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

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

data_1SH785
_database_code_depnum_ccdc_archive 'CCDC 1040994'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cu N2 O4 S1, C2 H6 O1 S1'
_chemical_formula_sum            'C20 H19 Cu N2 O5 S2'
_chemical_formula_weight         495.03

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7839(3)
_cell_length_b                   12.0077(4)
_cell_length_c                   14.7160(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.4910(10)
_cell_angle_gamma                90
_cell_volume                     2075.88(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      26.35

_exptl_crystal_description       cubic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.289
_shelx_estimated_absorpt_T_min   0.765
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7648
_exptl_absorpt_correction_T_max  0.8197
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38434
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4254
_reflns_number_gt                3285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0597P)²+0.9549P] 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_number_reflns         4254
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.46785(3) 0.05157(2) 0.09365(2) 0.03197(12) Uani 1 1 d . . . . .
S2 S -0.06077(9) 0.30105(11) 0.97258(8) 0.0838(4) Uani 1 1 d . . . . .
S1 S 0.28719(6) 0.05091(6) 0.22788(5) 0.04193(19) Uani 1 1 d . . . . .
O5 O -0.1355(3) 0.3817(4) 1.0147(3) 0.1251(14) Uani 1 1 d . . . . .
O3 O 0.3689(2) 0.0895(2) 0.29712(18) 0.0774(8) Uani 1 1 d . . . . .
O2 O 0.31898(18) 0.08282(17) 0.13622(15) 0.0517(6) Uani 1 1 d . . . . .
O4 O 0.1714(2) 0.0800(2) 0.23725(19) 0.0707(7) Uani 1 1 d . . . . .
O1 O 0.60844(15) 0.02230(14) 0.04125(12) 0.0356(4) Uani 1 1 d . . . . .
N2 N 0.47861(18) 0.21407(17) 0.05700(15) 0.0334(5) Uani 1 1 d . . . . .
C11 C 0.2101(3) -0.2710(3) 0.2578(2) 0.0619(9) Uani 1 1 d . . . . .
H11 H 0.1510 -0.3114 0.2804 0.074 Uiso 1 1 calc R U . . .
C19 C 0.0497(5) 0.2713(6) 1.0580(4) 0.136(2) Uani 1 1 d . . . . .
H19A H 0.0866 0.3393 1.0779 0.203 Uiso 1 1 calc R U . . .
H19B H 0.1042 0.2224 1.0336 0.203 Uiso 1 1 calc R U . . .
H19C H 0.0181 0.2359 1.1088 0.203 Uiso 1 1 calc R U . . .
C20 C 0.0191(5) 0.3785(5) 0.8993(3) 0.120(2) Uani 1 1 d . . . . .
H20A H -0.0314 0.4171 0.8556 0.181 Uiso 1 1 calc R U . . .
H20B H 0.0671 0.3293 0.8680 0.181 Uiso 1 1 calc R U . . .
H20C H 0.0654 0.4316 0.9341 0.181 Uiso 1 1 calc R U . . .
C14 C 0.3865(2) 0.2770(2) 0.0383(2) 0.0500(8) Uani 1 1 d . . . . .
H14 H 0.3153 0.2444 0.0411 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3915(2) 0.3876(2) 0.0152(2) 0.0520(8) Uani 1 1 d . . . . .
H15 H 0.3246 0.4273 0.0014 0.062 Uiso 1 1 calc R U . . .
C16 C 0.4955(2) 0.44021(19) 0.01236(17) 0.0308(5) Uani 1 1 d . . . . .
C17 C 0.5909(2) 0.3749(2) 0.03211(19) 0.0383(6) Uani 1 1 d . . . . .
H17 H 0.6631 0.4059 0.0313 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5789(2) 0.2639(2) 0.05302(19) 0.0390(6) Uani 1 1 d . . . . .
H18 H 0.6444 0.2215 0.0650 0.047 Uiso 1 1 calc R U . . .
N1 N 0.48494(18) -0.08970(17) 0.16566(14) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.3894(2) -0.1505(2) 0.19506(17) 0.0347(6) Uani 1 1 d . . . . .
C13 C 0.2962(2) -0.0961(2) 0.22674(17) 0.0354(6) Uani 1 1 d . . . . .
C12 C 0.2085(3) -0.1566(3) 0.2600(2) 0.0485(7) Uani 1 1 d . . . . .
H12 H 0.1482 -0.1197 0.2838 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2992(3) -0.3259(3) 0.2222(2) 0.0588(9) Uani 1 1 d . . . . .
H10 H 0.2991 -0.4032 0.2192 0.071 Uiso 1 1 calc R U . . .
C9 C 0.3892(3) -0.2665(2) 0.1909(2) 0.0464(7) Uani 1 1 d . . . . .
H9 H 0.4493 -0.3039 0.1672 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5846(2) -0.1298(2) 0.19081(18) 0.0391(6) Uani 1 1 d . . . . .
H7 H 0.5871 -0.1896 0.2311 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6909(2) -0.0910(2) 0.1626(2) 0.0398(6) Uani 1 1 d . . . . .
C5 C 0.7918(3) -0.1310(3) 0.2101(2) 0.0582(9) Uani 1 1 d . . . . .
H5 H 0.7867 -0.1808 0.2580 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8951(3) -0.0983(4) 0.1871(3) 0.0740(11) Uani 1 1 d . . . . .
H4 H 0.9606 -0.1229 0.2205 0.089 Uiso 1 1 calc R U . . .
C3 C 0.9034(3) -0.0272(3) 0.1128(3) 0.0667(10) Uani 1 1 d . . . . .
H3 H 0.9749 -0.0060 0.0965 0.080 Uiso 1 1 calc R U . . .
C2 C 0.8088(2) 0.0115(3) 0.0639(2) 0.0510(8) Uani 1 1 d . . . . .
H2 H 0.8165 0.0579 0.0141 0.061 Uiso 1 1 calc R U . . .
C1 C 0.6994(2) -0.0180(2) 0.08805(19) 0.0369(6) 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 1.9140(17) . ?
Cu1 O2 1.9449(19) . ?
Cu1 N1 2.002(2) . ?
Cu1 N2 2.031(2) . ?
Cu1 O1 2.2928(19) 3_655 ?
S2 O5 1.477(4) . ?
S2 C20 1.753(5) . ?
S2 C19 1.774(5) . ?
S1 O4 1.426(2) . ?
S1 O3 1.424(3) . ?
S1 O2 1.478(2) . ?
S1 C13 1.769(3) . ?
O1 C1 1.320(3) . ?
O1 Cu1 2.2927(19) 3_655 ?
N2 C18 1.330(3) . ?
N2 C14 1.334(3) . ?
C11 C12 1.374(5) . ?
C11 C10 1.378(5) . ?
C11 H11 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C16 1.487(4) 3_665 ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 C7 1.296(3) . ?
N1 C8 1.437(3) . ?
C8 C13 1.389(4) . ?
C8 C9 1.394(4) . ?
C13 C12 1.383(4) . ?
C12 H12 0.9300 . ?
C10 C9 1.386(4) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C7 C6 1.428(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.415(4) . ?
C6 C1 1.415(4) . ?
C5 C4 1.348(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.395(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.361(5) . ?
C3 H3 0.9300 . ?
C2 C1 1.409(4) . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 175.04(8) . . ?
O1 Cu1 N1 90.18(8) . . ?
O2 Cu1 N1 92.80(8) . . ?
O1 Cu1 N2 89.74(8) . . ?
O2 Cu1 N2 88.67(8) . . ?
N1 Cu1 N2 161.60(9) . . ?
O1 Cu1 O1 82.72(7) . 3_655 ?
O2 Cu1 O1 92.93(8) . 3_655 ?
N1 Cu1 O1 98.45(7) . 3_655 ?
N2 Cu1 O1 99.80(8) . 3_655 ?
O5 S2 C20 106.1(3) . . ?
O5 S2 C19 105.3(3) . . ?
C20 S2 C19 98.3(3) . . ?
O4 S1 O3 116.74(17) . . ?
O4 S1 O2 109.73(14) . . ?
O3 S1 O2 111.29(15) . . ?
O4 S1 C13 107.68(14) . . ?
O3 S1 C13 107.10(15) . . ?
O2 S1 C13 103.32(12) . . ?
S1 O2 Cu1 122.90(13) . . ?
C1 O1 Cu1 123.40(17) . . ?
C1 O1 Cu1 123.88(15) . 3_655 ?
Cu1 O1 Cu1 97.28(7) . 3_655 ?
C18 N2 C14 116.6(2) . . ?
C18 N2 Cu1 121.19(17) . . ?
C14 N2 Cu1 122.18(18) . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
S2 C19 H19A 109.5 . . ?
S2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
S2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C14 C15 123.3(3) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 116.3(2) . . ?
C17 C16 C16 121.8(3) . 3_665 ?
C15 C16 C16 121.9(3) . 3_665 ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N2 C18 C17 123.5(2) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C7 N1 C8 116.0(2) . . ?
C7 N1 Cu1 121.16(18) . . ?
C8 N1 Cu1 122.77(16) . . ?
C13 C8 C9 119.0(3) . . ?
C13 C8 N1 121.4(2) . . ?
C9 C8 N1 119.6(3) . . ?
C12 C13 C8 120.3(3) . . ?
C12 C13 S1 118.3(2) . . ?
C8 C13 S1 121.4(2) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N1 C7 C6 126.3(2) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 117.9(3) . . ?
C1 C6 C7 123.0(2) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O1 C1 C2 119.9(3) . . ?
O1 C1 C6 121.8(2) . . ?
C2 C1 C6 118.3(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
O4 S1 O2 Cu1 -177.13(16) . . . . ?
O3 S1 O2 Cu1 52.1(2) . . . . ?
C13 S1 O2 Cu1 -62.52(18) . . . . ?
C18 N2 C14 C15 0.5(5) . . . . ?
Cu1 N2 C14 C15 178.6(3) . . . . ?
N2 C14 C15 C16 -1.5(5) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
C14 C15 C16 C16 180.0(3) . . . 3_665 ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C16 C17 C18 -178.8(3) 3_665 . . . ?
C14 N2 C18 C17 0.8(4) . . . . ?
Cu1 N2 C18 C17 -177.3(2) . . . . ?
C16 C17 C18 N2 -1.1(5) . . . . ?
C7 N1 C8 C13 138.3(3) . . . . ?
Cu1 N1 C8 C13 -39.7(3) . . . . ?
C7 N1 C8 C9 -42.4(3) . . . . ?
Cu1 N1 C8 C9 139.6(2) . . . . ?
C9 C8 C13 C12 4.8(4) . . . . ?
N1 C8 C13 C12 -176.0(2) . . . . ?
C9 C8 C13 S1 -176.4(2) . . . . ?
N1 C8 C13 S1 2.8(3) . . . . ?
O4 S1 C13 C12 -18.3(3) . . . . ?
O3 S1 C13 C12 108.1(2) . . . . ?
O2 S1 C13 C12 -134.3(2) . . . . ?
O4 S1 C13 C8 162.9(2) . . . . ?
O3 S1 C13 C8 -70.8(3) . . . . ?
O2 S1 C13 C8 46.8(2) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C8 C13 C12 C11 -3.2(4) . . . . ?
S1 C13 C12 C11 178.0(2) . . . . ?
C12 C11 C10 C9 1.9(5) . . . . ?
C11 C10 C9 C8 -0.3(5) . . . . ?
C13 C8 C9 C10 -3.0(4) . . . . ?
N1 C8 C9 C10 177.7(3) . . . . ?
C8 N1 C7 C6 173.3(3) . . . . ?
Cu1 N1 C7 C6 -8.7(4) . . . . ?
N1 C7 C6 C5 168.3(3) . . . . ?
N1 C7 C6 C1 -13.9(4) . . . . ?
C1 C6 C5 C4 1.9(5) . . . . ?
C7 C6 C5 C4 179.8(3) . . . . ?
C6 C5 C4 C3 -2.7(6) . . . . ?
C5 C4 C3 C2 1.2(6) . . . . ?
C4 C3 C2 C1 1.0(5) . . . . ?
Cu1 O1 C1 C2 -148.8(2) . . . . ?
Cu1 O1 C1 C2 82.5(3) 3_655 . . . ?
Cu1 O1 C1 C6 31.3(3) . . . . ?
Cu1 O1 C1 C6 -97.4(3) 3_655 . . . ?
C3 C2 C1 O1 178.5(3) . . . . ?
C3 C2 C1 C6 -1.7(4) . . . . ?
C5 C6 C1 O1 -179.9(3) . . . . ?
C7 C6 C1 O1 2.4(4) . . . . ?
C5 C6 C1 C2 0.3(4) . . . . ?
C7 C6 C1 C2 -177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20B O4 0.96 2.60 3.134(5) 115.3 4_566
C20 H20C O5 0.96 2.49 3.392(7) 157.2 3_567
C14 H14 O2 0.93 2.39 2.886(3) 113.1 .
C17 H17 O5 0.93 2.42 3.255(4) 149.1 1_654
C18 H18 O1 0.93 2.45 2.928(3) 112.0 .
C9 H9 O3 0.93 2.52 3.327(4) 146.0 2_645

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_2SH784
_database_code_depnum_ccdc_archive 'CCDC 1040995'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cu2 N4 O8 S2, 3(C1 H3 N1 O1), H2 O'
_chemical_formula_sum            'C39 H37 Cu2 N7 O12 S2'
_chemical_formula_weight         986.95

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.636(4)
_cell_length_b                   11.838(3)
_cell_length_c                   24.374(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.236(8)
_cell_angle_gamma                90
_cell_volume                     4142.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9800
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             2024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.200
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8132
_exptl_absorpt_correction_T_max  0.8694
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            72609
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         25.670
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7824
_reflns_number_gt                5921
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+4.5093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7824
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.15567(3) 0.55519(3) 0.27268(2) 0.02907(13) Uani 1 1 d . . . . .
Cu2 Cu 0.34349(3) 0.46576(3) 0.23901(2) 0.02930(13) Uani 1 1 d . . . . .
S1 S 0.03800(7) 0.54870(7) 0.36030(4) 0.0368(2) Uani 1 1 d . . . . .
S2 S 0.45388(6) 0.47648(7) 0.14538(4) 0.0349(2) Uani 1 1 d . . . . .
O12 O 0.1509(3) 0.3531(4) 0.5565(2) 0.1123(15) Uani 1 1 d . . . . .
O5 O 0.30532(16) 0.49490(18) 0.30867(9) 0.0319(5) Uani 1 1 d . . . . .
O1 O 0.19426(16) 0.52775(18) 0.20323(9) 0.0313(5) Uani 1 1 d . . . . .
O4 O 0.0326(2) 0.5811(2) 0.41607(11) 0.0521(7) Uani 1 1 d . . . . .
O3 O -0.0397(2) 0.5804(2) 0.31782(13) 0.0571(8) Uani 1 1 d . . . . .
O2 O 0.12754(18) 0.5875(2) 0.34665(10) 0.0412(6) Uani 1 1 d . . . . .
O8 O 0.4465(2) 0.4493(2) 0.08741(11) 0.0523(7) Uani 1 1 d . . . . .
O7 O 0.5387(2) 0.4425(2) 0.18119(13) 0.0575(8) Uani 1 1 d . . . . .
O6 O 0.37131(19) 0.4343(2) 0.16525(11) 0.0459(7) Uani 1 1 d . . . . .
N6 N 0.3762(3) 0.9541(5) 0.4529(2) 0.1005(17) Uani 1 1 d . . . . .
H6A H 0.3679 1.0258 0.4553 0.121 Uiso 1 1 calc R U . . .
H6B H 0.4261 0.9288 0.4435 0.121 Uiso 1 1 calc R U . . .
O10 O 0.2414(3) 0.9060(4) 0.4767(3) 0.136(2) Uani 1 1 d . . . . .
O9 O 0.3434(3) 0.1989(5) 0.4453(2) 0.1220(17) Uani 1 1 d . . . . .
N2 N 0.1883(2) 0.7217(2) 0.26703(11) 0.0313(6) Uani 1 1 d . . . . .
C16 C 0.2360(2) 0.9503(2) 0.25854(14) 0.0292(7) Uani 1 1 d . . . . .
C19 C 0.2630(2) 1.0710(3) 0.25385(14) 0.0297(7) Uani 1 1 d . . . . .
N3 N 0.30974(19) 0.3000(2) 0.24486(11) 0.0296(6) Uani 1 1 d . . . . .
N4 N 0.41412(19) 0.6121(2) 0.24600(11) 0.0306(6) Uani 1 1 d . . . . .
O11 O 0.2062(4) 0.5693(5) 0.5777(2) 0.1320(19) Uani 1 1 d . . . . .
C37 C 0.2915(4) 0.2378(6) 0.4738(3) 0.0901(18) Uani 1 1 d . . . . .
H37 H 0.2544 0.2982 0.4586 0.108 Uiso 1 1 calc R U . . .
N5 N 0.2823(4) 0.2050(4) 0.5218(2) 0.0966(15) Uani 1 1 d . . . . .
H5A H 0.3151 0.1494 0.5377 0.116 Uiso 1 1 calc R U . . .
H5B H 0.2434 0.2384 0.5386 0.116 Uiso 1 1 calc R U . . .
C1 C 0.1399(2) 0.4816(3) 0.15892(14) 0.0311(7) Uani 1 1 d . . . . .
C6 C 0.0657(2) 0.4078(3) 0.16349(14) 0.0329(8) Uani 1 1 d . . . . .
C7 C 0.0483(2) 0.3698(3) 0.21602(14) 0.0334(8) Uani 1 1 d . . . . .
H7 H 0.0068 0.3100 0.2150 0.040 Uiso 1 1 calc R U . . .
N1 N 0.08390(19) 0.4094(2) 0.26488(11) 0.0297(6) Uani 1 1 d . . . . .
C8 C 0.0682(2) 0.3455(3) 0.31243(14) 0.0335(8) Uani 1 1 d . . . . .
C13 C 0.0474(2) 0.3996(3) 0.35947(15) 0.0357(8) Uani 1 1 d . . . . .
C12 C 0.0331(3) 0.3364(4) 0.40518(17) 0.0511(10) Uani 1 1 d . . . . .
H12 H 0.0178 0.3723 0.4361 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0415(3) 0.2206(4) 0.40450(19) 0.0625(13) Uani 1 1 d . . . . .
H11 H 0.0328 0.1785 0.4353 0.075 Uiso 1 1 calc R U . . .
C10 C 0.0625(3) 0.1671(3) 0.35856(19) 0.0550(11) Uani 1 1 d . . . . .
H10 H 0.0678 0.0888 0.3585 0.066 Uiso 1 1 calc R U . . .
C9 C 0.0759(3) 0.2280(3) 0.31256(17) 0.0434(9) Uani 1 1 d . . . . .
H9A H 0.0901 0.1908 0.2817 0.052 Uiso 1 1 calc R U . . .
C5 C 0.0099(3) 0.3637(3) 0.11424(16) 0.0445(9) Uani 1 1 d . . . . .
H5 H -0.0392 0.3155 0.1170 0.053 Uiso 1 1 calc R U . . .
C4 C 0.0266(3) 0.3903(4) 0.06281(16) 0.0539(11) Uani 1 1 d . . . . .
H4 H -0.0116 0.3621 0.0308 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1012(3) 0.4599(3) 0.05851(16) 0.0511(11) Uani 1 1 d . . . . .
H3 H 0.1139 0.4760 0.0234 0.061 Uiso 1 1 calc R U . . .
C2 C 0.1570(3) 0.5057(3) 0.10551(15) 0.0403(9) Uani 1 1 d . . . . .
H2 H 0.2062 0.5528 0.1017 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2209(3) 0.7843(3) 0.31244(15) 0.0400(9) Uani 1 1 d . . . . .
H14 H 0.2273 0.7506 0.3474 0.048 Uiso 1 1 calc R U . . .
C15 C 0.2455(3) 0.8962(3) 0.30977(15) 0.0416(9) Uani 1 1 d . . . . .
H15 H 0.2687 0.9357 0.3425 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2958(2) 1.1369(3) 0.30055(15) 0.0354(8) Uani 1 1 d . . . . .
H20 H 0.3032 1.1054 0.3361 0.042 Uiso 1 1 calc R U . . .
C21 C 0.3176(2) 0.2493(3) 0.29449(14) 0.0350(8) Uani 1 1 d . . . . .
H21 H 0.3388 0.2917 0.3266 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3594(2) 0.5411(3) 0.35262(13) 0.0304(7) Uani 1 1 d . . . . .
C29 C 0.4342(2) 0.6147(3) 0.34786(14) 0.0330(8) Uani 1 1 d . . . . .
C30 C 0.4509(2) 0.6521(3) 0.29484(14) 0.0342(8) Uani 1 1 d . . . . .
H30 H 0.4926 0.7115 0.2955 0.041 Uiso 1 1 calc R U . . .
C31 C 0.4293(2) 0.6772(3) 0.19895(14) 0.0337(8) Uani 1 1 d . . . . .
C36 C 0.4468(2) 0.6257(3) 0.14991(14) 0.0314(7) Uani 1 1 d . . . . .
C35 C 0.4625(3) 0.6916(3) 0.10577(15) 0.0430(9) Uani 1 1 d . . . . .
H35 H 0.4753 0.6572 0.0738 0.052 Uiso 1 1 calc R U . . .
C34 C 0.4594(3) 0.8076(3) 0.10862(17) 0.0515(11) Uani 1 1 d . . . . .
H34 H 0.4719 0.8512 0.0792 0.062 Uiso 1 1 calc R U . . .
C33 C 0.4375(3) 0.8597(3) 0.15564(17) 0.0483(10) Uani 1 1 d . . . . .
H33 H 0.4325 0.9380 0.1570 0.058 Uiso 1 1 calc R U . . .
C32 C 0.4231(3) 0.7947(3) 0.20031(16) 0.0413(9) Uani 1 1 d . . . . .
H32 H 0.4091 0.8299 0.2318 0.050 Uiso 1 1 calc R U . . .
C28 C 0.4897(3) 0.6607(3) 0.39667(16) 0.0467(10) Uani 1 1 d . . . . .
H28 H 0.5385 0.7091 0.3936 0.056 Uiso 1 1 calc R U . . .
C27 C 0.4726(3) 0.6353(4) 0.44816(16) 0.0552(11) Uani 1 1 d . . . . .
H27 H 0.5103 0.6650 0.4801 0.066 Uiso 1 1 calc R U . . .
C26 C 0.3984(3) 0.5645(4) 0.45284(16) 0.0536(11) Uani 1 1 d . . . . .
H26 H 0.3863 0.5480 0.4880 0.064 Uiso 1 1 calc R U . . .
C25 C 0.3429(3) 0.5189(3) 0.40613(15) 0.0437(9) Uani 1 1 d . . . . .
H25 H 0.2934 0.4724 0.4102 0.052 Uiso 1 1 calc R U . . .
C22 C 0.2791(3) 0.2363(3) 0.19950(15) 0.0386(9) Uani 1 1 d . . . . .
H22 H 0.2739 0.2694 0.1644 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2550(3) 1.1243(3) 0.20228(14) 0.0390(9) Uani 1 1 d . . . . .
H23 H 0.2333 1.0842 0.1695 0.047 Uiso 1 1 calc R U . . .
C17 C 0.2006(3) 0.8855(3) 0.21178(15) 0.0362(8) Uani 1 1 d . . . . .
H17 H 0.1916 0.9177 0.1763 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1787(2) 0.7736(3) 0.21779(15) 0.0355(8) Uani 1 1 d . . . . .
H18 H 0.1560 0.7319 0.1857 0.043 Uiso 1 1 calc R U . . .
C39 C 0.2118(4) 0.6622(6) 0.5560(3) 0.0897(18) Uani 1 1 d . . . . .
H39 H 0.2475 0.7168 0.5778 0.108 Uiso 1 1 calc R U . . .
N7 N 0.1734(3) 0.6910(5) 0.5064(2) 0.0944(15) Uani 1 1 d . . . . .
H7A H 0.1397 0.6432 0.4848 0.113 Uiso 1 1 calc R U . . .
H7B H 0.1811 0.7581 0.4946 0.113 Uiso 1 1 calc R U . . .
C38 C 0.3145(5) 0.8856(6) 0.4632(3) 0.0938(19) Uani 1 1 d . . . . .
H38 H 0.3279 0.8093 0.4599 0.113 Uiso 1 1 calc R U . . .
H12A H 0.1633 0.4258 0.5620 0.141 Uiso 1 1 d R U . . .
H12B H 0.0953 0.3442 0.5626 0.141 Uiso 1 1 d R U . . .


_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 1.914(2) . ?
Cu1 O2 1.963(2) . ?
Cu1 N1 2.010(3) . ?
Cu1 N2 2.039(3) . ?
Cu1 O5 2.308(2) . ?
Cu2 O5 1.919(2) . ?
Cu2 O6 1.955(2) . ?
Cu2 N4 2.008(3) . ?
Cu2 N3 2.035(3) . ?
Cu2 O1 2.308(2) . ?
S1 O4 1.429(3) . ?
S1 O3 1.430(3) . ?
S1 O2 1.486(3) . ?
S1 C13 1.771(4) . ?
S2 O7 1.429(3) . ?
S2 O8 1.432(3) . ?
S2 O6 1.474(3) . ?
S2 C36 1.774(3) . ?
O12 H12A 0.8841 . ?
O12 H12B 0.8623 . ?
O5 C24 1.320(4) . ?
O1 C1 1.327(4) . ?
N6 C38 1.275(8) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
O10 C38 1.204(7) . ?
O9 C37 1.216(7) . ?
N2 C18 1.331(4) . ?
N2 C14 1.340(4) . ?
C16 C15 1.386(5) . ?
C16 C17 1.388(5) . ?
C16 C19 1.492(4) . ?
C19 C20 1.387(5) . ?
C19 C23 1.391(5) . ?
N3 C21 1.335(4) . ?
N3 C22 1.341(4) . ?
N4 C30 1.296(4) . ?
N4 C31 1.434(4) . ?
O11 C39 1.231(7) . ?
C37 N5 1.265(7) . ?
C37 H37 0.9300 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
C1 C2 1.402(5) . ?
C1 C6 1.416(5) . ?
C6 C5 1.414(5) . ?
C6 C7 1.426(5) . ?
C7 N1 1.291(4) . ?
C7 H7 0.9300 . ?
N1 C8 1.439(4) . ?
C8 C9 1.396(5) . ?
C8 C13 1.397(5) . ?
C13 C12 1.391(5) . ?
C12 C11 1.376(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.373(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.379(5) . ?
C10 H10 0.9300 . ?
C9 H9A 0.9300 . ?
C5 C4 1.360(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.388(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.381(5) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C20 C21 1.383(5) 1_565 ?
C20 H20 0.9300 . ?
C21 C20 1.383(5) 1_545 ?
C21 H21 0.9300 . ?
C24 C25 1.397(5) . ?
C24 C29 1.421(5) . ?
C29 C28 1.412(5) . ?
C29 C30 1.431(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.395(5) . ?
C31 C36 1.409(5) . ?
C36 C35 1.384(5) . ?
C35 C34 1.376(5) . ?
C35 H35 0.9300 . ?
C34 C33 1.393(6) . ?
C34 H34 0.9300 . ?
C33 C32 1.382(5) . ?
C33 H33 0.9300 . ?
C32 H32 0.9300 . ?
C28 C27 1.360(5) . ?
C28 H28 0.9300 . ?
C27 C26 1.394(6) . ?
C27 H27 0.9300 . ?
C26 C25 1.374(6) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C22 C23 1.377(5) 1_545 ?
C22 H22 0.9300 . ?
C23 C22 1.377(5) 1_565 ?
C23 H23 0.9300 . ?
C17 C18 1.378(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C39 N7 1.276(7) . ?
C39 H39 0.9300 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
C38 H38 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 174.90(10) . . ?
O1 Cu1 N1 90.53(10) . . ?
O2 Cu1 N1 93.15(10) . . ?
O1 Cu1 N2 89.49(10) . . ?
O2 Cu1 N2 88.13(10) . . ?
N1 Cu1 N2 161.54(11) . . ?
O1 Cu1 O5 82.06(9) . . ?
O2 Cu1 O5 93.70(10) . . ?
N1 Cu1 O5 102.13(10) . . ?
N2 Cu1 O5 96.16(10) . . ?
O5 Cu2 O6 175.18(10) . . ?
O5 Cu2 N4 90.21(10) . . ?
O6 Cu2 N4 92.67(10) . . ?
O5 Cu2 N3 89.71(10) . . ?
O6 Cu2 N3 88.70(10) . . ?
N4 Cu2 N3 162.58(11) . . ?
O5 Cu2 O1 81.95(9) . . ?
O6 Cu2 O1 93.70(10) . . ?
N4 Cu2 O1 101.02(10) . . ?
N3 Cu2 O1 96.22(10) . . ?
O4 S1 O3 115.74(18) . . ?
O4 S1 O2 110.17(16) . . ?
O3 S1 O2 111.57(17) . . ?
O4 S1 C13 107.31(17) . . ?
O3 S1 C13 107.81(17) . . ?
O2 S1 C13 103.37(16) . . ?
O7 S2 O8 115.40(19) . . ?
O7 S2 O6 111.94(18) . . ?
O8 S2 O6 109.81(16) . . ?
O7 S2 C36 107.27(16) . . ?
O8 S2 C36 106.91(16) . . ?
O6 S2 C36 104.80(15) . . ?
H12A O12 H12B 105.4 . . ?
C24 O5 Cu2 124.1(2) . . ?
C24 O5 Cu1 123.7(2) . . ?
Cu2 O5 Cu1 97.91(9) . . ?
C1 O1 Cu1 123.8(2) . . ?
C1 O1 Cu2 123.33(19) . . ?
Cu1 O1 Cu2 98.07(9) . . ?
S1 O2 Cu1 119.82(15) . . ?
S2 O6 Cu2 124.65(15) . . ?
C38 N6 H6A 120.0 . . ?
C38 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C18 N2 C14 116.6(3) . . ?
C18 N2 Cu1 121.4(2) . . ?
C14 N2 Cu1 122.0(2) . . ?
C15 C16 C17 116.1(3) . . ?
C15 C16 C19 122.0(3) . . ?
C17 C16 C19 121.9(3) . . ?
C20 C19 C23 116.2(3) . . ?
C20 C19 C16 122.0(3) . . ?
C23 C19 C16 121.8(3) . . ?
C21 N3 C22 116.8(3) . . ?
C21 N3 Cu2 121.2(2) . . ?
C22 N3 Cu2 122.1(2) . . ?
C30 N4 C31 115.9(3) . . ?
C30 N4 Cu2 120.5(2) . . ?
C31 N4 Cu2 123.6(2) . . ?
O9 C37 N5 127.2(6) . . ?
O9 C37 H37 116.4 . . ?
N5 C37 H37 116.4 . . ?
C37 N5 H5A 120.0 . . ?
C37 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 118.5(3) . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 118.1(3) . . ?
C1 C6 C7 122.6(3) . . ?
N1 C7 C6 127.1(3) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
C7 N1 C8 116.9(3) . . ?
C7 N1 Cu1 120.6(2) . . ?
C8 N1 Cu1 122.5(2) . . ?
C9 C8 C13 119.0(3) . . ?
C9 C8 N1 120.0(3) . . ?
C13 C8 N1 121.0(3) . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 S1 120.1(3) . . ?
C8 C13 S1 119.7(3) . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C9 C8 119.9(4) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N2 C14 C15 123.2(3) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C21 C20 C19 120.3(3) 1_565 . ?
C21 C20 H20 119.9 1_565 . ?
C19 C20 H20 119.9 . . ?
N3 C21 C20 123.2(3) . 1_545 ?
N3 C21 H21 118.4 . . ?
C20 C21 H21 118.4 1_545 . ?
O5 C24 C25 119.6(3) . . ?
O5 C24 C29 122.5(3) . . ?
C25 C24 C29 117.9(3) . . ?
C28 C29 C24 119.5(3) . . ?
C28 C29 C30 118.1(3) . . ?
C24 C29 C30 122.2(3) . . ?
N4 C30 C29 127.1(3) . . ?
N4 C30 H30 116.5 . . ?
C29 C30 H30 116.5 . . ?
C32 C31 C36 118.3(3) . . ?
C32 C31 N4 119.7(3) . . ?
C36 C31 N4 121.9(3) . . ?
C35 C36 C31 120.1(3) . . ?
C35 C36 S2 119.5(3) . . ?
C31 C36 S2 120.4(2) . . ?
C34 C35 C36 120.7(4) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C34 C33 119.9(4) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C32 C33 C34 119.7(4) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C32 C31 121.1(4) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C27 C28 C29 120.9(4) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C27 C26 119.6(4) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C25 C26 C27 120.9(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
N3 C22 C23 123.2(3) . 1_545 ?
N3 C22 H22 118.4 . . ?
C23 C22 H22 118.4 1_545 . ?
C22 C23 C19 120.3(3) 1_565 . ?
C22 C23 H23 119.9 1_565 . ?
C19 C23 H23 119.9 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N2 C18 C17 123.6(3) . . ?
N2 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
O11 C39 N7 126.3(6) . . ?
O11 C39 H39 116.8 . . ?
N7 C39 H39 116.8 . . ?
C39 N7 H7A 120.0 . . ?
C39 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O10 C38 N6 128.8(7) . . ?
O10 C38 H38 115.6 . . ?
N6 C38 H38 115.6 . . ?

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
O4 S1 O2 Cu1 179.88(17) . . . . ?
O3 S1 O2 Cu1 -50.1(2) . . . . ?
C13 S1 O2 Cu1 65.5(2) . . . . ?
O7 S2 O6 Cu2 57.6(2) . . . . ?
O8 S2 O6 Cu2 -172.85(18) . . . . ?
C36 S2 O6 Cu2 -58.3(2) . . . . ?
C15 C16 C19 C20 -2.6(5) . . . . ?
C17 C16 C19 C20 178.0(3) . . . . ?
C15 C16 C19 C23 178.7(3) . . . . ?
C17 C16 C19 C23 -0.7(5) . . . . ?
Cu1 O1 C1 C2 154.1(2) . . . . ?
Cu2 O1 C1 C2 -75.9(3) . . . . ?
Cu1 O1 C1 C6 -26.6(4) . . . . ?
Cu2 O1 C1 C6 103.4(3) . . . . ?
O1 C1 C6 C5 178.9(3) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
O1 C1 C6 C7 -5.4(5) . . . . ?
C2 C1 C6 C7 174.0(3) . . . . ?
C5 C6 C7 N1 -171.3(3) . . . . ?
C1 C6 C7 N1 12.9(5) . . . . ?
C6 C7 N1 C8 -169.9(3) . . . . ?
C6 C7 N1 Cu1 11.2(5) . . . . ?
C7 N1 C8 C9 42.7(5) . . . . ?
Cu1 N1 C8 C9 -138.4(3) . . . . ?
C7 N1 C8 C13 -139.0(3) . . . . ?
Cu1 N1 C8 C13 39.9(4) . . . . ?
C9 C8 C13 C12 -1.2(5) . . . . ?
N1 C8 C13 C12 -179.6(3) . . . . ?
C9 C8 C13 S1 179.6(3) . . . . ?
N1 C8 C13 S1 1.3(5) . . . . ?
O4 S1 C13 C12 10.6(4) . . . . ?
O3 S1 C13 C12 -114.7(3) . . . . ?
O2 S1 C13 C12 127.0(3) . . . . ?
O4 S1 C13 C8 -170.3(3) . . . . ?
O3 S1 C13 C8 64.4(3) . . . . ?
O2 S1 C13 C8 -53.8(3) . . . . ?
C8 C13 C12 C11 1.5(6) . . . . ?
S1 C13 C12 C11 -179.3(3) . . . . ?
C13 C12 C11 C10 -1.0(7) . . . . ?
C12 C11 C10 C9 0.2(7) . . . . ?
C11 C10 C9 C8 0.0(6) . . . . ?
C13 C8 C9 C10 0.5(6) . . . . ?
N1 C8 C9 C10 178.8(3) . . . . ?
C1 C6 C5 C4 0.4(6) . . . . ?
C7 C6 C5 C4 -175.5(4) . . . . ?
C6 C5 C4 C3 1.6(6) . . . . ?
C5 C4 C3 C2 -2.2(6) . . . . ?
C4 C3 C2 C1 0.7(6) . . . . ?
O1 C1 C2 C3 -179.4(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C18 N2 C14 C15 -1.1(6) . . . . ?
Cu1 N2 C14 C15 178.5(3) . . . . ?
N2 C14 C15 C16 0.9(6) . . . . ?
C17 C16 C15 C14 0.3(5) . . . . ?
C19 C16 C15 C14 -179.1(3) . . . . ?
C23 C19 C20 C21 0.7(5) . . . 1_565 ?
C16 C19 C20 C21 -178.1(3) . . . 1_565 ?
C22 N3 C21 C20 -0.1(5) . . . 1_545 ?
Cu2 N3 C21 C20 -179.8(3) . . . 1_545 ?
Cu2 O5 C24 C25 -154.2(3) . . . . ?
Cu1 O5 C24 C25 75.2(4) . . . . ?
Cu2 O5 C24 C29 26.6(4) . . . . ?
Cu1 O5 C24 C29 -104.0(3) . . . . ?
O5 C24 C29 C28 -179.7(3) . . . . ?
C25 C24 C29 C28 1.1(5) . . . . ?
O5 C24 C29 C30 5.8(5) . . . . ?
C25 C24 C29 C30 -173.4(3) . . . . ?
C31 N4 C30 C29 169.2(3) . . . . ?
Cu2 N4 C30 C29 -12.2(5) . . . . ?
C28 C29 C30 N4 172.7(3) . . . . ?
C24 C29 C30 N4 -12.8(6) . . . . ?
C30 N4 C31 C32 -41.5(5) . . . . ?
Cu2 N4 C31 C32 140.0(3) . . . . ?
C30 N4 C31 C36 141.1(3) . . . . ?
Cu2 N4 C31 C36 -37.4(4) . . . . ?
C32 C31 C36 C35 3.6(5) . . . . ?
N4 C31 C36 C35 -179.0(3) . . . . ?
C32 C31 C36 S2 -179.2(3) . . . . ?
N4 C31 C36 S2 -1.8(5) . . . . ?
O7 S2 C36 C35 106.2(3) . . . . ?
O8 S2 C36 C35 -18.2(3) . . . . ?
O6 S2 C36 C35 -134.7(3) . . . . ?
O7 S2 C36 C31 -71.1(3) . . . . ?
O8 S2 C36 C31 164.6(3) . . . . ?
O6 S2 C36 C31 48.1(3) . . . . ?
C31 C36 C35 C34 -1.4(6) . . . . ?
S2 C36 C35 C34 -178.6(3) . . . . ?
C36 C35 C34 C33 -1.9(6) . . . . ?
C35 C34 C33 C32 2.9(6) . . . . ?
C34 C33 C32 C31 -0.7(6) . . . . ?
C36 C31 C32 C33 -2.6(6) . . . . ?
N4 C31 C32 C33 180.0(3) . . . . ?
C24 C29 C28 C27 0.2(6) . . . . ?
C30 C29 C28 C27 174.9(4) . . . . ?
C29 C28 C27 C26 -1.2(6) . . . . ?
C28 C27 C26 C25 0.8(7) . . . . ?
C27 C26 C25 C24 0.5(6) . . . . ?
O5 C24 C25 C26 179.3(3) . . . . ?
C29 C24 C25 C26 -1.5(5) . . . . ?
C21 N3 C22 C23 0.9(5) . . . 1_545 ?
Cu2 N3 C22 C23 -179.4(3) . . . 1_545 ?
C20 C19 C23 C22 0.1(5) . . . 1_565 ?
C16 C19 C23 C22 178.9(3) . . . 1_565 ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C19 C16 C17 C18 178.3(3) . . . . ?
C14 N2 C18 C17 0.2(5) . . . . ?
Cu1 N2 C18 C17 -179.4(3) . . . . ?
C16 C17 C18 N2 0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O9 0.86 2.09 2.937(8) 169.6 1_565
N6 H6B O8 0.86 2.16 2.949(5) 152.8 2_655
N5 H5A O8 0.86 2.37 3.189(6) 158.7 4_566
N5 H5B O12 0.86 2.02 2.849(6) 160.6 .
C14 H14 O2 0.93 2.42 2.905(4) 112.5 .
C21 H21 O5 0.93 2.48 2.937(4) 110.7 .
C32 H32 O7 0.93 2.50 3.329(5) 149.3 2_655
C22 H22 O6 0.93 2.41 2.907(4) 113.0 .
C17 H17 O11 0.93 2.46 3.328(6) 155.6 4_575
N7 H7A O4 0.86 2.19 3.003(6) 158.5 .
N7 H7B O10 0.86 2.05 2.877(7) 162.3 .
O12 H12A O11 0.88 1.83 2.704(7) 171.6 .
O12 H12B O4 0.86 2.22 2.995(5) 149.2 3_566

_refine_diff_density_max         0.929
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.104

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_3SH774
_database_code_depnum_ccdc_archive 'CCDC 1040996'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cu N2 O4 S, C2 H5 N O'
_chemical_formula_sum            'C20 H18 Cu N3 O5 S'
_chemical_formula_weight         475.97

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3925(15)
_cell_length_b                   11.7576(12)
_cell_length_c                   14.4447(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.399(4)
_cell_angle_gamma                90
_cell_volume                     2037.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7552
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.28

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.212
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7942
_exptl_absorpt_correction_T_max  0.8491
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35054
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         25.673
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3861
_reflns_number_gt                2868
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²] 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_number_reflns         3861
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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 0.46333(3) -0.04327(3) 0.88490(3) 0.02878(13) Uani 1 1 d . . . . .
S1 S 0.28315(6) -0.03208(6) 0.66715(6) 0.0358(2) Uani 1 1 d . . . . .
O1 O 0.60433(16) -0.01667(16) 1.00174(15) 0.0307(5) Uani 1 1 d . . . . .
O2 O 0.31339(18) -0.07372(18) 0.77302(17) 0.0414(5) Uani 1 1 d . . . . .
O3 O 0.3656(2) -0.06320(19) 0.6345(2) 0.0523(6) Uani 1 1 d . . . . .
O4 O 0.16984(19) -0.0618(2) 0.59912(18) 0.0527(6) Uani 1 1 d . . . . .
N3 N 0.9936(4) 0.6082(5) 0.1596(3) 0.1007(15) Uani 1 1 d . . . . .
H3N H 1.0462 0.6015 0.1412 0.121 Uiso 1 1 calc R U . . .
O5 O 0.8545(3) 0.5172(5) 0.1745(4) 0.1486(19) Uani 1 1 d . . . . .
N1 N 0.47745(19) 0.10446(19) 0.82289(17) 0.0289(5) Uani 1 1 d . . . . .
C17 C 0.5881(2) -0.3740(2) 0.9992(2) 0.0355(7) Uani 1 1 d . . . . .
H17 H 0.6588 -0.4062 1.0304 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2873(2) 0.1180(3) 0.6821(2) 0.0339(7) Uani 1 1 d . . . . .
C8 C 0.3825(2) 0.1704(2) 0.7559(2) 0.0316(7) Uani 1 1 d . . . . .
C7 C 0.5753(2) 0.1447(2) 0.8411(2) 0.0356(7) Uani 1 1 d . . . . .
H7 H 0.5762 0.2063 0.8011 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6806(2) 0.1045(2) 0.9155(2) 0.0352(7) Uani 1 1 d . . . . .
C1 C 0.6924(2) 0.0278(2) 0.9952(2) 0.0311(7) Uani 1 1 d . . . . .
C2 C 0.8005(3) 0.0013(3) 1.0694(3) 0.0442(8) Uani 1 1 d . . . . .
H2 H 0.8101 -0.0470 1.1238 0.053 Uiso 1 1 calc R U . . .
C3 C 0.8928(3) 0.0451(3) 1.0636(3) 0.0592(10) Uani 1 1 d . . . . .
H3 H 0.9638 0.0254 1.1132 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8802(3) 0.1188(4) 0.9837(3) 0.0639(11) Uani 1 1 d . . . . .
H4 H 0.9427 0.1472 0.9793 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7776(3) 0.1489(3) 0.9129(3) 0.0520(9) Uani 1 1 d . . . . .
H5 H 0.7702 0.2000 0.8612 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3849(3) 0.2877(3) 0.7668(3) 0.0405(8) Uani 1 1 d . . . . .
H9 H 0.4488 0.3233 0.8152 0.049 Uiso 1 1 calc R U . . .
C10 C 0.2922(3) 0.3519(3) 0.7057(3) 0.0538(9) Uani 1 1 d . . . . .
H10 H 0.2935 0.4303 0.7143 0.065 Uiso 1 1 calc R U . . .
C11 C 0.1976(3) 0.3001(3) 0.6318(3) 0.0586(10) Uani 1 1 d . . . . .
H11 H 0.1358 0.3436 0.5903 0.070 Uiso 1 1 calc R U . . .
C12 C 0.1953(3) 0.1838(3) 0.6199(3) 0.0492(9) Uani 1 1 d . . . . .
H12 H 0.1319 0.1489 0.5700 0.059 Uiso 1 1 calc R U . . .
N2 N 0.47554(19) -0.21049(19) 0.92336(19) 0.0304(6) Uani 1 1 d . . . . .
C18 C 0.5752(3) -0.2623(2) 0.9692(2) 0.0362(7) Uani 1 1 d . . . . .
H18 H 0.6386 -0.2202 0.9812 0.043 Uiso 1 1 calc R U . . .
C16 C 0.4951(3) -0.4393(2) 0.9830(2) 0.0305(7) Uani 1 1 d . . . . .
C15 C 0.3914(3) -0.3862(3) 0.9347(2) 0.0386(7) Uani 1 1 d . . . . .
H15 H 0.3268 -0.4265 0.9218 0.046 Uiso 1 1 calc R U . . .
C14 C 0.3852(3) -0.2735(2) 0.9059(2) 0.0368(7) Uani 1 1 d . . . . .
H14 H 0.3153 -0.2396 0.8729 0.044 Uiso 1 1 calc R U . . .
C20 C 0.9780(6) 0.7148(6) 0.1972(6) 0.162(3) Uani 1 1 d . . . . .
H20A H 0.9113 0.7125 0.2064 0.243 Uiso 1 1 calc R U . . .
H20B H 0.9714 0.7733 0.1485 0.243 Uiso 1 1 calc R U . . .
H20C H 1.0407 0.7307 0.2623 0.243 Uiso 1 1 calc R U . . .
C19 C 0.9302(5) 0.5183(7) 0.1515(4) 0.1019(18) Uani 1 1 d . . . . .
H19 H 0.9457 0.4513 0.1263 0.122 Uiso 1 1 calc R U . . .


_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 1.9179(19) . ?
Cu1 O2 1.971(2) . ?
Cu1 N1 2.001(2) . ?
Cu1 N2 2.030(2) . ?
Cu1 O1 2.3061(19) 3_657 ?
S1 O3 1.427(2) . ?
S1 O4 1.437(2) . ?
S1 O2 1.481(2) . ?
S1 C13 1.775(3) . ?
O1 C1 1.330(3) . ?
O1 Cu1 2.3061(19) 3_657 ?
N3 C19 1.328(7) . ?
N3 C20 1.418(7) . ?
N3 H3N 0.8600 . ?
O5 C19 1.198(6) . ?
N1 C7 1.305(3) . ?
N1 C8 1.435(3) . ?
C17 C18 1.370(4) . ?
C17 C16 1.391(4) . ?
C17 H17 0.9300 . ?
C13 C8 1.391(4) . ?
C13 C12 1.392(4) . ?
C8 C9 1.387(4) . ?
C7 C6 1.421(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.415(4) . ?
C6 C1 1.417(4) . ?
C1 C2 1.401(4) . ?
C2 C3 1.376(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.345(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N2 C14 1.343(3) . ?
N2 C18 1.344(4) . ?
C18 H18 0.9300 . ?
C16 C15 1.394(4) . ?
C16 C16 1.496(5) 3_647 ?
C15 C14 1.381(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 175.23(8) . . ?
O1 Cu1 N1 90.02(9) . . ?
O2 Cu1 N1 93.17(9) . . ?
O1 Cu1 N2 89.38(9) . . ?
O2 Cu1 N2 88.69(9) . . ?
N1 Cu1 N2 161.98(9) . . ?
O1 Cu1 O1 82.49(8) . 3_657 ?
O2 Cu1 O1 93.38(8) . 3_657 ?
N1 Cu1 O1 101.40(8) . 3_657 ?
N2 Cu1 O1 96.37(8) . 3_657 ?
O3 S1 O4 116.64(15) . . ?
O3 S1 O2 111.10(14) . . ?
O4 S1 O2 110.27(13) . . ?
O3 S1 C13 107.94(14) . . ?
O4 S1 C13 106.93(14) . . ?
O2 S1 C13 102.93(13) . . ?
C1 O1 Cu1 123.97(18) . . ?
C1 O1 Cu1 124.78(17) . 3_657 ?
Cu1 O1 Cu1 97.51(8) . 3_657 ?
S1 O2 Cu1 119.85(12) . . ?
C19 N3 C20 122.6(5) . . ?
C19 N3 H3N 118.7 . . ?
C20 N3 H3N 118.7 . . ?
C7 N1 C8 116.7(2) . . ?
C7 N1 Cu1 120.70(19) . . ?
C8 N1 Cu1 122.58(18) . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C8 C13 C12 119.7(3) . . ?
C8 C13 S1 120.1(2) . . ?
C12 C13 S1 120.2(3) . . ?
C9 C8 C13 119.6(3) . . ?
C9 C8 N1 119.5(3) . . ?
C13 C8 N1 120.9(3) . . ?
N1 C7 C6 127.0(3) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 118.2(3) . . ?
C1 C6 C7 122.7(3) . . ?
O1 C1 C2 120.4(3) . . ?
O1 C1 C6 121.8(3) . . ?
C2 C1 C6 117.8(3) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 N2 C18 117.2(2) . . ?
C14 N2 Cu1 121.75(19) . . ?
C18 N2 Cu1 121.01(18) . . ?
N2 C18 C17 123.2(3) . . ?
N2 C18 H18 118.4 . . ?
C17 C18 H18 118.4 . . ?
C17 C16 C15 117.0(3) . . ?
C17 C16 C16 122.0(3) . 3_647 ?
C15 C16 C16 121.0(3) . 3_647 ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N2 C14 C15 123.0(3) . . ?
N2 C14 H14 118.5 . . ?
C15 C14 H14 118.5 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C19 N3 124.9(7) . . ?
O5 C19 H19 117.6 . . ?
N3 C19 H19 117.6 . . ?

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
O3 S1 O2 Cu1 50.27(19) . . . . ?
O4 S1 O2 Cu1 -178.82(14) . . . . ?
C13 S1 O2 Cu1 -65.03(17) . . . . ?
O3 S1 C13 C8 -63.5(3) . . . . ?
O4 S1 C13 C8 170.3(2) . . . . ?
O2 S1 C13 C8 54.1(3) . . . . ?
O3 S1 C13 C12 116.5(3) . . . . ?
O4 S1 C13 C12 -9.7(3) . . . . ?
O2 S1 C13 C12 -125.9(3) . . . . ?
C12 C13 C8 C9 -0.1(4) . . . . ?
S1 C13 C8 C9 179.9(2) . . . . ?
C12 C13 C8 N1 178.4(3) . . . . ?
S1 C13 C8 N1 -1.7(4) . . . . ?
C7 N1 C8 C9 -42.4(4) . . . . ?
Cu1 N1 C8 C9 138.5(2) . . . . ?
C7 N1 C8 C13 139.2(3) . . . . ?
Cu1 N1 C8 C13 -39.9(3) . . . . ?
C8 N1 C7 C6 170.1(3) . . . . ?
Cu1 N1 C7 C6 -10.7(4) . . . . ?
N1 C7 C6 C5 170.8(3) . . . . ?
N1 C7 C6 C1 -13.1(5) . . . . ?
Cu1 O1 C1 C2 -152.2(2) . . . . ?
Cu1 O1 C1 C2 76.6(3) 3_657 . . . ?
Cu1 O1 C1 C6 29.2(4) . . . . ?
Cu1 O1 C1 C6 -102.1(3) 3_657 . . . ?
C5 C6 C1 O1 179.9(3) . . . . ?
C7 C6 C1 O1 3.9(4) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
C7 C6 C1 C2 -174.7(3) . . . . ?
O1 C1 C2 C3 179.2(3) . . . . ?
C6 C1 C2 C3 -2.1(5) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -2.0(6) . . . . ?
C1 C6 C5 C4 0.8(5) . . . . ?
C7 C6 C5 C4 176.9(3) . . . . ?
C13 C8 C9 C10 1.2(5) . . . . ?
N1 C8 C9 C10 -177.3(3) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C8 C13 C12 C11 -0.7(5) . . . . ?
S1 C13 C12 C11 179.4(3) . . . . ?
C14 N2 C18 C17 -0.8(4) . . . . ?
Cu1 N2 C18 C17 178.1(2) . . . . ?
C16 C17 C18 N2 -0.3(5) . . . . ?
C18 C17 C16 C15 0.8(4) . . . . ?
C18 C17 C16 C16 -178.3(3) . . . 3_647 ?
C17 C16 C15 C14 -0.3(4) . . . . ?
C16 C16 C15 C14 178.8(3) 3_647 . . . ?
C18 N2 C14 C15 1.3(4) . . . . ?
Cu1 N2 C14 C15 -177.6(2) . . . . ?
C16 C15 C14 N2 -0.8(5) . . . . ?
C20 N3 C19 O5 0.1(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3N O4 0.86 2.06 2.909(5) 172.1 4_665
C9 H9 O3 0.93 2.62 3.470(4) 151.6 2_656
C15 H15 O5 0.93 2.44 3.329(5) 159.6 3_656
C14 H14 O2 0.93 2.42 2.912(4) 113.1 .

_refine_diff_density_max         0.689
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.097

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_4SH638
_database_code_depnum_ccdc_archive 'CCDC 1040997'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cu N2 O4 S, C3 H7 N O'
_chemical_formula_sum            'C21 H20 Cu N3 O5 S'
_chemical_formula_weight         490.00

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.169(4)
_cell_length_b                   12.142(4)
_cell_length_c                   14.346(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.212(13)
_cell_angle_gamma                90
_cell_volume                     2086.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9757
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.58

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.186
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8153
_exptl_absorpt_correction_T_max  0.8712
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71194
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.389
_diffrn_reflns_theta_max         30.657
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6436
_reflns_number_gt                5211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.6897P] 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_number_reflns         6436
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.53489(2) 0.44537(2) 0.90935(2) 0.02864(7) Uani 1 1 d . . . . .
S1 S 0.71082(4) 0.44258(3) 0.78759(4) 0.03710(11) Uani 1 1 d . . . . .
C21 C 0.0203(5) 0.7210(4) 1.0282(4) 0.1350(18) Uani 1 1 d . . . . .
H21A H -0.0340 0.7136 1.0689 0.203 Uiso 1 1 calc R U . . .
H21B H 0.0936 0.7253 1.0660 0.203 Uiso 1 1 calc R U . . .
H21C H 0.0161 0.6582 0.9870 0.203 Uiso 1 1 calc R U . . .
O4 O 0.82315(14) 0.41044(15) 0.78285(14) 0.0614(5) Uani 1 1 d . . . . .
O2 O 0.68301(12) 0.41236(12) 0.88124(11) 0.0437(3) Uani 1 1 d . . . . .
O3 O 0.62518(17) 0.40671(15) 0.71196(13) 0.0659(5) Uani 1 1 d . . . . .
O1 O 0.39442(10) 0.47628(10) 0.94702(9) 0.0322(2) Uani 1 1 d . . . . .
N3 N -0.0024(2) 0.8208(2) 0.97171(19) 0.0758(7) Uani 1 1 d . . . . .
N2 N 0.52287(12) 0.28445(11) 0.94691(10) 0.0312(3) Uani 1 1 d . . . . .
C20 C 0.0686(3) 0.8385(4) 0.9010(3) 0.1010(12) Uani 1 1 d . . . . .
H20A H 0.0556 0.9110 0.8745 0.151 Uiso 1 1 calc R U . . .
H20B H 0.0513 0.7846 0.8516 0.151 Uiso 1 1 calc R U . . .
H20C H 0.1455 0.8316 0.9304 0.151 Uiso 1 1 calc R U . . .
C19 C -0.0838(3) 0.8888(5) 0.9804(3) 0.1122(15) Uani 1 1 d . . . . .
H19 H -0.0951 0.9476 0.9382 0.135 Uiso 1 1 calc R U . . .
O5 O -0.1438(3) 0.8832(5) 1.0358(3) 0.182(2) Uani 1 1 d . . . . .
C18 C 0.42360(15) 0.23551(14) 0.94169(14) 0.0373(4) Uani 1 1 d . . . . .
H18 H 0.3596 0.2779 0.9244 0.045 Uiso 1 1 calc R U . . .
C17 C 0.41115(15) 0.12482(14) 0.96069(15) 0.0381(4) Uani 1 1 d . . . . .
H17 H 0.3401 0.0944 0.9548 0.046 Uiso 1 1 calc R U . . .
C16 C 0.50460(15) 0.05944(12) 0.98842(12) 0.0296(3) Uani 1 1 d . . . . .
C15 C 0.60738(16) 0.11070(16) 0.99432(18) 0.0483(5) Uani 1 1 d . . . . .
H15 H 0.6727 0.0704 1.0123 0.058 Uiso 1 1 calc R U . . .
C14 C 0.61312(16) 0.22144(16) 0.97358(17) 0.0455(5) Uani 1 1 d . . . . .
H14 H 0.6832 0.2538 0.9784 0.055 Uiso 1 1 calc R U . . .
N1 N 0.52002(12) 0.58450(11) 0.83163(10) 0.0304(3) Uani 1 1 d . . . . .
C8 C 0.61506(14) 0.64371(13) 0.81180(12) 0.0318(3) Uani 1 1 d . . . . .
C13 C 0.70709(15) 0.58785(15) 0.78908(13) 0.0349(4) Uani 1 1 d . . . . .
C12 C 0.79663(18) 0.64631(19) 0.76607(17) 0.0499(5) Uani 1 1 d . . . . .
H12 H 0.8567 0.6089 0.7490 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7965(2) 0.7602(2) 0.76854(19) 0.0611(7) Uani 1 1 d . . . . .
H11 H 0.8564 0.7994 0.7529 0.073 Uiso 1 1 calc R U . . .
C10 C 0.7080(2) 0.81527(18) 0.79403(18) 0.0577(6) Uani 1 1 d . . . . .
H10 H 0.7091 0.8918 0.7969 0.069 Uiso 1 1 calc R U . . .
C9 C 0.61677(18) 0.75861(15) 0.81559(15) 0.0435(4) Uani 1 1 d . . . . .
H9 H 0.5571 0.7969 0.8325 0.052 Uiso 1 1 calc R U . . .
C7 C 0.42309(15) 0.62402(14) 0.79462(13) 0.0345(3) Uani 1 1 d . . . . .
H7 H 0.4223 0.6830 0.7532 0.041 Uiso 1 1 calc R U . . .
C6 C 0.31696(15) 0.58526(14) 0.81161(14) 0.0351(4) Uani 1 1 d . . . . .
C1 C 0.30669(14) 0.51429(13) 0.88783(13) 0.0324(3) Uani 1 1 d . . . . .
C2 C 0.19870(16) 0.48413(18) 0.90074(16) 0.0441(4) Uani 1 1 d . . . . .
H2 H 0.1897 0.4405 0.9521 0.053 Uiso 1 1 calc R U . . .
C3 C 0.10584(17) 0.5189(2) 0.83751(19) 0.0548(6) Uani 1 1 d . . . . .
H3 H 0.0353 0.4959 0.8458 0.066 Uiso 1 1 calc R U . . .
C4 C 0.11573(18) 0.5875(2) 0.76189(19) 0.0566(6) Uani 1 1 d . . . . .
H4 H 0.0526 0.6095 0.7196 0.068 Uiso 1 1 calc R U . . .
C5 C 0.21990(17) 0.62222(18) 0.75030(16) 0.0475(5) Uani 1 1 d . . . . .
H5 H 0.2267 0.6707 0.7015 0.057 Uiso 1 1 calc R U . . .


_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 1.9191(13) . ?
Cu1 O2 1.9570(14) . ?
Cu1 N1 2.0146(14) . ?
Cu1 N2 2.0390(14) . ?
Cu1 O1 2.2941(14) 3_667 ?
S1 O3 1.4325(19) . ?
S1 O4 1.4347(16) . ?
S1 O2 1.4885(14) . ?
S1 C13 1.7646(19) . ?
C21 N3 1.457(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O1 C1 1.324(2) . ?
O1 Cu1 2.2941(14) 3_667 ?
N3 C19 1.313(5) . ?
N3 C20 1.460(4) . ?
N2 C18 1.336(2) . ?
N2 C14 1.338(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 O5 1.172(5) . ?
C19 H19 0.9300 . ?
C18 C17 1.385(2) . ?
C18 H18 0.9300 . ?
C17 C16 1.386(2) . ?
C17 H17 0.9300 . ?
C16 C15 1.386(3) . ?
C16 C16 1.490(3) 3_657 ?
C15 C14 1.382(3) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
N1 C7 1.297(2) . ?
N1 C8 1.432(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.396(3) . ?
C13 C12 1.388(3) . ?
C12 C11 1.383(3) . ?
C12 H12 0.9300 . ?
C11 C10 1.371(4) . ?
C11 H11 0.9300 . ?
C10 C9 1.386(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C7 C6 1.435(3) . ?
C7 H7 0.9300 . ?
C6 C5 1.415(3) . ?
C6 C1 1.415(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 175.60(6) . . ?
O1 Cu1 N1 89.70(6) . . ?
O2 Cu1 N1 93.06(6) . . ?
O1 Cu1 N2 90.22(6) . . ?
O2 Cu1 N2 88.29(6) . . ?
N1 Cu1 N2 161.13(6) . . ?
O1 Cu1 O1 82.92(5) . 3_667 ?
O2 Cu1 O1 93.30(6) . 3_667 ?
N1 Cu1 O1 97.59(6) . 3_667 ?
N2 Cu1 O1 101.13(5) . 3_667 ?
O3 S1 O4 116.92(12) . . ?
O3 S1 O2 110.94(11) . . ?
O4 S1 O2 110.28(10) . . ?
O3 S1 C13 107.23(10) . . ?
O4 S1 C13 107.41(10) . . ?
O2 S1 C13 103.01(9) . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 O2 Cu1 120.04(8) . . ?
C1 O1 Cu1 123.02(11) . . ?
C1 O1 Cu1 124.26(10) . 3_667 ?
Cu1 O1 Cu1 97.07(5) . 3_667 ?
C19 N3 C21 122.8(4) . . ?
C19 N3 C20 121.5(4) . . ?
C21 N3 C20 115.6(4) . . ?
C18 N2 C14 116.74(15) . . ?
C18 N2 Cu1 121.19(11) . . ?
C14 N2 Cu1 122.00(12) . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C19 N3 126.8(6) . . ?
O5 C19 H19 116.6 . . ?
N3 C19 H19 116.6 . . ?
N2 C18 C17 123.36(16) . . ?
N2 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C18 C17 C16 119.96(16) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C16 C15 116.48(15) . . ?
C17 C16 C16 121.9(2) . 3_657 ?
C15 C16 C16 121.60(19) . 3_657 ?
C14 C15 C16 120.22(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N2 C14 C15 123.23(17) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C7 N1 C8 116.15(14) . . ?
C7 N1 Cu1 121.53(12) . . ?
C8 N1 Cu1 122.30(11) . . ?
C9 C8 C13 119.17(17) . . ?
C9 C8 N1 120.05(17) . . ?
C13 C8 N1 120.78(15) . . ?
C12 C13 C8 120.19(18) . . ?
C12 C13 S1 119.03(16) . . ?
C8 C13 S1 120.78(13) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N1 C7 C6 126.13(16) . . ?
N1 C7 H7 116.9 . . ?
C6 C7 H7 116.9 . . ?
C5 C6 C1 119.68(18) . . ?
C5 C6 C7 117.88(18) . . ?
C1 C6 C7 122.43(16) . . ?
O1 C1 C2 119.37(17) . . ?
O1 C1 C6 122.44(16) . . ?
C2 C1 C6 118.20(17) . . ?
C3 C2 C1 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?

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
O3 S1 O2 Cu1 -48.71(14) . . . . ?
O4 S1 O2 Cu1 -179.87(11) . . . . ?
C13 S1 O2 Cu1 65.75(12) . . . . ?
C21 N3 C19 O5 4.4(7) . . . . ?
C20 N3 C19 O5 -178.4(4) . . . . ?
C14 N2 C18 C17 -1.1(3) . . . . ?
Cu1 N2 C18 C17 175.83(15) . . . . ?
N2 C18 C17 C16 1.2(3) . . . . ?
C18 C17 C16 C15 -0.8(3) . . . . ?
C18 C17 C16 C16 178.7(2) . . . 3_657 ?
C17 C16 C15 C14 0.3(3) . . . . ?
C16 C16 C15 C14 -179.1(2) 3_657 . . . ?
C18 N2 C14 C15 0.7(3) . . . . ?
Cu1 N2 C14 C15 -176.29(19) . . . . ?
C16 C15 C14 N2 -0.3(4) . . . . ?
C7 N1 C8 C9 43.0(2) . . . . ?
Cu1 N1 C8 C9 -138.69(15) . . . . ?
C7 N1 C8 C13 -137.39(18) . . . . ?
Cu1 N1 C8 C13 40.9(2) . . . . ?
C9 C8 C13 C12 -3.1(3) . . . . ?
N1 C8 C13 C12 177.25(17) . . . . ?
C9 C8 C13 S1 177.71(14) . . . . ?
N1 C8 C13 S1 -1.9(2) . . . . ?
O3 S1 C13 C12 -113.12(18) . . . . ?
O4 S1 C13 C12 13.3(2) . . . . ?
O2 S1 C13 C12 129.77(17) . . . . ?
O3 S1 C13 C8 66.06(18) . . . . ?
O4 S1 C13 C8 -167.50(16) . . . . ?
O2 S1 C13 C8 -51.05(17) . . . . ?
C8 C13 C12 C11 2.1(3) . . . . ?
S1 C13 C12 C11 -178.75(19) . . . . ?
C13 C12 C11 C10 0.2(4) . . . . ?
C12 C11 C10 C9 -1.4(4) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C13 C8 C9 C10 1.9(3) . . . . ?
N1 C8 C9 C10 -178.44(18) . . . . ?
C8 N1 C7 C6 -173.82(17) . . . . ?
Cu1 N1 C7 C6 7.8(3) . . . . ?
N1 C7 C6 C5 -166.70(19) . . . . ?
N1 C7 C6 C1 14.7(3) . . . . ?
Cu1 O1 C1 C2 147.73(14) . . . . ?
Cu1 O1 C1 C2 -83.92(18) 3_667 . . . ?
Cu1 O1 C1 C6 -32.7(2) . . . . ?
Cu1 O1 C1 C6 95.70(18) 3_667 . . . ?
C5 C6 C1 O1 179.42(17) . . . . ?
C7 C6 C1 O1 -2.0(3) . . . . ?
C5 C6 C1 C2 -1.0(3) . . . . ?
C7 C6 C1 C2 177.62(17) . . . . ?
O1 C1 C2 C3 -177.21(19) . . . . ?
C6 C1 C2 C3 3.2(3) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 2.8(4) . . . . ?
C1 C6 C5 C4 -2.1(3) . . . . ?
C7 C6 C5 C4 179.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18 O1 0.93 2.46 2.948(2) 113.0 .
C17 H17 O5 0.93 2.43 3.264(4) 149.0 3_567
C14 H14 O2 0.93 2.38 2.873(2) 113.1 .
C9 H9 O3 0.93 2.57 3.413(3) 151.0 2_656
C18 H18 O1 0.93 2.46 2.948(2) 113.0 .
C17 H17 O5 0.93 2.43 3.264(4) 149.0 3_567
C14 H14 O2 0.93 2.38 2.873(2) 113.1 .
C9 H9 O3 0.93 2.57 3.413(3) 151.0 2_656

_refine_diff_density_max         0.754
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.106

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_5SH205twin5
_database_code_depnum_ccdc_archive 'CCDC 1040998'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H26 Cu2 N4 O8 S2, C2 H8 O2'
_chemical_formula_sum            'C38 H34 Cu2 N4 O10 S2'
_chemical_formula_weight         897.89

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   11.7425(7)
_cell_length_b                   13.9180(8)
_cell_length_c                   14.0079(9)
_cell_angle_alpha                61.461(2)
_cell_angle_beta                 71.523(3)
_cell_angle_gamma                71.386(2)
_cell_volume                     1868.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    971
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.02

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.315
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.585774
_exptl_absorpt_correction_T_max  0.745160
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6478
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             6478
_reflns_number_gt                4557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'BrukerD8 Quest'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL '

_refine_special_details          
;
 Refined as a 2-component 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)+(0.0313P)²+15.0151P] 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_number_reflns         6478
_refine_ls_number_parameters     520
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.0268(7) 0.8504(6) 0.8883(6) 0.0155(17) Uani 1 1 d . . . . .
C2 C 0.0503(8) 0.9265(7) 0.9136(7) 0.026(2) Uani 1 1 d . . . . .
H2 H -0.0131 0.9860 0.9225 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1676(8) 0.9146(7) 0.9257(7) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.1846 0.9649 0.9448 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2592(8) 0.8293(7) 0.9099(7) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.3396 0.8220 0.9172 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2364(7) 0.7545(7) 0.8838(6) 0.0200(18) Uani 1 1 d . . . . .
H5 H 0.3007 0.6962 0.8735 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1189(7) 0.7644(6) 0.8726(6) 0.0137(16) Uani 1 1 d . . . . .
C7 C 0.1752(6) 0.6560(6) 0.7745(6) 0.0156(17) Uani 1 1 d . . . . .
H7 H 0.2398 0.6961 0.7358 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1783(7) 0.5696(7) 0.7452(6) 0.0209(18) Uani 1 1 d . . . . .
C9 C 0.1051(7) 0.4879(6) 0.8110(6) 0.0176(17) Uani 1 1 d . . . . .
C10 C 0.1197(8) 0.4031(7) 0.7783(7) 0.0248(19) Uani 1 1 d . . . . .
H10 H 0.0729 0.3464 0.8221 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2004(8) 0.4012(7) 0.6843(7) 0.033(2) Uani 1 1 d . . . . .
H11 H 0.2073 0.3440 0.6628 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2732(8) 0.4813(8) 0.6189(8) 0.034(2) Uani 1 1 d . . . . .
H12 H 0.3296 0.4785 0.5539 0.041 Uiso 1 1 calc R U . . .
C13 C 0.2620(7) 0.5638(7) 0.6499(7) 0.0256(19) Uani 1 1 d . . . . .
H13 H 0.3117 0.6182 0.6062 0.031 Uiso 1 1 calc R U . . .
C14 C -0.3214(7) 0.6097(7) 1.0171(7) 0.0240(19) Uani 1 1 d . . . . .
H14 H -0.3159 0.6503 1.0534 0.029 Uiso 1 1 calc R U . . .
C15 C -0.4323(7) 0.5802(7) 1.0384(7) 0.028(2) Uani 1 1 d . . . . .
H15 H -0.5010 0.6017 1.0874 0.033 Uiso 1 1 calc R U . . .
C16 C -0.4424(8) 0.5193(7) 0.9882(6) 0.025(2) Uani 1 1 d . . . . .
C17 C -0.3377(7) 0.4911(7) 0.9163(6) 0.026(2) Uani 1 1 d . . . . .
H17 H -0.3402 0.4493 0.8800 0.031 Uiso 1 1 calc R U . . .
C18 C -0.2313(8) 0.5241(7) 0.8985(6) 0.025(2) Uani 1 1 d . . . . .
H18 H -0.1614 0.5041 0.8494 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2975(7) 0.3463(6) 0.3749(6) 0.0151(17) Uani 1 1 d . . . . .
C20 C 0.1960(7) 0.4210(7) 0.3991(6) 0.0238(19) Uani 1 1 d . . . . .
H20 H 0.2064 0.4816 0.4070 0.029 Uiso 1 1 calc R U . . .
C21 C 0.0783(7) 0.4080(7) 0.4120(7) 0.028(2) Uani 1 1 d . . . . .
H21 H 0.0084 0.4584 0.4303 0.034 Uiso 1 1 calc R U . . .
C22 C 0.0645(7) 0.3209(7) 0.3980(6) 0.0233(19) Uani 1 1 d . . . . .
H22 H -0.0157 0.3124 0.4061 0.028 Uiso 1 1 calc R U . . .
C23 C 0.1645(7) 0.2459(6) 0.3724(6) 0.0163(17) Uani 1 1 d . . . . .
H23 H 0.1530 0.1868 0.3627 0.020 Uiso 1 1 calc R U . . .
C24 C 0.2829(7) 0.2571(6) 0.3610(6) 0.0149(17) Uani 1 1 d . . . . .
C25 C 0.3882(7) 0.1431(6) 0.2683(6) 0.0142(16) Uani 1 1 d . . . . .
H25 H 0.3241 0.1802 0.2275 0.017 Uiso 1 1 calc R U . . .
C26 C 0.4763(7) 0.0556(6) 0.2445(6) 0.0143(16) Uani 1 1 d . . . . .
C27 C 0.5587(7) -0.0232(6) 0.3154(6) 0.0153(17) Uani 1 1 d . . . . .
C28 C 0.6392(7) -0.1090(6) 0.2875(6) 0.0192(17) Uani 1 1 d . . . . .
H28 H 0.6911 -0.1651 0.3366 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6443(8) -0.1130(7) 0.1899(7) 0.027(2) Uani 1 1 d . . . . .
H29 H 0.7031 -0.1691 0.1702 0.032 Uiso 1 1 calc R U . . .
C30 C 0.5637(8) -0.0354(7) 0.1196(7) 0.031(2) Uani 1 1 d . . . . .
H30 H 0.5669 -0.0388 0.0526 0.037 Uiso 1 1 calc R U . . .
C31 C 0.4802(8) 0.0456(7) 0.1485(7) 0.027(2) Uani 1 1 d . . . . .
H31 H 0.4233 0.0965 0.1022 0.032 Uiso 1 1 calc R U . . .
C32 C 0.7258(8) 0.1071(6) 0.5160(7) 0.0221(19) Uani 1 1 d . . . . .
H32 H 0.6613 0.1474 0.5522 0.027 Uiso 1 1 calc R U . . .
C33 C 0.8399(7) 0.0769(7) 0.5392(6) 0.0208(18) Uani 1 1 d . . . . .
H33 H 0.8530 0.0954 0.5915 0.025 Uiso 1 1 calc R U . . .
C34 C 0.9374(7) 0.0187(6) 0.4866(6) 0.0160(17) Uani 1 1 d . . . . .
C35 C 0.9123(7) -0.0054(6) 0.4122(6) 0.0199(18) Uani 1 1 d . . . . .
H35 H 0.9759 -0.0439 0.3736 0.024 Uiso 1 1 calc R U . . .
C36 C 0.7942(7) 0.0263(6) 0.3932(6) 0.0184(18) Uani 1 1 d . . . . .
H36 H 0.7790 0.0074 0.3421 0.022 Uiso 1 1 calc R U . . .
N1 N 0.0942(5) 0.6850(5) 0.8476(5) 0.0163(14) Uani 1 1 d . . . . .
N2 N -0.2221(6) 0.5835(5) 0.9476(5) 0.0190(15) Uani 1 1 d . . . . .
N3 N 0.3869(5) 0.1771(5) 0.3405(5) 0.0163(14) Uani 1 1 d . . . . .
N4 N 0.7005(6) 0.0821(5) 0.4433(5) 0.0156(14) Uani 1 1 d . . . . .
O1 O -0.2031(5) 0.9471(4) 0.9157(5) 0.0280(14) Uani 1 1 d . . . . .
O2 O -0.1525(5) 0.7502(4) 0.9584(4) 0.0218(12) Uani 1 1 d . . . . .
O3 O -0.1237(5) 0.8845(4) 0.7673(4) 0.0246(13) Uani 1 1 d . . . . .
O4 O 0.0251(5) 0.4889(4) 0.9021(4) 0.0197(12) Uani 1 1 d . . . . .
O5 O 0.4333(5) 0.4510(4) 0.3890(5) 0.0238(13) Uani 1 1 d . . . . .
O6 O 0.5127(5) 0.3739(4) 0.2510(4) 0.0228(13) Uani 1 1 d . . . . .
O7 O 0.4973(5) 0.2527(4) 0.4463(4) 0.0180(12) Uani 1 1 d . . . . .
O8 O 0.5607(4) -0.0191(4) 0.4076(4) 0.0130(11) Uani 1 1 d . . . . .
S1 S -0.12556(17) 0.86323(16) 0.87864(16) 0.0173(4) Uani 1 1 d . . . . .
S2 S 0.44676(17) 0.36071(16) 0.36076(16) 0.0155(4) Uani 1 1 d . . . . .
Cu1 Cu -0.05944(8) 0.62267(8) 0.92320(8) 0.0157(2) Uani 1 1 d . . . . .
Cu2 Cu 0.52855(8) 0.11906(7) 0.41894(7) 0.0136(2) Uani 1 1 d . . . . .
C11A C 0.896(2) 0.228(2) 0.663(2) 0.067(4) Uani 0.5 1 d D U P A 1
H11A H 0.8425 0.1789 0.7233 0.100 Uiso 0.5 1 calc R U P A 1
H11B H 0.9372 0.1972 0.6080 0.100 Uiso 0.5 1 calc R U P A 1
H11C H 0.8473 0.3025 0.6282 0.100 Uiso 0.5 1 calc R U P A 1
O11A O 0.9869(16) 0.2351(15) 0.7076(14) 0.067(4) Uani 0.5 1 d D U P A 1
H11D H 1.0533 0.2398 0.6612 0.100 Uiso 0.5 1 calc R U P A 1
O10A O 0.4177(17) 0.7520(15) 0.1491(15) 0.078(3) Uani 0.5 1 d . . P B 1
H10G H 0.3692 0.8123 0.1212 0.116 Uiso 0.5 1 calc R U P B 1
O10B O 0.4282(18) 0.7317(15) 0.2360(14) 0.078(3) Uani 0.5 1 d . . P C 2
H10H H 0.4932 0.6947 0.2127 0.116 Uiso 0.5 1 calc R U P C 2
C10B C 0.420(3) 0.704(2) 0.340(2) 0.078(3) Uani 0.5 1 d . . P C 2
H10A H 0.4147 0.7696 0.3508 0.116 Uiso 0.5 1 calc R U P C 2
H10B H 0.4926 0.6476 0.3649 0.116 Uiso 0.5 1 calc R U P C 2
H10C H 0.3464 0.6722 0.3833 0.116 Uiso 0.5 1 calc R U P C 2
C10A C 0.352(3) 0.676(2) 0.2460(19) 0.078(3) Uani 0.5 1 d . . P B 1
H10D H 0.4039 0.6297 0.3011 0.116 Uiso 0.5 1 calc R U P B 1
H10E H 0.3276 0.6274 0.2259 0.116 Uiso 0.5 1 calc R U P B 1
H10F H 0.2781 0.7177 0.2771 0.116 Uiso 0.5 1 calc R U P B 1
O11B O 0.8791(17) 0.1620(15) 0.7150(15) 0.071(4) Uani 0.5 1 d D U P D 2
H11E H 0.8295 0.1244 0.7672 0.107 Uiso 0.5 1 calc R U P D 2
C11B C 0.911(3) 0.231(2) 0.749(2) 0.071(4) Uani 0.5 1 d D U P D 2
H11F H 0.8440 0.2480 0.8048 0.107 Uiso 0.5 1 calc R U P D 2
H11G H 0.9264 0.3010 0.6842 0.107 Uiso 0.5 1 calc R U P D 2
H11H H 0.9856 0.1917 0.7800 0.107 Uiso 0.5 1 calc R U P D 2


_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
C1 C6 1.387(11) . ?
C1 C2 1.391(11) . ?
C1 S1 1.783(8) . ?
C2 C3 1.388(12) . ?
C3 C4 1.379(12) . ?
C4 C5 1.375(11) . ?
C5 C6 1.394(10) . ?
C6 N1 1.437(9) . ?
C7 N1 1.284(9) . ?
C7 C8 1.432(11) . ?
C8 C13 1.405(11) . ?
C8 C9 1.415(11) . ?
C9 O4 1.327(9) . ?
C9 C10 1.402(11) . ?
C10 C11 1.363(12) . ?
C11 C12 1.396(13) . ?
C12 C13 1.367(12) . ?
C14 N2 1.337(10) . ?
C14 C15 1.390(11) . ?
C15 C16 1.383(12) . ?
C16 C17 1.401(12) . ?
C16 C16 1.496(16) 2_467 ?
C17 C18 1.375(11) . ?
C18 N2 1.348(10) . ?
C19 C20 1.381(11) . ?
C19 C24 1.413(10) . ?
C19 S2 1.766(8) . ?
C20 C21 1.396(12) . ?
C21 C22 1.381(12) . ?
C22 C23 1.380(11) . ?
C23 C24 1.399(10) . ?
C24 N3 1.424(10) . ?
C25 N3 1.300(9) . ?
C25 C26 1.425(10) . ?
C26 C31 1.402(11) . ?
C26 C27 1.420(10) . ?
C27 O8 1.328(8) . ?
C27 C28 1.401(10) . ?
C28 C29 1.376(11) . ?
C29 C30 1.398(12) . ?
C30 C31 1.370(12) . ?
C32 N4 1.357(10) . ?
C32 C33 1.365(11) . ?
C33 C34 1.398(11) . ?
C34 C35 1.371(11) . ?
C34 C34 1.499(15) 2_756 ?
C35 C36 1.385(11) . ?
C36 N4 1.339(10) . ?
N1 Cu1 2.010(6) . ?
N2 Cu1 2.034(6) . ?
N3 Cu2 2.019(6) . ?
N4 Cu2 2.016(6) . ?
O1 S1 1.437(6) . ?
O2 S1 1.495(5) . ?
O2 Cu1 1.961(5) . ?
O3 S1 1.436(5) . ?
O4 Cu1 1.924(5) . ?
O4 Cu1 2.271(5) 2_567 ?
O5 S2 1.439(5) . ?
O6 S2 1.437(5) . ?
O7 S2 1.486(5) . ?
O7 Cu2 1.975(5) . ?
O8 Cu2 1.911(5) . ?
O8 Cu2 2.241(5) 2_656 ?
Cu1 O4 2.271(5) 2_567 ?
Cu2 O8 2.241(5) 2_656 ?
C11A O11A 1.442(17) . ?
O10A C10A 1.43(3) . ?
O10B C10B 1.29(3) . ?
O11B C11B 1.440(17) . ?

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
C6 C1 C2 121.2(7) . . ?
C6 C1 S1 120.0(6) . . ?
C2 C1 S1 118.8(6) . . ?
C1 C2 C3 119.2(8) . . ?
C4 C3 C2 119.6(8) . . ?
C5 C4 C3 121.2(8) . . ?
C4 C5 C6 120.0(8) . . ?
C1 C6 C5 118.7(7) . . ?
C1 C6 N1 121.1(6) . . ?
C5 C6 N1 120.1(7) . . ?
N1 C7 C8 126.9(7) . . ?
C13 C8 C9 119.4(7) . . ?
C13 C8 C7 118.0(7) . . ?
C9 C8 C7 122.6(7) . . ?
O4 C9 C10 119.8(7) . . ?
O4 C9 C8 122.0(7) . . ?
C10 C9 C8 118.2(7) . . ?
C11 C10 C9 120.7(8) . . ?
C10 C11 C12 121.6(8) . . ?
C13 C12 C11 118.8(8) . . ?
C12 C13 C8 121.3(8) . . ?
N2 C14 C15 122.9(8) . . ?
C16 C15 C14 119.8(8) . . ?
C15 C16 C17 117.0(7) . . ?
C15 C16 C16 122.3(10) . 2_467 ?
C17 C16 C16 120.7(10) . 2_467 ?
C18 C17 C16 119.9(8) . . ?
N2 C18 C17 122.8(8) . . ?
C20 C19 C24 120.2(7) . . ?
C20 C19 S2 120.7(6) . . ?
C24 C19 S2 119.1(6) . . ?
C19 C20 C21 120.4(8) . . ?
C22 C21 C20 119.2(8) . . ?
C21 C22 C23 121.5(7) . . ?
C22 C23 C24 119.8(7) . . ?
C23 C24 C19 118.9(7) . . ?
C23 C24 N3 120.5(7) . . ?
C19 C24 N3 120.5(7) . . ?
N3 C25 C26 126.3(7) . . ?
C31 C26 C27 118.7(7) . . ?
C31 C26 C25 118.7(7) . . ?
C27 C26 C25 122.6(7) . . ?
O8 C27 C28 119.2(7) . . ?
O8 C27 C26 122.2(7) . . ?
C28 C27 C26 118.6(7) . . ?
C29 C28 C27 121.0(7) . . ?
C28 C29 C30 120.6(8) . . ?
C31 C30 C29 119.1(8) . . ?
C30 C31 C26 121.8(8) . . ?
N4 C32 C33 122.8(8) . . ?
C32 C33 C34 120.3(7) . . ?
C35 C34 C33 116.9(7) . . ?
C35 C34 C34 121.7(9) . 2_756 ?
C33 C34 C34 121.4(8) . 2_756 ?
C34 C35 C36 120.0(8) . . ?
N4 C36 C35 123.3(7) . . ?
C7 N1 C6 116.7(6) . . ?
C7 N1 Cu1 121.7(5) . . ?
C6 N1 Cu1 121.7(5) . . ?
C14 N2 C18 117.5(7) . . ?
C14 N2 Cu1 121.8(5) . . ?
C18 N2 Cu1 120.6(5) . . ?
C25 N3 C24 117.5(6) . . ?
C25 N3 Cu2 120.9(5) . . ?
C24 N3 Cu2 121.7(5) . . ?
C36 N4 C32 116.6(7) . . ?
C36 N4 Cu2 121.7(5) . . ?
C32 N4 Cu2 121.6(5) . . ?
S1 O2 Cu1 118.2(3) . . ?
C9 O4 Cu1 123.8(5) . . ?
C9 O4 Cu1 124.2(4) . 2_567 ?
Cu1 O4 Cu1 98.0(2) . 2_567 ?
S2 O7 Cu2 116.4(3) . . ?
C27 O8 Cu2 122.2(4) . . ?
C27 O8 Cu2 127.2(4) . 2_656 ?
Cu2 O8 Cu2 97.9(2) . 2_656 ?
O3 S1 O1 116.1(3) . . ?
O3 S1 O2 110.8(3) . . ?
O1 S1 O2 111.0(3) . . ?
O3 S1 C1 107.9(3) . . ?
O1 S1 C1 107.3(4) . . ?
O2 S1 C1 102.8(3) . . ?
O6 S2 O5 116.3(3) . . ?
O6 S2 O7 111.5(3) . . ?
O5 S2 O7 110.4(3) . . ?
O6 S2 C19 108.0(3) . . ?
O5 S2 C19 106.9(3) . . ?
O7 S2 C19 102.8(3) . . ?
O4 Cu1 O2 174.7(2) . . ?
O4 Cu1 N1 89.9(2) . . ?
O2 Cu1 N1 94.1(2) . . ?
O4 Cu1 N2 89.4(2) . . ?
O2 Cu1 N2 88.0(2) . . ?
N1 Cu1 N2 161.2(2) . . ?
O4 Cu1 O4 82.0(2) . 2_567 ?
O2 Cu1 O4 93.8(2) . 2_567 ?
N1 Cu1 O4 101.7(2) . 2_567 ?
N2 Cu1 O4 96.7(2) . 2_567 ?
O8 Cu2 O7 174.2(2) . . ?
O8 Cu2 N4 89.1(2) . . ?
O7 Cu2 N4 88.5(2) . . ?
O8 Cu2 N3 89.8(2) . . ?
O7 Cu2 N3 94.2(2) . . ?
N4 Cu2 N3 160.4(2) . . ?
O8 Cu2 O8 82.1(2) . 2_656 ?
O7 Cu2 O8 93.08(19) . 2_656 ?
N4 Cu2 O8 98.6(2) . 2_656 ?
N3 Cu2 O8 100.6(2) . 2_656 ?

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
C6 C1 C2 C3 -1.4(12) . . . . ?
S1 C1 C2 C3 177.4(6) . . . . ?
C1 C2 C3 C4 1.5(13) . . . . ?
C2 C3 C4 C5 -0.9(13) . . . . ?
C3 C4 C5 C6 0.2(12) . . . . ?
C2 C1 C6 C5 0.7(11) . . . . ?
S1 C1 C6 C5 -178.1(6) . . . . ?
C2 C1 C6 N1 179.3(7) . . . . ?
S1 C1 C6 N1 0.5(10) . . . . ?
C4 C5 C6 C1 -0.1(11) . . . . ?
C4 C5 C6 N1 -178.7(7) . . . . ?
N1 C7 C8 C13 168.9(8) . . . . ?
N1 C7 C8 C9 -14.1(12) . . . . ?
C13 C8 C9 O4 179.6(7) . . . . ?
C7 C8 C9 O4 2.7(12) . . . . ?
C13 C8 C9 C10 0.3(11) . . . . ?
C7 C8 C9 C10 -176.6(7) . . . . ?
O4 C9 C10 C11 179.3(7) . . . . ?
C8 C9 C10 C11 -1.4(12) . . . . ?
C9 C10 C11 C12 1.5(13) . . . . ?
C10 C11 C12 C13 -0.5(13) . . . . ?
C11 C12 C13 C8 -0.6(13) . . . . ?
C9 C8 C13 C12 0.7(12) . . . . ?
C7 C8 C13 C12 177.7(8) . . . . ?
N2 C14 C15 C16 1.1(13) . . . . ?
C14 C15 C16 C17 -0.4(12) . . . . ?
C14 C15 C16 C16 177.1(9) . . . 2_467 ?
C15 C16 C17 C18 -0.1(12) . . . . ?
C16 C16 C17 C18 -177.7(9) 2_467 . . . ?
C16 C17 C18 N2 0.0(12) . . . . ?
C24 C19 C20 C21 1.2(11) . . . . ?
S2 C19 C20 C21 -178.9(6) . . . . ?
C19 C20 C21 C22 -1.4(12) . . . . ?
C20 C21 C22 C23 0.6(12) . . . . ?
C21 C22 C23 C24 0.4(12) . . . . ?
C22 C23 C24 C19 -0.6(11) . . . . ?
C22 C23 C24 N3 176.6(7) . . . . ?
C20 C19 C24 C23 -0.2(11) . . . . ?
S2 C19 C24 C23 179.9(5) . . . . ?
C20 C19 C24 N3 -177.4(7) . . . . ?
S2 C19 C24 N3 2.7(9) . . . . ?
N3 C25 C26 C31 -166.2(7) . . . . ?
N3 C25 C26 C27 15.2(11) . . . . ?
C31 C26 C27 O8 179.9(7) . . . . ?
C25 C26 C27 O8 -1.4(11) . . . . ?
C31 C26 C27 C28 -1.1(11) . . . . ?
C25 C26 C27 C28 177.6(7) . . . . ?
O8 C27 C28 C29 -176.8(7) . . . . ?
C26 C27 C28 C29 4.1(11) . . . . ?
C27 C28 C29 C30 -4.0(13) . . . . ?
C28 C29 C30 C31 0.6(13) . . . . ?
C29 C30 C31 C26 2.5(13) . . . . ?
C27 C26 C31 C30 -2.3(12) . . . . ?
C25 C26 C31 C30 179.0(8) . . . . ?
N4 C32 C33 C34 0.8(12) . . . . ?
C32 C33 C34 C35 0.0(11) . . . . ?
C32 C33 C34 C34 -178.0(8) . . . 2_756 ?
C33 C34 C35 C36 -0.9(11) . . . . ?
C34 C34 C35 C36 177.1(8) 2_756 . . . ?
C34 C35 C36 N4 1.0(12) . . . . ?
C8 C7 N1 C6 172.2(7) . . . . ?
C8 C7 N1 Cu1 -7.9(11) . . . . ?
C1 C6 N1 C7 139.2(7) . . . . ?
C5 C6 N1 C7 -42.2(10) . . . . ?
C1 C6 N1 Cu1 -40.7(9) . . . . ?
C5 C6 N1 Cu1 137.9(6) . . . . ?
C15 C14 N2 C18 -1.2(11) . . . . ?
C15 C14 N2 Cu1 -177.5(6) . . . . ?
C17 C18 N2 C14 0.6(11) . . . . ?
C17 C18 N2 Cu1 176.9(6) . . . . ?
C26 C25 N3 C24 -172.9(7) . . . . ?
C26 C25 N3 Cu2 7.7(10) . . . . ?
C23 C24 N3 C25 43.2(9) . . . . ?
C19 C24 N3 C25 -139.6(7) . . . . ?
C23 C24 N3 Cu2 -137.4(6) . . . . ?
C19 C24 N3 Cu2 39.7(8) . . . . ?
C35 C36 N4 C32 -0.2(11) . . . . ?
C35 C36 N4 Cu2 -176.7(6) . . . . ?
C33 C32 N4 C36 -0.7(11) . . . . ?
C33 C32 N4 Cu2 175.8(6) . . . . ?
C10 C9 O4 Cu1 -150.6(6) . . . . ?
C8 C9 O4 Cu1 30.1(10) . . . . ?
C10 C9 O4 Cu1 78.2(8) . . . 2_567 ?
C8 C9 O4 Cu1 -101.0(7) . . . 2_567 ?
C28 C27 O8 Cu2 146.5(6) . . . . ?
C26 C27 O8 Cu2 -34.5(9) . . . . ?
C28 C27 O8 Cu2 -80.5(8) . . . 2_656 ?
C26 C27 O8 Cu2 98.5(7) . . . 2_656 ?
Cu1 O2 S1 O3 48.4(4) . . . . ?
Cu1 O2 S1 O1 178.9(3) . . . . ?
Cu1 O2 S1 C1 -66.6(4) . . . . ?
C6 C1 S1 O3 -63.3(7) . . . . ?
C2 C1 S1 O3 117.8(6) . . . . ?
C6 C1 S1 O1 171.0(6) . . . . ?
C2 C1 S1 O1 -7.9(7) . . . . ?
C6 C1 S1 O2 53.8(7) . . . . ?
C2 C1 S1 O2 -125.0(6) . . . . ?
Cu2 O7 S2 O6 -46.9(4) . . . . ?
Cu2 O7 S2 O5 -177.6(3) . . . . ?
Cu2 O7 S2 C19 68.6(4) . . . . ?
C20 C19 S2 O6 -120.5(6) . . . . ?
C24 C19 S2 O6 59.4(6) . . . . ?
C20 C19 S2 O5 5.3(7) . . . . ?
C24 C19 S2 O5 -174.9(6) . . . . ?
C20 C19 S2 O7 121.5(6) . . . . ?
C24 C19 S2 O7 -58.6(6) . . . . ?

_refine_diff_density_max         0.998
_refine_diff_density_min         -1.424
_refine_diff_density_rms         0.133

_shelxl_version_number           2014-3

