# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2083819'
loop_
_audit_author_name
_audit_author_address
'houcine naili'
;UNIVERSITY OF SFAX
Tunisia
;
#Added by publCIF



_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  ?
#Added by publCIF




_cell_special_details            ?

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H10 Cl4 Cu N2'
_chemical_formula_weight         315.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.331(3)
_cell_length_b                   7.7183(16)
_cell_length_c                   16.974(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2139.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1571
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      24.66

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.994
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  0.811
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9203
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.156
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2429
_reflns_number_gt                1717
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+4.8990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2429
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
N1 N 0.6474(2) 0.6443(4) 0.6820(2) 0.0153(8) Uani 1 1 d . . . . .
H1A H 0.650324 0.562295 0.720455 0.023 Uiso 1 1 calc R U . . .
H1B H 0.694912 0.706018 0.681044 0.023 Uiso 1 1 calc R U . . .
H1C H 0.604800 0.716929 0.692135 0.023 Uiso 1 1 calc R U . . .
C1 C 0.6349(3) 0.5593(6) 0.6047(3) 0.0174(10) Uani 1 1 d . . . . .
H1D H 0.583775 0.490349 0.606604 0.021 Uiso 1 1 calc R U . . .
H1E H 0.680804 0.478601 0.594662 0.021 Uiso 1 1 calc R U . . .
C2 C 0.6294(3) 0.6871(5) 0.5380(3) 0.0129(9) Uani 1 1 d . . . . .
C3 C 0.6955(3) 0.7526(6) 0.4984(3) 0.0152(9) Uani 1 1 d . . . . .
H3 H 0.749320 0.719842 0.513576 0.018 Uiso 1 1 calc R U . . .
C4 C 0.6841(3) 0.8664(5) 0.4364(3) 0.0174(10) Uani 1 1 d . . . . .
H4 H 0.729813 0.915161 0.409849 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6053(3) 0.9082(6) 0.4136(3) 0.0198(10) Uani 1 1 d . . . . .
H5 H 0.596198 0.984602 0.370612 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5408(3) 0.8386(6) 0.4535(3) 0.0173(10) Uani 1 1 d . . . . .
H6 H 0.486315 0.864272 0.437620 0.021 Uiso 1 1 calc R U . . .
N2 N 0.5542(2) 0.7340(4) 0.5150(2) 0.0144(8) Uani 1 1 d . . . . .
H2 H 0.511857 0.694271 0.541441 0.017 Uiso 1 1 calc R U . . .
Cu1 Cu 0.38388(3) 0.61347(7) 0.73238(3) 0.01335(16) Uani 1 1 d . . . . .
Cl1 Cl 0.34867(6) 0.58095(14) 0.86096(6) 0.0171(2) Uani 1 1 d . . . . .
Cl2 Cl 0.48486(7) 0.41026(14) 0.74562(7) 0.0198(3) Uani 1 1 d . . . . .
Cl3 Cl 0.28787(6) 0.82717(13) 0.71901(6) 0.0148(2) Uani 1 1 d . . . . .
Cl4 Cl 0.39876(6) 0.61001(14) 0.59834(6) 0.0183(2) 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
N1 C1 1.482(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C2 1.505(6) . ?
C1 H1D 0.9900 . ?
C1 H1E 0.9900 . ?
C2 N2 1.338(5) . ?
C2 C3 1.367(6) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(6) . ?
C5 H5 0.9500 . ?
C6 N2 1.338(5) . ?
C6 H6 0.9500 . ?
N2 H2 0.8800 . ?
Cu1 Cl1 2.2709(13) . ?
Cu1 Cl2 2.2870(12) . ?
Cu1 Cl3 2.2870(12) . ?
Cu1 Cl4 2.2882(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
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C1 C2 112.6(4) . . ?
N1 C1 H1D 109.1 . . ?
C2 C1 H1D 109.1 . . ?
N1 C1 H1E 109.1 . . ?
C2 C1 H1E 109.1 . . ?
H1D C1 H1E 107.8 . . ?
N2 C2 C3 118.8(4) . . ?
N2 C2 C1 116.8(4) . . ?
C3 C2 C1 124.4(4) . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N2 C6 C5 119.9(4) . . ?
N2 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C2 N2 C6 122.8(4) . . ?
C2 N2 H2 118.6 . . ?
C6 N2 H2 118.6 . . ?
Cl1 Cu1 Cl2 90.70(4) . . ?
Cl1 Cu1 Cl3 90.09(4) . . ?
Cl2 Cu1 Cl3 177.13(5) . . ?
Cl1 Cu1 Cl4 168.87(5) . . ?
Cl2 Cu1 Cl4 90.75(4) . . ?
Cl3 Cu1 Cl4 89.00(4) . . ?

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
N1 C1 C2 N2 -96.4(4) . . . . ?
N1 C1 C2 C3 85.8(5) . . . . ?
N2 C2 C3 C4 0.6(6) . . . . ?
C1 C2 C3 C4 178.4(4) . . . . ?
C2 C3 C4 C5 -2.1(7) . . . . ?
C3 C4 C5 C6 1.0(7) . . . . ?
C4 C5 C6 N2 1.4(7) . . . . ?
C3 C2 N2 C6 1.9(6) . . . . ?
C1 C2 N2 C6 -176.0(4) . . . . ?
C5 C6 N2 C2 -2.9(7) . . . . ?

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
N1 H1A Cl3 0.91 2.32 3.151(4) 152.3 3_646
N1 H1C Cl2 0.91 2.34 3.223(4) 162.8 3_656
N1 H1B Cl1 0.91 2.78 3.402(4) 126.3 6_657
N1 H1B Cl3 0.91 2.46 3.174(4) 135.3 6_657
C1 H1D Cl2 0.99 2.93 3.611(5) 127.2 .
C1 H1E Cl1 0.99 2.95 3.544(5) 119.4 6_657
C3 H3 Cl1 0.95 2.88 3.702(4) 145.0 6_657
C5 H5 Cl2 0.95 2.91 3.736(5) 146.2 7_575
C5 H5 Cl3 0.95 2.83 3.505(5) 128.8 5_676
C6 H6 Cl1 0.95 2.63 3.563(5) 166.7 7_575
N2 H2 Cl4 0.88 2.18 3.060(4) 174.1 .
N1 H1A Cl3 0.91 2.32 3.151(4) 152.3 3_646
N1 H1C Cl2 0.91 2.34 3.223(4) 162.8 3_656
N1 H1B Cl1 0.91 2.78 3.402(4) 126.3 6_657
N1 H1B Cl3 0.91 2.46 3.174(4) 135.3 6_657
C1 H1D Cl2 0.99 2.93 3.611(5) 127.2 .
C1 H1E Cl1 0.99 2.95 3.544(5) 119.4 6_657
C3 H3 Cl1 0.95 2.88 3.702(4) 145.0 6_657
C5 H5 Cl2 0.95 2.91 3.736(5) 146.2 7_575
C5 H5 Cl3 0.95 2.83 3.505(5) 128.8 5_676
C6 H6 Cl1 0.95 2.63 3.563(5) 166.7 7_575
N2 H2 Cl4 0.88 2.18 3.060(4) 174.1 .
N1 H1A Cl3 0.91 2.32 3.151(4) 152.3 3_646
N1 H1C Cl2 0.91 2.34 3.223(4) 162.8 3_656
N1 H1B Cl1 0.91 2.78 3.402(4) 126.3 6_657
N1 H1B Cl3 0.91 2.46 3.174(4) 135.3 6_657
C1 H1D Cl2 0.99 2.93 3.611(5) 127.2 .
C1 H1E Cl1 0.99 2.95 3.544(5) 119.4 6_657
C3 H3 Cl1 0.95 2.88 3.702(4) 145.0 6_657
C5 H5 Cl2 0.95 2.91 3.736(5) 146.2 7_575
C5 H5 Cl3 0.95 2.83 3.505(5) 128.8 5_676
C6 H6 Cl1 0.95 2.63 3.563(5) 166.7 7_575
N2 H2 Cl4 0.88 2.18 3.060(4) 174.1 .

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.146

