A 2
H20D H 0.769711 0.380060 0.568217 0.107 Uiso 0.441(3) 1 calc R U P A 2
H20E H 0.823628 0.358650 0.649350 0.107 Uiso 0.441(3) 1 calc R U P A 2
H20F H 0.837323 0.356588 0.569989 0.107 Uiso 0.441(3) 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
S1 O13 1.5051(17) . ?
S1 C13 1.765(3) . ?
S1 C14 1.768(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S2 O14 1.4971(18) . ?
S2 C15 1.768(3) . ?
S2 C16 1.781(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O3 N8 1.233(4) . ?
O4 N8 1.228(4) . ?
O5 N7 1.401(3) 2_655 ?
O5 N7 1.401(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C5 1.298(3) . ?
N3 N4 1.314(3) . ?
N3 C6 1.328(3) . ?
N4 C4 1.354(3) . ?
N5 N6 1.353(2) . ?
N5 C4 1.373(3) . ?
N5 C5 1.372(3) . ?
N6 C2 1.334(3) . ?
N7 C1 1.320(3) . ?
N7 O6 1.033(3) . ?
N8 C3 1.432(3) . ?
C1 C1 1.410(5) 2_655 ?
C1 C2 1.455(3) . ?
C2 C3 1.405(3) . ?
C3 C4 1.388(3) . ?
C5 C6 1.416(3) . ?
C6 N1 1.455(9) . ?
C6 N1A 1.463(11) . ?
O1 N1 1.264(12) . ?
O2 N1 1.223(9) . ?
O1A N1A 1.260(14) . ?
O2A N1A 1.225(11) . ?
O9 N15 1.225(3) . ?
O10 N15 1.220(3) . ?
O12 N16 1.412(3) . ?
O12 N16 1.412(3) 2_755 ?
N9 C12 1.449(3) . ?
N9 O7 1.245(7) . ?
N9 O8 1.235(10) . ?
N9 O7A 1.259(9) . ?
N9 O8A 1.234(12) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C11 1.295(3) . ?
N11 N12 1.315(3) . ?
N11 C12 1.322(3) . ?
N12 C10 1.356(3) . ?
N13 N14 1.360(2) . ?
N13 C10 1.375(3) . ?
N13 C11 1.374(3) . ?
N14 C8 1.331(3) . ?
N15 C9 1.430(3) . ?
N16 C7 1.316(3) . ?
N16 O11 1.135(4) . ?
C7 C7 1.415(4) 2_755 ?
C7 C8 1.458(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.384(3) . ?
C11 C12 1.420(3) . ?
S3 O15 1.531(6) . ?
S3 C17 1.737(8) . ?
S3 C18 1.816(8) . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S3A O15A 1.416(8) . ?
S3A C17A 1.772(8) . ?
S3A C18A 1.733(9) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
S4 O16 1.502(9) . ?
S4 C19 1.770(5) . ?
S4 C20 1.782(12) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S4A O16A 1.491(12) . ?
S4A C19A 1.766(8) . ?
S4A C20A 1.773(14) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 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
O13 S1 C13 106.04(14) . . ?
O13 S1 C14 105.86(13) . . ?
C13 S1 C14 98.07(15) . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O14 S2 C15 106.87(13) . . ?
O14 S2 C16 105.27(12) . . ?
C15 S2 C16 98.65(15) . . ?
S2 C15 H15A 109.5 . . ?
S2 C15 H15B 109.5 . . ?
S2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N7 O5 N7 107.6(2) . 2_655 ?
H2A N2 H2B 120.0 . . ?
C5 N2 H2A 120.0 . . ?
C5 N2 H2B 120.0 . . ?
N4 N3 C6 122.12(19) . . ?
N3 N4 C4 115.72(18) . . ?
N6 N5 C4 113.89(16) . . ?
N6 N5 C5 122.64(16) . . ?
C5 N5 C4 123.41(18) . . ?
C2 N6 N5 104.22(17) . . ?
C1 N7 O5 107.4(2) . . ?
O6 N7 O5 111.8(2) . . ?
O6 N7 C1 140.7(3) . . ?
O3 N8 C3 117.5(3) . . ?
O4 N8 O3 125.4(2) . . ?
O4 N8 C3 117.0(3) . . ?
N7 C1 C1 108.80(16) . 2_655 ?
N7 C1 C2 121.7(2) . . ?
C1 C1 C2 129.11(13) 2_655 . ?
N6 C2 C1 116.99(19) . . ?
N6 C2 C3 111.32(19) . . ?
C3 C2 C1 131.58(19) . . ?
C2 C3 N8 128.6(2) . . ?
C4 C3 N8 124.7(2) . . ?
C4 C3 C2 106.38(18) . . ?
N4 C4 N5 122.88(19) . . ?
N4 C4 C3 132.9(2) . . ?
N5 C4 C3 104.16(18) . . ?
N2 C5 N5 118.68(18) . . ?
N2 C5 C6 131.71(19) . . ?
N5 C5 C6 109.59(18) . . ?
N3 C6 C5 126.1(2) . . ?
N3 C6 N1 115.1(5) . . ?
N3 C6 N1A 111.9(7) . . ?
C5 C6 N1 118.4(5) . . ?
C5 C6 N1A 121.9(7) . . ?
O1 N1 C6 114.7(11) . . ?
O2 N1 C6 120.2(9) . . ?
O2 N1 O1 124.0(12) . . ?
O1A N1A C6 115.4(15) . . ?
O2A N1A C6 117.3(13) . . ?
O2A N1A O1A 125.2(15) . . ?
N16 O12 N16 107.9(2) 2_755 . ?
O7 N9 C12 116.9(5) . . ?
O8 N9 C12 120.6(11) . . ?
O8 N9 O7 121.9(12) . . ?
O7A N9 C12 118.8(6) . . ?
O8A N9 C12 112.7(14) . . ?
O8A N9 O7A 127.2(15) . . ?
H10A N10 H10B 120.0 . . ?
C11 N10 H10A 120.0 . . ?
C11 N10 H10B 120.0 . . ?
N12 N11 C12 122.1(2) . . ?
N11 N12 C10 116.18(19) . . ?
N14 N13 C10 113.71(17) . . ?
N14 N13 C11 123.03(16) . . ?
C11 N13 C10 123.21(18) . . ?
C8 N14 N13 103.92(16) . . ?
O9 N15 C9 117.1(2) . . ?
O10 N15 O9 124.7(2) . . ?
O10 N15 C9 118.2(2) . . ?
C7 N16 O12 106.8(2) . . ?
O11 N16 O12 114.8(3) . . ?
O11 N16 C7 138.3(3) . . ?
N16 C7 C7 109.26(14) . 2_755 ?
N16 C7 C8 122.4(2) . . ?
C7 C7 C8 128.13(12) 2_755 . ?
N14 C8 C7 116.99(18) . . ?
N14 C8 C9 111.65(19) . . ?
C9 C8 C7 131.34(19) . . ?
C8 C9 N15 128.0(2) . . ?
C10 C9 N15 125.3(2) . . ?
C10 C9 C8 106.59(18) . . ?
N12 C10 N13 122.5(2) . . ?
N12 C10 C9 133.4(2) . . ?
N13 C10 C9 104.11(18) . . ?
N10 C11 N13 118.65(19) . . ?
N10 C11 C12 131.4(2) . . ?
N13 C11 C12 109.90(18) . . ?
N11 C12 N9 113.6(2) . . ?
N11 C12 C11 126.0(2) . . ?
C11 C12 N9 120.4(2) . . ?
O15 S3 C17 101.9(5) . . ?
O15 S3 C18 104.6(5) . . ?
C17 S3 C18 97.4(5) . . ?
S3 C17 H17C 109.5 . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17C C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S3 C18 H18A 109.5 . . ?
S3 C18 H18B 109.5 . . ?
S3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O15A S3A C17A 113.2(5) . . ?
O15A S3A C18A 112.9(6) . . ?
C18A S3A C17A 99.2(5) . . ?
S3A C17A H17D 109.5 . . ?
S3A C17A H17E 109.5 . . ?
S3A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
S3A C18A H18D 109.5 . . ?
S3A C18A H18E 109.5 . . ?
S3A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
O16 S4 C19 101.8(7) . . ?
O16 S4 C20 104.4(9) . . ?
C19 S4 C20 99.7(8) . . ?
S4 C19 H19A 109.5 . . ?
S4 C19 H19B 109.5 . . ?
S4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S4 C20 H20A 109.5 . . ?
S4 C20 H20B 109.5 . . ?
S4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O16A S4A C19A 109.1(6) . . ?
O16A S4A C20A 107.4(12) . . ?
C19A S4A C20A 89.6(9) . . ?
S4A C19A H19D 109.5 . . ?
S4A C19A H19E 109.5 . . ?
S4A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
S4A C20A H20D 109.5 . . ?
S4A C20A H20E 109.5 . . ?
S4A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 N8 C3 C2 30.1(4) . . . . ?
O3 N8 C3 C4 -143.4(2) . . . . ?
O4 N8 C3 C2 -151.2(2) . . . . ?
O4 N8 C3 C4 35.3(3) . . . . ?
O5 N7 C1 C1 0.4(3) . . . 2_655 ?
O5 N7 C1 C2 174.17(17) . . . . ?
N2 C5 C6 N3 -173.4(2) . . . . ?
N2 C5 C6 N1 -0.8(10) . . . . ?
N2 C5 C6 N1A 9.3(14) . . . . ?
N3 N4 C4 N5 2.2(3) . . . . ?
N3 N4 C4 C3 177.8(2) . . . . ?
N3 C6 N1 O1 -149.2(15) . . . . ?
N3 C6 N1 O2 19(2) . . . . ?
N3 C6 N1A O1A -178(2) . . . . ?
N3 C6 N1A O2A 18(3) . . . . ?
N4 N3 C6 C5 -3.7(3) . . . . ?
N4 N3 C6 N1 -176.6(9) . . . . ?
N4 N3 C6 N1A 173.8(12) . . . . ?
N5 N6 C2 C1 178.13(19) . . . . ?
N5 N6 C2 C3 1.5(2) . . . . ?
N5 C5 C6 N3 4.6(3) . . . . ?
N5 C5 C6 N1 177.3(9) . . . . ?
N5 C5 C6 N1A -172.7(13) . . . . ?
N6 N5 C4 N4 176.24(19) . . . . ?
N6 N5 C4 C3 -0.5(2) . . . . ?
N6 N5 C5 N2 -0.8(3) . . . . ?
N6 N5 C5 C6 -179.13(18) . . . . ?
N6 C2 C3 N8 -176.2(2) . . . . ?
N6 C2 C3 C4 -1.8(3) . . . . ?
N7 O5 N7 C1 -0.17(11) 2_655 . . . ?
N7 O5 N7 O6 -178.3(3) 2_655 . . . ?
N7 C1 C2 N6 -141.8(2) . . . . ?
N7 C1 C2 C3 34.0(4) . . . . ?
N8 C3 C4 N4 -0.2(4) . . . . ?
N8 C3 C4 N5 176.0(2) . . . . ?
C1 C1 C2 N6 30.5(4) 2_655 . . . ?
C1 C1 C2 C3 -153.6(3) 2_655 . . . ?
C1 C2 C3 N8 7.8(4) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C2 C3 C4 N4 -174.9(2) . . . . ?
C2 C3 C4 N5 1.3(2) . . . . ?
C4 N5 N6 C2 -0.6(2) . . . . ?
C4 N5 C5 N2 176.05(19) . . . . ?
C4 N5 C5 C6 -2.3(3) . . . . ?
C5 N5 N6 C2 176.51(19) . . . . ?
C5 N5 C4 N4 -0.9(3) . . . . ?
C5 N5 C4 C3 -177.56(19) . . . . ?
C5 C6 N1 O1 37(2) . . . . ?
C5 C6 N1 O2 -154.2(12) . . . . ?
C5 C6 N1A O1A 0(3) . . . . ?
C5 C6 N1A O2A -164.3(15) . . . . ?
C6 N3 N4 C4 0.0(3) . . . . ?
O6 N7 C1 C1 177.7(4) . . . 2_655 ?
O6 N7 C1 C2 -8.6(5) . . . . ?
O9 N15 C9 C8 166.1(3) . . . . ?
O9 N15 C9 C10 -18.8(4) . . . . ?
O10 N15 C9 C8 -15.5(4) . . . . ?
O10 N15 C9 C10 159.6(2) . . . . ?
O12 N16 C7 C7 -0.8(3) . . . 2_755 ?
O12 N16 C7 C8 -175.67(17) . . . . ?
N10 C11 C12 N9 -0.2(4) . . . . ?
N10 C11 C12 N11 179.0(3) . . . . ?
N11 N12 C10 N13 -0.6(4) . . . . ?
N11 N12 C10 C9 -178.5(3) . . . . ?
N12 N11 C12 N9 -178.9(2) . . . . ?
N12 N11 C12 C11 1.9(4) . . . . ?
N13 N14 C8 C7 -179.62(17) . . . . ?
N13 N14 C8 C9 -1.1(2) . . . . ?
N13 C11 C12 N9 -178.9(2) . . . . ?
N13 C11 C12 N11 0.3(4) . . . . ?
N14 N13 C10 N12 -179.4(2) . . . . ?
N14 N13 C10 C9 -1.0(2) . . . . ?
N14 N13 C11 N10 1.1(3) . . . . ?
N14 N13 C11 C12 179.97(19) . . . . ?
N14 C8 C9 N15 176.5(2) . . . . ?
N14 C8 C9 C10 0.6(3) . . . . ?
N15 C9 C10 N12 2.4(4) . . . . ?
N15 C9 C10 N13 -175.8(2) . . . . ?
N16 O12 N16 C7 0.30(12) 2_755 . . . ?
N16 O12 N16 O11 177.1(3) 2_755 . . . ?
N16 C7 C8 N14 134.5(2) . . . . ?
N16 C7 C8 C9 -43.6(4) . . . . ?
C7 C7 C8 N14 -39.4(4) 2_755 . . . ?
C7 C7 C8 C9 142.5(3) 2_755 . . . ?
C7 C8 C9 N15 -5.4(4) . . . . ?
C7 C8 C9 C10 178.8(2) . . . . ?
C8 C9 C10 N12 178.4(3) . . . . ?
C8 C9 C10 N13 0.2(2) . . . . ?
C10 N13 N14 C8 1.3(2) . . . . ?
C10 N13 C11 N10 178.6(2) . . . . ?
C10 N13 C11 C12 -2.5(3) . . . . ?
C11 N13 N14 C8 179.02(19) . . . . ?
C11 N13 C10 N12 2.9(3) . . . . ?
C11 N13 C10 C9 -178.65(19) . . . . ?
C12 N11 N12 C10 -1.7(4) . . . . ?
O7 N9 C12 N11 7.3(5) . . . . ?
O7 N9 C12 C11 -173.4(4) . . . . ?
O8 N9 C12 N11 178.6(15) . . . . ?
O8 N9 C12 C11 -2.1(15) . . . . ?
O7A N9 C12 N11 -26.3(6) . . . . ?
O7A N9 C12 C11 153.0(5) . . . . ?
O8A N9 C12 N11 165.7(18) . . . . ?
O8A N9 C12 C11 -15.0(18) . . . . ?
O11 N16 C7 C7 -176.4(4) . . . 2_755 ?
O11 N16 C7 C8 8.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
