# Supplementary Information (SI) for Journal of Materials Chemistry A.
# 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_h2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2368016'
loop_
_audit_author_name
_audit_author_address
a-d
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-07-04 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_audit_creation_date             2024-04-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C6 H9 N10 O2), 4(Cl O4), 3(H2 O)'
_chemical_formula_sum            'C24 H42 Cl4 N40 O27'
_chemical_formula_weight         1464.77
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   14.2998(8)
_cell_length_b                   9.2251(4)
_cell_length_c                   20.3851(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.234(3)
_cell_angle_gamma                90
_cell_volume                     2677.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5793
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.266
_cell_measurement_theta_min      3.625
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.157
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1510 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.4906.
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    1.817
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1500
_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  0.0830
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.625
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                3845
_reflns_number_total             4900
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.093
_refine_diff_density_min         -1.548
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       0.0028(3)
_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   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         4900
_refine_ls_number_restraints     176
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0979
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+18.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2248
_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 O(H,H) groups
2. Restrained distances
 O4A-N20 \\sim O4B-N20
 with sigma of 0.02
 Cl3-O15 \\sim Cl3-O14 \\sim Cl3-O16 \\sim Cl3-O13
 with sigma of 0.02
 Cl2-O10 \\sim Cl2-O9 \\sim Cl2-O11 \\sim Cl2-O12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl3 \\sim O13 \\sim O14 \\sim O15 \\sim O16: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002 within 2A
Cl2 \\sim O9 \\sim O10 \\sim O11 \\sim O12: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002 within 2A
Uanis(O4B) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O1B) \\sim Ueq, Uanis(O1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O2A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N20, O3, O4B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Cl3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 Cl3, O13, O14, O15, O16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 Cl2, O9, O10, O11, O12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N9, O1B, O2B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N9, O1A, O2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N20, O3, O4A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Sof(O1B)=Sof(O2B)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=FVAR(1)
 Sof(O4B)=1-FVAR(2)
 Sof(O4A)=FVAR(2)
 Fixed Sof: Cl2(0.5) O9(0.5) O10(0.5) O11(0.5) O12(0.5) Cl3(0.5) O13(0.5)
 O14(0.5) O15(0.5) O16(0.5) H18C(0.5) H18D(0.5)
6.a Everything fixed:
 O17, H17A, H17B, O18, H18C, H18D
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N12(H12)
6.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N3(H3A,H3B), N8(H8A,H8B), N10(H10A,H10B), N11(H11A,H11B),
 N18(H18A,H18B), N19(H19A,H19B), N21(H21A,H21B)
;
_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 0.2073(4) 0.1233(6) 0.5446(3) 0.0320(12) Uani 1 1 d . . . . .
C2 C 0.2236(4) 0.1598(6) 0.4317(3) 0.0330(12) Uani 1 1 d . . . . .
C3 C 0.1732(3) 0.3365(5) 0.4949(2) 0.0255(10) Uani 1 1 d . . . . .
C4 C 0.1099(3) 0.5441(5) 0.5535(2) 0.0255(10) Uani 1 1 d . . . . .
C5 C 0.0769(3) 0.6794(5) 0.5301(2) 0.0235(10) Uani 1 1 d . . . . .
C6 C 0.0936(3) 0.6852(5) 0.4621(2) 0.0249(10) Uani 1 1 d . . . . .
N1 N 0.2158(3) 0.0382(5) 0.5975(3) 0.0417(12) Uani 1 1 d . . . . .
H1A H 0.202054 0.071350 0.635345 0.050 Uiso 1 1 calc R U . . .
H1B H 0.235167 -0.050723 0.594135 0.050 Uiso 1 1 calc R U . . .
N2 N 0.2314(3) 0.0714(5) 0.4863(2) 0.0348(11) Uani 1 1 d . . . . .
H2 H 0.251678 -0.017139 0.483407 0.042 Uiso 1 1 calc R U . . .
N3 N 0.2465(4) 0.1080(5) 0.3756(2) 0.0447(13) Uani 1 1 d . . . . .
H3A H 0.243255 0.163022 0.340812 0.054 Uiso 1 1 calc R U . . .
H3B H 0.265010 0.018451 0.373075 0.054 Uiso 1 1 calc R U . . .
N4 N 0.1954(3) 0.2969(5) 0.4352(2) 0.0314(10) Uani 1 1 d . . . . .
N5 N 0.1775(3) 0.2593(4) 0.5506(2) 0.0286(9) Uani 1 1 d . . . . .
N6 N 0.1416(3) 0.4762(4) 0.50012(19) 0.0249(9) Uani 1 1 d . . . . .
N7 N 0.1317(3) 0.5657(5) 0.44285(19) 0.0289(10) Uani 1 1 d . . . . .
N8 N 0.0756(4) 0.7999(5) 0.4211(2) 0.0375(11) Uani 1 1 d . . . . .
H8A H 0.089537 0.795269 0.380536 0.045 Uiso 1 1 calc R U . . .
H8B H 0.050103 0.878002 0.435490 0.045 Uiso 1 1 calc R U . . .
N9 N 0.0353(3) 0.7810(5) 0.5666(2) 0.0323(10) Uani 1 1 d . . . . .
N10 N 0.1127(4) 0.4902(5) 0.6141(2) 0.0398(12) Uani 1 1 d . . . . .
H10A H 0.136169 0.404526 0.622413 0.048 Uiso 1 1 calc R U . . .
H10B H 0.090936 0.540703 0.645367 0.048 Uiso 1 1 calc R U . . .
O1A O 0.031(7) 0.909(7) 0.543(3) 0.036(10) Uani 0.18(8) 1 d . U P A 1
O1B O -0.0001(18) 0.8910(15) 0.5397(7) 0.035(3) Uani 0.82(8) 1 d . U P A 2
O2A O 0.058(6) 0.772(7) 0.631(2) 0.037(10) Uani 0.18(8) 1 d . U P A 1
O2B O 0.021(3) 0.7523(15) 0.6238(7) 0.049(5) Uani 0.82(8) 1 d . . P A 2
C7 C 0.5207(4) 0.7888(6) 0.6902(3) 0.0351(13) Uani 1 1 d . . . . .
C8 C 0.5540(3) 0.7211(5) 0.5892(2) 0.0249(10) Uani 1 1 d . . . . .
C9 C 0.4914(4) 0.9427(6) 0.5992(2) 0.0272(11) Uani 1 1 d . . . . .
C10 C 0.6165(4) 0.4769(5) 0.5675(3) 0.0296(11) Uani 1 1 d . . . . .
C11 C 0.6419(3) 0.4149(5) 0.5092(3) 0.0289(11) Uani 1 1 d . . . . .
C12 C 0.6264(3) 0.5224(6) 0.4589(3) 0.0280(11) Uani 1 1 d . . . . .
N11 N 0.5212(5) 0.7685(7) 0.7543(2) 0.0589(17) Uani 1 1 d . . . . .
H11A H 0.543693 0.688577 0.772082 0.071 Uiso 1 1 calc R U . . .
H11B H 0.499070 0.835148 0.778871 0.071 Uiso 1 1 calc R U . . .
N12 N 0.4867(4) 0.9147(5) 0.6646(2) 0.0382(12) Uani 1 1 d . . . . .
H12 H 0.461921 0.977829 0.689496 0.046 Uiso 1 1 calc R U . . .
N14 N 0.5253(3) 0.8450(4) 0.55953(19) 0.0245(9) Uani 1 1 d . . . . .
N15 N 0.5543(3) 0.6877(5) 0.6531(2) 0.0324(10) Uani 1 1 d . . . . .
N16 N 0.5870(3) 0.6154(4) 0.55024(19) 0.0255(9) Uani 1 1 d . . . . .
N17 N 0.5944(3) 0.6437(5) 0.4819(2) 0.0277(9) Uani 1 1 d . . . . .
N18 N 0.6432(3) 0.5067(5) 0.3950(2) 0.0398(12) Uani 1 1 d . . . . .
H18A H 0.632851 0.578509 0.367680 0.048 Uiso 1 1 calc R U . . .
H18B H 0.664468 0.424754 0.381322 0.048 Uiso 1 1 calc R U . . .
N19 N 0.6183(4) 0.4215(5) 0.6275(2) 0.0435(12) Uani 1 1 d . . . . .
H19A H 0.599978 0.473458 0.659589 0.052 Uiso 1 1 calc R U . . .
H19B H 0.637828 0.333201 0.634873 0.052 Uiso 1 1 calc R U . . .
N20 N 0.6743(3) 0.2771(5) 0.5033(3) 0.0395(12) Uani 1 1 d D . . . .
N21 N 0.4607(3) 1.0695(5) 0.5769(2) 0.0374(11) Uani 1 1 d . . . . .
H21A H 0.462307 1.091065 0.535507 0.045 Uiso 1 1 calc R U . . .
H21B H 0.438773 1.131843 0.603668 0.045 Uiso 1 1 calc R U . . .
O3 O 0.6809(3) 0.1946(4) 0.5522(2) 0.0506(12) Uani 1 1 d . . . . .
O4A O 0.703(4) 0.234(4) 0.4495(15) 0.048(4) Uani 0.7(2) 1 d D U P B 1
O4B O 0.684(9) 0.238(8) 0.4442(19) 0.038(12) Uani 0.3(2) 1 d D U P B 2
Cl2 Cl 0.2462(9) 0.7845(3) 0.7501(7) 0.0574(7) Uani 0.5 1 d D U P C -1
O9 O 0.1785(7) 0.9020(11) 0.7421(5) 0.0586(12) Uani 0.5 1 d D U P C -1
O10 O 0.3136(8) 0.7984(12) 0.8042(5) 0.0653(13) Uani 0.5 1 d D U P C -1
O11 O 0.2784(7) 0.7659(11) 0.6869(5) 0.0591(12) Uani 0.5 1 d D U P C -1
O12 O 0.1867(7) 0.6582(11) 0.7600(5) 0.0615(12) Uani 0.5 1 d D U P C -1
Cl3 Cl 0.7505(11) 0.1650(3) 0.7491(7) 0.0546(6) Uani 0.5 1 d D U P D -1
O13 O 0.6783(7) 0.1365(11) 0.6970(4) 0.0569(12) Uani 0.5 1 d D U P D -1
O14 O 0.8102(7) 0.0433(10) 0.7581(4) 0.0589(12) Uani 0.5 1 d D U P D -1
O15 O 0.8053(8) 0.2825(11) 0.7257(5) 0.0626(12) Uani 0.5 1 d D U P D -1
O16 O 0.7116(8) 0.2018(11) 0.8075(5) 0.0585(12) Uani 0.5 1 d D U P D -1
Cl1 Cl 0.41698(11) 1.23349(18) 0.75407(7) 0.0474(4) Uani 1 1 d . . . . .
O5 O 0.3785(4) 1.2081(6) 0.6860(2) 0.0613(14) Uani 1 1 d . . . . .
O6 O 0.3448(3) 1.2399(5) 0.7960(2) 0.0551(12) Uani 1 1 d . . . . .
O7 O 0.4798(4) 1.1169(7) 0.7727(3) 0.0823(19) Uani 1 1 d . . . . .
O8 O 0.4672(5) 1.3654(8) 0.7569(3) 0.100(2) Uani 1 1 d . . . . .
O17 O 0.875870 0.535470 0.692610 0.066 Uani 1 1 d . . . . .
H17A H 0.885270 0.444900 0.700720 0.099 Uiso 1 1 d . U . . .
H17B H 0.848830 0.537510 0.653170 0.099 Uiso 1 1 d . U . . .
O18 O 0.750000 0.709320 0.750000 0.070 Uani 1 2 d S T P . .
H18C H 0.787260 0.641880 0.739300 0.105 Uiso 0.5 1 d . U P . .
H18D H 0.722070 0.673020 0.781820 0.105 Uiso 0.5 1 d . U P . .


_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 N1 1.329(7) . ?
C1 N2 1.355(7) . ?
C1 N5 1.334(7) . ?
C2 N2 1.376(7) . ?
C2 N3 1.309(7) . ?
C2 N4 1.332(7) . ?
C3 N4 1.337(7) . ?
C3 N5 1.338(7) . ?
C3 N6 1.373(6) . ?
C4 C5 1.402(7) . ?
C4 N6 1.367(6) . ?
C4 N10 1.329(6) . ?
C5 C6 1.428(7) . ?
C5 N9 1.366(6) . ?
C6 N7 1.306(6) . ?
C6 N8 1.359(6) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N2 H2 0.8700 . ?
N3 H3A 0.8700 . ?
N3 H3B 0.8700 . ?
N6 N7 1.426(5) . ?
N8 H8A 0.8700 . ?
N8 H8B 0.8700 . ?
N9 O1A 1.28(6) . ?
N9 O1B 1.240(11) . ?
N9 O2A 1.33(5) . ?
N9 O2B 1.232(10) . ?
N10 H10A 0.8700 . ?
N10 H10B 0.8700 . ?
C7 N11 1.320(7) . ?
C7 N12 1.346(7) . ?
C7 N15 1.319(7) . ?
C8 N14 1.339(6) . ?
C8 N15 1.337(6) . ?
C8 N16 1.369(6) . ?
C9 N12 1.365(6) . ?
C9 N14 1.331(6) . ?
C9 N21 1.316(7) . ?
C10 C11 1.396(7) . ?
C10 N16 1.381(6) . ?
C10 N19 1.324(7) . ?
C11 C12 1.430(7) . ?
C11 N20 1.362(7) . ?
C12 N17 1.312(6) . ?
C12 N18 1.353(7) . ?
N11 H11A 0.8700 . ?
N11 H11B 0.8700 . ?
N12 H12 0.8700 . ?
N16 N17 1.431(5) . ?
N18 H18A 0.8700 . ?
N18 H18B 0.8700 . ?
N19 H19A 0.8700 . ?
N19 H19B 0.8700 . ?
N20 O3 1.250(7) . ?
N20 O4A 1.270(10) . ?
N20 O4B 1.275(17) . ?
N21 H21A 0.8700 . ?
N21 H21B 0.8700 . ?
Cl2 O9 1.452(11) . ?
Cl2 O10 1.403(12) . ?
Cl2 O11 1.418(13) . ?
Cl2 O12 1.468(11) . ?
Cl3 O13 1.436(14) . ?
Cl3 O14 1.413(11) . ?
Cl3 O15 1.445(11) . ?
Cl3 O16 1.400(13) . ?
Cl1 O5 1.463(4) . ?
Cl1 O6 1.401(5) . ?
Cl1 O7 1.430(6) . ?
Cl1 O8 1.412(6) . ?
O17 H17A 0.8599 . ?
O17 H17B 0.8600 . ?
O18 H18C 0.8601 2_656 ?
O18 H18C 0.8601 . ?
O18 H18D 0.8601 2_656 ?
O18 H18D 0.8600 . ?

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
N1 C1 N2 119.4(5) . . ?
N1 C1 N5 119.2(5) . . ?
N5 C1 N2 121.4(5) . . ?
N3 C2 N2 118.8(5) . . ?
N3 C2 N4 119.7(5) . . ?
N4 C2 N2 121.5(5) . . ?
N4 C3 N5 129.1(5) . . ?
N4 C3 N6 115.8(4) . . ?
N5 C3 N6 115.1(4) . . ?
N6 C4 C5 105.3(4) . . ?
N10 C4 C5 129.0(5) . . ?
N10 C4 N6 125.8(5) . . ?
C4 C5 C6 106.4(4) . . ?
N9 C5 C4 125.1(4) . . ?
N9 C5 C6 128.5(4) . . ?
N7 C6 C5 111.8(4) . . ?
N7 C6 N8 122.2(4) . . ?
N8 C6 C5 125.9(4) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 119.5(4) . . ?
C1 N2 H2 120.3 . . ?
C2 N2 H2 120.3 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 N4 C3 114.0(5) . . ?
C1 N5 C3 114.5(4) . . ?
C3 N6 N7 119.2(4) . . ?
C4 N6 C3 128.8(4) . . ?
C4 N6 N7 111.8(4) . . ?
C6 N7 N6 104.7(4) . . ?
C6 N8 H8A 120.0 . . ?
C6 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
O1A N9 C5 116(3) . . ?
O1A N9 O2A 115(5) . . ?
O1B N9 C5 120.1(7) . . ?
O2A N9 C5 115(2) . . ?
O2B N9 C5 119.2(6) . . ?
O2B N9 O1B 119.8(11) . . ?
C4 N10 H10A 120.0 . . ?
C4 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N11 C7 N12 118.4(5) . . ?
N15 C7 N11 120.0(5) . . ?
N15 C7 N12 121.6(5) . . ?
N14 C8 N16 116.9(4) . . ?
N15 C8 N14 127.6(5) . . ?
N15 C8 N16 115.5(4) . . ?
N14 C9 N12 121.2(5) . . ?
N21 C9 N12 117.4(4) . . ?
N21 C9 N14 121.5(4) . . ?
N16 C10 C11 105.1(4) . . ?
N19 C10 C11 130.0(5) . . ?
N19 C10 N16 124.9(5) . . ?
C10 C11 C12 106.9(4) . . ?
N20 C11 C10 125.1(5) . . ?
N20 C11 C12 128.0(5) . . ?
N17 C12 C11 111.8(4) . . ?
N17 C12 N18 122.3(5) . . ?
N18 C12 C11 125.9(5) . . ?
C7 N11 H11A 120.0 . . ?
C7 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C7 N12 C9 119.6(4) . . ?
C7 N12 H12 120.2 . . ?
C9 N12 H12 120.2 . . ?
C9 N14 C8 114.6(4) . . ?
C7 N15 C8 115.3(4) . . ?
C8 N16 C10 128.7(4) . . ?
C8 N16 N17 119.7(4) . . ?
C10 N16 N17 111.6(4) . . ?
C12 N17 N16 104.6(4) . . ?
C12 N18 H18A 120.0 . . ?
C12 N18 H18B 120.0 . . ?
H18A N18 H18B 120.0 . . ?
C10 N19 H19A 120.0 . . ?
C10 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
O3 N20 C11 119.9(5) . . ?
O3 N20 O4A 119(2) . . ?
O3 N20 O4B 125(4) . . ?
O4A N20 C11 121(2) . . ?
O4B N20 C11 114(4) . . ?
C9 N21 H21A 120.0 . . ?
C9 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
O9 Cl2 O12 102.6(10) . . ?
O10 Cl2 O9 115.0(9) . . ?
O10 Cl2 O11 117.9(11) . . ?
O10 Cl2 O12 109.2(10) . . ?
O11 Cl2 O9 104.9(9) . . ?
O11 Cl2 O12 105.6(8) . . ?
O13 Cl3 O15 105.5(10) . . ?
O14 Cl3 O13 109.6(8) . . ?
O14 Cl3 O15 107.4(12) . . ?
O16 Cl3 O13 111.0(12) . . ?
O16 Cl3 O14 111.4(11) . . ?
O16 Cl3 O15 111.6(8) . . ?
O6 Cl1 O5 110.6(3) . . ?
O6 Cl1 O7 110.4(4) . . ?
O6 Cl1 O8 109.8(3) . . ?
O7 Cl1 O5 107.7(3) . . ?
O8 Cl1 O5 108.8(4) . . ?
O8 Cl1 O7 109.4(5) . . ?
H17A O17 H17B 104.5 . . ?
H18C O18 H18C 87.3 . 2_656 ?
H18C O18 H18D 104.5 2_656 2_656 ?
H18C O18 H18D 104.5 . . ?
H18C O18 H18D 35.5 . 2_656 ?
H18D O18 H18C 35.5 . 2_656 ?
H18D O18 H18D 134.2 . 2_656 ?

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
C3 N6 N7 C6 174.8(4) . . . . ?
C4 C5 C6 N7 1.1(6) . . . . ?
C4 C5 C6 N8 -177.2(5) . . . . ?
C4 C5 N9 O1A 163(5) . . . . ?
C4 C5 N9 O1B -172.6(16) . . . . ?
C4 C5 N9 O2A 24(4) . . . . ?
C4 C5 N9 O2B -4(2) . . . . ?
C4 N6 N7 C6 -0.6(6) . . . . ?
C5 C4 N6 C3 -173.6(5) . . . . ?
C5 C4 N6 N7 1.3(6) . . . . ?
C5 C6 N7 N6 -0.3(6) . . . . ?
C6 C5 N9 O1A -18(5) . . . . ?
C6 C5 N9 O1B 5.7(17) . . . . ?
C6 C5 N9 O2A -157(4) . . . . ?
C6 C5 N9 O2B 175(2) . . . . ?
N1 C1 N2 C2 -179.3(5) . . . . ?
N1 C1 N5 C3 178.8(5) . . . . ?
N2 C1 N5 C3 0.6(7) . . . . ?
N2 C2 N4 C3 -2.1(7) . . . . ?
N3 C2 N2 C1 -179.5(5) . . . . ?
N3 C2 N4 C3 179.4(5) . . . . ?
N4 C2 N2 C1 1.9(8) . . . . ?
N4 C3 N5 C1 -0.9(8) . . . . ?
N4 C3 N6 C4 176.6(5) . . . . ?
N4 C3 N6 N7 2.1(7) . . . . ?
N5 C1 N2 C2 -1.1(8) . . . . ?
N5 C3 N4 C2 1.7(8) . . . . ?
N5 C3 N6 C4 -3.5(7) . . . . ?
N5 C3 N6 N7 -178.1(4) . . . . ?
N6 C3 N4 C2 -178.5(4) . . . . ?
N6 C3 N5 C1 179.3(4) . . . . ?
N6 C4 C5 C6 -1.4(5) . . . . ?
N6 C4 C5 N9 177.3(5) . . . . ?
N8 C6 N7 N6 178.0(5) . . . . ?
N9 C5 C6 N7 -177.5(5) . . . . ?
N9 C5 C6 N8 4.3(9) . . . . ?
N10 C4 C5 C6 177.6(5) . . . . ?
N10 C4 C5 N9 -3.8(9) . . . . ?
N10 C4 N6 C3 7.4(9) . . . . ?
N10 C4 N6 N7 -177.7(5) . . . . ?
C8 N16 N17 C12 -179.2(4) . . . . ?
C10 C11 C12 N17 0.3(6) . . . . ?
C10 C11 C12 N18 179.2(5) . . . . ?
C10 C11 N20 O3 1.9(8) . . . . ?
C10 C11 N20 O4A -174(3) . . . . ?
C10 C11 N20 O4B 173(6) . . . . ?
C10 N16 N17 C12 1.1(5) . . . . ?
C11 C10 N16 C8 179.5(5) . . . . ?
C11 C10 N16 N17 -0.9(6) . . . . ?
C11 C12 N17 N16 -0.8(6) . . . . ?
C12 C11 N20 O3 -177.6(5) . . . . ?
C12 C11 N20 O4A 6(3) . . . . ?
C12 C11 N20 O4B -7(6) . . . . ?
N11 C7 N12 C9 175.4(6) . . . . ?
N11 C7 N15 C8 -177.4(6) . . . . ?
N12 C7 N15 C8 1.6(8) . . . . ?
N12 C9 N14 C8 -0.4(7) . . . . ?
N14 C8 N15 C7 1.2(8) . . . . ?
N14 C8 N16 C10 -176.8(5) . . . . ?
N14 C8 N16 N17 3.6(7) . . . . ?
N14 C9 N12 C7 2.9(8) . . . . ?
N15 C7 N12 C9 -3.6(9) . . . . ?
N15 C8 N14 C9 -1.7(8) . . . . ?
N15 C8 N16 C10 3.1(8) . . . . ?
N15 C8 N16 N17 -176.5(4) . . . . ?
N16 C8 N14 C9 178.1(4) . . . . ?
N16 C8 N15 C7 -178.6(5) . . . . ?
N16 C10 C11 C12 0.4(6) . . . . ?
N16 C10 C11 N20 -179.2(5) . . . . ?
N18 C12 N17 N16 -179.7(5) . . . . ?
N19 C10 C11 C12 -179.8(6) . . . . ?
N19 C10 C11 N20 0.6(10) . . . . ?
N19 C10 N16 C8 -0.4(9) . . . . ?
N19 C10 N16 N17 179.3(5) . . . . ?
N20 C11 C12 N17 179.8(5) . . . . ?
N20 C11 C12 N18 -1.3(9) . . . . ?
N21 C9 N12 C7 -177.4(5) . . . . ?
N21 C9 N14 C8 179.9(5) . . . . ?

_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_20240516_wq_nlg_h4_0m
_database_code_depnum_ccdc_archive 'CCDC 2368019'
loop_
_audit_author_name
_audit_author_address
a-d
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-07-04 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_audit_creation_date             2024-05-17
_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         '2(C11 H10 N14 O8), C3 H7 N O, 3(H2 O)'
_chemical_formula_sum            'C25 H33 N29 O20'
_chemical_formula_weight         1059.80
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.494(6)
_cell_length_b                   19.039(9)
_cell_length_c                   16.146(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.069(14)
_cell_angle_gamma                90
_cell_volume                     4041(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    167
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      55.360
_cell_measurement_theta_min      20.791
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    1.323
_exptl_absorpt_correction_T_max  0.3825
_exptl_absorpt_correction_T_min  0.2633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1819 before and 0.0739 after correction.
The Ratio of minimum to maximum transmission is 0.6884.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2184
_exptl_crystal_size_max          0.12
_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  0.0866
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23233
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.645
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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                4112
_reflns_number_total             7095
_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         0.409
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         7095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1761
_refine_ls_R_factor_gt           0.0999
_refine_ls_restrained_S_all      0.993
_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)+(0.0200P)²+28.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2246
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, 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:
 O17(H17A,H17B), O18(H18A,H18B), O19(H19A,H19B)
2.b Rotating group:
 N14(H14A,H14B), N15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), N10(H10), N11(H11), N17(H17), N19(H19), N24(H24), N26(H26),
 C25(H25)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N7(H7A,H7B), N21(H21A,H21B), N27(H27A,H27B)
2.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_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
O1 O 0.7774(4) 0.6918(3) 1.2379(3) 0.0673(15) Uani 1 1 d . . . . .
O2 O 0.7312(5) 0.5831(3) 1.2501(3) 0.0662(15) Uani 1 1 d . . . . .
O3 O 0.6747(4) 0.4415(3) 1.2460(3) 0.0663(15) Uani 1 1 d . . . . .
O4 O 0.6298(5) 0.3339(3) 1.2529(3) 0.0761(17) Uani 1 1 d . . . . .
O5 O 0.4744(5) 0.2123(3) 0.9764(4) 0.0785(18) Uani 1 1 d . . . . .
O6 O 0.4746(4) 0.2652(3) 0.8595(3) 0.0643(15) Uani 1 1 d . . . . .
O7 O 0.4658(5) 0.3417(3) 0.6942(3) 0.0707(16) Uani 1 1 d . . . . .
O8 O 0.4737(5) 0.4099(3) 0.5867(3) 0.087(2) Uani 1 1 d . . . . .
N1 N 0.7601(4) 0.7470(3) 1.0738(4) 0.0541(15) Uani 1 1 d . . . . .
H1A H 0.760894 0.774273 1.030726 0.065 Uiso 1 1 calc R U . . .
H1B H 0.782077 0.762539 1.125401 0.065 Uiso 1 1 calc R U . . .
N2 N 0.6902(4) 0.6534(3) 0.9838(3) 0.0460(14) Uani 1 1 d . . . . .
H2 H 0.686486 0.676088 0.936417 0.055 Uiso 1 1 calc R U . . .
N3 N 0.6599(4) 0.5828(3) 0.9886(3) 0.0456(13) Uani 1 1 d . . . . .
N4 N 0.7431(5) 0.6347(3) 1.2066(4) 0.0546(16) Uani 1 1 d . . . . .
N5 N 0.6595(4) 0.5057(3) 1.1071(3) 0.0446(13) Uani 1 1 d . . . . .
H5 H 0.675871 0.504860 1.162393 0.054 Uiso 1 1 calc R U . . .
N6 N 0.6400(5) 0.3868(3) 1.2095(4) 0.0590(17) Uani 1 1 d . . . . .
N7 N 0.5555(5) 0.2649(3) 1.1191(4) 0.0624(17) Uani 1 1 d . . . . .
H7A H 0.572773 0.264958 1.174411 0.075 Uiso 1 1 calc R U . . .
H7B H 0.530207 0.227179 1.092037 0.075 Uiso 1 1 calc R U . . .
N8 N 0.4975(5) 0.2652(3) 0.9383(4) 0.0564(16) Uani 1 1 d . . . . .
N9 N 0.5946(4) 0.4452(3) 0.9850(3) 0.0425(13) Uani 1 1 d . . . . .
N10 N 0.5338(4) 0.3923(3) 0.8575(3) 0.0486(14) Uani 1 1 d . . . . .
H10 H 0.510482 0.354487 0.829528 0.058 Uiso 1 1 calc R U . . .
N11 N 0.5782(5) 0.5132(3) 0.8376(4) 0.0511(15) Uani 1 1 d . . . . .
H11 H 0.598582 0.524296 0.891009 0.061 Uiso 1 1 calc R U . . .
N12 N 0.5776(5) 0.5592(3) 0.7701(4) 0.0569(16) Uani 1 1 d . . . . .
N13 N 0.4849(6) 0.3992(3) 0.6650(4) 0.0669(19) Uani 1 1 d . . . . .
N14 N 0.5317(6) 0.5530(4) 0.6214(4) 0.081(2) Uani 1 1 d . . . . .
H14A H 0.492378 0.526833 0.583222 0.097 Uiso 1 1 d R U . . .
H14B H 0.504888 0.594633 0.621183 0.097 Uiso 1 1 d R U . . .
C1 C 0.7252(5) 0.6812(3) 1.0608(4) 0.0469(16) Uani 1 1 d . . . . .
C2 C 0.7170(5) 0.6278(3) 1.1192(4) 0.0448(16) Uani 1 1 d . . . . .
C3 C 0.6772(5) 0.5686(3) 1.0706(4) 0.0425(15) Uani 1 1 d . . . . .
C4 C 0.6204(5) 0.4451(3) 1.0697(4) 0.0430(16) Uani 1 1 d . . . . .
C5 C 0.6089(5) 0.3846(3) 1.1186(4) 0.0467(17) Uani 1 1 d . . . . .
C6 C 0.5677(6) 0.3219(3) 1.0766(5) 0.0507(18) Uani 1 1 d . . . . .
C7 C 0.5412(5) 0.3241(3) 0.9854(4) 0.0456(16) Uani 1 1 d . . . . .
C8 C 0.5565(5) 0.3871(3) 0.9438(4) 0.0427(15) Uani 1 1 d . . . . .
C9 C 0.5436(5) 0.4507(3) 0.8094(4) 0.0460(16) Uani 1 1 d . . . . .
C10 C 0.5212(6) 0.4536(4) 0.7203(4) 0.0532(18) Uani 1 1 d . . . . .
C11 C 0.5408(6) 0.5238(4) 0.6993(5) 0.058(2) Uani 1 1 d . . . . .
O9 O 0.2849(4) 0.0476(2) 0.2347(3) 0.0582(14) Uani 1 1 d . . . . .
O10 O 0.3538(4) -0.0975(3) 0.2700(3) 0.0633(14) Uani 1 1 d . . . . .
O11 O 0.2215(4) 0.1534(3) 0.2289(3) 0.0621(14) Uani 1 1 d . . . . .
O12 O 0.4073(4) -0.2034(3) 0.2888(3) 0.0642(15) Uani 1 1 d . . . . .
O13 O 0.5291(5) -0.2882(2) 0.5922(3) 0.0699(16) Uani 1 1 d . . . . .
O14 O 0.5324(4) -0.2142(3) 0.6927(3) 0.0624(14) Uani 1 1 d . . . . .
O15 O 0.5195(4) -0.1252(3) 0.8345(3) 0.0641(15) Uani 1 1 d . . . . .
O16 O 0.5094(5) -0.0449(3) 0.9286(3) 0.0788(18) Uani 1 1 d . . . . .
O20 O 0.2180(8) 0.3060(4) 0.5194(4) 0.128(3) Uani 1 1 d . . . . .
N15 N 0.2345(5) 0.2268(3) 0.3829(4) 0.0538(15) Uani 1 1 d . . . . .
H15A H 0.179539 0.222342 0.342826 0.065 Uiso 1 1 d R U . . .
H15B H 0.219776 0.248672 0.426007 0.065 Uiso 1 1 d R U . . .
N16 N 0.3027(4) 0.1452(3) 0.4906(3) 0.0426(13) Uani 1 1 d . . . . .
N17 N 0.3374(4) 0.0756(3) 0.4922(3) 0.0430(13) Uani 1 1 d . . . . .
H17 H 0.362456 0.052144 0.538423 0.052 Uiso 1 1 calc R U . . .
N18 N 0.2636(5) 0.1013(3) 0.2698(3) 0.0515(15) Uani 1 1 d . . . . .
N19 N 0.3510(4) -0.0156(3) 0.3917(3) 0.0429(13) Uani 1 1 d . . . . .
H19 H 0.338672 -0.023790 0.337332 0.051 Uiso 1 1 calc R U . . .
N20 N 0.3904(4) -0.1463(3) 0.3191(3) 0.0481(14) Uani 1 1 d . . . . .
N21 N 0.4777(5) -0.2525(3) 0.4378(4) 0.0642(18) Uani 1 1 d . . . . .
H21A H 0.467226 -0.260516 0.383474 0.077 Uiso 1 1 calc R U . . .
H21B H 0.503498 -0.285125 0.473972 0.077 Uiso 1 1 calc R U . . .
N22 N 0.5124(5) -0.2280(3) 0.6148(4) 0.0501(14) Uani 1 1 d . . . . .
N23 N 0.4108(4) -0.0570(2) 0.5261(3) 0.0390(12) Uani 1 1 d . . . . .
N24 N 0.4644(4) -0.0905(3) 0.6646(3) 0.0396(12) Uani 1 1 d . . . . .
H24 H 0.488725 -0.123780 0.700240 0.047 Uiso 1 1 calc R U . . .
N25 N 0.4110(4) 0.0304(3) 0.6585(3) 0.0447(13) Uani 1 1 d . . . . .
N26 N 0.4067(5) 0.0805(3) 0.7216(4) 0.0548(16) Uani 1 1 d . . . . .
H26 H 0.385806 0.123470 0.711161 0.066 Uiso 1 1 calc R U . . .
N27 N 0.4418(6) 0.0907(3) 0.8711(4) 0.077(2) Uani 1 1 d . . . . .
H27A H 0.422125 0.134299 0.867839 0.092 Uiso 1 1 calc R U . . .
H27B H 0.463319 0.070989 0.920485 0.092 Uiso 1 1 calc R U . . .
N28 N 0.4989(5) -0.0638(3) 0.8535(4) 0.0595(17) Uani 1 1 d . . . . .
N29 N 0.2292(6) 0.4249(4) 0.5065(4) 0.080(2) Uani 1 1 d . . . . .
C12 C 0.2708(5) 0.1623(3) 0.4086(4) 0.0465(17) Uani 1 1 d . . . . .
C13 C 0.2843(5) 0.1043(3) 0.3575(4) 0.0403(15) Uani 1 1 d . . . . .
C14 C 0.3270(5) 0.0504(3) 0.4147(4) 0.0392(15) Uani 1 1 d . . . . .
C15 C 0.3916(5) -0.0702(3) 0.4430(4) 0.0382(14) Uani 1 1 d . . . . .
C16 C 0.4123(5) -0.1356(3) 0.4098(4) 0.0409(15) Uani 1 1 d . . . . .
C17 C 0.4542(5) -0.1901(3) 0.4656(4) 0.0436(16) Uani 1 1 d . . . . .
C18 C 0.4731(5) -0.1755(3) 0.5547(4) 0.0402(15) Uani 1 1 d . . . . .
C19 C 0.4490(5) -0.1075(3) 0.5810(4) 0.0363(14) Uani 1 1 d . . . . .
C20 C 0.4464(5) -0.0272(3) 0.7004(4) 0.0433(16) Uani 1 1 d . . . . .
C21 C 0.4638(6) -0.0161(4) 0.7891(4) 0.0496(17) Uani 1 1 d . . . . .
C22 C 0.4389(6) 0.0537(4) 0.7997(4) 0.057(2) Uani 1 1 d . . . . .
C23 C 0.2469(9) 0.4943(5) 0.5479(7) 0.115(4) Uani 1 1 d . . . . .
H23A H 0.188560 0.524296 0.526783 0.173 Uiso 1 1 calc R U . . .
H23B H 0.307158 0.515412 0.535320 0.173 Uiso 1 1 calc R U . . .
H23C H 0.256424 0.488671 0.608944 0.173 Uiso 1 1 calc R U . . .
C24 C 0.2220(10) 0.4218(6) 0.4174(6) 0.115(4) Uani 1 1 d . . . . .
H24A H 0.283411 0.400947 0.406564 0.173 Uiso 1 1 calc R U . . .
H24B H 0.213779 0.468849 0.393830 0.173 Uiso 1 1 calc R U . . .
H24C H 0.163711 0.393374 0.390900 0.173 Uiso 1 1 calc R U . . .
C25 C 0.2273(10) 0.3659(6) 0.5491(6) 0.109(4) Uani 1 1 d . . . . .
H25 H 0.233644 0.369924 0.608119 0.131 Uiso 1 1 calc R U . . .
O17 O 0.7264(7) 0.8379(5) 0.9366(5) 0.122(3) Uani 1 1 d G . . . .
H17A H 0.663329 0.848587 0.918492 0.183 Uiso 1 1 d G U . . .
H17B H 0.751529 0.840443 0.892180 0.183 Uiso 1 1 d G U . . .
O18 O 0.6727(5) 0.6880(3) 0.8167(3) 0.0675(15) Uani 1 1 d G . . . .
H18A H 0.648161 0.720417 0.780875 0.101 Uiso 1 1 d G U . . .
H18B H 0.640643 0.650576 0.796093 0.101 Uiso 1 1 d G U . . .
O19 O 0.3229(5) 0.2029(3) 0.6582(4) 0.0734(16) Uani 1 1 d G . . . .
H19A H 0.342242 0.244455 0.675562 0.110 Uiso 1 1 d G U . . .
H19B H 0.304999 0.206791 0.603718 0.110 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
O1 N4 1.242(7) . ?
O2 N4 1.239(7) . ?
O3 N6 1.237(7) . ?
O4 N6 1.251(7) . ?
O5 N8 1.255(8) . ?
O6 N8 1.240(8) . ?
O7 N13 1.241(8) . ?
O8 N13 1.256(8) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C1 1.338(8) . ?
N2 H2 0.8700 . ?
N2 N3 1.412(7) . ?
N2 C1 1.335(8) . ?
N3 C3 1.319(8) . ?
N4 C2 1.381(8) . ?
N5 H5 0.8700 . ?
N5 C3 1.380(8) . ?
N5 C4 1.352(8) . ?
N6 C5 1.432(9) . ?
N7 H7A 0.8700 . ?
N7 H7B 0.8700 . ?
N7 C6 1.313(9) . ?
N8 C7 1.407(8) . ?
N9 C4 1.334(8) . ?
N9 C8 1.332(8) . ?
N10 H10 0.8700 . ?
N10 C8 1.361(8) . ?
N10 C9 1.380(8) . ?
N11 H11 0.8700 . ?
N11 N12 1.395(8) . ?
N11 C9 1.321(8) . ?
N12 C11 1.322(9) . ?
N13 C10 1.384(9) . ?
N14 H14A 0.8721 . ?
N14 H14B 0.8719 . ?
N14 C11 1.356(9) . ?
C1 C2 1.408(9) . ?
C2 C3 1.409(9) . ?
C4 C5 1.424(9) . ?
C5 C6 1.424(9) . ?
C6 C7 1.435(10) . ?
C7 C8 1.413(9) . ?
C9 C10 1.403(9) . ?
C10 C11 1.418(10) . ?
O9 N18 1.235(7) . ?
O10 N20 1.248(7) . ?
O11 N18 1.255(7) . ?
O12 N20 1.235(7) . ?
O13 N22 1.239(7) . ?
O14 N22 1.253(7) . ?
O15 N28 1.256(8) . ?
O16 N28 1.241(7) . ?
O20 C25 1.231(11) . ?
N15 H15A 0.8718 . ?
N15 H15B 0.8719 . ?
N15 C12 1.351(8) . ?
N16 N17 1.403(7) . ?
N16 C12 1.337(8) . ?
N17 H17 0.8700 . ?
N17 C14 1.317(8) . ?
N18 C13 1.382(8) . ?
N19 H19 0.8700 . ?
N19 C14 1.370(8) . ?
N19 C15 1.365(8) . ?
N20 C16 1.440(8) . ?
N21 H21A 0.8700 . ?
N21 H21B 0.8700 . ?
N21 C17 1.333(8) . ?
N22 C18 1.411(8) . ?
N23 C15 1.332(7) . ?
N23 C19 1.330(8) . ?
N24 H24 0.8700 . ?
N24 C19 1.357(8) . ?
N24 C20 1.381(8) . ?
N25 N26 1.405(7) . ?
N25 C20 1.321(8) . ?
N26 H26 0.8700 . ?
N26 C22 1.339(9) . ?
N27 H27A 0.8700 . ?
N27 H27B 0.8700 . ?
N27 C22 1.343(9) . ?
N28 C21 1.382(9) . ?
N29 C23 1.474(11) . ?
N29 C24 1.421(11) . ?
N29 C25 1.322(11) . ?
C12 C13 1.413(9) . ?
C13 C14 1.414(8) . ?
C15 C16 1.409(9) . ?
C16 C17 1.407(9) . ?
C17 C18 1.429(9) . ?
C18 C19 1.424(8) . ?
C20 C21 1.413(9) . ?
C21 C22 1.390(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 H24C 0.9700 . ?
C25 H25 0.9400 . ?
O17 H17A 0.8598 . ?
O17 H17B 0.8603 . ?
O18 H18A 0.8597 . ?
O18 H18B 0.8604 . ?
O19 H19A 0.8596 . ?
O19 H19B 0.8604 . ?

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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N3 N2 H2 124.1 . . ?
C1 N2 H2 124.1 . . ?
C1 N2 N3 111.8(5) . . ?
C3 N3 N2 105.3(5) . . ?
O1 N4 C2 119.0(6) . . ?
O2 N4 O1 123.1(6) . . ?
O2 N4 C2 117.9(6) . . ?
C3 N5 H5 115.2 . . ?
C4 N5 H5 115.2 . . ?
C4 N5 C3 129.6(6) . . ?
O3 N6 O4 119.2(6) . . ?
O3 N6 C5 120.3(6) . . ?
O4 N6 C5 120.5(6) . . ?
H7A N7 H7B 120.0 . . ?
C6 N7 H7A 120.0 . . ?
C6 N7 H7B 120.0 . . ?
O5 N8 C7 119.7(6) . . ?
O6 N8 O5 118.1(6) . . ?
O6 N8 C7 122.1(6) . . ?
C8 N9 C4 119.5(6) . . ?
C8 N10 H10 116.3 . . ?
C8 N10 C9 127.3(6) . . ?
C9 N10 H10 116.3 . . ?
N12 N11 H11 124.6 . . ?
C9 N11 H11 124.6 . . ?
C9 N11 N12 110.9(6) . . ?
C11 N12 N11 106.9(6) . . ?
O7 N13 O8 122.5(6) . . ?
O7 N13 C10 119.3(6) . . ?
O8 N13 C10 118.2(7) . . ?
H14A N14 H14B 109.3 . . ?
C11 N14 H14A 109.6 . . ?
C11 N14 H14B 109.0 . . ?
N1 C1 C2 130.5(6) . . ?
N2 C1 N1 123.7(6) . . ?
N2 C1 C2 105.8(6) . . ?
N4 C2 C1 125.1(6) . . ?
N4 C2 C3 128.5(6) . . ?
C1 C2 C3 106.4(6) . . ?
N3 C3 N5 126.8(6) . . ?
N3 C3 C2 110.7(6) . . ?
N5 C3 C2 122.5(6) . . ?
N5 C4 C5 121.5(6) . . ?
N9 C4 N5 116.2(6) . . ?
N9 C4 C5 122.3(6) . . ?
C4 C5 N6 120.1(6) . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 N6 120.3(6) . . ?
N7 C6 C5 121.7(7) . . ?
N7 C6 C7 121.9(6) . . ?
C5 C6 C7 116.4(6) . . ?
N8 C7 C6 120.5(6) . . ?
N8 C7 C8 120.6(6) . . ?
C8 C7 C6 118.8(6) . . ?
N9 C8 N10 115.0(6) . . ?
N9 C8 C7 123.4(6) . . ?
N10 C8 C7 121.6(6) . . ?
N10 C9 C10 125.7(6) . . ?
N11 C9 N10 127.2(6) . . ?
N11 C9 C10 107.1(6) . . ?
N13 C10 C9 126.5(7) . . ?
N13 C10 C11 127.6(7) . . ?
C9 C10 C11 105.9(6) . . ?
N12 C11 N14 122.2(7) . . ?
N12 C11 C10 109.0(6) . . ?
N14 C11 C10 128.7(7) . . ?
H15A N15 H15B 109.2 . . ?
C12 N15 H15A 109.2 . . ?
C12 N15 H15B 108.8 . . ?
C12 N16 N17 106.2(5) . . ?
N16 N17 H17 124.3 . . ?
C14 N17 N16 111.3(5) . . ?
C14 N17 H17 124.3 . . ?
O9 N18 O11 122.6(5) . . ?
O9 N18 C13 119.4(6) . . ?
O11 N18 C13 118.0(6) . . ?
C14 N19 H19 115.8 . . ?
C15 N19 H19 115.8 . . ?
C15 N19 C14 128.4(5) . . ?
O10 N20 C16 120.1(5) . . ?
O12 N20 O10 119.0(5) . . ?
O12 N20 C16 120.9(6) . . ?
H21A N21 H21B 120.0 . . ?
C17 N21 H21A 120.0 . . ?
C17 N21 H21B 120.0 . . ?
O13 N22 O14 118.5(6) . . ?
O13 N22 C18 121.2(6) . . ?
O14 N22 C18 120.3(5) . . ?
C19 N23 C15 119.5(5) . . ?
C19 N24 H24 115.7 . . ?
C19 N24 C20 128.6(5) . . ?
C20 N24 H24 115.7 . . ?
C20 N25 N26 105.1(5) . . ?
N25 N26 H26 124.2 . . ?
C22 N26 N25 111.5(5) . . ?
C22 N26 H26 124.2 . . ?
H27A N27 H27B 120.0 . . ?
C22 N27 H27A 120.0 . . ?
C22 N27 H27B 120.0 . . ?
O15 N28 C21 119.0(6) . . ?
O16 N28 O15 121.7(6) . . ?
O16 N28 C21 119.3(6) . . ?
C24 N29 C23 117.7(9) . . ?
C25 N29 C23 123.1(8) . . ?
C25 N29 C24 119.1(9) . . ?
N15 C12 C13 128.0(6) . . ?
N16 C12 N15 122.5(6) . . ?
N16 C12 C13 109.4(6) . . ?
N18 C13 C12 127.5(6) . . ?
N18 C13 C14 126.7(6) . . ?
C12 C13 C14 105.8(6) . . ?
N17 C14 N19 127.7(6) . . ?
N17 C14 C13 107.2(6) . . ?
N19 C14 C13 125.1(6) . . ?
N19 C15 C16 121.9(5) . . ?
N23 C15 N19 115.3(5) . . ?
N23 C15 C16 122.8(6) . . ?
C15 C16 N20 120.0(6) . . ?
C17 C16 N20 120.5(6) . . ?
C17 C16 C15 119.5(5) . . ?
N21 C17 C16 122.2(6) . . ?
N21 C17 C18 120.7(6) . . ?
C16 C17 C18 117.2(6) . . ?
N22 C18 C17 120.6(6) . . ?
N22 C18 C19 121.0(6) . . ?
C19 C18 C17 118.5(5) . . ?
N23 C19 N24 116.0(5) . . ?
N23 C19 C18 122.6(5) . . ?
N24 C19 C18 121.4(5) . . ?
N24 C20 C21 123.4(6) . . ?
N25 C20 N24 125.9(6) . . ?
N25 C20 C21 110.6(6) . . ?
N28 C21 C20 127.9(6) . . ?
N28 C21 C22 125.9(6) . . ?
C22 C21 C20 106.2(6) . . ?
N26 C22 N27 123.3(7) . . ?
N26 C22 C21 106.4(6) . . ?
N27 C22 C21 130.2(7) . . ?
N29 C23 H23A 109.5 . . ?
N29 C23 H23B 109.5 . . ?
N29 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N29 C24 H24A 109.5 . . ?
N29 C24 H24B 109.5 . . ?
N29 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O20 C25 N29 126.6(9) . . ?
O20 C25 H25 116.7 . . ?
N29 C25 H25 116.7 . . ?
H17A O17 H17B 104.5 . . ?
H18A O18 H18B 104.5 . . ?
H19A O19 H19B 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 N4 C2 C1 -0.5(11) . . . . ?
O1 N4 C2 C3 180.0(7) . . . . ?
O2 N4 C2 C1 179.5(7) . . . . ?
O2 N4 C2 C3 0.0(12) . . . . ?
O3 N6 C5 C4 1.6(11) . . . . ?
O3 N6 C5 C6 -179.2(7) . . . . ?
O4 N6 C5 C4 179.8(7) . . . . ?
O4 N6 C5 C6 -1.1(11) . . . . ?
O5 N8 C7 C6 5.5(10) . . . . ?
O5 N8 C7 C8 -172.4(7) . . . . ?
O6 N8 C7 C6 -179.3(7) . . . . ?
O6 N8 C7 C8 2.8(10) . . . . ?
O7 N13 C10 C9 2.9(12) . . . . ?
O7 N13 C10 C11 -175.4(8) . . . . ?
O8 N13 C10 C9 -176.5(8) . . . . ?
O8 N13 C10 C11 5.3(13) . . . . ?
N1 C1 C2 N4 1.8(13) . . . . ?
N1 C1 C2 C3 -178.6(7) . . . . ?
N2 N3 C3 N5 179.9(6) . . . . ?
N2 N3 C3 C2 0.5(7) . . . . ?
N2 C1 C2 N4 -178.7(7) . . . . ?
N2 C1 C2 C3 0.9(8) . . . . ?
N3 N2 C1 N1 178.9(6) . . . . ?
N3 N2 C1 C2 -0.7(8) . . . . ?
N4 C2 C3 N3 178.7(7) . . . . ?
N4 C2 C3 N5 -0.8(12) . . . . ?
N5 C4 C5 N6 -0.7(10) . . . . ?
N5 C4 C5 C6 -179.8(6) . . . . ?
N6 C5 C6 N7 1.1(11) . . . . ?
N6 C5 C6 C7 -178.4(6) . . . . ?
N7 C6 C7 N8 2.2(11) . . . . ?
N7 C6 C7 C8 -179.9(7) . . . . ?
N8 C7 C8 N9 177.9(6) . . . . ?
N8 C7 C8 N10 -2.7(10) . . . . ?
N9 C4 C5 N6 178.6(6) . . . . ?
N9 C4 C5 C6 -0.5(10) . . . . ?
N10 C9 C10 N13 0.4(13) . . . . ?
N10 C9 C10 C11 179.0(7) . . . . ?
N11 N12 C11 N14 -178.7(7) . . . . ?
N11 N12 C11 C10 -2.4(9) . . . . ?
N11 C9 C10 N13 178.6(7) . . . . ?
N11 C9 C10 C11 -2.8(8) . . . . ?
N12 N11 C9 N10 179.6(7) . . . . ?
N12 N11 C9 C10 1.4(8) . . . . ?
N13 C10 C11 N12 -178.2(8) . . . . ?
N13 C10 C11 N14 -2.2(15) . . . . ?
C1 N2 N3 C3 0.2(8) . . . . ?
C1 C2 C3 N3 -0.9(8) . . . . ?
C1 C2 C3 N5 179.6(6) . . . . ?
C3 N5 C4 N9 -0.1(10) . . . . ?
C3 N5 C4 C5 179.2(7) . . . . ?
C4 N5 C3 N3 -0.7(12) . . . . ?
C4 N5 C3 C2 178.7(7) . . . . ?
C4 N9 C8 N10 -179.2(6) . . . . ?
C4 N9 C8 C7 0.3(10) . . . . ?
C4 C5 C6 N7 -179.8(7) . . . . ?
C4 C5 C6 C7 0.7(10) . . . . ?
C5 C6 C7 N8 -178.3(6) . . . . ?
C5 C6 C7 C8 -0.4(10) . . . . ?
C6 C7 C8 N9 -0.1(10) . . . . ?
C6 C7 C8 N10 179.3(6) . . . . ?
C8 N9 C4 N5 179.3(6) . . . . ?
C8 N9 C4 C5 0.1(10) . . . . ?
C8 N10 C9 N11 0.8(12) . . . . ?
C8 N10 C9 C10 178.7(7) . . . . ?
C9 N10 C8 N9 -1.7(10) . . . . ?
C9 N10 C8 C7 178.9(7) . . . . ?
C9 N11 N12 C11 0.6(8) . . . . ?
C9 C10 C11 N12 3.3(9) . . . . ?
C9 C10 C11 N14 179.2(8) . . . . ?
O9 N18 C13 C12 176.1(7) . . . . ?
O9 N18 C13 C14 -1.5(10) . . . . ?
O10 N20 C16 C15 0.5(10) . . . . ?
O10 N20 C16 C17 -179.6(6) . . . . ?
O11 N18 C13 C12 -5.3(10) . . . . ?
O11 N18 C13 C14 177.1(6) . . . . ?
O12 N20 C16 C15 -179.4(6) . . . . ?
O12 N20 C16 C17 0.5(10) . . . . ?
O13 N22 C18 C17 -1.9(10) . . . . ?
O13 N22 C18 C19 176.6(6) . . . . ?
O14 N22 C18 C17 177.3(6) . . . . ?
O14 N22 C18 C19 -4.2(10) . . . . ?
O15 N28 C21 C20 0.4(12) . . . . ?
O15 N28 C21 C22 -179.2(8) . . . . ?
O16 N28 C21 C20 -179.7(8) . . . . ?
O16 N28 C21 C22 0.7(12) . . . . ?
N15 C12 C13 N18 0.3(12) . . . . ?
N15 C12 C13 C14 178.2(7) . . . . ?
N16 N17 C14 N19 -178.8(6) . . . . ?
N16 N17 C14 C13 0.3(7) . . . . ?
N16 C12 C13 N18 -178.0(6) . . . . ?
N16 C12 C13 C14 0.0(8) . . . . ?
N17 N16 C12 N15 -178.2(6) . . . . ?
N17 N16 C12 C13 0.2(7) . . . . ?
N18 C13 C14 N17 177.8(6) . . . . ?
N18 C13 C14 N19 -3.1(11) . . . . ?
N19 C15 C16 N20 -0.1(10) . . . . ?
N19 C15 C16 C17 -180.0(6) . . . . ?
N20 C16 C17 N21 1.8(11) . . . . ?
N20 C16 C17 C18 -179.6(6) . . . . ?
N21 C17 C18 N22 -3.1(10) . . . . ?
N21 C17 C18 C19 178.4(6) . . . . ?
N22 C18 C19 N23 -179.2(6) . . . . ?
N22 C18 C19 N24 0.9(10) . . . . ?
N23 C15 C16 N20 -179.5(6) . . . . ?
N23 C15 C16 C17 0.6(10) . . . . ?
N24 C20 C21 N28 -0.9(12) . . . . ?
N24 C20 C21 C22 178.8(7) . . . . ?
N25 N26 C22 N27 -179.6(7) . . . . ?
N25 N26 C22 C21 -0.9(9) . . . . ?
N25 C20 C21 N28 178.9(7) . . . . ?
N25 C20 C21 C22 -1.4(9) . . . . ?
N26 N25 C20 N24 -179.4(6) . . . . ?
N26 N25 C20 C21 0.8(8) . . . . ?
N28 C21 C22 N26 -178.9(7) . . . . ?
N28 C21 C22 N27 -0.3(15) . . . . ?
C12 N16 N17 C14 -0.3(7) . . . . ?
C12 C13 C14 N17 -0.2(7) . . . . ?
C12 C13 C14 N19 178.9(6) . . . . ?
C14 N19 C15 N23 -0.5(10) . . . . ?
C14 N19 C15 C16 -179.9(6) . . . . ?
C15 N19 C14 N17 -0.6(11) . . . . ?
C15 N19 C14 C13 -179.5(6) . . . . ?
C15 N23 C19 N24 -178.6(6) . . . . ?
C15 N23 C19 C18 1.6(9) . . . . ?
C15 C16 C17 N21 -178.3(7) . . . . ?
C15 C16 C17 C18 0.3(10) . . . . ?
C16 C17 C18 N22 178.3(6) . . . . ?
C16 C17 C18 C19 -0.2(9) . . . . ?
C17 C18 C19 N23 -0.7(10) . . . . ?
C17 C18 C19 N24 179.4(6) . . . . ?
C19 N23 C15 N19 179.0(6) . . . . ?
C19 N23 C15 C16 -1.5(10) . . . . ?
C19 N24 C20 N25 -0.9(11) . . . . ?
C19 N24 C20 C21 178.8(7) . . . . ?
C20 N24 C19 N23 -0.7(10) . . . . ?
C20 N24 C19 C18 179.2(6) . . . . ?
C20 N25 N26 C22 0.1(8) . . . . ?
C20 C21 C22 N26 1.4(9) . . . . ?
C20 C21 C22 N27 179.9(9) . . . . ?
C23 N29 C25 O20 -176.2(13) . . . . ?
C24 N29 C25 O20 -1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20240514_zh_nlg_h3_0m
_database_code_depnum_ccdc_archive 'CCDC 2368017'
loop_
_audit_author_name
_audit_author_address
a-d
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-07-04 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_audit_creation_date             2024-05-15
_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         '3(Cl O4), C9 H12 N14 O4, C9 H11 N14 O4, H2 O'
_chemical_formula_sum            'C18 H25 Cl3 N28 O21'
_chemical_formula_weight         1076.01
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.686(2)
_cell_length_b                   11.614(3)
_cell_length_c                   44.234(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.115(17)
_cell_angle_gamma                90
_cell_volume                     3948.5(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    781
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      49.864
_cell_measurement_theta_min      3.998
_shelx_estimated_absorpt_T_max   0.740
_shelx_estimated_absorpt_T_min   0.681
_exptl_absorpt_coefficient_mu    3.199
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.1470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1081 before and 0.0800 after correction.
The Ratio of minimum to maximum transmission is 0.4592.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_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  0.0843
_diffrn_reflns_av_unetI/netI     0.0967
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12710
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.646
_diffrn_reflns_theta_min         3.935
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.960
_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                4470
_reflns_number_total             7003
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.00061(13)
_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   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         7003
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0874
_refine_ls_restrained_S_all      1.049
_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)+(0.1220P)²+4.1556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2570
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.500(3)
 0.500(3)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 O4_$1-O1
 2.85 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(O7) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(N28) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5.a Riding coordinates:
 N16(H16A,H16B), N17(H17A,H17B), N19(H19), N22(H22A,H22B), N25(H25), N26(H26A,
 H26B), N27(H27A,H27B), N2(H2A,H2B), N3(H3A,H3B), N8(H8A,H8B), N11(H11),
 N12(H12A,H12B), N13(H13A,H13B), O41(H41A,H41B)
;
_atom_sites_solution_hydrogens   difmap
_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
Cl3 Cl -0.5445(4) 1.14967(19) 0.23825(5) 0.0685(6) Uani 1 1 d . . . . .
O5 O -0.6680(13) 1.2661(6) 0.08892(14) 0.082(3) Uani 1 1 d . . . . .
O6 O -0.6986(11) 1.4507(6) 0.07989(13) 0.074(2) Uani 1 1 d . . . . .
O7 O -0.2916(14) 1.4427(9) 0.36095(16) 0.103(3) Uani 1 1 d . U . . .
O8 O -0.2910(14) 1.6300(9) 0.35399(16) 0.100(3) Uani 1 1 d . U . . .
O9 O -0.6608(18) 1.1156(8) 0.2164(2) 0.128(4) Uani 1 1 d . . . . .
O10 O -0.4527(15) 1.2535(7) 0.22848(19) 0.101(3) Uani 1 1 d . . . . .
O11 O -0.6203(15) 1.1767(8) 0.26725(19) 0.107(3) Uani 1 1 d . . . . .
O12 O -0.4173(17) 1.0598(7) 0.2424(2) 0.110(3) Uani 1 1 d . . . . .
N15 N -0.6667(13) 1.3675(7) 0.09658(16) 0.069(2) Uani 1 1 d . . . . .
N16 N -0.6113(12) 1.6044(6) 0.12651(15) 0.063(2) Uani 1 1 d . . . . .
H16A H -0.644716 1.611063 0.107770 0.076 Uiso 1 1 d R U . . .
H16B H -0.587776 1.665293 0.137120 0.076 Uiso 1 1 d R U . . .
N17 N -0.6384(13) 1.1991(6) 0.14925(17) 0.074(3) Uani 1 1 d . . . . .
H17A H -0.660443 1.165092 0.132070 0.088 Uiso 1 1 d R U . . .
H17B H -0.628583 1.158041 0.165650 0.088 Uiso 1 1 d R U . . .
N18 N -0.5866(13) 1.4876(5) 0.16992(15) 0.061(2) Uani 1 1 d . . . . .
N19 N -0.5949(11) 1.3694(5) 0.17655(15) 0.0544(18) Uani 1 1 d . . . . .
H19 H -0.583817 1.339370 0.194375 0.065 Uiso 1 1 d R U . . .
C19 C -0.6229(16) 1.3918(8) 0.12684(18) 0.067(3) Uani 1 1 d . . . . .
N20 N -0.5648(14) 1.6737(6) 0.18708(16) 0.068(2) Uani 1 1 d . . . . .
C20 C -0.6015(16) 1.5042(7) 0.13943(17) 0.062(2) Uani 1 1 d . . . . .
N21 N -0.5242(13) 1.5134(6) 0.21981(17) 0.064(2) Uani 1 1 d . . . . .
C21 C -0.6155(17) 1.3108(8) 0.1505(2) 0.073(3) Uani 1 1 d . . . . .
N22 N -0.5347(15) 1.8535(6) 0.20629(18) 0.081(3) Uani 1 1 d . . . . .
H22A H -0.557576 1.880031 0.188314 0.097 Uiso 1 1 d R U . . .
H22B H -0.519355 1.901621 0.221254 0.097 Uiso 1 1 d R U . . .
C22 C -0.5578(15) 1.5653(7) 0.19340(18) 0.061(2) Uani 1 1 d . . . . .
N23 N -0.4829(15) 1.7052(7) 0.23846(17) 0.080(3) Uani 1 1 d . . . . .
C23 C -0.5267(12) 1.7446(8) 0.2106(2) 0.058(2) Uani 1 1 d . . . . .
N24 N -0.4562(13) 1.5490(7) 0.26944(15) 0.066(2) Uani 1 1 d . . . . .
C24 C -0.4879(15) 1.5946(8) 0.24081(18) 0.063(3) Uani 1 1 d . . . . .
N25 N -0.4519(15) 1.4297(6) 0.27327(15) 0.077(3) Uani 1 1 d . . . . .
H25 H -0.478712 1.380330 0.259108 0.092 Uiso 1 1 d R U . . .
C25 C -0.4058(18) 1.6036(10) 0.2960(2) 0.079(3) Uani 1 1 d . . . . .
N26 N -0.3869(14) 1.2999(8) 0.31206(18) 0.079(3) Uani 1 1 d . . . . .
H26A H -0.361061 1.285905 0.330779 0.094 Uiso 1 1 d R U . . .
H26B H -0.411221 1.242995 0.299849 0.094 Uiso 1 1 d R U . . .
C26 C -0.3599(16) 1.5137(9) 0.31562(18) 0.071(3) Uani 1 1 d . . . . .
N27 N -0.4086(15) 1.7116(8) 0.29903(17) 0.080(3) Uani 1 1 d . . . . .
H27A H -0.471430 1.753421 0.286928 0.096 Uiso 1 1 d R U . . .
H27B H -0.361260 1.742691 0.315008 0.096 Uiso 1 1 d R U . . .
C27 C -0.399(2) 1.4054(10) 0.3022(2) 0.083(3) Uani 1 1 d . . . . .
N28 N -0.3144(13) 1.5268(10) 0.3454(2) 0.082(3) Uani 1 1 d . U . . .
O1 O -0.4068(10) 1.3283(4) -0.02362(10) 0.0616(16) Uani 1 1 d D . . . .
N1 N -0.4596(11) 1.2555(5) -0.04136(16) 0.0538(18) Uani 1 1 d . . . . .
C1 C -0.5582(12) 1.1671(6) -0.02961(17) 0.0458(18) Uani 1 1 d . . . . .
O2 O -0.4293(11) 1.2618(5) -0.06888(14) 0.071(2) Uani 1 1 d . . . . .
N2 N -0.5661(14) 1.2082(5) 0.02556(15) 0.066(2) Uani 1 1 d . . . . .
H2A H -0.551550 1.282961 0.021658 0.079 Uiso 1 1 d R U . . .
H2B H -0.467910 1.181181 0.033078 0.079 Uiso 1 1 d R U . . .
C2 C -0.6082(15) 1.1459(6) 0.00081(18) 0.055(2) Uani 1 1 d . . . . .
O3 O -1.3076(10) 0.4926(5) 0.07901(14) 0.0670(18) Uani 1 1 d . . . . .
N3 N -0.6283(13) 1.0609(6) -0.07688(15) 0.066(2) Uani 1 1 d . . . . .
H3A H -0.682405 1.002182 -0.084749 0.079 Uiso 1 1 d R U . . .
H3B H -0.569725 1.107412 -0.088399 0.079 Uiso 1 1 d R U . . .
C3 C -0.6337(14) 1.0798(6) -0.04754(17) 0.053(2) Uani 1 1 d . . . . .
O4 O -1.3582(10) 0.4355(5) 0.03372(11) 0.0652(18) Uani 1 1 d . . . . .
N4 N -0.7043(11) 1.0512(5) 0.00321(15) 0.0516(17) Uani 1 1 d . . . . .
C4 C -0.8113(13) 0.9080(7) -0.0325(2) 0.054(2) Uani 1 1 d . . . . .
N5 N -0.7208(10) 1.0101(5) -0.02720(13) 0.0440(14) Uani 1 1 d . . . . .
C5 C -0.8996(13) 0.7741(6) -0.06509(19) 0.054(2) Uani 1 1 d . . . . .
N6 N -0.8814(11) 0.8555(5) -0.00824(13) 0.0510(17) Uani 1 1 d . . . . .
C6 C -0.9563(14) 0.7584(6) -0.01634(18) 0.054(2) Uani 1 1 d . . . . .
N7 N -0.8162(11) 0.8733(5) -0.06106(14) 0.0539(19) Uani 1 1 d . . . . .
C7 C -1.1477(13) 0.6083(6) 0.00882(18) 0.055(2) Uani 1 1 d . . . . .
N8 N -0.9068(16) 0.7341(6) -0.09332(15) 0.077(3) Uani 1 1 d . . . . .
H8A H -0.964961 0.672063 -0.098287 0.093 Uiso 1 1 d R U . . .
H8B H -0.852281 0.772853 -0.107027 0.093 Uiso 1 1 d R U . . .
C8 C -1.1854(12) 0.5894(6) 0.03966(18) 0.0492(19) Uani 1 1 d . . . . .
N9 N -0.9823(11) 0.7138(5) -0.04291(15) 0.0551(18) Uani 1 1 d . . . . .
C9 C -1.0922(14) 0.6737(6) 0.05697(17) 0.054(2) Uani 1 1 d . . . . .
N10 N -1.0443(10) 0.7039(5) 0.00840(13) 0.0447(15) Uani 1 1 d . . . . .
N11 N -1.0137(13) 0.7413(6) 0.03740(15) 0.064(2) Uani 1 1 d . . . . .
H11 H -0.942363 0.797224 0.042018 0.077 Uiso 1 1 d R U . . .
N12 N -1.0943(14) 0.6904(6) 0.08662(15) 0.069(2) Uani 1 1 d . . . . .
H12A H -1.028085 0.745000 0.093739 0.083 Uiso 1 1 d R U . . .
H12B H -1.155775 0.648540 0.098859 0.083 Uiso 1 1 d R U . . .
N13 N -1.1997(12) 0.5505(5) -0.01469(15) 0.059(2) Uani 1 1 d . . . . .
H13A H -1.167247 0.571005 -0.032709 0.070 Uiso 1 1 d R U . . .
H13B H -1.269467 0.492405 -0.012269 0.070 Uiso 1 1 d R U . . .
N14 N -1.2860(12) 0.5003(5) 0.05154(18) 0.062(2) Uani 1 1 d . . . . .
O41 O -0.8757(12) 0.9395(5) 0.05180(14) 0.073(2) Uani 1 1 d . . . . .
H41A H -0.808015 0.959825 0.037428 0.109 Uiso 1 1 d R U . . .
H41B H -0.892935 1.001865 0.061988 0.109 Uiso 1 1 d R U . . .
Cl1 Cl -1.1024(4) 1.4906(2) 0.15574(6) 0.0778(7) Uani 1 1 d . . . . .
O13 O -0.9991(13) 1.4758(8) 0.1288(2) 0.100(3) Uani 1 1 d . . . . .
O14 O -0.9969(19) 1.5081(14) 0.1803(2) 0.164(6) Uani 1 1 d . . . . .
O15 O -1.2155(11) 1.3916(7) 0.1586(2) 0.096(3) Uani 1 1 d . . . . .
O16 O -1.2097(15) 1.5935(7) 0.1505(3) 0.120(4) Uani 1 1 d . . . . .
Cl2 Cl -0.7422(4) 0.91536(18) 0.13063(5) 0.0676(7) Uani 1 1 d . . . . .
O17 O -0.7397(16) 1.0079(5) 0.10836(14) 0.096(3) Uani 1 1 d . . . . .
O18 O -0.8683(12) 0.8299(7) 0.1238(2) 0.094(3) Uani 1 1 d . . . . .
O19 O -0.7816(14) 0.9640(6) 0.15991(14) 0.086(2) Uani 1 1 d . . . . .
O20 O -0.5742(11) 0.8648(6) 0.13120(15) 0.074(2) Uani 1 1 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
Cl3 O9 1.375(10) . ?
Cl3 O10 1.463(9) . ?
Cl3 O11 1.445(9) . ?
Cl3 O12 1.442(10) . ?
O5 N15 1.225(10) . ?
O6 N15 1.241(10) . ?
O7 N28 1.207(13) . ?
O8 N28 1.270(13) . ?
N15 C19 1.408(11) . ?
N16 H16A 0.8707 . ?
N16 H16B 0.8680 . ?
N16 C20 1.298(11) . ?
N17 H17A 0.8725 . ?
N17 H17B 0.8709 . ?
N17 C21 1.311(11) . ?
N18 N19 1.406(9) . ?
N18 C20 1.367(10) . ?
N18 C22 1.393(10) . ?
N19 H19 0.8658 . ?
N19 C21 1.347(11) . ?
C19 C20 1.429(12) . ?
C19 C21 1.408(13) . ?
N20 C22 1.291(11) . ?
N20 C23 1.359(11) . ?
N21 C22 1.339(11) . ?
N21 C24 1.353(11) . ?
N22 H22A 0.8705 . ?
N22 H22B 0.8738 . ?
N22 C23 1.280(11) . ?
N23 C23 1.356(12) . ?
N23 C24 1.289(12) . ?
N24 C24 1.394(11) . ?
N24 N25 1.396(11) . ?
N24 C25 1.389(12) . ?
N25 H25 0.8736 . ?
N25 C27 1.372(12) . ?
C25 C26 1.403(16) . ?
C25 N27 1.261(14) . ?
N26 H26A 0.8666 . ?
N26 H26B 0.8734 . ?
N26 C27 1.304(14) . ?
C26 C27 1.422(15) . ?
C26 N28 1.372(12) . ?
N27 H27A 0.8686 . ?
N27 H27B 0.8729 . ?
O1 N1 1.223(8) . ?
N1 C1 1.378(10) . ?
N1 O2 1.242(9) . ?
C1 C2 1.422(11) . ?
C1 C3 1.412(10) . ?
N2 H2A 0.8928 . ?
N2 H2B 0.8818 . ?
N2 C2 1.351(10) . ?
C2 N4 1.330(11) . ?
O3 N14 1.230(10) . ?
N3 H3A 0.8711 . ?
N3 H3B 0.8689 . ?
N3 C3 1.317(10) . ?
C3 N5 1.384(10) . ?
O4 N14 1.223(8) . ?
N4 N5 1.432(9) . ?
C4 N5 1.394(10) . ?
C4 N6 1.347(11) . ?
C4 N7 1.327(10) . ?
C5 N7 1.330(11) . ?
C5 N8 1.334(10) . ?
C5 N9 1.363(11) . ?
N6 C6 1.316(10) . ?
C6 N9 1.299(10) . ?
C6 N10 1.435(10) . ?
C7 C8 1.412(12) . ?
C7 N10 1.365(10) . ?
C7 N13 1.300(10) . ?
N8 H8A 0.8752 . ?
N8 H8B 0.8646 . ?
C8 C9 1.434(11) . ?
C8 N14 1.395(11) . ?
C9 N11 1.316(11) . ?
C9 N12 1.326(10) . ?
N10 N11 1.374(9) . ?
N11 H11 0.8740 . ?
N12 H12A 0.8715 . ?
N12 H12B 0.8683 . ?
N13 H13A 0.8691 . ?
N13 H13B 0.8682 . ?
O41 H41A 0.8556 . ?
O41 H41B 0.8639 . ?
Cl1 O13 1.444(9) . ?
Cl1 O14 1.368(10) . ?
Cl1 O15 1.447(8) . ?
Cl1 O16 1.470(10) . ?
Cl2 O17 1.458(6) . ?
Cl2 O18 1.419(7) . ?
Cl2 O19 1.446(7) . ?
Cl2 O20 1.418(9) . ?

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
O9 Cl3 O10 110.0(6) . . ?
O9 Cl3 O11 115.1(8) . . ?
O9 Cl3 O12 108.8(6) . . ?
O11 Cl3 O10 106.2(6) . . ?
O12 Cl3 O10 107.9(6) . . ?
O12 Cl3 O11 108.6(6) . . ?
O5 N15 O6 125.6(8) . . ?
O5 N15 C19 117.2(8) . . ?
O6 N15 C19 117.1(8) . . ?
H16A N16 H16B 120.2 . . ?
C20 N16 H16A 121.1 . . ?
C20 N16 H16B 118.7 . . ?
H17A N17 H17B 119.6 . . ?
C21 N17 H17A 120.7 . . ?
C21 N17 H17B 119.7 . . ?
C20 N18 N19 109.9(6) . . ?
C20 N18 C22 131.1(7) . . ?
C22 N18 N19 118.9(7) . . ?
N18 N19 H19 125.4 . . ?
C21 N19 N18 108.6(7) . . ?
C21 N19 H19 125.9 . . ?
N15 C19 C20 125.5(8) . . ?
C21 C19 N15 125.6(9) . . ?
C21 C19 C20 108.4(7) . . ?
C22 N20 C23 114.6(8) . . ?
N16 C20 N18 124.4(7) . . ?
N16 C20 C19 129.8(8) . . ?
N18 C20 C19 105.4(7) . . ?
C22 N21 C24 108.9(7) . . ?
N17 C21 N19 123.5(8) . . ?
N17 C21 C19 128.6(9) . . ?
N19 C21 C19 107.7(8) . . ?
H22A N22 H22B 119.5 . . ?
C23 N22 H22A 119.7 . . ?
C23 N22 H22B 120.8 . . ?
N20 C22 N18 117.6(8) . . ?
N20 C22 N21 129.5(8) . . ?
N21 C22 N18 112.9(7) . . ?
C24 N23 C23 113.7(8) . . ?
N22 C23 N20 118.3(8) . . ?
N22 C23 N23 118.7(8) . . ?
N23 C23 N20 122.9(8) . . ?
C24 N24 N25 119.4(7) . . ?
C25 N24 C24 130.0(8) . . ?
C25 N24 N25 110.1(8) . . ?
N21 C24 N24 113.2(8) . . ?
N23 C24 N21 130.2(8) . . ?
N23 C24 N24 116.5(7) . . ?
N24 N25 H25 124.0 . . ?
C27 N25 N24 108.9(7) . . ?
C27 N25 H25 127.1 . . ?
N24 C25 C26 104.6(9) . . ?
N27 C25 N24 122.7(11) . . ?
N27 C25 C26 132.7(9) . . ?
H26A N26 H26B 119.8 . . ?
C27 N26 H26A 120.8 . . ?
C27 N26 H26B 119.3 . . ?
C25 C26 C27 110.3(8) . . ?
N28 C26 C25 125.2(10) . . ?
N28 C26 C27 123.5(10) . . ?
C25 N27 H27A 120.0 . . ?
C25 N27 H27B 119.4 . . ?
H27A N27 H27B 119.8 . . ?
N25 C27 C26 105.6(9) . . ?
N26 C27 N25 121.7(9) . . ?
N26 C27 C26 132.6(9) . . ?
O7 N28 O8 125.0(10) . . ?
O7 N28 C26 119.6(11) . . ?
O8 N28 C26 115.3(10) . . ?
O1 N1 C1 117.1(7) . . ?
O1 N1 O2 121.7(7) . . ?
O2 N1 C1 121.2(6) . . ?
N1 C1 C2 129.5(7) . . ?
N1 C1 C3 123.3(7) . . ?
C3 C1 C2 107.2(7) . . ?
H2A N2 H2B 108.1 . . ?
C2 N2 H2A 113.2 . . ?
C2 N2 H2B 108.6 . . ?
N2 C2 C1 127.5(8) . . ?
N4 C2 C1 111.7(6) . . ?
N4 C2 N2 120.7(8) . . ?
H3A N3 H3B 120.0 . . ?
C3 N3 H3A 120.6 . . ?
C3 N3 H3B 119.4 . . ?
N3 C3 C1 131.3(8) . . ?
N3 C3 N5 124.0(7) . . ?
N5 C3 C1 104.7(6) . . ?
C2 N4 N5 104.4(6) . . ?
N6 C4 N5 116.9(7) . . ?
N7 C4 N5 115.6(8) . . ?
N7 C4 N6 127.6(8) . . ?
C3 N5 N4 112.0(6) . . ?
C3 N5 C4 129.1(6) . . ?
C4 N5 N4 118.9(6) . . ?
N7 C5 N8 116.5(8) . . ?
N7 C5 N9 125.0(7) . . ?
N8 C5 N9 118.4(8) . . ?
C6 N6 C4 110.3(6) . . ?
N6 C6 N10 112.2(7) . . ?
N9 C6 N6 130.8(7) . . ?
N9 C6 N10 116.3(7) . . ?
C4 N7 C5 113.8(7) . . ?
N10 C7 C8 105.1(7) . . ?
N13 C7 C8 129.0(8) . . ?
N13 C7 N10 125.9(8) . . ?
C5 N8 H8A 122.8 . . ?
C5 N8 H8B 117.1 . . ?
H8A N8 H8B 120.0 . . ?
C7 C8 C9 107.9(7) . . ?
N14 C8 C7 126.5(7) . . ?
N14 C8 C9 125.6(7) . . ?
C6 N9 C5 112.1(7) . . ?
N11 C9 C8 106.6(7) . . ?
N11 C9 N12 124.7(8) . . ?
N12 C9 C8 128.4(9) . . ?
C7 N10 C6 130.1(6) . . ?
C7 N10 N11 110.1(6) . . ?
N11 N10 C6 119.5(6) . . ?
C9 N11 N10 110.3(7) . . ?
C9 N11 H11 125.3 . . ?
N10 N11 H11 124.0 . . ?
C9 N12 H12A 117.1 . . ?
C9 N12 H12B 122.8 . . ?
H12A N12 H12B 120.0 . . ?
C7 N13 H13A 120.2 . . ?
C7 N13 H13B 119.4 . . ?
H13A N13 H13B 120.3 . . ?
O3 N14 C8 120.2(7) . . ?
O4 N14 O3 122.0(8) . . ?
O4 N14 C8 117.7(7) . . ?
H41A O41 H41B 104.5 . . ?
O13 Cl1 O15 108.0(5) . . ?
O13 Cl1 O16 106.0(6) . . ?
O14 Cl1 O13 110.2(7) . . ?
O14 Cl1 O15 113.8(7) . . ?
O14 Cl1 O16 109.6(8) . . ?
O15 Cl1 O16 108.8(6) . . ?
O18 Cl2 O17 112.5(5) . . ?
O18 Cl2 O19 108.5(6) . . ?
O19 Cl2 O17 108.7(4) . . ?
O20 Cl2 O17 107.7(6) . . ?
O20 Cl2 O18 109.6(5) . . ?
O20 Cl2 O19 109.8(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
O5 N15 C19 C20 175.0(11) . . . . ?
O5 N15 C19 C21 -13.9(19) . . . . ?
O6 N15 C19 C20 -4.2(18) . . . . ?
O6 N15 C19 C21 166.9(12) . . . . ?
N15 C19 C20 N16 -2(2) . . . . ?
N15 C19 C20 N18 170.9(12) . . . . ?
N15 C19 C21 N17 4(2) . . . . ?
N15 C19 C21 N19 -171.0(11) . . . . ?
N18 N19 C21 N17 -175.7(12) . . . . ?
N18 N19 C21 C19 -0.7(13) . . . . ?
N19 N18 C20 N16 174.7(11) . . . . ?
N19 N18 C20 C19 1.0(13) . . . . ?
N19 N18 C22 N20 -174.5(11) . . . . ?
N19 N18 C22 N21 6.2(15) . . . . ?
C20 N18 N19 C21 -0.2(13) . . . . ?
C20 N18 C22 N20 9(2) . . . . ?
C20 N18 C22 N21 -170.1(12) . . . . ?
C20 C19 C21 N17 176.0(13) . . . . ?
C20 C19 C21 N19 1.4(14) . . . . ?
C21 C19 C20 N16 -174.7(13) . . . . ?
C21 C19 C20 N18 -1.5(14) . . . . ?
C22 N18 N19 C21 -177.3(10) . . . . ?
C22 N18 C20 N16 -9(2) . . . . ?
C22 N18 C20 C19 177.6(12) . . . . ?
C22 N20 C23 N22 -178.4(11) . . . . ?
C22 N20 C23 N23 0.7(17) . . . . ?
C22 N21 C24 N23 0.2(19) . . . . ?
C22 N21 C24 N24 178.1(10) . . . . ?
C23 N20 C22 N18 -176.8(10) . . . . ?
C23 N20 C22 N21 2.4(19) . . . . ?
C23 N23 C24 N21 2(2) . . . . ?
C23 N23 C24 N24 -175.6(10) . . . . ?
N24 N25 C27 N26 178.6(13) . . . . ?
N24 N25 C27 C26 -3.6(15) . . . . ?
N24 C25 C26 C27 -5.9(15) . . . . ?
N24 C25 C26 N28 -174.7(11) . . . . ?
C24 N21 C22 N18 176.4(10) . . . . ?
C24 N21 C22 N20 -2.8(18) . . . . ?
C24 N23 C23 N20 -2.7(17) . . . . ?
C24 N23 C23 N22 176.4(11) . . . . ?
C24 N24 N25 C27 173.0(11) . . . . ?
C24 N24 C25 C26 -168.4(12) . . . . ?
C24 N24 C25 N27 12(2) . . . . ?
N25 N24 C24 N21 4.6(16) . . . . ?
N25 N24 C24 N23 -177.1(11) . . . . ?
N25 N24 C25 C26 3.6(14) . . . . ?
N25 N24 C25 N27 -175.7(13) . . . . ?
C25 N24 C24 N21 176.0(12) . . . . ?
C25 N24 C24 N23 -5.7(19) . . . . ?
C25 N24 N25 C27 0.0(15) . . . . ?
C25 C26 C27 N25 6.0(16) . . . . ?
C25 C26 C27 N26 -176.5(16) . . . . ?
C25 C26 N28 O7 173.7(12) . . . . ?
C25 C26 N28 O8 -9.8(19) . . . . ?
N27 C25 C26 C27 173.3(16) . . . . ?
N27 C25 C26 N28 4(3) . . . . ?
C27 C26 N28 O7 6.3(19) . . . . ?
C27 C26 N28 O8 -177.2(12) . . . . ?
N28 C26 C27 N25 175.0(12) . . . . ?
N28 C26 C27 N26 -7(3) . . . . ?
O1 N1 C1 C2 -0.8(14) . . . . ?
O1 N1 C1 C3 177.3(9) . . . . ?
N1 C1 C2 N2 -1.5(17) . . . . ?
N1 C1 C2 N4 180.0(9) . . . . ?
N1 C1 C3 N3 1.1(18) . . . . ?
N1 C1 C3 N5 -179.7(8) . . . . ?
C1 C2 N4 N5 -1.3(10) . . . . ?
C1 C3 N5 N4 0.6(10) . . . . ?
C1 C3 N5 C4 -176.7(8) . . . . ?
O2 N1 C1 C2 -179.2(9) . . . . ?
O2 N1 C1 C3 -1.2(14) . . . . ?
N2 C2 N4 N5 -180.0(9) . . . . ?
C2 C1 C3 N3 179.5(11) . . . . ?
C2 C1 C3 N5 -1.3(11) . . . . ?
C2 N4 N5 C3 0.4(10) . . . . ?
C2 N4 N5 C4 178.0(8) . . . . ?
N3 C3 N5 N4 179.9(9) . . . . ?
N3 C3 N5 C4 2.6(16) . . . . ?
C3 C1 C2 N2 -179.7(10) . . . . ?
C3 C1 C2 N4 1.7(11) . . . . ?
C4 N6 C6 N9 -5.9(15) . . . . ?
C4 N6 C6 N10 -175.6(8) . . . . ?
N5 C4 N6 C6 -177.4(8) . . . . ?
N5 C4 N7 C5 178.3(8) . . . . ?
N6 C4 N5 C3 178.5(9) . . . . ?
N6 C4 N5 N4 1.4(12) . . . . ?
N6 C4 N7 C5 -0.8(14) . . . . ?
N6 C6 N9 C5 8.0(15) . . . . ?
N6 C6 N10 C7 174.2(9) . . . . ?
N6 C6 N10 N11 -13.2(12) . . . . ?
C6 N10 N11 C9 -173.7(8) . . . . ?
N7 C4 N5 C3 -0.7(14) . . . . ?
N7 C4 N5 N4 -177.8(8) . . . . ?
N7 C4 N6 C6 1.7(14) . . . . ?
N7 C5 N9 C6 -6.3(13) . . . . ?
C7 C8 C9 N11 3.4(11) . . . . ?
C7 C8 C9 N12 177.4(10) . . . . ?
C7 C8 N14 O3 179.2(9) . . . . ?
C7 C8 N14 O4 -4.7(14) . . . . ?
C7 N10 N11 C9 0.3(11) . . . . ?
N8 C5 N7 C4 -179.2(10) . . . . ?
N8 C5 N9 C6 176.2(10) . . . . ?
C8 C7 N10 C6 175.0(9) . . . . ?
C8 C7 N10 N11 1.8(10) . . . . ?
C8 C9 N11 N10 -2.3(11) . . . . ?
N9 C5 N7 C4 3.3(13) . . . . ?
N9 C6 N10 C7 2.9(14) . . . . ?
N9 C6 N10 N11 175.5(8) . . . . ?
C9 C8 N14 O3 3.6(15) . . . . ?
C9 C8 N14 O4 179.7(9) . . . . ?
N10 C6 N9 C5 177.4(8) . . . . ?
N10 C7 C8 C9 -3.1(10) . . . . ?
N10 C7 C8 N14 -179.3(9) . . . . ?
N12 C9 N11 N10 -176.6(10) . . . . ?
N13 C7 C8 C9 177.9(10) . . . . ?
N13 C7 C8 N14 1.6(17) . . . . ?
N13 C7 N10 C6 -5.9(16) . . . . ?
N13 C7 N10 N11 -179.1(10) . . . . ?
N14 C8 C9 N11 179.6(9) . . . . ?
N14 C8 C9 N12 -6.4(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.500(3)
2 0.500(3)

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2368018'
loop_
_audit_author_name
_audit_author_address
a-d
;Nanjing University of science and technology
China
;
_audit_update_record             
;
2024-07-04 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;
_audit_creation_date             2024-06-14
_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         'C13 H12 N18 O8, 2.25(C3 H7 N O), H2 O'
_chemical_formula_sum            'C19.75 H29.75 N20.25 O11.25'
_chemical_formula_weight         730.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   29.9543(14)
_cell_length_b                   29.9543(14)
_cell_length_c                   14.6802(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13172.0(15)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      56.493
_cell_measurement_theta_min      2.950
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1387 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.8424.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             6080
_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  0.1089
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33633
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.691
_diffrn_reflns_theta_min         6.382
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_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                4465
_reflns_number_total             6028
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00019(3)
_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   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         6028
_refine_ls_number_restraints     318
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0808
_refine_ls_restrained_S_all      1.162
_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)+(0.0529P)²+37.7722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1833
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, H15 of C15, H22 of C22, H22A of C22A, H18 of C18, H18C
  of C18A
 At 1.5 times of:
  All C(H,H) groups, H19C of C18A, All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C22-O11
 1.22 with sigma of 0.02
 C22-N21A
 1.36 with sigma of 0.02
 N21A-C21
 1.45 with sigma of 0.02
 N21A-C20
 1.46 with sigma of 0.02
 O11-N21A
 2.3 with sigma of 0.02
 O3A-N4A
 2.3 with sigma of 0.02
 C22-C21
 2.46 with sigma of 0.04
 C22-C20
 2.45 with sigma of 0.04
 O10-C18 \\sim O10A-C18A
 with sigma of 0.02
 N20-C19 \\sim N20A-C19A
 with sigma of 0.02
 N20-C18 \\sim N20A-C18A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.04
 C19-C17 \\sim C19A-C17A
 with sigma of 0.04
 N20-C17 \\sim N20A-C17A
 with sigma of 0.02
 O10-N20 \\sim O10A-N20A
 with sigma of 0.04
 C18-C17 \\sim C18A-C17A
 with sigma of 0.04
 N21A-C21 \\sim N21A-C20
 with sigma of 0.02
 C22-O11 \\sim C22A-O3A
 with sigma of 0.02
 C22-N21A \\sim C22A-N4A
 with sigma of 0.02
 N21A-C21 \\sim N4A-C21A
 with sigma of 0.02
 N21A-C20 \\sim N4A-C20A
 with sigma of 0.02
 C22-C21 \\sim C22A-C21A
 with sigma of 0.04
 C22-C20 \\sim C22A-C20A
 with sigma of 0.04
 O11-N21A \\sim O3A-N4A
 with sigma of 0.04
 C21-C20 \\sim C21A-C20A
 with sigma of 0.04
3. Restrained planarity
 O11, N21A, C20, C21, C22
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O10 \\sim N20 \\sim C17 \\sim C18 \\sim C19 \\sim O10A \\sim N20A \\sim C17A
\\sim C18A \\sim C19A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
O11 \\sim N21A \\sim C20 \\sim C21 \\sim C22: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O11 \\sim N21A \\sim C20 \\sim C21 \\sim C22 \\sim O3A \\sim N4A \\sim C20A
\\sim C21A \\sim C22A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 O11, N21A, C20, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(O10A)=Sof(O12A)=Sof(H12C)=Sof(H12D)=
 Sof(N20A)=Sof(C17A)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18A)=Sof(H18C)=
 Sof(H19C)=1-FVAR(1)
 Sof(O10)=Sof(O12)=Sof(H12A)=Sof(H12B)=Sof(N20)=Sof(C17)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19D)=Sof(H19E)=Sof(H19F)=FVAR(1)
 Fixed Sof: O11(0.125) N21A(0.125) C20(0.125) H20A(0.125) H20B(0.125)
 H20C(0.125) C21(0.125) H21A(0.125) H21B(0.125) H21C(0.125) C22(0.125)
 H22(0.125) O3A(0.125) N4A(0.125) C20A(0.125) H20D(0.125) H20E(0.125)
 H20F(0.125) C21A(0.125) H21D(0.125) H21E(0.125) H21F(0.125) C22A(0.125)
 H22A(0.125)
7.a Everything fixed:
 H19A, H19B, H19C
7.b Free rotating group:
 O12(H12A,H12B), O12A(H12C,H12D)
7.c Rotating group:
 N16(H16A,H16B)
7.d Aromatic/amide H refined with riding coordinates:
 C15(H15), C22(H22), C18(H18), C18A(H18C), C22A(H22A)
7.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N5(H5A,H5B), N9(H9A,H9B), N11(H11A,H11B), N18(H18A,H18B)
7.f Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16C,H16D,H16E), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C17(H17D,H17E,H17F), C19(H19D,H19E,H19F), C17A(H17A,H17B,H17C),
 C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F)
;
_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
O1 O 0.52008(9) 0.54406(11) 0.1600(3) 0.0629(10) Uani 1 1 d . . . . .
O2 O 0.55546(10) 0.59616(10) 0.2344(3) 0.0630(10) Uani 1 1 d . . . . .
O3 O 0.77542(11) 0.71696(10) 0.1662(2) 0.0572(8) Uani 1 1 d . . . . .
O4 O 0.84414(11) 0.72451(10) 0.2132(3) 0.0615(9) Uani 1 1 d . . . . .
O5 O 0.67927(9) 0.41891(9) 0.3093(2) 0.0468(7) Uani 1 1 d . . . . .
O6 O 0.71394(10) 0.39871(9) 0.1862(2) 0.0480(7) Uani 1 1 d . . . . .
O7 O 0.93158(9) 0.39021(11) 0.2537(3) 0.0648(10) Uani 1 1 d . . . . .
O8 O 0.90451(11) 0.32796(11) 0.3044(3) 0.0775(12) Uani 1 1 d . . . . .
N1 N 0.56527(10) 0.46407(11) 0.1208(2) 0.0416(8) Uani 1 1 d . . . . .
H1A H 0.571270 0.437182 0.102030 0.050 Uiso 1 1 calc R U . . .
H1B H 0.538380 0.474697 0.115186 0.050 Uiso 1 1 calc R U . . .
N2 N 0.55434(11) 0.55928(11) 0.1961(3) 0.0447(8) Uani 1 1 d . . . . .
N3 N 0.63888(10) 0.47445(10) 0.1683(2) 0.0328(7) Uani 1 1 d . . . . .
N4 N 0.66132(9) 0.51033(9) 0.2120(2) 0.0301(7) Uani 1 1 d . . . . .
N5 N 0.64601(10) 0.58479(10) 0.2659(2) 0.0372(7) Uani 1 1 d . . . . .
H5A H 0.673327 0.588471 0.284535 0.045 Uiso 1 1 calc R U . . .
H5B H 0.626576 0.606119 0.272716 0.045 Uiso 1 1 calc R U . . .
N6 N 0.72757(9) 0.54666(9) 0.2298(2) 0.0311(7) Uani 1 1 d . . . . .
N7 N 0.79279(9) 0.58643(9) 0.2402(2) 0.0302(7) Uani 1 1 d . . . . .
N8 N 0.83679(9) 0.58964(10) 0.2744(2) 0.0343(7) Uani 1 1 d . . . . .
N9 N 0.88713(12) 0.64849(12) 0.2885(3) 0.0543(10) Uani 1 1 d . . . . .
H9A H 0.906908 0.630957 0.313049 0.065 Uiso 1 1 calc R U . . .
H9B H 0.893181 0.676608 0.280258 0.065 Uiso 1 1 calc R U . . .
N10 N 0.81005(12) 0.70139(11) 0.1999(3) 0.0447(8) Uani 1 1 d . . . . .
N11 N 0.73651(11) 0.63329(11) 0.1723(2) 0.0404(8) Uani 1 1 d . . . . .
H11A H 0.718050 0.611093 0.165836 0.048 Uiso 1 1 calc R U . . .
H11B H 0.728848 0.659916 0.154593 0.048 Uiso 1 1 calc R U . . .
N12 N 0.79669(9) 0.50972(9) 0.2568(2) 0.0299(7) Uani 1 1 d . . . . .
N13 N 0.70575(10) 0.42491(10) 0.2473(2) 0.0335(7) Uani 1 1 d . . . . .
N14 N 0.80290(9) 0.43450(9) 0.2792(2) 0.0292(6) Uani 1 1 d . . . . .
N15 N 0.78421(10) 0.39539(9) 0.3177(2) 0.0335(7) Uani 1 1 d . . . . .
N16 N 0.81400(12) 0.32597(11) 0.3577(3) 0.0475(9) Uani 1 1 d . . . . .
H16A H 0.837971 0.319025 0.388806 0.057 Uiso 1 1 d R U . . .
H16B H 0.790771 0.324266 0.393792 0.057 Uiso 1 1 d R U . . .
N17 N 0.90028(11) 0.36765(11) 0.2838(3) 0.0487(9) Uani 1 1 d . . . . .
N18 N 0.87375(10) 0.46238(10) 0.2302(2) 0.0372(7) Uani 1 1 d . . . . .
H18A H 0.862298 0.488080 0.215471 0.045 Uiso 1 1 calc R U . . .
H18B H 0.902149 0.457573 0.222516 0.045 Uiso 1 1 calc R U . . .
C1 C 0.59269(12) 0.53327(12) 0.1941(3) 0.0349(8) Uani 1 1 d . . . . .
C2 C 0.59752(12) 0.48918(12) 0.1584(2) 0.0323(8) Uani 1 1 d . . . . .
C3 C 0.63400(12) 0.54673(12) 0.2270(2) 0.0319(8) Uani 1 1 d . . . . .
C4 C 0.70650(11) 0.50751(11) 0.2303(2) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.72944(11) 0.46752(11) 0.2458(2) 0.0288(7) Uani 1 1 d . . . . .
C6 C 0.77567(11) 0.47087(11) 0.2595(2) 0.0273(7) Uani 1 1 d . . . . .
C7 C 0.77147(11) 0.54557(11) 0.2423(2) 0.0283(7) Uani 1 1 d . . . . .
C8 C 0.77616(12) 0.62655(11) 0.2091(3) 0.0317(8) Uani 1 1 d . . . . .
C9 C 0.81105(13) 0.65652(11) 0.2235(3) 0.0356(9) Uani 1 1 d . . . . .
C10 C 0.84718(12) 0.63210(12) 0.2631(3) 0.0365(9) Uani 1 1 d . . . . .
C11 C 0.84821(11) 0.43089(12) 0.2639(3) 0.0311(8) Uani 1 1 d . . . . .
C12 C 0.85851(12) 0.38752(12) 0.2918(3) 0.0337(8) Uani 1 1 d . . . . .
C13 C 0.81825(12) 0.36788(12) 0.3251(3) 0.0333(8) Uani 1 1 d . . . . .
O9 O 0.73123(12) 0.28800(9) 0.4207(3) 0.0652(10) Uani 1 1 d . . . . .
N19 N 0.72117(14) 0.21453(11) 0.3891(3) 0.0527(10) Uani 1 1 d . . . . .
C14 C 0.6909(2) 0.17637(15) 0.3940(4) 0.0669(15) Uani 1 1 d . . . . .
H14A H 0.674165 0.174109 0.337638 0.100 Uiso 1 1 calc R U . . .
H14B H 0.670431 0.180390 0.444503 0.100 Uiso 1 1 calc R U . . .
H14C H 0.708067 0.149268 0.403122 0.100 Uiso 1 1 calc R U . . .
C15 C 0.70968(17) 0.25350(14) 0.4252(3) 0.0545(12) Uani 1 1 d . . . . .
H15 H 0.682507 0.254613 0.457158 0.065 Uiso 1 1 calc R U . . .
C16 C 0.76214(18) 0.20967(16) 0.3384(4) 0.0619(13) Uani 1 1 d . . . . .
H16C H 0.778516 0.237598 0.339621 0.093 Uiso 1 1 calc R U . . .
H16D H 0.755300 0.201845 0.275775 0.093 Uiso 1 1 calc R U . . .
H16E H 0.780149 0.186297 0.365581 0.093 Uiso 1 1 calc R U . . .
O11 O 1.0722(9) 0.7562(11) 0.305(2) 0.090(6) Uani 0.125 1 d D U P A -1
N21A N 1.0079(8) 0.7270(10) 0.245(2) 0.087(5) Uani 0.125 1 d D U P A -1
C20 C 1.0041(16) 0.6873(14) 0.301(4) 0.092(7) Uani 0.125 1 d D U P A -1
H20A H 0.974113 0.685489 0.325611 0.139 Uiso 0.125 1 calc R U P A -1
H20B H 1.025498 0.688787 0.350187 0.139 Uiso 0.125 1 calc R U P A -1
H20C H 1.009975 0.661067 0.263930 0.139 Uiso 0.125 1 calc R U P A -1
C21 C 0.9743(12) 0.7361(17) 0.177(3) 0.092(7) Uani 0.125 1 d D U P A -1
H21A H 0.987135 0.732283 0.116337 0.138 Uiso 0.125 1 calc R U P A -1
H21B H 0.963752 0.766510 0.183334 0.138 Uiso 0.125 1 calc R U P A -1
H21C H 0.949557 0.715572 0.184163 0.138 Uiso 0.125 1 calc R U P A -1
C22 C 1.0414(10) 0.7579(12) 0.250(3) 0.088(5) Uani 0.125 1 d D U P A -1
H22 H 1.040504 0.782207 0.209816 0.106 Uiso 0.125 1 calc R U P A -1
C19A C 0.5335(13) 0.294(2) 0.210(5) 0.117(7) Uani 0.133(5) 1 d D U P B 2
H19A H 0.525570 0.283680 0.271060 0.175 Uiso 0.1334 1 d . U P B 2
H19B H 0.512570 0.315210 0.188610 0.175 Uiso 0.1334 1 d . U P B 2
O10 O 0.5789(4) 0.36832(19) 0.0891(5) 0.0650(16) Uani 0.867(5) 1 d D U P B 1
O12 O 0.94453(11) 0.59455(14) 0.4022(3) 0.0576(11) Uani 0.867(5) 1 d G . P B 1
H12A H 0.963197 0.578903 0.371357 0.086 Uiso 0.867(5) 1 d G U P B 1
H12B H 0.955292 0.621229 0.400821 0.086 Uiso 0.867(5) 1 d G U P B 1
N20 N 0.5668(2) 0.3284(2) 0.2184(5) 0.0881(19) Uani 0.867(5) 1 d D U P B 1
C17 C 0.5368(3) 0.3114(4) 0.2871(9) 0.136(3) Uani 0.867(5) 1 d D U P B 1
H17D H 0.537536 0.279061 0.286781 0.204 Uiso 0.867(5) 1 calc R U P B 1
H17E H 0.506637 0.321535 0.274273 0.204 Uiso 0.867(5) 1 calc R U P B 1
H17F H 0.545913 0.322298 0.346507 0.204 Uiso 0.867(5) 1 calc R U P B 1
C18 C 0.5535(2) 0.3515(2) 0.1466(6) 0.0753(17) Uani 0.867(5) 1 d D U P B 1
H18 H 0.522662 0.355395 0.138391 0.090 Uiso 0.867(5) 1 calc R U P B 1
C19 C 0.6142(3) 0.3174(4) 0.2311(7) 0.120(3) Uani 0.867(5) 1 d D U P B 1
H19D H 0.631559 0.330114 0.181676 0.180 Uiso 0.867(5) 1 calc R U P B 1
H19E H 0.617909 0.285206 0.231380 0.180 Uiso 0.867(5) 1 calc R U P B 1
H19F H 0.624544 0.329540 0.288616 0.180 Uiso 0.867(5) 1 calc R U P B 1
O10A O 0.578(3) 0.3575(19) 0.087(3) 0.076(7) Uani 0.133(5) 1 d D U P B 2
O12A O 0.9886(6) 0.6334(6) 0.1667(17) 0.043(6) Uani 0.133(5) 1 d G . P B 2
H12C H 1.009147 0.618547 0.139183 0.065 Uiso 0.133(5) 1 d G U P B 2
H12D H 0.997928 0.660595 0.165515 0.065 Uiso 0.133(5) 1 d G U P B 2
N20A N 0.5795(13) 0.3124(16) 0.213(3) 0.094(3) Uani 0.133(5) 1 d D U P B 2
C17A C 0.6031(14) 0.2977(18) 0.293(3) 0.093(6) Uani 0.133(5) 1 d D U P B 2
H17A H 0.581849 0.292252 0.341888 0.140 Uiso 0.133(5) 1 calc R U P B 2
H17B H 0.623999 0.320647 0.312078 0.140 Uiso 0.133(5) 1 calc R U P B 2
H17C H 0.619175 0.270423 0.279773 0.140 Uiso 0.133(5) 1 calc R U P B 2
C18A C 0.5964(13) 0.3438(14) 0.158(3) 0.087(3) Uani 0.133(5) 1 d D U P B 2
H18C H 0.623891 0.356461 0.175113 0.104 Uiso 0.133(5) 1 calc R U P B 2
H19C H 0.535090 0.268270 0.169680 0.130 Uiso 0.1334 1 d . U P B 2
O3A O 1.0488(9) 0.7856(9) 0.242(2) 0.075(6) Uani 0.125 1 d D U P C -2
N4A N 0.9942(10) 0.7343(10) 0.267(3) 0.089(5) Uani 0.125 1 d D U P C -2
C20A C 0.9543(15) 0.7603(17) 0.285(5) 0.084(8) Uani 0.125 1 d D U P C -2
H20D H 0.935849 0.744688 0.329075 0.126 Uiso 0.125 1 calc R U P C -2
H20E H 0.937764 0.764235 0.228892 0.126 Uiso 0.125 1 calc R U P C -2
H20F H 0.962685 0.789208 0.309269 0.126 Uiso 0.125 1 calc R U P C -2
C21A C 0.9930(15) 0.6888(13) 0.236(4) 0.092(7) Uani 0.125 1 d D U P C -2
H21D H 0.983152 0.687885 0.173475 0.138 Uiso 0.125 1 calc R U P C -2
H21E H 0.972335 0.671871 0.273914 0.138 Uiso 0.125 1 calc R U P C -2
H21F H 1.022557 0.675868 0.241126 0.138 Uiso 0.125 1 calc R U P C -2
C22A C 1.0377(13) 0.7483(13) 0.264(5) 0.087(6) Uani 0.125 1 d D U P C -2
H22A H 1.060169 0.727808 0.279835 0.105 Uiso 0.125 1 calc R U P C -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 N2 1.242(4) . ?
O2 N2 1.240(4) . ?
O3 N10 1.240(4) . ?
O4 N10 1.249(4) . ?
O5 N13 1.220(4) . ?
O6 N13 1.217(4) . ?
O7 N17 1.237(4) . ?
O8 N17 1.233(4) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C2 1.343(5) . ?
N2 C1 1.388(5) . ?
N3 N4 1.421(4) . ?
N3 C2 1.323(5) . ?
N4 C3 1.381(4) . ?
N4 C4 1.382(4) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N5 C3 1.325(5) . ?
N6 C4 1.332(4) . ?
N6 C7 1.328(4) . ?
N7 N8 1.414(4) . ?
N7 C7 1.381(4) . ?
N7 C8 1.378(4) . ?
N8 C10 1.320(5) . ?
N9 H9A 0.8700 . ?
N9 H9B 0.8700 . ?
N9 C10 1.346(5) . ?
N10 C9 1.388(5) . ?
N11 H11A 0.8700 . ?
N11 H11B 0.8700 . ?
N11 C8 1.320(5) . ?
N12 C6 1.324(4) . ?
N12 C7 1.330(4) . ?
N13 C5 1.461(4) . ?
N14 N15 1.416(4) . ?
N14 C6 1.391(4) . ?
N14 C11 1.380(4) . ?
N15 C13 1.316(5) . ?
N16 H16A 0.8757 . ?
N16 H16B 0.8757 . ?
N16 C13 1.350(5) . ?
N17 C12 1.391(5) . ?
N18 H18A 0.8700 . ?
N18 H18B 0.8700 . ?
N18 C11 1.312(5) . ?
C1 C2 1.428(5) . ?
C1 C3 1.388(5) . ?
C4 C5 1.400(5) . ?
C5 C6 1.403(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.430(5) . ?
C11 C12 1.397(5) . ?
C12 C13 1.428(5) . ?
O9 C15 1.220(5) . ?
N19 C14 1.460(6) . ?
N19 C15 1.328(5) . ?
N19 C16 1.443(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 H15 0.9400 . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C16 H16E 0.9700 . ?
O11 C22 1.221(19) . ?
N21A C20 1.450(15) . ?
N21A C21 1.446(15) . ?
N21A C22 1.367(18) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22 0.9400 . ?
C19A H19A 0.9831 . ?
C19A H19B 0.9390 . ?
C19A N20A 1.48(2) . ?
C19A H19C 0.9803 . ?
O10 C18 1.244(11) . ?
O12 H12A 0.8586 . ?
O12 H12B 0.8620 . ?
N20 C17 1.445(10) . ?
N20 C18 1.321(9) . ?
N20 C19 1.471(11) . ?
C17 H17D 0.9700 . ?
C17 H17E 0.9700 . ?
C17 H17F 0.9700 . ?
C18 H18 0.9400 . ?
C19 H19D 0.9700 . ?
C19 H19E 0.9700 . ?
C19 H19F 0.9700 . ?
O10A C18A 1.25(2) . ?
O12A H12C 0.8601 . ?
O12A H12D 0.8601 . ?
N20A C17A 1.44(2) . ?
N20A C18A 1.33(2) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A H17C 0.9700 . ?
C18A H18C 0.9400 . ?
O3A C22A 1.21(3) . ?
N4A C20A 1.45(2) . ?
N4A C21A 1.44(2) . ?
N4A C22A 1.37(2) . ?
C20A H20D 0.9700 . ?
C20A H20E 0.9700 . ?
C20A H20F 0.9700 . ?
C21A H21D 0.9700 . ?
C21A H21E 0.9700 . ?
C21A H21F 0.9700 . ?
C22A H22A 0.9400 . ?

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
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
O1 N2 C1 117.9(3) . . ?
O2 N2 O1 122.9(3) . . ?
O2 N2 C1 119.2(3) . . ?
C2 N3 N4 103.9(3) . . ?
C3 N4 N3 112.9(3) . . ?
C3 N4 C4 126.7(3) . . ?
C4 N4 N3 120.3(3) . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
C7 N6 C4 116.5(3) . . ?
C7 N7 N8 118.9(3) . . ?
C8 N7 N8 113.3(3) . . ?
C8 N7 C7 127.8(3) . . ?
C10 N8 N7 103.9(3) . . ?
H9A N9 H9B 120.0 . . ?
C10 N9 H9A 120.0 . . ?
C10 N9 H9B 120.0 . . ?
O3 N10 O4 122.5(3) . . ?
O3 N10 C9 118.8(3) . . ?
O4 N10 C9 118.7(4) . . ?
H11A N11 H11B 120.0 . . ?
C8 N11 H11A 120.0 . . ?
C8 N11 H11B 120.0 . . ?
C6 N12 C7 116.4(3) . . ?
O5 N13 C5 117.1(3) . . ?
O6 N13 O5 125.8(3) . . ?
O6 N13 C5 117.1(3) . . ?
C6 N14 N15 119.9(3) . . ?
C11 N14 N15 112.9(3) . . ?
C11 N14 C6 127.2(3) . . ?
C13 N15 N14 104.2(3) . . ?
H16A N16 H16B 108.8 . . ?
C13 N16 H16A 109.2 . . ?
C13 N16 H16B 110.1 . . ?
O7 N17 C12 118.6(3) . . ?
O8 N17 O7 122.4(3) . . ?
O8 N17 C12 118.9(3) . . ?
H18A N18 H18B 120.0 . . ?
C11 N18 H18A 120.0 . . ?
C11 N18 H18B 120.0 . . ?
N2 C1 C2 127.6(3) . . ?
C3 C1 N2 124.5(3) . . ?
C3 C1 C2 107.8(3) . . ?
N1 C2 C1 126.6(3) . . ?
N3 C2 N1 122.1(3) . . ?
N3 C2 C1 111.3(3) . . ?
N4 C3 C1 104.1(3) . . ?
N5 C3 N4 126.0(3) . . ?
N5 C3 C1 129.9(3) . . ?
N4 C4 C5 124.4(3) . . ?
N6 C4 N4 114.1(3) . . ?
N6 C4 C5 121.5(3) . . ?
C4 C5 N13 120.8(3) . . ?
C4 C5 C6 116.5(3) . . ?
C6 C5 N13 122.7(3) . . ?
N12 C6 N14 114.6(3) . . ?
N12 C6 C5 121.9(3) . . ?
N14 C6 C5 123.5(3) . . ?
N6 C7 N7 115.6(3) . . ?
N6 C7 N12 127.2(3) . . ?
N12 C7 N7 117.2(3) . . ?
N7 C8 C9 103.9(3) . . ?
N11 C8 N7 126.4(3) . . ?
N11 C8 C9 129.6(3) . . ?
N10 C9 C8 124.7(4) . . ?
N10 C9 C10 127.8(3) . . ?
C8 C9 C10 107.4(3) . . ?
N8 C10 N9 121.7(3) . . ?
N8 C10 C9 111.5(3) . . ?
N9 C10 C9 126.8(3) . . ?
N14 C11 C12 104.0(3) . . ?
N18 C11 N14 125.4(3) . . ?
N18 C11 C12 130.6(3) . . ?
N17 C12 C11 124.9(3) . . ?
N17 C12 C13 127.8(3) . . ?
C11 C12 C13 107.3(3) . . ?
N15 C13 N16 122.6(3) . . ?
N15 C13 C12 111.6(3) . . ?
N16 C13 C12 125.8(3) . . ?
C15 N19 C14 120.5(4) . . ?
C15 N19 C16 121.0(4) . . ?
C16 N19 C14 118.3(4) . . ?
N19 C14 H14A 109.5 . . ?
N19 C14 H14B 109.5 . . ?
N19 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 N19 125.9(5) . . ?
O9 C15 H15 117.1 . . ?
N19 C15 H15 117.1 . . ?
N19 C16 H16C 109.5 . . ?
N19 C16 H16D 109.5 . . ?
N19 C16 H16E 109.5 . . ?
H16C C16 H16D 109.5 . . ?
H16C C16 H16E 109.5 . . ?
H16D C16 H16E 109.5 . . ?
C21 N21A C20 119(3) . . ?
C22 N21A C20 125(2) . . ?
C22 N21A C21 115(2) . . ?
N21A C20 H20A 109.5 . . ?
N21A C20 H20B 109.5 . . ?
N21A C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N21A C21 H21A 109.5 . . ?
N21A C21 H21B 109.5 . . ?
N21A C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O11 C22 N21A 124(2) . . ?
O11 C22 H22 117.8 . . ?
N21A C22 H22 117.8 . . ?
H19A C19A H19B 111.0 . . ?
H19A C19A H19C 107.6 . . ?
H19B C19A H19C 111.2 . . ?
N20A C19A H19A 108.5 . . ?
N20A C19A H19B 112.9 . . ?
N20A C19A H19C 105.4 . . ?
H12A O12 H12B 104.5 . . ?
C17 N20 C19 115.7(8) . . ?
C18 N20 C17 123.7(7) . . ?
C18 N20 C19 120.6(7) . . ?
N20 C17 H17D 109.5 . . ?
N20 C17 H17E 109.5 . . ?
N20 C17 H17F 109.5 . . ?
H17D C17 H17E 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
O10 C18 N20 124.8(7) . . ?
O10 C18 H18 117.6 . . ?
N20 C18 H18 117.6 . . ?
N20 C19 H19D 109.5 . . ?
N20 C19 H19E 109.5 . . ?
N20 C19 H19F 109.5 . . ?
H19D C19 H19E 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 109.5 . . ?
H12C O12A H12D 104.4 . . ?
C17A N20A C19A 112(2) . . ?
C18A N20A C19A 126(3) . . ?
C18A N20A C17A 121(3) . . ?
N20A C17A H17A 109.5 . . ?
N20A C17A H17B 109.5 . . ?
N20A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
O10A C18A N20A 125(4) . . ?
O10A C18A H18C 117.5 . . ?
N20A C18A H18C 117.5 . . ?
C21A N4A C20A 123(3) . . ?
C22A N4A C20A 129(3) . . ?
C22A N4A C21A 108(3) . . ?
N4A C20A H20D 109.5 . . ?
N4A C20A H20E 109.5 . . ?
N4A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
N4A C21A H21D 109.5 . . ?
N4A C21A H21E 109.5 . . ?
N4A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
O3A C22A N4A 124(3) . . ?
O3A C22A H22A 118.2 . . ?
N4A C22A H22A 118.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 C1 C2 -3.1(6) . . . . ?
O1 N2 C1 C3 176.3(4) . . . . ?
O2 N2 C1 C2 176.1(4) . . . . ?
O2 N2 C1 C3 -4.5(6) . . . . ?
O3 N10 C9 C8 2.4(6) . . . . ?
O3 N10 C9 C10 -179.8(4) . . . . ?
O4 N10 C9 C8 -177.4(4) . . . . ?
O4 N10 C9 C10 0.5(6) . . . . ?
O5 N13 C5 C4 -66.5(4) . . . . ?
O5 N13 C5 C6 113.6(4) . . . . ?
O6 N13 C5 C4 112.9(4) . . . . ?
O6 N13 C5 C6 -67.0(5) . . . . ?
O7 N17 C12 C11 3.6(6) . . . . ?
O7 N17 C12 C13 -179.6(4) . . . . ?
O8 N17 C12 C11 -174.4(4) . . . . ?
O8 N17 C12 C13 2.4(7) . . . . ?
N2 C1 C2 N1 -1.1(7) . . . . ?
N2 C1 C2 N3 -179.7(4) . . . . ?
N2 C1 C3 N4 179.1(4) . . . . ?
N2 C1 C3 N5 0.3(7) . . . . ?
N3 N4 C3 N5 -179.6(3) . . . . ?
N3 N4 C3 C1 1.5(4) . . . . ?
N3 N4 C4 N6 149.8(3) . . . . ?
N3 N4 C4 C5 -28.4(5) . . . . ?
N4 N3 C2 N1 -178.6(3) . . . . ?
N4 N3 C2 C1 0.1(4) . . . . ?
N4 C4 C5 N13 -2.6(5) . . . . ?
N4 C4 C5 C6 177.3(3) . . . . ?
N6 C4 C5 N13 179.3(3) . . . . ?
N6 C4 C5 C6 -0.8(5) . . . . ?
N7 N8 C10 N9 179.6(4) . . . . ?
N7 N8 C10 C9 0.6(4) . . . . ?
N7 C8 C9 N10 178.1(4) . . . . ?
N7 C8 C9 C10 0.0(4) . . . . ?
N8 N7 C7 N6 164.7(3) . . . . ?
N8 N7 C7 N12 -15.0(5) . . . . ?
N8 N7 C8 N11 178.8(3) . . . . ?
N8 N7 C8 C9 0.4(4) . . . . ?
N10 C9 C10 N8 -178.5(4) . . . . ?
N10 C9 C10 N9 2.5(7) . . . . ?
N11 C8 C9 N10 -0.1(7) . . . . ?
N11 C8 C9 C10 -178.3(4) . . . . ?
N13 C5 C6 N12 179.1(3) . . . . ?
N13 C5 C6 N14 -2.6(5) . . . . ?
N14 N15 C13 N16 -178.6(4) . . . . ?
N14 N15 C13 C12 -0.6(4) . . . . ?
N14 C11 C12 N17 175.8(4) . . . . ?
N14 C11 C12 C13 -1.6(4) . . . . ?
N15 N14 C6 N12 155.9(3) . . . . ?
N15 N14 C6 C5 -22.4(5) . . . . ?
N15 N14 C11 N18 -178.9(3) . . . . ?
N15 N14 C11 C12 1.4(4) . . . . ?
N17 C12 C13 N15 -175.8(4) . . . . ?
N17 C12 C13 N16 2.1(7) . . . . ?
N18 C11 C12 N17 -3.9(7) . . . . ?
N18 C11 C12 C13 178.7(4) . . . . ?
C2 N3 N4 C3 -1.0(4) . . . . ?
C2 N3 N4 C4 -177.4(3) . . . . ?
C2 C1 C3 N4 -1.4(4) . . . . ?
C2 C1 C3 N5 179.8(4) . . . . ?
C3 N4 C4 N6 -26.0(5) . . . . ?
C3 N4 C4 C5 155.7(4) . . . . ?
C3 C1 C2 N1 179.5(4) . . . . ?
C3 C1 C2 N3 0.9(5) . . . . ?
C4 N4 C3 N5 -3.5(6) . . . . ?
C4 N4 C3 C1 177.6(3) . . . . ?
C4 N6 C7 N7 179.1(3) . . . . ?
C4 N6 C7 N12 -1.2(6) . . . . ?
C4 C5 C6 N12 -0.8(5) . . . . ?
C4 C5 C6 N14 177.5(3) . . . . ?
C6 N12 C7 N6 -0.4(6) . . . . ?
C6 N12 C7 N7 179.3(3) . . . . ?
C6 N14 N15 C13 178.4(3) . . . . ?
C6 N14 C11 N18 2.3(6) . . . . ?
C6 N14 C11 C12 -177.5(3) . . . . ?
C7 N6 C4 N4 -176.6(3) . . . . ?
C7 N6 C4 C5 1.7(5) . . . . ?
C7 N7 N8 C10 -179.8(3) . . . . ?
C7 N7 C8 N11 -2.2(6) . . . . ?
C7 N7 C8 C9 179.4(3) . . . . ?
C7 N12 C6 N14 -177.0(3) . . . . ?
C7 N12 C6 C5 1.4(5) . . . . ?
C8 N7 N8 C10 -0.7(4) . . . . ?
C8 N7 C7 N6 -14.2(5) . . . . ?
C8 N7 C7 N12 166.0(3) . . . . ?
C8 C9 C10 N8 -0.4(5) . . . . ?
C8 C9 C10 N9 -179.3(4) . . . . ?
C11 N14 N15 C13 -0.5(4) . . . . ?
C11 N14 C6 N12 -25.3(5) . . . . ?
C11 N14 C6 C5 156.3(4) . . . . ?
C11 C12 C13 N15 1.5(4) . . . . ?
C11 C12 C13 N16 179.4(4) . . . . ?
C14 N19 C15 O9 -175.8(5) . . . . ?
C16 N19 C15 O9 -0.4(8) . . . . ?
C20 N21A C22 O11 -1(3) . . . . ?
C21 N21A C22 O11 179(2) . . . . ?
C19A N20A C18A O10A -12(10) . . . . ?
C17 N20 C18 O10 176.2(9) . . . . ?
C19 N20 C18 O10 -5.7(13) . . . . ?
C17A N20A C18A O10A 179(6) . . . . ?
C20A N4A C22A O3A -29(9) . . . . ?
C21A N4A C22A O3A 143(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
