# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1055317'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 N8 Na2 O18 S2'
_chemical_formula_sum            'C20 H26 N8 Na2 O18 S2'
_chemical_formula_weight         776.59

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'
Na Na 0.0362 0.0249 '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'

_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                   8.2720(9)
_cell_length_b                   10.0598(8)
_cell_length_c                   10.6312(8)
_cell_angle_alpha                63.001(4)
_cell_angle_beta                 74.356(5)
_cell_angle_gamma                76.484(5)
_cell_volume                     752.64(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3245
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.905
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7194
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         25.744
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.768
_diffrn_measured_fraction_theta_full 0.767
_diffrn_reflns_Laue_measured_fraction_max 0.768
_diffrn_reflns_Laue_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_point_group_measured_fraction_full 0.767
_reflns_number_total             2203
_reflns_number_gt                1752
_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-2013 (Sheldrick, 2013)'
_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)+(0.0656P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     253
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_restrained_S_all      0.957
_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
C1 C 0.3192(3) 0.5698(3) 0.1108(2) 0.0246(6) Uani 1 1 d . . . . .
C2 C 0.3468(3) 0.5370(3) 0.2468(2) 0.0254(6) Uani 1 1 d . . . . .
C3 C 0.4027(4) 0.6452(3) 0.2669(3) 0.0340(7) Uani 1 1 d . . . . .
H3 H 0.4214 0.6238 0.3589 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4308(4) 0.7826(3) 0.1548(3) 0.0410(8) Uani 1 1 d . . . . .
H4 H 0.4666 0.8567 0.1696 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4067(4) 0.8123(3) 0.0202(3) 0.0404(8) Uani 1 1 d . . . . .
H5 H 0.4288 0.9063 -0.0578 0.048 Uiso 1 1 calc R U . . .
C6 C 0.3513(4) 0.7077(3) -0.0019(3) 0.0338(7) Uani 1 1 d . . . . .
H6 H 0.3348 0.7298 -0.0948 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1748(3) 0.4002(3) -0.0618(2) 0.0245(6) Uani 1 1 d . . . . .
C8 C 0.1417(3) 0.2492(3) 0.0408(2) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.1466(3) 0.4575(3) -0.2103(2) 0.0269(6) Uani 1 1 d . . . . .
C10 C 0.0701(4) 0.2113(3) -0.1487(2) 0.0284(6) Uani 1 1 d . . . . .
N1 N 0.2582(3) 0.4625(2) 0.0897(2) 0.0269(5) Uani 1 1 d . . . . .
N2 N 0.2261(3) 0.4981(2) -0.0359(2) 0.0251(5) Uani 1 1 d . . . . .
N3 N 0.1004(3) 0.3537(2) -0.2411(2) 0.0290(6) Uani 1 1 d D . . . .
N4 N 0.0914(3) 0.1647(2) -0.0097(2) 0.0311(6) Uani 1 1 d D . . . .
O1 O 0.1558(3) 0.1957(2) 0.16733(17) 0.0399(6) Uani 1 1 d . . . . .
O2 O 0.0284(3) 0.1262(2) -0.18387(18) 0.0400(6) Uani 1 1 d . . . . .
O3 O 0.1626(3) 0.5843(2) -0.30132(18) 0.0418(6) Uani 1 1 d . . . . .
O10 O 0.5109(3) -0.0373(3) 0.3250(2) 0.0477(6) Uani 1 1 d . . . . .
O11 O 0.3308(3) 0.2526(2) 0.34803(18) 0.0411(6) Uani 1 1 d . . . . .
O12 O 0.1303(3) 0.3956(2) 0.46666(18) 0.0415(5) Uani 1 1 d . . . . .
O13 O 0.4223(3) 0.3402(2) 0.4901(2) 0.0505(7) Uani 1 1 d . . . . .
O20 O 0.2763(3) -0.1426(3) 0.6449(2) 0.0520(7) Uani 1 1 d D . . . .
O30 O -0.0463(3) 0.1384(2) 0.5531(2) 0.0465(6) Uani 1 1 d D . . . .
Na2 Na 0.21705(16) 0.03564(12) 0.40917(10) 0.0391(3) Uani 1 1 d . . . . .
S2 S 0.30363(9) 0.36840(7) 0.40040(6) 0.0272(2) Uani 1 1 d . . . . .
H1N H 0.245(4) 0.375(4) 0.161(3) 0.041 Uiso 1 1 d . U . . .
H3N H 0.087(4) 0.382(3) -0.328(2) 0.041 Uiso 1 1 d D U . . .
H4N H 0.059(4) 0.077(3) 0.051(3) 0.041 Uiso 1 1 d D U . . .
H10A H 0.548(4) -0.125(4) 0.374(3) 0.041 Uiso 1 1 d . U . . .
H10B H 0.573(4) 0.017(4) 0.328(3) 0.041 Uiso 1 1 d . U . . .
H20A H 0.202(3) -0.204(3) 0.705(3) 0.041 Uiso 1 1 d D U . . .
H20B H 0.371(3) -0.205(3) 0.634(3) 0.041 Uiso 1 1 d D U . . .
H30A H -0.013(4) 0.144(4) 0.620(3) 0.041 Uiso 1 1 d D U . . .
H30B H -0.051(5) 0.214(4) 0.499(3) 0.041 Uiso 1 1 d . 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
C1 C6 1.386(4) . ?
C1 C2 1.400(3) . ?
C1 N1 1.416(3) . ?
C2 C3 1.394(3) . ?
C2 S2 1.768(2) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.315(3) . ?
C7 C8 1.450(3) . ?
C7 C9 1.480(3) . ?
C8 O1 1.229(3) . ?
C8 N4 1.373(3) . ?
C9 O3 1.213(3) . ?
C9 N3 1.381(3) . ?
C10 O2 1.221(3) . ?
C10 N3 1.355(3) . ?
C10 N4 1.381(3) . ?
N1 N2 1.301(3) . ?
N1 H1N 0.87(3) . ?
N3 H3N 0.866(17) . ?
N4 H4N 0.874(18) . ?
O1 Na2 2.4539(19) . ?
O10 Na2 2.416(3) . ?
O10 H10A 0.83(4) . ?
O10 H10B 0.85(3) . ?
O11 S2 1.4550(18) . ?
O11 Na2 2.3265(17) . ?
O12 S2 1.440(2) . ?
O13 S2 1.4428(19) . ?
O20 Na2 2.431(2) . ?
O20 H20A 0.880(17) . ?
O20 H20B 0.902(18) . ?
O30 Na2 2.3315(19) 2_556 ?
O30 Na2 2.596(3) . ?
O30 H30A 0.855(17) . ?
O30 H30B 0.71(3) . ?
Na2 O30 2.3315(19) 2_556 ?
Na2 Na2 3.653(2) 2_556 ?

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 119.5(2) . . ?
C6 C1 N1 120.6(2) . . ?
C2 C1 N1 119.9(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 S2 116.77(17) . . ?
C1 C2 S2 123.88(16) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N2 C7 C8 126.09(19) . . ?
N2 C7 C9 114.1(2) . . ?
C8 C7 C9 119.76(18) . . ?
O1 C8 N4 119.9(2) . . ?
O1 C8 C7 123.6(2) . . ?
N4 C8 C7 116.50(19) . . ?
O3 C9 N3 120.7(2) . . ?
O3 C9 C7 124.48(19) . . ?
N3 C9 C7 114.8(2) . . ?
O2 C10 N3 123.2(2) . . ?
O2 C10 N4 120.6(2) . . ?
N3 C10 N4 116.13(19) . . ?
N2 N1 C1 118.8(2) . . ?
N2 N1 H1N 122.7(17) . . ?
C1 N1 H1N 118.5(17) . . ?
N1 N2 C7 120.9(2) . . ?
C10 N3 C9 127.02(19) . . ?
C10 N3 H3N 115.6(19) . . ?
C9 N3 H3N 117.3(19) . . ?
C8 N4 C10 125.7(2) . . ?
C8 N4 H4N 119.0(18) . . ?
C10 N4 H4N 115.0(18) . . ?
C8 O1 Na2 166.2(2) . . ?
Na2 O10 H10A 114(2) . . ?
Na2 O10 H10B 110(2) . . ?
H10A O10 H10B 105(3) . . ?
S2 O11 Na2 137.59(12) . . ?
Na2 O20 H20A 119(2) . . ?
Na2 O20 H20B 109(2) . . ?
H20A O20 H20B 104(3) . . ?
Na2 O30 Na2 95.54(8) 2_556 . ?
Na2 O30 H30A 124.7(19) 2_556 . ?
Na2 O30 H30A 107(2) . . ?
Na2 O30 H30B 124(3) 2_556 . ?
Na2 O30 H30B 95(3) . . ?
H30A O30 H30B 104(3) . . ?
O11 Na2 O30 165.58(10) . 2_556 ?
O11 Na2 O10 79.52(8) . . ?
O30 Na2 O10 111.66(9) 2_556 . ?
O11 Na2 O20 107.10(7) . . ?
O30 Na2 O20 83.69(8) 2_556 . ?
O10 Na2 O20 84.32(9) . . ?
O11 Na2 O1 77.68(7) . . ?
O30 Na2 O1 91.98(7) 2_556 . ?
O10 Na2 O1 94.56(8) . . ?
O20 Na2 O1 174.74(8) . . ?
O11 Na2 O30 87.06(8) . . ?
O30 Na2 O30 84.46(8) 2_556 . ?
O10 Na2 O30 159.16(8) . . ?
O20 Na2 O30 84.49(9) . . ?
O1 Na2 O30 98.09(9) . . ?
O11 Na2 Na2 125.57(8) . 2_556 ?
O30 Na2 Na2 45.02(7) 2_556 2_556 ?
O10 Na2 Na2 154.13(8) . 2_556 ?
O20 Na2 Na2 82.05(7) . 2_556 ?
O1 Na2 Na2 97.01(7) . 2_556 ?
O30 Na2 Na2 39.44(5) . 2_556 ?
O12 S2 O13 112.96(13) . . ?
O12 S2 O11 112.79(11) . . ?
O13 S2 O11 111.92(14) . . ?
O12 S2 C2 106.09(13) . . ?
O13 S2 C2 106.36(11) . . ?
O11 S2 C2 106.07(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
C3 H3 O13 0.95 2.50 3.355(3) 149.9 2_666
C6 H6 O20 0.95 2.60 3.526(3) 166.0 1_564
N1 H1N O1 0.87(3) 2.07(3) 2.698(3) 128(2) .
N1 H1N O11 0.87(3) 2.02(3) 2.719(3) 136(2) .
N1 H1N S2 0.87(3) 2.68(3) 3.100(2) 111(2) .
N3 H3N O12 0.866(17) 2.058(19) 2.887(3) 160(3) 1_554
N3 H3N O12 0.866(17) 2.64(3) 3.237(3) 127(3) 2_565
N3 H3N S2 0.866(17) 3.00(3) 3.677(2) 136(3) 1_554
N4 H4N O2 0.874(18) 2.055(18) 2.928(3) 176(3) 2
O10 H10A O13 0.83(4) 1.98(3) 2.795(3) 166(3) 2_656
O10 H10A S2 0.83(4) 2.85(4) 3.628(2) 158(2) 2_656
O10 H10B O20 0.85(3) 2.12(3) 2.965(3) 175(3) 2_656
O20 H20A O3 0.880(17) 2.26(3) 2.872(3) 127(2) 1_546
O20 H20B O11 0.902(18) 2.44(2) 3.189(4) 140(2) 2_656
O20 H20B O13 0.902(18) 2.41(2) 3.251(4) 155(3) 2_656
O20 H20B S2 0.902(18) 2.831(18) 3.724(3) 171(2) 2_656
O30 H30A O2 0.855(17) 2.127(19) 2.966(3) 167(3) 1_556
O30 H30B O3 0.71(3) 2.38(4) 3.038(3) 153(3) 2_565
O30 H30B O12 0.71(3) 2.48(3) 2.925(3) 122(3) .

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.081

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1055319'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 Cu N6 O5, 3(H2 O)'
_chemical_formula_sum            'C13 H18 Cu N6 O8'
_chemical_formula_weight         449.87

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'
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                   7.7709(9)
_cell_length_b                   9.7428(14)
_cell_length_c                   12.4498(15)
_cell_angle_alpha                80.753(6)
_cell_angle_beta                 73.757(6)
_cell_angle_gamma                75.927(7)
_cell_volume                     873.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2251
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      21.24


_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.309
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 The crystal (the largest available) diffracted quite weakly at high angle. 
 On repeated recrystallisation we could get only small sized crystals.  
;

_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6216
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         21.239
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.554
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.554
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.554
_reflns_number_total             1751
_reflns_number_gt                1442
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 The hydrogen atoms bonded to N and O atoms were located from the
 difference Fourier synthesis and refined isotropically.
 The other hydrogen atoms were placed in calculated positions
 and refined by using a riding model. The positions of the O3W
 hydrogen atoms were fixed. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²+0.7444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1751
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.002
_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 0.3349(7) 0.6892(6) 0.0201(5) 0.0271(15) Uani 1 1 d . . . . .
C2 C 0.3887(7) 0.8045(6) -0.0529(5) 0.0315(15) Uani 1 1 d . . . . .
H2 H 0.4139 0.8782 -0.0247 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4046(8) 0.8096(7) -0.1658(6) 0.0372(16) Uani 1 1 d . . . . .
H3 H 0.4402 0.8873 -0.2133 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3687(8) 0.7018(7) -0.2105(5) 0.0365(16) Uani 1 1 d . . . . .
H4 H 0.3837 0.7059 -0.2876 0.044 Uiso 1 1 calc R U . . .
C5 C 0.3109(8) 0.5887(6) -0.1410(5) 0.0330(15) Uani 1 1 d . . . . .
H5 H 0.2841 0.5169 -0.1706 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2925(7) 0.5821(6) -0.0257(5) 0.0241(14) Uani 1 1 d . . . . .
C7 C 0.1445(7) 0.2621(6) 0.0967(5) 0.0217(14) Uani 1 1 d . . . . .
C8 C 0.1002(7) 0.1523(6) 0.0495(5) 0.0231(14) Uani 1 1 d . . . . .
C9 C 0.1284(8) 0.2466(6) 0.2135(5) 0.0271(15) Uani 1 1 d . . . . .
C10 C 0.0301(8) 0.0242(7) 0.2356(5) 0.0313(15) Uani 1 1 d . . . . .
C11 C 0.2613(10) 0.6497(8) 0.3984(6) 0.0505(19) Uani 1 1 d . . . . .
H11 H 0.2771 0.7353 0.3555 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2486(11) 0.6240(9) 0.5088(6) 0.061(2) Uani 1 1 d . . . . .
H12 H 0.2532 0.6872 0.5560 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2255(10) 0.4373(8) 0.4463(6) 0.0493(19) Uani 1 1 d . . . . .
H13 H 0.2101 0.3461 0.4443 0.059 Uiso 1 1 calc R U . . .
N1 N 0.2384(6) 0.4720(5) 0.0549(4) 0.0257(12) Uani 1 1 d . . . . .
N2 N 0.1967(6) 0.3702(5) 0.0206(4) 0.0246(12) Uani 1 1 d . . . . .
N3 N 0.0467(7) 0.0413(5) 0.1234(4) 0.0279(13) Uani 1 1 d . . . . .
N4 N 0.0778(7) 0.1273(5) 0.2761(4) 0.0306(13) Uani 1 1 d . . . . .
N5 N 0.2476(6) 0.5321(5) 0.3578(4) 0.0318(13) Uani 1 1 d . . . . .
N6 N 0.2278(8) 0.4878(7) 0.5384(5) 0.0524(17) Uani 1 1 d . . . . .
O1 O 0.3208(5) 0.6780(4) 0.1304(3) 0.0347(11) Uani 1 1 d . . . . .
O2 O 0.1563(6) 0.3347(4) 0.2673(3) 0.0371(11) Uani 1 1 d . . . . .
O1W O 0.4960(8) 0.1468(6) -0.1883(4) 0.0681(16) Uani 1 1 d . . . . .
O3 O 0.1110(5) 0.1507(4) -0.0509(3) 0.0331(10) Uani 1 1 d . . . . .
O2W O 0.1894(9) 0.0802(7) 0.4745(4) 0.077(2) Uani 1 1 d . . . . .
O4 O -0.0226(6) -0.0779(5) 0.2970(3) 0.0450(12) Uani 1 1 d . . . . .
O3W O 0.4936(9) 0.1125(7) 0.5913(5) 0.100(2) Uani 1 1 d . . . . .
O4W O -0.0865(6) 0.6609(5) 0.2458(4) 0.0446(12) Uani 1 1 d . . . . .
Cu1 Cu 0.23671(10) 0.50898(7) 0.20582(6) 0.0320(4) Uani 1 1 d . . . . .
H1W1 H 0.380(8) 0.163(6) -0.147(5) 0.048 Uiso 1 1 d D U . . .
H1W2 H 0.564(7) 0.203(7) -0.164(5) 0.048 Uiso 1 1 d D U . . .
H3N H 0.007(9) -0.019(7) 0.102(5) 0.048 Uiso 1 1 d . U . . .
H2N H 0.085(8) 0.107(6) 0.353(6) 0.048 Uiso 1 1 d . U . . .
H6N H 0.200(8) 0.450(7) 0.610(6) 0.048 Uiso 1 1 d . U . . .
H4W1 H -0.106(8) 0.667(6) 0.176(5) 0.048 Uiso 1 1 d D U . . .
H4W2 H -0.067(9) 0.730(7) 0.272(5) 0.048 Uiso 1 1 d D U . . .
H2W1 H 0.287(10) 0.021(7) 0.460(5) 0.048 Uiso 1 1 d . U . . .
H2W2 H 0.131(10) 0.080(8) 0.532(6) 0.048 Uiso 1 1 d . U . . .
H3W1 H 0.4576 0.1191 0.6637 0.048 Uiso 1 1 d . U . . .
H3W2 H 0.4426 0.1941 0.5623 0.048 Uiso 1 1 d . 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
C1 O1 1.335(7) . ?
C1 C2 1.397(8) . ?
C1 C6 1.409(8) . ?
C2 C3 1.370(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(8) . ?
C5 H5 0.9300 . ?
C6 N1 1.405(7) . ?
C7 N2 1.358(7) . ?
C7 C9 1.411(8) . ?
C7 C8 1.450(8) . ?
C8 O3 1.231(6) . ?
C8 N3 1.370(7) . ?
C9 O2 1.260(7) . ?
C9 N4 1.368(7) . ?
C10 O4 1.233(7) . ?
C10 N3 1.353(8) . ?
C10 N4 1.359(8) . ?
C11 C12 1.338(9) . ?
C11 N5 1.362(8) . ?
C11 H11 0.9300 . ?
C12 N6 1.355(9) . ?
C12 H12 0.9300 . ?
C13 N5 1.320(8) . ?
C13 N6 1.324(9) . ?
C13 H13 0.9300 . ?
N1 N2 1.280(6) . ?
N1 Cu1 1.965(5) . ?
N3 H3N 0.84(7) . ?
N4 H2N 0.96(7) . ?
N5 Cu1 1.968(5) . ?
N6 H6N 0.89(6) . ?
O1 Cu1 1.925(4) . ?
O2 Cu1 1.921(4) . ?
O1W H1W1 0.89(6) . ?
O1W H1W2 0.98(6) . ?
O2W H2W1 0.83(7) . ?
O2W H2W2 0.73(6) . ?
O3W H3W1 0.870 . ?
O3W H3W2 0.870 . ?
O4W H4W1 0.91(6) . ?
O4W H4W2 0.85(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 122.6(5) . . ?
O1 C1 C6 119.5(5) . . ?
C2 C1 C6 117.9(6) . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.6(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 N1 125.9(5) . . ?
C5 C6 C1 120.8(5) . . ?
N1 C6 C1 113.3(5) . . ?
N2 C7 C9 127.5(5) . . ?
N2 C7 C8 114.5(5) . . ?
C9 C7 C8 118.0(5) . . ?
O3 C8 N3 118.6(5) . . ?
O3 C8 C7 125.1(5) . . ?
N3 C8 C7 116.3(5) . . ?
O2 C9 N4 115.7(5) . . ?
O2 C9 C7 125.5(5) . . ?
N4 C9 C7 118.8(5) . . ?
O4 C10 N3 122.7(6) . . ?
O4 C10 N4 122.1(6) . . ?
N3 C10 N4 115.1(6) . . ?
C12 C11 N5 110.0(6) . . ?
C12 C11 H11 125.0 . . ?
N5 C11 H11 125.0 . . ?
C11 C12 N6 106.6(7) . . ?
C11 C12 H12 126.7 . . ?
N6 C12 H12 126.7 . . ?
N5 C13 N6 111.8(6) . . ?
N5 C13 H13 124.1 . . ?
N6 C13 H13 124.1 . . ?
N2 N1 C6 117.5(5) . . ?
N2 N1 Cu1 131.7(4) . . ?
C6 N1 Cu1 110.8(4) . . ?
N1 N2 C7 118.8(5) . . ?
C10 N3 C8 126.7(6) . . ?
C10 N3 H3N 113(4) . . ?
C8 N3 H3N 120(4) . . ?
C10 N4 C9 124.9(5) . . ?
C10 N4 H2N 115(4) . . ?
C9 N4 H2N 120(4) . . ?
C13 N5 C11 104.7(5) . . ?
C13 N5 Cu1 126.0(5) . . ?
C11 N5 Cu1 129.0(5) . . ?
C13 N6 C12 107.0(6) . . ?
C13 N6 H6N 129(4) . . ?
C12 N6 H6N 123(4) . . ?
C1 O1 Cu1 111.5(3) . . ?
C9 O2 Cu1 126.7(4) . . ?
H1W1 O1W H1W2 109(5) . . ?
H2W1 O2W H2W2 120(8) . . ?
H3W1 O3W H3W2 104.00 . . ?
H4W1 O4W H4W2 124(5) . . ?
O2 Cu1 O1 174.59(17) . . ?
O2 Cu1 N1 89.79(18) . . ?
O1 Cu1 N1 84.87(18) . . ?
O2 Cu1 N5 87.84(19) . . ?
O1 Cu1 N5 97.4(2) . . ?
N1 Cu1 N5 175.7(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
C11 H11 O1W 0.93 2.63 3.423(9) 143.4 2_665
C13 H13 O2W 0.93 2.60 3.513(10) 168.7 .
O1W H1W1 O3 0.89(6) 2.12(6) 2.997(7) 167(5) .
O1W H1W2 O1 0.98(6) 1.78(6) 2.759(6) 173(5) 2_665
N3 H3N O3 0.84(7) 2.01(7) 2.845(6) 175(6) 2
N4 H2N O2W 0.96(7) 1.86(7) 2.776(8) 157(5) .
N6 H6N O4W 0.89(6) 2.03(7) 2.897(7) 163(6) 2_566
O4W H4W1 O3 0.91(6) 2.17(6) 2.820(6) 128(5) 2_565
O4W H4W2 O4 0.85(6) 2.07(7) 2.906(6) 166(6) 1_565

_refine_diff_density_max         0.540
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.097

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1055320'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C20 H12 Co N8 O8), Co H12 O6, 8(H2 O)'
_chemical_formula_sum            'C40 H52 Co3 N16 O30'
_chemical_formula_weight         1413.76

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'
Co Co 0.3494 0.9721 '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                   10.8762(18)
_cell_length_b                   12.0409(17)
_cell_length_c                   12.2165(19)
_cell_angle_alpha                79.360(8)
_cell_angle_beta                 65.192(8)
_cell_angle_gamma                68.570(8)
_cell_volume                     1350.9(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2790
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.82

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             725
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.022
_shelx_estimated_absorpt_T_min   0.679
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 Absorption corrections were applied and all possible
 sources of error were carefuly examined and ruled out as
 causes for alert DIFMX02_ALERT_2_B. The residual electron
 density under question is close to O8 and could be neither
 ascertained not removed by using PLATON SQUEEZE routine. 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13738
_diffrn_reflns_av_unetI/netI     0.1385
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         26.244
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             13738
_reflns_number_gt                8108
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refined as a 2-component perfect twin.
 The hydrogen atoms bonded to N atoms were located from the
 difference Fourier synthesis and refined isotropically.
 The hydrogen atoms bonded to water O atoms were inserted in
 calculated positions by means of the CALC-OH routine of WinGX
 but their distances were fixed to achieve a reasonable result.
 The other hydrogen atoms were placed in calculated positions
 and refined by using a riding model. Several NH and OH bonds were
 restrained by means of DFIX and DANG.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13738
_refine_ls_number_parameters     433
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.1054
_refine_ls_wR_factor_ref         0.3259
_refine_ls_wR_factor_gt          0.3017
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_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 0.1880(13) -0.0188(10) 0.5238(10) 0.011(3) Uani 1 1 d . U . . .
C2 C 0.1037(14) -0.0768(11) 0.6202(11) 0.018(3) Uani 1 1 d . . . . .
H2 H 0.0565 -0.1222 0.6064 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0910(14) -0.0665(11) 0.7342(11) 0.020(3) Uani 1 1 d . . . . .
H3 H 0.0365 -0.1072 0.7998 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1562(14) 0.0024(10) 0.7561(11) 0.018(3) Uani 1 1 d . . . . .
H4 H 0.1436 0.0090 0.8367 0.021 Uiso 1 1 calc R U . . .
C5 C 0.2367(13) 0.0598(10) 0.6660(10) 0.013(3) Uani 1 1 d . . . . .
H5 H 0.2806 0.1068 0.6820 0.016 Uiso 1 1 calc R U . . .
C6 C 0.2542(13) 0.0486(10) 0.5476(10) 0.010(3) Uani 1 1 d . . . . .
C7 C 0.4888(13) 0.2078(10) 0.3496(10) 0.011(3) Uani 1 1 d . . . . .
C8 C 0.5508(13) 0.2875(10) 0.3708(11) 0.014(3) Uani 1 1 d . . . . .
C9 C 0.5273(12) 0.1802(9) 0.2294(10) 0.008(2) Uani 1 1 d . U . . .
C10 C 0.6691(13) 0.3127(10) 0.1521(11) 0.013(3) Uani 1 1 d . . . . .
C11 C 0.1835(13) 0.1954(10) 0.1871(11) 0.013(3) Uani 1 1 d . . . . .
C12 C 0.0965(14) 0.2935(11) 0.1495(11) 0.017(3) Uani 1 1 d . . . . .
H12 H 0.0478 0.3631 0.1959 0.021 Uiso 1 1 calc R U . . .
C13 C 0.0782(13) 0.2928(11) 0.0434(11) 0.018(3) Uani 1 1 d . . . . .
H13 H 0.0175 0.3618 0.0175 0.021 Uiso 1 1 calc R U . . .
C14 C 0.1474(14) 0.1928(11) -0.0234(11) 0.017(3) Uani 1 1 d . . . . .
H14 H 0.1335 0.1934 -0.0953 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2366(13) 0.0915(10) 0.0105(10) 0.011(3) Uani 1 1 d . . . . .
H15 H 0.2862 0.0231 -0.0376 0.013 Uiso 1 1 calc R U . . .
C16 C 0.2520(13) 0.0924(10) 0.1186(10) 0.010(3) Uani 1 1 d . . . . .
C17 C 0.4864(13) -0.1941(10) 0.1645(10) 0.010(2) Uani 1 1 d . U . . .
C18 C 0.5266(12) -0.1864(10) 0.2562(11) 0.012(3) Uani 1 1 d . . . . .
C19 C 0.5405(13) -0.3077(10) 0.1081(11) 0.014(3) Uani 1 1 d . . . . .
C20 C 0.6763(13) -0.3928(11) 0.2365(11) 0.014(3) Uani 1 1 d . . . . .
N1 N 0.3386(10) 0.0988(8) 0.4421(8) 0.010(2) Uani 1 1 d . . . . .
N2 N 0.4033(10) 0.1650(8) 0.4507(8) 0.009(2) Uani 1 1 d . U . . .
N3 N 0.6416(11) 0.3307(8) 0.2688(8) 0.010(2) Uani 1 1 d D U . . .
N4 N 0.6161(10) 0.2323(8) 0.1383(8) 0.010(2) Uani 1 1 d D U . . .
N5 N 0.3377(10) -0.0018(8) 0.1673(8) 0.008(2) Uani 1 1 d . . . . .
N6 N 0.3954(10) -0.1039(8) 0.1203(8) 0.007(2) Uani 1 1 d . U . . .
N7 N 0.6186(11) -0.2849(9) 0.2875(8) 0.013(2) Uani 1 1 d D . . . .
N8 N 0.6382(11) -0.3947(8) 0.1440(9) 0.012(2) Uani 1 1 d D U . . .
O1 O 0.2060(9) -0.0234(7) 0.4080(7) 0.0122(18) Uani 1 1 d . . . . .
O2 O 0.4849(9) 0.1128(6) 0.1961(7) 0.0118(18) Uani 1 1 d . . . . .
O1W O 0.6388(15) -0.4811(11) -0.1594(11) 0.067(4) Uani 1 1 d . . . . .
O3 O 0.5248(9) 0.3183(7) 0.4697(7) 0.0167(19) Uani 1 1 d . U . . .
O2W O 0.8938(14) 0.2927(13) -0.1787(10) 0.075(4) Uani 1 1 d . . . . .
O4 O 0.7402(9) 0.3644(7) 0.0660(7) 0.0158(19) Uani 1 1 d . . . . .
O3W O 0.1539(11) -0.2116(9) 0.3558(9) 0.034(3) Uani 1 1 d D . . . .
O5 O 0.2024(9) 0.1902(7) 0.2899(7) 0.0123(18) Uani 1 1 d . . . . .
O4W O 0.6291(12) 0.4048(10) 0.6008(9) 0.042(3) Uani 1 1 d D . . . .
O6 O 0.4870(9) -0.0956(7) 0.3164(7) 0.0123(18) Uani 1 1 d . . . . .
O7 O 0.5039(9) -0.3278(7) 0.0325(7) 0.0171(19) Uani 1 1 d . U . . .
O8 O 0.7554(9) -0.4805(7) 0.2710(7) 0.0131(18) Uani 1 1 d . U . . .
O10 O 0.0200(13) 0.3303(8) 0.4746(9) 0.044(3) Uani 1 1 d D . . . .
O11 O 0.2161(15) 0.4719(13) 0.3977(15) 0.096(5) Uani 1 1 d . . . . .
O12 O -0.0477(18) 0.5619(13) 0.3484(12) 0.084(5) Uani 1 1 d . . . . .
Co1 Co 0.34322(17) 0.04640(13) 0.30345(14) 0.0094(4) Uani 1 1 d . . . . .
Co2 Co 0.0000 0.5000 0.5000 0.0140(6) Uani 1 2 d S . P . .
H3N H 0.708(10) 0.364(9) 0.262(10) 0.021 Uiso 1 1 d D U . . .
H4N H 0.609(13) 0.234(10) 0.067(6) 0.021 Uiso 1 1 d D U . . .
H7N H 0.622(14) -0.245(9) 0.340(8) 0.021 Uiso 1 1 d D U . . .
H8N H 0.694(10) -0.465(6) 0.107(10) 0.021 Uiso 1 1 d D U . . .
H11W H 0.5912 -0.5318 -0.1300 0.021 Uiso 1 1 d . U . . .
H12W H 0.8350 0.2979 -0.1029 0.021 Uiso 1 1 d . U . . .
H13W H 0.150(14) -0.137(5) 0.362(9) 0.021 Uiso 1 1 d D U . . .
H14W H 0.622(12) 0.355(8) 0.559(8) 0.021 Uiso 1 1 d D U . . .
H21W H 0.6068 -0.4349 -0.0997 0.021 Uiso 1 1 d . U . . .
H22W H 0.9571 0.2220 -0.1813 0.021 Uiso 1 1 d . U . . .
H23W H 0.130(14) -0.196(8) 0.291(8) 0.021 Uiso 1 1 d D U . . .
H24W H 0.699(10) 0.428(10) 0.538(6) 0.021 Uiso 1 1 d D U . . .
H110 H 0.095(8) 0.283(7) 0.417(7) 0.021 Uiso 1 1 d D U . . .
H111 H 0.2764 0.4193 0.4242 0.021 Uiso 1 1 d . U . . .
H112 H -0.1079 0.5648 0.3200 0.021 Uiso 1 1 d . U . . .
H210 H -0.008(11) 0.274(7) 0.527(7) 0.021 Uiso 1 1 d D U . . .
H211 H 0.2355 0.4419 0.3281 0.021 Uiso 1 1 d . U . . .
H212 H 0.0312 0.5629 0.2792 0.021 Uiso 1 1 d . 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
C1 O1 1.354(13) . ?
C1 C6 1.398(14) . ?
C1 C2 1.405(16) . ?
C2 C3 1.365(16) . ?
C3 C4 1.391(16) . ?
C4 C5 1.346(16) . ?
C5 C6 1.402(15) . ?
C6 N1 1.412(14) . ?
C7 N2 1.344(14) . ?
C7 C9 1.416(15) . ?
C7 C8 1.467(14) . ?
C8 O3 1.216(13) . ?
C8 N3 1.379(15) . ?
C9 O2 1.261(12) . ?
C9 N4 1.359(14) . ?
C10 O4 1.232(14) . ?
C10 N4 1.359(13) . ?
C10 N3 1.370(14) . ?
C11 O5 1.342(13) . ?
C11 C12 1.360(16) . ?
C11 C16 1.407(16) . ?
C12 C13 1.394(16) . ?
C13 C14 1.366(17) . ?
C14 C15 1.374(16) . ?
C15 C16 1.401(15) . ?
C16 N5 1.398(14) . ?
C17 N6 1.377(14) . ?
C17 C18 1.391(15) . ?
C17 C19 1.453(16) . ?
C18 O6 1.268(13) . ?
C18 N7 1.357(15) . ?
C19 O7 1.239(13) . ?
C19 N8 1.352(15) . ?
C20 O8 1.228(14) . ?
C20 N7 1.359(14) . ?
C20 N8 1.363(14) . ?
N1 N2 1.283(12) . ?
N1 Co1 1.889(9) . ?
N5 N6 1.277(12) . ?
N5 Co1 1.890(9) . ?
O1 Co1 1.867(8) . ?
O2 Co1 1.884(7) . ?
O5 Co1 1.882(8) . ?
O6 Co1 1.884(8) . ?
O10 Co2 2.043(8) . ?
O11 Co2 2.076(14) . ?
O12 Co2 2.066(12) . ?
Co2 O10 2.043(8) 2_566 ?
Co2 O12 2.066(12) 2_566 ?
Co2 O11 2.076(14) 2_566 ?

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 C1 C6 118.1(10) . . ?
O1 C1 C2 122.7(10) . . ?
C6 C1 C2 119.2(11) . . ?
C3 C2 C1 118.5(10) . . ?
C2 C3 C4 121.3(11) . . ?
C5 C4 C3 121.6(11) . . ?
C4 C5 C6 118.3(10) . . ?
C1 C6 C5 121.0(10) . . ?
C1 C6 N1 112.9(10) . . ?
C5 C6 N1 126.1(10) . . ?
N2 C7 C9 127.0(9) . . ?
N2 C7 C8 114.3(10) . . ?
C9 C7 C8 118.7(10) . . ?
O3 C8 N3 119.7(10) . . ?
O3 C8 C7 124.6(11) . . ?
N3 C8 C7 115.6(10) . . ?
O2 C9 N4 115.0(10) . . ?
O2 C9 C7 126.5(10) . . ?
N4 C9 C7 118.4(9) . . ?
O4 C10 N4 122.8(10) . . ?
O4 C10 N3 121.7(10) . . ?
N4 C10 N3 115.5(10) . . ?
O5 C11 C12 123.0(11) . . ?
O5 C11 C16 118.0(10) . . ?
C12 C11 C16 118.9(11) . . ?
C11 C12 C13 120.5(11) . . ?
C14 C13 C12 120.0(11) . . ?
C13 C14 C15 121.8(11) . . ?
C14 C15 C16 117.8(11) . . ?
N5 C16 C15 125.9(10) . . ?
N5 C16 C11 113.0(10) . . ?
C15 C16 C11 121.0(11) . . ?
N6 C17 C18 126.7(10) . . ?
N6 C17 C19 114.1(10) . . ?
C18 C17 C19 119.2(11) . . ?
O6 C18 N7 114.1(10) . . ?
O6 C18 C17 127.3(11) . . ?
N7 C18 C17 118.6(10) . . ?
O7 C19 N8 120.2(10) . . ?
O7 C19 C17 125.0(11) . . ?
N8 C19 C17 114.8(10) . . ?
O8 C20 N7 122.9(11) . . ?
O8 C20 N8 123.3(10) . . ?
N7 C20 N8 113.9(11) . . ?
N2 N1 C6 119.6(9) . . ?
N2 N1 Co1 129.9(8) . . ?
C6 N1 Co1 110.4(7) . . ?
N1 N2 C7 119.3(9) . . ?
C10 N3 C8 125.7(9) . . ?
C10 N4 C9 125.4(10) . . ?
N6 N5 C16 119.4(9) . . ?
N6 N5 Co1 129.7(7) . . ?
C16 N5 Co1 110.9(7) . . ?
N5 N6 C17 118.9(9) . . ?
C18 N7 C20 125.4(10) . . ?
C19 N8 C20 127.6(10) . . ?
C1 O1 Co1 110.5(6) . . ?
C9 O2 Co1 122.9(7) . . ?
C11 O5 Co1 110.5(7) . . ?
C18 O6 Co1 122.3(7) . . ?
O1 Co1 O5 92.2(3) . . ?
O1 Co1 O6 88.9(3) . . ?
O5 Co1 O6 178.7(3) . . ?
O1 Co1 O2 178.4(4) . . ?
O5 Co1 O2 89.0(3) . . ?
O6 Co1 O2 89.9(3) . . ?
O1 Co1 N1 87.1(4) . . ?
O5 Co1 N1 91.0(4) . . ?
O6 Co1 N1 88.5(4) . . ?
O2 Co1 N1 93.7(3) . . ?
O1 Co1 N5 91.3(3) . . ?
O5 Co1 N5 86.6(4) . . ?
O6 Co1 N5 94.0(4) . . ?
O2 Co1 N5 87.9(3) . . ?
N1 Co1 N5 177.1(4) . . ?
O10 Co2 O10 180.00(7) . 2_566 ?
O10 Co2 O12 89.2(5) . 2_566 ?
O10 Co2 O12 90.8(5) 2_566 2_566 ?
O10 Co2 O12 90.8(5) . . ?
O10 Co2 O12 89.2(5) 2_566 . ?
O12 Co2 O12 180.0 2_566 . ?
O10 Co2 O11 88.4(5) . 2_566 ?
O10 Co2 O11 91.6(5) 2_566 2_566 ?
O12 Co2 O11 90.8(7) 2_566 2_566 ?
O12 Co2 O11 89.2(7) . 2_566 ?
O10 Co2 O11 91.6(5) . . ?
O10 Co2 O11 88.4(5) 2_566 . ?
O12 Co2 O11 89.2(7) 2_566 . ?
O12 Co2 O11 90.8(7) . . ?
O11 Co2 O11 180.0 2_566 . ?

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
C5 H5 O6 0.95 2.49 3.284(13) 141.1 2_656
C15 H15 O2 0.95 2.60 3.468(14) 151.7 2_655
N3 H3N O8 0.91(3) 2.15(7) 2.968(11) 148(10) 1_565
N4 H4N O7 0.90(3) 2.00(8) 2.771(12) 143(11) 2_655
N8 H8N O4 0.91(3) 2.03(6) 2.887(12) 156(11) 1_545
O1W H11W O7 0.870 2.200 3.062(14) 168.4(9) 2_645
O2W H12W O4 0.8700) 2.050 2.860(14) 155.0 .
O3W H13W O1 0.90(3) 1.94(5) 2.764(11) 153(9) .
O4W H14W N7 0.89(3) 2.84(9) 3.199(13) 106(7) 2_656
O4W H14W O3 0.89(3) 2.00(6) 2.818(12) 151(11) .
O1W H21W O7 0.8700 1.930 2.790(14) 170.0 .
O3W H23W O2W 0.90(3) 2.10(6) 2.827(16) 137(8) 2_655
O10 H110 O5 0.90(3) 1.79(5) 2.661(12) 163(12) .
O12 H112 O8 0.8500 2.080 2.902(14) 162.8(9) 1_465
O10 H210 O3W 0.88(3) 1.92(6) 2.739(13) 152(10) 2_556
O11 H211 O1W 0.900 2.020 2.67(2) 128.1(10) 2_655
O12 H212 O2W 0.920 2.150 2.837(19) 131.2(9) 2_665
C5 H5 O6 0.95 2.49 3.284(13) 141.1 2_656
C15 H15 O2 0.95 2.60 3.468(14) 151.7 2_655
N3 H3N O8 0.91(3) 2.15(7) 2.968(11) 148(10) 1_565
N4 H4N O7 0.90(3) 2.00(8) 2.771(12) 143(11) 2_655
N8 H8N O4 0.91(3) 2.03(6) 2.887(12) 156(11) 1_545
O1W H11W O7 0.870 2.200 3.062(14) 168.4(9) 2_645
O2W H12W O4 0.8700 2.050 2.860(14) 155.0 .
O3W H13W O1 0.90(3) 1.94(5) 2.764(11) 153(9) .
O4W H14W O3 0.89(3) 2.00(6) 2.818(12) 151(11) .
O1W H21W O7 0.8700 1.930 2.790(14) 170.0 .
O3W H23W O2W 0.90(3) 2.10(6) 2.827(16) 137(8) 2_655
O4W H24W O3 0.91(3) 3.15(12) 3.276(14) 90(8) 2_666
O10 H110 O5 0.90(3) 1.79(5) 2.661(12) 163(12) .
O12 H112 O8 0.8500 2.080 2.902(14) 162.8(9) 1_465
O10 H210 O3W 0.88(3) 1.92(6) 2.739(13) 152(10) 2_556
O11 H211 O1W 0.900 2.020 2.67(2) 128.1(10) 2_655
O12 H212 O2W 0.920 2.150 2.837(19) 131.2(9) 2_665

_refine_diff_density_max         3.763
_refine_diff_density_min         -1.609
_refine_diff_density_rms         0.306

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1055321'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Co N10 O6 S'
_chemical_formula_sum            'C19 H18 Co N10 O6 S'
_chemical_formula_weight         573.42

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'
Co Co 0.3494 0.9721 '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                   18.9274(10)
_cell_length_b                   8.6362(5)
_cell_length_c                   16.9906(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.753(2)
_cell_angle_gamma                90
_cell_volume                     2673.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5120
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.28

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_F_000             1172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.773
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.955
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29502
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_av_R_equivalents  0.1126
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4798
_reflns_number_gt                2949
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1317P)²+2.7927P] 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         4798
_refine_ls_number_parameters     334
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1410
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2114
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 -0.028 0.250 210 68 ' '
2 1.000 -0.023 0.750 211 68 ' '
_platon_squeeze_details          
;
 There were disordered molecules present in the structure of 5.
 Since no obvious major site occupations were found for those molecules,
 it was not possible to model them. PLATON/SQUEEZE was used to correct
 the data but the assignement is dubious. Thus, they were simply
 removed from the model. 
;

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
Co1 Co 0.70351(5) 0.44345(10) 0.29133(5) 0.0268(3) Uani 1 1 d . . . . .
S1 S 0.64508(9) 0.42410(18) 0.45660(9) 0.0263(4) Uani 1 1 d . . . . .
O1 O 0.7950(2) 0.5783(5) 0.3509(3) 0.0427(13) Uani 1 1 d . . . . .
O2 O 1.0375(5) 0.6685(10) 0.3974(5) 0.104(2) Uani 1 1 d . U . . .
O3 O 0.9693(3) 0.1721(7) 0.4269(5) 0.089(2) Uani 1 1 d . . . . .
O11 O 0.6430(2) 0.5044(5) 0.3804(3) 0.0297(11) Uani 1 1 d . . . . .
O12 O 0.5760(3) 0.4388(6) 0.4767(3) 0.0414(12) Uani 1 1 d . . . . .
O13 O 0.7078(3) 0.4691(6) 0.5229(3) 0.0429(13) Uani 1 1 d . . . . .
N1 N 0.7576(3) 0.2861(6) 0.3837(3) 0.0266(12) Uani 1 1 d . . . . .
N2 N 0.8266(3) 0.2536(6) 0.4069(4) 0.0369(14) Uani 1 1 d . . . . .
N3 N 0.9150(4) 0.6169(9) 0.3753(4) 0.063(2) Uani 1 1 d . U . . .
H3 H 0.9056 0.7136 0.3659 0.094 Uiso 1 1 calc R U . . .
N4 N 1.0013(5) 0.4142(10) 0.4094(5) 0.078(2) Uani 1 1 d . U . . .
H4 H 1.0459 0.3830 0.4185 0.117 Uiso 1 1 calc R U . . .
N11 N 0.6127(3) 0.3048(6) 0.2325(3) 0.0293(13) Uani 1 1 d . . . . .
N12 N 0.5392(4) 0.1659(7) 0.1359(4) 0.0541(19) Uani 1 1 d . . . . .
H12 H 0.5233 0.1125 0.0919 0.081 Uiso 1 1 calc R U . . .
N21 N 0.6628(3) 0.6396(7) 0.2200(3) 0.0376(15) Uani 1 1 d . . . . .
N22 N 0.6637(4) 0.8413(7) 0.1432(4) 0.0538(19) Uani 1 1 d . . . . .
H22 H 0.6791 0.9216 0.1230 0.081 Uiso 1 1 calc R U . . .
N31 N 0.7642(3) 0.3632(8) 0.2103(4) 0.0461(16) Uani 1 1 d . . . . .
N32 N 0.8260(6) 0.3438(13) 0.1218(6) 0.109(3) Uani 1 1 d . U . . .
H32 H 0.8458 0.3697 0.0837 0.164 Uiso 1 1 calc R U . . .
C1 C 0.7129(4) 0.1714(7) 0.4078(4) 0.0281(15) Uani 1 1 d . . . . .
C2 C 0.6559(4) 0.2227(7) 0.4396(3) 0.0252(15) Uani 1 1 d . . . . .
C3 C 0.6100(4) 0.1148(9) 0.4597(4) 0.0365(17) Uani 1 1 d . . . . .
H3A H 0.5723 0.1475 0.4813 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6194(5) -0.0414(9) 0.4481(5) 0.048(2) Uani 1 1 d . . . . .
H4A H 0.5875 -0.1130 0.4609 0.058 Uiso 1 1 calc R U . . .
C5 C 0.6756(5) -0.0912(8) 0.4179(5) 0.048(2) Uani 1 1 d . . . . .
H5 H 0.6819 -0.1965 0.4105 0.058 Uiso 1 1 calc R U . . .
C6 C 0.7226(4) 0.0140(8) 0.3984(5) 0.0393(18) Uani 1 1 d . . . . .
H6 H 0.7612 -0.0205 0.3788 0.047 Uiso 1 1 calc R U . . .
C7 C 0.8745(4) 0.3593(9) 0.3923(5) 0.046(2) Uani 1 1 d . . . . .
C8 C 0.8566(4) 0.5181(9) 0.3703(4) 0.0394(18) Uani 1 1 d . U . . .
C9 C 0.9485(4) 0.3041(10) 0.4109(7) 0.069(3) Uani 1 1 d . . . . .
C10 C 0.9880(6) 0.5704(13) 0.3946(7) 0.081(3) Uani 1 1 d . U . . .
C11 C 0.5464(4) 0.2908(9) 0.2478(4) 0.0393(18) Uani 1 1 d . . . . .
H11 H 0.5341 0.3356 0.2921 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5005(4) 0.2032(8) 0.1902(4) 0.0391(18) Uani 1 1 d . . . . .
H12A H 0.4527 0.1743 0.1881 0.047 Uiso 1 1 calc R U . . .
C13 C 0.6051(4) 0.2262(9) 0.1628(4) 0.0431(19) Uani 1 1 d . . . . .
H13 H 0.6421 0.2156 0.1365 0.052 Uiso 1 1 calc R U . . .
C21 C 0.5950(4) 0.6559(9) 0.1650(4) 0.0386(18) Uani 1 1 d . . . . .
H21 H 0.5550 0.5905 0.1607 0.046 Uiso 1 1 calc R U . . .
C22 C 0.5955(5) 0.7795(9) 0.1190(5) 0.051(2) Uani 1 1 d . . . . .
H22A H 0.5563 0.8168 0.0776 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7019(5) 0.7548(9) 0.2039(5) 0.054(2) Uani 1 1 d . . . . .
H23 H 0.7506 0.7733 0.2319 0.065 Uiso 1 1 calc R U . . .
C31 C 0.7947(5) 0.2215(13) 0.2123(6) 0.073(3) Uani 1 1 d . . . . .
H31 H 0.7897 0.1415 0.2470 0.087 Uiso 1 1 calc R U . . .
C32 C 0.8338(6) 0.2131(13) 0.1560(6) 0.072(3) Uani 1 1 d . U . . .
H32A H 0.8604 0.1291 0.1452 0.087 Uiso 1 1 calc R U . . .
C33 C 0.7821(6) 0.4402(13) 0.1526(6) 0.081(3) Uani 1 1 d . . . . .
H33 H 0.7680 0.5406 0.1356 0.098 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
Co1 O1 2.104(5) . ?
Co1 N21 2.104(6) . ?
Co1 N11 2.110(5) . ?
Co1 N1 2.118(5) . ?
Co1 N31 2.134(6) . ?
Co1 O11 2.195(4) . ?
S1 O12 1.445(5) . ?
S1 O13 1.450(5) . ?
S1 O11 1.460(4) . ?
S1 C2 1.784(6) . ?
O1 C8 1.237(8) . ?
O2 C10 1.255(12) . ?
O3 C9 1.213(10) . ?
N1 N2 1.289(7) . ?
N1 C1 1.432(8) . ?
N2 C7 1.355(9) . ?
N3 C8 1.381(10) . ?
N3 C10 1.389(13) . ?
N3 H3 0.8600 . ?
N4 C10 1.383(13) . ?
N4 C9 1.384(11) . ?
N4 H4 0.8600 . ?
N11 C13 1.339(9) . ?
N11 C11 1.354(9) . ?
N12 C13 1.314(10) . ?
N12 C12 1.363(10) . ?
N12 H12 0.8600 . ?
N21 C23 1.312(10) . ?
N21 C21 1.375(9) . ?
N22 C23 1.319(9) . ?
N22 C22 1.352(11) . ?
N22 H22 0.8600 . ?
N31 C33 1.303(11) . ?
N31 C31 1.349(12) . ?
N32 C32 1.260(13) . ?
N32 C33 1.377(13) . ?
N32 H32 0.8600 . ?
C1 C6 1.387(9) . ?
C1 C2 1.403(9) . ?
C2 C3 1.379(9) . ?
C3 C4 1.383(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(11) . ?
C4 H4A 0.9300 . ?
C5 C6 1.374(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C9 1.433(11) . ?
C7 C8 1.438(10) . ?
C11 C12 1.350(9) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?
C21 C22 1.325(10) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9300 . ?
C23 H23 0.9300 . ?
C31 C32 1.360(13) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9300 . ?
C33 H33 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 Co1 N21 87.5(2) . . ?
O1 Co1 N11 179.02(19) . . ?
N21 Co1 N11 93.5(2) . . ?
O1 Co1 N1 80.20(18) . . ?
N21 Co1 N1 166.3(2) . . ?
N11 Co1 N1 98.9(2) . . ?
O1 Co1 N31 88.5(2) . . ?
N21 Co1 N31 93.8(2) . . ?
N11 Co1 N31 91.3(2) . . ?
N1 Co1 N31 91.9(2) . . ?
O1 Co1 O11 92.91(19) . . ?
N21 Co1 O11 91.50(19) . . ?
N11 Co1 O11 87.27(19) . . ?
N1 Co1 O11 83.14(18) . . ?
N31 Co1 O11 174.6(2) . . ?
O12 S1 O13 113.3(3) . . ?
O12 S1 O11 111.1(3) . . ?
O13 S1 O11 112.4(3) . . ?
O12 S1 C2 106.0(3) . . ?
O13 S1 C2 106.3(3) . . ?
O11 S1 C2 107.2(3) . . ?
C8 O1 Co1 119.2(5) . . ?
S1 O11 Co1 127.1(3) . . ?
N2 N1 C1 113.0(5) . . ?
N2 N1 Co1 127.7(4) . . ?
C1 N1 Co1 116.9(4) . . ?
N1 N2 C7 118.0(6) . . ?
C8 N3 C10 124.4(8) . . ?
C8 N3 H3 117.8 . . ?
C10 N3 H3 117.8 . . ?
C10 N4 C9 125.2(9) . . ?
C10 N4 H4 117.4 . . ?
C9 N4 H4 117.4 . . ?
C13 N11 C11 104.0(6) . . ?
C13 N11 Co1 125.7(5) . . ?
C11 N11 Co1 129.6(5) . . ?
C13 N12 C12 107.8(6) . . ?
C13 N12 H12 126.1 . . ?
C12 N12 H12 126.1 . . ?
C23 N21 C21 104.8(6) . . ?
C23 N21 Co1 126.3(5) . . ?
C21 N21 Co1 127.0(5) . . ?
C23 N22 C22 106.8(7) . . ?
C23 N22 H22 126.6 . . ?
C22 N22 H22 126.6 . . ?
C33 N31 C31 106.6(8) . . ?
C33 N31 Co1 127.9(6) . . ?
C31 N31 Co1 125.4(6) . . ?
C32 N32 C33 111.8(11) . . ?
C32 N32 H32 124.1 . . ?
C33 N32 H32 124.1 . . ?
C6 C1 C2 119.5(6) . . ?
C6 C1 N1 122.6(6) . . ?
C2 C1 N1 117.8(6) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 S1 120.7(5) . . ?
C1 C2 S1 120.3(5) . . ?
C2 C3 C4 120.6(7) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 120.3(7) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.1(7) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.4(7) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N2 C7 C9 113.5(6) . . ?
N2 C7 C8 124.7(6) . . ?
C9 C7 C8 121.4(7) . . ?
O1 C8 N3 116.0(7) . . ?
O1 C8 C7 127.5(7) . . ?
N3 C8 C7 116.4(7) . . ?
O3 C9 N4 117.3(8) . . ?
O3 C9 C7 126.9(8) . . ?
N4 C9 C7 115.8(8) . . ?
O2 C10 N4 123.6(11) . . ?
O2 C10 N3 119.9(10) . . ?
N4 C10 N3 116.4(10) . . ?
C12 C11 N11 111.0(7) . . ?
C12 C11 H11 124.5 . . ?
N11 C11 H11 124.5 . . ?
C11 C12 N12 105.3(6) . . ?
C11 C12 H12A 127.3 . . ?
N12 C12 H12A 127.3 . . ?
N12 C13 N11 111.8(7) . . ?
N12 C13 H13 124.1 . . ?
N11 C13 H13 124.1 . . ?
C22 C21 N21 109.1(7) . . ?
C22 C21 H21 125.4 . . ?
N21 C21 H21 125.4 . . ?
C21 C22 N22 107.3(7) . . ?
C21 C22 H22A 126.3 . . ?
N22 C22 H22A 126.3 . . ?
N21 C23 N22 111.8(8) . . ?
N21 C23 H23 124.1 . . ?
N22 C23 H23 124.1 . . ?
N31 C31 C32 110.0(10) . . ?
N31 C31 H31 125.0 . . ?
C32 C31 H31 125.0 . . ?
N32 C32 C31 105.0(11) . . ?
N32 C32 H32A 127.5 . . ?
C31 C32 H32A 127.5 . . ?
N31 C33 N32 106.6(10) . . ?
N31 C33 H33 126.7 . . ?
N32 C33 H33 126.7 . . ?

_refine_diff_density_max         1.159
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.119

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1055322'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 Cu N8 O6 S, H2 O'
_chemical_formula_sum            'C16 H16 Cu N8 O7 S'
_chemical_formula_weight         527.97

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.6884(17)
_cell_length_b                   11.586(2)
_cell_length_c                   20.943(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.642(7)
_cell_angle_gamma                90
_cell_volume                     2089.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6370
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.22

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             1076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.204
_shelx_estimated_absorpt_T_min   0.714
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.922
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20644
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         25.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3840
_reflns_number_gt                3004
_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-2013 (Sheldrick, 2013)'
_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)+(0.0956P)²+2.2829P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3840
_refine_ls_number_parameters     305
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1603
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.003
_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 0.57611(6) 0.12196(5) 0.21574(2) 0.0304(2) Uani 1 1 d . . . . .
S1 S 0.56976(14) -0.13488(10) 0.14933(6) 0.0411(3) Uani 1 1 d . . . . .
O1W O 0.2419(5) 0.1488(5) 0.3955(3) 0.0767(14) Uani 1 1 d D . . . .
O1 O 0.5189(3) 0.0856(3) 0.30038(14) 0.0389(7) Uani 1 1 d . . . . .
O3 O 0.5989(4) 0.1117(3) 0.51627(16) 0.0556(10) Uani 1 1 d . . . . .
O2 O 1.0064(4) -0.0029(3) 0.41889(15) 0.0503(9) Uani 1 1 d . . . . .
N4 N 0.5628(4) 0.0943(3) 0.40766(16) 0.0346(8) Uani 1 1 d . . . . .
H4 H 0.4660 0.1109 0.4065 0.042 Uiso 1 1 calc R U . . .
N3 N 0.8015(5) 0.0549(3) 0.46553(16) 0.0396(9) Uani 1 1 d . . . . .
H3 H 0.8594 0.0496 0.5020 0.048 Uiso 1 1 calc R U . . .
N11 N 0.3926(4) 0.2249(3) 0.20457(17) 0.0366(9) Uani 1 1 d . . . . .
C11 C 0.2875(6) 0.2347(5) 0.2445(2) 0.0534(14) Uani 1 1 d . . . . .
H11 H 0.2885 0.1914 0.2820 0.064 Uiso 1 1 calc R U . . .
C12 C 0.1828(5) 0.3117(5) 0.2254(2) 0.0441(12) Uani 1 1 d . . . . .
H12 H 0.0995 0.3323 0.2466 0.053 Uiso 1 1 calc R U . . .
N12 N 0.2152(8) 0.3554(6) 0.1707(4) 0.106(2) Uani 1 1 d . . . . .
H13 H 0.1635 0.4076 0.1478 0.127 Uiso 1 1 calc R U . . .
C14 C 0.3448(8) 0.3023(6) 0.1579(3) 0.080(2) Uani 1 1 d . . . . .
H14 H 0.3946 0.3168 0.1221 0.096 Uiso 1 1 calc R U . . .
C7 C 0.6185(5) 0.0762(4) 0.35004(19) 0.0301(9) Uani 1 1 d . . . . .
C10 C 0.6512(6) 0.0876(4) 0.4670(2) 0.0380(10) Uani 1 1 d . . . . .
C9 C 0.8697(5) 0.0297(4) 0.4120(2) 0.0344(10) Uani 1 1 d . . . . .
C8 C 0.7745(5) 0.0442(4) 0.35097(19) 0.0294(9) Uani 1 1 d . . . . .
N2 N 0.8387(4) 0.0101(3) 0.29858(16) 0.0292(8) Uani 1 1 d . . . . .
N1 N 0.7654(4) 0.0233(3) 0.24236(15) 0.0295(8) Uani 1 1 d . . . . .
C6 C 0.8455(5) -0.0227(4) 0.1924(2) 0.0314(9) Uani 1 1 d . . . . .
C1 C 0.7616(5) -0.0875(4) 0.1431(2) 0.0332(10) Uani 1 1 d . . . . .
O11 O 0.4766(4) -0.0340(3) 0.15792(18) 0.0516(9) Uani 1 1 d . . . . .
O13 O 0.5179(5) -0.1967(4) 0.09070(19) 0.0653(11) Uani 1 1 d . . . . .
O12 O 0.5857(5) -0.2088(4) 0.20545(19) 0.0621(11) Uani 1 1 d . . . . .
C2 C 0.8337(6) -0.1226(4) 0.0911(2) 0.0471(12) Uani 1 1 d . . . . .
H2 H 0.7786 -0.1645 0.0577 0.057 Uiso 1 1 calc R U . . .
C3 C 0.9877(7) -0.0951(5) 0.0891(3) 0.0586(15) Uani 1 1 d . . . . .
H3A H 1.0353 -0.1177 0.0539 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0713(6) -0.0346(5) 0.1386(3) 0.0600(15) Uani 1 1 d . . . . .
H4A H 1.1757 -0.0184 0.1372 0.072 Uiso 1 1 calc R U . . .
C5 C 1.0002(6) 0.0021(5) 0.1903(2) 0.0459(12) Uani 1 1 d . . . . .
H5 H 1.0565 0.0434 0.2237 0.055 Uiso 1 1 calc R U . . .
N21 N 0.6584(4) 0.1816(3) 0.13791(17) 0.0373(9) Uani 1 1 d . . . . .
C21 C 0.5928(8) 0.1641(5) 0.0776(2) 0.0601(15) Uani 1 1 d . . . . .
H21 H 0.5011 0.1232 0.0661 0.072 Uiso 1 1 calc R U . . .
N22 N 0.6744(9) 0.2118(5) 0.0368(2) 0.085(2) Uani 1 1 d . . . . .
H22 H 0.6529 0.2112 -0.0045 0.103 Uiso 1 1 calc R U . . .
C23 C 0.8015(10) 0.2637(5) 0.0720(3) 0.073(2) Uani 1 1 d . . . . .
H23 H 0.8809 0.3039 0.0560 0.088 Uiso 1 1 calc R U . . .
C24 C 0.7866(7) 0.2442(5) 0.1336(3) 0.0529(13) Uani 1 1 d . . . . .
H24 H 0.8551 0.2702 0.1685 0.064 Uiso 1 1 calc R U . . .
H1W1 H 0.182(6) 0.211(3) 0.392(3) 0.079 Uiso 1 1 d D U . . .
H1W2 H 0.189(7) 0.083(3) 0.396(4) 0.10(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.950(3) . ?
Cu1 N11 1.980(4) . ?
Cu1 N21 1.989(4) . ?
Cu1 N1 2.020(3) . ?
Cu1 O11 2.281(3) . ?
S1 O13 1.441(4) . ?
S1 O12 1.446(4) . ?
S1 O11 1.446(4) . ?
S1 C1 1.776(5) . ?
O1W H1W1 0.88(2) . ?
O1W H1W2 0.89(2) . ?
O1 C7 1.266(5) . ?
O3 C10 1.213(5) . ?
O2 C9 1.236(5) . ?
N4 C10 1.374(6) . ?
N4 C7 1.375(5) . ?
N4 H4 0.8600 . ?
N3 C10 1.364(6) . ?
N3 C9 1.368(6) . ?
N3 H3 0.8600 . ?
N11 C11 1.323(6) . ?
N11 C14 1.350(6) . ?
C11 C12 1.299(7) . ?
C11 H11 0.9300 . ?
C12 N12 1.316(8) . ?
C12 H12 0.9300 . ?
N12 C14 1.341(8) . ?
N12 H13 0.8600 . ?
C14 H14 0.9300 . ?
C7 C8 1.403(6) . ?
C9 C8 1.436(6) . ?
C8 N2 1.354(5) . ?
N2 N1 1.271(5) . ?
N1 C6 1.435(5) . ?
C6 C5 1.380(6) . ?
C6 C1 1.401(6) . ?
C1 C2 1.387(6) . ?
C2 C3 1.381(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(7) . ?
C4 H4A 0.9300 . ?
C5 H5 0.9300 . ?
N21 C21 1.330(6) . ?
N21 C24 1.342(7) . ?
C21 N22 1.305(8) . ?
C21 H21 0.9300 . ?
N22 C23 1.382(10) . ?
N22 H22 0.8600 . ?
C23 C24 1.334(8) . ?
C23 H23 0.9300 . ?
C24 H24 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 N11 86.48(14) . . ?
O1 Cu1 N21 169.45(15) . . ?
N11 Cu1 N21 93.76(15) . . ?
O1 Cu1 N1 85.62(13) . . ?
N11 Cu1 N1 170.75(14) . . ?
N21 Cu1 N1 93.12(14) . . ?
O1 Cu1 O11 100.79(14) . . ?
N11 Cu1 O11 99.92(14) . . ?
N21 Cu1 O11 89.56(15) . . ?
N1 Cu1 O11 86.29(13) . . ?
O13 S1 O12 112.6(3) . . ?
O13 S1 O11 113.0(2) . . ?
O12 S1 O11 111.8(2) . . ?
O13 S1 C1 106.3(2) . . ?
O12 S1 C1 104.7(2) . . ?
O11 S1 C1 107.8(2) . . ?
H1W1 O1W H1W2 114(4) . . ?
C7 O1 Cu1 122.4(3) . . ?
C10 N4 C7 124.5(4) . . ?
C10 N4 H4 117.8 . . ?
C7 N4 H4 117.8 . . ?
C10 N3 C9 126.8(4) . . ?
C10 N3 H3 116.6 . . ?
C9 N3 H3 116.6 . . ?
C11 N11 C14 103.2(4) . . ?
C11 N11 Cu1 126.1(3) . . ?
C14 N11 Cu1 130.6(3) . . ?
C12 C11 N11 112.2(5) . . ?
C12 C11 H11 123.9 . . ?
N11 C11 H11 123.9 . . ?
C11 C12 N12 108.1(5) . . ?
C11 C12 H12 125.9 . . ?
N12 C12 H12 125.9 . . ?
C12 N12 C14 106.2(5) . . ?
C12 N12 H13 126.9 . . ?
C14 N12 H13 126.9 . . ?
N12 C14 N11 110.2(5) . . ?
N12 C14 H14 124.9 . . ?
N11 C14 H14 124.9 . . ?
O1 C7 N4 115.2(4) . . ?
O1 C7 C8 126.0(4) . . ?
N4 C7 C8 118.7(4) . . ?
O3 C10 N3 123.5(4) . . ?
O3 C10 N4 121.9(5) . . ?
N3 C10 N4 114.6(4) . . ?
O2 C9 N3 118.9(4) . . ?
O2 C9 C8 124.8(4) . . ?
N3 C9 C8 116.3(4) . . ?
N2 C8 C7 124.5(4) . . ?
N2 C8 C9 115.8(4) . . ?
C7 C8 C9 119.0(4) . . ?
N1 N2 C8 120.4(4) . . ?
N2 N1 C6 113.5(3) . . ?
N2 N1 Cu1 127.8(3) . . ?
C6 N1 Cu1 117.7(3) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 N1 120.9(4) . . ?
C1 C6 N1 118.8(4) . . ?
C2 C1 C6 119.4(4) . . ?
C2 C1 S1 119.6(4) . . ?
C6 C1 S1 120.8(3) . . ?
S1 O11 Cu1 121.84(19) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C21 N21 C24 105.9(5) . . ?
C21 N21 Cu1 124.7(4) . . ?
C24 N21 Cu1 129.4(3) . . ?
N22 C21 N21 110.8(6) . . ?
N22 C21 H21 124.6 . . ?
N21 C21 H21 124.6 . . ?
C21 N22 C23 107.5(5) . . ?
C21 N22 H22 126.3 . . ?
C23 N22 H22 126.3 . . ?
C24 C23 N22 105.6(6) . . ?
C24 C23 H23 127.2 . . ?
N22 C23 H23 127.2 . . ?
C23 C24 N21 110.2(6) . . ?
C23 C24 H24 124.9 . . ?
N21 C24 H24 124.9 . . ?

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
N4 H4 O1W 0.86 1.98 2.837(5) 175.0 .
N3 H3 O2 0.86 1.97 2.817(5) 168.0 3_756
C11 H11 O1W 0.93 2.51 3.388(7) 156.8 .
C12 H12 S1 0.93 2.81 3.690(5) 157.8 2
C12 H12 O12 0.93 2.06 2.915(6) 151.7 2
C14 H14 O2 0.93 2.46 3.147(7) 131.1 2_655
N22 H22 O13 0.86 2.19 2.960(7) 149.7 3_655
C23 H23 O3 0.93 2.38 3.305(8) 174.0 4_665
C24 H24 O12 0.93 2.63 3.449(7) 147.0 2_655
O1W H1W1 S1 0.88(2) 2.87(3) 3.717(4) 162(5) 2
O1W H1W1 O13 0.88(2) 2.12(4) 2.925(6) 152(6) 2
O1W H1W2 O2 0.89(2) 1.99(4) 2.790(6) 150(6) 1_455

_refine_diff_density_max         1.158
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.153

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1055325'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10 H7 N4 O6 S), Co H12 O6, 8(H2 O)'
_chemical_formula_sum            'C20 H42 Co N8 O26 S2'
_chemical_formula_weight         933.66

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'
Co Co 0.3494 0.9721 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.8042(6)
_cell_length_b                   6.5960(2)
_cell_length_c                   18.5585(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.6090(10)
_cell_angle_gamma                90
_cell_volume                     1921.77(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9850
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      26.40

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             970
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    0.659
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.845
_exptl_absorpt_correction_T_max  0.954
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43754
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3893
_reflns_number_gt                3326
_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-2013 (Sheldrick, 2013)'
_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)+(0.0718P)²+2.0652P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3893
_refine_ls_number_parameters     304
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1331
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.003
_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 0.60990(16) 0.3400(4) 0.66286(14) 0.0316(5) Uani 1 1 d . . . . .
C2 C 0.61503(17) 0.5075(4) 0.70945(14) 0.0318(5) Uani 1 1 d . . . . .
C3 C 0.68147(19) 0.6448(4) 0.70805(16) 0.0416(6) Uani 1 1 d . . . . .
H3 H 0.6849 0.7563 0.7389 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7427(2) 0.6174(5) 0.66112(18) 0.0478(7) Uani 1 1 d . . . . .
H4 H 0.7870 0.7100 0.6605 0.057 Uiso 1 1 calc R U . . .
C5 C 0.73739(19) 0.4517(5) 0.61537(18) 0.0465(7) Uani 1 1 d . . . . .
H5 H 0.7783 0.4329 0.5838 0.056 Uiso 1 1 calc R U . . .
C6 C 0.67202(18) 0.3138(4) 0.61605(16) 0.0403(6) Uani 1 1 d . . . . .
H6 H 0.6693 0.2026 0.5851 0.048 Uiso 1 1 calc R U . . .
C7 C 0.47745(15) -0.0881(4) 0.61705(14) 0.0308(5) Uani 1 1 d . . . . .
C8 C 0.48559(16) -0.2576(4) 0.56778(14) 0.0318(5) Uani 1 1 d . . . . .
C9 C 0.40233(17) -0.0736(4) 0.65587(15) 0.0354(6) Uani 1 1 d . . . . .
C10 C 0.34975(17) -0.3900(5) 0.59965(15) 0.0389(6) Uani 1 1 d . . . . .
N3 N 0.54193(14) 0.2010(3) 0.66249(12) 0.0335(5) Uani 1 1 d D . . . .
N4 N 0.54089(13) 0.0418(3) 0.62113(12) 0.0306(5) Uani 1 1 d . . . . .
N5 N 0.34263(14) -0.2237(4) 0.64224(13) 0.0374(5) Uani 1 1 d D . . . .
N6 N 0.42071(14) -0.3975(4) 0.56356(12) 0.0368(5) Uani 1 1 d D . . . .
O1 O 0.39219(14) 0.0636(4) 0.69841(13) 0.0529(6) Uani 1 1 d . . . . .
O2 O 0.29638(15) -0.5228(4) 0.59307(14) 0.0588(7) Uani 1 1 d . . . . .
O1W O 0.3396(2) 0.7786(6) 0.83184(16) 0.0823(9) Uani 1 1 d D . . . .
O3 O 0.54487(12) -0.2808(3) 0.53116(11) 0.0427(5) Uani 1 1 d . . . . .
O2W O 0.3181(2) 0.3177(7) 0.8081(2) 0.1136(14) Uani 1 1 d D . . . .
O3W O 0.34940(17) 0.4789(4) 0.03341(14) 0.0492(6) Uani 1 1 d . . . . .
O4W O 0.80985(15) 0.3957(4) 0.01036(14) 0.0560(6) Uani 1 1 d D . . . .
O11 O 0.45859(15) 0.4938(4) 0.73727(13) 0.0576(6) Uani 1 1 d . . . . .
O12 O 0.56843(16) 0.4136(4) 0.83314(12) 0.0575(6) Uani 1 1 d . . . . .
O13 O 0.5471(2) 0.7588(4) 0.79293(14) 0.0683(8) Uani 1 1 d . . . . .
O21 O 0.38836(15) 0.1502(4) -0.03814(13) 0.0578(6) Uani 1 1 d D . . . .
O22 O 0.54914(15) 0.2747(3) 0.04222(12) 0.0465(5) Uani 1 1 d D . . . .
O23 O 0.54332(19) 0.0416(3) -0.10108(12) 0.0567(7) Uani 1 1 d D . . . .
S1 S 0.54134(4) 0.54655(10) 0.77367(3) 0.03350(18) Uani 1 1 d . . . . .
Co1 Co 0.5000 0.0000 0.0000 0.03185(16) Uani 1 2 d S . P . .
H1W1 H 0.343(2) 0.664(3) 0.8134(19) 0.048 Uiso 1 1 d D U . . .
H1W2 H 0.2950(17) 0.851(5) 0.8351(19) 0.048 Uiso 1 1 d D U . . .
H2W1 H 0.289(2) 0.396(5) 0.7701(16) 0.048 Uiso 1 1 d D U . . .
H2W2 H 0.3547(17) 0.266(5) 0.7815(15) 0.048 Uiso 1 1 d D U . . .
H3N H 0.4964(16) 0.222(5) 0.6873(16) 0.048 Uiso 1 1 d D U . . .
H3W1 H 0.362(3) 0.491(5) 0.073(2) 0.048 Uiso 1 1 d . U . . .
H3W2 H 0.297(3) 0.508(5) 0.030(2) 0.048 Uiso 1 1 d . U . . .
H4W1 H 0.8500(17) 0.359(5) -0.0170(15) 0.048 Uiso 1 1 d D U . . .
H4W2 H 0.804(2) 0.293(4) 0.0411(15) 0.048 Uiso 1 1 d D U . . .
H5N H 0.2949(15) -0.221(5) 0.6626(17) 0.048 Uiso 1 1 d D U . . .
H6N H 0.426(2) -0.509(4) 0.5366(17) 0.048 Uiso 1 1 d D U . . .
H21A H 0.3682 0.2590 -0.0126 0.048 Uiso 1 1 d D U . . .
H21B H 0.4230 0.2232 -0.0689 0.048 Uiso 1 1 d D U . . .
H22A H 0.5799(19) 0.343(5) 0.0134(15) 0.048 Uiso 1 1 d D U . . .
H22B H 0.5872(17) 0.259(5) 0.0810(13) 0.048 Uiso 1 1 d D U . . .
H23A H 0.544(2) 0.153(4) -0.1265(16) 0.048 Uiso 1 1 d D U . . .
H23B H 0.545(2) -0.056(4) -0.1328(16) 0.048 Uiso 1 1 d D 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
C1 C6 1.395(4) . ?
C1 C2 1.400(3) . ?
C1 N3 1.412(3) . ?
C2 C3 1.389(4) . ?
C2 S1 1.778(3) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N4 1.314(3) . ?
C7 C8 1.459(3) . ?
C7 C9 1.461(3) . ?
C8 O3 1.229(3) . ?
C8 N6 1.375(3) . ?
C9 O1 1.224(3) . ?
C9 N5 1.371(4) . ?
C10 O2 1.212(3) . ?
C10 N5 1.364(4) . ?
C10 N6 1.372(3) . ?
N3 N4 1.300(3) . ?
N3 H3N 0.909(18) . ?
N5 H5N 0.881(18) . ?
N6 H6N 0.899(18) . ?
O1W H1W1 0.833(17) . ?
O1W H1W2 0.860(17) . ?
O2W H2W1 0.952(17) . ?
O2W H2W2 0.873(18) . ?
O3W H3W1 0.74(4) . ?
O3W H3W2 0.84(4) . ?
O4W H4W1 0.890(18) . ?
O4W H4W2 0.897(18) . ?
O11 S1 1.444(3) . ?
O12 S1 1.436(2) . ?
O13 S1 1.445(2) . ?
O21 Co1 2.075(2) . ?
O21 H21A 0.940 . ?
O21 H21B 0.960 . ?
O22 Co1 2.088(2) . ?
O22 H22A 0.888(18) . ?
O22 H22B 0.890(18) . ?
O23 Co1 2.088(2) . ?
O23 H23A 0.876(18) . ?
O23 H23B 0.874(18) . ?
Co1 O21 2.075(2) 3_655 ?
Co1 O23 2.088(2) 3_655 ?
Co1 O22 2.088(2) 3_655 ?

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 119.2(2) . . ?
C6 C1 N3 120.4(2) . . ?
C2 C1 N3 120.4(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 S1 118.2(2) . . ?
C1 C2 S1 122.2(2) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N4 C7 C8 114.4(2) . . ?
N4 C7 C9 125.9(2) . . ?
C8 C7 C9 119.6(2) . . ?
O3 C8 N6 119.7(2) . . ?
O3 C8 C7 124.7(2) . . ?
N6 C8 C7 115.5(2) . . ?
O1 C9 N5 121.0(2) . . ?
O1 C9 C7 122.7(3) . . ?
N5 C9 C7 116.3(2) . . ?
O2 C10 N5 122.4(3) . . ?
O2 C10 N6 121.6(3) . . ?
N5 C10 N6 116.0(2) . . ?
N4 N3 C1 119.0(2) . . ?
N4 N3 H3N 118(2) . . ?
C1 N3 H3N 123(2) . . ?
N3 N4 C7 121.2(2) . . ?
C10 N5 C9 125.9(2) . . ?
C10 N5 H5N 113(2) . . ?
C9 N5 H5N 121(2) . . ?
C10 N6 C8 126.5(2) . . ?
C10 N6 H6N 116(2) . . ?
C8 N6 H6N 117(2) . . ?
H1W1 O1W H1W2 129(3) . . ?
H2W1 O2W H2W2 96(3) . . ?
H3W1 O3W H3W2 101(4) . . ?
H4W1 O4W H4W2 107(3) . . ?
Co1 O21 H21A 121.00 . . ?
Co1 O21 H21B 86.00 . . ?
H21A O21 H21B 100.00 . . ?
Co1 O22 H22A 115(2) . . ?
Co1 O22 H22B 113(2) . . ?
H22A O22 H22B 101(3) . . ?
Co1 O23 H23A 128(2) . . ?
Co1 O23 H23B 123(2) . . ?
H23A O23 H23B 105(3) . . ?
O12 S1 O11 112.72(16) . . ?
O12 S1 O13 113.38(16) . . ?
O11 S1 O13 112.19(17) . . ?
O12 S1 C2 105.45(13) . . ?
O11 S1 C2 106.22(13) . . ?
O13 S1 C2 106.15(13) . . ?
O21 Co1 O21 180.0 . 3_655 ?
O21 Co1 O23 90.88(11) . 3_655 ?
O21 Co1 O23 89.12(11) 3_655 3_655 ?
O21 Co1 O23 89.12(11) . . ?
O21 Co1 O23 90.88(11) 3_655 . ?
O23 Co1 O23 180.0 3_655 . ?
O21 Co1 O22 91.22(9) . 3_655 ?
O21 Co1 O22 88.78(9) 3_655 3_655 ?
O23 Co1 O22 94.40(9) 3_655 3_655 ?
O23 Co1 O22 85.60(9) . 3_655 ?
O21 Co1 O22 88.78(9) . . ?
O21 Co1 O22 91.22(9) 3_655 . ?
O23 Co1 O22 85.60(9) 3_655 . ?
O23 Co1 O22 94.40(9) . . ?
O22 Co1 O22 180.0 3_655 . ?

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
O1W H1W1 O2W 0.833(17) 2.32(2) 3.085(6) 153(3) .
O1W H1W2 O2 0.860(17) 2.24(2) 2.994(4) 147(3) 2_566
O2W H2W2 O1 0.873(18) 2.17(2) 2.978(4) 154(3) .
O2W H2W2 O11 0.873(18) 2.44(3) 2.946(4) 118(3) .
N3 H3N O1 0.909(18) 1.98(3) 2.689(3) 133(3) .
N3 H3N O11 0.909(18) 2.13(3) 2.795(3) 129(3) .
O3W H3W1 O12 0.74(4) 2.05(4) 2.754(4) 158(4) 3_666
O3W H3W2 O4W 0.84(4) 1.88(4) 2.685(3) 159(3) 3_665
O4W H4W1 O3 0.890(18) 1.95(2) 2.762(3) 152(3) 2_655
O4W H4W2 O2 0.897(18) 2.04(2) 2.920(3) 168(3) 4_655
N5 H5N O2W 0.881(18) 1.943(19) 2.813(4) 169(3) 2_546
N6 H6N O3 0.899(18) 1.960(19) 2.848(3) 169(3) 3_646
O21 H21A O3W 0.940 1.730 2.652(3) 169.33 .
O21 H21B O22 0.960 2.720 2.913(3) 92.00 .
O21 H21B O23 0.960 2.380 2.921(3) 115.00 .
O22 H22A O3W 0.888(18) 1.90(2) 2.775(3) 170(3) 3_665
O22 H22B O1W 0.890(18) 1.893(19) 2.780(4) 175(3) 3_666
O23 H23A O12 0.876(18) 1.93(2) 2.789(3) 166(3) 1_554
O23 H23B O13 0.874(18) 1.846(19) 2.717(3) 174(3) 1_544

_refine_diff_density_max         0.737
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.093

_shelxl_version_number           2013-4

