# 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 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_20130228lt_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H20 Cl2 Cu2 N4 S4'
_chemical_formula_weight         570.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5271(9)
_cell_length_b                   10.7784(9)
_cell_length_c                   10.9396(9)
_cell_angle_alpha                68.855(4)
_cell_angle_beta                 65.795(4)
_cell_angle_gamma                78.787(5)
_cell_volume                     1054.33(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    7983
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      28.18

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6169
_exptl_absorpt_correction_T_max  0.6305
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17096
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         28.30
_reflns_number_total             5169
_reflns_number_gt                4419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0959P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5169
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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 0.70134(4) 0.07988(4) 0.68108(4) 0.01904(13) Uani 1 1 d . . .
Cu2 Cu 1.73690(4) -0.52624(4) -0.20857(4) 0.02388(14) Uani 1 1 d . . .
Cl1 Cl 1.56489(8) -0.46628(8) -0.27319(9) 0.02742(19) Uani 1 1 d . . .
Cl2 Cl 1.91918(8) -0.57994(8) -0.15976(8) 0.02653(19) Uani 1 1 d . . .
S1 S 0.79559(8) -0.11309(7) 0.63406(8) 0.01923(18) Uani 1 1 d . . .
S2 S 0.96368(8) -0.15489(7) 0.35550(8) 0.01950(18) Uani 1 1 d . . .
N1 N 0.8581(2) 0.0805(2) 0.3872(2) 0.0163(5) Uani 1 1 d . . .
N2 N 0.7949(3) 0.1662(2) 0.4682(3) 0.0176(5) Uani 1 1 d . . .
C1 C 0.8705(3) -0.0541(3) 0.4592(3) 0.0166(6) Uani 1 1 d . . .
C2 C 0.8949(3) 0.1531(3) 0.2429(3) 0.0185(6) Uani 1 1 d . . .
C3 C 0.8537(3) 0.2817(3) 0.2373(3) 0.0216(6) Uani 1 1 d . . .
H3A H 0.8644 0.3555 0.1541 0.026 Uiso 1 1 calc R . .
C4 C 0.7917(3) 0.2866(3) 0.3778(3) 0.0197(6) Uani 1 1 d . . .
C5 C 0.9474(4) -0.3179(3) 0.4832(3) 0.0260(7) Uani 1 1 d . . .
H5A H 0.9973 -0.3841 0.4352 0.039 Uiso 1 1 calc R . .
H5B H 0.8486 -0.3373 0.5332 0.039 Uiso 1 1 calc R . .
H5C H 0.9875 -0.3212 0.5510 0.039 Uiso 1 1 calc R . .
C6 C 0.9613(3) 0.0980(3) 0.1228(3) 0.0247(7) Uani 1 1 d . . .
H6A H 0.9753 0.1706 0.0338 0.037 Uiso 1 1 calc R . .
H6B H 0.9007 0.0339 0.1323 0.037 Uiso 1 1 calc R . .
H6C H 1.0516 0.0532 0.1233 0.037 Uiso 1 1 calc R . .
C7 C 0.7285(4) 0.4035(3) 0.4276(4) 0.0266(7) Uani 1 1 d . . .
H7A H 0.6948 0.3752 0.5308 0.040 Uiso 1 1 calc R . .
H7B H 0.6502 0.4431 0.3969 0.040 Uiso 1 1 calc R . .
H7C H 0.7987 0.4696 0.3878 0.040 Uiso 1 1 calc R . .
S11 S 0.70101(8) 0.12069(8) 0.87072(8) 0.02118(18) Uani 1 1 d . . .
S12 S 0.47316(8) 0.24611(8) 1.06872(8) 0.02182(19) Uani 1 1 d . . .
N11 N 0.4511(2) 0.2028(2) 0.8555(3) 0.0163(5) Uani 1 1 d . . .
N12 N 0.5003(3) 0.1517(2) 0.7427(3) 0.0169(5) Uani 1 1 d . . .
C11 C 0.5397(3) 0.1885(3) 0.9257(3) 0.0174(6) Uani 1 1 d . . .
C12 C 0.3177(3) 0.2635(3) 0.8713(3) 0.0179(6) Uani 1 1 d . . .
C13 C 0.2843(3) 0.2475(3) 0.7700(3) 0.0198(6) Uani 1 1 d . . .
H13A H 0.1995 0.2766 0.7543 0.024 Uiso 1 1 calc R . .
C14 C 0.4011(3) 0.1791(3) 0.6925(3) 0.0192(6) Uani 1 1 d . . .
C15 C 0.6121(3) 0.1996(3) 1.1353(3) 0.0249(7) Uani 1 1 d . . .
H15A H 0.5852 0.2280 1.2186 0.037 Uiso 1 1 calc R . .
H15B H 0.6968 0.2429 1.0622 0.037 Uiso 1 1 calc R . .
H15C H 0.6298 0.1027 1.1612 0.037 Uiso 1 1 calc R . .
C16 C 0.2337(3) 0.3370(3) 0.9736(4) 0.0243(7) Uani 1 1 d . . .
H16A H 0.1441 0.3692 0.9626 0.036 Uiso 1 1 calc R . .
H16B H 0.2845 0.4129 0.9554 0.036 Uiso 1 1 calc R . .
H16C H 0.2174 0.2773 1.0699 0.036 Uiso 1 1 calc R . .
C17 C 0.4212(3) 0.1409(3) 0.5670(3) 0.0239(7) Uani 1 1 d . . .
H17A H 0.5127 0.0942 0.5372 0.036 Uiso 1 1 calc R . .
H17B H 0.4160 0.2213 0.4896 0.036 Uiso 1 1 calc R . .
H17C H 0.3480 0.0823 0.5919 0.036 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 N12 2.026(2) . ?
Cu1 N2 2.042(3) . ?
Cu1 S1 2.2640(8) . ?
Cu1 S11 2.2692(8) . ?
Cu2 Cl1 2.1121(9) . ?
Cu2 Cl2 2.1184(9) . ?
S1 C1 1.663(3) . ?
S2 C1 1.729(3) . ?
S2 C5 1.794(3) . ?
N1 C1 1.389(4) . ?
N1 N2 1.396(3) . ?
N1 C2 1.407(4) . ?
N2 C4 1.322(4) . ?
C2 C3 1.357(4) . ?
C2 C6 1.489(4) . ?
C3 C4 1.419(4) . ?
C3 H3A 0.9500 . ?
C4 C7 1.483(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
S11 C11 1.666(3) . ?
S12 C11 1.719(3) . ?
S12 C15 1.801(3) . ?
N11 C11 1.390(4) . ?
N11 N12 1.396(3) . ?
N11 C12 1.398(3) . ?
N12 C14 1.308(4) . ?
C12 C13 1.364(4) . ?
C12 C16 1.489(4) . ?
C13 C14 1.420(4) . ?
C13 H13A 0.9500 . ?
C14 C17 1.495(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
N12 Cu1 N2 108.30(10) . . ?
N12 Cu1 S1 130.53(7) . . ?
N2 Cu1 S1 84.52(7) . . ?
N12 Cu1 S11 84.39(7) . . ?
N2 Cu1 S11 133.25(7) . . ?
S1 Cu1 S11 121.61(3) . . ?
Cl1 Cu2 Cl2 175.70(4) . . ?
C1 S1 Cu1 99.51(10) . . ?
C1 S2 C5 102.46(14) . . ?
C1 N1 N2 117.2(2) . . ?
C1 N1 C2 132.8(2) . . ?
N2 N1 C2 109.9(2) . . ?
C4 N2 N1 106.2(2) . . ?
C4 N2 Cu1 135.6(2) . . ?
N1 N2 Cu1 116.89(19) . . ?
N1 C1 S1 121.2(2) . . ?
N1 C1 S2 115.9(2) . . ?
S1 C1 S2 122.89(18) . . ?
C3 C2 N1 105.7(2) . . ?
C3 C2 C6 127.7(3) . . ?
N1 C2 C6 126.6(3) . . ?
C2 C3 C4 107.9(3) . . ?
C2 C3 H3A 126.0 . . ?
C4 C3 H3A 126.0 . . ?
N2 C4 C3 110.3(3) . . ?
N2 C4 C7 121.1(3) . . ?
C3 C4 C7 128.6(3) . . ?
S2 C5 H5A 109.5 . . ?
S2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 S11 Cu1 99.56(10) . . ?
C11 S12 C15 102.24(14) . . ?
C11 N11 N12 117.2(2) . . ?
C11 N11 C12 132.9(2) . . ?
N12 N11 C12 109.9(2) . . ?
C14 N12 N11 106.0(2) . . ?
C14 N12 Cu1 135.7(2) . . ?
N11 N12 Cu1 117.69(17) . . ?
N11 C11 S11 120.8(2) . . ?
N11 C11 S12 116.0(2) . . ?
S11 C11 S12 123.14(18) . . ?
C13 C12 N11 106.2(2) . . ?
C13 C12 C16 127.5(3) . . ?
N11 C12 C16 126.2(3) . . ?
C12 C13 C14 106.6(3) . . ?
C12 C13 H13A 126.7 . . ?
C14 C13 H13A 126.7 . . ?
N12 C14 C13 111.3(3) . . ?
N12 C14 C17 120.1(3) . . ?
C13 C14 C17 128.6(3) . . ?
S12 C15 H15A 109.5 . . ?
S12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
N12 Cu1 S1 C1 107.28(14) . . . . ?
N2 Cu1 S1 C1 -2.18(12) . . . . ?
S11 Cu1 S1 C1 -140.69(10) . . . . ?
C1 N1 N2 C4 -178.4(2) . . . . ?
C2 N1 N2 C4 0.4(3) . . . . ?
C1 N1 N2 Cu1 -9.4(3) . . . . ?
C2 N1 N2 Cu1 169.37(19) . . . . ?
N12 Cu1 N2 C4 40.1(3) . . . . ?
S1 Cu1 N2 C4 171.1(3) . . . . ?
S11 Cu1 N2 C4 -59.6(3) . . . . ?
N12 Cu1 N2 N1 -124.58(19) . . . . ?
S1 Cu1 N2 N1 6.40(18) . . . . ?
S11 Cu1 N2 N1 135.65(16) . . . . ?
N2 N1 C1 S1 7.5(4) . . . . ?
C2 N1 C1 S1 -171.0(3) . . . . ?
N2 N1 C1 S2 -174.20(19) . . . . ?
C2 N1 C1 S2 7.3(4) . . . . ?
Cu1 S1 C1 N1 -2.0(2) . . . . ?
Cu1 S1 C1 S2 179.77(16) . . . . ?
C5 S2 C1 N1 -176.7(2) . . . . ?
C5 S2 C1 S1 1.6(2) . . . . ?
C1 N1 C2 C3 178.5(3) . . . . ?
N2 N1 C2 C3 -0.1(3) . . . . ?
C1 N1 C2 C6 0.1(5) . . . . ?
N2 N1 C2 C6 -178.4(3) . . . . ?
N1 C2 C3 C4 -0.3(3) . . . . ?
C6 C2 C3 C4 178.0(3) . . . . ?
N1 N2 C4 C3 -0.6(3) . . . . ?
Cu1 N2 C4 C3 -166.4(2) . . . . ?
N1 N2 C4 C7 178.9(3) . . . . ?
Cu1 N2 C4 C7 13.0(5) . . . . ?
C2 C3 C4 N2 0.6(4) . . . . ?
C2 C3 C4 C7 -178.9(3) . . . . ?
N12 Cu1 S11 C11 -2.77(13) . . . . ?
N2 Cu1 S11 C11 107.15(14) . . . . ?
S1 Cu1 S11 C11 -137.70(11) . . . . ?
C11 N11 N12 C14 -178.8(3) . . . . ?
C12 N11 N12 C14 -0.4(3) . . . . ?
C11 N11 N12 Cu1 -6.2(3) . . . . ?
C12 N11 N12 Cu1 172.18(19) . . . . ?
N2 Cu1 N12 C14 41.1(3) . . . . ?
S1 Cu1 N12 C14 -57.6(3) . . . . ?
S11 Cu1 N12 C14 174.9(3) . . . . ?
N2 Cu1 N12 N11 -128.7(2) . . . . ?
S1 Cu1 N12 N11 132.63(17) . . . . ?
S11 Cu1 N12 N11 5.13(19) . . . . ?
N12 N11 C11 S11 3.4(4) . . . . ?
C12 N11 C11 S11 -174.5(3) . . . . ?
N12 N11 C11 S12 -177.3(2) . . . . ?
C12 N11 C11 S12 4.8(4) . . . . ?
Cu1 S11 C11 N11 0.6(3) . . . . ?
Cu1 S11 C11 S12 -178.70(17) . . . . ?
C15 S12 C11 N11 176.2(2) . . . . ?
C15 S12 C11 S11 -4.5(2) . . . . ?
C11 N11 C12 C13 179.0(3) . . . . ?
N12 N11 C12 C13 1.0(3) . . . . ?
C11 N11 C12 C16 2.1(5) . . . . ?
N12 N11 C12 C16 -175.9(3) . . . . ?
N11 C12 C13 C14 -1.2(3) . . . . ?
C16 C12 C13 C14 175.7(3) . . . . ?
N11 N12 C14 C13 -0.4(3) . . . . ?
Cu1 N12 C14 C13 -170.9(2) . . . . ?
N11 N12 C14 C17 178.4(3) . . . . ?
Cu1 N12 C14 C17 7.8(5) . . . . ?
C12 C13 C14 N12 1.0(4) . . . . ?
C12 C13 C14 C17 -177.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.490
_refine_diff_density_min         -2.156
_refine_diff_density_rms         0.195
_database_code_depnum_ccdc_archive 'CCDC 996834'
