# Supplementary Information (SI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2447067'
loop_
_audit_author_name
_audit_author_address
'zeyu xu'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2025-12-01 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H10 N O, Cl O4'
_chemical_formula_sum            'C4 H10 Cl N O5'
_chemical_formula_weight         187.58
_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   8.284(6)
_cell_length_b                   9.770(7)
_cell_length_c                   9.568(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     774.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1274 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.6993.
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    1.609
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5938
_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         27.483
_diffrn_reflns_theta_min         2.980
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_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           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                725
_reflns_number_total             942
_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       'Bruker SMART APEX II diffractometer'
_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         0.812
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         942
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      1.164
_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)+(0.1050P)²+1.1069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1879
_refine_ls_wR_factor_ref         0.2119
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 Cl2-O3 = Cl2-O4 = Cl2-O5 = Cl2-O6
 1.5 with sigma of 0.02
 Cl2-O3 \\sim Cl2-O4 \\sim Cl2-O5 \\sim Cl2-O6
 with sigma of 0.02
 O3-O5 \\sim O4-O6 \\sim O3-O6 \\sim O4-O5 \\sim O3-O4 \\sim O5-O6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O3 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(O5) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4. Rigid body (RIGU) restrains
 Cl2, O3, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: Cl2(0.5) O3(0.5) O4(0.5) O5(0.5) O6(0.5)
6.a Secondary CH2 refined with riding coordinates:
 N003(H00A,H00B), C005(H00C,H00D), C006(H00E,H00F)
;
_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
O002 O 0.0206(4) 0.750000 0.7561(4) 0.0508(9) Uani 1 2 d S T P . .
N003 N 0.2583(4) 0.750000 0.5452(4) 0.0404(9) Uani 1 2 d S T P . .
H00A H 0.284194 0.750000 0.454915 0.048 Uiso 1 2 calc R U P . .
H00B H 0.349365 0.749999 0.594474 0.048 Uiso 1 2 calc R U P . .
C005 C 0.1651(4) 0.6260(4) 0.5778(4) 0.0486(9) Uani 1 1 d . . . . .
H00C H 0.230556 0.545335 0.560973 0.058 Uiso 1 1 calc R U . . .
H00D H 0.070401 0.621084 0.518381 0.058 Uiso 1 1 calc R U . . .
C006 C 0.1147(5) 0.6313(4) 0.7297(4) 0.0544(10) Uani 1 1 d . . . . .
H00E H 0.052346 0.550254 0.752478 0.065 Uiso 1 1 calc R U . . .
H00F H 0.209917 0.632306 0.788704 0.065 Uiso 1 1 calc R U . . .
Cl2 Cl 0.34028(19) 0.2638(12) 0.63779(17) 0.0489(15) Uani 0.5 1 d D U P A -1
O3 O 0.4460(7) 0.3602(7) 0.5734(7) 0.0664(17) Uani 0.5 1 d D U P A -1
O4 O 0.3048(10) 0.3308(9) 0.7635(6) 0.103(3) Uani 0.5 1 d D U P A -1
O5 O 0.4276(17) 0.1421(12) 0.6553(15) 0.142(4) Uani 0.5 1 d D U P A -1
O6 O 0.2029(6) 0.243(3) 0.5540(5) 0.083(2) Uani 0.5 1 d D U P A -1

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
O002 0.0391(17) 0.066(2) 0.0470(18) 0.000 0.0144(14) 0.000
N003 0.0332(19) 0.060(2) 0.0275(16) 0.000 0.0008(14) 0.000
C005 0.051(2) 0.0423(19) 0.052(2) -0.0033(15) -0.0006(15) 0.0044(16)
C006 0.055(2) 0.054(2) 0.055(2) 0.0148(17) 0.0054(17) -0.0037(18)
Cl2 0.0441(8) 0.050(4) 0.0524(8) -0.0023(13) -0.0127(5) 0.0036(14)
O3 0.048(3) 0.086(4) 0.066(4) -0.014(3) 0.020(3) -0.015(3)
O4 0.125(6) 0.149(6) 0.034(3) -0.022(4) 0.017(3) -0.022(5)
O5 0.146(6) 0.115(5) 0.164(7) 0.006(5) -0.026(5) 0.023(5)
O6 0.051(3) 0.122(6) 0.077(3) -0.001(10) -0.022(2) -0.032(8)

_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
O002 C006 1.420(5) 7_575 ?
O002 C006 1.420(4) . ?
N003 H00A 0.8900 . ?
N003 H00B 0.8900 . ?
N003 C005 1.470(4) 7_575 ?
N003 C005 1.470(4) . ?
C005 H00C 0.9700 . ?
C005 H00D 0.9700 . ?
C005 C006 1.514(6) . ?
C006 H00E 0.9700 . ?
C006 H00F 0.9700 . ?
Cl2 O3 1.426(8) . ?
Cl2 O4 1.401(7) . ?
Cl2 O5 1.402(10) . ?
Cl2 O6 1.406(5) . ?

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
C006 O002 C006 109.5(4) 7_575 . ?
H00A N003 H00B 108.0 . . ?
C005 N003 H00A 109.4 . . ?
C005 N003 H00A 109.4 7_575 . ?
C005 N003 H00B 109.4 7_575 . ?
C005 N003 H00B 109.4 . . ?
C005 N003 C005 111.0(4) . 7_575 ?
N003 C005 H00C 109.9 . . ?
N003 C005 H00D 109.9 . . ?
N003 C005 C006 108.7(3) . . ?
H00C C005 H00D 108.3 . . ?
C006 C005 H00C 109.9 . . ?
C006 C005 H00D 109.9 . . ?
O002 C006 C005 110.5(3) . . ?
O002 C006 H00E 109.6 . . ?
O002 C006 H00F 109.6 . . ?
C005 C006 H00E 109.6 . . ?
C005 C006 H00F 109.6 . . ?
H00E C006 H00F 108.1 . . ?
O4 Cl2 O3 101.0(7) . . ?
O4 Cl2 O5 113.7(7) . . ?
O4 Cl2 O6 112.7(7) . . ?
O5 Cl2 O3 107.1(6) . . ?
O5 Cl2 O6 111.4(13) . . ?
O6 Cl2 O3 110.2(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N003 H00A O4 0.89 2.13 2.856(8) 138.8 8_665 yes
N003 H00A O4 0.89 2.13 2.856(8) 138.8 2_564 yes
N003 H00B O002 0.89 2.01 2.888(5) 166.8 4_566 yes

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
N003 C005 C006 O002 58.8(4) . . . . ?
C005 N003 C005 C006 -56.2(5) 7_575 . . . ?
C006 O002 C006 C005 -62.2(5) 7_575 . . . ?

_shelx_res_file                  
;
TITL 1_a.res in Pnma
    1.res
    created by SHELXL-2018/3 at 09:09:49 on 01-Dec-2025
REM Old TITL 1_a.res in Pnma
REM SHELXT solution in Pnma
REM R1 0.213, Rweak 0.075, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C8 Cl O3
CELL 0.71073 8.2837 9.7697 9.5683 90 90 90
ZERR 4 0.0058 0.0065 0.0072 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H Cl N O
UNIT 16 40 4 4 20
EQIV $1 0.5+X,1.5-Y,1.5-Z
EQIV $2 0.5-X,1-Y,-0.5+Z
EQIV $3 0.5-X,0.5+Y,-0.5+Z
DFIX 1.5 Cl2 O3 Cl2 O4 Cl2 O5 Cl2 O6
SADI Cl2 O3 Cl2 O4 Cl2 O5 Cl2 O6
SADI 0.04 O3 O5 O4 O6 O3 O6 O4 O5 O3 O4 O5 O6
SIMU Cl2 O3 O4 O5 O6
RIGU Cl2 O3 O4 O5 O6
ISOR 0.003 0.006 O5

L.S. 20
PLAN  5
TEMP 19.85
CONF
HTAB N003 O002_$1
HTAB N003 O4_$2
HTAB N003 O4_$3
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\1.hkl">
REM </olex2.extras>

WGHT    0.105000    1.106900
FVAR       1.62776
O002  5    0.020609    0.750000    0.756112    10.50000    0.03915    0.06615 =
         0.04701    0.00000    0.01438    0.00000
N003  4    0.258254    0.750000    0.545179    10.50000    0.03320    0.06045 =
         0.02751    0.00000    0.00082    0.00000
AFIX  23
H00A  2    0.284194    0.750000    0.454915    10.50000   -1.20000
H00B  2    0.349365    0.749999    0.594474    10.50000   -1.20000
AFIX   0
C005  1    0.165118    0.626010    0.577775    11.00000    0.05136    0.04232 =
         0.05226   -0.00327   -0.00059    0.00442
AFIX  23
H00C  2    0.230556    0.545335    0.560973    11.00000   -1.20000
H00D  2    0.070401    0.621084    0.518381    11.00000   -1.20000
AFIX   0
C006  1    0.114680    0.631296    0.729728    11.00000    0.05495    0.05378 =
         0.05454    0.01476    0.00544   -0.00370
AFIX  23
H00E  2    0.052346    0.550254    0.752478    11.00000   -1.20000
H00F  2    0.209917    0.632306    0.788704    11.00000   -1.20000
AFIX   0

PART -1
CL2   3    0.340284    0.263810    0.637791    10.50000    0.04414    0.05001 =
         0.05241   -0.00234   -0.01269    0.00356
O3    5    0.446036    0.360221    0.573439    10.50000    0.04763    0.08581 =
         0.06583   -0.01413    0.01977   -0.01479
O4    5    0.304757    0.330772    0.763522    10.50000    0.12451    0.14946 =
         0.03439   -0.02244    0.01745   -0.02234
O5    5    0.427645    0.142060    0.655266    10.50000    0.14644    0.11544 =
         0.16409    0.00583   -0.02570    0.02309
O6    5    0.202912    0.243342    0.553985    10.50000    0.05132    0.12155 =
         0.07728   -0.00127   -0.02156   -0.03150
HKLF 4




REM  1_a.res in Pnma
REM wR2 = 0.2119, GooF = S = 1.073, Restrained GooF = 1.164 for all data
REM R1 = 0.0743 for 725 Fo > 4sig(Fo) and 0.0961 for all 942 data
REM 76 parameters refined using 81 restraints

END

WGHT      0.1050      1.1069

REM Highest difference peak  0.812,  deepest hole -0.477,  1-sigma level  0.080
Q1    1   0.3386  0.2500  0.7715  10.50000  0.05    0.81
Q2    1   0.4822  0.2500  0.5830  10.50000  0.05    0.67
Q3    1   0.3426  0.3694  0.7264  11.00000  0.05    0.58
Q4    1   0.2347  0.3352  0.7398  11.00000  0.05    0.39
Q5    1   0.3802  0.3556  0.5490  11.00000  0.05    0.27
;
_shelx_res_checksum              95098
_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_xzy
_database_code_depnum_ccdc_archive 'CCDC 2474280'
loop_
_audit_author_name
_audit_author_address
'zeyu xu'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2025-12-10 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl O4), H2 O, C5 H14 N2'
_chemical_formula_sum            'C5 H16 Cl2 N2 O9'
_chemical_formula_weight         319.10
_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/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                   7.7982(5)
_cell_length_b                   10.6867(8)
_cell_length_c                   14.9073(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.435(2)
_cell_angle_gamma                90
_cell_volume                     1228.89(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4606
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.7733.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11007
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.354
_diffrn_ambient_temperature      193.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_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           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2263
_reflns_number_total             2802
_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       'Bruker SMART APEX II diffractometer'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.057
_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)+(0.0299P)²+1.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0983
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 Cl01-O00E \\sim Cl01-O00F
 with sigma of 0.02
 Cl01-O00H \\sim Cl01-O1
 with sigma of 0.02
 Cl01-O00I \\sim Cl01-O00J
 with sigma of 0.02
 Cl02-O004 \\sim Cl02-O2
 with sigma of 0.02
 Cl02-O007 \\sim Cl02-O0
 with sigma of 0.02
 Cl02-O00C \\sim Cl02-O00D
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O00D) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(O00F)=Sof(O00J)=Sof(O1)=1-FVAR(1)
 Sof(O00E)=Sof(O00H)=Sof(O00I)=FVAR(1)
 Sof(O0)=Sof(O00D)=Sof(O2)=1-FVAR(2)
 Sof(O004)=Sof(O007)=Sof(O00C)=FVAR(2)
5.a Free rotating group:
 O003(H00N,H00O)
5.b Ternary CH refined with riding coordinates:
 N005(H005)
5.c Secondary CH2 refined with riding coordinates:
 N008(H00A,H00B), C009(H00C,H00D), C00B(H00E,H00F), C00D(H00G,H00H), C00F(H00I,
 H00J)
5.d Idealised Me refined as rotating group:
 C00G(H00K,H00L,H00M)
;
_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
Cl01 Cl 0.66905(7) 0.68230(5) 0.59048(3) 0.02760(15) Uani 1 1 d D . . . .
Cl02 Cl 0.64448(6) 0.58003(6) 0.21829(3) 0.02739(15) Uani 1 1 d D . . . .
O003 O 0.7913(2) 0.43777(18) 0.43381(11) 0.0345(4) Uani 1 1 d G . . . .
H00N H 0.776763 0.401831 0.380902 0.052 Uiso 1 1 d G U . . .
H00O H 0.689109 0.466149 0.439981 0.052 Uiso 1 1 d G U . . .
O004 O 0.6576(8) 0.6482(5) 0.3016(3) 0.0311(10) Uani 0.887(12) 1 d D . P A 1
N005 N 0.7471(2) 0.16375(17) 0.64312(12) 0.0226(4) Uani 1 1 d . . . . .
H005 H 0.830156 0.123630 0.692209 0.027 Uiso 1 1 calc R U . . .
O006 O 0.7367(2) 0.4645(2) 0.23423(13) 0.0504(5) Uani 1 1 d . . . . .
O007 O 0.4661(3) 0.5589(3) 0.1830(3) 0.0378(8) Uani 0.887(12) 1 d D . P A 1
N008 N 0.9937(2) 0.32881(19) 0.57797(13) 0.0307(4) Uani 1 1 d . . . . .
H00A H 0.927848 0.370578 0.532064 0.037 Uiso 1 1 calc R U . . .
H00B H 1.104263 0.357912 0.582187 0.037 Uiso 1 1 calc R U . . .
C009 C 0.9912(3) 0.1930(2) 0.55682(16) 0.0326(5) Uani 1 1 d . . . . .
H00C H 1.072393 0.148395 0.603327 0.039 Uiso 1 1 calc R U . . .
H00D H 1.030013 0.179688 0.497217 0.039 Uiso 1 1 calc R U . . .
O00A O 0.8488(2) 0.6531(2) 0.60287(16) 0.0618(6) Uani 1 1 d . . . . .
C00B C 0.9257(3) 0.3539(2) 0.66501(16) 0.0331(5) Uani 1 1 d . . . . .
H00E H 0.923534 0.445265 0.675834 0.040 Uiso 1 1 calc R U . . .
H00F H 1.003414 0.315148 0.715925 0.040 Uiso 1 1 calc R U . . .
O00C O 0.7236(5) 0.6543(4) 0.1544(2) 0.0659(12) Uani 0.887(12) 1 d D . P A 1
C00D C 0.7451(3) 0.3013(2) 0.66131(15) 0.0281(5) Uani 1 1 d . . . . .
H00G H 0.702464 0.316773 0.719692 0.034 Uiso 1 1 calc R U . . .
H00H H 0.665634 0.343512 0.612729 0.034 Uiso 1 1 calc R U . . .
O00E O 0.5926(14) 0.6356(8) 0.5061(4) 0.068(2) Uani 0.68(2) 1 d D . P B 1
C00F C 0.8108(3) 0.1410(2) 0.55474(15) 0.0281(5) Uani 1 1 d . . . . .
H00I H 0.731366 0.181227 0.505190 0.034 Uiso 1 1 calc R U . . .
H00J H 0.811680 0.049920 0.542532 0.034 Uiso 1 1 calc R U . . .
C00G C 0.5715(3) 0.1073(2) 0.64463(18) 0.0355(6) Uani 1 1 d . . . . .
H00K H 0.533185 0.125119 0.703070 0.053 Uiso 1 1 calc R U . . .
H00L H 0.577694 0.016595 0.636190 0.053 Uiso 1 1 calc R U . . .
H00M H 0.488737 0.143430 0.595625 0.053 Uiso 1 1 calc R U . . .
O00H O 0.5995(7) 0.6170(7) 0.6614(5) 0.0542(17) Uani 0.68(2) 1 d D . P B 1
O00I O 0.6398(8) 0.8107(5) 0.5984(6) 0.0613(18) Uani 0.68(2) 1 d D . P B 1
O00F O 0.6539(19) 0.8049(15) 0.5480(19) 0.086(6) Uani 0.32(2) 1 d D . P B 2
O00J O 0.6001(18) 0.691(4) 0.6687(8) 0.104(9) Uani 0.32(2) 1 d D . P B 2
O1 O 0.5580(16) 0.604(2) 0.5295(14) 0.076(6) Uani 0.32(2) 1 d D . P B 2
O0 O 0.470(2) 0.525(2) 0.228(3) 0.032(7) Uani 0.113(12) 1 d D . P A 2
O00D O 0.647(5) 0.604(3) 0.1266(12) 0.059(9) Uani 0.113(12) 1 d D U P A 2
O2 O 0.684(7) 0.672(4) 0.286(3) 0.040(10) Uani 0.113(12) 1 d D . P A 2

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
Cl01 0.0266(3) 0.0329(3) 0.0237(3) -0.0020(2) 0.0050(2) -0.0002(2)
Cl02 0.0219(3) 0.0395(3) 0.0204(3) -0.0017(2) 0.00206(19) 0.0020(2)
O003 0.0301(8) 0.0443(11) 0.0279(8) 0.0057(7) 0.0004(7) 0.0016(7)
O004 0.029(2) 0.034(2) 0.0294(13) -0.0086(15) 0.0010(12) 0.0027(15)
N005 0.0188(8) 0.0262(10) 0.0228(9) 0.0024(7) 0.0031(7) 0.0027(7)
O006 0.0454(10) 0.0513(13) 0.0518(12) -0.0179(9) -0.0022(9) 0.0235(9)
O007 0.0246(10) 0.0428(15) 0.0423(18) -0.0071(13) -0.0078(11) -0.0016(9)
N008 0.0238(9) 0.0349(11) 0.0316(10) 0.0106(8) -0.0015(8) -0.0040(8)
C009 0.0292(11) 0.0364(14) 0.0342(12) 0.0085(10) 0.0115(10) 0.0063(10)
O00A 0.0315(10) 0.0701(16) 0.0862(16) 0.0283(13) 0.0162(10) 0.0148(10)
C00B 0.0314(12) 0.0348(14) 0.0316(12) -0.0039(10) -0.0006(10) -0.0058(10)
O00C 0.0587(18) 0.106(3) 0.0340(15) 0.0165(17) 0.0116(13) -0.0258(17)
C00D 0.0278(11) 0.0265(12) 0.0297(11) -0.0042(9) 0.0029(9) 0.0052(9)
O00E 0.096(5) 0.078(4) 0.023(2) -0.019(2) -0.019(3) 0.034(3)
C00F 0.0340(12) 0.0275(12) 0.0243(11) -0.0013(9) 0.0094(9) 0.0017(9)
C00G 0.0252(11) 0.0388(15) 0.0433(14) 0.0044(11) 0.0080(10) -0.0058(10)
O00H 0.052(2) 0.075(4) 0.037(2) 0.012(2) 0.0129(17) -0.021(2)
O00I 0.076(3) 0.029(2) 0.074(4) -0.008(2) -0.006(3) 0.0149(17)
O00F 0.061(6) 0.074(7) 0.108(14) 0.042(8) -0.039(8) -0.002(5)
O00J 0.078(7) 0.21(3) 0.031(4) -0.043(9) 0.029(4) -0.026(11)
O1 0.032(4) 0.122(12) 0.077(10) -0.061(9) 0.017(5) -0.027(6)
O0 0.018(7) 0.027(11) 0.055(17) -0.026(10) 0.015(9) -0.003(7)
O00D 0.092(17) 0.072(15) 0.015(9) 0.018(8) 0.013(10) -0.009(12)
O2 0.027(12) 0.026(14) 0.07(2) -0.007(14) 0.015(13) -0.014(9)

_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
Cl01 O00A 1.4215(19) . ?
Cl01 O00E 1.403(6) . ?
Cl01 O00H 1.438(4) . ?
Cl01 O00I 1.399(5) . ?
Cl01 O00F 1.452(10) . ?
Cl01 O00J 1.357(9) . ?
Cl01 O1 1.432(13) . ?
Cl02 O004 1.430(3) . ?
Cl02 O006 1.431(2) . ?
Cl02 O007 1.431(2) . ?
Cl02 O00C 1.446(3) . ?
Cl02 O0 1.507(14) . ?
Cl02 O00D 1.394(13) . ?
Cl02 O2 1.413(18) . ?
O003 H00N 0.8696 . ?
O003 H00O 0.8701 . ?
N005 H005 1.0000 . ?
N005 C00D 1.495(3) . ?
N005 C00F 1.495(3) . ?
N005 C00G 1.499(3) . ?
N008 H00A 0.9100 . ?
N008 H00B 0.9100 . ?
N008 C009 1.484(3) . ?
N008 C00B 1.496(3) . ?
C009 H00C 0.9900 . ?
C009 H00D 0.9900 . ?
C009 C00F 1.509(3) . ?
C00B H00E 0.9900 . ?
C00B H00F 0.9900 . ?
C00B C00D 1.510(3) . ?
C00D H00G 0.9900 . ?
C00D H00H 0.9900 . ?
C00F H00I 0.9900 . ?
C00F H00J 0.9900 . ?
C00G H00K 0.9800 . ?
C00G H00L 0.9800 . ?
C00G H00M 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
O00A Cl01 O00H 105.6(2) . . ?
O00A Cl01 O00F 105.7(7) . . ?
O00A Cl01 O1 116.5(7) . . ?
O00E Cl01 O00A 108.6(4) . . ?
O00E Cl01 O00H 109.3(4) . . ?
O00I Cl01 O00A 112.0(3) . . ?
O00I Cl01 O00E 111.8(4) . . ?
O00I Cl01 O00H 109.3(3) . . ?
O00J Cl01 O00A 114.2(8) . . ?
O00J Cl01 O00F 107.3(9) . . ?
O00J Cl01 O1 107.8(8) . . ?
O1 Cl01 O00F 104.4(9) . . ?
O004 Cl02 O006 109.0(3) . . ?
O004 Cl02 O007 109.9(3) . . ?
O004 Cl02 O00C 108.0(2) . . ?
O006 Cl02 O00C 109.30(17) . . ?
O006 Cl02 O0 94.7(11) . . ?
O007 Cl02 O006 111.27(16) . . ?
O007 Cl02 O00C 109.31(17) . . ?
O00D Cl02 O006 103.9(10) . . ?
O00D Cl02 O0 107.9(13) . . ?
O00D Cl02 O2 123(2) . . ?
O2 Cl02 O006 116(3) . . ?
O2 Cl02 O0 108.2(18) . . ?
H00N O003 H00O 104.5 . . ?
C00D N005 H005 108.2 . . ?
C00D N005 C00G 111.02(17) . . ?
C00F N005 H005 108.2 . . ?
C00F N005 C00D 109.49(17) . . ?
C00F N005 C00G 111.72(17) . . ?
C00G N005 H005 108.2 . . ?
H00A N008 H00B 108.0 . . ?
C009 N008 H00A 109.4 . . ?
C009 N008 H00B 109.4 . . ?
C009 N008 C00B 111.36(18) . . ?
C00B N008 H00A 109.4 . . ?
C00B N008 H00B 109.4 . . ?
N008 C009 H00C 109.6 . . ?
N008 C009 H00D 109.6 . . ?
N008 C009 C00F 110.35(19) . . ?
H00C C009 H00D 108.1 . . ?
C00F C009 H00C 109.6 . . ?
C00F C009 H00D 109.6 . . ?
N008 C00B H00E 109.6 . . ?
N008 C00B H00F 109.6 . . ?
N008 C00B C00D 110.42(18) . . ?
H00E C00B H00F 108.1 . . ?
C00D C00B H00E 109.6 . . ?
C00D C00B H00F 109.6 . . ?
N005 C00D C00B 109.77(18) . . ?
N005 C00D H00G 109.7 . . ?
N005 C00D H00H 109.7 . . ?
C00B C00D H00G 109.7 . . ?
C00B C00D H00H 109.7 . . ?
H00G C00D H00H 108.2 . . ?
N005 C00F C009 110.56(18) . . ?
N005 C00F H00I 109.5 . . ?
N005 C00F H00J 109.5 . . ?
C009 C00F H00I 109.5 . . ?
C009 C00F H00J 109.5 . . ?
H00I C00F H00J 108.1 . . ?
N005 C00G H00K 109.5 . . ?
N005 C00G H00L 109.5 . . ?
N005 C00G H00M 109.5 . . ?
H00K C00G H00L 109.5 . . ?
H00K C00G H00M 109.5 . . ?
H00L C00G H00M 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
N008 C009 C00F N005 -57.4(2) . . . . ?
N008 C00B C00D N005 58.1(2) . . . . ?
C009 N008 C00B C00D -56.5(2) . . . . ?
C00B N008 C009 C00F 55.8(2) . . . . ?
C00D N005 C00F C009 59.4(2) . . . . ?
C00F N005 C00D C00B -59.6(2) . . . . ?
C00G N005 C00D C00B 176.57(18) . . . . ?
C00G N005 C00F C009 -177.16(19) . . . . ?

_shelx_res_file                  
;
TITL xzy_a.res in P2(1)/n
    xzy.res
    created by SHELXL-2018/3 at 16:21:29 on 10-Dec-2025
REM Old TITL xzy_a.res in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.177, Rweak 0.010, Alpha 0.042
REM <I/s> 0.489 for 146 systematic absences, Orientation as input
REM Formula found by SHELXT: C13 Cl2 N2 O
CELL 0.71073 7.7982 10.6867 14.9073 90 98.435 90
ZERR 4 0.0005 0.0008 0.001 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 20 64 8 8 36
SADI Cl01 O00E Cl01 O00F
SADI Cl01 O00H Cl01 O1
SADI Cl01 O00I Cl01 O00J
SADI Cl02 O004 Cl02 O2
SADI Cl02 O007 Cl02 O0
SADI Cl02 O00C Cl02 O00D
ISOR 0.01 0.02 O00D

L.S. 20
PLAN  5
TEMP -80.15
CONF
BOND
list 4
fmap 2 53
acta
MORE -1
BOND $H
REM <olex2.extras>
REM <HklSrc "%.\\xzy.hkl">
REM </olex2.extras>

WGHT    0.029900    1.086300
FVAR       0.74117   0.67949   0.88719
CL01  3    0.669050    0.682299    0.590482    11.00000    0.02659    0.03291 =
         0.02369   -0.00198    0.00501   -0.00016
CL02  3    0.644482    0.580027    0.218288    11.00000    0.02193    0.03947 =
         0.02044   -0.00171    0.00206    0.00200
AFIX   6
O003  5    0.791310    0.437771    0.433812    11.00000    0.03014    0.04432 =
         0.02787    0.00570    0.00041    0.00162
H00N  2    0.776763    0.401831    0.380902    11.00000   -1.50000
H00O  2    0.689109    0.466149    0.439981    11.00000   -1.50000
AFIX   0

PART 1
O004  5    0.657605    0.648215    0.301552    31.00000    0.02895    0.03398 =
         0.02940   -0.00861    0.00104    0.00271

PART 0
N005  4    0.747074    0.163753    0.643121    11.00000    0.01877    0.02624 =
         0.02283    0.00241    0.00312    0.00268
AFIX  13
H005  2    0.830156    0.123630    0.692209    11.00000   -1.20000
AFIX   0

O006  5    0.736703    0.464467    0.234227    11.00000    0.04536    0.05125 =
         0.05183   -0.01792   -0.00225    0.02348
PART 1
O007  5    0.466096    0.558946    0.183050    31.00000    0.02460    0.04283 =
         0.04230   -0.00706   -0.00778   -0.00156

PART 0
N008  4    0.993703    0.328811    0.577966    11.00000    0.02384    0.03486 =
         0.03164    0.01061   -0.00147   -0.00397
AFIX  23
H00A  2    0.927848    0.370578    0.532064    11.00000   -1.20000
H00B  2    1.104263    0.357912    0.582187    11.00000   -1.20000
AFIX   0
C009  1    0.991224    0.193027    0.556819    11.00000    0.02915    0.03640 =
         0.03422    0.00845    0.01145    0.00634
AFIX  23
H00C  2    1.072393    0.148395    0.603327    11.00000   -1.20000
H00D  2    1.030013    0.179688    0.497217    11.00000   -1.20000
AFIX   0

O00A  5    0.848831    0.653136    0.602867    11.00000    0.03148    0.07007 =
         0.08617    0.02829    0.01616    0.01479
C00B  1    0.925705    0.353918    0.665007    11.00000    0.03140    0.03480 =
         0.03161   -0.00385   -0.00064   -0.00577
AFIX  23
H00E  2    0.923534    0.445265    0.675834    11.00000   -1.20000
H00F  2    1.003414    0.315148    0.715925    11.00000   -1.20000
AFIX   0

PART 1
O00C  5    0.723637    0.654330    0.154423    31.00000    0.05868    0.10633 =
         0.03398    0.01653    0.01157   -0.02577

PART 0
C00D  1    0.745078    0.301304    0.661308    11.00000    0.02782    0.02651 =
         0.02972   -0.00417    0.00289    0.00518
AFIX  23
H00G  2    0.702464    0.316773    0.719692    11.00000   -1.20000
H00H  2    0.665634    0.343512    0.612729    11.00000   -1.20000
AFIX   0

PART 1
O00E  5    0.592623    0.635566    0.506079    21.00000    0.09593    0.07765 =
         0.02291   -0.01897   -0.01894    0.03381

PART 0
C00F  1    0.810783    0.140960    0.554739    11.00000    0.03403    0.02753 =
         0.02427   -0.00134    0.00938    0.00169
AFIX  23
H00I  2    0.731366    0.181227    0.505190    11.00000   -1.20000
H00J  2    0.811680    0.049920    0.542532    11.00000   -1.20000
AFIX   0
C00G  1    0.571463    0.107338    0.644632    11.00000    0.02525    0.03877 =
         0.04334    0.00445    0.00802   -0.00576
AFIX 137
H00K  2    0.533185    0.125119    0.703070    11.00000   -1.50000
H00L  2    0.577694    0.016595    0.636190    11.00000   -1.50000
H00M  2    0.488737    0.143430    0.595625    11.00000   -1.50000
AFIX   0

PART 1
O00H  5    0.599483    0.616963    0.661372    21.00000    0.05230    0.07523 =
         0.03705    0.01229    0.01289   -0.02081
O00I  5    0.639767    0.810739    0.598352    21.00000    0.07606    0.02903 =
         0.07374   -0.00790   -0.00609    0.01489
PART 2
O00F  5    0.653882    0.804881    0.548035   -21.00000    0.06137    0.07405 =
         0.10791    0.04184   -0.03883   -0.00158
O00J  5    0.600137    0.690728    0.668706   -21.00000    0.07825    0.20922 =
         0.03065   -0.04295    0.02943   -0.02649
O1    5    0.558013    0.603710    0.529474   -21.00000    0.03167    0.12238 =
         0.07693   -0.06146    0.01729   -0.02673

O0    5    0.470405    0.524521    0.227676   -31.00000    0.01807    0.02663 =
         0.05490   -0.02608    0.01484   -0.00313
O00D  5    0.647225    0.603830    0.126558   -31.00000    0.09186    0.07159 =
         0.01516    0.01800    0.01317   -0.00921
O2    5    0.683862    0.672313    0.286092   -31.00000    0.02666    0.02579 =
         0.06900   -0.00683    0.01491   -0.01415
HKLF 4




REM  xzy_a.res in P2(1)/n
REM wR2 = 0.0983, GooF = S = 1.052, Restrained GooF = 1.057 for all data
REM R1 = 0.0385 for 2263 Fo > 4sig(Fo) and 0.0539 for all 2802 data
REM 223 parameters refined using 12 restraints

END

WGHT      0.0299      1.0862

REM Highest difference peak  0.333,  deepest hole -0.349,  1-sigma level  0.062
Q1    1   0.6877  0.7397  0.4995  11.00000  0.05    0.33
Q2    1   0.7873  0.6369  0.6450  11.00000  0.05    0.32
Q3    1   0.5739  0.5647  0.5954  11.00000  0.05    0.32
Q4    1   0.5481  0.7620  0.6226  11.00000  0.05    0.29
Q5    1   0.9816  0.2574  0.5611  11.00000  0.05    0.28
;
_shelx_res_checksum              48752
_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_324xzy4_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2474279'
loop_
_audit_author_name
_audit_author_address
'zeyu xu'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2025-12-01 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl O4), C6 H16 N2'
_chemical_formula_sum            'C6 H16 Cl2 N2 O8'
_chemical_formula_weight         315.11
_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                   6.1177(4)
_cell_length_b                   14.9480(11)
_cell_length_c                   6.9688(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.692(2)
_cell_angle_gamma                90
_cell_volume                     624.06(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3769
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.556
_exptl_absorpt_correction_T_max  0.093178
_exptl_absorpt_correction_T_min  0.059408
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 16706 reflections, Rint = 0.0810
 (5968 with I > 3sig(I), Rint = 0.0625)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            1281
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.376
_diffrn_reflns_theta_min         2.725
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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           1.4
_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                1053
_reflns_number_total             1281
_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 (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.41 (?, 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.165
_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)+3.6953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1527
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Riding coordinates:
 C009(C008,H00G)
;
_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
Cl01 Cl 0.11212(19) 0.63722(7) 0.50460(16) 0.0240(3) Uani 1 1 d . . . . .
O003 O 0.0460(8) 0.6127(3) 0.6818(6) 0.0539(12) Uani 1 1 d . . . . .
O004 O 0.3273(7) 0.5955(3) 0.5115(6) 0.0597(14) Uani 1 1 d . . . . .
O005 O -0.0340(8) 0.6059(3) 0.3350(6) 0.0604(14) Uani 1 1 d . . . . .
O006 O 0.1395(8) 0.7310(3) 0.4993(7) 0.0552(12) Uani 1 1 d . . . . .
N002 N 0.5316(7) 0.5878(3) 0.9201(6) 0.0224(9) Uani 1 1 d . . . . .
H002 H 0.431(10) 0.583(4) 0.827(9) 0.036(16) Uiso 1 1 d . . . . .
C007 C 0.3084(9) 0.4870(3) 1.0844(8) 0.0274(11) Uani 1 1 d . . . . .
H00A H 0.192(9) 0.483(3) 0.976(8) 0.027(14) Uiso 1 1 d . . . . .
H00B H 0.247(9) 0.479(4) 1.184(9) 0.036(16) Uiso 1 1 d . . . . .
H00F H 0.536(8) 0.583(3) 1.204(7) 0.021(12) Uiso 1 1 d . . . . .
C009 C 0.6402(6) 0.6770(2) 0.9190(5) 0.0280(11) Uani 1 1 d . . . . .
C008 C 0.4225(6) 0.5761(2) 1.0911(5) 0.0259(11) Uani 1 1 d R . . . .
H00G H 0.345072 0.623140 1.125930 0.035(15) Uiso 1 1 d R . . . .
H00C H 0.758(8) 0.681(3) 1.033(7) 0.018(12) Uiso 1 1 d . . . . .
H00D H 0.714(9) 0.681(4) 0.813(8) 0.031(14) Uiso 1 1 d . . . . .
H00E H 0.529(8) 0.720(3) 0.930(7) 0.023(13) Uiso 1 1 d . . . . .

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
Cl01 0.0270(6) 0.0244(5) 0.0196(5) 0.0014(5) 0.0025(4) 0.0004(5)
O003 0.072(3) 0.059(3) 0.038(2) 0.006(2) 0.030(2) -0.015(2)
O004 0.043(2) 0.093(4) 0.038(2) -0.012(2) -0.0023(19) 0.038(2)
O005 0.055(3) 0.067(3) 0.046(3) -0.010(2) -0.022(2) -0.007(2)
O006 0.073(3) 0.029(2) 0.067(3) 0.003(2) 0.022(2) -0.013(2)
N002 0.023(2) 0.027(2) 0.0161(18) 0.0023(16) -0.0010(16) 0.0011(17)
C007 0.027(3) 0.029(3) 0.029(3) 0.002(2) 0.013(2) 0.004(2)
C009 0.029(3) 0.029(3) 0.027(3) 0.005(2) 0.008(2) -0.001(2)
C008 0.028(3) 0.029(3) 0.023(2) -0.001(2) 0.011(2) 0.003(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
Cl01 O003 1.423(4) . ?
Cl01 O004 1.448(4) . ?
Cl01 O005 1.410(4) . ?
Cl01 O006 1.413(4) . ?
N002 H002 0.80(6) . ?
N002 C007 1.491(6) 3_667 ?
N002 C009 1.490(5) . ?
N002 C008 1.490(5) . ?
C007 H00A 0.93(5) . ?
C007 H00B 0.86(6) . ?
C007 C008 1.500(6) . ?
C009 H00C 0.96(5) . ?
C009 H00D 0.94(5) . ?
C009 H00E 0.95(5) . ?
C008 H00F 0.94(5) . ?
C008 H00G 0.9079 . ?

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
O003 Cl01 O004 106.1(3) . . ?
O005 Cl01 O003 113.5(3) . . ?
O005 Cl01 O004 107.6(3) . . ?
O005 Cl01 O006 111.4(3) . . ?
O006 Cl01 O003 109.5(3) . . ?
O006 Cl01 O004 108.4(3) . . ?
C007 N002 H002 109(4) 3_667 . ?
C009 N002 H002 110(4) . . ?
C009 N002 C007 112.1(4) . 3_667 ?
C008 N002 H002 104(4) . . ?
C008 N002 C007 109.3(3) . 3_667 ?
C008 N002 C009 112.4(3) . . ?
N002 C007 H00A 109(3) 3_667 . ?
N002 C007 H00B 108(4) 3_667 . ?
N002 C007 C008 111.3(4) 3_667 . ?
H00A C007 H00B 105(5) . . ?
C008 C007 H00A 111(3) . . ?
C008 C007 H00B 112(4) . . ?
N002 C009 H00C 108(3) . . ?
N002 C009 H00D 110(3) . . ?
N002 C009 H00E 106(3) . . ?
H00C C009 H00D 104(4) . . ?
H00C C009 H00E 108(4) . . ?
H00D C009 H00E 119(4) . . ?
N002 C008 C007 111.2(3) . . ?
N002 C008 H00F 106(3) . . ?
N002 C008 H00G 117.7 . . ?
C007 C008 H00F 112(3) . . ?
C007 C008 H00G 115.5 . . ?
H00F C008 H00G 91.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N002 H002 O004 0.80(6) 2.17(6) 2.870(6) 147(5) . yes

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
N002 C007 C008 N002 57.9(5) 3_667 . . . ?
C007 N002 C008 C007 -56.7(5) 3_667 . . . ?
C009 N002 C008 C007 178.1(3) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_file                  
;
TITL 324xzy4_0m_4_a.res in P2(1)/c
    324xzy4_0m_4.res
    created by SHELXL-2018/3 at 09:05:27 on 01-Dec-2025
REM Old TITL 324xzy4_0m_4_a.res in P2(1)/n New:P21/c
REM SHELXT solution in P2(1)/c: R1 0.185, Rweak 0.029, Alpha 0.034
REM <I/s> 0.981 for 58 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 Cl N
CELL 0.71073 6.1177 14.948 6.9688 90 101.692 90
ZERR 2 0.0004 0.0011 0.0004 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 12 32 4 4 16

L.S. 40
PLAN  5
SIZE 0.02 0.02 0.02
TEMP -123
CONF
HTAB N002 O004
LIST 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\324XZY4_0m_4.hkl">
REM </olex2.extras>

WGHT    0.000000    3.695300
FVAR       0.86763
CL01  3    0.112124    0.637223    0.504599    11.00000    0.02701    0.02436 =
         0.01958    0.00141    0.00251    0.00045
O003  5    0.046013    0.612748    0.681783    11.00000    0.07220    0.05919 =
         0.03841    0.00575    0.03010   -0.01515
O004  5    0.327326    0.595548    0.511543    11.00000    0.04339    0.09334 =
         0.03797   -0.01246   -0.00228    0.03772
O005  5   -0.034036    0.605946    0.334958    11.00000    0.05461    0.06706 =
         0.04562   -0.01004   -0.02239   -0.00656
O006  5    0.139525    0.731014    0.499315    11.00000    0.07294    0.02906 =
         0.06669    0.00255    0.02150   -0.01258
N002  4    0.531647    0.587840    0.920075    11.00000    0.02254    0.02652 =
         0.01615    0.00226   -0.00101    0.00111
H002  2    0.431398    0.583471    0.826589    11.00000    0.03614
C007  1    0.308441    0.487037    1.084431    11.00000    0.02734    0.02880 =
         0.02912    0.00197    0.01283    0.00432
H00A  2    0.191795    0.482689    0.975569    11.00000    0.02723
H00B  2    0.247335    0.478730    1.183521    11.00000    0.03604
H00F  2    0.535975    0.582906    1.203554    11.00000    0.02091
C009  1    0.640162    0.677050    0.918969    11.00000    0.02942    0.02853 =
         0.02697    0.00509    0.00795   -0.00130
AFIX   3
C008  1    0.422532    0.576110    1.091110    11.00000    0.02846    0.02903 =
         0.02292   -0.00085    0.01140    0.00281
H00G  2    0.345072    0.623140    1.125930    11.00000    0.03507
AFIX   0
H00C  2    0.758440    0.681140    1.033477    11.00000    0.01844
H00D  2    0.713622    0.681005    0.813420    11.00000    0.03065
H00E  2    0.529160    0.720303    0.930236    11.00000    0.02289
HKLF 4




REM  324xzy4_0m_4_a.res in P2(1)/c
REM wR2 = 0.1527, GooF = S = 1.165, Restrained GooF = 1.165 for all data
REM R1 = 0.0716 for 1053 Fo > 4sig(Fo) and 0.0969 for all 1281 data
REM 108 parameters refined using 0 restraints

END

WGHT      0.0000      3.6953

REM Highest difference peak  0.745,  deepest hole -0.516,  1-sigma level  0.125
Q1    1  -0.1078  0.6123  0.5683  11.00000  0.05    0.74
Q2    1   0.0935  0.6340  0.8817  11.00000  0.05    0.54
Q3    1   0.1421  0.5641  0.6219  11.00000  0.05    0.53
Q4    1   0.3582  0.6726  0.4996  11.00000  0.05    0.49
Q5    1  -0.0221  0.6365  0.4298  11.00000  0.05    0.44
;
_shelx_res_checksum              92363
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT881_324xzy4_0m_4        
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !  
RESPONSE:Twinned structure
;
# end Validation Reply Form
####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2474281'
loop_
_audit_author_name
_audit_author_address
'zeyu xu'
;Northwestern Polytechnical University
China
;
_audit_update_record             
;
2025-12-01 deposited with the CCDC.	2025-12-15 downloaded from the CCDC.
;
_audit_creation_date             2025-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl O4), C4 H12 N2, 2(H2 O)'
_chemical_formula_sum            'C4 H16 Cl2 N2 O10'
_chemical_formula_weight         323.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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/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                   7.1870(5)
_cell_length_b                   6.4760(4)
_cell_length_c                   13.3062(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.000(2)
_cell_angle_gamma                90
_cell_volume                     615.92(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1970
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1043 before and 0.0725 after correction.
The Ratio of minimum to maximum transmission is 0.6474.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4361
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.507
_diffrn_reflns_theta_max         24.507
_diffrn_reflns_theta_min         3.079
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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                859
_reflns_number_total             1012
_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 (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.41 (?, 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.074
_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)+(0.0366P)²+0.8094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O003(H00G,H00H)
2.b Secondary CH2 refined with riding coordinates:
 N00A(H00A,H00B), C00C(H00C,H00D), C00F(H00E,H00F)
;
_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
Cl01 Cl 0.55608(9) 0.39574(11) 0.34154(5) 0.0207(3) Uani 1 1 d . . . . .
O004 O 0.6785(3) 0.4728(4) 0.42511(16) 0.0289(6) Uani 1 1 d . . . . .
O007 O 0.6663(3) 0.3326(3) 0.26234(16) 0.0276(5) Uani 1 1 d . . . . .
O00E O 0.4550(3) 0.2206(4) 0.37355(18) 0.0391(6) Uani 1 1 d . . . . .
O00G O 0.4256(3) 0.5524(4) 0.30458(19) 0.0450(7) Uani 1 1 d . . . . .
N00A N 0.5267(3) 0.2961(4) 0.03941(18) 0.0214(6) Uani 1 1 d . . . . .
H00A H 0.550154 0.207482 0.092267 0.026 Uiso 1 1 calc R U . . .
H00B H 0.512651 0.220325 -0.018473 0.026 Uiso 1 1 calc R U . . .
C00C C 0.3500(4) 0.4114(4) 0.0503(2) 0.0211(7) Uani 1 1 d . . . . .
H00C H 0.361778 0.487915 0.115018 0.025 Uiso 1 1 calc R U . . .
H00D H 0.244587 0.313055 0.050708 0.025 Uiso 1 1 calc R U . . .
C00F C 0.6882(4) 0.4397(4) 0.0365(2) 0.0221(7) Uani 1 1 d . . . . .
H00E H 0.803010 0.359688 0.028193 0.027 Uiso 1 1 calc R U . . .
H00F H 0.708441 0.517047 0.100834 0.027 Uiso 1 1 calc R U . . .
O003 O 0.0471(3) 0.4265(3) 0.35444(15) 0.0220(5) Uani 1 1 d G . . . .
H00G H -0.033489 0.388530 0.304514 0.033 Uiso 1 1 d G U . . .
H00H H 0.154462 0.422994 0.329811 0.033 Uiso 1 1 d G 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
Cl01 0.0182(4) 0.0262(4) 0.0178(4) 0.0014(3) 0.0018(3) -0.0011(3)
O004 0.0253(12) 0.0400(13) 0.0204(12) -0.0054(10) -0.0020(10) -0.0050(10)
O007 0.0232(11) 0.0419(13) 0.0191(11) -0.0056(10) 0.0081(10) -0.0017(9)
O00E 0.0352(14) 0.0421(14) 0.0417(14) -0.0008(11) 0.0124(12) -0.0184(11)
O00G 0.0394(14) 0.0552(16) 0.0395(15) 0.0107(12) -0.0006(13) 0.0236(12)
N00A 0.0290(14) 0.0165(12) 0.0185(13) 0.0009(10) 0.0013(11) 0.0016(10)
C00C 0.0234(16) 0.0233(16) 0.0172(16) -0.0007(12) 0.0053(13) 0.0001(12)
C00F 0.0203(15) 0.0231(16) 0.0228(16) 0.0015(12) 0.0019(14) 0.0012(12)
O003 0.0176(11) 0.0281(12) 0.0206(12) -0.0010(9) 0.0029(9) -0.0001(9)

_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
Cl01 O004 1.434(2) . ?
Cl01 O007 1.442(2) . ?
Cl01 O00E 1.435(2) . ?
Cl01 O00G 1.433(2) . ?
N00A H00A 0.9100 . ?
N00A H00B 0.9100 . ?
N00A C00C 1.493(4) . ?
N00A C00F 1.491(4) . ?
C00C H00C 0.9900 . ?
C00C H00D 0.9900 . ?
C00C C00F 1.507(4) 3_665 ?
C00F H00E 0.9900 . ?
C00F H00F 0.9900 . ?
O003 H00G 0.8698 . ?
O003 H00H 0.8698 . ?

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
O004 Cl01 O007 109.02(13) . . ?
O004 Cl01 O00E 109.49(14) . . ?
O00E Cl01 O007 109.07(14) . . ?
O00G Cl01 O004 110.26(15) . . ?
O00G Cl01 O007 109.84(14) . . ?
O00G Cl01 O00E 109.13(15) . . ?
H00A N00A H00B 108.0 . . ?
C00C N00A H00A 109.4 . . ?
C00C N00A H00B 109.4 . . ?
C00F N00A H00A 109.4 . . ?
C00F N00A H00B 109.4 . . ?
C00F N00A C00C 111.3(2) . . ?
N00A C00C H00C 109.8 . . ?
N00A C00C H00D 109.8 . . ?
N00A C00C C00F 109.5(2) . 3_665 ?
H00C C00C H00D 108.2 . . ?
C00F C00C H00C 109.8 3_665 . ?
C00F C00C H00D 109.8 3_665 . ?
N00A C00F C00C 109.8(2) . 3_665 ?
N00A C00F H00E 109.7 . . ?
N00A C00F H00F 109.7 . . ?
C00C C00F H00E 109.7 3_665 . ?
C00C C00F H00F 109.7 3_665 . ?
H00E C00F H00F 108.2 . . ?
H00G O003 H00H 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N00A H00A O003 0.91 2.10 2.857(3) 140.1 2_545 yes
N00A H00B O003 0.91 1.98 2.869(3) 166.0 4_665 yes

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
C00C N00A C00F C00C -58.5(3) . . . 3_665 ?
C00F N00A C00C C00F 58.3(3) . . . 3_665 ?

_shelx_res_file                  
;
TITL 111_a.res in Pn New:P21/n
    111.res
    created by SHELXL-2018/3 at 08:54:38 on 01-Dec-2025
CELL 0.71073 7.187 6.476 13.3062 90 96 90
ZERR 2 0.0005 0.0004 0.001 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl N O
UNIT 8 32 4 4 20
EQIV $1 0.5-X,-0.5+Y,0.5-Z
EQIV $2 0.5+X,0.5-Y,-0.5+Z

L.S. 5
PLAN  5
TEMP -103
CONF
HTAB N00A O003_$1
HTAB N00A O003_$2
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\111.hkl">
REM </olex2.extras>

WGHT    0.036600    0.809400
FVAR       0.87060
CL01  3    0.556083    0.395741    0.341542    11.00000    0.01819    0.02619 =
         0.01782    0.00135    0.00178   -0.00106
O004  5    0.678525    0.472797    0.425106    11.00000    0.02529    0.04000 =
         0.02043   -0.00536   -0.00196   -0.00496
O007  5    0.666299    0.332635    0.262340    11.00000    0.02319    0.04194 =
         0.01906   -0.00558    0.00810   -0.00165
O00E  5    0.454982    0.220649    0.373552    11.00000    0.03525    0.04205 =
         0.04168   -0.00075    0.01245   -0.01839
O00G  5    0.425629    0.552381    0.304578    11.00000    0.03942    0.05517 =
         0.03952    0.01068   -0.00055    0.02360
N00A  4    0.526659    0.296141    0.039405    11.00000    0.02895    0.01646 =
         0.01851    0.00091    0.00132    0.00162
AFIX  23
H00A  2    0.550154    0.207482    0.092267    11.00000   -1.20000
H00B  2    0.512651    0.220325   -0.018473    11.00000   -1.20000
AFIX   0
C00C  1    0.349975    0.411377    0.050259    11.00000    0.02338    0.02327 =
         0.01725   -0.00069    0.00527    0.00009
AFIX  23
H00C  2    0.361778    0.487915    0.115018    11.00000   -1.20000
H00D  2    0.244587    0.313055    0.050708    11.00000   -1.20000
AFIX   0
C00F  1    0.688207    0.439671    0.036452    11.00000    0.02032    0.02309 =
         0.02280    0.00151    0.00188    0.00121
AFIX  23
H00E  2    0.803010    0.359688    0.028193    11.00000   -1.20000
H00F  2    0.708441    0.517047    0.100834    11.00000   -1.20000
AFIX   6

O003  5    0.047064    0.426491    0.354443    11.00000    0.01763    0.02809 =
         0.02057   -0.00099    0.00288   -0.00007
H00G  2   -0.033489    0.388530    0.304514    11.00000   -1.50000
H00H  2    0.154462    0.422994    0.329811    11.00000   -1.50000
AFIX   0
HKLF 4




REM  111_a.res in Pn New:P21/n
REM wR2 = 0.1000, GooF = S = 1.074, Restrained GooF = 1.074 for all data
REM R1 = 0.0405 for 859 Fo > 4sig(Fo) and 0.0531 for all 1012 data
REM 85 parameters refined using 0 restraints

END

WGHT      0.0366      0.8094

REM Highest difference peak  0.346,  deepest hole -0.452,  1-sigma level  0.076
Q1    1   0.5465  0.5739  0.3185  11.00000  0.05    0.35
Q2    1   0.4684  0.6785  0.3056  11.00000  0.05    0.31
Q3    1   0.3588  0.2893  0.3410  11.00000  0.05    0.28
Q4    1   0.7008  0.4684  0.2839  11.00000  0.05    0.26
Q5    1   0.6022  0.2016  0.4379  11.00000  0.05    0.26
;
_shelx_res_checksum              52895
_olex2_submission_special_instructions 'No special instructions were received'
