# 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 2022

####################################################################### 
# 
# 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_20211345_0m
_database_code_depnum_ccdc_archive 'CCDC 2129989'
loop_
_audit_author_name
_audit_author_address
'VENTURE '
;Nanjing University of Science and Technology
Germany
;
_audit_update_record             
;
2022-05-22 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_chemical_formula_moiety         'C4 H N7 O7'
_chemical_formula_sum            'C4 H N7 O7'
_chemical_formula_weight         259.096
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.4325(3)
_cell_length_b                   13.6955(8)
_cell_length_c                   12.3557(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.876(2)
_cell_angle_gamma                90
_cell_volume                     917.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2309
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.97
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6566
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.8809.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_description       block
_exptl_crystal_F_000             520.382
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.9874
_diffrn_reflns_Laue_measured_fraction_max 0.9788
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6875
_diffrn_reflns_point_group_measured_fraction_full 0.9874
_diffrn_reflns_point_group_measured_fraction_max 0.9788
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9874
_diffrn_measured_fraction_theta_max 0.9788
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                1456
_reflns_number_total             1848
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.3288
_refine_diff_density_min         -0.3071
_refine_diff_density_rms         0.0772
_refine_ls_d_res_high            0.7984
_refine_ls_d_res_low             9.1624
_refine_ls_goodness_of_fit_ref   1.0825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.0825
_refine_ls_shift/su_max          -0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.3513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0938
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C1(H1)
;
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_refinement_flags_posn
O7 O 1.0264(2) 0.47916(10) 0.38254(11) 0.0266(3) Uani 1.000000 .
O4 O 0.6415(3) 0.17095(10) 0.55748(12) 0.0334(4) Uani 1.000000 .
O1 O 0.2026(3) 0.43817(11) 0.13693(12) 0.0363(4) Uani 1.000000 .
O6 O 0.7142(3) 0.34242(11) 0.69136(12) 0.0366(4) Uani 1.000000 .
O5 O 0.4295(3) 0.38867(12) 0.57097(13) 0.0419(4) Uani 1.000000 .
N3 N 0.7202(3) 0.36277(11) 0.40823(12) 0.0234(4) Uani 1.000000 .
O2 O 0.1331(3) 0.29497(12) 0.20474(13) 0.0437(4) Uani 1.000000 .
N1 N 0.5024(3) 0.32815(11) 0.35721(13) 0.0243(4) Uani 1.000000 .
N5 N 0.6311(3) 0.35494(12) 0.59895(14) 0.0266(4) Uani 1.000000 .
N4 N 0.7854(3) 0.21372(12) 0.50357(13) 0.0263(4) Uani 1.000000 .
N2 N 0.2513(3) 0.37038(13) 0.19937(13) 0.0284(4) Uani 1.000000 .
O3 O 0.9211(3) 0.17784(11) 0.44120(13) 0.0477(5) Uani 1.000000 .
N6 N 0.6647(3) 0.52420(13) 0.18921(14) 0.0282(4) Uani 1.000000 .
C4 C 0.8318(3) 0.44103(13) 0.35432(15) 0.0214(4) Uani 1.000000 .
C2 C 0.4677(3) 0.38333(13) 0.27305(15) 0.0220(4) Uani 1.000000 .
C1 C 0.7976(3) 0.32520(13) 0.50981(15) 0.0228(4) Uani 1.000000 .
H1 H 0.9709(3) 0.34631(13) 0.52988(15) 0.0274(5) Uiso 1.000000 R
N7 N 0.6735(3) 0.58325(15) 0.12843(16) 0.0432(5) Uani 1.000000 .
C3 C 0.6538(3) 0.45431(13) 0.26381(15) 0.0226(4) Uani 1.000000 .


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
O7 C4 1.209(2) . ?
O4 N4 1.212(2) . ?
O1 N2 1.225(2) . ?
O6 N5 1.211(2) . ?
O5 N5 1.217(2) . ?
N3 N1 1.386(2) . ?
N3 C4 1.419(2) . ?
N3 C1 1.395(2) . ?
O2 N2 1.221(2) . ?
N1 C2 1.289(2) . ?
N5 C1 1.527(2) . ?
N4 O3 1.206(2) . ?
N4 C1 1.530(2) . ?
N2 C2 1.448(2) . ?
N6 N7 1.107(2) . ?
N6 C3 1.333(2) . ?
C4 C3 1.440(3) . ?
C2 C3 1.413(2) . ?
C1 H1 1.0000 . ?

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
C4 N3 N1 115.05(15) . . ?
C1 N3 N1 118.62(15) . . ?
C1 N3 C4 126.06(16) . . ?
C2 N1 N3 103.89(15) . . ?
O5 N5 O6 126.33(17) . . ?
C1 N5 O6 116.16(16) . . ?
C1 N5 O5 117.51(16) . . ?
O3 N4 O4 126.80(18) . . ?
C1 N4 O4 118.81(15) . . ?
C1 N4 O3 114.36(16) . . ?
O2 N2 O1 125.70(17) . . ?
C2 N2 O1 115.79(16) . . ?
C2 N2 O2 118.51(16) . . ?
C3 N6 N7 179.0(2) . . ?
N3 C4 O7 125.70(17) . . ?
C3 C4 O7 134.24(17) . . ?
C3 C4 N3 100.03(15) . . ?
N2 C2 N1 120.24(16) . . ?
C3 C2 N1 113.72(16) . . ?
C3 C2 N2 126.04(17) . . ?
N5 C1 N3 113.18(15) . . ?
N4 C1 N3 108.27(15) . . ?
N4 C1 N5 106.08(14) . . ?
H1 C1 N3 109.74(10) . . ?
H1 C1 N5 109.74(10) . . ?
H1 C1 N4 109.74(9) . . ?
C4 C3 N6 124.69(17) . . ?
C2 C3 N6 127.99(17) . . ?
C2 C3 C4 107.28(16) . . ?


_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_K
_database_code_depnum_ccdc_archive 'CCDC 2127242'
loop_
_audit_author_name
_audit_author_address
'VENTURE '
;Nanjing University of Science and Technology
Germany
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-05-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_chemical_formula_moiety         'C4 H2 Cl K N6 O9'
_chemical_formula_sum            'C4 H2 Cl K N6 O9'
_chemical_formula_weight         352.646
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
K 0.21174 0.26561 8.21860 7.43980 1.05190 0.86590 12.79490 0.77480 213.18700
41.68410 1.42280 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.100(3)
_cell_length_b                   15.461(3)
_cell_length_c                   6.9205(19)
_cell_angle_alpha                90
_cell_angle_beta                 102.99(1)
_cell_angle_gamma                90
_cell_volume                     1157.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1796
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.30
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1322 before and 0.0751 after correction.
The Ratio of minimum to maximum transmission is 0.8680.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.024
_exptl_crystal_description       needle
_exptl_crystal_F_000             705.915
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9939
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7926
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9939
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.88
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1419
_reflns_number_total             2128
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.7131
_refine_diff_density_min         -0.8166
_refine_diff_density_rms         0.1989
_refine_ls_d_res_high            0.8274
_refine_ls_d_res_low             10.8160
_refine_ls_goodness_of_fit_ref   1.1287
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2128
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.1282
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+0.7005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.1027
_olex2_refinement_description    
;
1. Restrained distances
 O9-H9a
 0.87 with sigma of 0.02
 O9-H9b
 0.87 with sigma of 0.02
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
K1 K 1.03064(9) 0.35849(7) 0.36873(14) 0.0252(3) Uani 1.000000 .
O7 O 0.3108(3) 0.3022(2) 0.4546(4) 0.0278(8) Uani 1.000000 .
O1 O 0.7468(3) 0.5211(2) 0.6608(4) 0.0286(8) Uani 1.000000 .
O4 O 0.7616(3) 0.2356(2) 0.7586(4) 0.0296(8) Uani 1.000000 .
O3 O 0.9201(3) 0.2901(2) 0.6635(5) 0.0314(8) Uani 1.000000 .
O2 O 0.9143(3) 0.4586(2) 0.6172(5) 0.0318(8) Uani 1.000000 .
O6 O 0.6821(3) 0.4465(2) 1.2400(4) 0.0315(8) Uani 1.000000 .
N2 N 0.8162(3) 0.2980(2) 0.7014(5) 0.0219(9) Uani 1.000000 .
O8 O 0.2462(3) 0.3580(2) 0.7007(4) 0.0308(8) Uani 1.000000 .
O5 O 0.8224(3) 0.4272(2) 1.0689(4) 0.0353(9) Uani 1.000000 .
N1 N 0.8090(3) 0.4542(2) 0.6522(5) 0.0221(9) Uani 1.000000 .
N4 N 0.6430(3) 0.3790(2) 0.7429(5) 0.0202(9) Uani 1.000000 .
N6 N 0.3279(3) 0.3366(2) 0.6178(5) 0.0214(9) Uani 1.000000 .
N5 N 0.5398(3) 0.3547(2) 0.6139(5) 0.0205(9) Uani 1.000000 .
N3 N 0.7153(4) 0.4249(2) 1.0898(5) 0.0254(9) Uani 1.000000 .
C2 C 0.6213(4) 0.3943(3) 0.9266(6) 0.0187(10) Uani 1.000000 .
C3 C 0.4986(4) 0.3804(3) 0.9185(6) 0.0182(10) Uani 1.000000 .
C1 C 0.7559(4) 0.3760(3) 0.6837(6) 0.0210(10) Uani 1.000000 .
O9 O 1.0968(4) 0.3456(4) 0.0159(6) 0.0610(13) Uani 1.000000 D
C4 C 0.4542(4) 0.3568(3) 0.7196(6) 0.0209(10) Uani 1.000000 .
Cl1 Cl 0.42254(10) 0.38892(8) 1.10372(16) 0.0261(3) Uani 1.000000 .
H9a H 1.166(4) 0.366(5) 0.000(11) 0.12(3) Uiso 1.000000 D
H9b H 1.045(6) 0.364(6) -0.089(8) 0.16(4) Uiso 1.000000 D


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
K1 O7 3.154(3) 1_655 ?
K1 O1 3.136(3) 3_766 ?
K1 O4 3.255(3) 4_565 ?
K1 O3 2.831(3) 4_565 ?
K1 O3 2.812(3) . ?
K1 O2 2.831(3) . ?
K1 O2 2.891(3) 3_766 ?
K1 O8 2.921(3) 1_655 ?
K1 O5 2.936(3) 1_554 ?
K1 N6 3.379(4) 1_655 ?
K1 O9 3.346(5) 4_566 ?
K1 O9 2.710(4) . ?
O7 N6 1.224(4) . ?
O1 N1 1.253(4) . ?
O4 N2 1.250(4) . ?
O3 N2 1.246(4) . ?
O2 N1 1.247(4) . ?
O6 N3 1.225(4) . ?
N2 C1 1.371(5) . ?
O8 N6 1.224(4) . ?
O5 N3 1.230(4) . ?
N1 C1 1.384(5) . ?
N4 N5 1.338(5) . ?
N4 C2 1.367(5) . ?
N4 C1 1.404(5) . ?
N6 C4 1.454(5) . ?
N5 C4 1.323(5) . ?
N3 C2 1.434(5) . ?
C2 C3 1.367(6) . ?
C3 C4 1.402(6) . ?
C3 Cl1 1.692(4) . ?
O9 H9a 0.857(19) . ?
O9 H9b 0.867(19) . ?

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
O1 K1 O7 54.44(8) 3_766 1_655 ?
O4 K1 O7 137.27(9) 4_565 1_655 ?
O4 K1 O1 160.86(8) 4_565 3_766 ?
O3 K1 O7 99.69(9) 4_565 1_655 ?
O3 K1 O7 109.38(9) . 1_655 ?
O3 K1 O1 138.50(9) . 3_766 ?
O3 K1 O1 135.04(8) 4_565 3_766 ?
O3 K1 O4 41.28(8) 4_565 4_565 ?
O3 K1 O4 58.32(9) . 4_565 ?
O2 K1 O7 126.97(9) . 1_655 ?
O2 K1 O7 94.10(9) 3_766 1_655 ?
O2 K1 O1 42.08(8) 3_766 3_766 ?
O2 K1 O1 100.89(9) . 3_766 ?
O2 K1 O4 82.33(8) . 4_565 ?
O2 K1 O4 128.41(9) 3_766 4_565 ?
O2 K1 O3 122.86(9) . 4_565 ?
O2 K1 O3 151.08(10) 3_766 4_565 ?
O2 K1 O3 55.40(9) . . ?
O2 K1 O3 117.84(9) 3_766 . ?
O8 K1 O7 41.64(8) 1_655 1_655 ?
O8 K1 O1 62.28(8) 1_655 3_766 ?
O8 K1 O4 136.83(9) 1_655 4_565 ?
O8 K1 O3 80.92(9) 1_655 . ?
O8 K1 O3 125.35(10) 1_655 4_565 ?
O8 K1 O2 85.90(9) 1_655 . ?
O8 K1 O2 81.15(10) 1_655 3_766 ?
O5 K1 O7 145.00(9) 1_554 1_655 ?
O5 K1 O1 104.22(9) 1_554 3_766 ?
O5 K1 O4 57.39(9) 1_554 4_565 ?
O5 K1 O3 75.85(10) 1_554 4_565 ?
O5 K1 O3 104.25(9) 1_554 . ?
O5 K1 O2 80.63(10) 1_554 . ?
O5 K1 O2 78.27(10) 1_554 3_766 ?
O5 K1 O8 158.79(10) 1_554 1_655 ?
N6 K1 O7 21.23(7) 1_655 1_655 ?
N6 K1 O1 53.10(8) 1_655 3_766 ?
N6 K1 O4 144.50(9) 1_655 4_565 ?
N6 K1 O3 97.33(9) 1_655 . ?
N6 K1 O3 115.97(10) 1_655 4_565 ?
N6 K1 O2 105.76(9) 1_655 . ?
N6 K1 O2 84.60(9) 1_655 3_766 ?
N6 K1 O8 20.81(8) 1_655 1_655 ?
N6 K1 O5 156.95(9) 1_655 1_554 ?
O9 K1 O7 72.19(11) . 1_655 ?
O9 K1 O7 62.80(9) 4_566 1_655 ?
O9 K1 O1 66.93(11) . 3_766 ?
O9 K1 O1 117.22(10) 4_566 3_766 ?
O9 K1 O4 100.15(11) . 4_565 ?
O9 K1 O4 77.10(10) 4_566 4_565 ?
O9 K1 O3 70.29(12) . 4_565 ?
O9 K1 O3 55.14(10) 4_566 4_565 ?
O9 K1 O3 151.20(13) . . ?
O9 K1 O3 61.71(9) 4_566 . ?
O9 K1 O2 147.17(14) . . ?
O9 K1 O2 151.89(11) 4_566 3_766 ?
O9 K1 O2 90.25(13) . 3_766 ?
O9 K1 O2 115.41(9) 4_566 . ?
O9 K1 O8 111.63(11) . 1_655 ?
O9 K1 O8 70.93(11) 4_566 1_655 ?
O9 K1 O5 73.73(12) . 1_554 ?
O9 K1 O5 129.82(11) 4_566 1_554 ?
O9 K1 N6 68.15(10) 4_566 1_655 ?
O9 K1 N6 91.19(11) . 1_655 ?
N6 O7 K1 89.8(2) . 1_455 ?
N1 O1 K1 92.1(2) . 3_766 ?
N2 O4 K1 86.2(2) . 4_566 ?
N2 O3 K1 107.0(2) . 4_566 ?
N2 O3 K1 133.8(3) . . ?
N1 O2 K1 131.6(3) . . ?
N1 O2 K1 104.3(2) . 3_766 ?
O3 N2 O4 121.9(4) . . ?
C1 N2 O4 116.4(3) . . ?
C1 N2 O3 121.6(4) . . ?
N6 O8 K1 101.2(2) . 1_455 ?
N3 O5 K1 122.3(3) . 1_556 ?
O2 N1 O1 121.0(4) . . ?
C1 N1 O1 117.1(3) . . ?
C1 N1 O2 122.0(4) . . ?
C2 N4 N5 111.4(3) . . ?
C1 N4 N5 118.8(3) . . ?
C1 N4 C2 129.3(4) . . ?
O7 N6 K1 69.0(2) . 1_455 ?
O8 N6 K1 58.0(2) . 1_455 ?
O8 N6 O7 124.9(4) . . ?
C4 N6 K1 161.8(3) . 1_455 ?
C4 N6 O7 118.3(3) . . ?
C4 N6 O8 116.8(4) . . ?
C4 N5 N4 103.8(3) . . ?
O5 N3 O6 125.1(4) . . ?
C2 N3 O6 117.0(4) . . ?
C2 N3 O5 117.9(4) . . ?
N3 C2 N4 122.7(4) . . ?
C3 C2 N4 108.5(4) . . ?
C3 C2 N3 128.7(4) . . ?
C4 C3 C2 102.0(3) . . ?
Cl1 C3 C2 128.3(3) . . ?
Cl1 C3 C4 129.7(3) . . ?
N1 C1 N2 124.4(4) . . ?
N4 C1 N2 117.0(4) . . ?
N4 C1 N1 117.2(4) . . ?
H9a O9 K1 116(5) . 4_565 ?
H9a O9 K1 121(5) . . ?
H9b O9 K1 118(6) . . ?
H9b O9 K1 89(6) . 4_565 ?
H9b O9 H9a 103(7) . . ?
N5 C4 N6 117.4(4) . . ?
C3 C4 N6 128.3(4) . . ?
C3 C4 N5 114.3(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 O7 N6 O8 16.0(3) 1_455 . . . ?
K1 O7 N6 C4 -161.6(2) 1_455 . . . ?
K1 O1 N1 O2 -7.4(2) 3_766 . . . ?
K1 O1 N1 C1 172.4(2) 3_766 . . . ?
K1 O4 N2 O3 18.2(2) 4_566 . . . ?
K1 O4 N2 C1 -161.5(2) 4_566 . . . ?
K1 O3 N2 O4 -22.0(3) 4_566 . . . ?
K1 O3 N2 O4 140.9(3) . . . . ?
K1 O3 N2 C1 157.7(3) 4_566 . . . ?
K1 O3 N2 C1 -39.5(4) . . . . ?
K1 O2 N1 O1 8.3(3) 3_766 . . . ?
K1 O2 N1 O1 -137.2(3) . . . . ?
K1 O2 N1 C1 -171.5(2) 3_766 . . . ?
K1 O2 N1 C1 43.0(4) . . . . ?
K1 O8 N6 O7 -17.7(3) 1_455 . . . ?
K1 O8 N6 C4 160.0(2) 1_455 . . . ?
K1 O5 N3 O6 47.4(3) 1_556 . . . ?
K1 O5 N3 C2 -132.5(3) 1_556 . . . ?
K1 N6 C4 N5 -94.8(8) 1_455 . . . ?
K1 N6 C4 C3 83.8(8) 1_455 . . . ?
O7 N6 C4 N5 14.6(4) . . . . ?
O7 N6 C4 C3 -166.8(4) . . . . ?
O1 N1 C1 N2 -172.3(3) . . . . ?
O1 N1 C1 N4 -6.5(4) . . . . ?
O4 N2 C1 N1 169.7(3) . . . . ?
O4 N2 C1 N4 3.8(4) . . . . ?
O3 N2 C1 N1 -10.0(5) . . . . ?
O3 N2 C1 N4 -175.8(4) . . . . ?
O2 N1 C1 N2 7.5(5) . . . . ?
O2 N1 C1 N4 173.3(4) . . . . ?
O6 N3 C2 N4 171.1(4) . . . . ?
O6 N3 C2 C3 -4.6(5) . . . . ?
N2 C1 N4 N5 -84.3(4) . . . . ?
N2 C1 N4 C2 87.2(5) . . . . ?
O8 N6 C4 N5 -163.2(4) . . . . ?
O8 N6 C4 C3 15.4(5) . . . . ?
O5 N3 C2 N4 -9.0(4) . . . . ?
O5 N3 C2 C3 175.2(4) . . . . ?
N1 C1 N4 N5 108.8(4) . . . . ?
N1 C1 N4 C2 -79.7(5) . . . . ?
N4 N5 C4 N6 177.6(3) . . . . ?
N4 N5 C4 C3 -1.2(4) . . . . ?
N4 C2 C3 C4 -0.1(4) . . . . ?
N4 C2 C3 Cl1 179.3(2) . . . . ?
N6 C4 C3 C2 -177.8(5) . . . . ?
N6 C4 C3 Cl1 2.8(6) . . . . ?
N5 C4 C3 C2 0.9(4) . . . . ?
N5 C4 C3 Cl1 -178.6(3) . . . . ?
N3 C2 C3 C4 176.2(5) . . . . ?
N3 C2 C3 Cl1 -4.4(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O9 H9a 1 0.8700 0.0200 0.0126
O9 H9b 1 0.8700 0.0200 0.0033

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2127241'
loop_
_audit_author_name
_audit_author_address
'VENTURE '
;Nanjing University of Science and Technology
Germany
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;
_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_chemical_formula_moiety         'C4 H2 N7 O8, H2 O, H4 N'
_chemical_formula_sum            'C4 H8 N8 O9'
_chemical_formula_weight         312.157
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.9418(19)
_cell_length_b                   15.988(3)
_cell_length_c                   6.7678(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.161(6)
_cell_angle_gamma                90
_cell_volume                     1165.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2137
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.688
_cell_measurement_theta_min      2.281
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1127 before and 0.0677 after correction. The Ratio of minimum to maximum transmission is 0.9067. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_description       block
_exptl_crystal_F_000             640.681
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.9881
_diffrn_reflns_Laue_measured_fraction_max 0.9853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11341
_diffrn_reflns_point_group_measured_fraction_full 0.9881
_diffrn_reflns_point_group_measured_fraction_max 0.9853
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         2.28
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.9881
_diffrn_measured_fraction_theta_max 0.9853
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1542
_reflns_number_total             2274
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.4097
_refine_diff_density_min         -0.5242
_refine_diff_density_rms         0.1191
_refine_ls_d_res_high            0.8096
_refine_ls_d_res_low             8.9324
_refine_ls_goodness_of_fit_ref   1.1145
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.1120
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0040P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0604
_refine_special_details          
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      cc-pVTZ
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2022-05-17_16-35-23
;
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 N5, H5a, H5b
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
O5 O 0.07399(13) 0.30962(8) 0.3159(2) 0.0280(4) Uani 1.000000 . .
O6 O 0.23193(14) 0.24327(8) 0.2388(2) 0.0289(4) Uani 1.000000 . .
O4 O 0.11692(14) 0.46688(8) 0.4244(2) 0.0316(4) Uani 1.000000 . .
O1 O 0.70217(13) 0.30246(8) 0.5943(2) 0.0316(4) Uani 1.000000 . .
O3 O 0.29163(14) 0.51492(8) 0.3627(2) 0.0296(4) Uani 1.000000 . .
O7 O 0.21815(14) 0.42610(8) -0.0616(2) 0.0292(4) Uani 1.000000 . .
O2 O 0.77741(14) 0.34317(9) 0.3357(2) 0.0342(4) Uani 1.000000 . .
O8 O 0.37351(14) 0.43352(9) -0.2234(2) 0.0340(4) Uani 1.000000 . .
N3 N 0.37726(16) 0.37129(9) 0.2790(2) 0.0199(4) Uani 1.000000 . .
N2 N 0.47497(16) 0.34813(9) 0.4134(2) 0.0209(4) Uani 1.000000 . .
O9 O -0.0884(2) 0.41591(17) 1.0346(3) 0.0451(6) Uani 1.000000 . .
N8 N 0.18530(16) 0.30777(10) 0.2950(2) 0.0203(4) Uani 1.000000 . .
N6 N 0.21973(17) 0.45613(10) 0.3750(2) 0.0218(4) Uani 1.000000 . .
N1 N 0.69076(17) 0.33000(10) 0.4236(3) 0.0232(4) Uani 1.000000 . .
N4 N 0.32952(18) 0.41733(10) -0.0724(2) 0.0238(4) Uani 1.000000 . .
N7 N -0.0124(3) 0.36081(19) 0.6819(5) 0.0262(6) Uani 1.000000 . .
N5 N 0.6115(2) 0.38567(12) -0.0253(3) 0.0297(5) Uani 1.000000 . U
H5a H 0.699(2) 0.3739(15) 0.006(3) 0.044(8) Uani 1.000000 . U
H5b H 0.568(2) 0.4020(16) -0.168(4) 0.057(8) Uani 1.000000 . U
C1 C 0.26063(19) 0.37682(11) 0.3322(3) 0.0200(5) Uani 1.000000 . .
C4 C 0.56995(19) 0.35016(11) 0.3173(3) 0.0200(5) Uani 1.000000 . .
C2 C 0.4111(2) 0.38808(11) 0.0950(3) 0.0207(5) Uani 1.000000 . .
C3 C 0.5388(2) 0.37557(11) 0.1120(3) 0.0206(5) Uani 1.000000 . .
H7a H 0.033(4) 0.309(2) 0.712(5) 0.082(12) Uani 1.000000 . .
H7b H 0.037(3) 0.399(2) 0.619(5) 0.074(12) Uani 1.000000 . .
H7c H -0.035(3) 0.3852(14) 0.803(4) 0.048(9) Uani 1.000000 . .
H7d H -0.077(3) 0.345(2) 0.577(6) 0.089(13) Uani 1.000000 . .
H9a H -0.101(4) 0.4707(19) 1.066(5) 0.110(17) Uani 1.000000 . .
H9b H -0.038(3) 0.398(2) 1.154(5) 0.088(14) Uani 1.000000 . .


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
O5 N8 1.251(2) . ?
O6 N8 1.2396(18) . ?
O4 N6 1.241(2) . ?
O1 N1 1.222(2) . ?
O3 N6 1.2378(19) . ?
O7 N4 1.242(2) . ?
O2 N1 1.223(2) . ?
O8 N4 1.2312(19) . ?
N3 N2 1.328(2) . ?
N3 C1 1.388(2) . ?
N3 C2 1.387(2) . ?
N2 C4 1.320(2) . ?
O9 H9a 0.92(3) . ?
O9 H9b 0.94(3) . ?
N8 C1 1.374(2) . ?
N6 C1 1.392(2) . ?
N1 C4 1.426(3) . ?
N4 C2 1.393(2) . ?
N7 H7a 0.97(3) . ?
N7 H7b 0.97(3) . ?
N7 H7c 0.98(2) . ?
N7 H7d 0.94(3) . ?
N5 H5a 0.96(2) . ?
N5 H5b 1.03(2) . ?
N5 C3 1.336(3) . ?
C4 C3 1.430(2) . ?
C2 C3 1.396(3) . ?

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
C1 N3 N2 120.41(16) . . ?
C2 N3 N2 111.02(16) . . ?
C2 N3 C1 128.57(17) . . ?
C4 N2 N3 105.34(16) . . ?
H9b O9 H9a 100(3) . . ?
O6 N8 O5 121.06(16) . . ?
C1 N8 O5 121.64(16) . . ?
C1 N8 O6 117.29(17) . . ?
O3 N6 O4 122.00(16) . . ?
C1 N6 O4 121.49(17) . . ?
C1 N6 O3 116.51(17) . . ?
O2 N1 O1 124.28(18) . . ?
C4 N1 O1 119.30(17) . . ?
C4 N1 O2 116.40(17) . . ?
O8 N4 O7 123.82(18) . . ?
C2 N4 O7 118.97(16) . . ?
C2 N4 O8 117.21(18) . . ?
H7b N7 H7a 110(3) . . ?
H7c N7 H7a 111(2) . . ?
H7c N7 H7b 111(2) . . ?
H7d N7 H7a 102(3) . . ?
H7d N7 H7b 104(3) . . ?
H7d N7 H7c 118(3) . . ?
H5b N5 H5a 122(2) . . ?
C3 N5 H5a 120.9(14) . . ?
C3 N5 H5b 116.9(14) . . ?
N8 C1 N3 116.76(16) . . ?
N6 C1 N3 117.12(16) . . ?
N6 C1 N8 124.44(18) . . ?
N1 C4 N2 119.09(18) . . ?
C3 C4 N2 114.34(18) . . ?
C3 C4 N1 126.55(18) . . ?
N4 C2 N3 124.14(18) . . ?
C3 C2 N3 108.66(17) . . ?
C3 C2 N4 127.09(17) . . ?
C4 C3 N5 129.9(2) . . ?
C2 C3 N5 129.5(2) . . ?
C2 C3 C4 100.63(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7c O9 0.98(2) 1.83(3) 2.805(4) 172(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
O5 N8 C1 N3 -171.72(17) . . . . ?
O5 N8 C1 N6 -7.0(2) . . . . ?
O6 N8 C1 N3 7.98(18) . . . . ?
O6 N8 C1 N6 172.75(15) . . . . ?
O4 N6 C1 N3 -179.75(17) . . . . ?
O4 N6 C1 N8 15.5(2) . . . . ?
O1 N1 C4 N2 8.00(18) . . . . ?
O1 N1 C4 C3 -173.92(16) . . . . ?
O3 N6 C1 N3 -0.36(19) . . . . ?
O3 N6 C1 N8 -165.07(15) . . . . ?
O7 N4 C2 N3 -3.07(19) . . . . ?
O7 N4 C2 C3 -178.94(16) . . . . ?
O2 N1 C4 N2 -170.88(16) . . . . ?
O2 N1 C4 C3 7.19(19) . . . . ?
O8 N4 C2 N3 176.49(15) . . . . ?
O8 N4 C2 C3 0.6(2) . . . . ?
N3 N2 C4 N1 178.59(13) . . . . ?
N3 N2 C4 C3 0.29(16) . . . . ?
N3 C2 C3 N5 -178.68(15) . . . . ?
N3 C2 C3 C4 0.57(16) . . . . ?
N2 C4 C3 N5 178.71(16) . . . . ?
N2 C4 C3 C2 -0.54(17) . . . . ?
N1 C4 C3 N5 0.5(2) . . . . ?
N1 C4 C3 C2 -178.7(2) . . . . ?
N4 C2 C3 N5 -2.3(2) . . . . ?
N4 C2 C3 C4 177.0(2) . . . . ?



_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
N5 H5a 0.004000 0.001585 -0.000142 -0.003007
N5 H5b 0.004000 -0.000783 0.000919 -0.000820
H5a H5b 0.004000 0.001865 -0.007833 -0.001075

