# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1916668'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_date             2019-05-17T15:56:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C21 H22 Cu N4 S4'
_chemical_formula_weight         522.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2020(6)
_cell_length_b                   9.8519(9)
_cell_length_c                   13.1757(13)
_cell_angle_alpha                78.592(8)
_cell_angle_beta                 80.289(7)
_cell_angle_gamma                77.953(7)
_cell_volume                     1134.93(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3306
_cell_measurement_theta_min      5.29
_cell_measurement_theta_max      61.31
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538

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

_exptl_absorpt_coefficient_mu    4.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  1
_shelx_estimated_absorpt_T_min   0.439
_shelx_estimated_absorpt_T_max   0.866

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

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_orient_matrix_ub_11      -0.070585
_diffrn_orient_matrix_ub_12      0.094721
_diffrn_orient_matrix_ub_13      0.082139
_diffrn_orient_matrix_ub_21      0.156578
_diffrn_orient_matrix_ub_22      -0.005093
_diffrn_orient_matrix_ub_23      0.029052
_diffrn_orient_matrix_ub_31      0.018228
_diffrn_orient_matrix_ub_32      0.131592
_diffrn_orient_matrix_ub_33      -0.083024
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_number            8440
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.453
_diffrn_reflns_theta_max         61.606
_diffrn_reflns_theta_full        61.606
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             3493
_reflns_number_gt                2912
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.0075P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3493
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.088

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C1 C 0.5826(4) 0.4889(4) 0.3171(3) 0.0248(8) Uani 1 1 d . . . . .
C2 C 0.6918(4) 0.2703(3) 0.5355(3) 0.0257(8) Uani 1 1 d . . . . .
C3 C 0.7735(4) 0.2569(4) 0.6270(3) 0.0274(8) Uani 1 1 d . . . . .
H3A H 0.70291 0.229322 0.68952 0.033 Uiso 1 1 calc R U . . .
H3B H 0.85553 0.174593 0.622042 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8423(4) 0.3682(4) 0.6530(3) 0.0269(8) Uani 1 1 d . . . . .
C5 C 0.8959(4) 0.7079(4) 0.5796(3) 0.0244(8) Uani 1 1 d . . . . .
C6 C 0.6387(4) 0.1402(4) 0.5273(3) 0.0355(9) Uani 1 1 d . . . . .
H6A H 0.533675 0.164365 0.514763 0.053 Uiso 1 1 calc R U . . .
H6B H 0.647461 0.07289 0.592528 0.053 Uiso 1 1 calc R U . . .
H6C H 0.700111 0.097927 0.469216 0.053 Uiso 1 1 calc R U . . .
C7 C 0.9113(4) 0.3282(4) 0.7515(3) 0.0323(8) Uani 1 1 d . . . . .
H7A H 1.01432 0.345769 0.737541 0.048 Uiso 1 1 calc R U . . .
H7B H 0.91198 0.228046 0.778737 0.048 Uiso 1 1 calc R U . . .
H7C H 0.85285 0.384451 0.80316 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4498(4) 0.3205(4) 0.2242(3) 0.0353(9) Uani 1 1 d . . . . .
H8A H 0.418091 0.285551 0.298748 0.042 Uiso 1 1 calc R U . . .
H8B H 0.365974 0.32336 0.18509 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5834(4) 0.2196(4) 0.1848(3) 0.0293(8) Uani 1 1 d . . . . .
C10 C 0.6659(5) 0.2526(4) 0.0882(3) 0.0406(10) Uani 1 1 d . . . . .
H10 H 0.639448 0.342039 0.046468 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7865(5) 0.1567(5) 0.0516(3) 0.0466(11) Uani 1 1 d . . . . .
H11 H 0.842026 0.180481 -0.014914 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8260(5) 0.0273(5) 0.1114(3) 0.0427(10) Uani 1 1 d . . . . .
H12 H 0.908788 -0.038349 0.086235 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7461(5) -0.0074(4) 0.2075(4) 0.0450(10) Uani 1 1 d . . . . .
H13 H 0.773165 -0.097199 0.248694 0.054 Uiso 1 1 calc R U . . .
C14 C 0.6261(5) 0.0885(4) 0.2444(3) 0.0386(9) Uani 1 1 d . . . . .
H14 H 0.572109 0.064289 0.311471 0.046 Uiso 1 1 calc R U . . .
C15 C 1.0365(4) 0.7476(4) 0.7414(3) 0.0326(9) Uani 1 1 d . . . . .
H15A H 1.080769 0.647836 0.737776 0.039 Uiso 1 1 calc R U . . .
H15B H 1.115816 0.793177 0.755162 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9115(4) 0.7532(4) 0.8317(3) 0.0302(8) Uani 1 1 d . . . . .
C17 C 0.8970(5) 0.6359(5) 0.9074(3) 0.0438(10) Uani 1 1 d . . . . .
H17 H 0.963293 0.549346 0.900618 0.053 Uiso 1 1 calc R U . . .
C18 C 0.7877(5) 0.6430(6) 0.9924(4) 0.0568(13) Uani 1 1 d . . . . .
H18 H 0.779931 0.561525 1.043982 0.068 Uiso 1 1 calc R U . . .
C19 C 0.6891(5) 0.7672(6) 1.0035(4) 0.0526(12) Uani 1 1 d . . . . .
H19 H 0.614342 0.772255 1.062562 0.063 Uiso 1 1 calc R U . . .
C20 C 0.7011(5) 0.8819(5) 0.9285(4) 0.0507(11) Uani 1 1 d . . . . .
H20 H 0.632579 0.967351 0.934997 0.061 Uiso 1 1 calc R U . . .
C21 C 0.8106(5) 0.8772(4) 0.8429(3) 0.0409(10) Uani 1 1 d . . . . .
H21 H 0.816809 0.959016 0.791464 0.049 Uiso 1 1 calc R U . . .
Cu1 Cu 0.74330(5) 0.56174(5) 0.46674(4) 0.02376(18) Uani 1 1 d . . . . .
N1 N 0.5924(3) 0.3772(3) 0.3870(2) 0.0269(7) Uani 1 1 d . . . . .
N2 N 0.6725(3) 0.3850(3) 0.4682(2) 0.0256(6) Uani 1 1 d . . . . .
N3 N 0.8392(3) 0.4907(3) 0.5955(2) 0.0250(6) Uani 1 1 d . . . . .
N4 N 0.9093(3) 0.5816(3) 0.6339(2) 0.0257(6) Uani 1 1 d . . . . .
S1 S 0.65339(10) 0.63958(9) 0.31289(7) 0.0311(2) Uani 1 1 d . . . . .
S2 S 0.80540(10) 0.76999(9) 0.47031(7) 0.0296(2) Uani 1 1 d . . . . .
S3 S 0.48632(10) 0.49879(10) 0.21098(7) 0.0317(2) Uani 1 1 d . . . . .
S4 S 0.97777(10) 0.83283(9) 0.61560(7) 0.0291(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.286(5) . ?
C1 S1 1.729(3) . ?
C1 S3 1.754(4) . ?
C2 N2 1.292(5) . ?
C2 C6 1.492(5) . ?
C2 C3 1.495(5) . ?
C3 C4 1.494(5) . ?
C4 N3 1.289(5) . ?
C4 C7 1.488(5) . ?
C5 N4 1.299(5) . ?
C5 S2 1.728(4) . ?
C5 S4 1.745(3) . ?
C8 C9 1.499(6) . ?
C8 S3 1.826(4) . ?
C9 C10 1.384(6) . ?
C9 C14 1.390(6) . ?
C10 C11 1.386(6) . ?
C11 C12 1.372(6) . ?
C12 C13 1.371(6) . ?
C13 C14 1.383(6) . ?
C15 C16 1.509(5) . ?
C15 S4 1.819(4) . ?
C16 C17 1.383(6) . ?
C16 C21 1.388(6) . ?
C17 C18 1.376(7) . ?
C18 C19 1.380(8) . ?
C19 C20 1.356(7) . ?
C20 C21 1.381(6) . ?
Cu1 N2 1.978(3) . ?
Cu1 N3 1.981(3) . ?
Cu1 S1 2.2511(10) . ?
Cu1 S2 2.2528(10) . ?
N1 N2 1.420(4) . ?
N3 N4 1.416(4) . ?

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 C1 S1 127.9(3) . . ?
N1 C1 S3 119.4(3) . . ?
S1 C1 S3 112.7(2) . . ?
N2 C2 C6 123.2(3) . . ?
N2 C2 C3 122.1(3) . . ?
C6 C2 C3 114.7(3) . . ?
C4 C3 C2 126.3(3) . . ?
N3 C4 C7 122.6(3) . . ?
N3 C4 C3 122.5(3) . . ?
C7 C4 C3 114.9(3) . . ?
N4 C5 S2 127.0(3) . . ?
N4 C5 S4 119.2(3) . . ?
S2 C5 S4 113.8(2) . . ?
C9 C8 S3 113.1(3) . . ?
C10 C9 C14 118.1(4) . . ?
C10 C9 C8 121.5(4) . . ?
C14 C9 C8 120.4(4) . . ?
C9 C10 C11 120.8(4) . . ?
C12 C11 C10 120.1(4) . . ?
C13 C12 C11 120.1(4) . . ?
C12 C13 C14 119.9(4) . . ?
C13 C14 C9 121.0(4) . . ?
C16 C15 S4 114.1(3) . . ?
C17 C16 C21 118.0(4) . . ?
C17 C16 C15 120.9(4) . . ?
C21 C16 C15 121.0(3) . . ?
C18 C17 C16 120.8(4) . . ?
C17 C18 C19 120.6(4) . . ?
C20 C19 C18 118.8(5) . . ?
C19 C20 C21 121.5(5) . . ?
C20 C21 C16 120.2(4) . . ?
N2 Cu1 N3 94.69(12) . . ?
N2 Cu1 S1 86.35(9) . . ?
N3 Cu1 S1 175.28(9) . . ?
N2 Cu1 S2 175.48(9) . . ?
N3 Cu1 S2 86.21(9) . . ?
S1 Cu1 S2 93.11(4) . . ?
C1 N1 N2 112.9(3) . . ?
C2 N2 N1 113.7(3) . . ?
C2 N2 Cu1 127.4(2) . . ?
N1 N2 Cu1 118.9(2) . . ?
C4 N3 N4 113.9(3) . . ?
C4 N3 Cu1 127.1(2) . . ?
N4 N3 Cu1 119.0(2) . . ?
C5 N4 N3 113.3(3) . . ?
C1 S1 Cu1 93.80(12) . . ?
C5 S2 Cu1 94.38(12) . . ?
C1 S3 C8 103.41(18) . . ?
C5 S4 C15 103.58(17) . . ?



# END of CIF
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1916670'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_date             2019-05-17T15:33:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C9 H12 Cu N4 O S4'
_chemical_formula_weight         384.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnam
_symmetry_space_group_name_Hall  '-P 2c 2n'
_symmetry_Int_Tables_number      62
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   17.3466(5)
_cell_length_b                   12.2444(4)
_cell_length_c                   6.9842(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1483.44(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1329
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      62.35
_cell_measurement_wavelength     1.5418

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

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780

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

_exptl_absorpt_coefficient_mu    7.324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.044361
_diffrn_orient_matrix_ub_12      -0.10886
_diffrn_orient_matrix_ub_13      -0.007222
_diffrn_orient_matrix_ub_21      -0.076895
_diffrn_orient_matrix_ub_22      0.062935
_diffrn_orient_matrix_ub_23      -0.003418
_diffrn_orient_matrix_ub_31      0.00263
_diffrn_orient_matrix_ub_32      0.002584
_diffrn_orient_matrix_ub_33      -0.220514
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_number            3990
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         62.499
_diffrn_reflns_theta_full        62.499
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             1283
_reflns_number_gt                958
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1283
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 C 0.5864(3) 0.5771(4) 0.25 0.0505(11) Uani 1 2 d S T P . .
C2 C 0.3911(2) 0.5624(4) 0.25 0.0517(11) Uani 1 2 d S T P . .
C3 C 0.3243(3) 0.4856(4) 0.25 0.0569(13) Uani 1 2 d S T P . .
C4 C 0.3276(2) 0.3632(4) 0.25 0.0521(12) Uani 1 2 d S T P . .
C5 C 0.4492(3) 0.1461(4) 0.25 0.0554(12) Uani 1 2 d S T P . .
C6 C 0.3718(3) 0.6807(4) 0.25 0.0641(14) Uani 1 2 d S T P . .
H6A H 0.315608 0.689601 0.25 0.096 Uiso 1 2 calc R U P . .
H6B H 0.393434 0.715204 0.364568 0.096 Uiso 0.5 1 calc R U P . .
H6C H 0.393434 0.715204 0.135432 0.096 Uiso 0.5 1 calc R U P . .
C7 C 0.2517(2) 0.3058(5) 0.25 0.0711(16) Uani 1 2 d S T P . .
H7A H 0.20998 0.359807 0.25 0.107 Uiso 1 2 calc R U P . .
H7B H 0.247602 0.259952 0.135432 0.107 Uiso 0.5 1 calc R U P . .
H7C H 0.247602 0.259952 0.364568 0.107 Uiso 0.5 1 calc R U P . .
C8 C 0.6072(3) 0.8009(4) 0.25 0.0736(16) Uani 1 2 d S T P . .
H8A H 0.643622 0.862062 0.25 0.11 Uiso 1 2 calc R U P . .
H8B H 0.5747 0.80481 0.135432 0.11 Uiso 0.5 1 calc R U P . .
H8C H 0.5747 0.80481 0.364568 0.11 Uiso 0.5 1 calc R U P . .
C9 C 0.3441(4) -0.0207(5) 0.25 0.120(3) Uani 1 2 d S T P . .
H9A H 0.334908 -0.099653 0.25 0.18 Uiso 1 2 calc R U P . .
H9B H 0.320834 0.011766 0.364568 0.18 Uiso 0.5 1 calc R U P . .
H9C H 0.320834 0.011766 0.135432 0.18 Uiso 0.5 1 calc R U P . .
O1 O 0.2608(2) 0.5255(3) 0.25 0.1085(18) Uani 1 2 d S T P . .
Cu1 Cu 0.49832(3) 0.37348(5) 0.25 0.0489(2) Uani 1 2 d S T P . .
N1 N 0.5160(2) 0.6104(3) 0.25 0.0578(10) Uani 1 2 d S T P . .
N2 N 0.46140(19) 0.5269(3) 0.25 0.0510(10) Uani 1 2 d S T P . .
N3 N 0.39250(18) 0.3111(3) 0.25 0.0479(9) Uani 1 2 d S T P . .
N4 N 0.3844(2) 0.1996(3) 0.25 0.0549(10) Uani 1 2 d S T P . .
S1 S 0.61817(6) 0.44345(10) 0.25 0.0604(4) Uani 1 2 d S T P . .
S2 S 0.54026(6) 0.20045(10) 0.25 0.0716(4) Uani 1 2 d S T P . .
S3 S 0.65947(7) 0.67458(11) 0.25 0.0632(4) Uani 1 2 d S T P . .
S4 S 0.44532(9) 0.00500(11) 0.25 0.0857(5) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.289(6) . ?
C1 S1 1.727(5) . ?
C1 S3 1.741(4) . ?
C2 N2 1.294(6) . ?
C2 C6 1.486(6) . ?
C2 C3 1.493(7) . ?
C3 O1 1.206(6) . ?
C3 C4 1.500(7) . ?
C4 N3 1.294(6) . ?
C4 C7 1.492(6) . ?
C5 N4 1.300(6) . ?
C5 S2 1.714(5) . ?
C5 S4 1.730(5) . ?
C8 S3 1.793(6) . ?
C9 S4 1.784(7) . ?
Cu1 N2 1.984(3) . ?
Cu1 N3 1.988(3) . ?
Cu1 S2 2.2401(13) . ?
Cu1 S1 2.2487(12) . ?
N1 N2 1.394(5) . ?
N3 N4 1.373(5) . ?

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 C1 S1 127.1(4) . . ?
N1 C1 S3 118.3(4) . . ?
S1 C1 S3 114.7(3) . . ?
N2 C2 C6 122.7(4) . . ?
N2 C2 C3 121.3(4) . . ?
C6 C2 C3 116.0(4) . . ?
O1 C3 C2 117.0(4) . . ?
O1 C3 C4 116.1(4) . . ?
C2 C3 C4 126.9(4) . . ?
N3 C4 C7 122.4(4) . . ?
N3 C4 C3 121.6(4) . . ?
C7 C4 C3 116.0(4) . . ?
N4 C5 S2 126.9(3) . . ?
N4 C5 S4 118.0(3) . . ?
S2 C5 S4 115.1(3) . . ?
N2 Cu1 N3 93.76(14) . . ?
N2 Cu1 S2 179.87(11) . . ?
N3 Cu1 S2 86.37(11) . . ?
N2 Cu1 S1 86.43(11) . . ?
N3 Cu1 S1 179.81(11) . . ?
S2 Cu1 S1 93.44(5) . . ?
C1 N1 N2 114.3(4) . . ?
C2 N2 N1 113.1(4) . . ?
C2 N2 Cu1 128.5(3) . . ?
N1 N2 Cu1 118.4(3) . . ?
C4 N3 N4 113.6(3) . . ?
C4 N3 Cu1 127.9(3) . . ?
N4 N3 Cu1 118.4(3) . . ?
C5 N4 N3 114.4(4) . . ?
C1 S1 Cu1 93.79(15) . . ?
C5 S2 Cu1 93.87(16) . . ?
C1 S3 C8 102.9(2) . . ?
C5 S4 C9 102.4(3) . . ?



# END of CIF
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1916669'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_date             2019-05-17T15:44:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C9 H13 Cu N4 S4'
_chemical_formula_weight         369.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5839(7)
_cell_length_b                   8.7981(6)
_cell_length_c                   11.6005(9)
_cell_angle_alpha                106.962(6)
_cell_angle_beta                 107.126(7)
_cell_angle_gamma                90.272(6)
_cell_volume                     704.04(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    1891
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      61.99
_cell_measurement_wavelength     1.54184

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

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376

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

_exptl_absorpt_coefficient_mu    7.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.381
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.088468
_diffrn_orient_matrix_ub_12      0.082139
_diffrn_orient_matrix_ub_13      -0.100727
_diffrn_orient_matrix_ub_21      -0.189484
_diffrn_orient_matrix_ub_22      -0.021367
_diffrn_orient_matrix_ub_23      0.019994
_diffrn_orient_matrix_ub_31      0.043595
_diffrn_orient_matrix_ub_32      0.163225
_diffrn_orient_matrix_ub_33      0.103782
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_number            4546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.19
_diffrn_reflns_theta_max         62.468
_diffrn_reflns_theta_full        62.468
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             2215
_reflns_number_gt                1939
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_cell_refinement       
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_data_reduction        
'CrysalisPro  Version 1.171.36.28 (Agilent Technologies, 2013)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0738P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2215
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.106
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.124

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
C1 C 1.1288(5) 0.3427(4) 0.4025(3) 0.0324(8) Uani 1 1 d . . . . .
C2 C 1.0510(5) 0.6566(4) 0.2820(3) 0.0327(8) Uani 1 1 d . . . . .
C3 C 0.9407(5) 0.6961(4) 0.1759(3) 0.0341(8) Uani 1 1 d . . . . .
H3 H 0.956444 0.805234 0.180689 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8122(5) 0.6000(4) 0.0649(3) 0.0312(7) Uani 1 1 d . . . . .
C5 C 0.6452(5) 0.2085(4) -0.0964(3) 0.0308(7) Uani 1 1 d . . . . .
C6 C 1.1694(6) 0.7880(5) 0.3939(4) 0.0412(9) Uani 1 1 d . . . . .
H6A H 1.148809 0.890891 0.377934 0.062 Uiso 1 1 calc R U . . .
H6B H 1.136424 0.788934 0.469672 0.062 Uiso 1 1 calc R U . . .
H6C H 1.300315 0.769896 0.407147 0.062 Uiso 1 1 calc R U . . .
C7 C 0.7183(5) 0.6730(4) -0.0367(3) 0.0363(8) Uani 1 1 d . . . . .
H7A H 0.764836 0.785927 -0.009662 0.054 Uiso 1 1 calc R U . . .
H7B H 0.744796 0.616815 -0.115196 0.054 Uiso 1 1 calc R U . . .
H7C H 0.584111 0.663687 -0.051382 0.054 Uiso 1 1 calc R U . . .
C8 C 1.3971(5) 0.4639(5) 0.6377(4) 0.0408(9) Uani 1 1 d . . . . .
H8A H 1.475967 0.443359 0.714166 0.061 Uiso 1 1 calc R U . . .
H8B H 1.474991 0.501506 0.595517 0.061 Uiso 1 1 calc R U . . .
H8C H 1.315654 0.545649 0.661001 0.061 Uiso 1 1 calc R U . . .
C9 C 0.5282(6) -0.0997(5) -0.2594(4) 0.0474(10) Uani 1 1 d . . . . .
H9A H 0.43638 -0.169957 -0.335409 0.071 Uiso 1 1 calc R U . . .
H9B H 0.651224 -0.105679 -0.270804 0.071 Uiso 1 1 calc R U . . .
H9C H 0.529314 -0.13373 -0.185923 0.071 Uiso 1 1 calc R U . . .
N1 N 1.1563(4) 0.4846(4) 0.3982(3) 0.0330(7) Uani 1 1 d . . . . .
N2 N 1.0563(4) 0.5054(3) 0.2827(3) 0.0301(6) Uani 1 1 d . . . . .
N3 N 0.7679(4) 0.4445(3) 0.0467(3) 0.0306(6) Uani 1 1 d . . . . .
N4 N 0.6557(4) 0.3630(4) -0.0728(3) 0.0323(7) Uani 1 1 d . . . . .
S1 S 0.96275(12) 0.19349(10) 0.29010(8) 0.0358(3) Uani 1 1 d . . . . .
S2 S 0.79186(13) 0.11150(10) -0.00243(8) 0.0370(3) Uani 1 1 d . . . . .
S3 S 1.25857(13) 0.28271(11) 0.53178(8) 0.0385(3) Uani 1 1 d . . . . .
S4 S 0.46890(13) 0.10169(11) -0.23389(9) 0.0412(3) Uani 1 1 d . . . . .
Cu1 Cu 0.89724(7) 0.32906(6) 0.15530(4) 0.0299(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.282(5) . ?
C1 S1 1.740(4) . ?
C1 S3 1.759(4) . ?
C2 N2 1.334(5) . ?
C2 C3 1.408(5) . ?
C2 C6 1.502(5) . ?
C3 C4 1.393(5) . ?
C4 N3 1.347(5) . ?
C4 C7 1.503(5) . ?
C5 N4 1.303(5) . ?
C5 S2 1.730(3) . ?
C5 S4 1.753(4) . ?
C8 S3 1.799(4) . ?
C9 S4 1.792(4) . ?
N1 N2 1.397(4) . ?
N2 Cu1 1.908(3) . ?
N3 N4 1.371(4) . ?
N3 Cu1 1.900(3) . ?
S1 Cu1 2.1797(10) . ?
S2 Cu1 2.1752(10) . ?

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 C1 S1 126.0(3) . . ?
N1 C1 S3 121.1(3) . . ?
S1 C1 S3 112.9(2) . . ?
N2 C2 C3 121.2(3) . . ?
N2 C2 C6 120.0(3) . . ?
C3 C2 C6 118.7(3) . . ?
C4 C3 C2 130.0(3) . . ?
N3 C4 C3 122.0(3) . . ?
N3 C4 C7 119.1(3) . . ?
C3 C4 C7 118.9(3) . . ?
N4 C5 S2 124.0(3) . . ?
N4 C5 S4 114.8(3) . . ?
S2 C5 S4 121.2(2) . . ?
C1 N1 N2 113.1(3) . . ?
C2 N2 N1 115.1(3) . . ?
C2 N2 Cu1 124.7(2) . . ?
N1 N2 Cu1 118.6(2) . . ?
C4 N3 N4 114.5(3) . . ?
C4 N3 Cu1 123.8(2) . . ?
N4 N3 Cu1 119.6(2) . . ?
C5 N4 N3 113.3(3) . . ?
C1 S1 Cu1 92.83(12) . . ?
C5 S2 Cu1 93.56(12) . . ?
C1 S3 C8 102.80(18) . . ?
C5 S4 C9 103.19(18) . . ?
N3 Cu1 N2 97.30(12) . . ?
N3 Cu1 S2 87.88(9) . . ?
N2 Cu1 S2 163.03(9) . . ?
N3 Cu1 S1 162.18(9) . . ?
N2 Cu1 S1 88.66(9) . . ?
S2 Cu1 S1 91.25(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
N2 C2 C3 C4 6.6(6) . . . . ?
C6 C2 C3 C4 -175.7(3) . . . . ?
C2 C3 C4 N3 3.3(6) . . . . ?
C2 C3 C4 C7 -177.5(3) . . . . ?
S1 C1 N1 N2 -8.9(4) . . . . ?
S3 C1 N1 N2 173.1(2) . . . . ?
C3 C2 N2 N1 -173.8(3) . . . . ?
C6 C2 N2 N1 8.5(4) . . . . ?
C3 C2 N2 Cu1 -8.7(5) . . . . ?
C6 C2 N2 Cu1 173.7(2) . . . . ?
C1 N1 N2 C2 167.2(3) . . . . ?
C1 N1 N2 Cu1 1.1(4) . . . . ?
C3 C4 N3 N4 -172.8(3) . . . . ?
C7 C4 N3 N4 8.0(4) . . . . ?
C3 C4 N3 Cu1 -9.6(5) . . . . ?
C7 C4 N3 Cu1 171.3(2) . . . . ?
S2 C5 N4 N3 -12.9(4) . . . . ?
S4 C5 N4 N3 167.5(2) . . . . ?
C4 N3 N4 C5 166.9(3) . . . . ?
Cu1 N3 N4 C5 2.9(4) . . . . ?
N1 C1 S1 Cu1 10.5(3) . . . . ?
S3 C1 S1 Cu1 -171.30(17) . . . . ?
N4 C5 S2 Cu1 14.4(3) . . . . ?
S4 C5 S2 Cu1 -166.11(19) . . . . ?
N1 C1 S3 C8 4.4(3) . . . . ?
S1 C1 S3 C8 -173.92(19) . . . . ?
N4 C5 S4 C9 166.1(3) . . . . ?
S2 C5 S4 C9 -13.4(3) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1916671'
loop_
_audit_author_name
_audit_author_address
'Paul Bernhardt' 'University of Queensland'
_audit_update_record             
;
2019-05-17 deposited with the CCDC.	2019-07-02 downloaded from the CCDC.
;

_audit_creation_date             2019-05-17T15:52:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_sum            'C42 H40 Cu2 N8 S8'
_chemical_formula_weight         1040.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   31.3989(8)
_cell_length_b                   9.4317(2)
_cell_length_c                   15.6907(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.795(2)
_cell_angle_gamma                90
_cell_volume                     4531.34(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4586
_cell_measurement_theta_min      4.91
_cell_measurement_theta_max      62.54
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2136

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

_exptl_absorpt_coefficient_mu    4.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.07
_diffrn_orient_matrix_ub_11      -0.049916
_diffrn_orient_matrix_ub_12      0.0077
_diffrn_orient_matrix_ub_13      -0.034031
_diffrn_orient_matrix_ub_21      0.003687
_diffrn_orient_matrix_ub_22      0.158886
_diffrn_orient_matrix_ub_23      -0.019759
_diffrn_orient_matrix_ub_31      0.00542
_diffrn_orient_matrix_ub_32      -0.036649
_diffrn_orient_matrix_ub_33      -0.09268
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Agilent Technologies Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_number            12713
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.906
_diffrn_reflns_theta_max         62.448
_diffrn_reflns_theta_full        62.448
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             3593
_reflns_number_gt                3099
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

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

_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/1
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+0.5732P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3593
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0834
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
C1 C 0.49423(8) 0.3406(2) 0.55294(15) 0.0253(5) Uani 1 1 d . . . . .
C2 C 0.48641(8) 0.2006(3) 0.35013(14) 0.0247(5) Uani 1 1 d . . . . .
C3 C 0.50911(8) 0.1185(2) 0.29892(15) 0.0230(5) Uani 1 1 d . . . . .
C4 C 0.54703(8) 0.0355(3) 0.33078(14) 0.0255(5) Uani 1 1 d . . . . .
C5 C 0.62660(9) -0.0367(3) 0.51341(16) 0.0337(6) Uani 1 1 d . . . . .
C6 C 0.44641(9) 0.2823(3) 0.30779(16) 0.0335(6) Uani 1 1 d . . . . .
H6A H 0.420679 0.239016 0.322874 0.05 Uiso 1 1 calc R U . . .
H6B H 0.443121 0.280893 0.244213 0.05 Uiso 1 1 calc R U . . .
H6C H 0.449266 0.380591 0.32859 0.05 Uiso 1 1 calc R U . . .
C7 C 0.56010(10) -0.0754(3) 0.27312(16) 0.0368(6) Uani 1 1 d . . . . .
H7A H 0.590794 -0.061969 0.270993 0.055 Uiso 1 1 calc R U . . .
H7B H 0.54177 -0.067069 0.214041 0.055 Uiso 1 1 calc R U . . .
H7C H 0.556273 -0.169646 0.296624 0.055 Uiso 1 1 calc R U . . .
C8 C 0.41036(8) 0.4245(3) 0.56104(16) 0.0319(6) Uani 1 1 d . . . . .
H8A H 0.406416 0.469563 0.502839 0.038 Uiso 1 1 calc R U . . .
H8B H 0.401442 0.323819 0.552872 0.038 Uiso 1 1 calc R U . . .
C9 C 0.38330(8) 0.5001(3) 0.61543(16) 0.0305(5) Uani 1 1 d . . . . .
C10 C 0.37742(9) 0.4416(3) 0.69338(16) 0.0352(6) Uani 1 1 d . . . . .
H10 H 0.390497 0.352949 0.712507 0.042 Uiso 1 1 calc R U . . .
C11 C 0.35272(9) 0.5110(4) 0.74340(18) 0.0422(7) Uani 1 1 d . . . . .
H11 H 0.348513 0.469135 0.795985 0.051 Uiso 1 1 calc R U . . .
C12 C 0.33426(10) 0.6404(4) 0.7172(2) 0.0496(8) Uani 1 1 d . . . . .
H12 H 0.317187 0.687758 0.751416 0.06 Uiso 1 1 calc R U . . .
C13 C 0.34058(11) 0.7008(4) 0.6415(2) 0.0546(8) Uani 1 1 d . . . . .
H13 H 0.328073 0.790762 0.623792 0.066 Uiso 1 1 calc R U . . .
C14 C 0.36519(9) 0.6316(3) 0.59027(19) 0.0418(7) Uani 1 1 d . . . . .
H14 H 0.369533 0.674703 0.538123 0.05 Uiso 1 1 calc R U . . .
C15 C 0.69071(10) -0.1918(3) 0.4553(2) 0.0453(7) Uani 1 1 d . . . . .
H15A H 0.710436 -0.274373 0.469832 0.054 Uiso 1 1 calc R U . . .
H15B H 0.664566 -0.22409 0.412045 0.054 Uiso 1 1 calc R U . . .
C16 C 0.71344(9) -0.0823(3) 0.41247(19) 0.0423(7) Uani 1 1 d . . . . .
C17 C 0.74305(11) 0.0145(4) 0.4593(2) 0.0545(8) Uani 1 1 d . . . . .
H17 H 0.74816 0.016085 0.521302 0.065 Uiso 1 1 calc R U . . .
C18 C 0.76518(13) 0.1085(5) 0.4169(4) 0.0770(13) Uani 1 1 d . . . . .
H18 H 0.785112 0.17471 0.449533 0.092 Uiso 1 1 calc R U . . .
C19 C 0.75817(17) 0.1055(6) 0.3275(4) 0.0926(18) Uani 1 1 d . . . . .
H19 H 0.773723 0.168361 0.298094 0.111 Uiso 1 1 calc R U . . .
C20 C 0.7288(2) 0.0120(7) 0.2807(3) 0.0916(17) Uani 1 1 d . . . . .
H20 H 0.723775 0.011179 0.218723 0.11 Uiso 1 1 calc R U . . .
C21 C 0.70638(13) -0.0814(5) 0.3226(2) 0.0623(10) Uani 1 1 d . . . . .
H21 H 0.685939 -0.145487 0.289192 0.075 Uiso 1 1 calc R U . . .
N1 N 0.47412(7) 0.2943(2) 0.47722(12) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.49900(6) 0.2046(2) 0.43810(12) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.57219(7) 0.0521(2) 0.41103(12) 0.0264(4) Uani 1 1 d . . . . .
N4 N 0.60654(7) -0.0416(2) 0.43233(13) 0.0316(5) Uani 1 1 d . . . . .
S1 S 0.54992(2) 0.31963(7) 0.59644(4) 0.02928(16) Uani 1 1 d . . . . .
S2 S 0.60940(2) 0.05661(8) 0.59454(4) 0.04028(19) Uani 1 1 d . . . . .
S3 S 0.46704(2) 0.43752(7) 0.61987(4) 0.03079(17) Uani 1 1 d . . . . .
S4 S 0.67367(2) -0.13870(9) 0.55293(5) 0.0493(2) Uani 1 1 d . . . . .
Cu1 Cu 0.55579(2) 0.15668(4) 0.50216(2) 0.02511(13) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 N1 1.292(3) . ?
C1 S1 1.742(3) . ?
C1 S3 1.751(2) . ?
C2 N2 1.350(3) . ?
C2 C3 1.417(3) . ?
C2 C6 1.498(4) . ?
C3 C4 1.420(4) . ?
C3 C3 1.515(5) 2_655 ?
C4 N3 1.339(3) . ?
C4 C7 1.498(3) . ?
C5 N4 1.289(4) . ?
C5 S2 1.729(3) . ?
C5 S4 1.757(3) . ?
C8 C9 1.510(4) . ?
C8 S3 1.819(3) . ?
C9 C14 1.386(4) . ?
C9 C10 1.391(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.374(5) . ?
C12 C13 1.371(5) . ?
C13 C14 1.394(5) . ?
C15 C16 1.496(5) . ?
C15 S4 1.802(3) . ?
C16 C21 1.378(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.385(6) . ?
C18 C19 1.371(8) . ?
C19 C20 1.366(9) . ?
C20 C21 1.382(7) . ?
N1 N2 1.384(3) . ?
N2 Cu1 1.898(2) . ?
N3 N4 1.377(3) . ?
N3 Cu1 1.8995(19) . ?
S1 Cu1 2.1692(7) . ?
S2 Cu1 2.1781(7) . ?

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 C1 S1 124.47(18) . . ?
N1 C1 S3 121.62(19) . . ?
S1 C1 S3 113.88(13) . . ?
N2 C2 C3 121.7(2) . . ?
N2 C2 C6 117.8(2) . . ?
C3 C2 C6 120.5(2) . . ?
C2 C3 C4 126.1(2) . . ?
C2 C3 C3 116.8(2) . 2_655 ?
C4 C3 C3 117.1(2) . 2_655 ?
N3 C4 C3 122.7(2) . . ?
N3 C4 C7 117.8(2) . . ?
C3 C4 C7 119.5(2) . . ?
N4 C5 S2 125.5(2) . . ?
N4 C5 S4 121.1(2) . . ?
S2 C5 S4 113.21(14) . . ?
C9 C8 S3 106.93(16) . . ?
C14 C9 C10 118.7(2) . . ?
C14 C9 C8 120.6(2) . . ?
C10 C9 C8 120.7(2) . . ?
C11 C10 C9 120.7(3) . . ?
C12 C11 C10 120.2(3) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 120.7(3) . . ?
C9 C14 C13 120.0(3) . . ?
C16 C15 S4 116.8(2) . . ?
C21 C16 C17 118.3(3) . . ?
C21 C16 C15 118.6(3) . . ?
C17 C16 C15 123.0(3) . . ?
C18 C17 C16 120.9(4) . . ?
C19 C18 C17 119.7(5) . . ?
C20 C19 C18 120.0(4) . . ?
C19 C20 C21 120.7(4) . . ?
C16 C21 C20 120.5(4) . . ?
C1 N1 N2 113.9(2) . . ?
C2 N2 N1 113.88(19) . . ?
C2 N2 Cu1 124.27(16) . . ?
N1 N2 Cu1 117.87(14) . . ?
C4 N3 N4 114.85(19) . . ?
C4 N3 Cu1 124.51(17) . . ?
N4 N3 Cu1 118.61(15) . . ?
C5 N4 N3 113.7(2) . . ?
C1 S1 Cu1 92.45(8) . . ?
C5 S2 Cu1 92.97(9) . . ?
C1 S3 C8 102.28(12) . . ?
C5 S4 C15 103.70(14) . . ?
N2 Cu1 N3 96.01(8) . . ?
N2 Cu1 S1 88.88(6) . . ?
N3 Cu1 S1 163.61(7) . . ?
N2 Cu1 S2 162.33(6) . . ?
N3 Cu1 S2 88.72(6) . . ?
S1 Cu1 S2 91.32(3) . . ?

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
N2 C2 C3 C4 -1.5(4) . . . . ?
C6 C2 C3 C4 -179.4(2) . . . . ?
N2 C2 C3 C3 177.9(2) . . . 2_655 ?
C6 C2 C3 C3 0.0(3) . . . 2_655 ?
C2 C3 C4 N3 -17.0(4) . . . . ?
C3 C3 C4 N3 163.5(2) 2_655 . . . ?
C2 C3 C4 C7 163.2(2) . . . . ?
C3 C3 C4 C7 -16.2(3) 2_655 . . . ?
S3 C8 C9 C14 106.2(2) . . . . ?
S3 C8 C9 C10 -71.4(3) . . . . ?
C14 C9 C10 C11 2.2(4) . . . . ?
C8 C9 C10 C11 179.8(2) . . . . ?
C9 C10 C11 C12 -1.1(4) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C10 C9 C14 C13 -1.8(4) . . . . ?
C8 C9 C14 C13 -179.4(3) . . . . ?
C12 C13 C14 C9 0.4(5) . . . . ?
S4 C15 C16 C21 -145.0(3) . . . . ?
S4 C15 C16 C17 38.3(4) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
C15 C16 C17 C18 176.2(3) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C17 C18 C19 C20 1.3(6) . . . . ?
C18 C19 C20 C21 -0.9(7) . . . . ?
C17 C16 C21 C20 1.0(5) . . . . ?
C15 C16 C21 C20 -175.9(3) . . . . ?
C19 C20 C21 C16 -0.3(6) . . . . ?
S1 C1 N1 N2 10.3(3) . . . . ?
S3 C1 N1 N2 -172.07(16) . . . . ?
C3 C2 N2 N1 177.7(2) . . . . ?
C6 C2 N2 N1 -4.3(3) . . . . ?
C3 C2 N2 Cu1 20.7(3) . . . . ?
C6 C2 N2 Cu1 -161.28(18) . . . . ?
C1 N1 N2 C2 -155.2(2) . . . . ?
C1 N1 N2 Cu1 3.3(3) . . . . ?
C3 C4 N3 N4 177.2(2) . . . . ?
C7 C4 N3 N4 -3.0(3) . . . . ?
C3 C4 N3 Cu1 13.7(3) . . . . ?
C7 C4 N3 Cu1 -166.52(18) . . . . ?
S2 C5 N4 N3 9.0(4) . . . . ?
S4 C5 N4 N3 -175.62(18) . . . . ?
C4 N3 N4 C5 -171.0(2) . . . . ?
Cu1 N3 N4 C5 -6.4(3) . . . . ?
N1 C1 S1 Cu1 -15.7(2) . . . . ?
S3 C1 S1 Cu1 166.47(12) . . . . ?
N4 C5 S2 Cu1 -6.5(3) . . . . ?
S4 C5 S2 Cu1 177.76(14) . . . . ?
N1 C1 S3 C8 7.3(2) . . . . ?
S1 C1 S3 C8 -174.82(14) . . . . ?
C9 C8 S3 C1 177.62(18) . . . . ?
N4 C5 S4 C15 16.0(3) . . . . ?
S2 C5 S4 C15 -168.10(16) . . . . ?
C16 C15 S4 C5 77.0(2) . . . . ?
C2 N2 Cu1 N3 -19.1(2) . . . . ?
N1 N2 Cu1 N3 -175.20(16) . . . . ?
C2 N2 Cu1 S1 145.24(19) . . . . ?
N1 N2 Cu1 S1 -10.89(16) . . . . ?
C2 N2 Cu1 S2 -123.9(2) . . . . ?
N1 N2 Cu1 S2 79.9(3) . . . . ?
C4 N3 Cu1 N2 2.1(2) . . . . ?
N4 N3 Cu1 N2 -160.88(18) . . . . ?
C4 N3 Cu1 S1 -104.7(3) . . . . ?
N4 N3 Cu1 S1 92.4(3) . . . . ?
C4 N3 Cu1 S2 165.0(2) . . . . ?
N4 N3 Cu1 S2 2.05(17) . . . . ?



# END of CIF
