# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20241022_zh_nlg_cly202419_0
_database_code_depnum_ccdc_archive 'CCDC 2444771'
loop_
_audit_author_name
_audit_author_address
'Luyao Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H8 N5 O, Cl O4'
_chemical_formula_sum            'C4 H8 Cl N5 O5'
_chemical_formula_weight         241.60
_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'
Cl Cl 0.1484 0.1585 '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                   7.8315(3)
_cell_length_b                   8.8391(3)
_cell_length_c                   12.7423(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.950(2)
_cell_angle_gamma                90
_cell_volume                     880.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.449
_exptl_absorpt_correction_T_max  0.2616
_exptl_absorpt_correction_T_min  0.2288
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.8746.
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    1.822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12120
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.604
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                1726
_reflns_number_total             2016
_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 (Bruker AXS LLC)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.071
_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)+(0.0416P)²+0.6393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E)
;
_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 0.9280(2) 0.3330(2) 0.71990(14) 0.0241(4) Uani 1 1 d . . . . .
H1A H 1.052443 0.323379 0.729758 0.029 Uiso 1 1 calc R U . . .
H1B H 0.879668 0.231044 0.712394 0.029 Uiso 1 1 calc R U . . .
O1 O 0.96542(17) 0.21634(15) 0.92904(10) 0.0256(3) Uani 1 1 d . . . . .
N1 N 0.8854(2) 0.42094(18) 0.62328(12) 0.0239(3) Uani 1 1 d . . . . .
H1C H 0.918653 0.369189 0.567034 0.029 Uiso 1 1 calc R U . . .
H1D H 0.939784 0.510605 0.626965 0.029 Uiso 1 1 calc R U . . .
H1E H 0.771724 0.436513 0.617059 0.029 Uiso 1 1 calc R U . . .
N2 N 0.7777(2) 0.53320(18) 0.79979(12) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.8592(2) 0.40797(19) 0.81412(13) 0.0197(4) Uani 1 1 d . . . . .
C3 C 0.8821(2) 0.3361(2) 0.91843(13) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.7114(2) 0.59535(19) 0.88586(13) 0.0289(4) Uani 1 1 d . . . . .
H3 H 0.651(4) 0.668(4) 0.876(2) 0.051(8) Uiso 1 1 d . . . . .
N4 N 0.8121(2) 0.40444(17) 1.00099(12) 0.0234(3) Uani 1 1 d . . . . .
C4 C 0.7284(2) 0.5331(2) 0.98235(15) 0.0235(4) Uani 1 1 d . . . . .
N5 N 0.6555(2) 0.6053(2) 1.06027(14) 0.0324(4) Uani 1 1 d . . . . .
H5A H 0.662717 0.568115 1.123559 0.039 Uiso 1 1 calc R U . . .
H5B H 0.600763 0.689562 1.047832 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl 0.61826(6) -0.01147(5) 0.86121(4) 0.02541(15) Uani 1 1 d . . . . .
O2 O 0.6976(3) 0.0305(2) 0.76693(13) 0.0583(6) Uani 1 1 d . . . . .
O3 O 0.4986(2) -0.13269(18) 0.83897(15) 0.0455(4) Uani 1 1 d . . . . .
O4 O 0.5341(3) 0.1151(2) 0.90109(18) 0.0648(6) Uani 1 1 d . . . . .
O5 O 0.7465(2) -0.06604(18) 0.93585(13) 0.0404(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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 N1 1.480(2) . ?
C1 C2 1.496(2) . ?
O1 C3 1.247(2) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N1 H1E 0.9000 . ?
N2 C2 1.286(2) . ?
N2 N3 1.354(2) . ?
C2 C3 1.476(2) . ?
C3 N4 1.353(2) . ?
N3 H3 0.81(3) . ?
N3 C4 1.347(2) . ?
N4 C4 1.328(2) . ?
C4 N5 1.333(2) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
Cl1 O2 1.4295(17) . ?
Cl1 O3 1.4417(16) . ?
Cl1 O4 1.4067(18) . ?
Cl1 O5 1.4308(16) . ?

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 C1 H1B 108.0 . . ?
N1 C1 H1A 109.4 . . ?
N1 C1 H1B 109.4 . . ?
N1 C1 C2 111.09(15) . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C2 N2 N3 116.25(16) . . ?
N2 C2 C1 117.64(16) . . ?
N2 C2 C3 122.34(16) . . ?
C3 C2 C1 120.00(15) . . ?
O1 C3 C2 120.12(16) . . ?
O1 C3 N4 121.68(16) . . ?
N4 C3 C2 118.20(16) . . ?
N2 N3 H3 117(2) . . ?
C4 N3 N2 123.35(17) . . ?
C4 N3 H3 120(2) . . ?
C4 N4 C3 117.34(16) . . ?
N4 C4 N3 122.51(17) . . ?
N4 C4 N5 120.19(18) . . ?
N5 C4 N3 117.30(17) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O2 Cl1 O3 109.50(11) . . ?
O2 Cl1 O5 109.02(12) . . ?
O4 Cl1 O2 109.21(13) . . ?
O4 Cl1 O3 110.50(13) . . ?
O4 Cl1 O5 110.71(12) . . ?
O5 Cl1 O3 107.87(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 O1 3.3(3) . . . . ?
C1 C2 C3 N4 -177.43(16) . . . . ?
O1 C3 N4 C4 178.73(17) . . . . ?
N1 C1 C2 N2 -0.6(2) . . . . ?
N1 C1 C2 C3 177.84(15) . . . . ?
N2 C2 C3 O1 -178.35(17) . . . . ?
N2 C2 C3 N4 1.0(3) . . . . ?
N2 N3 C4 N4 -0.1(3) . . . . ?
N2 N3 C4 N5 -179.40(18) . . . . ?
C2 N2 N3 C4 0.4(3) . . . . ?
C2 C3 N4 C4 -0.6(2) . . . . ?
C3 N4 C4 N3 0.2(3) . . . . ?
C3 N4 C4 N5 179.48(17) . . . . ?
N3 N2 C2 C1 177.58(16) . . . . ?
N3 N2 C2 C3 -0.8(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_1
_database_code_depnum_ccdc_archive 'CCDC 2444776'
loop_
_audit_author_name
_audit_author_address
'Luyao Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-10-23
_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         'C4 H8 N5 O, N O3'
_chemical_formula_sum            'C4 H8 N6 O4'
_chemical_formula_weight         204.16
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   9.9288(4)
_cell_length_b                   6.5054(3)
_cell_length_c                   24.7500(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1598.62(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    223.00
_cell_measurement_theta_max      68.256
_cell_measurement_theta_min      3.571
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  0.5210
_exptl_absorpt_correction_T_min  0.3747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0734 after correction.
The Ratio of minimum to maximum transmission is 0.7192.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9854
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.462
_diffrn_reflns_theta_min         3.572
_diffrn_ambient_temperature      223.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_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                1258
_reflns_number_total             1444
_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 (Bruker AXS LLC)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.9399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1246
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 N5(H5A,H5B,H5C)
;
_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 0.14951(14) 0.2493(3) 0.39771(6) 0.0412(4) Uani 1 1 d . . . . .
N1 N 0.38505(18) 0.2165(3) 0.55626(7) 0.0397(5) Uani 1 1 d . . . . .
H1A H 0.312327 0.198319 0.575276 0.048 Uiso 1 1 calc R U . . .
H1B H 0.463148 0.221264 0.572147 0.048 Uiso 1 1 calc R U . . .
C1 C 0.37692(18) 0.2368(3) 0.50349(8) 0.0290(5) Uani 1 1 d . . . . .
N2 N 0.25794(16) 0.2300(3) 0.47813(6) 0.0299(4) Uani 1 1 d . . . . .
C2 C 0.25669(19) 0.2526(3) 0.42405(8) 0.0292(5) Uani 1 1 d . . . . .
N3 N 0.49327(16) 0.2632(3) 0.47561(6) 0.0323(4) Uani 1 1 d . . . . .
H3 H 0.568472 0.264933 0.493651 0.039 Uiso 1 1 calc R U . . .
C3 C 0.38608(19) 0.2823(3) 0.39590(8) 0.0293(5) Uani 1 1 d . . . . .
N4 N 0.49904(16) 0.2870(3) 0.42132(6) 0.0319(4) Uani 1 1 d . . . . .
C4 C 0.3848(2) 0.3087(4) 0.33571(8) 0.0359(5) Uani 1 1 d . . . . .
H4A H 0.403525 0.176016 0.318548 0.043 Uiso 1 1 calc R U . . .
H4B H 0.294869 0.353023 0.324286 0.043 Uiso 1 1 calc R U . . .
N5 N 0.48452(17) 0.4600(3) 0.31727(6) 0.0366(5) Uani 1 1 d . . . . .
H5A H 0.462785 0.584965 0.330182 0.044 Uiso 1 1 calc R U . . .
H5B H 0.485217 0.463564 0.280918 0.044 Uiso 1 1 calc R U . . .
H5C H 0.566663 0.424046 0.329402 0.044 Uiso 1 1 calc R U . . .
O2 O 0.75464(16) 0.3764(3) 0.34260(5) 0.0456(5) Uani 1 1 d . . . . .
O3 O 0.94318(15) 0.3988(3) 0.29871(6) 0.0482(5) Uani 1 1 d . . . . .
O4 O 0.75985(16) 0.5195(3) 0.26397(5) 0.0443(4) Uani 1 1 d . . . . .
N6 N 0.81879(18) 0.4336(3) 0.30173(6) 0.0350(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 C2 1.248(2) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N1 C1 1.315(3) . ?
C1 N2 1.338(2) . ?
C1 N3 1.357(2) . ?
N2 C2 1.347(3) . ?
C2 C3 1.474(3) . ?
N3 H3 0.8700 . ?
N3 N4 1.354(2) . ?
C3 N4 1.286(2) . ?
C3 C4 1.500(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 N5 1.468(3) . ?
N5 H5A 0.9000 . ?
N5 H5B 0.9000 . ?
N5 H5C 0.9000 . ?
O2 N6 1.252(2) . ?
O3 N6 1.258(2) . ?
O4 N6 1.236(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
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N1 C1 N2 121.10(17) . . ?
N1 C1 N3 117.75(17) . . ?
N2 C1 N3 121.15(17) . . ?
C1 N2 C2 118.07(16) . . ?
O1 C2 N2 121.68(17) . . ?
O1 C2 C3 119.88(17) . . ?
N2 C2 C3 118.44(16) . . ?
C1 N3 H3 118.1 . . ?
N4 N3 C1 123.74(16) . . ?
N4 N3 H3 118.1 . . ?
C2 C3 C4 118.51(16) . . ?
N4 C3 C2 122.12(17) . . ?
N4 C3 C4 119.37(17) . . ?
C3 N4 N3 116.48(15) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
N5 C4 C3 112.33(16) . . ?
N5 C4 H4A 109.1 . . ?
N5 C4 H4B 109.1 . . ?
C4 N5 H5A 109.5 . . ?
C4 N5 H5B 109.5 . . ?
C4 N5 H5C 109.5 . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
O2 N6 O3 119.61(17) . . ?
O4 N6 O2 120.28(17) . . ?
O4 N6 O3 120.08(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
O1 C2 C3 N4 179.9(2) . . . . ?
O1 C2 C3 C4 0.2(3) . . . . ?
N1 C1 N2 C2 179.74(19) . . . . ?
N1 C1 N3 N4 -179.64(19) . . . . ?
C1 N2 C2 O1 -179.53(19) . . . . ?
C1 N2 C2 C3 0.3(3) . . . . ?
C1 N3 N4 C3 -0.4(3) . . . . ?
N2 C1 N3 N4 0.9(3) . . . . ?
N2 C2 C3 N4 0.1(3) . . . . ?
N2 C2 C3 C4 -179.65(19) . . . . ?
C2 C3 N4 N3 0.0(3) . . . . ?
C2 C3 C4 N5 142.04(19) . . . . ?
N3 C1 N2 C2 -0.8(3) . . . . ?
N4 C3 C4 N5 -37.7(3) . . . . ?
C4 C3 N4 N3 179.69(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_cu_20250214_zzh_nlg_cly_2025_1
_database_code_depnum_ccdc_archive 'CCDC 2444777'
loop_
_audit_author_name
_audit_author_address
'Luyao Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_audit_creation_date             2025-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H8 N5 O, C N3 O6'
_chemical_formula_sum            'C5 H8 N8 O7'
_chemical_formula_weight         292.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   7.3547(2)
_cell_length_b                   17.5020(4)
_cell_length_c                   8.7636(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.7340(10)
_cell_angle_gamma                90
_cell_volume                     1061.82(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8875
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      68.203
_cell_measurement_theta_min      2.525
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.807
_exptl_absorpt_coefficient_mu    1.494
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1384 before and 0.0472 after correction.
The Ratio of minimum to maximum transmission is 0.8371.
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    1.828
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_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  0.0299
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12759
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         5.054
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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                1832
_reflns_number_total             1925
_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 (Bruker AXS LLC)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0026(4)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1925
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.103
_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)+(0.0415P)²+0.5140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 O6_$1-O6
 2.86 with sigma of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3)
3.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
3.d Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 1.0541(2) 0.35098(8) 0.63281(17) 0.0233(3) Uani 1 1 d . . . . .
H1A H 1.168210 0.319455 0.644672 0.028 Uiso 1 1 calc R U . . .
H1B H 1.017701 0.376653 0.527358 0.028 Uiso 1 1 calc R U . . .
N1 N 1.10173(16) 0.40890(7) 0.76337(15) 0.0223(3) Uani 1 1 d . . . . .
H1C H 1.000630 0.440623 0.747151 0.027 Uiso 1 1 calc R U . . .
H1D H 1.205600 0.435875 0.762590 0.027 Uiso 1 1 calc R U . . .
H1E H 1.127937 0.385437 0.859807 0.027 Uiso 1 1 calc R U . . .
O1 O 0.92040(15) 0.22293(6) 0.42916(13) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.89126(18) 0.30097(7) 0.63872(16) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.80375(16) 0.31782(6) 0.73871(14) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.83702(19) 0.23548(8) 0.52813(16) 0.0182(3) Uani 1 1 d . . . . .
N3 N 0.65594(16) 0.27143(6) 0.73762(14) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.592839 0.281853 0.803039 0.023 Uiso 1 1 calc R U . . .
C4 C 0.60188(19) 0.21010(7) 0.64048(16) 0.0179(3) Uani 1 1 d . . . . .
N4 N 0.69234(16) 0.18989(6) 0.53793(13) 0.0191(3) Uani 1 1 d . . . . .
N5 N 0.45358(18) 0.16882(7) 0.64907(15) 0.0270(3) Uani 1 1 d . . . . .
H5A H 0.415784 0.128731 0.587837 0.032 Uiso 1 1 calc R U . . .
H5B H 0.394475 0.181947 0.715916 0.032 Uiso 1 1 calc R U . . .
O2 O 0.66946(16) 0.44961(6) 0.17473(15) 0.0341(3) Uani 1 1 d . . . . .
O3 O 0.63695(17) 0.35502(6) 0.32294(15) 0.0361(3) Uani 1 1 d . . . . .
O4 O 0.36421(17) 0.37045(7) 0.44893(15) 0.0381(3) Uani 1 1 d . . . . .
C5 C 0.4271(2) 0.45468(8) 0.27593(17) 0.0225(3) Uani 1 1 d . . . . .
O5 O 0.21627(17) 0.48046(6) 0.40490(14) 0.0337(3) Uani 1 1 d . . . . .
N6 N 0.58457(17) 0.41775(7) 0.25914(14) 0.0223(3) Uani 1 1 d . . . . .
O6 O 0.19086(8) 0.52339(6) 0.09319(11) 0.0277(3) Uani 1 1 d D . . . .
N7 N 0.33125(17) 0.43289(7) 0.38055(15) 0.0240(3) Uani 1 1 d . . . . .
O7 O 0.47008(15) 0.57548(6) 0.19040(15) 0.0330(3) Uani 1 1 d . . . . .
N8 N 0.35877(16) 0.52265(6) 0.18047(14) 0.0202(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 N1 1.4795(18) . ?
C1 C2 1.4985(18) . ?
N1 H1C 0.9000 . ?
N1 H1D 0.9000 . ?
N1 H1E 0.9000 . ?
O1 C3 1.2393(17) . ?
C2 N2 1.2845(18) . ?
C2 C3 1.4667(19) . ?
N2 N3 1.3543(15) . ?
C3 N4 1.3558(18) . ?
N3 H3 0.8700 . ?
N3 C4 1.3441(18) . ?
C4 N4 1.3339(18) . ?
C4 N5 1.3313(18) . ?
N5 H5A 0.8700 . ?
N5 H5B 0.8700 . ?
O2 N6 1.2489(16) . ?
O3 N6 1.2331(16) . ?
O4 N7 1.2304(17) . ?
C5 N6 1.3771(18) . ?
C5 N7 1.3854(18) . ?
C5 N8 1.4434(18) . ?
O5 N7 1.2553(16) . ?
O6 N8 1.2134(13) . ?
O7 N8 1.2185(15) . ?

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 C1 H1B 108.0 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 C2 110.90(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1D 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
N2 C2 C1 118.68(12) . . ?
N2 C2 C3 122.89(12) . . ?
C3 C2 C1 118.42(12) . . ?
C2 N2 N3 116.33(11) . . ?
O1 C3 C2 120.83(12) . . ?
O1 C3 N4 121.63(13) . . ?
N4 C3 C2 117.53(11) . . ?
N2 N3 H3 118.4 . . ?
C4 N3 N2 123.25(11) . . ?
C4 N3 H3 118.4 . . ?
N4 C4 N3 122.03(12) . . ?
N5 C4 N3 118.05(12) . . ?
N5 C4 N4 119.92(12) . . ?
C4 N4 C3 117.86(11) . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N6 C5 N7 125.15(12) . . ?
N6 C5 N8 117.75(12) . . ?
N7 C5 N8 117.08(12) . . ?
O2 N6 C5 117.41(11) . . ?
O3 N6 O2 121.60(12) . . ?
O3 N6 C5 120.98(12) . . ?
O4 N7 C5 120.42(12) . . ?
O4 N7 O5 122.65(12) . . ?
O5 N7 C5 116.89(12) . . ?
O6 N8 C5 117.07(11) . . ?
O6 N8 O7 123.58(12) . . ?
O7 N8 C5 119.35(12) . . ?

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 N3 179.10(11) . . . . ?
C1 C2 C3 O1 -1.89(19) . . . . ?
C1 C2 C3 N4 178.50(11) . . . . ?
N1 C1 C2 N2 6.77(17) . . . . ?
N1 C1 C2 C3 -174.10(11) . . . . ?
O1 C3 N4 C4 -175.81(12) . . . . ?
C2 N2 N3 C4 0.92(19) . . . . ?
C2 C3 N4 C4 3.80(18) . . . . ?
N2 C2 C3 O1 177.20(13) . . . . ?
N2 C2 C3 N4 -2.42(19) . . . . ?
N2 N3 C4 N4 0.6(2) . . . . ?
N2 N3 C4 N5 -179.60(12) . . . . ?
C3 C2 N2 N3 0.02(19) . . . . ?
N3 C4 N4 C3 -3.08(19) . . . . ?
N5 C4 N4 C3 177.15(12) . . . . ?
N6 C5 N7 O4 -11.5(2) . . . . ?
N6 C5 N7 O5 166.26(13) . . . . ?
N6 C5 N8 O6 123.90(14) . . . . ?
N6 C5 N8 O7 -55.82(18) . . . . ?
N7 C5 N6 O2 -171.37(13) . . . . ?
N7 C5 N6 O3 9.9(2) . . . . ?
N7 C5 N8 O6 -57.67(17) . . . . ?
N7 C5 N8 O7 122.61(14) . . . . ?
N8 C5 N6 O2 6.92(19) . . . . ?
N8 C5 N6 O3 -171.85(12) . . . . ?
N8 C5 N7 O4 170.15(12) . . . . ?
N8 C5 N7 O5 -12.04(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_cly2024_28_0m
_database_code_depnum_ccdc_archive 'CCDC 2444772'
loop_
_audit_author_name
_audit_author_address
'Luyao Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-06-16 deposited with the CCDC.	2025-06-18 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_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         'C4 H8 N5 O, C2 H3 O2'
_chemical_formula_sum            'C6 H11 N5 O3'
_chemical_formula_weight         201.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.5773(8)
_cell_length_b                   6.4537(5)
_cell_length_c                   12.6350(9)
_cell_angle_alpha                90
_cell_angle_beta                 117.101(2)
_cell_angle_gamma                90
_cell_volume                     840.39(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1160
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      24.941
_cell_measurement_theta_min      3.640
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_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  0.0781
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9437
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         1.981
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1352
_reflns_number_total             1944
_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 (Bruker AXS LLC)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.039
_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)+(0.0639P)²+0.8410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_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 0.10661(15) 0.1645(3) 0.21223(15) 0.0260(4) Uani 1 1 d . . . . .
N1 N 0.34404(18) 0.3585(3) 0.54162(17) 0.0216(5) Uani 1 1 d . . . . .
H1A H 0.328662 0.479011 0.499933 0.026 Uiso 1 1 calc R U . . .
H1B H 0.431143 0.338351 0.583736 0.026 Uiso 1 1 calc R U . . .
H1C H 0.308314 0.365675 0.592464 0.026 Uiso 1 1 calc R U . . .
N2 N 0.44635(19) 0.1922(3) 0.38786(18) 0.0215(5) Uani 1 1 d . . . . .
N3 N 0.47791(18) 0.1923(3) 0.29697(17) 0.0206(5) Uani 1 1 d . . . . .
H3 H 0.560439 0.197554 0.313752 0.025 Uiso 1 1 calc R U . . .
N4 N 0.26119(18) 0.1719(3) 0.14850(17) 0.0191(4) Uani 1 1 d . . . . .
N5 N 0.42905(19) 0.1873(3) 0.09961(19) 0.0247(5) Uani 1 1 d . . . . .
H5A H 0.372420 0.180765 0.023947 0.030 Uiso 1 1 calc R U . . .
H5B H 0.512507 0.195564 0.120351 0.030 Uiso 1 1 calc R U . . .
C1 C 0.2853(2) 0.1831(4) 0.4578(2) 0.0241(5) Uani 1 1 d . . . . .
H1D H 0.189557 0.191631 0.423115 0.029 Uiso 1 1 calc R U . . .
H1E H 0.313004 0.050779 0.501971 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3243(2) 0.1851(4) 0.3596(2) 0.0193(5) Uani 1 1 d . . . . .
C3 C 0.2227(2) 0.1735(4) 0.2346(2) 0.0178(5) Uani 1 1 d . . . . .
C4 C 0.3887(2) 0.1846(4) 0.1823(2) 0.0186(5) Uani 1 1 d . . . . .
O2 O 0.73037(16) 0.2294(3) 0.36390(15) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.70697(17) 0.1950(3) 0.17938(15) 0.0262(4) Uani 1 1 d . . . . .
C5 C 0.7750(2) 0.2065(4) 0.2897(2) 0.0212(5) Uani 1 1 d . . . . .
C6 C 0.9202(2) 0.1903(5) 0.3393(3) 0.0334(7) Uani 1 1 d . . . . .
H6A H 0.957199 0.329078 0.345821 0.050 Uiso 1 1 calc R U . . .
H6B H 0.941312 0.105330 0.286149 0.050 Uiso 1 1 calc R U . . .
H6C H 0.956557 0.125847 0.418123 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.243(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.486(3) . ?
N2 N3 1.355(3) . ?
N2 C2 1.291(3) . ?
N3 H3 0.8800 . ?
N3 C4 1.344(3) . ?
N4 C3 1.350(3) . ?
N4 C4 1.339(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C4 1.325(3) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C1 C2 1.502(3) . ?
C2 C3 1.480(3) . ?
O2 C5 1.268(3) . ?
O3 C5 1.252(3) . ?
C5 C6 1.507(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C2 N2 N3 116.7(2) . . ?
N2 N3 H3 118.6 . . ?
C4 N3 N2 122.85(19) . . ?
C4 N3 H3 118.6 . . ?
C4 N4 C3 117.6(2) . . ?
H5A N5 H5B 120.0 . . ?
C4 N5 H5A 120.0 . . ?
C4 N5 H5B 120.0 . . ?
N1 C1 H1D 109.3 . . ?
N1 C1 H1E 109.3 . . ?
N1 C1 C2 111.68(19) . . ?
H1D C1 H1E 107.9 . . ?
C2 C1 H1D 109.3 . . ?
C2 C1 H1E 109.3 . . ?
N2 C2 C1 118.4(2) . . ?
N2 C2 C3 122.3(2) . . ?
C3 C2 C1 119.3(2) . . ?
O1 C3 N4 122.4(2) . . ?
O1 C3 C2 119.7(2) . . ?
N4 C3 C2 117.85(19) . . ?
N4 C4 N3 122.7(2) . . ?
N5 C4 N3 118.4(2) . . ?
N5 C4 N4 118.9(2) . . ?
O2 C5 C6 117.0(2) . . ?
O3 C5 O2 124.6(2) . . ?
O3 C5 C6 118.4(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
N1 C1 C2 N2 53.4(3) . . . . ?
N1 C1 C2 C3 -128.2(2) . . . . ?
N2 N3 C4 N4 -1.4(4) . . . . ?
N2 N3 C4 N5 179.4(2) . . . . ?
N2 C2 C3 O1 179.1(2) . . . . ?
N2 C2 C3 N4 -0.5(4) . . . . ?
N3 N2 C2 C1 179.5(2) . . . . ?
N3 N2 C2 C3 1.1(3) . . . . ?
C1 C2 C3 O1 0.8(3) . . . . ?
C1 C2 C3 N4 -178.8(2) . . . . ?
C2 N2 N3 C4 -0.3(3) . . . . ?
C3 N4 C4 N3 2.1(3) . . . . ?
C3 N4 C4 N5 -178.7(2) . . . . ?
C4 N4 C3 O1 179.3(2) . . . . ?
C4 N4 C3 C2 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
