# Supplementary Information (SI) for Journal of Materials Chemistry A.
# 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. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2q0tsc
_database_code_depnum_ccdc_archive 'CCDC 2503243'
loop_
_audit_author_name
_audit_author_address
'Zhiyu King'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-11-16 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_audit_creation_date             2025-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7311)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C8 H18 N12 O4), N5, H1.2 O0.3'
_chemical_formula_sum            'C4 H10.20 N11 O2.30'
_chemical_formula_weight         249.23
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        Pnma
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.1617(8)
_cell_length_b                   6.6935(10)
_cell_length_c                   20.236(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1105.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1466
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      67.50
_cell_measurement_theta_min      4.37
_shelx_estimated_absorpt_T_max   0.882
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.1739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1559 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.5434.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1106
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.396
_diffrn_reflns_theta_min         4.370
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                778
_reflns_number_total             1106
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.41 (Bruker AXS LLC)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (Bruker AXS LLC)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1106
_refine_ls_number_restraints     242
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0831
_refine_ls_restrained_S_all      0.999
_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)+(0.1046P)²+1.3419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2263
_refine_ls_wR_factor_ref         0.2451
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.976(9)
 0.024(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Restrained distances
 N9A-N7A = N9A-N11A = N8A-N11A = N7A-N10A
 2.29 with sigma of 0.04
 N7A-N10A \\sim N8A-N11A \\sim N9A-N11A \\sim N9A-N7A \\sim N8A-N10A
 with sigma of 0.01
 N8A-N7A \\sim N8-N7 \\sim N7A-N11A \\sim N7-N11 \\sim N11-N10 \\sim N11A-N10A
\\sim N9-N10 \\sim N9A-N10A
 \\sim N9-N8 \\sim N9A-N8A
 with sigma of 0.02
 N4-N3 \\sim N2-N1
 with sigma of 0.02
4. Restrained planarity
 N7A, N8A, N9A, N10A, N11A
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
N7 \\sim N8 \\sim N9 \\sim N10 \\sim N11 \\sim N7A \\sim N8A \\sim N9A \\sim
N10A \\sim N11A: within 2A with sigma of 0.015 and sigma for terminal atoms of
0.03 within 2A
N4 \\sim N3 \\sim N2 \\sim N1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
N8 \\sim N9 \\sim N8A \\sim N9A: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
6. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H4A(0.5) H4B(0.5) H4C(0.5) N1(0.5) N2(0.5)
 N3(0.5) N4(0.5) N5(0.5) H5A(0.5) H5B(0.5) N6(0.5) H6A(0.5) H6B(0.5) C1(0.5)
 N7(0.4) N8(0.4) N9(0.4) N10(0.4) N11(0.4) N7A(0.1) N8A(0.1) N9A(0.1) N10A(0.1)
 N11A(0.1) O3(0.15) H3A(0.3) H3B(0.3)
7.a Free rotating group:
 O3(H3A,H3B)
7.b Rotating group:
 N5(H5A,H5B), N6(H6A,H6B)
7.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
7.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.9454(5) 0.250000 0.4072(2) 0.0931(15) Uani 1 2 d S T P . .
O2 O 0.7632(5) 0.250000 0.3246(2) 0.0823(13) Uani 1 2 d S T P . .
C2 C 0.6567(7) 0.250000 0.4302(3) 0.0856(19) Uani 1 2 d S T P . .
H2A H 0.576332 0.348358 0.413324 0.103 Uiso 0.5 1 calc R U P A .
H2B H 0.604959 0.116257 0.429535 0.103 Uiso 0.5 1 calc R U P . .
C3 C 0.8076(7) 0.250000 0.3868(3) 0.0718(15) Uani 1 2 d S T P A .
C4 C 0.8982(11) 0.250000 0.2765(5) 0.115(3) Uani 1 2 d S T P A 1
H4A H 0.946447 0.116135 0.274122 0.173 Uiso 0.5 1 calc R U P A 1
H4B H 0.981971 0.346102 0.290333 0.173 Uiso 0.5 1 calc R U P A 1
H4C H 0.856041 0.287762 0.232867 0.173 Uiso 0.5 1 calc R U P A 1
N1 N 0.7052(7) 0.3026(8) 0.4987(4) 0.069(2) Uani 0.5 1 d D U P A -1
N2 N 0.7069(10) 0.4850(13) 0.5304(5) 0.073(2) Uani 0.5 1 d D U P A -1
N3 N 0.7575(8) 0.4618(10) 0.5879(4) 0.0770(18) Uani 0.5 1 d D U P A -1
N4 N 0.7976(6) 0.263(4) 0.5952(3) 0.067(2) Uani 0.5 1 d D U P A -1
N5 N 0.8464(7) 0.1728(10) 0.6528(3) 0.0732(19) Uani 0.5 1 d . . P A -1
H5A H 0.795521 0.227830 0.686682 0.088 Uiso 0.5 1 d R U P A -1
H5B H 0.953455 0.214769 0.662532 0.088 Uiso 0.5 1 d R U P A -1
N6 N 0.7855(10) -0.0296(15) 0.5297(6) 0.078(3) Uani 0.5 1 d . . P A -1
H6A H 0.724079 -0.099236 0.557478 0.094 Uiso 0.5 1 d R U P A -1
H6B H 0.755896 -0.059364 0.488761 0.094 Uiso 0.5 1 d R U P A -1
C1 C 0.7638(9) 0.1661(12) 0.5394(4) 0.0600(17) Uani 0.5 1 d . . P A -1
N7 N 0.7976(14) -0.250000 0.3434(7) 0.086(2) Uani 0.8 2 d DS TU P B 1
N8 N 0.7209(11) -0.250000 0.3991(5) 0.111(3) Uani 0.8 2 d DS TU P B 1
N9 N 0.5616(10) -0.250000 0.3866(5) 0.106(3) Uani 0.8 2 d DS TU P B 1
N10 N 0.5436(12) -0.250000 0.3221(5) 0.088(2) Uani 0.8 2 d DS TU P B 1
N11 N 0.6912(16) -0.250000 0.2966(5) 0.085(3) Uani 0.8 2 d DS TU P B 1
N7A N 0.787(5) -0.260(11) 0.347(3) 0.091(4) Uani 0.1 1 d D U P B -1
N8A N 0.718(4) -0.354(7) 0.398(2) 0.085(4) Uani 0.1 1 d D U P B -1
N9A N 0.556(4) -0.357(7) 0.388(2) 0.089(4) Uani 0.1 1 d D U P B -1
N10A N 0.525(6) -0.260(12) 0.332(2) 0.092(4) Uani 0.1 1 d D U P B -1
N11A N 0.669(8) -0.213(11) 0.304(2) 0.094(4) Uani 0.1 1 d D U P B -1
O3 O 0.852(2) 0.250000 0.2196(11) 0.139(10) Uani 0.3 2 d GS T P C 2
H3A H 0.924989 0.315243 0.196930 0.208 Uiso 0.3 1 d G U P C 2
H3B H 0.760034 0.315756 0.219345 0.208 Uiso 0.3 1 d G U P C 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 C3 1.197(7) . ?
O2 C3 1.311(7) . ?
O2 C4 1.470(8) . ?
C2 H2A 0.9900 . ?
C2 H2A 0.9900 7_565 ?
C2 H2B 0.9900 7_565 ?
C2 H2B 0.9900 . ?
C2 C3 1.512(8) . ?
C2 N1 1.484(10) . ?
C4 H4A 0.98(5) 7_565 ?
C4 H4A 0.9800 . ?
C4 H4B 0.98(10) 7_565 ?
C4 H4B 0.9800 . ?
C4 H4C 0.98(5) 7_565 ?
C4 H4C 0.9800 . ?
N1 N2 1.379(10) . ?
N1 C1 1.320(9) . ?
N2 N3 1.244(12) . ?
N3 N4 1.38(2) . ?
N4 N5 1.372(14) . ?
N4 C1 1.333(15) . ?
N5 H5A 0.8822 . ?
N5 H5B 0.9388 . ?
N6 H6A 0.8860 . ?
N6 H6B 0.8853 . ?
N6 C1 1.337(12) . ?
N7 N8 1.290(10) . ?
N7 N11 1.286(9) . ?
N7 N8A 1.46(5) . ?
N7 N11A 1.35(7) . ?
N8 N9 1.325(8) . ?
N8 N7A 1.19(6) . ?
N8 N8A 0.70(5) . ?
N8 N9A 1.55(4) . ?
N9 N10 1.313(10) . ?
N9 N8A 1.47(4) . ?
N9 N9A 0.72(5) . ?
N9 N10A 1.15(5) . ?
N10 N11 1.312(8) . ?
N10 N9A 1.51(4) . ?
N10 N11A 1.11(6) . ?
N11 N7A 1.28(7) . ?
N11 N10A 1.54(6) . ?
N7A N8A 1.337(14) . ?
N7A N11A 1.337(14) . ?
N8A N9A 1.338(13) . ?
N9A N10A 1.333(14) . ?
N10A N11A 1.340(14) . ?
O3 H3A 0.87(18) 7_565 ?
O3 H3A 0.8700 . ?
O3 H3B 0.87(19) 7_565 ?
O3 H3B 0.8700 . ?

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
C3 O2 C4 115.4(6) . . ?
H2A C2 H2A 83.4 . 7_565 ?
H2A C2 H2B 27.3 . 7_565 ?
H2A C2 H2B 108.3 . . ?
H2A C2 H2B 108.3 7_565 7_565 ?
H2B C2 H2A 27.3 . 7_565 ?
H2B C2 H2B 129.4 . 7_565 ?
C3 C2 H2A 109.9(2) . 7_565 ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C3 C2 H2B 109.89(9) . 7_565 ?
N1 C2 H2A 131.0(3) . 7_565 ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 H2B 84.9(2) . 7_565 ?
N1 C2 C3 109.0(5) . . ?
O1 C3 O2 126.2(6) . . ?
O1 C3 C2 124.4(6) . . ?
O2 C3 C2 109.4(5) . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4A 109.5(10) . 7_565 ?
O2 C4 H4B 109(2) . 7_565 ?
O2 C4 H4B 109.5 . . ?
O2 C4 H4C 109.5 . . ?
O2 C4 H4C 109.5(12) . 7_565 ?
H4A C4 H4A 132.2 . 7_565 ?
H4A C4 H4B 109.5 7_565 7_565 ?
H4A C4 H4B 29.9 . 7_565 ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 7_565 7_565 ?
H4A C4 H4C 109.5 . . ?
H4A C4 H4C 82.1 . 7_565 ?
H4B C4 H4A 29.9 . 7_565 ?
H4B C4 H4B 82.1 . 7_565 ?
H4B C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 7_565 7_565 ?
H4B C4 H4C 132.2 . 7_565 ?
H4C C4 H4A 82.1 . 7_565 ?
H4C C4 H4B 132.2 . 7_565 ?
H4C C4 H4C 29.9 . 7_565 ?
N2 N1 C2 130.4(7) . . ?
C1 N1 C2 121.0(5) . . ?
C1 N1 N2 108.5(8) . . ?
N3 N2 N1 109.2(9) . . ?
N2 N3 N4 107.5(7) . . ?
N5 N4 N3 126.0(13) . . ?
C1 N4 N3 109.3(10) . . ?
C1 N4 N5 124(2) . . ?
N4 N5 H5A 109.8 . . ?
N4 N5 H5B 108.4 . . ?
H5A N5 H5B 98.6 . . ?
H6A N6 H6B 108.7 . . ?
C1 N6 H6A 110.3 . . ?
C1 N6 H6B 108.8 . . ?
N1 C1 N4 105.5(12) . . ?
N1 C1 N6 129.4(8) . . ?
N4 C1 N6 125.1(13) . . ?
N8 N7 N8A 29(2) . . ?
N8 N7 N11A 98(2) . . ?
N11 N7 N8 108.5(7) . . ?
N11 N7 N8A 104.8(16) . . ?
N11 N7 N11A 15(3) . . ?
N11A N7 N8A 101(3) . . ?
N7 N8 N9 108.0(7) . . ?
N7 N8 N9A 107.1(18) . . ?
N9 N8 N9A 27.7(18) . . ?
N7A N8 N7 4(3) . . ?
N7A N8 N9 106(3) . . ?
N7A N8 N9A 104(3) . . ?
N8A N8 N7 89(4) . . ?
N8A N8 N9 87(3) . . ?
N8A N8 N7A 86(5) . . ?
N8A N8 N9A 60(3) . . ?
N8 N9 N8A 28.3(18) . . ?
N10 N9 N8 107.5(7) . . ?
N10 N9 N8A 104.6(19) . . ?
N9A N9 N8 93(3) . . ?
N9A N9 N10 91(4) . . ?
N9A N9 N8A 65(3) . . ?
N9A N9 N10A 88(5) . . ?
N10A N9 N8 116(3) . . ?
N10A N9 N10 9(3) . . ?
N10A N9 N8A 110(3) . . ?
N9 N10 N9A 28.4(19) . . ?
N11 N10 N9 106.8(7) . . ?
N11 N10 N9A 106.7(14) . . ?
N11A N10 N9 103(3) . . ?
N11A N10 N11 13(4) . . ?
N11A N10 N9A 110(3) . . ?
N7 N11 N10 109.2(7) . . ?
N7 N11 N10A 104.8(19) . . ?
N10 N11 N10A 5.0(16) . . ?
N7A N11 N7 5.8(18) . . ?
N7A N11 N10 104(2) . . ?
N7A N11 N10A 100(3) . . ?
N8 N7A N11 115(4) . . ?
N8 N7A N8A 31(2) . . ?
N8 N7A N11A 104(3) . . ?
N11 N7A N8A 112(3) . . ?
N11 N7A N11A 15(3) . . ?
N8A N7A N11A 108.0(6) . . ?
N7 N8A N9 93(3) . . ?
N8 N8A N7 62(3) . . ?
N8 N8A N9 64(3) . . ?
N8 N8A N7A 63(5) . . ?
N8 N8A N9A 93(4) . . ?
N7A N8A N7 2(3) . . ?
N7A N8A N9 91.4(19) . . ?
N7A N8A N9A 107.9(6) . . ?
N9A N8A N7 110(3) . . ?
N9A N8A N9 29(2) . . ?
N9 N9A N8 59(3) . . ?
N9 N9A N10 60(3) . . ?
N9 N9A N8A 85(4) . . ?
N9 N9A N10A 60(4) . . ?
N10 N9A N8 88(2) . . ?
N8A N9A N8 27(2) . . ?
N8A N9A N10 101(2) . . ?
N10A N9A N8 94(2) . . ?
N10A N9A N10 7(2) . . ?
N10A N9A N8A 108.0(6) . . ?
N9 N10A N11 102(4) . . ?
N9 N10A N9A 33(2) . . ?
N9 N10A N11A 99(3) . . ?
N9A N10A N11 104(2) . . ?
N9A N10A N11A 107.9(7) . . ?
N11A N10A N11 11(3) . . ?
N10 N11A N7 119(3) . . ?
N10 N11A N7A 113(2) . . ?
N10 N11A N10A 6(2) . . ?
N7A N11A N7 5.5(18) . . ?
N7A N11A N10A 107.7(6) . . ?
N10A N11A N7 113.0(19) . . ?
H4C O3 H3A 88.7 7_565 7_565 ?
H4C O3 H3B 74.7 7_565 7_565 ?
H3A O3 H3B 109.5 . . ?
H3A O3 H3B 109.5 7_565 7_565 ?
H3A O3 H3B 147.3 . 7_565 ?
H3B O3 H3B 60.8 . 7_565 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 -179.6(6) . . . . ?
C2 N1 C1 N4 178.6(6) . . . . ?
C2 N1 C1 N6 -2.1(12) . . . . ?
C3 C2 N1 N2 94.1(7) . . . . ?
C3 C2 N1 C1 -82.9(6) . . . . ?
C4 O2 C3 O1 0.000(1) . . . . ?
C4 O2 C3 C2 180.000(1) . . . . ?
N1 C2 C3 O1 14.5(2) . . . . ?
N1 C2 C3 O2 -165.5(2) . . . . ?
N1 N2 N3 N4 2.5(10) . . . . ?
N2 N1 C1 N4 1.1(8) . . . . ?
N2 N1 C1 N6 -179.6(9) . . . . ?
N2 N3 N4 N5 -174.7(8) . . . . ?
N2 N3 N4 C1 -1.9(9) . . . . ?
N3 N4 C1 N1 0.4(8) . . . . ?
N3 N4 C1 N6 -179.0(8) . . . . ?
N5 N4 C1 N1 173.4(6) . . . . ?
N5 N4 C1 N6 -6.0(12) . . . . ?
C1 N1 N2 N3 -2.4(10) . . . . ?
N7 N8 N9 N10 0.000(2) . . . . ?
N7 N8 N9 N8A 88(4) . . . . ?
N7 N8 N9 N9A 93(4) . . . . ?
N7 N8 N9 N10A 4(4) . . . . ?
N7 N8 N7A N11 -118(51) . . . . ?
N7 N8 N7A N8A 150(47) . . . . ?
N7 N8 N7A N11A -108(50) . . . . ?
N7 N8 N8A N9 -108.1(8) . . . . ?
N7 N8 N8A N7A -2(3) . . . . ?
N7 N8 N8A N9A -110(2) . . . . ?
N7 N8 N9A N9 -96(3) . . . . ?
N7 N8 N9A N10 -41(2) . . . . ?
N7 N8 N9A N8A 79(4) . . . . ?
N7 N8 N9A N10A -45(3) . . . . ?
N7 N11 N7A N8 143(39) . . . . ?
N7 N11 N7A N8A 178(37) . . . . ?
N7 N11 N7A N11A 102(34) . . . . ?
N7 N11 N10A N9 4(5) . . . . ?
N7 N11 N10A N9A -29(5) . . . . ?
N7 N11 N10A N11A 81(13) . . . . ?
N7 N8A N9A N8 -62(3) . . . . ?
N7 N8A N9A N9 -57(5) . . . . ?
N7 N8A N9A N10 1(4) . . . . ?
N7 N8A N9A N10A -1(4) . . . . ?
N8 N7 N11 N10 0.000(3) . . . . ?
N8 N7 N11 N7A -32(34) . . . . ?
N8 N7 N11 N10A -3(3) . . . . ?
N8 N7 N8A N9 59(3) . . . . ?
N8 N7 N8A N7A 108(100) . . . . ?
N8 N7 N8A N9A 83(4) . . . . ?
N8 N7 N11A N10 -23(7) . . . . ?
N8 N7 N11A N7A -36(35) . . . . ?
N8 N7 N11A N10A -21(5) . . . . ?
N8 N9 N10 N11 0.000(2) . . . . ?
N8 N9 N10 N9A 94(3) . . . . ?
N8 N9 N10 N11A -13(4) . . . . ?
N8 N9 N8A N7 -57(3) . . . . ?
N8 N9 N8A N7A -59(5) . . . . ?
N8 N9 N8A N9A 175(5) . . . . ?
N8 N9 N9A N10 -107.6(8) . . . . ?
N8 N9 N9A N8A -2(2) . . . . ?
N8 N9 N9A N10A -116(3) . . . . ?
N8 N9 N10A N11 -5(6) . . . . ?
N8 N9 N10A N9A 93(4) . . . . ?
N8 N9 N10A N11A -16(6) . . . . ?
N8 N7A N8A N7 -71(99) . . . . ?
N8 N7A N8A N9 60(3) . . . . ?
N8 N7A N8A N9A 85(4) . . . . ?
N8 N7A N11A N7 140(39) . . . . ?
N8 N7A N11A N10 -28(6) . . . . ?
N8 N7A N11A N10A -26(5) . . . . ?
N8 N8A N9A N9 4(4) . . . . ?
N8 N8A N9A N10 63(5) . . . . ?
N8 N8A N9A N10A 60(5) . . . . ?
N8 N9A N10A N9 -50(3) . . . . ?
N8 N9A N10A N11 40(4) . . . . ?
N8 N9A N10A N11A 29(4) . . . . ?
N9 N8 N7A N11 6(6) . . . . ?
N9 N8 N7A N8A -86(3) . . . . ?
N9 N8 N7A N11A 16(4) . . . . ?
N9 N8 N8A N7 108.1(8) . . . . ?
N9 N8 N8A N7A 106(3) . . . . ?
N9 N8 N8A N9A -2(2) . . . . ?
N9 N8 N9A N10 56(3) . . . . ?
N9 N8 N9A N8A 175(5) . . . . ?
N9 N8 N9A N10A 51(4) . . . . ?
N9 N10 N11 N7 0.000(2) . . . . ?
N9 N10 N11 N7A 3(3) . . . . ?
N9 N10 N11 N10A 29(37) . . . . ?
N9 N10 N9A N8 -55(2) . . . . ?
N9 N10 N9A N8A -78(3) . . . . ?
N9 N10 N9A N10A 85(28) . . . . ?
N9 N10 N11A N7 23(7) . . . . ?
N9 N10 N11A N7A 24(5) . . . . ?
N9 N10 N11A N10A 10(38) . . . . ?
N9 N8A N9A N8 -4(4) . . . . ?
N9 N8A N9A N10 58(3) . . . . ?
N9 N8A N9A N10A 56(4) . . . . ?
N9 N9A N10A N11 90(5) . . . . ?
N9 N9A N10A N11A 79(5) . . . . ?
N9 N10A N11A N7 24(6) . . . . ?
N9 N10A N11A N10 -169(43) . . . . ?
N9 N10A N11A N7A 25(6) . . . . ?
N10 N9 N8A N7 43(2) . . . . ?
N10 N9 N8A N8 100(4) . . . . ?
N10 N9 N8A N7A 41(3) . . . . ?
N10 N9 N8A N9A -85(4) . . . . ?
N10 N9 N9A N8 107.6(8) . . . . ?
N10 N9 N9A N8A 105(2) . . . . ?
N10 N9 N9A N10A -8(3) . . . . ?
N10 N9 N10A N11 17(19) . . . . ?
N10 N9 N10A N9A 114(22) . . . . ?
N10 N9 N10A N11A 6(20) . . . . ?
N10 N11 N7A N8 -6(6) . . . . ?
N10 N11 N7A N8A 28(5) . . . . ?
N10 N11 N7A N11A -47(10) . . . . ?
N10 N11 N10A N9 -147(41) . . . . ?
N10 N11 N10A N9A 179(100) . . . . ?
N10 N11 N10A N11A -71(42) . . . . ?
N10 N9A N10A N9 -91(28) . . . . ?
N10 N9A N10A N11 -1(24) . . . . ?
N10 N9A N10A N11A -12(25) . . . . ?
N11 N7 N8 N9 0.000(2) . . . . ?
N11 N7 N8 N7A 57(48) . . . . ?
N11 N7 N8 N8A 87(3) . . . . ?
N11 N7 N8 N9A 29.1(19) . . . . ?
N11 N7 N8A N8 -102(3) . . . . ?
N11 N7 N8A N9 -43(2) . . . . ?
N11 N7 N8A N7A 6(99) . . . . ?
N11 N7 N8A N9A -18(4) . . . . ?
N11 N7 N11A N10 113(14) . . . . ?
N11 N7 N11A N7A 100(34) . . . . ?
N11 N7 N11A N10A 115(12) . . . . ?
N11 N10 N9A N8 40(2) . . . . ?
N11 N10 N9A N9 95(3) . . . . ?
N11 N10 N9A N8A 16(4) . . . . ?
N11 N10 N9A N10A 179(28) . . . . ?
N11 N10 N11A N7 -85(12) . . . . ?
N11 N10 N11A N7A -83(12) . . . . ?
N11 N10 N11A N10A -97(42) . . . . ?
N11 N7A N8A N7 -173(100) . . . . ?
N11 N7A N8A N8 -102(6) . . . . ?
N11 N7A N8A N9 -42(4) . . . . ?
N11 N7A N8A N9A -18(4) . . . . ?
N11 N7A N11A N7 -78(34) . . . . ?
N11 N7A N11A N10 114(14) . . . . ?
N11 N7A N11A N10A 116(12) . . . . ?
N11 N10A N11A N7 -82(12) . . . . ?
N11 N10A N11A N10 86(43) . . . . ?
N11 N10A N11A N7A -81(12) . . . . ?
N7A N8 N9 N10 -3(3) . . . . ?
N7A N8 N9 N8A 85(5) . . . . ?
N7A N8 N9 N9A 89(4) . . . . ?
N7A N8 N9 N10A 0(6) . . . . ?
N7A N8 N8A N7 2(3) . . . . ?
N7A N8 N8A N9 -106(3) . . . . ?
N7A N8 N8A N9A -108(2) . . . . ?
N7A N8 N9A N9 -98(4) . . . . ?
N7A N8 N9A N10 -42(4) . . . . ?
N7A N8 N9A N8A 77(5) . . . . ?
N7A N8 N9A N10A -47(4) . . . . ?
N7A N11 N10A N9 7(6) . . . . ?
N7A N11 N10A N9A -26(6) . . . . ?
N7A N11 N10A N11A 84(13) . . . . ?
N7A N8A N9A N8 -62(5) . . . . ?
N7A N8A N9A N9 -58(4) . . . . ?
N7A N8A N9A N10 0(3) . . . . ?
N7A N8A N9A N10A -2(3) . . . . ?
N8A N7 N8 N9 -87(3) . . . . ?
N8A N7 N8 N7A -30(47) . . . . ?
N8A N7 N8 N9A -58(3) . . . . ?
N8A N7 N11 N10 30(2) . . . . ?
N8A N7 N11 N7A -2(33) . . . . ?
N8A N7 N11 N10A 27(4) . . . . ?
N8A N7 N11A N10 6(7) . . . . ?
N8A N7 N11A N7A -7(34) . . . . ?
N8A N7 N11A N10A 7(6) . . . . ?
N8A N8 N9 N10 -88(4) . . . . ?
N8A N8 N9 N9A 4(4) . . . . ?
N8A N8 N9 N10A -85(6) . . . . ?
N8A N8 N7A N11 92(6) . . . . ?
N8A N8 N7A N11A 102(4) . . . . ?
N8A N8 N9A N9 -175(5) . . . . ?
N8A N8 N9A N10 -119(5) . . . . ?
N8A N8 N9A N10A -124(4) . . . . ?
N8A N9 N10 N11 -29.3(19) . . . . ?
N8A N9 N10 N9A 65(3) . . . . ?
N8A N9 N10 N11A -43(4) . . . . ?
N8A N9 N9A N8 2(2) . . . . ?
N8A N9 N9A N10 -105(2) . . . . ?
N8A N9 N9A N10A -114(2) . . . . ?
N8A N9 N10A N11 -35(5) . . . . ?
N8A N9 N10A N9A 62(3) . . . . ?
N8A N9 N10A N11A -46(5) . . . . ?
N8A N7A N11A N7 172(38) . . . . ?
N8A N7A N11A N10 5(5) . . . . ?
N8A N7A N11A N10A 6(5) . . . . ?
N8A N9A N10A N9 -73(4) . . . . ?
N8A N9A N10A N11 17(5) . . . . ?
N8A N9A N10A N11A 6(5) . . . . ?
N9A N8 N9 N10 -93(4) . . . . ?
N9A N8 N9 N8A -4(4) . . . . ?
N9A N8 N9 N10A -89(5) . . . . ?
N9A N8 N7A N11 34(6) . . . . ?
N9A N8 N7A N8A -58(2) . . . . ?
N9A N8 N7A N11A 44(4) . . . . ?
N9A N8 N8A N7 110(2) . . . . ?
N9A N8 N8A N9 2(2) . . . . ?
N9A N8 N8A N7A 108(2) . . . . ?
N9A N9 N10 N11 -94(3) . . . . ?
N9A N9 N10 N11A -107(5) . . . . ?
N9A N9 N8A N7 127(4) . . . . ?
N9A N9 N8A N8 -175(5) . . . . ?
N9A N9 N8A N7A 126(3) . . . . ?
N9A N9 N10A N11 -97(5) . . . . ?
N9A N9 N10A N11A -109(4) . . . . ?
N9A N10 N11 N7 -30(2) . . . . ?
N9A N10 N11 N7A -27(4) . . . . ?
N9A N10 N11 N10A -1(36) . . . . ?
N9A N10 N11A N7 -6(8) . . . . ?
N9A N10 N11A N7A -5(6) . . . . ?
N9A N10 N11A N10A -19(37) . . . . ?
N9A N10A N11A N7 -9(6) . . . . ?
N9A N10A N11A N10 159(42) . . . . ?
N9A N10A N11A N7A -7(6) . . . . ?
N10A N9 N10 N11 -160(23) . . . . ?
N10A N9 N10 N9A -66(22) . . . . ?
N10A N9 N10 N11A -173(25) . . . . ?
N10A N9 N8A N7 50(4) . . . . ?
N10A N9 N8A N8 107(5) . . . . ?
N10A N9 N8A N7A 49(4) . . . . ?
N10A N9 N8A N9A -77(5) . . . . ?
N10A N9 N9A N8 116(3) . . . . ?
N10A N9 N9A N10 8(3) . . . . ?
N10A N9 N9A N8A 114(2) . . . . ?
N10A N11 N7A N8 -8(7) . . . . ?
N10A N11 N7A N8A 26(6) . . . . ?
N10A N11 N7A N11A -49(9) . . . . ?
N11A N7 N8 N9 11(3) . . . . ?
N11A N7 N8 N7A 68(49) . . . . ?
N11A N7 N8 N8A 98(5) . . . . ?
N11A N7 N8 N9A 40(4) . . . . ?
N11A N7 N11 N10 -47(9) . . . . ?
N11A N7 N11 N7A -78(34) . . . . ?
N11A N7 N11 N10A -49(8) . . . . ?
N11A N7 N8A N8 -87(4) . . . . ?
N11A N7 N8A N9 -28(4) . . . . ?
N11A N7 N8A N7A 21(98) . . . . ?
N11A N7 N8A N9A -4(5) . . . . ?
N11A N10 N11 N7 76(13) . . . . ?
N11A N10 N11 N7A 79(13) . . . . ?
N11A N10 N11 N10A 105(42) . . . . ?
N11A N10 N9A N8 26(5) . . . . ?
N11A N10 N9A N9 81(5) . . . . ?
N11A N10 N9A N8A 3(5) . . . . ?
N11A N10 N9A N10A 166(30) . . . . ?
N11A N7A N8A N7 -158(100) . . . . ?
N11A N7A N8A N8 -87(5) . . . . ?
N11A N7A N8A N9 -27(3) . . . . ?
N11A N7A N8A N9A -2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.976(9)
2 0.024(9)

####################################################################### 
# 
# 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_nlg_tong_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2p28dg
_database_code_depnum_ccdc_archive 'CCDC 2474835'
loop_
_audit_author_name
_audit_author_address
'Zhiyu King' 'Nanjing University of Science and Technology'
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_audit_creation_date             2025-07-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H9 N6 O, N5'
_chemical_formula_sum            'C4 H9 N11 O'
_chemical_formula_weight         227.22
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   20.246(4)
_cell_length_b                   5.1030(12)
_cell_length_c                   11.589(2)
_cell_angle_alpha                90
_cell_angle_beta                 123.767(11)
_cell_angle_gamma                90
_cell_volume                     995.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    799
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      62.947
_cell_measurement_theta_min      4.590
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    1.034
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.5701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1423 before and 0.0802 after correction.
The Ratio of minimum to maximum transmission is 0.7571.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1008
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.765
_diffrn_reflns_theta_min         4.589
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker D8 Veture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                689
_reflns_number_total             1008
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1008
_refine_ls_number_restraints     205
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0883
_refine_ls_restrained_S_all      0.959
_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)+(0.0600P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2184
_refine_ls_wR_factor_ref         0.2376
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.604(9)
 0.396(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N6-C1
 1.35 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N7 \\sim N8 \\sim N9 \\sim N10 \\sim N11: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
O1 \\sim N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5 \\sim N6 \\sim C1 \\sim C2
\\sim C3 \\sim C4: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
5. Rigid body (RIGU) restrains
 N7, N8, N9, N10, N11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O1, N1, N2, N3, N4, N5, N6, C1, C2, C3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Others
 Fixed Sof: O1(0.5) N1(0.5) H1A(0.5) H1B(0.5) N2(0.5) N3(0.5) N4(0.5) N5(0.5)
 N6(0.5) H6A(0.5) H6B(0.5) C1(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) C4(0.5)
 H4A(0.5) H4B(0.5) H4C(0.5) N7(0.5) N8(0.5) N9(0.5) N10(0.5) N11(0.5)
7.a Rotating group:
 N1(H1A,H1B), N6(H6A,H6B)
7.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
7.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.5973(4) 0.022(12) 0.5529(6) 0.043(5) Uani 0.5 1 d . U P A -1
N1 N 0.4888(4) 0.051(2) 0.8604(8) 0.040(3) Uani 0.5 1 d . U P A -1
H1A H 0.525073 -0.069329 0.909347 0.048 Uiso 0.5 1 d R U P A -1
H1B H 0.486184 0.159392 0.916775 0.048 Uiso 0.5 1 d R U P A -1
N2 N 0.5111(4) 0.1899(15) 0.7838(7) 0.0368(16) Uani 0.5 1 d . U P A -1
N3 N 0.4681(4) 0.3896(17) 0.6974(8) 0.0437(18) Uani 0.5 1 d . U P A -1
N4 N 0.5074(4) 0.480(7) 0.6517(7) 0.042(3) Uani 0.5 1 d . U P A -1
N5 N 0.5765(4) 0.3469(15) 0.7091(7) 0.0347(15) Uani 0.5 1 d . U P A -1
N6 N 0.6352(4) -0.029(4) 0.8685(7) 0.030(3) Uani 0.5 1 d D U P A -1
H6A H 0.678547 -0.010863 0.878938 0.036 Uiso 0.5 1 d R U P A -1
H6B H 0.644211 -0.030381 0.952084 0.036 Uiso 0.5 1 d R U P A -1
C1 C 0.5801(5) 0.1579(17) 0.7941(8) 0.0313(17) Uani 0.5 1 d D U P A -1
C2 C 0.6355(5) 0.4107(18) 0.6776(9) 0.0356(18) Uani 0.5 1 d . U P A -1
H2A H 0.688479 0.428363 0.765384 0.043 Uiso 0.5 1 calc R U P A -1
H2B H 0.621780 0.580766 0.628382 0.043 Uiso 0.5 1 calc R U P A -1
C3 C 0.6388(5) 0.1973(19) 0.5871(9) 0.0380(19) Uani 0.5 1 d . U P A -1
C4 C 0.6932(6) 0.259(2) 0.5434(11) 0.050(3) Uani 0.5 1 d . U P A -1
H4A H 0.665102 0.365174 0.458727 0.075 Uiso 0.5 1 calc R U P A -1
H4B H 0.711356 0.095595 0.525221 0.075 Uiso 0.5 1 calc R U P A -1
H4C H 0.739031 0.356574 0.617264 0.075 Uiso 0.5 1 calc R U P A -1
N7 N 0.6553(5) 0.5868(17) 1.0622(8) 0.049(2) Uani 0.5 1 d . U P B -1
N8 N 0.6050(4) 0.527(5) 1.0941(8) 0.050(3) Uani 0.5 1 d . U P B -1
N9 N 0.6404(5) 0.3096(18) 1.1839(9) 0.048(2) Uani 0.5 1 d . U P B -1
N10 N 0.7090(5) 0.2722(19) 1.2046(9) 0.052(2) Uani 0.5 1 d . U P B -1
N11 N 0.7180(4) 0.4446(18) 1.1273(8) 0.046(2) Uani 0.5 1 d . U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.13(5) . ?
N1 H1A 0.8802 . ?
N1 H1B 0.8800 . ?
N1 N2 1.393(10) . ?
N2 N3 1.353(11) . ?
N2 C1 1.343(10) . ?
N3 N4 1.263(17) . ?
N4 N5 1.35(2) . ?
N5 C1 1.352(11) . ?
N5 C2 1.466(10) . ?
N6 H6A 0.8212 . ?
N6 H6B 0.8809 . ?
N6 C1 1.352(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.539(13) . ?
C3 C4 1.478(12) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N7 N8 1.298(11) . ?
N7 N11 1.282(10) . ?
N8 N9 1.41(2) . ?
N9 N10 1.285(11) . ?
N10 N11 1.338(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 109.4 . . ?
N2 N1 H1A 108.4 . . ?
N2 N1 H1B 109.2 . . ?
N3 N2 N1 123.5(7) . . ?
C1 N2 N1 124.8(7) . . ?
C1 N2 N3 111.5(7) . . ?
N4 N3 N2 106.9(13) . . ?
N3 N4 N5 109(2) . . ?
N4 N5 C2 121.9(12) . . ?
C1 N5 N4 109.8(11) . . ?
C1 N5 C2 128.3(7) . . ?
H6A N6 H6B 106.7 . . ?
C1 N6 H6A 116.9 . . ?
C1 N6 H6B 107.5 . . ?
N2 C1 N5 102.5(7) . . ?
N2 C1 N6 126.3(7) . . ?
N6 C1 N5 131.1(8) . . ?
N5 C2 H2A 109.4 . . ?
N5 C2 H2B 109.4 . . ?
N5 C2 C3 111.3(7) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
O1 C3 C2 119.3(14) . . ?
O1 C3 C4 126.5(13) . . ?
C4 C3 C2 113.9(8) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N11 N7 N8 112.1(11) . . ?
N7 N8 N9 103.7(10) . . ?
N10 N9 N8 107.9(8) . . ?
N9 N10 N11 108.2(8) . . ?
N7 N11 N10 107.9(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 N4 176.2(14) . . . . ?
N1 N2 C1 N5 -175.4(8) . . . . ?
N1 N2 C1 N6 7.0(15) . . . . ?
N2 N3 N4 N5 -1(2) . . . . ?
N3 N2 C1 N5 -0.3(9) . . . . ?
N3 N2 C1 N6 -177.9(10) . . . . ?
N3 N4 N5 C1 1(2) . . . . ?
N3 N4 N5 C2 -179.0(12) . . . . ?
N4 N5 C1 N2 -0.5(14) . . . . ?
N4 N5 C1 N6 177.0(15) . . . . ?
N4 N5 C2 C3 -108.8(15) . . . . ?
N5 C2 C3 O1 1(2) . . . . ?
N5 C2 C3 C4 175.9(7) . . . . ?
C1 N2 N3 N4 1.0(15) . . . . ?
C1 N5 C2 C3 71.0(11) . . . . ?
C2 N5 C1 N2 179.7(8) . . . . ?
C2 N5 C1 N6 -2.9(16) . . . . ?
N7 N8 N9 N10 4.4(15) . . . . ?
N8 N7 N11 N10 2.2(14) . . . . ?
N8 N9 N10 N11 -3.3(13) . . . . ?
N9 N10 N11 N7 0.9(11) . . . . ?
N11 N7 N8 N9 -4.0(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.604(9)
2 0.396(9)

####################################################################### 
# 
# 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_nlg_n4n5_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2lrhc7
_database_code_depnum_ccdc_archive 'CCDC 2405859'
loop_
_audit_author_name
_audit_author_address
'Zhiyu King'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2024-11-27 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_audit_creation_date             2024-11-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H7 N6, N5'
_chemical_formula_sum            'C2 H7 N11'
_chemical_formula_weight         185.19
_chemical_absolute_configuration ad
_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6423(2)
_cell_length_b                   10.7594(3)
_cell_length_c                   13.1479(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     798.18(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3014
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.019
_cell_measurement_theta_min      5.312
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0530 after correction.
The Ratio of minimum to maximum transmission is 0.8822.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5900
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.381
_diffrn_reflns_theta_min         5.312
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1352
_reflns_number_total             1458
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.072
_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)+(0.0410P)²+0.1311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N6(H6A,H6B)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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
C1 C 0.2478(4) 0.46560(19) 0.40322(15) 0.0272(5) Uani 1 1 d . . . . .
C2 C -0.0054(5) 0.3140(2) 0.3082(2) 0.0404(6) Uani 1 1 d . . . . .
H2A H -0.033071 0.256142 0.363551 0.061 Uiso 1 1 calc R U . . .
H2B H 0.123425 0.283730 0.266112 0.061 Uiso 1 1 calc R U . . .
H2C H -0.147958 0.321380 0.267460 0.061 Uiso 1 1 calc R U . . .
N1 N 0.2199(3) 0.58716(16) 0.42110(13) 0.0284(4) Uani 1 1 d . . . . .
N2 N 0.0144(4) 0.62837(17) 0.37885(15) 0.0347(5) Uani 1 1 d . . . . .
N3 N -0.0833(4) 0.53636(18) 0.33447(15) 0.0348(5) Uani 1 1 d . . . . .
N4 N 0.0567(3) 0.43481(16) 0.34950(13) 0.0285(4) Uani 1 1 d . . . . .
N5 N 0.4221(3) 0.39423(17) 0.43480(15) 0.0336(4) Uani 1 1 d . . . . .
H5A H 0.421257 0.315207 0.420782 0.040 Uiso 1 1 calc R U . . .
H5B H 0.538172 0.426024 0.469713 0.040 Uiso 1 1 calc R U . . .
N6 N 0.3790(4) 0.66210(17) 0.47468(17) 0.0388(5) Uani 1 1 d . . . . .
H6A H 0.324196 0.678861 0.539183 0.047 Uiso 1 1 d R U . . .
H6B H 0.374594 0.737415 0.450351 0.047 Uiso 1 1 d R U . . .
N7 N 0.4519(4) 0.12785(19) 0.38274(18) 0.0427(5) Uani 1 1 d . . . . .
N8 N 0.6099(4) 0.0754(2) 0.32237(18) 0.0515(6) Uani 1 1 d . . . . .
N9 N 0.5749(4) -0.0458(2) 0.32669(17) 0.0470(5) Uani 1 1 d . . . . .
N10 N 0.4000(4) -0.06721(19) 0.38762(16) 0.0433(5) Uani 1 1 d . . . . .
N11 N 0.3224(4) 0.04003(19) 0.42303(15) 0.0399(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.338(3) . ?
C1 N4 1.331(3) . ?
C1 N5 1.315(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C2 N4 1.451(3) . ?
N1 N2 1.360(3) . ?
N1 N6 1.397(3) . ?
N2 N3 1.275(3) . ?
N3 N4 1.363(3) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
N6 H6A 0.9205 . ?
N6 H6B 0.8716 . ?
N7 N8 1.320(3) . ?
N7 N11 1.306(3) . ?
N8 N9 1.320(3) . ?
N9 N10 1.292(3) . ?
N10 N11 1.319(3) . ?

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
N4 C1 N1 103.95(19) . . ?
N5 C1 N1 127.1(2) . . ?
N5 C1 N4 128.9(2) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N4 C2 H2A 109.5 . . ?
N4 C2 H2B 109.5 . . ?
N4 C2 H2C 109.5 . . ?
C1 N1 N2 110.33(18) . . ?
C1 N1 N6 125.23(19) . . ?
N2 N1 N6 124.44(17) . . ?
N3 N2 N1 107.62(17) . . ?
N2 N3 N4 107.79(17) . . ?
C1 N4 C2 128.1(2) . . ?
C1 N4 N3 110.31(18) . . ?
N3 N4 C2 121.60(18) . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N1 N6 H6A 111.2 . . ?
N1 N6 H6B 109.5 . . ?
H6A N6 H6B 98.4 . . ?
N11 N7 N8 108.19(19) . . ?
N9 N8 N7 107.2(2) . . ?
N10 N9 N8 108.5(2) . . ?
N9 N10 N11 108.45(19) . . ?
N7 N11 N10 107.70(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 -0.8(2) . . . . ?
N1 C1 N4 C2 179.3(2) . . . . ?
N1 C1 N4 N3 0.5(2) . . . . ?
N1 N2 N3 N4 1.1(2) . . . . ?
N2 N3 N4 C1 -1.0(2) . . . . ?
N2 N3 N4 C2 -179.94(19) . . . . ?
N4 C1 N1 N2 0.2(2) . . . . ?
N4 C1 N1 N6 -179.33(19) . . . . ?
N5 C1 N1 N2 -178.1(2) . . . . ?
N5 C1 N1 N6 2.5(3) . . . . ?
N5 C1 N4 C2 -2.5(4) . . . . ?
N5 C1 N4 N3 178.7(2) . . . . ?
N6 N1 N2 N3 178.69(19) . . . . ?
N7 N8 N9 N10 0.2(3) . . . . ?
N8 N7 N11 N10 0.0(3) . . . . ?
N8 N9 N10 N11 -0.2(3) . . . . ?
N9 N10 N11 N7 0.2(3) . . . . ?
N11 N7 N8 N9 -0.1(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_mo_20250619_zz_nlg_xa_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2nv7zr
_database_code_depnum_ccdc_archive 'CCDC 2468095'
loop_
_audit_author_name
_audit_author_address
'Zhiyu King'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-06-28 deposited with the CCDC.	2026-03-19 downloaded from the CCDC.
;
_audit_creation_date             2025-06-19
_audit_creation_method           
;
Olex2 1.5
(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         'C3 H8 N7 O, N5'
_chemical_formula_sum            'C3 H8 N12 O'
_chemical_formula_weight         228.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   9.9792(7)
_cell_length_b                   10.7261(7)
_cell_length_c                   10.1674(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.243(2)
_cell_angle_gamma                90
_cell_volume                     999.97(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      25.19
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.9022.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11626
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1553
_reflns_number_total             2287
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.038
_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)+(0.0399P)²+0.4786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1152
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Rotating group:
 N6(H6A,H6B)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c X=CH2 refined with riding coordinates:
 N7(H7A,H7B)
;
_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
C1 C 0.7542(2) 0.67166(16) 0.3911(2) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.7280(2) 0.73090(18) 0.5145(2) 0.0339(4) Uani 1 1 d . . . . .
H2A H 0.772857 0.678514 0.601104 0.041 Uiso 1 1 calc R U . . .
H2B H 0.775067 0.813921 0.535484 0.041 Uiso 1 1 calc R U . . .
C3 C 0.48456(19) 0.83421(16) 0.4064(2) 0.0284(4) Uani 1 1 d . . . . .
N1 N 0.8932(2) 0.65539(19) 0.4154(2) 0.0452(5) Uani 1 1 d . . . . .
N2 N 0.57406(17) 0.74421(14) 0.48091(17) 0.0320(4) Uani 1 1 d . . . . .
N3 N 0.4984(2) 0.65804(15) 0.5242(2) 0.0424(4) Uani 1 1 d . . . . .
N4 N 0.36628(19) 0.69308(16) 0.4803(2) 0.0433(4) Uani 1 1 d . . . . .
N5 N 0.35482(16) 0.80261(15) 0.40639(18) 0.0338(4) Uani 1 1 d . . . . .
N6 N 0.22945(17) 0.87273(16) 0.3430(2) 0.0421(4) Uani 1 1 d . . . . .
H6A H 0.163498 0.827850 0.276062 0.051 Uiso 1 1 d R U . . .
H6B H 0.196005 0.893869 0.408107 0.051 Uiso 1 1 d R U . . .
N7 N 0.51511(17) 0.93332(15) 0.34862(18) 0.0353(4) Uani 1 1 d . . . . .
H7A H 0.605100 0.946749 0.356926 0.042 Uiso 1 1 calc R U . . .
H7B H 0.445693 0.986605 0.301429 0.042 Uiso 1 1 calc R U . . .
O1 O 0.65184(15) 0.64299(13) 0.28017(16) 0.0423(4) Uani 1 1 d . . . . .
N8 N 1.0999(2) 0.46672(18) 0.2243(2) 0.0516(5) Uani 1 1 d . . . . .
N9 N 1.03115(19) 0.57228(18) 0.2142(2) 0.0456(5) Uani 1 1 d . . . . .
N10 N 1.08055(19) 0.65218(17) 0.1466(2) 0.0463(5) Uani 1 1 d . . . . .
N11 N 1.1812(2) 0.59568(19) 0.1157(2) 0.0512(5) Uani 1 1 d . . . . .
N12 N 1.1933(2) 0.48104(17) 0.1628(2) 0.0464(5) Uani 1 1 d . . . . .
H1A H 0.961(3) 0.691(2) 0.492(3) 0.061(8) Uiso 1 1 d . . . . .
H1B H 0.917(3) 0.623(2) 0.349(3) 0.059(8) 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
C1 C2 1.519(3) . ?
C1 N1 1.321(3) . ?
C1 O1 1.225(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 N2 1.443(2) . ?
C3 N2 1.330(2) . ?
C3 N5 1.338(2) . ?
C3 N7 1.308(2) . ?
N1 H1A 0.89(3) . ?
N1 H1B 0.87(3) . ?
N2 N3 1.371(2) . ?
N3 N4 1.270(2) . ?
N4 N5 1.375(2) . ?
N5 N6 1.382(2) . ?
N6 H6A 0.8802 . ?
N6 H6B 0.8802 . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8800 . ?
N8 N9 1.307(2) . ?
N8 N12 1.321(2) . ?
N9 N10 1.310(2) . ?
N10 N11 1.313(2) . ?
N11 N12 1.308(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 114.28(18) . . ?
O1 C1 C2 120.86(17) . . ?
O1 C1 N1 124.9(2) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C2 C1 111.10(16) . . ?
N2 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
N2 C3 N5 104.38(15) . . ?
N7 C3 N2 128.51(16) . . ?
N7 C3 N5 127.09(17) . . ?
C1 N1 H1A 119.6(16) . . ?
C1 N1 H1B 119.6(16) . . ?
H1A N1 H1B 120(2) . . ?
C3 N2 C2 128.27(16) . . ?
C3 N2 N3 109.93(15) . . ?
N3 N2 C2 121.79(16) . . ?
N4 N3 N2 108.32(16) . . ?
N3 N4 N5 107.21(15) . . ?
C3 N5 N4 110.15(15) . . ?
C3 N5 N6 124.06(16) . . ?
N4 N5 N6 125.78(15) . . ?
N5 N6 H6A 109.0 . . ?
N5 N6 H6B 109.4 . . ?
H6A N6 H6B 109.4 . . ?
C3 N7 H7A 120.0 . . ?
C3 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
N9 N8 N12 107.98(17) . . ?
N8 N9 N10 108.28(16) . . ?
N9 N10 N11 107.77(17) . . ?
N12 N11 N10 108.36(17) . . ?
N11 N12 N8 107.60(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N2 C3 -82.6(2) . . . . ?
C1 C2 N2 N3 96.5(2) . . . . ?
C2 N2 N3 N4 179.94(17) . . . . ?
C3 N2 N3 N4 -0.8(2) . . . . ?
N1 C1 C2 N2 -179.27(17) . . . . ?
N2 C3 N5 N4 -0.4(2) . . . . ?
N2 C3 N5 N6 178.43(17) . . . . ?
N2 N3 N4 N5 0.5(2) . . . . ?
N3 N4 N5 C3 -0.1(2) . . . . ?
N3 N4 N5 N6 -178.88(18) . . . . ?
N5 C3 N2 C2 179.89(17) . . . . ?
N5 C3 N2 N3 0.7(2) . . . . ?
N7 C3 N2 C2 -1.7(3) . . . . ?
N7 C3 N2 N3 179.13(19) . . . . ?
N7 C3 N5 N4 -178.84(19) . . . . ?
N7 C3 N5 N6 0.0(3) . . . . ?
O1 C1 C2 N2 0.8(3) . . . . ?
N8 N9 N10 N11 -0.4(2) . . . . ?
N9 N8 N12 N11 0.1(2) . . . . ?
N9 N10 N11 N12 0.5(2) . . . . ?
N10 N11 N12 N8 -0.4(2) . . . . ?
N12 N8 N9 N10 0.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
