# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_znz0186_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2068607'
loop_
_audit_author_name
_audit_author_address
'XIE HAN'
;WUST
China
;
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C48 H48 N32 O16, 2(C11 H6 N4 O4)'
_chemical_formula_sum            'C70 H60 N40 O24'
_chemical_formula_weight         1845.58
_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                   13.794(3)
_cell_length_b                   19.827(5)
_cell_length_c                   16.822(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.599(7)
_cell_angle_gamma                90
_cell_volume                     4452.1(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.108
_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            ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27742
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.054
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_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_source_current           40.0
_diffrn_source_power             2.0
_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                5247
_reflns_number_total             7783
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         7783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.1090
_refine_ls_restrained_S_all      1.114
_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)+(0.0700P)²+17.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2652
_refine_ls_wR_factor_ref         0.2868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B),
 C22(H22A,H22B), C24(H24A,H24B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11)
;
_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
C1_1 C 0.2951(4) 0.6698(3) 0.1822(4) 0.0465(13) Uani 1 1 d . . . . .
C2_1 C 0.2865(4) 0.7644(3) 0.0991(3) 0.0410(12) Uani 1 1 d . . . . .
H2_1 H 0.244447 0.803366 0.103237 0.049 Uiso 1 1 calc R U . . .
C3_1 C 0.3859(4) 0.7652(3) 0.1671(3) 0.0415(12) Uani 1 1 d . . . . .
H3_1 H 0.388636 0.803299 0.204644 0.050 Uiso 1 1 calc R U . . .
C4_1 C 0.4218(4) 0.7756(3) 0.0385(4) 0.0449(13) Uani 1 1 d . . . . .
C5_1 C 0.4456(4) 0.6920(3) 0.2917(3) 0.0475(13) Uani 1 1 d . . . . .
H5A_1 H 0.445772 0.733692 0.321968 0.057 Uiso 1 1 calc R U . . .
H5B_1 H 0.414786 0.657486 0.318082 0.057 Uiso 1 1 calc R U . . .
C6_1 C 0.6238(4) 0.7195(3) 0.2886(3) 0.0406(12) Uani 1 1 d . . . . .
H6_1 H 0.624365 0.759401 0.323059 0.049 Uiso 1 1 calc R U . . .
C7_1 C 0.7208(4) 0.6782(3) 0.3182(3) 0.0424(12) Uani 1 1 d . . . . .
H7_1 H 0.763561 0.696409 0.369243 0.051 Uiso 1 1 calc R U . . .
C8_1 C 0.5843(4) 0.6111(3) 0.3250(3) 0.0443(13) Uani 1 1 d . . . . .
C9_1 C 0.1344(4) 0.6884(3) 0.0797(3) 0.0465(13) Uani 1 1 d . . . . .
H9A_1 H 0.112810 0.654859 0.113631 0.056 Uiso 1 1 calc R U . . .
H9B_1 H 0.096337 0.729231 0.081482 0.056 Uiso 1 1 calc R U . . .
C10_1 C 0.8980(4) 0.2940(3) 0.0748(3) 0.0436(12) Uani 1 1 d . . . . .
H10_1 H 0.941821 0.255360 0.073539 0.052 Uiso 1 1 calc R U . . .
C11_1 C 0.9447(4) 0.3428(3) 0.1471(3) 0.0416(12) Uani 1 1 d . . . . .
H11_1 H 1.014275 0.330777 0.173585 0.050 Uiso 1 1 calc R U . . .
N12_1 N 0.9379(4) 0.4079(2) 0.1059(3) 0.0469(11) Uani 1 1 d . . . . .
C13_1 C 0.9075(4) 0.4028(3) 0.0225(4) 0.0454(13) Uani 1 1 d . . . . .
C14_1 C 0.7478(4) 0.2170(3) 0.0536(3) 0.0454(13) Uani 1 1 d . . . . .
H14A_1 H 0.792839 0.181745 0.044964 0.054 Uiso 1 1 calc R U . . .
H14B_1 H 0.709189 0.199101 0.089744 0.054 Uiso 1 1 calc R U . . .
C15_1 C 0.8018(4) 0.2934(3) 0.1706(3) 0.0435(12) Uani 1 1 d . . . . .
C16_1 C 0.5615(4) 0.7919(3) 0.1618(4) 0.0454(13) Uani 1 1 d . . . . .
H16A_1 H 0.557887 0.827855 0.200065 0.055 Uiso 1 1 calc R U . . .
H16B_1 H 0.592904 0.810044 0.120958 0.055 Uiso 1 1 calc R U . . .
C17_1 C 0.7101(4) 0.7200(3) 0.1861(3) 0.0424(12) Uani 1 1 d . . . . .
C18_1 C 0.7507(4) 0.5595(3) 0.3761(3) 0.0429(12) Uani 1 1 d . . . . .
H18A_1 H 0.798638 0.580756 0.421371 0.051 Uiso 1 1 calc R U . . .
H18B_1 H 0.710880 0.528394 0.399166 0.051 Uiso 1 1 calc R U . . .
C19_1 C 0.8968(4) 0.5475(3) 0.3113(3) 0.0417(12) Uani 1 1 d . . . . .
H19_1 H 0.942653 0.565331 0.361074 0.050 Uiso 1 1 calc R U . . .
C20_1 C 0.9407(4) 0.4852(3) 0.2781(3) 0.0413(12) Uani 1 1 d . . . . .
H20_1 H 1.009473 0.476156 0.309574 0.050 Uiso 1 1 calc R U . . .
C21_1 C 0.8003(4) 0.4528(3) 0.3213(3) 0.0428(12) Uani 1 1 d . . . . .
C22_1 C 0.9912(4) 0.4671(3) 0.1454(4) 0.0474(13) Uani 1 1 d . . . . .
H22A_1 H 1.055387 0.453230 0.180149 0.057 Uiso 1 1 calc R U . . .
H22B_1 H 1.003855 0.497051 0.103578 0.057 Uiso 1 1 calc R U . . .
C23_1 C 0.9102(4) 0.5701(3) 0.1789(4) 0.0459(13) Uani 1 1 d . . . . .
C24_1 C 0.9032(5) 0.3615(3) 0.2842(3) 0.0466(13) Uani 1 1 d . . . . .
H24A_1 H 0.974457 0.357372 0.309012 0.056 Uiso 1 1 calc R U . . .
H24B_1 H 0.868289 0.334657 0.316448 0.056 Uiso 1 1 calc R U . . .
C25_1 C 0.8702(4) 0.6661(3) 0.2569(4) 0.0483(14) Uani 1 1 d . . . . .
H25A_1 H 0.910841 0.678513 0.310823 0.058 Uiso 1 1 calc R U . . .
H25B_1 H 0.894238 0.691460 0.216381 0.058 Uiso 1 1 calc R U . . .
N1_1 N 0.3861(3) 0.7013(2) 0.2088(3) 0.0432(10) Uani 1 1 d . . . . .
N2_1 N 0.2407(3) 0.7024(2) 0.1139(3) 0.0441(11) Uani 1 1 d . . . . .
N3_1 N 0.3196(3) 0.7659(2) 0.0241(3) 0.0452(11) Uani 1 1 d . . . . .
N4_1 N 0.4610(3) 0.7708(2) 0.1215(3) 0.0427(10) Uani 1 1 d . . . . .
N5_1 N 0.5466(3) 0.6730(2) 0.2960(3) 0.0433(10) Uani 1 1 d . . . . .
N6_1 N 0.6854(3) 0.6109(2) 0.3300(3) 0.0409(10) Uani 1 1 d . . . . .
N7_1 N 0.8874(4) 0.3357(2) 0.0033(3) 0.0484(11) Uani 1 1 d . . . . .
N8_1 N 0.8063(3) 0.2736(2) 0.0934(3) 0.0435(11) Uani 1 1 d . . . . .
N9_1 N 0.8814(3) 0.3348(2) 0.2014(3) 0.0457(11) Uani 1 1 d . . . . .
N10_1 N 0.6240(3) 0.7382(2) 0.2061(3) 0.0445(11) Uani 1 1 d . . . . .
N11_1 N 0.7673(3) 0.6842(2) 0.2510(3) 0.0451(11) Uani 1 1 d . . . . .
N16_1 N 0.8043(3) 0.5222(2) 0.3275(3) 0.0428(10) Uani 1 1 d . . . . .
N13_1 N 0.8740(4) 0.4320(2) 0.2875(3) 0.0434(11) Uani 1 1 d . . . . .
N14_1 N 0.9367(4) 0.5030(2) 0.1941(3) 0.0455(11) Uani 1 1 d . . . . .
N15_1 N 0.8823(3) 0.5945(2) 0.2439(3) 0.0423(10) Uani 1 1 d . . . . .
O1_1 O 0.2685(3) 0.6200(2) 0.2138(3) 0.0529(10) Uani 1 1 d . . . . .
O2_1 O 0.4664(3) 0.7853(2) -0.0138(2) 0.0539(10) Uani 1 1 d . . . . .
O3_1 O 0.5350(3) 0.56496(19) 0.3433(3) 0.0507(10) Uani 1 1 d . . . . .
O4_1 O 0.8996(3) 0.4482(2) -0.0273(3) 0.0527(10) Uani 1 1 d . . . . .
O5_1 O 0.7384(3) 0.2768(2) 0.2063(3) 0.0548(10) Uani 1 1 d . . . . .
O6_1 O 0.7340(3) 0.7331(2) 0.1232(3) 0.0509(10) Uani 1 1 d . . . . .
O7_1 O 0.7395(3) 0.41670(19) 0.3420(3) 0.0537(10) Uani 1 1 d . . . . .
O8_1 O 0.9119(3) 0.5998(2) 0.1157(3) 0.0565(11) Uani 1 1 d . . . . .
C1_2 C 0.7526(6) 0.5892(4) -0.0749(5) 0.079(2) Uani 1 1 d . . . . .
H1_2 H 0.764821 0.598581 -0.019077 0.095 Uiso 1 1 calc R U . . .
C2_2 C 0.7909(6) 0.6288(4) -0.1224(5) 0.076(2) Uani 1 1 d . . . . .
H2_2 H 0.829793 0.665342 -0.098728 0.091 Uiso 1 1 calc R U . . .
C3_2 C 0.7752(5) 0.6178(4) -0.2075(5) 0.0652(18) Uani 1 1 d . . . . .
C4_2 C 0.7129(6) 0.5626(3) -0.2392(5) 0.0690(19) Uani 1 1 d . . . . .
H4_2 H 0.697845 0.553201 -0.295191 0.083 Uiso 1 1 calc R U . . .
C5_2 C 0.6753(6) 0.5236(4) -0.1893(5) 0.0703(19) Uani 1 1 d . . . . .
H5_2 H 0.634082 0.487803 -0.212090 0.084 Uiso 1 1 calc R U . . .
C6_2 C 0.6573(6) 0.4911(4) -0.0538(6) 0.081(2) Uani 1 1 d . . . . .
C7_2 C 0.5667(8) 0.4569(4) -0.0816(6) 0.081(2) Uani 1 1 d . . . . .
C8_2 C 0.5265(7) 0.4152(4) -0.0208(7) 0.086(3) Uani 1 1 d . . . . .
C9_2 C 0.5828(8) 0.4149(4) 0.0587(6) 0.085(2) Uani 1 1 d . . . . .
C10_2 C 0.6681(8) 0.4454(6) 0.0839(8) 0.111(3) Uani 1 1 d . . . . .
H10_2 H 0.702965 0.442980 0.138897 0.133 Uiso 1 1 calc R U . . .
C11_2 C 0.7083(8) 0.4823(5) 0.0276(6) 0.108(4) Uani 1 1 d . . . . .
H11_2 H 0.771501 0.501491 0.046092 0.129 Uiso 1 1 calc R U . . .
N1_2 N 0.6945(5) 0.5338(3) -0.1070(4) 0.0676(16) Uani 1 1 d . . . . .
N2_2 N 0.5039(7) 0.4578(4) -0.1523(5) 0.104(3) Uani 1 1 d . . . . .
N3_2 N 0.4379(8) 0.3958(4) -0.0644(6) 0.107(3) Uani 1 1 d . . . . .
N4_2 N 0.5355(8) 0.3783(5) 0.1182(6) 0.105(3) Uani 1 1 d . . . . .
O1_2 O 0.8159(4) 0.6539(3) -0.2509(3) 0.0759(14) Uani 1 1 d . . . . .
O2_2 O 0.4239(6) 0.4199(4) -0.1419(4) 0.123(3) Uani 1 1 d . . . . .
O3_2 O 0.5746(7) 0.3874(5) 0.1915(6) 0.151(3) Uani 1 1 d . . . . .
O4_2 O 0.4624(7) 0.3471(4) 0.0916(6) 0.122(3) 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_1 N1_1 1.372(7) . ?
C1_1 N2_1 1.366(7) . ?
C1_1 O1_1 1.221(7) . ?
C2_1 H2_1 0.9800 . ?
C2_1 C3_1 1.548(7) . ?
C2_1 N2_1 1.431(7) . ?
C2_1 N3_1 1.445(7) . ?
C3_1 H3_1 0.9800 . ?
C3_1 N1_1 1.447(7) . ?
C3_1 N4_1 1.441(7) . ?
C4_1 N3_1 1.383(7) . ?
C4_1 N4_1 1.367(7) . ?
C4_1 O2_1 1.210(7) . ?
C5_1 H5A_1 0.9700 . ?
C5_1 H5B_1 0.9700 . ?
C5_1 N1_1 1.441(7) . ?
C5_1 N5_1 1.428(7) . ?
C6_1 H6_1 0.9800 . ?
C6_1 C7_1 1.540(7) . ?
C6_1 N5_1 1.437(7) . ?
C6_1 N10_1 1.436(7) . ?
C7_1 H7_1 0.9800 . ?
C7_1 N6_1 1.450(7) . ?
C7_1 N11_1 1.438(7) . ?
C8_1 N5_1 1.374(7) . ?
C8_1 N6_1 1.377(7) . ?
C8_1 O3_1 1.223(7) . ?
C9_1 H9A_1 0.9700 . ?
C9_1 H9B_1 0.9700 . ?
C9_1 N2_1 1.461(7) . ?
C9_1 N7_1 1.433(7) 3_665 ?
C10_1 H10_1 0.9800 . ?
C10_1 C11_1 1.560(7) . ?
C10_1 N7_1 1.435(7) . ?
C10_1 N8_1 1.436(7) . ?
C11_1 H11_1 0.9800 . ?
C11_1 N12_1 1.457(7) . ?
C11_1 N9_1 1.424(7) . ?
N12_1 C13_1 1.364(7) . ?
N12_1 C22_1 1.452(7) . ?
C13_1 N7_1 1.382(7) . ?
C13_1 O4_1 1.215(7) . ?
C14_1 H14A_1 0.9700 . ?
C14_1 H14B_1 0.9700 . ?
C14_1 N3_1 1.441(7) 3_665 ?
C14_1 N8_1 1.444(7) . ?
C15_1 N8_1 1.374(7) . ?
C15_1 N9_1 1.364(7) . ?
C15_1 O5_1 1.224(7) . ?
C16_1 H16A_1 0.9700 . ?
C16_1 H16B_1 0.9700 . ?
C16_1 N4_1 1.443(7) . ?
C16_1 N10_1 1.452(7) . ?
C17_1 N10_1 1.362(7) . ?
C17_1 N11_1 1.373(7) . ?
C17_1 O6_1 1.214(6) . ?
C18_1 H18A_1 0.9700 . ?
C18_1 H18B_1 0.9700 . ?
C18_1 N6_1 1.449(7) . ?
C18_1 N16_1 1.437(7) . ?
C19_1 H19_1 0.9800 . ?
C19_1 C20_1 1.541(7) . ?
C19_1 N16_1 1.460(7) . ?
C19_1 N15_1 1.442(7) . ?
C20_1 H20_1 0.9800 . ?
C20_1 N13_1 1.434(7) . ?
C20_1 N14_1 1.444(7) . ?
C21_1 N16_1 1.380(7) . ?
C21_1 N13_1 1.348(7) . ?
C21_1 O7_1 1.218(7) . ?
C22_1 H22A_1 0.9700 . ?
C22_1 H22B_1 0.9700 . ?
C22_1 N14_1 1.432(7) . ?
C23_1 N14_1 1.387(7) . ?
C23_1 N15_1 1.336(7) . ?
C23_1 O8_1 1.221(7) . ?
C24_1 H24A_1 0.9700 . ?
C24_1 H24B_1 0.9700 . ?
C24_1 N9_1 1.449(7) . ?
C24_1 N13_1 1.459(7) . ?
C25_1 H25A_1 0.9700 . ?
C25_1 H25B_1 0.9700 . ?
C25_1 N11_1 1.444(7) . ?
C25_1 N15_1 1.454(7) . ?
C1_2 H1_2 0.9300 . ?
C1_2 C2_2 1.322(11) . ?
C1_2 N1_2 1.386(10) . ?
C2_2 H2_2 0.9300 . ?
C2_2 C3_2 1.409(11) . ?
C3_2 C4_2 1.412(10) . ?
C3_2 O1_2 1.252(8) . ?
C4_2 H4_2 0.9300 . ?
C4_2 C5_2 1.338(10) . ?
C5_2 H5_2 0.9300 . ?
C5_2 N1_2 1.357(10) . ?
C6_2 C7_2 1.394(13) . ?
C6_2 C11_2 1.383(13) . ?
C6_2 N1_2 1.420(10) . ?
C7_2 C8_2 1.524(12) . ?
C7_2 N2_2 1.283(11) . ?
C8_2 C9_2 1.367(13) . ?
C8_2 N3_2 1.315(12) . ?
C9_2 C10_2 1.295(14) . ?
C9_2 N4_2 1.510(13) . ?
C10_2 H10_2 0.9300 . ?
C10_2 C11_2 1.416(13) . ?
C11_2 H11_2 0.9300 . ?
N2_2 O2_2 1.382(10) . ?
N3_2 O2_2 1.356(10) . ?
N4_2 O3_2 1.229(12) . ?
N4_2 O4_2 1.171(12) . ?

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_1 C1_1 N1_1 108.8(5) . . ?
O1_1 C1_1 N1_1 125.2(6) . . ?
O1_1 C1_1 N2_1 126.0(5) . . ?
C3_1 C2_1 H2_1 111.6 . . ?
N2_1 C2_1 H2_1 111.6 . . ?
N2_1 C2_1 C3_1 103.1(4) . . ?
N2_1 C2_1 N3_1 114.9(4) . . ?
N3_1 C2_1 H2_1 111.6 . . ?
N3_1 C2_1 C3_1 103.3(4) . . ?
C2_1 C3_1 H3_1 111.6 . . ?
N1_1 C3_1 C2_1 104.1(4) . . ?
N1_1 C3_1 H3_1 111.6 . . ?
N4_1 C3_1 C2_1 103.2(4) . . ?
N4_1 C3_1 H3_1 111.6 . . ?
N4_1 C3_1 N1_1 114.3(4) . . ?
N4_1 C4_1 N3_1 106.9(5) . . ?
O2_1 C4_1 N3_1 125.4(5) . . ?
O2_1 C4_1 N4_1 127.7(5) . . ?
H5A_1 C5_1 H5B_1 107.8 . . ?
N1_1 C5_1 H5A_1 109.0 . . ?
N1_1 C5_1 H5B_1 109.0 . . ?
N5_1 C5_1 H5A_1 109.0 . . ?
N5_1 C5_1 H5B_1 109.0 . . ?
N5_1 C5_1 N1_1 113.1(5) . . ?
C7_1 C6_1 H6_1 111.2 . . ?
N5_1 C6_1 H6_1 111.2 . . ?
N5_1 C6_1 C7_1 103.5(4) . . ?
N10_1 C6_1 H6_1 111.2 . . ?
N10_1 C6_1 C7_1 103.7(4) . . ?
N10_1 C6_1 N5_1 115.5(4) . . ?
C6_1 C7_1 H7_1 111.6 . . ?
N6_1 C7_1 C6_1 103.8(4) . . ?
N6_1 C7_1 H7_1 111.6 . . ?
N11_1 C7_1 C6_1 103.0(4) . . ?
N11_1 C7_1 H7_1 111.6 . . ?
N11_1 C7_1 N6_1 114.5(4) . . ?
N5_1 C8_1 N6_1 108.0(5) . . ?
O3_1 C8_1 N5_1 125.0(5) . . ?
O3_1 C8_1 N6_1 127.0(5) . . ?
H9A_1 C9_1 H9B_1 107.8 . . ?
N2_1 C9_1 H9A_1 109.0 . . ?
N2_1 C9_1 H9B_1 109.0 . . ?
N7_1 C9_1 H9A_1 109.0 3_665 . ?
N7_1 C9_1 H9B_1 109.0 3_665 . ?
N7_1 C9_1 N2_1 113.0(5) 3_665 . ?
C11_1 C10_1 H10_1 111.4 . . ?
N7_1 C10_1 H10_1 111.4 . . ?
N7_1 C10_1 C11_1 103.4(4) . . ?
N7_1 C10_1 N8_1 115.8(5) . . ?
N8_1 C10_1 H10_1 111.4 . . ?
N8_1 C10_1 C11_1 102.6(4) . . ?
C10_1 C11_1 H11_1 111.7 . . ?
N12_1 C11_1 C10_1 102.4(4) . . ?
N12_1 C11_1 H11_1 111.7 . . ?
N9_1 C11_1 C10_1 103.4(4) . . ?
N9_1 C11_1 H11_1 111.7 . . ?
N9_1 C11_1 N12_1 115.2(5) . . ?
C13_1 N12_1 C11_1 112.9(4) . . ?
C13_1 N12_1 C22_1 121.3(5) . . ?
C22_1 N12_1 C11_1 122.3(5) . . ?
N12_1 C13_1 N7_1 107.6(5) . . ?
O4_1 C13_1 N12_1 127.2(5) . . ?
O4_1 C13_1 N7_1 125.1(5) . . ?
H14A_1 C14_1 H14B_1 107.7 . . ?
N3_1 C14_1 H14A_1 108.9 3_665 . ?
N3_1 C14_1 H14B_1 108.9 3_665 . ?
N3_1 C14_1 N8_1 113.2(4) 3_665 . ?
N8_1 C14_1 H14A_1 108.9 . . ?
N8_1 C14_1 H14B_1 108.9 . . ?
N9_1 C15_1 N8_1 107.9(5) . . ?
O5_1 C15_1 N8_1 126.5(5) . . ?
O5_1 C15_1 N9_1 125.5(5) . . ?
H16A_1 C16_1 H16B_1 107.7 . . ?
N4_1 C16_1 H16A_1 108.8 . . ?
N4_1 C16_1 H16B_1 108.8 . . ?
N4_1 C16_1 N10_1 113.9(4) . . ?
N10_1 C16_1 H16A_1 108.8 . . ?
N10_1 C16_1 H16B_1 108.8 . . ?
N10_1 C17_1 N11_1 107.6(5) . . ?
O6_1 C17_1 N10_1 127.2(5) . . ?
O6_1 C17_1 N11_1 125.2(5) . . ?
H18A_1 C18_1 H18B_1 107.7 . . ?
N6_1 C18_1 H18A_1 108.9 . . ?
N6_1 C18_1 H18B_1 108.9 . . ?
N16_1 C18_1 H18A_1 108.9 . . ?
N16_1 C18_1 H18B_1 108.9 . . ?
N16_1 C18_1 N6_1 113.4(4) . . ?
C20_1 C19_1 H19_1 111.8 . . ?
N16_1 C19_1 H19_1 111.8 . . ?
N16_1 C19_1 C20_1 103.5(4) . . ?
N15_1 C19_1 H19_1 111.8 . . ?
N15_1 C19_1 C20_1 102.8(4) . . ?
N15_1 C19_1 N16_1 114.5(4) . . ?
C19_1 C20_1 H20_1 111.5 . . ?
N13_1 C20_1 C19_1 103.2(4) . . ?
N13_1 C20_1 H20_1 111.5 . . ?
N13_1 C20_1 N14_1 114.9(4) . . ?
N14_1 C20_1 C19_1 103.7(4) . . ?
N14_1 C20_1 H20_1 111.5 . . ?
N13_1 C21_1 N16_1 108.4(5) . . ?
O7_1 C21_1 N16_1 125.5(5) . . ?
O7_1 C21_1 N13_1 126.0(5) . . ?
N12_1 C22_1 H22A_1 109.1 . . ?
N12_1 C22_1 H22B_1 109.1 . . ?
H22A_1 C22_1 H22B_1 107.8 . . ?
N14_1 C22_1 N12_1 112.7(5) . . ?
N14_1 C22_1 H22A_1 109.1 . . ?
N14_1 C22_1 H22B_1 109.1 . . ?
N15_1 C23_1 N14_1 108.2(5) . . ?
O8_1 C23_1 N14_1 124.1(5) . . ?
O8_1 C23_1 N15_1 127.7(5) . . ?
H24A_1 C24_1 H24B_1 107.7 . . ?
N9_1 C24_1 H24A_1 108.9 . . ?
N9_1 C24_1 H24B_1 108.9 . . ?
N9_1 C24_1 N13_1 113.2(4) . . ?
N13_1 C24_1 H24A_1 108.9 . . ?
N13_1 C24_1 H24B_1 108.9 . . ?
H25A_1 C25_1 H25B_1 107.9 . . ?
N11_1 C25_1 H25A_1 109.1 . . ?
N11_1 C25_1 H25B_1 109.1 . . ?
N11_1 C25_1 N15_1 112.4(5) . . ?
N15_1 C25_1 H25A_1 109.1 . . ?
N15_1 C25_1 H25B_1 109.1 . . ?
C1_1 N1_1 C3_1 110.5(4) . . ?
C1_1 N1_1 C5_1 120.6(5) . . ?
C5_1 N1_1 C3_1 120.8(4) . . ?
C1_1 N2_1 C2_1 112.3(4) . . ?
C1_1 N2_1 C9_1 121.7(5) . . ?
C2_1 N2_1 C9_1 122.6(5) . . ?
C4_1 N3_1 C2_1 112.5(4) . . ?
C4_1 N3_1 C14_1 121.4(5) . 3_665 ?
C14_1 N3_1 C2_1 121.6(5) 3_665 . ?
C3_1 N4_1 C16_1 120.4(5) . . ?
C4_1 N4_1 C3_1 113.4(4) . . ?
C4_1 N4_1 C16_1 123.1(5) . . ?
C5_1 N5_1 C6_1 124.1(4) . . ?
C8_1 N5_1 C5_1 122.0(5) . . ?
C8_1 N5_1 C6_1 112.5(4) . . ?
C8_1 N6_1 C7_1 111.1(4) . . ?
C8_1 N6_1 C18_1 121.1(4) . . ?
C18_1 N6_1 C7_1 122.3(4) . . ?
C9_1 N7_1 C10_1 125.2(5) 3_665 . ?
C13_1 N7_1 C9_1 121.9(5) . 3_665 ?
C13_1 N7_1 C10_1 112.7(5) . . ?
C10_1 N8_1 C14_1 122.6(5) . . ?
C15_1 N8_1 C10_1 112.2(4) . . ?
C15_1 N8_1 C14_1 120.5(4) . . ?
C11_1 N9_1 C24_1 124.4(5) . . ?
C15_1 N9_1 C11_1 112.8(4) . . ?
C15_1 N9_1 C24_1 122.5(5) . . ?
C6_1 N10_1 C16_1 122.6(5) . . ?
C17_1 N10_1 C6_1 112.6(4) . . ?
C17_1 N10_1 C16_1 120.6(5) . . ?
C7_1 N11_1 C25_1 123.4(5) . . ?
C17_1 N11_1 C7_1 112.8(4) . . ?
C17_1 N11_1 C25_1 122.7(5) . . ?
C18_1 N16_1 C19_1 121.9(4) . . ?
C21_1 N16_1 C18_1 122.7(5) . . ?
C21_1 N16_1 C19_1 110.4(4) . . ?
C20_1 N13_1 C24_1 120.6(5) . . ?
C21_1 N13_1 C20_1 113.3(4) . . ?
C21_1 N13_1 C24_1 123.6(5) . . ?
C22_1 N14_1 C20_1 122.9(5) . . ?
C23_1 N14_1 C20_1 110.9(4) . . ?
C23_1 N14_1 C22_1 121.6(5) . . ?
C19_1 N15_1 C25_1 120.7(5) . . ?
C23_1 N15_1 C19_1 113.5(4) . . ?
C23_1 N15_1 C25_1 123.0(5) . . ?
C2_2 C1_2 H1_2 119.5 . . ?
C2_2 C1_2 N1_2 120.9(8) . . ?
N1_2 C1_2 H1_2 119.5 . . ?
C1_2 C2_2 H2_2 118.6 . . ?
C1_2 C2_2 C3_2 122.7(8) . . ?
C3_2 C2_2 H2_2 118.6 . . ?
C2_2 C3_2 C4_2 115.2(7) . . ?
O1_2 C3_2 C2_2 121.9(7) . . ?
O1_2 C3_2 C4_2 122.9(8) . . ?
C3_2 C4_2 H4_2 119.8 . . ?
C5_2 C4_2 C3_2 120.4(8) . . ?
C5_2 C4_2 H4_2 119.8 . . ?
C4_2 C5_2 H5_2 118.4 . . ?
C4_2 C5_2 N1_2 123.2(8) . . ?
N1_2 C5_2 H5_2 118.4 . . ?
C7_2 C6_2 N1_2 120.9(8) . . ?
C11_2 C6_2 C7_2 117.4(8) . . ?
C11_2 C6_2 N1_2 121.6(9) . . ?
C6_2 C7_2 C8_2 119.0(9) . . ?
N2_2 C7_2 C6_2 130.0(9) . . ?
N2_2 C7_2 C8_2 110.7(9) . . ?
C9_2 C8_2 C7_2 116.5(9) . . ?
N3_2 C8_2 C7_2 103.3(9) . . ?
N3_2 C8_2 C9_2 139.8(10) . . ?
C8_2 C9_2 N4_2 114.6(10) . . ?
C10_2 C9_2 C8_2 124.3(10) . . ?
C10_2 C9_2 N4_2 121.1(10) . . ?
C9_2 C10_2 H10_2 120.0 . . ?
C9_2 C10_2 C11_2 119.9(11) . . ?
C11_2 C10_2 H10_2 120.0 . . ?
C6_2 C11_2 C10_2 122.6(11) . . ?
C6_2 C11_2 H11_2 118.7 . . ?
C10_2 C11_2 H11_2 118.7 . . ?
C1_2 N1_2 C6_2 119.5(7) . . ?
C5_2 N1_2 C1_2 117.4(6) . . ?
C5_2 N1_2 C6_2 123.1(7) . . ?
C7_2 N2_2 O2_2 104.5(8) . . ?
C8_2 N3_2 O2_2 108.7(8) . . ?
O3_2 N4_2 C9_2 116.2(12) . . ?
O4_2 N4_2 C9_2 118.4(10) . . ?
O4_2 N4_2 O3_2 125.3(11) . . ?
N3_2 O2_2 N2_2 112.9(7) . . ?

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
C2_1 C3_1 N1_1 C1_1 -9.1(6) . . . . ?
C2_1 C3_1 N1_1 C5_1 -157.9(5) . . . . ?
C2_1 C3_1 N4_1 C4_1 2.1(6) . . . . ?
C2_1 C3_1 N4_1 C16_1 162.6(4) . . . . ?
C3_1 C2_1 N2_1 C1_1 3.5(6) . . . . ?
C3_1 C2_1 N2_1 C9_1 162.9(5) . . . . ?
C3_1 C2_1 N3_1 C4_1 -7.3(6) . . . . ?
C3_1 C2_1 N3_1 C14_1 -163.8(4) . . . 3_665 ?
C6_1 C7_1 N6_1 C8_1 -10.5(6) . . . . ?
C6_1 C7_1 N6_1 C18_1 -164.7(5) . . . . ?
C6_1 C7_1 N11_1 C17_1 -2.7(6) . . . . ?
C6_1 C7_1 N11_1 C25_1 166.2(5) . . . . ?
C7_1 C6_1 N5_1 C5_1 166.6(5) . . . . ?
C7_1 C6_1 N5_1 C8_1 -0.3(6) . . . . ?
C7_1 C6_1 N10_1 C16_1 -163.2(4) . . . . ?
C7_1 C6_1 N10_1 C17_1 -6.0(6) . . . . ?
C10_1 C11_1 N12_1 C13_1 -7.7(6) . . . . ?
C10_1 C11_1 N12_1 C22_1 -166.8(5) . . . . ?
C10_1 C11_1 N9_1 C15_1 -4.2(6) . . . . ?
C10_1 C11_1 N9_1 C24_1 169.6(5) . . . . ?
C11_1 C10_1 N7_1 C9_1 167.4(5) . . . 3_665 ?
C11_1 C10_1 N7_1 C13_1 -8.3(6) . . . . ?
C11_1 C10_1 N8_1 C14_1 -165.9(5) . . . . ?
C11_1 C10_1 N8_1 C15_1 -10.3(6) . . . . ?
C11_1 N12_1 C13_1 N7_1 3.0(6) . . . . ?
C11_1 N12_1 C13_1 O4_1 -176.4(6) . . . . ?
C11_1 N12_1 C22_1 N14_1 -85.8(6) . . . . ?
N12_1 C11_1 N9_1 C15_1 106.7(5) . . . . ?
N12_1 C11_1 N9_1 C24_1 -79.5(6) . . . . ?
N12_1 C13_1 N7_1 C9_1 -172.1(5) . . . 3_665 ?
N12_1 C13_1 N7_1 C10_1 3.8(6) . . . . ?
N12_1 C22_1 N14_1 C20_1 84.9(6) . . . . ?
N12_1 C22_1 N14_1 C23_1 -121.4(6) . . . . ?
C13_1 N12_1 C22_1 N14_1 116.8(6) . . . . ?
C19_1 C20_1 N13_1 C21_1 -0.8(6) . . . . ?
C19_1 C20_1 N13_1 C24_1 -163.4(5) . . . . ?
C19_1 C20_1 N14_1 C22_1 164.7(5) . . . . ?
C19_1 C20_1 N14_1 C23_1 8.6(6) . . . . ?
C20_1 C19_1 N16_1 C18_1 165.8(4) . . . . ?
C20_1 C19_1 N16_1 C21_1 10.3(6) . . . . ?
C20_1 C19_1 N15_1 C23_1 -0.1(6) . . . . ?
C20_1 C19_1 N15_1 C25_1 -161.6(5) . . . . ?
C22_1 N12_1 C13_1 N7_1 162.3(5) . . . . ?
C22_1 N12_1 C13_1 O4_1 -17.1(9) . . . . ?
N1_1 C1_1 N2_1 C2_1 -9.5(6) . . . . ?
N1_1 C1_1 N2_1 C9_1 -169.1(5) . . . . ?
N1_1 C3_1 N4_1 C4_1 114.4(5) . . . . ?
N1_1 C3_1 N4_1 C16_1 -85.1(6) . . . . ?
N1_1 C5_1 N5_1 C6_1 79.9(6) . . . . ?
N1_1 C5_1 N5_1 C8_1 -114.4(6) . . . . ?
N2_1 C1_1 N1_1 C3_1 11.7(6) . . . . ?
N2_1 C1_1 N1_1 C5_1 160.5(5) . . . . ?
N2_1 C2_1 C3_1 N1_1 3.3(5) . . . . ?
N2_1 C2_1 C3_1 N4_1 123.0(4) . . . . ?
N2_1 C2_1 N3_1 C4_1 -118.8(5) . . . . ?
N2_1 C2_1 N3_1 C14_1 84.7(6) . . . 3_665 ?
N3_1 C2_1 C3_1 N1_1 -116.6(4) . . . . ?
N3_1 C2_1 C3_1 N4_1 3.0(5) . . . . ?
N3_1 C2_1 N2_1 C1_1 115.1(5) . . . . ?
N3_1 C2_1 N2_1 C9_1 -85.5(6) . . . . ?
N3_1 C4_1 N4_1 C3_1 -6.6(6) . . . . ?
N3_1 C4_1 N4_1 C16_1 -166.5(5) . . . . ?
N3_1 C14_1 N8_1 C10_1 -84.4(6) 3_665 . . . ?
N3_1 C14_1 N8_1 C15_1 121.9(5) 3_665 . . . ?
N4_1 C3_1 N1_1 C1_1 -120.9(5) . . . . ?
N4_1 C3_1 N1_1 C5_1 90.3(6) . . . . ?
N4_1 C4_1 N3_1 C2_1 8.8(6) . . . . ?
N4_1 C4_1 N3_1 C14_1 165.3(5) . . . 3_665 ?
N4_1 C16_1 N10_1 C6_1 -84.5(6) . . . . ?
N4_1 C16_1 N10_1 C17_1 120.1(6) . . . . ?
N5_1 C5_1 N1_1 C1_1 128.9(5) . . . . ?
N5_1 C5_1 N1_1 C3_1 -85.4(6) . . . . ?
N5_1 C6_1 C7_1 N6_1 6.2(5) . . . . ?
N5_1 C6_1 C7_1 N11_1 125.9(4) . . . . ?
N5_1 C6_1 N10_1 C16_1 84.4(6) . . . . ?
N5_1 C6_1 N10_1 C17_1 -118.5(5) . . . . ?
N5_1 C8_1 N6_1 C7_1 10.6(6) . . . . ?
N5_1 C8_1 N6_1 C18_1 165.2(5) . . . . ?
N6_1 C7_1 N11_1 C17_1 109.3(5) . . . . ?
N6_1 C7_1 N11_1 C25_1 -81.9(6) . . . . ?
N6_1 C8_1 N5_1 C5_1 -173.5(5) . . . . ?
N6_1 C8_1 N5_1 C6_1 -6.2(6) . . . . ?
N6_1 C18_1 N16_1 C19_1 82.8(6) . . . . ?
N6_1 C18_1 N16_1 C21_1 -124.7(5) . . . . ?
N7_1 C9_1 N2_1 C1_1 -120.1(6) 3_665 . . . ?
N7_1 C9_1 N2_1 C2_1 82.5(6) 3_665 . . . ?
N7_1 C10_1 C11_1 N12_1 9.1(5) . . . . ?
N7_1 C10_1 C11_1 N9_1 129.2(5) . . . . ?
N7_1 C10_1 N8_1 C14_1 82.2(6) . . . . ?
N7_1 C10_1 N8_1 C15_1 -122.2(5) . . . . ?
N8_1 C10_1 C11_1 N12_1 -111.7(5) . . . . ?
N8_1 C10_1 C11_1 N9_1 8.4(5) . . . . ?
N8_1 C10_1 N7_1 C9_1 -81.2(7) . . . 3_665 ?
N8_1 C10_1 N7_1 C13_1 103.1(5) . . . . ?
N8_1 C15_1 N9_1 C11_1 -2.0(6) . . . . ?
N8_1 C15_1 N9_1 C24_1 -176.0(5) . . . . ?
N9_1 C11_1 N12_1 C13_1 -119.2(5) . . . . ?
N9_1 C11_1 N12_1 C22_1 81.7(6) . . . . ?
N9_1 C15_1 N8_1 C10_1 8.2(6) . . . . ?
N9_1 C15_1 N8_1 C14_1 164.4(5) . . . . ?
N9_1 C24_1 N13_1 C20_1 -86.0(6) . . . . ?
N9_1 C24_1 N13_1 C21_1 113.3(6) . . . . ?
N10_1 C6_1 C7_1 N6_1 -114.7(4) . . . . ?
N10_1 C6_1 C7_1 N11_1 5.0(5) . . . . ?
N10_1 C6_1 N5_1 C5_1 -80.8(6) . . . . ?
N10_1 C6_1 N5_1 C8_1 112.3(5) . . . . ?
N10_1 C16_1 N4_1 C3_1 81.2(6) . . . . ?
N10_1 C16_1 N4_1 C4_1 -120.2(6) . . . . ?
N10_1 C17_1 N11_1 C7_1 -0.9(6) . . . . ?
N10_1 C17_1 N11_1 C25_1 -169.9(5) . . . . ?
N11_1 C7_1 N6_1 C8_1 -121.9(5) . . . . ?
N11_1 C7_1 N6_1 C18_1 83.8(6) . . . . ?
N11_1 C17_1 N10_1 C6_1 4.6(6) . . . . ?
N11_1 C17_1 N10_1 C16_1 162.2(5) . . . . ?
N11_1 C25_1 N15_1 C19_1 -87.0(6) . . . . ?
N11_1 C25_1 N15_1 C23_1 113.3(6) . . . . ?
N16_1 C18_1 N6_1 C7_1 -85.9(6) . . . . ?
N16_1 C18_1 N6_1 C8_1 122.3(5) . . . . ?
N16_1 C19_1 C20_1 N13_1 -5.6(5) . . . . ?
N16_1 C19_1 C20_1 N14_1 114.6(4) . . . . ?
N16_1 C19_1 N15_1 C23_1 -111.7(5) . . . . ?
N16_1 C19_1 N15_1 C25_1 86.8(6) . . . . ?
N16_1 C21_1 N13_1 C20_1 7.4(6) . . . . ?
N16_1 C21_1 N13_1 C24_1 169.4(5) . . . . ?
N13_1 C20_1 N14_1 C22_1 -83.4(6) . . . . ?
N13_1 C20_1 N14_1 C23_1 120.4(5) . . . . ?
N13_1 C21_1 N16_1 C18_1 -166.5(5) . . . . ?
N13_1 C21_1 N16_1 C19_1 -11.2(6) . . . . ?
N13_1 C24_1 N9_1 C11_1 83.6(7) . . . . ?
N13_1 C24_1 N9_1 C15_1 -103.2(6) . . . . ?
N14_1 C20_1 N13_1 C21_1 -113.0(5) . . . . ?
N14_1 C20_1 N13_1 C24_1 84.5(6) . . . . ?
N14_1 C23_1 N15_1 C19_1 5.5(6) . . . . ?
N14_1 C23_1 N15_1 C25_1 166.5(5) . . . . ?
N15_1 C19_1 C20_1 N13_1 -125.1(4) . . . . ?
N15_1 C19_1 C20_1 N14_1 -5.0(5) . . . . ?
N15_1 C19_1 N16_1 C18_1 -83.0(6) . . . . ?
N15_1 C19_1 N16_1 C21_1 121.5(5) . . . . ?
N15_1 C23_1 N14_1 C20_1 -9.0(6) . . . . ?
N15_1 C23_1 N14_1 C22_1 -165.5(5) . . . . ?
N15_1 C25_1 N11_1 C7_1 83.9(7) . . . . ?
N15_1 C25_1 N11_1 C17_1 -108.3(6) . . . . ?
O1_1 C1_1 N1_1 C3_1 -169.6(5) . . . . ?
O1_1 C1_1 N1_1 C5_1 -20.7(9) . . . . ?
O1_1 C1_1 N2_1 C2_1 171.8(6) . . . . ?
O1_1 C1_1 N2_1 C9_1 12.2(9) . . . . ?
O2_1 C4_1 N3_1 C2_1 -172.5(5) . . . . ?
O2_1 C4_1 N3_1 C14_1 -15.9(8) . . . 3_665 ?
O2_1 C4_1 N4_1 C3_1 174.7(5) . . . . ?
O2_1 C4_1 N4_1 C16_1 14.8(9) . . . . ?
O3_1 C8_1 N5_1 C5_1 6.2(9) . . . . ?
O3_1 C8_1 N5_1 C6_1 173.4(5) . . . . ?
O3_1 C8_1 N6_1 C7_1 -169.0(6) . . . . ?
O3_1 C8_1 N6_1 C18_1 -14.4(9) . . . . ?
O4_1 C13_1 N7_1 C9_1 7.4(9) . . . 3_665 ?
O4_1 C13_1 N7_1 C10_1 -176.7(5) . . . . ?
O5_1 C15_1 N8_1 C10_1 -171.5(5) . . . . ?
O5_1 C15_1 N8_1 C14_1 -15.3(8) . . . . ?
O5_1 C15_1 N9_1 C11_1 177.7(5) . . . . ?
O5_1 C15_1 N9_1 C24_1 3.7(9) . . . . ?
O6_1 C17_1 N10_1 C6_1 -174.6(5) . . . . ?
O6_1 C17_1 N10_1 C16_1 -16.9(8) . . . . ?
O6_1 C17_1 N11_1 C7_1 178.3(5) . . . . ?
O6_1 C17_1 N11_1 C25_1 9.3(8) . . . . ?
O7_1 C21_1 N16_1 C18_1 14.4(9) . . . . ?
O7_1 C21_1 N16_1 C19_1 169.7(5) . . . . ?
O7_1 C21_1 N13_1 C20_1 -173.5(5) . . . . ?
O7_1 C21_1 N13_1 C24_1 -11.6(9) . . . . ?
O8_1 C23_1 N14_1 C20_1 171.8(5) . . . . ?
O8_1 C23_1 N14_1 C22_1 15.3(9) . . . . ?
O8_1 C23_1 N15_1 C19_1 -175.3(6) . . . . ?
O8_1 C23_1 N15_1 C25_1 -14.4(9) . . . . ?
C1_2 C2_2 C3_2 C4_2 1.9(11) . . . . ?
C1_2 C2_2 C3_2 O1_2 -176.5(7) . . . . ?
C2_2 C1_2 N1_2 C5_2 -2.6(10) . . . . ?
C2_2 C1_2 N1_2 C6_2 177.9(7) . . . . ?
C2_2 C3_2 C4_2 C5_2 -1.8(10) . . . . ?
C3_2 C4_2 C5_2 N1_2 -0.5(11) . . . . ?
C4_2 C5_2 N1_2 C1_2 2.7(10) . . . . ?
C4_2 C5_2 N1_2 C6_2 -177.8(7) . . . . ?
C6_2 C7_2 C8_2 C9_2 0.9(11) . . . . ?
C6_2 C7_2 C8_2 N3_2 174.3(7) . . . . ?
C6_2 C7_2 N2_2 O2_2 -174.2(8) . . . . ?
C7_2 C6_2 C11_2 C10_2 -5.5(13) . . . . ?
C7_2 C6_2 N1_2 C1_2 149.6(7) . . . . ?
C7_2 C6_2 N1_2 C5_2 -29.9(10) . . . . ?
C7_2 C8_2 C9_2 C10_2 -2.7(13) . . . . ?
C7_2 C8_2 C9_2 N4_2 174.6(7) . . . . ?
C7_2 C8_2 N3_2 O2_2 1.3(9) . . . . ?
C7_2 N2_2 O2_2 N3_2 0.1(11) . . . . ?
C8_2 C7_2 N2_2 O2_2 0.8(10) . . . . ?
C8_2 C9_2 C10_2 C11_2 0.4(15) . . . . ?
C8_2 C9_2 N4_2 O3_2 -167.1(9) . . . . ?
C8_2 C9_2 N4_2 O4_2 8.6(12) . . . . ?
C8_2 N3_2 O2_2 N2_2 -1.0(11) . . . . ?
C9_2 C8_2 N3_2 O2_2 172.1(10) . . . . ?
C9_2 C10_2 C11_2 C6_2 4.0(15) . . . . ?
C10_2 C9_2 N4_2 O3_2 10.2(13) . . . . ?
C10_2 C9_2 N4_2 O4_2 -174.0(9) . . . . ?
C11_2 C6_2 C7_2 C8_2 3.0(11) . . . . ?
C11_2 C6_2 C7_2 N2_2 177.6(9) . . . . ?
C11_2 C6_2 N1_2 C1_2 -29.5(10) . . . . ?
C11_2 C6_2 N1_2 C5_2 151.0(8) . . . . ?
N1_2 C1_2 C2_2 C3_2 0.3(12) . . . . ?
N1_2 C6_2 C7_2 C8_2 -176.1(6) . . . . ?
N1_2 C6_2 C7_2 N2_2 -1.5(14) . . . . ?
N1_2 C6_2 C11_2 C10_2 173.6(8) . . . . ?
N2_2 C7_2 C8_2 C9_2 -174.7(8) . . . . ?
N2_2 C7_2 C8_2 N3_2 -1.4(10) . . . . ?
N3_2 C8_2 C9_2 C10_2 -172.7(11) . . . . ?
N3_2 C8_2 C9_2 N4_2 4.6(16) . . . . ?
N4_2 C9_2 C10_2 C11_2 -176.7(8) . . . . ?
O1_2 C3_2 C4_2 C5_2 176.6(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_t
_database_code_depnum_ccdc_archive 'CCDC 2107309'
loop_
_audit_author_name
_audit_author_address
'XIE HAN'
;WUST
China
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_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         'C11 H6 N4 O4'
_chemical_formula_sum            'C11 H6 N4 O4'
_chemical_formula_weight         258.20
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7743(5)
_cell_length_b                   11.8277(7)
_cell_length_c                   21.4669(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2227.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2285
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.91
_cell_measurement_theta_min      2.85
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.597
_diffrn_reflns_theta_min         1.897
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1394
_reflns_number_total             2319
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0021(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.004
_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)+(0.0496P)²+0.3126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1123
_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), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8) 
;
_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
C1 C 0.6242(2) 0.89079(14) 0.55423(9) 0.0542(5) Uani 1 1 d . . . . .
H1 H 0.6493 0.9267 0.5914 0.065 Uiso 1 1 calc R . . . .
C2 C 0.6681(2) 0.93732(15) 0.50017(10) 0.0585(5) Uani 1 1 d . . . . .
H2 H 0.7252 1.0035 0.5010 0.070 Uiso 1 1 calc R . . . .
C3 C 0.6301(2) 0.88843(16) 0.44110(10) 0.0578(5) Uani 1 1 d . . . . .
C4 C 0.5535(3) 0.78206(17) 0.44612(10) 0.0677(6) Uani 1 1 d . . . . .
H4 H 0.5312 0.7422 0.4099 0.081 Uiso 1 1 calc R . . . .
C5 C 0.5126(3) 0.73771(17) 0.50103(9) 0.0648(6) Uani 1 1 d . . . . .
H5 H 0.4621 0.6686 0.5018 0.078 Uiso 1 1 calc R . . . .
C6 C 0.4853(2) 0.74997(15) 0.61355(8) 0.0508(5) Uani 1 1 d . . . . .
C7 C 0.4289(2) 0.81997(16) 0.65787(9) 0.0597(5) Uani 1 1 d . . . . .
H7 H 0.4217 0.8969 0.6495 0.072 Uiso 1 1 calc R . . . .
C8 C 0.3806(2) 0.77883(17) 0.71656(9) 0.0621(5) Uani 1 1 d . . . . .
H8 H 0.3442 0.8299 0.7460 0.075 Uiso 1 1 calc R . . . .
C9 C 0.3856(2) 0.66751(16) 0.73123(9) 0.0550(5) Uani 1 1 d . . . . .
C10 C 0.4398(2) 0.58985(15) 0.68574(9) 0.0530(5) Uani 1 1 d . . . . .
C11 C 0.4887(2) 0.63161(15) 0.62715(9) 0.0504(5) Uani 1 1 d . . . . .
N1 N 0.54305(17) 0.79150(12) 0.55616(7) 0.0518(4) Uani 1 1 d . . . . .
N2 N 0.5366(2) 0.54745(13) 0.59261(8) 0.0680(5) Uani 1 1 d . . . . .
N3 N 0.4573(2) 0.47960(14) 0.68741(9) 0.0716(5) Uani 1 1 d . . . . .
N4 N 0.3345(2) 0.62887(18) 0.79200(8) 0.0710(5) Uani 1 1 d . . . . .
O1 O 0.66064(17) 0.93287(12) 0.39023(7) 0.0760(5) Uani 1 1 d . . . . .
O2 O 0.5168(2) 0.45387(12) 0.62956(8) 0.0829(5) Uani 1 1 d . . . . .
O3 O 0.3253(2) 0.52687(16) 0.80033(8) 0.0981(6) Uani 1 1 d . . . . .
O4 O 0.30192(19) 0.70062(16) 0.83110(8) 0.0930(6) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.341(3) . ?
C1 N1 1.374(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.433(3) . ?
C3 C4 1.430(3) . ?
C3 O1 1.241(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.339(3) . ?
C5 H5 0.9300 . ?
C5 N1 1.370(2) . ?
C6 C7 1.355(2) . ?
C6 C11 1.430(2) . ?
C6 N1 1.420(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.416(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.355(3) . ?
C9 C10 1.422(3) . ?
C9 N4 1.453(2) . ?
C10 C11 1.418(3) . ?
C10 N3 1.314(2) . ?
C11 N2 1.311(2) . ?
N2 O2 1.373(2) . ?
N3 O2 1.381(2) . ?
N4 O3 1.222(2) . ?
N4 O4 1.227(2) . ?

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
C2 C1 H1 119.1 . . ?
C2 C1 N1 121.72(18) . . ?
N1 C1 H1 119.1 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.22(17) . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 113.44(18) . . ?
O1 C3 C2 123.86(18) . . ?
O1 C3 C4 122.7(2) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 C3 122.46(19) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 N1 121.74(18) . . ?
N1 C5 H5 119.1 . . ?
C7 C6 C11 117.54(17) . . ?
C7 C6 N1 121.89(17) . . ?
N1 C6 C11 120.56(16) . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.63(18) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.08(18) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 118.62(17) . . ?
C8 C9 N4 120.28(19) . . ?
C10 C9 N4 121.09(18) . . ?
C11 C10 C9 119.03(17) . . ?
N3 C10 C9 131.40(19) . . ?
N3 C10 C11 109.57(18) . . ?
C10 C11 C6 121.05(17) . . ?
N2 C11 C6 129.38(19) . . ?
N2 C11 C10 109.54(17) . . ?
C1 N1 C6 120.45(15) . . ?
C5 N1 C1 118.17(16) . . ?
C5 N1 C6 121.28(15) . . ?
C11 N2 O2 104.16(16) . . ?
C10 N3 O2 103.78(16) . . ?
O3 N4 C9 117.5(2) . . ?
O3 N4 O4 124.54(19) . . ?
O4 N4 C9 117.93(19) . . ?
N2 O2 N3 112.95(14) . . ?

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 C2 C3 C4 -5.0(3) . . . . ?
C1 C2 C3 O1 175.35(19) . . . . ?
C2 C1 N1 C5 2.6(3) . . . . ?
C2 C1 N1 C6 -173.83(17) . . . . ?
C2 C3 C4 C5 4.5(3) . . . . ?
C3 C4 C5 N1 -0.6(3) . . . . ?
C4 C5 N1 C1 -3.1(3) . . . . ?
C4 C5 N1 C6 173.2(2) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C11 N2 O2 178.47(18) . . . . ?
C7 C6 C11 C10 -2.2(3) . . . . ?
C7 C6 C11 N2 179.80(19) . . . . ?
C7 C6 N1 C1 37.7(3) . . . . ?
C7 C6 N1 C5 -138.7(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 N4 -179.85(18) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 N3 179.6(2) . . . . ?
C8 C9 N4 O3 171.91(19) . . . . ?
C8 C9 N4 O4 -7.2(3) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C9 C10 C11 N2 178.83(17) . . . . ?
C9 C10 N3 O2 -178.88(19) . . . . ?
C10 C9 N4 O3 -7.2(3) . . . . ?
C10 C9 N4 O4 173.67(18) . . . . ?
C10 C11 N2 O2 0.3(2) . . . . ?
C10 N3 O2 N2 0.3(2) . . . . ?
C11 C6 C7 C8 2.5(3) . . . . ?
C11 C6 N1 C1 -140.67(17) . . . . ?
C11 C6 N1 C5 43.0(3) . . . . ?
C11 C10 N3 O2 -0.1(2) . . . . ?
C11 N2 O2 N3 -0.4(2) . . . . ?
N1 C1 C2 C3 1.7(3) . . . . ?
N1 C6 C7 C8 -175.86(17) . . . . ?
N1 C6 C11 C10 176.20(16) . . . . ?
N1 C6 C11 N2 -1.8(3) . . . . ?
N3 C10 C11 C6 -178.47(17) . . . . ?
N3 C10 C11 N2 -0.1(2) . . . . ?
N4 C9 C10 C11 -179.88(17) . . . . ?
N4 C9 C10 N3 -1.2(3) . . . . ?
O1 C3 C4 C5 -175.9(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_t_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2107308'
loop_
_audit_author_name
_audit_author_address
'XIE HAN'
;WUST
China
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-08-04
_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         'C11 H6 N4 O4, H2 O'
_chemical_formula_sum            'C11 H8 N4 O5'
_chemical_formula_weight         276.21
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.774(2)
_cell_length_b                   6.9990(11)
_cell_length_c                   23.662(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2281.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4307
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            16732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.435
_diffrn_reflns_theta_min         2.269
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2364
_reflns_number_total             3339
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.041
_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          0.1368
_refine_ls_wR_factor_ref         0.1533
_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.a Free rotating group: 
 O5(H5A,H5B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8) 
;
_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
C1 C 0.48341(10) -0.14509(18) 0.43934(6) 0.0384(3) Uani 1 1 d . . . . .
H1 H 0.4183 -0.1526 0.4292 0.046 Uiso 1 1 calc R . . . .
C2 C 0.51587(11) -0.2520(2) 0.48227(6) 0.0420(3) Uani 1 1 d . . . . .
H2 H 0.4732 -0.3350 0.5003 0.050 Uiso 1 1 calc R . . . .
C3 C 0.61479(11) -0.2419(2) 0.50119(6) 0.0430(3) Uani 1 1 d . . . . .
C4 C 0.67607(11) -0.1226(2) 0.46722(6) 0.0436(3) Uani 1 1 d . . . . .
H4 H 0.7420 -0.1163 0.4754 0.052 Uiso 1 1 calc R . . . .
C5 C 0.64059(10) -0.0191(2) 0.42365(6) 0.0395(3) Uani 1 1 d . . . . .
H5 H 0.6826 0.0571 0.4027 0.047 Uiso 1 1 calc R . . . .
C6 C 0.50409(9) 0.09960(19) 0.36817(5) 0.0333(3) Uani 1 1 d . . . . .
C7 C 0.42727(10) 0.0476(2) 0.33539(6) 0.0397(3) Uani 1 1 d . . . . .
H7 H 0.4037 -0.0767 0.3377 0.048 Uiso 1 1 calc R . . . .
C8 C 0.38218(10) 0.1791(2) 0.29773(6) 0.0410(3) Uani 1 1 d . . . . .
H8 H 0.3300 0.1379 0.2760 0.049 Uiso 1 1 calc R . . . .
C9 C 0.41280(9) 0.3620(2) 0.29258(5) 0.0371(3) Uani 1 1 d . . . . .
C10 C 0.49423(9) 0.42324(18) 0.32482(5) 0.0336(3) Uani 1 1 d . . . . .
C11 C 0.53982(9) 0.29094(19) 0.36217(5) 0.0326(3) Uani 1 1 d . . . . .
N1 N 0.54386(8) -0.02403(16) 0.40970(4) 0.0344(3) Uani 1 1 d . . . . .
N2 N 0.61299(9) 0.37516(18) 0.38737(5) 0.0412(3) Uani 1 1 d . . . . .
N3 N 0.54070(9) 0.58758(18) 0.32722(5) 0.0429(3) Uani 1 1 d . . . . .
N4 N 0.36402(9) 0.4924(2) 0.25419(6) 0.0470(3) Uani 1 1 d . . . . .
O1 O 0.64442(10) -0.32847(19) 0.54424(5) 0.0618(4) Uani 1 1 d . . . . .
O2 O 0.61411(8) 0.55652(15) 0.36577(5) 0.0472(3) Uani 1 1 d . . . . .
O3 O 0.38896(9) 0.6601(2) 0.25498(5) 0.0594(3) Uani 1 1 d . . . . .
O4 O 0.30156(10) 0.4287(2) 0.22305(7) 0.0776(4) Uani 1 1 d . . . . .
O5 O 0.70576(10) -0.6439(2) 0.61224(6) 0.0680(4) Uani 1 1 d . . . . .
H5A H 0.6895 -0.5499 0.5916 0.102 Uiso 1 1 d G . . . .
H5B H 0.7492 -0.7016 0.5933 0.102 Uiso 1 1 d G . . . .


_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 H1 0.9300 . ?
C1 C2 1.339(2) . ?
C1 N1 1.3794(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.436(2) . ?
C3 C4 1.434(2) . ?
C3 O1 1.2533(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.352(2) . ?
C5 H5 0.9300 . ?
C5 N1 1.3730(18) . ?
C6 C7 1.3613(18) . ?
C6 C11 1.4337(18) . ?
C6 N1 1.4195(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.424(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.354(2) . ?
C9 C10 1.4225(19) . ?
C9 N4 1.4525(18) . ?
C10 C11 1.4259(18) . ?
C10 N3 1.3176(18) . ?
C11 N2 1.3110(17) . ?
N2 O2 1.3685(16) . ?
N3 O2 1.3789(16) . ?
N4 O3 1.223(2) . ?
N4 O4 1.2175(18) . ?
O5 H5A 0.8498 . ?
O5 H5B 0.8500 . ?

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
C2 C1 H1 119.1 . . ?
C2 C1 N1 121.83(13) . . ?
N1 C1 H1 119.1 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.75(13) . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 114.34(13) . . ?
O1 C3 C2 122.60(14) . . ?
O1 C3 C4 123.05(15) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.80(14) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 N1 121.38(13) . . ?
N1 C5 H5 119.3 . . ?
C7 C6 C11 117.39(13) . . ?
C7 C6 N1 122.10(12) . . ?
N1 C6 C11 120.36(11) . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.54(13) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.13(13) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 118.83(12) . . ?
C8 C9 N4 120.45(13) . . ?
C10 C9 N4 120.72(13) . . ?
C9 C10 C11 118.95(12) . . ?
N3 C10 C9 132.00(13) . . ?
N3 C10 C11 109.03(12) . . ?
C10 C11 C6 121.11(12) . . ?
N2 C11 C6 129.71(13) . . ?
N2 C11 C10 109.18(12) . . ?
C1 N1 C6 119.57(11) . . ?
C5 N1 C1 118.63(12) . . ?
C5 N1 C6 121.70(11) . . ?
C11 N2 O2 104.83(11) . . ?
C10 N3 O2 104.31(11) . . ?
O3 N4 C9 117.61(13) . . ?
O4 N4 C9 118.36(15) . . ?
O4 N4 O3 124.03(14) . . ?
N2 O2 N3 112.65(10) . . ?
H5A O5 H5B 104.5 . . ?

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
O5 H5A O1 0.85 2.01 2.8598(19) 177.3 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -5.3(2) . . . . ?
C1 C2 C3 O1 173.77(14) . . . . ?
C2 C1 N1 C5 2.3(2) . . . . ?
C2 C1 N1 C6 -173.99(13) . . . . ?
C2 C3 C4 C5 4.4(2) . . . . ?
C3 C4 C5 N1 -0.3(2) . . . . ?
C4 C5 N1 C1 -3.3(2) . . . . ?
C4 C5 N1 C6 172.97(13) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C6 C11 N2 O2 179.97(13) . . . . ?
C7 C6 C11 C10 2.24(19) . . . . ?
C7 C6 C11 N2 -178.45(14) . . . . ?
C7 C6 N1 C1 -34.67(18) . . . . ?
C7 C6 N1 C5 149.13(14) . . . . ?
C7 C8 C9 C10 1.6(2) . . . . ?
C7 C8 C9 N4 -179.20(12) . . . . ?
C8 C9 C10 C11 -1.06(19) . . . . ?
C8 C9 C10 N3 177.92(14) . . . . ?
C8 C9 N4 O3 173.50(14) . . . . ?
C8 C9 N4 O4 -7.0(2) . . . . ?
C9 C10 C11 C6 -0.88(18) . . . . ?
C9 C10 C11 N2 179.69(12) . . . . ?
C9 C10 N3 O2 -179.13(13) . . . . ?
C10 C9 N4 O3 -7.35(19) . . . . ?
C10 C9 N4 O4 172.19(14) . . . . ?
C10 C11 N2 O2 -0.66(15) . . . . ?
C10 N3 O2 N2 -0.35(15) . . . . ?
C11 C6 C7 C8 -1.7(2) . . . . ?
C11 C6 N1 C1 140.82(13) . . . . ?
C11 C6 N1 C5 -35.39(18) . . . . ?
C11 C10 N3 O2 -0.07(14) . . . . ?
C11 N2 O2 N3 0.65(15) . . . . ?
N1 C1 C2 C3 2.2(2) . . . . ?
N1 C6 C7 C8 173.89(12) . . . . ?
N1 C6 C11 C10 -173.45(11) . . . . ?
N1 C6 C11 N2 5.9(2) . . . . ?
N3 C10 C11 C6 179.92(11) . . . . ?
N3 C10 C11 N2 0.49(15) . . . . ?
N4 C9 C10 C11 179.77(11) . . . . ?
N4 C9 C10 N3 -1.2(2) . . . . ?
O1 C3 C4 C5 -174.69(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
