# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
#TrackingRef '1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H42 N6 Ni S4'
_chemical_formula_weight         721.69

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'
Ni Ni 0.3393 1.1124 '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                   7.217(2)
_cell_length_b                   8.617(3)
_cell_length_c                   16.124(5)
_cell_angle_alpha                87.616(4)
_cell_angle_beta                 87.800(5)
_cell_angle_gamma                72.222(4)
_cell_volume                     953.7(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    714
_cell_measurement_theta_min      2.5295
_cell_measurement_theta_max      15.861

_exptl_crystal_description       Plate
_exptl_crystal_colour            Dark-red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7986
_exptl_absorpt_correction_T_max  0.9239
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7258
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_sigmaI/netI    0.1048
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3527
_reflns_number_gt                1450
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0913P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3527
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1886
_refine_ls_wR_factor_gt          0.1367
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_restrained_S_all      0.883
_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
Ni1 Ni 0.5000 0.0000 0.5000 0.0755(4) Uani 1 2 d S . .
S1 S 0.5467(2) 0.20814(19) 0.55653(11) 0.0885(6) Uani 1 1 d . . .
S2 S 0.2620(2) 0.0012(2) 0.58667(10) 0.0909(6) Uani 1 1 d . . .
N1 N 0.3274(8) 0.5253(7) 0.7094(4) 0.1109(19) Uani 1 1 d . . .
N2 N -0.0457(11) 0.2464(9) 0.7531(4) 0.150(3) Uani 1 1 d . . .
N3 N 1.2290(7) 0.2462(6) 0.3368(3) 0.0814(13) Uani 1 1 d . . .
C1 C 0.3405(9) 0.4074(8) 0.6765(4) 0.0852(18) Uani 1 1 d . . .
C2 C 0.3613(8) 0.2620(7) 0.6319(3) 0.0783(16) Uani 1 1 d . . .
C3 C 0.2351(8) 0.1723(7) 0.6446(4) 0.0828(17) Uani 1 1 d . . .
C4 C 0.0788(11) 0.2151(9) 0.7059(5) 0.102(2) Uani 1 1 d . . .
C5 C 0.4766(15) 0.2597(14) -0.1170(6) 0.207(5) Uani 1 1 d . . .
H5A H 0.3598 0.2293 -0.1206 0.311 Uiso 1 1 calc R . .
H5B H 0.5729 0.1990 -0.1559 0.311 Uiso 1 1 calc R . .
H5C H 0.4486 0.3743 -0.1298 0.311 Uiso 1 1 calc R . .
C6 C 0.5477(17) 0.2254(13) -0.0358(7) 0.183(4) Uani 1 1 d . . .
H6A H 0.5712 0.1100 -0.0232 0.220 Uiso 1 1 calc R . .
H6B H 0.4474 0.2850 0.0028 0.220 Uiso 1 1 calc R . .
C7 C 0.7283(15) 0.2662(12) -0.0216(6) 0.163(4) Uani 1 1 d . . .
H7A H 0.7041 0.3822 -0.0321 0.196 Uiso 1 1 calc R . .
H7B H 0.8281 0.2092 -0.0611 0.196 Uiso 1 1 calc R . .
C8 C 0.8037(15) 0.2232(12) 0.0647(6) 0.174(4) Uani 1 1 d . . .
H8A H 0.7042 0.2823 0.1037 0.208 Uiso 1 1 calc R . .
H8B H 0.8233 0.1078 0.0755 0.208 Uiso 1 1 calc R . .
C9 C 0.9876(15) 0.2579(12) 0.0815(6) 0.169(4) Uani 1 1 d . . .
H9A H 0.9661 0.3747 0.0775 0.203 Uiso 1 1 calc R . .
H9B H 1.0857 0.2075 0.0398 0.203 Uiso 1 1 calc R . .
C10 C 1.0650(15) 0.1903(11) 0.1718(6) 0.155(3) Uani 1 1 d . . .
H10A H 0.9722 0.2468 0.2139 0.186 Uiso 1 1 calc R . .
H10B H 1.0782 0.0750 0.1775 0.186 Uiso 1 1 calc R . .
C11 C 1.2471(15) 0.2148(13) 0.1832(5) 0.160(4) Uani 1 1 d . . .
H11A H 1.2325 0.3306 0.1802 0.192 Uiso 1 1 calc R . .
H11B H 1.3379 0.1630 0.1393 0.192 Uiso 1 1 calc R . .
C12 C 1.3268(10) 0.1434(8) 0.2669(4) 0.104(2) Uani 1 1 d . . .
H12A H 1.3108 0.0360 0.2751 0.125 Uiso 1 1 calc R . .
H12B H 1.4650 0.1307 0.2670 0.125 Uiso 1 1 calc R . .
C13 C 1.2827(9) 0.3766(8) 0.3533(4) 0.098(2) Uani 1 1 d . . .
H13A H 1.3799 0.4008 0.3206 0.118 Uiso 1 1 calc R . .
C14 C 1.1975(9) 0.4758(8) 0.4174(4) 0.0939(19) Uani 1 1 d . . .
H14A H 1.2409 0.5636 0.4287 0.113 Uiso 1 1 calc R . .
C15 C 1.0481(8) 0.4469(7) 0.4654(3) 0.0720(15) Uani 1 1 d . . .
C16 C 0.9989(9) 0.3098(8) 0.4474(4) 0.0870(18) Uani 1 1 d . . .
H16A H 0.9024 0.2826 0.4791 0.104 Uiso 1 1 calc R . .
C17 C 1.0897(9) 0.2131(8) 0.3834(4) 0.0887(18) Uani 1 1 d . . .
H17A H 1.0526 0.1219 0.3724 0.106 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 0.0727(7) 0.0741(7) 0.0893(8) -0.0034(6) -0.0006(5) -0.0368(6)
S1 0.0861(11) 0.0873(11) 0.1066(13) -0.0160(9) 0.0120(9) -0.0479(9)
S2 0.0902(11) 0.0915(11) 0.1067(13) -0.0065(10) 0.0094(9) -0.0520(10)
N1 0.114(5) 0.100(4) 0.124(5) -0.023(4) 0.017(4) -0.040(4)
N2 0.140(6) 0.174(7) 0.140(6) -0.003(5) 0.042(5) -0.060(5)
N3 0.083(3) 0.083(3) 0.080(4) -0.007(3) -0.002(3) -0.028(3)
C1 0.078(4) 0.095(5) 0.087(5) -0.009(4) 0.004(3) -0.034(4)
C2 0.076(4) 0.080(4) 0.081(4) -0.003(3) 0.003(3) -0.027(3)
C3 0.084(4) 0.083(4) 0.087(4) 0.001(3) 0.003(3) -0.036(4)
C4 0.112(6) 0.102(5) 0.101(6) -0.002(4) 0.010(4) -0.046(5)
C5 0.187(11) 0.268(13) 0.148(9) -0.025(9) -0.039(8) -0.035(9)
C6 0.182(11) 0.218(12) 0.150(10) -0.001(8) -0.009(8) -0.061(9)
C7 0.172(10) 0.182(9) 0.119(8) -0.024(7) -0.019(7) -0.025(8)
C8 0.152(9) 0.204(10) 0.133(9) -0.023(7) -0.017(7) -0.003(8)
C9 0.139(8) 0.223(11) 0.123(8) -0.015(7) -0.007(6) -0.020(8)
C10 0.163(9) 0.176(9) 0.131(8) -0.055(7) 0.032(7) -0.057(7)
C11 0.174(9) 0.231(10) 0.102(7) -0.054(7) 0.035(6) -0.100(8)
C12 0.106(5) 0.114(5) 0.093(5) -0.028(5) 0.011(4) -0.033(4)
C13 0.103(5) 0.114(5) 0.094(5) -0.007(4) 0.013(4) -0.059(5)
C14 0.104(5) 0.097(5) 0.099(5) -0.019(4) 0.012(4) -0.058(4)
C15 0.073(4) 0.082(4) 0.072(4) 0.006(3) -0.006(3) -0.041(3)
C16 0.089(4) 0.101(5) 0.085(5) -0.004(4) 0.005(4) -0.050(4)
C17 0.088(4) 0.092(5) 0.097(5) 0.002(4) -0.002(4) -0.045(4)

_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 S1 2.1656(16) 2_656 ?
Ni1 S1 2.1656(16) . ?
Ni1 S2 2.1698(16) 2_656 ?
Ni1 S2 2.1698(16) . ?
S1 C2 1.740(6) . ?
S2 C3 1.735(6) . ?
N1 C1 1.143(7) . ?
N2 C4 1.130(8) . ?
N3 C17 1.325(7) . ?
N3 C13 1.335(7) . ?
N3 C12 1.480(7) . ?
C1 C2 1.435(8) . ?
C2 C3 1.368(7) . ?
C3 C4 1.440(8) . ?
C5 C6 1.411(11) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.478(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.503(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.483(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.602(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.413(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.519(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.371(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.381(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(8) . ?
C15 C15 1.483(11) 2_766 ?
C16 C17 1.369(8) . ?
C16 H16A 0.9300 . ?
C17 H17A 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
S1 Ni1 S1 180.00(8) 2_656 . ?
S1 Ni1 S2 91.98(6) 2_656 2_656 ?
S1 Ni1 S2 88.02(6) . 2_656 ?
S1 Ni1 S2 88.02(6) 2_656 . ?
S1 Ni1 S2 91.98(6) . . ?
S2 Ni1 S2 180.0 2_656 . ?
C2 S1 Ni1 103.5(2) . . ?
C3 S2 Ni1 103.8(2) . . ?
C17 N3 C13 118.9(5) . . ?
C17 N3 C12 122.2(5) . . ?
C13 N3 C12 118.9(5) . . ?
N1 C1 C2 177.4(7) . . ?
C3 C2 C1 121.9(5) . . ?
C3 C2 S1 120.5(5) . . ?
C1 C2 S1 117.6(4) . . ?
C2 C3 C4 121.7(6) . . ?
C2 C3 S2 120.0(5) . . ?
C4 C3 S2 118.3(4) . . ?
N2 C4 C3 178.5(8) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C5 C6 C7 115.2(10) . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 113.9(10) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 116.0(10) . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C8 C9 C10 111.5(9) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 109.8(8) . . ?
C11 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 110.3(8) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N3 C12 C11 112.7(6) . . ?
N3 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 121.4(6) . . ?
N3 C13 H13A 119.3 . . ?
C14 C13 H13A 119.3 . . ?
C13 C14 C15 120.9(5) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 116.0(5) . . ?
C16 C15 C15 121.9(6) . 2_766 ?
C14 C15 C15 122.1(6) . 2_766 ?
C17 C16 C15 121.1(5) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
N3 C17 C16 121.7(6) . . ?
N3 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.143


_database_code_depnum_ccdc_archive 'CCDC 929581'