# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_Glycol-T173K
_audit_block_doi                 10.5517/ccdc.csd.cc20623f
_database_code_depnum_ccdc_archive 'CCDC 1852873'
_audit_update_record             
;
2018-06-30 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Cu N4 O6 S'
_chemical_formula_weight         582.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   17.674(9)
_cell_length_b                   11.958(5)
_cell_length_c                   13.124(7)
_cell_angle_alpha                90
_cell_angle_beta                 120.998(7)
_cell_angle_gamma                90
_cell_volume                     2378(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3768
_cell_measurement_theta_min      3.2120
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLUE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    1.060
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku saturn 724'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12698
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.240
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5374
_reflns_number_gt                5153
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.5521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.484(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     344
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.01213(3) 0.21779(3) 0.23902(4) 0.01528(12) Uani 1 1 d . . . . .
S1 S -0.00009(6) -0.04383(8) 0.25015(8) 0.0140(2) Uani 1 1 d . . . . .
O1 O -0.0180(2) 0.0622(2) 0.1801(3) 0.0214(6) Uani 1 1 d . . . . .
O2 O 0.00666(19) -0.0190(2) 0.3638(2) 0.0183(6) Uani 1 1 d . . . . .
O3 O 0.0826(2) -0.0946(3) 0.2695(3) 0.0213(7) Uani 1 1 d . . . . .
O4 O -0.0750(2) -0.1202(3) 0.1780(3) 0.0181(7) Uani 1 1 d . . . . .
O5 O 0.0640(3) -0.3075(3) 0.1719(4) 0.0321(9) Uani 1 1 d . . . . .
H5A H 0.0693 -0.2471 0.2077 0.048 Uiso 1 1 calc R U . . .
O6 O -0.0457(3) -0.3251(3) 0.2897(4) 0.0335(9) Uani 1 1 d . . . . .
H6B H -0.0541 -0.2639 0.2540 0.050 Uiso 1 1 calc R U . . .
C1 C -0.0892(3) 0.3548(4) -0.0058(4) 0.0220(10) Uani 1 1 d . . . . .
H1A H -0.0416 0.3392 -0.0176 0.026 Uiso 1 1 calc R U . . .
C2 C -0.1623(4) 0.4164(4) -0.0932(5) 0.0222(11) Uani 1 1 d . . . . .
H2A H -0.1634 0.4410 -0.1628 0.027 Uiso 1 1 calc R U . . .
C3 C -0.2309(3) 0.4405(4) -0.0778(4) 0.0213(10) Uani 1 1 d . . . . .
H3A H -0.2799 0.4824 -0.1359 0.026 Uiso 1 1 calc R U . . .
C4 C -0.2980(3) 0.4226(4) 0.0490(5) 0.0221(11) Uani 1 1 d . . . . .
H4A H -0.3485 0.4638 -0.0069 0.027 Uiso 1 1 calc R U . . .
C5 C -0.2286(3) 0.4021(4) 0.0264(4) 0.0166(10) Uani 1 1 d . . . . .
C6 C -0.2928(3) 0.3838(4) 0.1505(5) 0.0208(10) Uani 1 1 d . . . . .
H6A H -0.3392 0.3994 0.1650 0.025 Uiso 1 1 calc R U . . .
C7 C -0.2181(3) 0.3198(4) 0.2352(4) 0.0172(9) Uani 1 1 d . . . . .
C8 C -0.2095(3) 0.2760(4) 0.3407(5) 0.0193(10) Uani 1 1 d . . . . .
H8A H -0.2544 0.2893 0.3586 0.023 Uiso 1 1 calc R U . . .
C9 C -0.1370(4) 0.2150(4) 0.4168(5) 0.0193(11) Uani 1 1 d . . . . .
H9A H -0.1305 0.1863 0.4884 0.023 Uiso 1 1 calc R U . . .
C10 C -0.0710(3) 0.1947(4) 0.3874(4) 0.0187(10) Uani 1 1 d . . . . .
H10A H -0.0209 0.1510 0.4399 0.022 Uiso 1 1 calc R U . . .
C11 C -0.1485(3) 0.2975(4) 0.2144(4) 0.0141(9) Uani 1 1 d . . . . .
C12 C -0.1538(3) 0.3408(4) 0.1084(4) 0.0150(9) Uani 1 1 d . . . . .
C13 C 0.0925(3) 0.1819(4) 0.0875(4) 0.0184(9) Uani 1 1 d . . . . .
H13A H 0.0443 0.1336 0.0398 0.022 Uiso 1 1 calc R U . . .
C14 C 0.1528(4) 0.2028(4) 0.0534(5) 0.0205(10) Uani 1 1 d . . . . .
H14A H 0.1445 0.1715 -0.0182 0.025 Uiso 1 1 calc R U . . .
C15 C 0.2258(4) 0.2696(4) 0.1235(5) 0.0201(10) Uani 1 1 d . . . . .
H15A H 0.2682 0.2837 0.1011 0.024 Uiso 1 1 calc R U . . .
C16 C 0.2359(3) 0.3164(4) 0.2292(4) 0.0168(9) Uani 1 1 d . . . . .
C17 C 0.3105(3) 0.3836(4) 0.3115(4) 0.0200(10) Uani 1 1 d . . . . .
H17A H 0.3562 0.3991 0.2956 0.024 Uiso 1 1 calc R U . . .
C18 C 0.3159(3) 0.4248(4) 0.4111(5) 0.0181(10) Uani 1 1 d . . . . .
H18A H 0.3658 0.4683 0.4643 0.022 Uiso 1 1 calc R U . . .
C19 C 0.2483(3) 0.4046(4) 0.4385(4) 0.0170(10) Uani 1 1 d . . . . .
C20 C 0.2505(3) 0.4434(4) 0.5411(4) 0.0205(10) Uani 1 1 d . . . . .
H20A H 0.2990 0.4869 0.5979 0.025 Uiso 1 1 calc R U . . .
C21 C 0.1824(4) 0.4182(4) 0.5587(5) 0.0245(11) Uani 1 1 d . . . . .
H21A H 0.1835 0.4442 0.6279 0.029 Uiso 1 1 calc R U . . .
C22 C 0.1115(3) 0.3543(4) 0.4749(4) 0.0201(10) Uani 1 1 d . . . . .
H22A H 0.0648 0.3378 0.4885 0.024 Uiso 1 1 calc R U . . .
C23 C 0.1751(3) 0.3394(4) 0.3595(4) 0.0148(9) Uani 1 1 d . . . . .
C24 C 0.1701(3) 0.2938(4) 0.2544(5) 0.0152(9) Uani 1 1 d . . . . .
C25 C -0.0272(4) -0.4095(4) 0.2293(6) 0.0324(13) Uani 1 1 d . . . . .
H25A H -0.0738 -0.4080 0.1441 0.039 Uiso 1 1 calc R U . . .
H25B H -0.0298 -0.4833 0.2614 0.039 Uiso 1 1 calc R U . . .
C26 C 0.0601(4) -0.3979(5) 0.2392(6) 0.0344(14) Uani 1 1 d . . . . .
H26A H 0.1060 -0.3871 0.3238 0.041 Uiso 1 1 calc R U . . .
H26B H 0.0738 -0.4682 0.2121 0.041 Uiso 1 1 calc R U . . .
N1 N -0.0854(2) 0.3182(3) 0.0926(3) 0.0147(8) Uani 1 1 d . . . . .
N2 N -0.0772(3) 0.2348(3) 0.2894(4) 0.0155(8) Uani 1 1 d . . . . .
N3 N 0.1065(3) 0.3149(3) 0.3757(4) 0.0167(8) Uani 1 1 d . . . . .
N4 N 0.0990(3) 0.2270(3) 0.1852(4) 0.0148(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.979(3) . ?
Cu1 N4 1.997(4) . ?
Cu1 N2 2.012(4) . ?
Cu1 N3 2.066(4) . ?
Cu1 N1 2.167(4) . ?
S1 O2 1.464(3) . ?
S1 O3 1.479(3) . ?
S1 O4 1.481(3) . ?
S1 O1 1.501(3) . ?
O5 C26 1.420(6) . ?
O6 C25 1.421(6) . ?
C1 N1 1.332(6) . ?
C1 C2 1.414(7) . ?
C2 C3 1.360(7) . ?
C3 C5 1.422(7) . ?
C4 C6 1.369(7) . ?
C4 C5 1.425(7) . ?
C5 C12 1.406(7) . ?
C6 C7 1.432(7) . ?
C7 C8 1.413(7) . ?
C7 C11 1.415(6) . ?
C8 C9 1.362(8) . ?
C9 C10 1.426(7) . ?
C10 N2 1.323(7) . ?
C11 N2 1.357(6) . ?
C11 C12 1.442(6) . ?
C12 N1 1.356(5) . ?
C13 N4 1.340(6) . ?
C13 C14 1.374(7) . ?
C14 C15 1.388(8) . ?
C15 C16 1.420(7) . ?
C16 C24 1.391(6) . ?
C16 C17 1.444(7) . ?
C17 C18 1.353(7) . ?
C18 C19 1.434(7) . ?
C19 C20 1.406(7) . ?
C19 C23 1.406(7) . ?
C20 C21 1.372(7) . ?
C21 C22 1.395(7) . ?
C22 N3 1.344(6) . ?
C23 N3 1.366(6) . ?
C23 C24 1.442(7) . ?
C24 N4 1.365(6) . ?
C25 C26 1.486(7) . ?

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 N4 90.88(13) . . ?
O1 Cu1 N2 97.14(14) . . ?
N4 Cu1 N2 170.95(12) . . ?
O1 Cu1 N3 143.34(14) . . ?
N4 Cu1 N3 81.50(16) . . ?
N2 Cu1 N3 94.41(16) . . ?
O1 Cu1 N1 104.09(13) . . ?
N4 Cu1 N1 93.47(15) . . ?
N2 Cu1 N1 80.53(16) . . ?
N3 Cu1 N1 112.10(11) . . ?
O2 S1 O3 110.72(18) . . ?
O2 S1 O4 110.70(17) . . ?
O3 S1 O4 109.63(16) . . ?
O2 S1 O1 109.43(17) . . ?
O3 S1 O1 109.27(18) . . ?
O4 S1 O1 107.01(18) . . ?
S1 O1 Cu1 128.73(18) . . ?
N1 C1 C2 121.8(4) . . ?
C3 C2 C1 120.1(4) . . ?
C2 C3 C5 119.2(5) . . ?
C6 C4 C5 120.7(5) . . ?
C12 C5 C3 117.0(4) . . ?
C12 C5 C4 120.1(4) . . ?
C3 C5 C4 122.9(5) . . ?
C4 C6 C7 120.6(4) . . ?
C8 C7 C11 116.9(5) . . ?
C8 C7 C6 123.3(5) . . ?
C11 C7 C6 119.8(4) . . ?
C9 C8 C7 120.2(5) . . ?
C8 C9 C10 119.0(5) . . ?
N2 C10 C9 122.1(5) . . ?
N2 C11 C7 122.6(4) . . ?
N2 C11 C12 118.2(4) . . ?
C7 C11 C12 119.2(4) . . ?
N1 C12 C5 123.2(4) . . ?
N1 C12 C11 117.2(4) . . ?
C5 C12 C11 119.6(4) . . ?
N4 C13 C14 122.6(5) . . ?
C13 C14 C15 120.1(5) . . ?
C14 C15 C16 118.7(5) . . ?
C24 C16 C15 117.2(4) . . ?
C24 C16 C17 118.9(4) . . ?
C15 C16 C17 123.9(4) . . ?
C18 C17 C16 120.5(4) . . ?
C17 C18 C19 121.9(5) . . ?
C20 C19 C23 116.8(4) . . ?
C20 C19 C18 124.7(5) . . ?
C23 C19 C18 118.6(4) . . ?
C21 C20 C19 119.7(5) . . ?
C20 C21 C22 119.8(5) . . ?
N3 C22 C21 122.7(4) . . ?
N3 C23 C19 123.9(4) . . ?
N3 C23 C24 116.5(4) . . ?
C19 C23 C24 119.6(4) . . ?
N4 C24 C16 123.4(4) . . ?
N4 C24 C23 116.1(4) . . ?
C16 C24 C23 120.5(4) . . ?
O6 C25 C26 114.3(5) . . ?
O5 C26 C25 113.4(5) . . ?
C1 N1 C12 118.6(4) . . ?
C1 N1 Cu1 131.5(3) . . ?
C12 N1 Cu1 109.8(3) . . ?
C10 N2 C11 119.1(4) . . ?
C10 N2 Cu1 126.6(4) . . ?
C11 N2 Cu1 114.2(3) . . ?
C22 N3 C23 117.1(4) . . ?
C22 N3 Cu1 131.2(3) . . ?
C23 N3 Cu1 111.7(3) . . ?
C13 N4 C24 117.9(4) . . ?
C13 N4 Cu1 127.8(3) . . ?
C24 N4 Cu1 114.1(3) . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_global
_audit_block_doi                 10.5517/ccdc.csd.cc12s7lp
_database_code_depnum_ccdc_archive 'CCDC 1006402'
_audit_update_record             
;
2018-06-23 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Cu0.50 N O4 S0.50'
_chemical_formula_weight         293.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.6404(14)
_cell_length_b                   12.0146(8)
_cell_length_c                   13.1577(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.947(7)
_cell_angle_gamma                90.00
_cell_volume                     2391.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1204
_exptl_absorpt_coefficient_mu    1.058
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7779
_exptl_absorpt_correction_T_max  0.8006
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5168
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2346
_reflns_number_gt                2046
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0141P)²+10.6924P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00128(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2346
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.28490(4) 0.2500 0.02893(18) Uani 1 2 d S . .
S1 S 0.0000 0.54390(10) 0.2500 0.0641(5) Uani 1 2 d S . .
O1 O 0.0002(3) 0.5209(4) 0.3781(4) 0.0350(14) Uani 0.487(5) 1 d P A 1
O1' O 0.0269(3) 0.4383(4) 0.3039(4) 0.0419(14) Uani 0.513(5) 1 d P . 2
O2 O -0.07867(16) 0.6073(2) 0.2040(2) 0.0574(7) Uani 1 1 d . A .
N2 N 0.08826(16) 0.2714(2) 0.1985(2) 0.0293(6) Uani 1 1 d . A .
N1 N 0.09558(16) 0.1854(2) 0.3907(2) 0.0283(6) Uani 1 1 d . A .
C10 C 0.1004(2) 0.1469(3) 0.4883(3) 0.0372(8) Uani 1 1 d . . .
H10 H 0.0543 0.1625 0.5009 0.045 Uiso 1 1 calc R A .
C9 C 0.1713(2) 0.0841(3) 0.5728(3) 0.0437(8) Uani 1 1 d . A .
H9 H 0.1722 0.0593 0.6403 0.052 Uiso 1 1 calc R . .
C8 C 0.2392(2) 0.0593(3) 0.5558(3) 0.0393(8) Uani 1 1 d . . .
H8 H 0.2867 0.0171 0.6114 0.047 Uiso 1 1 calc R A .
C7 C 0.23683(19) 0.0980(2) 0.4537(3) 0.0302(7) Uani 1 1 d . A .
C11 C 0.16362(18) 0.1617(2) 0.3739(3) 0.0253(6) Uani 1 1 d . . .
C12 C 0.15852(18) 0.2058(2) 0.2697(3) 0.0255(6) Uani 1 1 d . A .
C6 C 0.3048(2) 0.0777(3) 0.4277(3) 0.0386(8) Uani 1 1 d . . .
H6 H 0.3540 0.0363 0.4806 0.046 Uiso 1 1 calc R A .
C4 C 0.22580(19) 0.1829(3) 0.2461(3) 0.0308(7) Uani 1 1 d . . .
C3 C 0.2166(2) 0.2287(3) 0.1422(3) 0.0382(8) Uani 1 1 d . A .
H3 H 0.2594 0.2150 0.1225 0.046 Uiso 1 1 calc R . .
C2 C 0.1453(2) 0.2931(3) 0.0702(3) 0.0404(8) Uani 1 1 d . . .
H2 H 0.1386 0.3228 0.0007 0.048 Uiso 1 1 calc R A .
C1 C 0.0825(2) 0.3139(3) 0.1019(3) 0.0367(8) Uani 1 1 d . A .
H1 H 0.0346 0.3595 0.0534 0.044 Uiso 1 1 calc R . .
C5 C 0.2995(2) 0.1172(3) 0.3286(3) 0.0393(8) Uani 1 1 d . A .
H5 H 0.3445 0.1015 0.3135 0.047 Uiso 1 1 calc R . .
O3 O 0.4459(3) 0.3162(3) 0.3090(3) 0.0762(10) Uani 1 1 d . . .
H3A H 0.4396 0.2572 0.2742 0.114 Uiso 1 1 calc R . .
C13 C 0.4586(4) 0.4011(4) 0.2489(5) 0.0845(17) Uani 1 1 d . . .
H13A H 0.4536 0.4712 0.2815 0.101 Uiso 1 1 calc R . .
H13B H 0.4109 0.3984 0.1668 0.101 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1' 1.944(4) . ?
Cu1 O1' 1.944(4) 2 ?
Cu1 N2 1.998(2) . ?
Cu1 N2 1.998(2) 2 ?
Cu1 N1 2.119(2) 2 ?
Cu1 N1 2.119(2) . ?
S1 O1' 1.411(4) 2 ?
S1 O1' 1.411(4) . ?
S1 O2 1.417(3) 2 ?
S1 O2 1.417(3) . ?
S1 O1 1.707(4) 2 ?
S1 O1 1.707(4) . ?
O1' O1' 1.236(8) 2 ?
N2 C1 1.325(4) . ?
N2 C12 1.356(4) . ?
N1 C10 1.325(4) . ?
N1 C11 1.358(4) . ?
C10 C9 1.392(5) . ?
C10 H10 0.9300 . ?
C9 C8 1.359(5) . ?
C9 H9 0.9300 . ?
C8 C7 1.403(4) . ?
C8 H8 0.9300 . ?
C7 C11 1.401(4) . ?
C7 C6 1.427(4) . ?
C11 C12 1.430(4) . ?
C12 C4 1.400(4) . ?
C6 C5 1.345(5) . ?
C6 H6 0.9300 . ?
C4 C3 1.402(4) . ?
C4 C5 1.429(4) . ?
C3 C2 1.362(5) . ?
C3 H3 0.9300 . ?
C2 C1 1.393(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C5 H5 0.9300 . ?
O3 C13 1.378(5) . ?
O3 H3A 0.8200 . ?
C13 C13 1.445(10) 2_655 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1' Cu1 O1' 37.1(3) . 2 ?
O1' Cu1 N2 96.57(16) . . ?
O1' Cu1 N2 92.29(16) 2 . ?
O1' Cu1 N2 92.29(16) . 2 ?
O1' Cu1 N2 96.57(16) 2 2 ?
N2 Cu1 N2 170.66(15) . 2 ?
O1' Cu1 N1 142.07(15) . 2 ?
O1' Cu1 N1 106.31(15) 2 2 ?
N2 Cu1 N1 93.81(10) . 2 ?
N2 Cu1 N1 80.89(9) 2 2 ?
O1' Cu1 N1 106.31(15) . . ?
O1' Cu1 N1 142.07(15) 2 . ?
N2 Cu1 N1 80.90(9) . . ?
N2 Cu1 N1 93.81(10) 2 . ?
N1 Cu1 N1 111.33(14) 2 . ?
O1' S1 O1' 52.0(3) 2 . ?
O1' S1 O2 134.4(2) 2 2 ?
O1' S1 O2 105.4(2) . 2 ?
O1' S1 O2 105.4(2) 2 . ?
O1' S1 O2 134.4(2) . . ?
O2 S1 O2 115.0(2) 2 . ?
O1' S1 O1 61.9(2) 2 2 ?
O1' S1 O1 100.4(2) . 2 ?
O2 S1 O1 90.74(19) 2 2 ?
O2 S1 O1 99.29(19) . 2 ?
O1' S1 O1 100.4(2) 2 . ?
O1' S1 O1 61.9(2) . . ?
O2 S1 O1 99.29(19) 2 . ?
O2 S1 O1 90.74(19) . . ?
O1 S1 O1 161.3(3) 2 . ?
O1' O1' S1 64.02(17) 2 . ?
O1' O1' Cu1 71.47(13) 2 . ?
S1 O1' Cu1 135.5(3) . . ?
C1 N2 C12 118.6(3) . . ?
C1 N2 Cu1 127.2(2) . . ?
C12 N2 Cu1 114.09(19) . . ?
C10 N1 C11 117.5(3) . . ?
C10 N1 Cu1 132.0(2) . . ?
C11 N1 Cu1 110.42(18) . . ?
N1 C10 C9 123.2(3) . . ?
N1 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C11 C7 C8 117.4(3) . . ?
C11 C7 C6 118.6(3) . . ?
C8 C7 C6 124.0(3) . . ?
N1 C11 C7 123.0(3) . . ?
N1 C11 C12 117.0(3) . . ?
C7 C11 C12 120.0(3) . . ?
N2 C12 C4 122.6(3) . . ?
N2 C12 C11 117.5(2) . . ?
C4 C12 C11 119.9(3) . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C12 C4 C3 116.9(3) . . ?
C12 C4 C5 118.9(3) . . ?
C3 C4 C5 124.1(3) . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
N2 C1 C2 122.5(3) . . ?
N2 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C13 O3 H3A 109.5 . . ?
O3 C13 C13 116.7(4) . 2_655 ?
O3 C13 H13A 108.1 . . ?
C13 C13 H13A 108.1 2_655 . ?
O3 C13 H13B 108.1 . . ?
C13 C13 H13B 108.1 2_655 . ?
H13A C13 H13B 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S1 O1' O1' -134.9(4) 2 . . 2 ?
O2 S1 O1' O1' 72.9(5) . . . 2 ?
O1 S1 O1' O1' -41.2(5) 2 . . 2 ?
O1 S1 O1' O1' 132.7(5) . . . 2 ?
O1' S1 O1' Cu1 0.0 2 . . . ?
O2 S1 O1' Cu1 -134.9(4) 2 . . . ?
O2 S1 O1' Cu1 72.9(5) . . . . ?
O1 S1 O1' Cu1 -41.2(5) 2 . . . ?
O1 S1 O1' Cu1 132.7(5) . . . . ?
N2 Cu1 O1' O1' 85.1(4) . . . 2 ?
N2 Cu1 O1' O1' -97.9(4) 2 . . 2 ?
N1 Cu1 O1' O1' -19.8(6) 2 . . 2 ?
N1 Cu1 O1' O1' 167.5(4) . . . 2 ?
O1' Cu1 O1' S1 0.0 2 . . . ?
N2 Cu1 O1' S1 85.1(4) . . . . ?
N2 Cu1 O1' S1 -97.9(4) 2 . . . ?
N1 Cu1 O1' S1 -19.8(6) 2 . . . ?
N1 Cu1 O1' S1 167.5(4) . . . . ?
O1' Cu1 N2 C1 -75.3(3) . . . . ?
O1' Cu1 N2 C1 -38.3(3) 2 . . . ?
N2 Cu1 N2 C1 123.3(3) 2 . . . ?
N1 Cu1 N2 C1 68.2(3) 2 . . . ?
N1 Cu1 N2 C1 179.2(3) . . . . ?
O1' Cu1 N2 C12 108.5(2) . . . . ?
O1' Cu1 N2 C12 145.4(2) 2 . . . ?
N2 Cu1 N2 C12 -53.01(19) 2 . . . ?
N1 Cu1 N2 C12 -108.1(2) 2 . . . ?
N1 Cu1 N2 C12 2.9(2) . . . . ?
O1' Cu1 N1 C10 82.6(3) . . . . ?
O1' Cu1 N1 C10 94.9(4) 2 . . . ?
N2 Cu1 N1 C10 176.8(3) . . . . ?
N2 Cu1 N1 C10 -10.9(3) 2 . . . ?
N1 Cu1 N1 C10 -92.6(3) 2 . . . ?
O1' Cu1 N1 C11 -95.8(2) . . . . ?
O1' Cu1 N1 C11 -83.5(3) 2 . . . ?
N2 Cu1 N1 C11 -1.53(19) . . . . ?
N2 Cu1 N1 C11 170.72(19) 2 . . . ?
N1 Cu1 N1 C11 89.02(19) 2 . . . ?
C11 N1 C10 C9 0.0(5) . . . . ?
Cu1 N1 C10 C9 -178.2(3) . . . . ?
N1 C10 C9 C8 -0.6(5) . . . . ?
C10 C9 C8 C7 0.3(5) . . . . ?
C9 C8 C7 C11 0.4(5) . . . . ?
C9 C8 C7 C6 179.4(3) . . . . ?
C10 N1 C11 C7 0.8(4) . . . . ?
Cu1 N1 C11 C7 179.4(2) . . . . ?
C10 N1 C11 C12 -178.7(3) . . . . ?
Cu1 N1 C11 C12 -0.1(3) . . . . ?
C8 C7 C11 N1 -1.0(4) . . . . ?
C6 C7 C11 N1 180.0(3) . . . . ?
C8 C7 C11 C12 178.4(3) . . . . ?
C6 C7 C11 C12 -0.5(4) . . . . ?
C1 N2 C12 C4 1.1(4) . . . . ?
Cu1 N2 C12 C4 177.7(2) . . . . ?
C1 N2 C12 C11 179.5(3) . . . . ?
Cu1 N2 C12 C11 -3.9(3) . . . . ?
N1 C11 C12 N2 2.6(4) . . . . ?
C7 C11 C12 N2 -176.9(3) . . . . ?
N1 C11 C12 C4 -179.0(3) . . . . ?
C7 C11 C12 C4 1.5(4) . . . . ?
C11 C7 C6 C5 -0.8(5) . . . . ?
C8 C7 C6 C5 -179.7(3) . . . . ?
N2 C12 C4 C3 -1.7(4) . . . . ?
C11 C12 C4 C3 179.9(3) . . . . ?
N2 C12 C4 C5 177.1(3) . . . . ?
C11 C12 C4 C5 -1.2(4) . . . . ?
C12 C4 C3 C2 0.7(5) . . . . ?
C5 C4 C3 C2 -178.1(3) . . . . ?
C4 C3 C2 C1 0.8(5) . . . . ?
C12 N2 C1 C2 0.6(5) . . . . ?
Cu1 N2 C1 C2 -175.5(2) . . . . ?
C3 C2 C1 N2 -1.6(5) . . . . ?
C7 C6 C5 C4 1.1(5) . . . . ?
C12 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C6 178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.922
_refine_diff_density_min         -1.321
_refine_diff_density_rms         0.072
