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

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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
#  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_compound_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            1
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Co N4 O5'
_chemical_formula_sum            'C20 H15 Co N4 O5'
_chemical_formula_weight         450.29

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'
Co Co 0.3494 0.9721 '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                   8.157(3)
_cell_length_b                   9.405(4)
_cell_length_c                   12.802(8)
_cell_angle_alpha                105.220(8)
_cell_angle_beta                 98.276(8)
_cell_angle_gamma                107.826(6)
_cell_volume                     874.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2419
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      24.6

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    1.026
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8210
_exptl_absorpt_correction_T_max  0.9043
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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_reflns_number            9176
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3099
_reflns_number_gt                2568
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0329P)²+0.2695P] 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         3099
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_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
Co1 Co 0.28460(4) 0.45024(4) 0.46325(3) 0.01804(12) Uani 1 1 d . . .
O1 O 0.4872(2) 0.42483(19) 0.57918(13) 0.0201(4) Uani 1 1 d . . .
O2 O 0.3252(3) 0.2206(2) 0.62205(15) 0.0346(5) Uani 1 1 d . . .
O3 O 0.8639(2) 0.4644(2) 0.63080(14) 0.0278(4) Uani 1 1 d . . .
O4 O 1.0048(2) 0.3964(2) 0.75903(15) 0.0291(4) Uani 1 1 d . . .
O5 O 0.0750(3) 0.3253(2) 0.52007(17) 0.0287(5) Uani 1 1 d . . .
H5A H 0.0269 0.3848 0.5490 0.043 Uiso 1 1 calc R . .
H5B H 0.112(5) 0.282(4) 0.559(3) 0.051(11) Uiso 1 1 d . . .
N1 N 0.3161(3) 0.6613(2) 0.59318(16) 0.0219(5) Uani 1 1 d . . .
N2 N 0.3037(3) 0.8227(2) 0.74934(17) 0.0224(5) Uani 1 1 d . . .
N3 N 0.2237(3) 1.0527(2) 1.18347(17) 0.0231(5) Uani 1 1 d . . .
N4 N 0.2348(3) 1.2297(2) 1.33945(17) 0.0245(5) Uani 1 1 d . . .
C1 C 0.3654(4) 0.8128(3) 0.5878(2) 0.0291(6) Uani 1 1 d . . .
H1 H 0.3993 0.8415 0.5277 0.035 Uiso 1 1 calc R . .
C2 C 0.3573(4) 0.9129(3) 0.6820(2) 0.0304(7) Uani 1 1 d . . .
H2 H 0.3827 1.0209 0.6986 0.036 Uiso 1 1 calc R . .
C3 C 0.2797(3) 0.6720(3) 0.6911(2) 0.0211(6) Uani 1 1 d . . .
H3 H 0.2423 0.5869 0.7171 0.025 Uiso 1 1 calc R . .
C4 C 0.2788(3) 0.8777(3) 0.8586(2) 0.0220(6) Uani 1 1 d . . .
C5 C 0.2318(4) 1.0097(3) 0.8885(2) 0.0283(6) Uani 1 1 d . . .
H5 H 0.2133 1.0605 0.8372 0.034 Uiso 1 1 calc R . .
C6 C 0.2128(4) 1.0650(3) 0.9955(2) 0.0279(6) Uani 1 1 d . . .
H6 H 0.1813 1.1536 1.0160 0.034 Uiso 1 1 calc R . .
C7 C 0.2399(3) 0.9905(3) 1.0721(2) 0.0228(6) Uani 1 1 d . . .
C8 C 0.2855(4) 0.8579(3) 1.0420(2) 0.0276(6) Uani 1 1 d . . .
H8 H 0.3029 0.8067 1.0933 0.033 Uiso 1 1 calc R . .
C9 C 0.3051(4) 0.8020(3) 0.9350(2) 0.0285(6) Uani 1 1 d . . .
H9 H 0.3362 0.7132 0.9144 0.034 Uiso 1 1 calc R . .
C10 C 0.1543(4) 0.9699(3) 1.2512(2) 0.0292(6) Uani 1 1 d . . .
H10 H 0.1112 0.8609 1.2350 0.035 Uiso 1 1 calc R . .
C11 C 0.1620(4) 1.0798(3) 1.3459(2) 0.0302(7) Uani 1 1 d . . .
H11 H 0.1236 1.0578 1.4068 0.036 Uiso 1 1 calc R . .
C12 C 0.2699(3) 1.2075(3) 1.2409(2) 0.0242(6) Uani 1 1 d . . .
H12 H 0.3208 1.2888 1.2138 0.029 Uiso 1 1 calc R . .
C13 C 0.4549(3) 0.3419(3) 0.6442(2) 0.0185(5) Uani 1 1 d . . .
C14 C 0.5714(3) 0.4094(3) 0.76271(19) 0.0178(5) Uani 1 1 d . . .
C15 C 0.7569(3) 0.4577(3) 0.7968(2) 0.0184(5) Uani 1 1 d . . .
C16 C 0.8833(3) 0.4373(3) 0.7230(2) 0.0195(5) Uani 1 1 d . . .
C17 C 0.8351(3) 0.5239(3) 0.9108(2) 0.0220(6) Uani 1 1 d . . .
H17 H 0.9579 0.5565 0.9347 0.026 Uiso 1 1 calc R . .
C18 C 0.7389(3) 0.5431(3) 0.9899(2) 0.0212(6) Uani 1 1 d . . .
H18 H 0.7974 0.5904 1.0651 0.025 Uiso 1 1 calc R . .
C19 C 0.5534(3) 0.4920(3) 0.9579(2) 0.0195(5) Uani 1 1 d . . .
C20 C 0.4750(3) 0.4247(3) 0.8439(2) 0.0212(6) Uani 1 1 d . . .
H20 H 0.3518 0.3880 0.8207 0.025 Uiso 1 1 calc 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
Co1 O3 2.0605(18) 2_666 ?
Co1 O5 2.100(2) . ?
Co1 O1 2.1042(18) 2_666 ?
Co1 N4 2.133(2) 1_544 ?
Co1 N1 2.146(2) . ?
Co1 O1 2.1711(18) . ?
O1 C13 1.285(3) . ?
O1 Co1 2.1042(17) 2_666 ?
O2 C13 1.227(3) . ?
O3 C16 1.269(3) . ?
O3 Co1 2.0605(19) 2_666 ?
O4 C16 1.241(3) . ?
O5 H5A 0.8200 . ?
O5 H5B 0.80(3) . ?
N1 C3 1.315(3) . ?
N1 C1 1.381(3) . ?
N2 C3 1.355(3) . ?
N2 C2 1.386(3) . ?
N2 C4 1.426(3) . ?
N3 C12 1.350(3) . ?
N3 C10 1.380(3) . ?
N3 C7 1.434(3) . ?
N4 C12 1.311(3) . ?
N4 C11 1.382(3) . ?
N4 Co1 2.133(2) 1_566 ?
C1 C2 1.346(4) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C9 1.381(4) . ?
C4 C5 1.385(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.384(3) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.350(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.522(3) . ?
C14 C20 1.395(3) . ?
C14 C15 1.404(3) . ?
C15 C17 1.392(3) . ?
C15 C16 1.516(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.400(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(3) . ?
C19 C19 1.486(5) 2_667 ?
C20 H20 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
O3 Co1 O5 96.09(9) 2_666 . ?
O3 Co1 O1 89.54(7) 2_666 2_666 ?
O5 Co1 O1 173.96(8) . 2_666 ?
O3 Co1 N4 97.88(8) 2_666 1_544 ?
O5 Co1 N4 86.07(8) . 1_544 ?
O1 Co1 N4 95.34(8) 2_666 1_544 ?
O3 Co1 N1 82.67(8) 2_666 . ?
O5 Co1 N1 88.91(8) . . ?
O1 Co1 N1 89.65(8) 2_666 . ?
N4 Co1 N1 174.98(8) 1_544 . ?
O3 Co1 O1 164.92(7) 2_666 . ?
O5 Co1 O1 93.77(8) . . ?
O1 Co1 O1 80.29(7) 2_666 . ?
N4 Co1 O1 94.16(8) 1_544 . ?
N1 Co1 O1 86.13(8) . . ?
C13 O1 Co1 135.64(16) . 2_666 ?
C13 O1 Co1 124.42(15) . . ?
Co1 O1 Co1 99.71(7) 2_666 . ?
C16 O3 Co1 141.47(16) . 2_666 ?
Co1 O5 H5A 109.5 . . ?
Co1 O5 H5B 109(3) . . ?
H5A O5 H5B 115.7 . . ?
C3 N1 C1 105.6(2) . . ?
C3 N1 Co1 127.31(17) . . ?
C1 N1 Co1 126.93(17) . . ?
C3 N2 C2 106.6(2) . . ?
C3 N2 C4 126.7(2) . . ?
C2 N2 C4 126.7(2) . . ?
C12 N3 C10 106.7(2) . . ?
C12 N3 C7 125.4(2) . . ?
C10 N3 C7 127.9(2) . . ?
C12 N4 C11 104.9(2) . . ?
C12 N4 Co1 127.20(18) . 1_566 ?
C11 N4 Co1 127.88(17) . 1_566 ?
C2 C1 N1 110.1(2) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
C1 C2 N2 106.2(2) . . ?
C1 C2 H2 126.9 . . ?
N2 C2 H2 126.9 . . ?
N1 C3 N2 111.5(2) . . ?
N1 C3 H3 124.2 . . ?
N2 C3 H3 124.2 . . ?
C9 C4 C5 120.2(2) . . ?
C9 C4 N2 120.2(2) . . ?
C5 C4 N2 119.6(2) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 N3 119.6(2) . . ?
C8 C7 N3 120.4(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C4 C9 C8 120.2(2) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 N3 105.8(2) . . ?
C11 C10 H10 127.1 . . ?
N3 C10 H10 127.1 . . ?
C10 C11 N4 110.4(2) . . ?
C10 C11 H11 124.8 . . ?
N4 C11 H11 124.8 . . ?
N4 C12 N3 112.2(2) . . ?
N4 C12 H12 123.9 . . ?
N3 C12 H12 123.9 . . ?
O2 C13 O1 124.6(2) . . ?
O2 C13 C14 117.1(2) . . ?
O1 C13 C14 117.8(2) . . ?
C20 C14 C15 118.9(2) . . ?
C20 C14 C13 113.0(2) . . ?
C15 C14 C13 128.1(2) . . ?
C17 C15 C14 117.5(2) . . ?
C17 C15 C16 115.3(2) . . ?
C14 C15 C16 127.0(2) . . ?
O4 C16 O3 123.4(2) . . ?
O4 C16 C15 116.3(2) . . ?
O3 C16 C15 120.3(2) . . ?
C18 C17 C15 123.0(2) . . ?
C18 C17 H17 118.5 . . ?
C15 C17 H17 118.5 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 116.7(2) . . ?
C20 C19 C19 122.0(3) . 2_667 ?
C18 C19 C19 121.4(3) . 2_667 ?
C19 C20 C14 123.5(2) . . ?
C19 C20 H20 118.3 . . ?
C14 C20 H20 118.3 . . ?

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 Co1 O1 C13 136.5(2) 2_666 . . . ?
O5 Co1 O1 C13 5.78(18) . . . . ?
O1 Co1 O1 C13 -175.3(2) 2_666 . . . ?
N4 Co1 O1 C13 -80.55(18) 1_544 . . . ?
N1 Co1 O1 C13 94.43(18) . . . . ?
O3 Co1 O1 Co1 -48.2(3) 2_666 . . 2_666 ?
O5 Co1 O1 Co1 -178.96(7) . . . 2_666 ?
O1 Co1 O1 Co1 0.0 2_666 . . 2_666 ?
N4 Co1 O1 Co1 94.72(8) 1_544 . . 2_666 ?
N1 Co1 O1 Co1 -90.31(8) . . . 2_666 ?
O3 Co1 N1 C3 125.2(2) 2_666 . . . ?
O5 Co1 N1 C3 28.9(2) . . . . ?
O1 Co1 N1 C3 -145.2(2) 2_666 . . . ?
N4 Co1 N1 C3 28.6(11) 1_544 . . . ?
O1 Co1 N1 C3 -64.9(2) . . . . ?
O3 Co1 N1 C1 -49.2(2) 2_666 . . . ?
O5 Co1 N1 C1 -145.4(2) . . . . ?
O1 Co1 N1 C1 40.4(2) 2_666 . . . ?
N4 Co1 N1 C1 -145.8(9) 1_544 . . . ?
O1 Co1 N1 C1 120.7(2) . . . . ?
C3 N1 C1 C2 -0.3(3) . . . . ?
Co1 N1 C1 C2 175.03(18) . . . . ?
N1 C1 C2 N2 0.7(3) . . . . ?
C3 N2 C2 C1 -0.9(3) . . . . ?
C4 N2 C2 C1 179.0(2) . . . . ?
C1 N1 C3 N2 -0.2(3) . . . . ?
Co1 N1 C3 N2 -175.57(16) . . . . ?
C2 N2 C3 N1 0.7(3) . . . . ?
C4 N2 C3 N1 -179.2(2) . . . . ?
C3 N2 C4 C9 29.6(4) . . . . ?
C2 N2 C4 C9 -150.2(3) . . . . ?
C3 N2 C4 C5 -151.8(3) . . . . ?
C2 N2 C4 C5 28.3(4) . . . . ?
C9 C4 C5 C6 0.4(4) . . . . ?
N2 C4 C5 C6 -178.2(2) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 N3 178.4(2) . . . . ?
C12 N3 C7 C6 -34.9(4) . . . . ?
C10 N3 C7 C6 142.8(3) . . . . ?
C12 N3 C7 C8 143.9(3) . . . . ?
C10 N3 C7 C8 -38.3(4) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
N3 C7 C8 C9 -178.3(2) . . . . ?
C5 C4 C9 C8 -0.2(4) . . . . ?
N2 C4 C9 C8 178.3(2) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C12 N3 C10 C11 0.3(3) . . . . ?
C7 N3 C10 C11 -177.8(3) . . . . ?
N3 C10 C11 N4 -0.2(3) . . . . ?
C12 N4 C11 C10 0.0(3) . . . . ?
Co1 N4 C11 C10 -178.97(19) 1_566 . . . ?
C11 N4 C12 N3 0.2(3) . . . . ?
Co1 N4 C12 N3 179.19(17) 1_566 . . . ?
C10 N3 C12 N4 -0.3(3) . . . . ?
C7 N3 C12 N4 177.8(2) . . . . ?
Co1 O1 C13 O2 -141.2(2) 2_666 . . . ?
Co1 O1 C13 O2 32.1(3) . . . . ?
Co1 O1 C13 C14 47.3(3) 2_666 . . . ?
Co1 O1 C13 C14 -139.43(17) . . . . ?
O2 C13 C14 C20 -50.2(3) . . . . ?
O1 C13 C14 C20 122.0(2) . . . . ?
O2 C13 C14 C15 130.9(3) . . . . ?
O1 C13 C14 C15 -57.0(3) . . . . ?
C20 C14 C15 C17 -2.3(3) . . . . ?
C13 C14 C15 C17 176.7(2) . . . . ?
C20 C14 C15 C16 174.0(2) . . . . ?
C13 C14 C15 C16 -7.1(4) . . . . ?
Co1 O3 C16 O4 -172.66(18) 2_666 . . . ?
Co1 O3 C16 C15 6.1(4) 2_666 . . . ?
C17 C15 C16 O4 38.1(3) . . . . ?
C14 C15 C16 O4 -138.2(3) . . . . ?
C17 C15 C16 O3 -140.7(2) . . . . ?
C14 C15 C16 O3 43.0(4) . . . . ?
C14 C15 C17 C18 0.1(4) . . . . ?
C16 C15 C17 C18 -176.5(2) . . . . ?
C15 C17 C18 C19 1.6(4) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C17 C18 C19 C19 178.5(3) . . . 2_667 ?
C18 C19 C20 C14 -1.2(4) . . . . ?
C19 C19 C20 C14 179.3(3) 2_667 . . . ?
C15 C14 C20 C19 2.9(4) . . . . ?
C13 C14 C20 C19 -176.2(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 H5B O2 0.80(3) 2.12(3) 2.824(3) 148(3) .
O5 H5A O3 0.82 2.01 2.792(3) 160.5 1_455

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 999232'
#######################################################################
#
#                 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_compound_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            2
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 N4 Ni O5'
_chemical_formula_sum            'C20 H15 N4 Ni O5'
_chemical_formula_weight         450.07

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'
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  '-P 1'

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

_cell_length_a                   8.1587(9)
_cell_length_b                   9.3411(12)
_cell_length_c                   12.7338(12)
_cell_angle_alpha                105.254(2)
_cell_angle_beta                 98.139(2)
_cell_angle_gamma                107.777(2)
_cell_volume                     865.16(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    646
_cell_measurement_theta_min      2.473
_cell_measurement_theta_max      21.5

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    1.167
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.7590
_exptl_absorpt_correction_T_max  0.8001
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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_reflns_number            5257
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.1318
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3397
_reflns_number_gt                2012
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1000P)²+0.0000P] 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         3397
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_restrained_S_all      0.851
_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 0.28768(10) 0.45233(9) 0.46343(6) 0.0206(2) Uani 1 1 d . . .
O1 O 0.5134(5) 0.5755(4) 0.4230(3) 0.0213(9) Uani 1 1 d . . .
O2 O 0.6801(6) 0.7754(5) 0.3766(4) 0.0418(12) Uani 1 1 d . . .
O3 O 0.1311(5) 0.5293(5) 0.3694(3) 0.0289(10) Uani 1 1 d . . .
O4 O -0.0042(6) 0.6036(5) 0.2430(4) 0.0362(11) Uani 1 1 d . . .
O5 O 0.0774(5) 0.3293(5) 0.5170(3) 0.0291(10) Uani 1 1 d . . .
H5A H 0.0152 0.3732 0.5471 0.044 Uiso 1 1 d R . .
H5B H 0.1156 0.2894 0.5604 0.044 Uiso 1 1 d R . .
N1 N 0.3193(6) 0.6596(5) 0.5903(4) 0.0220(11) Uani 1 1 d . . .
N2 N 0.3045(6) -0.1774(6) -0.2525(4) 0.0265(11) Uani 1 1 d . . .
N3 N 0.2396(6) 0.2352(6) 0.3413(4) 0.0248(11) Uani 1 1 d . . .
N4 N 0.2255(6) 0.0558(6) 0.1848(4) 0.0261(11) Uani 1 1 d . . .
C1 C 0.5475(8) 0.6584(7) 0.3577(4) 0.0227(13) Uani 1 1 d . . .
C2 C 0.4291(8) 0.5915(7) 0.2397(5) 0.0299(15) Uani 1 1 d . . .
C3 C 0.5261(9) 0.5758(8) 0.1562(5) 0.0307(14) Uani 1 1 d . . .
H3 H 0.6492 0.6129 0.1788 0.037 Uiso 1 1 calc R . .
C4 C 0.4463(8) 0.5076(7) 0.0425(5) 0.0304(15) Uani 1 1 d . . .
C5 C 0.2601(8) 0.4568(7) 0.0088(5) 0.0307(15) Uani 1 1 d . . .
H5 H 0.2020 0.4096 -0.0668 0.037 Uiso 1 1 calc R . .
C6 C 0.1638(9) 0.4782(8) 0.0907(5) 0.0342(16) Uani 1 1 d . . .
H6 H 0.0414 0.4487 0.0677 0.041 Uiso 1 1 calc R . .
C7 C 0.2437(8) 0.5418(7) 0.2048(5) 0.0286(14) Uani 1 1 d . . .
C8 C 0.1153(8) 0.5593(7) 0.2788(5) 0.0267(14) Uani 1 1 d . . .
C9 C 0.2742(8) 0.2112(7) 0.2420(5) 0.0281(14) Uani 1 1 d . . .
H9 H 0.3264 0.2923 0.2143 0.034 Uiso 1 1 calc R . .
C10 C 0.1651(8) 0.0847(7) 0.3480(5) 0.0307(15) Uani 1 1 d . . .
H10 H 0.1272 0.0634 0.4097 0.037 Uiso 1 1 calc R . .
C11 C 0.1548(8) -0.0285(8) 0.2517(5) 0.0314(15) Uani 1 1 d . . .
H11 H 0.1099 -0.1383 0.2349 0.038 Uiso 1 1 calc R . .
C12 C 0.2420(8) -0.0074(7) 0.0725(5) 0.0278(14) Uani 1 1 d . . .
C13 C 0.2133(8) 0.0670(7) -0.0051(5) 0.0283(14) Uani 1 1 d . . .
H13 H 0.1808 0.1557 0.0152 0.034 Uiso 1 1 calc R . .
C14 C 0.2326(8) 0.0112(7) -0.1120(5) 0.0304(15) Uani 1 1 d . . .
H14 H 0.2144 0.0626 -0.1636 0.036 Uiso 1 1 calc R . .
C15 C 0.2792(8) -0.1216(7) -0.1426(5) 0.0253(14) Uani 1 1 d . . .
C16 C 0.3057(8) -0.1980(7) -0.0662(5) 0.0285(14) Uani 1 1 d . . .
H16 H 0.3368 -0.2875 -0.0869 0.034 Uiso 1 1 calc R . .
C17 C 0.2857(8) -0.1409(7) 0.0418(5) 0.0295(14) Uani 1 1 d . . .
H17 H 0.3019 -0.1929 0.0932 0.035 Uiso 1 1 calc R . .
C18 C 0.2827(8) 0.6723(7) 0.6892(5) 0.0249(13) Uani 1 1 d . . .
H18 H 0.2460 0.5869 0.7158 0.030 Uiso 1 1 calc R . .
C19 C 0.3657(9) 0.8122(7) 0.5850(5) 0.0340(16) Uani 1 1 d . . .
H19 H 0.3991 0.8413 0.5246 0.041 Uiso 1 1 calc R . .
C20 C 0.3558(9) -0.0874(7) -0.3212(5) 0.0331(15) Uani 1 1 d . . .
H20 H 0.3788 0.0209 -0.3054 0.040 Uiso 1 1 calc 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 O3 2.040(4) . ?
Ni1 O1 2.066(4) . ?
Ni1 O5w 2.066(4) . ?
Ni1 N1 2.087(4) . ?
Ni1 N3 2.090(4) . ?
Ni1 O1 2.141(4) 2_666 ?
O1 C1 1.281(6) . ?
O1 Ni1 2.141(4) 2_666 ?
O2 C1 1.221(7) . ?
O3 C8 1.256(7) . ?
O4 C8 1.245(7) . ?
O5 H5A 0.8200 . ?
O5 H5B 0.8200 . ?
N1 C18 1.319(7) . ?
N1 C19 1.382(7) . ?
N2 C18 1.347(7) 1_544 ?
N2 C20 1.388(7) . ?
N2 C15 1.427(7) . ?
N3 C9 1.312(7) . ?
N3 C10 1.382(7) . ?
N4 C9 1.344(7) . ?
N4 C11 1.375(7) . ?
N4 C12 1.439(7) . ?
C1 C2 1.519(8) . ?
C2 C7 1.405(9) . ?
C2 C3 1.416(8) . ?
C3 C4 1.387(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(9) . ?
C4 C4 1.490(11) 2_665 ?
C5 C6 1.401(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.521(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.375(8) . ?
C12 C13 1.382(8) . ?
C13 C14 1.373(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(8) . ?
C16 C17 1.391(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N2 1.347(7) 1_566 ?
C18 H18 0.9300 . ?
C19 C20 1.340(8) 1_566 ?
C19 H19 0.9300 . ?
C20 C19 1.340(8) 1_544 ?
C20 H20 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
O3 Ni1 O1 92.54(15) . . ?
O3 Ni1 O5 92.47(16) . . ?
O1 Ni1 O5 174.59(15) . . ?
O3 Ni1 N1 83.72(17) . . ?
O1 Ni1 N1 89.16(16) . . ?
O5 Ni1 N1 89.37(16) . . ?
O3 Ni1 N3 96.62(18) . . ?
O1 Ni1 N3 95.38(17) . . ?
O5 Ni1 N3 86.06(17) . . ?
N1 Ni1 N3 175.42(18) . . ?
O3 Ni1 O1 167.71(16) . 2_666 ?
O1 Ni1 O1 79.70(15) . 2_666 ?
O5 Ni1 O1 95.02(15) . 2_666 ?
N1 Ni1 O1 86.62(16) . 2_666 ?
N3 Ni1 O1 93.61(16) . 2_666 ?
C1 O1 Ni1 135.6(4) . . ?
C1 O1 Ni1 124.0(4) . 2_666 ?
Ni1 O1 Ni1 100.30(15) . 2_666 ?
C8 O3 Ni1 139.9(4) . . ?
Ni1 O5 H5A 121.4 . . ?
Ni1 O5 H5B 108.0 . . ?
H5A O5 H5B 106.9 . . ?
C18 N1 C19 104.4(5) . . ?
C18 N1 Ni1 127.8(4) . . ?
C19 N1 Ni1 127.6(4) . . ?
C18 N2 C20 106.1(5) 1_544 . ?
C18 N2 C15 127.2(5) 1_544 . ?
C20 N2 C15 126.8(5) . . ?
C9 N3 C10 104.7(5) . . ?
C9 N3 Ni1 127.9(4) . . ?
C10 N3 Ni1 127.4(4) . . ?
C9 N4 C11 107.8(5) . . ?
C9 N4 C12 124.9(5) . . ?
C11 N4 C12 127.3(5) . . ?
O2 C1 O1 125.4(5) . . ?
O2 C1 C2 116.4(5) . . ?
O1 C1 C2 117.4(5) . . ?
C7 C2 C3 118.1(6) . . ?
C7 C2 C1 129.4(5) . . ?
C3 C2 C1 112.5(5) . . ?
C4 C3 C2 123.1(6) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3 C4 C5 118.0(6) . . ?
C3 C4 C4 121.3(7) . 2_665 ?
C5 C4 C4 120.6(7) . 2_665 ?
C6 C5 C4 119.1(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 122.6(6) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C6 C7 C2 118.8(6) . . ?
C6 C7 C8 114.0(6) . . ?
C2 C7 C8 127.0(5) . . ?
O4 C8 O3 123.3(5) . . ?
O4 C8 C7 115.7(5) . . ?
O3 C8 C7 121.0(5) . . ?
N3 C9 N4 112.1(5) . . ?
N3 C9 H9 123.9 . . ?
N4 C9 H9 123.9 . . ?
C11 C10 N3 110.7(5) . . ?
C11 C10 H10 124.7 . . ?
N3 C10 H10 124.7 . . ?
C10 C11 N4 104.7(5) . . ?
C10 C11 H11 127.6 . . ?
N4 C11 H11 127.6 . . ?
C17 C12 C13 119.8(5) . . ?
C17 C12 N4 120.7(5) . . ?
C13 C12 N4 119.6(5) . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 119.7(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 N2 119.9(5) . . ?
C14 C15 N2 120.0(5) . . ?
C15 C16 C17 119.8(5) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 119.9(6) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
N1 C18 N2 112.6(5) . 1_566 ?
N1 C18 H18 123.7 . . ?
N2 C18 H18 123.7 1_566 . ?
C20 C19 N1 110.8(5) 1_566 . ?
C20 C19 H19 124.6 1_566 . ?
N1 C19 H19 124.6 . . ?
C19 C20 N2 106.2(5) 1_544 . ?
C19 C20 H20 126.9 1_544 . ?
N2 C20 H20 126.9 . . ?

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 Ni1 O1 C1 -5.2(5) . . . . ?
O5 Ni1 O1 C1 -163.1(15) . . . . ?
N1 Ni1 O1 C1 -88.9(5) . . . . ?
N3 Ni1 O1 C1 91.6(5) . . . . ?
O1 Ni1 O1 C1 -175.6(6) 2_666 . . . ?
O3 Ni1 O1 Ni1 170.40(16) . . . 2_666 ?
O5 Ni1 O1 Ni1 12.5(17) . . . 2_666 ?
N1 Ni1 O1 Ni1 86.72(17) . . . 2_666 ?
N3 Ni1 O1 Ni1 -92.71(18) . . . 2_666 ?
O1 Ni1 O1 Ni1 0.0 2_666 . . 2_666 ?
O1 Ni1 O3 C8 36.9(7) . . . . ?
O5 Ni1 O3 C8 -145.1(6) . . . . ?
N1 Ni1 O3 C8 125.8(7) . . . . ?
N3 Ni1 O3 C8 -58.8(7) . . . . ?
O1 Ni1 O3 C8 87.3(9) 2_666 . . . ?
O3 Ni1 N1 C18 122.4(5) . . . . ?
O1 Ni1 N1 C18 -144.9(5) . . . . ?
O5 Ni1 N1 C18 29.8(5) . . . . ?
N3 Ni1 N1 C18 28(3) . . . . ?
O1 Ni1 N1 C18 -65.2(5) 2_666 . . . ?
O3 Ni1 N1 C19 -50.2(5) . . . . ?
O1 Ni1 N1 C19 42.4(5) . . . . ?
O5 Ni1 N1 C19 -142.8(5) . . . . ?
N3 Ni1 N1 C19 -145(2) . . . . ?
O1 Ni1 N1 C19 122.2(5) 2_666 . . . ?
O3 Ni1 N3 C9 60.9(5) . . . . ?
O1 Ni1 N3 C9 -32.3(5) . . . . ?
O5 Ni1 N3 C9 152.9(5) . . . . ?
N1 Ni1 N3 C9 155(2) . . . . ?
O1 Ni1 N3 C9 -112.3(5) 2_666 . . . ?
O3 Ni1 N3 C10 -119.7(5) . . . . ?
O1 Ni1 N3 C10 147.1(5) . . . . ?
O5 Ni1 N3 C10 -27.6(5) . . . . ?
N1 Ni1 N3 C10 -26(3) . . . . ?
O1 Ni1 N3 C10 67.2(5) 2_666 . . . ?
Ni1 O1 C1 O2 145.1(5) . . . . ?
Ni1 O1 C1 O2 -29.7(8) 2_666 . . . ?
Ni1 O1 C1 C2 -45.3(7) . . . . ?
Ni1 O1 C1 C2 139.9(4) 2_666 . . . ?
O2 C1 C2 C7 -134.5(7) . . . . ?
O1 C1 C2 C7 54.9(8) . . . . ?
O2 C1 C2 C3 47.3(7) . . . . ?
O1 C1 C2 C3 -123.2(6) . . . . ?
C7 C2 C3 C4 -2.8(9) . . . . ?
C1 C2 C3 C4 175.5(6) . . . . ?
C2 C3 C4 C5 2.2(9) . . . . ?
C2 C3 C4 C4 -179.5(7) . . . 2_665 ?
C3 C4 C5 C6 0.6(9) . . . . ?
C4 C4 C5 C6 -177.7(7) 2_665 . . . ?
C4 C5 C6 C7 -2.8(10) . . . . ?
C5 C6 C7 C2 2.2(9) . . . . ?
C5 C6 C7 C8 178.3(6) . . . . ?
C3 C2 C7 C6 0.6(9) . . . . ?
C1 C2 C7 C6 -177.4(6) . . . . ?
C3 C2 C7 C8 -174.9(5) . . . . ?
C1 C2 C7 C8 7.0(10) . . . . ?
Ni1 O3 C8 O4 178.4(4) . . . . ?
Ni1 O3 C8 C7 -1.2(10) . . . . ?
C6 C7 C8 O4 -39.0(8) . . . . ?
C2 C7 C8 O4 136.7(6) . . . . ?
C6 C7 C8 O3 140.5(6) . . . . ?
C2 C7 C8 O3 -43.7(9) . . . . ?
C10 N3 C9 N4 0.5(7) . . . . ?
Ni1 N3 C9 N4 -179.9(4) . . . . ?
C11 N4 C9 N3 -0.4(7) . . . . ?
C12 N4 C9 N3 178.1(5) . . . . ?
C9 N3 C10 C11 -0.4(7) . . . . ?
Ni1 N3 C10 C11 -180.0(4) . . . . ?
N3 C10 C11 N4 0.2(7) . . . . ?
C9 N4 C11 C10 0.1(7) . . . . ?
C12 N4 C11 C10 -178.4(6) . . . . ?
C9 N4 C12 C17 143.5(6) . . . . ?
C11 N4 C12 C17 -38.2(9) . . . . ?
C9 N4 C12 C13 -36.5(9) . . . . ?
C11 N4 C12 C13 141.7(6) . . . . ?
C17 C12 C13 C14 -1.7(10) . . . . ?
N4 C12 C13 C14 178.4(5) . . . . ?
C12 C13 C14 C15 0.7(10) . . . . ?
C13 C14 C15 C16 0.2(9) . . . . ?
C13 C14 C15 N2 -178.1(6) . . . . ?
C18 N2 C15 C16 29.2(9) 1_544 . . . ?
C20 N2 C15 C16 -151.3(6) . . . . ?
C18 N2 C15 C14 -152.5(6) 1_544 . . . ?
C20 N2 C15 C14 27.1(9) . . . . ?
C14 C15 C16 C17 -0.1(9) . . . . ?
N2 C15 C16 C17 178.2(5) . . . . ?
C13 C12 C17 C16 1.7(9) . . . . ?
N4 C12 C17 C16 -178.3(5) . . . . ?
C15 C16 C17 C12 -0.9(9) . . . . ?
C19 N1 C18 N2 -0.7(7) . . . 1_566 ?
Ni1 N1 C18 N2 -174.7(4) . . . 1_566 ?
C18 N1 C19 C20 -0.2(7) . . . 1_566 ?
Ni1 N1 C19 C20 173.7(4) . . . 1_566 ?
C18 N2 C20 C19 -1.4(7) 1_544 . . 1_544 ?
C15 N2 C20 C19 179.0(6) . . . 1_544 ?

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 H5A O3 0.82 1.97 2.792(5) 174.8 2_566
O5 H5B O2 0.82 2.07 2.797(6) 147.9 2_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.105
_database_code_depnum_ccdc_archive 'CCDC 999233'
#######################################################################
#
#                 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_compound_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            3
_chemical_melting_point          ?
_chemical_formula_moiety         C20H17CoN4O6
_chemical_formula_sum            'C20 H17 Co N4 O6'
_chemical_formula_weight         468.31

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.0648(16)
_cell_length_b                   12.6093(17)
_cell_length_c                   15.0869(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.371(8)
_cell_angle_gamma                90.00
_cell_volume                     1834.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1176
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      22.2

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7562
_exptl_absorpt_correction_T_max  0.7905
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            10033
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3216
_reflns_number_gt                2187
_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 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)+(0.0307P)²+0.0376P] 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         3216
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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
N4 N -0.5896(3) 0.9504(2) 0.1237(2) 0.0291(7) Uani 1 1 d . . .
C10 C -0.5020(4) 1.0042(3) 0.2041(3) 0.0317(9) Uani 1 1 d . . .
C12 C -0.5522(4) 0.8459(3) 0.1485(3) 0.0331(9) Uani 1 1 d . . .
Co1 Co 0.28796(5) 1.01663(3) 0.97460(3) 0.02384(15) Uani 1 1 d . . .
O1 O 0.3589(2) 0.90939(18) 0.90901(17) 0.0312(6) Uani 1 1 d . . .
O2 O 0.5811(2) 0.85810(17) 0.99709(17) 0.0320(6) Uani 1 1 d . . .
O3 O 0.1025(2) 0.6350(2) 0.62555(17) 0.0357(7) Uani 1 1 d . . .
O4 O 0.1331(2) 0.46528(19) 0.67417(17) 0.0350(6) Uani 1 1 d . . .
O5 O 0.1292(3) 0.9037(2) 0.9541(2) 0.0304(7) Uani 1 1 d . . .
H5A H 0.120(4) 0.893(3) 1.012(4) 0.075(17) Uiso 1 1 d . . .
H5B H 0.057(4) 0.927(3) 0.914(3) 0.055(15) Uiso 1 1 d . . .
O6 O 0.1789(3) 1.1230(2) 1.0254(2) 0.0348(7) Uani 1 1 d . . .
H6A H 0.104(5) 1.129(3) 0.982(3) 0.063(17) Uiso 1 1 d . . .
H6B H 0.168(4) 1.097(3) 1.076(3) 0.057(15) Uiso 1 1 d . . .
N1 N 0.1635(3) 1.0764(2) 0.8262(2) 0.0279(7) Uani 1 1 d . . .
N2 N 0.0080(3) 1.0797(2) 0.66291(19) 0.0269(7) Uani 1 1 d . . .
N3 N -0.4091(3) 0.9405(2) 0.2784(2) 0.0279(7) Uani 1 1 d . . .
C1 C 0.0822(3) 1.0191(3) 0.7463(2) 0.0288(9) Uani 1 1 d . . .
H1 H 0.0764 0.9456 0.7469 0.035 Uiso 1 1 calc R . .
C2 C 0.1408(4) 1.1789(3) 0.7919(3) 0.0380(10) Uani 1 1 d . . .
H2 H 0.1848 1.2379 0.8318 0.046 Uiso 1 1 calc R . .
C3 C 0.0463(4) 1.1825(3) 0.6928(3) 0.0426(11) Uani 1 1 d . . .
H4 H 0.0134 1.2428 0.6524 0.051 Uiso 1 1 calc R . .
C4 C -0.0938(4) 1.0428(3) 0.5647(2) 0.0274(9) Uani 1 1 d . . .
C5 C -0.1294(4) 0.9381(3) 0.5476(3) 0.0347(10) Uani 1 1 d . . .
H5 H -0.0835 0.8895 0.6001 0.042 Uiso 1 1 calc R . .
C6 C -0.2320(4) 0.9029(3) 0.4541(3) 0.0337(9) Uani 1 1 d . . .
H6 H -0.2558 0.8314 0.4442 0.040 Uiso 1 1 calc R . .
C7 C -0.2992(3) 0.9742(3) 0.3753(2) 0.0265(8) Uani 1 1 d . . .
C8 C -0.2598(4) 1.0793(3) 0.3914(3) 0.0404(11) Uani 1 1 d . . .
H8 H -0.3018 1.1275 0.3381 0.048 Uiso 1 1 calc R . .
C9 C -0.1582(4) 1.1136(3) 0.4860(3) 0.0382(10) Uani 1 1 d . . .
H9 H -0.1335 1.1849 0.4964 0.046 Uiso 1 1 calc R . .
H10 H -0.5036 1.0776 0.2093 0.046 Uiso 1 1 d R . .
C11 C -0.4420(4) 0.8385(3) 0.2429(3) 0.0334(9) Uani 1 1 d . . .
H11 H -0.3974 0.7768 0.2770 0.040 Uiso 1 1 calc R . .
H12 H -0.5968 0.7884 0.1062 0.040 Uiso 1 1 d R . .
C13 C 0.4535(4) 0.8414(3) 0.9435(2) 0.0241(8) Uani 1 1 d . . .
C14 C 0.4133(3) 0.7277(3) 0.9155(2) 0.0219(8) Uani 1 1 d . . .
C15 C 0.4907(3) 0.6490(3) 0.9836(2) 0.0255(8) Uani 1 1 d . . .
H15 H 0.5661 0.6681 1.0457 0.031 Uiso 1 1 calc R . .
C16 C 0.4588(3) 0.5419(2) 0.9619(2) 0.0227(8) Uani 1 1 d . . .
C17 C 0.3496(3) 0.5167(3) 0.8656(2) 0.0260(8) Uani 1 1 d . . .
H17 H 0.3284 0.4457 0.8482 0.031 Uiso 1 1 calc R . .
C18 C 0.2718(3) 0.5937(3) 0.7951(2) 0.0237(8) Uani 1 1 d . . .
C19 C 0.3021(3) 0.7000(3) 0.8219(2) 0.0257(8) Uani 1 1 d . . .
H19 H 0.2475 0.7527 0.7768 0.031 Uiso 1 1 calc R . .
C20 C 0.1606(4) 0.5624(3) 0.6904(3) 0.0284(9) Uani 1 1 d . . .


_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
N4 C10 1.311(4) . ?
N4 C12 1.377(4) . ?
N4 Co1 2.145(3) 1_454 ?
C10 N3 1.352(4) . ?
C10 H10 0.9297 . ?
C12 C11 1.349(5) . ?
C12 H12 0.9319 . ?
Co1 O2 2.042(2) 3_677 ?
Co1 O1 2.046(2) . ?
Co1 N1 2.110(3) . ?
Co1 N4 2.145(3) 1_656 ?
Co1 O5 2.163(3) . ?
Co1 O6 2.180(3) . ?
O1 C13 1.251(4) . ?
O2 C13 1.254(4) . ?
O2 Co1 2.042(2) 3_677 ?
O3 C20 1.262(4) . ?
O4 C20 1.256(4) . ?
O5 H5A 0.94(5) . ?
O5 H5B 0.79(4) . ?
O6 H6A 0.77(4) . ?
O6 H6B 0.89(4) . ?
N1 C1 1.311(4) . ?
N1 C2 1.369(4) . ?
N2 C1 1.351(4) . ?
N2 C3 1.370(4) . ?
N2 C4 1.429(4) . ?
N3 C11 1.371(4) . ?
N3 C7 1.433(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.341(5) . ?
C2 H2 0.9300 . ?
C3 H4 0.9300 . ?
C4 C5 1.366(5) . ?
C4 C9 1.373(4) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(5) . ?
C8 C9 1.384(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C13 C14 1.499(4) . ?
C14 C15 1.382(4) . ?
C14 C19 1.388(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 C16 1.498(6) 3_667 ?
C17 C18 1.385(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.393(4) . ?
C18 C20 1.503(4) . ?
C19 H19 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
C10 N4 C12 104.9(3) . . ?
C10 N4 Co1 124.7(2) . 1_454 ?
C12 N4 Co1 127.5(2) . 1_454 ?
N4 C10 N3 112.1(3) . . ?
N4 C10 H10 123.9 . . ?
N3 C10 H10 124.0 . . ?
C11 C12 N4 110.4(3) . . ?
C11 C12 H12 124.8 . . ?
N4 C12 H12 124.8 . . ?
O2 Co1 O1 102.20(10) 3_677 . ?
O2 Co1 N1 88.45(10) 3_677 . ?
O1 Co1 N1 85.90(10) . . ?
O2 Co1 N4 93.64(10) 3_677 1_656 ?
O1 Co1 N4 93.13(10) . 1_656 ?
N1 Co1 N4 177.85(11) . 1_656 ?
O2 Co1 O5 169.27(10) 3_677 . ?
O1 Co1 O5 88.47(10) . . ?
N1 Co1 O5 91.24(11) . . ?
N4 Co1 O5 86.81(11) 1_656 . ?
O2 Co1 O6 84.75(10) 3_677 . ?
O1 Co1 O6 170.70(11) . . ?
N1 Co1 O6 88.15(12) . . ?
N4 Co1 O6 92.58(12) 1_656 . ?
O5 Co1 O6 84.52(11) . . ?
C13 O1 Co1 133.8(2) . . ?
C13 O2 Co1 136.4(2) . 3_677 ?
Co1 O5 H5A 114(3) . . ?
Co1 O5 H5B 108(3) . . ?
H5A O5 H5B 103(4) . . ?
Co1 O6 H6A 108(3) . . ?
Co1 O6 H6B 114(3) . . ?
H6A O6 H6B 103(4) . . ?
C1 N1 C2 104.8(3) . . ?
C1 N1 Co1 125.2(2) . . ?
C2 N1 Co1 129.9(2) . . ?
C1 N2 C3 106.2(3) . . ?
C1 N2 C4 126.2(3) . . ?
C3 N2 C4 127.5(3) . . ?
C10 N3 C11 106.6(3) . . ?
C10 N3 C7 126.1(3) . . ?
C11 N3 C7 127.3(3) . . ?
N1 C1 N2 112.0(3) . . ?
N1 C1 H1 124.0 . . ?
N2 C1 H1 124.0 . . ?
C3 C2 N1 110.6(3) . . ?
C3 C2 H2 124.7 . . ?
N1 C2 H2 124.7 . . ?
C2 C3 N2 106.4(3) . . ?
C2 C3 H4 126.8 . . ?
N2 C3 H4 126.8 . . ?
C5 C4 C9 119.1(3) . . ?
C5 C4 N2 121.2(3) . . ?
C9 C4 N2 119.7(3) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 N3 120.1(3) . . ?
C6 C7 N3 120.9(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 120.2(3) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C11 N3 106.1(3) . . ?
C12 C11 H11 127.0 . . ?
N3 C11 H11 127.0 . . ?
O1 C13 O2 126.9(3) . . ?
O1 C13 C14 117.8(3) . . ?
O2 C13 C14 115.3(3) . . ?
C15 C14 C19 119.5(3) . . ?
C15 C14 C13 119.2(3) . . ?
C19 C14 C13 121.3(3) . . ?
C14 C15 C16 121.9(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 117.1(3) . . ?
C15 C16 C16 121.0(4) . 3_667 ?
C17 C16 C16 121.9(4) . 3_667 ?
C18 C17 C16 122.3(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C19 118.8(3) . . ?
C17 C18 C20 120.2(3) . . ?
C19 C18 C20 120.9(3) . . ?
C14 C19 C18 120.3(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
O4 C20 O3 125.0(3) . . ?
O4 C20 C18 117.1(3) . . ?
O3 C20 C18 117.9(3) . . ?

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
C12 N4 C10 N3 1.1(4) . . . . ?
Co1 N4 C10 N3 -160.7(2) 1_454 . . . ?
C10 N4 C12 C11 -0.7(4) . . . . ?
Co1 N4 C12 C11 160.4(3) 1_454 . . . ?
O2 Co1 O1 C13 84.6(3) 3_677 . . . ?
N1 Co1 O1 C13 172.1(3) . . . . ?
N4 Co1 O1 C13 -9.8(3) 1_656 . . . ?
O5 Co1 O1 C13 -96.5(3) . . . . ?
O6 Co1 O1 C13 -137.5(6) . . . . ?
O2 Co1 N1 C1 153.2(3) 3_677 . . . ?
O1 Co1 N1 C1 50.9(3) . . . . ?
N4 Co1 N1 C1 -12(3) 1_656 . . . ?
O5 Co1 N1 C1 -37.5(3) . . . . ?
O6 Co1 N1 C1 -122.0(3) . . . . ?
O2 Co1 N1 C2 -31.4(3) 3_677 . . . ?
O1 Co1 N1 C2 -133.8(3) . . . . ?
N4 Co1 N1 C2 163(3) 1_656 . . . ?
O5 Co1 N1 C2 137.8(3) . . . . ?
O6 Co1 N1 C2 53.4(3) . . . . ?
N4 C10 N3 C11 -1.1(4) . . . . ?
N4 C10 N3 C7 179.4(3) . . . . ?
C2 N1 C1 N2 -0.5(4) . . . . ?
Co1 N1 C1 N2 175.8(2) . . . . ?
C3 N2 C1 N1 0.4(4) . . . . ?
C4 N2 C1 N1 -177.4(3) . . . . ?
C1 N1 C2 C3 0.4(5) . . . . ?
Co1 N1 C2 C3 -175.6(3) . . . . ?
N1 C2 C3 N2 -0.2(5) . . . . ?
C1 N2 C3 C2 -0.1(4) . . . . ?
C4 N2 C3 C2 177.7(3) . . . . ?
C1 N2 C4 C5 2.6(6) . . . . ?
C3 N2 C4 C5 -174.8(4) . . . . ?
C1 N2 C4 C9 -178.1(3) . . . . ?
C3 N2 C4 C9 4.5(6) . . . . ?
C9 C4 C5 C6 -2.3(6) . . . . ?
N2 C4 C5 C6 177.0(3) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C5 C6 C7 C8 1.4(6) . . . . ?
C5 C6 C7 N3 -178.0(3) . . . . ?
C10 N3 C7 C8 -15.2(5) . . . . ?
C11 N3 C7 C8 165.5(4) . . . . ?
C10 N3 C7 C6 164.2(4) . . . . ?
C11 N3 C7 C6 -15.1(6) . . . . ?
C6 C7 C8 C9 -2.5(6) . . . . ?
N3 C7 C8 C9 177.0(4) . . . . ?
C5 C4 C9 C8 1.2(6) . . . . ?
N2 C4 C9 C8 -178.1(3) . . . . ?
C7 C8 C9 C4 1.1(6) . . . . ?
N4 C12 C11 N3 0.0(4) . . . . ?
C10 N3 C11 C12 0.6(4) . . . . ?
C7 N3 C11 C12 -179.9(3) . . . . ?
Co1 O1 C13 O2 -63.2(5) . . . . ?
Co1 O1 C13 C14 119.5(3) . . . . ?
Co1 O2 C13 O1 -21.0(6) 3_677 . . . ?
Co1 O2 C13 C14 156.4(2) 3_677 . . . ?
O1 C13 C14 C15 -148.7(3) . . . . ?
O2 C13 C14 C15 33.6(5) . . . . ?
O1 C13 C14 C19 32.7(5) . . . . ?
O2 C13 C14 C19 -145.0(3) . . . . ?
C19 C14 C15 C16 -1.2(5) . . . . ?
C13 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 3.5(5) . . . . ?
C14 C15 C16 C16 -178.0(4) . . . 3_667 ?
C15 C16 C17 C18 -2.4(5) . . . . ?
C16 C16 C17 C18 179.1(4) 3_667 . . . ?
C16 C17 C18 C19 -1.1(5) . . . . ?
C16 C17 C18 C20 176.5(3) . . . . ?
C15 C14 C19 C18 -2.4(5) . . . . ?
C13 C14 C19 C18 176.1(3) . . . . ?
C17 C18 C19 C14 3.5(5) . . . . ?
C20 C18 C19 C14 -174.0(3) . . . . ?
C17 C18 C20 O4 7.1(5) . . . . ?
C19 C18 C20 O4 -175.4(3) . . . . ?
C17 C18 C20 O3 -172.7(3) . . . . ?
C19 C18 C20 O3 4.8(5) . . . . ?

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 H5A O3 0.94(5) 1.84(5) 2.786(4) 177(4) 4_576
O5 H5B O4 0.79(4) 1.91(4) 2.695(3) 169(4) 2_556
O6 H6A O3 0.77(4) 2.05(4) 2.820(4) 174(5) 2_556
O6 H6B O4 0.89(4) 1.88(4) 2.765(4) 175(4) 4_576

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 999234'
#######################################################################
#
#                 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_compound_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            4
_chemical_melting_point          ?
_chemical_formula_moiety         2(C20H19N6NiO5)6(HO0.50)
_chemical_formula_sum            'C40 H48 N12 Ni2 O15'
_chemical_formula_weight         1054.32

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'
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
_symmetry_space_group_name_Hall  '-C 2yc'

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                   24.343(9)
_cell_length_b                   12.291(4)
_cell_length_c                   18.868(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.369(10)
_cell_angle_gamma                90.00
_cell_volume                     4820(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2192
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8335
_exptl_absorpt_correction_T_max  0.8819
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            24993
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4220
_reflns_number_gt                2712
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_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 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)+(0.0906P)²+5.7455P] 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         4220
_refine_ls_number_parameters     316
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.034
_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 0.26657(3) 0.29503(5) 0.36729(4) 0.0387(2) Uani 1 1 d . . .
N1 N 0.20249(18) 0.4164(3) 0.3533(2) 0.0417(10) Uani 1 1 d . . .
N2 N 0.12343(18) 0.5039(3) 0.3525(2) 0.0406(10) Uani 1 1 d . . .
N3 N -0.08437(18) 0.5866(3) 0.3953(2) 0.0392(10) Uani 1 1 d . . .
N4 N -0.16676(19) 0.6732(3) 0.3868(3) 0.0440(10) Uani 1 1 d . . .
N5 N 0.2217(2) 0.2814(3) 0.2387(3) 0.0451(10) Uani 1 1 d . . .
N6 N 0.2116(2) 0.2629(4) 0.1161(2) 0.0452(10) Uani 1 1 d . . .
O1 O 0.32568(19) 0.4084(3) 0.3582(3) 0.0608(11) Uani 1 1 d . . .
O2 O 0.3959(3) 0.4548(6) 0.4872(4) 0.122(2) Uani 1 1 d . . .
O3 O 0.20762(17) 0.1813(3) 0.3765(2) 0.0502(9) Uani 1 1 d . . .
O4 O 0.1383(3) 0.0439(4) 0.3307(4) 0.0988(16) Uani 1 1 d . . .
O5 O 0.31838(19) 0.3064(3) 0.4975(2) 0.0634(11) Uani 1 1 d . . .
H5C H 0.3391 0.3616 0.5001 0.095 Uiso 1 1 d R . .
H5D H 0.2952 0.3237 0.5155 0.095 Uiso 1 1 d R . .
O6 O 0.4145(3) 0.3495(5) 0.2536(4) 0.1095(18) Uani 1 1 d U . .
H6C H 0.3954 0.4083 0.2412 0.164 Uiso 1 1 d R . .
H6D H 0.4290 0.3415 0.2233 0.164 Uiso 1 1 d R . .
O7 O 0.4555(3) 0.4038(6) 0.1214(5) 0.150(3) Uani 1 1 d U . .
H7C H 0.4376 0.4612 0.0953 0.224 Uiso 1 1 d R . .
H7D H 0.4971 0.4166 0.1526 0.224 Uiso 1 1 d R . .
O8 O -0.0085(8) 0.1891(13) 0.4164(12) 0.175(6) Uani 0.50 1 d PU . .
H8C H 0.0242 0.1555 0.4518 0.263 Uiso 0.50 1 d PR . .
H8D H -0.0117 0.1776 0.3716 0.263 Uiso 0.50 1 d PR . .
C1 C 0.1580(2) 0.4102(4) 0.3734(3) 0.0447(13) Uani 1 1 d . . .
H1 H 0.1514 0.3504 0.3982 0.054 Uiso 1 1 calc R . .
C2 C 0.1950(2) 0.5170(4) 0.3168(3) 0.0462(13) Uani 1 1 d . . .
H2 H 0.2195 0.5431 0.2957 0.055 Uiso 1 1 calc R . .
C3 C 0.1467(2) 0.5717(4) 0.3163(3) 0.0442(12) Uani 1 1 d . . .
H3 H 0.1321 0.6412 0.2956 0.053 Uiso 1 1 calc R . .
C4 C 0.0701(2) 0.5248(4) 0.3637(3) 0.0404(12) Uani 1 1 d . . .
C5 C 0.0593(2) 0.6292(4) 0.3791(3) 0.0457(12) Uani 1 1 d . . .
H5A H 0.0860 0.6856 0.3822 0.055 Uiso 1 1 calc R . .
C6 C 0.0080(2) 0.6496(4) 0.3899(3) 0.0454(12) Uani 1 1 d . . .
H6 H 0.0001 0.7200 0.4006 0.054 Uiso 1 1 calc R . .
C7 C 0.0315(2) 0.4403(4) 0.3591(3) 0.0488(13) Uani 1 1 d . . .
H7 H 0.0395 0.3699 0.3488 0.059 Uiso 1 1 calc R . .
H8 H -0.0460 0.4040 0.3672 0.059 Uiso 1 1 d R . .
H10 H -0.0992 0.4475 0.4427 0.059 Uiso 1 1 d R . .
H11 H -0.1885 0.5435 0.4362 0.059 Uiso 1 1 d R . .
H12 H -0.1105 0.7405 0.3510 0.059 Uiso 1 1 d R . .
C8 C -0.0196(2) 0.4608(4) 0.3700(3) 0.0489(13) Uani 1 1 d . . .
C9 C -0.0313(2) 0.5652(4) 0.3849(3) 0.0403(11) Uani 1 1 d . . .
C10 C -0.1122(3) 0.5182(4) 0.4238(3) 0.0504(14) Uani 1 1 d . . .
C11 C -0.1616(3) 0.5714(5) 0.4195(3) 0.0497(13) Uani 1 1 d . . .
C12 C -0.1192(2) 0.6799(4) 0.3731(3) 0.0435(12) Uani 1 1 d . . .
C13 C 0.2508(3) 0.2911(4) 0.1967(3) 0.0453(12) Uani 1 1 d . . .
H13 H 0.2930 0.3144 0.2195 0.054 Uiso 1 1 calc R . .
C14 C 0.1600(3) 0.2461(5) 0.1812(3) 0.0523(14) Uani 1 1 d . . .
H14 H 0.1278 0.2327 0.1926 0.063 Uiso 1 1 calc R . .
C15 C 0.1536(3) 0.2341(5) 0.1062(4) 0.0544(14) Uani 1 1 d . . .
H15 H 0.1171 0.2110 0.0574 0.065 Uiso 1 1 calc R . .
C16 C 0.2305(2) 0.2569(4) 0.0559(3) 0.0432(12) Uani 1 1 d . . .
C17 C 0.2705(3) 0.3343(4) 0.0559(3) 0.0503(13) Uani 1 1 d . . .
H17 H 0.2844 0.3914 0.0938 0.060 Uiso 1 1 calc R . .
C18 C 0.2093(3) 0.1719(4) 0.0006(3) 0.0493(13) Uani 1 1 d . . .
H18 H 0.1820 0.1194 0.0010 0.059 Uiso 1 1 calc R . .
C19 C 0.3733(4) 0.4575(6) 0.4097(6) 0.078(2) Uani 1 1 d . . .
H19 H 0.3947 0.5002 0.3909 0.094 Uiso 1 1 calc R . .
C20 C 0.1802(3) 0.1001(5) 0.3309(4) 0.0627(16) Uani 1 1 d . . .
H20 H 0.1927 0.0808 0.2937 0.075 Uiso 1 1 calc 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 O1 2.073(4) . ?
Ni1 N1 2.074(4) . ?
Ni1 O3 2.075(4) . ?
Ni1 N5 2.086(4) . ?
Ni1 N4 2.095(4) 3_545 ?
Ni1 O5 2.102(4) . ?
N1 C1 1.322(6) . ?
N1 C2 1.379(6) . ?
N2 C1 1.358(6) . ?
N2 C3 1.372(6) . ?
N2 C4 1.443(6) . ?
N3 C10 1.355(6) . ?
N3 C12 1.355(6) . ?
N3 C9 1.429(6) . ?
N4 C12 1.315(6) . ?
N4 C11 1.372(7) . ?
N4 Ni1 2.095(4) 3_455 ?
N5 C13 1.313(6) . ?
N5 C14 1.389(7) . ?
N6 C13 1.354(6) . ?
N6 C15 1.370(7) . ?
N6 C16 1.433(6) . ?
O1 C19 1.217(8) . ?
O2 C19 1.266(9) . ?
O3 C20 1.258(7) . ?
O4 C20 1.230(7) . ?
O5 H5C 0.8321 . ?
O5 H5D 0.8248 . ?
O6 H6C 0.8237 . ?
O6 H6D 0.8206 . ?
O7 H7C 0.8414 . ?
O7 H7D 0.8800 . ?
O8 H8C 0.8346 . ?
O8 H8D 0.8205 . ?
C1 H1 0.9300 . ?
C2 C3 1.350(7) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.371(7) . ?
C4 C7 1.373(7) . ?
C5 C6 1.391(7) . ?
C5 H5A 0.9300 . ?
C6 C9 1.380(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.385(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(7) . ?
C8 H8 0.9304 . ?
C10 C11 1.334(7) . ?
C10 H10 0.9293 . ?
C11 H11 0.9292 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.349(8) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.362(7) . ?
C16 C18 1.373(7) . ?
C17 C18 1.388(7) 7 ?
C17 H17 0.9300 . ?
C18 C17 1.388(7) 7 ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 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
O1 Ni1 N1 90.82(16) . . ?
O1 Ni1 O3 179.84(14) . . ?
N1 Ni1 O3 89.33(15) . . ?
O1 Ni1 N5 85.57(17) . . ?
N1 Ni1 N5 90.35(16) . . ?
O3 Ni1 N5 94.47(16) . . ?
O1 Ni1 N4 89.28(16) . 3_545 ?
N1 Ni1 N4 177.61(16) . 3_545 ?
O3 Ni1 N4 90.56(16) . 3_545 ?
N5 Ni1 N4 92.03(16) . 3_545 ?
O1 Ni1 O5 91.84(17) . . ?
N1 Ni1 O5 93.14(16) . . ?
O3 Ni1 O5 88.12(15) . . ?
N5 Ni1 O5 175.68(15) . . ?
N4 Ni1 O5 84.47(15) 3_545 . ?
C1 N1 C2 106.2(4) . . ?
C1 N1 Ni1 126.6(3) . . ?
C2 N1 Ni1 127.2(3) . . ?
C1 N2 C3 107.7(4) . . ?
C1 N2 C4 125.3(4) . . ?
C3 N2 C4 126.9(4) . . ?
C10 N3 C12 106.6(4) . . ?
C10 N3 C9 127.9(4) . . ?
C12 N3 C9 125.3(4) . . ?
C12 N4 C11 105.2(4) . . ?
C12 N4 Ni1 127.0(4) . 3_455 ?
C11 N4 Ni1 127.8(3) . 3_455 ?
C13 N5 C14 105.1(4) . . ?
C13 N5 Ni1 125.1(4) . . ?
C14 N5 Ni1 129.2(3) . . ?
C13 N6 C15 107.0(4) . . ?
C13 N6 C16 125.0(4) . . ?
C15 N6 C16 127.8(4) . . ?
C19 O1 Ni1 132.9(5) . . ?
C20 O3 Ni1 128.4(4) . . ?
Ni1 O5 H5C 95.8 . . ?
Ni1 O5 H5D 112.1 . . ?
H5C O5 H5D 106.9 . . ?
H6C O6 H6D 106.9 . . ?
H7C O7 H7D 107.8 . . ?
H8C O8 H8D 106.1 . . ?
N1 C1 N2 110.2(4) . . ?
N1 C1 H1 124.9 . . ?
N2 C1 H1 124.9 . . ?
C3 C2 N1 109.8(4) . . ?
C3 C2 H2 125.1 . . ?
N1 C2 H2 125.1 . . ?
C2 C3 N2 106.1(4) . . ?
C2 C3 H3 127.0 . . ?
N2 C3 H3 127.0 . . ?
C5 C4 C7 121.4(4) . . ?
C5 C4 N2 118.9(4) . . ?
C7 C4 N2 119.7(4) . . ?
C4 C5 C6 119.0(5) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C9 C6 C5 119.8(5) . . ?
C9 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C4 C7 C8 119.4(5) . . ?
C4 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C6 120.5(4) . . ?
C8 C9 N3 119.8(5) . . ?
C6 C9 N3 119.7(4) . . ?
C11 C10 N3 107.0(4) . . ?
C11 C10 H10 126.7 . . ?
N3 C10 H10 126.3 . . ?
C10 C11 N4 110.1(5) . . ?
C10 C11 H11 124.9 . . ?
N4 C11 H11 125.0 . . ?
N4 C12 N3 111.1(4) . . ?
N4 C12 H12 124.5 . . ?
N3 C12 H12 124.4 . . ?
N5 C13 N6 111.6(5) . . ?
N5 C13 H13 124.2 . . ?
N6 C13 H13 124.2 . . ?
C15 C14 N5 109.9(5) . . ?
C15 C14 H14 125.1 . . ?
N5 C14 H14 125.1 . . ?
C14 C15 N6 106.3(5) . . ?
C14 C15 H15 126.8 . . ?
N6 C15 H15 126.8 . . ?
C17 C16 C18 121.2(5) . . ?
C17 C16 N6 119.3(4) . . ?
C18 C16 N6 119.6(5) . . ?
C16 C17 C18 120.0(5) . 7 ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 7 . ?
C16 C18 C17 118.9(5) . 7 ?
C16 C18 H18 120.6 . . ?
C17 C18 H18 120.6 7 . ?
O1 C19 O2 124.8(7) . . ?
O1 C19 H19 117.6 . . ?
O2 C19 H19 117.6 . . ?
O4 C20 O3 126.3(6) . . ?
O4 C20 H20 116.9 . . ?
O3 C20 H20 116.9 . . ?

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 Ni1 N1 C1 -161.4(4) . . . . ?
O3 Ni1 N1 C1 18.6(4) . . . . ?
N5 Ni1 N1 C1 113.1(4) . . . . ?
N4 Ni1 N1 C1 -69(4) 3_545 . . . ?
O5 Ni1 N1 C1 -69.5(4) . . . . ?
O1 Ni1 N1 C2 22.9(4) . . . . ?
O3 Ni1 N1 C2 -157.2(4) . . . . ?
N5 Ni1 N1 C2 -62.7(4) . . . . ?
N4 Ni1 N1 C2 115(4) 3_545 . . . ?
O5 Ni1 N1 C2 114.8(4) . . . . ?
O1 Ni1 N5 C13 33.4(4) . . . . ?
N1 Ni1 N5 C13 124.2(4) . . . . ?
O3 Ni1 N5 C13 -146.4(4) . . . . ?
N4 Ni1 N5 C13 -55.7(4) 3_545 . . . ?
O5 Ni1 N5 C13 -20(2) . . . . ?
O1 Ni1 N5 C14 -156.8(4) . . . . ?
N1 Ni1 N5 C14 -66.0(4) . . . . ?
O3 Ni1 N5 C14 23.4(4) . . . . ?
N4 Ni1 N5 C14 114.1(4) 3_545 . . . ?
O5 Ni1 N5 C14 150(2) . . . . ?
N1 Ni1 O1 C19 95.9(6) . . . . ?
O3 Ni1 O1 C19 -72(52) . . . . ?
N5 Ni1 O1 C19 -173.8(6) . . . . ?
N4 Ni1 O1 C19 -81.7(6) 3_545 . . . ?
O5 Ni1 O1 C19 2.7(6) . . . . ?
O1 Ni1 O3 C20 -72(59) . . . . ?
N1 Ni1 O3 C20 120.2(5) . . . . ?
N5 Ni1 O3 C20 29.9(5) . . . . ?
N4 Ni1 O3 C20 -62.2(5) 3_545 . . . ?
O5 Ni1 O3 C20 -146.7(5) . . . . ?
C2 N1 C1 N2 -1.2(6) . . . . ?
Ni1 N1 C1 N2 -177.7(3) . . . . ?
C3 N2 C1 N1 1.0(6) . . . . ?
C4 N2 C1 N1 178.6(4) . . . . ?
C1 N1 C2 C3 1.0(6) . . . . ?
Ni1 N1 C2 C3 177.5(3) . . . . ?
N1 C2 C3 N2 -0.4(6) . . . . ?
C1 N2 C3 C2 -0.3(6) . . . . ?
C4 N2 C3 C2 -177.8(5) . . . . ?
C1 N2 C4 C5 148.8(5) . . . . ?
C3 N2 C4 C5 -34.1(7) . . . . ?
C1 N2 C4 C7 -31.0(7) . . . . ?
C3 N2 C4 C7 146.1(5) . . . . ?
C7 C4 C5 C6 -0.2(8) . . . . ?
N2 C4 C5 C6 -180.0(4) . . . . ?
C4 C5 C6 C9 -0.2(8) . . . . ?
C5 C4 C7 C8 0.2(8) . . . . ?
N2 C4 C7 C8 180.0(5) . . . . ?
C4 C7 C8 C9 0.3(8) . . . . ?
C7 C8 C9 C6 -0.7(8) . . . . ?
C7 C8 C9 N3 179.4(5) . . . . ?
C5 C6 C9 C8 0.7(8) . . . . ?
C5 C6 C9 N3 -179.4(4) . . . . ?
C10 N3 C9 C8 27.7(8) . . . . ?
C12 N3 C9 C8 -148.1(5) . . . . ?
C10 N3 C9 C6 -152.3(5) . . . . ?
C12 N3 C9 C6 31.9(7) . . . . ?
C12 N3 C10 C11 -1.0(6) . . . . ?
C9 N3 C10 C11 -177.4(5) . . . . ?
N3 C10 C11 N4 1.2(6) . . . . ?
C12 N4 C11 C10 -1.0(6) . . . . ?
Ni1 N4 C11 C10 -178.6(4) 3_455 . . . ?
C11 N4 C12 N3 0.3(6) . . . . ?
Ni1 N4 C12 N3 178.0(3) 3_455 . . . ?
C10 N3 C12 N4 0.4(6) . . . . ?
C9 N3 C12 N4 177.0(4) . . . . ?
C14 N5 C13 N6 -0.7(6) . . . . ?
Ni1 N5 C13 N6 171.1(3) . . . . ?
C15 N6 C13 N5 0.5(6) . . . . ?
C16 N6 C13 N5 -175.1(5) . . . . ?
C13 N5 C14 C15 0.7(6) . . . . ?
Ni1 N5 C14 C15 -170.6(4) . . . . ?
N5 C14 C15 N6 -0.5(6) . . . . ?
C13 N6 C15 C14 0.0(6) . . . . ?
C16 N6 C15 C14 175.4(5) . . . . ?
C13 N6 C16 C17 -40.1(7) . . . . ?
C15 N6 C16 C17 145.3(6) . . . . ?
C13 N6 C16 C18 138.3(5) . . . . ?
C15 N6 C16 C18 -36.3(8) . . . . ?
C18 C16 C17 C18 -0.1(9) . . . 7 ?
N6 C16 C17 C18 178.3(5) . . . 7 ?
C17 C16 C18 C17 0.1(9) . . . 7 ?
N6 C16 C18 C17 -178.3(5) . . . 7 ?
Ni1 O1 C19 O2 -6.0(11) . . . . ?
Ni1 O3 C20 O4 -168.6(5) . . . . ?

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
C17 H17 O4 0.93 2.51 3.346(8) 149.8 4
C14 H14 O8 0.93 2.59 3.226(17) 125.6 2
C1 H1 O5 0.93 2.57 3.450(7) 157.2 7_556
O7 H7D O6 0.88 2.12 2.872(9) 143.5 2_655
O7 H7C O2 0.84 2.03 2.778(10) 148.5 6_565
O6 H6D O7 0.82 2.45 3.203(10) 153.7 .
O6 H6C O4 0.82 2.03 2.786(7) 151.6 4
O8 H8C O2 0.83 2.15 2.959(17) 164.0 7_556
O5 H5D O3 0.82 2.07 2.764(5) 141.0 7_556
O5 H5C O2 0.83 1.91 2.704(7) 160.2 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 999235'
#######################################################################
#
#                 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_compound_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N6 Ni O5'
_chemical_formula_sum            'C26 H20 N6 Ni O5'
_chemical_formula_weight         555.19

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'
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
_symmetry_space_group_name_Hall  '-C 2yc'

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                   24.579(5)
_cell_length_b                   11.8337(18)
_cell_length_c                   18.816(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.090(5)
_cell_angle_gamma                90.00
_cell_volume                     4686.8(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1284
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      17.79

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8792
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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_reflns_number            24491
_diffrn_reflns_av_R_equivalents  0.1495
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4162
_reflns_number_gt                2468
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1700P)²+0.2275P] 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         4162
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1322
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2673
_refine_ls_wR_factor_gt          0.2206
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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 0.23066(4) 0.72588(8) 0.12713(6) 0.0332(4) Uani 1 1 d . . .
O1 O 0.1553(3) 0.6078(5) 0.0849(3) 0.0458(14) Uani 1 1 d . . .
O2 O 0.1749(2) 0.6875(5) -0.0050(3) 0.0421(13) Uani 1 1 d . . .
O3 O -0.1414(3) 0.4924(6) -0.2826(4) 0.076(2) Uani 1 1 d . . .
O4 O -0.0984(3) 0.3224(6) -0.2547(4) 0.0710(19) Uani 1 1 d . . .
O5 O 0.2846(3) 0.8491(4) 0.1148(4) 0.0468(14) Uani 1 1 d . . .
H5A H 0.2820 0.8422 0.0698 0.070 Uiso 1 1 calc R . .
H5B H 0.3158 0.8866 0.1622 0.070 Uiso 1 1 d R . .
N1 N 0.2955(3) 0.6011(5) 0.1441(4) 0.0386(15) Uani 1 1 d . . .
N2 N 0.3733(3) 0.5100(5) 0.1458(4) 0.0380(15) Uani 1 1 d . . .
N3 N 0.5832(3) 0.4333(6) 0.1067(4) 0.0412(16) Uani 1 1 d . . .
N4 N 0.6641(3) 0.3495(5) 0.1084(4) 0.0390(15) Uani 1 1 d . . .
N5 N 0.2712(3) 0.7409(5) 0.2535(4) 0.0379(15) Uani 1 1 d . . .
N6 N 0.2836(3) 0.7540(5) 0.3779(4) 0.0408(17) Uani 1 1 d . . .
C1 C 0.3033(4) 0.4962(6) 0.1815(5) 0.0409(19) Uani 1 1 d . . .
H1 H 0.2787 0.4693 0.2024 0.049 Uiso 1 1 calc R . .
C2 C 0.3510(4) 0.4395(7) 0.1833(5) 0.045(2) Uani 1 1 d . . .
H2 H 0.3658 0.3679 0.2052 0.054 Uiso 1 1 calc R . .
C3 C 0.3383(4) 0.6029(7) 0.1226(5) 0.0399(19) Uani 1 1 d . . .
H3 H 0.3435 0.6624 0.0943 0.048 Uiso 1 1 calc R . .
C4 C 0.4271(4) 0.4892(7) 0.1351(5) 0.0403(19) Uani 1 1 d . . .
C5 C 0.4446(4) 0.3807(7) 0.1321(6) 0.048(2) Uani 1 1 d . . .
H5 H 0.4223 0.3200 0.1360 0.057 Uiso 1 1 calc R . .
C6 C 0.4970(4) 0.3628(8) 0.1229(6) 0.055(2) Uani 1 1 d . . .
H6 H 0.5096 0.2895 0.1204 0.066 Uiso 1 1 calc R . .
C7 C 0.5296(3) 0.4529(7) 0.1176(5) 0.0392(19) Uani 1 1 d . . .
C8 C 0.5115(4) 0.5604(8) 0.1217(6) 0.056(2) Uani 1 1 d . . .
H8 H 0.5328 0.6217 0.1164 0.068 Uiso 1 1 calc R . .
C9 C 0.4616(4) 0.5776(7) 0.1335(6) 0.054(2) Uani 1 1 d . . .
H9 H 0.4513 0.6507 0.1406 0.065 Uiso 1 1 calc R . .
C10 C 0.6125(5) 0.5115(7) 0.0842(6) 0.057(2) Uani 1 1 d . . .
H10 H 0.6009 0.5868 0.0708 0.069 Uiso 1 1 calc R . .
C11 C 0.6612(4) 0.4588(8) 0.0854(6) 0.054(2) Uani 1 1 d . . .
H11 H 0.6890 0.4925 0.0721 0.065 Uiso 1 1 calc R . .
C12 C 0.6169(4) 0.3360(7) 0.1220(5) 0.0416(19) Uani 1 1 d . . .
H12 H 0.6079 0.2690 0.1397 0.050 Uiso 1 1 calc R . .
C13 C 0.3289(4) 0.7928(7) 0.3079(5) 0.048(2) Uani 1 1 d . . .
H13 H 0.3581 0.8180 0.2940 0.058 Uiso 1 1 calc R . .
C14 C 0.3361(4) 0.8008(8) 0.3831(6) 0.056(2) Uani 1 1 d . . .
H14 H 0.3705 0.8324 0.4302 0.067 Uiso 1 1 calc R . .
C15 C 0.2455(4) 0.7172(7) 0.2979(5) 0.0430(19) Uani 1 1 d . . .
H15 H 0.2068 0.6806 0.2779 0.052 Uiso 1 1 calc R . .
C16 C 0.2665(4) 0.7495(7) 0.4409(5) 0.044(2) Uani 1 1 d . . .
C17 C 0.2906(4) 0.8341(7) 0.5015(5) 0.049(2) Uani 1 1 d . . .
H17 H 0.3177 0.8897 0.5023 0.059 Uiso 1 1 calc R . .
C18 C 0.2271(4) 0.6675(7) 0.4399(5) 0.045(2) Uani 1 1 d . . .
H18 H 0.2119 0.6120 0.3992 0.054 Uiso 1 1 calc R . .
C19 C 0.1392(4) 0.6257(7) 0.0079(6) 0.048(2) Uani 1 1 d . . .
C20 C 0.0825(4) 0.5726(8) -0.0581(5) 0.053(2) Uani 1 1 d . . .
C21 C 0.0640(4) 0.5832(7) -0.1425(5) 0.047(2) Uani 1 1 d . . .
H21 H 0.0899 0.6230 -0.1563 0.057 Uiso 1 1 calc R . .
C22 C 0.0075(4) 0.5351(7) -0.2057(5) 0.047(2) Uani 1 1 d . . .
C23 C -0.0319(4) 0.4761(8) -0.1856(6) 0.057(2) Uani 1 1 d . . .
C24 C -0.0106(5) 0.4569(11) -0.1020(6) 0.081(4) Uani 1 1 d . . .
H24 H -0.0341 0.4105 -0.0877 0.097 Uiso 1 1 calc R . .
C25 C 0.0447(5) 0.5055(10) -0.0403(6) 0.078(3) Uani 1 1 d . . .
H25 H 0.0570 0.4930 0.0148 0.094 Uiso 1 1 calc R . .
C26 C -0.0954(4) 0.4249(8) -0.2465(6) 0.051(2) Uani 1 1 d . . .


_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 N5 2.056(6) . ?
Ni1 O5 2.063(5) . ?
Ni1 N1 2.074(6) . ?
Ni1 N4 2.084(6) 3_455 ?
Ni1 O1 2.120(5) . ?
Ni1 O2 2.178(5) . ?
Ni1 C19 2.506(9) . ?
O1 C19 1.306(10) . ?
O2 C19 1.258(9) . ?
O3 C26 1.260(10) . ?
O4 C26 1.220(11) . ?
O5 H5A 0.8200 . ?
O5 H5B 0.9351 . ?
N1 C3 1.307(9) . ?
N1 C1 1.391(9) . ?
N2 C3 1.324(9) . ?
N2 C2 1.378(10) . ?
N2 C4 1.455(9) . ?
N3 C12 1.360(10) . ?
N3 C10 1.367(10) . ?
N3 C7 1.451(9) . ?
N4 C12 1.321(9) . ?
N4 C11 1.354(10) . ?
N4 Ni1 2.084(6) 3_545 ?
N5 C15 1.313(9) . ?
N5 C13 1.392(10) . ?
N6 C14 1.362(10) . ?
N6 C15 1.370(10) . ?
N6 C16 1.448(9) . ?
C1 C2 1.336(10) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C9 1.357(11) . ?
C4 C5 1.365(11) . ?
C5 C6 1.401(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.364(12) . ?
C8 C9 1.370(11) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.340(11) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.337(11) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C18 1.365(11) . ?
C16 C17 1.399(11) . ?
C17 C18 1.376(10) 7_566 ?
C17 H17 0.9300 . ?
C18 C17 1.376(10) 7_566 ?
C18 H18 0.9300 . ?
C19 C20 1.446(12) . ?
C20 C25 1.390(12) . ?
C20 C21 1.413(11) . ?
C21 C22 1.401(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.396(11) . ?
C22 C22 1.509(16) 2_554 ?
C23 C24 1.396(13) . ?
C23 C26 1.506(12) . ?
C24 C25 1.376(13) . ?
C24 H24 0.9300 . ?
C25 H25 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
N5 Ni1 O5 96.5(2) . . ?
N5 Ni1 N1 90.5(2) . . ?
O5 Ni1 N1 91.9(2) . . ?
N5 Ni1 N4 90.2(2) . 3_455 ?
O5 Ni1 N4 88.8(2) . 3_455 ?
N1 Ni1 N4 179.0(3) . 3_455 ?
N5 Ni1 O1 107.4(2) . . ?
O5 Ni1 O1 155.7(2) . . ?
N1 Ni1 O1 92.4(2) . . ?
N4 Ni1 O1 86.7(2) 3_455 . ?
N5 Ni1 O2 168.8(2) . . ?
O5 Ni1 O2 94.7(2) . . ?
N1 Ni1 O2 90.5(2) . . ?
N4 Ni1 O2 88.7(2) 3_455 . ?
O1 Ni1 O2 61.4(2) . . ?
N5 Ni1 C19 138.6(3) . . ?
O5 Ni1 C19 124.4(3) . . ?
N1 Ni1 C19 93.7(3) . . ?
N4 Ni1 C19 85.3(3) 3_455 . ?
O1 Ni1 C19 31.4(2) . . ?
O2 Ni1 C19 30.1(2) . . ?
C19 O1 Ni1 90.9(5) . . ?
C19 O2 Ni1 89.5(5) . . ?
Ni1 O5 H5A 109.5 . . ?
Ni1 O5 H5B 119.1 . . ?
H5A O5 H5B 128.4 . . ?
C3 N1 C1 104.5(6) . . ?
C3 N1 Ni1 128.2(5) . . ?
C1 N1 Ni1 127.3(5) . . ?
C3 N2 C2 107.9(6) . . ?
C3 N2 C4 125.2(6) . . ?
C2 N2 C4 126.8(6) . . ?
C12 N3 C10 106.1(6) . . ?
C12 N3 C7 127.1(7) . . ?
C10 N3 C7 126.7(7) . . ?
C12 N4 C11 105.7(7) . . ?
C12 N4 Ni1 125.0(5) . 3_545 ?
C11 N4 Ni1 129.2(5) . 3_545 ?
C15 N5 C13 105.6(6) . . ?
C15 N5 Ni1 127.8(6) . . ?
C13 N5 Ni1 126.1(5) . . ?
C14 N6 C15 107.0(6) . . ?
C14 N6 C16 128.4(7) . . ?
C15 N6 C16 124.4(7) . . ?
C2 C1 N1 110.5(7) . . ?
C2 C1 H1 124.8 . . ?
N1 C1 H1 124.8 . . ?
C1 C2 N2 105.1(7) . . ?
C1 C2 H2 127.5 . . ?
N2 C2 H2 127.5 . . ?
N1 C3 N2 112.0(7) . . ?
N1 C3 H3 124.0 . . ?
N2 C3 H3 124.0 . . ?
C9 C4 C5 120.6(7) . . ?
C9 C4 N2 119.7(7) . . ?
C5 C4 N2 119.6(7) . . ?
C4 C5 C6 118.6(8) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.1(8) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.1(7) . . ?
C8 C7 N3 120.2(7) . . ?
C6 C7 N3 119.6(7) . . ?
C7 C8 C9 119.6(8) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C4 C9 C8 120.7(8) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 N3 106.8(7) . . ?
C11 C10 H10 126.6 . . ?
N3 C10 H10 126.6 . . ?
C10 C11 N4 110.5(8) . . ?
C10 C11 H11 124.8 . . ?
N4 C11 H11 124.8 . . ?
N4 C12 N3 110.9(7) . . ?
N4 C12 H12 124.5 . . ?
N3 C12 H12 124.5 . . ?
C14 C13 N5 109.7(7) . . ?
C14 C13 H13 125.2 . . ?
N5 C13 H13 125.2 . . ?
C13 C14 N6 107.1(8) . . ?
C13 C14 H14 126.5 . . ?
N6 C14 H14 126.5 . . ?
N5 C15 N6 110.6(7) . . ?
N5 C15 H15 124.7 . . ?
N6 C15 H15 124.7 . . ?
C18 C16 C17 121.2(7) . . ?
C18 C16 N6 121.2(7) . . ?
C17 C16 N6 117.5(7) . . ?
C18 C17 C16 117.8(8) 7_566 . ?
C18 C17 H17 121.1 7_566 . ?
C16 C17 H17 121.1 . . ?
C16 C18 C17 121.0(8) . 7_566 ?
C16 C18 H18 119.5 . . ?
C17 C18 H18 119.5 7_566 . ?
O2 C19 O1 117.7(8) . . ?
O2 C19 C20 123.0(8) . . ?
O1 C19 C20 119.2(7) . . ?
O2 C19 Ni1 60.4(4) . . ?
O1 C19 Ni1 57.7(4) . . ?
C20 C19 Ni1 174.4(6) . . ?
C25 C20 C21 117.0(8) . . ?
C25 C20 C19 120.6(8) . . ?
C21 C20 C19 122.4(8) . . ?
C22 C21 C20 121.5(8) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 119.6(8) . . ?
C23 C22 C22 119.5(8) . 2_554 ?
C21 C22 C22 120.5(8) . 2_554 ?
C22 C23 C24 118.6(8) . . ?
C22 C23 C26 125.8(8) . . ?
C24 C23 C26 115.5(8) . . ?
C25 C24 C23 121.0(10) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C20 121.9(9) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
O4 C26 O3 125.7(8) . . ?
O4 C26 C23 117.9(9) . . ?
O3 C26 C23 116.4(8) . . ?

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
N5 Ni1 O1 C19 175.6(5) . . . . ?
O5 Ni1 O1 C19 6.8(8) . . . . ?
N1 Ni1 O1 C19 -93.2(5) . . . . ?
N4 Ni1 O1 C19 86.4(5) 3_455 . . . ?
O2 Ni1 O1 C19 -3.9(4) . . . . ?
N5 Ni1 O2 C19 1.7(14) . . . . ?
O5 Ni1 O2 C19 -171.5(5) . . . . ?
N1 Ni1 O2 C19 96.5(5) . . . . ?
N4 Ni1 O2 C19 -82.9(5) 3_455 . . . ?
O1 Ni1 O2 C19 4.1(5) . . . . ?
N5 Ni1 N1 C3 -117.6(7) . . . . ?
O5 Ni1 N1 C3 -21.1(7) . . . . ?
N4 Ni1 N1 C3 109(14) 3_455 . . . ?
O1 Ni1 N1 C3 135.0(7) . . . . ?
O2 Ni1 N1 C3 73.6(7) . . . . ?
C19 Ni1 N1 C3 103.6(7) . . . . ?
N5 Ni1 N1 C1 62.2(7) . . . . ?
O5 Ni1 N1 C1 158.7(6) . . . . ?
N4 Ni1 N1 C1 -71(14) 3_455 . . . ?
O1 Ni1 N1 C1 -45.2(6) . . . . ?
O2 Ni1 N1 C1 -106.6(6) . . . . ?
C19 Ni1 N1 C1 -76.7(7) . . . . ?
O5 Ni1 N5 C15 153.4(7) . . . . ?
N1 Ni1 N5 C15 -114.6(7) . . . . ?
N4 Ni1 N5 C15 64.6(7) 3_455 . . . ?
O1 Ni1 N5 C15 -22.0(7) . . . . ?
O2 Ni1 N5 C15 -19.8(16) . . . . ?
C19 Ni1 N5 C15 -18.5(9) . . . . ?
O5 Ni1 N5 C13 -17.4(7) . . . . ?
N1 Ni1 N5 C13 74.5(7) . . . . ?
N4 Ni1 N5 C13 -106.2(7) 3_455 . . . ?
O1 Ni1 N5 C13 167.2(6) . . . . ?
O2 Ni1 N5 C13 169.4(10) . . . . ?
C19 Ni1 N5 C13 170.7(6) . . . . ?
C3 N1 C1 C2 1.5(9) . . . . ?
Ni1 N1 C1 C2 -178.3(6) . . . . ?
N1 C1 C2 N2 -0.4(9) . . . . ?
C3 N2 C2 C1 -0.9(9) . . . . ?
C4 N2 C2 C1 177.4(7) . . . . ?
C1 N1 C3 N2 -2.1(9) . . . . ?
Ni1 N1 C3 N2 177.7(5) . . . . ?
C2 N2 C3 N1 2.0(9) . . . . ?
C4 N2 C3 N1 -176.4(7) . . . . ?
C3 N2 C4 C9 28.3(12) . . . . ?
C2 N2 C4 C9 -149.7(9) . . . . ?
C3 N2 C4 C5 -155.9(8) . . . . ?
C2 N2 C4 C5 26.1(12) . . . . ?
C9 C4 C5 C6 -3.3(13) . . . . ?
N2 C4 C5 C6 -179.1(8) . . . . ?
C4 C5 C6 C7 0.3(14) . . . . ?
C5 C6 C7 C8 0.3(14) . . . . ?
C5 C6 C7 N3 -179.0(8) . . . . ?
C12 N3 C7 C8 162.1(8) . . . . ?
C10 N3 C7 C8 -13.2(13) . . . . ?
C12 N3 C7 C6 -18.6(12) . . . . ?
C10 N3 C7 C6 166.1(9) . . . . ?
C6 C7 C8 C9 1.9(14) . . . . ?
N3 C7 C8 C9 -178.8(8) . . . . ?
C5 C4 C9 C8 5.7(14) . . . . ?
N2 C4 C9 C8 -178.5(8) . . . . ?
C7 C8 C9 C4 -5.0(14) . . . . ?
C12 N3 C10 C11 1.1(10) . . . . ?
C7 N3 C10 C11 177.2(8) . . . . ?
N3 C10 C11 N4 -0.4(11) . . . . ?
C12 N4 C11 C10 -0.4(10) . . . . ?
Ni1 N4 C11 C10 -177.0(6) 3_545 . . . ?
C11 N4 C12 N3 1.1(9) . . . . ?
Ni1 N4 C12 N3 177.9(5) 3_545 . . . ?
C10 N3 C12 N4 -1.4(9) . . . . ?
C7 N3 C12 N4 -177.5(7) . . . . ?
C15 N5 C13 C14 -1.1(10) . . . . ?
Ni1 N5 C13 C14 171.4(6) . . . . ?
N5 C13 C14 N6 0.3(11) . . . . ?
C15 N6 C14 C13 0.5(10) . . . . ?
C16 N6 C14 C13 -175.0(8) . . . . ?
C13 N5 C15 N6 1.4(9) . . . . ?
Ni1 N5 C15 N6 -170.9(5) . . . . ?
C14 N6 C15 N5 -1.2(9) . . . . ?
C16 N6 C15 N5 174.5(7) . . . . ?
C14 N6 C16 C18 -155.3(9) . . . . ?
C15 N6 C16 C18 29.9(12) . . . . ?
C14 N6 C16 C17 26.3(13) . . . . ?
C15 N6 C16 C17 -148.5(8) . . . . ?
C18 C16 C17 C18 -0.4(14) . . . 7_566 ?
N6 C16 C17 C18 178.0(8) . . . 7_566 ?
C17 C16 C18 C17 0.4(15) . . . 7_566 ?
N6 C16 C18 C17 -177.9(8) . . . 7_566 ?
Ni1 O2 C19 O1 -6.6(7) . . . . ?
Ni1 O2 C19 C20 174.8(8) . . . . ?
Ni1 O1 C19 O2 6.8(7) . . . . ?
Ni1 O1 C19 C20 -174.6(7) . . . . ?
N5 Ni1 C19 O2 -179.5(4) . . . . ?
O5 Ni1 C19 O2 10.3(6) . . . . ?
N1 Ni1 C19 O2 -84.6(5) . . . . ?
N4 Ni1 C19 O2 95.5(5) 3_455 . . . ?
O1 Ni1 C19 O2 -173.1(8) . . . . ?
N5 Ni1 C19 O1 -6.4(7) . . . . ?
O5 Ni1 C19 O1 -176.6(4) . . . . ?
N1 Ni1 C19 O1 88.5(5) . . . . ?
N4 Ni1 C19 O1 -91.4(5) 3_455 . . . ?
O2 Ni1 C19 O1 173.1(8) . . . . ?
N5 Ni1 C19 C20 52(7) . . . . ?
O5 Ni1 C19 C20 -118(7) . . . . ?
N1 Ni1 C19 C20 147(7) . . . . ?
N4 Ni1 C19 C20 -33(7) 3_455 . . . ?
O1 Ni1 C19 C20 59(7) . . . . ?
O2 Ni1 C19 C20 -128(7) . . . . ?
O2 C19 C20 C25 -179.7(9) . . . . ?
O1 C19 C20 C25 1.7(14) . . . . ?
Ni1 C19 C20 C25 -54(7) . . . . ?
O2 C19 C20 C21 2.1(14) . . . . ?
O1 C19 C20 C21 -176.5(8) . . . . ?
Ni1 C19 C20 C21 128(7) . . . . ?
C25 C20 C21 C22 4.6(14) . . . . ?
C19 C20 C21 C22 -177.2(8) . . . . ?
C20 C21 C22 C23 0.6(13) . . . . ?
C20 C21 C22 C22 -172.5(7) . . . 2_554 ?
C21 C22 C23 C24 -6.4(14) . . . . ?
C22 C22 C23 C24 166.7(9) 2_554 . . . ?
C21 C22 C23 C26 176.8(9) . . . . ?
C22 C22 C23 C26 -10.1(13) 2_554 . . . ?
C22 C23 C24 C25 7.2(17) . . . . ?
C26 C23 C24 C25 -175.7(11) . . . . ?
C23 C24 C25 C20 -2.0(19) . . . . ?
C21 C20 C25 C24 -3.9(17) . . . . ?
C19 C20 C25 C24 177.8(11) . . . . ?
C22 C23 C26 O4 105.7(12) . . . . ?
C24 C23 C26 O4 -71.2(12) . . . . ?
C22 C23 C26 O3 -76.6(12) . . . . ?
C24 C23 C26 O3 106.5(11) . . . . ?

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 H5A O2 0.82 2.02 2.753(7) 149.0 7_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.106
_database_code_depnum_ccdc_archive 'CCDC 999236'
