# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_C1
_database_code_depnum_ccdc_archive 'CCDC 1014554'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N2 Ni O2 S4'
_chemical_formula_weight         663.55

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4945(7)
_cell_length_b                   11.1068(10)
_cell_length_c                   11.7301(13)
_cell_angle_alpha                101.467(9)
_cell_angle_beta                 102.098(9)
_cell_angle_gamma                106.947(9)
_cell_volume                     760.24(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5443
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.49

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  1.000
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            5443
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3340
_reflns_number_gt                2509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'


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

The -OMe was disordered over two sites and the occupancies were given 
as x, and 1-x, with x refining to 0.519(5).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.0183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     209
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S -0.07973(11) 0.54535(6) 0.17334(6) 0.0524(2) Uani 1 1 d . . .
S13 S -0.34025(11) 0.35677(6) -0.04681(6) 0.0509(2) Uani 1 1 d . . .
Ni1 Ni 0.0000 0.5000 0.0000 0.04174(16) Uani 1 2 d S . .
C12 C -0.3368(4) 0.4238(2) 0.0992(2) 0.0442(6) Uani 1 1 d . . .
C21 C -0.4883(5) 0.4554(3) 0.2713(3) 0.0585(7) Uani 1 1 d . . .
H21A H -0.6277 0.4709 0.2712 0.070 Uiso 1 1 calc R . .
H21B H -0.3686 0.5400 0.2971 0.070 Uiso 1 1 calc R . .
C22 C -0.4447(5) 0.3800(3) 0.3617(3) 0.0550(7) Uani 1 1 d . E .
C23 C -0.2487(6) 0.3544(4) 0.3902(3) 0.0817(10) Uani 1 1 d . . .
H23 H -0.1381 0.3847 0.3532 0.098 Uiso 1 1 calc R . .
C24 C -0.2132(6) 0.2851(4) 0.4721(4) 0.0972(12) Uani 1 1 d . E .
H24 H -0.0797 0.2684 0.4911 0.117 Uiso 1 1 calc R . .
C25 C -0.3787(7) 0.2405(4) 0.5260(3) 0.0920(12) Uani 1 1 d . . .
H25 H -0.3561 0.1934 0.5818 0.110 Uiso 1 1 calc R A 1
C27 C -0.6023(5) 0.3329(3) 0.4189(3) 0.0651(8) Uani 1 1 d . . .
H27 H -0.7364 0.3491 0.4012 0.078 Uiso 1 1 calc R B 1
C31 C -0.7178(4) 0.2846(3) 0.0756(3) 0.0552(7) Uani 1 1 d . . .
H31A H -0.7207 0.2629 -0.0092 0.066 Uiso 1 1 calc R . .
H31B H -0.8393 0.3174 0.0818 0.066 Uiso 1 1 calc R . .
C32 C -0.7565(4) 0.1626(2) 0.1174(2) 0.0468(6) Uani 1 1 d . E .
C33 C -0.6074(5) 0.0967(3) 0.1198(3) 0.0658(8) Uani 1 1 d . . .
H33 H -0.4796 0.1277 0.0951 0.079 Uiso 1 1 calc R . .
C34 C -0.6451(7) -0.0136(3) 0.1580(3) 0.0818(10) Uani 1 1 d . E .
H34 H -0.5437 -0.0580 0.1597 0.098 Uiso 1 1 calc R . .
C35 C -0.8324(7) -0.0579(3) 0.1934(3) 0.0861(12) Uani 1 1 d . . .
H35 H -0.8575 -0.1333 0.2194 0.103 Uiso 1 1 calc R C 1
C37 C -0.9430(5) 0.1138(3) 0.1535(3) 0.0631(8) Uani 1 1 d . . .
H37 H -1.0463 0.1569 0.1517 0.076 Uiso 1 1 calc R D 1
N14 N -0.5030(4) 0.3883(2) 0.1465(2) 0.0474(5) Uani 1 1 d . . .
C36A C -0.9821(6) 0.0030(3) 0.1922(3) 0.0753(10) Uani 0.519(5) 1 d P E 1
H36A H -1.1094 -0.0290 0.2169 0.090 Uiso 0.519(5) 1 calc PR E 1
C26A C -0.5706(6) 0.2639(4) 0.4997(3) 0.0733(9) Uani 0.519(5) 1 d P E 1
O28 O -0.7550(8) 0.1992(5) 0.5367(4) 0.0901(18) Uani 0.519(5) 1 d PD E 1
C29 C -0.7277(17) 0.1202(10) 0.6180(9) 0.112(3) Uani 0.519(5) 1 d PD E 1
H29A H -0.7272 0.0377 0.5738 0.168 Uiso 0.519(5) 1 calc PR E 1
H29B H -0.8496 0.1053 0.6539 0.168 Uiso 0.519(5) 1 calc PR E 1
H29C H -0.5882 0.1647 0.6807 0.168 Uiso 0.519(5) 1 calc PR E 1
C36B C -0.9821(6) 0.0030(3) 0.1922(3) 0.0753(10) Uani 0.481(5) 1 d P E 2
C26B C -0.5706(6) 0.2639(4) 0.4997(3) 0.0733(9) Uani 0.481(5) 1 d P E 2
H26B H -0.6813 0.2331 0.5364 0.088 Uiso 0.481(5) 1 calc PR E 2
O38 O -1.1385(10) -0.0163(6) 0.2539(7) 0.118(3) Uani 0.481(5) 1 d PD E 2
C39 C -1.1516(19) -0.1101(11) 0.3252(11) 0.128(4) Uani 0.481(5) 1 d PD E 2
H39A H -1.1889 -0.1962 0.2725 0.192 Uiso 0.481(5) 1 calc PR E 2
H39B H -1.2652 -0.1094 0.3658 0.192 Uiso 0.481(5) 1 calc PR E 2
H39C H -1.0092 -0.0865 0.3842 0.192 Uiso 0.481(5) 1 calc PR E 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 C12 1.725(3) . ?
S11 Ni1 2.2006(7) . ?
S13 C12 1.719(3) . ?
S13 Ni1 2.1932(7) . ?
Ni1 S13 2.1932(7) 2_565 ?
Ni1 S11 2.2006(7) 2_565 ?
C12 N14 1.311(3) . ?
C21 N14 1.473(3) . ?
C21 C22 1.508(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.372(4) . ?
C22 C27 1.373(4) . ?
C23 C24 1.369(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.378(5) . ?
C24 H24 0.9300 . ?
C25 C26B 1.332(5) . ?
C25 C26A 1.332(5) . ?
C25 H25 0.9300 . ?
C27 C26B 1.352(4) . ?
C27 C26A 1.352(4) . ?
C27 H27 0.9300 . ?
C31 N14 1.470(3) . ?
C31 C32 1.503(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C37 1.365(4) . ?
C32 C33 1.373(4) . ?
C33 C34 1.360(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.356(5) . ?
C34 H34 0.9300 . ?
C35 C36B 1.336(5) . ?
C35 C36A 1.336(5) . ?
C35 H35 0.9300 . ?
C37 C36B 1.368(4) . ?
C37 C36A 1.368(4) . ?
C37 H37 0.9300 . ?
C36A H36A 0.9300 . ?
C26A O28 1.407(5) . ?
O28 C29 1.436(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C36B O38 1.359(6) . ?
C26B H26B 0.9300 . ?
O38 C39 1.454(7) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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
C12 S11 Ni1 85.57(9) . . ?
C12 S13 Ni1 85.96(9) . . ?
S13 Ni1 S13 180.0 2_565 . ?
S13 Ni1 S11 100.64(3) 2_565 . ?
S13 Ni1 S11 79.36(3) . . ?
S13 Ni1 S11 79.36(3) 2_565 2_565 ?
S13 Ni1 S11 100.64(3) . 2_565 ?
S11 Ni1 S11 180.00(4) . 2_565 ?
N14 C12 S13 125.4(2) . . ?
N14 C12 S11 125.5(2) . . ?
S13 C12 S11 109.09(14) . . ?
N14 C21 C22 113.8(2) . . ?
N14 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N14 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C27 117.0(3) . . ?
C23 C22 C21 122.1(3) . . ?
C27 C22 C21 120.9(3) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 118.8(4) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26B C25 C26A 0.00(11) . . ?
C26B C25 C24 121.1(4) . . ?
C26A C25 C24 121.1(4) . . ?
C26B C25 H25 119.4 . . ?
C26A C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C26B C27 C26A 0.0(3) . . ?
C26B C27 C22 122.7(3) . . ?
C26A C27 C22 122.7(3) . . ?
C26B C27 H27 118.6 . . ?
C26A C27 H27 118.6 . . ?
C22 C27 H27 118.6 . . ?
N14 C31 C32 112.8(2) . . ?
N14 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
N14 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C37 C32 C33 118.1(3) . . ?
C37 C32 C31 120.6(2) . . ?
C33 C32 C31 121.3(2) . . ?
C34 C33 C32 120.5(3) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.1(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C36B C35 C36A 0.0(3) . . ?
C36B C35 C34 122.3(3) . . ?
C36A C35 C34 122.3(3) . . ?
C36B C35 H35 118.8 . . ?
C36A C35 H35 118.8 . . ?
C34 C35 H35 118.8 . . ?
C32 C37 C36B 121.7(3) . . ?
C32 C37 C36A 121.7(3) . . ?
C36B C37 C36A 0.0(3) . . ?
C32 C37 H37 119.1 . . ?
C36B C37 H37 119.1 . . ?
C36A C37 H37 119.1 . . ?
C12 N14 C31 121.6(2) . . ?
C12 N14 C21 121.6(2) . . ?
C31 N14 C21 116.6(2) . . ?
C35 C36A C37 118.2(3) . . ?
C35 C36A H36A 120.9 . . ?
C37 C36A H36A 120.9 . . ?
C25 C26A C27 119.2(3) . . ?
C25 C26A O28 121.2(4) . . ?
C27 C26A O28 118.7(4) . . ?
C26A O28 C29 119.6(5) . . ?
C35 C36B O38 124.1(4) . . ?
C35 C36B C37 118.2(3) . . ?
O38 C36B C37 115.6(4) . . ?
C25 C26B C27 119.2(3) . . ?
C25 C26B H26B 120.4 . . ?
C27 C26B H26B 120.4 . . ?
C36B O38 C39 119.7(7) . . ?
O38 C39 H39A 109.5 . . ?
O38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 1014555'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N3 Pd S4'
_chemical_formula_weight         654.19

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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7086(10)
_cell_length_b                   10.3187(18)
_cell_length_c                   10.8136(12)
_cell_angle_alpha                74.967(12)
_cell_angle_beta                 84.813(10)
_cell_angle_gamma                72.281(14)
_cell_volume                     688.59(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4823
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_T_max  1.000


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_device_type  'CCD diffractometer'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            4823
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0937
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.23
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3838
_reflns_number_gt                2704
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'


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

In the ligand, one ring was disordered being either N-methyl-2-pyrole or phenyl. The two superimposing alternatives were refined with occupancies of 0.5.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1412P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3838
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.0931
_refine_ls_wR_factor_ref         0.2487
_refine_ls_wR_factor_gt          0.2176
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N14 N 0.4087(8) 0.1335(6) 0.1643(5) 0.0413(12) Uani 1 1 d . B .
Pd1 Pd 0.0000 0.0000 0.0000 0.0373(3) Uani 1 2 d S . .
S11 S 0.1551(3) -0.03163(17) 0.19325(14) 0.0423(4) Uani 1 1 d . . .
S13 S 0.2123(3) 0.14774(17) -0.04666(14) 0.0401(4) Uani 1 1 d . . .
C12 C 0.2811(9) 0.0876(7) 0.1131(6) 0.0373(12) Uani 1 1 d . . .
C21 C 0.4754(11) 0.0697(8) 0.2983(6) 0.0506(17) Uani 1 1 d . . .
H21A H 0.6242 0.0565 0.3028 0.061 Uiso 1 1 calc R . .
H21B H 0.4529 -0.0221 0.3249 0.061 Uiso 1 1 calc R . .
C22 C 0.3622(12) 0.1551(7) 0.3898(6) 0.0499(16) Uani 1 1 d . . .
C23 C 0.4559(14) 0.2342(9) 0.4403(7) 0.062(2) Uani 1 1 d . . .
H23 H 0.5928 0.2342 0.4169 0.075 Uiso 1 1 calc R . .
C25 C 0.1581(12) 0.1569(9) 0.4293(7) 0.0558(18) Uani 1 1 d . . .
H25 H 0.0927 0.1043 0.3984 0.067 Uiso 1 1 calc R . .
C26 C 0.0502(13) 0.2358(10) 0.5140(8) 0.063(2) Uani 1 1 d . . .
H26 H -0.0859 0.2357 0.5395 0.076 Uiso 1 1 calc R . .
C27 C 0.1432(15) 0.3116(9) 0.5583(7) 0.067(2) Uani 1 1 d . . .
H27 H 0.0692 0.3656 0.6135 0.081 Uiso 1 1 calc R . .
C28 C 0.3476(15) 0.3122(9) 0.5243(7) 0.065(2) Uani 1 1 d . . .
H28 H 0.4105 0.3644 0.5576 0.079 Uiso 1 1 calc R . .
C31 C 0.5213(10) 0.2301(8) 0.0844(7) 0.0487(16) Uani 1 1 d . . .
H31A H 0.4462 0.2751 0.0046 0.058 Uiso 1 1 calc R A 1
H31B H 0.6581 0.1734 0.0633 0.058 Uiso 1 1 calc R A 1
C32A C 0.5531(19) 0.3423(12) 0.1366(14) 0.032(3) Uani 0.50 1 d PG B 1
C33A C 0.7430(13) 0.3543(15) 0.1740(17) 0.037(3) Uani 0.50 1 d PG B 1
H33A H 0.8760 0.2940 0.1666 0.044 Uiso 0.50 1 calc PR B 1
C34A C 0.694(2) 0.4743(15) 0.2247(18) 0.055(6) Uani 0.50 1 d PG B 1
H34A H 0.7894 0.5065 0.2564 0.066 Uiso 0.50 1 calc PR B 1
C35A C 0.474(2) 0.5366(9) 0.2186(13) 0.054(5) Uani 0.50 1 d PG B 1
H35A H 0.3997 0.6168 0.2456 0.065 Uiso 0.50 1 calc PR B 1
N36A N 0.3868(13) 0.4551(10) 0.1641(9) 0.041(3) Uani 0.50 1 d PG B 1
C37A C 0.168(2) 0.4755(15) 0.1484(14) 0.054(4) Uani 0.50 1 d P B 1
H37A H 0.1106 0.4320 0.2271 0.082 Uiso 0.50 1 calc PR B 1
H37B H 0.1510 0.4341 0.0816 0.082 Uiso 0.50 1 calc PR B 1
H37C H 0.0961 0.5742 0.1259 0.082 Uiso 0.50 1 calc PR B 1
C32B C 0.493(2) 0.3466(14) 0.1417(17) 0.049(5) Uani 0.50 1 d PG B 2
C33B C 0.6660(15) 0.3747(16) 0.1777(18) 0.047(4) Uani 0.50 1 d PG B 2
H33B H 0.7985 0.3118 0.1757 0.056 Uiso 0.50 1 calc PR B 2
C34B C 0.641(2) 0.4969(17) 0.2168(19) 0.060(6) Uani 0.50 1 d PG B 2
H34B H 0.7571 0.5157 0.2409 0.072 Uiso 0.50 1 calc PR B 2
C35B C 0.443(3) 0.5910(11) 0.2198(16) 0.082(8) Uani 0.50 1 d PG B 2
H35B H 0.4265 0.6727 0.2460 0.098 Uiso 0.50 1 calc PR B 2
C36B C 0.2700(19) 0.5629(12) 0.1838(12) 0.078(6) Uani 0.50 1 d PG B 2
H36B H 0.1375 0.6258 0.1858 0.093 Uiso 0.50 1 calc PR B 2
C37B C 0.2948(17) 0.4406(16) 0.1447(13) 0.059(5) Uani 0.50 1 d PG B 2
H37D H 0.1789 0.4218 0.1206 0.071 Uiso 0.50 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N14 C12 1.316(8) . ?
N14 C21 1.475(8) . ?
N14 C31 1.485(9) . ?
Pd1 S11 2.3213(16) 2 ?
Pd1 S11 2.3213(16) . ?
Pd1 S13 2.3239(16) 2 ?
Pd1 S13 2.3239(16) . ?
S11 C12 1.711(7) . ?
S13 C12 1.731(6) . ?
C21 C22 1.497(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C25 1.393(10) . ?
C22 C23 1.402(10) . ?
C23 C28 1.380(11) . ?
C23 H23 0.9300 . ?
C25 C26 1.390(10) . ?
C25 H25 0.9300 . ?
C26 C27 1.333(12) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(12) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C31 C32B 1.446(11) . ?
C31 C32A 1.489(11) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32A C33A 1.4200 . ?
C32A N36A 1.4200 . ?
C33A C34A 1.4200 . ?
C33A H33A 0.9300 . ?
C34A C35A 1.4200 . ?
C34A H34A 0.9300 . ?
C35A N36A 1.4200 . ?
C35A H35A 0.9300 . ?
N36A C37A 1.437(16) . ?
C37A H37A 0.9600 . ?
C37A H37B 0.9600 . ?
C37A H37C 0.9600 . ?
C32B C33B 1.3900 . ?
C32B C37B 1.3900 . ?
C33B C34B 1.3900 . ?
C33B H33B 0.9300 . ?
C34B C35B 1.3900 . ?
C34B H34B 0.9300 . ?
C35B C36B 1.3900 . ?
C35B H35B 0.9300 . ?
C36B C37B 1.3900 . ?
C36B H36B 0.9300 . ?
C37B H37D 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
C12 N14 C21 120.5(6) . . ?
C12 N14 C31 121.3(6) . . ?
C21 N14 C31 117.2(6) . . ?
S11 Pd1 S11 180.00(8) 2 . ?
S11 Pd1 S13 75.38(6) 2 2 ?
S11 Pd1 S13 104.62(6) . 2 ?
S11 Pd1 S13 104.62(6) 2 . ?
S11 Pd1 S13 75.38(6) . . ?
S13 Pd1 S13 180.0 2 . ?
C12 S11 Pd1 87.0(2) . . ?
C12 S13 Pd1 86.4(2) . . ?
N14 C12 S11 125.7(5) . . ?
N14 C12 S13 123.0(5) . . ?
S11 C12 S13 111.2(4) . . ?
N14 C21 C22 113.7(6) . . ?
N14 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N14 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C25 C22 C23 117.4(7) . . ?
C25 C22 C21 120.5(7) . . ?
C23 C22 C21 122.1(7) . . ?
C28 C23 C22 120.8(8) . . ?
C28 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C26 C25 C22 121.4(7) . . ?
C26 C25 H25 119.3 . . ?
C22 C25 H25 119.3 . . ?
C27 C26 C25 119.5(8) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 121.8(8) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C23 C28 C27 119.1(8) . . ?
C23 C28 H28 120.5 . . ?
C27 C28 H28 120.5 . . ?
C32B C31 N14 108.6(8) . . ?
C32B C31 C32A 15.3(8) . . ?
N14 C31 C32A 118.9(7) . . ?
C32B C31 H31A 102.3 . . ?
N14 C31 H31A 107.6 . . ?
C32A C31 H31A 107.6 . . ?
C32B C31 H31B 122.8 . . ?
N14 C31 H31B 107.6 . . ?
C32A C31 H31B 107.6 . . ?
H31A C31 H31B 107.0 . . ?
C33A C32A N36A 108.0 . . ?
C33A C32A C31 128.4(9) . . ?
N36A C32A C31 123.5(9) . . ?
C34A C33A C32A 108.0 . . ?
C34A C33A H33A 126.0 . . ?
C32A C33A H33A 126.0 . . ?
C33A C34A C35A 108.0 . . ?
C33A C34A H34A 126.0 . . ?
C35A C34A H34A 126.0 . . ?
N36A C35A C34A 108.0 . . ?
N36A C35A H35A 126.0 . . ?
C34A C35A H35A 126.0 . . ?
C35A N36A C32A 108.0 . . ?
C35A N36A C37A 126.4(11) . . ?
C32A N36A C37A 125.5(11) . . ?
C33B C32B C37B 120.0 . . ?
C33B C32B C31 120.0(11) . . ?
C37B C32B C31 119.5(11) . . ?
C34B C33B C32B 120.0 . . ?
C34B C33B H33B 120.0 . . ?
C32B C33B H33B 120.0 . . ?
C35B C34B C33B 120.0 . . ?
C35B C34B H34B 120.0 . . ?
C33B C34B H34B 120.0 . . ?
C34B C35B C36B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C36B C35B H35B 120.0 . . ?
C37B C36B C35B 120.0 . . ?
C37B C36B H36B 120.0 . . ?
C35B C36B H36B 120.0 . . ?
C36B C37B C32B 120.0 . . ?
C36B C37B H37D 120.0 . . ?
C32B C37B H37D 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         3.079
_refine_diff_density_min         -1.631
_refine_diff_density_rms         0.213
####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 1014556'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H38 N4 Ni O6 S4'
_chemical_formula_weight         785.63

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0268(10)
_cell_length_b                   10.6267(18)
_cell_length_c                   13.7577(16)
_cell_angle_alpha                104.768(12)
_cell_angle_beta                 103.014(11)
_cell_angle_gamma                105.644(14)
_cell_volume                     907.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6893
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'

_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  1.000
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            6893
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0833
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3961
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'SHELXL-97, PLATON, WINGX(Farrugia,2012)'







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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0461P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3961
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.20016(12) -0.12123(10) -0.03763(7) 0.0456(3) Uani 1 1 d . . .
S13 S 0.19794(14) 0.03701(12) 0.15930(7) 0.0540(3) Uani 1 1 d . . .
Ni1 Ni 0.0000 0.0000 0.0000 0.0410(2) Uani 1 2 d S . .
C12 C 0.3101(5) -0.0698(4) 0.0974(3) 0.0381(8) Uani 1 1 d . . .
N44 N 0.4568(4) -0.1077(3) 0.1463(2) 0.0387(7) Uani 1 1 d . . .
O24 O 1.1029(4) 0.3836(3) 0.3780(3) 0.0811(10) Uani 1 1 d . . .
O25 O 1.3825(3) 0.2762(3) 0.4533(2) 0.0665(8) Uani 1 1 d . . .
C21 C 0.5338(4) -0.0644(4) 0.2625(2) 0.0439(9) Uani 1 1 d . . .
H21A H 0.5129 -0.1464 0.2834 0.053 Uiso 1 1 calc R . .
H21B H 0.4523 -0.0134 0.2916 0.053 Uiso 1 1 calc R . .
C22 C 0.7607(4) 0.0251(4) 0.3094(2) 0.0394(8) Uani 1 1 d . . .
C23 C 0.8213(5) 0.1615(4) 0.3163(3) 0.0495(10) Uani 1 1 d . . .
H23 H 0.7233 0.1971 0.2878 0.059 Uiso 1 1 calc R . .
C24 C 1.0282(6) 0.2474(4) 0.3657(3) 0.0548(10) Uani 1 1 d . . .
C25 C 1.1745(5) 0.1934(4) 0.4073(3) 0.0456(9) Uani 1 1 d . . .
C26 C 1.1143(5) 0.0552(4) 0.3984(2) 0.0397(9) Uani 1 1 d . . .
C27 C 0.9059(4) -0.0301(4) 0.3491(2) 0.0394(8) Uani 1 1 d . . .
H27 H 0.8648 -0.1234 0.3431 0.047 Uiso 1 1 calc R . .
O28 O 1.2690(3) 0.0098(3) 0.43864(18) 0.0501(7) Uani 1 1 d . . .
C241 C 0.9579(7) 0.4456(5) 0.3421(5) 0.120(2) Uani 1 1 d . . .
H24A H 0.8816 0.3954 0.2686 0.180 Uiso 1 1 calc R . .
H24B H 1.0313 0.5402 0.3508 0.180 Uiso 1 1 calc R . .
H24C H 0.8630 0.4432 0.3826 0.180 Uiso 1 1 calc R . .
C251 C 1.4303(6) 0.3581(5) 0.5600(3) 0.0804(15) Uani 1 1 d . . .
H25A H 1.3305 0.4038 0.5658 0.121 Uiso 1 1 calc R . .
H25B H 1.5673 0.4264 0.5835 0.121 Uiso 1 1 calc R . .
H25C H 1.4254 0.2999 0.6032 0.121 Uiso 1 1 calc R . .
C281 C 1.2138(5) -0.1335(4) 0.4251(3) 0.0522(10) Uani 1 1 d . . .
H28A H 1.1143 -0.1579 0.4609 0.078 Uiso 1 1 calc R . .
H28B H 1.3358 -0.1529 0.4542 0.078 Uiso 1 1 calc R . .
H28C H 1.1537 -0.1867 0.3510 0.078 Uiso 1 1 calc R . .
C51 C 0.5429(5) -0.2020(4) 0.0884(3) 0.0450(9) Uani 1 1 d . . .
H51A H 0.6928 -0.1579 0.1089 0.054 Uiso 1 1 calc R . .
H51B H 0.4859 -0.2204 0.0130 0.054 Uiso 1 1 calc R . .
C52 C 0.4941(5) -0.3358(3) 0.1100(2) 0.0558(11) Uani 1 1 d G . .
C53 C 0.2929(4) -0.4092(4) 0.1038(3) 0.0916(17) Uani 1 1 d G . .
H53 H 0.1855 -0.3760 0.0844 0.110 Uiso 1 1 calc R . .
C54 C 0.2522(6) -0.5321(4) 0.1265(3) 0.144(3) Uani 1 1 d G . .
H54 H 0.1175 -0.5812 0.1224 0.172 Uiso 1 1 calc R . .
C55 C 0.4127(9) -0.5816(3) 0.1554(3) 0.160(4) Uani 1 1 d G . .
H55 H 0.3854 -0.6638 0.1706 0.192 Uiso 1 1 calc R . .
N56 N 0.6139(7) -0.5082(4) 0.1616(2) 0.132(2) Uani 1 1 d G . .
C57 C 0.6546(4) -0.3853(4) 0.1389(2) 0.0872(16) Uani 1 1 d G . .
H57 H 0.7893 -0.3362 0.1430 0.105 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 C12 1.719(3) . ?
S11 Ni1 2.2070(10) . ?
S13 C12 1.710(3) . ?
S13 Ni1 2.1875(10) . ?
Ni1 S13 2.1875(10) 2 ?
Ni1 S11 2.2070(10) 2 ?
C12 N44 1.315(4) . ?
N44 C51 1.463(4) . ?
N44 C21 1.471(4) . ?
O24 C24 1.350(5) . ?
O24 C241 1.421(5) . ?
O25 C25 1.384(4) . ?
O25 C251 1.413(5) . ?
C21 C22 1.506(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.368(5) . ?
C22 C27 1.385(4) . ?
C23 C24 1.390(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.391(5) . ?
C25 C26 1.379(5) . ?
C26 O28 1.367(4) . ?
C26 C27 1.396(4) . ?
C27 H27 0.9300 . ?
O28 C281 1.416(4) . ?
C241 H24A 0.9600 . ?
C241 H24B 0.9600 . ?
C241 H24C 0.9600 . ?
C251 H25A 0.9600 . ?
C251 H25B 0.9600 . ?
C251 H25C 0.9600 . ?
C281 H28A 0.9600 . ?
C281 H28B 0.9600 . ?
C281 H28C 0.9600 . ?
C51 C52 1.492(4) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C52 C53 1.3900 . ?
C52 C57 1.3900 . ?
C53 C54 1.3900 . ?
C53 H53 0.9300 . ?
C54 C55 1.3900 . ?
C54 H54 0.9300 . ?
C55 N56 1.3900 . ?
C55 H55 0.9300 . ?
N56 C57 1.3900 . ?
C57 H57 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
C12 S11 Ni1 84.93(12) . . ?
C12 S13 Ni1 85.74(11) . . ?
S13 Ni1 S13 180.00(6) 2 . ?
S13 Ni1 S11 79.39(4) 2 2 ?
S13 Ni1 S11 100.61(4) . 2 ?
S13 Ni1 S11 100.61(4) 2 . ?
S13 Ni1 S11 79.39(4) . . ?
S11 Ni1 S11 180.00(2) 2 . ?
N44 C12 S13 124.8(2) . . ?
N44 C12 S11 125.3(3) . . ?
S13 C12 S11 109.88(19) . . ?
C12 N44 C51 122.0(3) . . ?
C12 N44 C21 121.5(3) . . ?
C51 N44 C21 116.4(3) . . ?
C24 O24 C241 117.7(3) . . ?
C25 O25 C251 112.9(3) . . ?
N44 C21 C22 113.3(2) . . ?
N44 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N44 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C27 120.4(3) . . ?
C23 C22 C21 119.9(3) . . ?
C27 C22 C21 119.6(3) . . ?
C22 C23 C24 120.5(4) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
O24 C24 C23 125.0(4) . . ?
O24 C24 C25 115.4(3) . . ?
C23 C24 C25 119.5(4) . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 O25 119.6(3) . . ?
C24 C25 O25 120.3(4) . . ?
C25 C26 O28 116.2(3) . . ?
C25 C26 C27 120.0(3) . . ?
O28 C26 C27 123.8(3) . . ?
C22 C27 C26 119.5(3) . . ?
C22 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C26 O28 C281 117.4(3) . . ?
O24 C241 H24A 109.5 . . ?
O24 C241 H24B 109.5 . . ?
H24A C241 H24B 109.5 . . ?
O24 C241 H24C 109.5 . . ?
H24A C241 H24C 109.5 . . ?
H24B C241 H24C 109.5 . . ?
O25 C251 H25A 109.5 . . ?
O25 C251 H25B 109.5 . . ?
H25A C251 H25B 109.5 . . ?
O25 C251 H25C 109.5 . . ?
H25A C251 H25C 109.5 . . ?
H25B C251 H25C 109.5 . . ?
O28 C281 H28A 109.5 . . ?
O28 C281 H28B 109.5 . . ?
H28A C281 H28B 109.5 . . ?
O28 C281 H28C 109.5 . . ?
H28A C281 H28C 109.5 . . ?
H28B C281 H28C 109.5 . . ?
N44 C51 C52 111.6(3) . . ?
N44 C51 H51A 109.3 . . ?
C52 C51 H51A 109.3 . . ?
N44 C51 H51B 109.3 . . ?
C52 C51 H51B 109.3 . . ?
H51A C51 H51B 108.0 . . ?
C53 C52 C57 120.0 . . ?
C53 C52 C51 121.1(3) . . ?
C57 C52 C51 118.9(3) . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 N56 120.0 . . ?
C54 C55 H55 120.0 . . ?
N56 C55 H55 120.0 . . ?
C57 N56 C55 120.0 . . ?
N56 C57 C52 120.0 . . ?
N56 C57 H57 120.0 . . ?
C52 C57 H57 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 1014557'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N2 Ni O2 S4'
_chemical_formula_weight         663.55

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   8.3049(6)
_cell_length_b                   21.4036(11)
_cell_length_c                   9.1470(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.609(7)
_cell_angle_gamma                90.00
_cell_volume                     1580.27(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7133
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            brown-green
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.63606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a
_diffrn_reflns_number            7133
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3467
_reflns_number_gt                1927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON(Spek, 2004)'
_computing_publication_material  'SHELXL-97, PLATON, WINGX (Ferrugia, 2012)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.6375P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3467
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S -0.13207(17) 0.00653(6) 0.18042(15) 0.0607(4) Uani 1 1 d . . .
S13 S 0.15716(16) 0.06805(6) 0.14927(15) 0.0613(4) Uani 1 1 d . . .
Ni1 Ni 0.0000 0.0000 0.0000 0.0520(3) Uani 1 2 d S . .
N14 N 0.0166(4) 0.09264(18) 0.3819(4) 0.0529(10) Uani 1 1 d . . .
C12 C 0.0151(5) 0.0615(2) 0.2594(5) 0.0507(11) Uani 1 1 d . . .
C21 C -0.1083(6) 0.0818(2) 0.4714(5) 0.0547(12) Uani 1 1 d . . .
H21A H -0.0522 0.0788 0.5770 0.066 Uiso 1 1 calc R . .
H21B H -0.1632 0.0423 0.4417 0.066 Uiso 1 1 calc R . .
C22 C -0.2357(6) 0.1322(2) 0.4524(5) 0.0522(12) Uani 1 1 d . . .
C23 C -0.2445(6) 0.1711(3) 0.5685(6) 0.0614(14) Uani 1 1 d . . .
H23 H -0.1657 0.1672 0.6590 0.074 Uiso 1 1 calc R . .
C24 C -0.3660(6) 0.2157(3) 0.5561(6) 0.0670(15) Uani 1 1 d . . .
H24 H -0.3702 0.2414 0.6371 0.080 Uiso 1 1 calc R . .
C25 C -0.4808(6) 0.2216(2) 0.4221(7) 0.0617(14) Uani 1 1 d . . .
C26 C -0.4732(7) 0.1837(3) 0.3028(6) 0.0715(16) Uani 1 1 d . . .
H26 H -0.5504 0.1883 0.2115 0.086 Uiso 1 1 calc R . .
C27 C -0.3529(7) 0.1396(3) 0.3184(6) 0.0662(14) Uani 1 1 d . . .
H27 H -0.3491 0.1139 0.2373 0.079 Uiso 1 1 calc R . .
C31 C 0.1403(6) 0.1420(2) 0.4399(6) 0.0592(13) Uani 1 1 d . . .
H31A H 0.0828 0.1796 0.4581 0.071 Uiso 1 1 calc R . .
H31B H 0.2004 0.1516 0.3637 0.071 Uiso 1 1 calc R . .
C32 C 0.2625(6) 0.1237(3) 0.5829(6) 0.0603(14) Uani 1 1 d . . .
C33 C 0.2594(8) 0.1536(3) 0.7183(7) 0.0831(19) Uani 1 1 d . . .
H33 H 0.1810 0.1844 0.7208 0.100 Uiso 1 1 calc R . .
C34 C 0.3729(11) 0.1371(4) 0.8473(8) 0.107(3) Uani 1 1 d . . .
H34 H 0.3719 0.1572 0.9373 0.128 Uiso 1 1 calc R . .
C35 C 0.4857(10) 0.0922(5) 0.8449(9) 0.112(3) Uani 1 1 d . . .
H35 H 0.5610 0.0811 0.9334 0.135 Uiso 1 1 calc R . .
C36 C 0.4904(7) 0.0624(4) 0.7113(9) 0.096(2) Uani 1 1 d . . .
H36 H 0.5692 0.0317 0.7100 0.115 Uiso 1 1 calc R . .
C37 C 0.3789(7) 0.0783(3) 0.5820(6) 0.0676(15) Uani 1 1 d . . .
H37 H 0.3817 0.0583 0.4924 0.081 Uiso 1 1 calc R . .
C281 C -0.6357(10) 0.3010(3) 0.5179(9) 0.124(3) Uani 1 1 d . . .
H281 H -0.5461 0.3304 0.5424 0.186 Uiso 1 1 calc R . .
H282 H -0.6381 0.2763 0.6051 0.186 Uiso 1 1 calc R . .
H283 H -0.7385 0.3231 0.4858 0.186 Uiso 1 1 calc R . .
O28 O -0.6121(5) 0.2607(2) 0.3987(5) 0.0910(13) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S11 C12 1.728(5) . ?
S11 Ni1 2.1904(12) . ?
S13 C12 1.727(4) . ?
S13 Ni1 2.2024(13) . ?
Ni1 S11 2.1904(12) 3 ?
Ni1 S13 2.2024(13) 3 ?
N14 C12 1.301(5) . ?
N14 C21 1.483(5) . ?
N14 C31 1.482(6) . ?
C21 C22 1.492(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.364(6) . ?
C22 C27 1.384(7) . ?
C23 C24 1.375(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(7) . ?
C24 H24 0.9300 . ?
C25 O28 1.351(6) . ?
C25 C26 1.373(7) . ?
C26 C27 1.358(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C31 C32 1.506(7) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C37 1.372(7) . ?
C32 C33 1.399(7) . ?
C33 C34 1.372(9) . ?
C33 H33 0.9300 . ?
C34 C35 1.346(10) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(10) . ?
C35 H35 0.9300 . ?
C36 C37 1.363(8) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C281 O28 1.439(7) . ?
C281 H281 0.9600 . ?
C281 H282 0.9600 . ?
C281 H283 0.9600 . ?

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
C12 S11 Ni1 85.87(16) . . ?
C12 S13 Ni1 85.51(16) . . ?
S11 Ni1 S11 180.00(5) 3 . ?
S11 Ni1 S13 79.60(4) 3 3 ?
S11 Ni1 S13 100.40(4) . 3 ?
S11 Ni1 S13 100.40(4) 3 . ?
S11 Ni1 S13 79.60(4) . . ?
S13 Ni1 S13 180.00(8) 3 . ?
C12 N14 C21 122.0(4) . . ?
C12 N14 C31 122.5(4) . . ?
C21 N14 C31 115.5(4) . . ?
N14 C12 S13 126.3(3) . . ?
N14 C12 S11 124.8(3) . . ?
S13 C12 S11 108.9(3) . . ?
N14 C21 C22 113.1(4) . . ?
N14 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N14 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C27 117.7(5) . . ?
C23 C22 C21 121.1(4) . . ?
C27 C22 C21 121.2(5) . . ?
C22 C23 C24 122.1(5) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C23 C24 C25 118.7(5) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
O28 C25 C26 115.2(5) . . ?
O28 C25 C24 124.4(5) . . ?
C26 C25 C24 120.3(5) . . ?
C27 C26 C25 119.8(5) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C22 121.3(5) . . ?
C26 C27 H27 119.3 . . ?
C22 C27 H27 119.3 . . ?
N14 C31 C32 113.2(4) . . ?
N14 C31 H31A 108.9 . . ?
C32 C31 H31A 108.9 . . ?
N14 C31 H31B 108.9 . . ?
C32 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C37 C32 C33 119.3(5) . . ?
C37 C32 C31 120.7(5) . . ?
C33 C32 C31 120.1(5) . . ?
C34 C33 C32 119.4(7) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C35 C34 C33 120.6(7) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.4(7) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 119.7(7) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C32 120.5(6) . . ?
C36 C37 H37 119.7 . . ?
C32 C37 H37 119.7 . . ?
O28 C281 H281 109.5 . . ?
O28 C281 H282 109.5 . . ?
H281 C281 H282 109.5 . . ?
O28 C281 H283 109.5 . . ?
H281 C281 H283 109.5 . . ?
H282 C281 H283 109.5 . . ?
C25 O28 C281 120.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.064
