# 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_ld07
_database_code_depnum_ccdc_archive 'CCDC 2420747'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roller'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-01-31 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_ld07                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.857 Why?
RESPONSE: the result was not the expected one and the measurement stopped, but the quality is fine and some bondlength will be compared in the related paper
;
_vrf_PLAT910_ld07                
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).        242 Note
RESPONSE: the result was not the expected one and the measurement stopped, but the quality is fine and some bondlength will be compared in the related paper
;
# Added during the CSD deposition process: Friday 31 January 2025 09:13 AM
# end Validation Reply Form

_audit_creation_date             2025-01-31
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.01.22 svn.rc7346086 for OlexSys, GUI svn.r7128)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Cl2 N2 O'
_chemical_formula_sum            'C13 H8 Cl2 N2 O'
_chemical_formula_weight         279.11
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.7331(9)
_cell_length_b                   7.2792(6)
_cell_length_c                   13.7801(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.101(6)
_cell_angle_gamma                90
_cell_volume                     1141.46(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.02
_cell_measurement_theta_min      26.78
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.306
_exptl_absorpt_coefficient_mu    5.013
_exptl_absorpt_correction_T_max  0.0448
_exptl_absorpt_correction_T_min  0.0221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.857
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5166
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.558
_diffrn_reflns_theta_min         26.987
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.857
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
 3372 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Primux 100 micro'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1494
_reflns_number_total             1782
_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       'X-Area Recipe 2.0.2 (STOE, 2024)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.194.0 (STOE, 2023)'
_computing_data_reduction        
;
X-Area Integrate 2.5.18.0 (STOE, 2024)
X-Area LANA 2.8.4 (STOE, 2024)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1782
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.058
_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)+(0.1224P)²+0.0936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1570
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Cl1 Cl 0.87762(6) 0.63606(10) 0.48500(6) 0.0253(4) Uani 1 1 d . . . . .
Cl2 Cl 0.69691(6) 0.49575(9) 0.79915(5) 0.0225(3) Uani 1 1 d . . . . .
O1 O 0.48150(19) 0.6465(3) 0.67481(17) 0.0219(5) Uani 1 1 d . . . . .
H1 H 0.418(4) 0.690(6) 0.634(3) 0.033 Uiso 1 1 calc R U . . .
N1 N 0.3504(2) 0.7838(4) 0.51404(19) 0.0193(6) Uani 1 1 d . . . . .
N2 N 0.4156(2) 0.8438(3) 0.37838(19) 0.0182(6) Uani 1 1 d . . . . .
H2 H 0.464477 0.854038 0.339368 0.022 Uiso 1 1 calc R U . . .
C1 C 0.7591(3) 0.6434(4) 0.5395(2) 0.0195(7) Uani 1 1 d . . . . .
C2 C 0.6522(3) 0.7074(4) 0.4858(2) 0.0192(6) Uani 1 1 d . . . . .
H2A H 0.643316 0.748643 0.419017 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5566(2) 0.7119(4) 0.5292(2) 0.0176(6) Uani 1 1 d . . . . .
C4 C 0.5701(2) 0.6466(4) 0.6284(2) 0.0183(6) Uani 1 1 d . . . . .
C5 C 0.6800(3) 0.5792(4) 0.6794(2) 0.0193(6) Uani 1 1 d . . . . .
C6 C 0.7743(2) 0.5782(4) 0.6367(2) 0.0204(7) Uani 1 1 d . . . . .
H6 H 0.848642 0.533738 0.672952 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4421(2) 0.7797(4) 0.4742(2) 0.0183(6) Uani 1 1 d . . . . .
C8 C 0.2577(3) 0.8502(4) 0.4398(2) 0.0188(6) Uani 1 1 d . . . . .
C9 C 0.1403(3) 0.8793(4) 0.4396(2) 0.0233(7) Uani 1 1 d . . . . .
H9 H 0.111977 0.853535 0.497166 0.028 Uiso 1 1 calc R U . . .
C10 C 0.0668(3) 0.9463(5) 0.3537(3) 0.0268(7) Uani 1 1 d . . . . .
H10 H -0.013683 0.966367 0.352045 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1078(3) 0.9862(5) 0.2679(3) 0.0259(7) Uani 1 1 d . . . . .
H11 H 0.054695 1.033280 0.209871 0.031 Uiso 1 1 calc R U . . .
C12 C 0.2247(3) 0.9577(5) 0.2668(2) 0.0231(7) Uani 1 1 d . . . . .
H12 H 0.253022 0.983719 0.209268 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2976(2) 0.8896(4) 0.3538(2) 0.0198(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.735(3) . ?
Cl2 C5 1.724(3) . ?
O1 H1 0.88(6) . ?
O1 C4 1.346(4) . ?
N1 C7 1.321(4) . ?
N1 C8 1.386(4) . ?
N2 H2 0.8800 . ?
N2 C7 1.363(4) . ?
N2 C13 1.383(4) . ?
C1 C2 1.373(4) . ?
C1 C6 1.391(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.394(4) . ?
C3 C4 1.419(4) . ?
C3 C7 1.459(4) . ?
C4 C5 1.398(4) . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.394(4) . ?
C8 C13 1.406(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.412(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(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
C4 O1 H1 109.5 . . ?
C7 N1 C8 105.8(2) . . ?
C7 N2 H2 126.3 . . ?
C7 N2 C13 107.4(2) . . ?
C13 N2 H2 126.3 . . ?
C2 C1 Cl1 120.1(2) . . ?
C2 C1 C6 121.4(3) . . ?
C6 C1 Cl1 118.6(2) . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 C7 121.4(3) . . ?
C4 C3 C7 119.1(2) . . ?
O1 C4 C3 122.7(3) . . ?
O1 C4 C5 119.0(3) . . ?
C5 C4 C3 118.3(2) . . ?
C4 C5 Cl2 118.8(2) . . ?
C6 C5 Cl2 119.4(2) . . ?
C6 C5 C4 121.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
N1 C7 N2 112.2(2) . . ?
N1 C7 C3 122.1(3) . . ?
N2 C7 C3 125.6(2) . . ?
N1 C8 C9 130.7(3) . . ?
N1 C8 C13 109.3(2) . . ?
C9 C8 C13 120.0(3) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.9(3) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 121.7 . . ?
C13 C12 C11 116.5(3) . . ?
C13 C12 H12 121.7 . . ?
N2 C13 C8 105.2(3) . . ?
N2 C13 C12 132.0(3) . . ?
C12 C13 C8 122.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 179.4(2) . . . . ?
Cl1 C1 C6 C5 -178.3(2) . . . . ?
Cl2 C5 C6 C1 179.1(2) . . . . ?
O1 C4 C5 Cl2 0.9(4) . . . . ?
O1 C4 C5 C6 -179.0(3) . . . . ?
N1 C8 C9 C10 -179.5(3) . . . . ?
N1 C8 C13 N2 0.4(3) . . . . ?
N1 C8 C13 C12 179.8(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C2 C3 C7 179.8(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C3 C4 O1 -179.8(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C3 C7 N1 179.6(3) . . . . ?
C2 C3 C7 N2 0.1(5) . . . . ?
C3 C4 C5 Cl2 -178.9(2) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
C4 C3 C7 N1 0.5(5) . . . . ?
C4 C3 C7 N2 -178.9(3) . . . . ?
C4 C5 C6 C1 -1.1(5) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C7 N1 C8 C9 178.5(3) . . . . ?
C7 N1 C8 C13 -1.1(3) . . . . ?
C7 N2 C13 C8 0.4(3) . . . . ?
C7 N2 C13 C12 -178.9(3) . . . . ?
C7 C3 C4 O1 -0.8(4) . . . . ?
C7 C3 C4 C5 178.9(3) . . . . ?
C8 N1 C7 N2 1.4(3) . . . . ?
C8 N1 C7 C3 -178.2(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C8 C13 N2 -179.2(3) . . . . ?
C9 C8 C13 C12 0.1(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 N2 179.1(3) . . . . ?
C11 C12 C13 C8 -0.1(5) . . . . ?
C13 N2 C7 N1 -1.1(3) . . . . ?
C13 N2 C7 C3 178.4(3) . . . . ?
C13 C8 C9 C10 0.1(5) . . . . ?

####################################################################### 
# 
# 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_ld07_2
_database_code_depnum_ccdc_archive 'CCDC 2420748'
loop_
_audit_author_name
_audit_author_address
'Alexander Prado-Roller'
;University of Vienna
Austria
;
_audit_update_record             
;
2025-01-31 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;
_audit_creation_date             2025-01-31
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.01.22 svn.rc7346086 for OlexSys, GUI svn.r7128)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Cl2 N2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O'
_chemical_formula_weight         281.13
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.962(8)
_cell_length_b                   3.7880(6)
_cell_length_c                   23.455(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.90(2)
_cell_angle_gamma                90
_cell_volume                     2370.4(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9496
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.5947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14790
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.025
_diffrn_reflns_theta_min         2.851
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
 2360 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             3402
_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       'X-Area Recipe 1.37.0.0 (STOE, 2021)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)'
_computing_data_reduction        
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.031
_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)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          
;
_olex2_refinement_description

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-H2AB ∼ N2-H2B ∼ N2-H2AA
 with sigma of 0.02
3. Others
 Fixed Sof: H1(0.51) H1A(0.49) H2AA(0.72) H2AB(0.64) H2B(0.64)
 Fixed X: H1(0.5799)
 Fixed Y: H1(0.3542)
 Fixed Z: H1(0.497396)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
Cl1 Cl 0.72129(2) 0.77984(15) 0.37655(3) 0.02278(16) Uani 1 1 d . . . . .
Cl2 Cl 0.52472(2) 0.82179(17) 0.33423(3) 0.02836(18) Uani 1 1 d . . . . .
O1 O 0.55765(6) 0.4707(4) 0.45596(7) 0.0240(4) Uani 1 1 d . . . . .
H1 H 0.579900 0.354200 0.497396 0.006(10) Uiso 0.51 1 d . . P A 1
N1 N 0.62156(8) 0.1906(5) 0.55307(9) 0.0195(4) Uani 1 1 d . . . . .
H1A H 0.5854(17) 0.201(11) 0.534(2) 0.010(12) Uiso 0.49 1 d . . P B 2
N2 N 0.54243(9) -0.1282(7) 0.56973(11) 0.0327(6) Uani 1 1 d D . . . .
H2AA H 0.5176(11) -0.282(8) 0.5795(16) 0.032(10) Uiso 0.72 1 d D . P . .
H2AB H 0.5326(14) 0.120(7) 0.5763(18) 0.029(11) Uiso 0.64 1 d D . P . .
H2B H 0.5404(13) -0.116(9) 0.5248(11) 0.024(10) Uiso 0.64 1 d D . P C 2
C1 C 0.67256(8) 0.6824(6) 0.39999(10) 0.0167(5) Uani 1 1 d . . . . .
C2 C 0.68356(9) 0.5201(6) 0.45624(10) 0.0173(5) Uani 1 1 d . . . . .
H2 H 0.717207 0.461385 0.481654 0.021 Uiso 1 1 calc R U . . .
C3 C 0.64509(9) 0.4431(6) 0.47552(10) 0.0161(5) Uani 1 1 d . . . . .
C4 C 0.59481(9) 0.5366(6) 0.43793(10) 0.0178(5) Uani 1 1 d . . . . .
C5 C 0.58550(8) 0.7016(6) 0.38085(10) 0.0192(5) Uani 1 1 d . . . . .
C6 C 0.62375(9) 0.7709(6) 0.36171(10) 0.0177(5) Uani 1 1 d . . . . .
H6 H 0.616902 0.878369 0.322659 0.021 Uiso 1 1 calc R U . . .
C7 C 0.65667(9) 0.2666(6) 0.53445(10) 0.0187(5) Uani 1 1 d . . . . .
H7 H 0.690393 0.206974 0.559400 0.022 Uiso 1 1 calc R U . . .
C8 C 0.63064(9) 0.0366(6) 0.61116(10) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.67693(9) 0.0401(6) 0.66077(10) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.704965 0.141497 0.655391 0.022 Uiso 1 1 calc R U . . .
C10 C 0.68307(9) -0.0994(6) 0.71728(11) 0.0224(5) Uani 1 1 d . . . . .
H10 H 0.714944 -0.095448 0.750647 0.027 Uiso 1 1 calc R U . . .
C11 C 0.64212(9) -0.2457(6) 0.72479(11) 0.0214(5) Uani 1 1 d . . . . .
H11 H 0.645939 -0.342533 0.763735 0.026 Uiso 1 1 calc R U . . .
C12 C 0.59578(9) -0.2531(6) 0.67655(11) 0.0212(5) Uani 1 1 d . . . . .
H12 H 0.568081 -0.352560 0.682974 0.025 Uiso 1 1 calc R U . . .
C13 C 0.58880(9) -0.1175(6) 0.61860(11) 0.0226(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.742(2) . ?
Cl2 C5 1.733(2) . ?
O1 H1 1.0329(16) . ?
O1 C4 1.324(3) . ?
N1 H1A 0.97(4) . ?
N1 C7 1.286(3) . ?
N1 C8 1.410(3) . ?
N2 H2AA 1.02(2) . ?
N2 H2AB 1.01(2) . ?
N2 H2B 1.03(2) . ?
N2 C13 1.386(3) . ?
C1 C2 1.376(3) . ?
C1 C6 1.389(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 C4 1.423(3) . ?
C3 C7 1.452(3) . ?
C4 C5 1.405(3) . ?
C5 C6 1.373(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.392(3) . ?
C8 C13 1.416(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(3) . ?

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
C4 O1 H1 95.40(16) . . ?
C7 N1 H1A 133(2) . . ?
C7 N1 C8 123.1(2) . . ?
C8 N1 H1A 103(2) . . ?
H2AA N2 H2AB 104(3) . . ?
H2AA N2 H2B 119(3) . . ?
H2AB N2 H2B 102(3) . . ?
C13 N2 H2AA 112(2) . . ?
C13 N2 H2AB 95(2) . . ?
C13 N2 H2B 120(2) . . ?
C2 C1 Cl1 118.93(18) . . ?
C2 C1 C6 121.7(2) . . ?
C6 C1 Cl1 119.39(17) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 C7 119.3(2) . . ?
C4 C3 C7 120.4(2) . . ?
O1 C4 C3 121.2(2) . . ?
O1 C4 C5 120.6(2) . . ?
C5 C4 C3 118.1(2) . . ?
C4 C5 Cl2 119.28(18) . . ?
C6 C5 Cl2 119.61(18) . . ?
C6 C5 C4 121.1(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C3 120.4(2) . . ?
N1 C7 H7 119.8 . . ?
C3 C7 H7 119.8 . . ?
N1 C8 C13 116.3(2) . . ?
C9 C8 N1 124.1(2) . . ?
C9 C8 C13 119.5(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.6 . . ?
C9 C10 C11 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
N2 C13 C8 120.7(2) . . ?
N2 C13 C12 121.5(2) . . ?
C12 C13 C8 117.8(2) . . ?

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
Cl1 C1 C2 C3 179.65(17) . . . . ?
Cl1 C1 C6 C5 -178.48(17) . . . . ?
Cl2 C5 C6 C1 178.31(17) . . . . ?
O1 C4 C5 Cl2 0.5(3) . . . . ?
O1 C4 C5 C6 -180.0(2) . . . . ?
N1 C8 C9 C10 176.9(2) . . . . ?
N1 C8 C13 N2 3.0(3) . . . . ?
N1 C8 C13 C12 -176.2(2) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C7 179.0(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C3 C4 O1 -178.88(19) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C7 N1 -179.6(2) . . . . ?
C3 C4 C5 Cl2 -179.53(17) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C3 C7 N1 0.5(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 N1 C8 C9 18.8(3) . . . . ?
C7 N1 C8 C13 -163.5(2) . . . . ?
C7 C3 C4 O1 1.0(3) . . . . ?
C7 C3 C4 C5 -178.9(2) . . . . ?
C8 N1 C7 C3 -176.5(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C8 C13 N2 -179.2(2) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 N2 179.2(2) . . . . ?
C11 C12 C13 C8 -1.6(3) . . . . ?
C13 C8 C9 C10 -0.7(3) . . . . ?

