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

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

data_rrk413_0m
_database_code_depnum_ccdc_archive 'CCDC 1032855'
_audit_update_record             
;
2015-06-10 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 N4 Ni O4 S2'
_chemical_formula_sum            'C26 H22 N4 Ni O4 S2'
_chemical_formula_weight         577.29

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   13.5191(10)
_cell_length_b                   5.4599(4)
_cell_length_c                   18.3237(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.169(4)
_cell_angle_gamma                90.00
_cell_volume                     1285.09(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    36
_cell_measurement_theta_min      25
_cell_measurement_theta_max      27

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Bruker Smart apex II'
_diffrn_measurement_method       'Ω and π scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14043
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         30.39
_reflns_number_total             3876
_reflns_number_gt                2054
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0721P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3830
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1512
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.0000 0.0000 0.0000 0.0523(2) Uani 1 2 d S . .
S1 S 0.22176(6) 0.72011(14) -0.03241(4) 0.0589(3) Uani 1 1 d . . .
O1 O 0.09707(17) 0.0155(3) 0.09592(12) 0.0564(5) Uani 1 1 d . . .
O2 O 0.47011(18) 0.3344(5) 0.38441(14) 0.0794(7) Uani 1 1 d . . .
N1 N 0.07137(18) 0.2674(4) -0.02024(14) 0.0513(6) Uani 1 1 d . . .
N2 N 0.15710(18) 0.3390(4) 0.04125(13) 0.0522(6) Uani 1 1 d . . .
C1 C 0.1624(2) 0.1950(5) 0.09998(17) 0.0499(7) Uani 1 1 d . . .
C2 C 0.2448(2) 0.2366(5) 0.17312(17) 0.0496(7) Uani 1 1 d . . .
C3 C 0.2576(2) 0.0760(5) 0.23440(19) 0.0574(8) Uani 1 1 d . . .
H3 H 0.2136 -0.0586 0.2284 0.069 Uiso 1 1 calc R . .
C4 C 0.3331(3) 0.1111(6) 0.30306(19) 0.0638(8) Uani 1 1 d . . .
H4 H 0.3402 0.0009 0.3431 0.077 Uiso 1 1 calc R . .
C5 C 0.3997(2) 0.3117(6) 0.31335(18) 0.0580(8) Uani 1 1 d . . .
C8 C 0.5390(3) 0.5377(8) 0.3992(3) 0.1064(16) Uani 1 1 d . . .
H8C H 0.5792 0.5346 0.3643 0.160 Uiso 1 1 calc R . .
H8A H 0.5848 0.5290 0.4511 0.160 Uiso 1 1 calc R . .
H8B H 0.4995 0.6868 0.3923 0.160 Uiso 1 1 calc R . .
C6 C 0.3890(3) 0.4724(5) 0.2530(2) 0.0618(8) Uani 1 1 d . . .
H6 H 0.4337 0.6056 0.2589 0.074 Uiso 1 1 calc R . .
C7 C 0.3124(2) 0.4351(5) 0.18425(18) 0.0576(8) Uani 1 1 d . . .
H7 H 0.3056 0.5451 0.1442 0.069 Uiso 1 1 calc R . .
C9 C 0.0540(2) 0.3916(5) -0.08350(16) 0.0511(7) Uani 1 1 d . . .
H9 H -0.0031 0.3432 -0.1243 0.061 Uiso 1 1 calc R . .
C10 C 0.1128(2) 0.5947(5) -0.09774(16) 0.0492(6) Uani 1 1 d . . .
C11 C 0.2320(3) 0.9310(6) -0.09817(19) 0.0611(8) Uani 1 1 d . . .
H11 H 0.2839 1.0496 -0.0879 0.073 Uiso 1 1 calc R . .
C12 C 0.1578(2) 0.9089(6) -0.16629(18) 0.0617(8) Uani 1 1 d . . .
H12 H 0.1528 1.0092 -0.2083 0.074 Uiso 1 1 calc R . .
C13 C 0.0884(2) 0.7167(5) -0.16686(18) 0.0589(8) Uani 1 1 d . . .
H13 H 0.0321 0.6762 -0.2093 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ni1 0.0613(4) 0.0420(3) 0.0621(4) -0.0043(2) 0.0316(3) -0.0084(2)
S1 0.0663(5) 0.0563(5) 0.0555(5) 0.0008(3) 0.0208(4) -0.0137(4)
O1 0.0654(13) 0.0458(11) 0.0658(13) -0.0014(9) 0.0317(11) -0.0122(9)
O2 0.0673(15) 0.0913(18) 0.0708(16) 0.0162(13) 0.0088(13) -0.0007(13)
N1 0.0572(14) 0.0455(13) 0.0576(15) -0.0061(10) 0.0272(12) -0.0053(11)
N2 0.0626(15) 0.0437(13) 0.0546(15) -0.0033(11) 0.0243(12) -0.0073(11)
C1 0.0591(17) 0.0394(14) 0.0602(18) -0.0052(12) 0.0316(15) -0.0013(12)
C2 0.0581(17) 0.0416(14) 0.0562(17) 0.0000(12) 0.0282(14) 0.0011(12)
C3 0.0641(19) 0.0435(15) 0.072(2) 0.0027(14) 0.0314(17) -0.0022(14)
C4 0.075(2) 0.0539(18) 0.069(2) 0.0124(15) 0.0308(18) 0.0084(16)
C5 0.0556(18) 0.0628(19) 0.0580(19) 0.0020(15) 0.0210(16) 0.0077(14)
C8 0.078(3) 0.125(4) 0.092(3) 0.013(3) -0.009(2) -0.017(3)
C6 0.067(2) 0.0510(18) 0.069(2) -0.0005(14) 0.0247(18) -0.0068(14)
C7 0.072(2) 0.0484(15) 0.0566(19) 0.0056(13) 0.0251(17) -0.0028(14)
C9 0.0548(17) 0.0480(15) 0.0553(18) -0.0036(13) 0.0238(14) -0.0032(13)
C10 0.0525(16) 0.0464(14) 0.0515(16) -0.0033(12) 0.0203(13) -0.0037(13)
C11 0.067(2) 0.0550(17) 0.067(2) 0.0009(15) 0.0291(17) -0.0149(15)
C12 0.074(2) 0.0567(18) 0.061(2) 0.0089(15) 0.0299(18) -0.0032(16)
C13 0.0617(19) 0.0589(18) 0.0572(19) 0.0021(14) 0.0203(15) -0.0036(14)

_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
Ni1 O1 1.839(2) . ?
Ni1 O1 1.839(2) 3 ?
Ni1 N1 1.850(2) 3 ?
Ni1 N1 1.850(2) . ?
S1 C11 1.703(3) . ?
S1 C10 1.724(3) . ?
O1 C1 1.306(3) . ?
O2 C5 1.358(4) . ?
O2 C8 1.419(4) . ?
N1 C9 1.300(3) . ?
N1 N2 1.397(3) . ?
N2 C1 1.317(3) . ?
C1 C2 1.469(4) . ?
C2 C7 1.392(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.364(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C8 H8C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.435(4) . ?
C9 H9 0.9300 . ?
C10 C13 1.377(4) . ?
C11 C12 1.341(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.406(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.0 . 3 ?
O1 Ni1 N1 96.09(9) . 3 ?
O1 Ni1 N1 83.91(9) 3 3 ?
O1 Ni1 N1 83.91(9) . . ?
O1 Ni1 N1 96.09(9) 3 . ?
N1 Ni1 N1 180.0 3 . ?
C11 S1 C10 91.02(15) . . ?
C1 O1 Ni1 110.95(18) . . ?
C5 O2 C8 118.5(3) . . ?
C9 N1 N2 116.5(2) . . ?
C9 N1 Ni1 129.1(2) . . ?
N2 N1 Ni1 114.37(17) . . ?
C1 N2 N1 108.2(2) . . ?
O1 C1 N2 122.6(3) . . ?
O1 C1 C2 118.3(2) . . ?
N2 C1 C2 119.1(2) . . ?
C7 C2 C3 117.5(3) . . ?
C7 C2 C1 122.0(3) . . ?
C3 C2 C1 120.5(3) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
O2 C5 C6 125.2(3) . . ?
O2 C5 C4 115.6(3) . . ?
C6 C5 C4 119.2(3) . . ?
O2 C8 H8C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 121.5(3) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N1 C9 C10 127.5(3) . . ?
N1 C9 H9 116.2 . . ?
C10 C9 H9 116.2 . . ?
C13 C10 C9 123.6(3) . . ?
C13 C10 S1 110.8(2) . . ?
C9 C10 S1 125.6(2) . . ?
C12 C11 S1 113.3(2) . . ?
C12 C11 H11 123.4 . . ?
S1 C11 H11 123.4 . . ?
C11 C12 C13 112.2(3) . . ?
C11 C12 H12 123.9 . . ?
C13 C12 H12 123.9 . . ?
C10 C13 C12 112.7(3) . . ?
C10 C13 H13 123.6 . . ?
C12 C13 H13 123.6 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        30.39
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.226
