# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Gamez, Patrick'
_publ_contact_author_email       patrick.gamez@qi.ub.es

_publ_section_title              
;
Supramolecular Assemblies Involving Anion[?]p and Lone
Pair[?]p Interactions: Experimental Observation and
Theoretical Analysis
;
_publ_author_name                P.Gamez

# Attachment 'Compound-1.cif'

data_m12m
_database_code_depnum_ccdc_archive 'CCDC 781939'
#TrackingRef 'Compound-1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H36 Cl2 N8 Ni O18'
_chemical_formula_weight         878.24

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'
Cl Cl 0.1484 0.1585 '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

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

_cell_length_a                   7.0471(12)
_cell_length_b                   11.314(2)
_cell_length_c                   11.747(2)
_cell_angle_alpha                86.321(3)
_cell_angle_beta                 83.933(3)
_cell_angle_gamma                72.684(3)
_cell_volume                     888.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    925
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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            7093
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         26.38
_reflns_number_total             3571
_reflns_number_gt                2921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0308P)^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         3571
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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 1.0000 0.5000 1.0000 0.01213(11) Uani 1 2 d S . .
Cl1 Cl 0.91385(8) 0.85865(5) 0.67430(4) 0.01751(14) Uani 1 1 d . . .
O1 O 0.7230(2) 0.61745(13) 1.02677(11) 0.0144(3) Uani 1 1 d . . .
O2 O 0.4032(2) 0.68428(13) 0.99818(12) 0.0181(3) Uani 1 1 d . . .
O3 O 0.7621(2) 0.44731(13) 0.70825(12) 0.0180(3) Uani 1 1 d . . .
O4 O 0.9238(2) 0.43538(13) 0.86201(12) 0.0146(3) Uani 1 1 d . . .
O5 O 1.1125(3) 0.62816(15) 0.89963(14) 0.0179(4) Uani 1 1 d . . .
H1O5 H 1.193(4) 0.648(3) 0.926(2) 0.044(10) Uiso 1 1 d . . .
H2O5 H 1.041(4) 0.689(2) 0.869(2) 0.031(8) Uiso 1 1 d . . .
O6 O 0.8609(2) 0.84257(14) 0.79558(13) 0.0241(4) Uani 1 1 d . . .
O7 O 0.8846(2) 0.98737(14) 0.64723(14) 0.0277(4) Uani 1 1 d . . .
O8 O 0.7860(3) 0.81409(17) 0.61129(14) 0.0355(5) Uani 1 1 d . . .
O9 O 1.1174(2) 0.78957(15) 0.64645(14) 0.0310(4) Uani 1 1 d . . .
N1 N 0.6126(3) 0.1997(2) 0.78161(18) 0.0201(4) Uani 1 1 d . . .
H1N1 H 0.611(3) 0.224(2) 0.842(2) 0.019(7) Uiso 1 1 d . . .
H2N1 H 0.704(4) 0.134(2) 0.762(2) 0.031(7) Uiso 1 1 d . . .
N2 N 0.3708(3) 0.37954(16) 0.73591(16) 0.0155(4) Uani 1 1 d . . .
H1N2 H 0.348(3) 0.388(2) 0.808(2) 0.020(6) Uiso 1 1 d . . .
N3 N 0.0603(3) 0.23116(19) 0.63731(18) 0.0193(4) Uani 1 1 d . . .
H1N3 H 0.093(4) 0.216(2) 0.565(2) 0.035(8) Uiso 1 1 d . . .
H2N3 H -0.021(4) 0.299(3) 0.654(2) 0.034(8) Uiso 1 1 d . . .
N4 N 0.1072(3) 0.18575(18) 0.82781(16) 0.0177(4) Uani 1 1 d . . .
H1N4 H 0.042(4) 0.257(2) 0.841(2) 0.026(7) Uiso 1 1 d . . .
C1 C 0.5814(3) 0.63764(18) 0.96222(18) 0.0136(4) Uani 1 1 d . . .
C2 C 0.6313(3) 0.6102(2) 0.83638(18) 0.0154(5) Uani 1 1 d . . .
H2 H 0.516(3) 0.6190(18) 0.8048(17) 0.011(5) Uiso 1 1 d . . .
H2B H 0.688(3) 0.673(2) 0.8020(19) 0.022(6) Uiso 1 1 d . . .
C3 C 0.7813(3) 0.48842(19) 0.79956(17) 0.0137(4) Uani 1 1 d . . .
C4 C 0.1469(3) 0.1523(2) 0.71770(19) 0.0171(5) Uani 1 1 d . . .
C5 C 0.2800(3) 0.0336(2) 0.6958(2) 0.0226(5) Uani 1 1 d . . .
H5 H 0.308(3) 0.0131(19) 0.6236(19) 0.013(6) Uiso 1 1 d . . .
C6 C 0.3551(4) -0.0428(2) 0.7834(2) 0.0271(6) Uani 1 1 d . . .
H6 H 0.434(4) -0.120(2) 0.769(2) 0.030(7) Uiso 1 1 d . . .
C7 C 0.3050(4) -0.0059(2) 0.8970(2) 0.0288(6) Uani 1 1 d . . .
H7 H 0.348(4) -0.055(2) 0.962(2) 0.034(7) Uiso 1 1 d . . .
C8 C 0.1837(4) 0.1094(2) 0.9159(2) 0.0246(5) Uani 1 1 d . . .
H8 H 0.143(4) 0.139(2) 0.985(2) 0.028(7) Uiso 1 1 d . . .
C9 C 0.5158(3) 0.2768(2) 0.70206(18) 0.0156(5) Uani 1 1 d . . .
C10 C 0.5529(3) 0.2562(2) 0.58350(18) 0.0179(5) Uani 1 1 d . . .
H10 H 0.652(3) 0.185(2) 0.5596(18) 0.017(6) Uiso 1 1 d . . .
C11 C 0.4471(3) 0.3405(2) 0.5089(2) 0.0206(5) Uani 1 1 d . . .
H11 H 0.465(3) 0.336(2) 0.428(2) 0.027(7) Uiso 1 1 d . . .
C12 C 0.3005(3) 0.4479(2) 0.5476(2) 0.0201(5) Uani 1 1 d . . .
H12 H 0.232(3) 0.508(2) 0.4967(19) 0.018(6) Uiso 1 1 d . . .
C13 C 0.2668(3) 0.4644(2) 0.6616(2) 0.0176(5) Uani 1 1 d . . .
H13 H 0.187(3) 0.530(2) 0.6945(18) 0.015(6) Uiso 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 0.0090(2) 0.0158(2) 0.0122(2) -0.00261(16) -0.00231(15) -0.00370(15)
Cl1 0.0183(3) 0.0180(3) 0.0169(3) -0.0031(2) -0.0002(2) -0.0063(2)
O1 0.0111(7) 0.0187(8) 0.0138(8) -0.0029(6) -0.0036(6) -0.0035(6)
O2 0.0099(8) 0.0248(9) 0.0193(8) -0.0065(7) -0.0008(6) -0.0036(6)
O3 0.0170(8) 0.0234(8) 0.0147(8) -0.0048(7) -0.0043(6) -0.0056(7)
O4 0.0120(8) 0.0163(8) 0.0156(8) -0.0025(6) -0.0037(6) -0.0034(6)
O5 0.0157(9) 0.0209(9) 0.0195(9) 0.0024(7) -0.0071(7) -0.0079(7)
O6 0.0224(9) 0.0307(9) 0.0164(8) -0.0005(7) -0.0020(7) -0.0036(7)
O7 0.0251(9) 0.0186(8) 0.0362(10) 0.0032(7) 0.0000(8) -0.0036(7)
O8 0.0404(11) 0.0550(12) 0.0241(10) -0.0137(8) -0.0014(8) -0.0318(10)
O9 0.0236(9) 0.0239(9) 0.0384(11) -0.0050(8) 0.0090(8) 0.0005(7)
N1 0.0214(11) 0.0228(11) 0.0156(11) -0.0040(9) -0.0027(9) -0.0045(9)
N2 0.0157(10) 0.0196(10) 0.0123(10) -0.0021(8) -0.0002(8) -0.0070(8)
N3 0.0194(11) 0.0199(11) 0.0178(11) -0.0056(9) -0.0001(9) -0.0041(9)
N4 0.0171(10) 0.0154(10) 0.0203(11) -0.0025(8) -0.0014(8) -0.0040(8)
C1 0.0127(11) 0.0108(10) 0.0188(11) -0.0004(9) -0.0033(9) -0.0051(8)
C2 0.0108(11) 0.0193(12) 0.0164(12) -0.0004(9) -0.0044(9) -0.0039(9)
C3 0.0120(11) 0.0174(11) 0.0142(11) 0.0005(9) -0.0009(9) -0.0082(9)
C4 0.0142(11) 0.0178(11) 0.0231(12) -0.0031(10) -0.0016(9) -0.0099(9)
C5 0.0177(12) 0.0230(13) 0.0284(14) -0.0107(11) 0.0008(11) -0.0069(10)
C6 0.0199(13) 0.0177(13) 0.0437(17) -0.0039(12) -0.0071(12) -0.0034(10)
C7 0.0310(14) 0.0224(13) 0.0337(15) 0.0043(12) -0.0109(12) -0.0074(11)
C8 0.0279(14) 0.0252(13) 0.0217(14) -0.0003(11) -0.0045(11) -0.0086(11)
C9 0.0126(11) 0.0183(11) 0.0193(12) -0.0031(9) -0.0007(9) -0.0096(9)
C10 0.0166(12) 0.0216(12) 0.0183(12) -0.0060(10) 0.0017(9) -0.0099(10)
C11 0.0221(13) 0.0295(13) 0.0156(12) -0.0031(10) 0.0011(10) -0.0162(10)
C12 0.0201(12) 0.0250(13) 0.0180(12) 0.0036(10) -0.0036(10) -0.0115(10)
C13 0.0145(11) 0.0179(12) 0.0225(13) -0.0022(10) -0.0009(10) -0.0077(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
Ni1 O4 2.0050(14) 2_767 ?
Ni1 O4 2.0050(14) . ?
Ni1 O1 2.0137(14) 2_767 ?
Ni1 O1 2.0137(14) . ?
Ni1 O5 2.0949(16) 2_767 ?
Ni1 O5 2.0949(16) . ?
Cl1 O7 1.4284(16) . ?
Cl1 O9 1.4288(16) . ?
Cl1 O8 1.4398(16) . ?
Cl1 O6 1.4482(16) . ?
O1 C1 1.275(2) . ?
O2 C1 1.247(2) . ?
O3 C3 1.232(2) . ?
O4 C3 1.284(2) . ?
O5 H1O5 0.77(3) . ?
O5 H2O5 0.81(3) . ?
N1 C9 1.332(3) . ?
N1 H1N1 0.77(2) . ?
N1 H2N1 0.85(3) . ?
N2 C9 1.349(3) . ?
N2 C13 1.353(3) . ?
N2 H1N2 0.86(2) . ?
N3 C4 1.323(3) . ?
N3 H1N3 0.87(3) . ?
N3 H2N3 0.83(3) . ?
N4 C4 1.348(3) . ?
N4 C8 1.354(3) . ?
N4 H1N4 0.81(2) . ?
C1 C2 1.513(3) . ?
C2 C3 1.522(3) . ?
C2 H2 0.90(2) . ?
C2 H2B 0.97(2) . ?
C4 C5 1.412(3) . ?
C5 C6 1.347(3) . ?
C5 H5 0.88(2) . ?
C6 C7 1.402(4) . ?
C6 H6 0.90(2) . ?
C7 C8 1.348(3) . ?
C7 H7 0.93(2) . ?
C8 H8 0.89(2) . ?
C9 C10 1.411(3) . ?
C10 C11 1.357(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.405(3) . ?
C11 H11 0.95(2) . ?
C12 C13 1.350(3) . ?
C12 H12 0.93(2) . ?
C13 H13 0.87(2) . ?

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 O4 180.00(7) 2_767 . ?
O4 Ni1 O1 90.82(5) 2_767 2_767 ?
O4 Ni1 O1 89.18(5) . 2_767 ?
O4 Ni1 O1 89.18(5) 2_767 . ?
O4 Ni1 O1 90.82(5) . . ?
O1 Ni1 O1 180.00(5) 2_767 . ?
O4 Ni1 O5 91.95(6) 2_767 2_767 ?
O4 Ni1 O5 88.05(6) . 2_767 ?
O1 Ni1 O5 94.38(6) 2_767 2_767 ?
O1 Ni1 O5 85.62(6) . 2_767 ?
O4 Ni1 O5 88.05(6) 2_767 . ?
O4 Ni1 O5 91.95(6) . . ?
O1 Ni1 O5 85.62(6) 2_767 . ?
O1 Ni1 O5 94.38(6) . . ?
O5 Ni1 O5 180.0 2_767 . ?
O7 Cl1 O9 110.54(10) . . ?
O7 Cl1 O8 109.46(10) . . ?
O9 Cl1 O8 109.74(10) . . ?
O7 Cl1 O6 109.00(10) . . ?
O9 Cl1 O6 109.45(10) . . ?
O8 Cl1 O6 108.62(10) . . ?
C1 O1 Ni1 127.11(13) . . ?
C3 O4 Ni1 128.38(13) . . ?
Ni1 O5 H1O5 114(2) . . ?
Ni1 O5 H2O5 122.5(19) . . ?
H1O5 O5 H2O5 108(3) . . ?
C9 N1 H1N1 119.0(18) . . ?
C9 N1 H2N1 120.3(17) . . ?
H1N1 N1 H2N1 118(2) . . ?
C9 N2 C13 123.06(19) . . ?
C9 N2 H1N2 115.8(15) . . ?
C13 N2 H1N2 121.2(15) . . ?
C4 N3 H1N3 121.4(17) . . ?
C4 N3 H2N3 121.0(17) . . ?
H1N3 N3 H2N3 117(2) . . ?
C4 N4 C8 122.9(2) . . ?
C4 N4 H1N4 117.8(17) . . ?
C8 N4 H1N4 119.1(17) . . ?
O2 C1 O1 122.22(19) . . ?
O2 C1 C2 118.66(18) . . ?
O1 C1 C2 119.05(18) . . ?
C1 C2 C3 120.11(18) . . ?
C1 C2 H2 108.3(13) . . ?
C3 C2 H2 108.9(13) . . ?
C1 C2 H2B 106.5(13) . . ?
C3 C2 H2B 104.8(13) . . ?
H2 C2 H2B 107.6(18) . . ?
O3 C3 O4 123.11(19) . . ?
O3 C3 C2 117.47(18) . . ?
O4 C3 C2 119.39(18) . . ?
N3 C4 N4 118.9(2) . . ?
N3 C4 C5 124.0(2) . . ?
N4 C4 C5 117.1(2) . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 123.3(14) . . ?
C4 C5 H5 116.7(14) . . ?
C5 C6 C7 121.0(2) . . ?
C5 C6 H6 119.6(15) . . ?
C7 C6 H6 119.3(15) . . ?
C8 C7 C6 118.1(2) . . ?
C8 C7 H7 116.5(15) . . ?
C6 C7 H7 125.4(15) . . ?
C7 C8 N4 120.8(2) . . ?
C7 C8 H8 123.3(16) . . ?
N4 C8 H8 115.8(16) . . ?
N1 C9 N2 118.7(2) . . ?
N1 C9 C10 123.8(2) . . ?
N2 C9 C10 117.49(19) . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 122.5(13) . . ?
C9 C10 H10 118.0(13) . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 125.3(14) . . ?
C12 C11 H11 113.5(14) . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 H12 120.5(14) . . ?
C11 C12 H12 121.5(14) . . ?
C12 C13 N2 120.7(2) . . ?
C12 C13 H13 125.5(14) . . ?
N2 C13 H13 113.6(14) . . ?

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
O4 Ni1 O1 C1 173.84(16) 2_767 . . . ?
O4 Ni1 O1 C1 -6.16(16) . . . . ?
O1 Ni1 O1 C1 -1(37) 2_767 . . . ?
O5 Ni1 O1 C1 -94.14(16) 2_767 . . . ?
O5 Ni1 O1 C1 85.86(16) . . . . ?
O4 Ni1 O4 C3 98(100) 2_767 . . . ?
O1 Ni1 O4 C3 -157.51(17) 2_767 . . . ?
O1 Ni1 O4 C3 22.49(17) . . . . ?
O5 Ni1 O4 C3 108.08(17) 2_767 . . . ?
O5 Ni1 O4 C3 -71.92(17) . . . . ?
Ni1 O1 C1 O2 159.95(15) . . . . ?
Ni1 O1 C1 C2 -23.2(3) . . . . ?
O2 C1 C2 C3 -136.6(2) . . . . ?
O1 C1 C2 C3 46.4(3) . . . . ?
Ni1 O4 C3 O3 170.70(14) . . . . ?
Ni1 O4 C3 C2 -7.2(3) . . . . ?
C1 C2 C3 O3 151.88(19) . . . . ?
C1 C2 C3 O4 -30.1(3) . . . . ?
C8 N4 C4 N3 177.7(2) . . . . ?
C8 N4 C4 C5 -2.2(3) . . . . ?
N3 C4 C5 C6 -177.3(2) . . . . ?
N4 C4 C5 C6 2.6(3) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C6 C7 C8 N4 2.2(4) . . . . ?
C4 N4 C8 C7 -0.2(4) . . . . ?
C13 N2 C9 N1 178.7(2) . . . . ?
C13 N2 C9 C10 -2.5(3) . . . . ?
N1 C9 C10 C11 -179.7(2) . . . . ?
N2 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 N2 -0.4(3) . . . . ?
C9 N2 C13 C12 1.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1O5 O2 0.77(3) 1.94(3) 2.704(2) 176(3) 1_655
N4 H1N4 O4 0.81(2) 1.96(2) 2.770(2) 171(2) 1_455
N1 H1N1 O2 0.77(2) 2.19(2) 2.952(3) 173(2) 2_667
N3 H2N3 O3 0.83(3) 1.99(3) 2.815(3) 172(3) 1_455
N2 H1N2 O1 0.86(2) 1.95(2) 2.796(2) 170(2) 2_667
N1 H2N1 O7 0.85(3) 2.20(3) 3.007(3) 157(2) 1_545
O5 H2O5 O6 0.81(3) 2.02(3) 2.835(2) 179(3) .
O5 H2O5 Cl1 0.81(3) 2.92(3) 3.6730(19) 154(2) .
N3 H1N3 O8 0.87(3) 2.16(3) 3.026(3) 171(2) 2_666

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.38
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.067

# Attachment 'Compound-2.cif'

data_m15a
_database_code_depnum_ccdc_archive 'CCDC 781940'
#TrackingRef 'Compound-2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
#------------------------------------------------------------------------------

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C6 H8 Ni O10, 4(C5 H7 N2), 2(F6 P)'
_chemical_formula_sum            'C26 H36 F12 N8 Ni O10 P2'
_chemical_formula_weight         969.28

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'
F F 0.0171 0.0103 '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_space_group_name_Hall  -P1

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

_cell_length_a                   7.0459(10)
_cell_length_b                   11.8570(17)
_cell_length_c                   11.8501(17)
_cell_angle_alpha                84.482(2)
_cell_angle_beta                 84.484(2)
_cell_angle_gamma                72.251(2)
_cell_volume                     936.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    994
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.32
_exptl_crystal_description       plate
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_max          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             494
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         '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            7510
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3768
_reflns_number_gt                3573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0440P)^2^+0.4867P] 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         3768
_refine_ls_number_parameters     340
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 1.0000 0.5000 1.0000 0.01425(9) Uani 1 2 d S . .
O1 O 0.72119(16) 0.61256(10) 1.02385(9) 0.0190(2) Uani 1 1 d . . .
O2 O 0.39937(17) 0.67951(11) 0.99631(10) 0.0212(3) Uani 1 1 d . . .
O3 O 0.75062(17) 0.44712(11) 0.71594(9) 0.0210(2) Uani 1 1 d . . .
O4 O 0.92501(16) 0.44185(10) 0.86310(9) 0.0175(2) Uani 1 1 d . . .
O5 O 1.1113(2) 0.62437(12) 0.90111(11) 0.0253(3) Uani 1 1 d . . .
H1O5 H 1.192(4) 0.649(2) 0.926(2) 0.041(7) Uiso 1 1 d . . .
H2O5 H 1.055(3) 0.675(2) 0.859(2) 0.029(6) Uiso 1 1 d . . .
C1 C 0.5767(2) 0.63150(14) 0.96110(13) 0.0162(3) Uani 1 1 d . . .
C2 C 0.6171(2) 0.60293(15) 0.83716(14) 0.0191(3) Uani 1 1 d . . .
H2A H 0.661(3) 0.664(2) 0.7985(19) 0.030(5) Uiso 1 1 d . . .
H2B H 0.497(3) 0.6067(18) 0.8060(17) 0.026(5) Uiso 1 1 d . . .
C3 C 0.7739(2) 0.48850(14) 0.80349(13) 0.0157(3) Uani 1 1 d . . .
P1 P 0.89224(7) 0.85378(4) 0.66088(4) 0.02051(11) Uani 1 1 d . . .
F1 F 0.9879(2) 0.87987(12) 0.53877(10) 0.0504(4) Uani 1 1 d . . .
F2 F 0.67710(19) 0.89415(12) 0.61563(12) 0.0481(3) Uani 1 1 d . . .
F3 F 0.8010(2) 0.82557(14) 0.78626(10) 0.0515(4) Uani 1 1 d . . .
F4 F 1.10960(19) 0.81004(11) 0.70836(13) 0.0464(3) Uani 1 1 d . . .
F5 F 0.91755(18) 0.72052(10) 0.63220(11) 0.0383(3) Uani 1 1 d . . .
F6 F 0.86703(17) 0.98604(10) 0.69153(10) 0.0346(3) Uani 1 1 d . . .
N1 N 0.6004(2) 0.20404(13) 0.79607(13) 0.0213(3) Uani 1 1 d . . .
H1N1 H 0.599(3) 0.234(2) 0.858(2) 0.028(5) Uiso 1 1 d . . .
H2N1 H 0.691(3) 0.140(2) 0.7806(19) 0.028(5) Uiso 1 1 d . . .
N2 N 0.3657(2) 0.37730(12) 0.73773(12) 0.0180(3) Uani 1 1 d . . .
H1N2 H 0.344(3) 0.3898(17) 0.8019(18) 0.017(5) Uiso 1 1 d . . .
N3 N 0.0457(2) 0.23500(15) 0.66317(14) 0.0257(3) Uani 1 1 d . . .
H1N3 H 0.057(3) 0.207(2) 0.601(2) 0.035(6) Uiso 1 1 d . . .
H2N3 H -0.035(4) 0.304(2) 0.677(2) 0.038(6) Uiso 1 1 d . . .
N4 N 0.0967(2) 0.19976(13) 0.85373(13) 0.0225(3) Uani 1 1 d . . .
H1N4 H 0.036(3) 0.274(2) 0.8572(18) 0.030(6) Uiso 1 1 d . . .
C4 C 0.1267(2) 0.16018(15) 0.74821(15) 0.0222(3) Uani 1 1 d . . .
C5 C 0.2438(3) 0.04138(17) 0.73534(18) 0.0298(4) Uani 1 1 d . . .
H5 H 0.264(3) 0.015(2) 0.664(2) 0.032(6) Uiso 1 1 d . . .
C6 C 0.3139(3) -0.02957(17) 0.8283(2) 0.0356(5) Uani 1 1 d . . .
H6 H 0.386(4) -0.104(2) 0.821(2) 0.048(7) Uiso 1 1 d . . .
C7 C 0.2754(3) 0.01389(18) 0.93706(19) 0.0352(4) Uani 1 1 d . . .
H7 H 0.321(4) -0.035(2) 1.001(2) 0.045(7) Uiso 1 1 d . . .
C8 C 0.1694(3) 0.12934(17) 0.94702(17) 0.0294(4) Uani 1 1 d . . .
H8 H 0.143(3) 0.1658(19) 1.0154(19) 0.028(5) Uiso 1 1 d . . .
C9 C 0.5069(2) 0.27654(15) 0.71137(14) 0.0188(3) Uani 1 1 d . . .
C10 C 0.5447(3) 0.25155(17) 0.59588(15) 0.0239(4) Uani 1 1 d . . .
H10 H 0.639(3) 0.179(2) 0.5795(18) 0.029(5) Uiso 1 1 d . . .
C11 C 0.4436(3) 0.33203(18) 0.51578(15) 0.0279(4) Uani 1 1 d . . .
H11 H 0.464(3) 0.315(2) 0.439(2) 0.039(6) Uiso 1 1 d . . .
C12 C 0.3020(3) 0.43819(18) 0.54656(15) 0.0269(4) Uani 1 1 d . . .
H12 H 0.232(3) 0.496(2) 0.4953(19) 0.030(5) Uiso 1 1 d . . .
C13 C 0.2648(3) 0.45846(16) 0.65860(15) 0.0219(3) Uani 1 1 d . . .
H13 H 0.174(3) 0.5263(18) 0.6874(17) 0.021(5) Uiso 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 0.01221(15) 0.01879(15) 0.01231(15) -0.00144(10) -0.00213(10) -0.00497(11)
O1 0.0150(5) 0.0251(6) 0.0163(5) -0.0045(4) -0.0033(4) -0.0036(4)
O2 0.0146(6) 0.0283(6) 0.0207(6) -0.0059(5) -0.0017(4) -0.0048(5)
O3 0.0224(6) 0.0261(6) 0.0159(6) -0.0034(5) -0.0048(4) -0.0077(5)
O4 0.0164(5) 0.0206(5) 0.0157(5) -0.0029(4) -0.0036(4) -0.0045(4)
O5 0.0228(6) 0.0323(7) 0.0251(7) 0.0111(6) -0.0116(5) -0.0155(6)
C1 0.0155(7) 0.0162(7) 0.0177(7) -0.0001(6) -0.0025(6) -0.0060(6)
C2 0.0158(8) 0.0254(8) 0.0156(8) 0.0008(6) -0.0042(6) -0.0049(6)
C3 0.0148(7) 0.0201(8) 0.0138(7) 0.0005(6) 0.0000(5) -0.0084(6)
P1 0.0240(2) 0.0191(2) 0.0174(2) -0.00160(16) -0.00134(16) -0.00485(17)
F1 0.0802(10) 0.0481(8) 0.0284(6) -0.0105(6) 0.0204(6) -0.0323(7)
F2 0.0354(7) 0.0444(7) 0.0630(9) -0.0111(6) -0.0246(6) -0.0011(6)
F3 0.0733(10) 0.0690(9) 0.0239(6) -0.0036(6) 0.0096(6) -0.0424(8)
F4 0.0351(7) 0.0315(6) 0.0743(9) -0.0030(6) -0.0233(6) -0.0066(5)
F5 0.0423(7) 0.0220(5) 0.0530(8) -0.0078(5) -0.0062(6) -0.0107(5)
F6 0.0387(6) 0.0232(5) 0.0403(6) -0.0116(5) -0.0029(5) -0.0041(5)
N1 0.0214(7) 0.0210(7) 0.0201(7) -0.0048(6) -0.0006(6) -0.0037(6)
N2 0.0184(7) 0.0223(7) 0.0145(7) -0.0027(5) 0.0000(5) -0.0076(5)
N3 0.0255(8) 0.0306(8) 0.0216(8) -0.0075(7) -0.0009(6) -0.0079(7)
N4 0.0224(7) 0.0193(7) 0.0260(8) -0.0034(6) -0.0019(6) -0.0056(6)
C4 0.0168(8) 0.0256(8) 0.0276(9) -0.0061(7) 0.0001(6) -0.0108(7)
C5 0.0251(9) 0.0272(9) 0.0397(11) -0.0130(8) 0.0004(8) -0.0092(7)
C6 0.0290(10) 0.0200(9) 0.0570(13) -0.0056(9) -0.0052(9) -0.0046(8)
C7 0.0355(11) 0.0273(10) 0.0416(12) 0.0076(9) -0.0088(9) -0.0088(8)
C8 0.0316(10) 0.0298(9) 0.0266(9) -0.0002(8) -0.0029(8) -0.0094(8)
C9 0.0165(7) 0.0230(8) 0.0201(8) -0.0027(6) 0.0000(6) -0.0106(6)
C10 0.0232(8) 0.0290(9) 0.0215(8) -0.0077(7) 0.0022(7) -0.0101(7)
C11 0.0307(10) 0.0405(11) 0.0167(8) -0.0038(7) 0.0011(7) -0.0174(8)
C12 0.0276(9) 0.0338(10) 0.0211(9) 0.0061(7) -0.0054(7) -0.0130(8)
C13 0.0194(8) 0.0235(8) 0.0235(8) 0.0008(7) -0.0018(6) -0.0079(7)

_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 1.9971(11) . ?
Ni1 O4 1.9972(11) 2_767 ?
Ni1 O1 2.0218(11) 2_767 ?
Ni1 O1 2.0218(11) . ?
Ni1 O5 2.0878(13) . ?
Ni1 O5 2.0878(13) 2_767 ?
O1 C1 1.2704(18) . ?
O2 C1 1.253(2) . ?
O3 C3 1.2344(19) . ?
O4 C3 1.2839(19) . ?
O5 H1O5 0.80(3) . ?
O5 H2O5 0.78(3) . ?
C1 C2 1.520(2) . ?
C2 C3 1.525(2) . ?
C2 H2A 0.94(2) . ?
C2 H2B 0.94(2) . ?
P1 F2 1.5745(13) . ?
P1 F1 1.5803(13) . ?
P1 F6 1.5968(11) . ?
P1 F4 1.5989(12) . ?
P1 F5 1.6012(11) . ?
P1 F3 1.6078(13) . ?
N1 C9 1.340(2) . ?
N1 H1N1 0.85(2) . ?
N1 H2N1 0.85(2) . ?
N2 C9 1.342(2) . ?
N2 C13 1.360(2) . ?
N2 H1N2 0.78(2) . ?
N3 C4 1.326(2) . ?
N3 H1N3 0.82(3) . ?
N3 H2N3 0.86(3) . ?
N4 C4 1.353(2) . ?
N4 C8 1.361(2) . ?
N4 H1N4 0.86(2) . ?
C4 C5 1.413(2) . ?
C5 C6 1.355(3) . ?
C5 H5 0.92(2) . ?
C6 C7 1.406(3) . ?
C6 H6 0.88(3) . ?
C7 C8 1.355(3) . ?
C7 H7 0.93(3) . ?
C8 H8 0.93(2) . ?
C9 C10 1.411(2) . ?
C10 C11 1.364(3) . ?
C10 H10 0.93(2) . ?
C11 C12 1.402(3) . ?
C11 H11 0.94(2) . ?
C12 C13 1.358(3) . ?
C12 H12 0.92(2) . ?
C13 H13 0.93(2) . ?

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 O4 179.999(1) . 2_767 ?
O4 Ni1 O1 88.90(4) . 2_767 ?
O4 Ni1 O1 91.10(4) 2_767 2_767 ?
O4 Ni1 O1 91.10(4) . . ?
O4 Ni1 O1 88.90(4) 2_767 . ?
O1 Ni1 O1 180.0 2_767 . ?
O4 Ni1 O5 92.02(5) . . ?
O4 Ni1 O5 87.98(5) 2_767 . ?
O1 Ni1 O5 85.44(5) 2_767 . ?
O1 Ni1 O5 94.56(5) . . ?
O4 Ni1 O5 87.98(5) . 2_767 ?
O4 Ni1 O5 92.02(5) 2_767 2_767 ?
O1 Ni1 O5 94.56(5) 2_767 2_767 ?
O1 Ni1 O5 85.44(5) . 2_767 ?
O5 Ni1 O5 180.0 . 2_767 ?
C1 O1 Ni1 127.52(10) . . ?
C3 O4 Ni1 129.30(10) . . ?
Ni1 O5 H1O5 119.2(18) . . ?
Ni1 O5 H2O5 128.0(17) . . ?
H1O5 O5 H2O5 105(2) . . ?
O2 C1 O1 122.01(14) . . ?
O2 C1 C2 117.82(14) . . ?
O1 C1 C2 120.05(14) . . ?
C1 C2 C3 120.20(13) . . ?
C1 C2 H2A 106.5(13) . . ?
C3 C2 H2A 105.1(14) . . ?
C1 C2 H2B 110.2(12) . . ?
C3 C2 H2B 108.0(13) . . ?
H2A C2 H2B 106.0(18) . . ?
O3 C3 O4 123.01(14) . . ?
O3 C3 C2 116.87(14) . . ?
O4 C3 C2 120.08(13) . . ?
F2 P1 F1 91.14(9) . . ?
F2 P1 F6 90.76(7) . . ?
F1 P1 F6 90.31(7) . . ?
F2 P1 F4 178.62(8) . . ?
F1 P1 F4 89.82(9) . . ?
F6 P1 F4 90.23(6) . . ?
F2 P1 F5 89.59(7) . . ?
F1 P1 F5 90.49(7) . . ?
F6 P1 F5 179.11(7) . . ?
F4 P1 F5 89.40(7) . . ?
F2 P1 F3 90.43(8) . . ?
F1 P1 F3 178.42(9) . . ?
F6 P1 F3 89.90(7) . . ?
F4 P1 F3 88.61(8) . . ?
F5 P1 F3 89.29(7) . . ?
C9 N1 H1N1 117.7(15) . . ?
C9 N1 H2N1 119.5(15) . . ?
H1N1 N1 H2N1 119(2) . . ?
C9 N2 C13 123.33(15) . . ?
C9 N2 H1N2 117.2(14) . . ?
C13 N2 H1N2 119.4(14) . . ?
C4 N3 H1N3 116.5(16) . . ?
C4 N3 H2N3 119.8(16) . . ?
H1N3 N3 H2N3 122(2) . . ?
C4 N4 C8 122.81(16) . . ?
C4 N4 H1N4 115.2(15) . . ?
C8 N4 H1N4 121.9(15) . . ?
N3 C4 N4 118.24(16) . . ?
N3 C4 C5 123.96(17) . . ?
N4 C4 C5 117.81(17) . . ?
C6 C5 C4 119.53(18) . . ?
C6 C5 H5 122.7(14) . . ?
C4 C5 H5 117.7(14) . . ?
C5 C6 C7 121.03(18) . . ?
C5 C6 H6 120.4(17) . . ?
C7 C6 H6 118.5(17) . . ?
C8 C7 C6 118.51(19) . . ?
C8 C7 H7 120.4(16) . . ?
C6 C7 H7 121.1(16) . . ?
C7 C8 N4 120.24(18) . . ?
C7 C8 H8 123.7(13) . . ?
N4 C8 H8 116.0(13) . . ?
N1 C9 N2 118.37(15) . . ?
N1 C9 C10 123.68(16) . . ?
N2 C9 C10 117.92(15) . . ?
C11 C10 C9 119.20(17) . . ?
C11 C10 H10 124.0(13) . . ?
C9 C10 H10 116.7(13) . . ?
C10 C11 C12 121.06(17) . . ?
C10 C11 H11 120.1(14) . . ?
C12 C11 H11 118.8(14) . . ?
C13 C12 C11 118.47(17) . . ?
C13 C12 H12 117.5(14) . . ?
C11 C12 H12 124.0(14) . . ?
C12 C13 N2 119.95(17) . . ?
C12 C13 H13 124.9(12) . . ?
N2 C13 H13 115.1(12) . . ?

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
O4 Ni1 O1 C1 -3.66(13) . . . . ?
O4 Ni1 O1 C1 176.34(13) 2_767 . . . ?
O1 Ni1 O1 C1 92(37) 2_767 . . . ?
O5 Ni1 O1 C1 88.46(13) . . . . ?
O5 Ni1 O1 C1 -91.54(13) 2_767 . . . ?
O4 Ni1 O4 C3 -52(80) 2_767 . . . ?
O1 Ni1 O4 C3 -163.53(13) 2_767 . . . ?
O1 Ni1 O4 C3 16.47(13) . . . . ?
O5 Ni1 O4 C3 -78.13(13) . . . . ?
O5 Ni1 O4 C3 101.87(13) 2_767 . . . ?
Ni1 O1 C1 O2 162.02(11) . . . . ?
Ni1 O1 C1 C2 -21.9(2) . . . . ?
O2 C1 C2 C3 -141.67(15) . . . . ?
O1 C1 C2 C3 42.1(2) . . . . ?
Ni1 O4 C3 O3 175.43(11) . . . . ?
Ni1 O4 C3 C2 -2.1(2) . . . . ?
C1 C2 C3 O3 153.03(15) . . . . ?
C1 C2 C3 O4 -29.3(2) . . . . ?
C8 N4 C4 N3 178.46(16) . . . . ?
C8 N4 C4 C5 -1.8(3) . . . . ?
N3 C4 C5 C6 -177.50(18) . . . . ?
N4 C4 C5 C6 2.8(3) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 N4 2.2(3) . . . . ?
C4 N4 C8 C7 -0.7(3) . . . . ?
C13 N2 C9 N1 178.43(15) . . . . ?
C13 N2 C9 C10 -3.2(2) . . . . ?
N1 C9 C10 C11 -179.00(16) . . . . ?
N2 C9 C10 C11 2.7(2) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 N2 0.8(3) . . . . ?
C9 N2 C13 C12 1.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H1O5 O2 0.80(3) 1.89(3) 2.6855(18) 170(3) 1_655
N4 H1N4 O4 0.86(2) 1.91(2) 2.7629(19) 175(2) 1_455
N1 H1N1 O2 0.85(2) 2.09(2) 2.9351(19) 175(2) 2_667
N3 H2N3 O3 0.86(3) 1.96(3) 2.812(2) 171(2) 1_455
N2 H1N2 O1 0.78(2) 2.07(2) 2.8388(19) 168(2) 2_667
O5 H2O5 F3 0.78(3) 2.28(3) 3.015(2) 159(2) .
O5 H2O5 F4 0.78(3) 2.36(2) 3.0142(19) 142(2) .
N1 H2N1 F6 0.85(2) 2.17(2) 2.9921(19) 161(2) 1_545
N3 H1N3 F1 0.82(3) 2.13(3) 2.928(2) 163(2) 2_666

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.055