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

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#                 Cambridge Crystallographic Data Centre
#                                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
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#  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 
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data_c:\einkris\lars\absc\lhs1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_formula_moiety         'C16 H20 Ca O12 P2'
_chemical_formula_sum            'C16 H20 Ca O12 P2'
_chemical_formula_weight         506.34

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   4.6806(9)
_cell_length_b                   6.1340(12)
_cell_length_c                   17.932(4)
_cell_angle_alpha                83.84(3)
_cell_angle_beta                 89.03(3)
_cell_angle_gamma                85.65(3)
_cell_volume                     510.38(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.1628
_exptl_crystal_size_mid          0.1075
_exptl_crystal_size_min          0.0676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             262
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_process_details   'X-Shape and X-Red32 (Stoe, 2008)'

_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  'Stoe IPSD-2'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2768
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         29.22
_reflns_number_total             2768
_reflns_number_gt                1938
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe, 2008)'
_computing_cell_refinement       'X-Area (Stoe, 2008)'
_computing_data_reduction        'X-Area (Stoe, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_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^)+(0.0000P)^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         2768
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0411
_refine_ls_wR_factor_gt          0.0388
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
Ca1 Ca 0.0000 0.5000 0.5000 0.02337(14) Uani 1 2 d S . .
P1 P -0.46371(10) 0.38144(8) 0.37073(3) 0.02182(11) Uani 1 1 d . . .
O1 O 0.3632(3) 0.54825(19) 0.41085(6) 0.0275(3) Uani 1 1 d . . .
O2 O -0.1955(2) 0.28316(19) 0.41190(7) 0.0274(3) Uani 1 1 d . . .
O3 O -0.6526(3) 0.1882(2) 0.35638(7) 0.0316(3) Uani 1 1 d . . .
H11 H -0.8210 0.2232 0.3656 0.058(8) Uiso 1 1 calc R . .
O4 O -0.2424(3) 0.8294(2) 0.45131(8) 0.0429(4) Uani 1 1 d . . .
H9 H -0.2155 0.9601 0.4420 0.051 Uiso 1 1 d R . .
H10 H -0.4015 0.8056 0.4370 0.051 Uiso 1 1 d R . .
C1 C -0.3476(4) 0.4940(3) 0.28014(10) 0.0316(4) Uani 1 1 d . . .
H1B H -0.2190 0.6069 0.2869 0.038 Uiso 1 1 calc R . .
H1A H -0.2377 0.3785 0.2569 0.038 Uiso 1 1 calc R . .
C5 C -0.9952(4) 0.7745(3) 0.12427(10) 0.0306(4) Uani 1 1 d . . .
O5 O -1.3117(4) 1.0684(3) 0.07361(10) 0.0544(5) Uani 1 1 d . . .
H13 H -1.4134 1.1259 0.0391 0.065 Uiso 0.50 1 d PR . .
C8 C -1.2144(4) 0.8745(4) 0.06979(11) 0.0340(4) Uani 1 1 d . . .
C2 C -0.5788(4) 0.5924(3) 0.22648(10) 0.0285(4) Uani 1 1 d . . .
O6 O -1.2934(3) 0.7564(3) 0.02094(9) 0.0547(5) Uani 1 1 d . . .
H12 H -1.4153 0.8185 -0.0079 0.066 Uiso 0.50 1 d PR . .
C6 C -0.8760(4) 0.5634(3) 0.12016(11) 0.0355(5) Uani 1 1 d . . .
H6A H -0.9345 0.4816 0.0832 0.043 Uiso 1 1 calc R . .
C3 C -0.7021(4) 0.8024(3) 0.23081(11) 0.0346(5) Uani 1 1 d . . .
H3A H -0.6458 0.8833 0.2683 0.041 Uiso 1 1 calc R . .
C7 C -0.6695(4) 0.4735(3) 0.17102(11) 0.0357(5) Uani 1 1 d . . .
H7A H -0.5902 0.3310 0.1679 0.043 Uiso 1 1 calc R . .
C4 C -0.9077(4) 0.8933(3) 0.18022(11) 0.0348(5) Uani 1 1 d . . .
H4A H -0.9882 1.0353 0.1836 0.042 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
Ca1 0.0252(3) 0.0223(3) 0.0223(3) -0.0022(2) 0.0021(2) -0.0007(2)
P1 0.0189(3) 0.0243(3) 0.0223(3) -0.0024(2) -0.0017(2) -0.0021(2)
O1 0.0279(7) 0.0258(6) 0.0295(7) -0.0057(5) 0.0051(5) -0.0032(5)
O2 0.0229(6) 0.0306(7) 0.0283(7) -0.0001(5) -0.0036(5) -0.0022(5)
O3 0.0234(7) 0.0324(7) 0.0414(8) -0.0129(6) -0.0013(6) -0.0042(5)
O4 0.0357(8) 0.0271(7) 0.0645(10) 0.0043(7) -0.0168(7) -0.0031(6)
C1 0.0223(10) 0.0434(11) 0.0281(10) -0.0003(8) -0.0003(8) -0.0005(8)
C5 0.0272(10) 0.0382(11) 0.0251(9) 0.0016(8) -0.0003(8) -0.0014(8)
O5 0.0571(11) 0.0507(9) 0.0525(10) -0.0017(7) -0.0214(8) 0.0145(8)
C8 0.0288(11) 0.0429(12) 0.0284(10) 0.0027(9) -0.0002(8) -0.0008(9)
C2 0.0236(9) 0.0375(11) 0.0230(9) 0.0030(8) 0.0021(7) -0.0030(8)
O6 0.0540(11) 0.0676(11) 0.0421(9) -0.0137(8) -0.0220(8) 0.0141(9)
C6 0.0352(11) 0.0434(12) 0.0285(10) -0.0090(9) -0.0056(8) 0.0009(9)
C3 0.0362(11) 0.0371(11) 0.0314(10) -0.0064(9) -0.0052(9) -0.0046(9)
C7 0.0375(11) 0.0379(12) 0.0308(10) -0.0043(9) -0.0023(9) 0.0047(9)
C4 0.0378(12) 0.0284(10) 0.0374(11) -0.0019(9) -0.0040(9) 0.0009(9)

_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
Ca1 O1 2.3271(14) . ?
Ca1 O1 2.3271(14) 2_566 ?
Ca1 O4 2.3323(14) 2_566 ?
Ca1 O4 2.3323(14) . ?
Ca1 O2 2.4056(13) 2_566 ?
Ca1 O2 2.4056(13) . ?
Ca1 P1 3.3742(11) . ?
Ca1 P1 3.3742(11) 2_566 ?
Ca1 P1 3.4771(12) 1_655 ?
Ca1 P1 3.4771(12) 2_466 ?
P1 O1 1.4944(13) 1_455 ?
P1 O2 1.5184(13) . ?
P1 O3 1.5761(14) . ?
P1 C1 1.7880(19) . ?
P1 Ca1 3.4771(12) 1_455 ?
O1 P1 1.4945(13) 1_655 ?
C1 C2 1.508(2) . ?
C5 C6 1.379(3) . ?
C5 C4 1.386(3) . ?
C5 C8 1.481(3) . ?
O5 C8 1.249(3) . ?
C8 O6 1.272(2) . ?
C2 C3 1.380(3) . ?
C2 C7 1.385(3) . ?
C6 C7 1.383(3) . ?
C3 C4 1.379(3) . ?

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 Ca1 O1 180.000(2) . 2_566 ?
O1 Ca1 O4 89.28(5) . 2_566 ?
O1 Ca1 O4 90.72(5) 2_566 2_566 ?
O1 Ca1 O4 90.72(5) . . ?
O1 Ca1 O4 89.28(5) 2_566 . ?
O4 Ca1 O4 180.0 2_566 . ?
O1 Ca1 O2 95.55(5) . 2_566 ?
O1 Ca1 O2 84.45(5) 2_566 2_566 ?
O4 Ca1 O2 94.80(5) 2_566 2_566 ?
O4 Ca1 O2 85.20(5) . 2_566 ?
O1 Ca1 O2 84.45(5) . . ?
O1 Ca1 O2 95.55(5) 2_566 . ?
O4 Ca1 O2 85.20(5) 2_566 . ?
O4 Ca1 O2 94.80(5) . . ?
O2 Ca1 O2 179.999(1) 2_566 . ?
O1 Ca1 P1 92.18(3) . . ?
O1 Ca1 P1 87.82(3) 2_566 . ?
O4 Ca1 P1 107.68(4) 2_566 . ?
O4 Ca1 P1 72.32(4) . . ?
O2 Ca1 P1 156.31(3) 2_566 . ?
O2 Ca1 P1 23.69(3) . . ?
O1 Ca1 P1 87.82(3) . 2_566 ?
O1 Ca1 P1 92.18(3) 2_566 2_566 ?
O4 Ca1 P1 72.32(4) 2_566 2_566 ?
O4 Ca1 P1 107.68(4) . 2_566 ?
O2 Ca1 P1 23.68(3) 2_566 2_566 ?
O2 Ca1 P1 156.32(3) . 2_566 ?
P1 Ca1 P1 180.0 . 2_566 ?
O1 Ca1 P1 19.31(3) . 1_655 ?
O1 Ca1 P1 160.69(3) 2_566 1_655 ?
O4 Ca1 P1 73.73(5) 2_566 1_655 ?
O4 Ca1 P1 106.27(5) . 1_655 ?
O2 Ca1 P1 107.77(4) 2_566 1_655 ?
O2 Ca1 P1 72.23(4) . 1_655 ?
P1 Ca1 P1 86.17(2) . 1_655 ?
P1 Ca1 P1 93.83(2) 2_566 1_655 ?
O1 Ca1 P1 160.68(3) . 2_466 ?
O1 Ca1 P1 19.31(3) 2_566 2_466 ?
O4 Ca1 P1 106.27(5) 2_566 2_466 ?
O4 Ca1 P1 73.73(5) . 2_466 ?
O2 Ca1 P1 72.23(4) 2_566 2_466 ?
O2 Ca1 P1 107.77(4) . 2_466 ?
P1 Ca1 P1 93.83(2) . 2_466 ?
P1 Ca1 P1 86.17(2) 2_566 2_466 ?
P1 Ca1 P1 180.0 1_655 2_466 ?
O1 P1 O2 114.16(7) 1_455 . ?
O1 P1 O3 109.96(7) 1_455 . ?
O2 P1 O3 108.30(7) . . ?
O1 P1 C1 111.95(9) 1_455 . ?
O2 P1 C1 106.27(8) . . ?
O3 P1 C1 105.77(9) . . ?
O1 P1 Ca1 77.61(5) 1_455 . ?
O2 P1 Ca1 39.53(5) . . ?
O3 P1 Ca1 138.45(5) . . ?
C1 P1 Ca1 108.70(7) . . ?
O1 P1 Ca1 31.00(5) 1_455 1_455 ?
O2 P1 Ca1 109.57(5) . 1_455 ?
O3 P1 Ca1 83.72(6) . 1_455 ?
C1 P1 Ca1 137.63(6) . 1_455 ?
Ca1 P1 Ca1 86.17(2) . 1_455 ?
P1 O1 Ca1 129.69(7) 1_655 . ?
P1 O2 Ca1 116.79(7) . . ?
C2 C1 P1 116.54(13) . . ?
C6 C5 C4 119.27(17) . . ?
C6 C5 C8 120.78(18) . . ?
C4 C5 C8 119.95(18) . . ?
O5 C8 O6 123.32(18) . . ?
O5 C8 C5 119.19(19) . . ?
O6 C8 C5 117.49(19) . . ?
C3 C2 C7 118.64(17) . . ?
C3 C2 C1 121.09(17) . . ?
C7 C2 C1 120.27(17) . . ?
C5 C6 C7 119.98(19) . . ?
C4 C3 C2 120.72(19) . . ?
C6 C7 C2 120.99(19) . . ?
C3 C4 C5 120.39(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ca1 P1 O1 -131.50(7) . . . 1_455 ?
O1 Ca1 P1 O1 48.50(7) 2_566 . . 1_455 ?
O4 Ca1 P1 O1 138.56(6) 2_566 . . 1_455 ?
O4 Ca1 P1 O1 -41.44(7) . . . 1_455 ?
O2 Ca1 P1 O1 -22.38(10) 2_566 . . 1_455 ?
O2 Ca1 P1 O1 157.63(10) . . . 1_455 ?
P1 Ca1 P1 O1 21(26) 2_566 . . 1_455 ?
P1 Ca1 P1 O1 -149.87(5) 1_655 . . 1_455 ?
P1 Ca1 P1 O1 30.13(5) 2_466 . . 1_455 ?
O1 Ca1 P1 O2 70.87(9) . . . . ?
O1 Ca1 P1 O2 -109.13(9) 2_566 . . . ?
O4 Ca1 P1 O2 -19.07(9) 2_566 . . . ?
O4 Ca1 P1 O2 160.93(9) . . . . ?
O2 Ca1 P1 O2 179.998(1) 2_566 . . . ?
P1 Ca1 P1 O2 -137(26) 2_566 . . . ?
P1 Ca1 P1 O2 52.51(8) 1_655 . . . ?
P1 Ca1 P1 O2 -127.49(8) 2_466 . . . ?
O1 Ca1 P1 O3 122.29(9) . . . . ?
O1 Ca1 P1 O3 -57.71(9) 2_566 . . . ?
O4 Ca1 P1 O3 32.36(9) 2_566 . . . ?
O4 Ca1 P1 O3 -147.64(9) . . . . ?
O2 Ca1 P1 O3 -128.58(11) 2_566 . . . ?
O2 Ca1 P1 O3 51.42(11) . . . . ?
P1 Ca1 P1 O3 -86(26) 2_566 . . . ?
P1 Ca1 P1 O3 103.93(8) 1_655 . . . ?
P1 Ca1 P1 O3 -76.07(8) 2_466 . . . ?
O1 Ca1 P1 C1 -22.25(7) . . . . ?
O1 Ca1 P1 C1 157.75(7) 2_566 . . . ?
O4 Ca1 P1 C1 -112.19(8) 2_566 . . . ?
O4 Ca1 P1 C1 67.81(8) . . . . ?
O2 Ca1 P1 C1 86.88(11) 2_566 . . . ?
O2 Ca1 P1 C1 -93.12(10) . . . . ?
P1 Ca1 P1 C1 130(26) 2_566 . . . ?
P1 Ca1 P1 C1 -40.62(7) 1_655 . . . ?
P1 Ca1 P1 C1 139.38(7) 2_466 . . . ?
O1 Ca1 P1 Ca1 -161.63(3) . . . 1_455 ?
O1 Ca1 P1 Ca1 18.37(3) 2_566 . . 1_455 ?
O4 Ca1 P1 Ca1 108.43(5) 2_566 . . 1_455 ?
O4 Ca1 P1 Ca1 -71.57(5) . . . 1_455 ?
O2 Ca1 P1 Ca1 -52.51(8) 2_566 . . 1_455 ?
O2 Ca1 P1 Ca1 127.49(8) . . . 1_455 ?
P1 Ca1 P1 Ca1 -10(26) 2_566 . . 1_455 ?
P1 Ca1 P1 Ca1 180.0 1_655 . . 1_455 ?
P1 Ca1 P1 Ca1 0.0 2_466 . . 1_455 ?
O1 Ca1 O1 P1 101(72) 2_566 . . 1_655 ?
O4 Ca1 O1 P1 35.77(9) 2_566 . . 1_655 ?
O4 Ca1 O1 P1 -144.23(9) . . . 1_655 ?
O2 Ca1 O1 P1 130.52(9) 2_566 . . 1_655 ?
O2 Ca1 O1 P1 -49.48(9) . . . 1_655 ?
P1 Ca1 O1 P1 -71.90(9) . . . 1_655 ?
P1 Ca1 O1 P1 108.10(9) 2_566 . . 1_655 ?
P1 Ca1 O1 P1 180.0 2_466 . . 1_655 ?
O1 P1 O2 Ca1 -24.04(10) 1_455 . . . ?
O3 P1 O2 Ca1 -146.90(7) . . . . ?
C1 P1 O2 Ca1 99.85(9) . . . . ?
Ca1 P1 O2 Ca1 -57.16(7) 1_455 . . . ?
O1 Ca1 O2 P1 -108.46(8) . . . . ?
O1 Ca1 O2 P1 71.54(8) 2_566 . . . ?
O4 Ca1 O2 P1 161.80(8) 2_566 . . . ?
O4 Ca1 O2 P1 -18.20(8) . . . . ?
O2 Ca1 O2 P1 -66(16) 2_566 . . . ?
P1 Ca1 O2 P1 180.0 2_566 . . . ?
P1 Ca1 O2 P1 -123.77(8) 1_655 . . . ?
P1 Ca1 O2 P1 56.23(8) 2_466 . . . ?
O1 P1 C1 C2 -57.73(18) 1_455 . . . ?
O2 P1 C1 C2 177.02(15) . . . . ?
O3 P1 C1 C2 62.03(17) . . . . ?
Ca1 P1 C1 C2 -141.53(14) . . . . ?
Ca1 P1 C1 C2 -36.1(2) 1_455 . . . ?
C6 C5 C8 O5 -177.8(2) . . . . ?
C4 C5 C8 O5 2.2(3) . . . . ?
C6 C5 C8 O6 2.0(3) . . . . ?
C4 C5 C8 O6 -178.0(2) . . . . ?
P1 C1 C2 C3 80.9(2) . . . . ?
P1 C1 C2 C7 -99.9(2) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C8 C5 C6 C7 179.3(2) . . . . ?
C7 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C3 C2 C7 C6 1.0(3) . . . . ?
C1 C2 C7 C6 -178.3(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C8 C5 C4 C3 -179.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.22
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 961688'
#######################################################################
#
#                 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_c:\einkris\nil6_ipds2\absc\nil6a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 bis(\m~2~-4-(Phosphatomethyl)benzoic acid)-tetraaqua-nickel
;
_chemical_formula_moiety         'C16 H24 Ni O14 P2'
_chemical_formula_sum            'C16 H24 Ni O14 P2'
_chemical_formula_weight         561.00

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'
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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   4.7713(10)
_cell_length_b                   6.8621(14)
_cell_length_c                   16.598(3)
_cell_angle_alpha                83.42(3)
_cell_angle_beta                 89.71(3)
_cell_angle_gamma                83.50(3)
_cell_volume                     536.36(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            'light green'
_exptl_crystal_size_max          0.1682
_exptl_crystal_size_mid          0.1136
_exptl_crystal_size_min          0.0822
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             290
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7625
_exptl_absorpt_correction_T_max  0.9005
_exptl_absorpt_process_details   'X-Shape and X-Red32 (Stoe, 2008)'

_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  'Stoe IPSD-2'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2458
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.94
_reflns_number_total             2458
_reflns_number_gt                2083
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (Stoe, 2008)'
_computing_cell_refinement       'X-Area (Stoe, 2008)'
_computing_data_reduction        'X-Area (Stoe, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
XP in SHELXTL (Sheldrick, 2008) 
;
_computing_publication_material  'XCIF in SHELXTL (Sheldrick, 2008)'

_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^)+(0.0000P)^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         2458
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0429
_refine_ls_wR_factor_gt          0.0427
_refine_ls_goodness_of_fit_ref   2.762
_refine_ls_restrained_S_all      2.762
_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 0.5000 0.5000 0.01830(10) Uani 1 2 d S . .
P1 P 0.34444(9) 0.76653(6) 0.64732(3) 0.01885(11) Uani 1 1 d . . .
O1 O 0.2562(2) 0.63184(17) 0.58896(7) 0.0228(3) Uani 1 1 d . . .
O2 O 0.0850(3) 0.91035(18) 0.66907(8) 0.0299(3) Uani 1 1 d . . .
H1 H -0.0722 0.8957 0.6527 0.036 Uiso 1 1 d R . .
O3 O 0.5741(3) 0.88994(17) 0.61515(7) 0.0233(3) Uani 1 1 d . . .
O4 O -0.4062(4) 0.2295(2) 0.98818(9) 0.0463(4) Uani 1 1 d . . .
O5 O -0.2881(4) -0.0172(2) 0.91411(11) 0.0528(5) Uani 1 1 d . . .
H2 H -0.3975 -0.0757 0.9435 0.082(11) Uiso 1 1 d R . .
O6 O 0.3288(3) 0.23525(17) 0.53114(8) 0.0240(3) Uani 1 1 d . . .
H3 H 0.3440 0.1921 0.4871 0.029 Uiso 1 1 d R . .
H4 H 0.4042 0.1467 0.5640 0.029 Uiso 1 1 d R . .
O7 O 0.1832(3) 0.58852(18) 0.41627(8) 0.0261(3) Uani 1 1 d . . .
H5 H 0.0764 0.6784 0.4320 0.031 Uiso 1 1 d R . .
H6 H 0.0810 0.4996 0.4202 0.031 Uiso 1 1 d R . .
C1 C 0.4736(4) 0.6338(3) 0.74137(12) 0.0291(4) Uani 1 1 d . . .
H1B H 0.6409 0.5469 0.7304 0.035 Uiso 1 1 calc R . .
H1A H 0.5307 0.7279 0.7757 0.035 Uiso 1 1 calc R . .
C2 C 0.2690(4) 0.5113(3) 0.78825(11) 0.0271(4) Uani 1 1 d . . .
C3 C 0.2329(5) 0.3235(3) 0.76917(12) 0.0335(5) Uani 1 1 d . . .
H3A H 0.3289 0.2743 0.7256 0.040 Uiso 1 1 calc R . .
C4 C 0.0546(5) 0.2094(3) 0.81474(12) 0.0328(5) Uani 1 1 d . . .
H4A H 0.0334 0.0834 0.8020 0.039 Uiso 1 1 calc R . .
C5 C -0.0924(4) 0.2816(3) 0.87924(12) 0.0281(4) Uani 1 1 d . . .
C6 C -0.0632(4) 0.4714(3) 0.89705(12) 0.0301(4) Uani 1 1 d . . .
H6A H -0.1645 0.5221 0.9395 0.036 Uiso 1 1 calc R . .
C7 C 0.1161(4) 0.5851(3) 0.85183(11) 0.0288(4) Uani 1 1 d . . .
H7A H 0.1346 0.7119 0.8641 0.035 Uiso 1 1 calc R . .
C8 C -0.2737(4) 0.1584(3) 0.93086(12) 0.0307(4) Uani 1 1 d . . .

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 0.01676(19) 0.01613(18) 0.0219(2) -0.00215(14) 0.00032(15) -0.00159(14)
P1 0.0158(2) 0.0192(2) 0.0216(3) -0.00275(18) -0.00104(19) -0.00174(19)
O1 0.0212(6) 0.0226(6) 0.0258(7) -0.0077(5) 0.0022(5) -0.0034(5)
O2 0.0175(7) 0.0328(7) 0.0414(8) -0.0164(6) -0.0030(6) 0.0008(5)
O3 0.0212(6) 0.0219(6) 0.0271(7) -0.0025(5) -0.0037(5) -0.0035(5)
O4 0.0570(10) 0.0428(9) 0.0415(9) -0.0073(7) 0.0175(8) -0.0141(8)
O5 0.0680(12) 0.0299(8) 0.0620(11) -0.0056(7) 0.0317(9) -0.0133(8)
O6 0.0252(7) 0.0191(6) 0.0270(7) 0.0004(5) -0.0002(5) -0.0024(5)
O7 0.0188(6) 0.0243(6) 0.0345(7) -0.0026(5) -0.0017(5) -0.0005(5)
C1 0.0234(10) 0.0333(10) 0.0300(11) -0.0005(8) -0.0045(8) -0.0043(8)
C2 0.0274(10) 0.0285(9) 0.0241(10) 0.0037(7) -0.0039(8) -0.0038(8)
C3 0.0405(12) 0.0305(10) 0.0292(11) -0.0057(8) 0.0083(9) -0.0010(9)
C4 0.0417(12) 0.0237(9) 0.0334(11) -0.0036(8) 0.0052(9) -0.0048(8)
C5 0.0300(10) 0.0260(9) 0.0268(10) 0.0016(7) 0.0005(8) -0.0017(8)
C6 0.0349(11) 0.0310(10) 0.0241(10) -0.0039(7) 0.0029(8) -0.0014(8)
C7 0.0337(11) 0.0264(9) 0.0266(10) -0.0027(7) -0.0019(8) -0.0048(8)
C8 0.0335(11) 0.0290(10) 0.0286(10) -0.0003(8) 0.0031(8) -0.0017(8)

_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 2.0507(14) 2_666 ?
Ni1 O7 2.0507(14) . ?
Ni1 O6 2.0860(13) . ?
Ni1 O6 2.0860(13) 2_666 ?
Ni1 O1 2.0983(13) . ?
Ni1 O1 2.0984(13) 2_666 ?
P1 O1 1.5057(13) . ?
P1 O3 1.5179(13) . ?
P1 O2 1.5611(14) . ?
P1 C1 1.790(2) . ?
O2 H1 0.8200 . ?
O4 C8 1.254(2) . ?
O5 C8 1.277(2) . ?
O5 H2 0.8200 . ?
O6 H3 0.8200 . ?
O6 H4 0.8199 . ?
O7 H5 0.8200 . ?
O7 H6 0.8200 . ?
C1 C2 1.514(3) . ?
C1 H1B 0.9700 . ?
C1 H1A 0.9700 . ?
C2 C7 1.390(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(3) . ?
C5 C8 1.480(3) . ?
C6 C7 1.384(3) . ?
C6 H6A 0.9300 . ?
C7 H7A 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
O7 Ni1 O7 180.00(5) 2_666 . ?
O7 Ni1 O6 89.93(6) 2_666 . ?
O7 Ni1 O6 90.07(6) . . ?
O7 Ni1 O6 90.07(6) 2_666 2_666 ?
O7 Ni1 O6 89.93(5) . 2_666 ?
O6 Ni1 O6 180.0 . 2_666 ?
O7 Ni1 O1 89.69(5) 2_666 . ?
O7 Ni1 O1 90.31(5) . . ?
O6 Ni1 O1 90.49(5) . . ?
O6 Ni1 O1 89.51(5) 2_666 . ?
O7 Ni1 O1 90.31(5) 2_666 2_666 ?
O7 Ni1 O1 89.69(5) . 2_666 ?
O6 Ni1 O1 89.51(5) . 2_666 ?
O6 Ni1 O1 90.49(5) 2_666 2_666 ?
O1 Ni1 O1 180.00(6) . 2_666 ?
O1 P1 O3 113.84(7) . . ?
O1 P1 O2 109.92(8) . . ?
O3 P1 O2 107.94(7) . . ?
O1 P1 C1 112.27(8) . . ?
O3 P1 C1 106.45(8) . . ?
O2 P1 C1 106.03(9) . . ?
P1 O1 Ni1 128.17(7) . . ?
P1 O2 H1 119.3 . . ?
C8 O5 H2 112.7 . . ?
Ni1 O6 H3 98.5 . . ?
Ni1 O6 H4 122.7 . . ?
H3 O6 H4 105.4 . . ?
Ni1 O7 H5 109.6 . . ?
Ni1 O7 H6 105.6 . . ?
H5 O7 H6 100.7 . . ?
C2 C1 P1 115.89(14) . . ?
C2 C1 H1B 108.3 . . ?
P1 C1 H1B 108.3 . . ?
C2 C1 H1A 108.3 . . ?
P1 C1 H1A 108.3 . . ?
H1B C1 H1A 107.4 . . ?
C7 C2 C3 119.02(17) . . ?
C7 C2 C1 120.12(17) . . ?
C3 C2 C1 120.85(18) . . ?
C4 C3 C2 120.33(19) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C5 C4 C3 120.47(19) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.39(17) . . ?
C4 C5 C8 121.17(18) . . ?
C6 C5 C8 119.42(17) . . ?
C7 C6 C5 120.17(18) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C2 120.57(18) . . ?
C6 C7 H7A 119.7 . . ?
C2 C7 H7A 119.7 . . ?
O4 C8 O5 123.02(18) . . ?
O4 C8 C5 119.42(17) . . ?
O5 C8 C5 117.56(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 O1 Ni1 29.54(11) . . . . ?
O2 P1 O1 Ni1 150.76(8) . . . . ?
C1 P1 O1 Ni1 -91.48(11) . . . . ?
O7 Ni1 O1 P1 47.81(9) 2_666 . . . ?
O7 Ni1 O1 P1 -132.19(9) . . . . ?
O6 Ni1 O1 P1 137.74(10) . . . . ?
O6 Ni1 O1 P1 -42.26(10) 2_666 . . . ?
O1 Ni1 O1 P1 -132(40) 2_666 . . . ?
O1 P1 C1 C2 -59.35(17) . . . . ?
O3 P1 C1 C2 175.46(14) . . . . ?
O2 P1 C1 C2 60.70(16) . . . . ?
P1 C1 C2 C7 -98.3(2) . . . . ?
P1 C1 C2 C3 82.3(2) . . . . ?
C7 C2 C3 C4 -2.2(3) . . . . ?
C1 C2 C3 C4 177.1(2) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 C8 -177.2(2) . . . . ?
C4 C5 C6 C7 -1.5(3) . . . . ?
C8 C5 C6 C7 176.86(19) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C3 C2 C7 C6 1.9(3) . . . . ?
C1 C2 C7 C6 -177.50(17) . . . . ?
C4 C5 C8 O4 -179.2(2) . . . . ?
C6 C5 C8 O4 2.5(3) . . . . ?
C4 C5 C8 O5 0.5(3) . . . . ?
C6 C5 C8 O5 -177.83(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 961689'