# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_20230901001_0m
_database_code_depnum_ccdc_archive 'CCDC 2331157'
loop_
_audit_author_name
_audit_author_address
'Qi Wu'
;Wuhan Textile University
China
;
_audit_update_record             
;
2024-02-06 deposited with the CCDC.	2024-08-25 downloaded from the CCDC.
;
_audit_creation_date             2024-02-06
_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        ?
_chemical_formula_moiety         'C3 H5 N5 O3 Zn'
_chemical_formula_sum            'C3 H5 N5 O3 Zn'
_chemical_formula_weight         224.49
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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           9
_space_group_name_H-M_alt        'C 1 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'

_cell_length_a                   9.4696(5)
_cell_length_b                   9.4104(4)
_cell_length_c                   7.9944(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.333(2)
_cell_angle_gamma                90
_cell_volume                     654.14(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4516
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      4.33
_shelx_estimated_absorpt_T_max   0.707
_shelx_estimated_absorpt_T_min   0.685
_exptl_absorpt_coefficient_mu    3.726
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic whiteish colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.279
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4648
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         4.331
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                1394
_reflns_number_total             1404
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.077(17)
_refine_ls_extinction_coef       0.022(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   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1404
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0175
_refine_ls_R_factor_gt           0.0174
_refine_ls_restrained_S_all      1.061
_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)+0.3497P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0469
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.923(17)
 0.077(17)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2)
;
_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
Zn1 Zn 0.23278(5) 0.58885(3) 0.48015(5) 0.01653(17) Uani 1 1 d . . . . .
O3 O 0.4191(3) 0.8121(3) 0.7513(4) 0.0263(6) Uani 1 1 d . . . . .
O1 O 0.4993(4) 0.3705(3) 0.5875(4) 0.0311(7) Uani 1 1 d . . . . .
N4 N 0.1787(4) 0.4054(3) 0.3285(4) 0.0173(6) Uani 1 1 d . . . . .
H4A H 0.265596 0.357778 0.351619 0.021 Uiso 1 1 calc R U . . .
H4B H 0.120569 0.352240 0.368303 0.021 Uiso 1 1 calc R U . . .
N2 N 0.7014(3) 0.5163(3) 0.7306(5) 0.0264(7) Uani 1 1 d . . . . .
H2 H 0.763661 0.450155 0.729541 0.032 Uiso 1 1 calc R U . . .
N3 N 0.6632(3) 0.7452(3) 0.8149(4) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.4498(3) 0.5939(3) 0.6537(4) 0.0182(6) Uani 1 1 d . . . . .
O2 O 0.9026(3) 0.6615(3) 0.8699(4) 0.0324(7) Uani 1 1 d . . . . .
N5 N 0.0992(3) 0.4186(3) 0.1316(4) 0.0174(6) Uani 1 1 d . . . . .
H5A H 0.048238 0.500580 0.107761 0.021 Uiso 1 1 calc R U . . .
H5B H 0.029711 0.349340 0.092652 0.021 Uiso 1 1 calc R U . . .
C1 C 0.5466(4) 0.4875(4) 0.6542(5) 0.0192(7) Uani 1 1 d . . . . .
C3 C 0.5084(4) 0.7191(3) 0.7392(5) 0.0153(7) Uani 1 1 d . . . . .
C2 C 0.7631(4) 0.6439(4) 0.8084(5) 0.0203(7) 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
Zn1 N4 2.055(3) . ?
Zn1 N3 1.982(3) 4_464 ?
Zn1 N1 1.973(3) . ?
Zn1 N5 2.070(3) 2_565 ?
O3 C3 1.247(5) . ?
O1 C1 1.228(4) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 N5 1.457(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.374(4) . ?
N2 C2 1.372(5) . ?
N3 C3 1.368(4) . ?
N3 C2 1.358(4) . ?
N1 C1 1.357(4) . ?
N1 C3 1.365(4) . ?
O2 C2 1.225(4) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?

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 Zn1 N5 104.44(12) . 2_565 ?
N3 Zn1 N4 109.25(13) 4_464 . ?
N3 Zn1 N5 107.30(11) 4_464 2_565 ?
N1 Zn1 N4 112.48(11) . . ?
N1 Zn1 N3 115.38(11) . 4_464 ?
N1 Zn1 N5 107.27(13) . 2_565 ?
Zn1 N4 H4A 107.8 . . ?
Zn1 N4 H4B 107.8 . . ?
H4A N4 H4B 107.2 . . ?
N5 N4 Zn1 117.86(18) . . ?
N5 N4 H4A 107.8 . . ?
N5 N4 H4B 107.8 . . ?
C1 N2 H2 117.9 . . ?
C2 N2 H2 117.9 . . ?
C2 N2 C1 124.2(3) . . ?
C3 N3 Zn1 116.8(2) . 4_565 ?
C2 N3 Zn1 121.7(2) . 4_565 ?
C2 N3 C3 119.8(3) . . ?
C1 N1 Zn1 119.9(2) . . ?
C1 N1 C3 119.7(3) . . ?
C3 N1 Zn1 118.5(2) . . ?
Zn1 N5 H5A 108.0 2_564 . ?
Zn1 N5 H5B 108.0 2_564 . ?
N4 N5 Zn1 117.1(2) . 2_564 ?
N4 N5 H5A 108.0 . . ?
N4 N5 H5B 108.0 . . ?
H5A N5 H5B 107.3 . . ?
O1 C1 N2 120.8(3) . . ?
O1 C1 N1 122.1(3) . . ?
N1 C1 N2 117.2(3) . . ?
O3 C3 N3 118.7(3) . . ?
O3 C3 N1 119.4(3) . . ?
N1 C3 N3 121.9(3) . . ?
N3 C2 N2 117.0(3) . . ?
O2 C2 N2 119.9(3) . . ?
O2 C2 N3 123.1(3) . . ?

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
Zn1 N4 N5 Zn1 96.8(2) . . . 2_564 ?
Zn1 N3 C3 O3 12.3(4) 4_565 . . . ?
Zn1 N3 C3 N1 -166.7(3) 4_565 . . . ?
Zn1 N3 C2 N2 162.5(3) 4_565 . . . ?
Zn1 N3 C2 O2 -16.7(5) 4_565 . . . ?
Zn1 N1 C1 O1 -19.9(5) . . . . ?
Zn1 N1 C1 N2 159.2(3) . . . . ?
Zn1 N1 C3 O3 21.7(5) . . . . ?
Zn1 N1 C3 N3 -159.4(3) . . . . ?
C1 N2 C2 N3 2.4(6) . . . . ?
C1 N2 C2 O2 -178.4(4) . . . . ?
C1 N1 C3 O3 -174.1(4) . . . . ?
C1 N1 C3 N3 4.8(5) . . . . ?
C3 N3 C2 N2 -2.5(5) . . . . ?
C3 N3 C2 O2 178.3(4) . . . . ?
C3 N1 C1 O1 176.1(4) . . . . ?
C3 N1 C1 N2 -4.8(5) . . . . ?
C2 N2 C1 O1 -179.7(4) . . . . ?
C2 N2 C1 N1 1.3(6) . . . . ?
C2 N3 C3 O3 178.0(3) . . . . ?
C2 N3 C3 N1 -1.0(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.923(17)
2 0.077(17)

