# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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. 
# 
#######################################################################

data_lz002_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2277514'
loop_
_audit_author_name
_audit_author_address
'Jingwen Li'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_audit_creation_date             2023-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
6-nitroamino-3-nitroimino-8-oxo-7,8-dihydro-[1,2,4]triazolo[3,4-f][1,2,4]triazine
_chemical_formula_moiety         'C4 H3 N9 O5'
_chemical_formula_sum            'C4 H3 N9 O5'
_chemical_formula_weight         257.15
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.078(6)
_cell_length_b                   6.215(5)
_cell_length_c                   8.920(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.188(10)
_cell_angle_gamma                90
_cell_volume                     437.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    509
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.951
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2468
_diffrn_reflns_point_group_measured_fraction_full 0.829
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.670
_diffrn_reflns_theta_min         2.336
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.532
_reflns_Friedel_fraction_full    0.659
_reflns_Friedel_fraction_max     0.620
_reflns_number_gt                1049
_reflns_number_total             1658
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Flack x determined using 268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.096
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5(0.039) H6(0.039) H9(0.043)
 Fixed X: H5(0.897254) H6(0.743623) H9(0.61677)
 Fixed Y: H5(0.624098) H6(0.848031) H9(0.239185)
 Fixed Z: H5(0.11237) H6(0.727404) H9(0.096559)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7424(9) 0.0825(13) -0.0716(8) 0.059(2) Uani 1 1 d . . . . .
O2 O 0.9551(7) 0.2814(12) 0.0419(7) 0.0447(17) Uani 1 1 d . . . . .
C2 C 0.9142(9) 0.7872(17) 0.3013(9) 0.0325(18) Uani 1 1 d . . . . .
O3 O 0.4395(7) 0.3818(12) 0.7985(7) 0.0414(16) Uani 1 1 d . . . . .
C3 C 0.8421(10) 0.7608(15) 0.4366(9) 0.0311(18) Uani 1 1 d . . . . .
O4 O 0.6105(7) 0.6509(11) 0.8463(6) 0.0385(16) Uani 1 1 d . . . . .
O5 O 1.0050(8) 0.9283(13) 0.2787(7) 0.0473(18) Uani 1 1 d . . . . .
N1 N 0.8086(9) 0.2175(13) 0.0205(8) 0.0372(18) Uani 1 1 d . . . . .
N2 N 0.5431(8) 0.5019(12) 0.7577(7) 0.0321(17) Uani 1 1 d . . . . .
N3 N 0.7371(8) 0.5933(12) 0.4470(7) 0.0297(16) Uani 1 1 d . . . . .
N4 N 0.8626(8) 0.6227(12) 0.1971(8) 0.0329(17) Uani 1 1 d . . . . .
H5 H 0.897254 0.624098 0.112370 0.039 Uiso 1 1 calc R U . . .
N5 N 0.8581(8) 0.8872(13) 0.5553(8) 0.0349(17) Uani 1 1 d . . . . .
N6 N 0.7575(8) 0.7952(13) 0.6418(7) 0.0326(16) Uani 1 1 d . . . . .
H6 H 0.743623 0.848031 0.727404 0.039 Uiso 1 1 calc R U . . .
N7 N 0.6945(8) 0.4284(12) 0.3423(7) 0.0343(18) Uani 1 1 d . . . . .
N8 N 0.5756(8) 0.4701(14) 0.6214(8) 0.0377(19) Uani 1 1 d . . . . .
N9 N 0.7038(8) 0.3113(13) 0.1043(7) 0.0360(18) Uani 1 1 d . . . . .
H9 H 0.616770 0.239185 0.096559 0.043 Uiso 1 1 d R U . . .
C1 C 0.7589(9) 0.4578(14) 0.2222(8) 0.0267(17) Uani 1 1 d . . . . .
C4 C 0.6821(9) 0.6144(15) 0.5806(9) 0.0304(19) 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
O1 N1 1.216(10) . ?
O2 N1 1.224(9) . ?
C2 C3 1.456(11) . ?
C2 O5 1.187(11) . ?
C2 N4 1.385(11) . ?
O3 N2 1.233(9) . ?
C3 N3 1.358(10) . ?
C3 N5 1.303(11) . ?
O4 N2 1.264(9) . ?
N1 N9 1.372(10) . ?
N2 N8 1.312(9) . ?
N3 N7 1.380(9) . ?
N3 C4 1.363(10) . ?
N4 H5 0.8600 . ?
N4 C1 1.371(10) . ?
N5 N6 1.359(9) . ?
N6 H6 0.8600 . ?
N6 C4 1.339(12) . ?
N7 C1 1.299(10) . ?
N8 C4 1.345(11) . ?
N9 H9 0.8244 . ?
N9 C1 1.391(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 C2 C3 126.4(9) . . ?
O5 C2 N4 122.7(7) . . ?
N4 C2 C3 110.9(8) . . ?
N3 C3 C2 120.5(8) . . ?
N5 C3 C2 128.1(8) . . ?
N5 C3 N3 111.3(7) . . ?
O1 N1 O2 127.0(7) . . ?
O1 N1 N9 115.3(7) . . ?
O2 N1 N9 117.6(7) . . ?
O3 N2 O4 119.2(7) . . ?
O3 N2 N8 117.7(7) . . ?
O4 N2 N8 123.1(7) . . ?
C3 N3 N7 126.4(6) . . ?
C3 N3 C4 108.0(7) . . ?
C4 N3 N7 125.6(7) . . ?
C2 N4 H5 118.3 . . ?
C1 N4 C2 123.4(7) . . ?
C1 N4 H5 118.3 . . ?
C3 N5 N6 103.9(7) . . ?
N5 N6 H6 123.3 . . ?
C4 N6 N5 113.4(7) . . ?
C4 N6 H6 123.3 . . ?
C1 N7 N3 111.6(7) . . ?
N2 N8 C4 114.5(7) . . ?
N1 N9 H9 109.7 . . ?
N1 N9 C1 123.7(6) . . ?
C1 N9 H9 123.4 . . ?
N4 C1 N9 118.3(6) . . ?
N7 C1 N4 127.2(7) . . ?
N7 C1 N9 114.3(7) . . ?
N6 C4 N3 103.5(7) . . ?
N6 C4 N8 135.4(7) . . ?
N8 C4 N3 121.2(8) . . ?

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 N1 N9 C1 175.4(8) . . . . ?
O2 N1 N9 C1 -6.8(12) . . . . ?
C2 C3 N3 N7 3.9(11) . . . . ?
C2 C3 N3 C4 -176.9(8) . . . . ?
C2 C3 N5 N6 176.2(8) . . . . ?
C2 N4 C1 N7 -0.1(13) . . . . ?
C2 N4 C1 N9 174.7(7) . . . . ?
O3 N2 N8 C4 176.3(7) . . . . ?
C3 C2 N4 C1 -0.7(11) . . . . ?
C3 N3 N7 C1 -4.4(11) . . . . ?
C3 N3 C4 N6 0.3(8) . . . . ?
C3 N3 C4 N8 -180.0(7) . . . . ?
C3 N5 N6 C4 0.9(9) . . . . ?
O4 N2 N8 C4 -2.4(11) . . . . ?
O5 C2 C3 N3 178.8(8) . . . . ?
O5 C2 C3 N5 2.2(15) . . . . ?
O5 C2 N4 C1 179.4(8) . . . . ?
N1 N9 C1 N4 46.7(11) . . . . ?
N1 N9 C1 N7 -137.9(8) . . . . ?
N2 N8 C4 N3 175.3(7) . . . . ?
N2 N8 C4 N6 -5.1(14) . . . . ?
N3 C3 N5 N6 -0.6(9) . . . . ?
N3 N7 C1 N4 2.5(11) . . . . ?
N3 N7 C1 N9 -172.5(6) . . . . ?
N4 C2 C3 N3 -1.0(10) . . . . ?
N4 C2 C3 N5 -177.6(8) . . . . ?
N5 C3 N3 N7 -179.0(7) . . . . ?
N5 C3 N3 C4 0.2(9) . . . . ?
N5 N6 C4 N3 -0.8(9) . . . . ?
N5 N6 C4 N8 179.6(9) . . . . ?
N7 N3 C4 N6 179.6(7) . . . . ?
N7 N3 C4 N8 -0.7(12) . . . . ?
C4 N3 N7 C1 176.5(8) . . . . ?

_shelx_SHELXL_version_number     2016/6
_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_mo_20221539_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2277515'
loop_
_audit_author_name
_audit_author_address
'Jingwen Li'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2023-06-28 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_audit_creation_date             2022-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'Diammonium 6-nitroamino-3-nitroimino-8-oxo-7,8-dihydro-[1,2,4]triazolo[3,4-f][1,2,4]triazine'
_chemical_formula_moiety         'C4 H N9 O5, H2 O, 2(H4 N)'
_chemical_formula_sum            'C4 H11 N11 O6'
_chemical_formula_weight         309.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.1297(10)
_cell_length_b                   8.7667(11)
_cell_length_c                   16.667(2)
_cell_angle_alpha                89.131(4)
_cell_angle_beta                 87.895(4)
_cell_angle_gamma                75.168(4)
_cell_volume                     1147.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1578
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 12687 reflections, Rint = 0.0565
 (5128 with I > 3sig(I), Rint = 0.0369)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1850
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            4633
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.403
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2778
_reflns_number_total             4633
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         4633
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.019
_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)+(0.0416P)²+1.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2. Restrained distances
 N4-H4D = N4-H4C = N4-H4B = N4-H4A
 0.87 with sigma of 0.02
 N11-H11B = N11-H11A = N11-H11C = N11-H11D
 0.87 with sigma of 0.02
 N13-H13D = N13-H13C = N13-H13A = N13-H13B
 0.87 with sigma of 0.02
 O7-H7B = O7-H7A
 0.87 with sigma of 0.02
 H7A-H7B
 1.46 with sigma of 0.02
 O6-H6A = O6-H6B
 0.87 with sigma of 0.02
 N12-H12B = N12-H12D = N12-H12A = N12-H12C
 0.87 with sigma of 0.02
 H12C-H12B
 1.46 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N20(H20), N3(H3)
;
_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
O3 O 0.7585(3) 0.7897(3) 0.62877(15) 0.0232(6) Uani 1 1 d . . . . .
O12 O 1.5788(3) 0.8891(3) 0.19949(15) 0.0248(6) Uani 1 1 d . . . . .
O10 O 1.2614(3) 0.8048(3) -0.12686(15) 0.0231(6) Uani 1 1 d . . . . .
O8 O 1.1745(3) 0.0741(3) 0.14491(16) 0.0283(6) Uani 1 1 d . . . . .
O11 O 1.5277(3) 0.9356(3) 0.07311(15) 0.0258(6) Uani 1 1 d . . . . .
O2 O 1.1070(3) 0.9007(3) 0.30218(15) 0.0300(7) Uani 1 1 d . . . . .
O4 O 0.5921(3) 0.1213(3) 0.46502(16) 0.0311(7) Uani 1 1 d . . . . .
O1 O 1.0414(3) 0.9375(3) 0.42932(15) 0.0287(6) Uani 1 1 d . . . . .
O5 O 0.7026(3) 0.0851(3) 0.34387(16) 0.0309(7) Uani 1 1 d . . . . .
O9 O 1.0855(3) 0.1211(3) 0.02254(16) 0.0297(6) Uani 1 1 d . . . . .
O6 O 0.5697(4) 0.4906(3) 0.25965(19) 0.0340(7) Uani 1 1 d D . . . .
N18 N 1.2649(3) 0.5074(3) 0.02056(17) 0.0169(6) Uani 1 1 d . . . . .
N19 N 1.3372(3) 0.5562(3) 0.08563(18) 0.0196(7) Uani 1 1 d . . . . .
N20 N 1.3575(3) 0.7705(3) 0.00080(17) 0.0192(7) Uani 1 1 d . . . . .
H20 H 1.393656 0.856767 -0.003262 0.023 Uiso 1 1 calc R . . . .
N6 N 0.7733(3) 0.5053(3) 0.47692(17) 0.0169(7) Uani 1 1 d . . . . .
N22 N 1.5186(4) 0.8561(3) 0.13489(19) 0.0223(7) Uani 1 1 d . . . . .
N1 N 1.0403(4) 0.8633(3) 0.36621(19) 0.0225(7) Uani 1 1 d . . . . .
N7 N 0.6362(4) 0.3653(3) 0.54959(18) 0.0219(7) Uani 1 1 d . . . . .
N3 N 0.8611(3) 0.7668(3) 0.49934(17) 0.0196(7) Uani 1 1 d . . . . .
H3 H 0.892880 0.854923 0.503793 0.024 Uiso 1 1 calc R . . . .
N16 N 1.1434(4) 0.3708(3) -0.05638(18) 0.0205(7) Uani 1 1 d . . . . .
N5 N 0.8565(4) 0.5559(3) 0.41243(17) 0.0199(7) Uani 1 1 d . . . . .
N15 N 1.2267(4) 0.2783(3) 0.08257(18) 0.0211(7) Uani 1 1 d . . . . .
N17 N 1.1600(4) 0.5031(3) -0.09898(18) 0.0206(7) Uani 1 1 d . . . . .
N10 N 0.6771(4) 0.1613(3) 0.4080(2) 0.0243(7) Uani 1 1 d . . . . .
N2 N 0.9743(4) 0.7401(3) 0.36076(18) 0.0223(7) Uani 1 1 d . . . . .
N21 N 1.4518(4) 0.7342(3) 0.13909(17) 0.0204(7) Uani 1 1 d . . . . .
N14 N 1.1597(4) 0.1562(3) 0.0809(2) 0.0230(7) Uani 1 1 d . . . . .
N8 N 0.6476(4) 0.4938(3) 0.59474(18) 0.0220(7) Uani 1 1 d . . . . .
N9 N 0.7444(4) 0.2825(3) 0.41135(18) 0.0217(7) Uani 1 1 d . . . . .
O7 O 1.1263(5) 0.5180(4) 0.2375(2) 0.0517(9) Uani 1 1 d D . . . .
N13 N 0.9392(5) 0.8716(4) 0.1500(3) 0.0298(8) Uani 1 1 d D . . . .
N4 N 0.5686(4) 0.7642(4) 0.7764(2) 0.0263(8) Uani 1 1 d D . . . .
N11 N 0.4526(5) 0.8853(4) 0.3644(2) 0.0297(8) Uani 1 1 d D . . . .
C6 C 1.2330(4) 0.5819(4) -0.0518(2) 0.0174(8) Uani 1 1 d . . . . .
C1 C 0.8963(4) 0.6893(4) 0.4267(2) 0.0179(8) Uani 1 1 d . . . . .
C5 C 1.2070(4) 0.3742(4) 0.0156(2) 0.0192(8) Uani 1 1 d . . . . .
C3 C 0.7296(4) 0.5752(4) 0.5493(2) 0.0174(8) Uani 1 1 d . . . . .
N12 N 0.9316(5) 0.2973(6) 0.2598(3) 0.0449(10) Uani 1 1 d D . . . .
C8 C 1.3813(4) 0.6885(4) 0.0724(2) 0.0174(8) Uani 1 1 d . . . . .
C4 C 0.7121(4) 0.3731(4) 0.4786(2) 0.0184(8) Uani 1 1 d . . . . .
C2 C 0.7809(4) 0.7183(4) 0.5653(2) 0.0191(8) Uani 1 1 d . . . . .
C7 C 1.2820(4) 0.7285(4) -0.0646(2) 0.0186(8) Uani 1 1 d . . . . .
H4A H 0.636(4) 0.766(4) 0.7330(17) 0.037(12) Uiso 1 1 d D . . . .
H4B H 0.518(4) 0.688(3) 0.767(2) 0.023(10) Uiso 1 1 d D . . . .
H4C H 0.495(4) 0.859(3) 0.779(3) 0.052(14) Uiso 1 1 d D . . . .
H4D H 0.632(5) 0.744(6) 0.820(2) 0.074(18) Uiso 1 1 d D . . . .
H11A H 0.353(4) 0.951(5) 0.354(3) 0.077(19) Uiso 1 1 d D . . . .
H11B H 0.443(6) 0.809(4) 0.399(2) 0.061(15) Uiso 1 1 d D . . . .
H11C H 0.523(4) 0.938(4) 0.383(3) 0.048(13) Uiso 1 1 d D . . . .
H11D H 0.504(6) 0.854(5) 0.3173(18) 0.064(17) Uiso 1 1 d D . . . .
H13A H 0.932(5) 0.797(4) 0.117(2) 0.041(13) Uiso 1 1 d D . . . .
H13B H 1.011(6) 0.923(6) 0.130(3) 0.10(2) Uiso 1 1 d D . . . .
H13C H 0.835(4) 0.932(6) 0.156(4) 0.10(2) Uiso 1 1 d D . . . .
H13D H 0.974(8) 0.844(8) 0.198(2) 0.13(3) Uiso 1 1 d D . . . .
H7A H 1.092(6) 0.589(5) 0.275(2) 0.075(18) Uiso 1 1 d D . . . .
H7B H 1.192(7) 0.545(6) 0.200(3) 0.12(3) Uiso 1 1 d D . . . .
H12A H 0.885(6) 0.292(6) 0.3077(18) 0.081(19) Uiso 1 1 d D . . . .
H12B H 0.985(6) 0.371(4) 0.255(3) 0.09(2) Uiso 1 1 d D . . . .
H6A H 0.505(5) 0.515(5) 0.3032(18) 0.054(15) Uiso 1 1 d D . . . .
H6B H 0.534(7) 0.575(4) 0.230(3) 0.10(2) Uiso 1 1 d D . . . .
H12C H 0.994(6) 0.202(3) 0.265(4) 0.13(3) Uiso 1 1 d D . . . .
H12D H 0.860(7) 0.293(8) 0.222(3) 0.11(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.222(4) . ?
O12 N22 1.266(4) . ?
O10 C7 1.219(4) . ?
O8 N14 1.270(4) . ?
O11 N22 1.245(4) . ?
O2 N1 1.256(4) . ?
O4 N10 1.252(4) . ?
O1 N1 1.247(4) . ?
O5 N10 1.252(4) . ?
O9 N14 1.245(4) . ?
O6 H6A 0.876(19) . ?
O6 H6B 0.87(2) . ?
N18 N19 1.377(4) . ?
N18 C6 1.364(4) . ?
N18 C5 1.370(4) . ?
N19 C8 1.312(4) . ?
N20 H20 0.8800 . ?
N20 C8 1.377(4) . ?
N20 C7 1.370(4) . ?
N6 N5 1.377(4) . ?
N6 C3 1.355(4) . ?
N6 C4 1.373(4) . ?
N22 N21 1.317(4) . ?
N1 N2 1.329(4) . ?
N7 N8 1.389(4) . ?
N7 C4 1.323(4) . ?
N3 H3 0.8800 . ?
N3 C1 1.382(4) . ?
N3 C2 1.375(4) . ?
N16 N17 1.384(4) . ?
N16 C5 1.328(5) . ?
N5 C1 1.318(4) . ?
N15 N14 1.321(4) . ?
N15 C5 1.376(5) . ?
N17 C6 1.307(4) . ?
N10 N9 1.316(4) . ?
N2 C1 1.373(4) . ?
N21 C8 1.379(4) . ?
N8 C3 1.311(4) . ?
N9 C4 1.363(4) . ?
O7 H7A 0.870(19) . ?
O7 H7B 0.875(19) . ?
N13 H13A 0.878(19) . ?
N13 H13B 0.88(2) . ?
N13 H13C 0.88(2) . ?
N13 H13D 0.87(2) . ?
N4 H4A 0.892(19) . ?
N4 H4B 0.890(18) . ?
N4 H4C 0.891(19) . ?
N4 H4D 0.90(2) . ?
N11 H11A 0.89(2) . ?
N11 H11B 0.892(19) . ?
N11 H11C 0.892(19) . ?
N11 H11D 0.887(19) . ?
C6 C7 1.451(5) . ?
C3 C2 1.450(5) . ?
N12 H12A 0.88(2) . ?
N12 H12B 0.870(19) . ?
N12 H12C 0.867(19) . ?
N12 H12D 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H6A O6 H6B 102(5) . . ?
C6 N18 N19 127.5(3) . . ?
C6 N18 C5 105.5(3) . . ?
C5 N18 N19 126.9(3) . . ?
C8 N19 N18 113.1(3) . . ?
C8 N20 H20 117.4 . . ?
C7 N20 H20 117.4 . . ?
C7 N20 C8 125.3(3) . . ?
C3 N6 N5 128.3(3) . . ?
C3 N6 C4 106.1(3) . . ?
C4 N6 N5 125.6(3) . . ?
O12 N22 N21 115.2(3) . . ?
O11 N22 O12 119.9(3) . . ?
O11 N22 N21 124.8(3) . . ?
O2 N1 N2 115.0(3) . . ?
O1 N1 O2 120.7(3) . . ?
O1 N1 N2 124.3(3) . . ?
C4 N7 N8 108.5(3) . . ?
C1 N3 H3 117.1 . . ?
C2 N3 H3 117.1 . . ?
C2 N3 C1 125.7(3) . . ?
C5 N16 N17 108.4(3) . . ?
C1 N5 N6 112.6(3) . . ?
N14 N15 C5 116.7(3) . . ?
C6 N17 N16 106.6(3) . . ?
O4 N10 N9 123.2(3) . . ?
O5 N10 O4 120.5(3) . . ?
O5 N10 N9 116.3(3) . . ?
N1 N2 C1 120.3(3) . . ?
N22 N21 C8 120.1(3) . . ?
O8 N14 N15 114.8(3) . . ?
O9 N14 O8 120.8(3) . . ?
O9 N14 N15 124.4(3) . . ?
C3 N8 N7 106.5(3) . . ?
N10 N9 C4 118.0(3) . . ?
H7A O7 H7B 114(3) . . ?
H13A N13 H13B 110(5) . . ?
H13A N13 H13C 105(4) . . ?
H13A N13 H13D 118(5) . . ?
H13B N13 H13C 113(5) . . ?
H13B N13 H13D 104(6) . . ?
H13C N13 H13D 107(6) . . ?
H4A N4 H4B 104(3) . . ?
H4A N4 H4C 107(4) . . ?
H4A N4 H4D 109(4) . . ?
H4B N4 H4C 112(4) . . ?
H4B N4 H4D 112(4) . . ?
H4C N4 H4D 111(4) . . ?
H11A N11 H11B 113(4) . . ?
H11A N11 H11C 110(4) . . ?
H11A N11 H11D 107(5) . . ?
H11B N11 H11C 110(4) . . ?
H11B N11 H11D 116(4) . . ?
H11C N11 H11D 100(4) . . ?
N18 C6 C7 118.2(3) . . ?
N17 C6 N18 110.9(3) . . ?
N17 C6 C7 130.9(3) . . ?
N5 C1 N3 123.2(3) . . ?
N5 C1 N2 111.6(3) . . ?
N2 C1 N3 125.3(3) . . ?
N18 C5 N15 116.1(3) . . ?
N16 C5 N18 108.5(3) . . ?
N16 C5 N15 135.4(3) . . ?
N6 C3 C2 118.4(3) . . ?
N8 C3 N6 110.7(3) . . ?
N8 C3 C2 130.9(3) . . ?
H12A N12 H12B 114(5) . . ?
H12A N12 H12C 90(5) . . ?
H12A N12 H12D 111(5) . . ?
H12B N12 H12C 117(3) . . ?
H12B N12 H12D 117(6) . . ?
H12C N12 H12D 105(6) . . ?
N19 C8 N20 123.5(3) . . ?
N19 C8 N21 111.4(3) . . ?
N20 C8 N21 125.1(3) . . ?
N7 C4 N6 108.3(3) . . ?
N7 C4 N9 135.7(3) . . ?
N9 C4 N6 116.0(3) . . ?
O3 C2 N3 122.5(3) . . ?
O3 C2 C3 125.8(3) . . ?
N3 C2 C3 111.7(3) . . ?
O10 C7 N20 123.5(3) . . ?
O10 C7 C6 124.1(3) . . ?
N20 C7 C6 112.3(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
