# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

# SUBMISSION DETAILS

_audit_creation_method           'manual editing of SHELXL-2012 template'

# CHEMICAL DATA 

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 Cl Cu3 N2 S2'
_chemical_formula_sum            'C4 H12 Cl Cu3 N2 S2'
_chemical_formula_weight         378.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

# Crystal Data

_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                   7.5510(4)
_cell_length_b                   16.9848(7)
_cell_length_c                   7.8364(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.798(3)
_cell_angle_gamma                90
_cell_volume                     971.70(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1355
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      30.03

_exptl_crystal_description       rod-like
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.586
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    7.152
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.535
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Nonius FR590D, fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'KappaCCD (BruKer AXS-Nonius, FR540C)'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            2516
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.037
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1314
_reflns_number_gt                1034
_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       'COLLECT, Bruker AXS/Nonius'
_computing_cell_refinement       'HKL DENZO and SCALEPACK, Bruker AXS/Nonius'
_computing_data_reduction        'HKL DENZO and SCALEPACK, Bruker AXS/Nonius'
_computing_structure_solution    'SHELXS ((Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.80.05 2009 (L. J. Farrugia)'


# REFINEMENT DATA

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0330P)²+0.8292P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1314
_refine_ls_number_parameters     68
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.12118(6) -0.04255(2) -0.07429(6) 0.02145(15) Uani 1 1 d . . . . .
Cu2 Cu 0.5000 -0.03852(3) 0.2500 0.01959(16) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 -0.17240(6) 0.2500 0.0225(3) Uani 1 2 d S T P . .
S1 S 0.23414(11) 0.02819(4) 0.18333(11) 0.01501(18) Uani 1 1 d . . . . .
N1 N -0.0595(4) 0.15480(16) 0.0055(4) 0.0176(6) Uani 1 1 d . . . . .
H1 H -0.144(6) 0.168(2) -0.085(6) 0.029(11) Uiso 1 1 d . . . . .
H2 H -0.062(6) 0.194(3) 0.082(6) 0.035(12) Uiso 1 1 d . . . . .
C1 C 0.2729(4) 0.12920(19) 0.1165(4) 0.0179(6) Uani 1 1 d . . . . .
H1A H 0.2866 0.1642 0.2221 0.029(11) Uiso 1 1 d R . . . .
H1B H 0.3960 0.1306 0.0926 0.031(11) Uiso 1 1 d R . . . .
C2 C 0.1195(4) 0.15546(19) -0.0376(4) 0.0186(7) Uani 1 1 d . . . . .
H2A H 0.1158 0.1191 -0.1346 0.014(9) Uiso 1 1 d R . . . .
H2B H 0.1508 0.2042 -0.0716 0.026(10) Uiso 1 1 d 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 S1 2.3167(9) . ?
Cu2 S1 2.2474(8) 2_655 ?
Cu2 S1 2.2474(8) . ?
Cu2 Cl1 2.2739(12) . ?
S1 C1 1.839(3) . ?
N1 C2 1.475(4) . ?
N1 H1 0.86(4) . ?
N1 H2 0.90(5) . ?
C1 C2 1.512(4) . ?
C1 H1A 1.0027 . ?
C1 H1B 0.9941 . ?
C2 H2A 0.9746 . ?
C2 H2B 0.9184 . ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cu1 N1 2.067(3) . 5 ?
Cu1 S1 2.2852(9) . 6 ?
Cu1 S1 2.6110(9) . 5 ?
Cu1 Cu1 2.8076(8) . 5 ?
Cu1 Cu1 2.8912(9) . 2_554 ?
S1 Cu1 2.2852(9) . 6_556 ?
S1 Cu1 2.6110(9) . 5 ?
N1 Cu1 2.067(3) . 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 Cu1 S1 118.17(8) 5 6 ?
N1 Cu1 S1 107.97(9) 5 . ?
S1 Cu1 S1 122.44(3) 6 . ?
N1 Cu1 S1 83.70(8) 5 5 ?
S1 Cu1 S1 106.77(3) 6 5 ?
S1 Cu1 S1 110.83(3) . 5 ?
N1 Cu1 Cu1 98.77(8) 5 5 ?
S1 Cu1 Cu1 135.31(3) 6 5 ?
S1 Cu1 Cu1 60.37(2) . 5 ?
S1 Cu1 Cu1 50.46(2) 5 5 ?
N1 Cu1 Cu1 96.80(8) 5 2_554 ?
S1 Cu1 Cu1 59.21(2) 6 2_554 ?
S1 Cu1 Cu1 146.37(2) . 2_554 ?
S1 Cu1 Cu1 48.75(2) 5 2_554 ?
Cu1 Cu1 Cu1 94.24(3) 5 2_554 ?
S1 Cu2 S1 119.45(4) 2_655 . ?
S1 Cu2 Cl1 120.27(2) 2_655 . ?
S1 Cu2 Cl1 120.27(2) . . ?
C1 S1 Cu2 109.81(11) . . ?
C1 S1 Cu1 104.92(11) . 6_556 ?
Cu2 S1 Cu1 111.19(4) . 6_556 ?
C1 S1 Cu1 106.60(11) . . ?
Cu2 S1 Cu1 92.83(3) . . ?
Cu1 S1 Cu1 130.32(4) 6_556 . ?
C1 S1 Cu1 92.56(10) . 5 ?
Cu2 S1 Cu1 154.87(4) . 5 ?
Cu1 S1 Cu1 72.03(3) 6_556 5 ?
Cu1 S1 Cu1 69.17(3) . 5 ?
C2 N1 Cu1 110.35(19) . 5 ?
C2 N1 H1 110(3) . . ?
Cu1 N1 H1 107(3) 5 . ?
C2 N1 H2 109(3) . . ?
Cu1 N1 H2 117(3) 5 . ?
H1 N1 H2 103(4) . . ?
C2 C1 S1 111.0(2) . . ?
C2 C1 H1A 112.4 . . ?
S1 C1 H1A 108.0 . . ?
C2 C1 H1B 113.9 . . ?
S1 C1 H1B 107.5 . . ?
H1A C1 H1B 103.7 . . ?
N1 C2 C1 112.0(3) . . ?
N1 C2 H2A 109.2 . . ?
C1 C2 H2A 107.4 . . ?
N1 C2 H2B 113.1 . . ?
C1 C2 H2B 107.2 . . ?
H2A C2 H2B 107.7 . . ?

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
Cu2 S1 C1 C2 139.7(2) . . . . ?
Cu1 S1 C1 C2 -100.7(2) 6_556 . . . ?
Cu1 S1 C1 C2 40.4(2) . . . . ?
Cu1 S1 C1 C2 -28.7(2) 5 . . . ?
Cu1 N1 C2 C1 -60.1(3) 5 . . . ?
S1 C1 C2 N1 60.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Cl1 5_555 0.86(4) 2.67(4) 3.429(3) 149(4) ?
N1 H2 Cl1 3_455 0.90(5) 2.61(5) 3.471(3) 162(4) ?

_refine_diff_density_max         0.844
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.156

_shelxl_version_number           2012-9



_database_code_depnum_ccdc_archive 'CCDC 982135'
