# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2022

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

data_0624z_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2142354'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_audit_creation_date             2022-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C6 H6 N8 O4'
_chemical_formula_sum            'C8 H12 N8 O5 S'
_chemical_formula_weight         332.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   6.973(19)
_cell_length_b                   10.12(3)
_cell_length_c                   11.10(3)
_cell_angle_alpha                70.53(3)
_cell_angle_beta                 79.60(3)
_cell_angle_gamma                75.78(3)
_cell_volume                     711(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    509
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.02
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5101
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.958
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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                1301
_reflns_number_total             2477
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.257
_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)+(0.0550P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2_$1-O2
 3.5 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N8(H8A,H8B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8C,H8D,H8E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
S1 S 0.2410(2) 0.70170(16) -0.06180(12) 0.0542(5) Uani 1 1 d . . . . .
O1 O 0.2119(5) 0.5470(4) -0.0197(3) 0.0560(10) Uani 1 1 d . . . . .
N1 N -0.2355(6) 0.5004(4) 0.2733(4) 0.0560(12) Uani 1 1 d . . . . .
H1A H -0.2436 0.5373 0.1920 0.067 Uiso 1 1 calc R . . . .
H1B H -0.3395 0.5110 0.3269 0.067 Uiso 1 1 calc R . . . .
C1 C -0.0599(7) 0.4259(5) 0.3168(5) 0.0437(13) Uani 1 1 d . . . . .
O2 O -0.3155(5) 0.4143(4) 0.5495(3) 0.0544(10) Uani 1 1 d D . . . .
N2 N 0.1119(6) 0.4029(4) 0.2413(4) 0.0485(11) Uani 1 1 d . . . . .
H2 H 0.1211 0.4326 0.1586 0.058 Uiso 1 1 calc R . . . .
C2 C -0.0094(6) 0.3595(5) 0.4450(4) 0.0361(12) Uani 1 1 d . . . . .
C3 C 0.1970(7) 0.2995(5) 0.4331(4) 0.0386(12) Uani 1 1 d . . . . .
O3 O -0.0724(5) 0.2947(4) 0.6646(3) 0.0556(10) Uani 1 1 d . . . . .
N3 N 0.2741(5) 0.3254(4) 0.3116(4) 0.0457(11) Uani 1 1 d . . . . .
N4 N -0.1378(6) 0.3562(4) 0.5581(4) 0.0423(11) Uani 1 1 d . . . . .
C4 C 0.5029(7) 0.1567(5) 0.5314(4) 0.0366(11) Uani 1 1 d . . . . .
N5 N 0.3085(6) 0.2191(5) 0.5362(4) 0.0453(11) Uani 1 1 d . . . . .
H5 H 0.236(7) 0.207(5) 0.607(5) 0.056(17) Uiso 1 1 d . . . . .
C5 C 0.5910(6) 0.0755(5) 0.6489(4) 0.0389(12) Uani 1 1 d . . . . .
O5 O 0.3006(6) 0.0926(5) 0.7863(3) 0.0870(14) Uani 1 1 d . . . . .
N6 N 0.4852(7) 0.0480(5) 0.7718(4) 0.0578(12) Uani 1 1 d . . . . .
C6 C 0.7961(8) 0.0118(5) 0.6477(4) 0.0451(13) Uani 1 1 d . . . . .
O6 O 0.5803(6) -0.0256(5) 0.8656(3) 0.0848(14) Uani 1 1 d . . . . .
C7 C 0.0072(8) 0.8042(7) -0.0196(6) 0.088(2) Uani 1 1 d . . . . .
H7A H 0.0151 0.9034 -0.0465 0.132 Uiso 1 1 calc GR . . . .
H7B H -0.0261 0.7722 0.0718 0.132 Uiso 1 1 calc GR . . . .
H7C H -0.0936 0.7923 -0.0616 0.132 Uiso 1 1 calc GR . . . .
N7 N 0.9643(7) -0.0399(5) 0.6436(4) 0.0690(14) Uani 1 1 d . . . . .
C8 C 0.3813(8) 0.7132(6) 0.0535(5) 0.0715(17) Uani 1 1 d . . . . .
H8C H 0.5134 0.6576 0.0459 0.107 Uiso 1 1 calc GR . . . .
H8D H 0.3175 0.6769 0.1386 0.107 Uiso 1 1 calc GR . . . .
H8E H 0.3880 0.8113 0.0377 0.107 Uiso 1 1 calc GR . . . .
N8 N 0.6127(5) 0.1707(4) 0.4183(4) 0.0462(11) Uani 1 1 d . . . . .
H8A H 0.5595 0.2194 0.3485 0.055 Uiso 1 1 calc R . . . .
H8B H 0.7368 0.1310 0.4149 0.055 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
S1 O1 1.531(6) . ?
S1 C7 1.781(6) . ?
S1 C8 1.792(6) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.348(6) . ?
C1 N2 1.349(6) . ?
C1 C2 1.423(7) . ?
O2 N4 1.240(5) . ?
N2 H2 0.8600 . ?
N2 N3 1.407(6) . ?
C2 C3 1.419(7) . ?
C2 N4 1.400(6) . ?
C3 N3 1.322(6) . ?
C3 N5 1.402(6) . ?
O3 N4 1.248(5) . ?
C4 N5 1.347(7) . ?
C4 C5 1.442(7) . ?
C4 N8 1.330(6) . ?
N5 H5 0.84(5) . ?
C5 N6 1.401(6) . ?
C5 C6 1.417(7) . ?
O5 N6 1.255(6) . ?
N6 O6 1.252(5) . ?
C6 N7 1.160(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8D 0.9600 . ?
C8 H8E 0.9600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C7 105.7(3) . . ?
O1 S1 C8 106.5(3) . . ?
C7 S1 C8 99.1(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N1 C1 N2 124.8(5) . . ?
N1 C1 C2 130.1(4) . . ?
N2 C1 C2 105.1(4) . . ?
C1 N2 H2 123.4 . . ?
C1 N2 N3 113.1(4) . . ?
N3 N2 H2 123.4 . . ?
C3 C2 C1 105.5(4) . . ?
N4 C2 C1 126.7(4) . . ?
N4 C2 C3 127.8(4) . . ?
N3 C3 C2 112.0(4) . . ?
N3 C3 N5 123.0(5) . . ?
N5 C3 C2 125.0(4) . . ?
C3 N3 N2 104.3(4) . . ?
O2 N4 C2 118.6(4) . . ?
O2 N4 O3 121.6(4) . . ?
O3 N4 C2 119.8(4) . . ?
N5 C4 C5 119.8(4) . . ?
N8 C4 N5 119.8(4) . . ?
N8 C4 C5 120.4(4) . . ?
C3 N5 H5 111(3) . . ?
C4 N5 C3 127.9(4) . . ?
C4 N5 H5 121(3) . . ?
N6 C5 C4 124.5(4) . . ?
N6 C5 C6 114.2(4) . . ?
C6 C5 C4 121.3(4) . . ?
O5 N6 C5 120.9(4) . . ?
O6 N6 C5 117.7(5) . . ?
O6 N6 O5 121.4(4) . . ?
N7 C6 C5 178.4(5) . . ?
S1 C7 H7A 109.5 . . ?
S1 C7 H7B 109.5 . . ?
S1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
S1 C8 H8C 109.5 . . ?
S1 C8 H8D 109.5 . . ?
S1 C8 H8E 109.5 . . ?
H8C C8 H8D 109.5 . . ?
H8C C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
C4 N8 H8A 120.0 . . ?
C4 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?

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
N1 H1A O1 0.86 2.30 2.978(9) 136.3 2_565
N2 H2 O1 0.86 2.01 2.820(8) 156.8 .
N5 H5 O3 0.84(5) 2.18(5) 2.834(8) 134(4) .
N5 H5 O5 0.84(5) 2.01(5) 2.637(9) 131(4) .
C7 H7C O6 0.96 2.61 3.292(10) 127.9 1_464
C8 H8E O6 0.96 2.50 3.215(9) 131.7 1_564
N8 H8A N3 0.86 2.06 2.717(8) 133.0 .
N8 H8B N7 0.86 2.14 2.980(9) 165.2 2_756

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 N2 N3 178.2(4) . . . . ?
N1 C1 C2 C3 -178.7(5) . . . . ?
N1 C1 C2 N4 0.6(9) . . . . ?
C1 N2 N3 C3 0.8(5) . . . . ?
C1 C2 C3 N3 0.9(6) . . . . ?
C1 C2 C3 N5 -177.6(4) . . . . ?
C1 C2 N4 O2 1.2(7) . . . . ?
C1 C2 N4 O3 -179.4(5) . . . . ?
N2 C1 C2 C3 -0.4(5) . . . . ?
N2 C1 C2 N4 178.9(4) . . . . ?
C2 C1 N2 N3 -0.2(5) . . . . ?
C2 C3 N3 N2 -1.0(5) . . . . ?
C2 C3 N5 C4 178.3(5) . . . . ?
C3 C2 N4 O2 -179.6(5) . . . . ?
C3 C2 N4 O3 -0.1(7) . . . . ?
N3 C3 N5 C4 -0.1(8) . . . . ?
N4 C2 C3 N3 -178.4(4) . . . . ?
N4 C2 C3 N5 3.0(8) . . . . ?
C4 C5 N6 O5 1.1(8) . . . . ?
C4 C5 N6 O6 179.2(5) . . . . ?
N5 C3 N3 N2 177.6(4) . . . . ?
N5 C4 C5 N6 4.0(7) . . . . ?
N5 C4 C5 C6 -178.2(5) . . . . ?
C5 C4 N5 C3 -178.9(4) . . . . ?
C6 C5 N6 O5 -176.8(5) . . . . ?
C6 C5 N6 O6 1.3(7) . . . . ?
N8 C4 N5 C3 1.3(8) . . . . ?
N8 C4 C5 N6 -176.2(4) . . . . ?
N8 C4 C5 C6 1.6(7) . . . . ?

_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_zzw_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2142356'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_audit_creation_date             2022-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 N8 O6, C H4 O'
_chemical_formula_sum            'C7 H8 N8 O7'
_chemical_formula_weight         316.21
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.849(5)
_cell_length_b                   9.328(4)
_cell_length_c                   12.780(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.352(7)
_cell_angle_gamma                90
_cell_volume                     1212.6(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    852
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.21
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7211
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                1576
_reflns_number_total             2759
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1949
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N6(H6A,H6B), N8(H8A,H8B), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.8807(2) 0.4778(3) 0.3741(2) 0.0759(9) Uani 1 1 d . . . . .
O2 O 0.7573(3) 0.5755(3) 0.2195(2) 0.0677(8) Uani 1 1 d . . . . .
O3 O 0.6678(2) 0.7873(2) 0.3495(2) 0.0660(8) Uani 1 1 d . . . . .
O4 O 0.4698(2) 0.7912(2) 0.3548(2) 0.0566(7) Uani 1 1 d . . . . .
O5 O 0.1247(2) 0.7486(3) 0.3907(2) 0.0620(7) Uani 1 1 d . . . . .
O6 O 0.1367(2) 0.1586(2) 0.3921(2) 0.0546(7) Uani 1 1 d . . . . .
O7 O 0.2946(2) 0.0168(2) 0.3951(2) 0.0533(7) Uani 1 1 d . . . . .
N1 N 0.6318(2) 0.3467(2) 0.3420(2) 0.0365(6) Uani 1 1 d . . . . .
N2 N 0.5122(2) 0.3522(2) 0.35710(19) 0.0303(6) Uani 1 1 d . . . . .
N3 N 0.3525(2) 0.5172(3) 0.3724(2) 0.0355(6) Uani 1 1 d . . . . .
N4 N 0.7756(3) 0.5157(3) 0.3081(3) 0.0455(7) Uani 1 1 d . . . . .
N5 N 0.5673(3) 0.7281(2) 0.3490(2) 0.0407(6) Uani 1 1 d . . . . .
N6 N 0.1683(2) 0.4375(3) 0.3943(2) 0.0457(7) Uani 1 1 d . . . . .
H6A H 0.1126 0.3724 0.4070 0.055 Uiso 1 1 d R . . . .
H6B H 0.1418 0.5406 0.3941 0.055 Uiso 1 1 d R . . . .
N7 N 0.2473(2) 0.1401(3) 0.3891(2) 0.0394(6) Uani 1 1 d . . . . .
N8 N 0.5047(2) 0.1108(2) 0.3617(2) 0.0393(6) Uani 1 1 d . . . . .
H8A H 0.5803 0.1151 0.3432 0.047 Uiso 1 1 d R . . . .
H8B H 0.4641 0.0333 0.3689 0.047 Uiso 1 1 d R . . . .
C1 C 0.6575(3) 0.4825(3) 0.3343(2) 0.0344(7) Uani 1 1 d . . . . .
C2 C 0.5624(3) 0.5782(3) 0.3440(2) 0.0324(7) Uani 1 1 d . . . . .
C3 C 0.4648(3) 0.4892(3) 0.3589(2) 0.0309(6) Uani 1 1 d . . . . .
C4 C 0.2796(3) 0.4022(3) 0.3815(2) 0.0323(6) Uani 1 1 d . . . . .
C5 C 0.3244(3) 0.2579(3) 0.3788(2) 0.0326(7) Uani 1 1 d . . . . .
H5 H 0.1986 0.8227 0.4078 0.039 Uiso 1 1 d R . . . .
C6 C 0.4459(3) 0.2308(3) 0.3657(2) 0.0293(6) Uani 1 1 d . . . . .
C7 C 0.0471(4) 0.8107(4) 0.4467(3) 0.0646(11) Uani 1 1 d . . . . .
H7A H 0.0412 0.9122 0.4336 0.097 Uiso 1 1 calc GR . . . .
H7B H 0.0865 0.7927 0.5253 0.097 Uiso 1 1 calc GR . . . .
H7C H -0.0394 0.7696 0.4194 0.097 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N4 1.211(3) . ?
O2 N4 1.215(4) . ?
O3 N5 1.220(3) . ?
O4 N5 1.235(3) . ?
O5 H5 1.0237 . ?
O5 C7 1.405(4) . ?
O6 N7 1.226(3) . ?
O7 N7 1.250(3) . ?
N1 N2 1.377(3) . ?
N1 C1 1.308(4) . ?
N2 C3 1.380(3) . ?
N2 C6 1.366(3) . ?
N3 C3 1.315(3) . ?
N3 C4 1.361(4) . ?
N4 C1 1.465(3) . ?
N5 C2 1.399(3) . ?
N6 H6A 0.9102 . ?
N6 H6B 1.0029 . ?
N6 C4 1.316(3) . ?
N7 C5 1.414(4) . ?
N8 H8A 0.9299 . ?
N8 H8B 0.8678 . ?
N8 C6 1.299(3) . ?
C1 C2 1.403(4) . ?
C2 C3 1.410(4) . ?
C4 C5 1.435(4) . ?
C5 C6 1.408(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C7 O5 H5 100.1 . . ?
C1 N1 N2 102.2(2) . . ?
N1 N2 C3 114.3(2) . . ?
C6 N2 N1 121.9(2) . . ?
C6 N2 C3 123.8(2) . . ?
C3 N3 C4 116.5(2) . . ?
O1 N4 O2 126.2(3) . . ?
O1 N4 C1 117.8(3) . . ?
O2 N4 C1 115.9(3) . . ?
O3 N5 O4 124.5(2) . . ?
O3 N5 C2 118.2(3) . . ?
O4 N5 C2 117.3(2) . . ?
H6A N6 H6B 115.7 . . ?
C4 N6 H6A 123.3 . . ?
C4 N6 H6B 120.9 . . ?
O6 N7 O7 120.8(2) . . ?
O6 N7 C5 120.7(3) . . ?
O7 N7 C5 118.5(2) . . ?
H8A N8 H8B 126.0 . . ?
C6 N8 H8A 117.5 . . ?
C6 N8 H8B 116.0 . . ?
N1 C1 N4 116.6(2) . . ?
N1 C1 C2 115.2(2) . . ?
C2 C1 N4 128.0(3) . . ?
N5 C2 C1 128.5(3) . . ?
N5 C2 C3 127.0(2) . . ?
C1 C2 C3 104.3(2) . . ?
N2 C3 C2 104.0(2) . . ?
N3 C3 N2 123.6(2) . . ?
N3 C3 C2 132.4(2) . . ?
N3 C4 C5 121.7(2) . . ?
N6 C4 N3 113.5(2) . . ?
N6 C4 C5 124.8(3) . . ?
N7 C5 C4 120.7(2) . . ?
C6 C5 N7 118.7(2) . . ?
C6 C5 C4 120.7(2) . . ?
N2 C6 C5 113.7(2) . . ?
N8 C6 N2 115.6(2) . . ?
N8 C6 C5 130.7(3) . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
N6 H6A O6 0.91 2.03 2.623(4) 121.6 .
N6 H6B O5 1.00 1.95 2.937(4) 168.4 .
N8 H8A O2 0.93 2.21 3.117(3) 166.3 2_645
N8 H8B O4 0.87 2.27 3.002(3) 142.4 1_545
N8 H8B O7 0.87 1.99 2.612(3) 128.0 .
O5 H5 O7 1.02 2.12 3.097(3) 158.3 1_565

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N4 C1 N1 -62.2(4) . . . . ?
O1 N4 C1 C2 123.1(4) . . . . ?
O2 N4 C1 N1 115.8(3) . . . . ?
O2 N4 C1 C2 -59.0(4) . . . . ?
O3 N5 C2 C1 -3.2(5) . . . . ?
O3 N5 C2 C3 170.1(3) . . . . ?
O4 N5 C2 C1 178.2(3) . . . . ?
O4 N5 C2 C3 -8.6(4) . . . . ?
O6 N7 C5 C4 5.4(4) . . . . ?
O6 N7 C5 C6 -174.4(3) . . . . ?
O7 N7 C5 C4 -174.5(3) . . . . ?
O7 N7 C5 C6 5.6(4) . . . . ?
N1 N2 C3 N3 -179.9(3) . . . . ?
N1 N2 C3 C2 -0.2(3) . . . . ?
N1 N2 C6 N8 1.8(4) . . . . ?
N1 N2 C6 C5 -178.9(2) . . . . ?
N1 C1 C2 N5 173.9(3) . . . . ?
N1 C1 C2 C3 -0.5(3) . . . . ?
N2 N1 C1 N4 -175.1(2) . . . . ?
N2 N1 C1 C2 0.4(3) . . . . ?
N3 C4 C5 N7 179.6(3) . . . . ?
N3 C4 C5 C6 -0.5(4) . . . . ?
N4 C1 C2 N5 -11.2(5) . . . . ?
N4 C1 C2 C3 174.3(3) . . . . ?
N5 C2 C3 N2 -174.2(3) . . . . ?
N5 C2 C3 N3 5.5(5) . . . . ?
N6 C4 C5 N7 0.7(4) . . . . ?
N6 C4 C5 C6 -179.4(3) . . . . ?
N7 C5 C6 N2 -179.7(2) . . . . ?
N7 C5 C6 N8 -0.5(5) . . . . ?
C1 N1 N2 C3 -0.1(3) . . . . ?
C1 N1 N2 C6 177.9(2) . . . . ?
C1 C2 C3 N2 0.4(3) . . . . ?
C1 C2 C3 N3 -179.9(3) . . . . ?
C3 N2 C6 N8 179.5(3) . . . . ?
C3 N2 C6 C5 -1.2(4) . . . . ?
C3 N3 C4 N6 -179.6(3) . . . . ?
C3 N3 C4 C5 1.3(4) . . . . ?
C4 N3 C3 N2 -2.1(4) . . . . ?
C4 N3 C3 C2 178.2(3) . . . . ?
C4 C5 C6 N2 0.4(4) . . . . ?
C4 C5 C6 N8 179.6(3) . . . . ?
C6 N2 C3 N3 2.2(4) . . . . ?
C6 N2 C3 C2 -178.1(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_cu_20210819_nlg_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2142355'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-01-16 deposited with the CCDC.	2022-03-16 downloaded from the CCDC.
;
_audit_creation_date             2022-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N8 O4'
_chemical_formula_sum            'C6 H6 N8 O4'
_chemical_formula_weight         254.19
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.484(9)
_cell_length_b                   7.966(11)
_cell_length_c                   18.00(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.59(4)
_cell_angle_gamma                90
_cell_volume                     929(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    426
_cell_measurement_temperature    307(2)
_cell_measurement_theta_max      58.891
_cell_measurement_theta_min      6.085
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.823
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1480 before and 0.0793 after correction. The Ratio of minimum to maximum transmission is 0.6238. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1203
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6115
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.667
_diffrn_reflns_theta_max         66.667
_diffrn_reflns_theta_min         4.914
_diffrn_ambient_temperature      307.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                706
_reflns_number_total             1623
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1623
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.015
_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)+(0.0800P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.2217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H10A,H10B} of N10, {H9A,H9B} of N9
 At 1.5 times of:
  {H2A,H2B} of N2
2. Restrained distances
 N2-H2A
 0.89 with sigma of 0.02
 N2-H2B
 0.89 with sigma of 0.02
 H2A-H2B
 1.5 with sigma of 0.04
 C4-H2A = C4-H2B
 2 with sigma of 0.04
3.a X=CH2 refined with riding coordinates:
 N9(H9A,H9B), N10(H10A,H10B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.5091(7) 0.1134(6) 0.6742(2) 0.0892(14) Uani 1 1 d . . . . .
C1 C 0.5637(8) 0.2897(7) 0.4914(3) 0.0585(14) Uani 1 1 d . . . . .
O2 O 0.7401(6) 0.2896(6) 0.6380(2) 0.0858(14) Uani 1 1 d . . . . .
N2 N 0.9216(7) 0.5343(7) 0.3994(3) 0.0755(15) Uani 1 1 d D . . . .
H2A H 0.958(8) 0.572(8) 0.3543(16) 0.113 Uiso 1 1 d DR . . . .
H2B H 1.016(7) 0.559(8) 0.435(2) 0.113 Uiso 1 1 d DR . . . .
C2 C 0.3036(9) 0.1245(7) 0.5330(3) 0.0644(15) Uani 1 1 d . . . . .
O3 O 0.7604(7) 0.5890(7) 0.2670(2) 0.0920(15) Uani 1 1 d . . . . .
N3 N 0.5853(8) 0.2022(7) 0.6252(3) 0.0696(14) Uani 1 1 d . . . . .
C3 C 0.4937(8) 0.2076(7) 0.5534(3) 0.0629(15) Uani 1 1 d . . . . .
O4 O 0.4860(7) 0.4589(6) 0.2301(2) 0.0874(14) Uani 1 1 d . . . . .
C4 C 0.7538(8) 0.4432(7) 0.4095(3) 0.0608(15) Uani 1 1 d D . . . .
N5 N 0.6196(8) 0.4893(7) 0.2790(3) 0.0713(14) Uani 1 1 d . . . . .
C5 C 0.6013(8) 0.4139(7) 0.3511(3) 0.0590(14) Uani 1 1 d . . . . .
N6 N 0.4182(6) 0.2533(6) 0.4370(3) 0.0596(12) Uani 1 1 d . . . . .
C6 C 0.4302(8) 0.3097(7) 0.3642(3) 0.0596(15) Uani 1 1 d . . . . .
N7 N 0.2567(7) 0.1518(6) 0.4603(3) 0.0659(13) Uani 1 1 d . . . . .
N8 N 0.7304(6) 0.3824(6) 0.4794(3) 0.0608(12) Uani 1 1 d . . . . .
N9 N 0.1875(8) 0.0290(7) 0.5764(3) 0.0789(15) Uani 1 1 d . . . . .
H9A H 0.0778 -0.0181 0.5584 0.095 Uiso 1 1 calc R . . . .
H9B H 0.2227 0.0147 0.6224 0.095 Uiso 1 1 calc R . . . .
N10 N 0.2781(7) 0.2650(6) 0.3178(3) 0.0761(15) Uani 1 1 d . . . . .
H10A H 0.1786 0.2041 0.3332 0.091 Uiso 1 1 calc R . . . .
H10B H 0.2789 0.2969 0.2721 0.091 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
O1 N3 1.244(6) . ?
C1 C3 1.382(8) . ?
C1 N6 1.372(7) . ?
C1 N8 1.332(7) . ?
O2 N3 1.238(6) . ?
N2 H2A 0.903(18) . ?
N2 H2B 0.894(18) . ?
N2 C4 1.324(7) . ?
C2 C3 1.438(8) . ?
C2 N7 1.352(7) . ?
C2 N9 1.338(8) . ?
O3 N5 1.233(6) . ?
N3 C3 1.407(8) . ?
O4 N5 1.242(6) . ?
C4 C5 1.442(7) . ?
C4 N8 1.360(8) . ?
N5 C5 1.438(8) . ?
C5 C6 1.411(8) . ?
N6 C6 1.390(8) . ?
N6 N7 1.397(6) . ?
C6 N10 1.324(6) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N6 C1 C3 104.0(5) . . ?
N8 C1 C3 132.8(5) . . ?
N8 C1 N6 123.1(5) . . ?
H2A N2 H2B 112(4) . . ?
C4 N2 H2A 123(3) . . ?
C4 N2 H2B 125(3) . . ?
N7 C2 C3 110.0(5) . . ?
N9 C2 C3 127.1(6) . . ?
N9 C2 N7 122.8(5) . . ?
O1 N3 C3 120.2(5) . . ?
O2 N3 O1 121.5(5) . . ?
O2 N3 C3 118.3(5) . . ?
C1 C3 C2 108.0(5) . . ?
C1 C3 N3 128.1(5) . . ?
N3 C3 C2 123.9(6) . . ?
N2 C4 C5 122.5(6) . . ?
N2 C4 N8 115.8(5) . . ?
N8 C4 C5 121.7(5) . . ?
O3 N5 O4 120.4(5) . . ?
O3 N5 C5 120.5(5) . . ?
O4 N5 C5 119.0(5) . . ?
N5 C5 C4 121.2(5) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 N5 118.8(5) . . ?
C1 N6 C6 123.4(5) . . ?
C1 N6 N7 114.4(5) . . ?
C6 N6 N7 122.2(4) . . ?
N6 C6 C5 114.4(4) . . ?
N10 C6 C5 129.0(6) . . ?
N10 C6 N6 116.6(5) . . ?
C2 N7 N6 103.5(4) . . ?
C1 N8 C4 117.3(4) . . ?
C2 N9 H9A 120.0 . . ?
C2 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?

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
N2 H2A O3 0.903(18) 2.01(4) 2.612(8) 123(4) .
N2 H2B N8 0.894(18) 2.27(2) 3.166(7) 177(6) 3_766
N9 H9A N7 0.86 2.43 3.271(7) 165.7 3_556
N9 H9B O1 0.86 2.20 2.774(7) 124.0 .
N9 H9B O4 0.86 2.52 3.094(10) 125.4 4_566
N10 H10A O4 0.86 2.49 3.088(7) 127.7 2_545
N10 H10B O1 0.86 2.55 3.226(8) 136.2 4_565
N10 H10B O2 0.86 2.52 3.267(10) 146.4 4_565
N10 H10B O4 0.86 2.02 2.610(8) 124.5 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 C3 C1 -175.4(6) . . . . ?
O1 N3 C3 C2 4.7(9) . . . . ?
C1 N6 C6 C5 -2.4(7) . . . . ?
C1 N6 C6 N10 -179.8(5) . . . . ?
C1 N6 N7 C2 0.3(6) . . . . ?
O2 N3 C3 C1 5.6(9) . . . . ?
O2 N3 C3 C2 -174.2(5) . . . . ?
N2 C4 C5 N5 -2.8(9) . . . . ?
N2 C4 C5 C6 177.2(6) . . . . ?
N2 C4 N8 C1 -179.7(5) . . . . ?
O3 N5 C5 C4 -4.3(8) . . . . ?
O3 N5 C5 C6 175.7(5) . . . . ?
C3 C1 N6 C6 -179.0(5) . . . . ?
C3 C1 N6 N7 0.0(6) . . . . ?
C3 C1 N8 C4 178.8(6) . . . . ?
C3 C2 N7 N6 -0.5(6) . . . . ?
O4 N5 C5 C4 179.1(5) . . . . ?
O4 N5 C5 C6 -0.9(8) . . . . ?
C4 C5 C6 N6 4.7(7) . . . . ?
C4 C5 C6 N10 -178.3(5) . . . . ?
N5 C5 C6 N6 -175.3(5) . . . . ?
N5 C5 C6 N10 1.7(9) . . . . ?
C5 C4 N8 C1 2.1(8) . . . . ?
N6 C1 C3 C2 -0.4(6) . . . . ?
N6 C1 C3 N3 179.7(5) . . . . ?
N6 C1 N8 C4 0.3(8) . . . . ?
C6 N6 N7 C2 179.4(5) . . . . ?
N7 C2 C3 C1 0.6(7) . . . . ?
N7 C2 C3 N3 -179.5(5) . . . . ?
N7 N6 C6 C5 178.6(4) . . . . ?
N7 N6 C6 N10 1.2(8) . . . . ?
N8 C1 C3 C2 -179.1(6) . . . . ?
N8 C1 C3 N3 1.0(11) . . . . ?
N8 C1 N6 C6 -0.1(8) . . . . ?
N8 C1 N6 N7 178.9(5) . . . . ?
N8 C4 C5 N5 175.2(5) . . . . ?
N8 C4 C5 C6 -4.8(8) . . . . ?
N9 C2 C3 C1 178.8(6) . . . . ?
N9 C2 C3 N3 -1.3(10) . . . . ?
N9 C2 N7 N6 -178.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
