# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1986426'
loop_
_audit_author_name
_audit_author_address
'Hong Su'
;Department of Chemistry, University of Cape Town
South Africa
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2020-10-09 downloaded from the CCDC.
;

_audit_creation_date             2020-09-29
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.09.11 svn.rc89507dd for OlexSys, GUI svn.r5830)
;
_chemical_formula_moiety         'C22 H14 N4 Ni O4, 2(H2 O)'
_chemical_formula_sum            'C22 H18 N4 Ni O6'
_chemical_formula_weight         493.105
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Ni 0.35663 1.12491 12.83760 7.29200 4.44380 2.38000 3.87850 0.25650 12.17630
66.34210 1.03410005569
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.2220(12)
_cell_length_b                   10.7213(15)
_cell_length_c                   12.7485(19)
_cell_angle_alpha                101.309(3)
_cell_angle_beta                 92.147(3)
_cell_angle_gamma                108.191(3)
_cell_volume                     1041.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3502
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69
_cell_measurement_theta_min      5
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_correction_T_min  0.8579
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       plate
_exptl_crystal_F_000             508.988
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9914
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4978
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9914
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         1.64
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9914
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3667
_reflns_number_total             4978
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_cell_refinement       
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_data_reduction        
'SAINT (7.60a, Bruker AXS Inc., Madison, WI, USA, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-dev (Bourhis et al., 2015)'
_refine_diff_density_max         0.6469
_refine_diff_density_min         -0.5926
_refine_diff_density_rms         0.1473
_refine_ls_d_res_high            0.7561
_refine_ls_d_res_low             12.4306
_refine_ls_goodness_of_fit_ref   1.0303
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4978
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.0303
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.5407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.912(2)
 0.088(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
3.a Free rotating group:
 O1G(H1Ga,H1Gb), O2G(H2Ga,H2Gb)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C15(H15),
 C16(H16), C17(H17), C18(H18), C23(H23), C24(H24), C25(H25)
;
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_refinement_flags_posn
Ni1 Ni 0.72398(5) 0.76509(4) 0.76935(3) 0.01752(11) Uani 1.000000 .
N1 N 0.9922(3) 0.8460(2) 0.80122(19) 0.0194(5) Uani 1.000000 .
N2 N 0.6980(3) 0.7791(2) 0.61849(18) 0.0171(5) Uani 1.000000 .
C2 C 1.1056(4) 0.8885(3) 0.7326(2) 0.0234(7) Uani 1.000000 .
H2 H 1.0650(4) 0.8769(3) 0.6594(2) 0.0281(8) Uiso 1.000000 R
C3 C 1.2793(4) 0.9485(3) 0.7648(3) 0.0261(7) Uani 1.000000 .
H3 H 1.3572(4) 0.9760(3) 0.7141(3) 0.0314(8) Uiso 1.000000 R
C4 C 1.3393(4) 0.9683(3) 0.8720(3) 0.0270(7) Uani 1.000000 .
H4 H 1.4582(4) 1.0116(3) 0.8959(3) 0.0323(8) Uiso 1.000000 R
C5 C 1.2239(4) 0.9241(3) 0.9430(2) 0.0239(7) Uani 1.000000 .
H5 H 1.2619(4) 0.9365(3) 1.0168(2) 0.0287(8) Uiso 1.000000 R
C6 C 1.0512(4) 0.8612(3) 0.9051(2) 0.0186(6) Uani 1.000000 .
N7 N 0.7565(3) 0.7577(2) 0.92337(18) 0.0178(5) Uani 1.000000 .
C8 C 0.9173(3) 0.8048(3) 0.9740(2) 0.0185(6) Uani 1.000000 .
C9 C 0.9467(4) 0.7970(3) 1.0803(2) 0.0234(7) Uani 1.000000 .
H9 H 1.0602(4) 0.8288(3) 1.1160(2) 0.0281(8) Uiso 1.000000 R
C10 C 0.8064(4) 0.7417(3) 1.1325(2) 0.0267(7) Uani 1.000000 .
H10 H 0.8236(4) 0.7350(3) 1.2050(2) 0.0320(8) Uiso 1.000000 R
C11 C 0.6402(4) 0.6959(3) 1.0802(2) 0.0240(7) Uani 1.000000 .
H11 H 0.5434(4) 0.6586(3) 1.1161(2) 0.0288(8) Uiso 1.000000 R
C12 C 0.6203(4) 0.7062(3) 0.9742(2) 0.0189(6) Uani 1.000000 .
N13 N 0.4691(3) 0.6804(2) 0.80297(19) 0.0198(5) Uani 1.000000 .
C14 C 0.4528(4) 0.6629(3) 0.9044(2) 0.0190(6) Uani 1.000000 .
C15 C 0.2942(4) 0.6089(3) 0.9404(2) 0.0245(7) Uani 1.000000 .
H15 H 0.2861(4) 0.5991(3) 1.0126(2) 0.0294(8) Uiso 1.000000 R
C16 C 0.1474(4) 0.5693(3) 0.8678(3) 0.0288(7) Uani 1.000000 .
H16 H 0.0371(4) 0.5310(3) 0.8898(3) 0.0345(9) Uiso 1.000000 R
C17 C 0.1628(4) 0.5861(3) 0.7638(3) 0.0260(7) Uani 1.000000 .
H17 H 0.0639(4) 0.5590(3) 0.7131(3) 0.0312(8) Uiso 1.000000 R
C18 C 0.3254(4) 0.6432(3) 0.7347(2) 0.0231(7) Uani 1.000000 .
H18 H 0.3358(4) 0.6566(3) 0.6635(2) 0.0278(8) Uiso 1.000000 R
O19 O 0.7363(3) 0.57744(19) 0.68569(15) 0.0234(5) Uani 1.000000 .
C20 C 0.7241(4) 0.5601(3) 0.5833(2) 0.0228(6) Uani 1.000000 .
O21 O 0.7334(3) 0.4624(2) 0.51801(18) 0.0375(6) Uani 1.000000 .
C22 C 0.6970(4) 0.6762(3) 0.5408(2) 0.0218(6) Uani 1.000000 .
C23 C 0.6718(4) 0.6809(3) 0.4337(2) 0.0302(7) Uani 1.000000 .
H23 H 0.6708(4) 0.6074(3) 0.3779(2) 0.0362(9) Uiso 1.000000 R
C24 C 0.6480(5) 0.7949(3) 0.4098(3) 0.0337(8) Uani 1.000000 .
H24 H 0.6252(5) 0.7987(3) 0.3371(3) 0.0404(10) Uiso 1.000000 R
C25 C 0.6574(4) 0.9039(3) 0.4922(2) 0.0276(7) Uani 1.000000 .
H25 H 0.6466(4) 0.9842(3) 0.4767(2) 0.0331(8) Uiso 1.000000 R
C26 C 0.6827(3) 0.8926(3) 0.5968(2) 0.0193(6) Uani 1.000000 .
C27 C 0.6953(4) 0.9995(3) 0.6979(2) 0.0204(6) Uani 1.000000 .
O28 O 0.6944(3) 1.1117(2) 0.68754(18) 0.0348(6) Uani 1.000000 .
O29 O 0.7061(2) 0.96293(19) 0.78638(15) 0.0211(4) Uani 1.000000 .
O1G O 0.7198(3) 0.3788(2) 0.80173(17) 0.0334(6) Uani 1.000000 .
H1Ga H 0.719(5) 0.424(2) 0.7518(16) 0.0502(8) Uiso 1.000000 G
H1Gb H 0.723(5) 0.3010(15) 0.768(2) 0.0502(8) Uiso 1.000000 G
O2G O 0.8417(5) 0.2361(3) 0.5132(2) 0.0698(10) Uani 1.000000 .
H2Ga H 0.816(6) 0.310(3) 0.520(3) 0.1047(14) Uiso 1.000000 G
H2Gb H 0.824(7) 0.212(4) 0.5743(18) 0.1047(14) Uiso 1.000000 G


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 N1 2.093(2) . y
Ni1 N2 1.967(2) . y
Ni1 N7 1.992(2) . y
Ni1 N13 2.105(2) . y
Ni1 O19 2.119(2) . y
Ni1 O29 2.141(2) . y
N1 C2 1.340(4) . ?
N1 C6 1.354(3) . ?
N2 C22 1.328(4) . ?
N2 C26 1.341(3) . ?
C2 C3 1.379(4) . ?
C3 C4 1.387(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.389(4) . ?
C6 C8 1.487(4) . ?
N7 C8 1.346(3) . ?
N7 C12 1.336(3) . ?
C8 C9 1.391(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.385(4) . ?
C12 C14 1.500(4) . ?
N13 C14 1.348(3) . ?
N13 C18 1.344(3) . ?
C14 C15 1.387(4) . ?
C15 C16 1.391(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.384(4) . ?
O19 C20 1.277(3) . ?
C20 O21 1.229(4) . ?
C20 C22 1.524(4) . ?
C22 C23 1.386(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.390(4) . ?
C25 C26 1.376(4) . ?
C26 C27 1.524(4) . ?
C27 O28 1.238(3) . ?
C27 O29 1.273(3) . ?

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 N1 99.65(9) . . y
N7 Ni1 N1 78.86(9) . . y
N7 Ni1 N2 177.91(9) . . y
N13 Ni1 N1 156.68(9) . . y
N13 Ni1 N2 103.67(9) . . y
N13 Ni1 N7 77.82(9) . . y
O19 Ni1 N1 92.18(9) . . y
O19 Ni1 N2 78.10(9) . . y
O19 Ni1 N7 103.36(8) . . y
O19 Ni1 N13 93.03(8) . . y
O29 Ni1 N1 90.48(8) . . y
O29 Ni1 N2 78.14(9) . . y
O29 Ni1 N7 100.36(8) . . y
O29 Ni1 N13 93.82(8) . . y
O29 Ni1 O19 156.20(7) . . y
C2 N1 Ni1 127.34(19) . . ?
C6 N1 Ni1 113.94(18) . . ?
C6 N1 C2 118.6(2) . . ?
C22 N2 Ni1 119.16(19) . . ?
C26 N2 Ni1 119.13(19) . . ?
C26 N2 C22 121.7(2) . . ?
C3 C2 N1 122.1(3) . . ?
C4 C3 C2 119.4(3) . . ?
C5 C4 C3 119.0(3) . . ?
C6 C5 C4 118.9(3) . . ?
C5 C6 N1 121.9(3) . . ?
C8 C6 N1 114.8(2) . . ?
C8 C6 C5 123.3(3) . . ?
C8 N7 Ni1 118.56(19) . . ?
C12 N7 Ni1 120.09(18) . . ?
C12 N7 C8 121.3(2) . . ?
N7 C8 C6 113.5(2) . . ?
C9 C8 C6 125.9(3) . . ?
C9 C8 N7 120.5(3) . . ?
C10 C9 C8 118.2(3) . . ?
C11 C10 C9 120.9(3) . . ?
C12 C11 C10 117.9(3) . . ?
C11 C12 N7 121.1(3) . . ?
C14 C12 N7 112.9(2) . . ?
C14 C12 C11 126.0(3) . . ?
C14 N13 Ni1 114.88(18) . . ?
C18 N13 Ni1 126.9(2) . . ?
C18 N13 C14 118.2(2) . . ?
N13 C14 C12 114.3(2) . . ?
C15 C14 C12 123.2(3) . . ?
C15 C14 N13 122.5(3) . . ?
C16 C15 C14 118.3(3) . . ?
C17 C16 C15 119.7(3) . . ?
C18 C17 C16 118.6(3) . . ?
C17 C18 N13 122.8(3) . . ?
C20 O19 Ni1 115.02(18) . . ?
O21 C20 O19 127.1(3) . . ?
C22 C20 O19 114.6(3) . . ?
C22 C20 O21 118.3(3) . . ?
C20 C22 N2 113.0(2) . . ?
C23 C22 N2 120.5(3) . . ?
C23 C22 C20 126.5(3) . . ?
C24 C23 C22 118.6(3) . . ?
C25 C24 C23 120.0(3) . . ?
C26 C25 C24 118.4(3) . . ?
C25 C26 N2 120.7(3) . . ?
C27 C26 N2 112.8(2) . . ?
C27 C26 C25 126.5(3) . . ?
O28 C27 C26 118.4(3) . . ?
O29 C27 C26 115.4(2) . . ?
O29 C27 O28 126.2(3) . . ?
C27 O29 Ni1 114.33(18) . . ?

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
O1G H1Ga O19 0.8700 1.965(10) 2.795(3) 159(3) .
O1G H1Gb O28 0.8700 2.022(6) 2.887(3) 172(3) 1_545
O2G H2Ga O21 0.8699 1.961(8) 2.824(4) 171(5) .


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.912(2)
2 0.088(2)
