# Electronic Supplementary Material (ESI) for Materials Horizons.
# This journal is © The Royal Society of Chemistry 2023

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

data_mo_20220601li_dyq_xm_0m
_database_code_depnum_ccdc_archive 'CCDC 2177265'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H2 N10 O12'
_chemical_formula_sum            'C7 H2 N10 O12'
_chemical_formula_weight         418.19
_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 0.0033 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                   15.4453(12)
_cell_length_b                   8.5038(5)
_cell_length_c                   12.4151(11)
_cell_angle_alpha                90
_cell_angle_beta                 113.671(3)
_cell_angle_gamma                90
_cell_volume                     1493.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2810
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.052
_cell_measurement_theta_min      2.795
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1216 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.9305.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.860
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.795
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2529
_reflns_number_total             3416
_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       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.067
_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)+(0.0445P)²+1.0643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1284
_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:
 C1(H1), C7(H7)
;
_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
O1 O 0.64221(12) 0.31231(19) 0.51188(15) 0.0327(4) Uani 1 1 d . . . . .
O2 O 0.56408(12) 0.16421(19) 0.58481(18) 0.0405(5) Uani 1 1 d . . . . .
O3 O 0.70640(13) 0.1854(2) 0.80582(17) 0.0409(5) Uani 1 1 d . . . . .
O4 O 0.74650(13) 0.4228(2) 0.87166(15) 0.0413(5) Uani 1 1 d . . . . .
O5 O 0.54215(14) 0.4139(2) 0.80132(18) 0.0446(5) Uani 1 1 d . . . . .
O6 O 0.46337(12) 0.4154(2) 0.61126(18) 0.0416(5) Uani 1 1 d . . . . .
O7 O 0.86236(11) 0.83123(19) 0.63453(17) 0.0349(4) Uani 1 1 d . . . . .
O8 O 0.76296(12) 1.01564(18) 0.62493(17) 0.0377(4) Uani 1 1 d . . . . .
O9 O 0.87226(14) 0.6113(2) 0.39654(17) 0.0435(5) Uani 1 1 d . . . . .
O10 O 0.74438(13) 0.6838(2) 0.41521(15) 0.0393(5) Uani 1 1 d . . . . .
O11 O 0.99899(13) 0.1205(2) 0.6798(2) 0.0479(5) Uani 1 1 d . . . . .
O12 O 0.94868(14) 0.1517(2) 0.8193(2) 0.0511(6) Uani 1 1 d . . . . .
N1 N 0.59568(13) 0.6720(2) 0.66859(17) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.65206(12) 0.5503(2) 0.66031(16) 0.0217(4) Uani 1 1 d . . . . .
N3 N 0.60982(13) 0.2794(2) 0.58288(18) 0.0274(4) Uani 1 1 d . . . . .
N4 N 0.70236(14) 0.3271(2) 0.79929(17) 0.0294(4) Uani 1 1 d . . . . .
N5 N 0.53433(14) 0.4097(2) 0.7008(2) 0.0303(5) Uani 1 1 d . . . . .
N6 N 0.78629(13) 0.8777(2) 0.63152(17) 0.0259(4) Uani 1 1 d . . . . .
N7 N 0.81712(13) 0.6067(2) 0.44476(17) 0.0272(4) Uani 1 1 d . . . . .
N8 N 0.83754(13) 0.3835(2) 0.70421(17) 0.0255(4) Uani 1 1 d . . . . .
N9 N 0.89721(13) 0.3143(2) 0.66429(18) 0.0277(4) Uani 1 1 d . . . . .
N10 N 0.95385(14) 0.1824(2) 0.7278(2) 0.0373(5) Uani 1 1 d . . . . .
C1 C 0.63723(15) 0.7997(2) 0.6545(2) 0.0253(5) Uani 1 1 d . . . . .
H1 H 0.614138 0.903245 0.654399 0.030 Uiso 1 1 calc R U . . .
C2 C 0.72031(15) 0.7636(2) 0.63953(19) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.72981(14) 0.6032(2) 0.64276(18) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.62757(15) 0.3982(2) 0.6831(2) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.80084(14) 0.5003(2) 0.62922(19) 0.0223(4) Uani 1 1 d . . . . .
C6 C 0.83930(14) 0.5026(2) 0.54383(19) 0.0228(4) Uani 1 1 d . . . . .
C7 C 0.90219(15) 0.3809(3) 0.5683(2) 0.0262(5) Uani 1 1 d . . . . .
H7 H 0.940152 0.350669 0.527663 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.208(3) . ?
O2 N3 1.213(2) . ?
O3 N4 1.208(3) . ?
O4 N4 1.201(3) . ?
O5 N5 1.206(3) . ?
O6 N5 1.208(3) . ?
O7 N6 1.226(2) . ?
O8 N6 1.220(2) . ?
O9 N7 1.223(3) . ?
O10 N7 1.223(2) . ?
O11 N10 1.206(3) . ?
O12 N10 1.198(3) . ?
N1 N2 1.383(2) . ?
N1 C1 1.308(3) . ?
N2 C3 1.379(3) . ?
N2 C4 1.408(3) . ?
N3 C4 1.540(3) . ?
N4 C4 1.563(3) . ?
N5 C4 1.544(3) . ?
N6 C2 1.439(3) . ?
N7 C6 1.441(3) . ?
N8 N9 1.345(3) . ?
N8 C5 1.323(3) . ?
N9 N10 1.446(3) . ?
N9 C7 1.349(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.402(3) . ?
C2 C3 1.371(3) . ?
C3 C5 1.465(3) . ?
C5 C6 1.408(3) . ?
C6 C7 1.367(3) . ?
C7 H7 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
C1 N1 N2 104.71(17) . . ?
N1 N2 C4 116.41(17) . . ?
C3 N2 N1 112.46(17) . . ?
C3 N2 C4 130.73(18) . . ?
O1 N3 O2 128.1(2) . . ?
O1 N3 C4 116.47(17) . . ?
O2 N3 C4 115.5(2) . . ?
O3 N4 C4 116.55(19) . . ?
O4 N4 O3 128.8(2) . . ?
O4 N4 C4 114.57(18) . . ?
O5 N5 O6 128.9(2) . . ?
O5 N5 C4 115.93(19) . . ?
O6 N5 C4 115.2(2) . . ?
O7 N6 C2 118.51(18) . . ?
O8 N6 O7 124.44(19) . . ?
O8 N6 C2 117.02(19) . . ?
O9 N7 O10 124.9(2) . . ?
O9 N7 C6 117.64(19) . . ?
O10 N7 C6 117.4(2) . . ?
C5 N8 N9 103.46(19) . . ?
N8 N9 N10 119.5(2) . . ?
N8 N9 C7 115.60(18) . . ?
C7 N9 N10 124.8(2) . . ?
O11 N10 N9 114.3(2) . . ?
O12 N10 O11 130.2(2) . . ?
O12 N10 N9 115.4(2) . . ?
N1 C1 H1 124.4 . . ?
N1 C1 C2 111.13(19) . . ?
C2 C1 H1 124.4 . . ?
C1 C2 N6 124.96(19) . . ?
C3 C2 N6 127.04(19) . . ?
C3 C2 C1 107.84(19) . . ?
N2 C3 C5 124.29(18) . . ?
C2 C3 N2 103.84(18) . . ?
C2 C3 C5 131.8(2) . . ?
N2 C4 N3 114.55(19) . . ?
N2 C4 N4 112.47(17) . . ?
N2 C4 N5 108.14(17) . . ?
N3 C4 N4 108.53(16) . . ?
N3 C4 N5 106.42(16) . . ?
N5 C4 N4 106.24(17) . . ?
N8 C5 C3 119.8(2) . . ?
N8 C5 C6 110.43(19) . . ?
C6 C5 C3 129.80(19) . . ?
C5 C6 N7 128.58(19) . . ?
C7 C6 N7 124.0(2) . . ?
C7 C6 C5 107.4(2) . . ?
N9 C7 C6 103.1(2) . . ?
N9 C7 H7 128.4 . . ?
C6 C7 H7 128.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N3 C4 N2 19.3(3) . . . . ?
O1 N3 C4 N4 -107.3(2) . . . . ?
O1 N3 C4 N5 138.74(18) . . . . ?
O2 N3 C4 N2 -160.12(18) . . . . ?
O2 N3 C4 N4 73.3(2) . . . . ?
O2 N3 C4 N5 -40.7(2) . . . . ?
O3 N4 C4 N2 -154.9(2) . . . . ?
O3 N4 C4 N3 -27.1(3) . . . . ?
O3 N4 C4 N5 87.0(2) . . . . ?
O4 N4 C4 N2 27.1(3) . . . . ?
O4 N4 C4 N3 154.85(19) . . . . ?
O4 N4 C4 N5 -91.1(2) . . . . ?
O5 N5 C4 N2 -98.2(2) . . . . ?
O5 N5 C4 N3 138.26(19) . . . . ?
O5 N5 C4 N4 22.7(2) . . . . ?
O6 N5 C4 N2 80.9(2) . . . . ?
O6 N5 C4 N3 -42.6(2) . . . . ?
O6 N5 C4 N4 -158.14(18) . . . . ?
O7 N6 C2 C1 170.2(2) . . . . ?
O7 N6 C2 C3 -4.6(3) . . . . ?
O8 N6 C2 C1 -8.1(3) . . . . ?
O8 N6 C2 C3 177.1(2) . . . . ?
O9 N7 C6 C5 164.4(2) . . . . ?
O9 N7 C6 C7 -17.9(3) . . . . ?
O10 N7 C6 C5 -15.6(3) . . . . ?
O10 N7 C6 C7 162.0(2) . . . . ?
N1 N2 C3 C2 -0.3(2) . . . . ?
N1 N2 C3 C5 -179.15(19) . . . . ?
N1 N2 C4 N3 123.83(19) . . . . ?
N1 N2 C4 N4 -111.6(2) . . . . ?
N1 N2 C4 N5 5.4(3) . . . . ?
N1 C1 C2 N6 -174.7(2) . . . . ?
N1 C1 C2 C3 1.0(3) . . . . ?
N2 N1 C1 C2 -1.2(2) . . . . ?
N2 C3 C5 N8 -47.8(3) . . . . ?
N2 C3 C5 C6 131.4(2) . . . . ?
N6 C2 C3 N2 175.2(2) . . . . ?
N6 C2 C3 C5 -6.1(4) . . . . ?
N7 C6 C7 N9 -177.72(19) . . . . ?
N8 N9 N10 O11 174.1(2) . . . . ?
N8 N9 N10 O12 -5.9(3) . . . . ?
N8 N9 C7 C6 -0.7(3) . . . . ?
N8 C5 C6 N7 178.1(2) . . . . ?
N8 C5 C6 C7 0.1(2) . . . . ?
N9 N8 C5 C3 178.86(18) . . . . ?
N9 N8 C5 C6 -0.5(2) . . . . ?
N10 N9 C7 C6 -177.51(19) . . . . ?
C1 N1 N2 C3 0.9(2) . . . . ?
C1 N1 N2 C4 174.44(19) . . . . ?
C1 C2 C3 N2 -0.4(2) . . . . ?
C1 C2 C3 C5 178.3(2) . . . . ?
C2 C3 C5 N8 133.7(2) . . . . ?
C2 C3 C5 C6 -47.0(4) . . . . ?
C3 N2 C4 N3 -64.1(3) . . . . ?
C3 N2 C4 N4 60.4(3) . . . . ?
C3 N2 C4 N5 177.4(2) . . . . ?
C3 C5 C6 N7 -1.2(4) . . . . ?
C3 C5 C6 C7 -179.2(2) . . . . ?
C4 N2 C3 C2 -172.6(2) . . . . ?
C4 N2 C3 C5 8.5(4) . . . . ?
C5 N8 N9 N10 177.77(18) . . . . ?
C5 N8 N9 C7 0.8(2) . . . . ?
C5 C6 C7 N9 0.3(2) . . . . ?
C7 N9 N10 O11 -9.2(3) . . . . ?
C7 N9 N10 O12 170.8(2) . . . . ?

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

data_cu_20230309_zm_nlg_dyq_4_0m
_database_code_depnum_ccdc_archive 'CCDC 2279507'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-03-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        123
_chemical_formula_moiety         'C8 H4 N6 O4'
_chemical_formula_sum            'C8 H4 N6 O4'
_chemical_formula_weight         248.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   5.0954(2)
_cell_length_b                   8.4208(4)
_cell_length_c                   11.6907(5)
_cell_angle_alpha                79.354(3)
_cell_angle_beta                 78.910(3)
_cell_angle_gamma                72.855(3)
_cell_volume                     465.97(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3017
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.89
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    1.277
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5687
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1090 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.7551.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6641
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.223
_diffrn_reflns_theta_min         3.889
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1447
_reflns_number_total             1689
_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       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1689
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.083
_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)+(0.0853P)²+1.3876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.1983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N6_$1-O1
 2.9 with sigma of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.1104(6) 0.9958(4) 0.1119(2) 0.0374(7) Uani 1 1 d D . . . .
C1 C 1.2051(8) 0.6575(5) 0.0788(3) 0.0297(8) Uani 1 1 d . . . . .
H1 H 1.345195 0.700062 0.027705 0.036 Uiso 1 1 calc R U . . .
N1 N 1.1995(7) 0.4988(4) 0.0951(3) 0.0321(8) Uani 1 1 d . . . . .
C2 C 0.9789(8) 0.7548(5) 0.1463(3) 0.0255(8) Uani 1 1 d . . . . .
N2 N 0.9691(7) 0.4937(4) 0.1751(3) 0.0273(7) Uani 1 1 d . . . . .
O2 O 0.6691(6) 1.0131(3) 0.1523(3) 0.0381(7) Uani 1 1 d . . . . .
C3 C 0.8254(7) 0.6473(4) 0.2097(3) 0.0236(8) Uani 1 1 d . . . . .
N3 N 0.5029(7) 0.5057(4) 0.3279(3) 0.0273(7) Uani 1 1 d . . . . .
O3 O 0.6193(6) 0.9514(4) 0.3806(3) 0.0350(7) Uani 1 1 d . . . . .
C4 C 0.8852(9) 0.3480(5) 0.2129(3) 0.0320(9) Uani 1 1 d . . . . .
H4 H 0.993227 0.245193 0.186183 0.038 Uiso 1 1 calc R U . . .
O4 O 0.1730(6) 1.0384(3) 0.3849(2) 0.0355(7) Uani 1 1 d . . . . .
N4 N 0.2649(7) 0.5216(4) 0.4064(3) 0.0305(7) Uani 1 1 d . . . . .
C5 C 0.6486(9) 0.3549(5) 0.2880(3) 0.0307(9) Uani 1 1 d . . . . .
H5 H 0.582369 0.257961 0.313315 0.037 Uiso 1 1 calc R U . . .
N5 N 0.3941(6) 0.9297(4) 0.3761(2) 0.0248(7) Uani 1 1 d . . . . .
N6 N 0.9130(7) 0.9325(4) 0.1383(2) 0.0274(7) Uani 1 1 d . . . . .
C6 C 0.5864(8) 0.6511(4) 0.2975(3) 0.0232(8) Uani 1 1 d . . . . .
C7 C 0.3897(7) 0.7640(4) 0.3633(3) 0.0238(8) Uani 1 1 d . . . . .
C8 C 0.1974(8) 0.6805(5) 0.4275(3) 0.0280(8) Uani 1 1 d . . . . .
H8 H 0.038931 0.730074 0.479528 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N6 1.235(4) . ?
C1 H1 0.9500 . ?
C1 N1 1.323(5) . ?
C1 C2 1.397(5) . ?
N1 N2 1.359(4) . ?
C2 C3 1.388(5) . ?
C2 N6 1.424(5) . ?
N2 C3 1.376(4) . ?
N2 C4 1.386(5) . ?
O2 N6 1.224(4) . ?
C3 C6 1.430(5) . ?
N3 N4 1.361(4) . ?
N3 C5 1.382(5) . ?
N3 C6 1.376(5) . ?
O3 N5 1.226(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.341(6) . ?
O4 N5 1.224(4) . ?
N4 C8 1.337(5) . ?
C5 H5 0.9500 . ?
N5 C7 1.438(5) . ?
C6 C7 1.383(5) . ?
C7 C8 1.395(5) . ?
C8 H8 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
N1 C1 H1 124.3 . . ?
N1 C1 C2 111.5(3) . . ?
C2 C1 H1 124.3 . . ?
C1 N1 N2 104.5(3) . . ?
C1 C2 N6 124.4(3) . . ?
C3 C2 C1 106.8(3) . . ?
C3 C2 N6 128.5(3) . . ?
N1 N2 C3 113.3(3) . . ?
N1 N2 C4 122.3(3) . . ?
C3 N2 C4 124.3(3) . . ?
C2 C3 C6 139.4(3) . . ?
N2 C3 C2 103.8(3) . . ?
N2 C3 C6 116.7(3) . . ?
N4 N3 C5 122.2(3) . . ?
N4 N3 C6 113.3(3) . . ?
C6 N3 C5 124.4(3) . . ?
N2 C4 H4 120.7 . . ?
C5 C4 N2 118.7(3) . . ?
C5 C4 H4 120.7 . . ?
C8 N4 N3 104.2(3) . . ?
N3 C5 H5 120.6 . . ?
C4 C5 N3 118.7(3) . . ?
C4 C5 H5 120.6 . . ?
O3 N5 C7 117.5(3) . . ?
O4 N5 O3 124.4(3) . . ?
O4 N5 C7 118.1(3) . . ?
O1 N6 C2 116.6(3) . . ?
O2 N6 O1 124.2(3) . . ?
O2 N6 C2 119.1(3) . . ?
N3 C6 C3 116.6(3) . . ?
N3 C6 C7 104.2(3) . . ?
C7 C6 C3 139.2(3) . . ?
C6 C7 N5 127.6(3) . . ?
C6 C7 C8 107.1(3) . . ?
C8 C7 N5 125.0(3) . . ?
N4 C8 C7 111.3(3) . . ?
N4 C8 H8 124.4 . . ?
C7 C8 H8 124.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.5(4) . . . . ?
C1 N1 N2 C4 177.9(3) . . . . ?
C1 C2 C3 N2 -0.4(4) . . . . ?
C1 C2 C3 C6 176.1(4) . . . . ?
C1 C2 N6 O1 -31.3(5) . . . . ?
C1 C2 N6 O2 145.4(4) . . . . ?
N1 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 N6 -173.2(3) . . . . ?
N1 N2 C3 C2 0.0(4) . . . . ?
N1 N2 C3 C6 -177.5(3) . . . . ?
N1 N2 C4 C5 -177.0(4) . . . . ?
C2 C1 N1 N2 -0.8(4) . . . . ?
C2 C3 C6 N3 175.7(4) . . . . ?
C2 C3 C6 C7 -0.3(8) . . . . ?
N2 C3 C6 N3 -8.1(5) . . . . ?
N2 C3 C6 C7 175.9(4) . . . . ?
N2 C4 C5 N3 -2.2(6) . . . . ?
C3 C2 N6 O1 156.0(4) . . . . ?
C3 C2 N6 O2 -27.3(5) . . . . ?
C3 N2 C4 C5 0.1(6) . . . . ?
C3 C6 C7 N5 -11.6(7) . . . . ?
C3 C6 C7 C8 175.3(4) . . . . ?
N3 N4 C8 C7 0.0(4) . . . . ?
N3 C6 C7 N5 172.1(3) . . . . ?
N3 C6 C7 C8 -1.1(4) . . . . ?
O3 N5 C7 C6 -37.1(5) . . . . ?
O3 N5 C7 C8 134.8(4) . . . . ?
C4 N2 C3 C2 -177.4(3) . . . . ?
C4 N2 C3 C6 5.2(5) . . . . ?
O4 N5 C7 C6 144.8(4) . . . . ?
O4 N5 C7 C8 -43.2(5) . . . . ?
N4 N3 C5 C4 -178.3(3) . . . . ?
N4 N3 C6 C3 -176.2(3) . . . . ?
N4 N3 C6 C7 1.1(4) . . . . ?
C5 N3 N4 C8 176.6(3) . . . . ?
C5 N3 C6 C3 6.6(5) . . . . ?
C5 N3 C6 C7 -176.1(3) . . . . ?
N5 C7 C8 N4 -172.7(3) . . . . ?
N6 C2 C3 N2 173.3(3) . . . . ?
N6 C2 C3 C6 -10.2(7) . . . . ?
C6 N3 N4 C8 -0.7(4) . . . . ?
C6 N3 C5 C4 -1.3(6) . . . . ?
C6 C7 C8 N4 0.7(4) . . . . ?

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

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2279509'
loop_
_audit_author_name
_audit_author_address
'Yongxing Tang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 N9 O10'
_chemical_formula_weight         373.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.144
_cell_length_b                   12.629
_cell_length_c                   12.031
_cell_angle_alpha                90
_cell_angle_beta                 99.17
_cell_angle_gamma                90
_cell_volume                     1371.7
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3098
_cell_measurement_theta_min      4.90
_cell_measurement_theta_max      49.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.525
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2381
_diffrn_reflns_av_unetI/netI     0.0949
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         5.112
_diffrn_reflns_theta_max         66.869
_diffrn_reflns_theta_full        66.869
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2381
_reflns_number_gt                1587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.9962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2290
_refine_ls_wR_factor_gt          0.2110
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1512(5) 0.5263(4) 0.2098(4) 0.0728(12) Uani 1 1 d . . . . .
H1 H 0.0744 0.4863 0.1706 0.087 Uiso 1 1 calc R U . . .
C2 C 0.3017(5) 0.5035(3) 0.2131(3) 0.0630(10) Uani 1 1 d . . . . .
C3 C 0.3814(5) 0.5797(3) 0.2782(3) 0.0586(10) Uani 1 1 d . . . . .
C4 C 0.5377(4) 0.5972(3) 0.3183(3) 0.0571(10) Uani 1 1 d . . . . .
C5 C 0.6650(5) 0.5946(3) 0.2639(3) 0.0604(10) Uani 1 1 d . . . . .
C6 C 0.7840(5) 0.6140(3) 0.3433(4) 0.0680(11) Uani 1 1 d . . . . .
H6 H 0.8830 0.6173 0.3342 0.082 Uiso 1 1 calc R U . . .
C7 C 0.2940(5) 0.7275(3) 0.3882(4) 0.0648(11) Uani 1 1 d . . . . .
H7 H 0.3891 0.7624 0.3858 0.078 Uiso 1 1 calc R U . . .
N1 N 0.2750(4) 0.6448(3) 0.3099(3) 0.0620(9) Uani 1 1 d . . . . .
N2 N 0.1316(4) 0.6113(3) 0.2691(3) 0.0739(10) Uani 1 1 d . . . . .
N3 N 0.2893(5) 0.6888(3) 0.5070(3) 0.0785(11) Uani 1 1 d . . . . .
N4 N 0.1683(5) 0.8074(3) 0.3571(5) 0.0830(12) Uani 1 1 d . . . . .
N5 N 0.3583(5) 0.4097(3) 0.1707(3) 0.0695(10) Uani 1 1 d . . . . .
N6 N 0.5789(4) 0.6187(3) 0.4274(3) 0.0606(9) Uani 1 1 d . . . . .
N7 N 0.7270(4) 0.6275(3) 0.4383(3) 0.0626(9) Uani 1 1 d . . . . .
N8 N 0.8087(5) 0.6546(3) 0.5468(3) 0.0828(12) Uani 1 1 d . . . . .
N9 N 0.6687(5) 0.5807(3) 0.1461(3) 0.0725(10) Uani 1 1 d . . . . .
O1 O 0.3257(7) 0.7535(4) 0.5799(4) 0.1344(19) Uani 1 1 d . . . . .
O2 O 0.2551(5) 0.5988(3) 0.5198(3) 0.0929(11) Uani 1 1 d . . . . .
O3 O 0.0774(6) 0.8158(4) 0.4182(5) 0.150(2) Uani 1 1 d . . . . .
O4 O 0.1715(5) 0.8566(3) 0.2733(4) 0.1018(12) Uani 1 1 d . . . . .
O5 O 0.2710(5) 0.3492(3) 0.1179(3) 0.0887(11) Uani 1 1 d . . . . .
O6 O 0.4919(4) 0.3922(3) 0.1928(3) 0.0886(10) Uani 1 1 d . . . . .
O7 O 0.5540(5) 0.5855(3) 0.0813(3) 0.0990(12) Uani 1 1 d . . . . .
O8 O 0.7911(4) 0.5683(3) 0.1188(3) 0.1006(12) Uani 1 1 d . . . . .
O9 O 0.9407(5) 0.6519(5) 0.5515(4) 0.1269(17) Uani 1 1 d . . . . .
O10 O 0.7357(5) 0.6769(3) 0.6182(3) 0.0951(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.318(6) . ?
C1 C2 1.401(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(6) . ?
C2 N5 1.419(5) . ?
C3 N1 1.373(5) . ?
C3 C4 1.451(6) . ?
C4 N6 1.335(5) . ?
C4 C5 1.424(5) . ?
C5 C6 1.352(6) . ?
C5 N9 1.434(6) . ?
C6 N7 1.340(5) . ?
C6 H6 0.9300 . ?
C7 N1 1.398(5) . ?
C7 N3 1.517(6) . ?
C7 N4 1.531(6) . ?
C7 H7 0.9800 . ?
N1 N2 1.391(5) . ?
N3 O2 1.196(5) . ?
N3 O1 1.207(5) . ?
N4 O4 1.188(6) . ?
N4 O3 1.198(5) . ?
N5 O5 1.209(5) . ?
N5 O6 1.228(5) . ?
N6 N7 1.345(5) . ?
N7 N8 1.438(5) . ?
N8 O9 1.199(6) . ?
N8 O10 1.203(5) . ?
N9 O7 1.205(5) . ?
N9 O8 1.225(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
N2 C1 C2 111.7(4) . . ?
N2 C1 H1 124.1 . . ?
C2 C1 H1 124.1 . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 N5 126.8(4) . . ?
C1 C2 N5 125.1(4) . . ?
N1 C3 C2 104.1(4) . . ?
N1 C3 C4 121.4(4) . . ?
C2 C3 C4 134.5(4) . . ?
N6 C4 C5 109.5(4) . . ?
N6 C4 C3 117.8(3) . . ?
C5 C4 C3 132.7(4) . . ?
C6 C5 C4 107.2(4) . . ?
C6 C5 N9 125.3(4) . . ?
C4 C5 N9 127.4(4) . . ?
N7 C6 C5 104.3(4) . . ?
N7 C6 H6 127.9 . . ?
C5 C6 H6 127.9 . . ?
N1 C7 N3 112.0(3) . . ?
N1 C7 N4 108.7(4) . . ?
N3 C7 N4 108.0(3) . . ?
N1 C7 H7 109.4 . . ?
N3 C7 H7 109.4 . . ?
N4 C7 H7 109.4 . . ?
C3 N1 N2 113.0(3) . . ?
C3 N1 C7 128.1(4) . . ?
N2 N1 C7 118.2(3) . . ?
C1 N2 N1 103.7(4) . . ?
O2 N3 O1 126.7(4) . . ?
O2 N3 C7 118.4(4) . . ?
O1 N3 C7 114.9(4) . . ?
O4 N4 O3 126.0(5) . . ?
O4 N4 C7 115.6(4) . . ?
O3 N4 C7 118.4(5) . . ?
O5 N5 O6 123.4(4) . . ?
O5 N5 C2 117.9(4) . . ?
O6 N5 C2 118.6(4) . . ?
C4 N6 N7 103.5(3) . . ?
C6 N7 N6 115.5(4) . . ?
C6 N7 N8 126.0(4) . . ?
N6 N7 N8 118.5(3) . . ?
O9 N8 O10 129.9(5) . . ?
O9 N8 N7 114.2(4) . . ?
O10 N8 N7 115.9(4) . . ?
O7 N9 O8 124.8(4) . . ?
O7 N9 C5 118.6(4) . . ?
O8 N9 C5 116.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -0.3(5) . . . . ?
N2 C1 C2 N5 171.0(4) . . . . ?
C1 C2 C3 N1 -0.5(4) . . . . ?
N5 C2 C3 N1 -171.6(4) . . . . ?
C1 C2 C3 C4 176.0(4) . . . . ?
N5 C2 C3 C4 4.9(7) . . . . ?
N1 C3 C4 N6 44.7(5) . . . . ?
C2 C3 C4 N6 -131.4(5) . . . . ?
N1 C3 C4 C5 -136.5(4) . . . . ?
C2 C3 C4 C5 47.4(7) . . . . ?
N6 C4 C5 C6 0.7(5) . . . . ?
C3 C4 C5 C6 -178.2(4) . . . . ?
N6 C4 C5 N9 -175.8(4) . . . . ?
C3 C4 C5 N9 5.3(7) . . . . ?
C4 C5 C6 N7 -0.3(4) . . . . ?
N9 C5 C6 N7 176.3(4) . . . . ?
C2 C3 N1 N2 1.2(4) . . . . ?
C4 C3 N1 N2 -175.9(3) . . . . ?
C2 C3 N1 C7 171.2(4) . . . . ?
C4 C3 N1 C7 -5.9(6) . . . . ?
N3 C7 N1 C3 -87.3(5) . . . . ?
N4 C7 N1 C3 153.5(4) . . . . ?
N3 C7 N1 N2 82.3(5) . . . . ?
N4 C7 N1 N2 -37.0(5) . . . . ?
C2 C1 N2 N1 1.0(5) . . . . ?
C3 N1 N2 C1 -1.4(5) . . . . ?
C7 N1 N2 C1 -172.5(4) . . . . ?
N1 C7 N3 O2 -7.9(6) . . . . ?
N4 C7 N3 O2 111.7(5) . . . . ?
N1 C7 N3 O1 170.0(5) . . . . ?
N4 C7 N3 O1 -70.4(5) . . . . ?
N1 C7 N4 O4 -69.3(5) . . . . ?
N3 C7 N4 O4 169.0(4) . . . . ?
N1 C7 N4 O3 111.3(5) . . . . ?
N3 C7 N4 O3 -10.4(6) . . . . ?
C3 C2 N5 O5 177.3(4) . . . . ?
C1 C2 N5 O5 7.7(6) . . . . ?
C3 C2 N5 O6 -0.1(6) . . . . ?
C1 C2 N5 O6 -169.7(4) . . . . ?
C5 C4 N6 N7 -0.7(4) . . . . ?
C3 C4 N6 N7 178.4(3) . . . . ?
C5 C6 N7 N6 -0.1(5) . . . . ?
C5 C6 N7 N8 -177.3(4) . . . . ?
C4 N6 N7 C6 0.6(4) . . . . ?
C4 N6 N7 N8 177.9(3) . . . . ?
C6 N7 N8 O9 -9.1(7) . . . . ?
N6 N7 N8 O9 173.9(4) . . . . ?
C6 N7 N8 O10 170.5(4) . . . . ?
N6 N7 N8 O10 -6.5(6) . . . . ?
C6 C5 N9 O7 -165.0(4) . . . . ?
C4 C5 N9 O7 10.9(6) . . . . ?
C6 C5 N9 O8 12.6(6) . . . . ?
C4 C5 N9 O8 -171.5(4) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.067

