# 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_151115f4_
_database_code_depnum_ccdc_archive 'CCDC 1493059'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C6 H20 Cu3 O16 S2'
_chemical_formula_moiety         'C6 H20 Cu3 O16 S2'
_chemical_formula_weight         602.97
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.6838(9)
_cell_length_b                   11.4266(19)
_cell_length_c                   13.585(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.904(4)
_cell_angle_gamma                90.0000
_cell_volume                     877.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3380
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       blocl
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606.00
_exptl_absorpt_coefficient_mu    3.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_T_max  0.456

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

_diffrn_ambient_temperature      150
_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            8148
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.015
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1953
_reflns_number_gt                1647
_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          0.0667
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1457
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1953
_refine_ls_number_parameters     145
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0692P)²+4.3455P] 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         1.85
_refine_diff_density_min         -1.12
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(17)

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 0.44419(11) 0.43309(6) 0.40658(5) 0.0185(3) Uani 1 1 d . . . . .
Cu2 Cu 0.0000 0.5000 0.5000 0.0191(3) Uani 1 2 d S . P . .
S3 S -0.0074(2) 0.37009(12) 0.11766(10) 0.0194(3) Uani 1 1 d . . . . .
O4 O -0.3304(7) 0.5523(3) 0.4613(3) 0.0178(8) Uani 1 1 d D . . . .
O5 O 0.2466(7) 0.2986(4) 0.3729(3) 0.0236(8) Uani 1 1 d . . . . .
O6 O 0.5357(7) 0.4292(4) 0.2732(3) 0.0239(9) Uani 1 1 d D . . . .
O7 O -0.0901(7) 0.3553(3) 0.4329(3) 0.0224(8) Uani 1 1 d . . . . .
O8 O 0.1566(8) 0.5838(4) 0.3589(3) 0.0233(9) Uani 1 1 d D . . . .
O9 O -0.0418(7) 0.4549(4) 0.1958(3) 0.0227(8) Uani 1 1 d . . . . .
O10 O -0.1738(7) 0.2733(4) 0.1165(3) 0.0264(9) Uani 1 1 d . . . . .
O11 O 0.2399(7) 0.3327(4) 0.1198(3) 0.0236(9) Uani 1 1 d . . . . .
C12 C 0.0330(9) 0.2843(5) 0.3890(4) 0.0208(11) Uani 1 1 d . . . . .
C13 C -0.0770(10) 0.4468(5) 0.0044(5) 0.0245(12) Uani 1 1 d . . . . .
H13A H -0.0578 0.3932 -0.0515 0.029 Uiso 1 1 calc R U . . .
H13B H -0.2447 0.4716 -0.0005 0.029 Uiso 1 1 calc R U . . .
C14 C -0.0860(10) 0.1738(5) 0.3514(5) 0.0269(12) Uani 1 1 d . . . . .
H14A H 0.0262 0.1259 0.3188 0.032 Uiso 1 1 calc R U . . .
H14B H -0.1401 0.1302 0.4069 0.032 Uiso 1 1 calc R U . . .
H14C H -0.2219 0.1931 0.3038 0.032 Uiso 1 1 calc R U . . .
H4 H -0.333(10) 0.614(3) 0.435(4) 0.008(14) Uiso 1 1 d D . . . .
H6A H 0.661(9) 0.434(8) 0.252(7) 0.06(3) Uiso 1 1 d D . . . .
H6B H 0.455(9) 0.403(5) 0.227(3) 0.011(14) Uiso 1 1 d D . . . .
H8A H 0.086(12) 0.570(6) 0.306(3) 0.03(2) Uiso 1 1 d D . . . .
H8B H 0.179(15) 0.648(8) 0.354(7) 0.05(3) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXT (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 1.931(4) . ?
Cu1 O6 1.937(4) . ?
Cu1 O4 1.963(4) 1_655 ?
Cu1 O4 1.976(4) 3_566 ?
Cu1 O8 2.416(4) . ?
Cu1 Cu1 2.9753(13) 3_666 ?
Cu1 Cu2 3.0378(7) . ?
Cu2 O7 1.932(4) . ?
Cu2 O7 1.932(4) 3_566 ?
Cu2 O4 1.989(4) . ?
Cu2 O4 1.989(4) 3_566 ?
Cu2 O8 2.395(4) . ?
Cu2 O8 2.395(4) 3_566 ?
Cu2 Cu1 3.0378(7) 3_566 ?
S3 O10 1.454(4) . ?
S3 O9 1.465(4) . ?
S3 O11 1.466(4) . ?
S3 C13 1.779(6) . ?
O4 Cu1 1.963(4) 1_455 ?
O4 Cu1 1.976(4) 3_566 ?
O4 H4 0.79(2) . ?
O5 C12 1.265(7) . ?
O6 H6A 0.80(2) . ?
O6 H6B 0.80(2) . ?
O7 C12 1.261(7) . ?
O8 H8A 0.797(15) . ?
O8 H8B 0.75(9) . ?
C12 C14 1.497(8) . ?
C13 C13 1.510(11) 3_565 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
O5 Cu1 O6 88.03(17) . . ?
O5 Cu1 O4 169.48(17) . 1_655 ?
O6 Cu1 O4 98.23(17) . 1_655 ?
O5 Cu1 O4 92.60(17) . 3_566 ?
O6 Cu1 O4 174.99(17) . 3_566 ?
O4 Cu1 O4 81.91(17) 1_655 3_566 ?
O5 Cu1 O8 98.22(16) . . ?
O6 Cu1 O8 90.27(16) . . ?
O4 Cu1 O8 90.24(16) 1_655 . ?
O4 Cu1 O8 84.71(15) 3_566 . ?
O5 Cu1 Cu1 132.76(13) . 3_666 ?
O6 Cu1 Cu1 139.12(13) . 3_666 ?
O4 Cu1 Cu1 41.11(11) 1_655 3_666 ?
O4 Cu1 Cu1 40.79(11) 3_566 3_666 ?
O8 Cu1 Cu1 86.65(11) . 3_666 ?
O5 Cu1 Cu2 79.11(12) . . ?
O6 Cu1 Cu2 135.35(13) . . ?
O4 Cu1 Cu2 101.83(11) 1_655 . ?
O4 Cu1 Cu2 40.15(11) 3_566 . ?
O8 Cu1 Cu2 50.54(10) . . ?
Cu1 Cu1 Cu2 68.14(2) 3_666 . ?
O7 Cu2 O7 180.0(2) . 3_566 ?
O7 Cu2 O4 86.30(16) . . ?
O7 Cu2 O4 93.70(16) 3_566 . ?
O7 Cu2 O4 93.70(16) . 3_566 ?
O7 Cu2 O4 86.30(16) 3_566 3_566 ?
O4 Cu2 O4 180.0 . 3_566 ?
O7 Cu2 O8 93.84(17) . . ?
O7 Cu2 O8 86.16(17) 3_566 . ?
O4 Cu2 O8 94.99(15) . . ?
O4 Cu2 O8 85.01(15) 3_566 . ?
O7 Cu2 O8 86.16(17) . 3_566 ?
O7 Cu2 O8 93.84(17) 3_566 3_566 ?
O4 Cu2 O8 85.01(15) . 3_566 ?
O4 Cu2 O8 94.99(15) 3_566 3_566 ?
O8 Cu2 O8 180.0 . 3_566 ?
O7 Cu2 Cu1 102.78(12) . 3_566 ?
O7 Cu2 Cu1 77.22(12) 3_566 3_566 ?
O4 Cu2 Cu1 39.83(11) . 3_566 ?
O4 Cu2 Cu1 140.16(11) 3_566 3_566 ?
O8 Cu2 Cu1 128.84(11) . 3_566 ?
O8 Cu2 Cu1 51.16(11) 3_566 3_566 ?
O7 Cu2 Cu1 77.22(12) . . ?
O7 Cu2 Cu1 102.78(12) 3_566 . ?
O4 Cu2 Cu1 140.17(11) . . ?
O4 Cu2 Cu1 39.84(11) 3_566 . ?
O8 Cu2 Cu1 51.16(11) . . ?
O8 Cu2 Cu1 128.84(11) 3_566 . ?
Cu1 Cu2 Cu1 180.0 3_566 . ?
O10 S3 O9 112.1(2) . . ?
O10 S3 O11 113.5(3) . . ?
O9 S3 O11 112.2(2) . . ?
O10 S3 C13 106.2(3) . . ?
O9 S3 C13 105.4(3) . . ?
O11 S3 C13 106.8(3) . . ?
Cu1 O4 Cu1 98.09(17) 1_455 3_566 ?
Cu1 O4 Cu2 116.94(19) 1_455 . ?
Cu1 O4 Cu2 100.01(17) 3_566 . ?
Cu1 O4 H4 118(4) 1_455 . ?
Cu1 O4 H4 110(4) 3_566 . ?
Cu2 O4 H4 111(4) . . ?
C12 O5 Cu1 127.3(4) . . ?
Cu1 O6 H6A 133(7) . . ?
Cu1 O6 H6B 124(5) . . ?
H6A O6 H6B 102(8) . . ?
C12 O7 Cu2 129.9(4) . . ?
Cu2 O8 Cu1 78.30(13) . . ?
Cu2 O8 H8A 116(6) . . ?
Cu1 O8 H8A 111(5) . . ?
Cu2 O8 H8B 123(7) . . ?
Cu1 O8 H8B 127(7) . . ?
H8A O8 H8B 101(9) . . ?
O7 C12 O5 126.0(5) . . ?
O7 C12 C14 116.8(5) . . ?
O5 C12 C14 117.2(5) . . ?
C13 C13 S3 112.7(5) 3_565 . ?
C13 C13 H13A 109.0 3_565 . ?
S3 C13 H13A 109.0 . . ?
C13 C13 H13B 109.0 3_565 . ?
S3 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu2 O7 C12 O5 -5.8(9) . . . . ?
Cu2 O7 C12 C14 175.0(4) . . . . ?
Cu1 O5 C12 O7 -2.0(9) . . . . ?
Cu1 O5 C12 C14 177.2(4) . . . . ?
O10 S3 C13 C13 178.2(6) . . . 3_565 ?
O9 S3 C13 C13 59.1(6) . . . 3_565 ?
O11 S3 C13 C13 -60.3(6) . . . 3_565 ?

#==============================================================================
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
O4 H4 O10 . . 2_455 2.738(6) 0.79(4) 1.95(4) 174(5) no
O6 H6A O9 . . 1_655 2.735(6) 0.80(6) 1.93(7) 176(9) no
O6 H6B O11 . . . 2.768(6) 0.80(5) 1.97(5) 176(5) no
O8 H8A O9 . . . 2.799(6) 0.80(5) 2.07(6) 152(7) no
O8 H8B O11 . . 2_555 2.913(6) 0.75(9) 2.18(9) 166(10) 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_141221f53
_database_code_depnum_ccdc_archive 'CCDC 1493060'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H50 Cu3 O16 S2'
_chemical_formula_moiety         'C20 H50 Cu3 O16 S2'
_chemical_formula_weight         801.36
_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                   5.6080(4)
_cell_length_b                   8.6585(7)
_cell_length_c                   17.5909(19)
_cell_angle_alpha                88.075(5)
_cell_angle_beta                 89.276(5)
_cell_angle_gamma                77.558(5)
_cell_volume                     833.62(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3632
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.005
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             417.00
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.545
_exptl_absorpt_correction_T_max  0.659

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

_diffrn_ambient_temperature      150
_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            7969
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3490
_reflns_number_gt                3184
_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          0.0351
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0784
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     202
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0375P)²+0.4449P] 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         0.53
_refine_diff_density_min         -0.59
_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 1.0000 0.01249(10) Uani 1 2 d S . P . .
Cu2 Cu 1.00096(4) 0.41417(3) 0.92726(2) 0.01377(9) Uani 1 1 d . . . . .
S3 S 0.78846(9) 0.95283(6) 0.85625(3) 0.01534(13) Uani 1 1 d . . . . .
O4 O 0.7950(3) 0.58740(18) 0.98309(9) 0.0140(3) Uani 1 1 d D . . . .
H4 H 0.756(4) 0.662(3) 0.9568(14) 0.017 Uiso 1 1 d D U . . .
O5 O 0.4291(3) 0.49549(19) 0.89152(9) 0.0172(3) Uani 1 1 d . . . . .
O6 O 0.8003(3) 0.46288(19) 0.83664(9) 0.0189(3) Uani 1 1 d . . . . .
O7 O 0.7650(3) 0.25439(19) 0.99300(10) 0.0168(3) Uani 1 1 d D . . . .
H7A H 0.809(5) 0.201(3) 1.0289(12) 0.020 Uiso 1 1 d D U . . .
H7B H 0.729(5) 0.206(3) 0.9616(13) 0.020 Uiso 1 1 d D U . . .
O8 O 0.6515(3) 0.8544(2) 0.89832(10) 0.0249(4) Uani 1 1 d . . . . .
O9 O 1.1853(3) 0.2225(2) 0.88008(11) 0.0244(4) Uani 1 1 d D . . . .
H9A H 1.326(3) 0.198(3) 0.8769(17) 0.029 Uiso 1 1 d D U . . .
H9B H 1.140(5) 0.142(3) 0.8832(17) 0.029 Uiso 1 1 d D U . . .
O10 O 1.0409(3) 0.93322(19) 0.88159(10) 0.0225(4) Uani 1 1 d . . . . .
O11 O 0.6653(3) 1.11999(18) 0.85487(10) 0.0213(4) Uani 1 1 d . . . . .
C12 C 0.5709(4) 0.4821(3) 0.83464(13) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.5591(5) 0.9040(3) 0.72383(15) 0.0284(6) Uani 1 1 d . . . . .
H13A H 0.4694 1.0158 0.7222 0.034 Uiso 1 1 calc R U . . .
H13B H 0.4618 0.8416 0.7545 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4546(4) 0.4838(3) 0.75830(14) 0.0267(5) Uani 1 1 d . . . . .
H14A H 0.2772 0.4995 0.7646 0.032 Uiso 1 1 calc R U . . .
H14B H 0.4928 0.5703 0.7263 0.032 Uiso 1 1 calc R U . . .
H14C H 0.5178 0.3828 0.7340 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3514(5) 0.8336(4) 0.60521(15) 0.0326(6) Uani 1 1 d . . . . .
H15A H 0.2417 0.9398 0.6044 0.039 Uiso 1 1 calc R U . . .
H15B H 0.2709 0.7613 0.6359 0.039 Uiso 1 1 calc R U . . .
C16 C 0.3864(5) 0.7756(4) 0.52434(15) 0.0353(6) Uani 1 1 d . . . . .
H16A H 0.4559 0.8526 0.4931 0.042 Uiso 1 1 calc R U . . .
H16B H 0.5072 0.6737 0.5250 0.042 Uiso 1 1 calc R U . . .
C17 C 0.5901(5) 0.8426(4) 0.64298(15) 0.0322(6) Uani 1 1 d . . . . .
H17A H 0.6722 0.9128 0.6114 0.039 Uiso 1 1 calc R U . . .
H17B H 0.6981 0.7358 0.6445 0.039 Uiso 1 1 calc R U . . .
C18 C 0.1551(5) 0.7527(4) 0.48644(16) 0.0352(6) Uani 1 1 d . . . . .
H18A H 0.0904 0.6711 0.5158 0.042 Uiso 1 1 calc R U . . .
H18B H 0.0308 0.8530 0.4880 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8067(4) 0.8914(3) 0.76111(14) 0.0271(6) Uani 1 1 d . . . . .
H19A H 0.9005 0.9567 0.7308 0.032 Uiso 1 1 calc R U . . .
H19B H 0.8982 0.7801 0.7599 0.032 Uiso 1 1 calc R U . . .
C20 C 0.1941(6) 0.7036(4) 0.40471(17) 0.0433(8) Uani 1 1 d . . . . .
H20A H 0.3242 0.6062 0.4032 0.052 Uiso 1 1 calc R U . . .
H20B H 0.2529 0.7875 0.3752 0.052 Uiso 1 1 calc R U . . .
C21 C -0.0314(6) 0.6729(4) 0.36584(19) 0.0499(9) Uani 1 1 d . . . . .
H21A H 0.0098 0.6419 0.3134 0.060 Uiso 1 1 calc R U . . .
H21B H -0.0889 0.5877 0.3936 0.060 Uiso 1 1 calc R U . . .
H21C H -0.1602 0.7695 0.3655 0.060 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXT Version 2014/5 (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 1.9576(15) 2_667 ?
Cu1 O5 1.9576(15) . ?
Cu1 O4 1.9773(14) . ?
Cu1 O4 1.9773(14) 2_667 ?
Cu1 O7 2.3231(16) 2_667 ?
Cu1 O7 2.3231(16) . ?
Cu1 Cu2 3.0258(3) 2_667 ?
Cu1 Cu2 3.0258(3) . ?
Cu2 O6 1.9445(16) . ?
Cu2 O4 1.9582(15) 2_767 ?
Cu2 O9 1.9604(17) . ?
Cu2 O4 1.9678(15) . ?
Cu2 O7 2.3760(17) . ?
Cu2 Cu2 3.0011(6) 2_767 ?
S3 O8 1.4452(17) . ?
S3 O11 1.4627(16) . ?
S3 O10 1.4626(16) . ?
S3 C19 1.768(3) . ?
O4 Cu2 1.9581(15) 2_767 ?
O4 H4 0.776(17) . ?
O5 C12 1.263(3) . ?
O6 C12 1.262(3) . ?
O7 H7A 0.780(17) . ?
O7 H7B 0.761(17) . ?
O9 H9A 0.774(17) . ?
O9 H9B 0.790(17) . ?
C12 C14 1.498(3) . ?
C13 C19 1.524(3) . ?
C13 C17 1.530(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.520(4) . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C18 1.519(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.513(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.521(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
O5 Cu1 O5 180.00(9) 2_667 . ?
O5 Cu1 O4 85.77(6) 2_667 . ?
O5 Cu1 O4 94.23(6) . . ?
O5 Cu1 O4 94.22(6) 2_667 2_667 ?
O5 Cu1 O4 85.78(6) . 2_667 ?
O4 Cu1 O4 180.0 . 2_667 ?
O5 Cu1 O7 90.03(6) 2_667 2_667 ?
O5 Cu1 O7 89.97(6) . 2_667 ?
O4 Cu1 O7 94.74(6) . 2_667 ?
O4 Cu1 O7 85.26(6) 2_667 2_667 ?
O5 Cu1 O7 89.97(6) 2_667 . ?
O5 Cu1 O7 90.03(6) . . ?
O4 Cu1 O7 85.26(6) . . ?
O4 Cu1 O7 94.74(6) 2_667 . ?
O7 Cu1 O7 180.0 2_667 . ?
O5 Cu1 Cu2 76.52(4) 2_667 2_667 ?
O5 Cu1 Cu2 103.48(4) . 2_667 ?
O4 Cu1 Cu2 140.20(4) . 2_667 ?
O4 Cu1 Cu2 39.80(4) 2_667 2_667 ?
O7 Cu1 Cu2 50.69(4) 2_667 2_667 ?
O7 Cu1 Cu2 129.31(4) . 2_667 ?
O5 Cu1 Cu2 103.48(4) 2_667 . ?
O5 Cu1 Cu2 76.51(4) . . ?
O4 Cu1 Cu2 39.80(4) . . ?
O4 Cu1 Cu2 140.20(4) 2_667 . ?
O7 Cu1 Cu2 129.31(4) 2_667 . ?
O7 Cu1 Cu2 50.69(4) . . ?
Cu2 Cu1 Cu2 180.0 2_667 . ?
O6 Cu2 O4 167.87(7) . 2_767 ?
O6 Cu2 O9 89.64(7) . . ?
O4 Cu2 O9 98.90(7) 2_767 . ?
O6 Cu2 O4 92.38(7) . . ?
O4 Cu2 O4 80.29(7) 2_767 . ?
O9 Cu2 O4 172.30(7) . . ?
O6 Cu2 O7 97.74(6) . . ?
O4 Cu2 O7 91.14(6) 2_767 . ?
O9 Cu2 O7 88.33(7) . . ?
O4 Cu2 O7 84.04(6) . . ?
O6 Cu2 Cu2 131.69(5) . 2_767 ?
O4 Cu2 Cu2 40.26(4) 2_767 2_767 ?
O9 Cu2 Cu2 138.66(6) . 2_767 ?
O4 Cu2 Cu2 40.03(4) . 2_767 ?
O7 Cu2 Cu2 86.84(4) . 2_767 ?
O6 Cu2 Cu1 80.05(5) . . ?
O4 Cu2 Cu1 99.86(4) 2_767 . ?
O9 Cu2 Cu1 133.40(5) . . ?
O4 Cu2 Cu1 40.03(4) . . ?
O7 Cu2 Cu1 49.15(4) . . ?
Cu2 Cu2 Cu1 67.023(10) 2_767 . ?
O8 S3 O11 112.32(10) . . ?
O8 S3 O10 113.79(10) . . ?
O11 S3 O10 110.52(9) . . ?
O8 S3 C19 106.92(12) . . ?
O11 S3 C19 106.98(12) . . ?
O10 S3 C19 105.81(11) . . ?
Cu2 O4 Cu2 99.71(7) 2_767 . ?
Cu2 O4 Cu1 115.46(8) 2_767 . ?
Cu2 O4 Cu1 100.17(7) . . ?
Cu2 O4 H4 122(2) 2_767 . ?
Cu2 O4 H4 111(2) . . ?
Cu1 O4 H4 106.4(19) . . ?
C12 O5 Cu1 130.19(14) . . ?
C12 O6 Cu2 125.75(15) . . ?
Cu1 O7 Cu2 80.16(5) . . ?
Cu1 O7 H7A 123(2) . . ?
Cu2 O7 H7A 124(2) . . ?
Cu1 O7 H7B 112(2) . . ?
Cu2 O7 H7B 103(2) . . ?
H7A O7 H7B 111(3) . . ?
Cu2 O9 H9A 126(2) . . ?
Cu2 O9 H9B 121(2) . . ?
H9A O9 H9B 105(3) . . ?
O6 C12 O5 126.0(2) . . ?
O6 C12 C14 117.6(2) . . ?
O5 C12 C14 116.4(2) . . ?
C19 C13 C17 110.8(2) . . ?
C19 C13 H13A 109.5 . . ?
C17 C13 H13A 109.5 . . ?
C19 C13 H13B 109.5 . . ?
C17 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C16 112.9(2) . . ?
C17 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C17 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C18 C16 C15 114.7(2) . . ?
C18 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C18 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C15 C17 C13 113.9(2) . . ?
C15 C17 H17A 108.8 . . ?
C13 C17 H17A 108.8 . . ?
C15 C17 H17B 108.8 . . ?
C13 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C20 C18 C16 113.3(2) . . ?
C20 C18 H18A 108.9 . . ?
C16 C18 H18A 108.9 . . ?
C20 C18 H18B 108.9 . . ?
C16 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C13 C19 S3 113.94(18) . . ?
C13 C19 H19A 108.8 . . ?
S3 C19 H19A 108.8 . . ?
C13 C19 H19B 108.8 . . ?
S3 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C18 C20 C21 114.8(3) . . ?
C18 C20 H20A 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C18 C20 H20B 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Cu2 O6 C12 O5 10.8(3) . . . . ?
Cu2 O6 C12 C14 -166.98(16) . . . . ?
Cu1 O5 C12 O6 2.5(3) . . . . ?
Cu1 O5 C12 C14 -179.71(16) . . . . ?
C17 C15 C16 C18 175.6(3) . . . . ?
C16 C15 C17 C13 178.8(2) . . . . ?
C19 C13 C17 C15 173.4(2) . . . . ?
C15 C16 C18 C20 176.9(3) . . . . ?
C17 C13 C19 S3 -177.71(19) . . . . ?
O8 S3 C19 C13 58.7(2) . . . . ?
O11 S3 C19 C13 -61.8(2) . . . . ?
O10 S3 C19 C13 -179.67(19) . . . . ?
C16 C18 C20 C21 177.6(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
O4 H4 O8 . . . 2.686(2) 0.78(2) 1.91(2) 176(2) no
O7 H7A O10 . . 2_767 2.784(2) 0.78(2) 2.01(2) 174(3) no
O7 H7B O11 . . 1_545 2.842(3) 0.76(3) 2.10(2) 164(3) no
O9 H9A O11 . . 1_645 2.683(2) 0.774(18) 1.916(18) 171(3) no
O9 H9B O10 . . 1_545 2.793(3) 0.79(3) 2.01(3) 175(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.


####################################################################### 
# 
# 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_150128f5
_database_code_depnum_ccdc_archive 'CCDC 1493061'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C18 H30 Cu3 O16 S2'
_chemical_formula_moiety         'C18 H30 Cu3 O16 S2'
_chemical_formula_weight         757.18
_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                   5.7415(4)
_cell_length_b                   8.7940(6)
_cell_length_c                   27.737(2)
_cell_angle_alpha                83.890(4)
_cell_angle_beta                 89.704(5)
_cell_angle_gamma                80.177(4)
_cell_volume                     1371.97(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4914
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             770.00
_exptl_absorpt_coefficient_mu    2.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_T_max  0.603

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

_diffrn_ambient_temperature      150
_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            12287
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_theta_max         25.364
_diffrn_reflns_theta_min         2.216
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4928
_reflns_number_gt                3557
_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          0.0498
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0890
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4928
_refine_ls_number_parameters     389
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0477P)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          0.001
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.78
_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 1.00823(6) 0.09637(4) 0.04089(2) 0.01515(12) Uani 1 1 d . . . . .
Cu2 Cu 1.5000 0.0000 0.0000 0.01398(14) Uani 1 2 d S . P . .
Cu3 Cu 0.49055(6) 0.42397(4) 0.45483(2) 0.01296(12) Uani 1 1 d . . . . .
Cu4 Cu 0.0000 0.5000 0.5000 0.01248(14) Uani 1 2 d S . P . .
S1 S 0.24418(13) 0.53154(9) 0.09040(3) 0.01622(18) Uani 1 1 d . . . . .
S2 S 0.74172(13) 0.02424(9) 0.58497(3) 0.01571(18) Uani 1 1 d . . . . .
O1 O 1.2021(4) 0.0712(3) 0.09895(9) 0.0227(5) Uani 1 1 d . . . . .
O2 O 1.5644(4) 0.0112(3) 0.06789(9) 0.0205(5) Uani 1 1 d . . . . .
O3 O 1.2009(4) -0.0799(3) 0.01339(10) 0.0168(5) Uani 1 1 d . . . . .
H3A H 1.232(7) -0.140(5) 0.0310(16) 0.020 Uiso 1 1 d . U . . .
O4 O 0.8254(5) 0.2805(3) 0.06450(12) 0.0330(7) Uani 1 1 d . . . . .
H4B H 0.876(8) 0.350(5) 0.0678(18) 0.040 Uiso 1 1 d . U . . .
H4A H 0.704(8) 0.318(5) 0.0573(18) 0.040 Uiso 1 1 d . U . . .
O5 O 1.2421(4) 0.2467(3) -0.00743(10) 0.0192(5) Uani 1 1 d . . . . .
H5A H 1.272(7) 0.305(5) 0.0084(16) 0.023 Uiso 1 1 d . U . . .
H5B H 1.211(7) 0.291(5) -0.0324(17) 0.023 Uiso 1 1 d . U . . .
O6 O 0.2946(4) 0.4770(3) 0.39730(8) 0.0178(5) Uani 1 1 d . . . . .
O7 O -0.0671(4) 0.5078(3) 0.43070(8) 0.0177(5) Uani 1 1 d . . . . .
O8 O 0.6670(4) 0.2462(3) 0.42482(10) 0.0188(5) Uani 1 1 d . . . . .
H8B H 0.621(7) 0.177(5) 0.4277(16) 0.023 Uiso 1 1 d . U . . .
H8A H 0.799(7) 0.206(5) 0.4254(15) 0.023 Uiso 1 1 d . U . . .
O9 O 0.7023(4) 0.4163(3) 0.51025(9) 0.0135(5) Uani 1 1 d . . . . .
H9A H 0.744(7) 0.344(5) 0.5243(15) 0.016 Uiso 1 1 d . U . . .
O10 O 0.2617(4) 0.2597(3) 0.49920(10) 0.0167(5) Uani 1 1 d . . . . .
H10B H 0.310(7) 0.206(5) 0.5235(16) 0.020 Uiso 1 1 d . U . . .
H10A H 0.216(7) 0.224(5) 0.4814(16) 0.020 Uiso 1 1 d . U . . .
O11 O -0.0111(4) 0.5397(3) 0.08593(9) 0.0215(5) Uani 1 1 d . . . . .
O12 O 0.3182(4) 0.6818(3) 0.08357(10) 0.0288(6) Uani 1 1 d . . . . .
O13 O 0.3698(4) 0.4213(3) 0.05957(9) 0.0272(6) Uani 1 1 d . . . . .
O14 O 0.4861(4) 0.0402(3) 0.57696(9) 0.0214(5) Uani 1 1 d . . . . .
O15 O 0.8524(4) 0.1304(3) 0.55256(9) 0.0238(6) Uani 1 1 d . . . . .
O16 O 0.8587(4) -0.1367(2) 0.58379(9) 0.0205(5) Uani 1 1 d . . . . .
C1 C 0.3206(5) 0.4567(4) 0.15088(13) 0.0174(7) Uani 1 1 d . . . . .
C2 C 0.5292(6) 0.4881(4) 0.17140(14) 0.0236(8) Uani 1 1 d . . . . .
H2 H 0.6281 0.5479 0.1530 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5869(6) 0.4300(4) 0.21887(14) 0.0252(8) Uani 1 1 d . . . . .
H3 H 0.7281 0.4497 0.2328 0.030 Uiso 1 1 calc R U . . .
C4 C 0.4446(6) 0.3436(4) 0.24678(13) 0.0230(8) Uani 1 1 d . . . . .
C5 C 0.2410(6) 0.3123(4) 0.22557(14) 0.0265(8) Uani 1 1 d . . . . .
H5 H 0.1428 0.2520 0.2441 0.032 Uiso 1 1 calc R U . . .
C6 C 0.1794(6) 0.3680(4) 0.17770(14) 0.0237(8) Uani 1 1 d . . . . .
H6 H 0.0408 0.3452 0.1635 0.028 Uiso 1 1 calc R U . . .
C7 C 0.5101(7) 0.2857(5) 0.29870(14) 0.0332(9) Uani 1 1 d . . . . .
H7A H 0.4392 0.1935 0.3084 0.040 Uiso 1 1 calc R U . . .
H7B H 0.4512 0.3670 0.3195 0.040 Uiso 1 1 calc R U . . .
H7C H 0.6824 0.2589 0.3020 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7818(5) 0.0704(4) 0.64434(13) 0.0182(7) Uani 1 1 d . . . . .
C9 C 1.0009(6) 0.0238(4) 0.66708(15) 0.0283(9) Uani 1 1 d . . . . .
H9 H 1.1262 -0.0358 0.6512 0.034 Uiso 1 1 calc R U . . .
C10 C 1.0356(7) 0.0643(5) 0.71269(15) 0.0333(9) Uani 1 1 d . . . . .
H10 H 1.1854 0.0304 0.7282 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8575(6) 0.1535(4) 0.73683(15) 0.0288(9) Uani 1 1 d . . . . .
C12 C 0.6402(7) 0.1993(5) 0.71328(16) 0.0353(10) Uani 1 1 d . . . . .
H12 H 0.5153 0.2601 0.7289 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6015(6) 0.1580(4) 0.66738(15) 0.0301(9) Uani 1 1 d . . . . .
H13 H 0.4512 0.1900 0.6519 0.036 Uiso 1 1 calc R U . . .
C14 C 0.9030(8) 0.2010(6) 0.78598(16) 0.0446(12) Uani 1 1 d . . . . .
H14A H 1.0424 0.2519 0.7846 0.054 Uiso 1 1 calc R U . . .
H14B H 0.9309 0.1089 0.8098 0.054 Uiso 1 1 calc R U . . .
H14C H 0.7654 0.2733 0.7955 0.054 Uiso 1 1 calc R U . . .
C15 C 1.4254(6) 0.0344(4) 0.10268(13) 0.0198(7) Uani 1 1 d . . . . .
C16 C 1.5360(7) 0.0148(5) 0.15205(14) 0.0353(10) Uani 1 1 d . . . . .
H16A H 1.6006 -0.0950 0.1611 0.042 Uiso 1 1 calc R U . . .
H16B H 1.4164 0.0506 0.1756 0.042 Uiso 1 1 calc R U . . .
H16C H 1.6636 0.0760 0.1519 0.042 Uiso 1 1 calc R U . . .
C17 C 0.0701(5) 0.5009(4) 0.39457(13) 0.0168(7) Uani 1 1 d . . . . .
C18 C -0.0401(6) 0.5179(5) 0.34533(14) 0.0295(9) Uani 1 1 d . . . . .
H18A H -0.0007 0.6105 0.3264 0.035 Uiso 1 1 calc R U . . .
H18B H -0.2121 0.5283 0.3483 0.035 Uiso 1 1 calc R U . . .
H18C H 0.0201 0.4260 0.3289 0.035 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_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 O1 1.934(2) . ?
Cu1 O4 1.947(3) . ?
Cu1 O3 1.963(2) 2_755 ?
Cu1 O3 1.966(2) . ?
Cu1 O5 2.357(3) . ?
Cu1 Cu1 2.9838(8) 2_755 ?
Cu1 Cu2 3.0548(4) . ?
Cu2 O2 1.937(2) . ?
Cu2 O2 1.937(2) 2_855 ?
Cu2 O3 1.982(2) 2_855 ?
Cu2 O3 1.982(2) . ?
Cu2 O5 2.398(2) . ?
Cu2 O5 2.398(2) 2_855 ?
Cu2 Cu1 3.0549(4) 2_855 ?
Cu3 O6 1.927(2) . ?
Cu3 O9 1.953(2) . ?
Cu3 O9 1.971(2) 2_666 ?
Cu3 O8 1.973(2) . ?
Cu3 O10 2.362(3) . ?
Cu3 Cu3 2.9738(8) 2_666 ?
Cu4 O7 1.954(2) . ?
Cu4 O7 1.954(2) 2_566 ?
Cu4 O9 1.981(2) 2_666 ?
Cu4 O9 1.981(2) 1_455 ?
Cu4 O10 2.377(2) . ?
Cu4 O10 2.377(2) 2_566 ?
S1 O12 1.449(3) . ?
S1 O13 1.457(2) . ?
S1 O11 1.461(2) . ?
S1 C1 1.765(4) . ?
S2 O15 1.450(3) . ?
S2 O16 1.463(2) . ?
S2 O14 1.466(2) . ?
S2 C8 1.763(4) . ?
O1 C15 1.270(4) . ?
O2 C15 1.260(4) . ?
O3 Cu1 1.963(2) 2_755 ?
O3 H3A 0.68(4) . ?
O4 H4B 0.73(5) . ?
O4 H4A 0.74(5) . ?
O5 H5A 0.75(4) . ?
O5 H5B 0.76(5) . ?
O6 C17 1.271(4) . ?
O7 C17 1.272(4) . ?
O8 H8B 0.70(4) . ?
O8 H8A 0.78(4) . ?
O9 Cu3 1.971(2) 2_666 ?
O9 Cu4 1.981(2) 1_655 ?
O9 H9A 0.72(4) . ?
O10 H10B 0.80(4) . ?
O10 H10A 0.69(4) . ?
C1 C6 1.380(5) . ?
C1 C2 1.410(5) . ?
C2 C3 1.381(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 C7 1.503(5) . ?
C5 C6 1.391(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.378(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.374(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(5) . ?
C11 C14 1.505(6) . ?
C12 C13 1.390(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.493(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.491(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O1 Cu1 O4 87.99(12) . . ?
O1 Cu1 O3 168.40(10) . 2_755 ?
O4 Cu1 O3 97.99(11) . 2_755 ?
O1 Cu1 O3 93.50(10) . . ?
O4 Cu1 O3 175.96(12) . . ?
O3 Cu1 O3 81.20(10) 2_755 . ?
O1 Cu1 O5 96.23(10) . . ?
O4 Cu1 O5 91.74(11) . . ?
O3 Cu1 O5 93.52(10) 2_755 . ?
O3 Cu1 O5 84.37(9) . . ?
O1 Cu1 Cu1 133.23(7) . 2_755 ?
O4 Cu1 Cu1 138.49(10) . 2_755 ?
O3 Cu1 Cu1 40.63(6) 2_755 2_755 ?
O3 Cu1 Cu1 40.56(7) . 2_755 ?
O5 Cu1 Cu1 88.61(7) . 2_755 ?
O1 Cu1 Cu2 78.92(7) . . ?
O4 Cu1 Cu2 137.50(9) . . ?
O3 Cu1 Cu2 102.70(7) 2_755 . ?
O3 Cu1 Cu2 39.51(7) . . ?
O5 Cu1 Cu2 50.63(6) . . ?
Cu1 Cu1 Cu2 68.663(13) 2_755 . ?
O2 Cu2 O2 180.0 . 2_855 ?
O2 Cu2 O3 86.55(10) . 2_855 ?
O2 Cu2 O3 93.45(10) 2_855 2_855 ?
O2 Cu2 O3 93.45(10) . . ?
O2 Cu2 O3 86.55(10) 2_855 . ?
O3 Cu2 O3 180.0 2_855 . ?
O2 Cu2 O5 92.36(9) . . ?
O2 Cu2 O5 87.64(9) 2_855 . ?
O3 Cu2 O5 97.05(9) 2_855 . ?
O3 Cu2 O5 82.95(9) . . ?
O2 Cu2 O5 87.64(9) . 2_855 ?
O2 Cu2 O5 92.36(9) 2_855 2_855 ?
O3 Cu2 O5 82.95(9) 2_855 2_855 ?
O3 Cu2 O5 97.05(9) . 2_855 ?
O5 Cu2 O5 180.0 . 2_855 ?
O2 Cu2 Cu1 76.94(6) . . ?
O2 Cu2 Cu1 103.07(6) 2_855 . ?
O3 Cu2 Cu1 140.87(6) 2_855 . ?
O3 Cu2 Cu1 39.13(6) . . ?
O5 Cu2 Cu1 49.45(6) . . ?
O5 Cu2 Cu1 130.55(6) 2_855 . ?
O2 Cu2 Cu1 103.07(6) . 2_855 ?
O2 Cu2 Cu1 76.93(6) 2_855 2_855 ?
O3 Cu2 Cu1 39.13(6) 2_855 2_855 ?
O3 Cu2 Cu1 140.87(6) . 2_855 ?
O5 Cu2 Cu1 130.55(6) . 2_855 ?
O5 Cu2 Cu1 49.45(6) 2_855 2_855 ?
Cu1 Cu2 Cu1 180.0 . 2_855 ?
O6 Cu3 O9 167.54(10) . . ?
O6 Cu3 O9 92.86(9) . 2_666 ?
O9 Cu3 O9 81.45(9) . 2_666 ?
O6 Cu3 O8 89.09(10) . . ?
O9 Cu3 O8 97.83(10) . . ?
O9 Cu3 O8 173.32(10) 2_666 . ?
O6 Cu3 O10 98.55(10) . . ?
O9 Cu3 O10 91.74(10) . . ?
O9 Cu3 O10 82.63(9) 2_666 . ?
O8 Cu3 O10 90.76(10) . . ?
O6 Cu3 Cu3 132.39(7) . 2_666 ?
O9 Cu3 Cu3 40.96(6) . 2_666 ?
O9 Cu3 Cu3 40.50(7) 2_666 2_666 ?
O8 Cu3 Cu3 138.40(8) . 2_666 ?
O10 Cu3 Cu3 86.27(7) . 2_666 ?
O7 Cu4 O7 180.00(3) . 2_566 ?
O7 Cu4 O9 93.84(10) . 2_666 ?
O7 Cu4 O9 86.16(10) 2_566 2_666 ?
O7 Cu4 O9 86.16(10) . 1_455 ?
O7 Cu4 O9 93.84(10) 2_566 1_455 ?
O9 Cu4 O9 180.0 2_666 1_455 ?
O7 Cu4 O10 91.33(9) . . ?
O7 Cu4 O10 88.67(9) 2_566 . ?
O9 Cu4 O10 82.06(8) 2_666 . ?
O9 Cu4 O10 97.94(9) 1_455 . ?
O7 Cu4 O10 88.66(9) . 2_566 ?
O7 Cu4 O10 91.34(9) 2_566 2_566 ?
O9 Cu4 O10 97.94(9) 2_666 2_566 ?
O9 Cu4 O10 82.06(8) 1_455 2_566 ?
O10 Cu4 O10 180.0 . 2_566 ?
O12 S1 O13 112.98(16) . . ?
O12 S1 O11 113.59(14) . . ?
O13 S1 O11 110.83(15) . . ?
O12 S1 C1 105.85(16) . . ?
O13 S1 C1 106.77(14) . . ?
O11 S1 C1 106.22(15) . . ?
O15 S2 O16 111.66(14) . . ?
O15 S2 O14 113.58(14) . . ?
O16 S2 O14 111.14(14) . . ?
O15 S2 C8 106.95(16) . . ?
O16 S2 C8 106.37(14) . . ?
O14 S2 C8 106.66(14) . . ?
C15 O1 Cu1 127.9(2) . . ?
C15 O2 Cu2 130.5(2) . . ?
Cu1 O3 Cu1 98.80(10) 2_755 . ?
Cu1 O3 Cu2 119.37(13) 2_755 . ?
Cu1 O3 Cu2 101.37(10) . . ?
Cu1 O3 H3A 121(4) 2_755 . ?
Cu1 O3 H3A 110(4) . . ?
Cu2 O3 H3A 104(4) . . ?
Cu1 O4 H4B 123(3) . . ?
Cu1 O4 H4A 127(4) . . ?
H4B O4 H4A 99(5) . . ?
Cu1 O5 Cu2 79.92(8) . . ?
Cu1 O5 H5A 105(3) . . ?
Cu2 O5 H5A 116(3) . . ?
Cu1 O5 H5B 128(3) . . ?
Cu2 O5 H5B 120(3) . . ?
H5A O5 H5B 106(5) . . ?
C17 O6 Cu3 127.7(2) . . ?
C17 O7 Cu4 131.0(2) . . ?
Cu3 O8 H8B 117(3) . . ?
Cu3 O8 H8A 134(3) . . ?
H8B O8 H8A 95(4) . . ?
Cu3 O9 Cu3 98.55(9) . 2_666 ?
Cu3 O9 Cu4 118.71(12) . 1_655 ?
Cu3 O9 Cu4 102.10(10) 2_666 1_655 ?
Cu3 O9 H9A 120(3) . . ?
Cu3 O9 H9A 116(3) 2_666 . ?
Cu4 O9 H9A 101(3) 1_655 . ?
Cu3 O10 Cu4 80.88(8) . . ?
Cu3 O10 H10B 123(3) . . ?
Cu4 O10 H10B 123(3) . . ?
Cu3 O10 H10A 103(4) . . ?
Cu4 O10 H10A 104(3) . . ?
H10B O10 H10A 117(5) . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 S1 120.7(3) . . ?
C2 C1 S1 119.0(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 120.4(4) . . ?
C5 C4 C7 121.1(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.7(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.9(3) . . ?
C13 C8 S2 120.7(3) . . ?
C9 C8 S2 119.4(3) . . ?
C10 C9 C8 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C12 C11 C10 117.4(4) . . ?
C12 C11 C14 121.8(3) . . ?
C10 C11 C14 120.8(3) . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 119.8(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O1 125.3(3) . . ?
O2 C15 C16 116.3(3) . . ?
O1 C15 C16 118.3(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 O7 125.0(3) . . ?
O6 C17 C18 117.4(3) . . ?
O7 C17 C18 117.6(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O12 S1 C1 C6 144.9(3) . . . . ?
O13 S1 C1 C6 -94.5(3) . . . . ?
O11 S1 C1 C6 23.8(3) . . . . ?
O12 S1 C1 C2 -35.5(3) . . . . ?
O13 S1 C1 C2 85.2(3) . . . . ?
O11 S1 C1 C2 -156.5(2) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
S1 C1 C2 C3 179.5(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C2 C3 C4 C7 -178.5(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C7 C4 C5 C6 179.1(3) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
S1 C1 C6 C5 -179.0(2) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
O15 S2 C8 C13 100.5(3) . . . . ?
O16 S2 C8 C13 -140.0(3) . . . . ?
O14 S2 C8 C13 -21.3(3) . . . . ?
O15 S2 C8 C9 -76.5(3) . . . . ?
O16 S2 C8 C9 42.9(3) . . . . ?
O14 S2 C8 C9 161.6(3) . . . . ?
C13 C8 C9 C10 0.6(6) . . . . ?
S2 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C9 C10 C11 C14 -177.7(4) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C14 C11 C12 C13 178.4(4) . . . . ?
C9 C8 C13 C12 0.1(6) . . . . ?
S2 C8 C13 C12 -177.0(3) . . . . ?
C11 C12 C13 C8 -0.3(6) . . . . ?
Cu2 O2 C15 O1 -7.3(5) . . . . ?
Cu2 O2 C15 C16 172.1(3) . . . . ?
Cu1 O1 C15 O2 2.1(5) . . . . ?
Cu1 O1 C15 C16 -177.3(3) . . . . ?
Cu3 O6 C17 O7 7.0(5) . . . . ?
Cu3 O6 C17 C18 -171.3(2) . . . . ?
Cu4 O7 C17 O6 4.5(5) . . . . ?
Cu4 O7 C17 C18 -177.2(2) . . . . ?



#==============================================================================
# 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_150321f1
_database_code_depnum_ccdc_archive 'CCDC 1493062'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H34 Cu3 O16 S2'
_chemical_formula_moiety         'C20 H34 Cu3 O16 S2'
_chemical_formula_weight         785.24
_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                   5.766(2)
_cell_length_b                   8.639(4)
_cell_length_c                   15.848(7)
_cell_angle_alpha                101.400(7)
_cell_angle_beta                 99.046(9)
_cell_angle_gamma                100.390(11)
_cell_volume                     745.8(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2757
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      25.00
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             401.00
_exptl_absorpt_coefficient_mu    2.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_T_max  0.628

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

_diffrn_ambient_temperature      150
_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            5999
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_theta_max         25.076
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_full        25.076
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_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_%        ?
_reflns_number_total             2546
_reflns_number_gt                2143
_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          0.0466
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1254
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2546
_refine_ls_number_parameters     202
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0867P)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          0.001
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.71
_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 0.5000 1.0000 0.0161(2) Uani 1 2 d S . P . .
Cu2 Cu 0.45560(8) 0.58076(6) 0.92627(3) 0.0174(2) Uani 1 1 d . . . . .
S3 S 0.16842(17) 0.99067(13) 0.82983(7) 0.0179(3) Uani 1 1 d . . . . .
O4 O 0.0999(6) 1.1449(4) 0.8475(2) 0.0307(8) Uani 1 1 d . . . . .
O5 O 0.2857(5) 0.4133(3) 0.97567(19) 0.0164(6) Uani 1 1 d D . . . .
H5 H 0.229(8) 0.329(4) 0.942(3) 0.020 Uiso 1 1 d D U . . .
O6 O 0.6194(6) 0.7615(5) 0.8865(3) 0.0428(10) Uani 1 1 d D . . . .
H6A H 0.759(5) 0.803(7) 0.893(4) 0.051 Uiso 1 1 d D U . . .
H6B H 0.548(10) 0.830(5) 0.880(4) 0.051 Uiso 1 1 d D U . . .
O7 O 0.2683(5) 0.7544(4) 1.0144(2) 0.0205(7) Uani 1 1 d D . . . .
H7A H 0.225(8) 0.809(5) 0.983(3) 0.025 Uiso 1 1 d D U . . .
H7B H 0.314(8) 0.811(5) 1.0625(18) 0.025 Uiso 1 1 d D U . . .
O8 O 0.4263(5) 1.0041(4) 0.8358(2) 0.0246(7) Uani 1 1 d . . . . .
O9 O 0.0761(5) 0.8839(4) 0.8836(2) 0.0281(8) Uani 1 1 d . . . . .
O10 O 0.2103(6) 0.5283(4) 0.8206(2) 0.0255(7) Uani 1 1 d . . . . .
O11 O 0.1220(5) 0.5171(4) 1.12340(19) 0.0220(7) Uani 1 1 d . . . . .
C12 C -0.0132(7) 0.4887(5) 0.8134(3) 0.0191(9) Uani 1 1 d . . . . .
C13 C 0.0296(8) 0.7257(6) 0.5797(3) 0.0281(11) Uani 1 1 d . . . . .
H13 H 0.1081 0.6590 0.5441 0.034 Uiso 1 1 calc R U . . .
C14 C 0.0287(8) 0.8959(5) 0.7198(3) 0.0201(9) Uani 1 1 d . . . . .
C15 C -0.2999(8) 0.8511(7) 0.5987(3) 0.0342(12) Uani 1 1 d . . . . .
H15 H -0.4514 0.8700 0.5751 0.041 Uiso 1 1 calc R U . . .
C16 C -0.1946(8) 0.9230(6) 0.6859(3) 0.0286(11) Uani 1 1 d . . . . .
H16 H -0.2731 0.9894 0.7218 0.034 Uiso 1 1 calc R U . . .
C17 C 0.1378(8) 0.7967(6) 0.6674(3) 0.0268(10) Uani 1 1 d . . . . .
H17 H 0.2882 0.7765 0.6911 0.032 Uiso 1 1 calc R U . . .
C18 C -0.1903(9) 0.7517(6) 0.5444(3) 0.0315(12) Uani 1 1 d . . . . .
C19 C -0.3044(10) 0.6849(7) 0.4489(3) 0.0396(14) Uani 1 1 d . . . . .
H19A H -0.4817 0.6635 0.4423 0.048 Uiso 1 1 calc R U . . .
H19B H -0.2596 0.5806 0.4282 0.048 Uiso 1 1 calc R U . . .
C20 C -0.1708(9) 0.4454(7) 0.7240(3) 0.0352(13) Uani 1 1 d . . . . .
H20A H -0.3397 0.4175 0.7290 0.042 Uiso 1 1 calc R U . . .
H20B H -0.1464 0.5379 0.6966 0.042 Uiso 1 1 calc R U . . .
H20C H -0.1297 0.3526 0.6876 0.042 Uiso 1 1 calc R U . . .
C21 C -0.2286(11) 0.7982(8) 0.3926(4) 0.0499(16) Uani 1 1 d . . . . .
H21A H -0.3072 0.7497 0.3311 0.060 Uiso 1 1 calc R U . . .
H21B H -0.2756 0.9009 0.4120 0.060 Uiso 1 1 calc R U . . .
H21C H -0.0535 0.8180 0.3978 0.060 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    'SIR2011 (Burla, et al., 2012)'
_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 O11 1.938(3) . ?
Cu1 O11 1.938(3) 2_567 ?
Cu1 O5 1.988(3) 2_567 ?
Cu1 O5 1.988(3) . ?
Cu1 O7 2.396(3) . ?
Cu1 O7 2.396(3) 2_567 ?
Cu2 O10 1.932(3) . ?
Cu2 O6 1.942(4) . ?
Cu2 O5 1.960(3) . ?
Cu2 O5 1.963(3) 2_667 ?
Cu2 O7 2.366(3) . ?
Cu2 Cu2 2.9733(14) 2_667 ?
S3 O4 1.445(4) . ?
S3 O8 1.457(3) . ?
S3 O9 1.461(3) . ?
S3 C14 1.766(4) . ?
O5 Cu2 1.963(3) 2_667 ?
O5 H5 0.79(2) . ?
O6 H6A 0.80(2) . ?
O6 H6B 0.79(2) . ?
O7 H7A 0.80(2) . ?
O7 H7B 0.80(2) . ?
O10 C12 1.253(5) . ?
O11 C12 1.267(5) 2_567 ?
C12 O11 1.267(5) 2_567 ?
C12 C20 1.496(6) . ?
C13 C18 1.379(7) . ?
C13 C17 1.395(6) . ?
C13 H13 0.9500 . ?
C14 C17 1.377(7) . ?
C14 C16 1.394(6) . ?
C15 C16 1.388(7) . ?
C15 C18 1.396(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.504(7) . ?
C19 C21 1.504(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
O11 Cu1 O11 180.0 . 2_567 ?
O11 Cu1 O5 92.70(12) . 2_567 ?
O11 Cu1 O5 87.30(12) 2_567 2_567 ?
O11 Cu1 O5 87.30(12) . . ?
O11 Cu1 O5 92.70(12) 2_567 . ?
O5 Cu1 O5 180.0 2_567 . ?
O11 Cu1 O7 87.73(12) . . ?
O11 Cu1 O7 92.26(12) 2_567 . ?
O5 Cu1 O7 97.31(12) 2_567 . ?
O5 Cu1 O7 82.69(12) . . ?
O11 Cu1 O7 92.27(12) . 2_567 ?
O11 Cu1 O7 87.73(12) 2_567 2_567 ?
O5 Cu1 O7 82.69(12) 2_567 2_567 ?
O5 Cu1 O7 97.31(12) . 2_567 ?
O7 Cu1 O7 180.0 . 2_567 ?
O10 Cu2 O6 89.15(16) . . ?
O10 Cu2 O5 93.18(13) . . ?
O6 Cu2 O5 174.63(17) . . ?
O10 Cu2 O5 167.63(13) . 2_667 ?
O6 Cu2 O5 97.17(15) . 2_667 ?
O5 Cu2 O5 81.46(12) . 2_667 ?
O10 Cu2 O7 96.90(13) . . ?
O6 Cu2 O7 90.86(15) . . ?
O5 Cu2 O7 84.06(12) . . ?
O5 Cu2 O7 93.64(12) 2_667 . ?
O10 Cu2 Cu2 132.97(10) . 2_667 ?
O6 Cu2 Cu2 137.63(12) . 2_667 ?
O5 Cu2 Cu2 40.77(8) . 2_667 ?
O5 Cu2 Cu2 40.70(8) 2_667 2_667 ?
O7 Cu2 Cu2 88.49(8) . 2_667 ?
O4 S3 O8 113.73(19) . . ?
O4 S3 O9 112.7(2) . . ?
O8 S3 O9 110.70(19) . . ?
O4 S3 C14 105.8(2) . . ?
O8 S3 C14 106.9(2) . . ?
O9 S3 C14 106.5(2) . . ?
Cu2 O5 Cu2 98.54(12) . 2_667 ?
Cu2 O5 Cu1 101.71(14) . . ?
Cu2 O5 Cu1 119.59(15) 2_667 . ?
Cu2 O5 H5 116(4) . . ?
Cu2 O5 H5 117(4) 2_667 . ?
Cu1 O5 H5 103(4) . . ?
Cu2 O6 H6A 132(5) . . ?
Cu2 O6 H6B 117(5) . . ?
H6A O6 H6B 106(7) . . ?
Cu2 O7 Cu1 80.04(10) . . ?
Cu2 O7 H7A 103(4) . . ?
Cu1 O7 H7A 116(4) . . ?
Cu2 O7 H7B 131(4) . . ?
Cu1 O7 H7B 117(4) . . ?
H7A O7 H7B 107(6) . . ?
C12 O10 Cu2 128.0(3) . . ?
C12 O11 Cu1 130.8(3) 2_567 . ?
O10 C12 O11 125.3(4) . 2_567 ?
O10 C12 C20 119.1(4) . . ?
O11 C12 C20 115.6(4) 2_567 . ?
C18 C13 C17 120.5(5) . . ?
C18 C13 H13 119.7 . . ?
C17 C13 H13 119.7 . . ?
C17 C14 C16 120.0(4) . . ?
C17 C14 S3 120.9(4) . . ?
C16 C14 S3 119.1(4) . . ?
C16 C15 C18 122.1(5) . . ?
C16 C15 H15 118.9 . . ?
C18 C15 H15 118.9 . . ?
C15 C16 C14 118.6(5) . . ?
C15 C16 H16 120.7 . . ?
C14 C16 H16 120.7 . . ?
C14 C17 C13 120.7(4) . . ?
C14 C17 H17 119.7 . . ?
C13 C17 H17 119.7 . . ?
C13 C18 C15 118.1(4) . . ?
C13 C18 C19 121.7(5) . . ?
C15 C18 C19 120.1(5) . . ?
C18 C19 C21 112.4(4) . . ?
C18 C19 H19A 109.1 . . ?
C21 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C21 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Cu2 O10 C12 O11 3.4(7) . . . 2_567 ?
Cu2 O10 C12 C20 -177.2(3) . . . . ?
O4 S3 C14 C17 146.5(4) . . . . ?
O8 S3 C14 C17 25.0(4) . . . . ?
O9 S3 C14 C17 -93.4(4) . . . . ?
O4 S3 C14 C16 -33.2(4) . . . . ?
O8 S3 C14 C16 -154.7(4) . . . . ?
O9 S3 C14 C16 86.9(4) . . . . ?
C18 C15 C16 C14 0.6(7) . . . . ?
C17 C14 C16 C15 -1.3(7) . . . . ?
S3 C14 C16 C15 178.4(4) . . . . ?
C16 C14 C17 C13 1.5(7) . . . . ?
S3 C14 C17 C13 -178.2(4) . . . . ?
C18 C13 C17 C14 -1.0(7) . . . . ?
C17 C13 C18 C15 0.2(7) . . . . ?
C17 C13 C18 C19 176.4(4) . . . . ?
C16 C15 C18 C13 -0.1(7) . . . . ?
C16 C15 C18 C19 -176.3(5) . . . . ?
C13 C18 C19 C21 -88.7(7) . . . . ?
C15 C18 C19 C21 87.3(6) . . . . ?

#==============================================================================
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 O4 . . 1_545 2.684(4) 0.79(3) 1.90(3) 170(4) no
O6 H6A O9 . . 1_655 2.666(5) 0.80(3) 1.88(3) 168(6) no
O6 H6B O8 . . . 2.739(6) 0.79(6) 1.98(6) 162(7) no
O7 H7A O9 . . . 2.724(5) 0.80(5) 1.95(5) 164(4) no
O7 H7B O8 . . 2_677 2.914(4) 0.80(3) 2.18(3) 154(4) 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_131127f2
_database_code_depnum_ccdc_archive 'CCDC 1493063'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C24 H32 Cu3 O17 S2'
_chemical_formula_moiety         'C24 H32 Cu3 O17 S2'
_chemical_formula_weight         847.26
_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                   17.2932(13)
_cell_length_b                   5.7712(2)
_cell_length_c                   31.2089(19)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.088(4)
_cell_angle_gamma                90.0000
_cell_volume                     3110.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6900
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1724.00
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, ????)'
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_T_max  0.894

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

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_reflns_number            22473
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       34
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7012
_reflns_number_gt                5179
_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          0.0756
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1018
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7012
_refine_ls_number_parameters     445
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0409P)²+3.9461P] 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         0.63
_refine_diff_density_min         -0.87
_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 0.71460(3) 0.81348(8) 0.44597(2) 0.01489(13) Uani 1 1 d . . . . .
Cu2 Cu 0.75809(3) 0.34555(8) 0.48786(2) 0.01418(12) Uani 1 1 d . . . . .
Cu3 Cu 0.79883(3) -0.12092(8) 0.53010(2) 0.01562(13) Uani 1 1 d . . . . .
S4 S 0.97927(6) 0.74147(17) 0.41612(3) 0.0169(2) Uani 1 1 d . . . . .
S5 S 0.52686(7) 0.96820(19) 0.09331(4) 0.0218(2) Uani 1 1 d . . . . .
O6 O 0.79889(16) -0.3332(5) 0.48126(9) 0.0146(6) Uani 1 1 d D . . . .
H6 H 0.8365(18) -0.353(8) 0.4690(13) 0.018 Uiso 1 1 d D U . . .
O7 O 0.71512(16) 1.0262(5) 0.49440(9) 0.0151(6) Uani 1 1 d D . . . .
H7 H 0.6741(15) 1.034(8) 0.5038(14) 0.018 Uiso 1 1 d D U . . .
O8 O 0.76235(16) 0.4100(5) 0.54901(9) 0.0170(6) Uani 1 1 d . . . . .
O9 O 0.75744(17) 0.2798(5) 0.42684(9) 0.0182(6) Uani 1 1 d . . . . .
O10 O 0.73434(18) 0.6281(5) 0.39643(9) 0.0209(7) Uani 1 1 d . . . . .
O11 O 0.63784(17) 0.5406(5) 0.48170(10) 0.0182(6) Uani 1 1 d D . . . .
H11A H 0.607(2) 0.493(8) 0.4635(11) 0.022 Uiso 1 1 d D U . . .
H11B H 0.619(3) 0.537(8) 0.5046(9) 0.022 Uiso 1 1 d D U . . .
O12 O 0.77737(17) 0.0596(5) 0.57986(9) 0.0207(7) Uani 1 1 d . . . . .
O13 O 0.62442(18) 0.9410(5) 0.41275(10) 0.0211(7) Uani 1 1 d D . . . .
H13A H 0.5873(19) 0.861(7) 0.4144(16) 0.025 Uiso 1 1 d D U . . .
H13B H 0.606(3) 1.056(5) 0.4214(15) 0.025 Uiso 1 1 d D U . . .
O14 O 0.87819(18) 0.1519(5) 0.49404(10) 0.0204(7) Uani 1 1 d D . . . .
H14A H 0.908(2) 0.211(8) 0.5113(12) 0.025 Uiso 1 1 d D U . . .
H14B H 0.894(3) 0.123(9) 0.4722(9) 0.025 Uiso 1 1 d D U . . .
O15 O 0.96627(17) 0.9886(5) 0.42178(10) 0.0227(7) Uani 1 1 d . . . . .
O16 O 1.06018(17) 0.6805(5) 0.42632(10) 0.0214(7) Uani 1 1 d . . . . .
O17 O 0.92712(17) 0.5958(5) 0.43872(10) 0.0236(7) Uani 1 1 d . . . . .
O18 O 0.8932(2) -0.2383(5) 0.56056(12) 0.0289(8) Uani 1 1 d D . . . .
H18A H 0.904(3) -0.371(4) 0.5580(17) 0.035 Uiso 1 1 d D U . . .
H18B H 0.929(2) -0.157(8) 0.5590(17) 0.035 Uiso 1 1 d D U . . .
O19 O 0.51533(19) 1.2182(5) 0.09516(10) 0.0282(8) Uani 1 1 d . . . . .
O20 O 0.4536(2) 0.8480(6) 0.08498(12) 0.0370(9) Uani 1 1 d . . . . .
O21 O 0.5720(2) 0.0614(7) 0.52243(12) 0.0429(10) Uani 1 1 d . . . . .
O22 O 0.5844(2) 0.9002(7) 0.06358(11) 0.0435(10) Uani 1 1 d . . . . .
C23 C 0.7525(2) 0.4156(7) 0.39518(13) 0.0185(9) Uani 1 1 d . . . . .
C24 C 0.7684(2) 0.2775(7) 0.58098(13) 0.0167(9) Uani 1 1 d . . . . .
C25 C 0.5833(2) 0.9589(7) 0.22051(14) 0.0189(9) Uani 1 1 d . . . . .
C26 C 0.9611(2) 0.6766(7) 0.36084(14) 0.0180(9) Uani 1 1 d . . . . .
C27 C 0.6225(2) 0.7421(7) 0.22559(15) 0.0207(9) Uani 1 1 d . . . . .
C28 C 0.5642(2) 0.8829(7) 0.14483(13) 0.0184(9) Uani 1 1 d . . . . .
C29 C 0.8930(3) 0.7612(8) 0.29325(14) 0.0218(9) Uani 1 1 d . . . . .
C30 C 0.6040(3) 0.6687(7) 0.14923(14) 0.0220(10) Uani 1 1 d . . . . .
H30 H 0.6107 0.5728 0.1250 0.026 Uiso 1 1 calc R U . . .
C31 C 0.5546(2) 1.0232(7) 0.17896(14) 0.0212(9) Uani 1 1 d . . . . .
H31 H 0.5282 1.1665 0.1749 0.025 Uiso 1 1 calc R U . . .
C32 C 0.9196(3) 0.5474(8) 0.27630(14) 0.0241(10) Uani 1 1 d . . . . .
C33 C 0.9150(3) 0.8209(7) 0.33599(14) 0.0208(9) Uani 1 1 d . . . . .
H33 H 0.8976 0.9627 0.3476 0.025 Uiso 1 1 calc R U . . .
C34 C 0.5722(3) 1.0967(8) 0.25695(15) 0.0247(10) Uani 1 1 d . . . . .
H34 H 0.5461 1.2411 0.2537 0.030 Uiso 1 1 calc R U . . .
C35 C 0.9887(3) 0.4672(7) 0.34440(15) 0.0255(10) Uani 1 1 d . . . . .
H35 H 1.0210 0.3688 0.3620 0.031 Uiso 1 1 calc R U . . .
C36 C 0.8439(3) 0.9046(8) 0.26619(15) 0.0276(11) Uani 1 1 d . . . . .
H36 H 0.8261 1.0483 0.2767 0.033 Uiso 1 1 calc R U . . .
C37 C 0.9688(3) 0.4064(8) 0.30312(15) 0.0278(11) Uani 1 1 d . . . . .
H37 H 0.9884 0.2662 0.2920 0.033 Uiso 1 1 calc R U . . .
C38 C 0.6326(3) 0.6029(7) 0.18908(14) 0.0245(10) Uani 1 1 d . . . . .
H38 H 0.6599 0.4606 0.1923 0.029 Uiso 1 1 calc R U . . .
C39 C 0.6495(3) 0.6752(8) 0.26712(15) 0.0290(11) Uani 1 1 d . . . . .
H39 H 0.6765 0.5327 0.2709 0.035 Uiso 1 1 calc R U . . .
C40 C 0.7647(3) 0.3863(8) 0.62466(14) 0.0300(11) Uani 1 1 d . . . . .
H40A H 0.7701 0.2657 0.6467 0.036 Uiso 1 1 calc R U . . .
H40B H 0.8068 0.4990 0.6290 0.036 Uiso 1 1 calc R U . . .
H40C H 0.7148 0.4650 0.6267 0.036 Uiso 1 1 calc R U . . .
C41 C 0.8491(3) 0.6250(9) 0.20887(15) 0.0316(12) Uani 1 1 d . . . . .
H41 H 0.8340 0.5806 0.1803 0.038 Uiso 1 1 calc R U . . .
C42 C 0.7699(3) 0.3163(8) 0.35265(14) 0.0283(11) Uani 1 1 d . . . . .
H42A H 0.7642 0.4370 0.3306 0.034 Uiso 1 1 calc R U . . .
H42B H 0.8231 0.2572 0.3539 0.034 Uiso 1 1 calc R U . . .
H42C H 0.7339 0.1893 0.3455 0.034 Uiso 1 1 calc R U . . .
C43 C 0.8959(3) 0.4848(9) 0.23370(15) 0.0300(11) Uani 1 1 d . . . . .
H43 H 0.9132 0.3423 0.2223 0.036 Uiso 1 1 calc R U . . .
C44 C 0.5983(3) 1.0255(9) 0.29668(15) 0.0290(11) Uani 1 1 d . . . . .
H44 H 0.5900 1.1199 0.3210 0.035 Uiso 1 1 calc R U . . .
C45 C 0.6377(3) 0.8112(9) 0.30207(15) 0.0306(11) Uani 1 1 d . . . . .
H45 H 0.6559 0.7622 0.3299 0.037 Uiso 1 1 calc R U . . .
C46 C 0.8226(3) 0.8373(9) 0.22550(16) 0.0325(12) Uani 1 1 d . . . . .
H46 H 0.7895 0.9339 0.2080 0.039 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 2014/5 (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 O10 1.926(3) . ?
Cu1 O7 1.947(3) . ?
Cu1 O13 1.968(3) . ?
Cu1 O6 1.970(3) 1_565 ?
Cu1 O11 2.376(3) . ?
Cu1 Cu3 2.9573(7) 1_565 ?
Cu2 O9 1.941(3) . ?
Cu2 O8 1.942(3) . ?
Cu2 O6 1.998(3) 1_565 ?
Cu2 O7 2.002(3) 1_545 ?
Cu2 O14 2.357(3) . ?
Cu2 O11 2.363(3) . ?
Cu3 O12 1.923(3) . ?
Cu3 O6 1.955(3) . ?
Cu3 O18 1.965(3) . ?
Cu3 O7 1.971(3) 1_545 ?
Cu3 O14 2.407(3) . ?
Cu3 Cu1 2.9572(7) 1_545 ?
S4 O17 1.445(3) . ?
S4 O15 1.456(3) . ?
S4 O16 1.461(3) . ?
S4 C26 1.777(4) . ?
S5 O22 1.451(4) . ?
S5 O20 1.455(3) . ?
S5 O19 1.458(3) . ?
S5 C28 1.770(4) . ?
O6 Cu1 1.970(3) 1_545 ?
O6 Cu2 1.998(3) 1_545 ?
O6 H6 0.781(19) . ?
O7 Cu3 1.971(3) 1_565 ?
O7 Cu2 2.002(3) 1_565 ?
O7 H7 0.784(19) . ?
O8 C24 1.257(5) . ?
O9 C23 1.260(5) . ?
O10 C23 1.267(5) . ?
O11 H11A 0.808(19) . ?
O11 H11B 0.799(19) . ?
O12 C24 1.268(5) . ?
O13 H13A 0.794(19) . ?
O13 H13B 0.792(19) . ?
O14 H14A 0.796(19) . ?
O14 H14B 0.770(19) . ?
O18 H18A 0.797(19) . ?
O18 H18B 0.78(2) . ?
C23 C42 1.492(6) . ?
C24 C40 1.505(6) . ?
C25 C34 1.409(6) . ?
C25 C31 1.413(6) . ?
C25 C27 1.428(6) . ?
C26 C33 1.366(6) . ?
C26 C35 1.406(6) . ?
C27 C39 1.408(6) . ?
C27 C38 1.413(6) . ?
C28 C31 1.355(6) . ?
C28 C30 1.418(6) . ?
C29 C33 1.410(6) . ?
C29 C36 1.428(6) . ?
C29 C32 1.428(6) . ?
C30 C38 1.367(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C43 1.417(6) . ?
C32 C37 1.418(6) . ?
C33 H33 0.9500 . ?
C34 C44 1.360(6) . ?
C34 H34 0.9500 . ?
C35 C37 1.361(6) . ?
C35 H35 0.9500 . ?
C36 C46 1.360(7) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C45 1.368(7) . ?
C39 H39 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 C43 1.358(7) . ?
C41 C46 1.416(7) . ?
C41 H41 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43 0.9500 . ?
C44 C45 1.418(7) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

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
O10 Cu1 O7 168.53(13) . . ?
O10 Cu1 O13 87.38(13) . . ?
O7 Cu1 O13 98.25(12) . . ?
O10 Cu1 O6 93.01(12) . 1_565 ?
O7 Cu1 O6 82.22(12) . 1_565 ?
O13 Cu1 O6 175.16(13) . 1_565 ?
O10 Cu1 O11 97.83(12) . . ?
O7 Cu1 O11 91.89(11) . . ?
O13 Cu1 O11 92.75(12) . . ?
O6 Cu1 O11 82.42(11) 1_565 . ?
O10 Cu1 Cu3 133.14(9) . 1_565 ?
O7 Cu1 Cu3 41.29(8) . 1_565 ?
O13 Cu1 Cu3 139.30(9) . 1_565 ?
O6 Cu1 Cu3 40.93(8) 1_565 1_565 ?
O11 Cu1 Cu3 85.94(7) . 1_565 ?
O9 Cu2 O8 178.14(12) . . ?
O9 Cu2 O6 93.65(12) . 1_565 ?
O8 Cu2 O6 85.91(12) . 1_565 ?
O9 Cu2 O7 86.41(12) . 1_545 ?
O8 Cu2 O7 94.07(12) . 1_545 ?
O6 Cu2 O7 178.89(12) 1_565 1_545 ?
O9 Cu2 O14 86.91(11) . . ?
O8 Cu2 O14 91.36(11) . . ?
O6 Cu2 O14 97.69(11) 1_565 . ?
O7 Cu2 O14 83.42(11) 1_545 . ?
O9 Cu2 O11 93.13(11) . . ?
O8 Cu2 O11 88.59(11) . . ?
O6 Cu2 O11 82.17(11) 1_565 . ?
O7 Cu2 O11 96.72(11) 1_545 . ?
O14 Cu2 O11 179.85(12) . . ?
O12 Cu3 O6 167.73(13) . . ?
O12 Cu3 O18 89.28(14) . . ?
O6 Cu3 O18 97.23(13) . . ?
O12 Cu3 O7 93.18(12) . 1_545 ?
O6 Cu3 O7 81.98(12) . 1_545 ?
O18 Cu3 O7 171.09(14) . 1_545 ?
O12 Cu3 O14 99.38(12) . . ?
O6 Cu3 O14 91.22(11) . . ?
O18 Cu3 O14 88.40(13) . . ?
O7 Cu3 O14 82.75(11) 1_545 . ?
O12 Cu3 Cu1 132.78(9) . 1_545 ?
O6 Cu3 Cu1 41.30(8) . 1_545 ?
O18 Cu3 Cu1 137.91(11) . 1_545 ?
O7 Cu3 Cu1 40.68(8) 1_545 1_545 ?
O14 Cu3 Cu1 86.26(7) . 1_545 ?
O17 S4 O15 113.98(19) . . ?
O17 S4 O16 111.67(18) . . ?
O15 S4 O16 111.21(18) . . ?
O17 S4 C26 105.61(19) . . ?
O15 S4 C26 107.67(19) . . ?
O16 S4 C26 106.14(19) . . ?
O22 S5 O20 112.2(2) . . ?
O22 S5 O19 113.1(2) . . ?
O20 S5 O19 111.1(2) . . ?
O22 S5 C28 106.0(2) . . ?
O20 S5 C28 107.5(2) . . ?
O19 S5 C28 106.5(2) . . ?
Cu3 O6 Cu1 97.76(12) . 1_545 ?
Cu3 O6 Cu2 119.08(14) . 1_545 ?
Cu1 O6 Cu2 101.63(12) 1_545 1_545 ?
Cu3 O6 H6 121(4) . . ?
Cu1 O6 H6 113(3) 1_545 . ?
Cu2 O6 H6 103(3) 1_545 . ?
Cu1 O7 Cu3 98.03(12) . 1_565 ?
Cu1 O7 Cu2 119.20(14) . 1_565 ?
Cu3 O7 Cu2 100.89(13) 1_565 1_565 ?
Cu1 O7 H7 111(3) . . ?
Cu3 O7 H7 118(3) 1_565 . ?
Cu2 O7 H7 110(4) 1_565 . ?
C24 O8 Cu2 131.4(3) . . ?
C23 O9 Cu2 130.1(3) . . ?
C23 O10 Cu1 128.1(3) . . ?
Cu2 O11 Cu1 80.94(10) . . ?
Cu2 O11 H11A 116(3) . . ?
Cu1 O11 H11A 105(3) . . ?
Cu2 O11 H11B 108(3) . . ?
Cu1 O11 H11B 134(4) . . ?
H11A O11 H11B 110(5) . . ?
C24 O12 Cu3 126.1(3) . . ?
Cu1 O13 H13A 112(4) . . ?
Cu1 O13 H13B 117(4) . . ?
H13A O13 H13B 97(5) . . ?
Cu2 O14 Cu3 80.00(10) . . ?
Cu2 O14 H14A 112(4) . . ?
Cu3 O14 H14A 109(4) . . ?
Cu2 O14 H14B 113(4) . . ?
Cu3 O14 H14B 121(4) . . ?
H14A O14 H14B 116(5) . . ?
Cu3 O18 H18A 119(4) . . ?
Cu3 O18 H18B 114(4) . . ?
H18A O18 H18B 112(5) . . ?
O9 C23 O10 125.7(4) . . ?
O9 C23 C42 116.8(4) . . ?
O10 C23 C42 117.5(4) . . ?
O8 C24 O12 125.9(4) . . ?
O8 C24 C40 117.3(4) . . ?
O12 C24 C40 116.7(4) . . ?
C34 C25 C31 122.4(4) . . ?
C34 C25 C27 119.3(4) . . ?
C31 C25 C27 118.2(4) . . ?
C33 C26 C35 121.1(4) . . ?
C33 C26 S4 119.4(3) . . ?
C35 C26 S4 119.3(3) . . ?
C39 C27 C38 122.5(4) . . ?
C39 C27 C25 118.3(4) . . ?
C38 C27 C25 119.2(4) . . ?
C31 C28 C30 121.6(4) . . ?
C31 C28 S5 119.6(3) . . ?
C30 C28 S5 118.8(3) . . ?
C33 C29 C36 122.6(4) . . ?
C33 C29 C32 119.0(4) . . ?
C36 C29 C32 118.3(4) . . ?
C38 C30 C28 118.7(4) . . ?
C38 C30 H30 120.7 . . ?
C28 C30 H30 120.7 . . ?
C28 C31 C25 120.9(4) . . ?
C28 C31 H31 119.6 . . ?
C25 C31 H31 119.6 . . ?
C43 C32 C37 122.8(4) . . ?
C43 C32 C29 119.0(4) . . ?
C37 C32 C29 118.2(4) . . ?
C26 C33 C29 120.5(4) . . ?
C26 C33 H33 119.7 . . ?
C29 C33 H33 119.7 . . ?
C44 C34 C25 120.8(4) . . ?
C44 C34 H34 119.6 . . ?
C25 C34 H34 119.6 . . ?
C37 C35 C26 119.6(4) . . ?
C37 C35 H35 120.2 . . ?
C26 C35 H35 120.2 . . ?
C46 C36 C29 120.6(5) . . ?
C46 C36 H36 119.7 . . ?
C29 C36 H36 119.7 . . ?
C35 C37 C32 121.6(4) . . ?
C35 C37 H37 119.2 . . ?
C32 C37 H37 119.2 . . ?
C30 C38 C27 121.4(4) . . ?
C30 C38 H38 119.3 . . ?
C27 C38 H38 119.3 . . ?
C45 C39 C27 121.3(4) . . ?
C45 C39 H39 119.3 . . ?
C27 C39 H39 119.3 . . ?
C24 C40 H40A 109.5 . . ?
C24 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C24 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C43 C41 C46 120.1(5) . . ?
C43 C41 H41 120.0 . . ?
C46 C41 H41 120.0 . . ?
C23 C42 H42A 109.5 . . ?
C23 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C23 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 C32 121.1(5) . . ?
C41 C43 H43 119.5 . . ?
C32 C43 H43 119.5 . . ?
C34 C44 C45 120.4(5) . . ?
C34 C44 H44 119.8 . . ?
C45 C44 H44 119.8 . . ?
C39 C45 C44 119.8(4) . . ?
C39 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C36 C46 C41 120.8(5) . . ?
C36 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu2 O9 C23 O10 -12.0(6) . . . . ?
Cu2 O9 C23 C42 167.7(3) . . . . ?
Cu1 O10 C23 O9 3.7(6) . . . . ?
Cu1 O10 C23 C42 -176.0(3) . . . . ?
Cu2 O8 C24 O12 3.9(7) . . . . ?
Cu2 O8 C24 C40 -176.1(3) . . . . ?
Cu3 O12 C24 O8 9.5(6) . . . . ?
Cu3 O12 C24 C40 -170.5(3) . . . . ?
O17 S4 C26 C33 99.6(4) . . . . ?
O15 S4 C26 C33 -22.6(4) . . . . ?
O16 S4 C26 C33 -141.8(4) . . . . ?
O17 S4 C26 C35 -74.8(4) . . . . ?
O15 S4 C26 C35 163.1(3) . . . . ?
O16 S4 C26 C35 43.9(4) . . . . ?
C34 C25 C27 C39 -0.8(6) . . . . ?
C31 C25 C27 C39 -178.5(4) . . . . ?
C34 C25 C27 C38 179.2(4) . . . . ?
C31 C25 C27 C38 1.4(6) . . . . ?
O22 S5 C28 C31 140.5(4) . . . . ?
O20 S5 C28 C31 -99.3(4) . . . . ?
O19 S5 C28 C31 19.8(4) . . . . ?
O22 S5 C28 C30 -39.1(4) . . . . ?
O20 S5 C28 C30 81.0(4) . . . . ?
O19 S5 C28 C30 -159.9(3) . . . . ?
C31 C28 C30 C38 0.5(7) . . . . ?
S5 C28 C30 C38 -179.8(4) . . . . ?
C30 C28 C31 C25 -0.8(7) . . . . ?
S5 C28 C31 C25 179.6(3) . . . . ?
C34 C25 C31 C28 -177.9(4) . . . . ?
C27 C25 C31 C28 -0.2(6) . . . . ?
C33 C29 C32 C43 178.5(4) . . . . ?
C36 C29 C32 C43 -0.6(6) . . . . ?
C33 C29 C32 C37 -1.5(6) . . . . ?
C36 C29 C32 C37 179.4(4) . . . . ?
C35 C26 C33 C29 0.9(7) . . . . ?
S4 C26 C33 C29 -173.3(3) . . . . ?
C36 C29 C33 C26 179.1(4) . . . . ?
C32 C29 C33 C26 0.0(7) . . . . ?
C31 C25 C34 C44 177.7(4) . . . . ?
C27 C25 C34 C44 0.0(7) . . . . ?
C33 C26 C35 C37 -0.4(7) . . . . ?
S4 C26 C35 C37 173.8(4) . . . . ?
C33 C29 C36 C46 -178.3(4) . . . . ?
C32 C29 C36 C46 0.7(7) . . . . ?
C26 C35 C37 C32 -1.2(7) . . . . ?
C43 C32 C37 C35 -177.9(5) . . . . ?
C29 C32 C37 C35 2.1(7) . . . . ?
C28 C30 C38 C27 0.8(7) . . . . ?
C39 C27 C38 C30 178.2(4) . . . . ?
C25 C27 C38 C30 -1.7(7) . . . . ?
C38 C27 C39 C45 -178.8(5) . . . . ?
C25 C27 C39 C45 1.1(7) . . . . ?
C46 C41 C43 C32 -0.3(7) . . . . ?
C37 C32 C43 C41 -179.6(5) . . . . ?
C29 C32 C43 C41 0.4(7) . . . . ?
C25 C34 C44 C45 0.4(7) . . . . ?
C27 C39 C45 C44 -0.7(7) . . . . ?
C34 C44 C45 C39 -0.1(7) . . . . ?
C29 C36 C46 C41 -0.7(7) . . . . ?
C43 C41 C46 C36 0.5(7) . . . . ?

#==============================================================================
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 H6 O17 . . 1_545 2.677(4) 0.78(4) 1.90(4) 179(4) no
O7 H7 O21 . . 1_565 2.676(5) 0.78(3) 1.89(3) 176(4) no
O11 H11A O20 . . 2_645 2.777(5) 0.81(4) 1.98(4) 170(4) no
O11 H11B O22 . . 4_576 2.785(5) 0.80(3) 2.00(3) 167(5) no
O13 H13A O19 . . 2_645 2.737(4) 0.79(4) 1.97(3) 164(4) no
O13 H13B O20 . . 2_655 2.712(4) 0.79(4) 1.98(4) 154(4) no
O14 H14A O16 . . 3_766 2.822(4) 0.80(4) 2.09(4) 152(4) no
O14 H14B O15 . . 1_545 2.943(4) 0.77(3) 2.20(4) 163(4) no
O18 H18A O16 . . 3_756 2.701(4) 0.80(3) 1.94(3) 159(5) no
O18 H18B O15 . . 3_766 2.853(4) 0.78(4) 2.11(4) 158(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_150228f2
_database_code_depnum_ccdc_archive 'CCDC 1493064'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H22 Cu3 O16 S2'
_chemical_formula_moiety         'C14 H22 Cu3 O16 S2'
_chemical_formula_weight         701.08
_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                   5.6096(2)
_cell_length_b                   8.9824(6)
_cell_length_c                   12.1172(9)
_cell_angle_alpha                86.288(6)
_cell_angle_beta                 77.183(6)
_cell_angle_gamma                77.676(6)
_cell_volume                     581.53(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2537
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             353.00
_exptl_absorpt_coefficient_mu    2.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_T_max  0.552

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

_diffrn_ambient_temperature      173
_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            5560
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         3.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2456
_reflns_number_gt                2245
_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          0.0333
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0752
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2456
_refine_ls_number_parameters     175
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0404P)²+0.3692P] 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         0.43
_refine_diff_density_min         -0.66
_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 1.0000 1.0000 0.01624(12) Uani 1 2 d S . P . .
Cu2 Cu 0.05108(5) 0.90292(3) 0.89817(2) 0.01737(11) Uani 1 1 d . . . . .
S3 S 0.87020(11) 0.45089(7) 0.79026(5) 0.01812(14) Uani 1 1 d . . . . .
O4 O 0.1910(3) 0.91879(19) 1.03041(15) 0.0167(3) Uani 1 1 d D . . . .
H4 H 0.196(5) 0.848(3) 1.071(2) 0.020 Uiso 1 1 d D U . . .
O5 O 0.7606(3) 0.7609(2) 1.00804(16) 0.0205(4) Uani 1 1 d D . . . .
H5A H 0.779(5) 0.714(3) 1.0632(19) 0.025 Uiso 1 1 d D U . . .
H5B H 0.740(6) 0.703(3) 0.966(2) 0.025 Uiso 1 1 d D U . . .
O6 O 0.5113(3) 0.9745(2) 0.83884(15) 0.0235(4) Uani 1 1 d . . . . .
O7 O 0.9208(3) 0.9264(2) 0.76188(16) 0.0254(4) Uani 1 1 d . . . . .
O8 O 0.7570(3) 0.6109(2) 0.81617(16) 0.0246(4) Uani 1 1 d . . . . .
O9 O 0.7217(3) 0.3480(2) 0.85406(16) 0.0259(4) Uani 1 1 d . . . . .
O10 O 0.2617(4) 0.7050(2) 0.8459(2) 0.0327(5) Uani 1 1 d D . . . .
H10A H 0.405(4) 0.679(4) 0.846(3) 0.039 Uiso 1 1 d D U . . .
H10B H 0.204(6) 0.631(3) 0.847(3) 0.039 Uiso 1 1 d D U . . .
O11 O 1.1295(3) 0.4174(2) 0.80220(16) 0.0293(4) Uani 1 1 d . . . . .
C12 C 0.6943(5) 0.9482(3) 0.7562(2) 0.0216(5) Uani 1 1 d . . . . .
C13 C 1.0072(4) 0.5108(3) 0.5569(2) 0.0188(5) Uani 1 1 d . . . . .
C14 C 0.8678(4) 0.4304(3) 0.6457(2) 0.0191(5) Uani 1 1 d . . . . .
C15 C 0.7220(5) 0.3377(3) 0.6221(2) 0.0279(6) Uani 1 1 d . . . . .
H15 H 0.6276 0.2873 0.6821 0.033 Uiso 1 1 calc R U . . .
C16 C 1.1565(5) 0.6107(3) 0.5778(2) 0.0269(6) Uani 1 1 d . . . . .
H16 H 1.1648 0.6272 0.6534 0.032 Uiso 1 1 calc R U . . .
C17 C 0.7112(6) 0.3166(4) 0.5101(3) 0.0333(7) Uani 1 1 d . . . . .
H17 H 0.6107 0.2509 0.4947 0.040 Uiso 1 1 calc R U . . .
C18 C 0.6374(6) 0.9365(4) 0.6422(2) 0.0340(7) Uani 1 1 d . . . . .
H18A H 0.4560 0.9557 0.6492 0.041 Uiso 1 1 calc R U . . .
H18B H 0.7070 1.0120 0.5900 0.041 Uiso 1 1 calc R U . . .
H18C H 0.7119 0.8340 0.6128 0.041 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SHELXT (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 1.9664(18) . ?
Cu1 O6 1.9664(18) 2_677 ?
Cu1 O4 1.9733(16) 2_677 ?
Cu1 O4 1.9733(16) . ?
Cu1 O5 2.3354(18) . ?
Cu1 O5 2.3354(18) 2_677 ?
Cu1 Cu2 3.0225(3) 2_577 ?
Cu1 Cu2 3.0225(3) 1_655 ?
Cu2 O7 1.9315(18) 1_455 ?
Cu2 O4 1.9594(18) . ?
Cu2 O10 1.968(2) . ?
Cu2 O4 1.9716(17) 2_577 ?
Cu2 O5 2.3997(19) 1_455 ?
Cu2 Cu2 2.9938(6) 2_577 ?
Cu2 Cu1 3.0225(3) 1_455 ?
S3 O9 1.4477(19) . ?
S3 O11 1.4589(18) . ?
S3 O8 1.4656(19) . ?
S3 C14 1.776(3) . ?
O4 Cu2 1.9716(17) 2_577 ?
O4 H4 0.779(18) . ?
O5 Cu2 2.3997(18) 1_655 ?
O5 H5A 0.780(18) . ?
O5 H5B 0.791(18) . ?
O6 C12 1.258(3) . ?
O7 C12 1.261(3) . ?
O7 Cu2 1.9314(18) 1_655 ?
O10 H10A 0.786(18) . ?
O10 H10B 0.794(18) . ?
C12 C18 1.500(4) . ?
C13 C16 1.419(3) . ?
C13 C13 1.427(5) 2_766 ?
C13 C14 1.435(3) . ?
C14 C15 1.367(4) . ?
C15 C17 1.399(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(4) 2_766 ?
C16 H16 0.9500 . ?
C17 C16 1.370(4) 2_766 ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 O6 180.0 . 2_677 ?
O6 Cu1 O4 93.77(7) . 2_677 ?
O6 Cu1 O4 86.23(7) 2_677 2_677 ?
O6 Cu1 O4 86.23(7) . . ?
O6 Cu1 O4 93.77(7) 2_677 . ?
O4 Cu1 O4 180.0 2_677 . ?
O6 Cu1 O5 90.84(7) . . ?
O6 Cu1 O5 89.16(7) 2_677 . ?
O4 Cu1 O5 85.78(7) 2_677 . ?
O4 Cu1 O5 94.22(7) . . ?
O6 Cu1 O5 89.16(7) . 2_677 ?
O6 Cu1 O5 90.84(7) 2_677 2_677 ?
O4 Cu1 O5 94.22(7) 2_677 2_677 ?
O4 Cu1 O5 85.78(7) . 2_677 ?
O5 Cu1 O5 180.0 . 2_677 ?
O6 Cu1 Cu2 103.77(5) . 2_577 ?
O6 Cu1 Cu2 76.23(5) 2_677 2_577 ?
O4 Cu1 Cu2 140.03(5) 2_677 2_577 ?
O4 Cu1 Cu2 39.97(5) . 2_577 ?
O5 Cu1 Cu2 128.72(5) . 2_577 ?
O5 Cu1 Cu2 51.28(5) 2_677 2_577 ?
O6 Cu1 Cu2 76.23(5) . 1_655 ?
O6 Cu1 Cu2 103.77(5) 2_677 1_655 ?
O4 Cu1 Cu2 39.97(5) 2_677 1_655 ?
O4 Cu1 Cu2 140.03(5) . 1_655 ?
O5 Cu1 Cu2 51.28(5) . 1_655 ?
O5 Cu1 Cu2 128.72(5) 2_677 1_655 ?
Cu2 Cu1 Cu2 180.0 2_577 1_655 ?
O7 Cu2 O4 169.20(8) 1_455 . ?
O7 Cu2 O10 90.17(9) 1_455 . ?
O4 Cu2 O10 97.19(8) . . ?
O7 Cu2 O4 93.20(8) 1_455 2_577 ?
O4 Cu2 O4 80.79(7) . 2_577 ?
O10 Cu2 O4 170.52(9) . 2_577 ?
O7 Cu2 O5 97.63(7) 1_455 1_455 ?
O4 Cu2 O5 90.71(7) . 1_455 ?
O10 Cu2 O5 86.69(8) . 1_455 ?
O4 Cu2 O5 84.08(7) 2_577 1_455 ?
O7 Cu2 Cu2 132.82(6) 1_455 2_577 ?
O4 Cu2 Cu2 40.55(5) . 2_577 ?
O10 Cu2 Cu2 137.01(7) . 2_577 ?
O4 Cu2 Cu2 40.25(5) 2_577 2_577 ?
O5 Cu2 Cu2 86.57(5) 1_455 2_577 ?
O7 Cu2 Cu1 80.28(5) 1_455 1_455 ?
O4 Cu2 Cu1 100.26(5) . 1_455 ?
O10 Cu2 Cu1 132.39(6) . 1_455 ?
O4 Cu2 Cu1 40.01(5) 2_577 1_455 ?
O5 Cu2 Cu1 49.40(4) 1_455 1_455 ?
Cu2 Cu2 Cu1 67.181(11) 2_577 1_455 ?
O9 S3 O11 113.93(11) . . ?
O9 S3 O8 112.17(11) . . ?
O11 S3 O8 110.11(12) . . ?
O9 S3 C14 106.26(12) . . ?
O11 S3 C14 108.15(12) . . ?
O8 S3 C14 105.75(11) . . ?
Cu2 O4 Cu2 99.21(7) . 2_577 ?
Cu2 O4 Cu1 115.64(9) . . ?
Cu2 O4 Cu1 100.02(8) 2_577 . ?
Cu2 O4 H4 115(2) . . ?
Cu2 O4 H4 112(2) 2_577 . ?
Cu1 O4 H4 113(2) . . ?
Cu1 O5 Cu2 79.32(6) . 1_655 ?
Cu1 O5 H5A 126(2) . . ?
Cu2 O5 H5A 125(2) 1_655 . ?
Cu1 O5 H5B 112(2) . . ?
Cu2 O5 H5B 106(2) 1_655 . ?
H5A O5 H5B 106(3) . . ?
C12 O6 Cu1 130.52(16) . . ?
C12 O7 Cu2 126.57(17) . 1_655 ?
Cu2 O10 H10A 126(3) . . ?
Cu2 O10 H10B 122(3) . . ?
H10A O10 H10B 108(4) . . ?
O7 C12 O6 125.4(2) . . ?
O7 C12 C18 117.5(2) . . ?
O6 C12 C18 117.0(2) . . ?
C16 C13 C13 119.1(3) . 2_766 ?
C16 C13 C14 122.8(2) . . ?
C13 C13 C14 118.1(3) 2_766 . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 S3 117.38(19) . . ?
C13 C14 S3 121.67(19) . . ?
C14 C15 C17 120.4(2) . . ?
C14 C15 H15 119.8 . . ?
C17 C15 H15 119.8 . . ?
C17 C16 C13 120.6(2) 2_766 . ?
C17 C16 H16 119.7 2_766 . ?
C13 C16 H16 119.7 . . ?
C16 C17 C15 120.9(3) 2_766 . ?
C16 C17 H17 119.6 2_766 . ?
C15 C17 H17 119.6 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Cu2 O7 C12 O6 7.9(4) 1_655 . . . ?
Cu2 O7 C12 C18 -169.74(19) 1_655 . . . ?
Cu1 O6 C12 O7 2.9(4) . . . . ?
Cu1 O6 C12 C18 -179.44(19) . . . . ?
C16 C13 C14 C15 178.6(3) . . . . ?
C13 C13 C14 C15 -1.1(4) 2_766 . . . ?
C16 C13 C14 S3 0.4(4) . . . . ?
C13 C13 C14 S3 -179.3(2) 2_766 . . . ?
O9 S3 C14 C15 4.7(2) . . . . ?
O11 S3 C14 C15 127.4(2) . . . . ?
O8 S3 C14 C15 -114.7(2) . . . . ?
O9 S3 C14 C13 -177.0(2) . . . . ?
O11 S3 C14 C13 -54.3(2) . . . . ?
O8 S3 C14 C13 63.6(2) . . . . ?
C13 C14 C15 C17 1.6(4) . . . . ?
S3 C14 C15 C17 179.9(2) . . . . ?
C13 C13 C16 C17 -1.2(5) 2_766 . . 2_766 ?
C14 C13 C16 C17 179.2(3) . . . 2_766 ?
C14 C15 C17 C16 -0.7(5) . . . 2_766 ?

#==============================================================================
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
O4 H4 O9 . . 2_667 2.704(3) 0.78(2) 1.94(2) 167(2) no
O5 H5A O11 . . 2_767 2.822(3) 0.78(3) 2.05(3) 173(3) no
O5 H5B O8 . . . 2.768(3) 0.79(3) 2.02(3) 157(3) no
O10 H10A O8 . . . 2.675(3) 0.79(2) 1.90(2) 170(4) no
O10 H10B O11 . . 1_455 2.945(3) 0.79(3) 2.18(3) 162(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.


####################################################################### 
# 
# 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_150205f34
_database_code_depnum_ccdc_archive 'CCDC 1493065'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C14 H18 Cu3 O14 S2'
_chemical_formula_moiety         'C14 H18 Cu3 O14 S2'
_chemical_formula_weight         665.05
_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                   9.2709(7)
_cell_length_b                   10.6339(17)
_cell_length_c                   11.848(2)
_cell_angle_alpha                82.673(16)
_cell_angle_beta                 70.523(14)
_cell_angle_gamma                69.251(12)
_cell_volume                     1029.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3839
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      25.00
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             666.00
_exptl_absorpt_coefficient_mu    3.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_T_max  0.512

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

_diffrn_ambient_temperature      150
_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            9927
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4369
_reflns_number_gt                3373
_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          0.0388
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0782
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4369
_refine_ls_number_parameters     316
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0412P)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          0.001
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.78
_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 0.13848(3) 0.53458(3) 0.41000(3) 0.01057(10) Uani 1 1 d . . . . .
Cu2 Cu 0.24673(3) 0.24546(3) 0.50694(3) 0.01023(10) Uani 1 1 d . . . . .
Cu3 Cu 0.37147(3) -0.04520(3) 0.59168(3) 0.01170(10) Uani 1 1 d . . . . .
S4 S 0.14616(7) 0.06160(6) 0.34570(6) 0.00959(14) Uani 1 1 d . . . . .
S5 S 0.35219(7) 0.44028(6) 0.65484(6) 0.00904(14) Uani 1 1 d . . . . .
O6 O 0.0631(2) 0.37927(17) 0.46297(17) 0.0099(4) Uani 1 1 d D . . . .
H6 H 0.047(3) 0.340(3) 0.419(2) 0.012 Uiso 1 1 d D U . . .
O7 O 0.4231(2) 0.54625(17) 0.63028(17) 0.0143(4) Uani 1 1 d . . . . .
O8 O 0.4347(2) 0.11643(17) 0.54619(17) 0.0105(4) Uani 1 1 d D . . . .
H8 H 0.457(3) 0.154(3) 0.586(2) 0.013 Uiso 1 1 d D U . . .
O9 O 0.0832(2) -0.04847(17) 0.36234(17) 0.0146(4) Uani 1 1 d . . . . .
O10 O 0.01840(19) 0.19266(17) 0.35462(17) 0.0131(4) Uani 1 1 d . . . . .
O11 O 0.47475(19) 0.30784(17) 0.65370(17) 0.0134(4) Uani 1 1 d . . . . .
O12 O 0.3027(2) 0.44860(18) 0.26613(17) 0.0140(4) Uani 1 1 d . . . . .
O13 O 0.2046(2) 0.03084(19) 0.73608(17) 0.0176(4) Uani 1 1 d . . . . .
O14 O 0.2893(2) -0.1901(2) 0.6005(2) 0.0247(5) Uani 1 1 d D . . . .
H14A H 0.198(2) -0.182(3) 0.611(3) 0.030 Uiso 1 1 d D U . . .
H14B H 0.332(3) -0.2681(18) 0.601(3) 0.030 Uiso 1 1 d D U . . .
O15 O 0.2519(2) 0.44614(18) 0.58090(16) 0.0132(4) Uani 1 1 d . . . . .
O16 O 0.2450(2) 0.05152(18) 0.42157(17) 0.0136(4) Uani 1 1 d . . . . .
O17 O 0.0935(2) 0.23612(17) 0.66450(17) 0.0140(4) Uani 1 1 d . . . . .
O18 O 0.2195(2) 0.6829(2) 0.3837(2) 0.0221(5) Uani 1 1 d D . . . .
H18A H 0.171(3) 0.7596(19) 0.393(3) 0.027 Uiso 1 1 d D U . . .
H18B H 0.310(2) 0.672(3) 0.381(3) 0.027 Uiso 1 1 d D U . . .
O19 O 0.4040(2) 0.24901(17) 0.34856(17) 0.0139(4) Uani 1 1 d . . . . .
C20 C 0.2246(3) 0.4630(3) 0.8040(2) 0.0125(5) Uani 1 1 d . . . . .
C21 C 0.2740(3) 0.0533(3) 0.1952(2) 0.0129(5) Uani 1 1 d . . . . .
C22 C 0.4039(3) 0.3312(3) 0.2618(2) 0.0128(5) Uani 1 1 d . . . . .
C23 C 0.0951(3) 0.1448(3) 0.7439(3) 0.0145(6) Uani 1 1 d . . . . .
C24 C -0.0359(3) 0.5021(2) 0.9548(2) 0.0120(5) Uani 1 1 d . . . . .
C25 C 0.5319(3) -0.0378(2) 0.0446(2) 0.0118(5) Uani 1 1 d . . . . .
C26 C 0.4325(3) -0.0292(3) 0.1647(2) 0.0144(6) Uani 1 1 d . . . . .
H26 H 0.4756 -0.0810 0.2247 0.017 Uiso 1 1 calc R U . . .
C27 C 0.0617(3) 0.4841(2) 0.8349(2) 0.0124(5) Uani 1 1 d . . . . .
H27 H 0.0144 0.4865 0.7744 0.015 Uiso 1 1 calc R U . . .
C28 C -0.0440(3) 0.1741(3) 0.8586(3) 0.0214(6) Uani 1 1 d . . . . .
H28A H -0.0285 0.0959 0.9125 0.026 Uiso 1 1 calc R U . . .
H28B H -0.0481 0.2522 0.8970 0.026 Uiso 1 1 calc R U . . .
H28C H -0.1459 0.1932 0.8411 0.026 Uiso 1 1 calc R U . . .
C29 C -0.2054(3) 0.5241(3) 0.9902(2) 0.0160(6) Uani 1 1 d . . . . .
H29 H -0.2550 0.5260 0.9313 0.019 Uiso 1 1 calc R U . . .
C30 C 0.6979(3) -0.1240(3) 0.0098(3) 0.0175(6) Uani 1 1 d . . . . .
H30 H 0.7428 -0.1768 0.0686 0.021 Uiso 1 1 calc R U . . .
C31 C 0.2973(3) 0.4577(3) 0.8930(2) 0.0148(6) Uani 1 1 d . . . . .
H31 H 0.4107 0.4413 0.8710 0.018 Uiso 1 1 calc R U . . .
C32 C 0.2082(3) 0.1309(3) 0.1071(3) 0.0188(6) Uani 1 1 d . . . . .
H32 H 0.0981 0.1880 0.1292 0.023 Uiso 1 1 calc R U . . .
C33 C 0.5336(3) 0.2828(3) 0.1452(3) 0.0194(6) Uani 1 1 d . . . . .
H33A H 0.5221 0.3542 0.0845 0.023 Uiso 1 1 calc R U . . .
H33B H 0.6406 0.2588 0.1559 0.023 Uiso 1 1 calc R U . . .
H33C H 0.5228 0.2036 0.1192 0.023 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_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 O18 1.9250(18) . ?
Cu1 O12 1.9338(19) . ?
Cu1 O6 1.9647(19) 2_566 ?
Cu1 O6 1.9674(16) . ?
Cu1 Cu1 2.9947(8) 2_566 ?
Cu2 O17 1.9486(19) . ?
Cu2 O8 1.9540(17) . ?
Cu2 O19 1.9609(19) . ?
Cu2 O6 1.9698(17) . ?
Cu2 O16 2.4173(18) . ?
Cu2 O15 2.4295(18) . ?
Cu2 Cu3 3.0576(7) . ?
Cu3 O13 1.917(2) . ?
Cu3 O14 1.9244(19) . ?
Cu3 O8 1.9634(16) . ?
Cu3 O8 1.9661(19) 2_656 ?
Cu3 Cu3 2.9936(8) 2_656 ?
S4 O9 1.4487(17) . ?
S4 O16 1.4538(18) . ?
S4 O10 1.4632(18) . ?
S4 C21 1.774(3) . ?
S5 O7 1.4495(17) . ?
S5 O15 1.4571(18) . ?
S5 O11 1.4613(18) . ?
S5 C20 1.758(3) . ?
O6 Cu1 1.9647(19) 2_566 ?
O6 H6 0.790(13) . ?
O8 Cu3 1.9661(19) 2_656 ?
O8 H8 0.772(17) . ?
O12 C22 1.263(3) . ?
O13 C23 1.266(3) . ?
O14 H14A 0.790(17) . ?
O14 H14B 0.782(18) . ?
O17 C23 1.263(3) . ?
O18 H18A 0.780(17) . ?
O18 H18B 0.792(17) . ?
O19 C22 1.261(3) . ?
C20 C27 1.371(3) . ?
C20 C31 1.414(4) . ?
C21 C26 1.369(4) . ?
C21 C32 1.411(4) . ?
C22 C33 1.502(4) . ?
C23 C28 1.503(4) . ?
C24 C27 1.402(4) . ?
C24 C29 1.423(3) . ?
C24 C24 1.426(5) 2_567 ?
C25 C25 1.406(5) 2_655 ?
C25 C26 1.407(4) . ?
C25 C30 1.432(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C31 1.358(4) 2_567 ?
C29 H29 0.9500 . ?
C30 C32 1.362(4) 2_655 ?
C30 H30 0.9500 . ?
C31 C29 1.358(4) 2_567 ?
C31 H31 0.9500 . ?
C32 C30 1.362(4) 2_655 ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
O18 Cu1 O12 90.80(8) . . ?
O18 Cu1 O6 95.93(8) . 2_566 ?
O12 Cu1 O6 166.66(7) . 2_566 ?
O18 Cu1 O6 170.30(9) . . ?
O12 Cu1 O6 94.31(8) . . ?
O6 Cu1 O6 80.79(8) 2_566 . ?
O18 Cu1 Cu1 135.67(7) . 2_566 ?
O12 Cu1 Cu1 133.45(5) . 2_566 ?
O6 Cu1 Cu1 40.43(5) 2_566 2_566 ?
O6 Cu1 Cu1 40.36(5) . 2_566 ?
O17 Cu2 O8 94.68(8) . . ?
O17 Cu2 O19 178.29(7) . . ?
O8 Cu2 O19 84.05(8) . . ?
O17 Cu2 O6 87.30(8) . . ?
O8 Cu2 O6 177.68(6) . . ?
O19 Cu2 O6 94.00(8) . . ?
O17 Cu2 O16 97.70(7) . . ?
O8 Cu2 O16 83.56(7) . . ?
O19 Cu2 O16 81.04(7) . . ?
O6 Cu2 O16 97.41(7) . . ?
O17 Cu2 O15 85.26(7) . . ?
O8 Cu2 O15 97.90(6) . . ?
O19 Cu2 O15 96.04(7) . . ?
O6 Cu2 O15 81.02(6) . . ?
O16 Cu2 O15 176.61(5) . . ?
O17 Cu2 Cu3 74.93(6) . . ?
O8 Cu2 Cu3 38.80(5) . . ?
O19 Cu2 Cu3 103.37(6) . . ?
O6 Cu2 Cu3 143.25(5) . . ?
O16 Cu2 Cu3 54.88(4) . . ?
O15 Cu2 Cu3 127.84(5) . . ?
O13 Cu3 O14 91.19(9) . . ?
O13 Cu3 O8 94.29(8) . . ?
O14 Cu3 O8 164.96(9) . . ?
O13 Cu3 O8 171.06(7) . 2_656 ?
O14 Cu3 O8 95.47(8) . 2_656 ?
O8 Cu3 O8 80.75(8) . 2_656 ?
O13 Cu3 Cu3 134.25(6) . 2_656 ?
O14 Cu3 Cu3 134.10(7) . 2_656 ?
O8 Cu3 Cu3 40.41(6) . 2_656 ?
O8 Cu3 Cu3 40.34(5) 2_656 2_656 ?
O13 Cu3 Cu2 80.43(6) . . ?
O14 Cu3 Cu2 129.43(7) . . ?
O8 Cu3 Cu2 38.58(5) . . ?
O8 Cu3 Cu2 99.77(5) 2_656 . ?
Cu3 Cu3 Cu2 66.344(19) 2_656 . ?
O9 S4 O16 113.55(11) . . ?
O9 S4 O10 112.03(10) . . ?
O16 S4 O10 112.28(11) . . ?
O9 S4 C21 106.38(12) . . ?
O16 S4 C21 107.04(11) . . ?
O10 S4 C21 104.84(12) . . ?
O7 S5 O15 114.42(11) . . ?
O7 S5 O11 111.41(10) . . ?
O15 S5 O11 112.47(10) . . ?
O7 S5 C20 105.65(11) . . ?
O15 S5 C20 107.13(11) . . ?
O11 S5 C20 104.97(12) . . ?
Cu1 O6 Cu1 99.21(8) 2_566 . ?
Cu1 O6 Cu2 119.21(10) 2_566 . ?
Cu1 O6 Cu2 102.74(7) . . ?
Cu1 O6 H6 111(2) 2_566 . ?
Cu1 O6 H6 122(2) . . ?
Cu2 O6 H6 103(2) . . ?
Cu2 O8 Cu3 102.61(7) . . ?
Cu2 O8 Cu3 115.28(9) . 2_656 ?
Cu3 O8 Cu3 99.25(8) . 2_656 ?
Cu2 O8 H8 106(2) . . ?
Cu3 O8 H8 126(2) . . ?
Cu3 O8 H8 108(2) 2_656 . ?
C22 O12 Cu1 124.89(18) . . ?
C23 O13 Cu3 125.28(18) . . ?
Cu3 O14 H14A 125(2) . . ?
Cu3 O14 H14B 131(2) . . ?
H14A O14 H14B 104(3) . . ?
S5 O15 Cu2 122.43(10) . . ?
S4 O16 Cu2 122.89(10) . . ?
C23 O17 Cu2 131.81(17) . . ?
Cu1 O18 H18A 129(2) . . ?
Cu1 O18 H18B 121(2) . . ?
H18A O18 H18B 107(3) . . ?
C22 O19 Cu2 133.35(17) . . ?
C27 C20 C31 120.4(2) . . ?
C27 C20 S5 122.4(2) . . ?
C31 C20 S5 117.16(18) . . ?
C26 C21 C32 120.6(2) . . ?
C26 C21 S4 120.6(2) . . ?
C32 C21 S4 118.78(19) . . ?
O19 C22 O12 124.9(3) . . ?
O19 C22 C33 116.4(2) . . ?
O12 C22 C33 118.7(2) . . ?
O17 C23 O13 125.7(3) . . ?
O17 C23 C28 117.4(2) . . ?
O13 C23 C28 116.9(2) . . ?
C27 C24 C29 122.2(2) . . ?
C27 C24 C24 119.4(3) . 2_567 ?
C29 C24 C24 118.5(3) . 2_567 ?
C25 C25 C26 120.0(3) 2_655 . ?
C25 C25 C30 118.4(3) 2_655 . ?
C26 C25 C30 121.6(2) . . ?
C21 C26 C25 120.3(3) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C20 C27 C24 120.6(2) . . ?
C20 C27 H27 119.7 . . ?
C24 C27 H27 119.7 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C31 C29 C24 120.9(2) 2_567 . ?
C31 C29 H29 119.6 2_567 . ?
C24 C29 H29 119.6 . . ?
C32 C30 C25 120.5(2) 2_655 . ?
C32 C30 H30 119.7 2_655 . ?
C25 C30 H30 119.7 . . ?
C29 C31 C20 120.2(2) 2_567 . ?
C29 C31 H31 119.9 2_567 . ?
C20 C31 H31 119.9 . . ?
C30 C32 C21 120.2(2) 2_655 . ?
C30 C32 H32 119.9 2_655 . ?
C21 C32 H32 119.9 . . ?
C22 C33 H33A 109.5 . . ?
C22 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C22 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
O7 S5 O15 Cu2 142.66(11) . . . . ?
O11 S5 O15 Cu2 14.23(15) . . . . ?
C20 S5 O15 Cu2 -100.60(13) . . . . ?
O9 S4 O16 Cu2 -144.43(11) . . . . ?
O10 S4 O16 Cu2 -16.05(15) . . . . ?
C21 S4 O16 Cu2 98.48(13) . . . . ?
O7 S5 C20 C27 121.3(2) . . . . ?
O15 S5 C20 C27 -1.0(2) . . . . ?
O11 S5 C20 C27 -120.8(2) . . . . ?
O7 S5 C20 C31 -59.2(2) . . . . ?
O15 S5 C20 C31 178.44(19) . . . . ?
O11 S5 C20 C31 58.7(2) . . . . ?
O9 S4 C21 C26 -84.6(2) . . . . ?
O16 S4 C21 C26 37.1(2) . . . . ?
O10 S4 C21 C26 156.58(19) . . . . ?
O9 S4 C21 C32 93.8(2) . . . . ?
O16 S4 C21 C32 -144.47(19) . . . . ?
O10 S4 C21 C32 -25.0(2) . . . . ?
Cu2 O19 C22 O12 11.9(4) . . . . ?
Cu2 O19 C22 C33 -167.20(17) . . . . ?
Cu1 O12 C22 O19 6.3(3) . . . . ?
Cu1 O12 C22 C33 -174.64(16) . . . . ?
Cu2 O17 C23 O13 -1.1(4) . . . . ?
Cu2 O17 C23 C28 178.26(16) . . . . ?
Cu3 O13 C23 O17 -13.1(3) . . . . ?
Cu3 O13 C23 C28 167.58(17) . . . . ?
C32 C21 C26 C25 0.0(4) . . . . ?
S4 C21 C26 C25 178.33(18) . . . . ?
C25 C25 C26 C21 -0.4(4) 2_655 . . . ?
C30 C25 C26 C21 -179.6(2) . . . . ?
C31 C20 C27 C24 0.7(4) . . . . ?
S5 C20 C27 C24 -179.87(19) . . . . ?
C29 C24 C27 C20 -180.0(2) . . . . ?
C24 C24 C27 C20 -0.2(4) 2_567 . . . ?
C27 C24 C29 C31 -179.4(2) . . . 2_567 ?
C24 C24 C29 C31 0.8(4) 2_567 . . 2_567 ?
C25 C25 C30 C32 0.7(4) 2_655 . . 2_655 ?
C26 C25 C30 C32 179.9(2) . . . 2_655 ?
C27 C20 C31 C29 -1.3(4) . . . 2_567 ?
S5 C20 C31 C29 179.3(2) . . . 2_567 ?
C26 C21 C32 C30 0.1(4) . . . 2_655 ?
S4 C21 C32 C30 -178.3(2) . . . 2_655 ?

#==============================================================================
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 H6 O10 . . . 2.710(3) 0.79(3) 1.96(3) 159(3) no
O8 H8 O11 . . . 2.723(3) 0.77(4) 1.99(3) 158(3) no
O14 H14A O10 . . 2_556 2.732(3) 0.79(2) 1.95(3) 171(3) no
O14 H14B O7 . . 1_545 2.664(3) 0.782(18) 1.890(19) 170(4) no
O18 H18A O9 . . 1_565 2.700(3) 0.780(18) 1.948(19) 162(3) no
O18 H18B O11 . . 2_666 2.755(3) 0.79(3) 1.99(3) 164(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.


