# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1442084'
_audit_update_record             
;
2015-12-12 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H34 Cu N4 O20 S4'
_chemical_formula_weight         674.15

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'
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                   8.044(2)
_cell_length_b                   9.357(2)
_cell_length_c                   9.822(2)
_cell_angle_alpha                111.230(2)
_cell_angle_beta                 107.301(2)
_cell_angle_gamma                104.268(2)
_cell_volume                     603.6(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4811
_cell_measurement_theta_min      2.4615
_cell_measurement_theta_max      27.5110

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.855
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             351
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7561
_exptl_absorpt_correction_T_max  0.7745
_exptl_absorpt_process_details   sadabs

_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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4836
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.09
_reflns_number_total             2140
_reflns_number_gt                2103
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0590P)²+0.5303P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     219
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.939
_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
Cu1 Cu 0.5000 0.5000 0.0000 0.0160(3) Uani 1 2 d S . .
S1 S 0.73704(14) 0.26460(12) -0.01734(13) 0.0204(3) Uani 1 1 d . . .
S2 S 0.28998(14) 0.25136(12) 0.36885(12) 0.0186(3) Uani 1 1 d . . .
O1 O 0.9012(5) 0.3160(5) -0.0507(5) 0.0413(9) Uani 1 1 d . . .
O2 O 0.7932(5) 0.3307(4) 0.1573(4) 0.0371(9) Uani 1 1 d . . .
O3 O 0.6460(4) 0.0796(4) -0.0979(4) 0.0267(7) Uani 1 1 d . . .
O4 O 0.5961(4) 0.3257(4) -0.0868(4) 0.0259(7) Uani 1 1 d . . .
O5 O 0.6664(4) 0.5702(4) 0.2219(4) 0.0227(7) Uani 1 1 d D . .
H5B H 0.703(9) 0.494(6) 0.230(8) 0.049(18) Uiso 1 1 d D . .
H5A H 0.630(8) 0.611(7) 0.296(5) 0.037(15) Uiso 1 1 d D . .
O6 O 0.7476(5) 0.7156(4) -0.0016(4) 0.0279(7) Uani 1 1 d D . .
H6B H 0.857(5) 0.710(8) 0.018(8) 0.049(18) Uiso 1 1 d D . .
H6A H 0.706(10) 0.708(9) -0.097(4) 0.06(2) Uiso 1 1 d D . .
O7 O 0.4163(5) 0.3235(5) 0.3110(4) 0.0345(8) Uani 1 1 d . . .
O8 O 0.3938(5) 0.2536(4) 0.5196(4) 0.0289(7) Uani 1 1 d . . .
O9 O 0.1696(5) 0.0638(4) 0.2402(4) 0.0340(8) Uani 1 1 d D . .
H9A H 0.2348 0.0258 0.1999 0.051 Uiso 1 1 calc RD . .
O10 O 0.1483(5) 0.3190(4) 0.3787(4) 0.0330(8) Uani 1 1 d . . .
N1 N 0.7571(6) 0.0306(5) 0.2076(5) 0.0268(8) Uani 1 1 d D A .
N2 N 0.8006(6) 0.4029(5) 0.6872(6) 0.0354(10) Uani 1 1 d D . .
H2WC H 0.680(3) 0.379(8) 0.656(7) 0.043(17) Uiso 1 1 d D . .
H2WB H 0.839(9) 0.402(8) 0.778(4) 0.040(17) Uiso 1 1 d D . .
H2WA H 0.855(10) 0.506(4) 0.709(9) 0.06(2) Uiso 1 1 d D . .
C1 C 0.8114(8) 0.0307(7) 0.3648(6) 0.0383(12) Uani 1 1 d DU . .
H1A H 0.7652 -0.0851 0.3422 0.046 Uiso 0.688(14) 1 calc PR A 1
H1B H 0.9489 0.0740 0.4161 0.046 Uiso 0.688(14) 1 calc PR A 1
H1C H 0.9398 0.0377 0.4102 0.046 Uiso 0.312(14) 1 d PR A 2
H1D H 0.7223 -0.0623 0.3626 0.046 Uiso 0.312(14) 1 d PR A 2
C2 C 0.7524(10) 0.1209(8) 0.4862(8) 0.0260(18) Uani 0.688(14) 1 d PDU A 1
H2A H 0.7918 0.0992 0.5775 0.031 Uiso 0.688(14) 1 calc PR A 1
H2B H 0.6152 0.0826 0.4396 0.031 Uiso 0.688(14) 1 calc PR A 1
C2' C 0.789(2) 0.2071(19) 0.4505(17) 0.027(4) Uani 0.312(14) 1 d PDU A 2
H2AA H 0.8797 0.2963 0.4492 0.032 Uiso 0.312(14) 1 calc PR A 2
H2AB H 0.6623 0.1967 0.3923 0.032 Uiso 0.312(14) 1 calc PR A 2
C3 C 0.8411(10) 0.3040(9) 0.5414(9) 0.0264(19) Uani 0.688(14) 1 d PDU A 1
H3A H 0.7890 0.3275 0.4532 0.032 Uiso 0.688(14) 1 calc PR A 1
H3B H 0.9769 0.3394 0.5749 0.032 Uiso 0.688(14) 1 calc PR A 1
C3' C 0.826(2) 0.2459(16) 0.6224(16) 0.029(4) Uani 0.312(14) 1 d PDU A 2
H3AA H 0.7356 0.1580 0.6255 0.034 Uiso 0.312(14) 1 calc PR A 2
H3AB H 0.9533 0.2597 0.6828 0.034 Uiso 0.312(14) 1 calc PR A 2
H1WC H 0.637(3) 0.009(8) 0.160(7) 0.047(18) Uiso 1 1 d D . .
H1WB H 0.822(9) 0.127(5) 0.219(9) 0.07(2) Uiso 1 1 d D . .
H1WA H 0.774(9) -0.050(6) 0.141(6) 0.045(17) Uiso 1 1 d D . .


_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 O5 1.941(3) 2_665 ?
Cu1 O5 1.941(3) . ?
Cu1 O4 1.997(3) 2_665 ?
Cu1 O4 1.997(3) . ?
S1 O1 1.463(4) . ?
S1 O2 1.471(4) . ?
S1 O3 1.482(3) . ?
S1 O4 1.490(3) . ?
S2 O10 1.444(3) . ?
S2 O7 1.447(3) . ?
S2 O8 1.458(3) . ?
S2 O9 1.563(3) . ?
O5 H5B 0.862(18) . ?
O5 H5A 0.864(18) . ?
O6 H6B 0.862(18) . ?
O6 H6A 0.863(18) . ?
O9 H9A 0.8200 . ?
N1 C1 1.474(7) . ?
N1 H1WC 0.872(18) . ?
N1 H1WB 0.869(18) . ?
N1 H1WA 0.872(18) . ?
N2 C3' 1.465(12) . ?
N2 C3 1.574(8) . ?
N2 H2WC 0.869(18) . ?
N2 H2WB 0.858(18) . ?
N2 H2WA 0.866(19) . ?
C1 C2 1.471(8) . ?
C1 C2' 1.641(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C2 C3 1.494(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2' C3' 1.509(14) . ?
C2' H2AA 0.9700 . ?
C2' H2AB 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3' H3AA 0.9700 . ?
C3' H3AB 0.9700 . ?

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
O5 Cu1 O5 180.00(18) 2_665 . ?
O5 Cu1 O4 92.25(12) 2_665 2_665 ?
O5 Cu1 O4 87.75(12) . 2_665 ?
O5 Cu1 O4 87.75(12) 2_665 . ?
O5 Cu1 O4 92.25(12) . . ?
O4 Cu1 O4 180.0 2_665 . ?
O1 S1 O2 111.2(2) . . ?
O1 S1 O3 109.3(2) . . ?
O2 S1 O3 109.3(2) . . ?
O1 S1 O4 108.9(2) . . ?
O2 S1 O4 110.07(19) . . ?
O3 S1 O4 107.91(19) . . ?
O10 S2 O7 114.6(2) . . ?
O10 S2 O8 111.8(2) . . ?
O7 S2 O8 111.9(2) . . ?
O10 S2 O9 103.3(2) . . ?
O7 S2 O9 107.6(2) . . ?
O8 S2 O9 106.8(2) . . ?
S1 O4 Cu1 136.24(19) . . ?
Cu1 O5 H5B 112(4) . . ?
Cu1 O5 H5A 118(4) . . ?
H5B O5 H5A 110(6) . . ?
H6B O6 H6A 106(6) . . ?
S2 O9 H9A 109.5 . . ?
C1 N1 H1WC 113(4) . . ?
C1 N1 H1WB 111(5) . . ?
H1WC N1 H1WB 108(7) . . ?
C1 N1 H1WA 110(4) . . ?
H1WC N1 H1WA 104(6) . . ?
H1WB N1 H1WA 111(7) . . ?
C3' N2 C3 43.5(6) . . ?
C3' N2 H2WC 108(4) . . ?
C3 N2 H2WC 110(4) . . ?
C3' N2 H2WB 86(4) . . ?
C3 N2 H2WB 124(4) . . ?
H2WC N2 H2WB 105(6) . . ?
C3' N2 H2WA 138(5) . . ?
C3 N2 H2WA 103(5) . . ?
H2WC N2 H2WA 107(7) . . ?
H2WB N2 H2WA 106(7) . . ?
C2 C1 N1 121.5(5) . . ?
C2 C1 C2' 37.2(6) . . ?
N1 C1 C2' 92.2(6) . . ?
C2 C1 H1A 106.9 . . ?
N1 C1 H1A 106.9 . . ?
C2' C1 H1A 142.4 . . ?
C2 C1 H1B 106.9 . . ?
N1 C1 H1B 106.9 . . ?
C2' C1 H1B 97.7 . . ?
H1A C1 H1B 106.7 . . ?
C2 C1 H1C 113.9 . . ?
N1 C1 H1C 113.2 . . ?
C2' C1 H1C 113.7 . . ?
H1A C1 H1C 88.4 . . ?
H1B C1 H1C 18.3 . . ?
C2 C1 H1D 79.5 . . ?
N1 C1 H1D 113.3 . . ?
C2' C1 H1D 112.8 . . ?
H1A C1 H1D 29.9 . . ?
H1B C1 H1D 127.4 . . ?
H1C C1 H1D 110.6 . . ?
C1 C2 C3 109.2(5) . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C3' C2' C1 107.9(9) . . ?
C3' C2' H2AA 110.1 . . ?
C1 C2' H2AA 110.1 . . ?
C3' C2' H2AB 110.1 . . ?
C1 C2' H2AB 110.1 . . ?
H2AA C2' H2AB 108.4 . . ?
C2 C3 N2 109.4(5) . . ?
C2 C3 H3A 109.8 . . ?
N2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
N2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N2 C3' C2' 103.7(10) . . ?
N2 C3' H3AA 111.0 . . ?
C2' C3' H3AA 111.0 . . ?
N2 C3' H3AB 111.0 . . ?
C2' C3' H3AB 111.0 . . ?
H3AA C3' H3AB 109.0 . . ?

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
O1 S1 O4 Cu1 -109.4(3) . . . . ?
O2 S1 O4 Cu1 12.7(4) . . . . ?
O3 S1 O4 Cu1 132.0(3) . . . . ?
O5 Cu1 O4 S1 -179.3(3) 2_665 . . . ?
O5 Cu1 O4 S1 0.7(3) . . . . ?
O4 Cu1 O4 S1 2(100) 2_665 . . . ?
N1 C1 C2 C3 -64.3(7) . . . . ?
C2' C1 C2 C3 -21.4(9) . . . . ?
C2 C1 C2' C3' 32.3(9) . . . . ?
N1 C1 C2' C3' 176.8(10) . . . . ?
C1 C2 C3 N2 -172.6(5) . . . . ?
C3' N2 C3 C2 30.1(10) . . . . ?
C3 N2 C3' C2' -19.8(7) . . . . ?
C1 C2' C3' N2 -179.4(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.134
####################################################################### 
# 
# 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_ee
_database_code_depnum_ccdc_archive 'CCDC 1442085'
_audit_update_record             
;
2016-01-20 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H34 Cu N4 O20 S4'
_chemical_formula_weight         674.15

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'
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                   10.649(4)
_cell_length_b                   10.677(4)
_cell_length_c                   10.799(4)
_cell_angle_alpha                94.771(4)
_cell_angle_beta                 100.757(4)
_cell_angle_gamma                95.748(4)
_cell_volume                     1193.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7560
_cell_measurement_theta_min      2.4661
_cell_measurement_theta_max      27.5142

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             702
_exptl_absorpt_coefficient_mu    1.362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7538
_exptl_absorpt_correction_T_max  0.7724
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9604
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_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         1.93
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4242
_reflns_number_gt                3991
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0486P)²+0.7849P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4242
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_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 0.5000 0.0000 0.5000 0.00713(10) Uani 1 2 d S . .
N1 N 0.45721(15) 0.29984(14) 0.26695(14) 0.0112(3) Uani 1 1 d . . .
H10 H 0.4520 0.3802 0.2529 0.013 Uiso 1 1 d R . .
H11 H 0.3810 0.2541 0.2391 0.013 Uiso 1 1 d R . .
H12 H 0.4840 0.2935 0.3493 0.013 Uiso 1 1 d R . .
N2 N 0.56125(15) 0.23989(14) -0.15662(14) 0.0123(3) Uani 1 1 d . . .
H7 H 0.4862 0.1936 -0.1833 0.015 Uiso 1 1 d R . .
H8 H 0.6135 0.2140 -0.2052 0.015 Uiso 1 1 d R . .
H9 H 0.5532 0.3202 -0.1664 0.015 Uiso 1 1 d R . .
N3 N -0.02366(14) 0.77968(14) 0.75525(14) 0.0102(3) Uani 1 1 d . . .
H4 H -0.0318 0.8560 0.7301 0.012 Uiso 1 1 d R . .
H5 H -0.0954 0.7280 0.7256 0.012 Uiso 1 1 d R . .
H6 H -0.0085 0.7866 0.8397 0.012 Uiso 1 1 d R . .
N4 N 0.03034(15) 0.76836(14) 0.35880(14) 0.0106(3) Uani 1 1 d . . .
H1 H -0.0292 0.7056 0.3277 0.013 Uiso 1 1 d R . .
H2 H 0.0146 0.8336 0.3191 0.013 Uiso 1 1 d R . .
H3 H 0.1027 0.7456 0.3444 0.013 Uiso 1 1 d R . .
C1 C 0.55321(18) 0.25483(17) 0.19516(17) 0.0125(4) Uani 1 1 d . . .
H1A H 0.5578 0.1634 0.2018 0.015 Uiso 1 1 calc R . .
H1B H 0.6394 0.3009 0.2313 0.015 Uiso 1 1 calc R . .
C2 C 0.51390(17) 0.27757(17) 0.05713(17) 0.0127(4) Uani 1 1 d . . .
H2A H 0.5160 0.3696 0.0503 0.015 Uiso 1 1 calc R . .
H2B H 0.4248 0.2375 0.0234 0.015 Uiso 1 1 calc R . .
C3 C 0.60440(18) 0.22274(18) -0.02064(17) 0.0144(4) Uani 1 1 d . . .
H3A H 0.6929 0.2658 0.0102 0.017 Uiso 1 1 calc R . .
H3B H 0.6056 0.1315 -0.0107 0.017 Uiso 1 1 calc R . .
C4 C 0.08939(17) 0.72891(17) 0.71398(17) 0.0118(4) Uani 1 1 d . . .
H4A H 0.1093 0.6537 0.7584 0.014 Uiso 1 1 calc R . .
H4B H 0.1653 0.7938 0.7384 0.014 Uiso 1 1 calc R . .
C5 C 0.06482(18) 0.69234(17) 0.57168(17) 0.0127(4) Uani 1 1 d . . .
H5D H -0.0087 0.6248 0.5480 0.015 Uiso 1 1 calc R . .
H5C H 0.1415 0.6578 0.5493 0.015 Uiso 1 1 calc R . .
C6 C 0.03577(18) 0.80361(17) 0.49606(16) 0.0117(4) Uani 1 1 d . . .
H6D H -0.0477 0.8307 0.5084 0.014 Uiso 1 1 calc R . .
H6C H 0.1034 0.8757 0.5273 0.014 Uiso 1 1 calc R . .
Cu2 Cu 0.0000 0.5000 0.0000 0.00763(10) Uani 1 2 d S . .
S1 S 0.26229(4) 0.00328(4) 0.26449(4) 0.00717(12) Uani 1 1 d . . .
S2 S 0.30246(4) 0.40643(4) 0.67437(4) 0.00819(12) Uani 1 1 d . . .
S3 S 0.22142(4) 0.51835(4) 0.25399(4) 0.00729(12) Uani 1 1 d . . .
S4 S 0.20695(4) 0.07815(4) 0.83765(4) 0.00771(12) Uani 1 1 d . . .
O1 O 0.25360(12) 0.09839(12) 0.17092(12) 0.0119(3) Uani 1 1 d . . .
O2 O 0.21461(12) -0.12314(12) 0.19882(12) 0.0125(3) Uani 1 1 d . . .
O3 O 0.18783(12) 0.03712(12) 0.36192(12) 0.0126(3) Uani 1 1 d . . .
O4 O 0.40170(12) 0.00550(12) 0.32427(12) 0.0116(3) Uani 1 1 d . . .
O5 O 0.51689(12) 0.23087(12) 0.52049(12) 0.0129(3) Uani 1 1 d . . .
H5B H 0.4559 0.2476 0.5564 0.019 Uiso 1 1 d R . .
H5A H 0.5866 0.2705 0.5626 0.019 Uiso 1 1 d R . .
O6 O 0.34334(12) -0.01169(12) 0.56933(12) 0.0109(3) Uani 1 1 d . . .
H6B H 0.3452 0.0179 0.6478 0.016 Uiso 1 1 d R . .
H6A H 0.2807 0.0165 0.5187 0.016 Uiso 1 1 d R . .
O7 O 0.17537(12) 0.43123(12) 0.69748(12) 0.0125(3) Uani 1 1 d . . .
O8 O 0.30113(13) 0.27782(12) 0.61703(13) 0.0164(3) Uani 1 1 d . . .
O9 O 0.33657(13) 0.49835(12) 0.57577(12) 0.0155(3) Uani 1 1 d . . .
H9A H 0.2964 0.4692 0.4964 0.023 Uiso 1 1 d R . .
O10 O 0.40347(13) 0.44421(12) 0.78446(13) 0.0153(3) Uani 1 1 d . . .
O11 O 0.22991(12) 0.41687(12) 0.34038(12) 0.0117(3) Uani 1 1 d . . .
O12 O 0.25407(12) 0.64240(12) 0.32920(12) 0.0125(3) Uani 1 1 d . . .
O13 O 0.31031(12) 0.50137(12) 0.16590(12) 0.0120(3) Uani 1 1 d . . .
O14 O 0.08574(12) 0.50712(12) 0.18180(12) 0.0116(3) Uani 1 1 d . . .
O15 O 0.01235(13) 0.73336(12) 0.01644(12) 0.0131(3) Uani 1 1 d . . .
H15B H -0.0565 0.7491 0.0462 0.020 Uiso 1 1 d R . .
H15A H 0.0813 0.7753 0.0647 0.020 Uiso 1 1 d R . .
O16 O 0.16304(12) 0.50816(12) -0.05779(12) 0.0110(3) Uani 1 1 d . . .
H16B H 0.1670 0.4725 -0.1301 0.016 Uiso 1 1 d R . .
H16A H 0.2247 0.4931 -0.0016 0.016 Uiso 1 1 d R . .
O17 O 0.20047(13) 0.20799(12) 0.88664(13) 0.0133(3) Uani 1 1 d . . .
O18 O 0.17492(13) -0.00921(12) 0.93999(12) 0.0145(3) Uani 1 1 d . . .
H18A H 0.2037 0.0285 1.0183 0.022 Uiso 1 1 d R . .
O19 O 0.33659(12) 0.05733(12) 0.81889(12) 0.0133(3) Uani 1 1 d . . .
O20 O 0.10934(12) 0.03184(12) 0.72629(12) 0.0130(3) Uani 1 1 d . . .


_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 O6 1.9492(14) . ?
Cu1 O6 1.9492(14) 2_656 ?
Cu1 O4 1.9974(14) . ?
Cu1 O4 1.9974(14) 2_656 ?
N1 C1 1.486(2) . ?
N1 H10 0.8886 . ?
N1 H11 0.8903 . ?
N1 H12 0.8923 . ?
N2 C3 1.487(2) . ?
N2 H7 0.8820 . ?
N2 H8 0.8812 . ?
N2 H9 0.8839 . ?
N3 C4 1.494(2) . ?
N3 H4 0.8873 . ?
N3 H5 0.8868 . ?
N3 H6 0.8913 . ?
N4 C6 1.488(2) . ?
N4 H1 0.8729 . ?
N4 H2 0.8620 . ?
N4 H3 0.8676 . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.520(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.521(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.521(2) . ?
C5 H5D 0.9900 . ?
C5 H5C 0.9900 . ?
C6 H6D 0.9900 . ?
C6 H6C 0.9900 . ?
Cu2 O16 1.9480(14) 2_565 ?
Cu2 O16 1.9480(14) . ?
Cu2 O14 1.9965(14) 2_565 ?
Cu2 O14 1.9965(14) . ?
S1 O2 1.4669(13) . ?
S1 O3 1.4738(14) . ?
S1 O1 1.4884(13) . ?
S1 O4 1.5012(14) . ?
S2 O10 1.4454(14) . ?
S2 O8 1.4562(14) . ?
S2 O7 1.4666(14) . ?
S2 O9 1.5734(14) . ?
S3 O12 1.4691(13) . ?
S3 O13 1.4751(14) . ?
S3 O11 1.4862(13) . ?
S3 O14 1.4963(14) . ?
S4 O20 1.4500(14) . ?
S4 O17 1.4550(14) . ?
S4 O19 1.4679(14) . ?
S4 O18 1.5672(14) . ?
O5 H5B 0.8426 . ?
O5 H5A 0.8457 . ?
O6 H6B 0.8757 . ?
O6 H6A 0.8747 . ?
O9 H9A 0.8983 . ?
O15 H15B 0.8789 . ?
O15 H15A 0.8739 . ?
O16 H16B 0.8503 . ?
O16 H16A 0.8445 . ?
O18 H18A 0.8904 . ?

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
O6 Cu1 O6 180.0 . 2_656 ?
O6 Cu1 O4 92.25(6) . . ?
O6 Cu1 O4 87.75(6) 2_656 . ?
O6 Cu1 O4 87.75(6) . 2_656 ?
O6 Cu1 O4 92.25(6) 2_656 2_656 ?
O4 Cu1 O4 180.0 . 2_656 ?
C1 N1 H10 106.3 . . ?
C1 N1 H11 110.1 . . ?
H10 N1 H11 110.1 . . ?
C1 N1 H12 109.5 . . ?
H10 N1 H12 110.8 . . ?
H11 N1 H12 110.1 . . ?
C3 N2 H7 107.4 . . ?
C3 N2 H8 113.5 . . ?
H7 N2 H8 107.1 . . ?
C3 N2 H9 110.8 . . ?
H7 N2 H9 109.9 . . ?
H8 N2 H9 108.1 . . ?
C4 N3 H4 110.1 . . ?
C4 N3 H5 111.2 . . ?
H4 N3 H5 110.4 . . ?
C4 N3 H6 107.5 . . ?
H4 N3 H6 108.5 . . ?
H5 N3 H6 109.1 . . ?
C6 N4 H1 112.0 . . ?
C6 N4 H2 108.3 . . ?
H1 N4 H2 109.4 . . ?
C6 N4 H3 111.9 . . ?
H1 N4 H3 107.1 . . ?
H2 N4 H3 108.1 . . ?
N1 C1 C2 109.31(14) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.3 . . ?
C1 C2 C3 110.43(15) . . ?
C1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C2 109.98(15) . . ?
N2 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N2 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N3 C4 C5 112.09(15) . . ?
N3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N3 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 112.56(15) . . ?
C4 C5 H5D 109.1 . . ?
C6 C5 H5D 109.1 . . ?
C4 C5 H5C 109.1 . . ?
C6 C5 H5C 109.1 . . ?
H5D C5 H5C 107.8 . . ?
N4 C6 C5 110.78(14) . . ?
N4 C6 H6D 109.5 . . ?
C5 C6 H6D 109.5 . . ?
N4 C6 H6C 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6D C6 H6C 108.1 . . ?
O16 Cu2 O16 180.0 2_565 . ?
O16 Cu2 O14 92.87(6) 2_565 2_565 ?
O16 Cu2 O14 87.13(6) . 2_565 ?
O16 Cu2 O14 87.13(6) 2_565 . ?
O16 Cu2 O14 92.87(6) . . ?
O14 Cu2 O14 180.0 2_565 . ?
O2 S1 O3 111.31(8) . . ?
O2 S1 O1 109.52(8) . . ?
O3 S1 O1 109.40(8) . . ?
O2 S1 O4 108.81(8) . . ?
O3 S1 O4 110.05(8) . . ?
O1 S1 O4 107.66(7) . . ?
O10 S2 O8 114.50(8) . . ?
O10 S2 O7 112.48(8) . . ?
O8 S2 O7 111.95(8) . . ?
O10 S2 O9 103.42(8) . . ?
O8 S2 O9 107.11(8) . . ?
O7 S2 O9 106.54(8) . . ?
O12 S3 O13 110.75(8) . . ?
O12 S3 O11 109.37(8) . . ?
O13 S3 O11 109.21(8) . . ?
O12 S3 O14 109.53(7) . . ?
O13 S3 O14 110.12(8) . . ?
O11 S3 O14 107.80(7) . . ?
O20 S4 O17 114.10(8) . . ?
O20 S4 O19 111.97(8) . . ?
O17 S4 O19 112.27(8) . . ?
O20 S4 O18 103.68(8) . . ?
O17 S4 O18 107.41(8) . . ?
O19 S4 O18 106.64(8) . . ?
S1 O4 Cu1 135.30(8) . . ?
H5B O5 H5A 109.3 . . ?
Cu1 O6 H6B 120.5 . . ?
Cu1 O6 H6A 110.8 . . ?
H6B O6 H6A 109.9 . . ?
S2 O9 H9A 111.6 . . ?
S3 O14 Cu2 136.03(8) . . ?
H15B O15 H15A 110.3 . . ?
Cu2 O16 H16B 120.3 . . ?
Cu2 O16 H16A 112.8 . . ?
H16B O16 H16A 111.2 . . ?
S4 O18 H18A 111.7 . . ?

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
N1 C1 C2 C3 -175.41(14) . . . . ?
C1 C2 C3 N2 177.21(15) . . . . ?
N3 C4 C5 C6 59.9(2) . . . . ?
C4 C5 C6 N4 172.15(15) . . . . ?
O2 S1 O4 Cu1 -103.63(12) . . . . ?
O3 S1 O4 Cu1 18.58(14) . . . . ?
O1 S1 O4 Cu1 137.75(11) . . . . ?
O6 Cu1 O4 S1 0.61(12) . . . . ?
O6 Cu1 O4 S1 -179.39(12) 2_656 . . . ?
O4 Cu1 O4 S1 119(100) 2_656 . . . ?
O12 S3 O14 Cu2 111.26(12) . . . . ?
O13 S3 O14 Cu2 -10.77(14) . . . . ?
O11 S3 O14 Cu2 -129.83(11) . . . . ?
O16 Cu2 O14 S3 -178.33(12) 2_565 . . . ?
O16 Cu2 O14 S3 1.67(12) . . . . ?
O14 Cu2 O14 S3 45(100) 2_565 . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.311
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.122
