# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lrn25111601_0m
_database_code_depnum_ccdc_archive 'CCDC 2521794'
loop_
_audit_author_name
_audit_author_address
b
;yangzhou university
China
;
_audit_update_record             
;
2026-01-11 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Zn, C4 H13 N5'
_chemical_formula_sum            'C4 H13 Cl4 N5 Zn'
_chemical_formula_weight         338.36
_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'
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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.8052(6)
_cell_length_b                   6.9176(5)
_cell_length_c                   14.1930(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.816(3)
_cell_angle_gamma                90
_cell_volume                     660.25(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7892
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.643
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5714
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.7664.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10700
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.029
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2844
_reflns_number_total             3020
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.221
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.027(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3020
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0231
_refine_ls_restrained_S_all      1.030
_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)+(0.0149P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0484
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.973(12)
 0.027(12)
2. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 C4(H4C,H4D,H4E), C3(H3A,H3B,H3C)
;
_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 -0.27755(4) 0.61747(5) 0.20432(2) 0.02792(10) Uani 1 1 d . . . . .
Cl4 Cl -0.48191(10) 0.47055(12) 0.08567(5) 0.03511(18) Uani 1 1 d . . . . .
Cl2 Cl 0.01911(10) 0.64055(12) 0.14937(5) 0.03352(17) Uani 1 1 d . . . . .
Cl3 Cl -0.22661(11) 0.43280(12) 0.33919(5) 0.03718(19) Uani 1 1 d . . . . .
Cl1 Cl -0.39151(11) 0.91325(12) 0.24121(7) 0.0440(2) Uani 1 1 d . . . . .
N1 N -0.1355(3) 0.1295(5) 0.06664(17) 0.0400(6) Uani 1 1 d . . . . .
H1A H -0.142136 0.123674 0.005711 0.048 Uiso 1 1 calc R U . . .
H1B H -0.241928 0.146175 0.091431 0.048 Uiso 1 1 calc R U . . .
N2 N 0.2007(4) 0.0876(5) 0.08804(17) 0.0375(7) Uani 1 1 d . . . . .
H2A H 0.199879 0.081076 0.027466 0.045 Uiso 1 1 calc R U . . .
H2B H 0.310998 0.077285 0.126401 0.045 Uiso 1 1 calc R U . . .
N3 N 0.0357(3) 0.1193(4) 0.21827(14) 0.0275(5) Uani 1 1 d . . . . .
H3 H -0.071938 0.084990 0.238493 0.033 Uiso 1 1 calc R U . . .
N5 N 0.2143(4) 0.0930(5) 0.37035(17) 0.0373(6) Uani 1 1 d . . . . .
N4 N 0.3105(4) 0.3112(4) 0.26458(18) 0.0333(6) Uani 1 1 d . . . . .
H4A H 0.406922 0.349827 0.306757 0.040 Uiso 1 1 calc R U . . .
H4B H 0.292522 0.362342 0.208688 0.040 Uiso 1 1 calc R U . . .
C1 C 0.0359(4) 0.1129(5) 0.12147(18) 0.0271(6) Uani 1 1 d . . . . .
C2 C 0.1919(4) 0.1754(4) 0.2853(2) 0.0253(6) Uani 1 1 d . . . . .
C4 C 0.3565(6) 0.1756(7) 0.4476(2) 0.0700(15) Uani 1 1 d . . . . .
H4C H 0.488586 0.135013 0.440844 0.105 Uiso 1 1 calc R U . . .
H4D H 0.325544 0.131824 0.507792 0.105 Uiso 1 1 calc R U . . .
H4E H 0.348876 0.314067 0.444792 0.105 Uiso 1 1 calc R U . . .
C3 C 0.1133(7) -0.0864(7) 0.3897(3) 0.0820(17) Uani 1 1 d . . . . .
H3A H -0.027051 -0.063177 0.384487 0.123 Uiso 1 1 calc R U . . .
H3B H 0.163628 -0.130443 0.452932 0.123 Uiso 1 1 calc R U . . .
H3C H 0.137046 -0.183270 0.344308 0.123 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.02665(17) 0.02853(17) 0.02954(18) -0.00131(16) 0.00737(12) -0.00142(16)
Cl4 0.0296(4) 0.0466(4) 0.0285(4) -0.0011(3) 0.0022(3) -0.0060(4)
Cl2 0.0275(3) 0.0371(4) 0.0383(4) 0.0024(4) 0.0126(3) 0.0006(3)
Cl3 0.0404(4) 0.0456(5) 0.0256(4) 0.0029(3) 0.0052(3) -0.0026(4)
Cl1 0.0336(4) 0.0336(4) 0.0667(6) -0.0089(4) 0.0142(4) 0.0042(3)
N1 0.0336(13) 0.0566(17) 0.0276(12) -0.0042(16) -0.0026(10) 0.0040(16)
N2 0.0345(14) 0.0545(19) 0.0250(13) -0.0082(13) 0.0097(10) -0.0078(14)
N3 0.0221(10) 0.0378(12) 0.0234(11) 0.0001(14) 0.0064(8) -0.0064(14)
N5 0.0414(14) 0.0456(17) 0.0233(12) 0.0059(13) -0.0006(10) -0.0122(14)
N4 0.0328(13) 0.0402(16) 0.0252(13) 0.0057(12) -0.0010(10) -0.0091(12)
C1 0.0296(14) 0.0252(13) 0.0263(13) -0.0004(14) 0.0036(11) -0.0048(15)
C2 0.0232(13) 0.0297(16) 0.0243(14) -0.0018(11) 0.0082(11) 0.0011(11)
C4 0.084(3) 0.090(4) 0.0291(19) 0.011(2) -0.0123(19) -0.044(3)
C3 0.108(4) 0.087(3) 0.043(2) 0.027(2) -0.014(2) -0.057(3)

_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 Cl4 2.2550(8) . ?
Zn1 Cl2 2.2786(7) . ?
Zn1 Cl3 2.2831(8) . ?
Zn1 Cl1 2.2774(8) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.304(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.295(4) . ?
N3 H3 0.8600 . ?
N3 C1 1.375(3) . ?
N3 C2 1.370(3) . ?
N5 C2 1.322(4) . ?
N5 C4 1.463(4) . ?
N5 C3 1.465(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.301(4) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?

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
Cl4 Zn1 Cl2 104.68(3) . . ?
Cl4 Zn1 Cl3 111.77(3) . . ?
Cl4 Zn1 Cl1 112.57(3) . . ?
Cl2 Zn1 Cl3 107.31(3) . . ?
Cl1 Zn1 Cl2 111.50(3) . . ?
Cl1 Zn1 Cl3 108.86(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
C1 N3 H3 117.1 . . ?
C2 N3 H3 117.1 . . ?
C2 N3 C1 125.7(2) . . ?
C2 N5 C4 119.0(3) . . ?
C2 N5 C3 123.0(3) . . ?
C4 N5 C3 117.8(3) . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
N1 C1 N3 117.1(2) . . ?
N2 C1 N1 122.6(2) . . ?
N2 C1 N3 120.3(2) . . ?
N5 C2 N3 118.7(3) . . ?
N4 C2 N3 119.3(3) . . ?
N4 C2 N5 122.0(3) . . ?
N5 C4 H4C 109.5 . . ?
N5 C4 H4D 109.5 . . ?
N5 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N5 C3 H3A 109.5 . . ?
N5 C3 H3B 109.5 . . ?
N5 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 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 N3 C2 N5 -147.4(3) . . . . ?
C1 N3 C2 N4 34.3(5) . . . . ?
C2 N3 C1 N1 -154.3(3) . . . . ?
C2 N3 C1 N2 27.0(5) . . . . ?
C4 N5 C2 N3 -168.8(3) . . . . ?
C4 N5 C2 N4 9.4(5) . . . . ?
C3 N5 C2 N3 15.7(5) . . . . ?
C3 N5 C2 N4 -166.1(4) . . . . ?

_shelx_res_file                  
;
TITL lrn25111601_0m_a.res in P2(1)
    lrn25111601_0m.res
    created by SHELXL-2018/3 at 22:29:43 on 10-Jan-2026
REM Old TITL LRN25111601_0m in P2(1)
REM SHELXT solution in P2(1): R1 0.163, Rweak 0.054, Alpha 0.003
REM <I/s> 0.512 for 4 systematic absences, Orientation as input
REM Flack x = -0.443 ( 0.052 ) from 1125 Parsons' quotients
REM Formula found by SHELXT: C7 O3 Cl3
CELL 0.71073 6.8052 6.9176 14.193 90 98.816 90
ZERR 2 0.0006 0.0005 0.0012 0 0.003 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N Zn
UNIT 8 26 8 10 2

L.S. 4 0 0
PLAN  6
TEMP 23
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
OMIT 0 0 2
REM <olex2.extras>
REM <HklSrc "%.\\LRN25111601_0m.hkl">
REM </olex2.extras>

WGHT    0.014900
BASF   0.02735
FVAR       1.04627
ZN1   5   -0.277551    0.617470    0.204318    11.00000    0.02665    0.02853 =
         0.02954   -0.00131    0.00737   -0.00142
CL4   3   -0.481907    0.470547    0.085672    11.00000    0.02956    0.04659 =
         0.02849   -0.00107    0.00222   -0.00601
CL2   3    0.019115    0.640547    0.149371    11.00000    0.02754    0.03707 =
         0.03831    0.00236    0.01258    0.00060
CL3   3   -0.226605    0.432803    0.339186    11.00000    0.04043    0.04558 =
         0.02559    0.00287    0.00522   -0.00260
CL1   3   -0.391509    0.913252    0.241212    11.00000    0.03363    0.03361 =
         0.06668   -0.00885    0.01417    0.00418
N1    4   -0.135516    0.129469    0.066644    11.00000    0.03361    0.05660 =
         0.02756   -0.00416   -0.00261    0.00398
AFIX  93
H1A   2   -0.142136    0.123674    0.005711    11.00000   -1.20000
H1B   2   -0.241928    0.146175    0.091431    11.00000   -1.20000
AFIX   0
N2    4    0.200712    0.087592    0.088035    11.00000    0.03445    0.05455 =
         0.02504   -0.00820    0.00971   -0.00775
AFIX  93
H2A   2    0.199879    0.081076    0.027466    11.00000   -1.20000
H2B   2    0.310998    0.077285    0.126401    11.00000   -1.20000
AFIX   0
N3    4    0.035695    0.119273    0.218268    11.00000    0.02212    0.03783 =
         0.02340    0.00010    0.00639   -0.00636
AFIX  43
H3    2   -0.071938    0.084990    0.238493    11.00000   -1.20000
AFIX   0
N5    4    0.214261    0.092964    0.370351    11.00000    0.04143    0.04558 =
         0.02327    0.00593   -0.00061   -0.01223
N4    4    0.310530    0.311217    0.264581    11.00000    0.03277    0.04015 =
         0.02524    0.00573   -0.00103   -0.00912
AFIX  93
H4A   2    0.406922    0.349827    0.306757    11.00000   -1.20000
H4B   2    0.292522    0.362342    0.208688    11.00000   -1.20000
AFIX   0
C1    1    0.035918    0.112921    0.121466    11.00000    0.02958    0.02524 =
         0.02631   -0.00044    0.00358   -0.00476
C2    1    0.191921    0.175435    0.285336    11.00000    0.02324    0.02975 =
         0.02429   -0.00182    0.00822    0.00114
C4    1    0.356546    0.175567    0.447583    11.00000    0.08385    0.09048 =
         0.02910    0.01069   -0.01227   -0.04377
AFIX 137
H4C   2    0.488586    0.135013    0.440844    11.00000   -1.50000
H4D   2    0.325544    0.131824    0.507792    11.00000   -1.50000
H4E   2    0.348876    0.314067    0.444792    11.00000   -1.50000
AFIX   0
C3    1    0.113270   -0.086438    0.389685    11.00000    0.10831    0.08673 =
         0.04301    0.02687   -0.01381   -0.05660
AFIX 137
H3A   2   -0.027051   -0.063177    0.384487    11.00000   -1.50000
H3B   2    0.163628   -0.130443    0.452932    11.00000   -1.50000
H3C   2    0.137046   -0.183270    0.344308    11.00000   -1.50000
AFIX   0
HKLF 4




REM  lrn25111601_0m_a.res in P2(1)
REM wR2 = 0.0484, GooF = S = 1.030, Restrained GooF = 1.030 for all data
REM R1 = 0.0231 for 2844 Fo > 4sig(Fo) and 0.0268 for all 3020 data
REM 130 parameters refined using 1 restraints

END

WGHT      0.0149      0.0000

REM Highest difference peak  0.221,  deepest hole -0.364,  1-sigma level  0.058
Q1    1   0.2756 -0.2214  0.4042  11.00000  0.05    0.22
Q2    1   0.0757 -0.3809  0.4293  11.00000  0.05    0.19
Q3    1   0.4605  0.3076  0.4369  11.00000  0.05    0.19
Q4    1  -0.3128  0.8967  0.2829  11.00000  0.05    0.19
Q5    1   0.1362  0.3465  0.4443  11.00000  0.05    0.18
Q6    1  -0.3439  0.2399 -0.0096  11.00000  0.05    0.18
;
_shelx_res_checksum              25936
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.973(12)
2 0.027(12)

####################################################################### 
# 
# 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_cl
_database_code_depnum_ccdc_archive 'CCDC 2522224'
loop_
_audit_author_name
_audit_author_address
b
;yangzhou university
China
;
_audit_update_record             
;
2026-01-11 deposited with the CCDC.	2026-04-16 downloaded from the CCDC.
;
_audit_creation_date             2026-01-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl), C4 H13 N5'
_chemical_formula_sum            'C4 H13 Cl2 N5'
_chemical_formula_weight         202.09
_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'
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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1245(5)
_cell_length_b                   5.7932(4)
_cell_length_c                   12.5446(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.077(2)
_cell_angle_gamma                90
_cell_volume                     499.94(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4093
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0475 after correction.
The Ratio of minimum to maximum transmission is 0.8840.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7342
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.465
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                1958
_reflns_number_total             2262
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.236
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.050
_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)+(0.0352P)²+0.0348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3)
2.b X=CH2 refined with riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B), N1(H1A,H1B)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4C,H4D,H4E)
;
_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
Cl2 Cl 1.33332(10) 0.42051(13) 0.55107(6) 0.0360(2) Uani 1 1 d . . . . .
Cl1 Cl 1.07060(11) 1.05134(13) 0.85711(6) 0.0424(2) Uani 1 1 d . . . . .
N2 N 1.0685(3) 0.6062(4) 0.7078(2) 0.0383(7) Uani 1 1 d . . . . .
H2A H 1.171600 0.579543 0.686351 0.046 Uiso 1 1 calc R U . . .
H2B H 1.073092 0.698803 0.762065 0.046 Uiso 1 1 calc R U . . .
N4 N 0.8425(3) 0.5059(4) 0.87858(19) 0.0368(6) Uani 1 1 d . . . . .
H4A H 0.834577 0.535681 0.944430 0.044 Uiso 1 1 calc R U . . .
H4B H 0.921478 0.401514 0.867883 0.044 Uiso 1 1 calc R U . . .
N3 N 0.7413(3) 0.5529(5) 0.69022(18) 0.0340(6) Uani 1 1 d . . . . .
H3 H 0.632327 0.539883 0.641090 0.041 Uiso 1 1 calc R U . . .
N5 N 0.6108(4) 0.7808(4) 0.8044(2) 0.0342(6) Uani 1 1 d . . . . .
N1 N 0.8931(4) 0.3648(4) 0.5756(2) 0.0387(7) Uani 1 1 d . . . . .
H1A H 0.994297 0.335397 0.552640 0.046 Uiso 1 1 calc R U . . .
H1B H 0.783734 0.300916 0.544177 0.046 Uiso 1 1 calc R U . . .
C2 C 0.7348(4) 0.6191(5) 0.7949(2) 0.0285(6) Uani 1 1 d . . . . .
C1 C 0.9056(4) 0.5066(5) 0.6584(2) 0.0308(7) Uani 1 1 d . . . . .
C3 C 0.5294(4) 0.9475(6) 0.7167(3) 0.0434(8) Uani 1 1 d . . . . .
H3A H 0.588870 1.095501 0.736428 0.065 Uiso 1 1 calc R U . . .
H3B H 0.391693 0.959834 0.707362 0.065 Uiso 1 1 calc R U . . .
H3C H 0.554310 0.896269 0.648906 0.065 Uiso 1 1 calc R U . . .
C4 C 0.5834(6) 0.8384(8) 0.9122(3) 0.0594(12) Uani 1 1 d . . . . .
H4C H 0.594746 0.701073 0.956271 0.089 Uiso 1 1 calc R U . . .
H4D H 0.456645 0.904481 0.903347 0.089 Uiso 1 1 calc R U . . .
H4E H 0.680578 0.947691 0.948203 0.089 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl2 0.0316(4) 0.0411(4) 0.0348(4) 0.0002(3) 0.0079(3) 0.0035(3)
Cl1 0.0506(5) 0.0362(4) 0.0372(4) -0.0085(3) 0.0059(3) 0.0079(3)
N2 0.0322(13) 0.0429(17) 0.0432(16) -0.0189(12) 0.0160(11) -0.0073(12)
N4 0.0426(14) 0.0393(17) 0.0294(13) 0.0028(11) 0.0106(11) 0.0154(12)
N3 0.0247(12) 0.0488(15) 0.0270(12) -0.0032(13) 0.0039(9) 0.0027(12)
N5 0.0352(14) 0.0372(15) 0.0316(14) 0.0049(11) 0.0113(11) 0.0107(11)
N1 0.0369(14) 0.0405(18) 0.0388(15) -0.0153(12) 0.0099(11) -0.0062(11)
C2 0.0255(14) 0.0313(17) 0.0294(16) 0.0003(12) 0.0081(11) -0.0001(12)
C1 0.0324(16) 0.0319(18) 0.0282(15) 0.0001(12) 0.0080(12) 0.0040(13)
C3 0.0478(18) 0.0370(18) 0.0437(18) 0.0096(15) 0.0091(14) 0.0087(16)
C4 0.064(2) 0.080(3) 0.040(2) 0.0063(18) 0.0242(18) 0.037(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.300(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.304(3) . ?
N3 H3 0.8600 . ?
N3 C2 1.381(3) . ?
N3 C1 1.358(3) . ?
N5 C2 1.314(4) . ?
N5 C3 1.465(4) . ?
N5 C4 1.455(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.309(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?

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
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
C2 N3 H3 117.3 . . ?
C1 N3 H3 117.3 . . ?
C1 N3 C2 125.4(2) . . ?
C2 N5 C3 123.1(2) . . ?
C2 N5 C4 120.2(3) . . ?
C4 N5 C3 115.1(3) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N4 C2 N3 117.9(3) . . ?
N4 C2 N5 123.7(3) . . ?
N5 C2 N3 118.3(2) . . ?
N2 C1 N3 120.2(3) . . ?
N2 C1 N1 121.7(3) . . ?
N1 C1 N3 118.1(3) . . ?
N5 C3 H3A 109.5 . . ?
N5 C3 H3B 109.5 . . ?
N5 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N5 C4 H4C 109.5 . . ?
N5 C4 H4D 109.5 . . ?
N5 C4 H4E 109.5 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 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
C2 N3 C1 N2 -28.0(5) . . . . ?
C2 N3 C1 N1 153.6(3) . . . . ?
C1 N3 C2 N4 -45.5(4) . . . . ?
C1 N3 C2 N5 139.3(3) . . . . ?
C3 N5 C2 N4 163.3(3) . . . . ?
C3 N5 C2 N3 -21.7(4) . . . . ?
C4 N5 C2 N4 -1.8(5) . . . . ?
C4 N5 C2 N3 173.2(3) . . . . ?

_shelx_res_file                  
;
TITL cl_a.res in P2(1)
    cl.res
    created by SHELXL-2018/3 at 20:25:14 on 11-Jan-2026
REM Old TITL Cl in P2(1)
REM SHELXT solution in P2(1): R1 0.097, Rweak 0.039, Alpha 0.001
REM <I/s> 0.439 for 4 systematic absences, Orientation as input
REM Flack x = 0.031 ( 0.030 ) from 759 Parsons' quotients
REM Formula found by SHELXT: C8 O Cl2
CELL 0.71073 7.1245 5.7932 12.5446 90 105.077 90
ZERR 2 0.0005 0.0004 0.0008 0 0.002 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Cl N
UNIT 8 26 4 10

L.S. 10 0 0
PLAN  3
TEMP 23
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\Cl.hkl">
REM </olex2.extras>

WGHT    0.035200    0.034800
FVAR       1.50597
CL2   3    1.333316    0.420512    0.551067    11.00000    0.03161    0.04106 =
         0.03481    0.00017    0.00792    0.00348
CL1   3    1.070596    1.051338    0.857109    11.00000    0.05056    0.03621 =
         0.03724   -0.00853    0.00587    0.00793
N2    4    1.068467    0.606230    0.707849    11.00000    0.03220    0.04286 =
         0.04320   -0.01888    0.01604   -0.00728
AFIX  93
H2A   2    1.171600    0.579543    0.686351    11.00000   -1.20000
H2B   2    1.073092    0.698803    0.762065    11.00000   -1.20000
AFIX   0
N4    4    0.842509    0.505912    0.878580    11.00000    0.04261    0.03925 =
         0.02938    0.00281    0.01064    0.01544
AFIX  93
H4A   2    0.834577    0.535681    0.944430    11.00000   -1.20000
H4B   2    0.921478    0.401514    0.867883    11.00000   -1.20000
AFIX   0
N3    4    0.741321    0.552902    0.690224    11.00000    0.02468    0.04880 =
         0.02701   -0.00323    0.00393    0.00269
AFIX  43
H3    2    0.632327    0.539883    0.641090    11.00000   -1.20000
AFIX   0
N5    4    0.610805    0.780807    0.804397    11.00000    0.03524    0.03718 =
         0.03162    0.00492    0.01127    0.01068
N1    4    0.893111    0.364755    0.575600    11.00000    0.03691    0.04052 =
         0.03881   -0.01534    0.00985   -0.00620
AFIX  93
H1A   2    0.994297    0.335397    0.552640    11.00000   -1.20000
H1B   2    0.783734    0.300916    0.544177    11.00000   -1.20000
AFIX   0
C2    1    0.734763    0.619110    0.794924    11.00000    0.02547    0.03127 =
         0.02942    0.00031    0.00811   -0.00008
C1    1    0.905581    0.506637    0.658392    11.00000    0.03239    0.03192 =
         0.02823    0.00014    0.00801    0.00401
C3    1    0.529404    0.947467    0.716716    11.00000    0.04777    0.03702 =
         0.04370    0.00956    0.00907    0.00870
AFIX 137
H3A   2    0.588870    1.095501    0.736428    11.00000   -1.50000
H3B   2    0.391693    0.959834    0.707362    11.00000   -1.50000
H3C   2    0.554310    0.896269    0.648906    11.00000   -1.50000
AFIX   0
C4    1    0.583359    0.838412    0.912225    11.00000    0.06388    0.08001 =
         0.04031    0.00629    0.02415    0.03674
AFIX 137
H4C   2    0.594746    0.701073    0.956271    11.00000   -1.50000
H4D   2    0.456645    0.904481    0.903347    11.00000   -1.50000
H4E   2    0.680578    0.947691    0.948203    11.00000   -1.50000
AFIX   0
HKLF 4




REM  cl_a.res in P2(1)
REM wR2 = 0.0714, GooF = S = 1.050, Restrained GooF = 1.050 for all data
REM R1 = 0.0330 for 1958 Fo > 4sig(Fo) and 0.0439 for all 2262 data
REM 102 parameters refined using 1 restraints

END

WGHT      0.0352      0.0348

REM Highest difference peak  0.236,  deepest hole -0.179,  1-sigma level  0.043
Q1    1   0.9813  1.0615  0.8971  11.00000  0.05    0.24
Q2    1   1.4404  0.4060  0.5207  11.00000  0.05    0.21
Q3    1   1.1763  0.3909  0.5424  11.00000  0.05    0.20
;
_shelx_res_checksum              29321
_olex2_submission_special_instructions 'No special instructions were received'
