# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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. 
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data_pcvgcv
_database_code_depnum_ccdc_archive 'CCDC 2520172'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2025-07-25
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9.7 H14.4 N5 O3.3'
_chemical_formula_sum            'C9.70 H14.40 N5 O3.30'
_chemical_formula_weight         253.86
_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                   11.6218(8)
_cell_length_b                   10.7919(7)
_cell_length_c                   8.7804(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.008(3)
_cell_angle_gamma                90
_cell_volume                     1087.67(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3948
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.188
_cell_measurement_theta_min      2.591
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1742 before and 0.1284 after correction.
The Ratio of minimum to maximum transmission is 0.7277.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11266
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.590
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1770
_reflns_number_total             2222
_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 V8.41 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.204
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0791
_refine_ls_restrained_S_all      1.127
_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)+(0.0637P)²+3.4708P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1821
_refine_ls_wR_factor_ref         0.1963
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O19-C17
 1.4 with sigma of 0.02
 C17-C13 \\sim C15-C13
 with sigma of 0.02
 C12-C11 \\sim O14-C11
 with sigma of 0.02
 C12-C13 \\sim O14-C13
 with sigma of 0.02
 O14-C11 \\sim O14-C13
 with sigma of 0.02
 C11-C12 \\sim C13-C12
 with sigma of 0.02
3. Rigid bond restraints
 O19, O14
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O19) \\sim Ueq, Uanis(O18) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
5. Others
 Sof(H17C)=Sof(H17D)=Sof(O19)=Sof(H19)=1-FVAR(1)
 Sof(O18)=Sof(H18)=Sof(H17A)=Sof(H17B)=FVAR(1)
 Fixed Sof: C12(0.7) H12A(0.7) H12B(0.7) H11A(0.7) H11B(0.7) H11C(0.3)
 H11D(0.3) H13(0.7) H13A(0.3) O14(0.3)
6.a Ternary CH refined with riding coordinates:
 C13(H13), C13(H13A)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C11(H11C,H11D), C15(H15A,H15B), C17(H17A,
 H17B), C17(H17C,H17D)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7)
6.d Tetrahedral OH refined with riding coordinates:
 O19(H19)
6.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
6.f Idealised tetrahedral OH refined as rotating group:
 O16(H16), O18(H18)
;
_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
O20 O -0.0677(2) 0.7119(2) 0.1879(3) 0.0152(6) Uani 1 1 d . . . . .
O16 O 0.7288(2) 0.7026(3) 0.8090(3) 0.0242(7) Uani 1 1 d . . . . .
H16 H 0.783825 0.728775 0.766299 0.036 Uiso 1 1 calc R U . . .
N3 N 0.0453(2) 0.8496(3) 0.3390(3) 0.0120(6) Uani 1 1 d . . . . .
H3 H 0.007761 0.910049 0.285195 0.014 Uiso 1 1 calc R U . . .
N8 N 0.2185(2) 0.5771(2) 0.5712(3) 0.0113(6) Uani 1 1 d . . . . .
N6 N 0.0856(2) 0.5126(3) 0.3735(3) 0.0126(6) Uani 1 1 d . . . . .
N10 N 0.1940(2) 0.7998(3) 0.5482(3) 0.0127(6) Uani 1 1 d . . . . .
N1 N 0.1426(2) 1.0035(3) 0.4899(4) 0.0163(7) Uani 1 1 d . . . . .
H1A H 0.195130 1.028774 0.566796 0.020 Uiso 1 1 calc R U . . .
H1B H 0.099327 1.057901 0.432195 0.020 Uiso 1 1 calc R U . . .
O18 O 0.6266(3) 0.4280(3) 0.7425(4) 0.0288(11) Uani 0.820(9) 1 d . U P A 1
H18 H 0.671876 0.376995 0.793379 0.043 Uiso 0.820(9) 1 calc R U P A 1
C2 C 0.1284(3) 0.8823(3) 0.4607(4) 0.0110(7) Uani 1 1 d . . . . .
C9 C 0.1684(3) 0.6818(3) 0.5033(4) 0.0113(7) Uani 1 1 d . . . . .
C5 C 0.0863(3) 0.6409(3) 0.3825(4) 0.0117(7) Uani 1 1 d . . . . .
C4 C 0.0156(3) 0.7300(3) 0.2936(4) 0.0119(7) Uani 1 1 d . . . . .
C12 C 0.4270(5) 0.6103(10) 0.6395(9) 0.008(2) Uani 0.7 1 d D U P B 1
H12A H 0.413023 0.688461 0.580567 0.010 Uiso 0.7 1 calc R U P B 1
H12B H 0.446167 0.545486 0.567679 0.010 Uiso 0.7 1 calc R U P B 1
C11 C 0.3171(3) 0.5740(3) 0.6979(4) 0.0147(7) Uani 1 1 d D . . . .
H11A H 0.325541 0.489554 0.742276 0.018 Uiso 0.7 1 calc R U P B 1
H11B H 0.302493 0.631940 0.780212 0.018 Uiso 0.7 1 calc R U P B 1
H11C H 0.320992 0.491320 0.747280 0.018 Uiso 0.3 1 calc R U P B 2
H11D H 0.304363 0.636198 0.776484 0.018 Uiso 0.3 1 calc R U P B 2
C7 C 0.1658(3) 0.4783(3) 0.4880(4) 0.0124(7) Uani 1 1 d . . . . .
H7 H 0.185541 0.394246 0.511249 0.015 Uiso 1 1 calc R U . . .
C13 C 0.5306(3) 0.6278(4) 0.7662(4) 0.0239(9) Uani 1 1 d D . . . .
H13 H 0.507930 0.685495 0.845509 0.029 Uiso 0.7 1 calc R U P B 1
H13A H 0.505373 0.685604 0.843608 0.029 Uiso 0.3 1 calc R U P B 2
C15 C 0.6282(3) 0.6858(4) 0.6964(5) 0.0235(9) Uani 1 1 d D . . . .
H15A H 0.647713 0.632063 0.612713 0.028 Uiso 1 1 calc R U . . .
H15B H 0.602451 0.767055 0.650914 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5730(4) 0.5036(4) 0.8459(5) 0.0331(10) Uani 1 1 d D . . . .
H17A H 0.629798 0.520747 0.939919 0.040 Uiso 0.820(9) 1 calc R U P A 1
H17B H 0.506022 0.458896 0.877028 0.040 Uiso 0.820(9) 1 calc R U P A 1
H17C H 0.656420 0.506089 0.834532 0.040 Uiso 0.180(9) 1 calc R U P A 2
H17D H 0.572525 0.525896 0.955176 0.040 Uiso 0.180(9) 1 calc R U P A 2
O19 O 0.5557(19) 0.3706(15) 0.853(3) 0.062(8) Uani 0.180(9) 1 d D U P A 2
H19 H 0.573402 0.346468 0.944755 0.093 Uiso 0.180(9) 1 calc R U P A 2
O14 O 0.4304(11) 0.600(3) 0.6431(18) 0.053(9) Uani 0.3 1 d D . P B 2


_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
O20 C4 1.248(4) . ?
O16 H16 0.8400 . ?
O16 C15 1.419(4) . ?
N3 H3 0.8800 . ?
N3 C2 1.369(4) . ?
N3 C4 1.379(4) . ?
N8 C9 1.365(4) . ?
N8 C11 1.467(4) . ?
N8 C7 1.380(4) . ?
N6 C5 1.388(4) . ?
N6 C7 1.313(4) . ?
N10 C2 1.334(4) . ?
N10 C9 1.352(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.338(4) . ?
O18 H18 0.8400 . ?
O18 C17 1.434(6) . ?
C9 C5 1.383(5) . ?
C5 C4 1.416(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.501(7) . ?
C12 C13 1.518(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 O14 1.498(13) . ?
C7 H7 0.9500 . ?
C13 H13 1.0000 . ?
C13 H13A 1.0000 . ?
C13 C15 1.507(5) . ?
C13 C17 1.557(6) . ?
C13 O14 1.490(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C17 O19 1.452(16) . ?
O19 H19 0.8400 . ?

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
C15 O16 H16 109.5 . . ?
C2 N3 H3 117.3 . . ?
C2 N3 C4 125.5(3) . . ?
C4 N3 H3 117.3 . . ?
C9 N8 C11 125.4(3) . . ?
C9 N8 C7 106.5(3) . . ?
C7 N8 C11 127.8(3) . . ?
C7 N6 C5 103.9(3) . . ?
C2 N10 C9 112.3(3) . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
C17 O18 H18 109.5 . . ?
N10 C2 N3 123.2(3) . . ?
N10 C2 N1 120.0(3) . . ?
N1 C2 N3 116.8(3) . . ?
N8 C9 C5 105.5(3) . . ?
N10 C9 N8 126.3(3) . . ?
N10 C9 C5 128.2(3) . . ?
N6 C5 C4 130.4(3) . . ?
C9 C5 N6 111.0(3) . . ?
C9 C5 C4 118.5(3) . . ?
O20 C4 N3 119.4(3) . . ?
O20 C4 C5 128.3(3) . . ?
N3 C4 C5 112.3(3) . . ?
H12A C12 H12B 107.7 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C11 C12 C13 113.7(5) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N8 C11 C12 109.9(4) . . ?
N8 C11 H11A 109.7 . . ?
N8 C11 H11B 109.7 . . ?
N8 C11 H11C 109.2 . . ?
N8 C11 H11D 109.2 . . ?
N8 C11 O14 111.9(7) . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
H11C C11 H11D 107.9 . . ?
O14 C11 H11C 109.2 . . ?
O14 C11 H11D 109.2 . . ?
N8 C7 H7 123.5 . . ?
N6 C7 N8 113.0(3) . . ?
N6 C7 H7 123.5 . . ?
C12 C13 H13 108.8 . . ?
C12 C13 C17 112.4(5) . . ?
C15 C13 C12 108.4(4) . . ?
C15 C13 H13 108.8 . . ?
C15 C13 H13A 109.7 . . ?
C15 C13 C17 109.6(3) . . ?
C17 C13 H13 108.8 . . ?
C17 C13 H13A 109.7 . . ?
O14 C13 H13A 109.7 . . ?
O14 C13 C15 109.9(7) . . ?
O14 C13 C17 108.2(11) . . ?
O16 C15 C13 111.1(3) . . ?
O16 C15 H15A 109.4 . . ?
O16 C15 H15B 109.4 . . ?
C13 C15 H15A 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O18 C17 C13 110.1(3) . . ?
O18 C17 H17A 109.6 . . ?
O18 C17 H17B 109.6 . . ?
C13 C17 H17A 109.6 . . ?
C13 C17 H17B 109.6 . . ?
C13 C17 H17C 100.2 . . ?
C13 C17 H17D 100.2 . . ?
H17A C17 H17B 108.2 . . ?
H17C C17 H17D 104.2 . . ?
O19 C17 C13 146.6(10) . . ?
O19 C17 H17C 100.2 . . ?
O19 C17 H17D 100.2 . . ?
C17 O19 H19 109.5 . . ?
C13 O14 C11 115.6(11) . . ?

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
N8 C9 C5 N6 -0.6(4) . . . . ?
N8 C9 C5 C4 177.2(3) . . . . ?
N8 C11 O14 C13 166.5(14) . . . . ?
N6 C5 C4 O20 2.6(6) . . . . ?
N6 C5 C4 N3 -179.5(3) . . . . ?
N10 C9 C5 N6 -179.8(3) . . . . ?
N10 C9 C5 C4 -2.0(5) . . . . ?
C2 N3 C4 O20 174.6(3) . . . . ?
C2 N3 C4 C5 -3.5(4) . . . . ?
C2 N10 C9 N8 -178.7(3) . . . . ?
C2 N10 C9 C5 0.3(5) . . . . ?
C9 N8 C11 C12 -72.2(6) . . . . ?
C9 N8 C11 O14 -76.4(12) . . . . ?
C9 N8 C7 N6 -0.5(4) . . . . ?
C9 N10 C2 N3 -0.3(4) . . . . ?
C9 N10 C2 N1 179.9(3) . . . . ?
C9 C5 C4 O20 -174.7(3) . . . . ?
C9 C5 C4 N3 3.2(4) . . . . ?
C5 N6 C7 N8 0.1(4) . . . . ?
C4 N3 C2 N10 2.2(5) . . . . ?
C4 N3 C2 N1 -178.0(3) . . . . ?
C12 C13 C15 O16 -178.9(5) . . . . ?
C12 C13 C17 O18 70.3(5) . . . . ?
C11 N8 C9 N10 -5.7(5) . . . . ?
C11 N8 C9 C5 175.1(3) . . . . ?
C11 N8 C7 N6 -174.8(3) . . . . ?
C11 C12 C13 C15 -169.9(6) . . . . ?
C11 C12 C13 C17 68.9(8) . . . . ?
C7 N8 C9 N10 179.8(3) . . . . ?
C7 N8 C9 C5 0.6(3) . . . . ?
C7 N8 C11 C12 101.1(6) . . . . ?
C7 N8 C11 O14 96.9(12) . . . . ?
C7 N6 C5 C9 0.3(4) . . . . ?
C7 N6 C5 C4 -177.2(3) . . . . ?
C13 C12 C11 N8 171.7(5) . . . . ?
C15 C13 C17 O18 -50.3(4) . . . . ?
C15 C13 C17 O19 -121.0(18) . . . . ?
C15 C13 O14 C11 -164.6(14) . . . . ?
C17 C13 C15 O16 -55.9(4) . . . . ?
C17 C13 O14 C11 75.8(19) . . . . ?
O14 C13 C15 O16 -174.7(12) . . . . ?
O14 C13 C17 O19 -1.1(19) . . . . ?


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

data_mo_20231624_0m
_database_code_depnum_ccdc_archive 'CCDC 2520168'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 N5 O4'
_chemical_formula_sum            'C9 H13 N5 O4'
_chemical_formula_weight         255.24
_chemical_absolute_configuration .
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.3553(3)
_cell_length_b                   10.7903(7)
_cell_length_c                   11.6008(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.684(2)
_cell_angle_gamma                90
_cell_volume                     538.93(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.009
_cell_measurement_theta_min      3.554
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1454 before and 0.0894 after correction.
The Ratio of minimum to maximum transmission is 0.6041.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6358
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.530
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.847
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                1593
_reflns_number_total             2051
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 522 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.087
_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)+(0.0858P)²+0.3173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1798
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups,
  All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O5) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Fixed Sof: O4(0.7) H4A(0.7) H8AA(0.7) H8AB(0.7) H8BC(0.3) H8BD(0.3) O5(0.3)
 H5(0.3)
4.a Ternary CH refined with riding coordinates:
 C7(H7)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C8(H8AA,H8AB), C8(H8BC,H8BD)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4)
4.d Tetrahedral OH refined with riding coordinates:
 O4(H4A), O5(H5)
4.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
4.f Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1295(9) 0.4749(4) -0.0655(3) 0.0304(11) Uani 1 1 d . . . . .
N2 N 0.1816(11) 0.6112(5) 0.0490(4) 0.0238(11) Uani 1 1 d . . . . .
O2 O 0.7510(10) 0.3732(5) 0.4296(4) 0.0395(13) Uani 1 1 d . . . . .
N3 N 0.2314(12) 0.2741(5) 0.0908(4) 0.0262(12) Uani 1 1 d . . . . .
H3 H 0.099382 0.227289 0.045104 0.031 Uiso 1 1 calc R U . . .
N5 N 0.5819(11) 0.5578(5) 0.2027(4) 0.0252(12) Uani 1 1 d . . . . .
O3 O 1.1118(10) 0.4650(6) 0.7211(4) 0.0512(16) Uani 1 1 d . . . . .
H3A H 1.039213 0.471908 0.783913 0.077 Uiso 1 1 calc R U . . .
N4 N 0.6153(10) 0.3347(5) 0.2279(4) 0.0266(11) Uani 1 1 d . . . . .
N1 N 0.4736(12) 0.7623(5) 0.1549(5) 0.0303(12) Uani 1 1 d . . . . .
H1A H 0.621670 0.786702 0.210461 0.036 Uiso 1 1 calc R U . . .
H1B H 0.362643 0.817554 0.110938 0.036 Uiso 1 1 calc R U . . .
C2 C 0.0843(13) 0.4926(6) 0.0193(5) 0.0256(13) Uani 1 1 d . . . . .
C5 C 0.4922(12) 0.4398(6) 0.1756(5) 0.0239(13) Uani 1 1 d . . . . .
C1 C 0.4177(14) 0.6424(6) 0.1375(5) 0.0268(14) Uani 1 1 d . . . . .
C4 C 0.4469(14) 0.2380(6) 0.1726(5) 0.0261(14) Uani 1 1 d . . . . .
H4 H 0.485332 0.153436 0.192676 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8663(12) 0.3291(6) 0.3269(5) 0.0255(13) Uani 1 1 d . . . . .
H6A H 0.940646 0.242682 0.339077 0.031 Uiso 1 1 calc R U . . .
H6B H 1.042565 0.381141 0.311287 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2522(14) 0.4023(6) 0.0901(5) 0.0272(15) Uani 1 1 d . . . . .
O4 O 0.8193(16) 0.6420(7) 0.4524(6) 0.0452(19) Uani 0.7 1 d . U P A 1
H4A H 0.679623 0.608488 0.404678 0.068 Uiso 0.7 1 calc R U P A 1
C9 C 0.8698(14) 0.4306(8) 0.6300(5) 0.0367(17) Uani 1 1 d . . . . .
H9A H 0.695138 0.489860 0.626514 0.044 Uiso 1 1 calc R U . . .
H9B H 0.791770 0.346924 0.645313 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9951(15) 0.4310(8) 0.5161(6) 0.0427(18) Uani 1 1 d . . . . .
H7 H 1.188772 0.379990 0.523526 0.051 Uiso 1 1 calc R U . . .
C8 C 1.064(2) 0.5627(8) 0.4768(7) 0.057(2) Uani 1 1 d . . . . .
H8AA H 1.216288 0.600777 0.538751 0.068 Uiso 0.7 1 calc R U P A 1
H8AB H 1.165695 0.555945 0.406325 0.068 Uiso 0.7 1 calc R U P A 1
H8BC H 0.925056 0.613986 0.517453 0.068 Uiso 0.3 1 calc R U P A 2
H8BD H 1.275116 0.578099 0.519497 0.068 Uiso 0.3 1 calc R U P A 2
O5 O 1.068(5) 0.624(2) 0.3793(18) 0.076(6) Uani 0.3 1 d . U P A 2
H5 H 1.064447 0.574062 0.323833 0.114 Uiso 0.3 1 calc R U P A 2


_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 1.263(7) . ?
N2 C2 1.376(8) . ?
N2 C1 1.380(7) . ?
O2 C6 1.441(7) . ?
O2 C7 1.485(8) . ?
N3 H3 0.8800 . ?
N3 C4 1.290(8) . ?
N3 C3 1.386(8) . ?
N5 C5 1.355(9) . ?
N5 C1 1.324(8) . ?
O3 H3A 0.8400 . ?
O3 C9 1.424(7) . ?
N4 C5 1.358(8) . ?
N4 C4 1.377(8) . ?
N4 C6 1.463(7) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.327(8) . ?
C2 C3 1.406(9) . ?
C5 C3 1.388(8) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O4 H4A 0.8400 . ?
O4 C8 1.362(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C7 1.504(9) . ?
C7 H7 1.0000 . ?
C7 C8 1.536(12) . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 O5 1.31(2) . ?
O5 H5 0.8400 . ?

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 N2 C1 125.4(5) . . ?
C6 O2 C7 113.2(5) . . ?
C4 N3 H3 127.3 . . ?
C4 N3 C3 105.4(5) . . ?
C3 N3 H3 127.3 . . ?
C1 N5 C5 113.8(5) . . ?
C9 O3 H3A 109.5 . . ?
C5 N4 C4 106.2(5) . . ?
C5 N4 C6 125.7(5) . . ?
C4 N4 C6 128.1(5) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
O1 C2 N2 119.9(6) . . ?
O1 C2 C3 127.4(6) . . ?
N2 C2 C3 112.7(5) . . ?
N5 C5 N4 126.9(5) . . ?
N5 C5 C3 126.8(5) . . ?
N4 C5 C3 106.2(5) . . ?
N5 C1 N2 122.3(6) . . ?
N5 C1 N1 121.0(6) . . ?
N1 C1 N2 116.7(6) . . ?
N3 C4 N4 113.0(6) . . ?
N3 C4 H4 123.5 . . ?
N4 C4 H4 123.5 . . ?
O2 C6 N4 108.9(4) . . ?
O2 C6 H6A 109.9 . . ?
O2 C6 H6B 109.9 . . ?
N4 C6 H6A 109.9 . . ?
N4 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N3 C3 C2 131.8(6) . . ?
N3 C3 C5 109.3(5) . . ?
C5 C3 C2 118.9(6) . . ?
C8 O4 H4A 109.5 . . ?
O3 C9 H9A 109.9 . . ?
O3 C9 H9B 109.9 . . ?
O3 C9 C7 109.0(5) . . ?
H9A C9 H9B 108.3 . . ?
C7 C9 H9A 109.9 . . ?
C7 C9 H9B 109.9 . . ?
O2 C7 C9 105.9(5) . . ?
O2 C7 H7 109.6 . . ?
O2 C7 C8 109.9(6) . . ?
C9 C7 H7 109.6 . . ?
C9 C7 C8 112.1(7) . . ?
C8 C7 H7 109.6 . . ?
O4 C8 C7 117.4(8) . . ?
O4 C8 H8AA 107.9 . . ?
O4 C8 H8AB 107.9 . . ?
C7 C8 H8AA 107.9 . . ?
C7 C8 H8AB 107.9 . . ?
C7 C8 H8BC 102.4 . . ?
C7 C8 H8BD 102.4 . . ?
H8AA C8 H8AB 107.2 . . ?
H8BC C8 H8BD 104.9 . . ?
O5 C8 C7 138.7(13) . . ?
O5 C8 H8BC 102.4 . . ?
O5 C8 H8BD 102.4 . . ?
C8 O5 H5 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 -1.8(10) . . . . ?
O1 C2 C3 C5 176.4(6) . . . . ?
N2 C2 C3 N3 179.9(6) . . . . ?
N2 C2 C3 C5 -1.9(7) . . . . ?
O2 C7 C8 O4 53.9(9) . . . . ?
O2 C7 C8 O5 -32(2) . . . . ?
N5 C5 C3 N3 -179.1(6) . . . . ?
N5 C5 C3 C2 2.3(9) . . . . ?
O3 C9 C7 O2 170.1(6) . . . . ?
O3 C9 C7 C8 -70.0(8) . . . . ?
N4 C5 C3 N3 -0.1(6) . . . . ?
N4 C5 C3 C2 -178.7(5) . . . . ?
C2 N2 C1 N5 1.4(9) . . . . ?
C2 N2 C1 N1 -178.5(5) . . . . ?
C5 N5 C1 N2 -1.2(7) . . . . ?
C5 N5 C1 N1 178.7(5) . . . . ?
C5 N4 C4 N3 0.2(6) . . . . ?
C5 N4 C6 O2 70.3(7) . . . . ?
C1 N2 C2 O1 -178.2(5) . . . . ?
C1 N2 C2 C3 0.2(8) . . . . ?
C1 N5 C5 N4 -179.4(5) . . . . ?
C1 N5 C5 C3 -0.6(8) . . . . ?
C4 N3 C3 C2 178.6(6) . . . . ?
C4 N3 C3 C5 0.2(7) . . . . ?
C4 N4 C5 N5 179.0(6) . . . . ?
C4 N4 C5 C3 0.0(6) . . . . ?
C4 N4 C6 O2 -106.2(7) . . . . ?
C6 O2 C7 C9 -160.8(6) . . . . ?
C6 O2 C7 C8 77.9(8) . . . . ?
C6 N4 C5 N5 1.8(9) . . . . ?
C6 N4 C5 C3 -177.2(5) . . . . ?
C6 N4 C4 N3 177.2(5) . . . . ?
C3 N3 C4 N4 -0.2(7) . . . . ?
C9 C7 C8 O4 -63.7(9) . . . . ?
C9 C7 C8 O5 -150(2) . . . . ?
C7 O2 C6 N4 -150.9(6) . . . . ?


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

data_cu_p_g_490k_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2520170'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H16 N5 O3, 2(C10 H15 N5 O3)'
_chemical_formula_sum            'C30 H46 N15 O9'
_chemical_formula_weight         760.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.6410(5)
_cell_length_b                   11.0691(4)
_cell_length_c                   23.4349(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.007(2)
_cell_angle_gamma                90
_cell_volume                     3533.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6291
_cell_measurement_temperature    490(2)
_cell_measurement_theta_max      67.157
_cell_measurement_theta_min      3.668
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1581 before and 0.0998 after correction. The Ratio of minimum to maximum transmission is 0.7128. 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    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1612
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29340
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.364
_diffrn_reflns_theta_min         3.668
_diffrn_ambient_temperature      490.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3935
_reflns_number_total             6420
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         6420
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0874
_refine_ls_restrained_S_all      1.062
_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)+(0.1932P)²+0.2773P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2672
_refine_ls_wR_factor_ref         0.3027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C12(H12), C29(H29), C46(H46)
3.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00I(H00C,H00D), C010(H01A,H01B), C11(H11A,H11B), C14(H14A,
 H14B), C13(H13A,H13B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B),
 C45(H45A,H45B), C48(H48A,H48B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), C10(H10), N20(H20), C27(H27), N36(H36), C44(H44)
3.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N18(H18A,H18B), N34(H34A,H34B)
3.e Idealised tetrahedral OH refined as rotating group:
 O32(H32), O33(H33), O49(H49), O1(H1), O2(H2), O0AA(H0AA)
;
_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
N1 N 0.7674(2) 0.4344(3) 0.39357(16) 0.1103(10) Uani 1 1 d . . . . .
H1A H 0.826016 0.410145 0.387989 0.132 Uiso 1 1 calc R . . . .
H1B H 0.721192 0.382530 0.397329 0.132 Uiso 1 1 calc R . . . .
N4 N 0.65361(19) 0.5842(3) 0.40479(12) 0.0855(7) Uani 1 1 d . . . . .
H4 H 0.612592 0.526399 0.409207 0.103 Uiso 1 1 calc R . . . .
N3 N 0.6895(2) 0.9106(3) 0.40128(14) 0.0977(9) Uani 1 1 d . . . . .
H3 H 0.639101 0.955967 0.405279 0.117 Uiso 1 1 calc R . . . .
C6 C 0.6173(2) 0.6999(3) 0.40689(15) 0.0840(9) Uani 1 1 d . . . . .
N5 N 0.8410(2) 0.8488(3) 0.38871(12) 0.0901(8) Uani 1 1 d . . . . .
C7 C 0.6926(2) 0.7853(3) 0.40175(14) 0.0813(8) Uani 1 1 d . . . . .
N008 N 0.8189(2) 0.6319(3) 0.39064(12) 0.0861(8) Uani 1 1 d . . . . .
C8 C 0.7860(2) 0.7478(3) 0.39348(13) 0.0797(8) Uani 1 1 d . . . . .
C9 C 0.7481(2) 0.5522(3) 0.39640(14) 0.0821(8) Uani 1 1 d . . . . .
C00H C 0.1635(2) 0.5978(4) 0.26942(14) 0.0897(10) Uani 1 1 d . . . . .
H00A H 0.154070 0.532526 0.296189 0.108 Uiso 1 1 calc R . . . .
H00B H 0.141307 0.671878 0.286720 0.108 Uiso 1 1 calc R . . . .
C00I C 0.1853(2) 0.3312(4) 0.39990(13) 0.0853(9) Uani 1 1 d . . . . .
H00C H 0.208687 0.259336 0.381214 0.102 Uiso 1 1 calc R . . . .
H00D H 0.194963 0.399098 0.374636 0.102 Uiso 1 1 calc R . . . .
C010 C 1.0031(3) 0.8350(4) 0.43569(15) 0.1005(11) Uani 1 1 d . . . . .
H01A H 0.984026 0.758851 0.452298 0.121 Uiso 1 1 calc R . . . .
H01B H 0.987040 0.898955 0.461925 0.121 Uiso 1 1 calc R . . . .
C10 C 0.7788(3) 0.9446(4) 0.39352(17) 0.0989(11) Uani 1 1 d . . . . .
H10 H 0.798261 1.024967 0.391477 0.119 Uiso 1 1 calc R . . . .
C11 C 0.9461(3) 0.8531(4) 0.38087(16) 0.0993(11) Uani 1 1 d . . . . .
H11A H 0.962888 0.930689 0.364834 0.119 Uiso 1 1 calc R . . . .
H11B H 0.963294 0.790740 0.354081 0.119 Uiso 1 1 calc R . . . .
C12 C 1.1129(3) 0.8345(4) 0.42907(19) 0.1067(12) Uani 1 1 d . U . . .
H12 H 1.121807 0.783060 0.395696 0.128 Uiso 1 1 calc R . . . .
C14 C 1.1576(6) 0.9550(8) 0.4134(3) 0.182(3) Uani 1 1 d . U . . .
H14A H 1.220730 0.942062 0.397140 0.218 Uiso 1 1 calc R . . . .
H14B H 1.114951 0.995941 0.385163 0.218 Uiso 1 1 calc R . . . .
C13 C 1.1628(4) 0.7698(7) 0.4764(3) 0.168(3) Uani 1 1 d . . . . .
H13A H 1.151935 0.812008 0.511734 0.202 Uiso 1 1 calc R . . . .
H13B H 1.134512 0.689707 0.479032 0.202 Uiso 1 1 calc R . . . .
N19 N 0.5388(2) 0.0823(3) 0.41982(12) 0.0862(8) Uani 1 1 d . . . . .
N18 N 0.4252(2) -0.0675(3) 0.43352(15) 0.1096(10) Uani 1 1 d . . . . .
H18A H 0.367332 -0.092413 0.440454 0.132 Uiso 1 1 calc R . . . .
H18B H 0.471060 -0.118803 0.427833 0.132 Uiso 1 1 calc R . . . .
N20 N 0.37539(19) 0.1307(3) 0.44011(12) 0.0860(8) Uani 1 1 d . . . . .
H20 H 0.316297 0.110976 0.447235 0.103 Uiso 1 1 calc R . . . .
N21 N 0.35091(19) 0.3481(3) 0.44437(12) 0.0838(7) Uani 1 1 d . . . . .
N22 N 0.5015(2) 0.4117(3) 0.42706(14) 0.0930(8) Uani 1 1 d . . . . .
C23 C 0.4441(2) 0.0514(3) 0.43158(14) 0.0829(9) Uani 1 1 d . . . . .
C24 C 0.4054(2) 0.2458(3) 0.43673(13) 0.0802(8) Uani 1 1 d . . . . .
C25 C 0.4985(2) 0.2867(3) 0.42615(14) 0.0839(9) Uani 1 1 d . . . . .
C26 C 0.5718(2) 0.2001(3) 0.41746(14) 0.0824(8) Uani 1 1 d . . . . .
C27 C 0.4118(3) 0.4429(3) 0.43813(16) 0.0928(10) Uani 1 1 d . . . . .
H27 H 0.391881 0.522821 0.441383 0.111 Uiso 1 1 calc R . . . .
C28 C 0.2458(2) 0.3504(4) 0.45342(14) 0.0901(10) Uani 1 1 d . . . . .
H28A H 0.228955 0.427765 0.469709 0.108 Uiso 1 1 calc R . . . .
H28B H 0.230661 0.288026 0.480671 0.108 Uiso 1 1 calc R . . . .
C29 C 0.0766(3) 0.3172(4) 0.40766(15) 0.0898(9) Uani 1 1 d . . . . .
H29 H 0.069448 0.254307 0.436579 0.108 Uiso 1 1 calc R . . . .
C30 C 0.0281(3) 0.4288(5) 0.4293(2) 0.1221(15) Uani 1 1 d . . . . .
H30A H -0.037570 0.408793 0.440235 0.146 Uiso 1 1 calc R . . . .
H30B H 0.064989 0.457848 0.463119 0.146 Uiso 1 1 calc R . . . .
C31 C 0.0262(3) 0.2720(5) 0.35371(19) 0.1144(13) Uani 1 1 d . . . . .
H31A H 0.035036 0.329818 0.323313 0.137 Uiso 1 1 calc R . . . .
H31B H 0.055818 0.196284 0.342901 0.137 Uiso 1 1 calc R . . . .
O32 O 0.0227(3) 0.5177(4) 0.3894(3) 0.1736(17) Uani 1 1 d . . . . .
H32 H -0.033272 0.544882 0.386898 0.260 Uiso 1 1 calc GR . . . .
O33 O -0.0753(2) 0.2541(5) 0.36009(17) 0.1547(15) Uani 1 1 d . . . . .
H33 H -0.099867 0.222225 0.331173 0.232 Uiso 1 1 calc GR . . . .
N34 N -0.0797(2) 0.9915(3) 0.22912(16) 0.1091(10) Uani 1 1 d . . . . .
H34A H -0.021109 1.016010 0.223578 0.131 Uiso 1 1 calc R . . . .
H34B H -0.126096 1.043078 0.232716 0.131 Uiso 1 1 calc R . . . .
O35 O -0.31600(17) 0.7062(3) 0.25014(13) 0.1075(8) Uani 1 1 d . . . . .
N36 N -0.19324(19) 0.8408(3) 0.24138(12) 0.0856(7) Uani 1 1 d . . . . .
H36 H -0.235073 0.897819 0.245652 0.103 Uiso 1 1 calc R . . . .
N37 N -0.02723(18) 0.7940(2) 0.22661(11) 0.0819(7) Uani 1 1 d . . . . .
N38 N -0.1551(2) 0.5135(3) 0.24119(13) 0.0883(8) Uani 1 1 d . . . . .
N39 N -0.00265(19) 0.5776(3) 0.22566(11) 0.0819(7) Uani 1 1 d . . . . .
C40 C -0.0985(2) 0.8738(3) 0.23212(14) 0.0818(8) Uani 1 1 d . . . . .
C41 C -0.2266(2) 0.7243(3) 0.24438(14) 0.0817(8) Uani 1 1 d . . . . .
C42 C -0.1520(2) 0.6372(3) 0.24043(14) 0.0792(8) Uani 1 1 d . . . . .
C43 C -0.0579(2) 0.6786(3) 0.23085(13) 0.0749(8) Uani 1 1 d . . . . .
C44 C -0.0648(3) 0.4822(3) 0.23209(15) 0.0912(9) Uani 1 1 d . . . . .
H44 H -0.044615 0.402132 0.230157 0.109 Uiso 1 1 calc R . . . .
C45 C 0.1018(2) 0.5742(4) 0.21591(15) 0.0919(10) Uani 1 1 d . . . . .
H45A H 0.116420 0.634293 0.187470 0.110 Uiso 1 1 calc R . . . .
H45B H 0.118316 0.495494 0.200942 0.110 Uiso 1 1 calc R . . . .
C46 C 0.2724(3) 0.6090(4) 0.25946(16) 0.0953(10) Uani 1 1 d . U . . .
H46 H 0.277897 0.666415 0.227938 0.114 Uiso 1 1 calc R . . . .
C48 C 0.3245(3) 0.6656(5) 0.3110(2) 0.1270(16) Uani 1 1 d . . . . .
H48A H 0.294738 0.743052 0.318766 0.152 Uiso 1 1 calc R . . . .
H48B H 0.317585 0.614097 0.344002 0.152 Uiso 1 1 calc R . . . .
O49 O 0.4240(3) 0.6821(5) 0.30200(19) 0.1635(16) Uani 1 1 d . . . . .
H49 H 0.451517 0.711109 0.330790 0.245 Uiso 1 1 calc GR . . . .
O1 O 1.2649(3) 0.7588(7) 0.4701(3) 0.211(2) Uani 1 1 d . . . . .
H1 H 1.288919 0.715448 0.495513 0.316 Uiso 1 1 calc GR . . . .
O2 O 1.1688(6) 1.0224(9) 0.4605(4) 0.270(3) Uani 1 1 d . . . . .
H2 H 1.124684 1.007083 0.481848 0.404 Uiso 1 1 calc GR . . . .
O0AA O 0.3274(3) 0.4152(5) 0.2844(3) 0.190(2) Uani 1 1 d . . . . .
H0AA H 0.385169 0.410464 0.295763 0.285 Uiso 1 1 calc GR . . . .
C2 C 0.3186(4) 0.4939(6) 0.2409(2) 0.1390(18) Uani 1 1 d . U . . .
H2A H 0.278747 0.458513 0.209793 0.167 Uiso 1 1 calc R . . . .
H2B H 0.383018 0.510988 0.227156 0.167 Uiso 1 1 calc R . . . .
O8 O 0.52893(18) 0.7172(2) 0.41193(13) 0.1100(9) Uani 1 1 d . . . . .
O11 O 0.65949(18) 0.2188(3) 0.40832(13) 0.1080(8) 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
N1 C9 1.334(5) . ?
N4 C6 1.375(4) . ?
N4 C9 1.361(4) . ?
N3 C7 1.387(5) . ?
N3 C10 1.297(5) . ?
C6 C7 1.406(5) . ?
C6 O8 1.232(4) . ?
N5 C8 1.354(4) . ?
N5 C10 1.367(5) . ?
N5 C11 1.455(4) . ?
C7 C8 1.364(5) . ?
N008 C8 1.362(4) . ?
N008 C9 1.320(4) . ?
C00H C45 1.496(5) . ?
C00H C46 1.521(4) . ?
C00I C28 1.480(5) . ?
C00I C29 1.512(4) . ?
C010 C11 1.480(5) . ?
C010 C12 1.514(5) . ?
C12 C14 1.520(9) . ?
C12 C13 1.458(7) . ?
C14 O2 1.335(9) . ?
C13 O1 1.413(7) . ?
N19 C23 1.378(4) . ?
N19 C26 1.381(5) . ?
N18 C23 1.342(5) . ?
N20 C23 1.307(4) . ?
N20 C24 1.342(4) . ?
N21 C24 1.371(4) . ?
N21 C27 1.351(5) . ?
N21 C28 1.461(4) . ?
N22 C25 1.384(5) . ?
N22 C27 1.310(5) . ?
C24 C25 1.382(5) . ?
C25 C26 1.407(5) . ?
C26 O11 1.244(4) . ?
C29 C30 1.502(6) . ?
C29 C31 1.494(5) . ?
C30 O32 1.356(7) . ?
C31 O33 1.413(5) . ?
N34 C40 1.330(5) . ?
O35 C41 1.250(4) . ?
N36 C40 1.372(4) . ?
N36 C41 1.371(4) . ?
N37 C40 1.325(4) . ?
N37 C43 1.350(4) . ?
N38 C42 1.370(5) . ?
N38 C44 1.308(4) . ?
N39 C43 1.357(4) . ?
N39 C44 1.367(5) . ?
N39 C45 1.455(4) . ?
C41 C42 1.409(5) . ?
C42 C43 1.391(4) . ?
C46 C48 1.505(6) . ?
C46 C2 1.496(7) . ?
C48 O49 1.396(5) . ?
O0AA C2 1.341(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N4 C6 126.4(3) . . ?
C10 N3 C7 105.2(3) . . ?
N4 C6 C7 110.9(3) . . ?
O8 C6 N4 120.3(3) . . ?
O8 C6 C7 128.8(3) . . ?
C8 N5 C10 106.5(3) . . ?
C8 N5 C11 126.2(3) . . ?
C10 N5 C11 127.2(3) . . ?
N3 C7 C6 130.6(3) . . ?
C8 C7 N3 109.4(3) . . ?
C8 C7 C6 120.0(3) . . ?
C9 N008 C8 112.3(3) . . ?
N5 C8 C7 106.6(3) . . ?
N5 C8 N008 126.1(3) . . ?
N008 C8 C7 127.3(3) . . ?
N1 C9 N4 116.9(3) . . ?
N008 C9 N1 120.1(3) . . ?
N008 C9 N4 123.0(3) . . ?
C45 C00H C46 113.4(3) . . ?
C28 C00I C29 114.8(3) . . ?
C11 C010 C12 112.9(3) . . ?
N3 C10 N5 112.2(4) . . ?
N5 C11 C010 111.3(3) . . ?
C010 C12 C14 115.7(5) . . ?
C13 C12 C010 110.4(4) . . ?
C13 C12 C14 116.0(5) . . ?
O2 C14 C12 108.7(7) . . ?
O1 C13 C12 112.7(5) . . ?
C23 N19 C26 123.6(3) . . ?
C23 N20 C24 113.9(3) . . ?
C24 N21 C28 125.2(3) . . ?
C27 N21 C24 106.6(3) . . ?
C27 N21 C28 128.0(3) . . ?
C27 N22 C25 103.9(3) . . ?
N18 C23 N19 115.7(3) . . ?
N20 C23 N19 123.4(3) . . ?
N20 C23 N18 120.9(3) . . ?
N20 C24 N21 127.3(3) . . ?
N20 C24 C25 127.4(3) . . ?
N21 C24 C25 105.3(3) . . ?
N22 C25 C26 131.5(3) . . ?
C24 C25 N22 110.5(3) . . ?
C24 C25 C26 118.0(3) . . ?
N19 C26 C25 113.7(3) . . ?
O11 C26 N19 118.9(3) . . ?
O11 C26 C25 127.5(3) . . ?
N22 C27 N21 113.7(3) . . ?
N21 C28 C00I 112.5(3) . . ?
C30 C29 C00I 114.1(3) . . ?
C31 C29 C00I 110.1(3) . . ?
C31 C29 C30 111.8(4) . . ?
O32 C30 C29 111.8(4) . . ?
O33 C31 C29 111.5(3) . . ?
C41 N36 C40 125.3(3) . . ?
C40 N37 C43 113.1(3) . . ?
C44 N38 C42 103.5(3) . . ?
C43 N39 C44 106.0(3) . . ?
C43 N39 C45 126.1(3) . . ?
C44 N39 C45 127.9(3) . . ?
N34 C40 N36 117.1(3) . . ?
N37 C40 N34 120.2(3) . . ?
N37 C40 N36 122.7(3) . . ?
O35 C41 N36 119.0(3) . . ?
O35 C41 C42 127.6(3) . . ?
N36 C41 C42 113.4(3) . . ?
N38 C42 C41 131.3(3) . . ?
N38 C42 C43 111.1(3) . . ?
C43 C42 C41 117.5(3) . . ?
N37 C43 N39 126.6(3) . . ?
N37 C43 C42 128.0(3) . . ?
N39 C43 C42 105.4(3) . . ?
N38 C44 N39 114.1(3) . . ?
N39 C45 C00H 112.1(3) . . ?
C48 C46 C00H 109.6(3) . . ?
C2 C46 C00H 113.9(4) . . ?
C2 C46 C48 113.5(4) . . ?
O49 C48 C46 110.8(4) . . ?
O0AA C2 C46 110.8(5) . . ?

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

data_cu_p_g_400k_1116_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2520169'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N5 O3'
_chemical_formula_sum            'C10 H15 N5 O3'
_chemical_formula_weight         253.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   11.7938(3)
_cell_length_b                   10.9225(3)
_cell_length_c                   8.9572(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.877(2)
_cell_angle_gamma                90
_cell_volume                     1136.74(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5482
_cell_measurement_temperature    400(2)
_cell_measurement_theta_max      68.299
_cell_measurement_theta_min      3.804
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1561 before and 0.1039 after correction.
The Ratio of minimum to maximum transmission is 0.6354.
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    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9922
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.293
_diffrn_reflns_theta_min         3.804
_diffrn_ambient_temperature      400.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1679
_reflns_number_total             2067
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0645
_refine_ls_restrained_S_all      1.073
_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)+(0.1192P)²+0.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O8-H8
 0.82 with sigma of 0.02
 O7-H7
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C13(H13)
4.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
4.e Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O7(H7), O8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8551(2) 1.0151(2) 0.5216(3) 0.0656(7) Uani 1 1 d . . . . .
H1A H 0.803462 1.040210 0.448334 0.079 Uiso 1 1 calc R . . . .
H1B H 0.897627 1.067090 0.577587 0.079 Uiso 1 1 calc R . . . .
N2 N 0.95320(17) 0.86278(19) 0.6677(2) 0.0489(5) Uani 1 1 d . . . . .
H2 H 0.990089 0.920732 0.720059 0.059 Uiso 1 1 calc R . . . .
N3 N 0.80398(17) 0.81442(19) 0.4631(2) 0.0475(5) Uani 1 1 d . . . . .
N4 N 0.91341(18) 0.5303(2) 0.6286(3) 0.0527(6) Uani 1 1 d . . . . .
O7 O 0.2732(2) 0.7107(3) 0.1921(3) 0.0972(9) Uani 1 1 d D U . . .
H7 H 0.217(2) 0.734(5) 0.2322(13) 0.146 Uiso 1 1 calc DGR . . . .
O6 O 1.06566(17) 0.72556(18) 0.8145(2) 0.0652(6) Uani 1 1 d . . . . .
N5 N 0.77909(17) 0.59484(19) 0.4375(2) 0.0479(5) Uani 1 1 d . . . . .
C9 C 0.8690(2) 0.8956(2) 0.5485(3) 0.0479(6) Uani 1 1 d . . . . .
O8 O 0.3781(3) 0.4411(3) 0.2542(3) 0.1102(11) Uani 1 1 d D U . . .
H8 H 0.356(5) 0.375(3) 0.208(3) 0.165 Uiso 1 1 calc DGR . . . .
C10 C 0.9830(2) 0.7441(2) 0.7099(3) 0.0483(6) Uani 1 1 d . . . . .
C11 C 0.9130(2) 0.6569(2) 0.6226(3) 0.0461(6) Uani 1 1 d . . . . .
C12 C 0.82976(19) 0.6982(2) 0.5052(3) 0.0437(6) Uani 1 1 d . . . . .
C13 C 0.8328(2) 0.4977(3) 0.5171(3) 0.0531(6) Uani 1 1 d . . . . .
H13 H 0.813634 0.416525 0.493920 0.064 Uiso 1 1 calc R . . . .
C14 C 0.6813(2) 0.5922(3) 0.3131(3) 0.0543(7) Uani 1 1 d . . . . .
H14A H 0.675413 0.511585 0.267044 0.065 Uiso 1 1 calc R . . . .
H14B H 0.693739 0.651065 0.236412 0.065 Uiso 1 1 calc R . . . .
C15 C 0.5709(2) 0.6220(3) 0.3676(3) 0.0554(7) Uani 1 1 d . . . . .
H15A H 0.581241 0.697361 0.425559 0.066 Uiso 1 1 calc R . . . .
H15B H 0.554670 0.557421 0.435300 0.066 Uiso 1 1 calc R . . . .
C16 C 0.4681(2) 0.6363(3) 0.2422(3) 0.0590(7) Uani 1 1 d . U . . .
H16 H 0.490280 0.692640 0.167100 0.071 Uiso 1 1 calc R . . . .
C17 C 0.3713(3) 0.6953(4) 0.3058(4) 0.0750(9) Uani 1 1 d . . . . .
H17A H 0.351440 0.644581 0.386407 0.090 Uiso 1 1 calc R . . . .
H17B H 0.396141 0.774381 0.348537 0.090 Uiso 1 1 calc R . . . .
C18 C 0.4300(3) 0.5161(4) 0.1605(4) 0.0814(10) Uani 1 1 d . U . . .
H18A H 0.376138 0.533222 0.068233 0.098 Uiso 1 1 calc R . . . .
H18B H 0.496256 0.474763 0.132985 0.098 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.332(3) . ?
N2 C9 1.375(3) . ?
N2 C10 1.378(3) . ?
N3 C9 1.326(3) . ?
N3 C12 1.344(3) . ?
N4 C11 1.383(3) . ?
N4 C13 1.305(3) . ?
O7 C17 1.414(4) . ?
O6 C10 1.248(3) . ?
N5 C12 1.370(3) . ?
N5 C13 1.371(3) . ?
N5 C14 1.460(3) . ?
O8 C18 1.388(5) . ?
C10 C11 1.407(3) . ?
C11 C12 1.385(3) . ?
C14 C15 1.503(4) . ?
C15 C16 1.513(3) . ?
C16 C17 1.505(4) . ?
C16 C18 1.533(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C10 125.0(2) . . ?
C9 N3 C12 112.9(2) . . ?
C13 N4 C11 104.2(2) . . ?
C12 N5 C13 106.27(19) . . ?
C12 N5 C14 125.6(2) . . ?
C13 N5 C14 128.0(2) . . ?
N1 C9 N2 116.5(2) . . ?
N3 C9 N1 120.6(2) . . ?
N3 C9 N2 122.9(2) . . ?
N2 C10 C11 112.8(2) . . ?
O6 C10 N2 119.2(2) . . ?
O6 C10 C11 128.0(2) . . ?
N4 C11 C10 131.1(2) . . ?
N4 C11 C12 110.6(2) . . ?
C12 C11 C10 118.2(2) . . ?
N3 C12 N5 126.4(2) . . ?
N3 C12 C11 128.1(2) . . ?
N5 C12 C11 105.4(2) . . ?
N4 C13 N5 113.4(2) . . ?
N5 C14 C15 111.3(2) . . ?
C14 C15 C16 114.2(2) . . ?
C15 C16 C18 113.4(3) . . ?
C17 C16 C15 109.1(2) . . ?
C17 C16 C18 111.6(2) . . ?
O7 C17 C16 111.0(3) . . ?
O8 C18 C16 109.8(3) . . ?

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

data_cu_20230531pcv_gcv_380k_0ma_a_pl_sq
_database_code_depnum_ccdc_archive 'CCDC 2520171'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2023-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N5 O3'
_chemical_formula_sum            'C10 H15 N5 O3'
_chemical_formula_weight         253.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   11.8369(3)
_cell_length_b                   10.8946(3)
_cell_length_c                   8.9309(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.8830(10)
_cell_angle_gamma                90
_cell_volume                     1134.62(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9727
_cell_measurement_temperature    380(2)
_cell_measurement_theta_max      68.272
_cell_measurement_theta_min      4.058
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1481 before and 0.0999 after correction. The Ratio of minimum to maximum transmission is 0.5430. 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    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13070
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.266
_diffrn_reflns_theta_min         6.466
_diffrn_ambient_temperature      380.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1930
_reflns_number_total             2050
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039
_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     165
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0470
_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)+(0.0650P)²+0.4535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_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 C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), C16(H16)
2.d X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 -0.62267(17) 0.44117(18) -0.74318(18) 0.0838(6) Uani 1 1 d . . . . .
H1 H -0.668093 0.395072 -0.795344 0.126 Uiso 1 1 calc GR . . . .
O2 O -0.72791(13) 0.71297(19) -0.8088(2) 0.0802(5) Uani 1 1 d . . . . .
H2 H -0.782250 0.735637 -0.769869 0.120 Uiso 1 1 calc GR . . . .
O10 O 0.06507(11) 0.72725(12) -0.18620(15) 0.0552(4) Uani 1 1 d . . . . .
N5 N -0.22135(11) 0.59654(12) -0.56335(15) 0.0396(4) Uani 1 1 d . . . . .
N6 N -0.08705(12) 0.53178(12) -0.37214(17) 0.0435(4) Uani 1 1 d . . . . .
N7 N -0.19640(11) 0.81725(12) -0.53815(15) 0.0390(3) Uani 1 1 d . . . . .
N8 N -0.04775(11) 0.86481(12) -0.33264(15) 0.0408(4) Uani 1 1 d . . . . .
H8 H -0.011501 0.923010 -0.279771 0.049 Uiso 1 1 calc R . . . .
N9 N -0.14482(13) 1.01751(13) -0.47908(19) 0.0549(4) Uani 1 1 d . . . . .
H9A H -0.196311 1.042742 -0.552479 0.066 Uiso 1 1 calc R . . . .
H9B H -0.102267 1.069617 -0.423082 0.066 Uiso 1 1 calc R . . . .
C11 C -0.57111(17) 0.5167(2) -0.8370(2) 0.0619(6) Uani 1 1 d . . . . .
H11A H -0.624751 0.532957 -0.929821 0.074 Uiso 1 1 calc R . . . .
H11B H -0.504931 0.475292 -0.864164 0.074 Uiso 1 1 calc R . . . .
C12 C -0.62957(16) 0.6985(2) -0.6942(3) 0.0596(5) Uani 1 1 d . . . . .
H12A H -0.649117 0.649064 -0.612039 0.072 Uiso 1 1 calc R . . . .
H12B H -0.604213 0.778242 -0.653301 0.072 Uiso 1 1 calc R . . . .
C13 C -0.53362(14) 0.63723(18) -0.7585(2) 0.0474(4) Uani 1 1 d . . . . .
H13 H -0.511983 0.692491 -0.835439 0.057 Uiso 1 1 calc R . . . .
C14 C -0.42988(14) 0.62512(18) -0.63199(19) 0.0457(4) Uani 1 1 d . . . . .
H14A H -0.419367 0.701884 -0.576319 0.055 Uiso 1 1 calc R . . . .
H14B H -0.445522 0.561899 -0.561839 0.055 Uiso 1 1 calc R . . . .
C15 C -0.31994(14) 0.59371(17) -0.68728(19) 0.0445(4) Uani 1 1 d . . . . .
H15A H -0.326556 0.512493 -0.732449 0.053 Uiso 1 1 calc R . . . .
H15B H -0.307683 0.651820 -0.765201 0.053 Uiso 1 1 calc R . . . .
C16 C -0.16761(14) 0.49886(16) -0.4837(2) 0.0437(4) Uani 1 1 d . . . . .
H16 H -0.186727 0.417441 -0.506890 0.052 Uiso 1 1 calc R . . . .
C17 C -0.17067(12) 0.69979(14) -0.49564(17) 0.0354(4) Uani 1 1 d . . . . .
C18 C -0.08790(13) 0.65854(14) -0.37809(18) 0.0375(4) Uani 1 1 d . . . . .
C19 C -0.01730(13) 0.74587(15) -0.29015(19) 0.0393(4) Uani 1 1 d . . . . .
C20 C -0.13099(13) 0.89771(14) -0.45211(18) 0.0383(4) 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
O1 H1 0.8200 . ?
O1 C11 1.388(3) . ?
O2 H2 0.8200 . ?
O2 C12 1.421(2) . ?
O10 C19 1.242(2) . ?
N5 C15 1.4644(19) . ?
N5 C16 1.374(2) . ?
N5 C17 1.366(2) . ?
N6 C16 1.305(2) . ?
N6 C18 1.382(2) . ?
N7 C17 1.355(2) . ?
N7 C20 1.324(2) . ?
N8 H8 0.8600 . ?
N8 C19 1.381(2) . ?
N8 C20 1.370(2) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N9 C20 1.332(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C13 1.519(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.513(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.525(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.508(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C18 C19 1.412(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
C11 O1 H1 109.5 . . ?
C12 O2 H2 109.5 . . ?
C16 N5 C15 127.81(14) . . ?
C17 N5 C15 125.76(13) . . ?
C17 N5 C16 106.22(13) . . ?
C16 N6 C18 104.22(14) . . ?
C20 N7 C17 112.44(13) . . ?
C19 N8 H8 117.3 . . ?
C20 N8 H8 117.3 . . ?
C20 N8 C19 125.35(13) . . ?
H9A N9 H9B 120.0 . . ?
C20 N9 H9A 120.0 . . ?
C20 N9 H9B 120.0 . . ?
O1 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
O1 C11 C13 110.96(17) . . ?
H11A C11 H11B 108.0 . . ?
C13 C11 H11A 109.4 . . ?
C13 C11 H11B 109.4 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 C13 110.57(17) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C13 H13 107.4 . . ?
C11 C13 C14 113.67(16) . . ?
C12 C13 C11 112.20(15) . . ?
C12 C13 H13 107.4 . . ?
C12 C13 C14 108.57(15) . . ?
C14 C13 H13 107.4 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.03(14) . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
N5 C15 C14 111.61(14) . . ?
N5 C15 H15A 109.3 . . ?
N5 C15 H15B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
N5 C16 H16 123.4 . . ?
N6 C16 N5 113.27(15) . . ?
N6 C16 H16 123.4 . . ?
N5 C17 C18 105.59(13) . . ?
N7 C17 N5 126.39(13) . . ?
N7 C17 C18 128.02(14) . . ?
N6 C18 C17 110.70(14) . . ?
N6 C18 C19 130.70(14) . . ?
C17 C18 C19 118.55(14) . . ?
O10 C19 N8 119.55(14) . . ?
O10 C19 C18 128.25(15) . . ?
N8 C19 C18 112.19(13) . . ?
N7 C20 N8 123.32(14) . . ?
N7 C20 N9 120.13(14) . . ?
N9 C20 N8 116.54(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
O1 C11 C13 C12 -51.4(2) . . . . ?
O1 C11 C13 C14 72.3(2) . . . . ?
O2 C12 C13 C11 -54.2(2) . . . . ?
O2 C12 C13 C14 179.37(17) . . . . ?
N5 C17 C18 N6 -0.16(18) . . . . ?
N5 C17 C18 C19 177.47(14) . . . . ?
N6 C18 C19 O10 1.3(3) . . . . ?
N6 C18 C19 N8 -179.55(17) . . . . ?
N7 C17 C18 N6 -179.27(15) . . . . ?
N7 C17 C18 C19 -1.6(3) . . . . ?
C11 C13 C14 C15 68.2(2) . . . . ?
C12 C13 C14 C15 -166.18(17) . . . . ?
C13 C14 C15 N5 173.74(15) . . . . ?
C15 N5 C16 N6 -175.32(16) . . . . ?
C15 N5 C17 N7 -5.5(3) . . . . ?
C15 N5 C17 C18 175.40(15) . . . . ?
C16 N5 C15 C14 100.1(2) . . . . ?
C16 N5 C17 N7 179.42(15) . . . . ?
C16 N5 C17 C18 0.29(17) . . . . ?
C16 N6 C18 C17 -0.04(19) . . . . ?
C16 N6 C18 C19 -177.29(18) . . . . ?
C17 N5 C15 C14 -73.9(2) . . . . ?
C17 N5 C16 N6 -0.3(2) . . . . ?
C17 N7 C20 N8 -0.7(2) . . . . ?
C17 N7 C20 N9 179.73(15) . . . . ?
C17 C18 C19 O10 -175.75(17) . . . . ?
C17 C18 C19 N8 3.4(2) . . . . ?
C18 N6 C16 N5 0.2(2) . . . . ?
C19 N8 C20 N7 3.1(3) . . . . ?
C19 N8 C20 N9 -177.35(16) . . . . ?
C20 N7 C17 N5 -178.81(15) . . . . ?
C20 N7 C17 C18 0.1(2) . . . . ?
C20 N8 C19 O10 174.98(16) . . . . ?
C20 N8 C19 C18 -4.2(2) . . . . ?

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

data_cu_20230530pcv_gcv_420k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2520174'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V118 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C9.95 H14.90 N5 O3.05'
_chemical_formula_moiety         ?
_chemical_formula_weight         253.37
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.117(4)
_cell_length_b                   10.951(5)
_cell_length_c                   11.800(4)
_cell_angle_alpha                87.02(3)
_cell_angle_beta                 80.55(2)
_cell_angle_gamma                86.23(4)
_cell_volume                     1158.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    420(2)
_cell_measurement_reflns_used    617
_cell_measurement_theta_min      5.673
_cell_measurement_theta_max      65.8235
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4087
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction:
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48
(2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      420(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.2
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            8605
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_theta_min         4.049
_diffrn_reflns_theta_max         66.864
_diffrn_reflns_theta_full        66.864
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             3919
_reflns_number_gt                2756
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker BIS V6.2.14/2020-05-01'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+2.4947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     336
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.2863
_refine_ls_wR_factor_gt          0.2742
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'

_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_
_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 0.4801(5) 0.7716(4) 0.3329(4) 0.0492(11) Uani 1 1 d . . . . .
C2_1 C 0.4331(5) 0.5762(4) 0.3689(4) 0.0515(11) Uani 1 1 d . . . . .
C3_1 C 0.2755(5) 0.7307(5) 0.4816(4) 0.0543(12) Uani 1 1 d . . . . .
C4_1 C 0.3653(5) 0.8148(4) 0.4155(4) 0.0528(12) Uani 1 1 d . . . . .
C5_1 C 0.4724(6) 0.9725(5) 0.3400(4) 0.0596(13) Uani 1 1 d . . . . .
H5_1 H 0.497301 1.053083 0.322557 0.072 Uiso 1 1 calc R U . . .
C6_1 C 0.6717(5) 0.8758(5) 0.1884(4) 0.0592(13) Uani 1 1 d D . . . .
H6A_1 H 0.746637 0.811587 0.200885 0.071 Uiso 1 1 calc R U . A 1
H6B_1 H 0.717420 0.953721 0.184416 0.071 Uiso 1 1 calc R U . A 1
C7_1 C 0.6186(6) 0.8576(6) 0.0754(4) 0.059(2) Uani 0.95 1 d . . P B 1
H7A_1 H 0.553065 0.927302 0.058924 0.070 Uiso 0.95 1 calc R U P B 1
H7B_1 H 0.561162 0.785265 0.083585 0.070 Uiso 0.95 1 calc R U P B 1
O4_1 O 0.647(6) 0.888(9) 0.0717(14) 0.059(2) Uani 0.05 1 d D . P B 2
C8_1 C 0.7457(5) 0.8430(5) -0.0263(4) 0.0580(13) Uani 1 1 d D . . . .
H8_1 H 0.813291 0.775649 -0.004789 0.070 Uiso 1 1 calc R U . B 1
C9_1 C 0.8361(7) 0.9529(7) -0.0536(5) 0.089(2) Uani 1 1 d . . . . .
H9A_1 H 0.867289 0.978190 0.015896 0.107 Uiso 1 1 calc R U . . .
H9B_1 H 0.924850 0.931938 -0.108146 0.107 Uiso 1 1 calc R U . . .
C10_1 C 0.6854(7) 0.8039(6) -0.1289(5) 0.0754(16) Uani 1 1 d . . . . .
H10A_1 H 0.633592 0.729323 -0.108724 0.090 Uiso 1 1 calc R U . . .
H10B_1 H 0.614244 0.866890 -0.150832 0.090 Uiso 1 1 calc R U . . .
N1_1 N 0.5194(4) 0.6534(4) 0.3068(3) 0.0538(10) Uani 1 1 d . . . . .
N2_1 N 0.3144(4) 0.6106(4) 0.4514(3) 0.0567(11) Uani 1 1 d . . . . .
H2_1 H 0.261042 0.553943 0.486475 0.068 Uiso 1 1 calc R U . . .
N3_1 N 0.3621(5) 0.9413(4) 0.4185(4) 0.0632(11) Uani 1 1 d . . . . .
N4_1 N 0.5486(5) 0.8733(4) 0.2853(3) 0.0554(10) Uani 1 1 d . . . . .
N5_1 N 0.4557(5) 0.4560(4) 0.3541(4) 0.0721(13) Uani 1 1 d . . . . .
H5A_1 H 0.527527 0.428903 0.303419 0.087 Uiso 1 1 calc R U . . .
H5B_1 H 0.398433 0.405702 0.395381 0.087 Uiso 1 1 calc R U . . .
O1_1 O 0.1704(4) 0.7513(3) 0.5634(3) 0.0709(11) Uani 1 1 d . . . . .
O2_1 O 0.7535(6) 1.0504(5) -0.1004(6) 0.128(2) Uani 1 1 d . . . . .
H2A_1 H 0.810666 1.096732 -0.139427 0.192 Uiso 1 1 calc R U . . .
O3_1 O 0.8010(5) 0.7834(6) -0.2231(4) 0.1057(17) Uani 1 1 d . . . . .
H3_1 H 0.768664 0.748611 -0.272871 0.159 Uiso 1 1 calc R U . . .
C1_2 C 0.0073(5) 0.2809(5) 0.6774(4) 0.0524(12) Uani 1 1 d . . . . .
C2_2 C 0.0474(5) 0.0846(5) 0.6398(4) 0.0542(12) Uani 1 1 d . . . . .
C3_2 C 0.2027(6) 0.2305(5) 0.5220(4) 0.0555(12) Uani 1 1 d . . . . .
C4_2 C 0.1200(5) 0.3207(4) 0.5919(4) 0.0503(11) Uani 1 1 d . . . . .
C5_2 C 0.0187(6) 0.4803(5) 0.6713(4) 0.0594(13) Uani 1 1 d . . . . .
H5_2 H -0.003052 0.561781 0.689679 0.071 Uiso 1 1 calc R U . . .
C6_2 C -0.1797(6) 0.3948(5) 0.8240(4) 0.0604(13) Uani 1 1 d D . . . .
H6A_2 H -0.255914 0.341044 0.812590 0.072 Uiso 1 1 calc R U . C 1
H6B_2 H -0.223667 0.477877 0.827019 0.072 Uiso 1 1 calc R U . C 1
C7_2 C -0.1272(6) 0.3592(16) 0.9367(5) 0.062(2) Uani 0.95 1 d . . P D 1
H7A_2 H -0.058939 0.418371 0.951841 0.074 Uiso 0.95 1 calc R U P D 1
H7B_2 H -0.073088 0.279898 0.930335 0.074 Uiso 0.95 1 calc R U P D 1
O4_2 O -0.147(3) 0.37(2) 0.938(3) 0.062(2) Uani 0.05 1 d D . P D 2
C8_2 C -0.2556(6) 0.3528(5) 1.0382(4) 0.0607(13) Uani 1 1 d D . . . .
H8_2 H -0.330200 0.303818 1.013994 0.073 Uiso 1 1 calc R U . D 1
C9_2 C -0.3350(8) 0.4774(7) 1.0711(5) 0.092(2) Uani 1 1 d . . . . .
H9A_2 H -0.357278 0.522800 1.002613 0.110 Uiso 1 1 calc R U . . .
H9B_2 H -0.428174 0.464821 1.122090 0.110 Uiso 1 1 calc R U . . .
C10_2 C -0.2011(7) 0.2824(7) 1.1371(5) 0.086(2) Uani 1 1 d . . . . .
H10A_2 H -0.164311 0.200953 1.113512 0.104 Uiso 1 1 calc R U . . .
H10B_2 H -0.119252 0.323133 1.158795 0.104 Uiso 1 1 calc R U . . .
N1_2 N -0.0340(4) 0.1657(4) 0.7052(3) 0.0543(10) Uani 1 1 d . . . . .
N2_2 N 0.1618(4) 0.1133(4) 0.5541(3) 0.0559(10) Uani 1 1 d . . . . .
H2_2 H 0.211681 0.053903 0.517820 0.067 Uiso 1 1 calc R U . . .
N3_2 N 0.1260(5) 0.4456(4) 0.5887(3) 0.0588(11) Uani 1 1 d . . . . .
N4_2 N -0.0574(4) 0.3870(4) 0.7271(3) 0.0544(10) Uani 1 1 d . . . . .
N5_2 N 0.0217(6) -0.0345(4) 0.6550(4) 0.0761(14) Uani 1 1 d . . . . .
H5A_2 H -0.048320 -0.058448 0.707854 0.091 Uiso 1 1 calc R U . . .
H5B_2 H 0.075320 -0.087043 0.612051 0.091 Uiso 1 1 calc R U . . .
O1_2 O 0.3038(4) 0.2482(3) 0.4380(3) 0.0718(11) Uani 1 1 d . . . . .
O2_2 O -0.2449(6) 0.5431(6) 1.1251(6) 0.124(2) Uani 1 1 d . . . . .
H2A_2 H -0.296557 0.585914 1.172996 0.185 Uiso 1 1 calc R U . . .
O3_2 O -0.3159(6) 0.2729(6) 1.2328(4) 0.1156(19) Uani 1 1 d . . . . .
H3_2 H -0.279368 0.254641 1.290896 0.173 Uiso 1 1 calc R U . . .


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 1.357(6) . ?
C1_1 N4_1 1.364(6) . ?
C1_1 C4_1 1.385(6) . ?
C2_1 N1_1 1.305(6) . ?
C2_1 N5_1 1.335(6) . ?
C2_1 N2_1 1.378(6) . ?
C3_1 O1_1 1.262(5) . ?
C3_1 N2_1 1.389(6) . ?
C3_1 C4_1 1.393(7) . ?
C4_1 N3_1 1.386(6) . ?
C5_1 N3_1 1.302(7) . ?
C5_1 N4_1 1.380(6) . ?
C6_1 O4_1 1.430(10) . ?
C6_1 N4_1 1.465(6) . ?
C6_1 C7_1 1.518(7) . ?
C7_1 C8_1 1.533(7) . ?
O4_1 C8_1 1.431(10) . ?
C8_1 C9_1 1.495(9) . ?
C8_1 C10_1 1.501(8) . ?
C9_1 O2_1 1.407(9) . ?
C10_1 O3_1 1.417(7) . ?
C1_2 N1_2 1.350(6) . ?
C1_2 N4_2 1.382(6) . ?
C1_2 C4_2 1.391(7) . ?
C2_2 N1_2 1.315(6) . ?
C2_2 N5_2 1.338(7) . ?
C2_2 N2_2 1.368(6) . ?
C3_2 O1_2 1.254(6) . ?
C3_2 N2_2 1.377(6) . ?
C3_2 C4_2 1.417(6) . ?
C4_2 N3_2 1.371(6) . ?
C5_2 N3_2 1.315(6) . ?
C5_2 N4_2 1.354(7) . ?
C6_2 O4_2 1.430(10) . ?
C6_2 N4_2 1.462(6) . ?
C6_2 C7_2 1.510(8) . ?
C7_2 C8_2 1.533(7) . ?
O4_2 C8_2 1.430(10) . ?
C8_2 C10_2 1.499(8) . ?
C8_2 C9_2 1.540(9) . ?
C9_2 O2_2 1.377(8) . ?
C10_2 O3_2 1.413(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1_1 C1_1 N4_1 127.1(4) . . ?
N1_1 C1_1 C4_1 127.8(4) . . ?
N4_1 C1_1 C4_1 105.1(4) . . ?
N1_1 C2_1 N5_1 120.5(4) . . ?
N1_1 C2_1 N2_1 123.9(4) . . ?
N5_1 C2_1 N2_1 115.6(4) . . ?
O1_1 C3_1 N2_1 119.0(4) . . ?
O1_1 C3_1 C4_1 128.2(5) . . ?
N2_1 C3_1 C4_1 112.8(4) . . ?
C1_1 C4_1 N3_1 110.9(4) . . ?
C1_1 C4_1 C3_1 118.7(4) . . ?
N3_1 C4_1 C3_1 130.4(4) . . ?
N3_1 C5_1 N4_1 112.9(5) . . ?
O4_1 C6_1 N4_1 122(2) . . ?
N4_1 C6_1 C7_1 111.5(4) . . ?
C6_1 C7_1 C8_1 113.5(4) . . ?
C6_1 O4_1 C8_1 126.2(13) . . ?
O4_1 C8_1 C9_1 98(5) . . ?
O4_1 C8_1 C10_1 120(2) . . ?
C9_1 C8_1 C10_1 112.2(5) . . ?
C9_1 C8_1 C7_1 114.2(5) . . ?
C10_1 C8_1 C7_1 109.6(4) . . ?
O2_1 C9_1 C8_1 111.0(5) . . ?
O3_1 C10_1 C8_1 111.2(5) . . ?
C2_1 N1_1 C1_1 112.6(4) . . ?
C2_1 N2_1 C3_1 124.2(4) . . ?
C5_1 N3_1 C4_1 104.3(4) . . ?
C1_1 N4_1 C5_1 106.8(4) . . ?
C1_1 N4_1 C6_1 125.8(4) . . ?
C5_1 N4_1 C6_1 127.3(4) . . ?
N1_2 C1_2 N4_2 126.8(4) . . ?
N1_2 C1_2 C4_2 128.6(4) . . ?
N4_2 C1_2 C4_2 104.5(4) . . ?
N1_2 C2_2 N5_2 120.4(4) . . ?
N1_2 C2_2 N2_2 124.1(5) . . ?
N5_2 C2_2 N2_2 115.5(4) . . ?
O1_2 C3_2 N2_2 120.0(4) . . ?
O1_2 C3_2 C4_2 126.9(5) . . ?
N2_2 C3_2 C4_2 113.1(4) . . ?
N3_2 C4_2 C1_2 111.4(4) . . ?
N3_2 C4_2 C3_2 131.3(4) . . ?
C1_2 C4_2 C3_2 117.2(4) . . ?
N3_2 C5_2 N4_2 114.1(4) . . ?
O4_2 C6_2 N4_2 119(3) . . ?
N4_2 C6_2 C7_2 111.7(4) . . ?
C6_2 C7_2 C8_2 112.8(4) . . ?
C6_2 O4_2 C8_2 124.8(13) . . ?
O4_2 C8_2 C10_2 116(4) . . ?
C10_2 C8_2 C7_2 109.0(5) . . ?
O4_2 C8_2 C9_2 108(10) . . ?
C10_2 C8_2 C9_2 113.4(5) . . ?
C7_2 C8_2 C9_2 114.6(8) . . ?
O2_2 C9_2 C8_2 109.5(6) . . ?
O3_2 C10_2 C8_2 111.3(5) . . ?
C2_2 N1_2 C1_2 112.2(4) . . ?
C2_2 N2_2 C3_2 124.6(4) . . ?
C5_2 N3_2 C4_2 103.7(4) . . ?
C5_2 N4_2 C1_2 106.4(4) . . ?
C5_2 N4_2 C6_2 127.4(4) . . ?
C1_2 N4_2 C6_2 126.2(4) . . ?

####################################################################### 
# 
# 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_91
_database_code_depnum_ccdc_archive 'CCDC 2520173'
loop_
_audit_author_name
_audit_author_address
'JIANTAO MENG'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2026-01-05 deposited with the CCDC.	2026-06-08 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N5 O3'
_chemical_formula_sum            'C10 H15 N5 O3'
_chemical_formula_weight         253.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.7031(5)
_cell_length_b                   10.7835(4)
_cell_length_c                   8.7394(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.188(2)
_cell_angle_gamma                90
_cell_volume                     1088.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2575
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.099
_cell_measurement_theta_min      2.583
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.3795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1550 before and 0.1033 after correction.
The Ratio of minimum to maximum transmission is 0.5091.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0842
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.584
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1662
_reflns_number_total             2234
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.036
_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)+(0.0715P)²+0.6637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1627
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.06783(15) 0.71224(16) 0.81177(19) 0.0204(4) Uani 1 1 d . . . . .
O3 O 0.26964(16) 0.70309(18) 0.1910(2) 0.0270(5) Uani 1 1 d . . . . .
H3 H 0.214900 0.727585 0.234844 0.040 Uiso 1 1 calc R U . . .
O2 O 0.37244(18) 0.42927(18) 0.2612(2) 0.0312(5) Uani 1 1 d . . . . .
H2 H 0.327703 0.377355 0.211173 0.047 Uiso 1 1 calc R U . . .
N4 N 0.78114(17) 0.57913(18) 0.4264(2) 0.0171(5) Uani 1 1 d . . . . .
N2 N 0.95460(18) 0.85152(19) 0.6608(2) 0.0172(5) Uani 1 1 d . . . . .
N5 N 0.80643(18) 0.80190(18) 0.4499(2) 0.0176(5) Uani 1 1 d . . . . .
N3 N 0.91291(17) 0.51409(19) 0.6248(2) 0.0182(5) Uani 1 1 d . . . . .
N1 N 0.8592(2) 1.0054(2) 0.5092(3) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.8719(2) 0.8842(2) 0.5378(3) 0.0170(5) Uani 1 1 d . . . . .
C5 C 0.8320(2) 0.6834(2) 0.4956(3) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.8329(2) 0.4803(2) 0.5103(3) 0.0167(5) Uani 1 1 d . . . . .
H4 H 0.812560 0.396311 0.487295 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5717(2) 0.6116(2) 0.3593(3) 0.0189(5) Uani 1 1 d . . . . .
H7A H 0.584438 0.690823 0.416657 0.023 Uiso 1 1 calc R U . . .
H7B H 0.554511 0.547420 0.433432 0.023 Uiso 1 1 calc R U . . .
C2 C 0.9849(2) 0.7309(2) 0.7054(3) 0.0183(5) Uani 1 1 d . . . . .
C6 C 0.6821(2) 0.5765(2) 0.3014(3) 0.0194(6) Uani 1 1 d . . . . .
H6A H 0.673953 0.492172 0.256028 0.023 Uiso 1 1 calc R U . . .
H6B H 0.695764 0.634879 0.218782 0.023 Uiso 1 1 calc R U . . .
C3 C 0.9134(2) 0.6426(2) 0.6167(3) 0.0172(5) Uani 1 1 d . . . . .
C8 C 0.4667(2) 0.6257(2) 0.2330(3) 0.0206(6) Uani 1 1 d . . . . .
H8 H 0.489050 0.681148 0.150972 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4250(2) 0.5027(3) 0.1564(3) 0.0244(6) Uani 1 1 d . . . . .
H10A H 0.368426 0.518923 0.061645 0.029 Uiso 1 1 calc R U . . .
H10B H 0.491435 0.457315 0.126007 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3715(2) 0.6902(2) 0.3028(3) 0.0239(6) Uani 1 1 d . . . . .
H9A H 0.353553 0.641359 0.391979 0.029 Uiso 1 1 calc R U . . .
H9B H 0.398627 0.773128 0.341340 0.029 Uiso 1 1 calc R U . . .
H1A H 0.815(2) 1.028(2) 0.434(3) 0.016(7) Uiso 1 1 d . . . . .
H1B H 0.897(3) 1.075(3) 0.579(4) 0.045(9) Uiso 1 1 d . . . . .
H2A H 0.999(3) 0.907(3) 0.726(4) 0.038(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.249(3) . ?
O3 H3 0.8400 . ?
O3 C9 1.423(3) . ?
O2 H2 0.8400 . ?
O2 C10 1.423(3) . ?
N4 C5 1.367(3) . ?
N4 C4 1.377(3) . ?
N4 C6 1.461(3) . ?
N2 C1 1.373(3) . ?
N2 C2 1.387(3) . ?
N2 H2A 0.92(3) . ?
N5 C1 1.333(3) . ?
N5 C5 1.358(3) . ?
N3 C4 1.309(3) . ?
N3 C3 1.388(3) . ?
N1 C1 1.335(3) . ?
N1 H1A 0.80(3) . ?
N1 H1B 1.02(3) . ?
C5 C3 1.378(3) . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.509(3) . ?
C7 C8 1.523(3) . ?
C2 C3 1.414(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 H8 1.0000 . ?
C8 C10 1.530(4) . ?
C8 C9 1.522(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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 . . ?
C10 O2 H2 109.5 . . ?
C5 N4 C4 106.11(19) . . ?
C5 N4 C6 125.8(2) . . ?
C4 N4 C6 127.7(2) . . ?
C1 N2 C2 125.2(2) . . ?
C1 N2 H2A 124.7(19) . . ?
C2 N2 H2A 110.1(19) . . ?
C1 N5 C5 112.2(2) . . ?
C4 N3 C3 104.3(2) . . ?
C1 N1 H1A 119.1(19) . . ?
C1 N1 H1B 125.5(18) . . ?
H1A N1 H1B 115(3) . . ?
N5 C1 N2 123.3(2) . . ?
N5 C1 N1 120.5(2) . . ?
N1 C1 N2 116.2(2) . . ?
N4 C5 C3 106.0(2) . . ?
N5 C5 N4 125.7(2) . . ?
N5 C5 C3 128.2(2) . . ?
N4 C4 H4 123.5 . . ?
N3 C4 N4 113.1(2) . . ?
N3 C4 H4 123.5 . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C6 C7 C8 114.63(19) . . ?
C8 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
O1 C2 N2 119.6(2) . . ?
O1 C2 C3 128.4(2) . . ?
N2 C2 C3 112.0(2) . . ?
N4 C6 C7 111.30(19) . . ?
N4 C6 H6A 109.4 . . ?
N4 C6 H6B 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N3 C3 C2 130.6(2) . . ?
C5 C3 N3 110.5(2) . . ?
C5 C3 C2 118.8(2) . . ?
C7 C8 H8 107.8 . . ?
C7 C8 C10 113.2(2) . . ?
C10 C8 H8 107.8 . . ?
C9 C8 C7 108.25(19) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C10 111.6(2) . . ?
O2 C10 C8 109.9(2) . . ?
O2 C10 H10A 109.7 . . ?
O2 C10 H10B 109.7 . . ?
C8 C10 H10A 109.7 . . ?
C8 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O3 C9 C8 110.9(2) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?

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 2.0(4) . . . . ?
O1 C2 C3 C5 -174.8(2) . . . . ?
N4 C5 C3 N3 -0.7(3) . . . . ?
N4 C5 C3 C2 176.7(2) . . . . ?
N2 C2 C3 N3 -178.8(2) . . . . ?
N2 C2 C3 C5 4.4(3) . . . . ?
N5 C5 C3 N3 -179.9(2) . . . . ?
N5 C5 C3 C2 -2.5(4) . . . . ?
C1 N2 C2 O1 174.3(2) . . . . ?
C1 N2 C2 C3 -5.0(3) . . . . ?
C1 N5 C5 N4 -178.7(2) . . . . ?
C1 N5 C5 C3 0.3(4) . . . . ?
C5 N4 C4 N3 -0.9(3) . . . . ?
C5 N4 C6 C7 -72.2(3) . . . . ?
C5 N5 C1 N2 -0.5(3) . . . . ?
C5 N5 C1 N1 179.6(2) . . . . ?
C4 N4 C5 N5 -179.9(2) . . . . ?
C4 N4 C5 C3 0.9(3) . . . . ?
C4 N4 C6 C7 99.4(3) . . . . ?
C4 N3 C3 C5 0.2(3) . . . . ?
C4 N3 C3 C2 -176.8(2) . . . . ?
C7 C8 C10 O2 71.4(3) . . . . ?
C7 C8 C9 O3 -178.4(2) . . . . ?
C2 N2 C1 N5 3.2(4) . . . . ?
C2 N2 C1 N1 -176.9(2) . . . . ?
C6 N4 C5 N5 -6.8(4) . . . . ?
C6 N4 C5 C3 174.0(2) . . . . ?
C6 N4 C4 N3 -173.7(2) . . . . ?
C6 C7 C8 C10 69.1(3) . . . . ?
C6 C7 C8 C9 -166.6(2) . . . . ?
C3 N3 C4 N4 0.4(3) . . . . ?
C8 C7 C6 N4 173.2(2) . . . . ?
C10 C8 C9 O3 -53.2(3) . . . . ?
C9 C8 C10 O2 -51.0(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
