# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_Ni
_database_code_depnum_ccdc_archive 'CCDC 1858717'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 N6 Ni O2, C10 H8 N2, 2(Cl O4), 2(O)'
_chemical_formula_sum            'C40 H36 Cl2 N8 Ni O12'
_chemical_formula_weight         950.36

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   17.9784(12)
_cell_length_b                   11.4346(8)
_cell_length_c                   24.4647(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.082(2)
_cell_angle_gamma                90.00
_cell_volume                     5026.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.62

_exptl_crystal_description       Block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960.0
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.125
_exptl_absorpt_correction_T_max  0.115
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23130
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         26.08
_reflns_number_total             4962
_reflns_number_gt                3845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.3000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4962
_refine_ls_number_parameters     270
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.1221
_refine_ls_wR_factor_ref         0.4153
_refine_ls_wR_factor_gt          0.3875
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_restrained_S_all      1.264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.92372(7) 0.7500 0.0257(5) Uani 1 2 d S . .
N1 N 0.5440(3) 0.9187(3) 0.67087(19) 0.0298(10) Uani 1 1 d . . .
N2 N 0.6199(3) 0.9733(6) 0.3898(2) 0.0520(15) Uani 1 1 d . . .
N3 N 0.5000 0.7364(5) 0.7500 0.0337(15) Uani 1 2 d S . .
N4 N 0.5000 0.1160(5) 0.7500 0.0281(13) Uani 1 2 d S . .
O1 O 0.3951(3) 0.9246(3) 0.71269(19) 0.0341(10) Uani 1 1 d . . .
C1 C 0.5935(3) 0.9952(5) 0.6534(2) 0.0435(15) Uani 1 1 d . . .
H1 H 0.6153 1.0466 0.6787 0.052 Uiso 1 1 calc R . .
C2 C 0.6143(4) 1.0026(5) 0.6000(2) 0.0434(15) Uani 1 1 d . . .
H2 H 0.6500 1.0569 0.5903 0.052 Uiso 1 1 calc R . .
C3 C 0.5828(3) 0.9304(4) 0.5609(2) 0.0329(13) Uani 1 1 d . . .
C4 C 0.5326(3) 0.8463(5) 0.5794(2) 0.0405(14) Uani 1 1 d . . .
H4 H 0.5114 0.7917 0.5553 0.049 Uiso 1 1 calc R . .
C5 C 0.5154(4) 0.8460(5) 0.6336(2) 0.0397(14) Uani 1 1 d . . .
H5 H 0.4812 0.7908 0.6450 0.048 Uiso 1 1 calc R . .
C6 C 0.5979(3) 0.9419(5) 0.5020(2) 0.0363(13) Uani 1 1 d . . .
C7 C 0.5647(4) 0.8706(6) 0.4630(2) 0.0501(16) Uani 1 1 d . . .
H7 H 0.5339 0.8102 0.4738 0.060 Uiso 1 1 calc R . .
C8 C 0.5762(4) 0.8869(7) 0.4079(2) 0.0494(16) Uani 1 1 d . . .
H8 H 0.5530 0.8368 0.3826 0.059 Uiso 1 1 calc R . .
C9 C 0.6525(5) 1.0429(9) 0.4281(3) 0.071(2) Uani 1 1 d . . .
H9 H 0.6824 1.1042 0.4169 0.085 Uiso 1 1 calc R . .
C10 C 0.6434(4) 1.0266(8) 0.4823(3) 0.060(2) Uani 1 1 d . . .
H10 H 0.6691 1.0750 0.5070 0.072 Uiso 1 1 calc R . .
C11 C 0.4375(4) 0.6757(5) 0.7576(3) 0.0392(14) Uani 1 1 d . . .
H11 H 0.3934 0.7165 0.7621 0.047 Uiso 1 1 calc R . .
C12 C 0.4358(4) 0.5548(5) 0.7589(3) 0.0448(16) Uani 1 1 d . . .
H12 H 0.3916 0.5161 0.7657 0.054 Uiso 1 1 calc R . .
C13 C 0.5000 0.4909(6) 0.7500 0.0353(18) Uani 1 2 d S . .
C14 C 0.5000 0.3617(7) 0.7500 0.0366(18) Uani 1 2 d S . .
C15 C 0.4373(3) 0.2985(5) 0.7341(3) 0.0402(14) Uani 1 1 d . . .
H15 H 0.3937 0.3372 0.7234 0.048 Uiso 1 1 calc R . .
C16 C 0.4396(3) 0.1779(5) 0.7343(2) 0.0382(14) Uani 1 1 d . . .
H16 H 0.3969 0.1374 0.7229 0.046 Uiso 1 1 calc R . .
N5 N 0.2466(7) 0.7911(10) 0.8563(4) 0.099(3) Uani 1 1 d . . .
C17 C 0.2810(8) 0.7113(14) 0.8780(5) 0.109(4) Uani 1 1 d . . .
H17 H 0.3059 0.6613 0.8549 0.131 Uiso 1 1 calc R . .
C18 C 0.2873(6) 0.6862(9) 0.9345(4) 0.091(3) Uani 1 1 d . . .
H18 H 0.3156 0.6233 0.9475 0.110 Uiso 1 1 calc R . .
C19 C 0.2487(4) 0.7607(7) 0.9710(3) 0.0575(19) Uani 1 1 d . . .
C20 C 0.2106(6) 0.8489(10) 0.9468(4) 0.089(3) Uani 1 1 d . . .
H20 H 0.1843 0.9006 0.9681 0.106 Uiso 1 1 calc R . .
C21 C 0.2099(7) 0.8647(13) 0.8892(5) 0.108(4) Uani 1 1 d . . .
H21 H 0.1836 0.9272 0.8738 0.129 Uiso 1 1 calc R . .
O1W O 0.2614(4) 0.8751(10) 0.7527(3) 0.124(3) Uani 1 1 d . . .
Cl1 Cl 0.145(2) 0.911(2) 0.6061(12) 0.69(2) Uiso 1 1 d D . .
O10 O 0.1671(7) 0.8058(12) 0.6348(5) 0.190(5) Uiso 1 1 d D . .
O11 O 0.154(7) 1.006(5) 0.644(4) 2.0(2) Uiso 1 1 d D . .
O12 O 0.0721(19) 0.909(2) 0.5807(13) 0.408(18) Uiso 1 1 d D . .
O13 O 0.198(4) 0.926(10) 0.564(3) 2.0(4) Uiso 1 1 d D . .
H1W H 0.366(3) 0.938(5) 0.726(3) 0.012(16) Uiso 1 1 d . . .
H2W H 0.389(3) 0.963(5) 0.678(3) 0.025(13) 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 O1 2.065(5) 2_656 ?
Ni1 O1 2.065(5) . ?
Ni1 N1 2.119(5) . ?
Ni1 N1 2.119(5) 2_656 ?
Ni1 N3 2.141(6) . ?
Ni1 N4 2.199(6) 1_565 ?
N1 C5 1.323(7) . ?
N1 C1 1.330(7) . ?
N2 C9 1.347(11) . ?
N2 C8 1.347(10) . ?
N3 C11 1.340(7) 2_656 ?
N3 C11 1.340(7) . ?
N4 C16 1.341(7) 2_656 ?
N4 C16 1.341(7) . ?
N4 Ni1 2.199(6) 1_545 ?
O1 H1W 0.65(6) . ?
O1 H2W 0.96(6) . ?
C1 C2 1.375(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(8) . ?
C3 C6 1.484(8) . ?
C4 C5 1.374(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C10 1.368(9) . ?
C6 C7 1.374(9) . ?
C7 C8 1.383(8) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.355(10) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.384(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(7) . ?
C12 H12 0.9300 . ?
C13 C12 1.390(7) 2_656 ?
C13 C14 1.478(12) . ?
C14 C15 1.382(7) . ?
C14 C15 1.382(7) 2_656 ?
C15 C16 1.379(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N5 C17 1.214(16) . ?
N5 C21 1.352(16) . ?
C17 C18 1.412(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.433(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.345(13) . ?
C19 C19 1.437(14) 7_567 ?
C20 C21 1.419(14) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
Cl1 O12 1.435(10) . ?
Cl1 O10 1.438(10) . ?
Cl1 O11 1.440(10) . ?
Cl1 O13 1.443(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 179.5(2) 2_656 . ?
O1 Ni1 N1 92.22(19) 2_656 . ?
O1 Ni1 N1 87.80(19) . . ?
O1 Ni1 N1 87.80(19) 2_656 2_656 ?
O1 Ni1 N1 92.22(19) . 2_656 ?
N1 Ni1 N1 176.9(2) . 2_656 ?
O1 Ni1 N3 90.27(11) 2_656 . ?
O1 Ni1 N3 90.27(11) . . ?
N1 Ni1 N3 88.43(11) . . ?
N1 Ni1 N3 88.43(11) 2_656 . ?
O1 Ni1 N4 89.73(11) 2_656 1_565 ?
O1 Ni1 N4 89.73(11) . 1_565 ?
N1 Ni1 N4 91.57(11) . 1_565 ?
N1 Ni1 N4 91.57(11) 2_656 1_565 ?
N3 Ni1 N4 180.000(3) . 1_565 ?
C5 N1 C1 116.1(5) . . ?
C5 N1 Ni1 119.8(4) . . ?
C1 N1 Ni1 123.5(4) . . ?
C9 N2 C8 116.7(6) . . ?
C11 N3 C11 117.6(7) 2_656 . ?
C11 N3 Ni1 121.2(3) 2_656 . ?
C11 N3 Ni1 121.2(3) . . ?
C16 N4 C16 116.3(7) 2_656 . ?
C16 N4 Ni1 121.9(3) 2_656 1_545 ?
C16 N4 Ni1 121.9(3) . 1_545 ?
Ni1 O1 H1W 121(5) . . ?
Ni1 O1 H2W 118(3) . . ?
H1W O1 H2W 106(6) . . ?
N1 C1 C2 123.6(5) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 116.3(5) . . ?
C2 C3 C6 122.7(5) . . ?
C4 C3 C6 121.0(5) . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 124.6(5) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C10 C6 C7 115.3(6) . . ?
C10 C6 C3 122.5(6) . . ?
C7 C6 C3 122.2(6) . . ?
C6 C7 C8 121.3(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
N2 C8 C7 121.9(7) . . ?
N2 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
N2 C9 C10 122.3(7) . . ?
N2 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C10 C6 122.5(7) . . ?
C9 C10 H10 118.8 . . ?
C6 C10 H10 118.8 . . ?
N3 C11 C12 122.7(6) . . ?
N3 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C12 116.6(7) 2_656 . ?
C12 C13 C14 121.7(4) 2_656 . ?
C12 C13 C14 121.7(4) . . ?
C15 C14 C15 116.9(7) . 2_656 ?
C15 C14 C13 121.5(4) . . ?
C15 C14 C13 121.5(4) 2_656 . ?
C16 C15 C14 119.9(6) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
N4 C16 C15 123.5(6) . . ?
N4 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C17 N5 C21 117.4(11) . . ?
N5 C17 C18 127.0(13) . . ?
N5 C17 H17 116.5 . . ?
C18 C17 H17 116.5 . . ?
C17 C18 C19 117.8(11) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 114.9(9) . . ?
C20 C19 C19 124.1(10) . 7_567 ?
C18 C19 C19 121.0(10) . 7_567 ?
C19 C20 C21 121.3(11) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
N5 C21 C20 121.6(12) . . ?
N5 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
O12 Cl1 O10 115(2) . . ?
O12 Cl1 O11 112(3) . . ?
O10 Cl1 O11 107(3) . . ?
O12 Cl1 O13 108(3) . . ?
O10 Cl1 O13 106(3) . . ?
O11 Cl1 O13 108(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.08
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.686
_refine_diff_density_min         -1.097
_refine_diff_density_rms         0.242
