# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1947089'
loop_
_audit_author_name
_audit_author_address
'Sitong Chen'
;CAEP
China
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_audit_creation_date             2019-07-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.08.17 svn.r3210 for OlexSys, GUI svn.r5083)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H2 Cl2 N4 O2'
_chemical_formula_sum            'C4 H2 Cl2 N4 O2'
_chemical_formula_weight         209.00
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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'

_cell_length_a                   16.0864(10)
_cell_length_b                   12.7175(8)
_cell_length_c                   7.1186(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.450(2)
_cell_angle_gamma                90.00
_cell_volume                     1436.55(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7375
_cell_measurement_temperature    227
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.03
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5370
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1193 before and 0.0847 after correction.
The Ratio of minimum to maximum transmission is 0.7202.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.933
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16870
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         2.57
_diffrn_ambient_temperature      227.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2683
_reflns_number_total             3286
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0330P)²+1.1250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl2 Cl 0.08925(3) 0.30079(4) 0.38891(9) 0.03174(17) Uani 1 d . . .
Cl4 Cl 0.58909(3) 0.58845(4) 0.85927(9) 0.02988(16) Uani 1 d . . .
Cl3 Cl 0.29967(4) 0.30970(4) 0.51146(9) 0.03297(17) Uani 1 d . . .
Cl1 Cl -0.19729(4) 0.56776(4) -0.01228(10) 0.03592(18) Uani 1 d . . .
O1 O -0.27936(10) 0.36731(13) 0.0579(2) 0.0307(4) Uani 1 d . . .
O2 O -0.21125(10) 0.24962(12) -0.0761(2) 0.0294(4) Uani 1 d . . .
N2 N -0.06679(13) 0.20616(14) 0.1826(3) 0.0245(4) Uani 1 d . . .
N7 N 0.51160(12) 0.41453(14) 0.7711(3) 0.0255(4) Uani 1 d . . .
N3 N 0.01242(12) 0.47147(14) 0.2709(3) 0.0258(4) Uani 1 d . . .
C7 C 0.42909(14) 0.57179(16) 0.6729(3) 0.0206(4) Uani 1 d . . .
O3 O 0.21876(10) 0.51982(14) 0.5407(3) 0.0391(5) Uani 1 d . . .
C4 C 0.00489(13) 0.36958(16) 0.2701(3) 0.0212(4) Uani 1 d . . .
C8 C 0.50273(13) 0.51635(17) 0.7604(3) 0.0208(4) Uani 1 d . . .
N8 N 0.44730(12) 0.35076(14) 0.6941(3) 0.0261(4) Uani 1 d . . .
C3 C -0.06693(13) 0.31117(15) 0.1815(3) 0.0193(4) Uani 1 d . . .
C5 C 0.37654(14) 0.39551(16) 0.6130(3) 0.0217(5) Uani 1 d . . .
N4 N -0.05124(12) 0.53187(14) 0.1801(3) 0.0262(4) Uani 1 d . . .
N6 N 0.42674(15) 0.67650(15) 0.6686(3) 0.0312(5) Uani 1 d . . .
C1 C -0.12154(14) 0.48516(16) 0.1034(3) 0.0218(5) Uani 1 d . . .
N5 N 0.28558(12) 0.54672(14) 0.4952(3) 0.0258(4) Uani 1 d . . .
C2 C -0.13360(13) 0.37605(16) 0.1037(3) 0.0189(4) Uani 1 d . . .
C6 C 0.36417(13) 0.50384(16) 0.5985(3) 0.0198(4) Uani 1 d . . .
O4 O 0.29238(12) 0.60897(15) 0.3673(3) 0.0425(5) Uani 1 d . . .
N1 N -0.21435(11) 0.32898(13) 0.0225(3) 0.0212(4) Uani 1 d . . .
H2A H -0.0235(18) 0.173(2) 0.240(4) 0.030(7) Uiso 1 d . . .
H6A H 0.3865(19) 0.705(2) 0.613(4) 0.034(8) Uiso 1 d . . .
H2B H -0.1099(19) 0.173(2) 0.129(4) 0.038(8) Uiso 1 d . . .
H6B H 0.4711(19) 0.711(2) 0.722(4) 0.038(8) Uiso 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl2 0.0196(3) 0.0270(3) 0.0448(4) 0.0056(2) -0.0060(2) 0.0035(2)
Cl4 0.0213(3) 0.0281(3) 0.0384(3) -0.0038(2) -0.0004(2) -0.0068(2)
Cl3 0.0251(3) 0.0195(3) 0.0498(4) -0.0014(2) -0.0072(3) -0.0047(2)
Cl1 0.0273(3) 0.0180(3) 0.0568(4) 0.0077(2) -0.0102(3) 0.0030(2)
O1 0.0168(8) 0.0346(9) 0.0397(10) 0.0037(7) 0.0019(7) 0.0015(7)
O2 0.0327(9) 0.0182(8) 0.0341(9) -0.0045(7) -0.0042(7) -0.0057(7)
N2 0.0214(10) 0.0141(9) 0.0365(11) 0.0015(8) 0.0001(9) 0.0017(8)
N7 0.0204(10) 0.0203(9) 0.0338(11) 0.0002(8) -0.0012(8) 0.0005(7)
N3 0.0206(10) 0.0179(9) 0.0361(11) 0.0001(8) -0.0034(8) -0.0010(7)
C7 0.0241(11) 0.0177(10) 0.0205(10) -0.0006(8) 0.0055(9) 0.0003(8)
O3 0.0189(9) 0.0323(9) 0.0635(13) -0.0058(9) -0.0010(8) 0.0001(7)
C4 0.0171(10) 0.0181(10) 0.0275(11) 0.0020(8) 0.0007(9) 0.0021(8)
C8 0.0190(10) 0.0207(10) 0.0228(10) -0.0017(8) 0.0036(8) -0.0019(8)
N8 0.0228(10) 0.0172(9) 0.0360(11) 0.0007(8) -0.0019(8) -0.0003(7)
C3 0.0216(11) 0.0137(9) 0.0228(10) 0.0007(8) 0.0045(9) 0.0011(8)
C5 0.0195(11) 0.0181(10) 0.0265(11) -0.0010(8) 0.0007(9) -0.0016(8)
N4 0.0214(10) 0.0158(8) 0.0391(11) 0.0008(8) -0.0023(8) -0.0013(7)
N6 0.0302(12) 0.0148(9) 0.0448(13) -0.0011(9) -0.0051(10) -0.0005(9)
C1 0.0215(11) 0.0144(10) 0.0284(11) 0.0005(8) 0.0003(9) 0.0019(8)
N5 0.0253(10) 0.0207(9) 0.0287(10) -0.0052(8) -0.0039(8) 0.0061(8)
C2 0.0172(10) 0.0162(10) 0.0226(10) -0.0019(8) 0.0009(8) -0.0029(8)
C6 0.0191(10) 0.0180(10) 0.0214(10) 0.0010(8) 0.0009(8) 0.0038(8)
O4 0.0492(12) 0.0432(11) 0.0326(10) 0.0116(8) -0.0011(8) 0.0168(9)
N1 0.0201(9) 0.0166(9) 0.0250(9) 0.0052(7) -0.0019(7) -0.0016(7)

_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
Cl2 C4 1.716(2) . ?
Cl4 C8 1.716(2) . ?
Cl3 C5 1.717(2) . ?
Cl1 C1 1.714(2) . ?
O1 N1 1.217(2) . ?
O2 N1 1.235(2) . ?
N2 C3 1.335(3) . ?
N2 H2A 0.86(3) . ?
N2 H2B 0.85(3) . ?
N7 C8 1.304(3) . ?
N7 N8 1.357(2) . ?
N3 C4 1.301(3) . ?
N3 N4 1.356(2) . ?
C7 C8 1.431(3) . ?
C7 N6 1.332(3) . ?
C7 C6 1.391(3) . ?
O3 N5 1.221(3) . ?
C4 C3 1.430(3) . ?
N8 C5 1.318(3) . ?
C3 C2 1.394(3) . ?
C5 C6 1.393(3) . ?
N4 C1 1.314(3) . ?
N6 H6A 0.79(3) . ?
N6 H6B 0.87(3) . ?
C1 C2 1.401(3) . ?
N5 C6 1.460(3) . ?
N5 O4 1.225(3) . ?
C2 N1 1.461(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
C3 N2 H2A 119.3(17) . . ?
C3 N2 H2B 119.4(19) . . ?
H2A N2 H2B 121(3) . . ?
C8 N7 N8 120.06(18) . . ?
C4 N3 N4 119.96(18) . . ?
N6 C7 C8 121.4(2) . . ?
N6 C7 C6 126.5(2) . . ?
C6 C7 C8 112.07(18) . . ?
N3 C4 Cl2 116.09(16) . . ?
N3 C4 C3 125.95(19) . . ?
C3 C4 Cl2 117.96(15) . . ?
N7 C8 Cl4 115.67(16) . . ?
N7 C8 C7 126.16(19) . . ?
C7 C8 Cl4 118.16(16) . . ?
C5 N8 N7 117.72(17) . . ?
N2 C3 C4 121.09(19) . . ?
N2 C3 C2 126.5(2) . . ?
C2 C3 C4 112.39(17) . . ?
N8 C5 Cl3 114.86(16) . . ?
N8 C5 C6 124.19(19) . . ?
C6 C5 Cl3 120.86(16) . . ?
C1 N4 N3 118.22(17) . . ?
C7 N6 H6A 119(2) . . ?
C7 N6 H6B 118.3(19) . . ?
H6A N6 H6B 123(3) . . ?
N4 C1 Cl1 114.71(15) . . ?
N4 C1 C2 123.85(19) . . ?
C2 C1 Cl1 121.33(16) . . ?
O3 N5 C6 119.26(19) . . ?
O3 N5 O4 124.6(2) . . ?
O4 N5 C6 116.12(19) . . ?
C3 C2 C1 119.28(19) . . ?
C3 C2 N1 119.40(18) . . ?
C1 C2 N1 121.31(18) . . ?
C7 C6 C5 119.79(19) . . ?
C7 C6 N5 119.56(18) . . ?
C5 C6 N5 120.53(18) . . ?
O1 N1 O2 124.13(18) . . ?
O1 N1 C2 119.51(17) . . ?
O2 N1 C2 116.33(18) . . ?

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
Cl2 C4 C3 N2 -3.4(3) . . . . ?
Cl2 C4 C3 C2 174.99(16) . . . . ?
Cl3 C5 C6 C7 -176.47(17) . . . . ?
Cl3 C5 C6 N5 -0.5(3) . . . . ?
Cl1 C1 C2 C3 172.99(17) . . . . ?
Cl1 C1 C2 N1 -6.4(3) . . . . ?
N2 C3 C2 C1 -175.8(2) . . . . ?
N2 C3 C2 N1 3.6(3) . . . . ?
N7 N8 C5 Cl3 177.75(16) . . . . ?
N7 N8 C5 C6 1.2(3) . . . . ?
N3 C4 C3 N2 177.2(2) . . . . ?
N3 C4 C3 C2 -4.4(3) . . . . ?
N3 N4 C1 Cl1 -178.68(16) . . . . ?
N3 N4 C1 C2 -2.5(3) . . . . ?
O3 N5 C6 C7 -128.3(2) . . . . ?
O3 N5 C6 C5 55.7(3) . . . . ?
C4 N3 N4 C1 4.3(3) . . . . ?
C4 C3 C2 C1 5.9(3) . . . . ?
C4 C3 C2 N1 -174.66(19) . . . . ?
C8 N7 N8 C5 -1.2(3) . . . . ?
C8 C7 C6 C5 -0.8(3) . . . . ?
C8 C7 C6 N5 -176.89(19) . . . . ?
N8 N7 C8 Cl4 -178.86(16) . . . . ?
N8 N7 C8 C7 0.3(4) . . . . ?
N8 C5 C6 C7 -0.1(4) . . . . ?
N8 C5 C6 N5 175.9(2) . . . . ?
C3 C2 N1 O1 135.9(2) . . . . ?
C3 C2 N1 O2 -42.5(3) . . . . ?
N4 N3 C4 Cl2 179.88(17) . . . . ?
N4 N3 C4 C3 -0.8(4) . . . . ?
N4 C1 C2 C3 -3.0(4) . . . . ?
N4 C1 C2 N1 177.6(2) . . . . ?
N6 C7 C8 Cl4 -0.5(3) . . . . ?
N6 C7 C8 N7 -179.6(2) . . . . ?
N6 C7 C6 C5 179.5(2) . . . . ?
N6 C7 C6 N5 3.5(4) . . . . ?
C1 C2 N1 O1 -44.7(3) . . . . ?
C1 C2 N1 O2 136.9(2) . . . . ?
C6 C7 C8 Cl4 179.88(16) . . . . ?
C6 C7 C8 N7 0.8(3) . . . . ?
O4 N5 C6 C7 51.2(3) . . . . ?
O4 N5 C6 C5 -124.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Deliquescent
####################################################################### 
# 
# 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_ff
_database_code_depnum_ccdc_archive 'CCDC 1947090'
loop_
_audit_author_name
_audit_author_address
'Sitong Chen'
;CAEP
China
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_audit_creation_date             2019-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'H2 O, 2(C4 H4 N8 O2)'
_chemical_formula_sum            'C8 H10 N16 O5'
_chemical_formula_weight         410.32
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.2036(15)
_cell_length_b                   4.6757(5)
_cell_length_c                   25.698(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.484(7)
_cell_angle_gamma                90.00
_cell_volume                     1463.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1376
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      3.18
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1764 before and 0.0698 after correction.
The Ratio of minimum to maximum transmission is 0.8055.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0913
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            5433
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1017
_reflns_number_total             1659
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.0035(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1287
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O3 O 0.5000 1.2932(6) 0.7500 0.0212(7) Uani 1 d . . 2 S T P
O1 O 0.49423(15) 0.9703(4) 0.55091(6) 0.0200(5) Uani 1 d . . 1 . . .
O2 O 0.47929(15) 1.1186(4) 0.62996(6) 0.0186(5) Uani 1 d . . 1 . . .
N7 N 0.22449(17) 0.3275(4) 0.61496(8) 0.0136(5) Uani 1 d . . 1 . . .
N2 N 0.45313(18) 0.9508(4) 0.59383(8) 0.0145(5) Uani 1 d . . 1 . . .
N4 N 0.20215(17) 0.3882(4) 0.69728(8) 0.0159(5) Uani 1 d . . 1 . . .
N1 N 0.3675(2) 0.5668(5) 0.51170(9) 0.0175(6) Uani 1 d . . 1 . . .
N3 N 0.36366(19) 0.8529(5) 0.69527(8) 0.0152(5) Uani 1 d . . 1 . . .
N5 N 0.13943(18) 0.1710(5) 0.67800(8) 0.0165(5) Uani 1 d . . 1 . . .
N6 N 0.15096(18) 0.1286(5) 0.62789(8) 0.0165(5) Uani 1 d . . 1 . . .
N8 N 0.25867(17) 0.3442(5) 0.56574(7) 0.0153(5) Uani 1 d . . 1 . . .
C4 C 0.2560(2) 0.4823(6) 0.65698(9) 0.0133(6) Uani 1 d . . 1 . . .
C2 C 0.3742(2) 0.7344(5) 0.60227(9) 0.0127(6) Uani 1 d . . 1 . . .
C1 C 0.3331(2) 0.5481(5) 0.55984(9) 0.0134(6) Uani 1 d . . 1 . . .
C3 C 0.3357(2) 0.7059(5) 0.65249(10) 0.0144(6) Uani 1 d . . 1 . . .
H3A H 0.413(3) 0.999(8) 0.6926(12) 0.047(10) Uiso 1 d . . 1 . . .
H1A H 0.336(2) 0.449(7) 0.4902(11) 0.026(9) Uiso 1 d . . 1 . . .
H3B H 0.328(2) 0.817(6) 0.7239(11) 0.021(7) Uiso 1 d . . 1 . . .
H1B H 0.420(3) 0.708(7) 0.5019(13) 0.052(11) Uiso 1 d . . 1 . . .
H3 H 0.538(3) 1.403(7) 0.7302(12) 0.046(11) Uiso 1 d . . 1 . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0240(17) 0.0175(15) 0.0227(15) 0.000 0.0064(13) 0.000
O1 0.0238(11) 0.0241(11) 0.0128(9) 0.0012(8) 0.0064(8) -0.0024(9)
O2 0.0238(11) 0.0150(10) 0.0169(9) -0.0043(8) 0.0005(8) -0.0030(9)
N7 0.0139(12) 0.0120(11) 0.0150(11) 0.0027(9) 0.0025(9) 0.0010(10)
N2 0.0151(12) 0.0118(12) 0.0169(11) 0.0031(9) 0.0022(9) 0.0005(10)
N4 0.0168(12) 0.0156(12) 0.0155(11) 0.0015(9) 0.0025(9) -0.0006(10)
N1 0.0213(14) 0.0183(13) 0.0130(11) -0.0013(10) 0.0030(10) -0.0021(11)
N3 0.0181(13) 0.0157(12) 0.0122(11) -0.0002(10) 0.0039(10) -0.0002(11)
N5 0.0187(13) 0.0144(12) 0.0166(11) 0.0004(9) 0.0018(9) 0.0007(10)
N6 0.0192(13) 0.0150(12) 0.0155(11) 0.0035(9) 0.0027(9) 0.0005(10)
N8 0.0184(12) 0.0177(12) 0.0101(10) 0.0005(9) 0.0038(9) -0.0006(10)
C4 0.0141(14) 0.0135(13) 0.0123(12) 0.0019(11) 0.0005(10) 0.0016(12)
C2 0.0117(13) 0.0121(13) 0.0146(12) 0.0022(10) 0.0027(10) 0.0005(11)
C1 0.0116(13) 0.0140(14) 0.0147(13) 0.0033(10) 0.0013(10) 0.0028(12)
C3 0.0134(13) 0.0119(13) 0.0178(13) 0.0009(10) 0.0011(11) 0.0054(11)

_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 H3 0.87(3) . ?
O1 N2 1.242(2) . ?
O2 N2 1.242(3) . ?
N7 N6 1.348(3) . ?
N7 N8 1.358(3) . ?
N7 C4 1.337(3) . ?
N2 C2 1.423(3) . ?
N4 N5 1.348(3) . ?
N4 C4 1.334(3) . ?
N1 C1 1.333(3) . ?
N1 H1A 0.85(3) . ?
N1 H1B 0.97(4) . ?
N3 C3 1.324(3) . ?
N3 H3A 0.91(4) . ?
N3 H3B 0.90(3) . ?
N5 N6 1.319(3) . ?
N8 C1 1.332(3) . ?
C4 C3 1.437(4) . ?
C2 C1 1.460(3) . ?
C2 C3 1.406(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
N6 N7 N8 121.1(2) . . ?
C4 N7 N6 109.73(19) . . ?
C4 N7 N8 129.2(2) . . ?
O1 N2 C2 120.1(2) . . ?
O2 N2 O1 121.2(2) . . ?
O2 N2 C2 118.72(19) . . ?
C4 N4 N5 105.0(2) . . ?
C1 N1 H1A 113.8(19) . . ?
C1 N1 H1B 123(2) . . ?
H1A N1 H1B 124(3) . . ?
C3 N3 H3A 118(2) . . ?
C3 N3 H3B 118.2(18) . . ?
H3A N3 H3B 124(3) . . ?
N6 N5 N4 112.35(18) . . ?
N5 N6 N7 104.4(2) . . ?
C1 N8 N7 113.4(2) . . ?
N7 C4 C3 119.5(2) . . ?
N4 C4 N7 108.5(2) . . ?
N4 C4 C3 132.0(2) . . ?
N2 C2 C1 121.0(2) . . ?
C3 C2 N2 118.3(2) . . ?
C3 C2 C1 120.7(2) . . ?
N1 C1 C2 122.7(2) . . ?
N8 C1 N1 114.1(2) . . ?
N8 C1 C2 123.2(2) . . ?
N3 C3 C4 116.9(2) . . ?
N3 C3 C2 129.0(3) . . ?
C2 C3 C4 114.1(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 C2 C1 -5.3(4) . . . . ?
O1 N2 C2 C3 175.4(2) . . . . ?
O2 N2 C2 C1 174.4(2) . . . . ?
O2 N2 C2 C3 -4.9(3) . . . . ?
N7 N8 C1 N1 179.9(2) . . . . ?
N7 N8 C1 C2 0.3(3) . . . . ?
N7 C4 C3 N3 179.8(2) . . . . ?
N7 C4 C3 C2 -0.9(4) . . . . ?
N2 C2 C1 N1 0.9(4) . . . . ?
N2 C2 C1 N8 -179.5(2) . . . . ?
N2 C2 C3 N3 -1.0(4) . . . . ?
N2 C2 C3 C4 179.8(2) . . . . ?
N4 N5 N6 N7 0.2(3) . . . . ?
N4 C4 C3 N3 -0.1(4) . . . . ?
N4 C4 C3 C2 179.2(3) . . . . ?
N5 N4 C4 N7 0.9(3) . . . . ?
N5 N4 C4 C3 -179.1(3) . . . . ?
N6 N7 N8 C1 -178.6(2) . . . . ?
N6 N7 C4 N4 -0.9(3) . . . . ?
N6 N7 C4 C3 179.2(2) . . . . ?
N8 N7 N6 N5 178.6(2) . . . . ?
N8 N7 C4 N4 -178.8(2) . . . . ?
N8 N7 C4 C3 1.2(4) . . . . ?
C4 N7 N6 N5 0.4(3) . . . . ?
C4 N7 N8 C1 -0.9(4) . . . . ?
C4 N4 N5 N6 -0.7(3) . . . . ?
C1 C2 C3 N3 179.6(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C3 C2 C1 N1 -179.8(2) . . . . ?
C3 C2 C1 N8 -0.1(4) . . . . ?

_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_22019879qcst3_0m
_database_code_depnum_ccdc_archive 'CCDC 1952871'
loop_
_audit_author_name
_audit_author_address
'Sitong Chen'
;China Academy Of Engineering Physics
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H2 N8 O4, H2 O'
_chemical_formula_sum            'C4 H4 N8 O5'
_chemical_formula_weight         244.15
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.411(3)
_cell_length_b                   5.0229(5)
_cell_length_c                   15.2453(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.545(4)
_cell_angle_gamma                90.00
_cell_volume                     1756.5(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1030
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.851
_cell_measurement_theta_min      2.728
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8379.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5703
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1168
_reflns_number_total             1771
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0531P)²+1.9760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1446
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O4 O 0.45118(9) 0.7448(4) 0.43219(15) 0.0260(6) Uani 1 d . . .
O2 O 0.40284(10) 0.3263(5) 0.18268(16) 0.0277(6) Uani 1 d . . .
O5 O 0.42032(10) 1.1849(5) 0.54232(16) 0.0264(6) Uani 1 d . . .
H5A H 0.4088 1.2298 0.5911 0.040 Uiso 1 d . . G
H5B H 0.4582 1.1754 0.5531 0.040 Uiso 1 d . . G
O1 O 0.41467(11) -0.0636(4) 0.24724(17) 0.0300(6) Uani 1 d . . .
N5 N 0.27424(11) 0.2291(5) 0.33896(17) 0.0157(6) Uani 1 d . . .
O3 O 0.47435(10) 0.4079(5) 0.35708(17) 0.0317(7) Uani 1 d . . .
N8 N 0.23449(11) 0.4732(5) 0.42703(17) 0.0169(6) Uani 1 d . . .
N1 N 0.34577(12) 0.7624(5) 0.47370(18) 0.0201(6) Uani 1 d . . .
H1A H 0.3795 0.8450 0.4877 0.024 Uiso 1 calc . . R
H1B H 0.3168 0.8092 0.4994 0.024 Uiso 1 calc . . R
N2 N 0.43846(12) 0.5427(5) 0.38555(18) 0.0211(7) Uani 1 d . . .
N4 N 0.31078(11) 0.1282(5) 0.28850(18) 0.0189(6) Uani 1 d . . .
N7 N 0.19711(11) 0.2795(5) 0.38799(18) 0.0196(6) Uani 1 d . . .
N6 N 0.22024(11) 0.1302(5) 0.33431(18) 0.0177(6) Uani 1 d . . .
N3 N 0.39754(12) 0.1646(5) 0.24008(19) 0.0216(7) Uani 1 d . . .
C2 C 0.33859(13) 0.5695(6) 0.4145(2) 0.0165(7) Uani 1 d . . .
C1 C 0.28273(14) 0.4381(6) 0.3954(2) 0.0166(7) Uani 1 d . . .
C3 C 0.37832(13) 0.4625(6) 0.3654(2) 0.0175(7) Uani 1 d . . .
C4 C 0.36071(13) 0.2527(6) 0.3046(2) 0.0187(7) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O4 0.0206(12) 0.0300(13) 0.0267(15) -0.0091(11) 0.0028(11) -0.0068(11)
O2 0.0302(14) 0.0293(13) 0.0261(15) 0.0060(11) 0.0112(12) 0.0023(10)
O5 0.0227(13) 0.0319(14) 0.0238(14) -0.0013(11) 0.0026(11) -0.0040(11)
O1 0.0320(14) 0.0239(13) 0.0335(16) 0.0009(11) 0.0053(12) 0.0036(11)
N5 0.0146(13) 0.0179(13) 0.0134(15) 0.0017(11) 0.0000(11) -0.0011(11)
O3 0.0182(13) 0.0381(15) 0.0386(16) -0.0138(12) 0.0052(12) 0.0018(11)
N8 0.0166(14) 0.0168(13) 0.0159(15) 0.0019(11) 0.0000(12) -0.0022(11)
N1 0.0176(14) 0.0228(14) 0.0200(16) -0.0033(12) 0.0037(12) -0.0048(11)
N2 0.0167(15) 0.0277(15) 0.0181(16) -0.0026(13) 0.0014(13) -0.0023(12)
N4 0.0198(15) 0.0177(13) 0.0187(16) -0.0021(12) 0.0026(13) 0.0007(11)
N7 0.0190(14) 0.0193(14) 0.0196(16) 0.0008(12) 0.0019(12) -0.0050(11)
N6 0.0150(14) 0.0166(13) 0.0207(16) -0.0002(11) 0.0011(12) -0.0012(11)
N3 0.0187(15) 0.0215(15) 0.0224(17) -0.0018(13) -0.0011(13) 0.0020(11)
C2 0.0181(17) 0.0162(16) 0.0137(17) 0.0026(13) -0.0003(14) -0.0023(12)
C1 0.0204(17) 0.0146(15) 0.0122(18) 0.0025(13) -0.0030(14) 0.0002(12)
C3 0.0141(16) 0.0199(16) 0.0178(18) -0.0017(14) 0.0018(14) -0.0022(13)
C4 0.0180(17) 0.0211(16) 0.0158(18) 0.0001(14) 0.0008(14) 0.0064(13)

_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
O4 N2 1.241(3) . ?
O2 N3 1.218(3) . ?
O5 H5A 0.8701 . ?
O5 H5B 0.8705 . ?
O1 N3 1.212(3) . ?
N5 N4 1.358(4) . ?
N5 N6 1.347(3) . ?
N5 C1 1.346(4) . ?
O3 N2 1.224(3) . ?
N8 N7 1.363(3) . ?
N8 C1 1.326(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.312(4) . ?
N2 C3 1.437(4) . ?
N4 C4 1.305(4) . ?
N7 N6 1.305(4) . ?
N3 C4 1.499(4) . ?
C2 C1 1.442(4) . ?
C2 C3 1.411(5) . ?
C3 C4 1.410(4) . ?

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
H5A O5 H5B 109.4 . . ?
N6 N5 N4 121.6(2) . . ?
C1 N5 N4 128.6(3) . . ?
C1 N5 N6 109.8(3) . . ?
C1 N8 N7 105.4(2) . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
O4 N2 C3 117.6(3) . . ?
O3 N2 O4 123.5(3) . . ?
O3 N2 C3 118.8(3) . . ?
C4 N4 N5 110.9(2) . . ?
N6 N7 N8 111.9(2) . . ?
N7 N6 N5 104.9(2) . . ?
O2 N3 C4 115.4(3) . . ?
O1 N3 O2 128.0(3) . . ?
O1 N3 C4 116.3(3) . . ?
N1 C2 C1 117.6(3) . . ?
N1 C2 C3 129.7(3) . . ?
C3 C2 C1 112.7(3) . . ?
N5 C1 C2 119.9(3) . . ?
N8 C1 N5 108.0(3) . . ?
N8 C1 C2 132.1(3) . . ?
C2 C3 N2 120.1(3) . . ?
C4 C3 N2 119.7(3) . . ?
C4 C3 C2 119.7(3) . . ?
N4 C4 N3 110.2(3) . . ?
N4 C4 C3 128.0(3) . . ?
C3 C4 N3 121.4(3) . . ?

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
O4 N2 C3 C2 -15.1(4) . . . . ?
O4 N2 C3 C4 172.9(3) . . . . ?
O2 N3 C4 N4 107.3(3) . . . . ?
O2 N3 C4 C3 -66.4(4) . . . . ?
O1 N3 C4 N4 -67.5(3) . . . . ?
O1 N3 C4 C3 118.8(3) . . . . ?
N5 N4 C4 N3 -172.5(2) . . . . ?
N5 N4 C4 C3 0.7(5) . . . . ?
O3 N2 C3 C2 164.0(3) . . . . ?
O3 N2 C3 C4 -8.0(5) . . . . ?
N8 N7 N6 N5 0.3(3) . . . . ?
N1 C2 C1 N5 -176.2(3) . . . . ?
N1 C2 C1 N8 -0.1(5) . . . . ?
N1 C2 C3 N2 8.0(5) . . . . ?
N1 C2 C3 C4 -180.0(3) . . . . ?
N2 C3 C4 N4 168.9(3) . . . . ?
N2 C3 C4 N3 -18.6(4) . . . . ?
N4 N5 N6 N7 -177.4(3) . . . . ?
N4 N5 C1 N8 177.1(3) . . . . ?
N4 N5 C1 C2 -6.0(5) . . . . ?
N7 N8 C1 N5 0.0(3) . . . . ?
N7 N8 C1 C2 -176.4(3) . . . . ?
N6 N5 N4 C4 -179.4(3) . . . . ?
N6 N5 C1 N8 0.1(3) . . . . ?
N6 N5 C1 C2 177.1(3) . . . . ?
C2 C3 C4 N4 -3.1(5) . . . . ?
C2 C3 C4 N3 169.4(3) . . . . ?
C1 N5 N4 C4 4.0(4) . . . . ?
C1 N5 N6 N7 -0.2(3) . . . . ?
C1 N8 N7 N6 -0.2(3) . . . . ?
C1 C2 C3 N2 -170.9(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C3 C2 C1 N5 2.9(4) . . . . ?
C3 C2 C1 N8 179.0(3) . . . . ?

_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_22019878qcst2_0m
_database_code_depnum_ccdc_archive 'CCDC 1952870'
loop_
_audit_author_name
_audit_author_address
'Sitong Chen'
;China Academy Of Engineering Physics
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_audit_creation_date             2019-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H2 N8 O4'
_chemical_formula_sum            'C4 H2 N8 O4'
_chemical_formula_weight         226.14
_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'

_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'

_cell_length_a                   11.6487(5)
_cell_length_b                   9.8870(5)
_cell_length_c                   14.4221(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.486(2)
_cell_angle_gamma                90.00
_cell_volume                     1592.72(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2998
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.53
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0944 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.9126.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'light green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.886
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12802
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.53
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2086
_reflns_number_total             3606
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1329
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0395P)²+1.0403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1415
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O5 O 0.2340(2) 0.6896(2) 0.66622(15) 0.0249(5) Uani 1 d . . .
O1 O 0.0717(2) 0.4961(2) 0.35915(15) 0.0272(6) Uani 1 d . . .
O8 O 0.3051(2) 1.1386(2) 0.81202(16) 0.0290(6) Uani 1 d . . .
O7 O 0.3930(2) 0.9678(2) 0.89805(15) 0.0313(6) Uani 1 d . . .
O6 O 0.2056(2) 0.8605(3) 0.75134(18) 0.0355(7) Uani 1 d . . .
O4 O 0.2011(2) 0.3758(2) 0.68635(16) 0.0362(7) Uani 1 d . . .
N5 N 0.1404(2) 0.0477(3) 0.49796(17) 0.0172(6) Uani 1 d . . .
N8 N 0.0506(2) -0.0315(3) 0.35683(17) 0.0181(6) Uani 1 d . . .
N1 N 0.0321(2) 0.2505(3) 0.28551(17) 0.0189(6) Uani 1 d . . .
H1A H 0.0267 0.3354 0.2664 0.023 Uiso 1 calc . . R
H1B H 0.0042 0.1855 0.2435 0.023 Uiso 1 calc . . R
N13 N 0.5412(2) 1.0214(3) 0.66477(16) 0.0180(6) Uani 1 d . . .
N10 N 0.2621(2) 0.8003(3) 0.70438(18) 0.0209(6) Uani 1 d . . .
N4 N 0.1963(2) 0.1291(3) 0.57344(17) 0.0190(6) Uani 1 d . . .
N7 N 0.0804(2) -0.1334(3) 0.42264(17) 0.0213(6) Uani 1 d . . .
N12 N 0.4906(2) 1.0692(3) 0.73221(17) 0.0189(6) Uani 1 d . . .
N14 N 0.6295(2) 1.0881(3) 0.64100(18) 0.0227(6) Uani 1 d . . .
N6 N 0.1358(2) -0.0875(3) 0.50912(17) 0.0197(6) Uani 1 d . . .
N9 N 0.3925(2) 0.7143(3) 0.56535(17) 0.0246(7) Uani 1 d . . .
H9A H 0.3318 0.6628 0.5678 0.029 Uiso 1 calc . . R
H9B H 0.4338 0.6951 0.5245 0.029 Uiso 1 calc . . R
N11 N 0.3630(2) 1.0346(3) 0.82359(18) 0.0200(6) Uani 1 d . . .
N2 N 0.1233(3) 0.4525(3) 0.44003(18) 0.0254(7) Uani 1 d . . .
N16 N 0.5918(2) 0.8950(3) 0.55981(17) 0.0226(6) Uani 1 d . . .
N3 N 0.2533(3) 0.3410(3) 0.62944(18) 0.0261(7) Uani 1 d . . .
N15 N 0.6589(2) 1.0099(3) 0.57782(18) 0.0247(7) Uani 1 d . . .
O2 O 0.1670(3) 0.5267(3) 0.50928(17) 0.0549(9) Uani 1 d . . .
O3 O 0.3579(2) 0.3618(3) 0.6354(2) 0.0571(9) Uani 1 d . . .
C2 C 0.0815(3) 0.2211(3) 0.3761(2) 0.0162(7) Uani 1 d . . .
C8 C 0.4085(3) 0.9873(3) 0.74259(19) 0.0160(7) Uani 1 d . . .
C1 C 0.0890(3) 0.0806(3) 0.4052(2) 0.0168(7) Uani 1 d . . .
C7 C 0.3669(3) 0.8662(3) 0.6920(2) 0.0180(7) Uani 1 d . . .
C6 C 0.4216(3) 0.8200(3) 0.6228(2) 0.0191(7) Uani 1 d . . .
C3 C 0.1314(3) 0.3099(3) 0.4542(2) 0.0179(7) Uani 1 d . . .
C5 C 0.5184(3) 0.9046(3) 0.6146(2) 0.0193(7) Uani 1 d . . .
C4 C 0.1876(3) 0.2546(3) 0.5463(2) 0.0196(7) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0308(13) 0.0178(14) 0.0240(11) -0.0033(10) 0.0046(10) -0.0067(11)
O1 0.0370(14) 0.0191(14) 0.0215(11) 0.0027(10) 0.0018(10) -0.0004(11)
O8 0.0359(14) 0.0219(15) 0.0312(13) -0.0040(11) 0.0126(11) 0.0070(12)
O7 0.0400(15) 0.0348(16) 0.0202(11) 0.0054(11) 0.0102(11) -0.0006(12)
O6 0.0278(14) 0.0336(16) 0.0517(16) -0.0203(13) 0.0218(12) -0.0066(12)
O4 0.0598(18) 0.0248(16) 0.0277(13) -0.0072(11) 0.0187(13) -0.0072(13)
N5 0.0186(14) 0.0143(16) 0.0183(13) -0.0001(11) 0.0044(11) 0.0000(11)
N8 0.0182(14) 0.0141(16) 0.0204(13) 0.0000(11) 0.0027(11) 0.0015(11)
N1 0.0209(15) 0.0154(16) 0.0169(12) 0.0000(10) -0.0003(11) -0.0017(11)
N13 0.0180(14) 0.0185(16) 0.0164(12) 0.0018(11) 0.0030(11) 0.0015(12)
N10 0.0219(15) 0.0159(17) 0.0232(14) -0.0013(12) 0.0037(12) -0.0020(12)
N4 0.0196(14) 0.0184(17) 0.0180(13) -0.0024(11) 0.0036(11) -0.0034(12)
N7 0.0217(15) 0.0197(17) 0.0209(13) 0.0026(12) 0.0037(12) 0.0000(12)
N12 0.0210(14) 0.0196(16) 0.0168(13) -0.0011(11) 0.0065(11) 0.0006(12)
N14 0.0183(14) 0.0298(18) 0.0212(13) 0.0018(12) 0.0075(12) -0.0031(12)
N6 0.0230(15) 0.0185(17) 0.0173(13) 0.0005(11) 0.0053(11) -0.0014(12)
N9 0.0363(17) 0.0181(17) 0.0200(13) -0.0043(12) 0.0090(13) -0.0011(13)
N11 0.0187(14) 0.0201(17) 0.0209(14) -0.0038(12) 0.0052(11) -0.0048(13)
N2 0.0381(17) 0.0181(17) 0.0216(14) -0.0032(12) 0.0111(13) -0.0085(13)
N16 0.0230(15) 0.0241(18) 0.0195(13) 0.0039(12) 0.0042(12) 0.0063(13)
N3 0.0306(17) 0.0252(18) 0.0203(14) -0.0026(12) 0.0038(13) -0.0042(13)
N15 0.0204(14) 0.0316(19) 0.0225(13) 0.0045(13) 0.0067(12) 0.0022(13)
O2 0.112(3) 0.0173(16) 0.0228(13) -0.0042(11) -0.0006(15) -0.0187(16)
O3 0.0308(16) 0.072(2) 0.0657(19) -0.0388(17) 0.0095(15) -0.0205(15)
C2 0.0129(15) 0.0179(19) 0.0184(15) -0.0005(13) 0.0055(12) -0.0021(13)
C8 0.0189(16) 0.0141(18) 0.0132(14) 0.0002(12) 0.0015(13) 0.0031(13)
C1 0.0153(16) 0.0205(19) 0.0141(14) -0.0005(13) 0.0037(13) -0.0013(13)
C7 0.0178(16) 0.0182(19) 0.0164(14) 0.0030(13) 0.0024(13) 0.0018(14)
C6 0.0193(17) 0.020(2) 0.0148(14) 0.0027(13) 0.0003(13) 0.0064(14)
C3 0.0212(17) 0.0110(18) 0.0206(15) 0.0000(12) 0.0046(13) -0.0013(13)
C5 0.0206(17) 0.021(2) 0.0152(14) 0.0015(13) 0.0029(13) 0.0050(14)
C4 0.0200(17) 0.023(2) 0.0152(15) -0.0047(13) 0.0046(13) -0.0046(14)

_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
O5 N10 1.226(3) . ?
O1 N2 1.229(3) . ?
O8 N11 1.215(3) . ?
O7 N11 1.224(3) . ?
O6 N10 1.224(3) . ?
O4 N3 1.202(3) . ?
N5 N4 1.362(3) . ?
N5 N6 1.349(4) . ?
N5 C1 1.342(3) . ?
N8 N7 1.360(4) . ?
N8 C1 1.318(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.302(4) . ?
N13 N12 1.357(3) . ?
N13 N14 1.346(3) . ?
N13 C5 1.348(4) . ?
N10 C7 1.439(4) . ?
N4 C4 1.296(4) . ?
N7 N6 1.312(3) . ?
N12 C8 1.293(4) . ?
N14 N15 1.312(4) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C6 1.317(4) . ?
N11 C8 1.488(4) . ?
N2 O2 1.227(3) . ?
N2 C3 1.425(4) . ?
N16 N15 1.362(4) . ?
N16 C5 1.322(4) . ?
N3 O3 1.214(4) . ?
N3 C4 1.494(4) . ?
C2 C1 1.446(4) . ?
C2 C3 1.417(4) . ?
C8 C7 1.415(4) . ?
C7 C6 1.404(4) . ?
C6 C5 1.436(4) . ?
C3 C4 1.413(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 N5 N4 121.1(2) . . ?
C1 N5 N4 129.1(3) . . ?
C1 N5 N6 109.7(2) . . ?
C1 N8 N7 105.8(2) . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
N14 N13 N12 122.1(3) . . ?
N14 N13 C5 109.3(2) . . ?
C5 N13 N12 128.6(3) . . ?
O5 N10 C7 118.4(3) . . ?
O6 N10 O5 124.4(3) . . ?
O6 N10 C7 117.1(3) . . ?
C4 N4 N5 110.2(2) . . ?
N6 N7 N8 111.5(3) . . ?
C8 N12 N13 110.5(3) . . ?
N15 N14 N13 104.9(3) . . ?
N7 N6 N5 104.8(2) . . ?
H9A N9 H9B 120.0 . . ?
C6 N9 H9A 120.0 . . ?
C6 N9 H9B 120.0 . . ?
O8 N11 O7 125.9(3) . . ?
O8 N11 C8 117.8(2) . . ?
O7 N11 C8 116.3(3) . . ?
O1 N2 C3 118.6(3) . . ?
O2 N2 O1 122.8(3) . . ?
O2 N2 C3 118.6(3) . . ?
C5 N16 N15 105.0(3) . . ?
O4 N3 O3 126.5(3) . . ?
O4 N3 C4 117.9(3) . . ?
O3 N3 C4 115.4(3) . . ?
N14 N15 N16 112.1(2) . . ?
N1 C2 C1 118.6(3) . . ?
N1 C2 C3 128.6(3) . . ?
C3 C2 C1 112.8(3) . . ?
N12 C8 N11 109.5(3) . . ?
N12 C8 C7 128.8(3) . . ?
C7 C8 N11 121.6(3) . . ?
N5 C1 C2 119.7(3) . . ?
N8 C1 N5 108.2(3) . . ?
N8 C1 C2 132.1(3) . . ?
C8 C7 N10 119.9(3) . . ?
C6 C7 N10 120.9(3) . . ?
C6 C7 C8 118.9(3) . . ?
N9 C6 C7 128.2(3) . . ?
N9 C6 C5 118.6(3) . . ?
C7 C6 C5 113.2(3) . . ?
C2 C3 N2 120.3(3) . . ?
C4 C3 N2 120.8(3) . . ?
C4 C3 C2 118.9(3) . . ?
N13 C5 C6 119.6(3) . . ?
N16 C5 N13 108.7(3) . . ?
N16 C5 C6 131.5(3) . . ?
N4 C4 N3 109.1(3) . . ?
N4 C4 C3 129.0(3) . . ?
C3 C4 N3 121.9(3) . . ?

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 N10 C7 C8 -173.8(3) . . . . ?
O5 N10 C7 C6 12.8(4) . . . . ?
O1 N2 C3 C2 0.4(4) . . . . ?
O1 N2 C3 C4 -178.6(3) . . . . ?
O8 N11 C8 N12 68.9(3) . . . . ?
O8 N11 C8 C7 -113.9(3) . . . . ?
O7 N11 C8 N12 -107.6(3) . . . . ?
O7 N11 C8 C7 69.6(4) . . . . ?
O6 N10 C7 C8 7.4(4) . . . . ?
O6 N10 C7 C6 -165.9(3) . . . . ?
O4 N3 C4 N4 -85.0(3) . . . . ?
O4 N3 C4 C3 97.2(4) . . . . ?
N5 N4 C4 N3 -178.0(2) . . . . ?
N5 N4 C4 C3 -0.4(4) . . . . ?
N8 N7 N6 N5 0.4(3) . . . . ?
N1 C2 C1 N5 179.4(3) . . . . ?
N1 C2 C1 N8 -2.6(5) . . . . ?
N1 C2 C3 N2 4.9(5) . . . . ?
N1 C2 C3 C4 -176.0(3) . . . . ?
N13 N12 C8 N11 174.4(2) . . . . ?
N13 N12 C8 C7 -2.6(4) . . . . ?
N13 N14 N15 N16 0.2(3) . . . . ?
N10 C7 C6 N9 -3.0(5) . . . . ?
N10 C7 C6 C5 174.9(3) . . . . ?
N4 N5 N6 N7 -177.7(2) . . . . ?
N4 N5 C1 N8 177.4(3) . . . . ?
N4 N5 C1 C2 -4.2(4) . . . . ?
N7 N8 C1 N5 -0.2(3) . . . . ?
N7 N8 C1 C2 -178.3(3) . . . . ?
N12 N13 N14 N15 177.3(2) . . . . ?
N12 N13 C5 N16 -177.0(3) . . . . ?
N12 N13 C5 C6 6.6(5) . . . . ?
N12 C8 C7 N10 -170.6(3) . . . . ?
N12 C8 C7 C6 2.9(5) . . . . ?
N14 N13 N12 C8 -179.7(3) . . . . ?
N14 N13 C5 N16 0.6(3) . . . . ?
N14 N13 C5 C6 -175.8(3) . . . . ?
N6 N5 N4 C4 -178.8(3) . . . . ?
N6 N5 C1 N8 0.5(3) . . . . ?
N6 N5 C1 C2 178.9(3) . . . . ?
N9 C6 C5 N13 172.6(3) . . . . ?
N9 C6 C5 N16 -2.8(5) . . . . ?
N11 C8 C7 N10 12.8(4) . . . . ?
N11 C8 C7 C6 -173.7(3) . . . . ?
N2 C3 C4 N4 175.2(3) . . . . ?
N2 C3 C4 N3 -7.5(4) . . . . ?
N15 N16 C5 N13 -0.5(3) . . . . ?
N15 N16 C5 C6 175.3(3) . . . . ?
O2 N2 C3 C2 179.7(3) . . . . ?
O2 N2 C3 C4 0.6(4) . . . . ?
O3 N3 C4 N4 90.6(4) . . . . ?
O3 N3 C4 C3 -87.2(4) . . . . ?
C2 C3 C4 N4 -3.9(5) . . . . ?
C2 C3 C4 N3 173.4(3) . . . . ?
C8 C7 C6 N9 -176.4(3) . . . . ?
C8 C7 C6 C5 1.5(4) . . . . ?
C1 N5 N4 C4 4.6(4) . . . . ?
C1 N5 N6 N7 -0.5(3) . . . . ?
C1 N8 N7 N6 -0.1(3) . . . . ?
C1 C2 C3 N2 -175.1(3) . . . . ?
C1 C2 C3 C4 4.0(4) . . . . ?
C7 C6 C5 N13 -5.5(4) . . . . ?
C7 C6 C5 N16 179.1(3) . . . . ?
C3 C2 C1 N5 -0.6(4) . . . . ?
C3 C2 C1 N8 177.4(3) . . . . ?
C5 N13 N12 C8 -2.3(4) . . . . ?
C5 N13 N14 N15 -0.5(3) . . . . ?
C5 N16 N15 N14 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
