# 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. 
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data_cu_20250409_zzh_nlg_qa_gm_0m
_database_code_depnum_ccdc_archive 'CCDC 2445937'
loop_
_audit_author_name
_audit_author_address
'Lei Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-04-23 deposited with the CCDC.	2025-07-07 downloaded from the CCDC.
;
_audit_creation_date             2025-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H24 O6, N5, H4 N O'
_chemical_formula_sum            'C12 H28 N6 O7'
_chemical_formula_weight         368.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           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                   8.7794(3)
_cell_length_b                   10.2396(4)
_cell_length_c                   20.7518(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1865.54(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4142
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      66.73
_cell_measurement_theta_min      4.26
_shelx_estimated_absorpt_T_max   0.906
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0983 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.8875.
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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.281
_diffrn_reflns_theta_min         4.261
_diffrn_ambient_temperature      193.00
_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           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         0.728
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2853
_reflns_number_total             3413
_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         0.285
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1041 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.043
_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)+(0.0592P)²+0.2269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.b Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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 0.4635(4) 0.8068(3) 0.68838(16) 0.0477(8) Uani 1 1 d . . . . .
H1A H 0.570052 0.776293 0.692376 0.057 Uiso 1 1 calc R U . . .
H1B H 0.433064 0.847708 0.729643 0.057 Uiso 1 1 calc R U . . .
O1 O 0.3658(3) 0.6995(2) 0.67418(10) 0.0442(5) Uani 1 1 d . . . . .
C2 C 0.4506(4) 0.9031(3) 0.63498(16) 0.0454(8) Uani 1 1 d . . . . .
H2A H 0.342800 0.928588 0.628877 0.055 Uiso 1 1 calc R U . . .
H2B H 0.510015 0.982565 0.645395 0.055 Uiso 1 1 calc R U . . .
O2 O 0.5080(2) 0.84451(18) 0.57764(10) 0.0417(5) Uani 1 1 d . . . . .
C3 C 0.4902(5) 0.9275(3) 0.52316(18) 0.0532(9) Uani 1 1 d . . . . .
H3A H 0.543809 1.011171 0.530653 0.064 Uiso 1 1 calc R U . . .
H3B H 0.380841 0.946504 0.516220 0.064 Uiso 1 1 calc R U . . .
O3 O 0.4588(3) 0.7537(2) 0.45008(10) 0.0462(5) Uani 1 1 d . . . . .
C4 C 0.5545(5) 0.8614(3) 0.46534(17) 0.0597(10) Uani 1 1 d . . . . .
H4A H 0.558522 0.922984 0.428623 0.072 Uiso 1 1 calc R U . . .
H4B H 0.659194 0.830529 0.474408 0.072 Uiso 1 1 calc R U . . .
O4 O 0.4192(3) 0.4851(2) 0.43074(10) 0.0462(5) Uani 1 1 d . . . . .
C5 C 0.5038(4) 0.6906(4) 0.39232(16) 0.0541(9) Uani 1 1 d . . . . .
H5A H 0.610269 0.659726 0.396240 0.065 Uiso 1 1 calc R U . . .
H5B H 0.498369 0.752756 0.355869 0.065 Uiso 1 1 calc R U . . .
O5 O 0.2881(3) 0.33083(19) 0.52734(11) 0.0460(6) Uani 1 1 d . . . . .
C6 C 0.4015(4) 0.5782(3) 0.38006(14) 0.0479(8) Uani 1 1 d . . . . .
H6A H 0.294406 0.608374 0.378251 0.057 Uiso 1 1 calc R U . . .
H6B H 0.427093 0.537476 0.338179 0.057 Uiso 1 1 calc R U . . .
O6 O 0.3149(3) 0.4314(2) 0.65520(11) 0.0469(6) Uani 1 1 d . . . . .
C7 C 0.3492(4) 0.3635(3) 0.41708(17) 0.0505(8) Uani 1 1 d . . . . .
H7A H 0.397251 0.323488 0.378714 0.061 Uiso 1 1 calc R U . . .
H7B H 0.239695 0.376904 0.407705 0.061 Uiso 1 1 calc R U . . .
C8 C 0.3667(4) 0.2751(3) 0.47381(18) 0.0518(8) Uani 1 1 d . . . . .
H8A H 0.323976 0.188018 0.463757 0.062 Uiso 1 1 calc R U . . .
H8B H 0.475994 0.264481 0.484334 0.062 Uiso 1 1 calc R U . . .
C9 C 0.2977(4) 0.2520(3) 0.58333(19) 0.0546(9) Uani 1 1 d . . . . .
H9A H 0.405797 0.234164 0.593644 0.065 Uiso 1 1 calc R U . . .
H9B H 0.245986 0.167472 0.575658 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2241(5) 0.3209(3) 0.63811(18) 0.0543(9) Uani 1 1 d . . . . .
H10A H 0.120625 0.349746 0.625625 0.065 Uiso 1 1 calc R U . . .
H10B H 0.214925 0.261155 0.675421 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2505(5) 0.5026(3) 0.70762(15) 0.0513(8) Uani 1 1 d . . . . .
H11A H 0.234073 0.443381 0.744696 0.062 Uiso 1 1 calc R U . . .
H11B H 0.150618 0.539052 0.694706 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3551(5) 0.6106(3) 0.72670(15) 0.0524(9) Uani 1 1 d . . . . .
H12A H 0.315006 0.655897 0.765279 0.063 Uiso 1 1 calc R U . . .
H12B H 0.457053 0.575145 0.737172 0.063 Uiso 1 1 calc R U . . .
N1 N 0.7588(4) 0.5132(4) 0.66964(17) 0.0673(9) Uani 1 1 d . . . . .
N2 N 0.8217(4) 0.4059(3) 0.68338(19) 0.0722(10) Uani 1 1 d . . . . .
N3 N 0.8786(5) 0.4162(4) 0.74280(18) 0.0747(10) Uani 1 1 d . . . . .
N4 N 0.8441(4) 0.5333(3) 0.76345(16) 0.0657(9) Uani 1 1 d . . . . .
N5 N 0.7735(5) 0.5916(4) 0.7196(2) 0.0804(11) Uani 1 1 d . . . . .
N6 N 0.4837(3) 0.5644(3) 0.55751(13) 0.0373(6) Uani 1 1 d . . . . .
O7 O 0.6296(3) 0.5111(3) 0.55365(12) 0.0656(7) Uani 1 1 d . . . . .
H7 H 0.671432 0.514605 0.590011 0.098 Uiso 1 1 calc R U . . .
H6C H 0.414(5) 0.527(4) 0.591(2) 0.068(12) Uiso 1 1 d . . . . .
H6D H 0.488(4) 0.646(4) 0.5664(17) 0.051(10) Uiso 1 1 d . . . . .
H6E H 0.442(5) 0.536(4) 0.518(2) 0.071(12) 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 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 O1 1.424(4) . ?
C1 C2 1.488(5) . ?
O1 C12 1.423(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 O2 1.425(4) . ?
O2 C3 1.423(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.489(5) . ?
O3 C4 1.422(4) . ?
O3 C5 1.418(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O4 C6 1.428(4) . ?
O4 C7 1.417(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.482(5) . ?
O5 C8 1.427(4) . ?
O5 C9 1.417(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O6 C10 1.429(4) . ?
O6 C11 1.426(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.493(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.486(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.491(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N1 N2 1.262(5) . ?
N1 N5 1.317(5) . ?
N2 N3 1.335(5) . ?
N3 N4 1.309(5) . ?
N4 N5 1.252(5) . ?
N6 O7 1.394(4) . ?
N6 H6C 0.99(4) . ?
N6 H6D 0.85(4) . ?
N6 H6E 0.94(5) . ?
O7 H7 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.4 . . ?
O1 C1 H1A 110.1 . . ?
O1 C1 H1B 110.1 . . ?
O1 C1 C2 108.2(3) . . ?
C2 C1 H1A 110.1 . . ?
C2 C1 H1B 110.1 . . ?
C12 O1 C1 112.0(3) . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O2 C2 C1 108.4(2) . . ?
O2 C2 H2A 110.0 . . ?
O2 C2 H2B 110.0 . . ?
C3 O2 C2 111.9(2) . . ?
O2 C3 H3A 109.9 . . ?
O2 C3 H3B 109.9 . . ?
O2 C3 C4 109.1(3) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C5 O3 C4 112.2(3) . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
O3 C4 C3 107.9(3) . . ?
O3 C4 H4A 110.1 . . ?
O3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C7 O4 C6 113.1(2) . . ?
O3 C5 H5A 109.8 . . ?
O3 C5 H5B 109.8 . . ?
O3 C5 C6 109.3(3) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C9 O5 C8 112.5(2) . . ?
O4 C6 C5 109.0(3) . . ?
O4 C6 H6A 109.9 . . ?
O4 C6 H6B 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C11 O6 C10 111.9(3) . . ?
O4 C7 H7A 109.8 . . ?
O4 C7 H7B 109.8 . . ?
O4 C7 C8 109.3(3) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
O5 C8 C7 108.8(3) . . ?
O5 C8 H8A 109.9 . . ?
O5 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
O5 C9 H9A 109.8 . . ?
O5 C9 H9B 109.8 . . ?
O5 C9 C10 109.3(3) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
O6 C10 C9 108.9(3) . . ?
O6 C10 H10A 109.9 . . ?
O6 C10 H10B 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
O6 C11 H11A 109.7 . . ?
O6 C11 H11B 109.7 . . ?
O6 C11 C12 109.7(3) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
O1 C12 C11 108.2(3) . . ?
O1 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N2 N1 N5 108.1(3) . . ?
N1 N2 N3 107.7(3) . . ?
N4 N3 N2 106.7(3) . . ?
N5 N4 N3 108.2(3) . . ?
N4 N5 N1 109.3(3) . . ?
O7 N6 H6C 117(2) . . ?
O7 N6 H6D 111(2) . . ?
O7 N6 H6E 101(3) . . ?
H6C N6 H6D 105(3) . . ?
H6C N6 H6E 104(3) . . ?
H6D N6 H6E 120(4) . . ?
N6 O7 H7 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
C1 O1 C12 C11 179.7(3) . . . . ?
C1 C2 O2 C3 176.0(3) . . . . ?
O1 C1 C2 O2 -64.8(3) . . . . ?
C2 C1 O1 C12 -172.1(3) . . . . ?
C2 O2 C3 C4 179.1(3) . . . . ?
O2 C3 C4 O3 69.0(4) . . . . ?
O3 C5 C6 O4 -63.7(4) . . . . ?
C4 O3 C5 C6 178.9(3) . . . . ?
O4 C7 C8 O5 63.2(4) . . . . ?
C5 O3 C4 C3 175.2(3) . . . . ?
O5 C9 C10 O6 -68.9(4) . . . . ?
C6 O4 C7 C8 -177.1(3) . . . . ?
O6 C11 C12 O1 64.3(4) . . . . ?
C7 O4 C6 C5 -168.4(3) . . . . ?
C8 O5 C9 C10 175.6(3) . . . . ?
C9 O5 C8 C7 179.3(3) . . . . ?
C10 O6 C11 C12 175.8(3) . . . . ?
C11 O6 C10 C9 179.9(3) . . . . ?
N1 N2 N3 N4 1.0(5) . . . . ?
N2 N1 N5 N4 -0.1(5) . . . . ?
N2 N3 N4 N5 -1.1(5) . . . . ?
N3 N4 N5 N1 0.8(5) . . . . ?
N5 N1 N2 N3 -0.6(5) . . . . ?

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

data_mo_20250407_ys_nlg_qa_aeo_0m
_database_code_depnum_ccdc_archive 'CCDC 2445981'
loop_
_audit_author_name
_audit_author_address
'Lei Chen'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2025-04-23 deposited with the CCDC.	2025-07-07 downloaded from the CCDC.
;
_audit_creation_date             2025-04-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'H4 N O, N5'
_chemical_formula_sum            'H4 N6 O'
_chemical_formula_weight         104.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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                   3.7631(2)
_cell_length_b                   14.7655(7)
_cell_length_c                   7.6847(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.582(2)
_cell_angle_gamma                90
_cell_volume                     424.18(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2755
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1189 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.9453.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10009
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.759
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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                821
_reflns_number_total             968
_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         0.158
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.077
_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)+(0.0412P)²+0.0754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All O(H) groups
2.a Rotating group:
 O1(H1), N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   difmap
_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 -0.0906(2) 0.60107(6) 0.38840(10) 0.0297(2) Uani 1 1 d . . . . .
H1 H 0.032908 0.611800 0.490780 0.036 Uiso 1 1 d R U . . .
N6 N 0.1357(2) 0.60810(6) 0.25519(12) 0.0229(2) Uani 1 1 d . . . . .
H6A H 0.304988 0.566130 0.269507 0.028 Uiso 1 1 d R U . . .
H6B H 0.010872 0.600480 0.151197 0.028 Uiso 1 1 d R U . . .
N5 N 0.3478(3) 0.70541(6) 0.79426(13) 0.0291(2) Uani 1 1 d . . . . .
N1 N 0.3388(2) 0.63266(6) 0.69462(12) 0.0258(2) Uani 1 1 d . . . . .
N2 N 0.5217(2) 0.56847(6) 0.78284(12) 0.0273(2) Uani 1 1 d . . . . .
N4 N 0.5360(3) 0.68647(7) 0.94435(12) 0.0310(3) Uani 1 1 d . . . . .
N3 N 0.6435(3) 0.60186(6) 0.93715(13) 0.0280(2) Uani 1 1 d . . . . .
H6C H 0.222(4) 0.6675(11) 0.254(2) 0.041(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8811 . ?
O1 N6 1.4085(12) . ?
N6 H6A 0.8866 . ?
N6 H6B 0.8865 . ?
N6 H6C 0.936(16) . ?
N5 N1 1.3173(13) . ?
N5 N4 1.3125(14) . ?
N1 N2 1.3133(13) . ?
N2 N3 1.3172(13) . ?
N4 N3 1.3163(14) . ?

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
N6 O1 H1 109.6 . . ?
O1 N6 H6A 110.1 . . ?
O1 N6 H6B 110.1 . . ?
O1 N6 H6C 108.6(10) . . ?
H6A N6 H6B 108.8 . . ?
H6A N6 H6C 114.2 . . ?
H6B N6 H6C 104.8 . . ?
N4 N5 N1 108.20(9) . . ?
N2 N1 N5 108.15(9) . . ?
N1 N2 N3 107.59(9) . . ?
N5 N4 N3 107.63(9) . . ?
N4 N3 N2 108.43(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
N5 N1 N2 N3 -0.01(12) . . . . ?
N5 N4 N3 N2 -0.06(13) . . . . ?
N1 N5 N4 N3 0.05(13) . . . . ?
N1 N2 N3 N4 0.05(12) . . . . ?
N4 N5 N1 N2 -0.02(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
