# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_140510f13
_database_code_depnum_ccdc_archive 'CCDC 1061268'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H26 Cu5 O20 S2'
_chemical_formula_moiety         'C10 H26 Cu5 O20 S2'
_chemical_formula_weight         848.15
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.4530(5)
_cell_length_b                   8.0998(9)
_cell_length_c                   14.4067(17)
_cell_angle_alpha                95.208(10)
_cell_angle_beta                 98.408(9)
_cell_angle_gamma                107.430(7)
_cell_volume                     594.44(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2398
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             423.00
_exptl_absorpt_coefficient_mu    4.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.618
_exptl_absorpt_correction_T_max  0.792

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            5801
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.206
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2616
_reflns_number_gt                2180
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0952
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2616
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0552P)²+0.2035P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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 0.5000 0.5000 0.5000 0.01019(15) Uani 1 2 d S . P . .
Cu2 Cu 0.92119(6) 0.30231(4) 0.50188(2) 0.00976(13) Uani 1 1 d . . . . .
Cu3 Cu 0.30101(6) 0.09474(4) 0.49468(2) 0.00996(13) Uani 1 1 d . . . . .
S1 S 0.30209(14) 0.43899(11) 0.81332(5) 0.0177(2) Uani 1 1 d . . . . .
O1 O 0.2950(4) 0.2709(3) 0.76243(16) 0.0245(5) Uani 1 1 d . . . . .
O2 O 0.5628(4) 0.5451(3) 0.85810(16) 0.0258(5) Uani 1 1 d . . . . .
O3 O 0.1701(4) 0.5318(3) 0.75014(15) 0.0211(5) Uani 1 1 d . . . . .
O4 O 0.7920(4) 0.4742(3) 0.43946(17) 0.0109(4) Uani 1 1 d . . . . .
H4A H 0.767(7) 0.459(5) 0.385(3) 0.013 Uiso 1 1 d . U . . .
O5 O 0.2516(4) 0.2847(3) 0.43102(16) 0.0122(5) Uani 1 1 d . . . . .
H5A H 0.253(7) 0.268(5) 0.379(3) 0.015 Uiso 1 1 d . U . . .
O6 O 1.0481(4) 0.1397(3) 0.57163(16) 0.0114(4) Uani 1 1 d . . . . .
H6A H 1.091(7) 0.173(5) 0.627(3) 0.014 Uiso 1 1 d . U . . .
O7 O 0.3806(4) -0.0938(3) 0.55818(16) 0.0112(4) Uani 1 1 d . . . . .
H7A H 0.390(6) -0.077(5) 0.618(3) 0.013 Uiso 1 1 d . U . . .
O8 O 0.6696(5) 0.3568(3) 0.63747(18) 0.0212(5) Uani 1 1 d . . . . .
H8A H 0.571(8) 0.327(5) 0.669(3) 0.025 Uiso 1 1 d . U . . .
H8B H 0.808(8) 0.412(5) 0.671(3) 0.025 Uiso 1 1 d . U . . .
O9 O 0.8175(5) 0.8098(4) 0.76314(19) 0.0288(6) Uani 1 1 d . . . . .
H9A H 0.790(8) 0.741(6) 0.797(3) 0.035 Uiso 1 1 d . U . . .
H9B H 0.689(8) 0.852(6) 0.761(3) 0.035 Uiso 1 1 d . U . . .
O10 O 0.3837(6) 0.9434(4) 0.7527(2) 0.0297(6) Uani 1 1 d . . . . .
H10A H 0.245(8) 0.873(6) 0.759(3) 0.036 Uiso 1 1 d . U . . .
H10B H 0.402(9) 1.023(6) 0.774(3) 0.036 Uiso 1 1 d . U . . .
C1 C 0.1135(6) 0.3881(4) 0.9033(2) 0.0173(6) Uani 1 1 d . . . . .
C2 C -0.0075(6) 0.2162(4) 0.9087(2) 0.0240(7) Uani 1 1 d . . . . .
H2 H 0.0165 0.1276 0.8665 0.029 Uiso 1 1 calc R U . . .
C3 C -0.1669(7) 0.1698(5) 0.9762(2) 0.0262(8) Uani 1 1 d . . . . .
H3 H -0.2491 0.0498 0.9797 0.031 Uiso 1 1 calc R U . . .
C4 C -0.2052(6) 0.2950(4) 1.0370(2) 0.0219(7) Uani 1 1 d . . . . .
H4 H -0.3158 0.2612 1.0818 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0817(6) 0.5245(4) 0.9659(2) 0.0153(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O5 1.934(2) . ?
Cu1 O5 1.934(2) 2_666 ?
Cu1 O4 1.978(2) . ?
Cu1 O4 1.978(2) 2_666 ?
Cu2 O6 1.951(2) . ?
Cu2 O4 1.968(2) . ?
Cu2 O7 1.991(2) 2_656 ?
Cu2 O4 2.019(2) 2_766 ?
Cu2 O5 2.231(2) 1_655 ?
Cu2 Cu3 3.0405(5) 1_655 ?
Cu3 O5 1.927(2) . ?
Cu3 O7 1.973(2) . ?
Cu3 O6 1.985(2) 1_455 ?
Cu3 O7 1.997(2) 2_656 ?
Cu3 O6 2.262(2) 2_656 ?
Cu3 Cu3 3.0049(6) 2_656 ?
Cu3 Cu2 3.0405(5) 1_455 ?
S1 O2 1.440(2) . ?
S1 O3 1.473(2) . ?
S1 O1 1.473(2) . ?
S1 C1 1.773(3) . ?
O4 Cu2 2.019(2) 2_766 ?
O4 H4A 0.76(4) . ?
O5 Cu2 2.231(2) 1_455 ?
O5 H5A 0.75(4) . ?
O6 Cu3 1.985(2) 1_655 ?
O6 Cu3 2.262(2) 2_656 ?
O6 H6A 0.80(4) . ?
O7 Cu2 1.991(2) 2_656 ?
O7 Cu3 1.997(2) 2_656 ?
O7 H7A 0.86(4) . ?
O8 H8A 0.76(4) . ?
O8 H8B 0.81(4) . ?
O9 H9A 0.77(5) . ?
O9 H9B 0.86(4) . ?
O10 H10A 0.82(4) . ?
O10 H10B 0.67(5) . ?
C1 C2 1.366(5) . ?
C1 C5 1.428(4) . ?
C2 C3 1.400(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.422(5) 2_567 ?
C4 H4 0.9500 . ?
C5 C4 1.422(5) 2_567 ?
C5 C5 1.427(6) 2_567 ?

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 180.0 . 2_666 ?
O5 Cu1 O4 94.14(9) . . ?
O5 Cu1 O4 85.86(10) 2_666 . ?
O5 Cu1 O4 85.86(10) . 2_666 ?
O5 Cu1 O4 94.14(9) 2_666 2_666 ?
O4 Cu1 O4 180.0 . 2_666 ?
O6 Cu2 O4 176.29(8) . . ?
O6 Cu2 O7 85.61(9) . 2_656 ?
O4 Cu2 O7 96.12(9) . 2_656 ?
O6 Cu2 O4 98.63(9) . 2_766 ?
O4 Cu2 O4 79.53(10) . 2_766 ?
O7 Cu2 O4 175.30(8) 2_656 2_766 ?
O6 Cu2 O5 78.34(9) . 1_655 ?
O4 Cu2 O5 104.28(9) . 1_655 ?
O7 Cu2 O5 105.48(9) 2_656 1_655 ?
O4 Cu2 O5 77.49(9) 2_766 1_655 ?
O6 Cu2 Cu3 39.82(6) . 1_655 ?
O4 Cu2 Cu3 143.14(7) . 1_655 ?
O7 Cu2 Cu3 91.62(6) 2_656 1_655 ?
O4 Cu2 Cu3 92.94(6) 2_766 1_655 ?
O5 Cu2 Cu3 39.22(6) 1_655 1_655 ?
O5 Cu3 O7 175.42(8) . . ?
O5 Cu3 O6 85.30(9) . 1_455 ?
O7 Cu3 O6 98.53(9) . 1_455 ?
O5 Cu3 O7 94.07(9) . 2_656 ?
O7 Cu3 O7 81.60(9) . 2_656 ?
O6 Cu3 O7 165.87(9) 1_455 2_656 ?
O5 Cu3 O6 104.97(8) . 2_656 ?
O7 Cu3 O6 78.16(8) . 2_656 ?
O6 Cu3 O6 81.83(9) 1_455 2_656 ?
O7 Cu3 O6 111.85(9) 2_656 2_656 ?
O5 Cu3 Cu3 134.55(7) . 2_656 ?
O7 Cu3 Cu3 41.10(6) . 2_656 ?
O6 Cu3 Cu3 137.89(7) 1_455 2_656 ?
O7 Cu3 Cu3 40.50(6) 2_656 2_656 ?
O6 Cu3 Cu3 96.47(5) 2_656 2_656 ?
O5 Cu3 Cu2 47.06(7) . 1_455 ?
O7 Cu3 Cu2 137.08(6) . 1_455 ?
O6 Cu3 Cu2 39.03(6) 1_455 1_455 ?
O7 Cu3 Cu2 140.83(6) 2_656 1_455 ?
O6 Cu3 Cu2 87.20(5) 2_656 1_455 ?
Cu3 Cu3 Cu2 174.88(2) 2_656 1_455 ?
O2 S1 O3 112.59(15) . . ?
O2 S1 O1 112.60(14) . . ?
O3 S1 O1 110.44(14) . . ?
O2 S1 C1 107.99(14) . . ?
O3 S1 C1 106.23(14) . . ?
O1 S1 C1 106.56(15) . . ?
Cu2 O4 Cu1 106.78(11) . . ?
Cu2 O4 Cu2 100.47(10) . 2_766 ?
Cu1 O4 Cu2 101.13(10) . 2_766 ?
Cu2 O4 H4A 116(3) . . ?
Cu1 O4 H4A 117(3) . . ?
Cu2 O4 H4A 114(3) 2_766 . ?
Cu3 O5 Cu1 107.99(11) . . ?
Cu3 O5 Cu2 93.72(9) . 1_455 ?
Cu1 O5 Cu2 95.42(9) . 1_455 ?
Cu3 O5 H5A 111(3) . . ?
Cu1 O5 H5A 116(3) . . ?
Cu2 O5 H5A 129(3) 1_455 . ?
Cu2 O6 Cu3 101.16(10) . 1_655 ?
Cu2 O6 Cu3 93.92(8) . 2_656 ?
Cu3 O6 Cu3 98.16(9) 1_655 2_656 ?
Cu2 O6 H6A 113(3) . . ?
Cu3 O6 H6A 121(3) 1_655 . ?
Cu3 O6 H6A 124(3) 2_656 . ?
Cu3 O7 Cu2 102.28(10) . 2_656 ?
Cu3 O7 Cu3 98.39(9) . 2_656 ?
Cu2 O7 Cu3 110.50(10) 2_656 2_656 ?
Cu3 O7 H7A 113(2) . . ?
Cu2 O7 H7A 111(2) 2_656 . ?
Cu3 O7 H7A 120(2) 2_656 . ?
H8A O8 H8B 107(4) . . ?
H9A O9 H9B 105(4) . . ?
H10A O10 H10B 113(5) . . ?
C2 C1 C5 121.3(3) . . ?
C2 C1 S1 118.3(2) . . ?
C5 C1 S1 120.4(2) . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.8(3) . 2_567 ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 2_567 . ?
C4 C5 C5 119.0(4) 2_567 2_567 ?
C4 C5 C1 123.1(3) 2_567 . ?
C5 C5 C1 117.9(4) 2_567 . ?

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
O2 S1 C1 C2 -123.6(3) . . . . ?
O3 S1 C1 C2 115.4(3) . . . . ?
O1 S1 C1 C2 -2.4(3) . . . . ?
O2 S1 C1 C5 58.8(3) . . . . ?
O3 S1 C1 C5 -62.2(3) . . . . ?
O1 S1 C1 C5 180.0(2) . . . . ?
C5 C1 C2 C3 0.1(5) . . . . ?
S1 C1 C2 C3 -177.5(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . 2_567 ?
C2 C1 C5 C4 179.6(3) . . . 2_567 ?
S1 C1 C5 C4 -2.9(4) . . . 2_567 ?
C2 C1 C5 C5 -0.3(5) . . . 2_567 ?
S1 C1 C5 C5 177.3(3) . . . 2_567 ?



#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


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

data_131120f1
_database_code_depnum_ccdc_archive 'CCDC 1061269'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H22 Cu4 O14 S'
_chemical_formula_moiety         'C12 H22 Cu4 O14 S'
_chemical_formula_weight         676.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.1058(6)
_cell_length_b                   8.5966(7)
_cell_length_c                   15.1429(12)
_cell_angle_alpha                90.034(4)
_cell_angle_beta                 95.059(5)
_cell_angle_gamma                99.868(5)
_cell_volume                     1035.40(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2485
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.00
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    2.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676.00
_exptl_absorpt_coefficient_mu    4.222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.919

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.706
_diffrn_reflns_number            6425
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_full        25.023
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             3504
_reflns_number_gt                2547
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1291
_refine_ls_number_restraints     88
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     320
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0646P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.20
_refine_diff_density_min         -1.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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 0.26981(8) 0.76464(7) 0.51654(5) 0.0069(2) Uani 1 1 d . U . . .
Cu2 Cu 0.63730(8) 0.87045(7) 0.51474(5) 0.0069(2) Uani 1 1 d . U . . .
Cu3 Cu 1.0000 1.0000 0.5000 0.0065(2) Uani 1 2 d S U P . .
Cu4 Cu 0.5000 0.5000 0.5000 0.0078(3) Uani 1 2 d S U P . .
Cu5 Cu 0.88037(8) 0.61514(7) 0.50541(4) 0.0067(2) Uani 1 1 d . U . . .
S1 S 1.2332(2) 0.70779(17) 0.24113(10) 0.0170(4) Uani 1 1 d . . . . .
O1 O 1.1423(6) 0.5693(5) 0.2837(3) 0.0261(11) Uani 1 1 d . . . . .
O2 O 1.4119(6) 0.7400(6) 0.2723(3) 0.0310(12) Uani 1 1 d . . . . .
O3 O 1.1501(6) 0.8449(5) 0.2537(3) 0.0316(12) Uani 1 1 d . . . . .
O4 O 0.0993(5) 0.7875(4) 0.5981(2) 0.0079(8) Uani 1 1 d . U . . .
O5 O 0.2680(5) 0.7741(5) 0.7214(3) 0.0185(10) Uani 1 1 d . U . . .
O6 O 0.4519(5) 0.9175(5) 0.5761(3) 0.0103(9) Uani 1 1 d D . . . .
H6A H 0.416(7) 0.917(8) 0.615(3) 0.012 Uiso 1 1 d D U . . .
O7 O 0.8145(5) 1.0395(5) 0.5646(2) 0.0068(8) Uani 1 1 d D . . . .
H7A H 0.787(7) 1.057(7) 0.604(3) 0.008 Uiso 1 1 d D U . . .
O8 O 0.4568(5) 0.7081(4) 0.4556(3) 0.0076(9) Uani 1 1 d D . . . .
H8A H 0.481(7) 0.661(6) 0.426(3) 0.009 Uiso 1 1 d D U . . .
O9 O 0.8322(5) 0.8179(4) 0.4532(2) 0.0068(8) Uani 1 1 d D . . . .
H9A H 0.841(8) 0.786(7) 0.414(3) 0.008 Uiso 1 1 d D U . . .
O10 O 0.3204(6) 0.5053(5) 0.6305(3) 0.0194(10) Uani 1 1 d D . . . .
H10A H 0.310(8) 0.435(5) 0.671(3) 0.023 Uiso 1 1 d D U . . .
H10B H 0.307(8) 0.589(4) 0.658(3) 0.023 Uiso 1 1 d D U . . .
O11 O 0.6900(5) 0.6181(4) 0.5728(2) 0.0073(9) Uani 1 1 d . . . . .
H11A H 0.712(8) 0.573(7) 0.610(4) 0.009 Uiso 1 1 d . U . . .
O12 O 1.0924(5) 0.6023(5) 0.4560(3) 0.0076(8) Uani 1 1 d D . . . .
H12D H 1.116(8) 0.584(7) 0.416(3) 0.009 Uiso 1 1 d D U . . .
O13 O 0.8053(6) 0.7665(5) 0.2773(3) 0.0226(11) Uani 1 1 d D . . . .
H13B H 0.902(3) 0.791(7) 0.257(4) 0.027 Uiso 1 1 d D U . . .
H13A H 0.724(5) 0.804(7) 0.251(4) 0.027 Uiso 1 1 d D U . . .
O14 O 0.6298(7) 0.9497(6) 0.1713(4) 0.0412(14) Uani 1 1 d D . . . .
H14A H 0.627(8) 0.998(2) 0.1217(8) 0.049 Uiso 1 1 d D U . . .
H14B H 0.539(5) 0.935(9) 0.199(4) 0.049 Uiso 1 1 d D U . . .
C1 C 1.2232(7) 0.6690(7) 0.1261(4) 0.0173(14) Uani 1 1 d . . . . .
C2 C 1.1640(9) 0.7757(8) 0.0692(4) 0.0299(17) Uani 1 1 d . . . . .
H2 H 1.1326 0.8678 0.0927 0.036 Uiso 1 1 calc R U . . .
C3 C 1.1496(10) 0.7512(10) -0.0210(5) 0.044(2) Uani 1 1 d . . . . .
H3 H 1.1094 0.8273 -0.0589 0.052 Uiso 1 1 calc R U . . .
C4 C 1.1923(9) 0.6181(10) -0.0577(5) 0.041(2) Uani 1 1 d . . . . .
H4 H 1.1827 0.6031 -0.1202 0.050 Uiso 1 1 calc R U . . .
C5 C 1.2512(9) 0.5032(9) -0.0006(5) 0.0314(17) Uani 1 1 d . . . . .
C6 C 1.2952(9) 0.3645(10) -0.0373(5) 0.043(2) Uani 1 1 d . . . . .
H6 H 1.2824 0.3475 -0.0997 0.052 Uiso 1 1 calc R U . . .
C7 C 1.3552(10) 0.2569(9) 0.0163(6) 0.046(2) Uani 1 1 d . . . . .
H7 H 1.3844 0.1648 -0.0085 0.055 Uiso 1 1 calc R U . . .
C8 C 1.3742(9) 0.2824(8) 0.1097(5) 0.0376(19) Uani 1 1 d . . . . .
H8 H 1.4143 0.2054 0.1469 0.045 Uiso 1 1 calc R U . . .
C9 C 1.3359(8) 0.4159(8) 0.1475(4) 0.0270(16) Uani 1 1 d . . . . .
H9 H 1.3532 0.4325 0.2099 0.032 Uiso 1 1 calc R U . . .
C10 C 1.2704(8) 0.5285(7) 0.0926(4) 0.0216(15) Uani 1 1 d . . . . .
C11 C 0.1299(7) 0.7913(6) 0.6846(4) 0.0096(11) Uani 1 1 d . U . . .
C12 C -0.0117(7) 0.8162(6) 0.7379(4) 0.0135(13) Uani 1 1 d . U . . .
H12A H 0.0233 0.9117 0.7750 0.016 Uiso 1 1 calc R U . . .
H12B H -0.0404 0.7249 0.7758 0.016 Uiso 1 1 calc R U . . .
H12C H -0.1101 0.8283 0.6977 0.016 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.954(4) . ?
Cu1 O4 1.967(4) . ?
Cu1 O8 1.971(4) . ?
Cu1 O12 1.983(4) 1_455 ?
Cu1 O7 2.250(4) 2_676 ?
Cu1 Cu2 2.9643(9) . ?
Cu2 O6 1.934(4) . ?
Cu2 O7 1.959(4) . ?
Cu2 O8 1.989(4) . ?
Cu2 O9 2.018(4) . ?
Cu2 O11 2.432(4) . ?
Cu2 Cu3 2.9878(7) . ?
Cu3 O7 1.941(4) 2_776 ?
Cu3 O7 1.941(4) . ?
Cu3 O9 1.975(4) 2_776 ?
Cu3 O9 1.975(4) . ?
Cu3 Cu2 2.9879(7) 2_776 ?
Cu4 O11 1.945(4) 2_666 ?
Cu4 O11 1.945(4) . ?
Cu4 O8 1.987(4) 2_666 ?
Cu4 O8 1.987(4) . ?
Cu4 H8A 1.80(6) . ?
Cu5 O11 1.927(4) . ?
Cu5 O12 1.953(4) . ?
Cu5 O9 1.999(4) . ?
Cu5 O12 2.001(4) 2_766 ?
Cu5 Cu5 3.0131(13) 2_766 ?
Cu5 H9A 2.07(6) . ?
S1 O2 1.462(4) . ?
S1 O1 1.470(4) . ?
S1 O3 1.475(4) . ?
S1 C1 1.766(6) . ?
O4 C11 1.310(6) . ?
O5 C11 1.238(6) . ?
O6 H6A 0.67(3) . ?
O7 Cu1 2.250(4) 2_676 ?
O7 H7A 0.68(3) . ?
O8 H8A 0.67(3) . ?
O9 H9A 0.67(3) . ?
O10 H10A 0.859(10) . ?
O10 H10B 0.860(10) . ?
O11 H11A 0.71(5) . ?
O12 Cu1 1.983(4) 1_655 ?
O12 Cu5 2.001(4) 2_766 ?
O12 H12D 0.67(3) . ?
O13 H13B 0.857(10) . ?
O13 H13A 0.852(10) . ?
O14 H14A 0.862(10) . ?
O14 H14B 0.867(10) . ?
C1 C2 1.375(8) . ?
C1 C10 1.433(8) . ?
C2 C3 1.375(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.428(10) . ?
C4 H4 0.9500 . ?
C5 C10 1.419(9) . ?
C5 C6 1.427(10) . ?
C6 C7 1.354(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.422(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(9) . ?
C9 H9 0.9500 . ?
C11 C12 1.504(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O4 96.85(16) . . ?
O6 Cu1 O8 81.80(16) . . ?
O4 Cu1 O8 166.77(16) . . ?
O6 Cu1 O12 177.31(17) . 1_455 ?
O4 Cu1 O12 84.92(16) . 1_455 ?
O8 Cu1 O12 96.01(16) . 1_455 ?
O6 Cu1 O7 89.51(16) . 2_676 ?
O4 Cu1 O7 88.68(15) . 2_676 ?
O8 Cu1 O7 104.44(16) . 2_676 ?
O12 Cu1 O7 92.56(15) 1_455 2_676 ?
O6 Cu1 Cu2 40.06(12) . . ?
O4 Cu1 Cu2 135.87(11) . . ?
O8 Cu1 Cu2 41.77(11) . . ?
O12 Cu1 Cu2 137.79(12) 1_455 . ?
O7 Cu1 Cu2 97.78(11) 2_676 . ?
O6 Cu2 O7 99.30(17) . . ?
O6 Cu2 O8 81.84(16) . . ?
O7 Cu2 O8 175.64(16) . . ?
O6 Cu2 O9 178.61(17) . . ?
O7 Cu2 O9 80.68(16) . . ?
O8 Cu2 O9 98.28(16) . . ?
O6 Cu2 O11 104.90(16) . . ?
O7 Cu2 O11 109.45(15) . . ?
O8 Cu2 O11 74.17(15) . . ?
O9 Cu2 O11 73.83(15) . . ?
O6 Cu2 Cu1 40.58(12) . . ?
O7 Cu2 Cu1 139.54(12) . . ?
O8 Cu2 Cu1 41.29(11) . . ?
O9 Cu2 Cu1 139.57(11) . . ?
O11 Cu2 Cu1 90.68(9) . . ?
O6 Cu2 Cu3 139.03(12) . . ?
O7 Cu2 Cu3 39.78(12) . . ?
O8 Cu2 Cu3 138.76(12) . . ?
O9 Cu2 Cu3 41.02(11) . . ?
O11 Cu2 Cu3 94.46(9) . . ?
Cu1 Cu2 Cu3 174.47(3) . . ?
O7 Cu3 O7 180.0 2_776 . ?
O7 Cu3 O9 82.22(16) 2_776 2_776 ?
O7 Cu3 O9 97.78(16) . 2_776 ?
O7 Cu3 O9 97.78(16) 2_776 . ?
O7 Cu3 O9 82.22(16) . . ?
O9 Cu3 O9 180.0 2_776 . ?
O7 Cu3 Cu2 139.77(11) 2_776 . ?
O7 Cu3 Cu2 40.23(11) . . ?
O9 Cu3 Cu2 137.89(12) 2_776 . ?
O9 Cu3 Cu2 42.11(12) . . ?
O7 Cu3 Cu2 40.23(11) 2_776 2_776 ?
O7 Cu3 Cu2 139.77(11) . 2_776 ?
O9 Cu3 Cu2 42.11(12) 2_776 2_776 ?
O9 Cu3 Cu2 137.89(12) . 2_776 ?
Cu2 Cu3 Cu2 180.0 . 2_776 ?
O11 Cu4 O11 180.0 2_666 . ?
O11 Cu4 O8 86.31(15) 2_666 2_666 ?
O11 Cu4 O8 93.69(15) . 2_666 ?
O11 Cu4 O8 93.69(15) 2_666 . ?
O11 Cu4 O8 86.31(15) . . ?
O8 Cu4 O8 180.0 2_666 . ?
O11 Cu4 H8A 86.2(19) 2_666 . ?
O11 Cu4 H8A 93.8(19) . . ?
O8 Cu4 H8A 160.5(11) 2_666 . ?
O8 Cu4 H8A 19.5(11) . . ?
O11 Cu5 O12 170.26(16) . . ?
O11 Cu5 O9 86.60(16) . . ?
O12 Cu5 O9 100.29(17) . . ?
O11 Cu5 O12 93.37(16) . 2_766 ?
O12 Cu5 O12 80.74(18) . 2_766 ?
O9 Cu5 O12 172.19(15) . 2_766 ?
O11 Cu5 Cu5 132.69(11) . 2_766 ?
O12 Cu5 Cu5 40.96(12) . 2_766 ?
O9 Cu5 Cu5 140.69(12) . 2_766 ?
O12 Cu5 Cu5 39.78(12) 2_766 2_766 ?
O11 Cu5 H9A 99.6(15) . . ?
O12 Cu5 H9A 88.8(15) . . ?
O9 Cu5 H9A 18.9(9) . . ?
O12 Cu5 H9A 154.8(10) 2_766 . ?
Cu5 Cu5 H9A 126.0(13) 2_766 . ?
O2 S1 O1 112.3(3) . . ?
O2 S1 O3 112.2(3) . . ?
O1 S1 O3 109.4(3) . . ?
O2 S1 C1 106.2(3) . . ?
O1 S1 C1 108.8(3) . . ?
O3 S1 C1 107.7(3) . . ?
C11 O4 Cu1 123.3(3) . . ?
Cu2 O6 Cu1 99.36(18) . . ?
Cu2 O6 H6A 147(6) . . ?
Cu1 O6 H6A 94(6) . . ?
Cu3 O7 Cu2 100.00(17) . . ?
Cu3 O7 Cu1 100.10(17) . 2_676 ?
Cu2 O7 Cu1 96.43(16) . 2_676 ?
Cu3 O7 H7A 148(5) . . ?
Cu2 O7 H7A 103(5) . . ?
Cu1 O7 H7A 99(5) 2_676 . ?
Cu1 O8 Cu4 108.03(19) . . ?
Cu1 O8 Cu2 96.93(16) . . ?
Cu4 O8 Cu2 106.64(18) . . ?
Cu1 O8 H8A 147(6) . . ?
Cu4 O8 H8A 64(5) . . ?
Cu2 O8 H8A 116(6) . . ?
Cu3 O9 Cu5 111.60(19) . . ?
Cu3 O9 Cu2 96.86(16) . . ?
Cu5 O9 Cu2 105.67(18) . . ?
Cu3 O9 H9A 119(6) . . ?
Cu5 O9 H9A 86(5) . . ?
Cu2 O9 H9A 135(5) . . ?
H10A O10 H10B 102(6) . . ?
Cu5 O11 Cu4 104.73(18) . . ?
Cu5 O11 Cu2 93.79(15) . . ?
Cu4 O11 Cu2 92.86(14) . . ?
Cu5 O11 H11A 100(5) . . ?
Cu4 O11 H11A 110(5) . . ?
Cu2 O11 H11A 148(5) . . ?
Cu5 O12 Cu1 108.13(18) . 1_655 ?
Cu5 O12 Cu5 99.26(18) . 2_766 ?
Cu1 O12 Cu5 111.27(19) 1_655 2_766 ?
Cu5 O12 H12D 136(6) . . ?
Cu1 O12 H12D 109(6) 1_655 . ?
Cu5 O12 H12D 88(6) 2_766 . ?
H13B O13 H13A 117(4) . . ?
H14A O14 H14B 118(4) . . ?
C2 C1 C10 120.7(6) . . ?
C2 C1 S1 117.9(5) . . ?
C10 C1 S1 121.3(5) . . ?
C3 C2 C1 121.0(7) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.2(7) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.3(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C10 C5 C6 119.7(7) . . ?
C10 C5 C4 120.1(7) . . ?
C6 C5 C4 120.1(7) . . ?
C7 C6 C5 120.5(7) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.7(7) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.6(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 119.5(7) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C5 119.0(6) . . ?
C9 C10 C1 123.4(6) . . ?
C5 C10 C1 117.6(6) . . ?
O5 C11 O4 122.1(5) . . ?
O5 C11 C12 121.0(5) . . ?
O4 C11 C12 116.9(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O2 S1 C1 C2 -112.7(5) . . . . ?
O1 S1 C1 C2 126.2(5) . . . . ?
O3 S1 C1 C2 7.7(6) . . . . ?
O2 S1 C1 C10 69.1(5) . . . . ?
O1 S1 C1 C10 -51.9(6) . . . . ?
O3 S1 C1 C10 -170.5(5) . . . . ?
C10 C1 C2 C3 -0.4(10) . . . . ?
S1 C1 C2 C3 -178.6(6) . . . . ?
C1 C2 C3 C4 0.7(12) . . . . ?
C2 C3 C4 C5 0.6(12) . . . . ?
C3 C4 C5 C10 -2.0(11) . . . . ?
C3 C4 C5 C6 179.7(7) . . . . ?
C10 C5 C6 C7 0.0(11) . . . . ?
C4 C5 C6 C7 178.3(7) . . . . ?
C5 C6 C7 C8 0.1(12) . . . . ?
C6 C7 C8 C9 -1.2(12) . . . . ?
C7 C8 C9 C10 2.2(11) . . . . ?
C8 C9 C10 C5 -2.1(10) . . . . ?
C8 C9 C10 C1 178.5(6) . . . . ?
C6 C5 C10 C9 1.0(10) . . . . ?
C4 C5 C10 C9 -177.3(6) . . . . ?
C6 C5 C10 C1 -179.5(6) . . . . ?
C4 C5 C10 C1 2.2(10) . . . . ?
C2 C1 C10 C9 178.5(6) . . . . ?
S1 C1 C10 C9 -3.4(9) . . . . ?
C2 C1 C10 C5 -1.0(9) . . . . ?
S1 C1 C10 C5 177.2(5) . . . . ?
Cu1 O4 C11 O5 -3.1(7) . . . . ?
Cu1 O4 C11 C12 177.5(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O6 H6a O5 . . . 2.921(6) 0.675 2.322 149.0 no
O7 H7a O3 . . 2_776 2.897(6) 0.677 2.298 148.6 no
O8 H8A O2 . . 1_455 2.787(6) 0.668 2.469 111.8 no
O9 H9a O13 . . . 2.683(6) 0.673 2.061 154.0 no
O10 H10b O5 . . . 2.802(6) 0.86(5) 1.94(5) 178(6) no
O10 H10a O13 . . 2_666 2.808(6) 0.859 2.018 152.5 no
O12 H12d O1 . . . 2.698(6) 0.674 2.044 163.9 no
O13 H13A O14 . . . 2.729(7) 0.852 1.942 152.9 no
O13 H13b O3 . . . 2.815(7) 0.857 1.993 160.2 no
O14 H14b O2 . . 1_455 2.845(7) 0.867 2.175 133.8 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


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

data_131120f21
_database_code_depnum_ccdc_archive 'CCDC 1061270'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C8 H12 Cu2 O6 S'
_chemical_formula_moiety         'C8 H12 Cu2 O6 S'
_chemical_formula_weight         363.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   16.769(12)
_cell_length_b                   6.450(4)
_cell_length_c                   10.595(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.894(7)
_cell_angle_gamma                90.0000
_cell_volume                     1139.9(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728.00
_exptl_absorpt_coefficient_mu    3.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_T_max  0.456

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_reflns_number            8154
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         3.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2611
_reflns_number_gt                1781
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1071
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2611
_refine_ls_number_parameters     202
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0452P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.88
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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 1.0000 0.5000 0.5000 0.0102(2) Uani 1 2 d S . P . .
Cu2 Cu 1.00813(4) 0.73448(9) 0.25204(6) 0.01076(18) Uani 1 1 d . . . . .
Cu3 Cu 1.0000 1.0000 0.5000 0.0113(2) Uani 1 2 d S . P . .
S4 S 0.81947(8) 0.5800(2) 0.10653(12) 0.0144(3) Uani 1 1 d . . . . .
O5 O 1.0466(2) 0.4769(5) 0.3378(3) 0.0125(8) Uani 1 1 d D . . . .
H5 H 1.0944(12) 0.467(8) 0.348(5) 0.015 Uiso 1 1 d D U . . .
O6 O 0.9013(2) 0.5093(5) 0.1547(3) 0.0138(8) Uani 1 1 d . . . . .
O7 O 0.9369(2) 1.2042(5) 0.3986(3) 0.0121(7) Uani 1 1 d D . . . .
H7 H 0.8913(14) 1.175(8) 0.387(5) 0.015 Uiso 1 1 d D U . . .
O8 O 0.8003(2) 0.5208(6) -0.0256(3) 0.0223(9) Uani 1 1 d . . . . .
O9 O 0.9516(2) 0.7545(5) 0.4075(3) 0.0122(8) Uani 1 1 d D . . . .
H9 H 0.9046(13) 0.764(7) 0.388(5) 0.015 Uiso 1 1 d D U . . .
O10 O 0.8095(2) 0.8013(5) 0.1306(4) 0.0205(9) Uani 1 1 d . . . . .
C11 C 0.4939(4) 0.2400(14) 0.3619(10) 0.050(2) Uani 1 1 d . . . . .
C12 C 0.7522(3) 0.4518(8) 0.1981(5) 0.0176(12) Uani 1 1 d . . . . .
C13 C 0.7207(3) 0.5576(9) 0.2958(5) 0.0203(12) Uani 1 1 d . . . . .
C14 C 0.6410(3) 0.2556(8) 0.3353(5) 0.0228(13) Uani 1 1 d . . . . .
C15 C 0.6650(3) 0.4558(9) 0.3637(5) 0.0231(13) Uani 1 1 d . . . . .
C16 C 0.7305(3) 0.2483(8) 0.1696(6) 0.0193(12) Uani 1 1 d . . . . .
C17 C 0.6755(3) 0.1520(9) 0.2382(6) 0.0252(14) Uani 1 1 d . . . . .
C18 C 0.5766(4) 0.1529(12) 0.4043(7) 0.0362(17) Uani 1 1 d . . . . .
H11A H 0.493(4) 0.389(10) 0.382(6) 0.05(2) Uiso 1 1 d . . . . .
H11B H 0.487(5) 0.198(12) 0.264(8) 0.08(3) Uiso 1 1 d . . . . .
H11C H 0.451(5) 0.172(12) 0.409(8) 0.09(3) Uiso 1 1 d . . . . .
H13 H 0.735(4) 0.699(9) 0.313(6) 0.034(18) Uiso 1 1 d . . . . .
H15 H 0.644(3) 0.544(8) 0.430(5) 0.025(16) Uiso 1 1 d . . . . .
H16 H 0.754(4) 0.184(9) 0.108(6) 0.04(2) Uiso 1 1 d . . . . .
H17 H 0.658(3) 0.019(8) 0.215(6) 0.032(18) Uiso 1 1 d . . . . .
H18A H 0.580(3) -0.015(9) 0.398(6) 0.039(19) Uiso 1 1 d . . . . .
H18B H 0.588(3) 0.181(8) 0.497(6) 0.027(17) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O5 1.964(4) 3_766 ?
Cu1 O5 1.964(4) . ?
Cu1 O9 2.037(3) 3_766 ?
Cu1 O9 2.037(3) . ?
Cu1 O7 2.384(4) 3_776 ?
Cu1 O7 2.384(4) 1_545 ?
Cu1 Cu2 3.0465(17) 3_766 ?
Cu1 Cu2 3.0465(17) . ?
Cu2 O7 1.933(4) 2_745 ?
Cu2 O5 1.970(3) . ?
Cu2 O9 1.987(4) . ?
Cu2 O5 2.004(3) 2_755 ?
Cu2 Cu3 3.0598(17) 2_745 ?
Cu3 O7 1.943(3) . ?
Cu3 O7 1.943(3) 3_776 ?
Cu3 O9 1.990(3) 3_776 ?
Cu3 O9 1.990(3) . ?
Cu3 Cu2 3.0598(17) 2_755 ?
Cu3 Cu2 3.0598(17) 4_576 ?
S4 O8 1.454(4) . ?
S4 O10 1.463(4) . ?
S4 O6 1.485(4) . ?
S4 C12 1.767(5) . ?
O5 Cu2 2.004(3) 2_745 ?
O5 H5 0.801(19) . ?
O7 Cu2 1.933(4) 2_755 ?
O7 Cu1 2.383(4) 1_565 ?
O7 H7 0.785(19) . ?
O9 H9 0.796(19) . ?
C11 C18 1.521(10) . ?
C11 H11A 0.98(6) . ?
C11 H11B 1.06(8) . ?
C11 H11C 1.01(9) . ?
C12 C16 1.387(7) . ?
C12 C13 1.389(8) . ?
C13 C15 1.400(8) . ?
C13 H13 0.96(6) . ?
C14 C15 1.376(8) . ?
C14 C17 1.401(8) . ?
C14 C18 1.517(8) . ?
C15 H15 0.99(5) . ?
C16 C17 1.379(8) . ?
C16 H16 0.89(6) . ?
C17 H17 0.93(5) . ?
C18 H18A 1.08(6) . ?
C18 H18B 0.99(6) . ?

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 180.0 3_766 . ?
O5 Cu1 O9 79.32(14) 3_766 3_766 ?
O5 Cu1 O9 100.68(14) . 3_766 ?
O5 Cu1 O9 100.68(14) 3_766 . ?
O5 Cu1 O9 79.32(14) . . ?
O9 Cu1 O9 180.0 3_766 . ?
O5 Cu1 O7 75.12(13) 3_766 3_776 ?
O5 Cu1 O7 104.88(13) . 3_776 ?
O9 Cu1 O7 106.97(14) 3_766 3_776 ?
O9 Cu1 O7 73.03(14) . 3_776 ?
O5 Cu1 O7 104.88(13) 3_766 1_545 ?
O5 Cu1 O7 75.12(13) . 1_545 ?
O9 Cu1 O7 73.03(14) 3_766 1_545 ?
O9 Cu1 O7 106.97(14) . 1_545 ?
O7 Cu1 O7 180.0 3_776 1_545 ?
O5 Cu1 Cu2 39.32(10) 3_766 3_766 ?
O5 Cu1 Cu2 140.68(10) . 3_766 ?
O9 Cu1 Cu2 40.18(10) 3_766 3_766 ?
O9 Cu1 Cu2 139.82(10) . 3_766 ?
O7 Cu1 Cu2 93.78(9) 3_776 3_766 ?
O7 Cu1 Cu2 86.22(9) 1_545 3_766 ?
O5 Cu1 Cu2 140.68(10) 3_766 . ?
O5 Cu1 Cu2 39.32(10) . . ?
O9 Cu1 Cu2 139.82(10) 3_766 . ?
O9 Cu1 Cu2 40.18(10) . . ?
O7 Cu1 Cu2 86.22(9) 3_776 . ?
O7 Cu1 Cu2 93.78(9) 1_545 . ?
Cu2 Cu1 Cu2 180.0 3_766 . ?
O7 Cu2 O5 97.74(16) 2_745 . ?
O7 Cu2 O9 177.93(14) 2_745 . ?
O5 Cu2 O9 80.42(15) . . ?
O7 Cu2 O5 85.43(15) 2_745 2_755 ?
O5 Cu2 O5 171.72(9) . 2_755 ?
O9 Cu2 O5 96.27(15) . 2_755 ?
O7 Cu2 Cu1 136.81(11) 2_745 . ?
O5 Cu2 Cu1 39.19(11) . . ?
O9 Cu2 Cu1 41.42(10) . . ?
O5 Cu2 Cu1 137.60(11) 2_755 . ?
O7 Cu2 Cu3 37.99(10) 2_745 2_745 ?
O5 Cu2 Cu3 88.23(11) . 2_745 ?
O9 Cu2 Cu3 140.66(10) . 2_745 ?
O5 Cu2 Cu3 89.64(11) 2_755 2_745 ?
Cu1 Cu2 Cu3 120.35(5) . 2_745 ?
O7 Cu3 O7 180.0 . 3_776 ?
O7 Cu3 O9 84.51(15) . 3_776 ?
O7 Cu3 O9 95.49(15) 3_776 3_776 ?
O7 Cu3 O9 95.49(15) . . ?
O7 Cu3 O9 84.51(15) 3_776 . ?
O9 Cu3 O9 180.0 3_776 . ?
O7 Cu3 Cu2 37.77(10) . 2_755 ?
O7 Cu3 Cu2 142.23(10) 3_776 2_755 ?
O9 Cu3 Cu2 90.91(11) 3_776 2_755 ?
O9 Cu3 Cu2 89.09(11) . 2_755 ?
O7 Cu3 Cu2 142.23(10) . 4_576 ?
O7 Cu3 Cu2 37.77(10) 3_776 4_576 ?
O9 Cu3 Cu2 89.09(11) 3_776 4_576 ?
O9 Cu3 Cu2 90.91(11) . 4_576 ?
Cu2 Cu3 Cu2 180.0 2_755 4_576 ?
O8 S4 O10 113.9(2) . . ?
O8 S4 O6 110.8(2) . . ?
O10 S4 O6 110.98(19) . . ?
O8 S4 C12 108.4(2) . . ?
O10 S4 C12 105.7(2) . . ?
O6 S4 C12 106.7(2) . . ?
Cu1 O5 Cu2 101.49(16) . . ?
Cu1 O5 Cu2 105.73(16) . 2_745 ?
Cu2 O5 Cu2 109.07(17) . 2_745 ?
Cu1 O5 H5 111(4) . . ?
Cu2 O5 H5 114(4) . . ?
Cu2 O5 H5 114(4) 2_745 . ?
Cu2 O7 Cu3 104.25(16) 2_755 . ?
Cu2 O7 Cu1 93.66(14) 2_755 1_565 ?
Cu3 O7 Cu1 95.85(14) . 1_565 ?
Cu2 O7 H7 116(4) 2_755 . ?
Cu3 O7 H7 113(4) . . ?
Cu1 O7 H7 130(4) 1_565 . ?
Cu2 O9 Cu3 104.78(16) . . ?
Cu2 O9 Cu1 98.40(15) . . ?
Cu3 O9 Cu1 106.40(16) . . ?
Cu2 O9 H9 110(4) . . ?
Cu3 O9 H9 114(4) . . ?
Cu1 O9 H9 121(4) . . ?
C18 C11 H11A 109(4) . . ?
C18 C11 H11B 102(4) . . ?
H11A C11 H11B 117(6) . . ?
C18 C11 H11C 111(5) . . ?
H11A C11 H11C 107(6) . . ?
H11B C11 H11C 111(6) . . ?
C16 C12 C13 121.1(5) . . ?
C16 C12 S4 119.4(4) . . ?
C13 C12 S4 119.5(4) . . ?
C12 C13 C15 118.5(5) . . ?
C12 C13 H13 120(4) . . ?
C15 C13 H13 122(4) . . ?
C15 C14 C17 118.3(5) . . ?
C15 C14 C18 120.8(6) . . ?
C17 C14 C18 120.9(5) . . ?
C14 C15 C13 121.6(6) . . ?
C14 C15 H15 125(3) . . ?
C13 C15 H15 113(3) . . ?
C17 C16 C12 119.1(6) . . ?
C17 C16 H16 123(4) . . ?
C12 C16 H16 118(4) . . ?
C16 C17 C14 121.4(5) . . ?
C16 C17 H17 119(4) . . ?
C14 C17 H17 120(4) . . ?
C14 C18 C11 111.6(6) . . ?
C14 C18 H18A 111(4) . . ?
C11 C18 H18A 113(3) . . ?
C14 C18 H18B 109(3) . . ?
C11 C18 H18B 108(3) . . ?
H18A C18 H18B 104(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
O8 S4 C12 C16 39.3(5) . . . . ?
O10 S4 C12 C16 161.7(4) . . . . ?
O6 S4 C12 C16 -80.1(4) . . . . ?
O8 S4 C12 C13 -139.5(4) . . . . ?
O10 S4 C12 C13 -17.0(5) . . . . ?
O6 S4 C12 C13 101.2(5) . . . . ?
C16 C12 C13 C15 -1.3(8) . . . . ?
S4 C12 C13 C15 177.4(4) . . . . ?
C17 C14 C15 C13 1.8(9) . . . . ?
C18 C14 C15 C13 -176.0(5) . . . . ?
C12 C13 C15 C14 -0.3(9) . . . . ?
C13 C12 C16 C17 1.2(8) . . . . ?
S4 C12 C16 C17 -177.5(4) . . . . ?
C12 C16 C17 C14 0.4(9) . . . . ?
C15 C14 C17 C16 -1.9(9) . . . . ?
C18 C14 C17 C16 175.9(5) . . . . ?
C15 C14 C18 C11 73.0(8) . . . . ?
C17 C14 C18 C11 -104.8(8) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H5 O10 . . 2_745 2.657(5) 0.80(2) 1.93(3) 151(5) no
O7 H7 O8 . . 4_576 2.893(5) 0.78(3) 2.25(4) 140(5) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


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

data_131101f13
_database_code_depnum_ccdc_archive 'CCDC 1061271'
_audit_update_record             
;
2015-10-05 deposited with the CCDC.
2015-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C7 H10 Cu2 O6 S'
_chemical_formula_moiety         'C7 H10 Cu2 O6 S'
_chemical_formula_weight         349.30
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.493(4)
_cell_length_b                   6.4490(14)
_cell_length_c                   10.597(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.476(7)
_cell_angle_gamma                90.0000
_cell_volume                     1049.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3304
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    200
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    2.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696.00
_exptl_absorpt_coefficient_mu    4.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_T_max  0.427

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      200
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            10476
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2360
_reflns_number_gt                1778
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0779
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2360
_refine_ls_number_parameters     182
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.82
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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 0.0000 1.0000 0.0000 0.01218(16) Uani 1 2 d S . P . .
Cu2 Cu 0.00889(3) 0.76614(5) 0.25261(3) 0.01184(13) Uani 1 1 d . . . . .
Cu3 Cu 0.0000 1.5000 0.0000 0.01143(15) Uani 1 2 d S . P . .
S4 S 0.19561(5) 0.42033(11) 0.40044(7) 0.0167(2) Uani 1 1 d . . . . .
O5 O 0.05083(16) 1.0237(3) 0.3401(2) 0.0120(5) Uani 1 1 d D . . . .
H5 H 0.1015(13) 1.054(5) 0.349(3) 0.018 Uiso 1 1 d D U . . .
O6 O 0.10664(16) 0.4929(3) 0.3499(2) 0.0172(5) Uani 1 1 d . . . . .
O7 O 0.05196(16) 1.2461(3) 0.0944(2) 0.0117(5) Uani 1 1 d D . . . .
H7 H 0.1033(13) 1.242(5) 0.109(3) 0.017 Uiso 1 1 d D U . . .
O8 O 0.06810(16) 0.7961(3) 0.1049(2) 0.0143(5) Uani 1 1 d D . . . .
H8 H 0.1175(14) 0.830(5) 0.115(3) 0.021 Uiso 1 1 d D U . . .
O9 O 0.20615(16) 0.2018(3) 0.3735(2) 0.0286(6) Uani 1 1 d . . . . .
O10 O 0.21631(17) 0.4731(3) 0.5339(2) 0.0278(6) Uani 1 1 d . . . . .
C11 C 0.3858(3) 0.7645(6) 0.1843(4) 0.0345(10) Uani 1 1 d . . . . .
C12 C 0.3037(3) 0.4532(6) 0.2171(3) 0.0260(8) Uani 1 1 d . . . . .
C13 C 0.2686(2) 0.5533(5) 0.3145(3) 0.0185(7) Uani 1 1 d . . . . .
C14 C 0.3620(3) 0.5605(7) 0.1528(4) 0.0364(9) Uani 1 1 d . . . . .
C15 C 0.4484(4) 0.8790(10) 0.1123(5) 0.0611(16) Uani 1 1 d . . . . .
H15A H 0.475(4) 0.774(7) 0.066(5) 0.073 Uiso 1 1 d . U . . .
H15B H 0.496(4) 0.947(7) 0.163(5) 0.073 Uiso 1 1 d . U . . .
H15C H 0.418(4) 0.950(8) 0.055(5) 0.073 Uiso 1 1 d . U . . .
C16 C 0.2901(3) 0.7565(5) 0.3460(3) 0.0255(8) Uani 1 1 d . . . . .
C17 C 0.3483(3) 0.8593(6) 0.2808(4) 0.0360(10) Uani 1 1 d . . . . .
H12 H 0.285(3) 0.318(5) 0.193(3) 0.029(10) Uiso 1 1 d . . . . .
H14 H 0.389(3) 0.486(6) 0.095(4) 0.050(14) Uiso 1 1 d . . . . .
H16 H 0.261(2) 0.820(5) 0.410(3) 0.023(9) Uiso 1 1 d . . . . .
H17 H 0.362(3) 0.999(5) 0.298(3) 0.034(11) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.1.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O8 1.942(2) . ?
Cu1 O8 1.942(2) 3_575 ?
Cu1 O7 1.990(2) . ?
Cu1 O7 1.990(2) 3_575 ?
Cu1 O6 2.438(3) 4_575 ?
Cu1 O6 2.438(3) 2 ?
Cu1 Cu2 3.0599(7) . ?
Cu1 Cu2 3.0600(8) 3_575 ?
Cu2 O8 1.924(2) . ?
Cu2 O5 1.971(2) . ?
Cu2 O7 1.983(2) 2_545 ?
Cu2 O5 2.008(2) 2_545 ?
Cu2 Cu3 3.0431(7) 2_545 ?
Cu3 O5 1.965(2) 4_585 ?
Cu3 O5 1.965(2) 2 ?
Cu3 O7 2.030(2) . ?
Cu3 O7 2.030(2) 3_585 ?
Cu3 O8 2.385(2) 3_575 ?
Cu3 O8 2.385(2) 1_565 ?
Cu3 Cu2 3.0431(7) 4_585 ?
Cu3 Cu2 3.0431(7) 2 ?
S4 O10 1.450(2) . ?
S4 O9 1.451(2) . ?
S4 O6 1.488(3) . ?
S4 C13 1.764(3) . ?
O5 Cu3 1.965(2) 2_545 ?
O5 Cu2 2.008(2) 2 ?
O5 H5 0.802(18) . ?
O6 Cu1 2.438(3) 2_545 ?
O7 Cu2 1.983(2) 2 ?
O7 H7 0.791(19) . ?
O8 Cu3 2.385(2) 1_545 ?
O8 H8 0.790(18) . ?
C11 C17 1.382(6) . ?
C11 C14 1.395(6) . ?
C11 C15 1.504(6) . ?
C12 C14 1.386(5) . ?
C12 C13 1.387(5) . ?
C12 H12 0.95(3) . ?
C13 C16 1.383(4) . ?
C14 H14 0.92(4) . ?
C15 H15A 0.96(5) . ?
C15 H15B 0.96(5) . ?
C15 H15C 0.85(5) . ?
C16 C17 1.376(6) . ?
C16 H16 0.95(4) . ?
C17 H17 0.94(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
O8 Cu1 O8 180.00(13) . 3_575 ?
O8 Cu1 O7 95.63(9) . . ?
O8 Cu1 O7 84.37(9) 3_575 . ?
O8 Cu1 O7 84.37(9) . 3_575 ?
O8 Cu1 O7 95.63(9) 3_575 3_575 ?
O7 Cu1 O7 180.0 . 3_575 ?
O8 Cu1 O6 91.27(8) . 4_575 ?
O8 Cu1 O6 88.72(8) 3_575 4_575 ?
O7 Cu1 O6 92.80(8) . 4_575 ?
O7 Cu1 O6 87.20(8) 3_575 4_575 ?
O8 Cu1 O6 88.73(8) . 2 ?
O8 Cu1 O6 91.28(8) 3_575 2 ?
O7 Cu1 O6 87.20(8) . 2 ?
O7 Cu1 O6 92.80(8) 3_575 2 ?
O6 Cu1 O6 180.00(8) 4_575 2 ?
O8 Cu1 Cu2 37.47(7) . . ?
O8 Cu1 Cu2 142.53(7) 3_575 . ?
O7 Cu1 Cu2 89.09(6) . . ?
O7 Cu1 Cu2 90.91(6) 3_575 . ?
O6 Cu1 Cu2 128.51(5) 4_575 . ?
O6 Cu1 Cu2 51.49(5) 2 . ?
O8 Cu1 Cu2 142.53(7) . 3_575 ?
O8 Cu1 Cu2 37.47(7) 3_575 3_575 ?
O7 Cu1 Cu2 90.91(6) . 3_575 ?
O7 Cu1 Cu2 89.09(6) 3_575 3_575 ?
O6 Cu1 Cu2 51.49(5) 4_575 3_575 ?
O6 Cu1 Cu2 128.51(5) 2 3_575 ?
Cu2 Cu1 Cu2 180.0 . 3_575 ?
O8 Cu2 O5 97.78(9) . . ?
O8 Cu2 O7 177.97(8) . 2_545 ?
O5 Cu2 O7 80.37(9) . 2_545 ?
O8 Cu2 O5 85.30(9) . 2_545 ?
O5 Cu2 O5 171.69(5) . 2_545 ?
O7 Cu2 O5 96.41(9) 2_545 2_545 ?
O8 Cu2 Cu3 136.96(7) . 2_545 ?
O5 Cu2 Cu3 39.28(6) . 2_545 ?
O7 Cu2 Cu3 41.26(6) 2_545 2_545 ?
O5 Cu2 Cu3 137.57(7) 2_545 2_545 ?
O8 Cu2 Cu1 37.90(7) . . ?
O5 Cu2 Cu1 88.34(6) . . ?
O7 Cu2 Cu1 140.83(6) 2_545 . ?
O5 Cu2 Cu1 89.44(6) 2_545 . ?
Cu3 Cu2 Cu1 120.49(2) 2_545 . ?
O5 Cu3 O5 180.00(11) 4_585 2 ?
O5 Cu3 O7 100.63(9) 4_585 . ?
O5 Cu3 O7 79.37(9) 2 . ?
O5 Cu3 O7 79.36(9) 4_585 3_585 ?
O5 Cu3 O7 100.64(9) 2 3_585 ?
O7 Cu3 O7 180.0 . 3_585 ?
O5 Cu3 O8 74.85(8) 4_585 3_575 ?
O5 Cu3 O8 105.15(8) 2 3_575 ?
O7 Cu3 O8 72.96(9) . 3_575 ?
O7 Cu3 O8 107.04(9) 3_585 3_575 ?
O5 Cu3 O8 105.15(8) 4_585 1_565 ?
O5 Cu3 O8 74.85(8) 2 1_565 ?
O7 Cu3 O8 107.04(9) . 1_565 ?
O7 Cu3 O8 72.96(9) 3_585 1_565 ?
O8 Cu3 O8 180.0 3_575 1_565 ?
O5 Cu3 Cu2 39.43(6) 4_585 4_585 ?
O5 Cu3 Cu2 140.57(6) 2 4_585 ?
O7 Cu3 Cu2 139.90(6) . 4_585 ?
O7 Cu3 Cu2 40.10(6) 3_585 4_585 ?
O8 Cu3 Cu2 93.56(5) 3_575 4_585 ?
O8 Cu3 Cu2 86.44(5) 1_565 4_585 ?
O5 Cu3 Cu2 140.57(6) 4_585 2 ?
O5 Cu3 Cu2 39.43(6) 2 2 ?
O7 Cu3 Cu2 40.10(6) . 2 ?
O7 Cu3 Cu2 139.90(6) 3_585 2 ?
O8 Cu3 Cu2 86.44(5) 3_575 2 ?
O8 Cu3 Cu2 93.56(5) 1_565 2 ?
Cu2 Cu3 Cu2 180.0 4_585 2 ?
O10 S4 O9 113.80(14) . . ?
O10 S4 O6 110.74(15) . . ?
O9 S4 O6 110.95(13) . . ?
O10 S4 C13 108.34(15) . . ?
O9 S4 C13 105.92(15) . . ?
O6 S4 C13 106.70(14) . . ?
Cu3 O5 Cu2 101.29(10) 2_545 . ?
Cu3 O5 Cu2 105.76(11) 2_545 2 ?
Cu2 O5 Cu2 108.85(10) . 2 ?
Cu3 O5 H5 115(3) 2_545 . ?
Cu2 O5 H5 121(3) . . ?
Cu2 O5 H5 104(3) 2 . ?
S4 O6 Cu1 116.49(12) . 2_545 ?
Cu2 O7 Cu1 105.00(10) 2 . ?
Cu2 O7 Cu3 98.64(9) 2 . ?
Cu1 O7 Cu3 106.69(10) . . ?
Cu2 O7 H7 115(3) 2 . ?
Cu1 O7 H7 113(2) . . ?
Cu3 O7 H7 117(2) . . ?
Cu2 O8 Cu1 104.63(11) . . ?
Cu2 O8 Cu3 94.01(9) . 1_545 ?
Cu1 O8 Cu3 95.79(9) . 1_545 ?
Cu2 O8 H8 118(3) . . ?
Cu1 O8 H8 110(3) . . ?
Cu3 O8 H8 130(3) 1_545 . ?
C17 C11 C14 118.1(4) . . ?
C17 C11 C15 121.2(4) . . ?
C14 C11 C15 120.6(4) . . ?
C14 C12 C13 118.5(3) . . ?
C14 C12 H12 122(2) . . ?
C13 C12 H12 120(2) . . ?
C16 C13 C12 121.0(3) . . ?
C16 C13 S4 119.1(3) . . ?
C12 C13 S4 119.9(3) . . ?
C12 C14 C11 121.4(4) . . ?
C12 C14 H14 117(3) . . ?
C11 C14 H14 122(3) . . ?
C11 C15 H15A 105(3) . . ?
C11 C15 H15B 116(3) . . ?
H15A C15 H15B 105(5) . . ?
C11 C15 H15C 107(4) . . ?
H15A C15 H15C 104(5) . . ?
H15B C15 H15C 118(5) . . ?
C17 C16 C13 119.2(4) . . ?
C17 C16 H16 123(2) . . ?
C13 C16 H16 117(2) . . ?
C16 C17 C11 121.6(4) . . ?
C16 C17 H17 121(3) . . ?
C11 C17 H17 117(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O10 S4 O6 Cu1 -31.18(16) . . . 2_545 ?
O9 S4 O6 Cu1 96.19(14) . . . 2_545 ?
C13 S4 O6 Cu1 -148.88(13) . . . 2_545 ?
C14 C12 C13 C16 0.9(5) . . . . ?
C14 C12 C13 S4 -178.8(3) . . . . ?
O10 S4 C13 C16 -40.8(3) . . . . ?
O9 S4 C13 C16 -163.3(3) . . . . ?
O6 S4 C13 C16 78.4(3) . . . . ?
O10 S4 C13 C12 138.9(3) . . . . ?
O9 S4 C13 C12 16.4(3) . . . . ?
O6 S4 C13 C12 -101.8(3) . . . . ?
C13 C12 C14 C11 0.1(6) . . . . ?
C17 C11 C14 C12 -1.0(6) . . . . ?
C15 C11 C14 C12 -179.2(4) . . . . ?
C12 C13 C16 C17 -1.0(5) . . . . ?
S4 C13 C16 C17 178.7(3) . . . . ?
C13 C16 C17 C11 0.0(6) . . . . ?
C14 C11 C17 C16 0.9(6) . . . . ?
C15 C11 C17 C16 179.1(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O5 H5 O9 . . 1_565 2.648(3) 0.80(2) 1.87(2) 163(3) no
O8 H8 O10 . . 4_575 2.916(4) 0.79(2) 2.25(3) 143(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


