# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22019414_0m
_database_code_depnum_ccdc_archive 'CCDC 1960094'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_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         'C8 H3 N9 O7, C3 H6 O'
_chemical_formula_sum            'C11 H9 N9 O8'
_chemical_formula_weight         395.27
_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                   13.6229(4)
_cell_length_b                   5.9755(2)
_cell_length_c                   19.6403(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.4370(10)
_cell_angle_gamma                90
_cell_volume                     1577.15(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6196
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.453
_cell_measurement_theta_min      2.787
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1458 before and 0.0759 after correction. The Ratio of minimum to maximum transmission is 0.5653. 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    1.665
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.19
_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  0.0781
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18206
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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                2780
_reflns_number_total             3629
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.046
_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)+(0.0436P)²+1.0797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7A)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.67431(10) 0.3789(2) 0.69605(6) 0.0167(3) Uani 1 1 d . . . . .
O8 O 0.78041(10) 0.6070(2) 0.59154(7) 0.0195(3) Uani 1 1 d . . . . .
O6 O 0.37635(11) 1.2551(2) 0.64134(7) 0.0242(3) Uani 1 1 d . . . . .
O4 O 1.06057(11) -0.2422(2) 0.84434(7) 0.0266(3) Uani 1 1 d . . . . .
O3 O 0.98001(11) -0.0472(3) 0.90997(7) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.92333(12) 0.3770(2) 0.85868(8) 0.0310(4) Uani 1 1 d . . . . .
O7 O 0.36492(12) 1.1166(3) 0.53756(7) 0.0293(4) Uani 1 1 d . . . . .
O1 O 0.76211(12) 0.3750(3) 0.83400(8) 0.0358(4) Uani 1 1 d . . . . .
N3 N 0.90054(12) -0.2159(3) 0.74352(8) 0.0180(3) Uani 1 1 d . . . . .
N4 N 0.82427(12) -0.1288(3) 0.69987(8) 0.0173(3) Uani 1 1 d . . . . .
N6 N 0.60273(12) 0.2817(3) 0.59046(8) 0.0182(3) Uani 1 1 d . . . . .
N9 N 0.39454(12) 1.1121(3) 0.59977(8) 0.0200(4) Uani 1 1 d . . . . .
N5 N 0.67416(12) 0.1196(3) 0.61561(8) 0.0184(3) Uani 1 1 d . . . . .
N7 N 0.54761(13) 0.7399(3) 0.70119(9) 0.0214(4) Uani 1 1 d . . . . .
N8 N 0.49038(13) 0.9215(3) 0.69357(8) 0.0225(4) Uani 1 1 d . . . . .
N1 N 0.99115(12) -0.1240(3) 0.85387(8) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.84471(14) 0.3000(3) 0.82942(8) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.60680(14) 0.4289(3) 0.63912(9) 0.0161(4) Uani 1 1 d . . . . .
C1 C 0.91526(14) -0.0725(3) 0.79545(9) 0.0164(4) Uani 1 1 d . . . . .
C3 C 0.78989(14) 0.0647(3) 0.72245(9) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.71281(14) 0.1840(3) 0.67697(9) 0.0163(4) Uani 1 1 d . . . . .
C8 C 0.45696(14) 0.9263(3) 0.62633(9) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.54928(14) 0.6311(3) 0.64065(9) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.84792(14) 0.1062(3) 0.78601(9) 0.0168(4) Uani 1 1 d . . . . .
C9 C 0.80731(14) 0.6219(3) 0.53508(9) 0.0180(4) Uani 1 1 d . . . . .
C11 C 0.78747(16) 0.4350(3) 0.48417(10) 0.0220(4) Uani 1 1 d . . . . .
H11A H 0.850609 0.365998 0.477815 0.033 Uiso 1 1 calc GR . . . .
H11B H 0.753580 0.493686 0.439903 0.033 Uiso 1 1 calc GR . . . .
H11C H 0.745207 0.322604 0.501378 0.033 Uiso 1 1 calc GR . . . .
C7 C 0.49070(14) 0.7515(3) 0.58950(10) 0.0183(4) Uani 1 1 d . . . . .
H7A H 0.476882 0.722401 0.541321 0.022 Uiso 1 1 calc R . . . .
C10 C 0.86276(16) 0.8228(3) 0.51632(10) 0.0236(4) Uani 1 1 d . . . . .
H10A H 0.858460 0.942677 0.549757 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.833423 0.874000 0.470038 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.932710 0.783336 0.516872 0.035 Uiso 1 1 calc GR . . . .
H7 H 0.571(2) 0.696(5) 0.7414(14) 0.042(8) Uiso 1 1 d . . . . .
H4 H 0.805(2) -0.200(5) 0.6598(14) 0.042(7) Uiso 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
O5 C5 1.359(2) . ?
O5 C4 1.355(2) . ?
O8 C9 1.227(2) . ?
O6 N9 1.235(2) . ?
O4 N1 1.219(2) . ?
O3 N1 1.226(2) . ?
O2 N2 1.220(2) . ?
O7 N9 1.222(2) . ?
O1 N2 1.228(2) . ?
N3 N4 1.339(2) . ?
N3 C1 1.322(2) . ?
N4 C3 1.349(2) . ?
N4 H4 0.89(3) . ?
N6 N5 1.404(2) . ?
N6 C5 1.293(2) . ?
N9 C8 1.443(2) . ?
N5 C4 1.292(2) . ?
N7 N8 1.330(2) . ?
N7 C6 1.359(2) . ?
N7 H7 0.85(3) . ?
N8 C8 1.325(2) . ?
N1 C1 1.446(2) . ?
N2 C2 1.443(2) . ?
C5 C6 1.443(3) . ?
C1 C2 1.400(3) . ?
C3 C4 1.449(3) . ?
C3 C2 1.386(3) . ?
C8 C7 1.391(3) . ?
C6 C7 1.379(3) . ?
C9 C11 1.494(3) . ?
C9 C10 1.496(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C7 H7A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C4 O5 C5 101.64(14) . . ?
C1 N3 N4 104.22(15) . . ?
N3 N4 C3 113.41(16) . . ?
N3 N4 H4 117.4(18) . . ?
C3 N4 H4 129.1(18) . . ?
C5 N6 N5 105.43(15) . . ?
O6 N9 C8 117.62(16) . . ?
O7 N9 O6 125.18(17) . . ?
O7 N9 C8 117.20(16) . . ?
C4 N5 N6 105.98(15) . . ?
N8 N7 C6 112.69(16) . . ?
N8 N7 H7 119.1(19) . . ?
C6 N7 H7 127.6(19) . . ?
C8 N8 N7 103.24(15) . . ?
O4 N1 O3 124.64(16) . . ?
O4 N1 C1 118.23(15) . . ?
O3 N1 C1 117.12(16) . . ?
O2 N2 O1 124.88(17) . . ?
O2 N2 C2 118.17(17) . . ?
O1 N2 C2 116.95(17) . . ?
O5 C5 C6 117.61(16) . . ?
N6 C5 O5 113.54(16) . . ?
N6 C5 C6 128.84(17) . . ?
N3 C1 N1 118.21(16) . . ?
N3 C1 C2 112.27(16) . . ?
C2 C1 N1 129.42(16) . . ?
N4 C3 C4 118.30(16) . . ?
N4 C3 C2 105.77(16) . . ?
C2 C3 C4 135.70(17) . . ?
O5 C4 C3 121.75(16) . . ?
N5 C4 O5 113.39(16) . . ?
N5 C4 C3 124.86(17) . . ?
N8 C8 N9 117.58(16) . . ?
N8 C8 C7 114.42(17) . . ?
C7 C8 N9 127.96(17) . . ?
N7 C6 C5 120.40(17) . . ?
N7 C6 C7 107.28(17) . . ?
C7 C6 C5 132.31(17) . . ?
C1 C2 N2 128.06(17) . . ?
C3 C2 N2 127.42(17) . . ?
C3 C2 C1 104.32(16) . . ?
O8 C9 C11 120.17(18) . . ?
O8 C9 C10 121.24(17) . . ?
C11 C9 C10 118.57(17) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C7 H7A 128.8 . . ?
C6 C7 C8 102.36(16) . . ?
C6 C7 H7A 128.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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_22019259_0m
_database_code_depnum_ccdc_archive 'CCDC 1960098'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-20
_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         '2(C2 H6 O S), C10 H4 N10 O6'
_chemical_formula_sum            'C14 H16 N10 O8 S2'
_chemical_formula_weight         516.49
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.5043(3)
_cell_length_b                   8.5821(4)
_cell_length_c                   10.4247(4)
_cell_angle_alpha                67.980(2)
_cell_angle_beta                 87.727(2)
_cell_angle_gamma                84.1360(10)
_cell_volume                     536.64(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4550
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.488
_cell_measurement_theta_min      3.148
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1455 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.9202. 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    1.598
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6598
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.648
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.982
_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                2130
_reflns_number_total             2431
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.044
_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)+(0.0241P)²+0.4342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0797
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S01 S 1.06132(6) 0.92076(5) 0.70588(4) 0.01773(12) Uani 1 1 d . . . . .
O3 O 0.20183(16) 0.45745(13) 0.62665(11) 0.0161(2) Uani 1 1 d . . . . .
O4 O 1.11482(17) 0.73080(14) 0.77967(12) 0.0189(3) Uani 1 1 d . . . . .
O2 O 0.20138(17) 0.32598(16) 0.90801(12) 0.0232(3) Uani 1 1 d . . . . .
O1 O 0.4534(2) 0.18420(18) 1.04507(14) 0.0384(4) Uani 1 1 d . . . . .
N3 N 0.6712(2) 0.61468(17) 0.68090(14) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.3847(2) 0.29896(18) 0.94008(14) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.7926(2) 0.55426(18) 0.79484(14) 0.0177(3) Uani 1 1 d . . . . .
N4 N 0.3281(2) 0.69731(17) 0.49735(14) 0.0189(3) Uani 1 1 d . . . . .
N5 N 0.1533(2) 0.68008(17) 0.43101(14) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.0878(2) 0.5390(2) 0.51031(16) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.3479(2) 0.5658(2) 0.61107(16) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.5061(2) 0.5276(2) 0.71624(16) 0.0160(3) Uani 1 1 d . . . . .
C1 C 0.7138(2) 0.4317(2) 0.90018(17) 0.0183(3) Uani 1 1 d . . . . .
H1 H 0.773695 0.371572 0.988858 0.022 Uiso 1 1 calc R . . . .
C7 C 1.0414(3) 1.0017(2) 0.84052(17) 0.0237(4) Uani 1 1 d . . . . .
H7A H 0.921352 0.960529 0.898661 0.036 Uiso 1 1 calc GR . . . .
H7B H 1.024979 1.125320 0.800026 0.036 Uiso 1 1 calc GR . . . .
H7C H 1.167042 0.963677 0.897025 0.036 Uiso 1 1 calc GR . . . .
C2 C 0.5269(2) 0.4104(2) 0.85366(16) 0.0170(3) Uani 1 1 d . . . . .
C6 C 1.2975(3) 1.0019(2) 0.63067(19) 0.0252(4) Uani 1 1 d . . . . .
H6A H 1.404713 0.965657 0.702045 0.038 Uiso 1 1 calc GR . . . .
H6B H 1.277616 1.125487 0.590817 0.038 Uiso 1 1 calc GR . . . .
H6C H 1.339967 0.959128 0.557763 0.038 Uiso 1 1 calc GR . . . .
H2 H 0.912(4) 0.605(3) 0.792(2) 0.038(6) Uiso 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
S01 O4 1.5282(11) . ?
S01 C7 1.7796(17) . ?
S01 C6 1.7810(18) . ?
O3 C5 1.3562(17) . ?
O3 C4 1.3598(18) . ?
O2 N1 1.2268(17) . ?
O1 N1 1.2281(18) . ?
N3 N2 1.3534(18) . ?
N3 C3 1.332(2) . ?
N1 C2 1.432(2) . ?
N2 C1 1.332(2) . ?
N2 H2 0.92(2) . ?
N4 N5 1.4024(18) . ?
N4 C4 1.294(2) . ?
N5 C5 1.287(2) . ?
C5 C5 1.444(3) 2_566 ?
C4 C3 1.455(2) . ?
C3 C2 1.410(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
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
O4 S01 C7 104.77(7) . . ?
O4 S01 C6 105.31(8) . . ?
C7 S01 C6 98.42(9) . . ?
C5 O3 C4 101.43(12) . . ?
C3 N3 N2 105.10(13) . . ?
O2 N1 O1 123.69(14) . . ?
O2 N1 C2 118.67(13) . . ?
O1 N1 C2 117.60(13) . . ?
N3 N2 H2 117.9(14) . . ?
C1 N2 N3 113.39(13) . . ?
C1 N2 H2 128.6(14) . . ?
C4 N4 N5 106.01(13) . . ?
C5 N5 N4 105.44(12) . . ?
O3 C5 C5 117.93(17) . 2_566 ?
N5 C5 O3 114.00(13) . . ?
N5 C5 C5 128.08(18) . 2_566 ?
O3 C4 C3 120.26(13) . . ?
N4 C4 O3 113.11(13) . . ?
N4 C4 C3 126.63(14) . . ?
N3 C3 C4 117.08(14) . . ?
N3 C3 C2 109.74(13) . . ?
C2 C3 C4 133.17(15) . . ?
N2 C1 H1 127.2 . . ?
N2 C1 C2 105.65(14) . . ?
C2 C1 H1 127.2 . . ?
S01 C7 H7A 109.5 . . ?
S01 C7 H7B 109.5 . . ?
S01 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C2 N1 130.36(14) . . ?
C1 C2 N1 123.29(14) . . ?
C1 C2 C3 106.11(14) . . ?
S01 C6 H6A 109.5 . . ?
S01 C6 H6B 109.5 . . ?
S01 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_ff
_database_code_depnum_ccdc_archive 'CCDC 1960097'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_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         'C10 H2 N12 O10'
_chemical_formula_sum            'C10 H2 N12 O10'
_chemical_formula_weight         450.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   12.6220(4)
_cell_length_b                   5.8838(2)
_cell_length_c                   11.1302(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.7500(10)
_cell_angle_gamma                90
_cell_volume                     787.24(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.345
_cell_measurement_theta_min      3.389
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.745370
_exptl_absorpt_correction_T_min  0.670623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 17104 reflections, Rint = 0.0348
 (11791 with I > 3sig(I), Rint = 0.0325)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.374
_diffrn_reflns_theta_min         3.389
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_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                1441
_reflns_number_total             1600
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.040
_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)+(0.0322P)²+0.4703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0754
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_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 0.61460(7) 0.55082(16) 0.14116(8) 0.0140(2) Uani 1 1 d . . . . .
O4 O 0.83222(8) 0.07854(17) 0.65169(9) 0.0208(2) Uani 1 1 d . . . . .
O3 O 0.97277(8) 0.31421(17) 0.70648(9) 0.0193(2) Uani 1 1 d . . . . .
O1 O 0.88934(8) 0.99346(17) 0.40071(9) 0.0202(2) Uani 1 1 d . . . . .
O2 O 0.74065(9) 0.92513(17) 0.24381(9) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.73726(9) 0.3218(2) 0.44944(10) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.82955(9) 0.3941(2) 0.53787(10) 0.0145(2) Uani 1 1 d . . . . .
N6 N 0.80908(9) 0.8749(2) 0.34439(11) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.88269(9) 0.2470(2) 0.64182(10) 0.0156(3) Uani 1 1 d . . . . .
N4 N 0.53624(9) 0.3212(2) 0.24698(10) 0.0173(3) Uani 1 1 d . . . . .
N5 N 0.46792(9) 0.3305(2) 0.12178(10) 0.0176(3) Uani 1 1 d . . . . .
C4 C 0.61966(11) 0.4523(2) 0.25279(12) 0.0136(3) Uani 1 1 d . . . . .
C5 C 0.51774(10) 0.4658(2) 0.06563(12) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.79726(11) 0.6619(2) 0.40260(12) 0.0139(3) Uani 1 1 d . . . . .
C1 C 0.71582(10) 0.4870(2) 0.36420(12) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.86992(11) 0.5963(2) 0.51527(12) 0.0148(3) Uani 1 1 d . . . . .
H3 H 0.933821 0.674614 0.565808 0.018 Uiso 1 1 calc R . . . .


_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 C4 1.3547(15) . ?
O5 C5 1.3509(15) . ?
O4 N3 1.2010(15) . ?
O3 N3 1.2118(15) . ?
O1 N6 1.2325(15) . ?
O2 N6 1.2236(15) . ?
N1 N2 1.3446(15) . ?
N1 C1 1.3272(17) . ?
N2 N3 1.4370(15) . ?
N2 C3 1.3478(17) . ?
N6 C2 1.4389(17) . ?
N4 N5 1.3984(15) . ?
N4 C4 1.2907(17) . ?
N5 C5 1.2882(18) . ?
C4 C1 1.4610(17) . ?
C5 C5 1.448(3) 3_665 ?
C2 C1 1.4253(18) . ?
C2 C3 1.3644(18) . ?
C3 H3 0.9500 . ?

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
C5 O5 C4 101.12(10) . . ?
C1 N1 N2 103.52(11) . . ?
N1 N2 N3 119.08(11) . . ?
N1 N2 C3 115.81(11) . . ?
C3 N2 N3 124.89(11) . . ?
O1 N6 C2 116.48(11) . . ?
O2 N6 O1 124.75(12) . . ?
O2 N6 C2 118.76(11) . . ?
O4 N3 O3 130.01(12) . . ?
O4 N3 N2 116.13(11) . . ?
O3 N3 N2 113.86(11) . . ?
C4 N4 N5 105.81(11) . . ?
C5 N5 N4 105.28(11) . . ?
O5 C4 C1 120.88(11) . . ?
N4 C4 O5 113.58(11) . . ?
N4 C4 C1 125.44(12) . . ?
O5 C5 C5 117.88(14) . 3_665 ?
N5 C5 O5 114.20(11) . . ?
N5 C5 C5 127.91(15) . 3_665 ?
C1 C2 N6 131.16(12) . . ?
C3 C2 N6 121.82(12) . . ?
C3 C2 C1 107.01(12) . . ?
N1 C1 C4 116.11(12) . . ?
N1 C1 C2 110.08(11) . . ?
C2 C1 C4 133.78(12) . . ?
N2 C3 C2 103.58(11) . . ?
N2 C3 H3 128.2 . . ?
C2 C3 H3 128.2 . . ?

_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_22019094_0m
_database_code_depnum_ccdc_archive 'CCDC 1960096'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_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         'C8 H4 N8 O5, H2 O'
_chemical_formula_sum            'C8 H6 N8 O6'
_chemical_formula_weight         310.21
_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                   13.9157(11)
_cell_length_b                   8.6591(7)
_cell_length_c                   18.9441(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2282.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.258
_cell_measurement_theta_min      2.601
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1576 before and 0.0945 after correction. The Ratio of minimum to maximum transmission is 0.8574. 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    1.805
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14525
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.601
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART'
_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                1380
_reflns_number_total             2019
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2019
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.066
_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)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1220
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N8-H8 = N5-H5
 0.84 with sigma of 0.02
3.a Free rotating group:
 O6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.64514(13) 0.5329(2) 0.59914(10) 0.0180(5) Uani 1 1 d . . . . .
O6 O 0.55507(14) 0.0047(3) 0.84191(11) 0.0266(6) Uani 1 1 d . . . . .
H6A H 0.543527 0.051915 0.881549 0.040 Uiso 1 1 d G . . . .
H6B H 0.504693 -0.048201 0.829399 0.040 Uiso 1 1 d G . . . .
O5 O 0.67457(14) 1.0253(2) 0.39085(11) 0.0250(5) Uani 1 1 d . . . . .
O4 O 0.77246(14) 0.8729(2) 0.44720(11) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.91753(14) 0.1792(2) 0.76971(11) 0.0260(5) Uani 1 1 d . . . . .
O1 O 0.92531(13) 0.3537(2) 0.68747(12) 0.0268(6) Uani 1 1 d . . . . .
N3 N 0.80345(16) 0.5369(3) 0.60167(12) 0.0189(6) Uani 1 1 d . . . . .
N5 N 0.62972(18) 0.2196(3) 0.75095(13) 0.0197(6) Uani 1 1 d D . . . .
N2 N 0.77112(16) 0.6446(3) 0.55108(13) 0.0183(6) Uani 1 1 d . . . . .
N8 N 0.46267(18) 0.7736(3) 0.48032(13) 0.0206(6) Uani 1 1 d D . . . .
N6 N 0.62339(16) 0.3258(3) 0.69970(12) 0.0196(6) Uani 1 1 d . . . . .
N1 N 0.69067(17) 0.9157(3) 0.43078(13) 0.0204(6) Uani 1 1 d . . . . .
N4 N 0.88012(17) 0.2708(3) 0.72795(12) 0.0192(6) Uani 1 1 d . . . . .
N7 N 0.51397(16) 0.6832(3) 0.52444(12) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.71393(19) 0.3628(3) 0.68391(15) 0.0159(7) Uani 1 1 d . . . . .
C4 C 0.67854(19) 0.6378(3) 0.55159(15) 0.0162(7) Uani 1 1 d . . . . .
C5 C 0.72757(19) 0.4759(3) 0.62878(15) 0.0151(6) Uani 1 1 d . . . . .
C2 C 0.61013(19) 0.8359(3) 0.45947(15) 0.0180(7) Uani 1 1 d . . . . .
C7 C 0.77716(19) 0.2765(3) 0.72690(15) 0.0162(7) Uani 1 1 d . . . . .
C3 C 0.60571(19) 0.7191(3) 0.51146(14) 0.0169(7) Uani 1 1 d . . . . .
C1 C 0.5167(2) 0.8662(3) 0.44030(15) 0.0200(7) Uani 1 1 d . . . . .
H1 H 0.495189 0.937894 0.405811 0.024 Uiso 1 1 calc R . . . .
C8 C 0.7198(2) 0.1857(3) 0.76896(15) 0.0184(7) Uani 1 1 d . . . . .
H8A H 0.740236 0.113694 0.803692 0.022 Uiso 1 1 calc R . . . .
H5 H 0.5814(19) 0.173(4) 0.7702(16) 0.042(11) Uiso 1 1 d D . . . .
H8 H 0.4007(13) 0.772(4) 0.4782(15) 0.029(9) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C4 1.361(3) . ?
O3 C5 1.369(3) . ?
O5 N1 1.234(3) . ?
O4 N1 1.237(3) . ?
O2 N4 1.235(3) . ?
O1 N4 1.224(3) . ?
N3 N2 1.411(3) . ?
N3 C5 1.288(3) . ?
N5 N6 1.340(3) . ?
N5 C8 1.332(4) . ?
N2 C4 1.290(3) . ?
N8 N7 1.349(3) . ?
N8 C1 1.336(4) . ?
N6 C6 1.334(3) . ?
N1 C2 1.424(4) . ?
N4 C7 1.434(3) . ?
N7 C3 1.337(4) . ?
C6 C5 1.444(4) . ?
C6 C7 1.413(4) . ?
C4 C3 1.449(4) . ?
C2 C3 1.414(4) . ?
C2 C1 1.374(4) . ?
C7 C8 1.375(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
C4 O3 C5 103.1(2) . . ?
C5 N3 N2 106.3(2) . . ?
C8 N5 N6 113.5(2) . . ?
C4 N2 N3 106.4(2) . . ?
C1 N8 N7 113.7(2) . . ?
C6 N6 N5 105.4(2) . . ?
O5 N1 O4 123.5(2) . . ?
O5 N1 C2 117.6(2) . . ?
O4 N1 C2 118.9(2) . . ?
O2 N4 C7 116.9(2) . . ?
O1 N4 O2 124.1(2) . . ?
O1 N4 C7 119.0(2) . . ?
C3 N7 N8 104.9(2) . . ?
N6 C6 C5 116.7(2) . . ?
N6 C6 C7 109.4(2) . . ?
C7 C6 C5 133.9(3) . . ?
O3 C4 C3 115.6(2) . . ?
N2 C4 O3 112.1(2) . . ?
N2 C4 C3 132.2(3) . . ?
O3 C5 C6 115.5(2) . . ?
N3 C5 O3 112.1(2) . . ?
N3 C5 C6 132.4(3) . . ?
C3 C2 N1 130.3(3) . . ?
C1 C2 N1 123.4(3) . . ?
C1 C2 C3 106.2(2) . . ?
C6 C7 N4 130.4(3) . . ?
C8 C7 N4 123.5(3) . . ?
C8 C7 C6 106.0(2) . . ?
N7 C3 C4 117.3(3) . . ?
N7 C3 C2 109.6(2) . . ?
C2 C3 C4 133.1(3) . . ?
N8 C1 C2 105.6(3) . . ?
N5 C8 C7 105.8(3) . . ?

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

data_22019407_0m
_database_code_depnum_ccdc_archive 'CCDC 1960095'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_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         'C8 H2 N10 O9'
_chemical_formula_sum            'C8 H2 N10 O9'
_chemical_formula_weight         382.20
_chemical_absolute_configuration unk
_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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   17.6045(9)
_cell_length_b                   30.8050(16)
_cell_length_c                   5.0463(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2736.6(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3521
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.451
_cell_measurement_theta_min      2.645
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1358 before and 0.0538 after correction. The Ratio of minimum to maximum transmission is 0.9339. 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    1.855
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8574
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.106
_diffrn_reflns_theta_min         2.645
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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         0.601
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.742
_reflns_number_gt                1306
_reflns_number_total             1614
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1614
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.108
_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)+(0.0644P)²+2.6698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1188
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0(3)
 1(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
;
_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
O3 O 0.250000 0.250000 0.5422(6) 0.0269(7) Uani 1 2 d S T P . .
O4 O 0.58440(13) 0.28583(8) 0.7606(5) 0.0344(6) Uani 1 1 d . . . . .
O5 O 0.59784(13) 0.32097(8) 0.3872(5) 0.0335(6) Uani 1 1 d . . . . .
O1 O 0.24542(14) 0.33674(7) 0.3467(6) 0.0382(6) Uani 1 1 d . . . . .
O2 O 0.32389(16) 0.36054(8) 0.0451(6) 0.0466(7) Uani 1 1 d . . . . .
N3 N 0.48119(14) 0.30389(8) 0.5239(6) 0.0248(6) Uani 1 1 d . . . . .
N2 N 0.43583(14) 0.28091(8) 0.6875(5) 0.0249(6) Uani 1 1 d . . . . .
N5 N 0.28394(15) 0.26215(9) 0.9568(6) 0.0280(6) Uani 1 1 d . . . . .
N4 N 0.56266(14) 0.30322(8) 0.5616(6) 0.0275(6) Uani 1 1 d . . . . .
N1 N 0.30891(16) 0.33966(9) 0.2471(6) 0.0332(7) Uani 1 1 d . . . . .
C3 C 0.36665(17) 0.28975(10) 0.5974(7) 0.0243(6) Uani 1 1 d . . . . .
C4 C 0.30076(17) 0.26801(10) 0.7103(7) 0.0257(6) Uani 1 1 d . . . . .
C2 C 0.37015(17) 0.31866(10) 0.3796(7) 0.0263(7) Uani 1 1 d . . . . .
C1 C 0.44527(19) 0.32671(10) 0.3351(7) 0.0288(7) Uani 1 1 d . . . . .
H1 H 0.467150 0.344410 0.201110 0.035 Uiso 1 1 calc R . . . .


_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 C4 1.351(4) . ?
O3 C4 1.351(4) 14 ?
O4 N4 1.201(4) . ?
O5 N4 1.207(4) . ?
O1 N1 1.229(4) . ?
O2 N1 1.234(4) . ?
N3 N2 1.349(4) . ?
N3 N4 1.447(4) . ?
N3 C1 1.342(4) . ?
N2 C3 1.328(4) . ?
N5 N5 1.410(5) 14 ?
N5 C4 1.291(4) . ?
N1 C2 1.424(4) . ?
C3 C4 1.456(4) . ?
C3 C2 1.416(5) . ?
C2 C1 1.364(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
C4 O3 C4 102.2(3) . 14 ?
N2 N3 N4 119.9(2) . . ?
C1 N3 N2 115.5(2) . . ?
C1 N3 N4 124.6(3) . . ?
C3 N2 N3 103.0(2) . . ?
C4 N5 N5 105.58(18) . 14 ?
O4 N4 O5 130.4(3) . . ?
O4 N4 N3 115.6(2) . . ?
O5 N4 N3 114.0(3) . . ?
O1 N1 O2 124.8(3) . . ?
O1 N1 C2 117.6(3) . . ?
O2 N1 C2 117.6(3) . . ?
N2 C3 C4 120.2(3) . . ?
N2 C3 C2 110.8(3) . . ?
C2 C3 C4 128.9(3) . . ?
O3 C4 C3 118.1(3) . . ?
N5 C4 O3 113.3(3) . . ?
N5 C4 C3 128.6(3) . . ?
C3 C2 N1 128.1(3) . . ?
C1 C2 N1 125.0(3) . . ?
C1 C2 C3 106.5(3) . . ?
N3 C1 C2 104.1(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0(3)
2 1(3)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_22019304_0m
_database_code_depnum_ccdc_archive 'CCDC 1960184'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_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 H2 N4 O6, H2 O'
_chemical_formula_sum            'C4 H4 N4 O7'
_chemical_formula_weight         220.11
_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                   8.5490(13)
_cell_length_b                   10.1040(14)
_cell_length_c                   9.1163(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.010(8)
_cell_angle_gamma                90
_cell_volume                     777.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3587
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.061
_cell_measurement_theta_min      2.262
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1268 before and 0.0754 after correction. The Ratio of minimum to maximum transmission is 0.7304. 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    1.880
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8057
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.704
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.852
_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                1257
_reflns_number_total             1545
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.039
_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)+(0.0487P)²+0.7151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O7(H7A)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.52558(18) 0.60632(14) 0.85925(18) 0.0215(4) Uani 1 1 d . . . . .
O5 O 0.51201(17) 0.40599(14) 0.74184(18) 0.0221(4) Uani 1 1 d . . . . .
O2 O 0.03856(17) 0.67281(15) 0.19108(17) 0.0244(4) Uani 1 1 d . . . . .
O4 O 0.31329(19) 0.30981(15) 0.40456(18) 0.0259(4) Uani 1 1 d . . . . .
O3 O 0.17019(19) 0.30817(15) 0.58423(19) 0.0271(4) Uani 1 1 d . . . . .
O1 O 0.02259(18) 0.46938(15) 0.2721(2) 0.0293(4) Uani 1 1 d . . . . .
N3 N 0.24685(19) 0.36367(17) 0.5003(2) 0.0183(4) Uani 1 1 d . . . . .
N1 N 0.3390(2) 0.70402(17) 0.5880(2) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.387815 0.768652 0.641529 0.022 Uiso 1 1 calc R . . . .
O7 O 0.7655(2) 0.51642(18) 1.0163(3) 0.0411(6) Uani 1 1 d . . . . .
H7A H 0.839667 0.569526 1.057617 0.062 Uiso 1 1 d G . . . .
N2 N 0.23623(19) 0.72482(17) 0.4610(2) 0.0187(4) Uani 1 1 d . . . . .
N4 N 0.0756(2) 0.58216(17) 0.2835(2) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.3598(2) 0.5747(2) 0.6251(2) 0.0173(5) Uani 1 1 d . . . . .
C1 C 0.1890(2) 0.6038(2) 0.4175(2) 0.0177(5) Uani 1 1 d . . . . .
C2 C 0.2622(2) 0.5069(2) 0.5149(2) 0.0174(5) Uani 1 1 d . . . . .
C4 C 0.4742(2) 0.5212(2) 0.7502(2) 0.0184(5) Uani 1 1 d . . . . .
H7B H 0.794(4) 0.447(3) 1.054(3) 0.044(9) Uiso 1 1 d . . . . .
H6 H 0.604(4) 0.569(3) 0.915(4) 0.060(10) Uiso 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
O6 C4 1.336(3) . ?
O6 H6 0.86(4) . ?
O5 C4 1.213(3) . ?
O2 N4 1.251(2) . ?
O4 N3 1.239(2) . ?
O3 N3 1.219(2) . ?
O1 N4 1.225(2) . ?
N3 C2 1.458(3) . ?
N1 H1 0.8800 . ?
N1 N2 1.356(2) . ?
N1 C3 1.355(3) . ?
O7 H7A 0.8699 . ?
O7 H7B 0.80(3) . ?
N2 C1 1.329(3) . ?
N4 C1 1.452(3) . ?
C3 C2 1.382(3) . ?
C3 C4 1.484(3) . ?
C1 C2 1.401(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O6 H6 107(2) . . ?
O4 N3 C2 117.10(17) . . ?
O3 N3 O4 126.20(18) . . ?
O3 N3 C2 116.70(18) . . ?
N2 N1 H1 123.1 . . ?
C3 N1 H1 123.1 . . ?
C3 N1 N2 113.85(17) . . ?
H7A O7 H7B 101.6 . . ?
C1 N2 N1 103.79(16) . . ?
O2 N4 C1 121.42(17) . . ?
O1 N4 O2 124.93(18) . . ?
O1 N4 C1 113.65(17) . . ?
N1 C3 C2 104.83(18) . . ?
N1 C3 C4 126.00(19) . . ?
C2 C3 C4 128.97(19) . . ?
N2 C1 N4 121.42(18) . . ?
N2 C1 C2 111.65(19) . . ?
C2 C1 N4 126.92(18) . . ?
C3 C2 N3 126.37(19) . . ?
C3 C2 C1 105.87(18) . . ?
C1 C2 N3 127.67(19) . . ?
O6 C4 C3 115.98(18) . . ?
O5 C4 O6 127.2(2) . . ?
O5 C4 C3 116.81(19) . . ?

_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_220191089_0m
_database_code_depnum_ccdc_archive 'CCDC 1961859'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-10-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H N6 O5), 2(H2 O)'
_chemical_formula_sum            'C10 H6 N12 O12'
_chemical_formula_weight         486.27
_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                   9.3522(3)
_cell_length_b                   11.3926(5)
_cell_length_c                   17.9538(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.4570(10)
_cell_angle_gamma                90
_cell_volume                     1892.10(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4818
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.155
_cell_measurement_theta_min      2.837
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1436 before and 0.0796 after correction. The Ratio of minimum to maximum transmission is 0.8074. 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    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14196
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.202
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  '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                2873
_reflns_number_total             3744
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.471
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.050
_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)+(0.0588P)²+1.8118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.52575(16) 0.43203(14) 0.59205(9) 0.0217(4) Uani 1 1 d . . . . .
O10 O 0.04247(17) 0.36160(14) 0.45880(9) 0.0222(4) Uani 1 1 d . . . . .
O11 O 1.04167(19) 0.49596(16) 0.72441(11) 0.0253(4) Uani 1 1 d . . . . .
O12 O 1.0809(2) 0.21452(18) 0.76655(12) 0.0327(5) Uani 1 1 d . . . . .
N3 N 0.8034(2) 0.36734(19) 0.75107(12) 0.0234(5) Uani 1 1 d . . . . .
O0AA O 0.3529(2) 0.3938(2) 0.71287(13) 0.0466(6) Uani 1 1 d . . . . .
N4 N 0.8046(2) 0.29931(19) 0.81152(12) 0.0266(5) Uani 1 1 d . . . . .
N12 N 0.0786(2) 0.40998(19) 0.57956(12) 0.0265(5) Uani 1 1 d . . . . .
N2 N 0.7463(2) 0.5057(2) 0.61342(12) 0.0276(5) Uani 1 1 d . . . . .
N1 N 0.6829(2) 0.5399(2) 0.54146(12) 0.0267(5) Uani 1 1 d . . . . .
N10 N 0.1518(2) 0.16173(19) 0.38959(12) 0.0282(5) Uani 1 1 d . . . . .
H10 H 0.125264 0.219231 0.357824 0.034 Uiso 1 1 calc R . . . .
O4 O 0.7150(2) 0.1290(2) 0.90140(14) 0.0513(6) Uani 1 1 d . . . . .
N11 N 0.1313(2) 0.29634(19) 0.57281(13) 0.0295(5) Uani 1 1 d . . . . .
O5 O 0.5054(2) 0.2118(2) 0.88450(14) 0.0563(7) Uani 1 1 d . . . . .
N5 N 0.4238(2) 0.3055(2) 0.72965(13) 0.0335(6) Uani 1 1 d . . . . .
O3 O 0.3754(2) 0.2059(2) 0.73090(15) 0.0569(7) Uani 1 1 d . . . . .
N6 N 0.6275(2) 0.1985(2) 0.87047(14) 0.0346(6) Uani 1 1 d . . . . .
O7 O 0.1158(3) 0.0377(2) 0.60765(15) 0.0615(7) Uani 1 1 d . . . . .
N9 N 0.1991(3) 0.0574(2) 0.36919(14) 0.0380(6) Uani 1 1 d . . . . .
C10 C 0.0304(2) 0.4435(2) 0.51190(14) 0.0213(5) Uani 1 1 d . . . . .
C3 C 0.6703(2) 0.3823(2) 0.71172(14) 0.0218(5) Uani 1 1 d . . . . .
C2 C 0.6509(2) 0.4435(2) 0.64028(14) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.1085(3) 0.2738(2) 0.50167(14) 0.0236(5) Uani 1 1 d . . . . .
C1 C 0.5554(2) 0.4948(2) 0.53235(13) 0.0209(5) Uani 1 1 d . . . . .
O6 O 0.3398(3) -0.0013(2) 0.60102(14) 0.0670(8) Uani 1 1 d . . . . .
N7 N 0.2197(3) 0.0298(2) 0.57436(16) 0.0467(7) Uani 1 1 d . . . . .
C4 C 0.5783(2) 0.3193(2) 0.74974(14) 0.0239(5) Uani 1 1 d . . . . .
C5 C 0.6683(3) 0.2693(2) 0.80998(14) 0.0251(5) Uani 1 1 d . . . . .
C8 C 0.1494(3) 0.1688(2) 0.46442(15) 0.0279(6) Uani 1 1 d . . . . .
C6 C 0.1985(3) 0.0624(2) 0.49482(16) 0.0379(7) Uani 1 1 d . . . . .
O8 O 0.2446(5) -0.1858(3) 0.4850(2) 0.1092(14) Uani 1 1 d . . . . .
C7 C 0.2274(4) -0.0021(3) 0.43270(18) 0.0468(8) Uani 1 1 d . . . . .
O9 O 0.3140(5) -0.1597(3) 0.37424(19) 0.1138(15) Uani 1 1 d . . . . .
N8 N 0.2668(5) -0.1250(3) 0.4299(2) 0.0793(12) Uani 1 1 d . . . . .
H11A H 1.068(3) 0.475(3) 0.682(2) 0.044(10) Uiso 1 1 d . . . . .
H11B H 1.113(4) 0.485(3) 0.754(2) 0.046(10) Uiso 1 1 d . . . . .
H3 H 0.882(3) 0.400(3) 0.7401(18) 0.041(9) Uiso 1 1 d . . . . .
H12A H 1.154(4) 0.201(3) 0.738(2) 0.059(11) Uiso 1 1 d . . . . .
H12B H 1.040(4) 0.146(4) 0.766(2) 0.059(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.356(3) . ?
O1 C1 1.351(3) . ?
O10 C10 1.351(3) . ?
O10 C9 1.354(3) . ?
O11 H11A 0.86(4) . ?
O11 H11B 0.80(4) . ?
O12 H12A 0.92(4) . ?
O12 H12B 0.87(4) . ?
N3 N4 1.332(3) . ?
N3 C3 1.349(3) . ?
N3 H3 0.87(3) . ?
O0AA N5 1.218(3) . ?
N4 C5 1.316(3) . ?
N12 N11 1.397(3) . ?
N12 C10 1.290(3) . ?
N2 N1 1.395(3) . ?
N2 C2 1.287(3) . ?
N1 C1 1.286(3) . ?
N10 H10 0.8800 . ?
N10 N9 1.338(3) . ?
N10 C8 1.349(3) . ?
O4 N6 1.213(3) . ?
N11 C9 1.289(3) . ?
O5 N6 1.214(3) . ?
N5 O3 1.223(3) . ?
N5 C4 1.446(3) . ?
N6 C5 1.448(3) . ?
O7 N7 1.216(4) . ?
N9 C7 1.319(4) . ?
C10 C10 1.445(5) 3_566 ?
C3 C2 1.448(3) . ?
C3 C4 1.376(3) . ?
C9 C8 1.449(4) . ?
C1 C1 1.444(5) 3_666 ?
O6 N7 1.208(4) . ?
N7 C6 1.460(4) . ?
C4 C5 1.391(3) . ?
C8 C6 1.380(4) . ?
C6 C7 1.395(4) . ?
O8 N8 1.249(5) . ?
C7 N8 1.450(4) . ?
O9 N8 1.217(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
C1 O1 C2 101.36(18) . . ?
C10 O10 C9 100.82(19) . . ?
H11A O11 H11B 103(3) . . ?
H12A O12 H12B 102(3) . . ?
N4 N3 C3 113.3(2) . . ?
N4 N3 H3 122(2) . . ?
C3 N3 H3 125(2) . . ?
C5 N4 N3 104.04(19) . . ?
C10 N12 N11 105.8(2) . . ?
C2 N2 N1 106.08(19) . . ?
C1 N1 N2 105.42(19) . . ?
N9 N10 H10 123.8 . . ?
N9 N10 C8 112.3(2) . . ?
C8 N10 H10 123.8 . . ?
C9 N11 N12 105.2(2) . . ?
O0AA N5 O3 125.6(2) . . ?
O0AA N5 C4 117.4(2) . . ?
O3 N5 C4 117.1(2) . . ?
O4 N6 O5 125.3(2) . . ?
O4 N6 C5 118.2(2) . . ?
O5 N6 C5 116.5(2) . . ?
C7 N9 N10 104.6(2) . . ?
O10 C10 C10 118.4(3) . 3_566 ?
N12 C10 O10 113.9(2) . . ?
N12 C10 C10 127.6(3) . 3_566 ?
N3 C3 C2 120.7(2) . . ?
N3 C3 C4 105.7(2) . . ?
C4 C3 C2 133.2(2) . . ?
O1 C2 C3 120.2(2) . . ?
N2 C2 O1 113.2(2) . . ?
N2 C2 C3 126.4(2) . . ?
O10 C9 C8 118.5(2) . . ?
N11 C9 O10 114.3(2) . . ?
N11 C9 C8 127.2(2) . . ?
O1 C1 C1 118.3(3) . 3_666 ?
N1 C1 O1 113.9(2) . . ?
N1 C1 C1 127.8(3) . 3_666 ?
O7 N7 C6 117.3(3) . . ?
O6 N7 O7 126.2(3) . . ?
O6 N7 C6 116.5(3) . . ?
C3 C4 N5 127.4(2) . . ?
C3 C4 C5 104.4(2) . . ?
C5 C4 N5 128.2(2) . . ?
N4 C5 N6 119.4(2) . . ?
N4 C5 C4 112.5(2) . . ?
C4 C5 N6 128.0(2) . . ?
N10 C8 C9 123.5(2) . . ?
N10 C8 C6 106.8(2) . . ?
C6 C8 C9 129.6(3) . . ?
C8 C6 N7 126.8(3) . . ?
C8 C6 C7 103.8(3) . . ?
C7 C6 N7 129.3(3) . . ?
N9 C7 C6 112.5(3) . . ?
N9 C7 N8 119.1(3) . . ?
C6 C7 N8 128.0(3) . . ?
O8 N8 C7 115.8(3) . . ?
O9 N8 O8 126.3(3) . . ?
O9 N8 C7 117.8(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N10 H10 O12 0.88 1.80 2.622(3) 155.4 4_465 yes
O11 H11A N12 0.86(4) 2.00(4) 2.847(3) 166(3) 1_655 yes
O11 H11B N9 0.80(4) 2.15(4) 2.858(3) 146(3) 4_666 yes
N3 H3 O11 0.87(3) 1.91(3) 2.767(3) 170(3) . yes
O12 H12B O11 0.87(4) 1.89(4) 2.756(3) 174(4) 2_746 yes

_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_22019183_0m
_database_code_depnum_ccdc_archive 'CCDC 1960185'
loop_
_audit_author_name
_audit_author_address
'Tingou Yan'
;nanjing university of science and technology
China
;
_audit_update_record             
;
2019-10-18 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-03-01
_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 H3 N3 O4, H2 O'
_chemical_formula_sum            'C4 H5 N3 O5'
_chemical_formula_weight         175.11
_chemical_absolute_configuration unk
_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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   12.792(7)
_cell_length_b                   3.5690(9)
_cell_length_c                   29.664(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1354.3(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3974
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.280
_cell_measurement_theta_min      2.748
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0901 before and 0.0675 after correction. The Ratio of minimum to maximum transmission is 0.8615. 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    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14143
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.747
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2302
_reflns_number_total             3088
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.5888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1371
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(3)
 0(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O2-H2 = O6-H6
 0.84 with sigma of 0.02
 N7-H7
 0.86 with sigma of 0.02
 O8-H8A = O8-H8B = O5-H5A = O5-H5B
 0.85 with sigma of 0.02
 H5B-H5A
 1.4 with sigma of 0.02
 H8A-H8B
 1.4 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.5683(5) 0.0047(12) 0.2653(2) 0.0408(14) Uani 1 1 d . . . . .
O6 O 0.6571(4) 0.0685(13) 0.54819(18) 0.0340(11) Uani 1 1 d D . . . .
O2 O 0.5979(4) 0.4267(13) 0.45094(17) 0.0318(11) Uani 1 1 d D . . . .
O7 O 0.7842(3) 0.3068(12) 0.59019(15) 0.0360(10) Uani 1 1 d . . . . .
O5 O 0.7982(5) 0.0054(15) 0.4881(2) 0.0417(16) Uani 1 1 d D . . . .
N7 N 0.4574(5) 0.4890(12) 0.6391(3) 0.0291(15) Uani 1 1 d D . . . .
O1 O 0.4678(3) 0.1893(13) 0.40953(15) 0.0383(10) Uani 1 1 d . . . . .
N6 N 0.5141(4) 0.3885(15) 0.60206(18) 0.0283(11) Uani 1 1 d . . . . .
O3 O 0.4783(3) 0.3233(13) 0.31480(15) 0.0407(10) Uani 1 1 d . . . . .
O9 O 0.7719(4) 0.1377(13) 0.68388(17) 0.0426(11) Uani 1 1 d . . . . .
O8 O 0.4539(6) 0.4947(14) 0.5111(2) 0.0440(16) Uani 1 1 d D . . . .
N2 N 0.5559(4) 0.1402(15) 0.30301(17) 0.0338(11) Uani 1 1 d . . . . .
N3 N 0.7367(4) 0.0999(14) 0.39679(18) 0.0275(11) Uani 1 1 d . . . . .
N8 N 0.6945(4) 0.3151(14) 0.69639(16) 0.0300(11) Uani 1 1 d . . . . .
O10 O 0.6837(5) 0.4402(16) 0.7342(2) 0.0486(16) Uani 1 1 d . . . . .
N4 N 0.7930(5) -0.0104(12) 0.3613(3) 0.0272(15) Uani 1 1 d . . . . .
C5 C 0.6927(4) 0.2250(15) 0.58457(18) 0.0238(11) Uani 1 1 d . . . . .
C7 C 0.6113(4) 0.3714(16) 0.66471(19) 0.0259(12) Uani 1 1 d . . . . .
C8 C 0.5139(7) 0.4842(14) 0.6772(3) 0.0248(17) Uani 1 1 d . . . . .
H8 H 0.490744 0.546382 0.706701 0.030 Uiso 1 1 calc R . . . .
C6 C 0.6096(4) 0.3145(15) 0.61765(18) 0.0248(11) Uani 1 1 d . . . . .
C4 C 0.7398(7) -0.0177(14) 0.3233(3) 0.0292(19) Uani 1 1 d . . . . .
H4A H 0.764853 -0.084327 0.294204 0.035 Uiso 1 1 calc R . . . .
C2 C 0.6417(4) 0.1690(14) 0.38130(19) 0.0259(11) Uani 1 1 d . . . . .
C3 C 0.6391(5) 0.0932(18) 0.33487(19) 0.0267(12) Uani 1 1 d . . . . .
C1 C 0.5589(4) 0.2621(16) 0.41473(19) 0.0289(12) Uani 1 1 d . . . . .
H6 H 0.702(3) 0.068(15) 0.5273(14) 0.017(14) Uiso 1 1 d D . . . .
H2 H 0.549(12) 0.45(11) 0.470(6) 0.36(15) Uiso 1 1 d D . . . .
H4 H 0.865(5) -0.041(19) 0.371(3) 0.04(2) Uiso 1 1 d . . . . .
H7 H 0.391(3) 0.541(19) 0.637(3) 0.05(3) Uiso 1 1 d D . . . .
H8A H 0.466(8) 0.45(3) 0.5388(14) 0.09(4) Uiso 1 1 d D . . . .
H5A H 0.780(6) 0.041(17) 0.4605(12) 0.03(2) Uiso 1 1 d D . . . .
H5B H 0.830(19) -0.20(4) 0.490(4) 0.36(17) Uiso 1 1 d D . . . .
H8B H 0.398(5) 0.63(3) 0.508(3) 0.09(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 N2 1.228(9) . ?
O6 C5 1.298(8) . ?
O6 H6 0.85(3) . ?
O2 C1 1.322(8) . ?
O2 H2 0.84(3) . ?
O7 C5 1.217(6) . ?
O5 H5A 0.86(3) . ?
O5 H5B 0.85(3) . ?
N7 N6 1.365(9) . ?
N7 C8 1.342(11) . ?
N7 H7 0.87(3) . ?
O1 C1 1.204(7) . ?
N6 C6 1.332(7) . ?
O3 N2 1.239(7) . ?
O9 N8 1.233(6) . ?
O8 H8A 0.85(3) . ?
O8 H8B 0.85(3) . ?
N2 C3 1.433(8) . ?
N3 N4 1.335(9) . ?
N3 C2 1.322(8) . ?
N8 O10 1.216(8) . ?
N8 C7 1.434(7) . ?
N4 C4 1.318(12) . ?
N4 H4 0.97(7) . ?
C5 C6 1.482(7) . ?
C7 C8 1.361(11) . ?
C7 C6 1.411(8) . ?
C8 H8 0.9500 . ?
C4 H4A 0.9500 . ?
C4 C3 1.391(11) . ?
C2 C3 1.404(8) . ?
C2 C1 1.488(7) . ?

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
C5 O6 H6 112(4) . . ?
C1 O2 H2 107(10) . . ?
H5A O5 H5B 110(5) . . ?
N6 N7 H7 121(6) . . ?
C8 N7 N6 112.8(6) . . ?
C8 N7 H7 126(6) . . ?
C6 N6 N7 105.1(5) . . ?
H8A O8 H8B 111(5) . . ?
O4 N2 O3 124.6(5) . . ?
O4 N2 C3 117.2(6) . . ?
O3 N2 C3 118.1(5) . . ?
C2 N3 N4 106.1(5) . . ?
O9 N8 C7 118.1(5) . . ?
O10 N8 O9 123.9(6) . . ?
O10 N8 C7 118.0(5) . . ?
N3 N4 H4 109(5) . . ?
C4 N4 N3 113.8(7) . . ?
C4 N4 H4 137(5) . . ?
O6 C5 C6 113.1(5) . . ?
O7 C5 O6 123.6(5) . . ?
O7 C5 C6 123.2(5) . . ?
C8 C7 N8 122.9(6) . . ?
C8 C7 C6 107.3(6) . . ?
C6 C7 N8 129.8(5) . . ?
N7 C8 C7 105.5(7) . . ?
N7 C8 H8 127.2 . . ?
C7 C8 H8 127.2 . . ?
N6 C6 C5 118.1(5) . . ?
N6 C6 C7 109.2(5) . . ?
C7 C6 C5 132.5(5) . . ?
N4 C4 H4A 127.4 . . ?
N4 C4 C3 105.1(7) . . ?
C3 C4 H4A 127.5 . . ?
N3 C2 C3 109.1(5) . . ?
N3 C2 C1 117.6(5) . . ?
C3 C2 C1 132.8(5) . . ?
C4 C3 N2 123.9(6) . . ?
C4 C3 C2 106.0(6) . . ?
C2 C3 N2 129.9(6) . . ?
O2 C1 C2 111.9(5) . . ?
O1 C1 O2 124.4(5) . . ?
O1 C1 C2 123.7(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 O5 0.85(3) 1.71(3) 2.547(9) 172(5) . yes
O2 H2 O8 0.84(3) 1.73(4) 2.575(8) 176(24) . yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(3)
2 0(3)

