# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  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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data_szg215

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H44 N6 Ni3 O22 P4'
_chemical_formula_weight         1116.70

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'
P P 0.1023 0.0942 '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   'C2/c  '

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

_cell_length_a                   27.790(3)
_cell_length_b                   8.1036(7)
_cell_length_c                   22.617(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.1290(10)
_cell_angle_gamma                90.00
_cell_volume                     4265.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4517
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2296
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_T_max  0.9265
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  ?
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11747
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unnetI/netI    0.0319
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.49
_reflns_number_total             4392
_reflns_number_gt                3598
_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 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)+(0.1418P)²+30.6108P] 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         4392
_refine_ls_number_parameters     285
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2091
_refine_ls_wR_factor_gt          0.1945
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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 0.17889(3) 0.71699(8) 0.25279(3) 0.0161(2) Uani 1 1 d . . .
Ni2 Ni 0.0000 0.49796(12) 0.2500 0.0196(3) Uani 1 2 d S . .
P1 P 0.29027(5) 0.85216(16) 0.24228(7) 0.0188(3) Uani 1 1 d . . .
P2 P 0.24778(6) 0.92486(17) 0.38854(7) 0.0248(3) Uani 1 1 d . . .
O1 O 0.25305(17) 0.7517(5) 0.2566(2) 0.0273(9) Uani 1 1 d . . .
O2 O 0.33428(17) 0.7394(5) 0.2384(2) 0.0284(9) Uani 1 1 d . . .
H2C H 0.3559 0.6922 0.2781 0.043 Uiso 1 1 d R . .
O3 O 0.32463(16) 0.9880(4) 0.29433(19) 0.0225(8) Uani 1 1 d . . .
O4 O 0.19379(17) 0.9310(5) 0.3143(2) 0.0275(8) Uani 1 1 d . . .
O5 O 0.2429(3) 0.9887(6) 0.4461(3) 0.0455(12) Uani 1 1 d . . .
O6 O 0.2974(2) 1.0230(5) 0.3902(2) 0.0365(10) Uani 1 1 d . . .
H6A H 0.2886 1.1248 0.3830 0.055 Uiso 1 1 d R . .
O7 O 0.11254(16) 0.6519(5) 0.26087(19) 0.0249(8) Uani 1 1 d . . .
O8 O 0.08809(16) 0.4848(4) 0.3179(2) 0.0258(8) Uani 1 1 d . . .
O9 O 0.00001(16) 0.7521(4) 0.2500(2) 0.0361(14) Uani 1 2 d SR . .
H9B H 0.0043 0.7951 0.2869 0.043 Uiso 0.50 1 d PR . .
H9C H -0.0282 0.7951 0.2127 0.043 Uiso 0.50 1 d PR . .
O10 O 0.0000 0.2372(8) 0.2500 0.0429(16) Uani 1 2 d S . .
H10B H -0.0002 0.2022 0.2144 0.064 Uiso 0.50 1 d PR . .
H10C H 0.0299 0.2022 0.2876 0.064 Uiso 0.50 1 d PR . .
O1W O 0.0885(3) 0.9804(10) 0.3177(4) 0.088(2) Uani 1 1 d . . .
H1WC H 0.1109 1.0022 0.3614 0.105 Uiso 1 1 d R . .
H1WD H 0.1073 0.9260 0.3046 0.105 Uiso 1 1 d R . .
O2W O 0.2051(5) 0.2081(14) 0.5008(6) 0.137(4) Uani 1 1 d U . .
H2WA H 0.2244 0.1238 0.5035 0.206 Uiso 1 1 d R . .
H2WB H 0.2223 0.2574 0.5404 0.206 Uiso 1 1 d R . .
N1 N 0.22758(17) 0.5947(5) 0.3525(2) 0.0175(9) Uani 1 1 d . . .
N2 N 0.11792(19) 0.8295(6) 0.1581(2) 0.0218(9) Uani 1 1 d . . .
N3 N 0.0005(2) 0.4970(6) 0.3429(2) 0.0248(10) Uani 1 1 d . . .
C1 C 0.2452(2) 0.9508(7) 0.1580(3) 0.0217(10) Uani 1 1 d . . .
H1A H 0.2350 0.8708 0.1210 0.026 Uiso 1 1 d R . .
H1B H 0.2100 0.9862 0.1534 0.026 Uiso 1 1 d R . .
C2 C 0.2720(2) 0.7108(6) 0.4044(3) 0.0264(12) Uani 1 1 d . . .
H2A H 0.3059 0.7019 0.4026 0.032 Uiso 1 1 d R . .
H2B H 0.2826 0.6793 0.4515 0.032 Uiso 1 1 d R . .
C3 C 0.1868(2) 0.5445(7) 0.3718(3) 0.0243(11) Uani 1 1 d . . .
H3A H 0.1933 0.6122 0.4109 0.029 Uiso 1 1 d R . .
H3B H 0.1944 0.4308 0.3878 0.029 Uiso 1 1 d R . .
C4 C 0.1248(2) 0.5604(6) 0.3116(3) 0.0193(10) Uani 1 1 d . . .
C5 C 0.1121(2) 0.8087(7) 0.0962(3) 0.0233(11) Uani 1 1 d . . .
H5 H 0.1397 0.7463 0.0950 0.028 Uiso 1 1 d R . .
C6 C 0.0676(2) 0.8744(7) 0.0336(3) 0.0267(12) Uani 1 1 d . . .
H6 H 0.0663 0.8587 -0.0080 0.032 Uiso 1 1 d R . .
C7 C 0.0246(2) 0.9648(6) 0.0331(3) 0.0223(11) Uani 1 1 d . . .
C8 C 0.0305(2) 0.9856(7) 0.0972(3) 0.0282(12) Uani 1 1 d . . .
H8 H 0.0029 1.0444 0.0997 0.034 Uiso 1 1 d R . .
C9 C 0.0773(3) 0.9196(8) 0.1576(3) 0.0299(13) Uani 1 1 d . . .
H9A H 0.0809 0.9387 0.2004 0.036 Uiso 1 1 d R . .
C10 C -0.0374(2) 0.4113(7) 0.3487(3) 0.0249(11) Uani 1 1 d . . .
H10A H -0.0642 0.3479 0.3104 0.030 Uiso 1 1 d R . .
C11 C -0.0394(2) 0.4107(7) 0.4084(3) 0.0263(12) Uani 1 1 d . . .
H11 H -0.0675 0.3500 0.4089 0.032 Uiso 1 1 d R . .
C12 C 0.0002(2) 0.4995(7) 0.4671(3) 0.0231(11) Uani 1 1 d . . .
C13 C 0.0396(3) 0.5912(9) 0.4611(3) 0.0377(15) Uani 1 1 d . . .
H13 H 0.0673 0.6545 0.4988 0.045 Uiso 1 1 d R . .
C14 C 0.0376(3) 0.5880(9) 0.3991(3) 0.0378(15) Uani 1 1 d . . .
H14 H 0.0637 0.6530 0.3960 0.045 Uiso 1 1 d 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
Ni1 O7 2.020(4) . ?
Ni1 O1 2.035(4) . ?
Ni1 N2 2.079(4) . ?
Ni1 O3 2.115(4) 4_545 ?
Ni1 O4 2.117(4) . ?
Ni1 N1 2.136(4) . ?
Ni2 O9 2.059(3) . ?
Ni2 O8 2.062(4) 2 ?
Ni2 O8 2.062(4) . ?
Ni2 N3 2.094(5) . ?
Ni2 N3 2.094(5) 2 ?
Ni2 O10 2.113(6) . ?
P1 O1 1.485(4) . ?
P1 O3 1.510(4) . ?
P1 O2 1.567(4) . ?
P1 C1 1.797(5) . ?
P2 O5 1.476(5) . ?
P2 O4 1.523(4) . ?
P2 O6 1.575(5) . ?
P2 C2 1.823(5) . ?
O2 H2C 0.8501 . ?
O3 Ni1 2.115(4) 4 ?
O6 H6A 0.8500 . ?
O7 C4 1.248(6) . ?
O8 C4 1.262(6) . ?
O9 H9B 0.8498 . ?
O9 H9C 0.8510 . ?
O10 H10B 0.8501 . ?
O10 H10C 0.8500 . ?
O1W H1WC 0.8500 . ?
O1W H1WD 0.8501 . ?
O2W H2WA 0.8501 . ?
O2W H2WB 0.8500 . ?
N1 C1 1.478(6) 4_545 ?
N1 C3 1.477(7) . ?
N1 C2 1.484(7) . ?
N2 C5 1.329(7) . ?
N2 C9 1.339(7) . ?
N3 C10 1.327(7) . ?
N3 C14 1.338(8) . ?
C1 N1 1.478(6) 4 ?
C1 H1A 0.9699 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9699 . ?
C2 H2B 0.9701 . ?
C3 C4 1.509(7) . ?
C3 H3A 0.9701 . ?
C3 H3B 0.9700 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9301 . ?
C6 C7 1.396(8) . ?
C6 H6 0.9302 . ?
C7 C8 1.377(8) . ?
C7 C7 1.484(10) 5_575 ?
C8 C9 1.380(8) . ?
C8 H8 0.9302 . ?
C9 H9A 0.9302 . ?
C10 C11 1.380(7) . ?
C10 H10A 0.9299 . ?
C11 C12 1.376(8) . ?
C11 H11 0.9302 . ?
C12 C13 1.392(8) . ?
C12 C12 1.494(10) 5_566 ?
C13 C14 1.370(8) . ?
C13 H13 0.9300 . ?
C14 H14 0.9302 . ?

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
O7 Ni1 O1 170.35(15) . . ?
O7 Ni1 N2 86.42(16) . . ?
O1 Ni1 N2 102.67(17) . . ?
O7 Ni1 O3 91.33(16) . 4_545 ?
O1 Ni1 O3 84.79(16) . 4_545 ?
N2 Ni1 O3 94.49(16) . 4_545 ?
O7 Ni1 O4 90.88(17) . . ?
O1 Ni1 O4 91.66(16) . . ?
N2 Ni1 O4 94.25(17) . . ?
O3 Ni1 O4 171.10(15) 4_545 . ?
O7 Ni1 N1 82.32(15) . . ?
O1 Ni1 N1 88.66(16) . . ?
N2 Ni1 N1 168.64(17) . . ?
O3 Ni1 N1 87.31(15) 4_545 . ?
O4 Ni1 N1 84.44(15) . . ?
O9 Ni2 O8 92.97(14) . 2 ?
O9 Ni2 O8 92.95(15) . . ?
O8 Ni2 O8 174.08(19) 2 . ?
O9 Ni2 N3 90.19(17) . . ?
O8 Ni2 N3 95.80(17) 2 . ?
O8 Ni2 N3 84.18(17) . . ?
O9 Ni2 N3 90.21(17) . 2 ?
O8 Ni2 N3 84.18(17) 2 2 ?
O8 Ni2 N3 95.80(17) . 2 ?
N3 Ni2 N3 179.6(3) . 2 ?
O9 Ni2 O10 180.0(2) . . ?
O8 Ni2 O10 87.04(10) 2 . ?
O8 Ni2 O10 87.04(10) . . ?
N3 Ni2 O10 89.80(13) . . ?
N3 Ni2 O10 89.80(13) 2 . ?
O1 P1 O3 116.7(2) . . ?
O1 P1 O2 110.5(2) . . ?
O3 P1 O2 106.8(2) . . ?
O1 P1 C1 108.1(2) . . ?
O3 P1 C1 106.2(2) . . ?
O2 P1 C1 108.2(2) . . ?
O5 P2 O4 116.8(3) . . ?
O5 P2 O6 107.7(3) . . ?
O4 P2 O6 109.4(2) . . ?
O5 P2 C2 111.2(3) . . ?
O4 P2 C2 106.4(2) . . ?
O6 P2 C2 104.6(3) . . ?
P1 O1 Ni1 151.3(3) . . ?
P1 O2 H2C 109.0 . . ?
P1 O3 Ni1 114.3(2) . 4 ?
P2 O4 Ni1 114.8(2) . . ?
P2 O6 H6A 109.2 . . ?
C4 O7 Ni1 115.8(3) . . ?
C4 O8 Ni2 126.5(3) . . ?
Ni2 O9 H9B 114.2 . . ?
Ni2 O9 H9C 114.2 . . ?
H9B O9 H9C 111.3 . . ?
Ni2 O10 H10B 109.5 . . ?
Ni2 O10 H10C 109.5 . . ?
H10B O10 H10C 109.5 . . ?
H1WC O1W H1WD 108.2 . . ?
H2WA O2W H2WB 109.5 . . ?
C1 N1 C3 111.9(4) 4_545 . ?
C1 N1 C2 110.5(4) 4_545 . ?
C3 N1 C2 112.3(4) . . ?
C1 N1 Ni1 106.3(3) 4_545 . ?
C3 N1 Ni1 107.1(3) . . ?
C2 N1 Ni1 108.3(3) . . ?
C5 N2 C9 116.4(5) . . ?
C5 N2 Ni1 126.2(4) . . ?
C9 N2 Ni1 117.1(4) . . ?
C10 N3 C14 115.8(5) . . ?
C10 N3 Ni2 122.1(4) . . ?
C14 N3 Ni2 122.0(4) . . ?
N1 C1 P1 113.6(3) 4 . ?
N1 C1 H1A 108.8 4 . ?
P1 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 4 . ?
P1 C1 H1B 108.8 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 P2 113.0(4) . . ?
N1 C2 H2A 109.0 . . ?
P2 C2 H2A 109.0 . . ?
N1 C2 H2B 108.9 . . ?
P2 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 113.1(4) . . ?
N1 C3 H3A 109.0 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O7 C4 O8 124.1(5) . . ?
O7 C4 C3 118.9(5) . . ?
O8 C4 C3 116.9(5) . . ?
N2 C5 C6 123.8(5) . . ?
N2 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C6 C7 119.7(5) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 116.5(5) . . ?
C8 C7 C7 121.9(6) . 5_575 ?
C6 C7 C7 121.6(6) . 5_575 ?
C7 C8 C9 120.0(5) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
N2 C9 C8 123.6(5) . . ?
N2 C9 H9A 118.2 . . ?
C8 C9 H9A 118.2 . . ?
N3 C10 C11 123.8(5) . . ?
N3 C10 H10A 118.1 . . ?
C11 C10 H10A 118.1 . . ?
C12 C11 C10 120.3(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 116.2(5) . . ?
C11 C12 C12 121.8(6) . 5_566 ?
C13 C12 C12 122.0(6) . 5_566 ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.2 . . ?
N3 C14 C13 124.1(6) . . ?
N3 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         4.237
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.181
_database_code_depnum_ccdc_archive 'CCDC 1011163'
