# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20240408_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2497509'
loop_
_audit_author_name
_audit_author_address
Hydroxyl-glutarimidedioxime
;Institute of Nuclear Physics and Chemistry, China Academy of Engineering Physics
China
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-14 downloaded from the CCDC.
;
_audit_creation_date             2025-06-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        Hydroxyl-glutarimidedioxime
_chemical_formula_moiety         'C5 H9 N3 O3'
_chemical_formula_sum            'C5 H9 N3 O3'
_chemical_formula_weight         159.15
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.463(2)
_cell_length_b                   4.9576(5)
_cell_length_c                   12.5387(12)
_cell_angle_alpha                90
_cell_angle_beta                 115.948(3)
_cell_angle_gamma                90
_cell_volume                     1367.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6029
_cell_measurement_temperature    298.30
_cell_measurement_theta_max      57.100
_cell_measurement_theta_min      3.496
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1476 before and 0.0850 after correction.
The Ratio of minimum to maximum transmission is 0.7823.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_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  0.0509
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7686
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.442
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_temperature      298.30
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                1269
_reflns_number_total             1374
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.060
_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)+(0.0566P)²+1.5555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1134
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C008(H008)
1.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D)
1.c Aromatic/amide H refined with riding coordinates:
 N005(H005)
1.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003)
;
_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
O001 O 0.63569(4) -0.0130(2) 0.23048(8) 0.0177(3) Uani 1 1 d . . . . .
H001 H 0.653918 -0.098916 0.200211 0.027 Uiso 1 1 calc R U . . .
O002 O 0.70104(4) 0.2661(2) 0.62964(8) 0.0171(3) Uani 1 1 d . . . . .
H002 H 0.738229 0.265601 0.656963 0.026 Uiso 1 1 calc R U . . .
O003 O 0.50438(4) -0.0114(2) 0.37167(8) 0.0191(3) Uani 1 1 d . . . . .
H003 H 0.484007 -0.110629 0.392514 0.029 Uiso 1 1 calc R U . . .
N004 N 0.67491(5) 0.1858(2) 0.30757(9) 0.0146(3) Uani 1 1 d . . . . .
N005 N 0.59411(5) 0.2375(2) 0.35958(10) 0.0156(3) Uani 1 1 d . . . . .
H005 H 0.569043 0.151319 0.298050 0.019 Uiso 1 1 calc R U . . .
N006 N 0.53260(5) 0.1912(2) 0.45941(10) 0.0168(3) Uani 1 1 d . . . . .
C007 C 0.65076(6) 0.3024(3) 0.36830(11) 0.0135(3) Uani 1 1 d . . . . .
C008 C 0.67776(6) 0.5131(3) 0.56653(12) 0.0153(3) Uani 1 1 d . . . . .
H008 H 0.698545 0.666944 0.617153 0.018 Uiso 1 1 calc R U . . .
C009 C 0.57624(6) 0.3069(3) 0.44714(11) 0.0147(3) Uani 1 1 d . . . . .
C00A C 0.61014(6) 0.5262(3) 0.53311(12) 0.0170(3) Uani 1 1 d . . . . .
H00A H 0.603896 0.508169 0.604023 0.020 Uiso 1 1 calc R U . . .
H00B H 0.594333 0.700356 0.497794 0.020 Uiso 1 1 calc R U . . .
C00B C 0.68633(6) 0.5216(3) 0.45249(12) 0.0155(3) Uani 1 1 d . . . . .
H00C H 0.673131 0.695504 0.414374 0.019 Uiso 1 1 calc R U . . .
H00D H 0.729120 0.500904 0.472209 0.019 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
O001 H001 0.8200 . ?
O001 N004 1.4195(14) . ?
O002 H002 0.8200 . ?
O002 C008 1.4338(16) . ?
O003 H003 0.8200 . ?
O003 N006 1.4252(14) . ?
N004 C007 1.2871(17) . ?
N005 H005 0.8600 . ?
N005 C007 1.3798(17) . ?
N005 C009 1.3910(16) . ?
N006 C009 1.2791(18) . ?
C007 C00B 1.4995(18) . ?
C008 H008 0.9800 . ?
C008 C00A 1.5197(19) . ?
C008 C00B 1.5338(17) . ?
C009 C00A 1.5000(19) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N004 O001 H001 109.5 . . ?
C008 O002 H002 109.5 . . ?
N006 O003 H003 109.5 . . ?
C007 N004 O001 111.47(11) . . ?
C007 N005 H005 119.0 . . ?
C007 N005 C009 122.10(12) . . ?
C009 N005 H005 119.0 . . ?
C009 N006 O003 111.79(11) . . ?
N004 C007 N005 123.61(12) . . ?
N004 C007 C00B 117.82(12) . . ?
N005 C007 C00B 118.57(11) . . ?
O002 C008 H008 109.8 . . ?
O002 C008 C00A 108.06(10) . . ?
O002 C008 C00B 110.78(10) . . ?
C00A C008 H008 109.8 . . ?
C00A C008 C00B 108.54(11) . . ?
C00B C008 H008 109.8 . . ?
N005 C009 C00A 118.73(12) . . ?
N006 C009 N005 123.43(13) . . ?
N006 C009 C00A 117.83(12) . . ?
C008 C00A H00A 109.4 . . ?
C008 C00A H00B 109.4 . . ?
C009 C00A C008 111.10(11) . . ?
C009 C00A H00A 109.4 . . ?
C009 C00A H00B 109.4 . . ?
H00A C00A H00B 108.0 . . ?
C007 C00B C008 111.26(11) . . ?
C007 C00B H00C 109.4 . . ?
C007 C00B H00D 109.4 . . ?
C008 C00B H00C 109.4 . . ?
C008 C00B H00D 109.4 . . ?
H00C C00B H00D 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
