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

#######################################################################
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#                                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.
#
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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_NidimalpH6

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 N4 Ni O9'
_chemical_formula_weight         396.99

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.4748(3)
_cell_length_b                   13.1587(3)
_cell_length_c                   12.2363(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.169(3)
_cell_angle_gamma                90
_cell_volume                     1525.57(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    14030
_cell_measurement_theta_min      3.1194
_cell_measurement_theta_max      31.9729

_exptl_crystal_description       prism
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Oxford Diff., SuperNova-Sapphire'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0267
_diffrn_reflns_number            30625
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.126
_diffrn_reflns_theta_max         32.045
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5060
_reflns_number_gt                4544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro (Oxford Diff., 2009)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diff., 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diff., 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalMaker 2.1.5 (1994-2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+0.8964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5060
_refine_ls_number_parameters     265
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.67848(2) 0.24024(2) 0.49026(2) 0.00997(5) Uani 1 1 d . . . . .
O1 O 0.08339(10) 0.30527(7) 0.40060(8) 0.01848(19) Uani 1 1 d . . . . .
O2 O 0.08522(9) 0.13757(7) 0.37485(8) 0.01548(17) Uani 1 1 d . . . . .
O3 O 0.72430(9) 0.27792(7) 0.65316(7) 0.01341(17) Uani 1 1 d . . . . .
O4 O 0.86970(11) 0.15101(8) 0.69979(8) 0.0221(2) Uani 1 1 d . . . . .
O5 O 0.53574(10) 0.36800(7) 0.49370(8) 0.01608(18) Uani 1 1 d D . . . .
H51 H 0.545(2) 0.4071(15) 0.4413(14) 0.039(6) Uiso 1 1 d D . . . .
H52 H 0.539(2) 0.4008(16) 0.5517(13) 0.037(6) Uiso 1 1 d D . . . .
O6 O 0.81939(10) 0.34914(7) 0.43705(8) 0.01523(17) Uani 1 1 d D . . . .
H61 H 0.9005(15) 0.3300(14) 0.4261(15) 0.025(5) Uiso 1 1 d D . . . .
H62 H 0.827(2) 0.3949(13) 0.4810(14) 0.028(5) Uiso 1 1 d D . . . .
O7 O 0.83623(9) 0.12531(7) 0.49178(8) 0.01333(17) Uani 1 1 d D . . . .
H71 H 0.862(2) 0.1259(16) 0.5563(12) 0.031(5) Uiso 1 1 d D . . . .
H72 H 0.9062(18) 0.1314(16) 0.4524(15) 0.035(6) Uiso 1 1 d D . . . .
C1 C 0.14303(12) 0.22296(9) 0.37562(10) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.29716(12) 0.23522(9) 0.34044(10) 0.0104(2) Uani 1 1 d . . . . .
H2 H 0.3404 0.2899 0.3863 0.011(4) Uiso 1 1 calc R . . . .
C3 C 0.79726(12) 0.22821(9) 0.72074(10) 0.0120(2) Uani 1 1 d . . . . .
C10 C 0.38816(12) 0.13797(9) 0.35405(10) 0.0106(2) Uani 1 1 d . . . . .
H10 H 0.3365 0.0795 0.3203 0.014(4) Uiso 1 1 calc R . . . .
N11 N 0.54593(11) 0.11951(8) 0.19200(9) 0.01353(19) Uani 1 1 d . . . . .
H11 H 0.4844 0.0865 0.1514 0.030(5) Uiso 1 1 calc R . . . .
C12 C 0.52545(12) 0.15179(9) 0.29526(10) 0.0110(2) Uani 1 1 d . . . . .
N13 N 0.63816(10) 0.20054(8) 0.33206(8) 0.01188(19) Uani 1 1 d . . . . .
C14 C 0.73630(13) 0.19725(10) 0.24821(10) 0.0154(2) Uani 1 1 d . . . . .
H14 H 0.8285 0.2256 0.2511 0.024(5) Uiso 1 1 calc R . . . .
C15 C 0.68010(13) 0.14732(10) 0.16139(10) 0.0165(2) Uani 1 1 d . . . . .
H15 H 0.7244 0.1342 0.0933 0.027(5) Uiso 1 1 calc R . . . .
N21 N 0.31479(11) 0.06353(8) 0.53308(9) 0.01289(19) Uani 1 1 d . . . . .
H21 H 0.2375 0.0348 0.5076 0.034(5) Uiso 1 1 calc R . . . .
C22 C 0.40946(12) 0.11606(9) 0.47373(10) 0.0105(2) Uani 1 1 d . . . . .
N23 N 0.51357(10) 0.14957(8) 0.53735(8) 0.01097(18) Uani 1 1 d . . . . .
C24 C 0.48190(13) 0.11563(9) 0.64160(10) 0.0134(2) Uani 1 1 d . . . . .
H24 H 0.5376 0.1277 0.7049 0.022(4) Uiso 1 1 calc R . . . .
C25 C 0.35905(13) 0.06238(9) 0.63950(10) 0.0139(2) Uani 1 1 d . . . . .
H25 H 0.3133 0.0308 0.6996 0.025(5) Uiso 1 1 calc R . . . .
O8 O 0.16915(10) 0.49934(7) 0.40589(8) 0.01725(18) Uani 1 1 d D . . . .
H81 H 0.149(2) 0.4395(12) 0.4036(17) 0.034(6) Uiso 1 1 d D . . . .
H82 H 0.2446(18) 0.5066(16) 0.3770(16) 0.033(5) Uiso 1 1 d D . . . .
O9 O 0.94450(12) -0.01426(8) 0.81355(9) 0.0235(2) Uani 1 1 d D . . . .
H92 H 0.934(3) 0.0415(14) 0.7805(19) 0.050(7) Uiso 1 1 d D . . . .
H91 H 0.943(2) -0.0582(15) 0.7647(16) 0.045(7) Uiso 1 1 d 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
Ni N13 2.0401(11) . ?
Ni N23 2.0499(10) . ?
Ni O6 2.0652(9) . ?
Ni O3 2.0982(9) . ?
Ni O7 2.1264(9) . ?
Ni O5 2.1581(9) . ?
O1 C1 1.2596(15) . ?
O2 C1 1.2500(15) . ?
O3 C3 1.2595(15) . ?
O4 C3 1.2529(15) . ?
C1 C2 1.5322(16) . ?
C2 C3 1.5418(17) 4_565 ?
C2 C10 1.5517(16) . ?
C3 C2 1.5418(17) 4_666 ?
C10 C12 1.4994(16) . ?
C10 C22 1.5056(16) . ?
N11 C12 1.3476(15) . ?
N11 C15 1.3759(16) . ?
C12 N13 1.3236(15) . ?
N13 C14 1.3874(15) . ?
C14 C15 1.3566(18) . ?
N21 C22 1.3467(15) . ?
N21 C25 1.3670(16) . ?
C22 N23 1.3300(15) . ?
N23 C24 1.3853(16) . ?
C24 C25 1.3588(17) . ?

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
N13 Ni N23 88.68(4) . . ?
N13 Ni O6 89.88(4) . . ?
N23 Ni O6 170.57(4) . . ?
N13 Ni O3 178.40(4) . . ?
N23 Ni O3 91.50(4) . . ?
O6 Ni O3 90.20(4) . . ?
N13 Ni O7 87.47(4) . . ?
N23 Ni O7 96.89(4) . . ?
O6 Ni O7 92.36(4) . . ?
O3 Ni O7 90.93(4) . . ?
N13 Ni O5 95.88(4) . . ?
N23 Ni O5 88.27(4) . . ?
O6 Ni O5 82.61(4) . . ?
O3 Ni O5 85.72(4) . . ?
O7 Ni O5 173.94(4) . . ?
C3 O3 Ni 127.78(8) . . ?
O2 C1 O1 125.29(11) . . ?
O2 C1 C2 120.69(11) . . ?
O1 C1 C2 113.97(10) . . ?
C1 C2 C3 107.64(9) . 4_565 ?
C1 C2 C10 114.38(9) . . ?
C3 C2 C10 110.95(9) 4_565 . ?
O4 C3 O3 125.93(12) . . ?
O4 C3 C2 116.70(11) . 4_666 ?
O3 C3 C2 117.37(11) . 4_666 ?
C12 C10 C22 112.08(9) . . ?
C12 C10 C2 109.33(9) . . ?
C22 C10 C2 109.58(9) . . ?
C12 N11 C15 107.88(10) . . ?
N13 C12 N11 110.70(10) . . ?
N13 C12 C10 126.57(11) . . ?
N11 C12 C10 122.62(10) . . ?
C12 N13 C14 105.97(10) . . ?
C12 N13 Ni 126.55(8) . . ?
C14 N13 Ni 125.86(8) . . ?
C15 C14 N13 109.38(11) . . ?
C14 C15 N11 106.05(11) . . ?
C22 N21 C25 108.44(10) . . ?
N23 C22 N21 110.40(10) . . ?
N23 C22 C10 127.08(10) . . ?
N21 C22 C10 122.35(10) . . ?
C22 N23 C24 105.65(10) . . ?
C22 N23 Ni 126.37(8) . . ?
C24 N23 Ni 127.87(8) . . ?
C25 C24 N23 109.68(11) . . ?
C24 C25 N21 105.82(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
N11 H11 O8 0.88 1.98 2.8414(14) 166.2 2_545
N21 H21 O2 0.88 2.56 3.0666(14) 117.7 .
N21 H21 O7 0.88 2.22 2.8830(14) 131.9 3_656
O5 H51 O9 0.827(14) 2.311(17) 3.0493(15) 149(2) 4_565
O5 H52 O9 0.831(14) 1.998(14) 2.8276(15) 177(2) 2_656
O6 H61 O1 0.820(13) 1.791(13) 2.6067(13) 173(2) 1_655
O6 H62 O8 0.811(14) 1.963(14) 2.7713(14) 175(2) 3_666
O7 H71 O4 0.825(14) 1.788(14) 2.5862(14) 162(2) .
O7 H72 O2 0.825(14) 1.948(14) 2.7675(13) 172(2) 1_655
O8 H81 O1 0.810(15) 1.874(15) 2.6806(13) 174(2) .
O8 H82 O9 0.804(15) 2.052(15) 2.8528(15) 174(2) 4_565
O9 H92 O4 0.843(16) 1.850(17) 2.6765(15) 166(2) .
O9 H91 O2 0.831(16) 2.020(16) 2.8326(14) 166(2) 3_656

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.068

_shelxl_version_number           2014-1

_database_code_depnum_ccdc_archive 'CCDC 996415'
