# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc24579w
_database_code_depnum_ccdc_archive 'CCDC 1971237'
loop_
_audit_author_name
_audit_author_address
'Wen-Xing Jiang'
;South China University of Technology
China
;
_audit_update_record             
;
2019-12-11 deposited with the CCDC.	2020-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        CuATSM
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H15 Cu N6 S2'
_chemical_formula_sum            'C8 H15 Cu N6 S2'
_chemical_formula_weight         322.92

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'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   12.3838(17)
_cell_length_b                   13.0495(13)
_cell_length_c                   8.3122(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.576(11)
_cell_angle_gamma                90
_cell_volume                     1343.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1148
_cell_measurement_theta_min      3.9610
_cell_measurement_theta_max      25.1720

_exptl_crystal_description       block
_exptl_crystal_colour            'reddish brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.925
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4486
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.695
_diffrn_reflns_point_group_measured_fraction_full 0.687
_reflns_number_total             1661
_reflns_number_gt                1284
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_max     0.409
_reflns_Friedel_fraction_full    0.404

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0116P)²]
 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.19(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1661
_refine_ls_number_parameters     154
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0616
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.010

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 0.9576(4) 0.07045(5) 0.3269(5) 0.0364(3) Uani 1 1 d . . . . .
S2 S 0.8351(3) 0.1689(4) 0.2047(3) 0.0405(16) Uani 1 1 d . . . . .
S1 S 1.0800(3) 0.1705(4) 0.4526(4) 0.0503(19) Uani 1 1 d . . . . .
N2 N 0.8774(14) -0.0451(13) 0.2455(18) 0.038(4) Uani 1 1 d . . . . .
N1 N 1.0420(14) -0.0435(13) 0.4256(17) 0.030(3) Uani 1 1 d . U . . .
N4 N 0.7872(13) -0.0299(12) 0.1424(18) 0.038(4) Uani 1 1 d . . . . .
H4A H 0.7521 -0.0795 0.0984 0.045 Uiso 1 1 calc R U . . .
C5 C 1.1533(15) 0.0633(14) 0.5294(19) 0.032(5) Uani 1 1 d . . . . .
C4 C 0.9064(15) -0.1315(14) 0.285(2) 0.036(5) Uani 1 1 d . . . . .
C3 C 1.0041(14) -0.1382(13) 0.3853(19) 0.035(5) Uani 1 1 d . . . . .
N3 N 1.1312(15) -0.0321(13) 0.5121(18) 0.046(5) Uani 1 1 d . . . . .
C6 C 0.7616(18) 0.0694(15) 0.119(2) 0.046(6) Uani 1 1 d . . . . .
N6 N 0.6805(14) 0.0877(13) 0.037(2) 0.058(5) Uani 1 1 d . . . . .
H6A H 0.6650 0.1513 0.0220 0.070 Uiso 1 1 calc R U . . .
N5 N 1.2465(13) 0.0904(12) 0.6207(16) 0.040(4) Uani 1 1 d . . . . .
H5A H 1.2621 0.1540 0.6338 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8436(14) -0.2283(13) 0.2353(18) 0.039(4) Uani 1 1 d . U . . .
H2A H 0.7825 -0.2092 0.1698 0.059 Uiso 1 1 calc R U . . .
H2B H 0.8191 -0.2631 0.3298 0.059 Uiso 1 1 calc R U . . .
H2C H 0.8898 -0.2728 0.1752 0.059 Uiso 1 1 calc R U . . .
C1 C 1.0536(15) -0.2327(12) 0.445(2) 0.055(5) Uani 1 1 d . . . . .
H1A H 1.1156 -0.2163 0.5101 0.082 Uiso 1 1 calc R U . . .
H1B H 1.0756 -0.2740 0.3553 0.082 Uiso 1 1 calc R U . . .
H1C H 1.0023 -0.2699 0.5079 0.082 Uiso 1 1 calc R U . . .
C8 C 0.6071(18) 0.0125(13) -0.040(2) 0.057(6) Uani 1 1 d . . . . .
H8A H 0.5505 0.0481 -0.0966 0.085 Uiso 1 1 calc R U . . .
H8B H 0.5762 -0.0305 0.0411 0.085 Uiso 1 1 calc R U . . .
H8C H 0.6469 -0.0288 -0.1143 0.085 Uiso 1 1 calc R U . . .
C7 C 1.314(2) 0.0147(13) 0.691(2) 0.066(6) Uani 1 1 d . . . . .
H7A H 1.3253 0.0297 0.8027 0.099 Uiso 1 1 calc R U . . .
H7B H 1.3828 0.0147 0.6372 0.099 Uiso 1 1 calc R U . . .
H7C H 1.2812 -0.0514 0.6794 0.099 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 1.925(16) . ?
Cu1 N1 1.990(16) . ?
Cu1 S2 2.226(6) . ?
Cu1 S1 2.249(6) . ?
S2 C6 1.73(2) . ?
S1 C5 1.782(17) . ?
N2 C4 1.23(3) . ?
N2 N4 1.41(2) . ?
N1 N3 1.32(2) . ?
N1 C3 1.36(3) . ?
N4 C6 1.35(2) . ?
C5 N3 1.28(2) . ?
C5 N5 1.42(2) . ?
C4 C3 1.466(10) . ?
C4 C2 1.54(2) . ?
C3 C1 1.46(3) . ?
C6 N6 1.23(2) . ?
N6 C8 1.48(2) . ?
N5 C7 1.42(2) . ?

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 80.0(2) . . ?
N2 Cu1 S2 86.8(6) . . ?
N1 Cu1 S2 166.5(6) . . ?
N2 Cu1 S1 163.9(6) . . ?
N1 Cu1 S1 83.9(5) . . ?
S2 Cu1 S1 109.25(7) . . ?
C6 S2 Cu1 96.1(7) . . ?
C5 S1 Cu1 92.8(6) . . ?
C4 N2 N4 121.2(18) . . ?
C4 N2 Cu1 118.5(14) . . ?
N4 N2 Cu1 120.3(13) . . ?
N3 N1 C3 121.4(18) . . ?
N3 N1 Cu1 125.0(14) . . ?
C3 N1 Cu1 113.5(12) . . ?
C6 N4 N2 113.8(16) . . ?
N3 C5 N5 118.2(15) . . ?
N3 C5 S1 127.9(14) . . ?
N5 C5 S1 113.9(13) . . ?
N2 C4 C3 116(2) . . ?
N2 C4 C2 122.5(18) . . ?
C3 C4 C2 121.1(19) . . ?
N1 C3 C1 122.7(16) . . ?
N1 C3 C4 111.5(19) . . ?
C1 C3 C4 125.8(18) . . ?
C5 N3 N1 110.3(16) . . ?
N6 C6 N4 117.0(18) . . ?
N6 C6 S2 120.3(16) . . ?
N4 C6 S2 122.7(16) . . ?
C6 N6 C8 127.2(17) . . ?
C7 N5 C5 121.5(15) . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-2

