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

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#
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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.
#
#  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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data_szg214

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H40 N4 Ni3 O20 P4'
_chemical_formula_weight         1076.67

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                   25.769(2)
_cell_length_b                   9.7059(9)
_cell_length_c                   17.2986(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.016(2)
_cell_angle_gamma                90.00
_cell_volume                     4197.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2752
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.78

_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    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_T_max  0.9300
_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            11590
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unnetI/netI    0.0555
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         26.49
_reflns_number_total             4338
_reflns_number_gt                3339
_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)+(0.0671P)²+15.3828P] 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         4338
_refine_ls_number_parameters     277
_refine_ls_number_restraints     372
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.056
_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 0.27579(2) 0.70343(5) 0.15585(3) 0.01192(15) Uani 1 1 d . . .
Ni2 Ni 0.2500 0.2500 0.0000 0.0175(2) Uani 1 2 d S . .
P1 P 0.22237(4) 0.56847(11) -0.00583(6) 0.0121(2) Uani 1 1 d . . .
P2 P 0.22456(5) 0.48158(11) 0.23531(6) 0.0147(2) Uani 1 1 d . . .
O1 O 0.27408(11) 0.5803(3) 0.05830(16) 0.0154(6) Uani 1 1 d U . .
O2 O 0.20146(11) 0.4200(3) -0.01576(17) 0.0157(6) Uani 1 1 d U . .
O3 O 0.22639(12) 0.6229(3) -0.08647(16) 0.0181(7) Uani 1 1 d U . .
O4 O 0.27732(12) 0.5359(3) 0.22629(18) 0.0217(7) Uani 1 1 d U . .
O5 O 0.20594(14) 0.5605(3) 0.30383(18) 0.0250(7) Uani 1 1 d U . .
H5A H 0.2274 0.5423 0.3482 0.037 Uiso 1 1 d RU . .
O6 O 0.22293(12) 0.3284(3) 0.24700(17) 0.0185(7) Uani 1 1 d U . .
O7 O -0.09729(15) 0.6346(5) 0.0809(3) 0.0481(11) Uani 1 1 d U . .
H7 H -0.1295 0.6305 0.0604 0.072 Uiso 1 1 d RU . .
O8 O -0.09794(17) 0.7744(7) -0.0213(3) 0.0799(19) Uani 1 1 d U . .
O9 O 0.30389(14) 0.3236(3) 0.1007(2) 0.0306(8) Uani 1 1 d U . .
H9B H 0.3354 0.3199 0.0935 0.037 Uiso 1 1 d RU . .
H9A H 0.2964 0.4035 0.1090 0.046 Uiso 1 1 d RU . .
O10 O 0.20313(13) 0.1691(4) 0.0732(2) 0.0315(8) Uani 1 1 d U . .
H10A H 0.2195 0.1790 0.1218 0.038 Uiso 1 1 d RU . .
H10B H 0.1982 0.0835 0.0639 0.038 Uiso 1 1 d RU . .
N1 N 0.18635(14) 0.6702(3) 0.11773(19) 0.0126(7) Uani 1 1 d . . .
N2 N 0.35910(15) 0.6989(4) 0.1865(2) 0.0228(8) Uani 1 1 d . . .
C1 C 0.17417(16) 0.6723(4) 0.0294(2) 0.0138(8) Uani 1 1 d U . .
H1A H 0.1753 0.7665 0.0110 0.017 Uiso 1 1 d RU . .
H1B H 0.1384 0.6366 0.0078 0.017 Uiso 1 1 d RU . .
C2 C 0.17550(17) 0.5305(4) 0.1460(2) 0.0158(8) Uani 1 1 d U . .
H2A H 0.1757 0.4636 0.1044 0.019 Uiso 1 1 d RU . .
H2B H 0.1402 0.5297 0.1567 0.019 Uiso 1 1 d RU . .
C3 C 0.15632(17) 0.7802(5) 0.1495(3) 0.0190(9) Uani 1 1 d U . .
H3A H 0.1669 0.8690 0.1327 0.023 Uiso 1 1 d RU . .
H3B H 0.1670 0.7777 0.2072 0.023 Uiso 1 1 d RU . .
C4 C 0.09592(19) 0.7695(5) 0.1237(3) 0.0238(9) Uani 1 1 d U . .
C5 C 0.0666(2) 0.6989(6) 0.1695(3) 0.0329(10) Uani 1 1 d U . .
H5 H 0.0843 0.6623 0.2185 0.040 Uiso 1 1 d RU . .
C6 C 0.0121(2) 0.6828(6) 0.1432(3) 0.0371(12) Uani 1 1 d U . .
H6 H -0.0063 0.6346 0.1746 0.045 Uiso 1 1 d RU . .
C7 C -0.0156(2) 0.7376(6) 0.0711(3) 0.0356(11) Uani 1 1 d U . .
C8 C 0.0129(2) 0.8126(6) 0.0270(3) 0.0380(12) Uani 1 1 d U . .
H8 H -0.0052 0.8533 -0.0206 0.046 Uiso 1 1 d RU . .
C9 C 0.0675(2) 0.8289(6) 0.0524(3) 0.0318(10) Uani 1 1 d U . .
H9 H 0.0856 0.8798 0.0217 0.038 Uiso 1 1 d RU . .
C10 C -0.0743(2) 0.7179(7) 0.0388(4) 0.0422(13) Uani 1 1 d U . .
C11 C 0.3885(2) 0.8113(7) 0.1819(5) 0.0544(16) Uani 1 1 d U . .
H11 H 0.3708 0.8917 0.1611 0.065 Uiso 1 1 d RU . .
C12 C 0.4438(2) 0.8126(7) 0.2060(5) 0.0590(16) Uani 1 1 d U . .
H12 H 0.4627 0.8926 0.2013 0.071 Uiso 1 1 d RU . .
C13 C 0.4704(2) 0.6953(6) 0.2363(4) 0.0416(13) Uani 1 1 d U . .
C14 C 0.4409(3) 0.5832(8) 0.2418(5) 0.0725(19) Uani 1 1 d U . .
H14 H 0.4574 0.5013 0.2621 0.087 Uiso 1 1 d RU . .
C15 C 0.3855(3) 0.5899(7) 0.2157(5) 0.0672(18) Uani 1 1 d U . .
H15 H 0.3661 0.5107 0.2200 0.081 Uiso 1 1 d RU . .


_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 O4 2.026(3) . ?
Ni1 O1 2.059(3) . ?
Ni1 O3 2.062(3) 7_565 ?
Ni1 O6 2.066(3) 4 ?
Ni1 N2 2.083(4) . ?
Ni1 N1 2.262(3) . ?
Ni2 O2 2.049(3) . ?
Ni2 O2 2.049(3) 7 ?
Ni2 O9 2.074(3) 7 ?
Ni2 O9 2.074(3) . ?
Ni2 O10 2.103(3) 7 ?
Ni2 O10 2.103(3) . ?
P1 O3 1.518(3) . ?
P1 O1 1.518(3) . ?
P1 O2 1.533(3) . ?
P1 C1 1.816(4) . ?
P2 O4 1.501(3) . ?
P2 O6 1.503(3) . ?
P2 O5 1.580(3) . ?
P2 C2 1.807(4) . ?
O3 Ni1 2.062(3) 7_565 ?
O5 H5A 0.8500 . ?
O6 Ni1 2.066(3) 4_545 ?
O7 C10 1.321(7) . ?
O7 H7 0.8201 . ?
O8 C10 1.203(7) . ?
O9 H9B 0.8499 . ?
O9 H9A 0.8200 . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8500 . ?
N1 C1 1.484(5) . ?
N1 C2 1.491(5) . ?
N1 C3 1.499(5) . ?
N2 C15 1.293(8) . ?
N2 C11 1.341(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9702 . ?
C3 C4 1.515(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.397(7) . ?
C4 C5 1.399(7) . ?
C5 C6 1.377(7) . ?
C5 H5 0.9299 . ?
C6 C7 1.385(8) . ?
C6 H6 0.9299 . ?
C7 C8 1.387(8) . ?
C7 C10 1.491(7) . ?
C8 C9 1.376(7) . ?
C8 H8 0.9301 . ?
C9 H9 0.9301 . ?
C11 C12 1.386(8) . ?
C11 H11 0.9301 . ?
C12 C13 1.366(8) . ?
C12 H12 0.9301 . ?
C13 C14 1.344(9) . ?
C13 C13 1.483(10) 2_655 ?
C14 C15 1.390(9) . ?
C14 H14 0.9299 . ?
C15 H15 0.9301 . ?

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
O4 Ni1 O1 91.18(13) . . ?
O4 Ni1 O3 178.45(13) . 7_565 ?
O1 Ni1 O3 90.30(12) . 7_565 ?
O4 Ni1 O6 89.29(13) . 4 ?
O1 Ni1 O6 179.44(13) . 4 ?
O3 Ni1 O6 89.22(12) 7_565 4 ?
O4 Ni1 N2 87.79(14) . . ?
O1 Ni1 N2 90.70(14) . . ?
O3 Ni1 N2 92.65(14) 7_565 . ?
O6 Ni1 N2 89.61(14) 4 . ?
O4 Ni1 N1 86.03(12) . . ?
O1 Ni1 N1 81.96(11) . . ?
O3 Ni1 N1 93.72(12) 7_565 . ?
O6 Ni1 N1 97.78(12) 4 . ?
N2 Ni1 N1 170.30(14) . . ?
O2 Ni2 O2 180.00(13) . 7 ?
O2 Ni2 O9 84.42(12) . 7 ?
O2 Ni2 O9 95.58(12) 7 7 ?
O2 Ni2 O9 95.58(12) . . ?
O2 Ni2 O9 84.42(12) 7 . ?
O9 Ni2 O9 180.0(2) 7 . ?
O2 Ni2 O10 92.31(12) . 7 ?
O2 Ni2 O10 87.69(12) 7 7 ?
O9 Ni2 O10 89.33(14) 7 7 ?
O9 Ni2 O10 90.67(14) . 7 ?
O2 Ni2 O10 87.69(12) . . ?
O2 Ni2 O10 92.31(12) 7 . ?
O9 Ni2 O10 90.67(14) 7 . ?
O9 Ni2 O10 89.33(14) . . ?
O10 Ni2 O10 180.00(16) 7 . ?
O3 P1 O1 113.71(17) . . ?
O3 P1 O2 108.92(17) . . ?
O1 P1 O2 112.07(17) . . ?
O3 P1 C1 108.63(18) . . ?
O1 P1 C1 105.27(17) . . ?
O2 P1 C1 108.00(18) . . ?
O4 P2 O6 114.66(19) . . ?
O4 P2 O5 110.79(19) . . ?
O6 P2 O5 110.82(18) . . ?
O4 P2 C2 106.42(18) . . ?
O6 P2 C2 109.77(19) . . ?
O5 P2 C2 103.72(19) . . ?
P1 O1 Ni1 118.93(17) . . ?
P1 O2 Ni2 123.74(17) . . ?
P1 O3 Ni1 145.15(19) . 7_565 ?
P2 O4 Ni1 117.27(17) . . ?
P2 O5 H5A 109.1 . . ?
P2 O6 Ni1 134.01(18) . 4_545 ?
C10 O7 H7 109.5 . . ?
Ni2 O9 H9B 109.4 . . ?
Ni2 O9 H9A 109.6 . . ?
H9B O9 H9A 109.8 . . ?
Ni2 O10 H10A 109.5 . . ?
Ni2 O10 H10B 109.4 . . ?
H10A O10 H10B 108.2 . . ?
C1 N1 C2 110.0(3) . . ?
C1 N1 C3 111.6(3) . . ?
C2 N1 C3 111.9(3) . . ?
C1 N1 Ni1 104.2(2) . . ?
C2 N1 Ni1 107.0(2) . . ?
C3 N1 Ni1 111.8(2) . . ?
C15 N2 C11 116.0(5) . . ?
C15 N2 Ni1 121.9(4) . . ?
C11 N2 Ni1 122.0(4) . . ?
N1 C1 P1 110.3(3) . . ?
N1 C1 H1A 109.6 . . ?
P1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
P1 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
N1 C2 P2 111.8(3) . . ?
N1 C2 H2A 109.3 . . ?
P2 C2 H2A 109.3 . . ?
N1 C2 H2B 109.2 . . ?
P2 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 C4 115.3(4) . . ?
N1 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C9 C4 C5 117.6(5) . . ?
C9 C4 C3 120.9(4) . . ?
C5 C4 C3 121.5(4) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 121.1(5) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 118.0(5) . . ?
C6 C7 C10 122.9(5) . . ?
C8 C7 C10 119.1(5) . . ?
C9 C8 C7 121.5(5) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 120.7(5) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.6 . . ?
O8 C10 O7 123.6(5) . . ?
O8 C10 C7 121.4(6) . . ?
O7 C10 C7 115.0(5) . . ?
N2 C11 C12 123.0(6) . . ?
N2 C11 H11 118.4 . . ?
C12 C11 H11 118.7 . . ?
C13 C12 C11 119.5(6) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 117.5(5) . . ?
C14 C13 C13 122.2(4) . 2_655 ?
C12 C13 C13 120.2(4) . 2_655 ?
C13 C14 C15 119.6(7) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.1 . . ?
N2 C15 C14 124.5(6) . . ?
N2 C15 H15 117.7 . . ?
C14 C15 H15 117.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.140
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.122
_database_code_depnum_ccdc_archive 'CCDC 1011162'
