# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 2268504'
loop_
_audit_author_name
_audit_author_address
'Lin Junqi'
;Huanggang Normal University
China
;
_audit_update_record             
;
2024-01-29 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_audit_creation_date             2024-01-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 Cl Cu N4 O4, Cl O4'
_chemical_formula_sum            'C16 H22 Cl2 Cu N4 O8'
_chemical_formula_weight         532.81
_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'
Cu Cu 0.3201 1.2651 '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                   13.3806(4)
_cell_length_b                   11.9359(4)
_cell_length_c                   12.9332(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2065.55(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9634
_cell_measurement_temperature    192.00
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            43215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      192.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1956
_reflns_number_total             2218
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     289
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.086
_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)+(0.0329P)²+1.7822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0761
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-O1 \\sim Cl1-O4 \\sim Cl1-O2 \\sim Cl1-O3
 with sigma of 0.02
 O1-O2 \\sim O1-O3 \\sim O1-O4 \\sim O2-O3 \\sim O2-O4 \\sim O3-O4
 with sigma of 0.02
 O5-O6 \\sim O5-O7 \\sim O5-O8 \\sim O6-O7 \\sim O6-O8 \\sim O7-O8
 with sigma of 0.02
 Cl2-O8 \\sim Cl2-O6 \\sim Cl2-O5 \\sim Cl2-O7
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl2 \\sim Cl1A \\sim O1 \\sim O2 \\sim O3 \\sim O4 \\sim O5 \\sim O7
\\sim O6 \\sim O1A \\sim O2A \\sim O3A \\sim O4A \\sim O8: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{Cl1A, O1A, O2A, O3A, O4A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{Cl1, O1, O2, O3, O4}
5. Others
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=0.5*(1-FVAR(2))
 Sof(Cl1)=Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=0.5*FVAR(2)
 Fixed Sof: O7(0.5) O6(0.5) O8(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
6.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C)
;
_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
Cu1 Cu 0.73339(2) 0.750000 0.49810(2) 0.02478(12) Uani 1 2 d S T P . .
Cl1 Cl 0.67054(15) 0.7460(11) 0.77026(15) 0.0282(6) Uani 0.401(3) 1 d D U P A
-1
O1 O 0.6613(3) 0.7711(5) 0.6608(3) 0.0389(16) Uani 0.401(3) 1 d D U P A -1
O2 O 0.6675(6) 0.6267(4) 0.7840(6) 0.065(2) Uani 0.401(3) 1 d D U P A -1
O3 O 0.7643(4) 0.7837(4) 0.8075(4) 0.0663(18) Uani 0.401(3) 1 d D U P A -1
O4 O 0.5894(5) 0.7962(5) 0.8215(4) 0.079(2) Uani 0.401(3) 1 d D U P A -1
N006 N 0.81713(14) 0.60637(18) 0.51016(14) 0.0399(5) Uani 1 1 d . . . . .
N7 N 0.63496(12) 0.64618(14) 0.44330(12) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.55538(14) 0.68826(18) 0.39295(14) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.50840(19) 0.5027(2) 0.34866(19) 0.0510(7) Uani 1 1 d . . . . .
H2 H 0.463935 0.452148 0.315477 0.061 Uiso 1 1 calc R U . . .
C3 C 0.87785(19) 0.5964(3) 0.4143(2) 0.0572(7) Uani 1 1 d . . . . .
H3A H 0.834611 0.606184 0.353844 0.086 Uiso 1 1 calc R U . . .
H3B H 0.909106 0.522185 0.411824 0.086 Uiso 1 1 calc R U . . .
H3C H 0.929844 0.654207 0.414171 0.086 Uiso 1 1 calc R U . . .
C4 C 0.48874(16) 0.6161(2) 0.34552(17) 0.0417(6) Uani 1 1 d . . . . .
H4 H 0.430864 0.643954 0.311618 0.050 Uiso 1 1 calc R U . . .
C5 C 0.74495(19) 0.5114(2) 0.51249(19) 0.0437(6) Uani 1 1 d . . . . .
H5A H 0.724215 0.496912 0.584745 0.052 Uiso 1 1 calc R U . . .
H5B H 0.777767 0.442921 0.485748 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5914(2) 0.4614(2) 0.39908(19) 0.0475(6) Uani 1 1 d . . . . .
H6 H 0.605204 0.383316 0.400380 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8839(2) 0.5969(3) 0.6019(2) 0.0658(9) Uani 1 1 d . . . . .
H7A H 0.937719 0.652207 0.596488 0.099 Uiso 1 1 calc R U . . .
H7B H 0.912593 0.521411 0.604523 0.099 Uiso 1 1 calc R U . . .
H7C H 0.845178 0.610762 0.664911 0.099 Uiso 1 1 calc R U . . .
C8 C 0.65414(16) 0.53737(18) 0.44784(16) 0.0340(5) Uani 1 1 d . . . . .
Cl2 Cl 0.70494(5) 0.750000 0.15642(6) 0.03360(18) Uani 1 2 d DS TU P . .
O5 O 0.77608(19) 0.750000 0.07389(19) 0.0501(6) Uani 1 2 d DS TU P B .
O7 O 0.7035(6) 0.6395(5) 0.2053(5) 0.065(2) Uani 0.5 1 d D U P B -1
O6 O 0.6089(2) 0.7730(6) 0.1174(3) 0.067(2) Uani 0.5 1 d D U P B -1
Cl1A Cl 0.6421(6) 0.7530(17) 0.7519(7) 0.0374(18) Uani 0.099(3) 1 d D U P A -2
O1A O 0.7046(11) 0.7898(16) 0.6687(11) 0.037(3) Uani 0.099(3) 1 d D U P A -2
O2A O 0.5440(8) 0.7334(17) 0.7125(13) 0.054(4) Uani 0.099(3) 1 d D U P A -2
O3A O 0.6843(17) 0.6566(19) 0.798(2) 0.057(5) Uani 0.099(3) 1 d D U P A -2
O4A O 0.6367(15) 0.8413(19) 0.8258(13) 0.040(4) Uani 0.099(3) 1 d D U P A -2
O8 O 0.7342(6) 0.8288(5) 0.2314(5) 0.0660(19) Uani 0.5 1 d D U P B -1


_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
Cu1 O1 2.328(4) . ?
Cu1 N006 2.0540(19) . ?
Cu1 N006 2.0540(19) 7_575 ?
Cu1 N7 1.9423(16) 7_575 ?
Cu1 N7 1.9423(16) . ?
Cu1 O1A 2.290(13) . ?
Cl1 O1 1.453(5) . ?
Cl1 O2 1.435(13) . ?
Cl1 O3 1.418(6) . ?
Cl1 O4 1.406(7) . ?
N006 C3 1.487(3) . ?
N006 C5 1.490(3) . ?
N006 C7 1.489(3) . ?
N7 C1 1.345(2) . ?
N7 C8 1.325(3) . ?
C1 C1 1.474(4) 7_575 ?
C1 C4 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C4 1.379(4) . ?
C2 C6 1.379(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C8 1.507(3) . ?
C6 H6 0.9500 . ?
C6 C8 1.387(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
Cl2 O5 1.430(2) . ?
Cl2 O7 1.463(6) . ?
Cl2 O6 1.408(3) . ?
Cl2 O8 1.406(6) . ?
Cl1A O1A 1.431(12) . ?
Cl1A O2A 1.428(11) . ?
Cl1A O3A 1.416(13) . ?
Cl1A O4A 1.424(13) . ?

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
N006 Cu1 O1 104.34(14) . . ?
N006 Cu1 O1 93.84(15) 7_575 . ?
N006 Cu1 N006 113.16(12) . 7_575 ?
N006 Cu1 O1A 81.1(4) 7_575 . ?
N006 Cu1 O1A 101.0(5) . . ?
N7 Cu1 O1 96.77(14) . . ?
N7 Cu1 O1 88.85(12) 7_575 . ?
N7 Cu1 N006 158.46(7) 7_575 . ?
N7 Cu1 N006 82.25(8) . . ?
N7 Cu1 N006 82.25(8) 7_575 7_575 ?
N7 Cu1 N006 158.46(7) . 7_575 ?
N7 Cu1 N7 79.29(10) 7_575 . ?
N7 Cu1 O1A 96.0(5) 7_575 . ?
N7 Cu1 O1A 111.7(4) . . ?
O2 Cl1 O1 108.8(7) . . ?
O3 Cl1 O1 109.9(5) . . ?
O3 Cl1 O2 107.4(6) . . ?
O4 Cl1 O1 107.8(6) . . ?
O4 Cl1 O2 110.0(6) . . ?
O4 Cl1 O3 112.8(7) . . ?
Cl1 O1 Cu1 145.4(4) . . ?
C3 N006 Cu1 107.56(16) . . ?
C3 N006 C5 108.1(2) . . ?
C3 N006 C7 109.3(2) . . ?
C5 N006 Cu1 106.45(13) . . ?
C7 N006 Cu1 116.82(17) . . ?
C7 N006 C5 108.3(2) . . ?
C1 N7 Cu1 118.36(14) . . ?
C8 N7 Cu1 118.54(14) . . ?
C8 N7 C1 122.73(18) . . ?
N7 C1 C1 111.92(11) . 7_575 ?
N7 C1 C4 119.5(2) . . ?
C4 C1 C1 128.51(14) . 7_575 ?
C4 C2 H2 119.4 . . ?
C6 C2 H2 119.4 . . ?
C6 C2 C4 121.2(2) . . ?
N006 C3 H3A 109.5 . . ?
N006 C3 H3B 109.5 . . ?
N006 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4 120.8 . . ?
C2 C4 C1 118.4(2) . . ?
C2 C4 H4 120.8 . . ?
N006 C5 H5A 109.5 . . ?
N006 C5 H5B 109.5 . . ?
N006 C5 C8 110.78(19) . . ?
H5A C5 H5B 108.1 . . ?
C8 C5 H5A 109.5 . . ?
C8 C5 H5B 109.5 . . ?
C2 C6 H6 121.0 . . ?
C2 C6 C8 117.9(2) . . ?
C8 C6 H6 121.0 . . ?
N006 C7 H7A 109.5 . . ?
N006 C7 H7B 109.5 . . ?
N006 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N7 C8 C5 112.48(19) . . ?
N7 C8 C6 120.2(2) . . ?
C6 C8 C5 127.2(2) . . ?
O5 Cl2 O7 109.4(3) . . ?
O6 Cl2 O5 109.9(2) . . ?
O6 Cl2 O7 108.6(4) . . ?
O8 Cl2 O5 109.2(3) . . ?
O8 Cl2 O7 108.0(3) . . ?
O8 Cl2 O6 111.8(4) . . ?
O2A Cl1A O1A 108.7(9) . . ?
O3A Cl1A O1A 109.7(11) . . ?
O3A Cl1A O2A 112.6(12) . . ?
O3A Cl1A O4A 109.6(10) . . ?
O4A Cl1A O1A 107.9(11) . . ?
O4A Cl1A O2A 108.3(10) . . ?
Cl1A O1A Cu1 139.3(11) . . ?

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
Cu1 N006 C5 C8 32.8(2) . . . . ?
Cu1 N7 C1 C1 -2.77(13) . . . 7_575 ?
Cu1 N7 C1 C4 174.47(14) . . . . ?
Cu1 N7 C8 C5 9.5(2) . . . . ?
Cu1 N7 C8 C6 -172.57(16) . . . . ?
O2 Cl1 O1 Cu1 -62.3(10) . . . . ?
O3 Cl1 O1 Cu1 55.0(15) . . . . ?
O4 Cl1 O1 Cu1 178.4(6) . . . . ?
N006 C5 C8 N7 -28.8(3) . . . . ?
N006 C5 C8 C6 153.5(2) . . . . ?
N7 C1 C4 C2 -2.2(3) . . . . ?
C1 N7 C8 C5 -177.55(18) . . . . ?
C1 N7 C8 C6 0.3(3) . . . . ?
C1 C1 C4 C2 174.54(14) 7_575 . . . ?
C2 C6 C8 N7 -1.5(3) . . . . ?
C2 C6 C8 C5 176.1(2) . . . . ?
C3 N006 C5 C8 -82.5(2) . . . . ?
C4 C2 C6 C8 0.8(3) . . . . ?
C6 C2 C4 C1 1.0(3) . . . . ?
C7 N006 C5 C8 159.16(19) . . . . ?
C8 N7 C1 C1 -175.69(15) . . . 7_575 ?
C8 N7 C1 C4 1.5(3) . . . . ?
O2A Cl1A O1A Cu1 -41(2) . . . . ?
O3A Cl1A O1A Cu1 82(2) . . . . ?
O4A Cl1A O1A Cu1 -158.2(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
