# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1576197'
_audit_update_record             
;
2017-09-24 deposited with the CCDC.
2017-11-13 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            'C26 H19 Cl2 N6 Ni O5'
_chemical_formula_weight         625.08

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

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

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

_cell_length_a                   11.5173(13)
_cell_length_b                   14.2819(16)
_cell_length_c                   15.8654(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.361(2)
_cell_angle_gamma                90
_cell_volume                     2581.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6643
_cell_measurement_theta_min      0.23
_cell_measurement_theta_max      22.68

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             1276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7366
_exptl_absorpt_correction_T_max  0.8536
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_diffrn_ambient_temperature      296(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 SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15487
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5883
_reflns_number_gt                4029
_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       'SMART (Bruker, 1998)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0500P)²+2.0566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5883
_refine_ls_number_parameters     361
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.38506(3) 0.60220(3) 0.70949(2) 0.02065(12) Uani 1 1 d . . . . .
Cl2 Cl 0.76351(8) 0.82782(6) 0.77605(7) 0.0477(3) Uani 1 1 d . . . . .
Cl1 Cl 1.00651(9) 0.45808(7) 0.69205(9) 0.0625(3) Uani 1 1 d . . . . .
O4 O 0.56687(17) 0.60241(15) 0.70580(14) 0.0288(5) Uani 1 1 d . . . . .
O1 O 1.20096(17) 0.60417(15) 0.70207(14) 0.0281(5) Uani 1 1 d . . . . .
O1W O 0.40868(18) 0.71897(15) 0.79161(14) 0.0315(5) Uani 1 1 d D . . . .
N1 N 0.3700(2) 0.48905(17) 0.62721(16) 0.0265(6) Uani 1 1 d . . . . .
N6 N 0.4064(2) 0.82560(18) 0.53906(16) 0.0266(6) Uani 1 1 d . . . . .
N5 N 0.3736(2) 0.69831(18) 0.61030(16) 0.0268(6) Uani 1 1 d . . . . .
O3 O 0.6316(2) 0.6515(2) 0.83800(16) 0.0495(7) Uani 1 1 d . . . . .
N4 N -0.1007(2) -0.01084(19) 0.31361(17) 0.0304(6) Uani 1 1 d . . . . .
N2 N 0.2944(2) 0.37119(19) 0.54805(18) 0.0322(6) Uani 1 1 d . . . . .
O2 O 1.1892(2) 0.7023(2) 0.80977(19) 0.0645(9) Uani 1 1 d . . . . .
N3 N -0.0250(2) 0.0996(2) 0.40211(18) 0.0373(7) Uani 1 1 d . . . . .
C19 C 0.6440(3) 0.6328(2) 0.7633(2) 0.0286(7) Uani 1 1 d . . . . .
C23 C 0.8335(3) 0.7234(2) 0.7571(2) 0.0280(7) Uani 1 1 d . . . . .
C16 C 0.4533(3) 0.9144(2) 0.5196(2) 0.0263(7) Uani 1 1 d . . . . .
C21 C 1.0132(3) 0.6439(2) 0.7392(2) 0.0270(7) Uani 1 1 d . . . . .
C14 C 0.4293(3) 0.7780(2) 0.6134(2) 0.0300(7) Uani 1 1 d . . . . .
H14 H 0.478783 0.799531 0.661039 0.036 Uiso 1 1 calc R U . . .
C22 C 0.9531(3) 0.7241(2) 0.7573(2) 0.0278(7) Uani 1 1 d . . . . .
H22 H 0.994519 0.779490 0.769793 0.033 Uiso 1 1 calc R U . . .
C26 C 0.9450(3) 0.5648(2) 0.7165(2) 0.0320(8) Uani 1 1 d . . . . .
C24 C 0.7680(2) 0.6425(2) 0.7427(2) 0.0268(7) Uani 1 1 d . . . . .
C25 C 0.8253(3) 0.5640(2) 0.7184(2) 0.0326(8) Uani 1 1 d . . . . .
H25 H 0.782684 0.509762 0.703079 0.039 Uiso 1 1 calc R U . . .
C20 C 1.1463(3) 0.6509(2) 0.7502(2) 0.0316(8) Uani 1 1 d . . . . .
C10 C 0.2757(3) 0.4392(2) 0.6028(2) 0.0339(8) Uani 1 1 d . . . . .
H10 H 0.203801 0.449764 0.621279 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2126(3) 0.3030(2) 0.5110(2) 0.0312(7) Uani 1 1 d . . . . .
C13 C 0.3096(3) 0.6937(2) 0.5297(2) 0.0317(7) Uani 1 1 d . . . . .
H13 H 0.260974 0.644312 0.509053 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0559(3) 0.1688(2) 0.4402(2) 0.0334(8) Uani 1 1 d . . . . .
C3 C -0.0109(3) 0.0441(2) 0.3361(2) 0.0360(8) Uani 1 1 d . . . . .
H3 H 0.055676 0.044687 0.309288 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3284(3) 0.7715(2) 0.4856(2) 0.0346(8) Uani 1 1 d . . . . .
H15 H 0.295259 0.785882 0.430118 0.042 Uiso 1 1 calc R U . . .
C8 C 0.0945(3) 0.3216(3) 0.4980(3) 0.0454(10) Uani 1 1 d . . . . .
H8 H 0.067315 0.379579 0.513244 0.055 Uiso 1 1 calc R U . . .
C9 C 0.0159(3) 0.2547(3) 0.4626(3) 0.0474(10) Uani 1 1 d . . . . .
H9 H -0.064042 0.267736 0.453824 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1731(3) 0.1504(3) 0.4530(3) 0.0493(10) Uani 1 1 d . . . . .
H5 H 0.200231 0.092419 0.437526 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4537(3) 0.4504(3) 0.5864(3) 0.0536(12) Uani 1 1 d . . . . .
H12 H 0.531224 0.470528 0.591797 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2521(3) 0.2171(3) 0.4886(3) 0.0496(11) Uani 1 1 d . . . . .
H6 H 0.332013 0.203953 0.497415 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4094(3) 0.3791(3) 0.5371(3) 0.0676(15) Uani 1 1 d . . . . .
H11 H 0.449143 0.342261 0.502325 0.081 Uiso 1 1 calc R U . . .
C2 C -0.1742(4) 0.0077(3) 0.3714(3) 0.0707(16) Uani 1 1 d . . . . .
H2 H -0.245765 -0.022042 0.372797 0.085 Uiso 1 1 calc R U . . .
C17 C 0.4164(5) 0.9568(3) 0.4451(3) 0.0826(19) Uani 1 1 d . . . . .
H17 H 0.358671 0.928858 0.406102 0.099 Uiso 1 1 calc R U . . .
C1 C -0.1291(4) 0.0751(4) 0.4263(3) 0.0789(18) Uani 1 1 d . . . . .
H1 H -0.162539 0.099610 0.471474 0.095 Uiso 1 1 calc R U . . .
C18 C 0.5362(4) 0.9580(3) 0.5741(3) 0.087(2) Uani 1 1 d . . . . .
H18 H 0.562574 0.930174 0.626340 0.105 Uiso 1 1 calc R U . . .
H1WA H 0.468045 0.704034 0.830436 0.131 Uiso 1 1 d DR U . . .
H1WB H 0.347545 0.705834 0.818536 0.131 Uiso 1 1 d DR 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 N1 2.069(3) . ?
Ni1 N5 2.078(3) . ?
Ni1 N4 2.093(3) 4_666 ?
Ni1 O4 2.103(2) . ?
Ni1 O1 2.107(2) 1_455 ?
Ni1 O1W 2.109(2) . ?
Cl2 C23 1.742(3) . ?
Cl1 C26 1.747(3) . ?
O4 C19 1.254(4) . ?
O1 C20 1.250(4) . ?
O1W H1WA 0.8775 . ?
O1W H1WB 0.8950 . ?
N1 C10 1.309(4) . ?
N1 C12 1.355(4) . ?
N6 C14 1.354(4) . ?
N6 C15 1.379(4) . ?
N6 C16 1.429(4) . ?
N5 C14 1.304(4) . ?
N5 C13 1.381(4) . ?
O3 C19 1.243(4) . ?
N4 C3 1.306(4) . ?
N4 C2 1.361(5) . ?
N2 C10 1.341(4) . ?
N2 C11 1.365(4) . ?
N2 C7 1.421(4) . ?
O2 C20 1.242(4) . ?
N3 C3 1.341(4) . ?
N3 C1 1.357(5) . ?
N3 C4 1.430(4) . ?
C19 C24 1.517(4) . ?
C23 C22 1.376(4) . ?
C23 C24 1.382(4) . ?
C16 C17 1.341(5) . ?
C16 C18 1.344(5) . ?
C21 C22 1.391(4) . ?
C21 C26 1.393(4) . ?
C21 C20 1.521(4) . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C26 C25 1.383(4) . ?
C24 C25 1.384(4) . ?
C25 H25 0.9300 . ?
C10 H10 0.9300 . ?
C7 C8 1.371(5) . ?
C7 C6 1.373(5) . ?
C13 C15 1.348(4) . ?
C13 H13 0.9300 . ?
C4 C5 1.362(5) . ?
C4 C9 1.375(5) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C8 C9 1.378(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C12 C11 1.338(5) . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C2 C1 1.351(5) . ?
C2 H2 0.9300 . ?
C17 C18 1.385(5) 3_676 ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?
C18 H18 0.9300 . ?

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
N1 Ni1 N5 92.74(10) . . ?
N1 Ni1 N4 90.04(11) . 4_666 ?
N5 Ni1 N4 177.15(11) . 4_666 ?
N1 Ni1 O4 88.63(9) . . ?
N5 Ni1 O4 86.10(9) . . ?
N4 Ni1 O4 93.38(9) 4_666 . ?
N1 Ni1 O1 89.07(9) . 1_455 ?
N5 Ni1 O1 89.78(9) . 1_455 ?
N4 Ni1 O1 90.86(9) 4_666 1_455 ?
O4 Ni1 O1 175.18(9) . 1_455 ?
N1 Ni1 O1W 177.15(9) . . ?
N5 Ni1 O1W 86.20(10) . . ?
N4 Ni1 O1W 90.99(10) 4_666 . ?
O4 Ni1 O1W 88.66(8) . . ?
O1 Ni1 O1W 93.57(8) 1_455 . ?
C19 O4 Ni1 125.6(2) . . ?
C20 O1 Ni1 124.4(2) . 1_655 ?
Ni1 O1W H1WA 105.0 . . ?
Ni1 O1W H1WB 95.1 . . ?
H1WA O1W H1WB 101.6 . . ?
C10 N1 C12 104.7(3) . . ?
C10 N1 Ni1 127.0(2) . . ?
C12 N1 Ni1 128.3(2) . . ?
C14 N6 C15 106.3(3) . . ?
C14 N6 C16 127.0(3) . . ?
C15 N6 C16 126.7(3) . . ?
C14 N5 C13 105.7(3) . . ?
C14 N5 Ni1 124.8(2) . . ?
C13 N5 Ni1 129.5(2) . . ?
C3 N4 C2 104.2(3) . . ?
C3 N4 Ni1 124.0(2) . 4_565 ?
C2 N4 Ni1 131.9(2) . 4_565 ?
C10 N2 C11 105.8(3) . . ?
C10 N2 C7 127.2(3) . . ?
C11 N2 C7 127.0(3) . . ?
C3 N3 C1 106.3(3) . . ?
C3 N3 C4 126.4(3) . . ?
C1 N3 C4 127.3(3) . . ?
O3 C19 O4 126.9(3) . . ?
O3 C19 C24 115.4(3) . . ?
O4 C19 C24 117.6(3) . . ?
C22 C23 C24 121.9(3) . . ?
C22 C23 Cl2 118.8(2) . . ?
C24 C23 Cl2 119.3(2) . . ?
C17 C16 C18 117.5(3) . . ?
C17 C16 N6 120.6(3) . . ?
C18 C16 N6 121.9(3) . . ?
C22 C21 C26 116.3(3) . . ?
C22 C21 C20 116.5(3) . . ?
C26 C21 C20 127.2(3) . . ?
N5 C14 N6 111.9(3) . . ?
N5 C14 H14 124.1 . . ?
N6 C14 H14 124.1 . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C25 C26 C21 121.8(3) . . ?
C25 C26 Cl1 115.8(2) . . ?
C21 C26 Cl1 122.2(2) . . ?
C23 C24 C25 116.9(3) . . ?
C23 C24 C19 123.3(3) . . ?
C25 C24 C19 119.3(3) . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
O2 C20 O1 126.9(3) . . ?
O2 C20 C21 114.2(3) . . ?
O1 C20 C21 118.9(3) . . ?
N1 C10 N2 112.4(3) . . ?
N1 C10 H10 123.8 . . ?
N2 C10 H10 123.8 . . ?
C8 C7 C6 119.5(3) . . ?
C8 C7 N2 120.9(3) . . ?
C6 C7 N2 119.6(3) . . ?
C15 C13 N5 109.7(3) . . ?
C15 C13 H13 125.2 . . ?
N5 C13 H13 125.2 . . ?
C5 C4 C9 119.7(3) . . ?
C5 C4 N3 120.0(3) . . ?
C9 C4 N3 120.3(3) . . ?
N4 C3 N3 112.8(3) . . ?
N4 C3 H3 123.6 . . ?
N3 C3 H3 123.6 . . ?
C13 C15 N6 106.4(3) . . ?
C13 C15 H15 126.8 . . ?
N6 C15 H15 126.8 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.9(3) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C11 C12 N1 110.6(3) . . ?
C11 C12 H12 124.7 . . ?
N1 C12 H12 124.7 . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C11 N2 106.5(3) . . ?
C12 C11 H11 126.8 . . ?
N2 C11 H11 126.8 . . ?
C1 C2 N4 110.8(3) . . ?
C1 C2 H2 124.6 . . ?
N4 C2 H2 124.6 . . ?
C16 C17 C18 120.4(4) . 3_676 ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 3_676 . ?
C2 C1 N3 105.9(4) . . ?
C2 C1 H1 127.0 . . ?
N3 C1 H1 127.0 . . ?
C16 C18 C17 122.1(4) . 3_676 ?
C16 C18 H18 118.9 . . ?
C17 C18 H18 118.9 3_676 . ?

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.080

