# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2051952'
loop_
_audit_author_name
_audit_author_address
'Ana Lago'
;Universidad de la Laguna
Spain
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 Cl Cu N2 S2'
_chemical_formula_sum            'C11 H10 Cl Cu N2 S2'
_chemical_formula_weight         333.32

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   7.1650(4)
_cell_length_b                   12.9313(8)
_cell_length_c                   13.5000(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.8316(18)
_cell_angle_gamma                90.00
_cell_volume                     1250.68(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.35

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    2.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5826
_exptl_absorpt_correction_T_max  0.8483
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35022
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         28.35
_reflns_number_total             3121
_reflns_number_gt                2775
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0200P)²+1.2104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3121
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0499
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.03284(3) 0.578858(16) 0.096176(14) 0.01259(6) Uani 1 1 d . . .
Cl1 Cl 0.13844(5) 0.58301(3) -0.07284(3) 0.01271(8) Uani 1 1 d . . .
S1 S -0.71329(6) 0.87031(3) 0.13174(3) 0.01452(9) Uani 1 1 d . . .
S2 S -0.77382(5) 0.92840(3) -0.08004(3) 0.01335(9) Uani 1 1 d . . .
N1 N -0.17898(18) 0.68381(10) 0.09803(10) 0.0108(3) Uani 1 1 d . . .
N2 N 0.24207(19) 0.57927(11) 0.19518(10) 0.0117(3) Uani 1 1 d . . .
C1 C -0.2137(2) 0.74666(12) 0.17570(12) 0.0119(3) Uani 1 1 d . . .
H1 H -0.1216 0.7517 0.2268 0.014 Uiso 1 1 calc R . .
C2 C -0.3750(2) 0.80385(12) 0.18515(12) 0.0119(3) Uani 1 1 d . . .
H2 H -0.3929 0.8466 0.2415 0.014 Uiso 1 1 calc R . .
C3 C -0.5114(2) 0.79782(12) 0.11041(11) 0.0099(3) Uani 1 1 d . . .
C4 C -0.4770(2) 0.73511(12) 0.02839(11) 0.0113(3) Uani 1 1 d . . .
H4 H -0.5653 0.7301 -0.0245 0.014 Uiso 1 1 calc R . .
C5 C -0.3108(2) 0.68041(12) 0.02616(11) 0.0110(3) Uani 1 1 d . . .
H5 H -0.2886 0.6377 -0.0297 0.013 Uiso 1 1 calc R . .
C6 C -0.8576(2) 0.85212(13) 0.02345(11) 0.0122(3) Uani 1 1 d . . .
H6A H -0.9873 0.8726 0.0383 0.015 Uiso 1 1 calc R . .
H6B H -0.8581 0.7780 0.0050 0.015 Uiso 1 1 calc R . .
C7 C -0.9635(2) 0.92025(12) -0.16402(11) 0.0103(3) Uani 1 1 d . . .
C8 C -1.1332(2) 0.87224(13) -0.14450(12) 0.0130(3) Uani 1 1 d . . .
H8 H -1.1519 0.8377 -0.0834 0.016 Uiso 1 1 calc R . .
C10 C 0.4089(2) 0.53528(12) 0.17611(12) 0.0117(3) Uani 1 1 d . . .
H10 H 0.4258 0.5044 0.1130 0.014 Uiso 1 1 calc R . .
C9 C 0.2259(2) 0.62423(13) 0.28432(12) 0.0134(3) Uani 1 1 d . . .
H9 H 0.1100 0.6557 0.2996 0.016 Uiso 1 1 calc R . .
C11 C -0.9438(2) 0.96731(12) -0.25675(12) 0.0116(3) Uani 1 1 d . . .
H11 H -0.8303 1.0007 -0.2733 0.014 Uiso 1 1 calc R . .


_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 N2 1.9938(14) . ?
Cu1 N1 2.0364(14) . ?
Cu1 Cl1 2.4148(4) . ?
Cu1 Cl1 2.4445(4) 3_565 ?
Cl1 Cu1 2.4445(4) 3_565 ?
S1 C3 1.7512(16) . ?
S1 C6 1.7937(16) . ?
S2 C7 1.7600(16) . ?
S2 C6 1.8191(16) . ?
N1 C5 1.345(2) . ?
N1 C1 1.353(2) . ?
N2 C9 1.343(2) . ?
N2 C10 1.352(2) . ?
C1 C2 1.379(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.397(2) . ?
C4 C5 1.386(2) . ?
C7 C8 1.394(2) . ?
C7 C11 1.401(2) . ?
C8 C9 1.384(2) 4_475 ?
C10 C11 1.381(2) 4_776 ?
C9 C8 1.384(2) 4_776 ?
C11 C10 1.381(2) 4_475 ?

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
N2 Cu1 N1 122.90(6) . . ?
N2 Cu1 Cl1 112.98(4) . . ?
N1 Cu1 Cl1 103.92(4) . . ?
N2 Cu1 Cl1 117.38(4) . 3_565 ?
N1 Cu1 Cl1 101.50(4) . 3_565 ?
Cl1 Cu1 Cl1 93.490(14) . 3_565 ?
Cu1 Cl1 Cu1 86.511(14) . 3_565 ?
C3 S1 C6 105.27(8) . . ?
C7 S2 C6 101.66(7) . . ?
C5 N1 C1 116.33(14) . . ?
C5 N1 Cu1 119.02(11) . . ?
C1 N1 Cu1 123.75(11) . . ?
C9 N2 C10 116.15(14) . . ?
C9 N2 Cu1 121.87(11) . . ?
C10 N2 Cu1 121.97(11) . . ?
N1 C1 C2 123.90(14) . . ?
C1 C2 C3 118.78(14) . . ?
C2 C3 C4 118.38(14) . . ?
C2 C3 S1 114.98(12) . . ?
C4 C3 S1 126.63(12) . . ?
C5 C4 C3 118.35(14) . . ?
N1 C5 C4 124.22(14) . . ?
S1 C6 S2 111.24(9) . . ?
C8 C7 C11 117.49(14) . . ?
C8 C7 S2 124.92(12) . . ?
C11 C7 S2 117.58(12) . . ?
C9 C8 C7 118.92(15) 4_475 . ?
N2 C10 C11 123.66(15) . 4_776 ?
N2 C9 C8 124.39(15) . 4_776 ?
C10 C11 C7 119.35(15) 4_475 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2051954'
loop_
_audit_author_name
_audit_author_address
'Ana Lago'
;Universidad de la Laguna
Spain
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 Cl Cu N2 S2'
_chemical_formula_weight         333.32

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   3.8383(2)
_cell_length_b                   22.1816(9)
_cell_length_c                   14.0252(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1194.10(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6685
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      28.26

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    2.376
_shelx_estimated_absorpt_T_min   0.585
_shelx_estimated_absorpt_T_max   0.928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12437
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         28.287
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1485
_reflns_number_gt                1340
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0169P)²+1.5180P] 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         1485
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0236
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0511
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.5000 0.44942(2) 0.2500 0.01018(9) Uani 1 2 d S T P . .
S1 S 0.32831(12) 0.30757(2) 0.65788(3) 0.00875(10) Uani 1 1 d . . . . .
Cl1 Cl 0.0000 0.51274(2) 0.2500 0.01158(13) Uani 1 2 d S T P . .
N1 N 0.5013(4) 0.40265(6) 0.37319(10) 0.0093(3) Uani 1 1 d . . . . .
C1 C 0.3475(5) 0.34852(7) 0.38174(12) 0.0100(3) Uani 1 1 d . . . . .
H1 H 0.2673 0.3291 0.3255 0.012 Uiso 1 1 calc R U . . .
C2 C 0.2996(4) 0.31951(7) 0.46787(11) 0.0085(3) Uani 1 1 d . . . . .
H2 H 0.1934 0.2809 0.4700 0.010 Uiso 1 1 calc R U . . .
C3 C 0.4094(4) 0.34771(7) 0.55202(11) 0.0074(3) Uani 1 1 d . . . . .
C4 C 0.5681(5) 0.40388(7) 0.54445(12) 0.0087(3) Uani 1 1 d . . . . .
H4 H 0.6451 0.4248 0.5997 0.010 Uiso 1 1 calc R U . . .
C5 C 0.6113(5) 0.42856(8) 0.45448(12) 0.0097(3) Uani 1 1 d . . . . .
H5 H 0.7264 0.4664 0.4499 0.012 Uiso 1 1 calc R U . . .
C6 C 0.5000 0.35622(10) 0.7500 0.0117(5) Uani 1 2 d S T P . .
H6A H 0.3134 0.3823 0.7760 0.014 Uiso 0.5 1 calc R U P . .
H6B H 0.6866 0.3823 0.7240 0.014 Uiso 0.5 1 calc R U P . .


_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 N1 2.0154(14) 3_655 ?
Cu1 N1 2.0154(14) . ?
Cu1 Cl1 2.3782(4) 1_655 ?
Cu1 Cl1 2.3782(4) . ?
S1 C3 1.7591(17) . ?
S1 C6 1.8078(14) . ?
Cl1 Cu1 2.3782(4) 1_455 ?
N1 C1 1.343(2) . ?
N1 C5 1.345(2) . ?
C1 C2 1.381(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.385(2) . ?
C6 S1 1.8078(14) 3_656 ?

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
N1 Cu1 N1 118.03(8) 3_655 . ?
N1 Cu1 Cl1 107.82(4) 3_655 1_655 ?
N1 Cu1 Cl1 107.58(4) . 1_655 ?
N1 Cu1 Cl1 107.58(4) 3_655 . ?
N1 Cu1 Cl1 107.82(4) . . ?
Cl1 Cu1 Cl1 107.61(2) 1_655 . ?
C3 S1 C6 103.68(8) . . ?
Cu1 Cl1 Cu1 107.61(2) 1_455 . ?
C1 N1 C5 116.38(14) . . ?
C1 N1 Cu1 122.38(11) . . ?
C5 N1 Cu1 120.50(11) . . ?
N1 C1 C2 123.58(15) . . ?
C1 C2 C3 119.27(15) . . ?
C4 C3 C2 117.87(15) . . ?
C4 C3 S1 126.54(13) . . ?
C2 C3 S1 115.59(12) . . ?
C5 C4 C3 118.41(15) . . ?
N1 C5 C4 124.46(16) . . ?
S1 C6 S1 106.69(12) . 3_656 ?

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
C2 H2 S1 0.95 3.00 3.7854(17) 140.4 4_456
C4 H4 Cl1 0.95 2.87 3.8053(17) 169.5 5_666
C6 H6A Cl1 0.99 2.65 3.483(2) 142.3 5_566
C6 H6B Cl1 0.99 2.65 3.483(2) 142.3 5_666

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2051953'
loop_
_audit_author_name
_audit_author_address
'Ana Lago'
;Universidad de la Laguna
Spain
;
_audit_update_record             
;
2020-12-22 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H9 Cl Cu N2 S2'
_chemical_formula_sum            'C11 H9 Cl Cu N2 S2'
_chemical_formula_weight         332.31

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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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                   13.0329(7)
_cell_length_b                   12.4106(6)
_cell_length_c                   14.8895(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.525(2)
_cell_angle_gamma                90
_cell_volume                     2406.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    276(2)
_cell_measurement_reflns_used    8145
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.29

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.037
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    2.359
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      276(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20532
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         28.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3003
_reflns_number_gt                2551
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0510P)²+15.4970P] 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         3003
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   0.785
_refine_ls_restrained_S_all      0.785
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.04580(2) 0.01578(2) 0.09260(2) 0.01065(9) Uani 1 1 d . . . . .
Cl1 Cl -0.13789(4) -0.03129(4) 0.04839(4) 0.01022(12) Uani 1 1 d . . . . .
S1 S 0.04063(4) -0.46916(4) 0.38223(4) 0.01010(13) Uani 1 1 d . . . . .
S2 S 0.21227(4) -0.44791(5) 0.24894(4) 0.01047(13) Uani 1 1 d . . . . .
N1 N 0.02629(15) 0.17043(15) 0.12207(13) 0.0092(4) Uani 1 1 d . . . . .
N2 N 0.10570(14) -0.11946(15) 0.14349(13) 0.0082(4) Uani 1 1 d . . . . .
C1 C 0.09425(18) 0.24527(19) 0.09681(16) 0.0103(4) Uani 1 1 d . . . . .
H1 H 0.1570 0.2217 0.0769 0.012 Uiso 1 1 calc R U . . .
C2 C -0.07625(18) -0.64526(18) 0.40124(16) 0.0096(4) Uani 1 1 d . . . . .
H2 H -0.1265 -0.5969 0.4179 0.012 Uiso 1 1 calc R U . . .
C3 C 0.01882(17) -0.60804(18) 0.37387(15) 0.0081(4) Uani 1 1 d . . . . .
C4 C 0.08837(17) -0.68439(18) 0.34375(15) 0.0089(4) Uani 1 1 d . . . . .
H4 H 0.1510 -0.6628 0.3221 0.011 Uiso 1 1 calc R U . . .
C5 C -0.06268(17) 0.20720(18) 0.15342(16) 0.0094(4) Uani 1 1 d . . . . .
C6 C 0.17591(18) -0.45488(19) 0.36467(16) 0.0105(4) Uani 1 1 d . . . . .
H6A H 0.2115 -0.5153 0.3931 0.013 Uiso 1 1 calc R U . . .
H6B H 0.2000 -0.3900 0.3952 0.013 Uiso 1 1 calc R U . . .
C7 C 0.16895(16) -0.32028(17) 0.21338(16) 0.0080(4) Uani 1 1 d . . . . .
C8 C 0.16410(17) -0.30088(18) 0.12095(16) 0.0092(4) Uani 1 1 d . . . . .
H8 H 0.1824 -0.3545 0.0811 0.011 Uiso 1 1 calc R U . . .
C9 C 0.13178(17) -0.20118(18) 0.08914(16) 0.0095(4) Uani 1 1 d . . . . .
H9 H 0.1278 -0.1899 0.0273 0.011 Uiso 1 1 calc R U . . .
C10 C 0.11359(17) -0.13827(18) 0.23246(16) 0.0092(4) Uani 1 1 d . . . . .
H10 H 0.0980 -0.0823 0.2711 0.011 Uiso 1 1 calc R U . . .
C11 C 0.14351(17) -0.23608(19) 0.27012(16) 0.0091(4) Uani 1 1 d . . . . .
H11 H 0.1465 -0.2453 0.3322 0.011 Uiso 1 1 calc R U . . .


_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 N2 1.9871(19) . ?
Cu1 N1 1.9877(19) . ?
Cu1 Cl1 2.4711(6) 5 ?
Cu1 Cl1 2.5233(6) . ?
Cu1 Cu1 2.9821(6) 5 ?
Cl1 Cu1 2.4711(6) 5 ?
S1 C3 1.750(2) . ?
S1 C6 1.802(2) . ?
S2 C7 1.756(2) . ?
S2 C6 1.809(2) . ?
N1 C1 1.348(3) . ?
N1 C5 1.348(3) . ?
N2 C10 1.345(3) . ?
N2 C9 1.350(3) . ?
C1 C2 1.379(3) 2_565 ?
C2 C1 1.379(3) 2_545 ?
C2 C3 1.400(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.388(3) 2_545 ?
C5 C4 1.388(3) 2_565 ?
C7 C11 1.393(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.384(3) . ?
C10 C11 1.386(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
N2 Cu1 N1 141.57(8) . . ?
N2 Cu1 Cl1 101.10(6) . 5 ?
N1 Cu1 Cl1 100.60(6) . 5 ?
N2 Cu1 Cl1 104.84(6) . . ?
N1 Cu1 Cl1 98.74(6) . . ?
Cl1 Cu1 Cl1 106.687(19) 5 . ?
N2 Cu1 Cu1 112.10(6) . 5 ?
N1 Cu1 Cu1 106.33(6) . 5 ?
Cl1 Cu1 Cu1 54.148(16) 5 5 ?
Cl1 Cu1 Cu1 52.539(15) . 5 ?
Cu1 Cl1 Cu1 73.313(19) 5 . ?
C3 S1 C6 104.08(11) . . ?
C7 S2 C6 103.66(11) . . ?
C1 N1 C5 116.7(2) . . ?
C1 N1 Cu1 120.77(16) . . ?
C5 N1 Cu1 121.57(16) . . ?
C10 N2 C9 116.7(2) . . ?
C10 N2 Cu1 122.28(15) . . ?
C9 N2 Cu1 120.72(16) . . ?
N1 C1 C2 123.9(2) . 2_565 ?
C1 C2 C3 119.0(2) 2_545 . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 S1 125.75(17) . . ?
C2 C3 S1 116.57(17) . . ?
C5 C4 C3 119.1(2) 2_545 . ?
N1 C5 C4 123.4(2) . 2_565 ?
S1 C6 S2 116.22(13) . . ?
C11 C7 C8 117.8(2) . . ?
C11 C7 S2 125.16(18) . . ?
C8 C7 S2 116.94(17) . . ?
C9 C8 C7 119.4(2) . . ?
N2 C9 C8 123.2(2) . . ?
N2 C10 C11 124.0(2) . . ?
C10 C11 C7 118.8(2) . . ?

_refine_diff_density_max         0.990
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.090

_shelxl_version_number           2013-3


