# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_cu_220811_10_0m
_database_code_depnum_ccdc_archive 'CCDC 2224969'
loop_
_audit_author_name
_audit_author_address
'XInyue Yuan'
;Qilu University of Technology, Shandong Analysis and Test Center
China
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-08-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O5, 4(H2 O)'
_chemical_formula_sum            'C14 H22 N4 O11'
_chemical_formula_weight         422.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.5643(12)
_cell_length_b                   15.1720(14)
_cell_length_c                   13.1988(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.662(3)
_cell_angle_gamma                90
_cell_volume                     3596.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.362
_cell_measurement_theta_min      3.813
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
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    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15585
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.814
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3049
_reflns_number_total             3164
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0827P)²+3.5363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9 \\sim O5: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
O11 \\sim O3: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
3. Others
 Sof(O5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(O9)=Sof(H9D)=Sof(H9E)=FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(H3B)=1-FVAR(2)
 Sof(O11)=Sof(H11A)=Sof(H11B)=FVAR(2)
4.a Riding coordinates:
 O13(H13D,H13E), O2(H2A,H2B), O9(H9D,H9E), O5(H5A,H5B), O11(H11A,H11B), O3(H3A,
 H3B)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C6(H6), C11(H11)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
4.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O10(H10), O12(H12), O7(H7)
;
_atom_sites_solution_hydrogens   mixed
_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 0.61465(6) 0.48570(7) 0.35495(10) 0.0273(3) Uani 1 1 d . . . . .
O4 O 0.85725(6) 0.42090(7) 0.38137(8) 0.0206(3) Uani 1 1 d . . . . .
O6 O 0.70960(6) 0.27948(7) 0.37599(8) 0.0219(3) Uani 1 1 d . . . . .
O8 O 0.69942(6) -0.13724(7) 0.37273(9) 0.0230(3) Uani 1 1 d . . . . .
H8 H 0.737054 -0.168245 0.373553 0.035 Uiso 1 1 calc R U . . .
O10 O 0.59017(6) -0.01933(7) 0.36645(9) 0.0242(3) Uani 1 1 d . . . . .
H10 H 0.589869 -0.074561 0.370829 0.036 Uiso 1 1 calc R U . . .
O12 O 0.82819(6) 0.24767(7) 0.38413(9) 0.0270(3) Uani 1 1 d . . . . .
H12 H 0.831211 0.302840 0.381880 0.041 Uiso 1 1 calc R U . . .
O13 O 0.50467(7) 0.17045(8) 0.64710(10) 0.0347(3) Uani 1 1 d . . . . .
H13D H 0.514156 0.216987 0.614196 0.052 Uiso 1 1 d R U . . .
H13E H 0.541156 0.134507 0.646856 0.052 Uiso 1 1 d R U . . .
O7 O 0.84400(6) -0.08283(7) 0.38844(10) 0.0257(3) Uani 1 1 d . . . . .
H7 H 0.884958 -0.058342 0.390701 0.039 Uiso 1 1 calc R U . . .
N1 N 0.88298(7) 0.62529(8) 0.38436(9) 0.0176(3) Uani 1 1 d . . . . .
N4 N 0.69202(7) 0.60361(8) 0.36583(9) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.78697(7) 0.71595(8) 0.37516(9) 0.0185(3) Uani 1 1 d . . . . .
O2 O 0.50522(7) 0.32088(10) 0.52568(12) 0.0457(4) Uani 1 1 d . . . . .
H2A H 0.520592 0.313797 0.469190 0.069 Uiso 1 1 d R U . . .
H2B H 0.517172 0.374907 0.544830 0.069 Uiso 1 1 d R U . . .
N3 N 0.73693(7) 0.45925(8) 0.37008(9) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.726583 0.402631 0.369770 0.021 Uiso 1 1 calc R U . . .
C1 C 0.76375(8) 0.63100(10) 0.37359(10) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.85941(8) 0.70849(10) 0.38185(12) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.891370 0.757819 0.384577 0.023 Uiso 1 1 calc R U . . .
C6 C 0.67438(8) 0.09879(10) 0.37537(11) 0.0171(3) Uani 1 1 d . . . . .
H6 H 0.635025 0.139360 0.373079 0.020 Uiso 1 1 calc R U . . .
C8 C 0.75909(8) 0.22488(10) 0.38039(11) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.81057(8) 0.48000(9) 0.37717(10) 0.0161(3) Uani 1 1 d . . . . .
C12 C 0.79064(8) -0.02005(10) 0.38388(11) 0.0181(3) Uani 1 1 d . . . . .
C14 C 0.82151(8) 0.57288(10) 0.37926(11) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.66100(8) 0.00906(10) 0.37280(11) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.74614(8) 0.12907(10) 0.38134(10) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.95853(8) 0.59495(11) 0.38741(13) 0.0251(4) Uani 1 1 d . . . . .
H9A H 0.990181 0.645859 0.383413 0.038 Uiso 1 1 calc R U . . .
H9B H 0.956894 0.555682 0.327921 0.038 Uiso 1 1 calc R U . . .
H9C H 0.978974 0.563039 0.452944 0.038 Uiso 1 1 calc R U . . .
C5 C 0.71832(8) -0.05127(9) 0.37639(11) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.80442(9) 0.06950(10) 0.38607(11) 0.0182(3) Uani 1 1 d . . . . .
H11 H 0.853349 0.090578 0.390779 0.022 Uiso 1 1 calc R U . . .
C3 C 0.67761(8) 0.51542(10) 0.36343(11) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.63073(9) 0.66692(11) 0.35526(14) 0.0258(4) Uani 1 1 d . . . . .
H13A H 0.641677 0.707143 0.415316 0.039 Uiso 1 1 calc R U . . .
H13B H 0.584398 0.635084 0.352908 0.039 Uiso 1 1 calc R U . . .
H13C H 0.625195 0.700784 0.290517 0.039 Uiso 1 1 calc R U . . .
O9 O 0.5480(3) 0.2784(6) 0.3485(4) 0.0372(11) Uani 0.469(15) 1 d . U P A 1
H9D H 0.596280 0.280053 0.361800 0.056 Uiso 0.469(15) 1 d R U P A 1
H9E H 0.533000 0.319033 0.301340 0.056 Uiso 0.469(15) 1 d R U P A 1
O5 O 0.5599(3) 0.3139(5) 0.3409(4) 0.0372(11) Uani 0.531(15) 1 d . U P A 2
H5A H 0.607479 0.303145 0.358196 0.056 Uiso 0.531(15) 1 d R U P A 2
H5B H 0.556029 0.365715 0.311686 0.056 Uiso 0.531(15) 1 d R U P A 2
O11 O 0.9756(4) -0.0016(6) 0.4064(9) 0.0390(14) Uani 0.364(14) 1 d . U P B 2
H11A H 0.968450 0.054165 0.392101 0.058 Uiso 0.364(14) 1 d R U P B 2
H11B H 0.957760 -0.028045 0.346831 0.058 Uiso 0.364(14) 1 d R U P B 2
O3 O 0.9670(2) 0.0125(3) 0.3634(5) 0.0370(9) Uani 0.636(14) 1 d . U P B 1
H3A H 0.961167 0.022724 0.296930 0.056 Uiso 0.636(14) 1 d R U P B 1
H3B H 1.006677 -0.020236 0.380900 0.056 Uiso 0.636(14) 1 d R U P B 1


_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 C3 1.2311(19) . ?
O4 C10 1.2384(18) . ?
O6 C8 1.2274(19) . ?
O8 H8 0.8400 . ?
O8 C5 1.3484(18) . ?
O10 H10 0.8400 . ?
O10 C7 1.3661(18) . ?
O12 H12 0.8400 . ?
O12 C8 1.3173(18) . ?
O13 H13D 0.8700 . ?
O13 H13E 0.8702 . ?
O7 H7 0.8400 . ?
O7 C12 1.3644(18) . ?
N1 C4 1.334(2) . ?
N1 C14 1.3784(19) . ?
N1 C9 1.4669(19) . ?
N4 C1 1.3738(19) . ?
N4 C3 1.363(2) . ?
N4 C13 1.4685(19) . ?
N2 C1 1.3575(19) . ?
N2 C4 1.330(2) . ?
O2 H2A 0.8698 . ?
O2 H2B 0.8699 . ?
N3 H3 0.8800 . ?
N3 C10 1.3827(19) . ?
N3 C3 1.3776(19) . ?
C1 C14 1.376(2) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.383(2) . ?
C6 C2 1.392(2) . ?
C8 C2 1.474(2) . ?
C10 C14 1.423(2) . ?
C12 C5 1.403(2) . ?
C12 C11 1.382(2) . ?
C7 C5 1.395(2) . ?
C2 C11 1.399(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O9 H9D 0.8699 . ?
O9 H9E 0.8700 . ?
O5 H5A 0.8703 . ?
O5 H5B 0.8700 . ?
O11 H11A 0.8698 . ?
O11 H11B 0.8700 . ?
O3 H3A 0.8700 . ?
O3 H3B 0.8702 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O8 H8 109.5 . . ?
C7 O10 H10 109.5 . . ?
C8 O12 H12 109.5 . . ?
H13D O13 H13E 104.5 . . ?
C12 O7 H7 109.5 . . ?
C4 N1 C14 106.40(12) . . ?
C4 N1 C9 127.09(13) . . ?
C14 N1 C9 126.46(13) . . ?
C1 N4 C13 121.50(13) . . ?
C3 N4 C1 118.65(13) . . ?
C3 N4 C13 119.80(13) . . ?
C4 N2 C1 103.42(12) . . ?
H2A O2 H2B 104.5 . . ?
C10 N3 H3 115.7 . . ?
C3 N3 H3 115.7 . . ?
C3 N3 C10 128.62(13) . . ?
N4 C1 C14 122.53(14) . . ?
N2 C1 N4 125.90(13) . . ?
N2 C1 C14 111.56(13) . . ?
N1 C4 H4 123.1 . . ?
N2 C4 N1 113.70(13) . . ?
N2 C4 H4 123.1 . . ?
C7 C6 H6 120.3 . . ?
C7 C6 C2 119.31(14) . . ?
C2 C6 H6 120.3 . . ?
O6 C8 O12 122.33(14) . . ?
O6 C8 C2 122.98(14) . . ?
O12 C8 C2 114.70(13) . . ?
O4 C10 N3 120.45(13) . . ?
O4 C10 C14 128.41(14) . . ?
N3 C10 C14 111.14(13) . . ?
O7 C12 C5 116.00(13) . . ?
O7 C12 C11 123.85(14) . . ?
C11 C12 C5 120.14(14) . . ?
N1 C14 C10 133.20(14) . . ?
C1 C14 N1 104.91(13) . . ?
C1 C14 C10 121.88(14) . . ?
O10 C7 C6 118.43(13) . . ?
O10 C7 C5 120.62(13) . . ?
C6 C7 C5 120.95(14) . . ?
C6 C2 C8 118.73(13) . . ?
C6 C2 C11 120.49(14) . . ?
C11 C2 C8 120.77(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O8 C5 C12 124.37(13) . . ?
O8 C5 C7 116.36(13) . . ?
C7 C5 C12 119.26(14) . . ?
C12 C11 C2 119.83(14) . . ?
C12 C11 H11 120.1 . . ?
C2 C11 H11 120.1 . . ?
O1 C3 N4 122.53(14) . . ?
O1 C3 N3 120.30(14) . . ?
N4 C3 N3 117.17(13) . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H9D O9 H9E 104.5 . . ?
H5A O5 H5B 104.5 . . ?
H11A O11 H11B 104.5 . . ?
H3A O3 H3B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C10 C14 N1 1.3(3) . . . . ?
O4 C10 C14 C1 179.79(14) . . . . ?
O6 C8 C2 C6 1.0(2) . . . . ?
O6 C8 C2 C11 179.77(13) . . . . ?
O10 C7 C5 O8 0.3(2) . . . . ?
O10 C7 C5 C12 -179.41(13) . . . . ?
O12 C8 C2 C6 -178.66(12) . . . . ?
O12 C8 C2 C11 0.1(2) . . . . ?
O7 C12 C5 O8 -0.6(2) . . . . ?
O7 C12 C5 C7 179.15(12) . . . . ?
O7 C12 C11 C2 -179.79(13) . . . . ?
N4 C1 C14 N1 179.02(12) . . . . ?
N4 C1 C14 C10 0.2(2) . . . . ?
N2 C1 C14 N1 -0.10(16) . . . . ?
N2 C1 C14 C10 -178.96(12) . . . . ?
N3 C10 C14 N1 -179.10(14) . . . . ?
N3 C10 C14 C1 -0.61(19) . . . . ?
C1 N4 C3 O1 -178.84(13) . . . . ?
C1 N4 C3 N3 0.64(19) . . . . ?
C1 N2 C4 N1 0.12(17) . . . . ?
C4 N1 C14 C1 0.17(15) . . . . ?
C4 N1 C14 C10 178.84(15) . . . . ?
C4 N2 C1 N4 -179.09(13) . . . . ?
C4 N2 C1 C14 0.00(16) . . . . ?
C6 C7 C5 O8 -179.56(13) . . . . ?
C6 C7 C5 C12 0.7(2) . . . . ?
C6 C2 C11 C12 0.6(2) . . . . ?
C8 C2 C11 C12 -178.17(13) . . . . ?
C10 N3 C3 O1 178.21(13) . . . . ?
C10 N3 C3 N4 -1.3(2) . . . . ?
C14 N1 C4 N2 -0.18(17) . . . . ?
C7 C6 C2 C8 177.94(13) . . . . ?
C7 C6 C2 C11 -0.8(2) . . . . ?
C2 C6 C7 O10 -179.71(12) . . . . ?
C2 C6 C7 C5 0.2(2) . . . . ?
C9 N1 C4 N2 177.45(14) . . . . ?
C9 N1 C14 C1 -177.49(13) . . . . ?
C9 N1 C14 C10 1.2(2) . . . . ?
C5 C12 C11 C2 0.3(2) . . . . ?
C11 C12 C5 O8 179.33(13) . . . . ?
C11 C12 C5 C7 -1.0(2) . . . . ?
C3 N4 C1 N2 178.84(13) . . . . ?
C3 N4 C1 C14 -0.2(2) . . . . ?
C3 N3 C10 O4 -179.14(13) . . . . ?
C3 N3 C10 C14 1.2(2) . . . . ?
C13 N4 C1 N2 1.7(2) . . . . ?
C13 N4 C1 C14 -177.29(13) . . . . ?
C13 N4 C3 O1 -1.7(2) . . . . ?
C13 N4 C3 N3 177.82(13) . . . . ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 2224972'
loop_
_audit_author_name
_audit_author_address
'Xinyue Yuan'
;Qilu University of Technology, Shandong Analysis and Test Cente
China
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.5-beta
(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 H6 O5, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O7'
_chemical_formula_weight         350.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.9228(2)
_cell_length_b                   6.33067(19)
_cell_length_c                   29.1969(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.122(2)
_cell_angle_gamma                90
_cell_volume                     1458.57(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    212.99(10)
_cell_measurement_theta_max      72.0430
_cell_measurement_theta_min      3.0080
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         3.039
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      212.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  66.00   1.00    0.70    --   48.67-124.00 116.00   25
  2  ω     70.00 106.00   1.00    0.70    --   48.67-147.00 -48.00   36
  3  ω     36.00  63.00   1.00    4.50    --  106.65 -57.00-120.00   27
  4  ω     80.00 152.00   1.00    4.50    --  106.65 147.00   1.00   72
  5  ω     80.00 106.00   1.00    4.50    --  106.65 -99.00 120.00   26
  6  ω     36.00 111.00   1.00    4.50    --  106.65-124.00 116.00   75
  7  ω     34.00  74.00   1.00    4.50    --  106.65 -99.00 120.00   40
  8  ω     35.00 103.00   1.00    4.50    --  106.65-125.00  30.00   68
  9  ω    101.00 127.00   1.00    4.50    --  106.65-147.00 -48.00   26
 10  ω    -85.00 -19.00   1.00    4.50    --  -91.75 125.00 150.00   66
 11  ω    -76.00 -51.00   1.00    4.50    --  -91.75 124.00-164.00   25
 12  ω    -82.00 -56.00   1.00    0.70    --  -48.67 124.00-164.00   26
 13  ω    -27.00  25.00   1.00    0.70    --  -48.67  19.00-120.00   52
 14  ω    -26.00  25.00   1.00    0.70    --  -48.67  19.00 -60.00   51
 15  ω    -65.00 -20.00   1.00    4.50    --  -91.75  57.00  30.00   45
 16  ω   -165.00 -79.00   1.00    4.50    --  -91.75 -19.00 120.00   86
 17  ω   -143.00-118.00   1.00    4.50    --  -91.75-124.00 116.00   25
 18  ω   -118.00 -74.00   1.00    0.70    --  -48.67-125.00 150.00   44
 19  ω   -114.00 -88.00   1.00    0.70    --  -48.67-124.00 116.00   26
 20  ω   -119.00 -61.00   1.00    0.70    --  -48.67-147.00 -48.00   58
 21  ω    -99.00 -70.00   1.00    4.50    --  -91.75-147.00 -48.00   29
 22  ω   -158.00-125.00   1.00    4.50    --  -91.75 -57.00-120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0360579000
_diffrn_orient_matrix_UB_12      -0.2218115000
_diffrn_orient_matrix_UB_13      -0.0185580000
_diffrn_orient_matrix_UB_21      0.1121261000
_diffrn_orient_matrix_UB_22      0.0981877000
_diffrn_orient_matrix_UB_23      -0.0348593000
_diffrn_orient_matrix_UB_31      0.1556242000
_diffrn_orient_matrix_UB_32      -0.0196481000
_diffrn_orient_matrix_UB_33      0.0353269000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             2591
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.5167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O7(H7), O3(H3A)
;
_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 0.37012(19) 0.8627(2) 0.31430(5) 0.0385(4) Uani 1 1 d . . . . .
H1 H 0.374503 0.880502 0.286272 0.058 Uiso 1 1 calc R U . . .
O4 O -0.0551(2) 1.6659(2) 0.36181(5) 0.0437(4) Uani 1 1 d . . . . .
H4 H -0.099386 1.760914 0.376237 0.066 Uiso 1 1 calc R U . . .
O6 O 0.59255(19) 1.4355(2) 0.27649(4) 0.0394(4) Uani 1 1 d . . . . .
O7 O 0.0486(2) 1.4848(3) 0.29175(5) 0.0441(4) Uani 1 1 d . . . . .
H7 H 0.002171 1.578735 0.305966 0.066 Uiso 1 1 calc R U . . .
N1 N 0.6944(2) 1.1942(3) 0.33013(5) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.6526(3) 1.2709(3) 0.40898(6) 0.0317(4) Uani 1 1 d . . . . .
N4 N 0.6947(2) 1.1689(3) 0.45041(6) 0.0396(4) Uani 1 1 d . . . . .
N2 N 0.5513(2) 1.4983(3) 0.35094(5) 0.0324(4) Uani 1 1 d . . . . .
H2 H 0.496711 1.611955 0.341712 0.039 Uiso 1 1 calc R U . . .
O2 O 0.0122(2) 1.5453(3) 0.43281(5) 0.0477(4) Uani 1 1 d . . . . .
O5 O 0.5057(2) 1.5887(3) 0.42420(5) 0.0470(4) Uani 1 1 d . . . . .
C4 C 0.1232(2) 1.3442(3) 0.32193(6) 0.0303(4) Uani 1 1 d . . . . .
C6 C 0.6121(2) 1.3783(3) 0.31657(6) 0.0301(4) Uani 1 1 d . . . . .
C8 C 0.0204(3) 1.5308(3) 0.39088(7) 0.0346(5) Uani 1 1 d . . . . .
C10 C 0.5645(3) 1.4642(3) 0.39813(7) 0.0328(5) Uani 1 1 d . . . . .
C12 C 0.2844(2) 1.0264(3) 0.33187(7) 0.0293(4) Uani 1 1 d . . . . .
C14 C 0.1918(3) 1.1988(3) 0.39775(6) 0.0328(4) Uani 1 1 d . . . . .
O3 O 0.1858(2) 1.2046(3) 0.44414(5) 0.0482(4) Uani 1 1 d . . . . .
H3A H 0.128462 1.307558 0.451088 0.072 Uiso 1 1 calc R U . . .
C7 C 0.1119(2) 1.3592(3) 0.37004(6) 0.0296(4) Uani 1 1 d . . . . .
C2 C 0.2090(2) 1.1799(3) 0.30331(6) 0.0310(4) Uani 1 1 d . . . . .
H2A H 0.216164 1.172608 0.271383 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7126(2) 1.1444(3) 0.37613(6) 0.0297(4) Uani 1 1 d . . . . .
N3 N 0.7898(2) 0.9717(3) 0.39572(6) 0.0359(4) Uani 1 1 d . . . . .
C5 C 0.2768(3) 1.0332(3) 0.37922(7) 0.0337(5) Uani 1 1 d . . . . .
H5 H 0.328411 0.927453 0.398248 0.040 Uiso 1 1 calc R U . . .
C11 C 0.7596(3) 1.0536(4) 0.29585(7) 0.0411(5) Uani 1 1 d . . . . .
H11A H 0.711745 0.913646 0.298618 0.062 Uiso 1 1 calc R U . . .
H11B H 0.882073 1.045800 0.301009 0.062 Uiso 1 1 calc R U . . .
H11C H 0.728025 1.108483 0.265260 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7755(3) 0.9930(4) 0.44070(7) 0.0417(5) Uani 1 1 d . . . . .
H3 H 0.817906 0.894633 0.462960 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6541(4) 1.2425(5) 0.49569(7) 0.0586(7) Uani 1 1 d . . . . .
H13A H 0.711451 1.375437 0.502818 0.088 Uiso 1 1 calc R U . . .
H13B H 0.691287 1.138321 0.518771 0.088 Uiso 1 1 calc R U . . .
H13C H 0.532637 1.262603 0.495471 0.088 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 H1 0.8300 . ?
O1 C12 1.364(2) . ?
O4 H4 0.8300 . ?
O4 C8 1.311(3) . ?
O6 C6 1.222(2) . ?
O7 H7 0.8300 . ?
O7 C4 1.351(2) . ?
N1 C6 1.376(3) . ?
N1 C9 1.375(2) . ?
N1 C11 1.467(3) . ?
C1 N4 1.385(3) . ?
C1 C10 1.430(3) . ?
C1 C9 1.367(3) . ?
N4 C3 1.328(3) . ?
N4 C13 1.464(3) . ?
N2 H2 0.8700 . ?
N2 C6 1.379(3) . ?
N2 C10 1.389(2) . ?
O2 C8 1.235(2) . ?
O5 C10 1.217(2) . ?
C4 C7 1.419(3) . ?
C4 C2 1.381(3) . ?
C8 C7 1.468(3) . ?
C12 C2 1.381(3) . ?
C12 C5 1.390(3) . ?
C14 O3 1.360(2) . ?
C14 C7 1.413(3) . ?
C14 C5 1.382(3) . ?
O3 H3A 0.8300 . ?
C2 H2A 0.9400 . ?
C9 N3 1.354(3) . ?
N3 C3 1.335(3) . ?
C5 H5 0.9400 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C3 H3 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?

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
C12 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C4 O7 H7 109.5 . . ?
C6 N1 C11 120.27(16) . . ?
C9 N1 C6 118.78(16) . . ?
C9 N1 C11 120.95(17) . . ?
N4 C1 C10 131.81(18) . . ?
C9 C1 N4 105.54(17) . . ?
C9 C1 C10 122.64(17) . . ?
C1 N4 C13 125.81(18) . . ?
C3 N4 C1 106.71(17) . . ?
C3 N4 C13 127.48(19) . . ?
C6 N2 H2 115.3 . . ?
C6 N2 C10 129.48(17) . . ?
C10 N2 H2 115.3 . . ?
O7 C4 C7 122.64(18) . . ?
O7 C4 C2 116.20(17) . . ?
C2 C4 C7 121.15(17) . . ?
O6 C6 N1 122.88(18) . . ?
O6 C6 N2 120.74(18) . . ?
N1 C6 N2 116.38(16) . . ?
O4 C8 C7 115.34(17) . . ?
O2 C8 O4 122.12(19) . . ?
O2 C8 C7 122.52(18) . . ?
N2 C10 C1 110.15(16) . . ?
O5 C10 C1 128.47(18) . . ?
O5 C10 N2 121.39(18) . . ?
O1 C12 C2 120.70(17) . . ?
O1 C12 C5 117.70(17) . . ?
C2 C12 C5 121.59(18) . . ?
O3 C14 C7 119.80(18) . . ?
O3 C14 C5 118.15(18) . . ?
C5 C14 C7 122.04(18) . . ?
C14 O3 H3A 109.5 . . ?
C4 C7 C8 122.49(17) . . ?
C14 C7 C4 117.00(18) . . ?
C14 C7 C8 120.51(17) . . ?
C4 C2 C12 119.61(17) . . ?
C4 C2 H2A 120.2 . . ?
C12 C2 H2A 120.2 . . ?
C1 C9 N1 122.54(18) . . ?
N3 C9 N1 127.04(17) . . ?
N3 C9 C1 110.42(17) . . ?
C3 N3 C9 105.05(17) . . ?
C12 C5 H5 120.7 . . ?
C14 C5 C12 118.61(18) . . ?
C14 C5 H5 120.7 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C3 N3 112.29(18) . . ?
N4 C3 H3 123.9 . . ?
N3 C3 H3 123.9 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C2 C4 -179.94(18) . . . . ?
O1 C12 C5 C14 179.47(18) . . . . ?
O4 C8 C7 C4 2.2(3) . . . . ?
O4 C8 C7 C14 -177.17(18) . . . . ?
O7 C4 C7 C8 -1.0(3) . . . . ?
O7 C4 C7 C14 178.36(18) . . . . ?
O7 C4 C2 C12 -178.14(18) . . . . ?
N1 C9 N3 C3 180.0(2) . . . . ?
C1 N4 C3 N3 0.0(3) . . . . ?
C1 C9 N3 C3 0.4(2) . . . . ?
N4 C1 C10 N2 -179.0(2) . . . . ?
N4 C1 C10 O5 0.8(4) . . . . ?
N4 C1 C9 N1 179.97(18) . . . . ?
N4 C1 C9 N3 -0.4(2) . . . . ?
O2 C8 C7 C4 -179.1(2) . . . . ?
O2 C8 C7 C14 1.5(3) . . . . ?
C6 N1 C9 C1 -0.2(3) . . . . ?
C6 N1 C9 N3 -179.79(19) . . . . ?
C6 N2 C10 C1 -1.5(3) . . . . ?
C6 N2 C10 O5 178.7(2) . . . . ?
C10 C1 N4 C3 179.5(2) . . . . ?
C10 C1 N4 C13 0.3(4) . . . . ?
C10 C1 C9 N1 0.6(3) . . . . ?
C10 C1 C9 N3 -179.69(19) . . . . ?
C10 N2 C6 O6 -178.0(2) . . . . ?
C10 N2 C6 N1 1.9(3) . . . . ?
O3 C14 C7 C4 179.85(18) . . . . ?
O3 C14 C7 C8 -0.8(3) . . . . ?
O3 C14 C5 C12 -179.68(19) . . . . ?
C7 C4 C2 C12 0.5(3) . . . . ?
C7 C14 C5 C12 0.5(3) . . . . ?
C2 C4 C7 C8 -179.48(19) . . . . ?
C2 C4 C7 C14 -0.1(3) . . . . ?
C2 C12 C5 C14 -0.2(3) . . . . ?
C9 N1 C6 O6 179.00(18) . . . . ?
C9 N1 C6 N2 -1.0(3) . . . . ?
C9 C1 N4 C3 0.2(2) . . . . ?
C9 C1 N4 C13 -178.9(2) . . . . ?
C9 C1 C10 N2 0.1(3) . . . . ?
C9 C1 C10 O5 179.9(2) . . . . ?
C9 N3 C3 N4 -0.2(3) . . . . ?
C5 C12 C2 C4 -0.3(3) . . . . ?
C5 C14 C7 C4 -0.4(3) . . . . ?
C5 C14 C7 C8 179.00(19) . . . . ?
C11 N1 C6 O6 -1.6(3) . . . . ?
C11 N1 C6 N2 178.45(18) . . . . ?
C11 N1 C9 C1 -179.59(19) . . . . ?
C11 N1 C9 N3 0.8(3) . . . . ?
C13 N4 C3 N3 179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# 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_220811_9_0m
_database_code_depnum_ccdc_archive 'CCDC 2292950'
loop_
_audit_author_name
_audit_author_address
'Xinyue Yuan'
;shandong Analysis and Testing Center
China
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H6 O5, C7 H8 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H18 N4 O9'
_chemical_formula_weight         386.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.746(4)
_cell_length_b                   6.6694(10)
_cell_length_c                   17.362(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.936(6)
_cell_angle_gamma                90
_cell_volume                     3208.5(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2688
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      70.531
_cell_measurement_theta_min      3.188
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    1.171
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.7837.
The λ/2 correction factor is Not present.
;
_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    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13188
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.335
_diffrn_reflns_theta_min         5.101
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2209
_reflns_number_total             3119
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.00036(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1518
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9 \\sim O2: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
3. Others
 Sof(O9)=Sof(H9A)=Sof(H9B)=1-FVAR(1)
 Sof(O2)=Sof(H2A)=Sof(H2B)=FVAR(1)
4.a Riding coordinates:
 O2(H2A,H2B)
4.b Free rotating group:
 O7(H7A,H7B), O9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1B), C12(H12), C11(H11)
4.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C13(H13A,H13B,H13C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O4(H4), O8(H8), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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 0.60809(5) -0.1568(2) -0.00064(9) 0.0297(4) Uani 1 1 d . . . . .
H1A H 0.6221 -0.1488 -0.0423 0.044 Uiso 1 1 calc R U . . .
O4 O 0.70390(6) -0.0874(2) -0.02449(9) 0.0319(4) Uani 1 1 d . . . . .
H4 H 0.7327 -0.0484 -0.0241 0.048 Uiso 1 1 calc R U . . .
O6 O 0.70912(5) 0.3998(2) 0.06100(9) 0.0292(4) Uani 1 1 d . . . . .
O8 O 0.57698(5) -0.1989(3) 0.14043(10) 0.0324(4) Uani 1 1 d . . . . .
H8 H 0.5709 -0.2070 0.1872 0.049 Uiso 1 1 calc R U . . .
O10 O 0.58519(6) 0.2941(3) 0.21879(10) 0.0360(4) Uani 1 1 d . . . . .
O5 O 0.78656(6) -0.1220(3) 0.24148(10) 0.0358(4) Uani 1 1 d . . . . .
O3 O 0.72551(6) -0.1087(3) 0.32045(9) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.7484 -0.1041 0.3540 0.050 Uiso 1 1 calc R U . . .
O7 O 0.63224(6) -0.1317(3) -0.14833(10) 0.0389(5) Uani 1 1 d G . . . .
H7A H 0.6193 -0.1820 -0.1908 0.058 Uiso 1 1 d G U . . .
H7B H 0.6628 -0.1219 -0.1568 0.058 Uiso 1 1 d G U . . .
N1 N 0.64530(6) 0.3476(3) 0.13563(11) 0.0249(4) Uani 1 1 d . . . . .
H1 H 0.6655 0.3603 0.1761 0.030 Uiso 1 1 calc R U . . .
N4 N 0.63484(7) 0.3509(3) 0.00103(11) 0.0264(4) Uani 1 1 d . . . . .
N2 N 0.55177(7) 0.2934(3) -0.04712(12) 0.0310(5) Uani 1 1 d . . . . .
N3 N 0.51976(7) 0.2537(3) 0.06823(12) 0.0326(5) Uani 1 1 d . . . . .
C1 C 0.65755(8) -0.1560(3) 0.19752(13) 0.0247(5) Uani 1 1 d . . . . .
H1B H 0.6465 -0.1703 0.2481 0.030 Uiso 1 1 calc R U . . .
C4 C 0.66504(8) 0.3680(3) 0.06501(13) 0.0236(5) Uani 1 1 d . . . . .
C6 C 0.70664(8) -0.1244(3) 0.18640(13) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.74306(8) -0.1189(3) 0.25080(13) 0.0256(5) Uani 1 1 d . . . . .
C10 C 0.56847(8) 0.2935(3) 0.08167(14) 0.0276(5) Uani 1 1 d . . . . .
C12 C 0.72260(8) -0.1019(3) 0.11276(13) 0.0240(5) Uani 1 1 d . . . . .
H12 H 0.7559 -0.0813 0.1055 0.029 Uiso 1 1 calc R U . . .
C14 C 0.62523(8) -0.1662(3) 0.13427(14) 0.0235(5) Uani 1 1 d . . . . .
C7 C 0.64123(8) -0.1440(3) 0.05941(13) 0.0224(5) Uani 1 1 d . . . . .
C2 C 0.69031(8) -0.1092(3) 0.04988(13) 0.0235(5) Uani 1 1 d . . . . .
C9 C 0.58657(8) 0.3156(3) 0.01073(13) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.59755(8) 0.3094(3) 0.15112(14) 0.0257(5) Uani 1 1 d . . . . .
C11 C 0.51213(9) 0.2563(4) -0.00871(14) 0.0329(6) Uani 1 1 d . . . . .
H11 H 0.4813 0.2338 -0.0337 0.039 Uiso 1 1 calc R U . . .
C3 C 0.65320(9) 0.3675(4) -0.07664(14) 0.0358(6) Uani 1 1 d . . . . .
H3A H 0.6478 0.5038 -0.0962 0.054 Uiso 1 1 calc R U . . .
H3B H 0.6362 0.2715 -0.1111 0.054 Uiso 1 1 calc R U . . .
H3C H 0.6879 0.3380 -0.0744 0.054 Uiso 1 1 calc R U . . .
C13 C 0.48488(9) 0.2161(4) 0.12709(16) 0.0424(7) Uani 1 1 d . . . . .
H13A H 0.4980 0.1159 0.1638 0.064 Uiso 1 1 calc R U . . .
H13B H 0.4547 0.1661 0.1024 0.064 Uiso 1 1 calc R U . . .
H13C H 0.4786 0.3411 0.1545 0.064 Uiso 1 1 calc R U . . .
O2 O 0.5407(3) 0.2263(15) -0.2160(4) 0.0412(15) Uani 0.399(11) 1 d . U P A 2
H2A H 0.5119 0.2752 -0.2256 0.062 Uiso 0.399(11) 1 d R U P A 2
H2B H 0.5501 0.2792 -0.1720 0.062 Uiso 0.399(11) 1 d R U P A 2
O9 O 0.55092(17) 0.3229(10) -0.2180(3) 0.0398(11) Uani 0.601(11) 1 d G U P A 1
H9A H 0.5662 0.4305 -0.2311 0.060 Uiso 0.601(11) 1 d G U P A 1
H9B H 0.5533 0.3225 -0.1679 0.060 Uiso 0.601(11) 1 d G U P A 1


_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 H1A 0.8400 . ?
O1 C7 1.357(3) . ?
O4 H4 0.8400 . ?
O4 C2 1.371(3) . ?
O6 C4 1.247(3) . ?
O8 H8 0.8400 . ?
O8 C14 1.366(2) . ?
O10 C5 1.245(3) . ?
O5 C8 1.226(3) . ?
O3 H3 0.8400 . ?
O3 C8 1.328(3) . ?
O7 H7A 0.8702 . ?
O7 H7B 0.8698 . ?
N1 H1 0.8800 . ?
N1 C4 1.375(3) . ?
N1 C5 1.389(3) . ?
N4 C4 1.361(3) . ?
N4 C9 1.379(3) . ?
N4 C3 1.470(3) . ?
N2 C9 1.365(3) . ?
N2 C11 1.338(3) . ?
N3 C10 1.385(3) . ?
N3 C11 1.342(3) . ?
N3 C13 1.465(3) . ?
C1 H1B 0.9500 . ?
C1 C6 1.401(3) . ?
C1 C14 1.383(3) . ?
C6 C8 1.469(3) . ?
C6 C12 1.383(3) . ?
C10 C9 1.362(3) . ?
C10 C5 1.420(3) . ?
C12 H12 0.9500 . ?
C12 C2 1.377(3) . ?
C14 C7 1.403(3) . ?
C7 C2 1.399(3) . ?
C11 H11 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O2 H2A 0.8698 . ?
O2 H2B 0.8699 . ?
O9 H9A 0.8699 . ?
O9 H9B 0.8698 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1A 109.5 . . ?
C2 O4 H4 109.5 . . ?
C14 O8 H8 109.5 . . ?
C8 O3 H3 109.5 . . ?
H7A O7 H7B 104.4 . . ?
C4 N1 H1 115.9 . . ?
C4 N1 C5 128.2(2) . . ?
C5 N1 H1 115.9 . . ?
C4 N4 C9 118.4(2) . . ?
C4 N4 C3 120.96(19) . . ?
C9 N4 C3 120.6(2) . . ?
C11 N2 C9 102.8(2) . . ?
C10 N3 C13 126.1(2) . . ?
C11 N3 C10 105.55(19) . . ?
C11 N3 C13 128.4(2) . . ?
C6 C1 H1B 120.2 . . ?
C14 C1 H1B 120.2 . . ?
C14 C1 C6 119.5(2) . . ?
O6 C4 N1 120.2(2) . . ?
O6 C4 N4 122.2(2) . . ?
N4 C4 N1 117.57(19) . . ?
C1 C6 C8 122.3(2) . . ?
C12 C6 C1 120.2(2) . . ?
C12 C6 C8 117.4(2) . . ?
O5 C8 O3 122.0(2) . . ?
O5 C8 C6 122.9(2) . . ?
O3 C8 C6 115.10(19) . . ?
N3 C10 C5 131.6(2) . . ?
C9 C10 N3 105.7(2) . . ?
C9 C10 C5 122.7(2) . . ?
C6 C12 H12 119.9 . . ?
C2 C12 C6 120.2(2) . . ?
C2 C12 H12 119.9 . . ?
O8 C14 C1 122.9(2) . . ?
O8 C14 C7 116.6(2) . . ?
C1 C14 C7 120.5(2) . . ?
O1 C7 C14 118.11(19) . . ?
O1 C7 C2 123.0(2) . . ?
C2 C7 C14 118.9(2) . . ?
O4 C2 C12 122.92(19) . . ?
O4 C2 C7 116.4(2) . . ?
C12 C2 C7 120.6(2) . . ?
N2 C9 N4 125.7(2) . . ?
C10 C9 N4 122.3(2) . . ?
C10 C9 N2 112.0(2) . . ?
O10 C5 N1 120.6(2) . . ?
O10 C5 C10 128.6(2) . . ?
N1 C5 C10 110.8(2) . . ?
N2 C11 N3 114.0(2) . . ?
N2 C11 H11 123.0 . . ?
N3 C11 H11 123.0 . . ?
N4 C3 H3A 109.5 . . ?
N4 C3 H3B 109.5 . . ?
N4 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
H2A O2 H2B 104.5 . . ?
H9A O9 H9B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C2 O4 0.2(3) . . . . ?
O1 C7 C2 C12 -178.61(19) . . . . ?
O8 C14 C7 O1 -0.1(3) . . . . ?
O8 C14 C7 C2 179.69(18) . . . . ?
N3 C10 C9 N4 -177.96(18) . . . . ?
N3 C10 C9 N2 0.4(2) . . . . ?
N3 C10 C5 O10 -1.5(4) . . . . ?
N3 C10 C5 N1 178.7(2) . . . . ?
C1 C6 C8 O5 168.6(2) . . . . ?
C1 C6 C8 O3 -11.9(3) . . . . ?
C1 C6 C12 C2 0.4(3) . . . . ?
C1 C14 C7 O1 179.52(19) . . . . ?
C1 C14 C7 C2 -0.7(3) . . . . ?
C4 N1 C5 O10 179.72(19) . . . . ?
C4 N1 C5 C10 -0.5(3) . . . . ?
C4 N4 C9 N2 -179.48(19) . . . . ?
C4 N4 C9 C10 -1.3(3) . . . . ?
C6 C1 C14 O8 179.20(18) . . . . ?
C6 C1 C14 C7 -0.4(3) . . . . ?
C6 C12 C2 O4 179.81(18) . . . . ?
C6 C12 C2 C7 -1.5(3) . . . . ?
C8 C6 C12 C2 178.85(18) . . . . ?
C10 N3 C11 N2 0.3(3) . . . . ?
C12 C6 C8 O5 -9.9(3) . . . . ?
C12 C6 C8 O3 169.63(18) . . . . ?
C14 C1 C6 C8 -177.86(19) . . . . ?
C14 C1 C6 C12 0.6(3) . . . . ?
C14 C7 C2 O4 -179.56(17) . . . . ?
C14 C7 C2 C12 1.6(3) . . . . ?
C9 N4 C4 O6 179.96(18) . . . . ?
C9 N4 C4 N1 0.3(3) . . . . ?
C9 N2 C11 N3 -0.1(3) . . . . ?
C9 C10 C5 O10 179.3(2) . . . . ?
C9 C10 C5 N1 -0.5(3) . . . . ?
C5 N1 C4 O6 -179.05(19) . . . . ?
C5 N1 C4 N4 0.6(3) . . . . ?
C5 C10 C9 N4 1.5(3) . . . . ?
C5 C10 C9 N2 179.84(19) . . . . ?
C11 N2 C9 N4 178.1(2) . . . . ?
C11 N2 C9 C10 -0.2(2) . . . . ?
C11 N3 C10 C9 -0.4(2) . . . . ?
C11 N3 C10 C5 -179.8(2) . . . . ?
C3 N4 C4 O6 0.6(3) . . . . ?
C3 N4 C4 N1 -178.97(18) . . . . ?
C3 N4 C9 N2 -0.2(3) . . . . ?
C3 N4 C9 C10 178.0(2) . . . . ?
C13 N3 C10 C9 179.2(2) . . . . ?
C13 N3 C10 C5 -0.1(4) . . . . ?
C13 N3 C11 N2 -179.3(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_2
_database_code_depnum_ccdc_archive 'CCDC 2224971'
loop_
_audit_author_name
_audit_author_address
'Xinyue Yuan'
;Qilu University of Technology, Shandong Analysis and Test Cente
China
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.5-beta
(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 H8 N4 O2, C9 H8 O3'
_chemical_formula_sum            'C16 H16 N4 O5'
_chemical_formula_weight         344.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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                   8.8706(5)
_cell_length_b                   9.1259(5)
_cell_length_c                   11.3422(4)
_cell_angle_alpha                80.367(4)
_cell_angle_beta                 69.633(4)
_cell_angle_gamma                67.650(5)
_cell_volume                     795.47(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    213.00(10)
_cell_measurement_theta_max      75.3810
_cell_measurement_theta_min      4.1610
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7567
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.161
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      213.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  59.00   1.00    0.10    --   48.42 -57.00 120.00   27
  2  ω    -21.00  21.00   1.00    0.10    --   48.42 -57.00 120.00   42
  3  ω    -28.00  26.00   1.00    0.10    --  -48.42  22.00 -11.00   54
  4  ω    -75.00 -22.00   1.00    0.20    --  -91.75 125.00-150.00   53
  5  ω    -78.00 -23.00   1.00    0.20    --  -91.75 125.00  30.00   55
  6  ω    -20.00  29.00   1.00    0.10    --   48.42 -22.00-177.00   49
  7  ω     37.00  95.00   1.00    0.10    --   48.42-125.00-120.00   58
  8  ω     80.00 110.00   1.00    0.20    --  106.65-125.00  90.00   30
  9  ω     70.00 104.00   1.00    0.20    --  106.65-125.00  60.00   34
 10  ω     38.00  66.00   1.00    0.20    --  106.65-125.00  60.00   28
 11  ω     39.00  68.00   1.00    0.20    --  106.65-125.00  90.00   29
 12  ω     77.00 103.00   1.00    0.20    --  106.65 -99.00 120.00   26
 13  ω     36.00 106.00   1.00    0.20    --  106.65 -99.00 150.00   70
 14  ω     41.00  71.00   1.00    0.20    --  106.65 -99.00 120.00   30
 15  ω     34.00  97.00   1.00    0.20    --  106.65 -99.00 -90.00   63
 16  ω     36.00 105.00   1.00    0.20    --  106.65 -99.00 -60.00   69
 17  ω     37.00  63.00   1.00    0.20    --  106.65 -57.00   0.00   26
 18  ω     36.00  65.00   1.00    0.20    --  106.65 -57.00 -30.00   29
 19  ω     45.00 105.00   1.00    0.20    --  106.65 -77.00 150.00   60
 20  ω    101.00 177.00   1.00    0.20    --  106.65  22.00 -11.00   76
 21  ω    123.00 177.00   1.00    0.20    --  106.65  38.00-150.00   54
 22  ω     94.00 120.00   1.00    0.20    --  106.65  38.00-150.00   26
 23  ω     63.00 105.00   1.00    0.10    --   48.42  22.00 -11.00   42
 24  ω   -117.00 -78.00   1.00    0.20    --  -91.75 -57.00 -30.00   39
 25  ω   -149.00-123.00   1.00    0.20    --  -91.75 -57.00 -30.00   26
 26  ω   -163.00-125.00   1.00    0.20    --  -91.75 -22.00-177.00   38
 27  ω   -110.00 -81.00   1.00    0.20    --  -91.75 -22.00-177.00   29
 28  ω   -122.00 -36.00   1.00    0.10    --  -48.42 -22.00-177.00   86
 29  ω   -154.00 -84.00   1.00    0.20    --  -91.75 -19.00 120.00   70
 30  ω   -102.00 -74.00   1.00    0.10    --  -48.42-125.00 120.00   28
 31  ω   -163.00 -88.00   1.00    0.20    --  -91.75 -99.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0991366000
_diffrn_orient_matrix_UB_12      0.1054434000
_diffrn_orient_matrix_UB_13      0.0027786000
_diffrn_orient_matrix_UB_21      -0.1701969000
_diffrn_orient_matrix_UB_22      0.1401986000
_diffrn_orient_matrix_UB_23      0.0408309000
_diffrn_orient_matrix_UB_31      -0.0162782000
_diffrn_orient_matrix_UB_32      -0.0509422000
_diffrn_orient_matrix_UB_33      0.1391063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2411
_reflns_number_total             2808
_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       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.040
_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)+(0.0697P)²+0.0854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_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 0.03115(12) 0.74523(12) 0.48803(9) 0.0342(3) Uani 1 1 d . . . . .
O2 O 0.44346(12) 0.70263(12) 0.44677(9) 0.0345(3) Uani 1 1 d . . . . .
O3 O 1.46708(13) 0.27364(14) -0.00244(10) 0.0435(3) Uani 1 1 d . . . . .
H3 H 1.481944 0.211927 -0.054849 0.065 Uiso 1 1 calc R U . . .
O4 O 0.34044(12) 0.58835(14) 0.34890(10) 0.0414(3) Uani 1 1 d . . . . .
H4 H 0.247916 0.638871 0.399556 0.062 Uiso 1 1 calc R U . . .
O5 O 0.19654(13) 0.97067(14) 0.72803(10) 0.0418(3) Uani 1 1 d . . . . .
N1 N -0.09192(14) 1.02672(13) 0.77810(10) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.10565(13) 0.86377(13) 0.61068(10) 0.0279(3) Uani 1 1 d . . . . .
H2 H 0.212160 0.821597 0.565311 0.033 Uiso 1 1 calc R U . . .
N3 N -0.33978(13) 0.90625(14) 0.65712(10) 0.0278(3) Uani 1 1 d . . . . .
N4 N -0.38974(14) 1.05782(14) 0.81156(11) 0.0282(3) Uani 1 1 d . . . . .
C1 C -0.21838(16) 1.00021(15) 0.75036(12) 0.0244(3) Uani 1 1 d . . . . .
C2 C -0.01329(17) 0.83056(16) 0.57698(12) 0.0271(3) Uani 1 1 d . . . . .
C3 C -0.18252(16) 0.90637(16) 0.65412(12) 0.0253(3) Uani 1 1 d . . . . .
C4 C 0.46702(17) 0.61441(16) 0.36734(12) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.95453(17) 0.46343(16) 0.20949(12) 0.0283(3) Uani 1 1 d . . . . .
C6 C 1.17239(18) 0.29527(16) 0.04164(12) 0.0296(3) Uani 1 1 d . . . . .
H6 H 1.202642 0.225868 -0.022033 0.036 Uiso 1 1 calc R U . . .
C7 C 1.00237(17) 0.36082(16) 0.11314(12) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.917828 0.336281 0.096944 0.034 Uiso 1 1 calc R U . . .
C8 C -0.45618(17) 0.99683(17) 0.75178(13) 0.0301(3) Uani 1 1 d . . . . .
H8 H -0.574298 1.015848 0.774219 0.036 Uiso 1 1 calc R U . . .
C9 C 1.29850(17) 0.33172(17) 0.06367(13) 0.0302(3) Uani 1 1 d . . . . .
C10 C 0.07697(17) 0.95575(17) 0.70758(13) 0.0293(3) Uani 1 1 d . . . . .
C11 C 0.77825(17) 0.53849(17) 0.28691(12) 0.0301(3) Uani 1 1 d . . . . .
H11 H 0.763131 0.603659 0.349121 0.036 Uiso 1 1 calc R U . . .
C12 C 0.63617(18) 0.52740(17) 0.28157(13) 0.0330(3) Uani 1 1 d . . . . .
H12 H 0.643547 0.462770 0.221908 0.040 Uiso 1 1 calc R U . . .
C13 C 1.08374(19) 0.49733(18) 0.23013(13) 0.0347(3) Uani 1 1 d . . . . .
H13 H 1.054587 0.565123 0.294667 0.042 Uiso 1 1 calc R U . . .
C14 C 1.25345(18) 0.43383(18) 0.15818(14) 0.0358(4) Uani 1 1 d . . . . .
H14 H 1.338090 0.459588 0.173096 0.043 Uiso 1 1 calc R U . . .
C15 C -0.13286(19) 1.12314(19) 0.88307(14) 0.0389(4) Uani 1 1 d . . . . .
H15A H -0.218248 1.225729 0.874559 0.058 Uiso 1 1 calc R U . . .
H15B H -0.029871 1.137542 0.882764 0.058 Uiso 1 1 calc R U . . .
H15C H -0.177676 1.070225 0.961650 0.058 Uiso 1 1 calc R U . . .
C16 C -0.37041(19) 0.82066(19) 0.57496(14) 0.0367(4) Uani 1 1 d . . . . .
H16A H -0.330943 0.857683 0.488366 0.055 Uiso 1 1 calc R U . . .
H16B H -0.492200 0.839420 0.598915 0.055 Uiso 1 1 calc R U . . .
H16C H -0.308421 0.708030 0.583033 0.055 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 C2 1.2379(16) . ?
O2 C4 1.2195(17) . ?
O3 H3 0.8300 . ?
O3 C9 1.3524(16) . ?
O4 H4 0.8300 . ?
O4 C4 1.3207(17) . ?
O5 C10 1.2202(17) . ?
N1 C1 1.3760(17) . ?
N1 C10 1.3802(18) . ?
N1 C15 1.4595(17) . ?
N2 H2 0.8700 . ?
N2 C2 1.3834(17) . ?
N2 C10 1.3890(18) . ?
N3 C3 1.3839(17) . ?
N3 C8 1.3336(17) . ?
N3 C16 1.4607(18) . ?
N4 C1 1.3597(17) . ?
N4 C8 1.3307(18) . ?
C1 C3 1.3748(19) . ?
C2 C3 1.4128(18) . ?
C4 C12 1.4712(19) . ?
C5 C7 1.4032(19) . ?
C5 C11 1.4548(19) . ?
C5 C13 1.395(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.3838(19) . ?
C6 C9 1.389(2) . ?
C7 H7 0.9400 . ?
C8 H8 0.9400 . ?
C9 C14 1.389(2) . ?
C11 H11 0.9400 . ?
C11 C12 1.325(2) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C13 C14 1.3812(19) . ?
C14 H14 0.9400 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
C9 O3 H3 109.5 . . ?
C4 O4 H4 109.5 . . ?
C1 N1 C10 118.94(11) . . ?
C1 N1 C15 121.24(11) . . ?
C10 N1 C15 119.78(11) . . ?
C2 N2 H2 115.8 . . ?
C2 N2 C10 128.37(11) . . ?
C10 N2 H2 115.8 . . ?
C3 N3 C16 126.68(11) . . ?
C8 N3 C3 106.01(11) . . ?
C8 N3 C16 127.29(12) . . ?
C8 N4 C1 103.70(11) . . ?
N4 C1 N1 126.57(12) . . ?
N4 C1 C3 111.13(12) . . ?
C3 C1 N1 122.29(12) . . ?
O1 C2 N2 121.38(12) . . ?
O1 C2 C3 126.84(13) . . ?
N2 C2 C3 111.77(11) . . ?
N3 C3 C2 132.38(12) . . ?
C1 C3 N3 105.34(11) . . ?
C1 C3 C2 122.27(12) . . ?
O2 C4 O4 122.73(12) . . ?
O2 C4 C12 124.50(13) . . ?
O4 C4 C12 112.76(12) . . ?
C7 C5 C11 123.80(13) . . ?
C13 C5 C7 117.78(12) . . ?
C13 C5 C11 118.41(13) . . ?
C7 C6 H6 119.9 . . ?
C7 C6 C9 120.20(12) . . ?
C9 C6 H6 119.9 . . ?
C5 C7 H7 119.6 . . ?
C6 C7 C5 120.86(13) . . ?
C6 C7 H7 119.6 . . ?
N3 C8 H8 123.1 . . ?
N4 C8 N3 113.81(11) . . ?
N4 C8 H8 123.1 . . ?
O3 C9 C6 123.87(12) . . ?
O3 C9 C14 116.38(13) . . ?
C6 C9 C14 119.75(12) . . ?
O5 C10 N1 122.87(13) . . ?
O5 C10 N2 120.79(12) . . ?
N1 C10 N2 116.34(12) . . ?
C5 C11 H11 115.6 . . ?
C12 C11 C5 128.76(14) . . ?
C12 C11 H11 115.6 . . ?
C4 C12 H12 119.4 . . ?
C11 C12 C4 121.20(13) . . ?
C11 C12 H12 119.4 . . ?
C5 C13 H13 119.2 . . ?
C14 C13 C5 121.69(13) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.71(13) . . ?
C13 C14 H14 120.1 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N3 1.9(2) . . . . ?
O1 C2 C3 C1 -179.45(13) . . . . ?
O2 C4 C12 C11 1.0(2) . . . . ?
O3 C9 C14 C13 -179.69(14) . . . . ?
O4 C4 C12 C11 -179.62(14) . . . . ?
N1 C1 C3 N3 178.97(11) . . . . ?
N1 C1 C3 C2 0.0(2) . . . . ?
N2 C2 C3 N3 -178.91(13) . . . . ?
N2 C2 C3 C1 -0.26(19) . . . . ?
N4 C1 C3 N3 -0.24(15) . . . . ?
N4 C1 C3 C2 -179.21(12) . . . . ?
C1 N1 C10 O5 -178.39(13) . . . . ?
C1 N1 C10 N2 1.21(19) . . . . ?
C1 N4 C8 N3 -0.47(15) . . . . ?
C2 N2 C10 O5 177.95(13) . . . . ?
C2 N2 C10 N1 -1.7(2) . . . . ?
C3 N3 C8 N4 0.33(16) . . . . ?
C5 C11 C12 C4 -179.18(13) . . . . ?
C5 C13 C14 C9 -0.9(2) . . . . ?
C6 C9 C14 C13 0.5(2) . . . . ?
C7 C5 C11 C12 -0.8(3) . . . . ?
C7 C5 C13 C14 0.5(2) . . . . ?
C7 C6 C9 O3 -179.53(13) . . . . ?
C7 C6 C9 C14 0.3(2) . . . . ?
C8 N3 C3 C1 -0.04(15) . . . . ?
C8 N3 C3 C2 178.77(14) . . . . ?
C8 N4 C1 N1 -178.75(13) . . . . ?
C8 N4 C1 C3 0.43(15) . . . . ?
C9 C6 C7 C5 -0.6(2) . . . . ?
C10 N1 C1 N4 178.58(12) . . . . ?
C10 N1 C1 C3 -0.5(2) . . . . ?
C10 N2 C2 O1 -179.62(13) . . . . ?
C10 N2 C2 C3 1.15(19) . . . . ?
C11 C5 C7 C6 178.98(13) . . . . ?
C11 C5 C13 C14 -178.28(14) . . . . ?
C13 C5 C7 C6 0.3(2) . . . . ?
C13 C5 C11 C12 177.90(15) . . . . ?
C15 N1 C1 N4 0.9(2) . . . . ?
C15 N1 C1 C3 -178.21(13) . . . . ?
C15 N1 C10 O5 -0.6(2) . . . . ?
C15 N1 C10 N2 178.95(12) . . . . ?
C16 N3 C3 C1 -178.63(13) . . . . ?
C16 N3 C3 C2 0.2(2) . . . . ?
C16 N3 C8 N4 178.91(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.848
