# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1579276'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H24 N7 Ni O9'
_chemical_formula_weight         445.0

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, 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                   12.8157(8)
_cell_length_b                   8.8179(5)
_cell_length_c                   15.3168(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.818(2)
_cell_angle_gamma                90
_cell_volume                     1656.88(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    23131
_cell_measurement_theta_min      2.779
_cell_measurement_theta_max      30.392

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             932
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.238
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23131
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         30.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2463
_reflns_number_gt                2271
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0269P)²+1.4485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2463
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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_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
Ni1 Ni 0.5000 0.0000 0.0000 0.00674(6) Uani 1 2 d S . P . .
O1 O 0.43397(7) 0.40092(10) 0.28144(6) 0.02137(18) Uani 1 1 d . . . . .
O2 O 0.5000 0.18754(12) 0.2500 0.0139(2) Uani 1 2 d S T P . .
O3 O 0.37135(6) 0.01911(8) 0.06130(5) 0.01165(15) Uani 1 1 d . . . . .
O4 O 0.36031(6) 0.26721(8) 0.06493(5) 0.01192(14) Uani 1 1 d . . . . .
O5 O 0.25749(6) 0.12652(9) 0.12249(5) 0.01355(15) Uani 1 1 d . . . . .
N1 N 0.5000 0.33212(15) 0.2500 0.0122(2) Uani 1 2 d S T P . .
N2 N 0.60084(7) 0.11560(10) 0.09998(6) 0.00965(16) Uani 1 1 d . . . . .
N3 N 0.54624(7) -0.17979(10) 0.07833(5) 0.00925(16) Uani 1 1 d . . . . .
N4 N 0.32889(7) 0.14122(10) 0.08376(5) 0.00919(15) Uani 1 1 d . . . . .
C1 C 0.67511(8) 0.00439(11) 0.16089(7) 0.01262(19) Uani 1 1 d . . . . .
H1B H 0.7110 0.0509 0.2209 0.015 Uiso 1 1 calc R U . . .
H1A H 0.7321 -0.0298 0.1333 0.015 Uiso 1 1 calc R U . . .
C2 C 0.60515(8) -0.12655(12) 0.17154(6) 0.01254(19) Uani 1 1 d . . . . .
H2B H 0.6508 -0.2091 0.2067 0.015 Uiso 1 1 calc R U . . .
H2A H 0.5527 -0.0941 0.2042 0.015 Uiso 1 1 calc R U . . .
C3 C 0.46320(8) -0.29558(12) 0.08126(7) 0.01290(19) Uani 1 1 d . . . . .
H3A H 0.4087 -0.2501 0.1079 0.015 Uiso 1 1 calc R U . . .
H3B H 0.4989 -0.3805 0.1210 0.015 Uiso 1 1 calc R U . . .
C4 C 0.59414(9) 0.35611(12) 0.01321(7) 0.01431(19) Uani 1 1 d . . . . .
H4A H 0.6401 0.4434 0.0072 0.017 Uiso 1 1 calc R U . . .
H4B H 0.5386 0.3935 0.0414 0.017 Uiso 1 1 calc R U . . .
C5 C 0.66491(8) 0.23982(12) 0.07602(7) 0.01334(19) Uani 1 1 d . . . . .
H5A H 0.7169 0.1964 0.0460 0.016 Uiso 1 1 calc R U . . .
H5B H 0.7077 0.2909 0.1326 0.016 Uiso 1 1 calc R U . . .
H2 H 0.5597(12) 0.1546(17) 0.1317(10) 0.019(4) Uiso 1 1 d . . . . .
H3 H 0.5917(12) -0.2233(17) 0.0550(10) 0.015(3) Uiso 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 N3 1.9729(8) 5_655 ?
Ni1 N3 1.9729(8) . ?
Ni1 N2 1.9771(8) 5_655 ?
Ni1 N2 1.9771(8) . ?
Ni1 O3 2.1270(7) 5_655 ?
Ni1 O3 2.1270(7) . ?
O1 N1 1.2457(10) . ?
O2 N1 1.2749(16) . ?
O3 N4 1.2970(11) . ?
O4 N4 1.2438(11) . ?
O5 N4 1.2329(11) . ?
N1 O1 1.2457(10) 2_655 ?
N2 C5 1.4775(13) . ?
N2 C1 1.4914(13) . ?
N2 H2 0.884(15) . ?
N3 C2 1.4849(12) . ?
N3 C3 1.4848(13) . ?
N3 H3 0.857(15) . ?
C1 C2 1.4994(15) . ?
C1 H1B 0.9900 . ?
C1 H1A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.5176(15) 5_655 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5149(15) . ?
C4 C3 1.5176(15) 5_655 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
N3 Ni1 N3 180.0 5_655 . ?
N3 Ni1 N2 85.95(3) 5_655 5_655 ?
N3 Ni1 N2 94.05(3) . 5_655 ?
N3 Ni1 N2 94.05(3) 5_655 . ?
N3 Ni1 N2 85.95(3) . . ?
N2 Ni1 N2 180.0 5_655 . ?
N3 Ni1 O3 85.99(3) 5_655 5_655 ?
N3 Ni1 O3 94.01(3) . 5_655 ?
N2 Ni1 O3 91.93(3) 5_655 5_655 ?
N2 Ni1 O3 88.07(3) . 5_655 ?
N3 Ni1 O3 94.01(3) 5_655 . ?
N3 Ni1 O3 85.99(3) . . ?
N2 Ni1 O3 88.07(3) 5_655 . ?
N2 Ni1 O3 91.93(3) . . ?
O3 Ni1 O3 180.0 5_655 . ?
N4 O3 Ni1 128.40(6) . . ?
O1 N1 O1 121.71(13) . 2_655 ?
O1 N1 O2 119.15(7) . . ?
O1 N1 O2 119.15(7) 2_655 . ?
C5 N2 C1 110.05(8) . . ?
C5 N2 Ni1 118.40(6) . . ?
C1 N2 Ni1 107.54(6) . . ?
C5 N2 H2 108.1(10) . . ?
C1 N2 H2 106.7(10) . . ?
Ni1 N2 H2 105.4(10) . . ?
C2 N3 C3 110.96(8) . . ?
C2 N3 Ni1 108.08(6) . . ?
C3 N3 Ni1 118.63(6) . . ?
C2 N3 H3 108.9(9) . . ?
C3 N3 H3 106.5(10) . . ?
Ni1 N3 H3 103.1(10) . . ?
O5 N4 O4 122.73(8) . . ?
O5 N4 O3 117.85(8) . . ?
O4 N4 O3 119.42(8) . . ?
N2 C1 C2 106.31(8) . . ?
N2 C1 H1B 110.5 . . ?
C2 C1 H1B 110.5 . . ?
N2 C1 H1A 110.5 . . ?
C2 C1 H1A 110.5 . . ?
H1B C1 H1A 108.7 . . ?
N3 C2 C1 107.01(8) . . ?
N3 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 . . ?
N3 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 . . ?
H2B C2 H2A 108.6 . . ?
N3 C3 C4 111.50(8) . 5_655 ?
N3 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 5_655 . ?
N3 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 5_655 . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 113.78(9) . 5_655 ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 5_655 . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 5_655 . ?
H4A C4 H4B 107.7 . . ?
N2 C5 C4 112.70(8) . . ?
N2 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?

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
Ni1 O3 N4 O5 -176.88(6) . . . . ?
Ni1 O3 N4 O4 3.86(12) . . . . ?
C5 N2 C1 C2 -172.75(8) . . . . ?
Ni1 N2 C1 C2 -42.49(9) . . . . ?
C3 N3 C2 C1 -172.11(8) . . . . ?
Ni1 N3 C2 C1 -40.44(9) . . . . ?
N2 C1 C2 N3 54.68(10) . . . . ?
C2 N3 C3 C4 -177.46(8) . . . 5_655 ?
Ni1 N3 C3 C4 56.54(10) . . . 5_655 ?
C1 N2 C5 C4 179.36(8) . . . . ?
Ni1 N2 C5 C4 55.17(10) . . . . ?
C3 C4 C5 N2 -66.98(11) 5_655 . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4


_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1579281'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H26 Co0.90 N9 Ni0.10 O15'
_chemical_formula_weight         571.29

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.371(5)
_cell_length_b                   8.496(4)
_cell_length_c                   9.080(5)
_cell_angle_alpha                89.163(3)
_cell_angle_beta                 76.951(5)
_cell_angle_gamma                81.894(4)
_cell_volume                     548.3(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15604
_cell_measurement_theta_min      2.303
_cell_measurement_theta_max      28.332

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             294.1
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.886
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15604
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0336
_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       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2723
_reflns_number_gt                2589
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 The H atoms on two nitric acids are not added to the crsyatl structure but taken into account on molecular formula.The cocrytalizes HNO3 results into solvent disorder
which is modeled in the stucture. The hydrogen bonding interaction between the solvent results into short contacts between O6 and O9, and, O6A and O7.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.3327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2723
_refine_ls_number_parameters     195
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.204
_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_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
Co1 Co 0.0000 0.0000 0.0000 0.01020(13) Uani 0.9 2 d S . P . .
Ni1 Ni 0.0000 0.0000 0.0000 0.01020(13) Uani 0.1 2 d S . P . .
O1 O -0.4396(2) 0.02869(19) 0.14016(18) 0.0226(3) Uani 1 1 d . . . . .
O3 O -0.18379(19) -0.14347(17) 0.05982(17) 0.0174(3) Uani 1 1 d . . . . .
O2 O -0.4507(2) -0.2259(2) 0.1402(2) 0.0290(4) Uani 1 1 d . . . . .
N1 N -0.1573(2) 0.1451(2) -0.10797(19) 0.0148(3) Uani 1 1 d . . . . .
H1 H -0.2851 0.1180 -0.0758 0.018 Uiso 1 1 calc R U . . .
N2 N -0.0836(2) 0.1267(2) 0.19059(19) 0.0166(3) Uani 1 1 d . . . . .
H2 H -0.2047 0.0957 0.2425 0.020 Uiso 1 1 calc R U . . .
N3 N -0.3647(2) -0.1110(2) 0.1157(2) 0.0185(4) Uani 1 1 d . . . . .
C2 C -0.2477(3) 0.3646(3) 0.0845(3) 0.0255(5) Uani 1 1 d . . . . .
H2A H -0.2745 0.4795 0.0946 0.031 Uiso 1 1 calc R U . . .
H2B H -0.3651 0.3224 0.1211 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0522(3) 0.0735(3) 0.2869(2) 0.0217(4) Uani 1 1 d . . . . .
H4A H -0.0024 0.1054 0.3915 0.026 Uiso 1 1 calc R U . . .
H4B H 0.1665 0.1209 0.2532 0.026 Uiso 1 1 calc R U . . .
C5 C -0.0954(3) 0.1048(3) -0.2726(2) 0.0210(4) Uani 1 1 d . . . . .
H5A H 0.0156 0.1529 -0.3173 0.025 Uiso 1 1 calc R U . . .
H5B H -0.1943 0.1439 -0.3241 0.025 Uiso 1 1 calc R U . . .
C1 C -0.1736(3) 0.3196(2) -0.0818(3) 0.0212(4) Uani 1 1 d . . . . .
H1A H -0.2577 0.3748 -0.1399 0.025 Uiso 1 1 calc R U . . .
H1B H -0.0510 0.3534 -0.1170 0.025 Uiso 1 1 calc R U . . .
C3 C -0.1123(3) 0.3037(3) 0.1826(3) 0.0247(5) Uani 1 1 d . . . . .
H3A H 0.0079 0.3399 0.1424 0.030 Uiso 1 1 calc R U . . .
H3B H -0.1607 0.3483 0.2840 0.030 Uiso 1 1 calc R U . . .
N6 N 0.5000 0.0000 0.5000 0.0511(11) Uani 1 2 d DS U P . .
O8 O 0.6461(5) 0.0118(6) 0.4659(4) 0.0305(8) Uani 0.5 1 d D U P . .
O9 O 0.4435(6) -0.1567(5) 0.5205(5) 0.0357(8) Uani 0.5 1 d . . P . .
O7 O 0.3509(5) 0.0909(5) 0.5694(5) 0.0338(8) Uani 0.5 1 d . . P . .
O5 O 0.6888(4) 0.6367(3) 0.6736(2) 0.0528(6) Uani 1 1 d . . . . .
O6 O 0.6149(8) 0.6116(6) 0.4427(5) 0.0452(9) Uani 0.5 1 d . . P A 1
O4 O 0.7082(9) 0.4143(6) 0.5720(6) 0.0595(8) Uani 0.5 1 d . . P A 1
N4 N 0.6681(10) 0.5545(6) 0.5695(6) 0.0402(12) Uani 0.5 1 d . . P A 1
O4A O 0.9036(7) 0.4476(6) 0.5373(5) 0.0526(11) Uani 0.5 1 d . . P A 2
O6A O 0.7274(7) 0.6212(5) 0.4329(5) 0.0421(4) Uani 0.5 1 d . . P A 2
N4A N 0.7836(8) 0.5614(6) 0.5592(5) 0.0314(9) Uani 0.5 1 d . . P A 2


_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 1.9313(16) 2 ?
Co1 O3 1.9313(16) . ?
Co1 N1 1.9747(18) 2 ?
Co1 N1 1.9748(18) . ?
Co1 N2 1.9795(18) . ?
Co1 N2 1.9796(18) 2 ?
O1 N3 1.237(2) . ?
O3 N3 1.306(2) . ?
O2 N3 1.229(2) . ?
N1 C1 1.489(3) . ?
N1 C5 1.491(3) . ?
N1 H1 0.9800 . ?
N2 C4 1.492(3) . ?
N2 C3 1.492(3) . ?
N2 H2 0.9800 . ?
C2 C3 1.516(3) . ?
C2 C1 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.505(3) 2 ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C4 1.505(3) 2 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N6 O8 1.070(3) . ?
N6 O8 1.070(3) 2_656 ?
N6 O7 1.290(4) 2_656 ?
N6 O7 1.290(4) . ?
N6 O9 1.447(4) 2_656 ?
N6 O9 1.447(4) . ?
O8 O7 0.930(5) 2_656 ?
O8 O9 1.305(6) 2_656 ?
O9 O8 1.305(6) 2_656 ?
O9 O7 1.715(6) 2_656 ?
O7 O8 0.930(5) 2_656 ?
O7 O9 1.715(6) 2_656 ?
O5 N4 1.233(5) . ?
O5 N4A 1.242(5) . ?
O6 N4 1.360(7) . ?
O4 N4 1.187(7) . ?
O4A N4A 1.201(6) . ?
O4A O4A 1.782(11) 2_766 ?
O6A N4A 1.372(6) . ?

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 O3 180.0 2 . ?
O3 Co1 N1 94.75(8) 2 2 ?
O3 Co1 N1 85.25(8) . 2 ?
O3 Co1 N1 85.25(8) 2 . ?
O3 Co1 N1 94.75(8) . . ?
N1 Co1 N1 180.0 2 . ?
O3 Co1 N2 86.04(7) 2 . ?
O3 Co1 N2 93.96(7) . . ?
N1 Co1 N2 86.48(8) 2 . ?
N1 Co1 N2 93.52(8) . . ?
O3 Co1 N2 93.96(7) 2 2 ?
O3 Co1 N2 86.04(7) . 2 ?
N1 Co1 N2 93.52(8) 2 2 ?
N1 Co1 N2 86.48(8) . 2 ?
N2 Co1 N2 180.0 . 2 ?
N3 O3 Co1 129.26(13) . . ?
C1 N1 C5 110.70(16) . . ?
C1 N1 Co1 118.84(13) . . ?
C5 N1 Co1 108.18(13) . . ?
C1 N1 H1 106.1 . . ?
C5 N1 H1 106.1 . . ?
Co1 N1 H1 106.1 . . ?
C4 N2 C3 110.15(17) . . ?
C4 N2 Co1 107.21(13) . . ?
C3 N2 Co1 118.86(14) . . ?
C4 N2 H2 106.7 . . ?
C3 N2 H2 106.7 . . ?
Co1 N2 H2 106.7 . . ?
O2 N3 O1 123.90(18) . . ?
O2 N3 O3 115.95(18) . . ?
O1 N3 O3 120.14(17) . . ?
C3 C2 C1 113.52(18) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N2 C4 C5 107.36(17) . 2 ?
N2 C4 H4A 110.2 . . ?
C5 C4 H4A 110.2 2 . ?
N2 C4 H4B 110.2 . . ?
C5 C4 H4B 110.2 2 . ?
H4A C4 H4B 108.5 . . ?
N1 C5 C4 107.05(16) . 2 ?
N1 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 2 . ?
N1 C5 H5B 110.3 . . ?
C4 C5 H5B 110.3 2 . ?
H5A C5 H5B 108.6 . . ?
N1 C1 C2 111.62(17) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N2 C3 C2 112.48(18) . . ?
N2 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N2 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O8 N6 O8 180.0 . 2_656 ?
O8 N6 O7 45.2(3) . 2_656 ?
O8 N6 O7 134.8(3) 2_656 2_656 ?
O8 N6 O7 134.8(3) . . ?
O8 N6 O7 45.2(3) 2_656 . ?
O7 N6 O7 180.0(3) 2_656 . ?
O8 N6 O9 60.3(3) . 2_656 ?
O8 N6 O9 119.7(3) 2_656 2_656 ?
O7 N6 O9 102.6(2) 2_656 2_656 ?
O7 N6 O9 77.4(2) . 2_656 ?
O8 N6 O9 119.7(3) . . ?
O8 N6 O9 60.3(3) 2_656 . ?
O7 N6 O9 77.4(2) 2_656 . ?
O7 N6 O9 102.6(2) . . ?
O9 N6 O9 180.0 2_656 . ?
O7 O8 N6 80.0(4) 2_656 . ?
O7 O8 O9 145.6(5) 2_656 2_656 ?
N6 O8 O9 74.3(3) . 2_656 ?
O8 O9 N6 45.4(2) 2_656 . ?
O8 O9 O7 91.4(3) 2_656 2_656 ?
N6 O9 O7 47.22(19) . 2_656 ?
O8 O7 N6 54.8(3) 2_656 . ?
O8 O7 O9 107.6(4) 2_656 2_656 ?
N6 O7 O9 55.41(19) . 2_656 ?
O4 N4 O5 119.2(5) . . ?
O4 N4 O6 115.5(5) . . ?
O5 N4 O6 125.2(5) . . ?
N4A O4A O4A 96.9(5) . 2_766 ?
O4A N4A O5 134.5(5) . . ?
O4A N4A O6A 115.3(4) . . ?
O5 N4A O6A 110.0(4) . . ?

_refine_diff_density_max         1.346
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.200

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1579280'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H26 N9 Ni O15'
_chemical_formula_weight         571.11

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.4549(13)
_cell_length_b                   9.0814(16)
_cell_length_c                   16.935(3)
_cell_angle_alpha                88.505(7)
_cell_angle_beta                 81.132(7)
_cell_angle_gamma                76.008(7)
_cell_volume                     1099.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5365
_cell_measurement_theta_min      28.222
_cell_measurement_theta_max      2.311

_exptl_crystal_description       parraleloprizm
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             594
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32361
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         28.222
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5365
_reflns_number_gt                4009
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0647P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5365
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.1241
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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_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
Ni1 Ni 0.05064(4) 0.01768(3) 0.24574(2) 0.00775(11) Uani 1 1 d . . . . .
O6 O -0.4158(3) 0.1819(2) 0.13166(11) 0.0209(5) Uani 1 1 d . . . . .
O5 O -0.3931(2) 0.1732(2) 0.25836(11) 0.0158(4) Uani 1 1 d . . . . .
O10 O -0.2937(2) 0.4929(2) 0.22440(11) 0.0192(4) Uani 1 1 d . . . . .
O3 O 0.5021(2) -0.1185(2) 0.23357(11) 0.0176(4) Uani 1 1 d . . . . .
O13 O -0.6726(3) 0.2973(2) 0.45075(12) 0.0227(5) Uani 1 1 d . . . . .
O12 O -0.5943(2) 0.5678(2) 0.26506(12) 0.0185(4) Uani 1 1 d . . . . .
O15 O -0.6910(3) 0.5426(2) 0.45930(12) 0.0261(5) Uani 1 1 d . . . . .
H15 H -0.6117 0.5206 0.4178 0.039 Uiso 1 1 calc R U . . .
O1 O 0.2479(2) -0.0616(2) 0.32267(11) 0.0124(4) Uani 1 1 d . . . . .
O8 O -0.1468(3) 0.4140(2) 0.05076(12) 0.0274(5) Uani 1 1 d . . . . .
O11 O -0.4045(3) 0.4664(2) 0.34821(11) 0.0190(4) Uani 1 1 d . . . . .
O7 O -0.3811(3) 0.6093(2) 0.09074(12) 0.0279(5) Uani 1 1 d . . . . .
H7 H -0.3467 0.5817 0.1349 0.042 Uiso 1 1 calc R U . . .
O9 O -0.3076(3) 0.5460(2) -0.03490(12) 0.0282(5) Uani 1 1 d . . . . .
O4 O -0.1468(2) 0.0871(2) 0.16826(10) 0.0128(4) Uani 1 1 d . . . . .
O2 O 0.5155(3) -0.1616(2) 0.35947(12) 0.0236(5) Uani 1 1 d . . . . .
O14 O -0.8588(3) 0.4343(2) 0.54775(12) 0.0249(5) Uani 1 1 d . . . . .
N4 N -0.1085(3) -0.0951(2) 0.31444(13) 0.0098(4) Uani 1 1 d . . . . .
H4 H -0.2362 -0.0612 0.2990 0.012 Uiso 1 1 calc R U . . .
N1 N 0.1419(3) -0.1688(2) 0.17818(12) 0.0103(4) Uani 1 1 d . . . . .
H1 H 0.2637 -0.2236 0.1945 0.012 Uiso 1 1 calc R U . . .
N9 N -0.7437(3) 0.4155(3) 0.48786(14) 0.0172(5) Uani 1 1 d . . . . .
N8 N -0.4344(3) 0.5104(2) 0.27925(14) 0.0148(5) Uani 1 1 d . . . . .
N2 N 0.2084(3) 0.1297(2) 0.17656(12) 0.0089(4) Uani 1 1 d . . . . .
H2 H 0.3374 0.0937 0.1904 0.011 Uiso 1 1 calc R U . . .
N3 N -0.0362(3) 0.2023(2) 0.31367(12) 0.0095(4) Uani 1 1 d . . . . .
H3 H -0.1584 0.2585 0.2982 0.011 Uiso 1 1 calc R U . . .
N7 N -0.2704(3) 0.5160(3) 0.03163(14) 0.0197(5) Uani 1 1 d . . . . .
N6 N -0.3232(3) 0.1494(2) 0.18662(13) 0.0116(5) Uani 1 1 d . . . . .
C2 C 0.3085(4) -0.0531(3) 0.06185(16) 0.0145(6) Uani 1 1 d . . . . .
H2A H 0.4270 -0.0914 0.0835 0.017 Uiso 1 1 calc R U . . .
H2B H 0.3381 -0.0584 0.0028 0.017 Uiso 1 1 calc R U . . .
C10 C 0.0080(4) -0.2671(3) 0.20224(16) 0.0130(5) Uani 1 1 d . . . . .
H10A H 0.0664 -0.3732 0.1845 0.016 Uiso 1 1 calc R U . . .
H10B H -0.1063 -0.2307 0.1773 0.016 Uiso 1 1 calc R U . . .
N5 N 0.4267(3) -0.1149(2) 0.30505(14) 0.0127(5) Uani 1 1 d . . . . .
C9 C -0.0407(4) -0.2590(3) 0.29169(16) 0.0123(5) Uani 1 1 d . . . . .
H9A H -0.1395 -0.3135 0.3097 0.015 Uiso 1 1 calc R U . . .
H9B H 0.0707 -0.3060 0.3167 0.015 Uiso 1 1 calc R U . . .
C3 C 0.2269(4) 0.1115(3) 0.08779(15) 0.0116(5) Uani 1 1 d . . . . .
H3A H 0.3089 0.1748 0.0611 0.014 Uiso 1 1 calc R U . . .
H3B H 0.1024 0.1473 0.0710 0.014 Uiso 1 1 calc R U . . .
C7 C -0.2083(4) 0.0908(3) 0.42918(16) 0.0138(6) Uani 1 1 d . . . . .
H7A H -0.3248 0.1336 0.4068 0.017 Uiso 1 1 calc R U . . .
H7B H -0.2396 0.0963 0.4882 0.017 Uiso 1 1 calc R U . . .
C8 C -0.1335(4) -0.0759(3) 0.40291(15) 0.0128(5) Uani 1 1 d . . . . .
H8A H -0.0119 -0.1166 0.4217 0.015 Uiso 1 1 calc R U . . .
H8B H -0.2217 -0.1354 0.4282 0.015 Uiso 1 1 calc R U . . .
C6 C -0.0686(4) 0.1864(3) 0.40231(15) 0.0126(5) Uani 1 1 d . . . . .
H6A H -0.1157 0.2884 0.4275 0.015 Uiso 1 1 calc R U . . .
H6B H 0.0517 0.1387 0.4207 0.015 Uiso 1 1 calc R U . . .
C5 C 0.0987(4) 0.3004(3) 0.29026(15) 0.0118(5) Uani 1 1 d . . . . .
H5A H 0.2138 0.2621 0.3144 0.014 Uiso 1 1 calc R U . . .
H5B H 0.0417 0.4061 0.3090 0.014 Uiso 1 1 calc R U . . .
C4 C 0.1444(4) 0.2942(3) 0.20014(15) 0.0121(5) Uani 1 1 d . . . . .
H4A H 0.0324 0.3434 0.1760 0.015 Uiso 1 1 calc R U . . .
H4B H 0.2444 0.3474 0.1818 0.015 Uiso 1 1 calc R U . . .
C1 C 0.1769(4) -0.1550(3) 0.08971(15) 0.0144(6) Uani 1 1 d . . . . .
H1A H 0.0562 -0.1137 0.0703 0.017 Uiso 1 1 calc R U . . .
H1B H 0.2312 -0.2573 0.0656 0.017 Uiso 1 1 calc R U . . .


_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 N2 1.970(2) . ?
Ni1 N3 1.975(2) . ?
Ni1 N4 1.977(2) . ?
Ni1 N1 1.986(2) . ?
Ni1 O4 2.0950(17) . ?
Ni1 O1 2.0997(17) . ?
O6 N6 1.231(3) . ?
O5 N6 1.248(3) . ?
O10 N8 1.271(3) . ?
O3 N5 1.251(3) . ?
O13 N9 1.219(3) . ?
O12 N8 1.237(3) . ?
O15 N9 1.361(3) . ?
O15 H15 0.8400 . ?
O1 N5 1.293(3) . ?
O8 N7 1.215(3) . ?
O11 N8 1.260(3) . ?
O7 N7 1.361(3) . ?
O7 H7 0.8400 . ?
O9 N7 1.210(3) . ?
O4 N6 1.292(3) . ?
O2 N5 1.224(3) . ?
O14 N9 1.210(3) . ?
N4 C8 1.490(3) . ?
N4 C9 1.492(3) . ?
N4 H4 1.0000 . ?
N1 C1 1.488(3) . ?
N1 C10 1.499(3) . ?
N1 H1 1.0000 . ?
N2 C3 1.498(3) . ?
N2 C4 1.499(3) . ?
N2 H2 1.0000 . ?
N3 C6 1.492(3) . ?
N3 C5 1.501(3) . ?
N3 H3 1.0000 . ?
C2 C3 1.519(3) . ?
C2 C1 1.522(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C10 C9 1.502(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 C6 1.522(4) . ?
C7 C8 1.534(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4 1.511(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
N2 Ni1 N3 86.77(9) . . ?
N2 Ni1 N4 179.56(8) . . ?
N3 Ni1 N4 93.49(9) . . ?
N2 Ni1 N1 93.02(9) . . ?
N3 Ni1 N1 179.06(8) . . ?
N4 Ni1 N1 86.73(9) . . ?
N2 Ni1 O4 86.69(8) . . ?
N3 Ni1 O4 95.04(8) . . ?
N4 Ni1 O4 92.93(8) . . ?
N1 Ni1 O4 85.87(8) . . ?
N2 Ni1 O1 94.78(8) . . ?
N3 Ni1 O1 87.04(8) . . ?
N4 Ni1 O1 85.59(8) . . ?
N1 Ni1 O1 92.06(8) . . ?
O4 Ni1 O1 177.52(7) . . ?
N9 O15 H15 109.5 . . ?
N5 O1 Ni1 128.90(15) . . ?
N7 O7 H7 109.5 . . ?
N6 O4 Ni1 127.92(15) . . ?
C8 N4 C9 110.38(19) . . ?
C8 N4 Ni1 119.25(15) . . ?
C9 N4 Ni1 107.84(15) . . ?
C8 N4 H4 106.2 . . ?
C9 N4 H4 106.2 . . ?
Ni1 N4 H4 106.2 . . ?
C1 N1 C10 110.66(19) . . ?
C1 N1 Ni1 119.44(16) . . ?
C10 N1 Ni1 106.72(15) . . ?
C1 N1 H1 106.4 . . ?
C10 N1 H1 106.4 . . ?
Ni1 N1 H1 106.4 . . ?
O14 N9 O13 127.4(2) . . ?
O14 N9 O15 115.2(2) . . ?
O13 N9 O15 117.4(2) . . ?
O12 N8 O11 121.6(2) . . ?
O12 N8 O10 121.1(2) . . ?
O11 N8 O10 117.3(2) . . ?
C3 N2 C4 110.50(19) . . ?
C3 N2 Ni1 118.52(15) . . ?
C4 N2 Ni1 108.19(15) . . ?
C3 N2 H2 106.3 . . ?
C4 N2 H2 106.3 . . ?
Ni1 N2 H2 106.3 . . ?
C6 N3 C5 110.12(19) . . ?
C6 N3 Ni1 119.10(16) . . ?
C5 N3 Ni1 107.29(15) . . ?
C6 N3 H3 106.5 . . ?
C5 N3 H3 106.5 . . ?
Ni1 N3 H3 106.5 . . ?
O9 N7 O8 127.5(3) . . ?
O9 N7 O7 115.0(2) . . ?
O8 N7 O7 117.5(2) . . ?
O6 N6 O5 122.7(2) . . ?
O6 N6 O4 117.8(2) . . ?
O5 N6 O4 119.5(2) . . ?
C3 C2 C1 112.9(2) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C10 C9 107.7(2) . . ?
N1 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 . . ?
N1 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O2 N5 O3 122.5(2) . . ?
O2 N5 O1 118.2(2) . . ?
O3 N5 O1 119.3(2) . . ?
N4 C9 C10 107.1(2) . . ?
N4 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
N4 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N2 C3 C2 111.3(2) . . ?
N2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C6 C7 C8 112.6(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N4 C8 C7 112.1(2) . . ?
N4 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N4 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C6 C7 112.1(2) . . ?
N3 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N3 C5 C4 107.06(19) . . ?
N3 C5 H5A 110.3 . . ?
C4 C5 H5A 110.3 . . ?
N3 C5 H5B 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
N2 C4 C5 106.7(2) . . ?
N2 C4 H4A 110.4 . . ?
C5 C4 H4A 110.4 . . ?
N2 C4 H4B 110.4 . . ?
C5 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
N1 C1 C2 113.0(2) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?

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
Ni1 O4 N6 O6 179.96(16) . . . . ?
Ni1 O4 N6 O5 -0.5(3) . . . . ?
C1 N1 C10 C9 -172.5(2) . . . . ?
Ni1 N1 C10 C9 -41.1(2) . . . . ?
Ni1 O1 N5 O2 -176.76(16) . . . . ?
Ni1 O1 N5 O3 2.4(3) . . . . ?
C8 N4 C9 C10 -171.76(19) . . . . ?
Ni1 N4 C9 C10 -39.9(2) . . . . ?
N1 C10 C9 N4 53.9(3) . . . . ?
C4 N2 C3 C2 174.8(2) . . . . ?
Ni1 N2 C3 C2 -59.6(2) . . . . ?
C1 C2 C3 N2 67.9(3) . . . . ?
C9 N4 C8 C7 -178.4(2) . . . . ?
Ni1 N4 C8 C7 55.9(3) . . . . ?
C6 C7 C8 N4 -66.8(3) . . . . ?
C5 N3 C6 C7 178.6(2) . . . . ?
Ni1 N3 C6 C7 -56.9(3) . . . . ?
C8 C7 C6 N3 67.3(3) . . . . ?
C6 N3 C5 C4 172.57(19) . . . . ?
Ni1 N3 C5 C4 41.5(2) . . . . ?
C3 N2 C4 C5 170.74(19) . . . . ?
Ni1 N2 C4 C5 39.5(2) . . . . ?
N3 C5 C4 N2 -53.4(2) . . . . ?
C10 N1 C1 C2 178.6(2) . . . . ?
Ni1 N1 C1 C2 54.1(3) . . . . ?
C3 C2 C1 N1 -65.5(3) . . . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.195

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1579279'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H24 Cl N6 Ni O4 S2'
_chemical_formula_weight         474.65

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.59(6)
_cell_length_b                   8.72(7)
_cell_length_c                   15.75(12)
_cell_angle_alpha                83.72(9)
_cell_angle_beta                 81.37(9)
_cell_angle_gamma                80.39(11)
_cell_volume                     1013(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3401
_cell_measurement_theta_min      2.378
_cell_measurement_theta_max      24.593

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   0.876
_exptl_transmission_factor_max   0.953
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.327
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12369
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         24.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.876
_reflns_number_total             3212
_reflns_number_gt                2332
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 The crystal was big and the data quality was moderate. We attempted to model by spliting the C and N of the SCN group in
two positions but that did not improve the quality of the stucture. The attmpt to model the C atoms with larger thermal ellipsoid in the macrocycles was not aslo succesful in order to 
decrease the value of refinment factors. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+6.8344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3212
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_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
Ni2 Ni 0.0000 0.0000 0.0000 0.0130(3) Uani 1 2 d S . P . .
Ni1 Ni 0.5000 0.5000 0.5000 0.0125(3) Uani 1 2 d S . P . .
Cl1 Cl 0.7413(3) 0.7122(2) 0.76243(12) 0.0392(5) Uani 1 1 d . . . . .
S2 S -0.4587(2) -0.3185(2) 0.08313(15) 0.0443(6) Uani 1 1 d . . . . .
S1 S 0.9467(2) 0.8302(2) 0.46408(17) 0.0496(7) Uani 1 1 d . . . . .
N1 N 0.3655(7) 0.7178(6) 0.4968(4) 0.0225(13) Uani 1 1 d . . . . .
H1 H 0.2401 0.7082 0.4882 0.027 Uiso 1 1 calc R U . . .
N2 N 0.4502(9) 0.4960(7) 0.6285(4) 0.0408(17) Uani 1 1 d . . . . .
H2 H 0.5617 0.5194 0.6479 0.049 Uiso 1 1 calc R U . . .
N5 N 0.1137(8) -0.2018(6) 0.0561(4) 0.0366(16) Uani 1 1 d . . . . .
H5 H 0.2433 -0.1920 0.0553 0.044 Uiso 1 1 calc R U . . .
N4 N 0.0471(9) -0.1058(9) -0.1086(4) 0.051(2) Uani 1 1 d . . . . .
H4 H -0.0704 -0.1380 -0.1150 0.061 Uiso 1 1 calc R U . . .
C12 C -0.3437(9) -0.1736(9) 0.0470(5) 0.039(2) Uani 1 1 d . . . . .
N6 N -0.2552(8) -0.0723(8) 0.0220(5) 0.0450(19) Uani 1 1 d . . . . .
C6 C 0.8318(9) 0.6810(8) 0.4887(6) 0.037(2) Uani 1 1 d . . . . .
N3 N 0.7449(8) 0.5785(7) 0.5057(5) 0.0464(19) Uani 1 1 d . . . . .
C3 C 0.4244(10) 0.8411(8) 0.4274(5) 0.0384(16) Uani 1 1 d . . . . .
H3A H 0.3358 0.9380 0.4321 0.046 Uiso 1 1 calc R U . . .
H3B H 0.5423 0.8652 0.4372 0.046 Uiso 1 1 calc R U . . .
C11 C 0.0390(12) -0.2470(10) 0.1545(6) 0.058(3) Uani 1 1 d . . . . .
H11A H -0.0832 -0.2746 0.1575 0.069 Uiso 1 1 calc R U . . .
H11B H 0.1179 -0.3404 0.1766 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4406(11) 0.7903(10) 0.3392(6) 0.058(3) Uani 1 1 d . . . . .
H4A H 0.4633 0.8798 0.2968 0.069 Uiso 1 1 calc R U . . .
H4B H 0.3243 0.7607 0.3310 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1757(13) -0.2655(10) -0.0845(7) 0.065(3) Uani 1 1 d . . . . .
H8A H 0.1732 -0.3425 -0.1259 0.078 Uiso 1 1 calc R U . . .
H8B H 0.3013 -0.2456 -0.0880 0.078 Uiso 1 1 calc R U . . .
C7 C 0.1130(13) -0.3294(10) 0.0044(7) 0.057(3) Uani 1 1 d . . . . .
H7A H -0.0096 -0.3567 0.0085 0.068 Uiso 1 1 calc R U . . .
H7B H 0.1962 -0.4232 0.0226 0.068 Uiso 1 1 calc R U . . .
C10 C 0.0306(14) -0.1191(12) 0.2104(6) 0.064(3) Uani 1 1 d . . . . .
H10A H 0.1520 -0.0888 0.2050 0.077 Uiso 1 1 calc R U . . .
H10B H -0.0012 -0.1593 0.2711 0.077 Uiso 1 1 calc R U . . .
C2 C 0.3493(14) 0.7702(10) 0.5853(6) 0.064(3) Uani 1 1 d . . . . .
H2A H 0.2524 0.8608 0.5928 0.077 Uiso 1 1 calc R U . . .
H2B H 0.4640 0.8011 0.5948 0.077 Uiso 1 1 calc R U . . .
C9 C 0.1043(14) -0.0269(14) -0.1904(7) 0.077(3) Uani 1 1 d . . . . .
H9A H 0.1160 -0.0986 -0.2362 0.093 Uiso 1 1 calc R U . . .
H9B H 0.2241 0.0032 -0.1896 0.093 Uiso 1 1 calc R U . . .
C5 C 0.4078(12) 0.3488(11) 0.6800(6) 0.064(3) Uani 1 1 d . . . . .
H5A H 0.2930 0.3245 0.6663 0.077 Uiso 1 1 calc R U . . .
H5B H 0.3921 0.3643 0.7422 0.077 Uiso 1 1 calc R U . . .
C1 C 0.3058(15) 0.6349(14) 0.6474(8) 0.095(4) Uani 1 1 d . . . . .
H1A H 0.1862 0.6100 0.6409 0.113 Uiso 1 1 calc R U . . .
H1B H 0.3024 0.6611 0.7073 0.113 Uiso 1 1 calc R U . . .
O3 O 0.7755(17) 0.5790(14) 0.7111(9) 0.086(4) Uani 0.6 1 d . . P A 1
O4A O 0.9100(16) 0.6516(17) 0.7376(10) 0.051(4) Uani 0.4 1 d . . P A 2
O2 O 0.5731(14) 0.7968(14) 0.7723(9) 0.075(4) Uani 0.6 1 d . . P A 1
O4 O 0.8642(18) 0.8294(17) 0.7072(11) 0.117(6) Uani 0.6 1 d . . P A 1
O1 O 0.830(2) 0.6725(14) 0.8375(8) 0.083(4) Uani 0.6 1 d . . P A 1
O3A O 0.6189(17) 0.5836(13) 0.7639(7) 0.028(3) Uani 0.4 1 d . . P A 2
O2A O 0.654(2) 0.8419(16) 0.7123(10) 0.052(4) Uani 0.4 1 d . . P A 2
O1A O 0.7008(19) 0.747(2) 0.8553(9) 0.044(4) Uani 0.4 1 d . . P A 2


_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
Ni2 N4 1.990(14) 2 ?
Ni2 N4 1.990(14) . ?
Ni2 N5 2.001(13) . ?
Ni2 N5 2.001(13) 2 ?
Ni2 N6 2.105(15) . ?
Ni2 N6 2.105(15) 2 ?
Ni1 N1 2.000(14) 2_666 ?
Ni1 N1 2.000(14) . ?
Ni1 N2 2.001(17) 2_666 ?
Ni1 N2 2.001(17) . ?
Ni1 N3 2.103(15) 2_666 ?
Ni1 N3 2.103(15) . ?
Cl1 O4A 1.319(15) . ?
Cl1 O2 1.360(13) . ?
Cl1 O1 1.428(14) . ?
Cl1 O2A 1.432(15) . ?
Cl1 O3 1.454(13) . ?
Cl1 O1A 1.503(17) . ?
Cl1 O3A 1.568(14) . ?
Cl1 O4 1.598(14) . ?
S2 C12 1.656(12) . ?
S1 C6 1.665(12) . ?
N1 C2 1.495(14) . ?
N1 C3 1.518(12) . ?
N1 H1 1.0000 . ?
N2 C5 1.497(14) . ?
N2 C1 1.515(12) . ?
N2 H2 1.0000 . ?
N5 C7 1.450(13) . ?
N5 C11 1.599(15) . ?
N5 H5 1.0000 . ?
N4 C9 1.435(15) . ?
N4 C8 1.606(14) . ?
N4 H4 1.0000 . ?
C12 N6 1.195(11) . ?
C6 N3 1.182(11) . ?
C3 C4 1.487(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 C10 1.483(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C4 C5 1.548(14) 2_666 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C7 1.488(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C10 C9 1.531(16) 2 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C2 C1 1.496(17) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C9 C10 1.531(16) 2 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C5 C4 1.548(14) 2_666 ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
N4 Ni2 N4 180.0 2 . ?
N4 Ni2 N5 93.6(6) 2 . ?
N4 Ni2 N5 86.4(6) . . ?
N4 Ni2 N5 86.4(6) 2 2 ?
N4 Ni2 N5 93.6(6) . 2 ?
N5 Ni2 N5 180.0 . 2 ?
N4 Ni2 N6 92.1(4) 2 . ?
N4 Ni2 N6 87.9(4) . . ?
N5 Ni2 N6 91.6(5) . . ?
N5 Ni2 N6 88.4(5) 2 . ?
N4 Ni2 N6 87.9(4) 2 2 ?
N4 Ni2 N6 92.1(4) . 2 ?
N5 Ni2 N6 88.4(5) . 2 ?
N5 Ni2 N6 91.6(5) 2 2 ?
N6 Ni2 N6 180.0(3) . 2 ?
N1 Ni1 N1 180.0 2_666 . ?
N1 Ni1 N2 86.9(3) 2_666 2_666 ?
N1 Ni1 N2 93.1(3) . 2_666 ?
N1 Ni1 N2 93.1(3) 2_666 . ?
N1 Ni1 N2 86.9(3) . . ?
N2 Ni1 N2 180.0 2_666 . ?
N1 Ni1 N3 92.0(5) 2_666 2_666 ?
N1 Ni1 N3 88.0(5) . 2_666 ?
N2 Ni1 N3 88.5(3) 2_666 2_666 ?
N2 Ni1 N3 91.5(3) . 2_666 ?
N1 Ni1 N3 88.0(5) 2_666 . ?
N1 Ni1 N3 92.0(5) . . ?
N2 Ni1 N3 91.5(3) 2_666 . ?
N2 Ni1 N3 88.5(3) . . ?
N3 Ni1 N3 180.0 2_666 . ?
O2 Cl1 O1 117.4(9) . . ?
O4A Cl1 O2A 120.2(10) . . ?
O2 Cl1 O3 119.0(8) . . ?
O1 Cl1 O3 109.1(8) . . ?
O4A Cl1 O1A 114.9(9) . . ?
O2A Cl1 O1A 107.6(10) . . ?
O4A Cl1 O3A 108.6(10) . . ?
O2A Cl1 O3A 103.2(10) . . ?
O1A Cl1 O3A 99.8(7) . . ?
O2 Cl1 O4 104.4(9) . . ?
O1 Cl1 O4 101.5(10) . . ?
O3 Cl1 O4 102.5(10) . . ?
C2 N1 C3 112.1(8) . . ?
C2 N1 Ni1 107.1(5) . . ?
C3 N1 Ni1 120.2(6) . . ?
C2 N1 H1 105.4 . . ?
C3 N1 H1 105.4 . . ?
Ni1 N1 H1 105.4 . . ?
C5 N2 C1 112.6(9) . . ?
C5 N2 Ni1 119.2(6) . . ?
C1 N2 Ni1 105.7(6) . . ?
C5 N2 H2 106.1 . . ?
C1 N2 H2 106.1 . . ?
Ni1 N2 H2 106.1 . . ?
C7 N5 C11 110.2(8) . . ?
C7 N5 Ni2 110.5(7) . . ?
C11 N5 Ni2 117.4(5) . . ?
C7 N5 H5 106.0 . . ?
C11 N5 H5 106.0 . . ?
Ni2 N5 H5 106.0 . . ?
C9 N4 C8 114.4(7) . . ?
C9 N4 Ni2 122.2(9) . . ?
C8 N4 Ni2 103.4(6) . . ?
C9 N4 H4 105.1 . . ?
C8 N4 H4 105.1 . . ?
Ni2 N4 H4 105.1 . . ?
N6 C12 S2 177.6(7) . . ?
C12 N6 Ni2 148.3(6) . . ?
N3 C6 S1 177.7(7) . . ?
C6 N3 Ni1 147.2(6) . . ?
C4 C3 N1 112.5(8) . . ?
C4 C3 H3A 109.1 . . ?
N1 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
N1 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C10 C11 N5 112.9(8) . . ?
C10 C11 H11A 109.0 . . ?
N5 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
N5 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C3 C4 C5 114.2(7) . 2_666 ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 2_666 . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 2_666 . ?
H4A C4 H4B 107.6 . . ?
C7 C8 N4 109.7(7) . . ?
C7 C8 H8A 109.7 . . ?
N4 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
N4 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N5 C7 C8 103.2(9) . . ?
N5 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
N5 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C11 C10 C9 114.9(10) . 2 ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 2 . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 2 . ?
H10A C10 H10B 107.5 . . ?
N1 C2 C1 106.8(9) . . ?
N1 C2 H2A 110.4 . . ?
C1 C2 H2A 110.4 . . ?
N1 C2 H2B 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
N4 C9 C10 111.0(8) . 2 ?
N4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 2 . ?
N4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 2 . ?
H9A C9 H9B 108.0 . . ?
N2 C5 C4 111.5(8) . 2_666 ?
N2 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 2_666 . ?
N2 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 2_666 . ?
H5A C5 H5B 108.0 . . ?
C2 C1 N2 108.3(9) . . ?
C2 C1 H1A 110.0 . . ?
N2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 . . ?
N2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?

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
C2 N1 C3 C4 -179.9(6) . . . . ?
Ni1 N1 C3 C4 53.0(8) . . . . ?
C7 N5 C11 C10 -178.1(8) . . . . ?
Ni2 N5 C11 C10 -50.4(10) . . . . ?
N1 C3 C4 C5 -65.9(10) . . . 2_666 ?
C9 N4 C8 C7 175.0(8) . . . . ?
Ni2 N4 C8 C7 39.8(9) . . . . ?
C11 N5 C7 C8 177.0(6) . . . . ?
Ni2 N5 C7 C8 45.6(8) . . . . ?
N4 C8 C7 N5 -56.1(10) . . . . ?
N5 C11 C10 C9 65.6(11) . . . 2 ?
C3 N1 C2 C1 -175.4(7) . . . . ?
Ni1 N1 C2 C1 -41.6(9) . . . . ?
C8 N4 C9 C10 177.0(8) . . . 2 ?
Ni2 N4 C9 C10 -57.1(11) . . . 2 ?
C1 N2 C5 C4 -178.8(8) . . . 2_666 ?
Ni1 N2 C5 C4 56.5(10) . . . 2_666 ?
N1 C2 C1 N2 55.6(11) . . . . ?
C5 N2 C1 C2 -173.0(8) . . . . ?
Ni1 N2 C1 C2 -41.2(10) . . . . ?

_refine_diff_density_max         1.356
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.121

_shelxl_version_number           2013-4


_exptl_crystal_preparation       'Magnetic properties'
