# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_WSA2
_database_code_depnum_ccdc_archive 'CCDC 2051341'
loop_
_audit_author_name
_audit_author_address
'Houcine Naili'
;University of Sfax
Tunisia
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 09 octobre 2018                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H14 Cl4 Cu N2'
_chemical_formula_sum            'C5 H14 Cl4 Cu N2'
_chemical_formula_weight         307.52
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   6.0751(3)
_cell_length_b                   15.6732(8)
_cell_length_c                   12.0466(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.521(2)
_cell_angle_gamma                90
_cell_volume                     1134.37(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8153
_cell_measurement_theta_min      2.5991
_cell_measurement_theta_max      27.5571
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.0229470
_diffrn_orient_matrix_UB_21      0.1025180
_diffrn_orient_matrix_UB_31      0.1291017
_diffrn_orient_matrix_UB_12      -0.0422361
_diffrn_orient_matrix_UB_22      0.0335105
_diffrn_orient_matrix_UB_32      -0.0341175
_diffrn_orient_matrix_UB_13      -0.0628720
_diffrn_orient_matrix_UB_23      -0.0410816
_diffrn_orient_matrix_UB_33      0.0374823


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             620
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.945

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS V6.2.1/2016-03-01                           #
# Number of scans            :  2                                              #
# Total length of scans  [*] :   207.00 (deg.)                                 #
# Total number of frames [*] :      207                                        #
# Rotation speed         [*] :   120.00 sec./deg.                              #
# Total exposition time  [*] :      6 h  54.0 min.                             #
#                                                                              #
#  [*] fast scan not included                                                  #
#                                                                              #
# Option                     : shutterless mode                                #
#                                                                              #
#     Scan Time(s)  Width  DX (mm)  Frames  Theta  Omega    Phi    Chi   T(K)  #
#                                                                              #
#  1 Phi     120.0   1.00     34.0     207   0.27 270.94 312.51  23.00 150.00  #
#  2 Fast     10.0   1.00     34.0     180   0.00 360.00   0.00  54.74 150.00  #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0275
_diffrn_reflns_av_r_equivalents  0.0294
_diffrn_reflns_number            9642
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.111
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2607
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  
'CRYSCALC (T. Roisnel, local program, ver. 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+5.0924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2607
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.778
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.144

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.21898(7) 0.47532(2) 0.39737(3) 0.00998(13) Uani 1 1 d . . . . .
Cl1 Cl 0.24207(12) 0.33441(4) 0.46183(6) 0.00964(17) Uani 1 1 d . . . . .
Cl2 Cl 0.27317(13) 0.52069(5) 0.57953(6) 0.01134(17) Uani 1 1 d . . . . .
Cl3 Cl 0.20791(12) 0.61708(5) 0.33791(6) 0.01108(17) Uani 1 1 d . . . . .
Cl4 Cl 0.16257(17) 0.42905(6) 0.21784(7) 0.0221(2) Uani 1 1 d . . . . .
N1 N 0.2255(5) 0.22010(18) 0.9214(2) 0.0124(5) Uani 1 1 d . . . . .
H1A H 0.116572 0.188253 0.945484 0.015 Uiso 1 1 calc R U . . .
H1B H 0.357883 0.194652 0.947278 0.015 Uiso 1 1 calc R U . . .
N2 N 0.3119(5) 0.36059(17) 0.7347(2) 0.0123(5) Uani 1 1 d . . . . .
H2A H 0.166290 0.366235 0.704277 0.015 Uiso 1 1 calc R U . . .
H2B H 0.394258 0.383176 0.684647 0.015 Uiso 1 1 calc R U . . .
C1 C 0.2242(10) 0.3058(3) 0.9734(4) 0.0411(13) Uani 1 1 d . . . . .
H1A H 0.076573 0.331913 0.949109 0.049 Uiso 1 1 calc R U . . .
H1B H 0.240723 0.298370 1.055847 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3936(9) 0.3652(3) 0.9486(4) 0.0350(10) Uani 1 1 d . . . . .
H2A H 0.534204 0.333085 0.949752 0.042 Uiso 1 1 calc R U . . .
H2B H 0.418221 0.407418 1.010349 0.042 Uiso 1 1 calc R U . . .
C3 C 0.3499(8) 0.4142(2) 0.8383(3) 0.0244(8) Uani 1 1 d . . . . .
H3A H 0.217839 0.450921 0.839603 0.029 Uiso 1 1 calc R U . . .
H3B H 0.478525 0.452089 0.833541 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3624(6) 0.2677(2) 0.7439(3) 0.0171(7) Uani 1 1 d . . . . .
H4A H 0.510449 0.259760 0.789478 0.021 Uiso 1 1 calc R U . . .
H4B H 0.369883 0.244701 0.667960 0.021 Uiso 1 1 calc R U . . .
C5 C 0.1928(6) 0.2175(2) 0.7961(3) 0.0189(7) Uani 1 1 d . . . . .
H5A H 0.042760 0.239962 0.767495 0.023 Uiso 1 1 calc R U . . .
H5B H 0.197794 0.157316 0.771733 0.023 Uiso 1 1 calc R U . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 Cl4 2.2585(9) . ?
Cu1 Cl2 2.2838(8) . ?
Cu1 Cl3 2.3323(8) . ?
Cu1 Cl1 2.3383(8) . ?
Cu1 Cl2 3.0442(9) 3_566 ?
Cu1 Cl2 3.0570(9) 3_666 ?
N1 C1 1.482(5) . ?
N1 C5 1.494(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N2 C4 1.489(4) . ?
N2 C3 1.493(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
C1 C2 1.452(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.523(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.506(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl4 Cu1 Cl2 179.25(4) . . ?
Cl4 Cu1 Cl3 91.05(3) . . ?
Cl2 Cu1 Cl3 89.54(3) . . ?
Cl4 Cu1 Cl1 90.45(3) . . ?
Cl2 Cu1 Cl1 88.96(3) . . ?
Cl3 Cu1 Cl1 177.83(3) . . ?
Cl4 Cu1 Cl2 94.73(3) . 3_566 ?
Cl2 Cu1 Cl2 84.80(3) . 3_566 ?
Cl3 Cu1 Cl2 91.40(3) . 3_566 ?
Cl1 Cu1 Cl2 90.03(3) . 3_566 ?
Cl4 Cu1 Cl2 95.84(3) . 3_666 ?
Cl2 Cu1 Cl2 84.62(3) . 3_666 ?
Cl3 Cu1 Cl2 89.50(3) . 3_666 ?
Cl1 Cu1 Cl2 88.80(3) . 3_666 ?
Cl2 Cu1 Cl2 169.38(3) 3_566 3_666 ?
C1 N1 C5 116.3(3) . . ?
C1 N1 H1A 108.2 . . ?
C5 N1 H1A 108.2 . . ?
C1 N1 H1B 108.2 . . ?
C5 N1 H1B 108.2 . . ?
H1A N1 H1B 107.4 . . ?
C4 N2 C3 118.9(3) . . ?
C4 N2 H2A 107.6 . . ?
C3 N2 H2A 107.6 . . ?
C4 N2 H2B 107.6 . . ?
C3 N2 H2B 107.6 . . ?
H2A N2 H2B 107.0 . . ?
C2 C1 N1 116.5(4) . . ?
C2 C1 H1A 108.2 . . ?
N1 C1 H1A 108.2 . . ?
C2 C1 H1B 108.2 . . ?
N1 C1 H1B 108.2 . . ?
H1A C1 H1B 107.3 . . ?
C1 C2 C3 117.8(4) . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C3 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
N2 C3 C2 115.6(3) . . ?
N2 C3 H3A 108.4 . . ?
C2 C3 H3A 108.4 . . ?
N2 C3 H3B 108.4 . . ?
C2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
N2 C4 C5 113.3(3) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N1 C5 C4 114.3(3) . . ?
N1 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?

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
C5 N1 C1 C2 -60.4(6) . . . . ?
N1 C1 C2 C3 82.1(6) . . . . ?
C4 N2 C3 C2 -11.9(5) . . . . ?
C1 C2 C3 N2 -58.6(6) . . . . ?
C3 N2 C4 C5 74.4(4) . . . . ?
C1 N1 C5 C4 58.1(4) . . . . ?
N2 C4 C5 N1 -81.8(4) . . . . ?

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
#
# Hydrogen bonding scheme
# -----------------------
#
# D       H       A       D-H         H...A       D...A      D-H...A   symm publ
# ------------------------------------------------------------------------------
N1 H1A Cl1 0.91 2.34 3.165(3) 150.7 4_566 yes
N1 H1B Cl1 0.91 2.36 3.219(3) 157.6 4_666 yes
N2 H2A Cl3 0.91 2.27 3.169(3) 169.3 3_566 yes
N2 H2B Cl1 0.91 2.81 3.277(3) 113.0 . yes
N2 H2B Cl2 0.91 2.55 3.117(3) 120.7 . yes
N2 H2B Cl3 0.91 2.47 3.186(3) 135.6 3_666 yes
C1 H1B Cl4 0.99 2.92 3.588(4) 125.9 1_556 yes
C2 H2A Cl1 0.99 2.91 3.768(5) 145.9 4_666 yes
C3 H3A Cl4 0.99 2.98 3.945(5) 165.0 3_566 yes
C4 H4A Cl1 0.99 2.76 3.603(4) 143.6 4_666 yes
C4 H4B Cl1 0.99 2.86 3.526(4) 125.4 . yes
C5 H5A Cl3 0.99 2.89 3.753(4) 145.6 3_566 yes
C5 H5B Cl2 0.99 2.78 3.422(4) 123.0 2_546 yes

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


