# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1456524'
_audit_update_record             
;
2016-02-28 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H38 Cu N8 O10 S2'
_chemical_formula_sum            'C26 H38 Cu N8 O10 S2'
_chemical_formula_weight         750.30

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

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

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

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

_cell_length_a                   7.4179(4)
_cell_length_b                   20.0875(12)
_cell_length_c                   11.2037(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.071(2)
_cell_angle_gamma                90
_cell_volume                     1604.19(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6570
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.21

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.879
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_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            16062
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.774
_diffrn_reflns_theta_max         27.307
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3597
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  ?
_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)+(0.0466P)²+1.2786P] 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         3597
_refine_ls_number_parameters     231
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.005
_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 0.5073(3) 0.14965(10) 0.2467(2) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.6254(3) 0.13240(12) 0.3623(2) 0.0371(5) Uani 1 1 d . . . . .
H2 H 0.6637 0.0884 0.3780 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6864(4) 0.17982(14) 0.4538(2) 0.0420(6) Uani 1 1 d . . . . .
H3 H 0.7658 0.1677 0.5306 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6300(4) 0.24510(13) 0.4318(2) 0.0401(6) Uani 1 1 d . . . . .
H4 H 0.6709 0.2767 0.4940 0.048 Uiso 1 1 calc R U . . .
C5 C 0.5129(3) 0.26387(12) 0.3180(2) 0.0352(5) Uani 1 1 d . . . . .
H5 H 0.4752 0.3080 0.3037 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4517(3) 0.21652(10) 0.2248(2) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.1929(3) 0.31647(11) -0.0272(2) 0.0309(5) Uani 1 1 d . . . . .
C8 C 0.0857(3) 0.27071(13) -0.1246(2) 0.0369(5) Uani 1 1 d . . . . .
C9 C -0.0106(4) 0.29400(15) -0.2532(2) 0.0477(6) Uani 1 1 d . . . . .
H9A H -0.0324 0.2567 -0.3090 0.072 Uiso 1 1 calc R U . . .
H9B H 0.0671 0.3260 -0.2789 0.072 Uiso 1 1 calc R U . . .
H9C H -0.1283 0.3142 -0.2541 0.072 Uiso 1 1 calc R U . . .
C10 C 0.1826(4) 0.38999(12) -0.0413(2) 0.0403(6) Uani 1 1 d . . . . .
C11 C 0.3214(5) 0.43209(14) 0.0500(3) 0.0573(8) Uani 1 1 d . . . . .
H11A H 0.2723 0.4763 0.0499 0.086 Uiso 1 1 calc R U . . .
H11B H 0.4368 0.4338 0.0271 0.086 Uiso 1 1 calc R U . . .
H11C H 0.3442 0.4132 0.1315 0.086 Uiso 1 1 calc R U . . .
C12 C -0.1714(4) 0.07723(15) -0.2137(3) 0.0512(7) Uani 1 1 d . . . . .
H12A H -0.2109 0.1207 -0.2490 0.061 Uiso 1 1 calc R U . . .
H12B H -0.2610 0.0444 -0.2581 0.061 Uiso 1 1 calc R U . . .
C13 C 0.0219(4) 0.06123(14) -0.2249(3) 0.0507(7) Uani 1 1 d . . . . .
H13A H 0.0175 0.0549 -0.3115 0.061 Uiso 1 1 calc R U . . .
H13B H 0.1069 0.0977 -0.1922 0.061 Uiso 1 1 calc R U . . .
N1 N 0.3302(3) 0.23421(9) 0.10827(18) 0.0304(4) Uani 1 1 d D . . . .
N2 N 0.3056(3) 0.29699(9) 0.07979(17) 0.0301(4) Uani 1 1 d . . . . .
N3 N 0.0892(3) -0.00031(11) -0.1540(2) 0.0395(5) Uani 1 1 d D . . . .
N4 N -0.1629(3) 0.07661(11) -0.0814(2) 0.0410(5) Uani 1 1 d D . . . .
O1 O 0.0803(3) 0.21145(10) -0.09895(19) 0.0595(6) Uani 1 1 d . . . . .
O2 O 0.0628(4) 0.41589(11) -0.1244(2) 0.0704(7) Uani 1 1 d . . . . .
O11 O 0.5144(3) 0.02561(9) 0.1855(2) 0.0511(5) Uani 1 1 d . . . . .
O12 O 0.2352(2) 0.09023(9) 0.09162(18) 0.0461(5) Uani 1 1 d . . . . .
O13 O 0.5179(3) 0.10920(11) 0.0308(2) 0.0584(6) Uani 1 1 d . . . . .
S1 S 0.43896(8) 0.08786(3) 0.12913(6) 0.03223(15) Uani 1 1 d . . . . .
Cu1 Cu 0.0000 0.0000 0.0000 0.03258(13) Uani 1 2 d S . P . .
H1N H 0.266(4) 0.2050(12) 0.058(2) 0.049 Uiso 1 1 d D U . . .
H3A H 0.208(3) -0.0057(14) -0.141(3) 0.049 Uiso 1 1 d D U . . .
H3B H 0.049(4) -0.0345(11) -0.199(2) 0.049 Uiso 1 1 d D U . . .
H4A H -0.276(3) 0.0734(15) -0.072(3) 0.049 Uiso 1 1 d D U . . .
H4B H -0.116(4) 0.1135(11) -0.046(3) 0.049 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 C2 1.392(3) . ?
C1 C6 1.407(3) . ?
C1 S1 1.778(2) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.411(3) . ?
C7 N2 1.317(3) . ?
C7 C8 1.479(3) . ?
C7 C10 1.485(3) . ?
C8 O1 1.228(3) . ?
C8 C9 1.495(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O2 1.212(3) . ?
C10 C11 1.496(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N4 1.466(4) . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N3 1.480(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 N2 1.301(3) . ?
N1 H1N 0.857(17) . ?
N3 Cu1 2.011(2) . ?
N3 H3A 0.861(18) . ?
N3 H3B 0.855(17) . ?
N4 Cu1 2.012(2) . ?
N4 H4A 0.873(17) . ?
N4 H4B 0.868(17) . ?
O11 S1 1.4421(19) . ?
O12 S1 1.4530(18) . ?
O13 S1 1.448(2) . ?
Cu1 N3 2.011(2) 3 ?
Cu1 N4 2.013(2) 3 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.6(2) . . ?
C2 C1 S1 119.49(17) . . ?
C6 C1 S1 121.85(16) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 N1 120.9(2) . . ?
C1 C6 N1 118.89(19) . . ?
N2 C7 C8 124.3(2) . . ?
N2 C7 C10 113.2(2) . . ?
C8 C7 C10 122.6(2) . . ?
O1 C8 C7 118.4(2) . . ?
O1 C8 C9 119.4(2) . . ?
C7 C8 C9 122.2(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 C7 120.9(2) . . ?
O2 C10 C11 120.1(2) . . ?
C7 C10 C11 118.9(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 C13 107.9(2) . . ?
N4 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N4 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N3 C13 C12 108.7(2) . . ?
N3 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
N3 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
N2 N1 C6 118.78(18) . . ?
N2 N1 H1N 119(2) . . ?
C6 N1 H1N 122(2) . . ?
N1 N2 C7 121.47(19) . . ?
C13 N3 Cu1 108.41(17) . . ?
C13 N3 H3A 112(2) . . ?
Cu1 N3 H3A 115(2) . . ?
C13 N3 H3B 110(2) . . ?
Cu1 N3 H3B 111(2) . . ?
H3A N3 H3B 100(3) . . ?
C12 N4 Cu1 108.47(17) . . ?
C12 N4 H4A 110(2) . . ?
Cu1 N4 H4A 111(2) . . ?
C12 N4 H4B 111(2) . . ?
Cu1 N4 H4B 109(2) . . ?
H4A N4 H4B 107(3) . . ?
O11 S1 O13 113.59(13) . . ?
O11 S1 O12 113.67(12) . . ?
O13 S1 O12 112.18(13) . . ?
O11 S1 C1 106.53(11) . . ?
O13 S1 C1 105.31(11) . . ?
O12 S1 C1 104.58(10) . . ?
N3 Cu1 N3 180.00(10) . 3 ?
N3 Cu1 N4 85.00(9) . . ?
N3 Cu1 N4 95.00(9) 3 . ?
N3 Cu1 N4 95.00(9) . 3 ?
N3 Cu1 N4 85.00(9) 3 3 ?
N4 Cu1 N4 180.0 . 3 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
S1 C1 C2 C3 177.60(19) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 N1 179.2(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
S1 C1 C6 C5 -177.97(17) . . . . ?
C2 C1 C6 N1 -179.3(2) . . . . ?
S1 C1 C6 N1 3.4(3) . . . . ?
N2 C7 C8 O1 10.3(4) . . . . ?
C10 C7 C8 O1 -169.5(2) . . . . ?
N2 C7 C8 C9 -168.0(2) . . . . ?
C10 C7 C8 C9 12.3(4) . . . . ?
N2 C7 C10 O2 -167.6(3) . . . . ?
C8 C7 C10 O2 12.2(4) . . . . ?
N2 C7 C10 C11 11.7(3) . . . . ?
C8 C7 C10 C11 -168.6(2) . . . . ?
N4 C12 C13 N3 51.4(3) . . . . ?
C5 C6 N1 N2 13.5(3) . . . . ?
C1 C6 N1 N2 -167.83(19) . . . . ?
C6 N1 N2 C7 -179.5(2) . . . . ?
C8 C7 N2 N1 -0.4(4) . . . . ?
C10 C7 N2 N1 179.4(2) . . . . ?
C12 C13 N3 Cu1 -36.8(3) . . . . ?
C13 C12 N4 Cu1 -40.4(3) . . . . ?
C2 C1 S1 O11 4.9(2) . . . . ?
C6 C1 S1 O11 -177.80(18) . . . . ?
C2 C1 S1 O13 -116.0(2) . . . . ?
C6 C1 S1 O13 61.3(2) . . . . ?
C2 C1 S1 O12 125.55(19) . . . . ?
C6 C1 S1 O12 -57.1(2) . . . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1456525'
_audit_update_record             
;
2016-05-03 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 Cu N4 O4 S'
_chemical_formula_sum            'C13 H16 Cu N4 O4 S'
_chemical_formula_weight         387.90

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

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1923(10)
_cell_length_b                   8.6543(16)
_cell_length_c                   16.704(3)
_cell_angle_alpha                81.729(5)
_cell_angle_beta                 88.354(6)
_cell_angle_gamma                78.606(6)
_cell_volume                     728.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4584
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.99

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.670
_shelx_estimated_absorpt_T_min   0.562
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_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            20570
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.425
_diffrn_reflns_theta_max         28.484
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3657
_reflns_number_gt                2708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  ?
_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)+(0.0433P)²+0.2724P] 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         3657
_refine_ls_number_parameters     216
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.995
_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 -0.0246(5) 0.5960(3) 0.72219(17) 0.0129(6) Uani 1 1 d . . . . .
C2 C -0.2509(6) 0.6974(3) 0.74499(18) 0.0173(6) Uani 1 1 d . . . . .
H2 H -0.3743 0.7533 0.7049 0.021 Uiso 1 1 calc R U . . .
C3 C -0.2965(6) 0.7171(4) 0.82434(19) 0.0225(7) Uani 1 1 d . . . . .
H3 H -0.4525 0.7843 0.8395 0.027 Uiso 1 1 calc R U . . .
C4 C -0.1136(6) 0.6384(4) 0.88218(19) 0.0224(7) Uani 1 1 d . . . . .
H4 H -0.1408 0.6552 0.9370 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1084(6) 0.5357(3) 0.86112(18) 0.0192(7) Uani 1 1 d . . . . .
H5 H 0.2305 0.4816 0.9020 0.023 Uiso 1 1 calc R U . . .
C6 C 0.1573(5) 0.5095(3) 0.78083(17) 0.0118(6) Uani 1 1 d . . . . .
C7 C 0.7410(6) 0.2242(3) 0.82914(17) 0.0150(6) Uani 1 1 d . . . . .
C8 C 0.8526(6) 0.1951(4) 0.91250(19) 0.0207(7) Uani 1 1 d . . . . .
C9 C 0.6679(7) 0.2345(4) 0.98076(19) 0.0299(8) Uani 1 1 d . . . . .
H9A H 0.7502 0.1823 1.0323 0.045 Uiso 1 1 calc R U . . .
H9B H 0.5050 0.1967 0.9739 0.045 Uiso 1 1 calc R U . . .
H9C H 0.6279 0.3500 0.9806 0.045 Uiso 1 1 calc R U . . .
C10 C 0.8669(5) 0.1409(3) 0.76402(17) 0.0132(6) Uani 1 1 d . . . . .
C11 C 1.1186(6) 0.0221(4) 0.78012(19) 0.0232(7) Uani 1 1 d . . . . .
H11A H 1.1241 -0.0639 0.7474 0.035 Uiso 1 1 calc R U . . .
H11B H 1.1284 -0.0223 0.8376 0.035 Uiso 1 1 calc R U . . .
H11C H 1.2677 0.0746 0.7659 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8758(6) 0.0848(3) 0.62658(17) 0.0156(6) Uani 1 1 d . . . . .
H12A H 0.9454 -0.0287 0.6466 0.019 Uiso 1 1 calc R U . . .
H12B H 1.0227 0.1335 0.6027 0.019 Uiso 1 1 calc R U . . .
C13 C 0.6653(6) 0.0994(3) 0.56385(18) 0.0175(6) Uani 1 1 d . . . . .
H13A H 0.7456 0.0657 0.5131 0.021 Uiso 1 1 calc R U . . .
H13B H 0.5395 0.0301 0.5836 0.021 Uiso 1 1 calc R U . . .
N1 N 0.3840(4) 0.3975(3) 0.76072(14) 0.0120(5) Uani 1 1 d . . . . .
N2 N 0.5207(5) 0.3315(3) 0.82612(14) 0.0146(5) Uani 1 1 d . . . . .
N3 N 0.7559(4) 0.1681(3) 0.69369(14) 0.0122(5) Uani 1 1 d . . . . .
N4 N 0.5271(5) 0.2677(3) 0.54880(14) 0.0136(5) Uani 1 1 d D . . . .
O1 O 1.0866(5) 0.1453(3) 0.92614(15) 0.0350(6) Uani 1 1 d . . . . .
O11 O 0.2954(4) 0.5593(2) 0.60311(11) 0.0125(4) Uani 1 1 d . . . . .
O12 O -0.0959(4) 0.4485(2) 0.60243(12) 0.0170(4) Uani 1 1 d . . . . .
O13 O -0.1202(4) 0.7345(2) 0.57491(12) 0.0174(5) Uani 1 1 d . . . . .
S1 S 0.00860(13) 0.58429(8) 0.61796(4) 0.01052(15) Uani 1 1 d . . . . .
Cu1 Cu 0.49256(7) 0.35215(4) 0.65381(2) 0.01096(11) Uani 1 1 d . . . . .
H41N H 0.370(6) 0.270(3) 0.5195(19) 0.016 Uiso 1 1 d D U . . .
H42N H 0.619(5) 0.328(3) 0.5160(16) 0.016 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 C2 1.400(4) . ?
C1 C6 1.405(4) . ?
C1 S1 1.760(3) . ?
C2 C3 1.369(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.380(4) . ?
C5 C6 1.400(4) . ?
C6 N1 1.434(3) . ?
C7 N2 1.321(3) . ?
C7 C10 1.459(4) . ?
C7 C8 1.492(4) . ?
C8 O1 1.223(4) . ?
C8 C9 1.502(4) . ?
C10 N3 1.294(4) . ?
C10 C11 1.499(4) . ?
C12 N3 1.476(3) . ?
C12 C13 1.511(4) . ?
C13 N4 1.480(4) . ?
N1 N2 1.315(3) . ?
N1 Cu1 1.928(2) . ?
N3 Cu1 1.933(2) . ?
N4 Cu1 1.986(2) . ?
O11 S1 1.481(2) . ?
O11 Cu1 1.9667(18) . ?
O12 S1 1.446(2) . ?
O13 S1 1.4383(19) . ?

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
C2 C1 C6 120.4(3) . . ?
C2 C1 S1 115.6(2) . . ?
C6 C1 S1 123.9(2) . . ?
C3 C2 C1 120.8(3) . . ?
C2 C3 C4 119.4(3) . . ?
C3 C4 C5 120.7(3) . . ?
C4 C5 C6 121.4(3) . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 N1 120.5(2) . . ?
C1 C6 N1 122.3(2) . . ?
N2 C7 C10 128.0(3) . . ?
N2 C7 C8 109.6(2) . . ?
C10 C7 C8 122.4(2) . . ?
O1 C8 C7 122.4(3) . . ?
O1 C8 C9 119.9(3) . . ?
C7 C8 C9 117.7(3) . . ?
N3 C10 C7 119.4(2) . . ?
N3 C10 C11 121.0(3) . . ?
C7 C10 C11 119.6(2) . . ?
N3 C12 C13 107.7(2) . . ?
N4 C13 C12 108.4(2) . . ?
N2 N1 C6 110.4(2) . . ?
N2 N1 Cu1 122.95(18) . . ?
C6 N1 Cu1 126.55(18) . . ?
N1 N2 C7 126.2(2) . . ?
C10 N3 C12 120.9(2) . . ?
C10 N3 Cu1 125.87(19) . . ?
C12 N3 Cu1 110.90(17) . . ?
C13 N4 Cu1 107.90(17) . . ?
S1 O11 Cu1 114.28(11) . . ?
O13 S1 O12 114.80(12) . . ?
O13 S1 O11 110.26(12) . . ?
O12 S1 O11 111.07(11) . . ?
O13 S1 C1 107.89(12) . . ?
O12 S1 C1 107.64(13) . . ?
O11 S1 C1 104.58(12) . . ?
N1 Cu1 N3 93.62(10) . . ?
N1 Cu1 O11 92.06(9) . . ?
N3 Cu1 O11 166.75(9) . . ?
N1 Cu1 N4 163.70(10) . . ?
N3 Cu1 N4 86.20(10) . . ?
O11 Cu1 N4 91.67(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
C9 H9B O1 0.98 2.48 3.438(4) 166.4 1_455
C12 H12A O13 0.99 2.60 3.266(3) 124.7 1_645
N4 H41N O13 0.96(3) 2.08(3) 3.002(3) 161(3) 2_566
N4 H41N S1 0.96(3) 3.03(3) 3.892(3) 150(2) 2_566
N4 H42N O11 0.895(17) 2.16(2) 2.975(3) 151(3) 2_666
N4 H42N O12 0.895(17) 2.56(3) 2.966(3) 109(2) 1_655

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_Compound2rev
_database_code_depnum_ccdc_archive 'CCDC 1456526'
_audit_update_record             
;
2016-05-30 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C11 H11 N2 O5 S), C6 H24 N6 Ni, C2 H6 O, 6(H2 O)'
_chemical_formula_sum            'C30 H64 N10 Ni O17 S2'
_chemical_formula_weight         959.74

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5824(7)
_cell_length_b                   13.5921(7)
_cell_length_c                   14.6115(9)
_cell_angle_alpha                72.171(3)
_cell_angle_beta                 75.626(4)
_cell_angle_gamma                85.530(3)
_cell_volume                     2121.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6908
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.64

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             1020
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.638
_shelx_estimated_absorpt_T_min   0.771
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            39682
_diffrn_reflns_av_unetI/netI     0.0797
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         25.740
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             7996
_reflns_number_gt                4331
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1'
_computing_publication_material  ?
_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)+(0.0852P)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         7996
_refine_ls_number_parameters     521
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 1.0201(4) 0.3739(3) 0.9027(3) 0.0310(9) Uani 1 1 d . . . . .
C2 C 1.1330(4) 0.3997(4) 0.9029(3) 0.0414(11) Uani 1 1 d . . . . .
H2 H 1.1896 0.3480 0.9151 0.050 Uiso 1 1 calc R U . . .
C3 C 1.1628(4) 0.5008(4) 0.8854(3) 0.0440(12) Uani 1 1 d . . . . .
H3 H 1.2391 0.5177 0.8852 0.053 Uiso 1 1 calc R U . . .
C4 C 1.0782(4) 0.5767(4) 0.8683(3) 0.0448(12) Uani 1 1 d . . . . .
H4 H 1.0974 0.6450 0.8583 0.054 Uiso 1 1 calc R U . . .
C5 C 0.9659(4) 0.5536(3) 0.8657(3) 0.0364(10) Uani 1 1 d . . . . .
H5 H 0.9104 0.6062 0.8528 0.044 Uiso 1 1 calc R U . . .
C6 C 0.9352(4) 0.4522(3) 0.8822(3) 0.0296(9) Uani 1 1 d . . . . .
C7 C 0.6317(4) 0.4800(3) 0.8693(3) 0.0425(11) Uani 1 1 d . . . . .
C8 C 0.5927(5) 0.3814(4) 0.8643(4) 0.0542(13) Uani 1 1 d . . . . .
C9 C 0.4726(5) 0.3682(4) 0.8493(5) 0.0712(17) Uani 1 1 d . . . . .
H9A H 0.4271 0.4305 0.8482 0.107 Uiso 1 1 calc R U . . .
H9B H 0.4815 0.3538 0.7875 0.107 Uiso 1 1 calc R U . . .
H9C H 0.4319 0.3119 0.9023 0.107 Uiso 1 1 calc R U . . .
C10 C 0.5523(4) 0.5722(4) 0.8695(4) 0.0502(12) Uani 1 1 d . . . . .
C11 C 0.6040(5) 0.6691(4) 0.8689(4) 0.0635(15) Uani 1 1 d . . . . .
H11A H 0.6869 0.6584 0.8688 0.095 Uiso 1 1 calc R U . . .
H11B H 0.5957 0.7233 0.8107 0.095 Uiso 1 1 calc R U . . .
H11C H 0.5628 0.6880 0.9267 0.095 Uiso 1 1 calc R U . . .
C12 C 0.7654(3) 0.6650(3) 0.6046(3) 0.0270(9) Uani 1 1 d . . . . .
C13 C 0.6522(4) 0.6432(3) 0.5995(3) 0.0352(10) Uani 1 1 d . . . . .
H13 H 0.5955 0.6955 0.5921 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6234(4) 0.5444(4) 0.6054(3) 0.0447(11) Uani 1 1 d . . . . .
H14 H 0.5480 0.5301 0.6011 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7077(4) 0.4675(3) 0.6176(3) 0.0431(11) Uani 1 1 d . . . . .
H15 H 0.6889 0.4009 0.6213 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8179(4) 0.4873(3) 0.6242(3) 0.0388(10) Uani 1 1 d . . . . .
H16 H 0.8733 0.4340 0.6329 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8487(3) 0.5861(3) 0.6180(3) 0.0299(9) Uani 1 1 d . . . . .
C18 C 1.1530(4) 0.5477(3) 0.6345(3) 0.0332(10) Uani 1 1 d . . . . .
C19 C 1.1958(4) 0.6492(4) 0.6318(3) 0.0394(11) Uani 1 1 d . . . . .
C20 C 1.3223(4) 0.6646(4) 0.6299(5) 0.0674(16) Uani 1 1 d . . . . .
H20A H 1.3657 0.6013 0.6309 0.101 Uiso 1 1 calc R U . . .
H20B H 1.3571 0.7178 0.5708 0.101 Uiso 1 1 calc R U . . .
H20C H 1.3257 0.6846 0.6867 0.101 Uiso 1 1 calc R U . . .
C21 C 1.2273(4) 0.4524(3) 0.6430(3) 0.0370(10) Uani 1 1 d . . . . .
C22 C 1.1710(4) 0.3553(3) 0.6504(4) 0.0491(12) Uani 1 1 d . . . . .
H22A H 1.0887 0.3679 0.6490 0.074 Uiso 1 1 calc R U . . .
H22B H 1.2112 0.3308 0.5957 0.074 Uiso 1 1 calc R U . . .
H22C H 1.1766 0.3042 0.7113 0.074 Uiso 1 1 calc R U . . .
C31 C 1.1300(5) -0.0722(4) 0.7152(5) 0.0694(16) Uani 1 1 d . . . . .
H31A H 1.1132 -0.1384 0.7657 0.083 Uiso 0.712(4) 1 calc R U P A 1
H31B H 1.2020 -0.0790 0.6667 0.083 Uiso 0.712(4) 1 calc R U P A 1
H31C H 1.1328 -0.0427 0.6453 0.083 Uiso 0.288(4) 1 calc R U P A 2
H31D H 1.1903 -0.1257 0.7237 0.083 Uiso 0.288(4) 1 calc R U P A 2
C32 C 1.1461(5) 0.0096(4) 0.7610(4) 0.0668(16) Uani 1 1 d . . . . .
H32A H 1.2115 -0.0085 0.7937 0.080 Uiso 0.712(4) 1 calc R U P A 1
H32B H 1.1632 0.0759 0.7107 0.080 Uiso 0.712(4) 1 calc R U P A 1
H32C H 1.2260 0.0379 0.7346 0.080 Uiso 0.288(4) 1 calc R U P A 2
H32D H 1.1331 -0.0192 0.8322 0.080 Uiso 0.288(4) 1 calc R U P A 2
C33 C 0.8198(6) 0.2034(4) 0.6271(4) 0.0687(16) Uani 1 1 d . . . . .
H33A H 0.7489 0.2173 0.6731 0.082 Uiso 0.712(4) 1 calc R U P A 1
H33B H 0.8399 0.2656 0.5718 0.082 Uiso 0.712(4) 1 calc R U P A 1
H33C H 0.9026 0.2247 0.6035 0.082 Uiso 0.288(4) 1 calc R U P A 2
H33D H 0.7689 0.2626 0.6086 0.082 Uiso 0.288(4) 1 calc R U P A 2
C34 C 0.7962(5) 0.1179(4) 0.5914(4) 0.0664(15) Uani 1 1 d . . . . .
H34A H 0.7312 0.1357 0.5582 0.080 Uiso 0.712(4) 1 calc R U P A 1
H34B H 0.8665 0.1029 0.5455 0.080 Uiso 0.712(4) 1 calc R U P A 1
H34C H 0.8012 0.1423 0.5208 0.080 Uiso 0.288(4) 1 calc R U P A 2
H34D H 0.7174 0.0895 0.6252 0.080 Uiso 0.288(4) 1 calc R U P A 2
C35 C 0.7228(6) -0.0286(4) 0.9609(4) 0.0713(17) Uani 1 1 d . . . . .
H35A H 0.6466 -0.0170 1.0024 0.086 Uiso 0.712(4) 1 calc R U P A 1
H35B H 0.7817 -0.0430 1.0004 0.086 Uiso 0.712(4) 1 calc R U P A 1
H35C H 0.6688 0.0264 0.9378 0.086 Uiso 0.288(4) 1 calc R U P A 2
H35D H 0.7049 -0.0489 1.0326 0.086 Uiso 0.288(4) 1 calc R U P A 2
C36 C 0.7137(6) -0.1192(4) 0.9246(4) 0.0787(19) Uani 1 1 d . . . . .
H36A H 0.6933 -0.1811 0.9802 0.094 Uiso 0.712(4) 1 calc R U P A 1
H36B H 0.6519 -0.1067 0.8880 0.094 Uiso 0.712(4) 1 calc R U P A 1
H36C H 0.6348 -0.1494 0.9526 0.094 Uiso 0.288(4) 1 calc R U P A 2
H36D H 0.7717 -0.1715 0.9449 0.094 Uiso 0.288(4) 1 calc R U P A 2
N1 N 0.8212(3) 0.4266(3) 0.8803(3) 0.0386(9) Uani 1 1 d D . . . .
N2 N 0.7393(3) 0.4980(3) 0.8763(2) 0.0364(8) Uani 1 1 d . . . . .
N3 N 1.0438(3) 0.5326(3) 0.6289(2) 0.0317(8) Uani 1 1 d . . . . .
N4 N 0.9642(3) 0.6077(2) 0.6224(3) 0.0318(8) Uani 1 1 d D . . . .
N5 N 1.0267(5) -0.0394(4) 0.6660(4) 0.0465(15) Uani 0.712(4) 1 d . . P A 1
H5A H 1.0002 -0.0928 0.6540 0.070 Uiso 0.712(4) 1 calc R U P A 1
H5B H 1.0495 0.0101 0.6089 0.070 Uiso 0.712(4) 1 calc R U P A 1
N6 N 1.0325(5) 0.0142(4) 0.8336(4) 0.0520(16) Uani 0.712(4) 1 d . . P A 1
H6A H 1.0304 0.0709 0.8524 0.078 Uiso 0.712(4) 1 calc R U P A 1
H6B H 1.0260 -0.0406 0.8869 0.078 Uiso 0.712(4) 1 calc R U P A 1
N7 N 0.9235(5) 0.1736(3) 0.6789(4) 0.0402(13) Uani 0.712(4) 1 d . . P A 1
H7A H 0.9242 0.2134 0.7171 0.060 Uiso 0.712(4) 1 calc R U P A 1
H7B H 0.9931 0.1798 0.6347 0.060 Uiso 0.712(4) 1 calc R U P A 1
N8 N 0.7650(5) 0.0304(4) 0.6786(4) 0.0445(14) Uani 0.712(4) 1 d . . P A 1
H8A H 0.7652 -0.0269 0.6613 0.067 Uiso 0.712(4) 1 calc R U P A 1
H8B H 0.6922 0.0391 0.7134 0.067 Uiso 0.712(4) 1 calc R U P A 1
N9 N 0.7577(5) 0.0650(4) 0.8756(4) 0.0461(14) Uani 0.712(4) 1 d . . P A 1
H9D H 0.7876 0.1124 0.8939 0.069 Uiso 0.712(4) 1 calc R U P A 1
H9E H 0.6948 0.0919 0.8518 0.069 Uiso 0.712(4) 1 calc R U P A 1
N10 N 0.8310(6) -0.1328(4) 0.8594(4) 0.0539(16) Uani 0.712(4) 1 d . . P A 1
H10A H 0.8235 -0.1733 0.8235 0.081 Uiso 0.712(4) 1 calc R U P A 1
H10B H 0.8832 -0.1618 0.8955 0.081 Uiso 0.712(4) 1 calc R U P A 1
O1 O 0.6644(4) 0.3092(3) 0.8678(4) 0.0878(14) Uani 1 1 d . . . . .
O2 O 0.4475(3) 0.5692(3) 0.8697(3) 0.0829(13) Uani 1 1 d . . . . .
O3 O 1.1253(3) 0.7218(2) 0.6308(2) 0.0507(8) Uani 1 1 d . . . . .
O4 O 1.3316(3) 0.4544(3) 0.6434(3) 0.0575(9) Uani 1 1 d . . . . .
O11 O 0.9206(3) 0.2348(2) 0.8628(2) 0.0595(10) Uani 1 1 d . . . . .
O12 O 0.9099(4) 0.2154(3) 1.0329(2) 0.0733(12) Uani 1 1 d . . . . .
O13 O 1.0928(3) 0.1859(3) 0.9270(4) 0.0831(13) Uani 1 1 d . . . . .
O21 O 0.6888(3) 0.8517(2) 0.5948(3) 0.0671(11) Uani 1 1 d . . . . .
O22 O 0.8837(3) 0.8290(3) 0.4981(3) 0.0711(11) Uani 1 1 d . . . . .
O23 O 0.8503(3) 0.7901(2) 0.6727(3) 0.0600(10) Uani 1 1 d . . . . .
S1 S 0.98299(11) 0.24174(8) 0.93408(8) 0.0404(3) Uani 1 1 d . . . . .
S2 S 0.79920(10) 0.79457(8) 0.59140(8) 0.0377(3) Uani 1 1 d . . . . .
Ni1 Ni 0.89031(5) 0.01662(4) 0.76550(4) 0.03832(19) Uani 1 1 d . . . . .
N9A N 0.8477(14) 0.0042(10) 0.9182(9) 0.053(4) Uani 0.288(4) 1 d . . P A 2
H9A1 H 0.8955 -0.0418 0.9486 0.063 Uiso 0.288(4) 1 calc R U P A 2
H9A2 H 0.8580 0.0650 0.9263 0.063 Uiso 0.288(4) 1 calc R U P A 2
N6A N 1.0532(13) 0.0936(9) 0.7343(10) 0.052(4) Uani 0.288(4) 1 d . . P A 2
H6A1 H 1.0744 0.1293 0.6706 0.063 Uiso 0.288(4) 1 calc R U P A 2
H6A2 H 1.0466 0.1370 0.7702 0.063 Uiso 0.288(4) 1 calc R U P A 2
N5A N 1.0086(14) -0.1133(11) 0.7725(10) 0.063(5) Uani 0.288(4) 1 d . . P A 2
H5A1 H 1.0095 -0.1466 0.8351 0.075 Uiso 0.288(4) 1 calc R U P A 2
H5A2 H 0.9850 -0.1570 0.7462 0.075 Uiso 0.288(4) 1 calc R U P A 2
N8A N 0.8977(13) 0.0313(10) 0.6156(9) 0.052(4) Uani 0.288(4) 1 d . . P A 2
H8A1 H 0.9692 0.0526 0.5771 0.063 Uiso 0.288(4) 1 calc R U P A 2
H8A2 H 0.8805 -0.0282 0.6084 0.063 Uiso 0.288(4) 1 calc R U P A 2
N7A N 0.7900(15) 0.1531(11) 0.7311(11) 0.065(5) Uani 0.288(4) 1 d . . P A 2
H7A1 H 0.7126 0.1380 0.7510 0.078 Uiso 0.288(4) 1 calc R U P A 2
H7A2 H 0.8046 0.1954 0.7629 0.078 Uiso 0.288(4) 1 calc R U P A 2
N10A N 0.7371(14) -0.0816(11) 0.8121(10) 0.059(4) Uani 0.288(4) 1 d . . P A 2
H10C H 0.6748 -0.0466 0.7929 0.071 Uiso 0.288(4) 1 calc R U P A 2
H10D H 0.7520 -0.1346 0.7871 0.071 Uiso 0.288(4) 1 calc R U P A 2
H1N H 0.800(5) 0.365(2) 0.881(4) 0.089 Uiso 1 1 d D U . . .
H4N H 0.985(5) 0.669(2) 0.622(4) 0.089 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 C2 1.381(6) . ?
C1 C6 1.406(6) . ?
C1 S1 1.772(4) . ?
C2 C3 1.374(6) . ?
C3 C4 1.376(7) . ?
C4 C5 1.374(6) . ?
C5 C6 1.384(5) . ?
C6 N1 1.400(5) . ?
C7 N2 1.323(5) . ?
C7 C8 1.475(6) . ?
C7 C10 1.497(6) . ?
C8 O1 1.232(6) . ?
C8 C9 1.494(7) . ?
C10 O2 1.217(6) . ?
C10 C11 1.484(7) . ?
C12 C17 1.387(5) . ?
C12 C13 1.391(5) . ?
C12 S2 1.776(4) . ?
C13 C14 1.380(6) . ?
C14 C15 1.375(6) . ?
C15 C16 1.357(6) . ?
C16 C17 1.387(5) . ?
C17 N4 1.413(5) . ?
C18 N3 1.323(5) . ?
C18 C19 1.488(6) . ?
C18 C21 1.489(6) . ?
C19 O3 1.230(5) . ?
C19 C20 1.488(6) . ?
C21 O4 1.212(5) . ?
C21 C22 1.480(6) . ?
C31 N5A 1.498(16) . ?
C31 C32 1.505(7) . ?
C31 N5 1.516(8) . ?
C32 N6 1.483(8) . ?
C32 N6A 1.535(14) . ?
C33 N7A 1.426(15) . ?
C33 C34 1.479(7) . ?
C33 N7 1.538(8) . ?
C34 N8 1.442(7) . ?
C34 N8A 1.622(15) . ?
C35 N9A 1.471(14) . ?
C35 N9 1.481(7) . ?
C35 C36 1.502(7) . ?
C36 N10 1.489(8) . ?
C36 N10A 1.524(14) . ?
N1 N2 1.302(5) . ?
N3 N4 1.318(4) . ?
N5 Ni1 2.130(5) . ?
N6 Ni1 2.118(5) . ?
N7 Ni1 2.129(5) . ?
N8 Ni1 2.117(5) . ?
N9 Ni1 2.155(5) . ?
N10 Ni1 2.126(5) . ?
O11 S1 1.435(3) . ?
O12 S1 1.433(3) . ?
O13 S1 1.427(4) . ?
O21 S2 1.441(3) . ?
O22 S2 1.433(3) . ?
O23 S2 1.436(3) . ?
Ni1 N7A 2.105(16) . ?
Ni1 N6A 2.110(14) . ?
Ni1 N8A 2.118(12) . ?
Ni1 N9A 2.118(12) . ?
Ni1 N5A 2.141(16) . ?
Ni1 N10A 2.146(13) . ?

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
C2 C1 C6 119.7(4) . . ?
C2 C1 S1 119.1(3) . . ?
C6 C1 S1 121.2(3) . . ?
C3 C2 C1 120.9(4) . . ?
C2 C3 C4 119.1(4) . . ?
C5 C4 C3 121.3(4) . . ?
C4 C5 C6 120.0(4) . . ?
C5 C6 N1 121.2(4) . . ?
C5 C6 C1 118.9(4) . . ?
N1 C6 C1 119.9(3) . . ?
N2 C7 C8 125.0(4) . . ?
N2 C7 C10 111.2(4) . . ?
C8 C7 C10 123.8(4) . . ?
O1 C8 C7 118.4(4) . . ?
O1 C8 C9 119.1(5) . . ?
C7 C8 C9 122.4(5) . . ?
O2 C10 C11 120.0(5) . . ?
O2 C10 C7 121.3(5) . . ?
C11 C10 C7 118.6(4) . . ?
C17 C12 C13 119.5(3) . . ?
C17 C12 S2 122.1(3) . . ?
C13 C12 S2 118.5(3) . . ?
C14 C13 C12 120.5(4) . . ?
C15 C14 C13 119.1(4) . . ?
C16 C15 C14 121.1(4) . . ?
C15 C16 C17 120.7(4) . . ?
C12 C17 C16 119.1(4) . . ?
C12 C17 N4 119.8(3) . . ?
C16 C17 N4 121.0(4) . . ?
N3 C18 C19 123.3(4) . . ?
N3 C18 C21 112.4(4) . . ?
C19 C18 C21 124.3(4) . . ?
O3 C19 C18 119.3(4) . . ?
O3 C19 C20 119.4(4) . . ?
C18 C19 C20 121.3(4) . . ?
O4 C21 C22 120.8(4) . . ?
O4 C21 C18 120.7(4) . . ?
C22 C21 C18 118.5(4) . . ?
N5A C31 C32 102.3(7) . . ?
C32 C31 N5 107.6(4) . . ?
N6 C32 C31 106.3(5) . . ?
C31 C32 N6A 106.0(6) . . ?
N7A C33 C34 99.5(6) . . ?
C34 C33 N7 109.6(4) . . ?
N8 C34 C33 105.5(4) . . ?
C33 C34 N8A 106.1(6) . . ?
N9A C35 C36 103.7(6) . . ?
N9 C35 C36 109.8(4) . . ?
N10 C36 C35 108.1(5) . . ?
C35 C36 N10A 108.6(6) . . ?
N2 N1 C6 118.4(3) . . ?
N1 N2 C7 121.1(4) . . ?
N4 N3 C18 121.3(3) . . ?
N3 N4 C17 118.5(3) . . ?
C31 N5 Ni1 106.9(3) . . ?
C32 N6 Ni1 108.3(4) . . ?
C33 N7 Ni1 104.6(3) . . ?
C34 N8 Ni1 109.1(4) . . ?
C35 N9 Ni1 106.6(4) . . ?
C36 N10 Ni1 107.1(4) . . ?
O13 S1 O12 112.6(3) . . ?
O13 S1 O11 112.1(2) . . ?
O12 S1 O11 112.9(2) . . ?
O13 S1 C1 106.6(2) . . ?
O12 S1 C1 106.08(19) . . ?
O11 S1 C1 105.9(2) . . ?
O22 S2 O23 111.9(2) . . ?
O22 S2 O21 113.3(2) . . ?
O23 S2 O21 112.5(2) . . ?
O22 S2 C12 105.43(19) . . ?
O23 S2 C12 106.06(19) . . ?
O21 S2 C12 107.07(19) . . ?
N7A Ni1 N6A 94.8(5) . . ?
N7A Ni1 N8A 80.8(5) . . ?
N6A Ni1 N8A 94.6(5) . . ?
N8 Ni1 N6 171.9(2) . . ?
N7A Ni1 N9A 92.7(6) . . ?
N6A Ni1 N9A 94.5(5) . . ?
N8A Ni1 N9A 169.2(6) . . ?
N8 Ni1 N10 94.0(2) . . ?
N6 Ni1 N10 92.5(2) . . ?
N8 Ni1 N7 81.8(2) . . ?
N6 Ni1 N7 92.3(2) . . ?
N10 Ni1 N7 171.5(2) . . ?
N8 Ni1 N5 93.1(2) . . ?
N6 Ni1 N5 81.7(2) . . ?
N10 Ni1 N5 94.7(2) . . ?
N7 Ni1 N5 92.9(2) . . ?
N7A Ni1 N5A 169.5(5) . . ?
N6A Ni1 N5A 80.9(5) . . ?
N8A Ni1 N5A 90.0(5) . . ?
N9A Ni1 N5A 97.2(6) . . ?
N7A Ni1 N10A 93.5(6) . . ?
N6A Ni1 N10A 170.9(6) . . ?
N8A Ni1 N10A 90.4(5) . . ?
N9A Ni1 N10A 81.4(5) . . ?
N5A Ni1 N10A 91.6(6) . . ?
N8 Ni1 N9 90.6(2) . . ?
N6 Ni1 N9 95.0(2) . . ?
N10 Ni1 N9 82.3(2) . . ?
N7 Ni1 N9 90.35(19) . . ?
N5 Ni1 N9 175.5(2) . . ?
C35 N9A Ni1 108.8(8) . . ?
C32 N6A Ni1 106.5(7) . . ?
C31 N5A Ni1 107.1(8) . . ?
C34 N8A Ni1 102.1(6) . . ?
C33 N7A Ni1 110.4(9) . . ?
C36 N10A Ni1 104.8(8) . . ?

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
C9 H9A O2 0.96 2.04 2.822(7) 137.1 .
C11 H11A N2 0.96 2.19 2.690(6) 110.8 .
C20 H20A O4 0.96 2.01 2.798(6) 138.0 .
C22 H22A N3 0.96 2.20 2.701(6) 110.9 .
C34 H34C O3 0.97 2.42 3.260(6) 144.8 2_766
C35 H35B O13 0.97 2.47 3.270(8) 140.3 2_757
N5 H5A O23 0.89 2.36 3.171(6) 152.3 1_545
N5 H5B O22 0.89 2.32 3.167(6) 158.3 2_766
N6 H6A O11 0.89 2.51 3.279(6) 145.7 .
N6 H6A O13 0.89 2.40 3.236(6) 156.4 .
N6 H6A S1 0.89 2.88 3.759(5) 170.0 .
N6 H6B O12 0.89 2.45 3.254(6) 149.8 2_757
N7 H7A O11 0.89 2.23 3.039(6) 151.8 .
N7 H7B O22 0.89 2.13 2.975(6) 157.2 2_766
N8 H8A O21 0.89 2.47 3.298(6) 155.6 1_545
N8 H8A O23 0.89 2.58 3.359(6) 147.3 1_545
N8 H8A S2 0.89 2.87 3.757(5) 172.1 1_545
N9 H9D O11 0.89 2.22 3.027(6) 150.2 .
N10 H10A O23 0.89 2.35 3.162(6) 152.4 1_545
N10 H10B O13 0.89 2.59 3.306(7) 137.5 2_757
N9A H9A1 O13 0.89 2.25 3.030(16) 146.4 2_757
N9A H9A2 O11 0.89 2.31 3.116(13) 150.8 .
N9A H9A2 S1 0.89 2.94 3.789(12) 159.0 .
N6A H6A1 O22 0.89 2.29 3.143(14) 161.5 2_766
N6A H6A2 O11 0.89 2.35 3.144(12) 147.8 .
N5A H5A1 O12 0.89 2.26 3.101(15) 156.8 2_757
N5A H5A2 O23 0.89 2.36 3.176(14) 151.9 1_545
N8A H8A1 O22 0.89 2.26 3.083(14) 153.3 2_766
N8A H8A2 O23 0.89 2.38 3.181(13) 150.2 1_545
N8A H8A2 S2 0.89 2.75 3.640(12) 173.2 1_545
N7A H7A2 O11 0.89 2.41 3.200(14) 148.7 .
N10A H10D O23 0.89 2.25 3.066(14) 152.4 1_545
N1 H1N O1 0.88(2) 1.88(4) 2.583(5) 136(5) .
N1 H1N O11 0.88(2) 2.21(5) 2.825(5) 126(5) .
N4 H4N O3 0.88(2) 1.87(4) 2.565(4) 134(5) .
N4 H4N O23 0.88(2) 2.34(5) 2.924(5) 124(4) .

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.072


