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

#######################################################################
#
#                 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_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C15 H17 N1 Co O9, C3 H7 N1 O1'
_chemical_formula_sum            'C18 H24 Co N2 O10'
_chemical_formula_weight         487.32

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Cmcm

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

_cell_length_a                   9.9021(7)
_cell_length_b                   27.824(2)
_cell_length_c                   7.5624(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2083.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1384
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      27.76

_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8104
_exptl_absorpt_correction_T_max  0.9518
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            9884
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         27.76
_reflns_number_total             1384
_reflns_number_gt                1142
_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    SHELXP-97
_computing_publication_material  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)+(0.1022P)²+3.5371P] 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         1384
_refine_ls_number_parameters     121
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.062
_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
Co1 Co 0.5000 0.0000 1.0000 0.0256(3) Uani 1 4 d S . .
O1 O 0.4709(5) 0.06529(11) 0.8931(5) 0.0376(18) Uani 0.50 1 d P . .
O2 O 0.2069(3) 0.39946(11) 0.7500 0.0560(10) Uani 1 2 d S . .
O3 O 0.3774(3) 0.45016(10) 0.7500 0.0484(9) Uani 1 2 d SD . .
H3A H 0.473(2) 0.455(3) 0.7500 0.058 Uiso 0.50 2 d SPD . .
O4 O 0.5000 -0.03909(12) 0.7500 0.0249(8) Uani 1 4 d S . .
H4 H 0.560(4) -0.0570(15) 0.7500 0.030 Uiso 1 2 d S . .
O5 O 0.7110(4) 0.0000 1.0000 0.0801(18) Uani 1 2 d SD . .
H5 H 0.756(5) -0.0164(17) 0.912(5) 0.096 Uiso 1 1 d D . .
N1 N 0.5000 0.29087(15) 0.7500 0.0301(10) Uani 1 4 d S . .
C1 C 0.5000 0.23896(17) 0.7500 0.0283(11) Uani 1 4 d S . .
C2 C 0.5000 0.21456(13) 0.9092(6) 0.0405(10) Uani 1 2 d S . .
H2 H 0.5000 0.2314 1.0155 0.049 Uiso 1 2 calc SR . .
C3 C 0.5000 0.16492(13) 0.9084(6) 0.0412(11) Uani 1 2 d S . .
H3 H 0.5000 0.1482 1.0150 0.049 Uiso 1 2 calc SR . .
C4 C 0.5000 0.13967(16) 0.7500 0.0291(11) Uani 1 4 d S . .
C5 C 0.5000 0.08527(17) 0.7500 0.0300(11) Uani 1 4 d S . .
C6 C 0.3863(4) 0.31873(12) 0.7500 0.0309(9) Uani 1 2 d S . .
C7 C 0.4275(4) 0.36600(12) 0.7500 0.0284(8) Uani 1 2 d S . .
C8 C 0.2519(5) 0.29583(17) 0.7500 0.0615(16) Uani 1 2 d S . .
H8A H 0.2622 0.2615 0.7500 0.092 Uiso 1 2 calc SR . .
H8B H 0.2030 0.3055 0.6464 0.092 Uiso 0.50 1 calc PR . .
H8C H 0.2030 0.3055 0.8536 0.092 Uiso 0.50 1 calc PR . .
C9 C 0.3289(4) 0.40611(13) 0.7500 0.0369(9) Uani 1 2 d S . .
O6 O 0.5000 0.2950(4) 0.2131 0.130(4) Uani 0.50 2 d SPU . .
N2 N 0.5000 0.3750(3) 0.2500 0.0628(18) Uani 1 4 d S . .
C10 C 0.4288(18) 0.3357(6) 0.2500 0.094(5) Uani 0.50 2 d SPU . .
C11 C 0.655(2) 0.3727(7) 0.2500 0.101(5) Uani 0.50 2 d SPU . .
C12 C 0.4473(17) 0.4230(7) 0.2500 0.103(5) Uani 0.50 2 d SPU . .


_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 O1 2.009(3) 12_655 ?
Co1 O1 2.009(3) . ?
Co1 O1 2.009(3) 4_557 ?
Co1 O1 2.009(3) 9_657 ?
Co1 O5 2.089(4) 9_657 ?
Co1 O5 2.089(4) . ?
Co1 O4 2.1811(17) 9_657 ?
Co1 O4 2.1811(17) . ?
O1 O1 0.575(10) 12_655 ?
O1 C5 1.250(4) . ?
O2 C9 1.222(6) . ?
O3 C9 1.316(5) . ?
O3 H3A 0.95(2) . ?
O4 Co1 2.1811(17) 2_654 ?
O4 H4 0.77(4) . ?
O5 H5 0.924(19) . ?
N1 C6 1.367(4) 3_656 ?
N1 C6 1.367(4) . ?
N1 C1 1.444(6) . ?
C1 C2 1.382(5) . ?
C1 C2 1.382(5) 10_557 ?
C2 C3 1.381(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C3 1.389(5) 10_557 ?
C4 C5 1.514(6) . ?
C5 O1 1.250(4) 10_557 ?
C5 O1 1.250(4) 3_656 ?
C5 O1 1.250(4) 12_655 ?
C6 C7 1.377(5) . ?
C6 C8 1.476(5) . ?
C7 C7 1.435(8) 3_656 ?
C7 C9 1.483(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O6 O6 0.5575 10_556 ?
O6 C10 1.364(17) 3_655 ?
O6 C10 1.364(17) . ?
N2 C10 1.301(18) . ?
N2 C10 1.301(18) 3_655 ?
N2 C12 1.435(18) 3_655 ?
N2 C12 1.435(18) . ?
N2 C11 1.54(2) 3_655 ?
N2 C11 1.54(2) . ?
C10 C11 1.32(2) 3_655 ?
C10 O6 1.364(17) 10_556 ?
C10 C10 1.41(4) 3_655 ?
C11 C10 1.32(2) 3_655 ?
C11 C12 1.73(2) 3_655 ?
C12 C12 1.04(3) 3_655 ?
C12 C11 1.73(2) 3_655 ?

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 Co1 O1 16.5(3) 12_655 . ?
O1 Co1 O1 180.00(8) 12_655 4_557 ?
O1 Co1 O1 163.5(3) . 4_557 ?
O1 Co1 O1 163.5(3) 12_655 9_657 ?
O1 Co1 O1 180.00(8) . 9_657 ?
O1 Co1 O1 16.5(3) 4_557 9_657 ?
O1 Co1 O5 98.23(15) 12_655 9_657 ?
O1 Co1 O5 81.77(15) . 9_657 ?
O1 Co1 O5 81.77(15) 4_557 9_657 ?
O1 Co1 O5 98.23(15) 9_657 9_657 ?
O1 Co1 O5 81.77(15) 12_655 . ?
O1 Co1 O5 98.23(15) . . ?
O1 Co1 O5 98.23(15) 4_557 . ?
O1 Co1 O5 81.77(15) 9_657 . ?
O5 Co1 O5 180.0 9_657 . ?
O1 Co1 O4 84.15(13) 12_655 9_657 ?
O1 Co1 O4 84.15(13) . 9_657 ?
O1 Co1 O4 95.85(13) 4_557 9_657 ?
O1 Co1 O4 95.85(13) 9_657 9_657 ?
O5 Co1 O4 90.0 9_657 9_657 ?
O5 Co1 O4 90.0 . 9_657 ?
O1 Co1 O4 95.85(13) 12_655 . ?
O1 Co1 O4 95.85(13) . . ?
O1 Co1 O4 84.15(13) 4_557 . ?
O1 Co1 O4 84.15(13) 9_657 . ?
O5 Co1 O4 90.0 9_657 . ?
O5 Co1 O4 90.0 . . ?
O4 Co1 O4 180.00(15) 9_657 . ?
O1 O1 C5 76.7(2) 12_655 . ?
O1 O1 Co1 81.77(15) 12_655 . ?
C5 O1 Co1 135.8(3) . . ?
C9 O3 H3A 119(5) . . ?
Co1 O4 Co1 120.18(15) 2_654 . ?
Co1 O4 H4 108.7(13) 2_654 . ?
Co1 O4 H4 108.7(13) . . ?
Co1 O5 H5 119(3) . . ?
C6 N1 C6 110.9(4) 3_656 . ?
C6 N1 C1 124.6(2) 3_656 . ?
C6 N1 C1 124.6(2) . . ?
C2 C1 C2 121.2(5) . 10_557 ?
C2 C1 N1 119.4(2) . . ?
C2 C1 N1 119.4(2) 10_557 . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C3 119.2(5) 10_557 . ?
C3 C4 C5 120.4(2) 10_557 . ?
C3 C4 C5 120.4(2) . . ?
O1 C5 O1 119.9(5) . 10_557 ?
O1 C5 O1 127.2(5) . 3_656 ?
O1 C5 O1 26.6(5) 10_557 3_656 ?
O1 C5 O1 26.6(5) . 12_655 ?
O1 C5 O1 127.2(5) 10_557 12_655 ?
O1 C5 O1 119.9(5) 3_656 12_655 ?
O1 C5 C4 116.4(2) . . ?
O1 C5 C4 116.4(2) 10_557 . ?
O1 C5 C4 116.4(2) 3_656 . ?
O1 C5 C4 116.4(2) 12_655 . ?
N1 C6 C7 107.3(3) . . ?
N1 C6 C8 119.9(3) . . ?
C7 C6 C8 132.8(4) . . ?
C6 C7 C7 107.3(2) . 3_656 ?
C6 C7 C9 121.5(3) . . ?
C7 C7 C9 131.2(2) 3_656 . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O3 120.1(4) . . ?
O2 C9 C7 122.5(4) . . ?
O3 C9 C7 117.4(4) . . ?
O6 O6 C10 78.21(16) 10_556 3_655 ?
O6 O6 C10 78.21(15) 10_556 . ?
C10 O6 C10 62.3(16) 3_655 . ?
C10 N2 C10 65.7(16) . 3_655 ?
C10 N2 C12 168.5(10) . 3_655 ?
C10 N2 C12 125.8(11) 3_655 3_655 ?
C10 N2 C12 125.8(11) . . ?
C10 N2 C12 168.5(10) 3_655 . ?
C12 N2 C12 42.7(14) 3_655 . ?
C10 N2 C11 54.8(10) . 3_655 ?
C10 N2 C11 120.5(12) 3_655 3_655 ?
C12 N2 C11 113.7(11) 3_655 3_655 ?
C12 N2 C11 71.0(10) . 3_655 ?
C10 N2 C11 120.5(12) . . ?
C10 N2 C11 54.8(10) 3_655 . ?
C12 N2 C11 71.0(10) 3_655 . ?
C12 N2 C11 113.7(11) . . ?
C11 N2 C11 175.3(16) 3_655 . ?
N2 C10 C11 71.7(13) . 3_655 ?
N2 C10 O6 114.7(13) . . ?
C11 C10 O6 166.3(9) 3_655 . ?
N2 C10 O6 114.7(13) . 10_556 ?
C11 C10 O6 166.3(9) 3_655 10_556 ?
O6 C10 O6 23.6(3) . 10_556 ?
N2 C10 C10 57.2(8) . 3_655 ?
C11 C10 C10 128.9(12) 3_655 3_655 ?
O6 C10 C10 58.9(8) . 3_655 ?
O6 C10 C10 58.9(8) 10_556 3_655 ?
C10 C11 N2 53.5(11) 3_655 . ?
C10 C11 C12 105.3(16) 3_655 3_655 ?
N2 C11 C12 51.8(9) . 3_655 ?
C12 C12 N2 68.7(7) 3_655 . ?
C12 C12 C11 125.9(9) 3_655 3_655 ?
N2 C12 C11 57.2(9) . 3_655 ?

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
O3 H3A O3 0.95(2) 1.49(3) 2.429(7) 168(9) 3_656
O4 H4 O2 0.77(4) 1.89(4) 2.669(4) 180(4) 5_545
O5 H5 O3 0.924(19) 1.95(2) 2.866(3) 171(5) 5_545
O5 H5 O2 0.924(19) 2.69(4) 3.377(3) 132(4) 5_545

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.76
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 989794'
#######################################################################
#
#                 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_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C15 H17 N1 Ni O9, C3 H7 N1 O1'
_chemical_formula_sum            'C18 H24 N2 Ni O10'
_chemical_formula_weight         487.10

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           Orthorhombic
_symmetry_space_group_name_H-M   Cmcm

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

_cell_length_a                   9.9158(2)
_cell_length_b                   27.7237(5)
_cell_length_c                   7.45820(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2050.28(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3899
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.47

_exptl_crystal_description       platelet
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.006
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7857
_exptl_absorpt_correction_T_max  0.9018
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9454
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1339
_reflns_number_gt                1172
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXP-97

_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)+(0.1042P)²+2.4986P] 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         1339
_refine_ls_number_parameters     133
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.0000 1.0000 0.0198(3) Uani 1 4 d S . .
O1 O 0.4696(4) 0.06516(10) 0.8950(4) 0.0316(14) Uani 0.50 1 d P . .
O2 O 0.2076(3) 0.40026(11) 0.7500 0.0506(9) Uani 0.50 1 d P A .
O3 O 0.3770(3) 0.45103(10) 0.7500 0.0496(9) Uani 0.50 1 d PD A .
H3A H 0.471(3) 0.456(3) 0.7500 0.059 Uiso 0.50 2 d SPD . .
O4 O 0.5000 -0.03777(11) 0.7500 0.0200(6) Uani 1 4 d S . .
H4 H 0.565(4) -0.0562(14) 0.7500 0.024 Uiso 1 2 d S . .
O5 O 0.7053(4) -0.0092(2) 1.0275(11) 0.0395(16) Uani 0.50 1 d PD . .
H5 H 0.745(4) -0.0109(13) 0.915(3) 0.047 Uiso 1 1 d D . .
N1 N 0.5000 0.29122(14) 0.7500 0.0239(8) Uani 1 4 d S . .
C1 C 0.5000 0.23927(15) 0.7500 0.0235(9) Uani 1 4 d S . .
C2 C 0.5000 0.21476(12) 0.9108(5) 0.0360(9) Uani 1 2 d S . .
H2A H 0.5000 0.2316 1.0187 0.043 Uiso 1 2 calc SR . .
C3 C 0.5000 0.16489(12) 0.9101(5) 0.0375(9) Uani 1 2 d S . .
H3B H 0.5000 0.1481 1.0181 0.045 Uiso 1 2 calc SR . .
C4 C 0.5000 0.13971(16) 0.7500 0.0253(10) Uani 1 4 d S . .
C5 C 0.5000 0.08512(16) 0.7500 0.0263(10) Uani 1 4 d S . .
C6 C 0.3864(3) 0.31906(11) 0.7500 0.0257(7) Uani 1 2 d S . .
C7 C 0.4271(3) 0.36665(11) 0.7500 0.0238(7) Uani 1 2 d S . .
C8 C 0.2517(15) 0.2967(5) 0.7920(9) 0.0272(12) Uani 0.35 1 d PDU A -1
H8A H 0.2577 0.2623 0.7788 0.041 Uiso 0.35 1 calc PRD A -1
H8B H 0.1849 0.3090 0.7109 0.041 Uiso 0.35 1 calc PRD A -1
H8C H 0.2266 0.3044 0.9129 0.041 Uiso 0.35 1 calc PRD A -1
C8' C 0.252(3) 0.2956(9) 0.7500 0.0272(12) Uani 0.15 1 d P A 2
H8'A H 0.1843 0.3190 0.7219 0.041 Uiso 0.15 1 calc PR A 2
H8'B H 0.2349 0.2821 0.8663 0.041 Uiso 0.15 1 calc PR A 2
H8'C H 0.2510 0.2703 0.6618 0.041 Uiso 0.15 1 calc PR A 2
C9 C 0.3292(4) 0.40691(12) 0.7500 0.0319(8) Uani 1 2 d S . .
O6 O 0.5000 0.2965(4) 0.266(5) 0.164(6) Uani 0.50 2 d SPU . .
N2 N 0.5000 0.3766(2) 0.2500 0.0562(15) Uani 1 4 d S . .
C10 C 0.4319(16) 0.3363(6) 0.2500 0.081(4) Uani 0.50 2 d SPU . .
C11 C 0.6548(17) 0.3722(6) 0.2500 0.089(4) Uani 0.50 2 d SPU . .
C12 C 0.4494(16) 0.4238(6) 0.2500 0.093(4) Uani 0.50 2 d SPU . .


_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 1.992(3) 12_655 ?
Ni1 O1 1.992(3) 4_557 ?
Ni1 O1 1.992(3) . ?
Ni1 O1 1.992(3) 9_657 ?
Ni1 O5 2.062(4) 12_655 ?
Ni1 O5 2.062(4) 4_557 ?
Ni1 O5 2.062(4) . ?
Ni1 O5 2.062(4) 9_657 ?
Ni1 O4 2.1385(15) . ?
Ni1 O4 2.1385(15) 9_657 ?
O1 O1 0.604(8) 12_655 ?
O1 C5 1.252(4) . ?
O2 C9 1.219(5) . ?
O3 C9 1.312(5) . ?
O3 H3A 0.95(2) . ?
O4 Ni1 2.1385(15) 2_654 ?
O4 H4 0.82(4) . ?
O5 O5 0.654(10) 4_557 ?
O5 H5 0.92(2) . ?
N1 C6 1.366(4) 3_656 ?
N1 C6 1.366(4) . ?
N1 C1 1.440(5) . ?
C1 C2 1.379(4) 10_557 ?
C1 C2 1.379(4) . ?
C2 C3 1.382(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(4) . ?
C3 H3B 0.9300 . ?
C4 C3 1.383(4) 10_557 ?
C4 C5 1.514(6) . ?
C5 O1 1.252(4) 10_557 ?
C5 O1 1.252(4) 3_656 ?
C5 O1 1.252(4) 12_655 ?
C6 C7 1.379(4) . ?
C6 C8' 1.48(3) . ?
C6 C8 1.506(14) 10_557 ?
C6 C8 1.506(14) . ?
C7 C7 1.446(7) 3_656 ?
C7 C9 1.479(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8' H8'A 0.9600 . ?
C8' H8'B 0.9600 . ?
C8' H8'C 0.9600 . ?
O6 O6 0.24(7) 10_556 ?
O6 C10 1.300(17) 3_655 ?
O6 C10 1.300(17) . ?
N2 C10 1.306(16) . ?
N2 C10 1.306(16) 3_655 ?
N2 C12 1.401(17) 3_655 ?
N2 C12 1.401(17) . ?
N2 C11 1.540(17) 3_655 ?
N2 C11 1.540(17) . ?
C10 O6 1.300(17) 10_556 ?
C10 C11 1.32(2) 3_655 ?
C10 C10 1.35(3) 3_655 ?
C11 C10 1.32(2) 3_655 ?
C11 C12 1.76(2) 3_655 ?
C12 C12 1.00(3) 3_655 ?
C12 C11 1.76(2) 3_655 ?

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 O1 180.00(7) 12_655 4_557 ?
O1 Ni1 O1 17.4(2) 12_655 . ?
O1 Ni1 O1 162.6(2) 4_557 . ?
O1 Ni1 O1 162.6(2) 12_655 9_657 ?
O1 Ni1 O1 17.4(2) 4_557 9_657 ?
O1 Ni1 O1 180.00(7) . 9_657 ?
O1 Ni1 O5 107.51(17) 12_655 12_655 ?
O1 Ni1 O5 72.49(17) 4_557 12_655 ?
O1 Ni1 O5 90.09(17) . 12_655 ?
O1 Ni1 O5 89.91(17) 9_657 12_655 ?
O1 Ni1 O5 72.49(17) 12_655 4_557 ?
O1 Ni1 O5 107.51(17) 4_557 4_557 ?
O1 Ni1 O5 89.91(17) . 4_557 ?
O1 Ni1 O5 90.09(17) 9_657 4_557 ?
O5 Ni1 O5 180.0 12_655 4_557 ?
O1 Ni1 O5 90.09(17) 12_655 . ?
O1 Ni1 O5 89.91(17) 4_557 . ?
O1 Ni1 O5 107.51(17) . . ?
O1 Ni1 O5 72.49(17) 9_657 . ?
O5 Ni1 O5 161.7(3) 12_655 . ?
O5 Ni1 O5 18.3(3) 4_557 . ?
O1 Ni1 O5 89.91(17) 12_655 9_657 ?
O1 Ni1 O5 90.09(17) 4_557 9_657 ?
O1 Ni1 O5 72.49(17) . 9_657 ?
O1 Ni1 O5 107.51(17) 9_657 9_657 ?
O5 Ni1 O5 18.3(3) 12_655 9_657 ?
O5 Ni1 O5 161.7(3) 4_557 9_657 ?
O5 Ni1 O5 180.0 . 9_657 ?
O1 Ni1 O4 95.81(11) 12_655 . ?
O1 Ni1 O4 84.19(11) 4_557 . ?
O1 Ni1 O4 95.81(11) . . ?
O1 Ni1 O4 84.19(11) 9_657 . ?
O5 Ni1 O4 91.5(3) 12_655 . ?
O5 Ni1 O4 88.5(3) 4_557 . ?
O5 Ni1 O4 91.5(3) . . ?
O5 Ni1 O4 88.5(3) 9_657 . ?
O1 Ni1 O4 84.19(11) 12_655 9_657 ?
O1 Ni1 O4 95.81(11) 4_557 9_657 ?
O1 Ni1 O4 84.19(11) . 9_657 ?
O1 Ni1 O4 95.81(11) 9_657 9_657 ?
O5 Ni1 O4 88.5(3) 12_655 9_657 ?
O5 Ni1 O4 91.5(3) 4_557 9_657 ?
O5 Ni1 O4 88.5(3) . 9_657 ?
O5 Ni1 O4 91.5(3) 9_657 9_657 ?
O4 Ni1 O4 180.0 . 9_657 ?
O1 O1 C5 76.04(18) 12_655 . ?
O1 O1 Ni1 81.28(11) 12_655 . ?
C5 O1 Ni1 134.8(3) . . ?
C9 O3 H3A 120(6) . . ?
Ni1 O4 Ni1 121.36(14) . 2_654 ?
Ni1 O4 H4 107.7(11) . . ?
Ni1 O4 H4 107.7(11) 2_654 . ?
O5 O5 Ni1 80.87(14) 4_557 . ?
O5 O5 H5 58(2) 4_557 . ?
Ni1 O5 H5 109(2) . . ?
C6 N1 C6 111.2(4) 3_656 . ?
C6 N1 C1 124.42(19) 3_656 . ?
C6 N1 C1 124.42(19) . . ?
C2 C1 C2 120.9(4) 10_557 . ?
C2 C1 N1 119.5(2) 10_557 . ?
C2 C1 N1 119.5(2) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3B 119.7 . . ?
C4 C3 H3B 119.7 . . ?
C3 C4 C3 119.4(4) . 10_557 ?
C3 C4 C5 120.3(2) . . ?
C3 C4 C5 120.3(2) 10_557 . ?
O1 C5 O1 27.9(4) 10_557 3_656 ?
O1 C5 O1 127.5(5) 10_557 12_655 ?
O1 C5 O1 119.5(4) 3_656 12_655 ?
O1 C5 O1 119.5(4) 10_557 . ?
O1 C5 O1 127.5(5) 3_656 . ?
O1 C5 O1 27.9(4) 12_655 . ?
O1 C5 C4 116.2(2) 10_557 . ?
O1 C5 C4 116.2(2) 3_656 . ?
O1 C5 C4 116.2(2) 12_655 . ?
O1 C5 C4 116.2(2) . . ?
N1 C6 C7 107.4(3) . . ?
N1 C6 C8' 119.5(10) . . ?
C7 C6 C8' 133.1(11) . . ?
N1 C6 C8 119.9(6) . 10_557 ?
C7 C6 C8 130.8(6) . 10_557 ?
C8' C6 C8 12.1(3) . 10_557 ?
N1 C6 C8 119.9(6) . . ?
C7 C6 C8 130.8(6) . . ?
C8' C6 C8 12.1(3) . . ?
C8 C6 C8 24.0(6) 10_557 . ?
C6 C7 C7 107.0(2) . 3_656 ?
C6 C7 C9 122.0(3) . . ?
C7 C7 C9 131.0(2) 3_656 . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
C6 C8' H8'A 109.5 . . ?
C6 C8' H8'B 109.5 . . ?
H8'A C8' H8'B 109.5 . . ?
C6 C8' H8'C 109.5 . . ?
H8'A C8' H8'C 109.5 . . ?
H8'B C8' H8'C 109.5 . . ?
O2 C9 O3 119.9(3) . . ?
O2 C9 C7 122.3(3) . . ?
O3 C9 C7 117.8(3) . . ?
O6 O6 C10 84.7(15) 10_556 3_655 ?
O6 O6 C10 84.7(16) 10_556 . ?
C10 O6 C10 62.6(14) 3_655 . ?
C10 N2 C10 62.3(14) . 3_655 ?
C10 N2 C12 169.8(9) . 3_655 ?
C10 N2 C12 127.8(10) 3_655 3_655 ?
C10 N2 C12 127.8(10) . . ?
C10 N2 C12 169.8(9) 3_655 . ?
C12 N2 C12 42.0(13) 3_655 . ?
C10 N2 C11 54.3(9) . 3_655 ?
C10 N2 C11 116.6(11) 3_655 3_655 ?
C12 N2 C11 115.5(10) 3_655 3_655 ?
C12 N2 C11 73.5(9) . 3_655 ?
C10 N2 C11 116.6(11) . . ?
C10 N2 C11 54.3(9) 3_655 . ?
C12 N2 C11 73.5(9) 3_655 . ?
C12 N2 C11 115.5(10) . . ?
C11 N2 C11 170.9(14) 3_655 . ?
O6 C10 O6 11(3) 10_556 . ?
O6 C10 N2 117.3(12) 10_556 . ?
O6 C10 N2 117.3(12) . . ?
O6 C10 C11 169.3(15) 10_556 3_655 ?
O6 C10 C11 169.3(15) . 3_655 ?
N2 C10 C11 71.9(11) . 3_655 ?
O6 C10 C10 58.7(7) 10_556 3_655 ?
O6 C10 C10 58.7(7) . 3_655 ?
N2 C10 C10 58.8(7) . 3_655 ?
C11 C10 C10 130.8(10) 3_655 3_655 ?
C10 C11 N2 53.7(10) 3_655 . ?
C10 C11 C12 103.4(14) 3_655 3_655 ?
N2 C11 C12 49.6(8) . 3_655 ?
C12 C12 N2 69.0(6) 3_655 . ?
C12 C12 C11 125.9(8) 3_655 3_655 ?
N2 C12 C11 56.9(8) . 3_655 ?

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
O3 H3A O3 0.95(2) 1.51(3) 2.439(6) 165(9) 3_656
O4 H4 O2 0.82(4) 1.86(4) 2.681(3) 178(4) 5_545
O5 H5 O3 0.92(2) 2.09(3) 2.898(8) 146(3) 5_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.723
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.127
_database_code_depnum_ccdc_archive 'CCDC 989795'
