# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_2017951-nlg-201_0m
_database_code_depnum_ccdc_archive 'CCDC 1881963'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2018-11-29 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2017-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 Cl N7 O10'
_chemical_formula_sum            'C4 Cl N7 O10'
_chemical_formula_weight         341.56
_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'
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'

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

_cell_length_a                   13.840(2)
_cell_length_b                   12.1903(18)
_cell_length_c                   14.668(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.697(4)
_cell_angle_gamma                90
_cell_volume                     2315.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1257
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.707
_cell_measurement_theta_min      2.295
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0802 before and 0.0615 after correction. The Ratio of minimum to maximum transmission is 0.8994. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18474
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         1.740
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2876
_reflns_number_total             5239
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0104(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     404
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O17-N9 \\sim O18-N9
 with sigma of 0.02
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O18) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: O17(0.67) O18(0.33)
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.08822(7) 0.01271(7) 0.21187(7) 0.0477(3) Uani 1 1 d . U . . .
Cl1 Cl 0.86231(7) 0.30632(9) 0.41845(7) 0.0593(3) Uani 1 1 d . U . . .
O2 O 0.51624(17) 0.29532(17) 0.35240(16) 0.0387(6) Uani 1 1 d . U . . .
O8 O 0.49814(18) 0.01713(18) 0.10809(17) 0.0430(6) Uani 1 1 d . U . . .
O10 O 0.50027(19) 0.26307(19) 0.15544(17) 0.0475(6) Uani 1 1 d . U . . .
N3 N 0.61700(18) 0.13462(18) 0.29261(17) 0.0252(6) Uani 1 1 d . U . . .
O14 O 0.39455(19) 0.41944(19) 0.47961(17) 0.0456(6) Uani 1 1 d . U . . .
N14 N 0.22321(18) 0.29075(19) 0.31618(17) 0.0273(6) Uani 1 1 d . U . . .
N13 N 0.23157(18) 0.23489(19) 0.39884(17) 0.0261(6) Uani 1 1 d . U . . .
O7 O 0.49060(19) -0.08216(18) 0.22929(18) 0.0507(7) Uani 1 1 d . U . . .
N2 N 0.68612(19) 0.06253(19) 0.28299(17) 0.0285(6) Uani 1 1 d . U . . .
N4 N 0.6071(2) 0.3134(2) 0.36601(19) 0.0338(6) Uani 1 1 d . U . . .
O1 O 0.6530(2) 0.39731(19) 0.39887(18) 0.0528(7) Uani 1 1 d . U . . .
N6 N 0.49844(19) 0.0028(2) 0.1900(2) 0.0333(6) Uani 1 1 d . U . . .
O12 O 0.11778(19) 0.1928(2) 0.08177(16) 0.0540(7) Uani 1 1 d . U . . .
O5 O 0.5310(2) 0.0615(2) 0.41134(19) 0.0543(7) Uani 1 1 d . U . . .
O11 O 0.1770(2) 0.3534(2) 0.13483(17) 0.0580(7) Uani 1 1 d . U . . .
O13 O 0.2356(2) 0.47398(19) 0.4400(2) 0.0612(8) Uani 1 1 d . U . . .
N5 N 0.4493(2) 0.1966(2) 0.17914(19) 0.0330(6) Uani 1 1 d . U . . .
O9 O 0.35652(18) 0.1874(2) 0.1491(2) 0.0605(8) Uani 1 1 d . U . . .
O21 O 0.1544(2) -0.03521(19) 0.42676(19) 0.0573(7) Uani 1 1 d . U . . .
N8 N 0.3054(2) 0.4081(2) 0.46758(19) 0.0359(7) Uani 1 1 d . U . . .
N10 N 0.3720(2) 0.2379(2) 0.5579(2) 0.0384(7) Uani 1 1 d . U . . .
O19 O 0.1044(2) 0.2835(2) 0.4884(2) 0.0604(8) Uani 1 1 d . U . . .
N11 N 0.1547(2) 0.2600(2) 0.14612(19) 0.0365(7) Uani 1 1 d . U . . .
N7 N 0.4669(2) 0.0812(2) 0.3329(2) 0.0386(7) Uani 1 1 d . U . . .
O20 O 0.2247(2) 0.0886(2) 0.53581(18) 0.0629(8) Uani 1 1 d . U . . .
O6 O 0.37449(19) 0.0787(2) 0.3097(2) 0.0649(8) Uani 1 1 d . U . . .
O15 O 0.4028(2) 0.2712(2) 0.64054(18) 0.0638(8) Uani 1 1 d . U . . .
N12 N 0.1888(2) 0.0555(2) 0.4517(2) 0.0397(7) Uani 1 1 d . U . . .
O16 O 0.4133(2) 0.1741(2) 0.5221(2) 0.0668(8) Uani 1 1 d . U . . .
O4 O 0.8588(2) -0.0386(3) 0.2946(2) 0.0719(9) Uani 1 1 d . U . . .
N9 N 0.1900(2) 0.3095(3) 0.5349(2) 0.0489(8) Uani 1 1 d D U . . .
C3 C 0.6646(2) 0.2272(2) 0.3416(2) 0.0270(7) Uani 1 1 d . U . . .
C7 C 0.1746(2) 0.2224(2) 0.2457(2) 0.0263(7) Uani 1 1 d . U . . .
C5 C 0.1877(2) 0.1323(2) 0.3768(2) 0.0283(7) Uani 1 1 d . U . . .
N1 N 0.8686(2) 0.0532(3) 0.3267(2) 0.0502(8) Uani 1 1 d . U . . .
C1 C 0.7759(2) 0.1105(3) 0.3252(2) 0.0320(7) Uani 1 1 d . U . . .
C6 C 0.1493(2) 0.1206(2) 0.2778(2) 0.0286(7) Uani 1 1 d . U . . .
C4 C 0.5104(2) 0.1079(2) 0.2517(2) 0.0254(6) Uani 1 1 d . U . . .
C8 C 0.2724(2) 0.2915(2) 0.4886(2) 0.0297(7) Uani 1 1 d . U . . .
C2 C 0.7684(2) 0.2151(3) 0.3623(2) 0.0329(7) Uani 1 1 d . U . . .
O3 O 0.9493(2) 0.1026(3) 0.3610(3) 0.0914(11) Uani 1 1 d . U . . .
O17 O 0.2183(5) 0.3727(4) 0.6054(4) 0.0684(16) Uani 0.67 1 d D U P A 1
O18 O 0.2214(10) 0.3091(9) 0.6267(7) 0.063(3) Uani 0.33 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C6 1.673(3) . ?
Cl1 C2 1.687(3) . ?
O2 N4 1.221(3) . ?
O8 N6 1.213(3) . ?
O10 N5 1.204(3) . ?
N3 N2 1.343(3) . ?
N3 C3 1.375(4) . ?
N3 C4 1.420(4) . ?
O14 N8 1.191(3) . ?
N14 N13 1.359(3) . ?
N14 C7 1.313(3) . ?
N13 C5 1.378(4) . ?
N13 C8 1.415(4) . ?
O7 N6 1.208(3) . ?
N2 C1 1.313(4) . ?
N4 O1 1.211(3) . ?
N4 C3 1.437(4) . ?
N6 C4 1.543(4) . ?
O12 N11 1.218(3) . ?
O5 N7 1.203(3) . ?
O11 N11 1.206(3) . ?
O13 N8 1.210(3) . ?
N5 O9 1.206(3) . ?
N5 C4 1.543(4) . ?
O21 N12 1.209(3) . ?
N8 C8 1.557(4) . ?
N10 O15 1.204(3) . ?
N10 O16 1.192(3) . ?
N10 C8 1.540(4) . ?
O19 N9 1.182(3) . ?
N11 C7 1.461(4) . ?
N7 O6 1.202(3) . ?
N7 C4 1.548(4) . ?
O20 N12 1.224(3) . ?
N12 C5 1.439(4) . ?
O4 N1 1.203(4) . ?
N9 C8 1.535(4) . ?
N9 O17 1.238(5) . ?
N9 O18 1.260(9) . ?
C3 C2 1.368(4) . ?
C7 C6 1.415(4) . ?
C5 C6 1.366(4) . ?
N1 C1 1.454(4) . ?
N1 O3 1.211(4) . ?
C1 C2 1.405(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
N2 N3 C3 111.4(2) . . ?
N2 N3 C4 118.5(2) . . ?
C3 N3 C4 130.0(2) . . ?
C7 N14 N13 104.1(2) . . ?
N14 N13 C5 110.7(2) . . ?
N14 N13 C8 117.7(2) . . ?
C5 N13 C8 131.2(2) . . ?
C1 N2 N3 104.5(2) . . ?
O2 N4 C3 117.1(2) . . ?
O1 N4 O2 125.7(3) . . ?
O1 N4 C3 117.2(3) . . ?
O8 N6 C4 115.0(2) . . ?
O7 N6 O8 128.8(3) . . ?
O7 N6 C4 116.1(3) . . ?
O10 N5 O9 127.8(3) . . ?
O10 N5 C4 115.9(2) . . ?
O9 N5 C4 116.2(3) . . ?
O14 N8 O13 129.4(3) . . ?
O14 N8 C8 116.0(3) . . ?
O13 N8 C8 114.6(3) . . ?
O15 N10 C8 116.0(3) . . ?
O16 N10 O15 127.5(3) . . ?
O16 N10 C8 116.3(3) . . ?
O12 N11 C7 116.3(3) . . ?
O11 N11 O12 125.9(3) . . ?
O11 N11 C7 117.8(3) . . ?
O5 N7 C4 115.0(3) . . ?
O6 N7 O5 128.1(3) . . ?
O6 N7 C4 116.8(3) . . ?
O21 N12 O20 125.6(3) . . ?
O21 N12 C5 117.9(3) . . ?
O20 N12 C5 116.6(3) . . ?
O19 N9 C8 117.1(3) . . ?
O19 N9 O17 127.3(4) . . ?
O19 N9 O18 120.9(6) . . ?
O17 N9 C8 113.1(4) . . ?
O18 N9 C8 116.2(6) . . ?
N3 C3 N4 121.7(3) . . ?
C2 C3 N3 107.4(3) . . ?
C2 C3 N4 130.9(3) . . ?
N14 C7 N11 116.8(3) . . ?
N14 C7 C6 114.4(3) . . ?
C6 C7 N11 128.8(3) . . ?
N13 C5 N12 121.7(3) . . ?
C6 C5 N13 108.5(3) . . ?
C6 C5 N12 129.7(3) . . ?
O4 N1 C1 117.7(3) . . ?
O4 N1 O3 125.8(3) . . ?
O3 N1 C1 116.5(3) . . ?
N2 C1 N1 118.4(3) . . ?
N2 C1 C2 113.6(3) . . ?
C2 C1 N1 128.0(3) . . ?
C7 C6 Cl2 129.2(2) . . ?
C5 C6 Cl2 128.6(2) . . ?
C5 C6 C7 102.3(2) . . ?
N3 C4 N6 108.6(2) . . ?
N3 C4 N5 111.4(2) . . ?
N3 C4 N7 110.6(2) . . ?
N6 C4 N5 105.0(2) . . ?
N6 C4 N7 106.7(2) . . ?
N5 C4 N7 114.2(2) . . ?
N13 C8 N8 108.1(2) . . ?
N13 C8 N10 112.1(2) . . ?
N13 C8 N9 111.5(3) . . ?
N10 C8 N8 105.1(2) . . ?
N9 C8 N8 105.9(2) . . ?
N9 C8 N10 113.6(2) . . ?
C3 C2 Cl1 127.2(3) . . ?
C3 C2 C1 103.1(3) . . ?
C1 C2 Cl1 129.6(2) . . ?

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

data_mo_20180264-nlg-236_0m
_database_code_depnum_ccdc_archive 'CCDC 2152126'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2018-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H5 Cl N4 O5'
_chemical_formula_sum            'C6 H5 Cl N4 O5'
_chemical_formula_weight         248.59
_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'

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

_cell_length_a                   12.292(3)
_cell_length_b                   5.0976(10)
_cell_length_c                   14.985(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.479(6)
_cell_angle_gamma                90
_cell_volume                     931.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    613
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.99
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0610 before and 0.0473 after correction. The Ratio of minimum to maximum transmission is 0.8967. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5830
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         1.671
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1492
_reflns_number_total             1886
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.3280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35159(6) 0.88010(13) 0.95203(4) 0.0320(2) Uani 1 1 d . . . . .
O5 O 0.58919(15) 0.3123(4) 0.83730(13) 0.0311(5) Uani 1 1 d . . . . .
O4 O 0.57314(16) 0.6545(4) 0.92085(13) 0.0380(5) Uani 1 1 d . . . . .
O1 O 0.15622(17) 0.6058(4) 0.62957(13) 0.0371(5) Uani 1 1 d . . . . .
O2 O 0.05818(15) 0.4519(4) 0.81024(15) 0.0405(5) Uani 1 1 d . . . . .
N2 N 0.26850(16) 0.3440(4) 0.77247(14) 0.0212(5) Uani 1 1 d . . . . .
O3 O 0.11476(17) 0.8326(4) 0.86276(14) 0.0403(5) Uani 1 1 d . . . . .
N4 N 0.53515(17) 0.4831(4) 0.86843(14) 0.0245(5) Uani 1 1 d . . . . .
N3 N 0.37701(16) 0.3089(4) 0.78103(13) 0.0215(5) Uani 1 1 d . . . . .
N1 N 0.13005(18) 0.6151(4) 0.83291(14) 0.0264(5) Uani 1 1 d . . . . .
C5 C 0.3370(2) 0.6401(5) 0.87315(15) 0.0215(5) Uani 1 1 d . . . . .
C4 C 0.2423(2) 0.5430(5) 0.82599(16) 0.0220(5) Uani 1 1 d . . . . .
C6 C 0.4177(2) 0.4827(5) 0.84230(16) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.2016(2) 0.1977(5) 0.70151(16) 0.0224(5) Uani 1 1 d . . . . .
H3A H 0.1384 0.1187 0.7264 0.027 Uiso 1 1 calc R . . . .
H3B H 0.2458 0.0533 0.6807 0.027 Uiso 1 1 calc R . . . .
C2 C 0.1596(2) 0.3699(5) 0.62207(17) 0.0240(6) Uani 1 1 d . . . . .
C1 C 0.1232(2) 0.2255(6) 0.53699(18) 0.0337(7) Uani 1 1 d . . . . .
H1A H 0.0677 0.3291 0.4995 0.051 Uiso 1 1 calc GR . . . .
H1B H 0.0917 0.0562 0.5511 0.051 Uiso 1 1 calc GR . . . .
H1C H 0.1862 0.1961 0.5044 0.051 Uiso 1 1 calc GR . . . .


_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
Cl1 C5 1.694(2) . ?
O5 N4 1.224(3) . ?
O4 N4 1.226(3) . ?
O1 C2 1.209(3) . ?
O2 N1 1.229(3) . ?
N2 N3 1.335(3) . ?
N2 C4 1.358(3) . ?
N2 C3 1.462(3) . ?
O3 N1 1.219(3) . ?
N4 C6 1.446(3) . ?
N3 C6 1.326(3) . ?
N1 C4 1.444(3) . ?
C5 C4 1.374(4) . ?
C5 C6 1.400(3) . ?
C3 C2 1.515(3) . ?
C2 C1 1.490(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
N3 N2 C4 110.8(2) . . ?
N3 N2 C3 117.54(19) . . ?
C4 N2 C3 131.0(2) . . ?
O5 N4 O4 124.8(2) . . ?
O5 N4 C6 117.9(2) . . ?
O4 N4 C6 117.3(2) . . ?
C6 N3 N2 105.00(19) . . ?
O2 N1 C4 117.8(2) . . ?
O3 N1 O2 125.3(2) . . ?
O3 N1 C4 116.9(2) . . ?
C4 C5 Cl1 128.7(2) . . ?
C4 C5 C6 102.3(2) . . ?
C6 C5 Cl1 129.0(2) . . ?
N2 C4 N1 122.3(2) . . ?
N2 C4 C5 108.8(2) . . ?
C5 C4 N1 128.7(2) . . ?
N3 C6 N4 117.5(2) . . ?
N3 C6 C5 113.1(2) . . ?
C5 C6 N4 129.4(2) . . ?
N2 C3 C2 112.2(2) . . ?
O1 C2 C3 121.0(2) . . ?
O1 C2 C1 124.1(3) . . ?
C1 C2 C3 114.8(2) . . ?

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 2205042'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-03 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2022-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N8 O10'
_chemical_formula_sum            'C4 H2 N8 O10'
_chemical_formula_weight         322.14
_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'

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

_cell_length_a                   15.6313(15)
_cell_length_b                   9.2702(8)
_cell_length_c                   15.7637(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.696(3)
_cell_angle_gamma                90
_cell_volume                     2258.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4207
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      23.66
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0845 after correction.
The Ratio of minimum to maximum transmission is 0.8851.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25214
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         1.991
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3391
_reflns_number_total             5126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 V2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (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  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0825P)²+3.0392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1947
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9115(15)
 0.0885(15)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
3.a X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O20 O 0.73532(17) 0.1582(3) 0.24100(19) 0.0344(7) Uani 1 1 d . . . . .
O10 O 0.7421(2) 0.6145(3) 0.73330(18) 0.0384(7) Uani 1 1 d . . . . .
O9 O 0.7507(2) 0.3906(3) 0.69231(19) 0.0397(7) Uani 1 1 d . . . . .
N7 N 0.7620(2) 0.5225(3) 0.6836(2) 0.0281(7) Uani 1 1 d . . . . .
O2 O 0.9017(2) 0.7579(4) 0.39036(19) 0.0463(8) Uani 1 1 d . . . . .
O1 O 0.8759(2) 0.9203(3) 0.4844(2) 0.0469(8) Uani 1 1 d . . . . .
N3 N 0.8257(2) 0.4757(3) 0.55333(19) 0.0265(7) Uani 1 1 d . . . . .
O18 O 0.6395(2) -0.3233(3) 0.3955(2) 0.0453(8) Uani 1 1 d . . . . .
N10 N 0.6867(2) 0.0674(3) 0.2641(2) 0.0280(7) Uani 1 1 d . . . . .
O6 O 0.67627(19) 0.3490(4) 0.5106(2) 0.0437(8) Uani 1 1 d . . . . .
O12 O 0.39446(19) 0.3053(4) 0.4085(2) 0.0449(8) Uani 1 1 d . . . . .
N15 N 0.49449(19) 0.0961(4) 0.3622(2) 0.0268(7) Uani 1 1 d . . . . .
N11 N 0.6344(2) -0.1937(4) 0.3907(2) 0.0291(7) Uani 1 1 d . . . . .
O13 O 0.41067(19) -0.2022(4) 0.3230(2) 0.0488(8) Uani 1 1 d . . . . .
O19 O 0.6954(2) -0.0642(3) 0.2555(2) 0.0440(8) Uani 1 1 d . . . . .
O16 O 0.5145(2) -0.1128(4) 0.1844(2) 0.0504(9) Uani 1 1 d . . . . .
O14 O 0.4866(2) -0.1826(4) 0.4495(2) 0.0469(8) Uani 1 1 d . . . . .
N14 N 0.55675(18) 0.0221(3) 0.33035(19) 0.0259(7) Uani 1 1 d . . . . .
O7 O 0.8876(2) 0.1292(4) 0.6336(2) 0.0512(9) Uani 1 1 d . . . . .
O8 O 0.9252(2) 0.3430(4) 0.6764(2) 0.0501(8) Uani 1 1 d . . . . .
O4 O 0.8147(2) 0.2453(4) 0.40867(19) 0.0489(9) Uani 1 1 d . . . . .
N2 N 0.8564(2) 0.5500(4) 0.4906(2) 0.0283(7) Uani 1 1 d . . . . .
N6 N 0.8847(2) 0.2574(4) 0.6292(2) 0.0316(7) Uani 1 1 d . . . . .
N13 N 0.4754(2) -0.1780(4) 0.3725(2) 0.0315(7) Uani 1 1 d . . . . .
O15 O 0.5546(2) -0.3231(3) 0.2345(2) 0.0466(8) Uani 1 1 d . . . . .
N9 N 0.6301(2) 0.3790(3) 0.3015(2) 0.0308(7) Uani 1 1 d . . . . .
H9A H 0.677746 0.378384 0.278075 0.037 Uiso 1 1 calc R U . . .
H9B H 0.607318 0.461483 0.314371 0.037 Uiso 1 1 calc R U . . .
O3 O 0.94303(19) 0.2656(4) 0.4821(2) 0.0477(8) Uani 1 1 d . . . . .
O11 O 0.4829(2) 0.4670(4) 0.3723(3) 0.0577(10) Uani 1 1 d . . . . .
O5 O 0.7236(2) 0.1361(4) 0.5527(2) 0.0512(9) Uani 1 1 d . . . . .
O17 O 0.6826(2) -0.1086(4) 0.4304(2) 0.0552(9) Uani 1 1 d . . . . .
N16 N 0.4598(2) 0.3419(4) 0.3812(2) 0.0338(8) Uani 1 1 d . . . . .
N5 N 0.7324(2) 0.2622(4) 0.5386(2) 0.0325(7) Uani 1 1 d . . . . .
N8 N 0.8022(2) 0.8329(4) 0.6291(2) 0.0369(8) Uani 1 1 d . . . . .
H8A H 0.780179 0.831589 0.677318 0.044 Uiso 1 1 calc R U . . .
H8B H 0.815343 0.915631 0.606970 0.044 Uiso 1 1 calc R U . . .
N4 N 0.8652(2) 0.2729(4) 0.4715(2) 0.0320(8) Uani 1 1 d . . . . .
N12 N 0.5416(2) -0.1959(4) 0.2409(2) 0.0317(7) Uani 1 1 d . . . . .
N1 N 0.8783(2) 0.7961(4) 0.4576(2) 0.0368(8) Uani 1 1 d . . . . .
C6 C 0.5928(2) 0.2562(4) 0.3174(2) 0.0233(7) Uani 1 1 d . . . . .
C3 C 0.7993(2) 0.5697(4) 0.6139(2) 0.0276(8) Uani 1 1 d . . . . .
C5 C 0.6171(2) 0.1161(4) 0.3027(2) 0.0246(7) Uani 1 1 d . . . . .
C1 C 0.8501(2) 0.6860(4) 0.5121(2) 0.0286(8) Uani 1 1 d . . . . .
C4 C 0.8256(2) 0.3246(4) 0.5507(2) 0.0277(8) Uani 1 1 d . . . . .
C2 C 0.8154(2) 0.7104(4) 0.5900(2) 0.0273(8) Uani 1 1 d . . . . .
C7 C 0.5154(2) 0.2322(4) 0.3550(2) 0.0260(8) Uani 1 1 d . . . . .
C8 C 0.5547(2) -0.1294(4) 0.3322(2) 0.0262(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O20 N10 1.225(4) . ?
O10 N7 1.230(4) . ?
O9 N7 1.246(4) . ?
N7 C3 1.390(5) . ?
O2 N1 1.224(5) . ?
O1 N1 1.229(5) . ?
N3 N2 1.351(4) . ?
N3 C3 1.400(5) . ?
N3 C4 1.401(5) . ?
O18 N11 1.205(4) . ?
N10 O19 1.238(4) . ?
N10 C5 1.398(4) . ?
O6 N5 1.223(5) . ?
O12 N16 1.214(4) . ?
N15 N14 1.349(4) . ?
N15 C7 1.312(5) . ?
N11 O17 1.200(4) . ?
N11 C8 1.553(5) . ?
O13 N13 1.202(4) . ?
O16 N12 1.204(5) . ?
O14 N13 1.200(4) . ?
N14 C5 1.402(5) . ?
N14 C8 1.405(5) . ?
O7 N6 1.191(5) . ?
O8 N6 1.202(5) . ?
O4 N4 1.198(4) . ?
N2 C1 1.313(5) . ?
N6 C4 1.557(5) . ?
N13 C8 1.544(5) . ?
O15 N12 1.203(5) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C6 1.320(5) . ?
O3 N4 1.204(4) . ?
O11 N16 1.229(5) . ?
O5 N5 1.202(5) . ?
N16 C7 1.439(5) . ?
N5 C4 1.552(5) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C2 1.324(5) . ?
N4 C4 1.550(5) . ?
N12 C8 1.551(5) . ?
N1 C1 1.445(5) . ?
C6 C5 1.383(5) . ?
C6 C7 1.443(5) . ?
C3 C2 1.391(5) . ?
C1 C2 1.433(5) . ?

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
O10 N7 O9 123.8(3) . . ?
O10 N7 C3 117.5(3) . . ?
O9 N7 C3 118.7(3) . . ?
N2 N3 C3 110.8(3) . . ?
N2 N3 C4 119.1(3) . . ?
C3 N3 C4 130.1(3) . . ?
O20 N10 O19 124.1(3) . . ?
O20 N10 C5 117.7(3) . . ?
O19 N10 C5 118.1(3) . . ?
C7 N15 N14 104.7(3) . . ?
O18 N11 C8 117.3(3) . . ?
O17 N11 O18 126.3(4) . . ?
O17 N11 C8 116.2(3) . . ?
N15 N14 C5 111.0(3) . . ?
N15 N14 C8 118.7(3) . . ?
C5 N14 C8 130.2(3) . . ?
C1 N2 N3 104.6(3) . . ?
O7 N6 O8 127.7(4) . . ?
O7 N6 C4 117.3(3) . . ?
O8 N6 C4 115.0(3) . . ?
O13 N13 C8 115.8(3) . . ?
O14 N13 O13 129.1(3) . . ?
O14 N13 C8 115.0(3) . . ?
H9A N9 H9B 120.0 . . ?
C6 N9 H9A 120.0 . . ?
C6 N9 H9B 120.0 . . ?
O12 N16 O11 125.6(3) . . ?
O12 N16 C7 118.7(3) . . ?
O11 N16 C7 115.7(3) . . ?
O6 N5 C4 114.1(3) . . ?
O5 N5 O6 127.6(4) . . ?
O5 N5 C4 118.2(3) . . ?
H8A N8 H8B 120.0 . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
O4 N4 O3 129.0(3) . . ?
O4 N4 C4 116.0(3) . . ?
O3 N4 C4 115.1(3) . . ?
O16 N12 C8 114.4(3) . . ?
O15 N12 O16 127.6(4) . . ?
O15 N12 C8 117.8(3) . . ?
O2 N1 O1 126.7(4) . . ?
O2 N1 C1 117.9(4) . . ?
O1 N1 C1 115.4(3) . . ?
N9 C6 C5 129.6(3) . . ?
N9 C6 C7 129.2(3) . . ?
C5 C6 C7 101.1(3) . . ?
N7 C3 N3 123.0(3) . . ?
N7 C3 C2 128.7(3) . . ?
C2 C3 N3 108.3(3) . . ?
N10 C5 N14 122.7(3) . . ?
C6 C5 N10 128.9(3) . . ?
C6 C5 N14 108.4(3) . . ?
N2 C1 N1 118.9(3) . . ?
N2 C1 C2 115.1(3) . . ?
C2 C1 N1 125.9(4) . . ?
N3 C4 N6 112.2(3) . . ?
N3 C4 N5 111.9(3) . . ?
N3 C4 N4 109.5(3) . . ?
N5 C4 N6 112.4(3) . . ?
N4 C4 N6 104.8(3) . . ?
N4 C4 N5 105.5(3) . . ?
N8 C2 C3 129.0(3) . . ?
N8 C2 C1 129.9(4) . . ?
C3 C2 C1 101.1(3) . . ?
N15 C7 N16 119.0(3) . . ?
N15 C7 C6 114.8(3) . . ?
N16 C7 C6 126.1(3) . . ?
N14 C8 N11 112.1(3) . . ?
N14 C8 N13 108.8(3) . . ?
N14 C8 N12 112.3(3) . . ?
N13 C8 N11 105.4(3) . . ?
N13 C8 N12 105.4(3) . . ?
N12 C8 N11 112.3(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
O20 N10 C5 N14 179.0(3) . . . . ?
O20 N10 C5 C6 1.7(6) . . . . ?
O10 N7 C3 N3 179.2(3) . . . . ?
O10 N7 C3 C2 -2.2(6) . . . . ?
O9 N7 C3 N3 -0.8(6) . . . . ?
O9 N7 C3 C2 177.8(4) . . . . ?
N7 C3 C2 N8 2.7(7) . . . . ?
N7 C3 C2 C1 -177.4(4) . . . . ?
O2 N1 C1 N2 4.8(5) . . . . ?
O2 N1 C1 C2 -175.8(4) . . . . ?
O1 N1 C1 N2 -175.4(4) . . . . ?
O1 N1 C1 C2 4.0(6) . . . . ?
N3 N2 C1 N1 179.8(3) . . . . ?
N3 N2 C1 C2 0.3(4) . . . . ?
N3 C3 C2 N8 -178.7(4) . . . . ?
N3 C3 C2 C1 1.3(4) . . . . ?
O18 N11 C8 N14 -178.8(3) . . . . ?
O18 N11 C8 N13 62.9(4) . . . . ?
O18 N11 C8 N12 -51.3(4) . . . . ?
O6 N5 C4 N3 18.9(4) . . . . ?
O6 N5 C4 N6 146.2(3) . . . . ?
O6 N5 C4 N4 -100.2(4) . . . . ?
O12 N16 C7 N15 -0.7(5) . . . . ?
O12 N16 C7 C6 176.7(4) . . . . ?
N15 N14 C5 N10 -177.7(3) . . . . ?
N15 N14 C5 C6 0.1(4) . . . . ?
N15 N14 C8 N11 -115.7(3) . . . . ?
N15 N14 C8 N13 0.5(5) . . . . ?
N15 N14 C8 N12 116.7(3) . . . . ?
O13 N13 C8 N11 -146.0(3) . . . . ?
O13 N13 C8 N14 93.6(4) . . . . ?
O13 N13 C8 N12 -27.0(4) . . . . ?
O19 N10 C5 N14 -1.0(6) . . . . ?
O19 N10 C5 C6 -178.3(4) . . . . ?
O16 N12 C8 N11 -144.8(3) . . . . ?
O16 N12 C8 N14 -17.3(4) . . . . ?
O16 N12 C8 N13 100.9(4) . . . . ?
O14 N13 C8 N11 35.8(4) . . . . ?
O14 N13 C8 N14 -84.6(4) . . . . ?
O14 N13 C8 N12 154.8(3) . . . . ?
N14 N15 C7 N16 178.0(3) . . . . ?
N14 N15 C7 C6 0.3(4) . . . . ?
O7 N6 C4 N3 178.6(3) . . . . ?
O7 N6 C4 N5 51.5(4) . . . . ?
O7 N6 C4 N4 -62.6(4) . . . . ?
O8 N6 C4 N3 -4.7(5) . . . . ?
O8 N6 C4 N5 -131.8(4) . . . . ?
O8 N6 C4 N4 114.1(4) . . . . ?
O4 N4 C4 N3 -96.0(4) . . . . ?
O4 N4 C4 N6 143.4(4) . . . . ?
O4 N4 C4 N5 24.5(5) . . . . ?
N2 N3 C3 N7 177.5(3) . . . . ?
N2 N3 C3 C2 -1.3(4) . . . . ?
N2 N3 C4 N6 117.1(3) . . . . ?
N2 N3 C4 N5 -115.5(3) . . . . ?
N2 N3 C4 N4 1.1(5) . . . . ?
N2 C1 C2 N8 178.9(4) . . . . ?
N2 C1 C2 C3 -1.0(4) . . . . ?
O15 N12 C8 N11 39.2(4) . . . . ?
O15 N12 C8 N14 166.6(3) . . . . ?
O15 N12 C8 N13 -75.1(4) . . . . ?
N9 C6 C5 N10 -2.3(7) . . . . ?
N9 C6 C5 N14 -179.9(4) . . . . ?
N9 C6 C7 N15 179.8(4) . . . . ?
N9 C6 C7 N16 2.2(6) . . . . ?
O3 N4 C4 N3 84.3(4) . . . . ?
O3 N4 C4 N6 -36.3(4) . . . . ?
O3 N4 C4 N5 -155.2(3) . . . . ?
O11 N16 C7 N15 -179.6(4) . . . . ?
O11 N16 C7 C6 -2.2(6) . . . . ?
O5 N5 C4 N3 -165.1(4) . . . . ?
O5 N5 C4 N6 -37.8(5) . . . . ?
O5 N5 C4 N4 75.9(4) . . . . ?
O17 N11 C8 N14 5.1(5) . . . . ?
O17 N11 C8 N13 -113.1(4) . . . . ?
O17 N11 C8 N12 132.7(4) . . . . ?
N1 C1 C2 N8 -0.5(7) . . . . ?
N1 C1 C2 C3 179.6(4) . . . . ?
C3 N3 N2 C1 0.6(4) . . . . ?
C3 N3 C4 N6 -61.7(5) . . . . ?
C3 N3 C4 N5 65.7(5) . . . . ?
C3 N3 C4 N4 -177.6(4) . . . . ?
C5 N14 C8 N11 61.5(5) . . . . ?
C5 N14 C8 N13 177.7(3) . . . . ?
C5 N14 C8 N12 -66.1(5) . . . . ?
C5 C6 C7 N15 -0.3(4) . . . . ?
C5 C6 C7 N16 -177.8(4) . . . . ?
C4 N3 N2 C1 -178.4(3) . . . . ?
C4 N3 C3 N7 -3.7(6) . . . . ?
C4 N3 C3 C2 177.5(4) . . . . ?
C7 N15 N14 C5 -0.2(4) . . . . ?
C7 N15 N14 C8 177.5(3) . . . . ?
C7 C6 C5 N10 177.7(4) . . . . ?
C7 C6 C5 N14 0.1(4) . . . . ?
C8 N14 C5 N10 5.0(6) . . . . ?
C8 N14 C5 C6 -177.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9115(15)
2 0.0885(15)

####################################################################### 
# 
# 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_DLJ_012_a
_database_code_depnum_ccdc_archive 'CCDC 2205331'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-03 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N6 O9, 2(H2 O)'
_chemical_formula_sum            'C4 H4 N6 O11'
_chemical_formula_weight         312.13

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6403(9)
_cell_length_b                   7.7898(8)
_cell_length_c                   11.2231(11)
_cell_angle_alpha                78.002(3)
_cell_angle_beta                 80.654(3)
_cell_angle_gamma                62.508(3)
_cell_volume                     577.88(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4206
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.75

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            8706
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.982
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2639
_reflns_number_gt                1961
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+0.5042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2639
_refine_ls_number_parameters     202
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9612(3) 0.7240(3) 0.0761(2) 0.0240(5) Uani 1 1 d . . . . .
C2 C 0.7715(3) 0.7555(3) 0.0558(2) 0.0259(5) Uani 1 1 d . . . . .
C3 C 0.6757(3) 0.7354(3) 0.1737(2) 0.0266(5) Uani 1 1 d . . . . .
C4 C 0.7948(4) 0.6591(3) 0.3764(2) 0.0299(5) Uani 1 1 d . . . . .
N1 N 0.8187(3) 0.6963(3) 0.25047(17) 0.0293(4) Uani 1 1 d . . . . .
N2 N 0.9955(3) 0.6881(3) 0.19044(17) 0.0288(4) Uani 1 1 d . . . . .
N3 N 1.1174(3) 0.7343(3) -0.01405(17) 0.0295(4) Uani 1 1 d . . . . .
N4 N 0.6931(3) 0.7819(3) -0.05420(18) 0.0301(5) Uani 1 1 d . . . . .
N6 N 0.7630(3) 0.8027(3) 0.44295(19) 0.0331(5) Uani 1 1 d . . . . .
N7 N 0.7956(3) 0.4813(3) 0.42937(18) 0.0331(5) Uani 1 1 d . . . . .
O1 O 1.2850(3) 0.6064(3) 0.00065(19) 0.0489(5) Uani 1 1 d . . . . .
O2 O 1.0725(3) 0.8684(3) -0.09956(16) 0.0443(5) Uani 1 1 d . . . . .
O3 O 0.8060(3) 0.7482(3) -0.14808(16) 0.0424(5) Uani 1 1 d . . . . .
O4 O 0.5146(3) 0.8306(3) -0.05326(18) 0.0412(5) Uani 1 1 d . . . . .
O5 O 0.8278(3) 0.3628(3) 0.35990(18) 0.0458(5) Uani 1 1 d . . . . .
O6 O 0.7649(4) 0.4420(3) 0.54070(17) 0.0588(6) Uani 1 1 d . . . . .
O7 O 0.7391(4) 0.7795(3) 0.55571(17) 0.0539(6) Uani 1 1 d . . . . .
O8 O 0.7664(3) 0.9568(3) 0.38450(19) 0.0490(5) Uani 1 1 d . . . . .
O9 O 0.5131(3) 0.7385(3) 0.21142(16) 0.0371(4) Uani 1 1 d . . . . .
O10 O 0.4755(4) 0.3746(4) 0.2479(2) 0.0585(6) Uani 1 1 d D . . . .
H10A H 0.501(6) 0.474(5) 0.238(4) 0.088 Uiso 1 1 d D U . . .
H10B H 0.384(5) 0.384(6) 0.306(3) 0.088 Uiso 1 1 d D U . . .
O11 O 0.1637(4) 0.9556(3) 0.3381(2) 0.0620(6) Uani 1 1 d D . . . .
H11A H 0.278(4) 0.902(6) 0.294(3) 0.093 Uiso 1 1 d D U . . .
H11B H 0.158(6) 0.862(5) 0.394(3) 0.093 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.299(3) . ?
C1 C2 1.403(3) . ?
C1 N3 1.455(3) . ?
C2 N4 1.395(3) . ?
C2 C3 1.421(3) . ?
C3 O9 1.236(3) . ?
C3 N1 1.385(3) . ?
C4 N6 1.380(3) . ?
C4 N1 1.382(3) . ?
C4 N7 1.386(3) . ?
N1 N2 1.388(3) . ?
N3 O1 1.217(3) . ?
N3 O2 1.220(3) . ?
N4 O4 1.235(3) . ?
N4 O3 1.238(3) . ?
N6 O7 1.236(3) . ?
N6 O8 1.252(3) . ?
N7 O6 1.234(3) . ?
N7 O5 1.244(3) . ?
O10 H10A 0.863(18) . ?
O10 H10B 0.863(18) . ?
O11 H11A 0.887(19) . ?
O11 H11B 0.869(18) . ?

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
N2 C1 C2 114.5(2) . . ?
N2 C1 N3 117.3(2) . . ?
C2 C1 N3 128.1(2) . . ?
N4 C2 C1 129.1(2) . . ?
N4 C2 C3 125.1(2) . . ?
C1 C2 C3 105.53(19) . . ?
O9 C3 N1 123.1(2) . . ?
O9 C3 C2 134.1(2) . . ?
N1 C3 C2 102.69(19) . . ?
N6 C4 N1 118.8(2) . . ?
N6 C4 N7 123.2(2) . . ?
N1 C4 N7 117.9(2) . . ?
C4 N1 C3 123.9(2) . . ?
C4 N1 N2 121.59(19) . . ?
C3 N1 N2 114.40(18) . . ?
C1 N2 N1 102.84(18) . . ?
O1 N3 O2 124.3(2) . . ?
O1 N3 C1 117.34(18) . . ?
O2 N3 C1 118.34(19) . . ?
O4 N4 O3 122.4(2) . . ?
O4 N4 C2 118.5(2) . . ?
O3 N4 C2 119.0(2) . . ?
O7 N6 O8 120.7(2) . . ?
O7 N6 C4 122.1(2) . . ?
O8 N6 C4 117.1(2) . . ?
O6 N7 O5 121.2(2) . . ?
O6 N7 C4 121.6(2) . . ?
O5 N7 C4 117.3(2) . . ?
H10A O10 H10B 110(3) . . ?
H11A O11 H11B 106(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
N2 C1 C2 N4 -174.4(2) . . . . ?
N3 C1 C2 N4 8.2(4) . . . . ?
N2 C1 C2 C3 -0.4(3) . . . . ?
N3 C1 C2 C3 -177.7(2) . . . . ?
N4 C2 C3 O9 -1.6(4) . . . . ?
C1 C2 C3 O9 -176.0(2) . . . . ?
N4 C2 C3 N1 175.0(2) . . . . ?
C1 C2 C3 N1 0.6(2) . . . . ?
N6 C4 N1 C3 -105.6(3) . . . . ?
N7 C4 N1 C3 71.8(3) . . . . ?
N6 C4 N1 N2 77.5(3) . . . . ?
N7 C4 N1 N2 -105.2(3) . . . . ?
O9 C3 N1 C4 -0.8(3) . . . . ?
C2 C3 N1 C4 -177.9(2) . . . . ?
O9 C3 N1 N2 176.4(2) . . . . ?
C2 C3 N1 N2 -0.7(2) . . . . ?
C2 C1 N2 N1 -0.1(2) . . . . ?
N3 C1 N2 N1 177.58(17) . . . . ?
C4 N1 N2 C1 177.7(2) . . . . ?
C3 N1 N2 C1 0.5(2) . . . . ?
N2 C1 N3 O1 45.7(3) . . . . ?
C2 C1 N3 O1 -137.0(2) . . . . ?
N2 C1 N3 O2 -135.0(2) . . . . ?
C2 C1 N3 O2 42.3(3) . . . . ?
C1 C2 N4 O4 -171.6(2) . . . . ?
C3 C2 N4 O4 15.4(3) . . . . ?
C1 C2 N4 O3 11.2(3) . . . . ?
C3 C2 N4 O3 -161.8(2) . . . . ?
N1 C4 N6 O7 179.5(2) . . . . ?
N7 C4 N6 O7 2.4(4) . . . . ?
N1 C4 N6 O8 -3.0(3) . . . . ?
N7 C4 N6 O8 179.8(2) . . . . ?
N6 C4 N7 O6 1.0(4) . . . . ?
N1 C4 N7 O6 -176.2(2) . . . . ?
N6 C4 N7 O5 -179.3(2) . . . . ?
N1 C4 N7 O5 3.5(3) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_DLJ_009_a
_database_code_depnum_ccdc_archive 'CCDC 2205048'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-03 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 Cl N7 O10'
_chemical_formula_sum            'C4 Cl N7 O10'
_chemical_formula_weight         341.56

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'
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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.9214(7)
_cell_length_b                   6.9287(3)
_cell_length_c                   13.9386(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.823(2)
_cell_angle_gamma                90
_cell_volume                     1220.26(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5926
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.389
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5309
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            10861
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2136
_reflns_number_gt                1831
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1180P)²+0.8180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.054(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2136
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1872
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7808(3) 0.4114(5) 0.6219(3) 0.0521(9) Uani 1 1 d . . . . .
C2 C 0.8529(3) 0.4078(5) 0.7291(3) 0.0464(8) Uani 1 1 d . . . . .
C3 C 0.8161(2) 0.5412(5) 0.7775(2) 0.0430(8) Uani 1 1 d . . . . .
C4 C 0.6566(3) 0.7557(5) 0.7068(3) 0.0496(8) Uani 1 1 d . . . . .
Cl1 Cl 0.86687(6) 0.61957(12) 0.90697(5) 0.0450(4) Uani 1 1 d . . . . .
N1 N 0.7036(2) 0.5323(5) 0.6024(2) 0.0525(8) Uani 1 1 d . . . . .
N2 N 0.7264(2) 0.6146(4) 0.6992(2) 0.0471(7) Uani 1 1 d . . . . .
N3 N 0.7784(3) 0.2903(6) 0.5360(3) 0.0710(10) Uani 1 1 d . . . . .
N4 N 0.9478(2) 0.2969(5) 0.7736(3) 0.0621(9) Uani 1 1 d . . . . .
N5 N 0.7052(3) 0.9581(5) 0.7286(3) 0.0593(8) Uani 1 1 d . . . . .
N6 N 0.6197(2) 0.7009(5) 0.7929(3) 0.0619(9) Uani 1 1 d . . . . .
N7 N 0.5581(3) 0.7666(5) 0.6012(3) 0.0663(10) Uani 1 1 d . . . . .
O1 O 0.7926(5) 0.3652(7) 0.4675(3) 0.1257(19) Uani 1 1 d . . . . .
O2 O 0.7597(4) 0.1209(6) 0.5397(4) 0.1143(15) Uani 1 1 d . . . . .
O3 O 0.9745(3) 0.2139(6) 0.7124(3) 0.1005(12) Uani 1 1 d . . . . .
O4 O 0.9943(3) 0.2869(6) 0.8677(3) 0.0958(12) Uani 1 1 d . . . . .
O5 O 0.6090(3) 0.5290(5) 0.8020(3) 0.0869(10) Uani 1 1 d . . . . .
O6 O 0.6040(3) 0.8285(6) 0.8420(3) 0.1010(12) Uani 1 1 d . . . . .
O7 O 0.7988(3) 0.9695(4) 0.7579(3) 0.0761(9) Uani 1 1 d . . . . .
O8 O 0.6431(3) 1.0889(5) 0.7136(3) 0.0922(11) Uani 1 1 d . . . . .
O9 O 0.4788(3) 0.6924(7) 0.5983(3) 0.1032(13) Uani 1 1 d . . . . .
O10 O 0.5726(3) 0.8510(6) 0.5320(3) 0.0912(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.299(5) . ?
C1 C2 1.407(5) . ?
C1 N3 1.451(5) . ?
C2 C3 1.364(5) . ?
C2 N4 1.426(5) . ?
C3 N2 1.366(4) . ?
C3 Cl1 1.727(3) . ?
C4 N2 1.413(4) . ?
C4 N5 1.531(5) . ?
C4 N7 1.535(5) . ?
C4 N6 1.538(5) . ?
N1 N2 1.374(4) . ?
N3 O1 1.174(5) . ?
N3 O2 1.208(6) . ?
N4 O4 1.196(5) . ?
N4 O3 1.209(5) . ?
N5 O7 1.194(4) . ?
N5 O8 1.208(5) . ?
N6 O6 1.193(5) . ?
N6 O5 1.213(5) . ?
N7 O9 1.203(5) . ?
N7 O10 1.216(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.1(3) . . ?
N1 C1 N3 118.0(3) . . ?
C2 C1 N3 128.7(3) . . ?
C3 C2 C1 105.4(3) . . ?
C3 C2 N4 128.4(3) . . ?
C1 C2 N4 126.1(3) . . ?
C2 C3 N2 105.3(3) . . ?
C2 C3 Cl1 131.0(3) . . ?
N2 C3 Cl1 123.6(3) . . ?
N2 C4 N5 112.8(3) . . ?
N2 C4 N7 109.1(3) . . ?
N5 C4 N7 106.7(3) . . ?
N2 C4 N6 110.6(3) . . ?
N5 C4 N6 109.6(3) . . ?
N7 C4 N6 107.7(3) . . ?
C1 N1 N2 103.4(3) . . ?
C3 N2 N1 112.7(3) . . ?
C3 N2 C4 128.7(3) . . ?
N1 N2 C4 118.5(3) . . ?
O1 N3 O2 125.3(4) . . ?
O1 N3 C1 117.6(4) . . ?
O2 N3 C1 117.2(4) . . ?
O4 N4 O3 124.1(4) . . ?
O4 N4 C2 119.0(4) . . ?
O3 N4 C2 116.9(3) . . ?
O7 N5 O8 127.5(4) . . ?
O7 N5 C4 117.1(3) . . ?
O8 N5 C4 115.4(3) . . ?
O6 N6 O5 127.4(4) . . ?
O6 N6 C4 117.8(4) . . ?
O5 N6 C4 114.8(3) . . ?
O9 N7 O10 129.4(4) . . ?
O9 N7 C4 116.7(4) . . ?
O10 N7 C4 113.9(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
N1 C1 C2 C3 -1.1(4) . . . . ?
N3 C1 C2 C3 -176.0(4) . . . . ?
N1 C1 C2 N4 -176.9(3) . . . . ?
N3 C1 C2 N4 8.1(7) . . . . ?
C1 C2 C3 N2 0.3(4) . . . . ?
N4 C2 C3 N2 176.0(3) . . . . ?
C1 C2 C3 Cl1 -177.4(3) . . . . ?
N4 C2 C3 Cl1 -1.7(6) . . . . ?
C2 C1 N1 N2 1.3(4) . . . . ?
N3 C1 N1 N2 176.8(3) . . . . ?
C2 C3 N2 N1 0.5(4) . . . . ?
Cl1 C3 N2 N1 178.4(2) . . . . ?
C2 C3 N2 C4 179.0(3) . . . . ?
Cl1 C3 N2 C4 -3.0(5) . . . . ?
C1 N1 N2 C3 -1.1(4) . . . . ?
C1 N1 N2 C4 -179.8(3) . . . . ?
N5 C4 N2 C3 70.5(4) . . . . ?
N7 C4 N2 C3 -171.0(3) . . . . ?
N6 C4 N2 C3 -52.7(4) . . . . ?
N5 C4 N2 N1 -111.0(3) . . . . ?
N7 C4 N2 N1 7.5(4) . . . . ?
N6 C4 N2 N1 125.8(3) . . . . ?
N1 C1 N3 O1 70.2(6) . . . . ?
C2 C1 N3 O1 -115.1(5) . . . . ?
N1 C1 N3 O2 -108.3(5) . . . . ?
C2 C1 N3 O2 66.5(6) . . . . ?
C3 C2 N4 O4 15.3(6) . . . . ?
C1 C2 N4 O4 -169.9(4) . . . . ?
C3 C2 N4 O3 -166.7(4) . . . . ?
C1 C2 N4 O3 8.2(6) . . . . ?
N2 C4 N5 O7 -15.0(5) . . . . ?
N7 C4 N5 O7 -134.9(3) . . . . ?
N6 C4 N5 O7 108.8(4) . . . . ?
N2 C4 N5 O8 164.8(4) . . . . ?
N7 C4 N5 O8 45.0(4) . . . . ?
N6 C4 N5 O8 -71.3(4) . . . . ?
N2 C4 N6 O6 146.3(4) . . . . ?
N5 C4 N6 O6 21.2(5) . . . . ?
N7 C4 N6 O6 -94.5(4) . . . . ?
N2 C4 N6 O5 -34.4(4) . . . . ?
N5 C4 N6 O5 -159.5(3) . . . . ?
N7 C4 N6 O5 84.8(4) . . . . ?
N2 C4 N7 O9 104.0(4) . . . . ?
N5 C4 N7 O9 -133.8(4) . . . . ?
N6 C4 N7 O9 -16.1(5) . . . . ?
N2 C4 N7 O10 -76.0(4) . . . . ?
N5 C4 N7 O10 46.2(4) . . . . ?
N6 C4 N7 O10 163.8(3) . . . . ?

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_2147_0m
_database_code_depnum_ccdc_archive 'CCDC 2152131'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H7 N5 O5'
_chemical_formula_sum            'C6 H7 N5 O5'
_chemical_formula_weight         229.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.4834(4)
_cell_length_b                   20.756(2)
_cell_length_c                   9.7107(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.924(3)
_cell_angle_gamma                90
_cell_volume                     895.02(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1815
_cell_measurement_temperature    110
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      3.627
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1043 before and 0.0671 after correction. The Ratio of minimum to maximum transmission is 0.8090. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8322
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.334
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1219
_reflns_number_total             1823
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.6589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1227
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.6153(4) 0.63370(8) 0.2153(2) 0.0226(5) Uani 1 1 d . . . . .
O002 O 0.8442(4) 0.78445(8) 0.4709(2) 0.0249(5) Uani 1 1 d . . . . .
O003 O 1.1208(4) 0.72375(9) 0.35405(19) 0.0239(5) Uani 1 1 d . . . . .
O004 O 0.3055(4) 0.61541(9) 0.7941(2) 0.0270(5) Uani 1 1 d . . . . .
O005 O 0.4788(5) 0.52107(9) 0.7448(2) 0.0301(5) Uani 1 1 d . . . . .
N4 N 0.9045(5) 0.61459(10) 0.4733(2) 0.0176(5) Uani 1 1 d . . . . .
N5 N 0.7756(5) 0.57314(10) 0.5516(2) 0.0189(5) Uani 1 1 d . . . . .
N2 N 0.5085(5) 0.72606(10) 0.6614(2) 0.0208(5) Uani 1 1 d . . . . .
H2A H 0.536272 0.765696 0.633666 0.025 Uiso 1 1 calc R . . . .
H2B H 0.393734 0.718857 0.726404 0.025 Uiso 1 1 calc R . . . .
N3 N 0.9386(5) 0.73138(10) 0.4379(2) 0.0207(5) Uani 1 1 d . . . . .
N1 N 0.4602(5) 0.57972(11) 0.7295(2) 0.0212(5) Uani 1 1 d . . . . .
C2 C 0.6408(6) 0.67668(12) 0.6048(3) 0.0175(6) Uani 1 1 d . . . . .
C1 C 0.8292(6) 0.67718(12) 0.5017(3) 0.0176(6) Uani 1 1 d . . . . .
C4 C 0.8434(6) 0.60136(12) 0.2191(3) 0.0191(6) Uani 1 1 d . . . . .
C3 C 0.6232(6) 0.61006(12) 0.6306(3) 0.0193(6) Uani 1 1 d . . . . .
C5 C 1.0416(6) 0.58888(13) 0.3568(3) 0.0201(6) Uani 1 1 d . . . . .
H5A H 1.073071 0.541922 0.369442 0.024 Uiso 1 1 calc R . . . .
H5B H 1.240700 0.609273 0.355287 0.024 Uiso 1 1 calc R . . . .
C6 C 0.9476(7) 0.57239(14) 0.0939(3) 0.0252(7) Uani 1 1 d . . . . .
H6A H 0.779216 0.570580 0.018090 0.038 Uiso 1 1 calc GR . . . .
H6B H 1.022613 0.528714 0.115822 0.038 Uiso 1 1 calc GR . . . .
H6C H 1.109638 0.598802 0.065387 0.038 Uiso 1 1 calc GR . . . .


_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
O001 C4 1.220(3) . ?
O002 N3 1.238(3) . ?
O003 N3 1.240(3) . ?
O004 N1 1.242(3) . ?
O005 N1 1.228(3) . ?
N4 N5 1.332(3) . ?
N4 C1 1.380(3) . ?
N4 C5 1.460(3) . ?
N5 C3 1.337(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C2 1.340(3) . ?
N3 C1 1.405(3) . ?
N1 C3 1.430(3) . ?
C2 C1 1.396(4) . ?
C2 C3 1.409(4) . ?
C4 C5 1.522(4) . ?
C4 C6 1.488(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 N4 C1 110.9(2) . . ?
N5 N4 C5 117.9(2) . . ?
C1 N4 C5 129.8(2) . . ?
N4 N5 C3 104.7(2) . . ?
H2A N2 H2B 120.0 . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
O002 N3 O003 124.3(2) . . ?
O002 N3 C1 116.4(2) . . ?
O003 N3 C1 119.3(2) . . ?
O004 N1 C3 116.7(2) . . ?
O005 N1 O004 124.3(2) . . ?
O005 N1 C3 119.0(2) . . ?
N2 C2 C1 129.4(2) . . ?
N2 C2 C3 129.7(2) . . ?
C1 C2 C3 100.9(2) . . ?
N4 C1 N3 123.7(2) . . ?
N4 C1 C2 109.0(2) . . ?
C2 C1 N3 127.2(2) . . ?
O001 C4 C5 120.4(2) . . ?
O001 C4 C6 123.6(3) . . ?
C6 C4 C5 116.0(2) . . ?
N5 C3 N1 118.8(2) . . ?
N5 C3 C2 114.5(2) . . ?
C2 C3 N1 126.7(2) . . ?
N4 C5 C4 111.2(2) . . ?
N4 C5 H5A 109.4 . . ?
N4 C5 H5B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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

data_2175_0m
_database_code_depnum_ccdc_archive 'CCDC 2205049'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-03 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H5 N5 O4'
_chemical_formula_sum            'C4 H5 N5 O4'
_chemical_formula_weight         187.13
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   4.0966(8)
_cell_length_b                   12.015(2)
_cell_length_c                   7.3348(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.207(6)
_cell_angle_gamma                90
_cell_volume                     355.30(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1157
_cell_measurement_temperature    170
_cell_measurement_theta_max      23.512
_cell_measurement_theta_min      3.292
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1117 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.8623. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4326
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.679
_diffrn_reflns_theta_min         3.292
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.860
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                990
_reflns_number_total             1482
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 340 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), N2(H2)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.8898(10) 0.5532(3) 0.6568(6) 0.0343(11) Uani 1 1 d . . . . .
O3 O 0.4836(10) 0.4601(3) 0.4898(6) 0.0364(11) Uani 1 1 d . . . . .
O2 O 0.5189(12) 0.9895(3) 0.3955(6) 0.0424(12) Uani 1 1 d . . . . .
O1 O 0.0841(11) 0.9570(3) 0.1843(6) 0.0438(13) Uani 1 1 d . . . . .
N5 N 0.1447(12) 0.7386(4) 0.2440(6) 0.0280(12) Uani 1 1 d . . . . .
N4 N 0.2275(11) 0.6409(4) 0.3187(7) 0.0262(12) Uani 1 1 d . . . . .
H4 H 0.131485 0.577980 0.277612 0.031 Uiso 1 1 calc R . . . .
N1 N 0.3125(12) 0.9263(4) 0.3044(7) 0.0333(14) Uani 1 1 d . . . . .
N3 N 0.6240(10) 0.5488(4) 0.5439(6) 0.0262(12) Uani 1 1 d . . . . .
N2 N 0.7849(12) 0.8134(4) 0.6261(7) 0.0301(12) Uani 1 1 d . . . . .
H2 H 0.857745 0.878317 0.594983 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3467(14) 0.8095(4) 0.3484(8) 0.0241(13) Uani 1 1 d . . . . .
C3 C 0.4814(13) 0.6482(4) 0.4682(7) 0.0222(13) Uani 1 1 d . . . . .
C2 C 0.5670(14) 0.7606(5) 0.4977(7) 0.0232(12) Uani 1 1 d . . . . .
C4 C 0.9132(15) 0.7736(5) 0.8126(8) 0.0337(15) Uani 1 1 d . . . . .
H4A H 1.112521 0.728777 0.811239 0.051 Uiso 1 1 calc GR . . . .
H4B H 0.744413 0.727997 0.856422 0.051 Uiso 1 1 calc GR . . . .
H4C H 0.968872 0.837359 0.895686 0.051 Uiso 1 1 calc GR . . . .


_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 N3 1.247(5) . ?
O3 N3 1.243(6) . ?
O2 N1 1.240(6) . ?
O1 N1 1.223(6) . ?
N5 N4 1.314(6) . ?
N5 C1 1.331(7) . ?
N4 H4 0.8800 . ?
N4 C3 1.374(7) . ?
N1 C1 1.441(7) . ?
N3 C3 1.400(7) . ?
N2 H2 0.8800 . ?
N2 C2 1.337(7) . ?
N2 C4 1.456(7) . ?
C1 C2 1.417(8) . ?
C3 C2 1.403(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N5 C1 104.1(4) . . ?
N5 N4 H4 123.9 . . ?
N5 N4 C3 112.2(4) . . ?
C3 N4 H4 123.9 . . ?
O2 N1 C1 116.5(5) . . ?
O1 N1 O2 124.4(5) . . ?
O1 N1 C1 119.1(5) . . ?
O4 N3 C3 118.8(4) . . ?
O3 N3 O4 123.3(5) . . ?
O3 N3 C3 117.9(4) . . ?
C2 N2 H2 116.9 . . ?
C2 N2 C4 126.2(5) . . ?
C4 N2 H2 116.9 . . ?
N5 C1 N1 117.9(5) . . ?
N5 C1 C2 115.1(5) . . ?
C2 C1 N1 126.9(5) . . ?
N4 C3 N3 117.7(5) . . ?
N4 C3 C2 108.5(5) . . ?
N3 C3 C2 133.2(5) . . ?
N2 C2 C1 127.0(5) . . ?
N2 C2 C3 133.1(5) . . ?
C3 C2 C1 99.9(5) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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

data_dlj003_0m
_database_code_depnum_ccdc_archive 'CCDC 2152132'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 N8 O9'
_chemical_formula_sum            'C4 N8 O9'
_chemical_formula_weight         304.12
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4799(7)
_cell_length_b                   11.5935(9)
_cell_length_c                   10.6812(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.431(3)
_cell_angle_gamma                90
_cell_volume                     1048.20(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2752
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.203
_cell_measurement_theta_min      2.595
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1080 before and 0.0517 after correction. The Ratio of minimum to maximum transmission is 0.9018. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10845
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.448
_diffrn_reflns_theta_min         2.595
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1543
_reflns_number_total             2151
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+0.8993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.4398(2) 0.44469(15) 0.87363(17) 0.0292(4) Uani 1 1 d . . . . .
O2 O 0.8403(2) 0.77159(17) 0.7634(2) 0.0385(5) Uani 1 1 d . . . . .
O4 O 0.3848(2) 0.36316(17) 0.6030(2) 0.0398(5) Uani 1 1 d . . . . .
O6 O 0.1480(3) 0.60227(18) 0.8350(2) 0.0413(5) Uani 1 1 d . . . . .
N5 N 0.4056(2) 0.57484(18) 0.7073(2) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.7429(3) 0.59210(18) 0.9125(2) 0.0250(5) Uani 1 1 d . . . . .
N4 N 0.4780(3) 0.66981(18) 0.6561(2) 0.0253(5) Uani 1 1 d . . . . .
O9 O 0.2807(3) 0.5341(2) 0.4368(2) 0.0457(6) Uani 1 1 d . . . . .
O1 O 0.6730(3) 0.84826(19) 0.6267(2) 0.0516(6) Uani 1 1 d . . . . .
O8 O 0.1667(3) 0.6809(2) 0.5210(2) 0.0518(6) Uani 1 1 d . . . . .
N1 N 0.7138(3) 0.77478(19) 0.7029(2) 0.0286(5) Uani 1 1 d . . . . .
O7 O -0.0101(2) 0.5510(2) 0.6771(2) 0.0549(7) Uani 1 1 d . . . . .
N6 N 0.2644(3) 0.40139(19) 0.6404(2) 0.0308(5) Uani 1 1 d . . . . .
N8 N 0.2316(3) 0.5882(2) 0.5231(2) 0.0336(6) Uani 1 1 d . . . . .
N7 N 0.1192(3) 0.5662(2) 0.7300(2) 0.0342(6) Uani 1 1 d . . . . .
N3 N 0.8416(3) 0.5847(2) 0.9848(2) 0.0326(6) Uani 1 1 d . . . . .
O5 O 0.1479(3) 0.34990(19) 0.6678(3) 0.0566(7) Uani 1 1 d . . . . .
C1 C 0.6048(3) 0.6822(2) 0.7271(2) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.6230(3) 0.6002(2) 0.8252(2) 0.0234(6) Uani 1 1 d . . . . .
C3 C 0.4866(3) 0.5256(2) 0.8162(2) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.2620(3) 0.5356(2) 0.6547(2) 0.0251(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C3 1.201(3) . ?
O2 N1 1.219(3) . ?
O4 N6 1.203(3) . ?
O6 N7 1.208(3) . ?
N5 N4 1.389(3) . ?
N5 C3 1.433(3) . ?
N5 C4 1.387(3) . ?
N2 N3 1.108(3) . ?
N2 C2 1.341(3) . ?
N4 C1 1.287(3) . ?
O9 N8 1.209(3) . ?
O1 N1 1.214(3) . ?
O8 N8 1.206(3) . ?
N1 C1 1.450(3) . ?
O7 N7 1.216(3) . ?
N6 O5 1.205(3) . ?
N6 C4 1.563(3) . ?
N8 C4 1.540(4) . ?
N7 C4 1.535(3) . ?
C1 C2 1.417(4) . ?
C2 C3 1.443(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
N4 N5 C3 115.7(2) . . ?
C4 N5 N4 119.9(2) . . ?
C4 N5 C3 124.4(2) . . ?
N3 N2 C2 179.5(3) . . ?
C1 N4 N5 103.3(2) . . ?
O2 N1 C1 115.6(2) . . ?
O1 N1 O2 125.7(2) . . ?
O1 N1 C1 118.6(2) . . ?
O4 N6 O5 128.5(3) . . ?
O4 N6 C4 114.5(2) . . ?
O5 N6 C4 117.0(2) . . ?
O9 N8 C4 116.4(2) . . ?
O8 N8 O9 128.7(3) . . ?
O8 N8 C4 114.9(2) . . ?
O6 N7 O7 127.4(3) . . ?
O6 N7 C4 116.4(2) . . ?
O7 N7 C4 116.2(2) . . ?
N4 C1 N1 119.8(2) . . ?
N4 C1 C2 114.3(2) . . ?
C2 C1 N1 125.9(2) . . ?
N2 C2 C1 127.3(2) . . ?
N2 C2 C3 125.2(2) . . ?
C1 C2 C3 107.5(2) . . ?
O3 C3 N5 124.7(2) . . ?
O3 C3 C2 136.2(3) . . ?
N5 C3 C2 99.2(2) . . ?
N5 C4 N6 110.5(2) . . ?
N5 C4 N8 109.6(2) . . ?
N5 C4 N7 114.4(2) . . ?
N8 C4 N6 107.9(2) . . ?
N7 C4 N6 107.2(2) . . ?
N7 C4 N8 107.0(2) . . ?

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

data_dlj002_0m
_database_code_depnum_ccdc_archive 'CCDC 2152133'
loop_
_audit_author_name
_audit_author_address
'Yuangang Xu'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-02-15 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N9 O12'
_chemical_formula_sum            'C5 H3 N9 O12'
_chemical_formula_weight         381.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.2349(6)
_cell_length_b                   19.5174(18)
_cell_length_c                   21.975(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.445
_cell_measurement_theta_min      2.284
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.0452
_exptl_absorpt_correction_T_min  0.0245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0761 before and 0.0492 after correction. The Ratio of minimum to maximum transmission is 0.5420. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11892
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.382
_diffrn_reflns_theta_min         2.087
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE '
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1507
_reflns_number_total             2702
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2702
_refine_ls_number_restraints     243
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+3.7423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Others
 Fixed Sof: O8(0.5) O9(0.5)
5.a Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.6469(5) 0.72999(14) 0.73647(11) 0.0428(7) Uani 1 1 d . U . . .
O2 O 0.0352(5) 0.74432(15) 0.63050(13) 0.0498(8) Uani 1 1 d . U . . .
O3 O 0.2280(5) 0.76633(16) 0.51430(13) 0.0531(8) Uani 1 1 d . U . . .
O1 O 0.0986(5) 0.84887(14) 0.66011(14) 0.0540(8) Uani 1 1 d . U . . .
N1 N 0.3717(5) 0.78050(14) 0.64072(13) 0.0333(7) Uani 1 1 d . U . . .
N2 N 0.1555(6) 0.79184(17) 0.64343(14) 0.0389(8) Uani 1 1 d . U . . .
N6 N 0.6764(6) 0.67776(16) 0.70768(15) 0.0397(8) Uani 1 1 d . U . . .
N5 N 0.5862(6) 0.61270(15) 0.61551(14) 0.0398(8) Uani 1 1 d . U . . .
N8 N 0.6171(7) 0.51099(17) 0.68123(16) 0.0459(9) Uani 1 1 d . U . . .
N4 N 0.4714(6) 0.61923(16) 0.56339(14) 0.0461(9) Uani 1 1 d . U . . .
N3 N 0.2663(7) 0.7053(2) 0.51542(15) 0.0507(10) Uani 1 1 d . U . . .
O7 O 0.4690(7) 0.53522(16) 0.70664(16) 0.0754(12) Uani 1 1 d . U . . .
O11 O 0.7078(6) 0.45802(15) 0.69257(19) 0.0810(12) Uani 1 1 d . U . . .
O13 O 0.4862(8) 0.46906(17) 0.57489(15) 0.0815(13) Uani 1 1 d . U . . .
C2 C 0.4378(6) 0.71585(17) 0.62133(15) 0.0302(8) Uani 1 1 d . U . . .
C3 C 0.5674(6) 0.67066(17) 0.65105(16) 0.0324(8) Uani 1 1 d . U . . .
O6 O 0.7944(7) 0.63154(16) 0.72303(19) 0.0921(15) Uani 1 1 d . U . . .
N9 N 0.6504(8) 0.50140(19) 0.57071(19) 0.0626(12) Uani 1 1 d . U . . .
C1 C 0.3880(7) 0.68020(19) 0.56717(16) 0.0378(9) Uani 1 1 d . U . . .
O4 O 0.2166(8) 0.66493(19) 0.47614(15) 0.0973(16) Uani 1 1 d . U . . .
O12 O 0.7817(8) 0.5016(2) 0.53072(18) 0.0955(15) Uani 1 1 d . U . . .
C4 C 0.5137(7) 0.83808(18) 0.65413(18) 0.0406(10) Uani 1 1 d . U . . .
H4A H 0.473698 0.877398 0.628817 0.061 Uiso 1 1 calc GR . . . .
H4B H 0.662330 0.825010 0.645375 0.061 Uiso 1 1 calc GR . . . .
H4C H 0.500495 0.850469 0.697182 0.061 Uiso 1 1 calc GR . . . .
O10 O 1.0503(6) 0.5153(2) 0.6438(2) 0.1064(16) Uani 1 1 d . U . . .
C5 C 0.6970(7) 0.55013(19) 0.6252(2) 0.0464(10) Uani 1 1 d . U . . .
N7 N 0.9393(8) 0.5604(2) 0.6259(3) 0.0987(19) Uani 1 1 d . U . . .
O8 O 1.0231(14) 0.6134(4) 0.6340(6) 0.113(4) Uani 0.5 1 d . U P A 1
O9 O 0.9716(11) 0.6117(4) 0.5798(4) 0.0596(18) Uani 0.5 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N6 1.214(4) . ?
O2 N2 1.226(4) . ?
O3 N3 1.215(4) . ?
O1 N2 1.224(4) . ?
N1 N2 1.367(5) . ?
N1 C2 1.394(4) . ?
N1 C4 1.461(5) . ?
N6 C3 1.425(5) . ?
N6 O6 1.212(4) . ?
N5 N4 1.356(5) . ?
N5 C3 1.380(4) . ?
N5 C5 1.419(5) . ?
N8 O7 1.178(5) . ?
N8 O11 1.205(4) . ?
N8 C5 1.532(6) . ?
N4 C1 1.301(5) . ?
N3 C1 1.452(5) . ?
N3 O4 1.209(4) . ?
O13 N9 1.206(6) . ?
C2 C3 1.363(5) . ?
C2 C1 1.413(5) . ?
N9 O12 1.201(5) . ?
N9 C5 1.557(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
O10 N7 1.188(6) . ?
C5 N7 1.524(7) . ?
N7 O8 1.171(8) . ?
N7 O9 1.440(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C2 116.8(3) . . ?
N2 N1 C4 117.7(3) . . ?
C2 N1 C4 125.4(3) . . ?
O2 N2 N1 118.1(3) . . ?
O1 N2 O2 125.4(4) . . ?
O1 N2 N1 116.5(3) . . ?
O5 N6 C3 117.7(3) . . ?
O6 N6 O5 124.9(3) . . ?
O6 N6 C3 117.4(3) . . ?
N4 N5 C3 110.9(3) . . ?
N4 N5 C5 117.7(3) . . ?
C3 N5 C5 131.4(4) . . ?
O7 N8 O11 127.9(4) . . ?
O7 N8 C5 115.8(3) . . ?
O11 N8 C5 116.2(4) . . ?
C1 N4 N5 104.1(3) . . ?
O3 N3 C1 116.7(3) . . ?
O4 N3 O3 125.0(4) . . ?
O4 N3 C1 118.3(4) . . ?
N1 C2 C1 129.6(3) . . ?
C3 C2 N1 127.9(3) . . ?
C3 C2 C1 102.4(3) . . ?
N5 C3 N6 122.3(3) . . ?
C2 C3 N6 129.7(3) . . ?
C2 C3 N5 108.0(3) . . ?
O13 N9 C5 114.8(4) . . ?
O12 N9 O13 129.5(5) . . ?
O12 N9 C5 115.7(5) . . ?
N4 C1 N3 117.8(3) . . ?
N4 C1 C2 114.6(4) . . ?
C2 C1 N3 127.5(4) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 N8 113.1(3) . . ?
N5 C5 N9 108.6(4) . . ?
N5 C5 N7 111.8(4) . . ?
N8 C5 N9 104.7(3) . . ?
N7 C5 N8 112.3(4) . . ?
N7 C5 N9 105.8(4) . . ?
O10 N7 C5 118.9(4) . . ?
O10 N7 O9 131.9(6) . . ?
O8 N7 O10 110.1(8) . . ?
O8 N7 C5 124.0(6) . . ?
O9 N7 C5 102.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
