# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1406752'
_audit_update_record             
;
2015-06-14 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H26 Cl2 Cu2 N8 O0 S2'
_chemical_formula_weight         736.71

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.670(4)
_cell_length_b                   9.585(5)
_cell_length_c                   9.816(4)
_cell_angle_alpha                69.619(19)
_cell_angle_beta                 71.22(2)
_cell_angle_gamma                81.89(2)
_cell_volume                     723.6(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             374
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7340
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.90
_reflns_number_total             3390
_reflns_number_gt                3179
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0969P)²+0.7647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3390
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.002

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 0.70349(4) 0.01522(3) 1.00062(4) 0.01761(18) Uani 1 1 d . . .
Cl1 Cl 0.49969(8) -0.12927(7) 1.18361(8) 0.0216(2) Uani 1 1 d . . .
S1 S 0.83997(9) -0.16567(7) 0.90591(8) 0.0203(2) Uani 1 1 d . . .
N1 N 0.6506(3) 0.1961(3) 1.0700(3) 0.0193(5) Uani 1 1 d . . .
N2 N 0.8928(3) 0.1380(3) 0.8605(3) 0.0180(5) Uani 1 1 d . . .
N3 N 1.0121(3) 0.0898(3) 0.7562(3) 0.0195(5) Uani 1 1 d . . .
N4 N 1.1131(3) -0.1096(3) 0.6781(3) 0.0229(5) Uani 1 1 d . . .
H4B H 1.1097 -0.2068 0.6905 0.028 Uiso 1 1 d R . .
C1 C 0.7596(3) 0.3055(3) 0.9876(3) 0.0180(5) Uani 1 1 d . . .
C2 C 0.7469(4) 0.4353(3) 1.0238(3) 0.0230(6) Uani 1 1 d . . .
H2A H 0.8230 0.5090 0.9675 0.028 Uiso 1 1 calc R . .
C3 C 0.6180(4) 0.4530(4) 1.1461(4) 0.0263(6) Uani 1 1 d . . .
H3A H 0.6063 0.5395 1.1716 0.032 Uiso 1 1 calc R . .
C4 C 0.5084(4) 0.3412(4) 1.2290(4) 0.0259(6) Uani 1 1 d . . .
H4A H 0.4228 0.3508 1.3119 0.031 Uiso 1 1 calc R . .
C5 C 0.5271(4) 0.2135(4) 1.1872(3) 0.0232(6) Uani 1 1 d . . .
H5A H 0.4520 0.1388 1.2421 0.028 Uiso 1 1 calc R . .
C6 C 0.9522(4) 0.5293(3) 0.6790(3) 0.0219(6) Uani 1 1 d . . .
H6A H 0.8427 0.5561 0.7122 0.026 Uiso 1 1 calc R . .
C7 C 1.0594(5) 0.6323(3) 0.5603(3) 0.0275(7) Uani 1 1 d . . .
H7A H 1.0204 0.7263 0.5131 0.033 Uiso 1 1 calc R . .
C8 C 1.2238(4) 0.5944(4) 0.5131(4) 0.0289(7) Uani 1 1 d . . .
H8A H 1.2954 0.6627 0.4343 0.035 Uiso 1 1 calc R . .
C9 C 1.2804(4) 0.4544(4) 0.5840(3) 0.0260(6) Uani 1 1 d . . .
H9A H 1.3909 0.4296 0.5536 0.031 Uiso 1 1 calc R . .
C10 C 1.1748(3) 0.3504(3) 0.6999(3) 0.0199(5) Uani 1 1 d . . .
H10A H 1.2147 0.2564 0.7458 0.024 Uiso 1 1 calc R . .
C11 C 1.0084(3) 0.3865(3) 0.7480(3) 0.0182(5) Uani 1 1 d . . .
C12 C 0.8923(3) 0.2731(3) 0.8620(3) 0.0173(5) Uani 1 1 d . . .
C13 C 0.9962(3) -0.0508(3) 0.7727(3) 0.0181(5) Uani 1 1 d . . .
C14 C 1.2443(4) -0.0232(4) 0.5553(4) 0.0304(7) Uani 1 1 d . . .
H14A H 1.3191 -0.0881 0.5075 0.046 Uiso 1 1 calc R . .
H14B H 1.3008 0.0245 0.5958 0.046 Uiso 1 1 calc R . .
H14C H 1.1996 0.0509 0.4818 0.046 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.983(3) . ?
Cu1 N1 2.019(2) . ?
Cu1 S1 2.2596(11) . ?
Cu1 Cl1 2.2761(12) . ?
Cu1 Cl1 2.7748(13) 2_657 ?
Cl1 Cu1 2.7748(13) 2_657 ?
S1 C13 1.742(3) . ?
N1 C5 1.338(4) . ?
N1 C1 1.357(4) . ?
N2 C12 1.300(4) . ?
N2 N3 1.358(3) . ?
N3 C13 1.321(4) . ?
N4 C13 1.344(3) . ?
N4 C14 1.456(4) . ?
N4 H4B 0.9000 . ?
C1 C2 1.389(4) . ?
C1 C12 1.481(4) . ?
C2 C3 1.394(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.394(4) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.399(4) . ?
C6 C11 1.396(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.387(5) . ?
C7 H7A 0.9300 . ?
C8 C9 1.382(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.387(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.399(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.477(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 80.11(10) . . ?
N2 Cu1 S1 84.74(8) . . ?
N1 Cu1 S1 162.68(8) . . ?
N2 Cu1 Cl1 173.24(8) . . ?
N1 Cu1 Cl1 97.60(8) . . ?
S1 Cu1 Cl1 96.49(5) . . ?
N2 Cu1 Cl1 96.22(8) . 2_657 ?
N1 Cu1 Cl1 89.81(8) . 2_657 ?
S1 Cu1 Cl1 100.19(4) . 2_657 ?
Cl1 Cu1 Cl1 90.11(4) . 2_657 ?
Cu1 Cl1 Cu1 89.89(4) . 2_657 ?
C13 S1 Cu1 94.23(10) . . ?
C5 N1 C1 119.8(2) . . ?
C5 N1 Cu1 126.9(2) . . ?
C1 N1 Cu1 113.32(18) . . ?
C12 N2 N3 120.1(2) . . ?
C12 N2 Cu1 117.51(19) . . ?
N3 N2 Cu1 122.07(18) . . ?
C13 N3 N2 112.2(2) . . ?
C13 N4 C14 123.1(2) . . ?
C13 N4 H4B 118.5 . . ?
C14 N4 H4B 118.4 . . ?
N1 C1 C2 121.3(3) . . ?
N1 C1 C12 115.0(2) . . ?
C2 C1 C12 123.7(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C7 C6 C11 120.5(3) . . ?
C7 C6 H6A 119.7 . . ?
C11 C6 H6A 119.7 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C7 C8 C9 119.5(3) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9A 119.5 . . ?
C10 C9 H9A 119.5 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C6 C11 C10 118.7(3) . . ?
C6 C11 C12 120.3(3) . . ?
C10 C11 C12 120.9(2) . . ?
N2 C12 C11 124.1(2) . . ?
N2 C12 C1 113.4(2) . . ?
C11 C12 C1 122.4(2) . . ?
N3 C13 N4 116.2(2) . . ?
N3 C13 S1 126.2(2) . . ?
N4 C13 S1 117.6(2) . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N2 Cu1 Cl1 Cu1 159.6(6) . . . 2_657 ?
N1 Cu1 Cl1 Cu1 89.83(8) . . . 2_657 ?
S1 Cu1 Cl1 Cu1 -100.27(4) . . . 2_657 ?
Cl1 Cu1 Cl1 Cu1 0.0 2_657 . . 2_657 ?
N2 Cu1 S1 C13 -4.70(12) . . . . ?
N1 Cu1 S1 C13 -33.7(3) . . . . ?
Cl1 Cu1 S1 C13 -178.02(10) . . . . ?
Cl1 Cu1 S1 C13 90.70(10) 2_657 . . . ?
N2 Cu1 N1 C5 -175.2(3) . . . . ?
S1 Cu1 N1 C5 -145.8(2) . . . . ?
Cl1 Cu1 N1 C5 -1.6(3) . . . . ?
Cl1 Cu1 N1 C5 88.5(3) 2_657 . . . ?
N2 Cu1 N1 C1 2.4(2) . . . . ?
S1 Cu1 N1 C1 31.8(4) . . . . ?
Cl1 Cu1 N1 C1 176.01(19) . . . . ?
Cl1 Cu1 N1 C1 -93.9(2) 2_657 . . . ?
N1 Cu1 N2 C12 -6.7(2) . . . . ?
S1 Cu1 N2 C12 -178.2(2) . . . . ?
Cl1 Cu1 N2 C12 -77.4(6) . . . . ?
Cl1 Cu1 N2 C12 82.1(2) 2_657 . . . ?
N1 Cu1 N2 N3 179.4(2) . . . . ?
S1 Cu1 N2 N3 7.8(2) . . . . ?
Cl1 Cu1 N2 N3 108.7(6) . . . . ?
Cl1 Cu1 N2 N3 -91.9(2) 2_657 . . . ?
C12 N2 N3 C13 178.6(3) . . . . ?
Cu1 N2 N3 C13 -7.5(3) . . . . ?
C5 N1 C1 C2 0.9(4) . . . . ?
Cu1 N1 C1 C2 -176.9(2) . . . . ?
C5 N1 C1 C12 179.2(3) . . . . ?
Cu1 N1 C1 C12 1.4(3) . . . . ?
N1 C1 C2 C3 -0.8(4) . . . . ?
C12 C1 C2 C3 -179.0(3) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C1 N1 C5 C4 -1.0(5) . . . . ?
Cu1 N1 C5 C4 176.5(2) . . . . ?
C3 C4 C5 N1 1.1(5) . . . . ?
C11 C6 C7 C8 -1.8(4) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C10 1.1(5) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C7 C6 C11 C10 2.3(4) . . . . ?
C7 C6 C11 C12 -173.5(3) . . . . ?
C9 C10 C11 C6 -1.1(4) . . . . ?
C9 C10 C11 C12 174.7(3) . . . . ?
N3 N2 C12 C11 4.9(4) . . . . ?
Cu1 N2 C12 C11 -169.2(2) . . . . ?
N3 N2 C12 C1 -176.8(2) . . . . ?
Cu1 N2 C12 C1 9.1(3) . . . . ?
C6 C11 C12 N2 131.7(3) . . . . ?
C10 C11 C12 N2 -44.1(4) . . . . ?
C6 C11 C12 C1 -46.5(4) . . . . ?
C10 C11 C12 C1 137.8(3) . . . . ?
N1 C1 C12 N2 -6.8(4) . . . . ?
C2 C1 C12 N2 171.5(3) . . . . ?
N1 C1 C12 C11 171.5(3) . . . . ?
C2 C1 C12 C11 -10.2(4) . . . . ?
N2 N3 C13 N4 -177.3(2) . . . . ?
N2 N3 C13 S1 2.0(4) . . . . ?
C14 N4 C13 N3 -4.7(5) . . . . ?
C14 N4 C13 S1 175.8(3) . . . . ?
Cu1 S1 C13 N3 3.0(3) . . . . ?
Cu1 S1 C13 N4 -177.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.848
_refine_diff_density_min         -1.798
_refine_diff_density_rms         0.145

####################################################################### 
# 
# 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_11111
_database_code_depnum_ccdc_archive 'CCDC 1406753'
_audit_update_record             
;
2015-06-14 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H11 Br2 Cu2 N8 S2'
_chemical_formula_weight         810.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.6615(19)
_cell_length_b                   11.803(2)
_cell_length_c                   15.561(3)
_cell_angle_alpha                110.40(3)
_cell_angle_beta                 93.32(3)
_cell_angle_gamma                109.26(3)
_cell_volume                     1539.8(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             395
_exptl_absorpt_coefficient_mu    2.072
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12514
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_av_sigmaI/netI    0.1819
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5382
_reflns_number_gt                2519
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1459P)²+23.3449P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5382
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.1162
_refine_ls_wR_factor_ref         0.3516
_refine_ls_wR_factor_gt          0.3408
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.003

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 0.0766(2) 0.5163(2) 0.11433(16) 0.0365(7) Uani 1 1 d . . .
Br2 Br -0.2050(2) -0.30314(18) 0.36915(15) 0.0475(7) Uani 1 1 d . . .
Cu2 Cu -0.0056(2) -0.1094(2) 0.38597(15) 0.0321(7) Uani 1 1 d . . .
S1A S -0.1402(5) 0.0195(4) 0.4184(3) 0.0351(11) Uani 1 1 d . . .
C19A C 0.295(2) -0.0864(19) 0.3666(11) 0.040(5) Uani 1 1 d . . .
N7A N 0.1208(14) 0.1487(13) 0.3769(9) 0.029(3) Uani 1 1 d . . .
H7AA H 0.1825 0.2106 0.3652 0.035 Uiso 1 1 calc R . .
N8A N -0.0520(18) 0.2464(15) 0.4018(11) 0.044(4) Uani 1 1 d . . .
N6A N 0.1465(14) 0.0459(14) 0.3757(10) 0.032(3) Uani 1 1 d . . .
N5A N 0.1598(14) -0.1792(12) 0.3579(9) 0.028(3) Uani 1 1 d . . .
C20A C 0.2833(18) 0.0368(16) 0.3669(11) 0.031(4) Uani 1 1 d . . .
C18A C 0.424(2) -0.1044(19) 0.3707(12) 0.040(4) Uani 1 1 d . . .
H18A H 0.5137 -0.0370 0.3785 0.049 Uiso 1 1 calc R . .
C27A C -0.007(2) 0.1468(18) 0.3975(12) 0.036(4) Uani 1 1 d . . .
C21A C 0.4038(19) 0.1425(19) 0.3585(13) 0.041(5) Uani 1 1 d . . .
C22A C 0.4858(19) 0.1171(18) 0.2884(14) 0.042(5) Uani 1 1 d . . .
H22A H 0.4592 0.0320 0.2452 0.050 Uiso 1 1 calc R . .
C24A C 0.659(3) 0.344(3) 0.346(2) 0.082(9) Uani 1 1 d . . .
H24A H 0.7425 0.4086 0.3426 0.098 Uiso 1 1 calc R . .
C17A C 0.4215(18) -0.2253(16) 0.3631(11) 0.030(4) Uani 1 1 d . . .
H17A H 0.5080 -0.2437 0.3602 0.036 Uiso 1 1 calc R . .
C23A C 0.608(2) 0.217(2) 0.2813(16) 0.050(5) Uani 1 1 d . . .
H23A H 0.6564 0.1963 0.2314 0.060 Uiso 1 1 calc R . .
C16A C 0.288(2) -0.3173(19) 0.3599(14) 0.048(5) Uani 1 1 d . . .
H16A H 0.2862 -0.3956 0.3617 0.058 Uiso 1 1 calc R . .
C25A C 0.573(2) 0.3690(19) 0.4174(16) 0.053(6) Uani 1 1 d . . .
H25A H 0.5993 0.4541 0.4606 0.064 Uiso 1 1 calc R . .
C26A C 0.4563(19) 0.2742(17) 0.4246(15) 0.045(5) Uani 1 1 d . . .
H26A H 0.4080 0.2952 0.4745 0.054 Uiso 1 1 calc R . .
Br1 Br -0.1032(2) 0.3470(2) 0.14342(16) 0.0525(7) Uani 1 1 d . . .
S1 S -0.0804(5) 0.6120(5) 0.0894(4) 0.0404(12) Uani 1 1 d . . .
N2 N 0.2359(13) 0.6780(11) 0.1186(10) 0.029(3) Uani 1 1 d . . .
N4 N 0.0175(15) 0.8552(15) 0.1058(11) 0.039(4) Uani 1 1 d . . .
C7 C 0.506(2) 0.7860(14) 0.1149(10) 0.031(4) Uani 1 1 d . . .
N3 N 0.2081(14) 0.7840(14) 0.1194(10) 0.039(4) Uani 1 1 d . . .
H3A H 0.2770 0.8572 0.1276 0.047 Uiso 1 1 calc R . .
C10 C 0.7384(18) 0.9842(18) 0.1004(17) 0.052(6) Uani 1 1 d . . .
H10A H 0.8195 1.0476 0.0935 0.062 Uiso 1 1 calc R . .
N1 N 0.2591(15) 0.4717(14) 0.1376(10) 0.036(4) Uani 1 1 d . . .
C13 C 0.0620(17) 0.7622(18) 0.1059(12) 0.036(4) Uani 1 1 d . . .
C5 C 0.3877(17) 0.5614(14) 0.1302(11) 0.027(4) Uani 1 1 d . . .
C6 C 0.3708(17) 0.6817(16) 0.1229(11) 0.028(4) Uani 1 1 d . . .
C12 C 0.485(2) 0.8230(19) 0.0405(16) 0.053(6) Uani 1 1 d . . .
H12A H 0.3945 0.7839 -0.0019 0.063 Uiso 1 1 calc R . .
C4 C 0.5212(19) 0.5453(17) 0.1395(13) 0.038(4) Uani 1 1 d . . .
H4B H 0.6090 0.6054 0.1357 0.046 Uiso 1 1 calc R . .
C3 C 0.520(2) 0.4381(19) 0.1547(16) 0.061(7) Uani 1 1 d . . .
H3B H 0.6097 0.4247 0.1588 0.074 Uiso 1 1 calc R . .
C8 C 0.636(2) 0.8530(19) 0.1819(14) 0.048(5) Uani 1 1 d . . .
H8A H 0.6473 0.8298 0.2324 0.057 Uiso 1 1 calc R . .
C1 C 0.262(2) 0.3724(18) 0.1491(17) 0.055(6) Uani 1 1 d . . .
H1A H 0.1714 0.3104 0.1479 0.066 Uiso 1 1 calc R . .
C11 C 0.607(2) 0.923(2) 0.0336(17) 0.060(6) Uani 1 1 d . . .
H11A H 0.6005 0.9479 -0.0164 0.072 Uiso 1 1 calc R . .
C9 C 0.749(2) 0.9534(19) 0.1740(15) 0.049(5) Uani 1 1 d . . .
H9A H 0.8343 1.0007 0.2208 0.059 Uiso 1 1 calc R . .
C15 C 0.155(2) -0.2972(19) 0.3540(12) 0.046(5) Uani 1 1 d . . .
H15A H 0.0643 -0.3630 0.3474 0.055 Uiso 1 1 calc R . .
C2 C 0.395(3) 0.349(2) 0.1640(17) 0.065(6) Uani 1 1 d . . .
H2A H 0.3970 0.2796 0.1788 0.077 Uiso 1 1 calc R . .
C28 C 0.050(2) 0.3613(19) 0.3890(17) 0.058(6) Uani 1 1 d . . .
H28A H 0.0018 0.4219 0.3939 0.086 Uiso 1 1 calc R . .
H28B H 0.0760 0.3343 0.3285 0.086 Uiso 1 1 calc R . .
H28C H 0.1393 0.4026 0.4364 0.086 Uiso 1 1 calc R . .
C14 C 0.121(2) 0.982(2) 0.1165(14) 0.054(5) Uani 1 1 d . . .
H14A H 0.0665 1.0365 0.1147 0.080 Uiso 1 1 calc R . .
H14B H 0.1758 0.9730 0.0667 0.080 Uiso 1 1 calc R . .
H14C H 0.1893 1.0213 0.1754 0.080 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.994(12) . ?
Cu1 N1 2.047(14) . ?
Cu1 S1 2.258(5) . ?
Cu1 Br1 2.376(3) . ?
Br2 Cu2 2.372(3) . ?
Cu2 N6A 2.000(14) . ?
Cu2 N5A 2.030(14) . ?
Cu2 S1A 2.260(5) . ?
S1A C27A 1.769(19) . ?
C19A C18A 1.33(3) . ?
C19A N5A 1.36(2) . ?
C19A C20A 1.49(2) . ?
N7A C27A 1.29(2) . ?
N7A N6A 1.311(18) . ?
N8A C27A 1.36(2) . ?
N8A C28 1.48(2) . ?
N6A C20A 1.372(19) . ?
N5A C15 1.36(2) . ?
C20A C21A 1.45(3) . ?
C18A C17A 1.38(2) . ?
C21A C22A 1.39(3) . ?
C21A C26A 1.43(3) . ?
C22A C23A 1.41(3) . ?
C24A C23A 1.38(3) . ?
C24A C25A 1.44(3) . ?
C17A C16A 1.37(3) . ?
C16A C15 1.38(3) . ?
C25A C26A 1.34(3) . ?
S1 C13 1.770(18) . ?
N2 C6 1.286(19) . ?
N2 N3 1.360(19) . ?
N4 C13 1.31(2) . ?
N4 C14 1.45(2) . ?
C7 C8 1.38(2) . ?
C7 C12 1.40(2) . ?
C7 C6 1.52(2) . ?
N3 C13 1.338(19) . ?
C10 C9 1.32(3) . ?
C10 C11 1.39(3) . ?
N1 C1 1.25(2) . ?
N1 C5 1.38(2) . ?
C5 C4 1.37(2) . ?
C5 C6 1.52(2) . ?
C12 C11 1.41(3) . ?
C4 C3 1.36(3) . ?
C3 C2 1.37(3) . ?
C8 C9 1.37(3) . ?
C1 C2 1.43(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 81.2(5) . . ?
N2 Cu1 S1 84.3(4) . . ?
N1 Cu1 S1 165.5(4) . . ?
N2 Cu1 Br1 168.1(4) . . ?
N1 Cu1 Br1 97.8(4) . . ?
S1 Cu1 Br1 96.40(15) . . ?
N6A Cu2 N5A 81.1(5) . . ?
N6A Cu2 S1A 83.0(4) . . ?
N5A Cu2 S1A 164.0(4) . . ?
N6A Cu2 Br2 169.4(4) . . ?
N5A Cu2 Br2 100.1(4) . . ?
S1A Cu2 Br2 95.80(14) . . ?
C27A S1A Cu2 94.2(6) . . ?
C18A C19A N5A 124.0(18) . . ?
C18A C19A C20A 123.0(18) . . ?
N5A C19A C20A 113.0(15) . . ?
C27A N7A N6A 112.5(14) . . ?
C27A N8A C28 120.0(16) . . ?
N7A N6A C20A 121.7(14) . . ?
N7A N6A Cu2 124.1(10) . . ?
C20A N6A Cu2 114.2(11) . . ?
C15 N5A C19A 118.6(15) . . ?
C15 N5A Cu2 125.4(12) . . ?
C19A N5A Cu2 114.1(11) . . ?
N6A C20A C21A 119.9(14) . . ?
N6A C20A C19A 115.2(15) . . ?
C21A C20A C19A 124.8(14) . . ?
C19A C18A C17A 118.6(17) . . ?
N7A C27A N8A 120.3(17) . . ?
N7A C27A S1A 125.4(14) . . ?
N8A C27A S1A 114.2(13) . . ?
C22A C21A C26A 115.7(18) . . ?
C22A C21A C20A 120.3(17) . . ?
C26A C21A C20A 123.7(17) . . ?
C21A C22A C23A 121.7(18) . . ?
C23A C24A C25A 115(2) . . ?
C16A C17A C18A 118.0(16) . . ?
C24A C23A C22A 122.3(19) . . ?
C17A C16A C15 122.0(17) . . ?
C26A C25A C24A 122(2) . . ?
C25A C26A C21A 122.3(19) . . ?
C13 S1 Cu1 95.4(5) . . ?
C6 N2 N3 119.3(13) . . ?
C6 N2 Cu1 117.8(10) . . ?
N3 N2 Cu1 122.9(9) . . ?
C13 N4 C14 122.2(14) . . ?
C8 C7 C12 120.9(16) . . ?
C8 C7 C6 123.3(15) . . ?
C12 C7 C6 115.3(15) . . ?
C13 N3 N2 112.8(14) . . ?
C9 C10 C11 120.7(18) . . ?
C1 N1 C5 120.7(15) . . ?
C1 N1 Cu1 127.8(13) . . ?
C5 N1 Cu1 111.2(10) . . ?
N4 C13 N3 120.0(16) . . ?
N4 C13 S1 116.1(11) . . ?
N3 C13 S1 123.9(14) . . ?
C4 C5 N1 120.0(15) . . ?
C4 C5 C6 124.4(14) . . ?
N1 C5 C6 115.2(13) . . ?
N2 C6 C7 127.2(14) . . ?
N2 C6 C5 113.7(14) . . ?
C7 C6 C5 119.0(13) . . ?
C7 C12 C11 116.3(18) . . ?
C3 C4 C5 117.6(17) . . ?
C4 C3 C2 124(2) . . ?
C9 C8 C7 120.1(18) . . ?
N1 C1 C2 123.9(18) . . ?
C10 C11 C12 121(2) . . ?
C10 C9 C8 120.8(18) . . ?
N5A C15 C16A 118.4(19) . . ?
C3 C2 C1 114(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.957
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.228
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1406754'
_audit_update_record             
;
2015-06-14 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Cl Cu N4 S'
_chemical_formula_weight         354.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   11.006(2)
_cell_length_b                   21.944(4)
_cell_length_c                   11.945(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.09(3)
_cell_angle_gamma                90.00
_cell_volume                     2742.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.8012
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12252
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.85
_reflns_number_total             3173
_reflns_number_gt                2560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0891P)²+2.2134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3173
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   0.741
_refine_ls_restrained_S_all      0.741
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.005

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 0.38508(2) 0.201450(11) 0.08213(2) 0.01487(13) Uani 1 1 d . . .
Cl1 Cl 0.39102(5) 0.30305(2) 0.06120(5) 0.01913(15) Uani 1 1 d . . .
S1 S 0.48699(6) 0.17748(2) -0.04699(5) 0.02025(16) Uani 1 1 d . . .
N4 N 0.37752(16) 0.11206(8) 0.10343(16) 0.0139(4) Uani 1 1 d . . .
N2 N 0.43128(17) 0.07110(8) 0.04591(16) 0.0152(4) Uani 1 1 d . . .
N3 N 0.30685(19) 0.19950(8) 0.21239(18) 0.0163(4) Uani 1 1 d . . .
C2 C 0.3057(2) 0.09379(9) 0.16431(19) 0.0144(4) Uani 1 1 d . . .
C12 C 0.2215(2) -0.06164(10) 0.2581(2) 0.0218(5) Uani 1 1 d . . .
H12A H 0.2359 -0.0850 0.3260 0.026 Uiso 1 1 calc R . .
C9 C 0.1805(2) 0.00717(10) 0.05448(19) 0.0165(4) Uani 1 1 d . . .
H9A H 0.1673 0.0298 -0.0140 0.020 Uiso 1 1 calc R . .
C8 C 0.25615(19) 0.03097(9) 0.16305(19) 0.0141(4) Uani 1 1 d . . .
N1 N 0.55317(18) 0.06471(8) -0.07697(17) 0.0206(4) Uani 1 1 d . . .
H1A H 0.5552 0.0258 -0.0678 0.025 Uiso 1 1 calc R . .
H1B H 0.5920 0.0813 -0.1215 0.025 Uiso 1 1 calc R . .
C5 C 0.1999(2) 0.24152(11) 0.3399(2) 0.0235(5) Uani 1 1 d . . .
H5A H 0.1802 0.2755 0.3774 0.028 Uiso 1 1 calc R . .
C1 C 0.4896(2) 0.09945(9) -0.02196(19) 0.0153(4) Uani 1 1 d . . .
C13 C 0.2764(2) -0.00392(10) 0.2646(2) 0.0187(5) Uani 1 1 d . . .
H13A H 0.3265 0.0113 0.3369 0.022 Uiso 1 1 calc R . .
C3 C 0.2645(2) 0.14322(9) 0.22945(19) 0.0150(4) Uani 1 1 d . . .
C6 C 0.1550(2) 0.18459(11) 0.3570(2) 0.0242(5) Uani 1 1 d . . .
H6A H 0.1037 0.1797 0.4053 0.029 Uiso 1 1 calc R . .
C7 C 0.1881(2) 0.13462(10) 0.3004(2) 0.0203(5) Uani 1 1 d . . .
H7A H 0.1589 0.0959 0.3104 0.024 Uiso 1 1 calc R . .
C10 C 0.1254(2) -0.05006(10) 0.0493(2) 0.0194(5) Uani 1 1 d . . .
H10A H 0.0748 -0.0655 -0.0226 0.023 Uiso 1 1 calc R . .
C11 C 0.1454(2) -0.08433(10) 0.1507(2) 0.0221(5) Uani 1 1 d . . .
H11A H 0.1079 -0.1226 0.1468 0.027 Uiso 1 1 calc R . .
C4 C 0.2747(2) 0.24727(10) 0.2664(2) 0.0203(5) Uani 1 1 d . . .
H4A H 0.3035 0.2858 0.2541 0.024 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 N4 1.9831(18) . ?
Cu1 N3 1.999(2) . ?
Cu1 S1 2.2333(8) . ?
Cu1 Cl1 2.2466(7) . ?
S1 C1 1.737(2) . ?
N4 C2 1.292(3) . ?
N4 N2 1.372(2) . ?
N2 C1 1.334(3) . ?
N3 C4 1.335(3) . ?
N3 C3 1.357(3) . ?
C2 C8 1.481(3) . ?
C2 C3 1.486(3) . ?
C12 C11 1.389(3) . ?
C12 C13 1.395(3) . ?
C12 H12A 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C8 1.406(3) . ?
C9 H9A 0.9300 . ?
C8 C13 1.393(3) . ?
N1 C1 1.337(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C5 C4 1.383(4) . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9300 . ?
C13 H13A 0.9300 . ?
C3 C7 1.380(3) . ?
C6 C7 1.395(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C4 H4A 0.9300 . ?

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
N4 Cu1 N3 80.42(7) . . ?
N4 Cu1 S1 84.59(6) . . ?
N3 Cu1 S1 164.27(5) . . ?
N4 Cu1 Cl1 178.59(6) . . ?
N3 Cu1 Cl1 98.18(5) . . ?
S1 Cu1 Cl1 96.82(2) . . ?
C1 S1 Cu1 95.63(8) . . ?
C2 N4 N2 120.84(18) . . ?
C2 N4 Cu1 115.87(14) . . ?
N2 N4 Cu1 122.81(14) . . ?
C1 N2 N4 111.25(17) . . ?
C4 N3 C3 119.1(2) . . ?
C4 N3 Cu1 127.03(16) . . ?
C3 N3 Cu1 112.79(15) . . ?
N4 C2 C8 124.80(19) . . ?
N4 C2 C3 114.07(18) . . ?
C8 C2 C3 120.88(19) . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C13 C8 C9 119.2(2) . . ?
C13 C8 C2 122.96(19) . . ?
C9 C8 C2 117.77(19) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
N2 C1 N1 117.17(19) . . ?
N2 C1 S1 125.40(17) . . ?
N1 C1 S1 117.41(17) . . ?
C8 C13 C12 120.1(2) . . ?
C8 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
N3 C3 C7 121.3(2) . . ?
N3 C3 C2 114.2(2) . . ?
C7 C3 C2 124.43(19) . . ?
C5 C6 C7 118.7(2) . . ?
C5 C6 H6A 120.7 . . ?
C7 C6 H6A 120.7 . . ?
C3 C7 C6 119.4(2) . . ?
C3 C7 H7A 120.3 . . ?
C6 C7 H7A 120.3 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
N3 C4 C5 122.3(2) . . ?
N3 C4 H4A 118.8 . . ?
C5 C4 H4A 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.85
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.094

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1406755'
_audit_update_record             
;
2015-06-14 deposited with the CCDC.
2016-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Br Cu N4 S'
_chemical_formula_weight         398.77

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   11.090(2)
_cell_length_b                   22.323(5)
_cell_length_c                   12.146(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.23(3)
_cell_angle_gamma                90.00
_cell_volume                     2901.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1576
_exptl_absorpt_coefficient_mu    4.397
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.4734
_exptl_absorpt_correction_T_max  0.6205
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14843
_diffrn_reflns_av_R_equivalents  0.1206
_diffrn_reflns_av_sigmaI/netI    0.1642
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         27.94
_reflns_number_total             3480
_reflns_number_gt                1351
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0375P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0076(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3480
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   0.778
_refine_ls_restrained_S_all      0.778
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.39866(5) 0.30496(2) 0.06053(5) 0.0382(2) Uani 1 1 d . . .
Cu1 Cu 0.38709(6) 0.19915(2) 0.08440(5) 0.0291(2) Uani 1 1 d . . .
S1 S 0.49136(15) 0.17486(6) -0.04273(14) 0.0448(5) Uani 1 1 d . . .
N1 N 0.3040(4) 0.19755(16) 0.2134(4) 0.0281(11) Uani 1 1 d . . .
C6 C 0.3074(4) 0.0935(2) 0.1679(4) 0.0226(12) Uani 1 1 d . . .
N2 N 0.3775(4) 0.11140(15) 0.1057(3) 0.0248(10) Uani 1 1 d . . .
N3 N 0.4310(4) 0.07083(16) 0.0485(3) 0.0238(10) Uani 1 1 d . . .
C7 C 0.2587(4) 0.03219(19) 0.1695(4) 0.0205(11) Uani 1 1 d . . .
N4 N 0.5547(4) 0.06401(17) -0.0756(3) 0.0402(13) Uani 1 1 d . . .
H4A H 0.5568 0.0257 -0.0672 0.048 Uiso 1 1 calc R . .
H4B H 0.5939 0.0806 -0.1200 0.048 Uiso 1 1 calc R . .
C12 C 0.1824(5) 0.0081(2) 0.0706(4) 0.0281(13) Uani 1 1 d . . .
H12A H 0.1672 0.0301 0.0033 0.034 Uiso 1 1 calc R . .
C3 C 0.1533(6) 0.1834(3) 0.3590(5) 0.0563(19) Uani 1 1 d . . .
H3B H 0.1033 0.1787 0.4090 0.068 Uiso 1 1 calc R . .
C13 C 0.4904(5) 0.0979(2) -0.0194(4) 0.0299(13) Uani 1 1 d . . .
C5 C 0.2634(5) 0.1426(2) 0.2309(4) 0.0268(13) Uani 1 1 d . . .
C4 C 0.1859(5) 0.1339(2) 0.3034(5) 0.0378(15) Uani 1 1 d . . .
H4C H 0.1567 0.0959 0.3144 0.045 Uiso 1 1 calc R . .
C8 C 0.2813(5) -0.0023(2) 0.2679(4) 0.0359(15) Uani 1 1 d . . .
H8A H 0.3323 0.0128 0.3355 0.043 Uiso 1 1 calc R . .
C1 C 0.2711(6) 0.2448(2) 0.2664(5) 0.0409(16) Uani 1 1 d . . .
H1A H 0.2999 0.2826 0.2538 0.049 Uiso 1 1 calc R . .
C9 C 0.2297(5) -0.0587(2) 0.2678(5) 0.0431(16) Uani 1 1 d . . .
H9A H 0.2469 -0.0813 0.3345 0.052 Uiso 1 1 calc R . .
C10 C 0.1525(5) -0.0816(2) 0.1684(5) 0.0455(16) Uani 1 1 d . . .
H10A H 0.1172 -0.1193 0.1684 0.055 Uiso 1 1 calc R . .
C11 C 0.1276(5) -0.0483(2) 0.0687(5) 0.0398(15) Uani 1 1 d . . .
H11A H 0.0752 -0.0633 0.0017 0.048 Uiso 1 1 calc R . .
C2 C 0.1950(6) 0.2387(3) 0.3398(5) 0.0522(19) Uani 1 1 d . . .
H2A H 0.1726 0.2721 0.3757 0.063 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
Br1 Cu1 2.3873(8) . ?
Cu1 N2 1.982(3) . ?
Cu1 N1 2.016(4) . ?
Cu1 S1 2.2257(16) . ?
S1 C13 1.742(5) . ?
N1 C1 1.335(5) . ?
N1 C5 1.344(6) . ?
C6 N2 1.282(6) . ?
C6 C7 1.474(6) . ?
C6 C5 1.489(6) . ?
N2 N3 1.368(5) . ?
N3 C13 1.329(6) . ?
C7 C12 1.385(6) . ?
C7 C8 1.388(6) . ?
N4 C13 1.342(6) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C12 C11 1.394(6) . ?
C12 H12A 0.9300 . ?
C3 C2 1.358(7) . ?
C3 C4 1.391(6) . ?
C3 H3B 0.9300 . ?
C5 C4 1.396(7) . ?
C4 H4C 0.9300 . ?
C8 C9 1.383(6) . ?
C8 H8A 0.9300 . ?
C1 C2 1.386(7) . ?
C1 H1A 0.9300 . ?
C9 C10 1.380(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(7) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C2 H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N1 80.21(16) . . ?
N2 Cu1 S1 84.57(13) . . ?
N1 Cu1 S1 164.12(11) . . ?
N2 Cu1 Br1 179.47(12) . . ?
N1 Cu1 Br1 99.32(11) . . ?
S1 Cu1 Br1 95.88(4) . . ?
C13 S1 Cu1 95.80(18) . . ?
C1 N1 C5 120.0(5) . . ?
C1 N1 Cu1 126.9(4) . . ?
C5 N1 Cu1 112.3(3) . . ?
N2 C6 C7 125.3(4) . . ?
N2 C6 C5 113.9(4) . . ?
C7 C6 C5 120.4(4) . . ?
C6 N2 N3 120.3(4) . . ?
C6 N2 Cu1 116.5(3) . . ?
N3 N2 Cu1 122.9(3) . . ?
C13 N3 N2 111.5(4) . . ?
C12 C7 C8 117.5(4) . . ?
C12 C7 C6 119.5(4) . . ?
C8 C7 C6 122.9(4) . . ?
C13 N4 H4A 120.0 . . ?
C13 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C7 C12 C11 122.0(5) . . ?
C7 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3B 120.2 . . ?
C4 C3 H3B 120.2 . . ?
N3 C13 N4 118.5(4) . . ?
N3 C13 S1 125.0(4) . . ?
N4 C13 S1 116.5(4) . . ?
N1 C5 C4 120.9(4) . . ?
N1 C5 C6 114.9(4) . . ?
C4 C5 C6 124.2(5) . . ?
C3 C4 C5 118.6(5) . . ?
C3 C4 H4C 120.7 . . ?
C5 C4 H4C 120.7 . . ?
C9 C8 C7 121.6(5) . . ?
C9 C8 H8A 119.2 . . ?
C7 C8 H8A 119.2 . . ?
N1 C1 C2 121.5(5) . . ?
N1 C1 H1A 119.2 . . ?
C2 C1 H1A 119.2 . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 120.1(5) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11A 120.5 . . ?
C12 C11 H11A 120.5 . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.165


