# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1979541'
loop_
_audit_author_name
_audit_author_address
'Samuel A Morris'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H24 N6 Ni O12'
_chemical_formula_weight         503.08

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'
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'
H H 0.0000 0.0000 '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                   7.3043(5)
_cell_length_b                   8.8329(6)
_cell_length_c                   9.7206(7)
_cell_angle_alpha                65.294(3)
_cell_angle_beta                 70.106(3)
_cell_angle_gamma                79.466(3)
_cell_volume                     535.14(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      34.30

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             262
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6692
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_process_details   'SADABS (G.M Sheldrick)'
_exptl_absorpt_special_details   ?

_diffrn_radiation_wavelength     0.71073
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43507
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.414
_diffrn_reflns_theta_max         34.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4466
_reflns_number_gt                4111
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0486P)²+0.1095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.079(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4466
_refine_ls_number_parameters     191
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.073
_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 0.500000 0.500000 0.500000 0.02778(7) Uani 1 2 d S U P . .
O2 O 0.46835(12) 0.75390(9) 0.38921(9) 0.03393(16) Uani 1 1 d . U . . .
O1 O 0.66389(18) 0.47621(11) 0.28787(11) 0.0498(3) Uani 1 1 d . U . . .
O1W O 0.74267(19) 0.52438(14) 0.54657(18) 0.0617(4) Uani 1 1 d . U . . .
N3 N 0.93802(15) 0.14180(12) 0.74327(11) 0.03425(17) Uani 1 1 d . U . . .
O4 O 1.03767(19) 0.18567(15) 0.60091(12) 0.0552(3) Uani 1 1 d . U . . .
O3 O 0.9365(2) -0.00816(13) 0.82950(13) 0.0589(3) Uani 1 1 d . U . . .
O5 O 0.8440(2) 0.24611(18) 0.79554(17) 0.0678(4) Uani 1 1 d . U . . .
N1 N 0.8632(2) 0.24398(15) 0.33048(13) 0.0452(3) Uani 1 1 d . U . . .
N2 N 0.6882(2) 0.82148(14) 0.14729(13) 0.0486(3) Uani 1 1 d . U . . .
C1 C 0.77158(17) 0.36863(13) 0.24251(12) 0.03324(19) Uani 1 1 d . U . . .
C4 C 0.55434(15) 0.86085(12) 0.25935(11) 0.02946(17) Uani 1 1 d . U . . .
C2 C 0.80302(18) 0.37877(15) 0.08058(14) 0.0365(2) Uani 1 1 d . U . . .
C5 C 0.5119(2) 1.04069(13) 0.22407(15) 0.0412(2) Uani 1 1 d . U . . .
C3 C 0.7286(3) 0.5019(2) -0.0221(2) 0.0527(3) Uani 1 1 d . U . . .
C6 C 0.4030(3) 1.09857(17) 0.3313(2) 0.0540(4) Uani 1 1 d . U . . .
H1OW H 0.802(3) 0.600(3) 0.503(3) 0.057(6) Uiso 1 1 d . . . . .
H1C3 H 0.748(3) 0.510(3) -0.132(3) 0.063(6) Uiso 1 1 d . . . . .
H1C2 H 0.879(3) 0.290(3) 0.053(2) 0.051(5) Uiso 1 1 d . . . . .
H2C3 H 0.646(3) 0.586(3) 0.013(3) 0.063(6) Uiso 1 1 d . . . . .
H2OW H 0.786(3) 0.454(3) 0.601(3) 0.062(6) Uiso 1 1 d . . . . .
H1N1 H 0.846(3) 0.230(3) 0.427(3) 0.062(6) Uiso 1 1 d . . . . .
H1C6 H 0.349(4) 1.028(3) 0.436(3) 0.067(6) Uiso 1 1 d . . . . .
H2N2 H 0.749(3) 0.888(3) 0.065(3) 0.059(6) Uiso 1 1 d . . . . .
H2C6 H 0.380(4) 1.209(3) 0.306(3) 0.075(7) Uiso 1 1 d . . . . .
H2N1 H 0.927(3) 0.181(3) 0.294(3) 0.059(6) Uiso 1 1 d . . . . .
H1N2 H 0.718(3) 0.718(3) 0.162(3) 0.068(7) Uiso 1 1 d . . . . .
H1C5 H 0.565(4) 1.108(3) 0.128(3) 0.066(6) 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 O1W 2.0397(11) . ?
Ni1 O1W 2.0397(11) 2_666 ?
Ni1 O2 2.0503(7) 2_666 ?
Ni1 O2 2.0503(7) . ?
Ni1 O1 2.0783(9) 2_666 ?
Ni1 O1 2.0784(9) . ?
O2 C4 1.2493(11) . ?
O1 C1 1.2478(13) . ?
N3 O5 1.2252(15) . ?
N3 O3 1.2362(14) . ?
N3 O4 1.2508(14) . ?
N1 C1 1.3132(16) . ?
N2 C4 1.3157(15) . ?
C1 C2 1.4772(16) . ?
C4 C5 1.4744(15) . ?
C2 C3 1.311(2) . ?
C5 C6 1.309(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1W Ni1 O1W 180.0 . 2_666 ?
O1W Ni1 O2 89.25(4) . 2_666 ?
O1W Ni1 O2 90.75(4) 2_666 2_666 ?
O1W Ni1 O2 90.75(4) . . ?
O1W Ni1 O2 89.25(4) 2_666 . ?
O2 Ni1 O2 180.0 2_666 . ?
O1W Ni1 O1 87.80(6) . 2_666 ?
O1W Ni1 O1 92.19(6) 2_666 2_666 ?
O2 Ni1 O1 91.91(3) 2_666 2_666 ?
O2 Ni1 O1 88.08(3) . 2_666 ?
O1W Ni1 O1 92.20(6) . . ?
O1W Ni1 O1 87.80(6) 2_666 . ?
O2 Ni1 O1 88.09(3) 2_666 . ?
O2 Ni1 O1 91.91(3) . . ?
O1 Ni1 O1 180.0 2_666 . ?
C4 O2 Ni1 135.00(7) . . ?
C1 O1 Ni1 138.37(8) . . ?
O5 N3 O3 120.94(12) . . ?
O5 N3 O4 120.31(12) . . ?
O3 N3 O4 118.75(11) . . ?
O1 C1 N1 123.85(11) . . ?
O1 C1 C2 119.78(11) . . ?
N1 C1 C2 116.37(10) . . ?
O2 C4 N2 122.79(10) . . ?
O2 C4 C5 121.20(10) . . ?
N2 C4 C5 116.01(10) . . ?
C3 C2 C1 122.52(12) . . ?
C6 C5 C4 122.70(11) . . ?

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.057

