# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_d1837_a
_database_code_depnum_ccdc_archive 'CCDC 1884791'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C26 H28 N2 Ni O4'
_chemical_formula_sum            'C26 H28 N2 Ni O4'
_chemical_formula_weight         491.21

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0764(17)
_cell_length_b                   9.6715(15)
_cell_length_c                   20.657(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.155(5)
_cell_angle_gamma                90
_cell_volume                     2411.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2895
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      22.18

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.839
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35050
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_av_R_equivalents  0.1140
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.687
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4251
_reflns_number_gt                2794
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0245P)²+1.8852P] 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         4251
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.26360(3) 0.77367(4) 0.61546(2) 0.02207(13) Uani 1 1 d . . . . .
O1 O 0.38695(16) 0.6590(2) 0.64137(11) 0.0230(6) Uani 1 1 d . . . . .
O2 O 0.51783(18) 1.0462(2) 0.59063(13) 0.0357(7) Uani 1 1 d . . . . .
O3 O 0.13230(16) 0.8216(2) 0.65922(11) 0.0242(6) Uani 1 1 d . . . . .
O4 O 0.02973(17) 0.6584(2) 0.47747(12) 0.0334(6) Uani 1 1 d . . . . .
N1 N 0.3580(2) 0.9312(3) 0.59979(13) 0.0212(6) Uani 1 1 d . . . . .
N2 N 0.17956(19) 0.6970(3) 0.54225(13) 0.0214(7) Uani 1 1 d . . . . .
C1 C 0.4655(3) 0.9268(3) 0.60535(17) 0.0242(8) Uani 1 1 d . . . . .
C2 C 0.5327(3) 0.8145(3) 0.62497(17) 0.0265(9) Uani 1 1 d . . . . .
H2A H 0.610833 0.825999 0.625107 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4918(2) 0.6897(3) 0.64386(16) 0.0207(8) Uani 1 1 d . . . . .
C4 C 0.4336(3) 1.1408(4) 0.56585(19) 0.0348(10) Uani 1 1 d . . . . .
H4A H 0.438799 1.152773 0.518465 0.042 Uiso 1 1 calc R U . . .
H4B H 0.441553 1.232283 0.586985 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3227(3) 1.0733(3) 0.58211(17) 0.0257(8) Uani 1 1 d . . . . .
C6 C 0.5662(2) 0.5782(3) 0.66964(16) 0.0223(8) Uani 1 1 d . . . . .
C7 C 0.5221(3) 0.4517(3) 0.68651(16) 0.0263(9) Uani 1 1 d . . . . .
H7A H 0.444578 0.436766 0.680818 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5885(3) 0.3467(4) 0.71147(17) 0.0334(9) Uani 1 1 d . . . . .
H8A H 0.556644 0.260575 0.722695 0.040 Uiso 1 1 calc R U . . .
C9 C 0.7006(3) 0.3671(4) 0.72003(17) 0.0340(10) Uani 1 1 d . . . . .
H9A H 0.746489 0.294918 0.737017 0.041 Uiso 1 1 calc R U . . .
C10 C 0.7464(3) 0.4916(4) 0.70405(19) 0.0355(10) Uani 1 1 d . . . . .
H10A H 0.823966 0.505398 0.710192 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6807(3) 0.5974(4) 0.67906(17) 0.0302(9) Uani 1 1 d . . . . .
H11A H 0.713230 0.683418 0.668250 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2436(3) 1.0696(4) 0.5238(2) 0.0486(12) Uani 1 1 d . . . . .
H12A H 0.176149 1.019925 0.534852 0.073 Uiso 1 1 calc R U . . .
H12B H 0.278806 1.022213 0.488079 0.073 Uiso 1 1 calc R U . . .
H12C H 0.224528 1.164316 0.510758 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2736(3) 1.1420(4) 0.6401(2) 0.0501(12) Uani 1 1 d . . . . .
H13A H 0.205265 1.094191 0.650963 0.075 Uiso 1 1 calc R U . . .
H13B H 0.257024 1.238931 0.629848 0.075 Uiso 1 1 calc R U . . .
H13C H 0.326827 1.137500 0.677029 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0307(2) 0.8194(3) 0.63647(17) 0.0241(8) Uani 1 1 d . . . . .
C15 C -0.0020(3) 0.7687(4) 0.57679(17) 0.0294(9) Uani 1 1 d . . . . .
H15A H -0.078195 0.773615 0.563800 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0726(3) 0.7097(3) 0.53398(17) 0.0242(8) Uani 1 1 d . . . . .
C17 C 0.1224(3) 0.6180(4) 0.43951(18) 0.0334(9) Uani 1 1 d . . . . .
H17A H 0.134012 0.685416 0.404335 0.040 Uiso 1 1 calc R U . . .
H17B H 0.109883 0.525432 0.420163 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2226(3) 0.6160(3) 0.48778(17) 0.0261(8) Uani 1 1 d . . . . .
C19 C -0.0518(2) 0.8771(3) 0.68108(18) 0.0276(9) Uani 1 1 d . . . . .
C20 C -0.0335(3) 0.8631(4) 0.7473(2) 0.0374(10) Uani 1 1 d . . . . .
H20A H 0.030535 0.815453 0.763448 0.045 Uiso 1 1 calc R U . . .
C21 C -0.1073(3) 0.9174(4) 0.7906(2) 0.0488(12) Uani 1 1 d . . . . .
H21A H -0.093667 0.907625 0.835919 0.059 Uiso 1 1 calc R U . . .
C22 C -0.2007(3) 0.9858(4) 0.7671(3) 0.0523(13) Uani 1 1 d . . . . .
H22A H -0.251720 1.022837 0.796364 0.063 Uiso 1 1 calc R U . . .
C23 C -0.2201(3) 1.0006(4) 0.7018(3) 0.0508(13) Uani 1 1 d . . . . .
H23A H -0.284583 1.047688 0.685847 0.061 Uiso 1 1 calc R U . . .
C24 C -0.1457(3) 0.9469(4) 0.6587(2) 0.0384(10) Uani 1 1 d . . . . .
H24A H -0.159445 0.958121 0.613411 0.046 Uiso 1 1 calc R U . . .
C25 C 0.3243(3) 0.6848(4) 0.46115(18) 0.0381(10) Uani 1 1 d . . . . .
H25A H 0.383142 0.688838 0.495063 0.057 Uiso 1 1 calc R U . . .
H25B H 0.305328 0.778793 0.446860 0.057 Uiso 1 1 calc R U . . .
H25C H 0.349937 0.631272 0.424340 0.057 Uiso 1 1 calc R U . . .
C26 C 0.2494(3) 0.4707(3) 0.51114(19) 0.0357(10) Uani 1 1 d . . . . .
H26A H 0.305937 0.474738 0.546398 0.054 Uiso 1 1 calc R U . . .
H26B H 0.277411 0.416151 0.475261 0.054 Uiso 1 1 calc R U . . .
H26C H 0.182223 0.427195 0.526859 0.054 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 O3 1.912(2) . ?
Ni1 O1 1.917(2) . ?
Ni1 N2 1.937(3) . ?
Ni1 N1 1.937(3) . ?
O1 C3 1.299(3) . ?
O2 C1 1.356(4) . ?
O2 C4 1.447(4) . ?
O3 C14 1.297(4) . ?
O4 C16 1.353(4) . ?
O4 C17 1.444(4) . ?
N1 C1 1.300(4) . ?
N1 C5 1.481(4) . ?
N2 C16 1.302(4) . ?
N2 C18 1.481(4) . ?
C1 C2 1.406(4) . ?
C2 C3 1.367(4) . ?
C2 H2A 0.9500 . ?
C3 C6 1.489(4) . ?
C4 C5 1.538(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.508(5) . ?
C5 C13 1.510(5) . ?
C6 C7 1.384(4) . ?
C6 C11 1.401(4) . ?
C7 C8 1.382(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.373(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.371(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.383(5) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.371(5) . ?
C14 C19 1.491(5) . ?
C15 C16 1.407(4) . ?
C15 H15A 0.9500 . ?
C17 C18 1.539(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C26 1.517(5) . ?
C18 C25 1.518(4) . ?
C19 C20 1.384(5) . ?
C19 C24 1.384(5) . ?
C20 C21 1.389(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.379(6) . ?
C21 H21A 0.9500 . ?
C22 C23 1.368(6) . ?
C22 H22A 0.9500 . ?
C23 C24 1.389(5) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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 Ni1 O1 131.15(9) . . ?
O3 Ni1 N2 92.44(10) . . ?
O1 Ni1 N2 112.04(10) . . ?
O3 Ni1 N1 113.07(10) . . ?
O1 Ni1 N1 92.62(10) . . ?
N2 Ni1 N1 117.71(11) . . ?
C3 O1 Ni1 128.7(2) . . ?
C1 O2 C4 106.9(2) . . ?
C14 O3 Ni1 127.9(2) . . ?
C16 O4 C17 106.8(2) . . ?
C1 N1 C5 109.3(3) . . ?
C1 N1 Ni1 123.5(2) . . ?
C5 N1 Ni1 127.2(2) . . ?
C16 N2 C18 109.0(3) . . ?
C16 N2 Ni1 123.6(2) . . ?
C18 N2 Ni1 127.37(19) . . ?
N1 C1 O2 115.1(3) . . ?
N1 C1 C2 127.9(3) . . ?
O2 C1 C2 117.0(3) . . ?
C3 C2 C1 123.6(3) . . ?
C3 C2 H2A 118.2 . . ?
C1 C2 H2A 118.2 . . ?
O1 C3 C2 123.5(3) . . ?
O1 C3 C6 115.0(3) . . ?
C2 C3 C6 121.4(3) . . ?
O2 C4 C5 105.1(3) . . ?
O2 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
O2 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C12 110.1(3) . . ?
N1 C5 C13 109.3(3) . . ?
C12 C5 C13 112.8(3) . . ?
N1 C5 C4 101.7(2) . . ?
C12 C5 C4 111.5(3) . . ?
C13 C5 C4 110.9(3) . . ?
C7 C6 C11 118.0(3) . . ?
C7 C6 C3 119.8(3) . . ?
C11 C6 C3 122.2(3) . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9A 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10A 119.7 . . ?
C11 C10 H10A 119.7 . . ?
C10 C11 C6 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C6 C11 H11A 119.9 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 C15 124.6(3) . . ?
O3 C14 C19 114.5(3) . . ?
C15 C14 C19 120.9(3) . . ?
C14 C15 C16 122.7(3) . . ?
C14 C15 H15A 118.6 . . ?
C16 C15 H15A 118.6 . . ?
N2 C16 O4 115.1(3) . . ?
N2 C16 C15 127.7(3) . . ?
O4 C16 C15 117.2(3) . . ?
O4 C17 C18 105.0(3) . . ?
O4 C17 H17A 110.8 . . ?
C18 C17 H17A 110.8 . . ?
O4 C17 H17B 110.8 . . ?
C18 C17 H17B 110.8 . . ?
H17A C17 H17B 108.8 . . ?
N2 C18 C26 109.0(3) . . ?
N2 C18 C25 110.8(3) . . ?
C26 C18 C25 110.8(3) . . ?
N2 C18 C17 101.3(2) . . ?
C26 C18 C17 111.8(3) . . ?
C25 C18 C17 112.7(3) . . ?
C20 C19 C24 118.5(3) . . ?
C20 C19 C14 119.2(3) . . ?
C24 C19 C14 122.3(3) . . ?
C19 C20 C21 121.1(4) . . ?
C19 C20 H20A 119.5 . . ?
C21 C20 H20A 119.5 . . ?
C22 C21 C20 119.4(4) . . ?
C22 C21 H21A 120.3 . . ?
C20 C21 H21A 120.3 . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C19 C24 C23 120.7(4) . . ?
C19 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
C5 N1 C1 O2 -3.5(4) . . . . ?
Ni1 N1 C1 O2 178.2(2) . . . . ?
C5 N1 C1 C2 176.1(3) . . . . ?
Ni1 N1 C1 C2 -2.3(5) . . . . ?
C4 O2 C1 N1 -6.0(4) . . . . ?
C4 O2 C1 C2 174.4(3) . . . . ?
N1 C1 C2 C3 -2.3(6) . . . . ?
O2 C1 C2 C3 177.2(3) . . . . ?
Ni1 O1 C3 C2 -2.6(5) . . . . ?
Ni1 O1 C3 C6 176.9(2) . . . . ?
C1 C2 C3 O1 4.9(6) . . . . ?
C1 C2 C3 C6 -174.6(3) . . . . ?
C1 O2 C4 C5 12.3(4) . . . . ?
C1 N1 C5 C12 128.9(3) . . . . ?
Ni1 N1 C5 C12 -52.9(4) . . . . ?
C1 N1 C5 C13 -106.7(3) . . . . ?
Ni1 N1 C5 C13 71.6(4) . . . . ?
C1 N1 C5 C4 10.6(4) . . . . ?
Ni1 N1 C5 C4 -171.1(2) . . . . ?
O2 C4 C5 N1 -13.6(4) . . . . ?
O2 C4 C5 C12 -130.8(3) . . . . ?
O2 C4 C5 C13 102.5(3) . . . . ?
O1 C3 C6 C7 2.3(5) . . . . ?
C2 C3 C6 C7 -178.1(3) . . . . ?
O1 C3 C6 C11 -176.2(3) . . . . ?
C2 C3 C6 C11 3.4(5) . . . . ?
C11 C6 C7 C8 -0.5(5) . . . . ?
C3 C6 C7 C8 -179.0(3) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C6 -0.2(6) . . . . ?
C7 C6 C11 C10 0.5(5) . . . . ?
C3 C6 C11 C10 179.0(3) . . . . ?
Ni1 O3 C14 C15 6.3(5) . . . . ?
Ni1 O3 C14 C19 -173.9(2) . . . . ?
O3 C14 C15 C16 1.6(5) . . . . ?
C19 C14 C15 C16 -178.1(3) . . . . ?
C18 N2 C16 O4 -5.1(4) . . . . ?
Ni1 N2 C16 O4 175.1(2) . . . . ?
C18 N2 C16 C15 174.2(3) . . . . ?
Ni1 N2 C16 C15 -5.5(5) . . . . ?
C17 O4 C16 N2 -6.6(4) . . . . ?
C17 O4 C16 C15 174.0(3) . . . . ?
C14 C15 C16 N2 -1.9(6) . . . . ?
C14 C15 C16 O4 177.5(3) . . . . ?
C16 O4 C17 C18 14.7(3) . . . . ?
C16 N2 C18 C26 -104.4(3) . . . . ?
Ni1 N2 C18 C26 75.3(3) . . . . ?
C16 N2 C18 C25 133.4(3) . . . . ?
Ni1 N2 C18 C25 -46.9(4) . . . . ?
C16 N2 C18 C17 13.6(3) . . . . ?
Ni1 N2 C18 C17 -166.7(2) . . . . ?
O4 C17 C18 N2 -16.7(3) . . . . ?
O4 C17 C18 C26 99.1(3) . . . . ?
O4 C17 C18 C25 -135.2(3) . . . . ?
O3 C14 C19 C20 -32.1(4) . . . . ?
C15 C14 C19 C20 147.7(3) . . . . ?
O3 C14 C19 C24 146.7(3) . . . . ?
C15 C14 C19 C24 -33.5(5) . . . . ?
C24 C19 C20 C21 0.0(5) . . . . ?
C14 C19 C20 C21 178.9(3) . . . . ?
C19 C20 C21 C22 0.4(6) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C21 C22 C23 C24 -0.1(6) . . . . ?
C20 C19 C24 C23 -0.4(5) . . . . ?
C14 C19 C24 C23 -179.3(3) . . . . ?
C22 C23 C24 C19 0.5(6) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_d1839_a
_database_code_depnum_ccdc_archive 'CCDC 1884792'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C22 H24 N2 Ni O6'
_chemical_formula_sum            'C22 H24 N2 Ni O6'
_chemical_formula_weight         471.14

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2574(8)
_cell_length_b                   8.8952(7)
_cell_length_c                   23.418(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.190(3)
_cell_angle_gamma                90
_cell_volume                     2127.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6851
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.36

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.953
_shelx_estimated_absorpt_T_min   0.847
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33572
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4920
_reflns_number_gt                3750
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0256P)²+1.2931P] 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         4920
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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 0.29245(2) 0.37583(3) 0.29373(2) 0.01626(7) Uani 1 1 d . . . . .
O1 O 0.27627(13) 0.34939(14) 0.21149(5) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.65050(13) 0.18449(16) 0.27586(6) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.42065(14) 0.25341(16) 0.08403(6) 0.0251(3) Uani 1 1 d . . . . .
O4 O 0.26653(13) 0.52585(14) 0.35099(5) 0.0186(3) Uani 1 1 d . . . . .
O5 O -0.00096(13) 0.17102(15) 0.37402(6) 0.0230(3) Uani 1 1 d . . . . .
O6 O 0.10512(15) 0.66297(16) 0.46947(6) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.47098(15) 0.29679(17) 0.30409(7) 0.0162(3) Uani 1 1 d . . . . .
N2 N 0.15331(15) 0.24752(17) 0.31817(7) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.36573(19) 0.2941(2) 0.18154(8) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.48735(19) 0.2453(2) 0.20234(8) 0.0188(4) Uani 1 1 d . . . . .
H2A H 0.544870 0.208773 0.175910 0.023 Uiso 1 1 calc R U . . .
C3 C 0.53141(19) 0.2465(2) 0.26130(8) 0.0177(4) Uani 1 1 d . . . . .
C4 C 0.6802(2) 0.2079(2) 0.33660(9) 0.0251(5) Uani 1 1 d . . . . .
H4A H 0.748698 0.285698 0.343845 0.030 Uiso 1 1 calc R U . . .
H4B H 0.711097 0.113489 0.355686 0.030 Uiso 1 1 calc R U . . .
C5 C 0.55036(19) 0.2600(2) 0.35883(8) 0.0191(4) Uani 1 1 d . . . . .
C6 C 0.3246(2) 0.2796(2) 0.12021(8) 0.0193(4) Uani 1 1 d . . . . .
C7 C 0.2061(2) 0.2746(3) 0.09002(9) 0.0306(5) Uani 1 1 d . . . . .
H7A H 0.123614 0.289629 0.104577 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2286(3) 0.2423(3) 0.03210(10) 0.0358(6) Uani 1 1 d . . . . .
H8A H 0.164247 0.231182 0.000585 0.043 Uiso 1 1 calc R U . . .
C9 C 0.3576(2) 0.2308(2) 0.03091(9) 0.0318(5) Uani 1 1 d . . . . .
H9A H 0.400179 0.209631 -0.002544 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5696(2) 0.3974(2) 0.39708(9) 0.0267(5) Uani 1 1 d . . . . .
H10A H 0.484310 0.432921 0.407320 0.040 Uiso 1 1 calc R U . . .
H10B H 0.612155 0.477008 0.376615 0.040 Uiso 1 1 calc R U . . .
H10C H 0.624657 0.370853 0.432014 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4841(2) 0.1334(2) 0.38900(9) 0.0248(4) Uani 1 1 d . . . . .
H11A H 0.396874 0.166054 0.397824 0.037 Uiso 1 1 calc R U . . .
H11B H 0.536778 0.107630 0.424653 0.037 Uiso 1 1 calc R U . . .
H11C H 0.475852 0.045024 0.363944 0.037 Uiso 1 1 calc R U . . .
C12 C 0.18225(19) 0.5222(2) 0.38911(8) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.09448(19) 0.4093(2) 0.39619(8) 0.0190(4) Uani 1 1 d . . . . .
H13A H 0.036508 0.419091 0.425401 0.023 Uiso 1 1 calc R U . . .
C14 C 0.08687(18) 0.2784(2) 0.36158(8) 0.0171(4) Uani 1 1 d . . . . .
C15 C 0.0247(2) 0.0408(2) 0.33905(9) 0.0235(5) Uani 1 1 d . . . . .
H15A H -0.058165 -0.005032 0.322434 0.028 Uiso 1 1 calc R U . . .
H15B H 0.075790 -0.035974 0.362080 0.028 Uiso 1 1 calc R U . . .
C16 C 0.10361(19) 0.1034(2) 0.29175(9) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.18902(19) 0.6543(2) 0.42702(8) 0.0177(4) Uani 1 1 d . . . . .
C18 C 0.2666(2) 0.7768(2) 0.42907(9) 0.0236(5) Uani 1 1 d . . . . .
H18A H 0.332946 0.798138 0.404451 0.028 Uiso 1 1 calc R U . . .
C19 C 0.2306(2) 0.8682(2) 0.47493(9) 0.0279(5) Uani 1 1 d . . . . .
H19A H 0.267894 0.962048 0.486926 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1339(2) 0.7954(3) 0.49775(10) 0.0324(5) Uani 1 1 d . . . . .
H20A H 0.090753 0.830758 0.529380 0.039 Uiso 1 1 calc R U . . .
C21 C 0.0159(2) 0.1373(2) 0.23739(9) 0.0292(5) Uani 1 1 d . . . . .
H21A H 0.064952 0.195734 0.211043 0.044 Uiso 1 1 calc R U . . .
H21B H -0.060279 0.195308 0.247139 0.044 Uiso 1 1 calc R U . . .
H21C H -0.013601 0.042818 0.218981 0.044 Uiso 1 1 calc R U . . .
C22 C 0.2166(2) 0.0018(2) 0.27872(10) 0.0290(5) Uani 1 1 d . . . . .
H22A H 0.267507 0.050657 0.250510 0.044 Uiso 1 1 calc R U . . .
H22B H 0.182001 -0.094010 0.263222 0.044 Uiso 1 1 calc R U . . .
H22C H 0.273102 -0.016734 0.314047 0.044 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 O4 1.9272(13) . ?
Ni1 O1 1.9325(13) . ?
Ni1 N2 1.9531(16) . ?
Ni1 N1 1.9560(16) . ?
O1 C1 1.301(2) . ?
O2 C3 1.356(2) . ?
O2 C4 1.443(2) . ?
O3 C9 1.364(3) . ?
O3 C6 1.376(2) . ?
O4 C12 1.298(2) . ?
O5 C14 1.362(2) . ?
O5 C15 1.457(2) . ?
O6 C20 1.370(2) . ?
O6 C17 1.375(2) . ?
N1 C3 1.304(2) . ?
N1 C5 1.492(2) . ?
N2 C14 1.303(2) . ?
N2 C16 1.493(2) . ?
C1 C2 1.368(3) . ?
C1 C6 1.466(3) . ?
C2 C3 1.414(3) . ?
C2 H2A 0.9500 . ?
C4 C5 1.544(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.518(3) . ?
C5 C11 1.522(3) . ?
C6 C7 1.350(3) . ?
C7 C8 1.426(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.329(3) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.369(3) . ?
C12 C17 1.470(3) . ?
C13 C14 1.417(3) . ?
C13 H13A 0.9500 . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.521(3) . ?
C16 C22 1.522(3) . ?
C17 C18 1.348(3) . ?
C18 C19 1.422(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.336(3) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
O4 Ni1 O1 140.61(6) . . ?
O4 Ni1 N2 92.89(6) . . ?
O1 Ni1 N2 102.81(6) . . ?
O4 Ni1 N1 110.44(6) . . ?
O1 Ni1 N1 94.29(6) . . ?
N2 Ni1 N1 117.02(7) . . ?
C1 O1 Ni1 125.60(12) . . ?
C3 O2 C4 107.11(14) . . ?
C9 O3 C6 106.20(17) . . ?
C12 O4 Ni1 127.12(12) . . ?
C14 O5 C15 106.29(14) . . ?
C20 O6 C17 106.05(16) . . ?
C3 N1 C5 108.94(16) . . ?
C3 N1 Ni1 122.19(13) . . ?
C5 N1 Ni1 128.15(12) . . ?
C14 N2 C16 108.72(15) . . ?
C14 N2 Ni1 123.58(13) . . ?
C16 N2 Ni1 127.70(12) . . ?
O1 C1 C2 126.38(18) . . ?
O1 C1 C6 114.01(17) . . ?
C2 C1 C6 119.56(17) . . ?
C1 C2 C3 123.08(17) . . ?
C1 C2 H2A 118.5 . . ?
C3 C2 H2A 118.5 . . ?
N1 C3 O2 115.25(17) . . ?
N1 C3 C2 128.40(18) . . ?
O2 C3 C2 116.33(16) . . ?
O2 C4 C5 105.32(16) . . ?
O2 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
O2 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C10 111.23(16) . . ?
N1 C5 C11 109.23(16) . . ?
C10 C5 C11 111.18(17) . . ?
N1 C5 C4 101.34(15) . . ?
C10 C5 C4 111.76(17) . . ?
C11 C5 C4 111.70(16) . . ?
C7 C6 O3 109.44(18) . . ?
C7 C6 C1 133.00(19) . . ?
O3 C6 C1 117.33(17) . . ?
C6 C7 C8 106.8(2) . . ?
C6 C7 H7A 126.6 . . ?
C8 C7 H7A 126.6 . . ?
C9 C8 C7 106.4(2) . . ?
C9 C8 H8A 126.8 . . ?
C7 C8 H8A 126.8 . . ?
C8 C9 O3 111.13(19) . . ?
C8 C9 H9A 124.4 . . ?
O3 C9 H9A 124.4 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C13 126.02(17) . . ?
O4 C12 C17 113.40(16) . . ?
C13 C12 C17 120.57(17) . . ?
C12 C13 C14 122.44(17) . . ?
C12 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
N2 C14 O5 114.96(16) . . ?
N2 C14 C13 127.84(18) . . ?
O5 C14 C13 117.19(16) . . ?
O5 C15 C16 104.55(15) . . ?
O5 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
O5 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
N2 C16 C21 109.27(16) . . ?
N2 C16 C22 110.80(16) . . ?
C21 C16 C22 110.72(17) . . ?
N2 C16 C15 101.25(15) . . ?
C21 C16 C15 111.43(17) . . ?
C22 C16 C15 112.96(17) . . ?
C18 C17 O6 109.56(16) . . ?
C18 C17 C12 131.54(17) . . ?
O6 C17 C12 118.90(16) . . ?
C17 C18 C19 107.26(18) . . ?
C17 C18 H18A 126.4 . . ?
C19 C18 H18A 126.4 . . ?
C20 C19 C18 106.13(19) . . ?
C20 C19 H19A 126.9 . . ?
C18 C19 H19A 126.9 . . ?
C19 C20 O6 111.01(18) . . ?
C19 C20 H20A 124.5 . . ?
O6 C20 H20A 124.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 O1 C1 C2 -0.3(3) . . . . ?
Ni1 O1 C1 C6 176.94(12) . . . . ?
O1 C1 C2 C3 1.2(3) . . . . ?
C6 C1 C2 C3 -175.93(17) . . . . ?
C5 N1 C3 O2 -4.0(2) . . . . ?
Ni1 N1 C3 O2 -174.96(12) . . . . ?
C5 N1 C3 C2 174.29(18) . . . . ?
Ni1 N1 C3 C2 3.3(3) . . . . ?
C4 O2 C3 N1 -5.8(2) . . . . ?
C4 O2 C3 C2 175.71(17) . . . . ?
C1 C2 C3 N1 -2.9(3) . . . . ?
C1 C2 C3 O2 175.31(17) . . . . ?
C3 O2 C4 C5 12.5(2) . . . . ?
C3 N1 C5 C10 130.00(18) . . . . ?
Ni1 N1 C5 C10 -59.7(2) . . . . ?
C3 N1 C5 C11 -106.90(18) . . . . ?
Ni1 N1 C5 C11 63.4(2) . . . . ?
C3 N1 C5 C4 11.1(2) . . . . ?
Ni1 N1 C5 C4 -178.61(13) . . . . ?
O2 C4 C5 N1 -13.95(19) . . . . ?
O2 C4 C5 C10 -132.48(17) . . . . ?
O2 C4 C5 C11 102.24(18) . . . . ?
C9 O3 C6 C7 -0.6(2) . . . . ?
C9 O3 C6 C1 174.61(17) . . . . ?
O1 C1 C6 C7 -20.0(3) . . . . ?
C2 C1 C6 C7 157.5(2) . . . . ?
O1 C1 C6 O3 166.25(15) . . . . ?
C2 C1 C6 O3 -16.3(3) . . . . ?
O3 C6 C7 C8 0.6(2) . . . . ?
C1 C6 C7 C8 -173.6(2) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 O3 0.0(3) . . . . ?
C6 O3 C9 C8 0.4(2) . . . . ?
Ni1 O4 C12 C13 0.2(3) . . . . ?
Ni1 O4 C12 C17 179.26(12) . . . . ?
O4 C12 C13 C14 0.6(3) . . . . ?
C17 C12 C13 C14 -178.38(18) . . . . ?
C16 N2 C14 O5 4.3(2) . . . . ?
Ni1 N2 C14 O5 -176.36(12) . . . . ?
C16 N2 C14 C13 -174.89(19) . . . . ?
Ni1 N2 C14 C13 4.5(3) . . . . ?
C15 O5 C14 N2 9.5(2) . . . . ?
C15 O5 C14 C13 -171.24(17) . . . . ?
C12 C13 C14 N2 -3.3(3) . . . . ?
C12 C13 C14 O5 177.57(18) . . . . ?
C14 O5 C15 C16 -18.4(2) . . . . ?
C14 N2 C16 C21 102.49(19) . . . . ?
Ni1 N2 C16 C21 -76.82(19) . . . . ?
C14 N2 C16 C22 -135.24(18) . . . . ?
Ni1 N2 C16 C22 45.5(2) . . . . ?
C14 N2 C16 C15 -15.2(2) . . . . ?
Ni1 N2 C16 C15 165.53(13) . . . . ?
O5 C15 C16 N2 19.88(19) . . . . ?
O5 C15 C16 C21 -96.20(19) . . . . ?
O5 C15 C16 C22 138.41(17) . . . . ?
C20 O6 C17 C18 0.0(2) . . . . ?
C20 O6 C17 C12 179.61(18) . . . . ?
O4 C12 C17 C18 -0.1(3) . . . . ?
C13 C12 C17 C18 179.1(2) . . . . ?
O4 C12 C17 O6 -179.57(16) . . . . ?
C13 C12 C17 O6 -0.4(3) . . . . ?
O6 C17 C18 C19 0.0(2) . . . . ?
C12 C17 C18 C19 -179.6(2) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C18 C19 C20 O6 -0.1(3) . . . . ?
C17 O6 C20 C19 0.0(3) . . . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_d1833_a
_database_code_depnum_ccdc_archive 'CCDC 1884793'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C26 H26 N4 Ni O8'
_chemical_formula_sum            'C26 H26 N4 Ni O8'
_chemical_formula_weight         581.22

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                   9.5476(10)
_cell_length_b                   10.5561(12)
_cell_length_c                   14.4705(16)
_cell_angle_alpha                74.720(3)
_cell_angle_beta                 70.961(3)
_cell_angle_gamma                70.689(3)
_cell_volume                     1281.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.99

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             604
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31731
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.512
_diffrn_reflns_theta_max         27.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5961
_reflns_number_gt                4997
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0292P)²+0.7962P] 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         5961
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.25820(3) 0.22831(2) 0.69064(2) 0.01741(7) Uani 1 1 d . . . . .
O1 O 0.29718(13) 0.14992(12) 0.81975(8) 0.0197(2) Uani 1 1 d . . . . .
O2 O 0.07788(16) -0.10011(13) 0.76474(9) 0.0277(3) Uani 1 1 d . . . . .
O3 O 0.40583(18) 0.06752(14) 1.27684(10) 0.0337(3) Uani 1 1 d . . . . .
O4 O 0.37166(16) -0.13402(13) 1.31547(9) 0.0285(3) Uani 1 1 d . . . . .
O5 O 0.36116(14) 0.28431(11) 0.55334(8) 0.0199(2) Uani 1 1 d . . . . .
O6 O 0.03214(16) 0.63689(13) 0.65338(10) 0.0350(3) Uani 1 1 d . . . . .
O7 O 0.6376(2) 0.36871(15) 0.04318(10) 0.0459(4) Uani 1 1 d . . . . .
O8 O 0.65871(18) 0.56613(14) 0.03967(9) 0.0351(3) Uani 1 1 d . . . . .
N1 N 0.17180(16) 0.08212(14) 0.69509(10) 0.0181(3) Uani 1 1 d . . . . .
N2 N 0.37489(17) -0.02519(14) 1.25832(10) 0.0206(3) Uani 1 1 d . . . . .
N3 N 0.12727(16) 0.41315(14) 0.70459(10) 0.0188(3) Uani 1 1 d . . . . .
N4 N 0.62420(18) 0.46059(15) 0.08473(11) 0.0235(3) Uani 1 1 d . . . . .
C1 C 0.24481(19) 0.05400(16) 0.88460(11) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.1670(2) -0.02249(17) 0.86823(12) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.128748 -0.087458 0.921603 0.025 Uiso 1 1 calc R U . . .
C3 C 0.14129(19) -0.00811(17) 0.77403(12) 0.0189(3) Uani 1 1 d . . . . .
C4 C 0.0538(3) -0.0614(2) 0.66648(14) 0.0328(5) Uani 1 1 d . . . . .
H4A H -0.057459 -0.027430 0.670254 0.039 Uiso 1 1 calc R U . . .
H4B H 0.098728 -0.140169 0.631283 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1343(2) 0.05140(18) 0.61269(12) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.27433(18) 0.03095(16) 0.98428(11) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.26690(19) -0.08964(17) 1.05340(12) 0.0191(3) Uani 1 1 d . . . . .
H7A H 0.239399 -0.159203 1.038503 0.023 Uiso 1 1 calc R U . . .
C8 C 0.29950(19) -0.10772(17) 1.14334(12) 0.0192(3) Uani 1 1 d . . . . .
H8A H 0.294913 -0.189333 1.190269 0.023 Uiso 1 1 calc R U . . .
C9 C 0.33887(18) -0.00478(16) 1.16363(11) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.34650(19) 0.11562(16) 1.09718(12) 0.0187(3) Uani 1 1 d . . . . .
H10A H 0.373287 0.185148 1.112664 0.022 Uiso 1 1 calc R U . . .
C11 C 0.31405(19) 0.13198(16) 1.00761(12) 0.0185(3) Uani 1 1 d . . . . .
H11A H 0.318990 0.213880 0.961083 0.022 Uiso 1 1 calc R U . . .
C12 C 0.0299(3) 0.1778(2) 0.56655(17) 0.0430(6) Uani 1 1 d . . . . .
H12A H 0.083483 0.249604 0.538200 0.064 Uiso 1 1 calc R U . . .
H12B H -0.063847 0.209533 0.617627 0.064 Uiso 1 1 calc R U . . .
H12C H 0.002704 0.155809 0.514028 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2826(2) -0.0007(2) 0.53668(15) 0.0366(5) Uani 1 1 d . . . . .
H13A H 0.339914 0.068560 0.511228 0.055 Uiso 1 1 calc R U . . .
H13B H 0.258520 -0.019759 0.481714 0.055 Uiso 1 1 calc R U . . .
H13C H 0.345130 -0.084463 0.568031 0.055 Uiso 1 1 calc R U . . .
C14 C 0.33829(19) 0.40615(17) 0.50193(12) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.2368(2) 0.52104(17) 0.53628(13) 0.0235(4) Uani 1 1 d . . . . .
H15A H 0.233881 0.606665 0.493333 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1363(2) 0.51717(17) 0.63315(13) 0.0219(4) Uani 1 1 d . . . . .
C17 C -0.0487(3) 0.6120(2) 0.75712(16) 0.0419(6) Uani 1 1 d . . . . .
H17A H -0.160964 0.651624 0.766579 0.050 Uiso 1 1 calc R U . . .
H17B H -0.013437 0.652229 0.797096 0.050 Uiso 1 1 calc R U . . .
C18 C -0.0104(2) 0.45740(18) 0.78703(13) 0.0220(4) Uani 1 1 d . . . . .
C19 C 0.42436(19) 0.41907(16) 0.39429(12) 0.0174(3) Uani 1 1 d . . . . .
C20 C 0.47018(19) 0.53688(17) 0.34161(12) 0.0193(3) Uani 1 1 d . . . . .
H20A H 0.453887 0.608249 0.375652 0.023 Uiso 1 1 calc R U . . .
C21 C 0.53897(19) 0.55053(17) 0.24050(12) 0.0191(3) Uani 1 1 d . . . . .
H21A H 0.570240 0.630318 0.204663 0.023 Uiso 1 1 calc R U . . .
C22 C 0.56098(19) 0.44468(17) 0.19296(12) 0.0182(3) Uani 1 1 d . . . . .
C23 C 0.5216(2) 0.32527(17) 0.24309(13) 0.0232(4) Uani 1 1 d . . . . .
H23A H 0.540845 0.253218 0.208971 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4537(2) 0.31318(17) 0.34409(12) 0.0217(4) Uani 1 1 d . . . . .
H24A H 0.426576 0.231537 0.379808 0.026 Uiso 1 1 calc R U . . .
C25 C 0.0246(2) 0.4096(3) 0.88802(15) 0.0408(5) Uani 1 1 d . . . . .
H25A H 0.115679 0.435522 0.885166 0.061 Uiso 1 1 calc R U . . .
H25B H 0.044244 0.310201 0.905678 0.061 Uiso 1 1 calc R U . . .
H25C H -0.063460 0.452155 0.938194 0.061 Uiso 1 1 calc R U . . .
C26 C -0.1366(2) 0.4006(2) 0.78621(16) 0.0345(5) Uani 1 1 d . . . . .
H26A H -0.163538 0.436939 0.722744 0.052 Uiso 1 1 calc R U . . .
H26B H -0.227383 0.427273 0.840586 0.052 Uiso 1 1 calc R U . . .
H26C H -0.100250 0.300954 0.794787 0.052 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 O1 1.9362(11) . ?
Ni1 O5 1.9377(11) . ?
Ni1 N1 1.9547(14) . ?
Ni1 N3 1.9597(14) . ?
O1 C1 1.2976(19) . ?
O2 C3 1.356(2) . ?
O2 C4 1.445(2) . ?
O3 N2 1.2238(18) . ?
O4 N2 1.2291(18) . ?
O5 C14 1.2927(19) . ?
O6 C16 1.358(2) . ?
O6 C17 1.445(2) . ?
O7 N4 1.2222(19) . ?
O8 N4 1.2226(19) . ?
N1 C3 1.300(2) . ?
N1 C5 1.488(2) . ?
N2 C9 1.465(2) . ?
N3 C16 1.299(2) . ?
N3 C18 1.494(2) . ?
N4 C22 1.469(2) . ?
C1 C2 1.369(2) . ?
C1 C6 1.501(2) . ?
C2 C3 1.423(2) . ?
C2 H2A 0.9500 . ?
C4 C5 1.530(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.518(3) . ?
C5 C13 1.518(3) . ?
C6 C11 1.391(2) . ?
C6 C7 1.403(2) . ?
C7 C8 1.386(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.384(2) . ?
C10 C11 1.384(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.372(2) . ?
C14 C19 1.499(2) . ?
C15 C16 1.416(2) . ?
C15 H15A 0.9500 . ?
C17 C18 1.523(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C26 1.517(3) . ?
C18 C25 1.523(3) . ?
C19 C24 1.394(2) . ?
C19 C20 1.401(2) . ?
C20 C21 1.385(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.386(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.382(2) . ?
C23 C24 1.382(2) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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 O5 141.83(5) . . ?
O1 Ni1 N1 92.16(5) . . ?
O5 Ni1 N1 107.53(5) . . ?
O1 Ni1 N3 104.36(5) . . ?
O5 Ni1 N3 93.04(5) . . ?
N1 Ni1 N3 121.31(6) . . ?
C1 O1 Ni1 127.32(11) . . ?
C3 O2 C4 106.79(13) . . ?
C14 O5 Ni1 127.15(11) . . ?
C16 O6 C17 106.50(14) . . ?
C3 N1 C5 108.79(14) . . ?
C3 N1 Ni1 123.38(11) . . ?
C5 N1 Ni1 127.81(11) . . ?
O3 N2 O4 123.26(14) . . ?
O3 N2 C9 118.25(14) . . ?
O4 N2 C9 118.49(13) . . ?
C16 N3 C18 108.08(14) . . ?
C16 N3 Ni1 122.88(12) . . ?
C18 N3 Ni1 128.40(11) . . ?
O7 N4 O8 122.68(15) . . ?
O7 N4 C22 118.60(14) . . ?
O8 N4 C22 118.70(14) . . ?
O1 C1 C2 125.21(15) . . ?
O1 C1 C6 114.59(14) . . ?
C2 C1 C6 120.19(14) . . ?
C1 C2 C3 122.30(15) . . ?
C1 C2 H2A 118.9 . . ?
C3 C2 H2A 118.9 . . ?
N1 C3 O2 115.57(14) . . ?
N1 C3 C2 128.10(15) . . ?
O2 C3 C2 116.33(14) . . ?
O2 C4 C5 105.81(14) . . ?
O2 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
O2 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
N1 C5 C12 110.00(14) . . ?
N1 C5 C13 109.12(15) . . ?
C12 C5 C13 111.52(17) . . ?
N1 C5 C4 101.97(13) . . ?
C12 C5 C4 112.58(17) . . ?
C13 C5 C4 111.21(16) . . ?
C11 C6 C7 119.04(15) . . ?
C11 C6 C1 118.49(14) . . ?
C7 C6 C1 122.45(14) . . ?
C8 C7 C6 120.28(15) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 118.88(15) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C10 C9 C8 122.22(15) . . ?
C10 C9 N2 119.18(14) . . ?
C8 C9 N2 118.60(14) . . ?
C11 C10 C9 118.21(15) . . ?
C11 C10 H10A 120.9 . . ?
C9 C10 H10A 120.9 . . ?
C10 C11 C6 121.36(15) . . ?
C10 C11 H11A 119.3 . . ?
C6 C11 H11A 119.3 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 C14 C15 125.59(15) . . ?
O5 C14 C19 116.06(14) . . ?
C15 C14 C19 118.24(14) . . ?
C14 C15 C16 122.68(15) . . ?
C14 C15 H15A 118.7 . . ?
C16 C15 H15A 118.7 . . ?
N3 C16 O6 115.45(15) . . ?
N3 C16 C15 128.54(16) . . ?
O6 C16 C15 115.98(15) . . ?
O6 C17 C18 105.16(15) . . ?
O6 C17 H17A 110.7 . . ?
C18 C17 H17A 110.7 . . ?
O6 C17 H17B 110.7 . . ?
C18 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
N3 C18 C26 108.24(14) . . ?
N3 C18 C25 112.31(15) . . ?
C26 C18 C25 109.91(17) . . ?
N3 C18 C17 101.77(14) . . ?
C26 C18 C17 112.23(17) . . ?
C25 C18 C17 112.12(17) . . ?
C24 C19 C20 119.02(15) . . ?
C24 C19 C14 119.01(14) . . ?
C20 C19 C14 121.90(14) . . ?
C21 C20 C19 120.77(15) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 118.23(15) . . ?
C20 C21 H21A 120.9 . . ?
C22 C21 H21A 120.9 . . ?
C23 C22 C21 122.55(15) . . ?
C23 C22 N4 118.23(14) . . ?
C21 C22 N4 119.20(14) . . ?
C22 C23 C24 118.40(15) . . ?
C22 C23 H23A 120.8 . . ?
C24 C23 H23A 120.8 . . ?
C23 C24 C19 120.96(15) . . ?
C23 C24 H24A 119.5 . . ?
C19 C24 H24A 119.5 . . ?
C18 C25 H25A 109.5 . . ?
C18 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C18 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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 O1 C1 C2 8.9(2) . . . . ?
Ni1 O1 C1 C6 -170.48(10) . . . . ?
O1 C1 C2 C3 3.1(3) . . . . ?
C6 C1 C2 C3 -177.54(15) . . . . ?
C5 N1 C3 O2 -3.2(2) . . . . ?
Ni1 N1 C3 O2 178.30(11) . . . . ?
C5 N1 C3 C2 176.37(17) . . . . ?
Ni1 N1 C3 C2 -2.1(3) . . . . ?
C4 O2 C3 N1 -3.8(2) . . . . ?
C4 O2 C3 C2 176.55(16) . . . . ?
C1 C2 C3 N1 -6.7(3) . . . . ?
C1 C2 C3 O2 172.91(16) . . . . ?
C3 O2 C4 C5 8.8(2) . . . . ?
C3 N1 C5 C12 127.93(17) . . . . ?
Ni1 N1 C5 C12 -53.7(2) . . . . ?
C3 N1 C5 C13 -109.43(17) . . . . ?
Ni1 N1 C5 C13 68.95(18) . . . . ?
C3 N1 C5 C4 8.27(19) . . . . ?
Ni1 N1 C5 C4 -173.35(12) . . . . ?
O2 C4 C5 N1 -10.16(19) . . . . ?
O2 C4 C5 C12 -127.99(17) . . . . ?
O2 C4 C5 C13 106.03(18) . . . . ?
O1 C1 C6 C11 17.0(2) . . . . ?
C2 C1 C6 C11 -162.43(16) . . . . ?
O1 C1 C6 C7 -161.44(15) . . . . ?
C2 C1 C6 C7 19.1(2) . . . . ?
C11 C6 C7 C8 -0.3(2) . . . . ?
C1 C6 C7 C8 178.11(15) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C7 C8 C9 N2 -179.32(15) . . . . ?
O3 N2 C9 C10 2.4(2) . . . . ?
O4 N2 C9 C10 -178.08(15) . . . . ?
O3 N2 C9 C8 -178.20(16) . . . . ?
O4 N2 C9 C8 1.4(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
N2 C9 C10 C11 179.14(15) . . . . ?
C9 C10 C11 C6 0.2(2) . . . . ?
C7 C6 C11 C10 0.1(2) . . . . ?
C1 C6 C11 C10 -178.35(15) . . . . ?
Ni1 O5 C14 C15 1.3(2) . . . . ?
Ni1 O5 C14 C19 -174.89(10) . . . . ?
O5 C14 C15 C16 -4.0(3) . . . . ?
C19 C14 C15 C16 172.02(16) . . . . ?
C18 N3 C16 O6 5.3(2) . . . . ?
Ni1 N3 C16 O6 176.86(12) . . . . ?
C18 N3 C16 C15 -172.44(18) . . . . ?
Ni1 N3 C16 C15 -0.9(3) . . . . ?
C17 O6 C16 N3 6.4(2) . . . . ?
C17 O6 C16 C15 -175.53(18) . . . . ?
C14 C15 C16 N3 3.9(3) . . . . ?
C14 C15 C16 O6 -173.83(17) . . . . ?
C16 O6 C17 C18 -14.9(2) . . . . ?
C16 N3 C18 C26 104.54(17) . . . . ?
Ni1 N3 C18 C26 -66.40(19) . . . . ?
C16 N3 C18 C25 -133.94(17) . . . . ?
Ni1 N3 C18 C25 55.1(2) . . . . ?
C16 N3 C18 C17 -13.86(19) . . . . ?
Ni1 N3 C18 C17 175.21(14) . . . . ?
O6 C17 C18 N3 17.1(2) . . . . ?
O6 C17 C18 C26 -98.44(19) . . . . ?
O6 C17 C18 C25 137.28(18) . . . . ?
O5 C14 C19 C24 33.1(2) . . . . ?
C15 C14 C19 C24 -143.32(17) . . . . ?
O5 C14 C19 C20 -149.76(16) . . . . ?
C15 C14 C19 C20 33.8(2) . . . . ?
C24 C19 C20 C21 2.2(3) . . . . ?
C14 C19 C20 C21 -174.96(15) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -2.2(3) . . . . ?
C20 C21 C22 N4 175.96(15) . . . . ?
O7 N4 C22 C23 1.0(3) . . . . ?
O8 N4 C22 C23 179.68(17) . . . . ?
O7 N4 C22 C21 -177.23(17) . . . . ?
O8 N4 C22 C21 1.5(2) . . . . ?
C21 C22 C23 C24 1.9(3) . . . . ?
N4 C22 C23 C24 -176.23(16) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C20 C19 C24 C23 -2.4(3) . . . . ?
C14 C19 C24 C23 174.77(16) . . . . ?

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_d18100
_database_code_depnum_ccdc_archive 'CCDC 1884796'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C16 H18 F6 N2 Ni O4'
_chemical_formula_sum            'C16 H18 F6 N2 Ni O4'
_chemical_formula_weight         475.03

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'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.1193(4)
_cell_length_b                   18.3316(8)
_cell_length_c                   19.0410(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3881.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3329
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.09

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_F_000             1936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.081
_shelx_estimated_absorpt_T_min   0.737
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26354
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4427
_reflns_number_gt                3021
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0239P)²+3.0323P] 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         4427
_refine_ls_number_parameters     294
_refine_ls_number_restraints     51
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      1.001
_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 0.38361(3) 0.16466(2) 0.37389(2) 0.02088(9) Uani 1 1 d . . . . .
F1 F 0.14331(14) 0.33919(10) 0.27147(12) 0.0625(6) Uani 1 1 d . . . . .
F2 F 0.27487(16) 0.37553(9) 0.19818(9) 0.0462(4) Uani 1 1 d . . . . .
F3 F 0.29851(18) 0.39850(9) 0.30678(10) 0.0562(5) Uani 1 1 d . . . . .
F4 F 0.1856(16) -0.0057(12) 0.5584(4) 0.067(3) Uani 0.51(4) 1 d D U P A 1
F5 F 0.2786(12) -0.0663(5) 0.4825(14) 0.073(3) Uani 0.51(4) 1 d D U P A 1
F6 F 0.1230(9) -0.0033(11) 0.4551(9) 0.049(3) Uani 0.51(4) 1 d D U P A 1
F4A F 0.1117(9) 0.0050(13) 0.4702(11) 0.061(4) Uani 0.49(4) 1 d D U P A 2
F5A F 0.217(2) -0.0243(12) 0.5582(4) 0.077(4) Uani 0.49(4) 1 d D U P A 2
F6A F 0.2652(15) -0.0593(6) 0.4547(10) 0.064(3) Uani 0.49(4) 1 d D U P A 2
O1 O 0.31269(15) 0.25156(9) 0.33598(10) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.50087(19) 0.14931(11) 0.17055(10) 0.0435(5) Uani 1 1 d . . . . .
O3 O 0.29085(14) 0.08672(9) 0.41502(9) 0.0262(4) Uani 1 1 d . . . . .
O4 O 0.51545(16) 0.17095(11) 0.57495(9) 0.0332(4) Uani 1 1 d . . . . .
N1 N 0.45506(17) 0.13828(11) 0.28444(11) 0.0225(5) Uani 1 1 d . . . . .
N2 N 0.46716(17) 0.18438(11) 0.46132(11) 0.0220(5) Uani 1 1 d . . . . .
C1 C 0.3266(2) 0.27611(13) 0.27330(14) 0.0242(6) Uani 1 1 d . . . . .
C2 C 0.3882(2) 0.24576(13) 0.21960(14) 0.0275(6) Uani 1 1 d . . . . .
H2A H 0.392292 0.270475 0.175813 0.033 Uiso 1 1 calc R U . . .
C3 C 0.4473(2) 0.17733(14) 0.22758(14) 0.0264(6) Uani 1 1 d . . . . .
C4 C 0.5378(3) 0.07542(17) 0.18882(17) 0.0511(9) Uani 1 1 d . . . . .
H4A H 0.621074 0.065822 0.172897 0.061 Uiso 1 1 calc R U . . .
H4B H 0.483464 0.038998 0.167220 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5296(2) 0.07269(13) 0.26870(14) 0.0271(6) Uani 1 1 d . . . . .
C6 C 0.2611(2) 0.34769(15) 0.26194(15) 0.0334(6) Uani 1 1 d . . . . .
C7 C 0.6502(2) 0.08181(18) 0.3044(2) 0.0529(10) Uani 1 1 d . . . . .
H7A H 0.700898 0.039379 0.294179 0.079 Uiso 1 1 calc R U . . .
H7B H 0.638384 0.085880 0.355228 0.079 Uiso 1 1 calc R U . . .
H7C H 0.689452 0.126067 0.286835 0.079 Uiso 1 1 calc R U . . .
C8 C 0.4675(3) 0.00350(15) 0.29355(18) 0.0435(8) Uani 1 1 d . . . . .
H8A H 0.515039 -0.039046 0.279424 0.065 Uiso 1 1 calc R U . . .
H8B H 0.387254 0.000459 0.272433 0.065 Uiso 1 1 calc R U . . .
H8C H 0.460058 0.004467 0.344831 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3013(2) 0.06259(13) 0.47787(14) 0.0241(5) Uani 1 1 d . . . . .
C10 C 0.3733(2) 0.08768(14) 0.53012(13) 0.0276(6) Uani 1 1 d . . . . .
H10A H 0.371401 0.064499 0.574728 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4519(2) 0.14820(13) 0.51934(13) 0.0241(6) Uani 1 1 d . . . . .
C12 C 0.5993(2) 0.22531(15) 0.54853(14) 0.0325(6) Uani 1 1 d . . . . .
H12A H 0.680981 0.204377 0.543559 0.039 Uiso 1 1 calc R U . . .
H12B H 0.603271 0.267861 0.580459 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5487(2) 0.24729(14) 0.47707(15) 0.0267(6) Uani 1 1 d . . . . .
C14 C 0.2228(2) -0.00377(15) 0.49217(14) 0.0350(7) Uani 1 1 d D . . . .
C15 C 0.6445(3) 0.25391(18) 0.42102(17) 0.0445(8) Uani 1 1 d . . . . .
H15A H 0.699165 0.293936 0.432968 0.067 Uiso 1 1 calc R U . . .
H15B H 0.606381 0.263877 0.375604 0.067 Uiso 1 1 calc R U . . .
H15C H 0.689869 0.208186 0.418174 0.067 Uiso 1 1 calc R U . . .
C16 C 0.4728(3) 0.31674(15) 0.48191(17) 0.0416(8) Uani 1 1 d . . . . .
H16A H 0.525243 0.358491 0.491690 0.062 Uiso 1 1 calc R U . . .
H16B H 0.413824 0.311597 0.519835 0.062 Uiso 1 1 calc R U . . .
H16C H 0.430764 0.324616 0.437319 0.062 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 O1 1.9185(17) . ?
Ni1 O3 1.9284(16) . ?
Ni1 N2 1.940(2) . ?
Ni1 N1 1.941(2) . ?
F1 C6 1.331(3) . ?
F2 C6 1.326(3) . ?
F3 C6 1.330(3) . ?
F4 C14 1.327(6) . ?
F5 C14 1.316(6) . ?
F6 C14 1.315(6) . ?
F4A C14 1.314(6) . ?
F5A C14 1.314(6) . ?
F6A C14 1.329(6) . ?
O1 C1 1.285(3) . ?
O2 C3 1.341(3) . ?
O2 C4 1.457(3) . ?
O3 C9 1.281(3) . ?
O4 C11 1.339(3) . ?
O4 C12 1.455(3) . ?
N1 C3 1.301(3) . ?
N1 C5 1.491(3) . ?
N2 C11 1.300(3) . ?
N2 C13 1.497(3) . ?
C1 C2 1.351(3) . ?
C1 C6 1.516(3) . ?
C2 C3 1.424(3) . ?
C2 H2A 0.9500 . ?
C4 C5 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C7 1.513(4) . ?
C5 C8 1.520(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.357(3) . ?
C9 C14 1.522(4) . ?
C10 C11 1.427(4) . ?
C10 H10A 0.9500 . ?
C12 C13 1.527(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.513(4) . ?
C13 C16 1.530(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 O3 123.24(7) . . ?
O1 Ni1 N2 111.40(8) . . ?
O3 Ni1 N2 92.62(8) . . ?
O1 Ni1 N1 92.58(8) . . ?
O3 Ni1 N1 113.00(8) . . ?
N2 Ni1 N1 127.11(8) . . ?
C1 O1 Ni1 126.23(16) . . ?
C3 O2 C4 106.7(2) . . ?
C9 O3 Ni1 125.91(16) . . ?
C11 O4 C12 106.14(19) . . ?
C3 N1 C5 108.3(2) . . ?
C3 N1 Ni1 124.48(17) . . ?
C5 N1 Ni1 127.24(17) . . ?
C11 N2 C13 107.6(2) . . ?
C11 N2 Ni1 124.88(17) . . ?
C13 N2 Ni1 127.24(17) . . ?
O1 C1 C2 128.3(2) . . ?
O1 C1 C6 112.2(2) . . ?
C2 C1 C6 119.5(2) . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 H2A 119.5 . . ?
N1 C3 O2 115.7(2) . . ?
N1 C3 C2 127.2(2) . . ?
O2 C3 C2 117.1(2) . . ?
O2 C4 C5 104.6(2) . . ?
O2 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
O2 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C7 108.3(2) . . ?
N1 C5 C8 111.0(2) . . ?
C7 C5 C8 110.8(3) . . ?
N1 C5 C4 102.0(2) . . ?
C7 C5 C4 113.0(3) . . ?
C8 C5 C4 111.4(3) . . ?
F2 C6 F3 106.4(2) . . ?
F2 C6 F1 106.5(2) . . ?
F3 C6 F1 107.6(2) . . ?
F2 C6 C1 114.1(2) . . ?
F3 C6 C1 111.4(2) . . ?
F1 C6 C1 110.6(2) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C10 128.4(2) . . ?
O3 C9 C14 113.0(2) . . ?
C10 C9 C14 118.6(2) . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10A 119.4 . . ?
C11 C10 H10A 119.4 . . ?
N2 C11 O4 116.4(2) . . ?
N2 C11 C10 126.8(2) . . ?
O4 C11 C10 116.8(2) . . ?
O4 C12 C13 104.61(19) . . ?
O4 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
O4 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
N2 C13 C15 110.3(2) . . ?
N2 C13 C12 101.5(2) . . ?
C15 C13 C12 113.0(2) . . ?
N2 C13 C16 108.6(2) . . ?
C15 C13 C16 111.4(3) . . ?
C12 C13 C16 111.7(2) . . ?
F5A C14 F4A 107.2(11) . . ?
F6 C14 F5 109.2(11) . . ?
F6 C14 F4 104.3(10) . . ?
F5 C14 F4 104.9(8) . . ?
F5A C14 F6A 108.1(8) . . ?
F4A C14 F6A 104.9(11) . . ?
F5A C14 C9 115.2(9) . . ?
F4A C14 C9 112.6(10) . . ?
F6 C14 C9 112.5(9) . . ?
F5 C14 C9 113.6(6) . . ?
F4 C14 C9 111.7(9) . . ?
F6A C14 C9 108.2(7) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 O1 C1 C2 3.2(4) . . . . ?
Ni1 O1 C1 C6 -177.88(16) . . . . ?
O1 C1 C2 C3 1.1(4) . . . . ?
C6 C1 C2 C3 -177.8(2) . . . . ?
C5 N1 C3 O2 2.6(3) . . . . ?
Ni1 N1 C3 O2 -178.83(16) . . . . ?
C5 N1 C3 C2 -177.6(2) . . . . ?
Ni1 N1 C3 C2 1.0(4) . . . . ?
C4 O2 C3 N1 8.4(3) . . . . ?
C4 O2 C3 C2 -171.4(2) . . . . ?
C1 C2 C3 N1 -3.3(4) . . . . ?
C1 C2 C3 O2 176.5(2) . . . . ?
C3 O2 C4 C5 -15.2(3) . . . . ?
C3 N1 C5 C7 107.7(3) . . . . ?
Ni1 N1 C5 C7 -70.8(3) . . . . ?
C3 N1 C5 C8 -130.5(2) . . . . ?
Ni1 N1 C5 C8 51.0(3) . . . . ?
C3 N1 C5 C4 -11.8(3) . . . . ?
Ni1 N1 C5 C4 169.76(19) . . . . ?
O2 C4 C5 N1 15.9(3) . . . . ?
O2 C4 C5 C7 -100.1(3) . . . . ?
O2 C4 C5 C8 134.4(2) . . . . ?
O1 C1 C6 F2 178.9(2) . . . . ?
C2 C1 C6 F2 -2.1(3) . . . . ?
O1 C1 C6 F3 58.5(3) . . . . ?
C2 C1 C6 F3 -122.5(3) . . . . ?
O1 C1 C6 F1 -61.1(3) . . . . ?
C2 C1 C6 F1 117.9(3) . . . . ?
Ni1 O3 C9 C10 3.7(4) . . . . ?
Ni1 O3 C9 C14 -174.84(15) . . . . ?
O3 C9 C10 C11 -0.5(4) . . . . ?
C14 C9 C10 C11 178.0(2) . . . . ?
C13 N2 C11 O4 -4.4(3) . . . . ?
Ni1 N2 C11 O4 -178.36(15) . . . . ?
C13 N2 C11 C10 174.5(2) . . . . ?
Ni1 N2 C11 C10 0.6(4) . . . . ?
C12 O4 C11 N2 -8.7(3) . . . . ?
C12 O4 C11 C10 172.3(2) . . . . ?
C9 C10 C11 N2 -1.8(4) . . . . ?
C9 C10 C11 O4 177.1(2) . . . . ?
C11 O4 C12 C13 17.4(3) . . . . ?
C11 N2 C13 C15 134.6(2) . . . . ?
Ni1 N2 C13 C15 -51.7(3) . . . . ?
C11 N2 C13 C12 14.7(2) . . . . ?
Ni1 N2 C13 C12 -171.62(16) . . . . ?
C11 N2 C13 C16 -103.1(3) . . . . ?
Ni1 N2 C13 C16 70.6(3) . . . . ?
O4 C12 C13 N2 -19.0(2) . . . . ?
O4 C12 C13 C15 -137.0(2) . . . . ?
O4 C12 C13 C16 96.5(2) . . . . ?
O3 C9 C14 F5A -170.8(13) . . . . ?
C10 C9 C14 F5A 10.5(13) . . . . ?
O3 C9 C14 F4A -47.4(12) . . . . ?
C10 C9 C14 F4A 133.9(12) . . . . ?
O3 C9 C14 F6 -30.9(10) . . . . ?
C10 C9 C14 F6 150.4(10) . . . . ?
O3 C9 C14 F5 93.8(13) . . . . ?
C10 C9 C14 F5 -84.9(13) . . . . ?
O3 C9 C14 F4 -147.8(10) . . . . ?
C10 C9 C14 F4 33.5(10) . . . . ?
O3 C9 C14 F6A 68.1(10) . . . . ?
C10 C9 C14 F6A -110.6(10) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_d18101_a
_database_code_depnum_ccdc_archive 'CCDC 1884795'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C28 H26 N4 Ni O4'
_chemical_formula_sum            'C28 H26 N4 Ni O4'
_chemical_formula_weight         541.24

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                   6.9179(6)
_cell_length_b                   9.6038(10)
_cell_length_c                   20.210(2)
_cell_angle_alpha                103.140(3)
_cell_angle_beta                 94.606(3)
_cell_angle_gamma                98.490(3)
_cell_volume                     1284.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      26.28

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.797
_shelx_estimated_absorpt_T_min   0.826
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52010
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         27.673
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5966
_reflns_number_gt                4939
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0239P)²+0.7976P] 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         5966
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0640
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.22383(3) 0.36939(2) 0.24913(2) 0.01734(6) Uani 1 1 d . . . . .
O1 O 0.37135(16) 0.33887(13) 0.32813(6) 0.0205(2) Uani 1 1 d . . . . .
O2 O -0.09408(18) 0.54433(14) 0.40036(6) 0.0264(3) Uani 1 1 d . . . . .
O3 O 0.27114(16) 0.45879(12) 0.17431(5) 0.0196(2) Uani 1 1 d . . . . .
O4 O 0.06653(19) 0.01235(13) 0.08772(6) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.04869(19) 0.46898(14) 0.30568(7) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.9216(3) 0.0614(2) 0.59011(9) 0.0455(5) Uani 1 1 d . . . . .
N3 N 0.1378(2) 0.18001(15) 0.18767(7) 0.0185(3) Uani 1 1 d . . . . .
N4 N 0.3811(2) 0.89642(18) -0.08785(8) 0.0334(4) Uani 1 1 d . . . . .
C1 C 0.3260(2) 0.35598(17) 0.39031(8) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.1758(2) 0.42453(18) 0.41411(8) 0.0210(4) Uani 1 1 d . . . . .
H2A H 0.156111 0.436382 0.460917 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0490(2) 0.47819(17) 0.37099(8) 0.0186(3) Uani 1 1 d . . . . .
C4 C -0.2085(3) 0.58665(19) 0.34707(8) 0.0221(4) Uani 1 1 d . . . . .
H4A H -0.195548 0.693600 0.356614 0.027 Uiso 1 1 calc R U . . .
H4B H -0.349407 0.544345 0.343781 0.027 Uiso 1 1 calc R U . . .
C5 C -0.1226(2) 0.52683(18) 0.28027(8) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.4532(2) 0.29379(18) 0.43578(8) 0.0190(3) Uani 1 1 d . . . . .
C7 C 0.4058(3) 0.2776(2) 0.49972(9) 0.0281(4) Uani 1 1 d . . . . .
H7A H 0.290701 0.308633 0.516238 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5252(3) 0.2166(2) 0.53924(9) 0.0324(4) Uani 1 1 d . . . . .
H8A H 0.491860 0.206141 0.582742 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6935(3) 0.17078(19) 0.51560(9) 0.0256(4) Uani 1 1 d . . . . .
C10 C 0.7421(3) 0.1845(2) 0.45174(10) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.856848 0.152718 0.435223 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6209(3) 0.2451(2) 0.41246(9) 0.0271(4) Uani 1 1 d . . . . .
H11A H 0.653155 0.253608 0.368569 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8201(3) 0.1088(2) 0.55732(10) 0.0317(4) Uani 1 1 d . . . . .
C13 C -0.2636(3) 0.4021(2) 0.23148(9) 0.0240(4) Uani 1 1 d . . . . .
H13A H -0.193902 0.355649 0.194483 0.036 Uiso 1 1 calc R U . . .
H13B H -0.373744 0.439575 0.212103 0.036 Uiso 1 1 calc R U . . .
H13C H -0.313963 0.330769 0.256472 0.036 Uiso 1 1 calc R U . . .
C14 C -0.0556(3) 0.6468(2) 0.24486(10) 0.0295(4) Uani 1 1 d . . . . .
H14A H 0.011630 0.607596 0.205682 0.044 Uiso 1 1 calc R U . . .
H14B H 0.034874 0.725438 0.277202 0.044 Uiso 1 1 calc R U . . .
H14C H -0.170396 0.684331 0.228927 0.044 Uiso 1 1 calc R U . . .
C15 C 0.2356(2) 0.39940(18) 0.10894(8) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.1677(3) 0.25493(18) 0.08073(8) 0.0216(4) Uani 1 1 d . . . . .
H16A H 0.147634 0.221220 0.032308 0.026 Uiso 1 1 calc R U . . .
C17 C 0.1262(2) 0.15360(18) 0.12135(8) 0.0201(3) Uani 1 1 d . . . . .
C18 C -0.0013(3) -0.06226(19) 0.13874(9) 0.0256(4) Uani 1 1 d . . . . .
H18A H 0.044250 -0.156891 0.132688 0.031 Uiso 1 1 calc R U . . .
H18B H -0.146746 -0.078972 0.135523 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0897(3) 0.03993(18) 0.20770(9) 0.0215(4) Uani 1 1 d . . . . .
C20 C 0.2725(2) 0.50447(18) 0.06444(8) 0.0172(3) Uani 1 1 d . . . . .
C21 C 0.3469(3) 0.64978(19) 0.09547(9) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.377057 0.679281 0.143817 0.029 Uiso 1 1 calc R U . . .
C22 C 0.3777(3) 0.75196(19) 0.05713(9) 0.0257(4) Uani 1 1 d . . . . .
H22A H 0.428059 0.850636 0.079040 0.031 Uiso 1 1 calc R U . . .
C23 C 0.3343(2) 0.70893(19) -0.01378(9) 0.0211(3) Uani 1 1 d . . . . .
C24 C 0.2625(3) 0.5639(2) -0.04546(9) 0.0247(4) Uani 1 1 d . . . . .
H24A H 0.234574 0.534129 -0.093868 0.030 Uiso 1 1 calc R U . . .
C25 C 0.2319(3) 0.46334(19) -0.00664(8) 0.0221(4) Uani 1 1 d . . . . .
H25A H 0.182439 0.364598 -0.028693 0.027 Uiso 1 1 calc R U . . .
C26 C 0.3618(3) 0.8147(2) -0.05468(9) 0.0251(4) Uani 1 1 d . . . . .
C27 C -0.0553(3) 0.0540(2) 0.26091(10) 0.0288(4) Uani 1 1 d . . . . .
H27A H 0.005524 0.127715 0.302150 0.043 Uiso 1 1 calc R U . . .
H27B H -0.090354 -0.039470 0.272526 0.043 Uiso 1 1 calc R U . . .
H27C H -0.174213 0.082786 0.242226 0.043 Uiso 1 1 calc R U . . .
C28 C 0.2818(3) -0.0008(2) 0.23443(10) 0.0284(4) Uani 1 1 d . . . . .
H28A H 0.341443 0.071706 0.276224 0.043 Uiso 1 1 calc R U . . .
H28B H 0.372973 -0.003886 0.199626 0.043 Uiso 1 1 calc R U . . .
H28C H 0.254037 -0.096380 0.244547 0.043 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 O1 1.9276(11) . ?
Ni1 O3 1.9282(11) . ?
Ni1 N3 1.9338(14) . ?
Ni1 N1 1.9381(13) . ?
O1 C1 1.2998(19) . ?
O2 C3 1.3580(19) . ?
O2 C4 1.452(2) . ?
O3 C15 1.3020(19) . ?
O4 C17 1.358(2) . ?
O4 C18 1.453(2) . ?
N1 C3 1.303(2) . ?
N1 C5 1.484(2) . ?
N2 C12 1.138(2) . ?
N3 C17 1.300(2) . ?
N3 C19 1.490(2) . ?
N4 C26 1.143(2) . ?
C1 C2 1.372(2) . ?
C1 C6 1.500(2) . ?
C2 C3 1.417(2) . ?
C2 H2A 0.9500 . ?
C4 C5 1.544(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C13 1.524(2) . ?
C5 C14 1.524(2) . ?
C6 C11 1.391(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.383(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C12 1.448(2) . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.370(2) . ?
C15 C20 1.505(2) . ?
C16 C17 1.422(2) . ?
C16 H16A 0.9500 . ?
C18 C19 1.535(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C27 1.526(2) . ?
C19 C28 1.532(2) . ?
C20 C25 1.394(2) . ?
C20 C21 1.394(2) . ?
C21 C22 1.385(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.393(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.391(2) . ?
C23 C26 1.449(2) . ?
C24 C25 1.380(2) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 O3 138.36(5) . . ?
O1 Ni1 N3 106.42(5) . . ?
O3 Ni1 N3 92.11(5) . . ?
O1 Ni1 N1 91.51(5) . . ?
O3 Ni1 N1 109.82(5) . . ?
N3 Ni1 N1 122.31(6) . . ?
C1 O1 Ni1 128.54(10) . . ?
C3 O2 C4 107.37(12) . . ?
C15 O3 Ni1 128.22(11) . . ?
C17 O4 C18 105.98(13) . . ?
C3 N1 C5 109.54(13) . . ?
C3 N1 Ni1 124.34(11) . . ?
C5 N1 Ni1 125.57(10) . . ?
C17 N3 C19 108.75(14) . . ?
C17 N3 Ni1 124.74(12) . . ?
C19 N3 Ni1 126.34(10) . . ?
O1 C1 C2 124.30(15) . . ?
O1 C1 C6 114.30(14) . . ?
C2 C1 C6 121.40(14) . . ?
C1 C2 C3 122.01(15) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
N1 C3 O2 115.18(14) . . ?
N1 C3 C2 128.11(15) . . ?
O2 C3 C2 116.69(14) . . ?
O2 C4 C5 105.45(13) . . ?
O2 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
O2 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C13 108.50(13) . . ?
N1 C5 C14 110.64(14) . . ?
C13 C5 C14 111.05(14) . . ?
N1 C5 C4 102.09(12) . . ?
C13 C5 C4 112.68(14) . . ?
C14 C5 C4 111.50(14) . . ?
C11 C6 C7 118.45(15) . . ?
C11 C6 C1 119.00(15) . . ?
C7 C6 C1 122.51(15) . . ?
C8 C7 C6 120.49(17) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 120.23(17) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C10 120.15(16) . . ?
C8 C9 C12 120.29(17) . . ?
C10 C9 C12 119.56(18) . . ?
C11 C10 C9 119.11(17) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C6 121.54(17) . . ?
C10 C11 H11A 119.2 . . ?
C6 C11 H11A 119.2 . . ?
N2 C12 C9 179.1(2) . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 C16 124.83(15) . . ?
O3 C15 C20 114.22(14) . . ?
C16 C15 C20 120.95(14) . . ?
C15 C16 C17 122.33(15) . . ?
C15 C16 H16A 118.8 . . ?
C17 C16 H16A 118.8 . . ?
N3 C17 O4 115.35(15) . . ?
N3 C17 C16 127.60(15) . . ?
O4 C17 C16 117.06(14) . . ?
O4 C18 C19 104.82(13) . . ?
O4 C18 H18A 110.8 . . ?
C19 C18 H18A 110.8 . . ?
O4 C18 H18B 110.8 . . ?
C19 C18 H18B 110.8 . . ?
H18A C18 H18B 108.9 . . ?
N3 C19 C27 109.86(13) . . ?
N3 C19 C28 108.39(14) . . ?
C27 C19 C28 112.17(15) . . ?
N3 C19 C18 101.08(13) . . ?
C27 C19 C18 112.82(15) . . ?
C28 C19 C18 111.88(14) . . ?
C25 C20 C21 118.36(15) . . ?
C25 C20 C15 122.79(15) . . ?
C21 C20 C15 118.84(14) . . ?
C22 C21 C20 121.25(16) . . ?
C22 C21 H21A 119.4 . . ?
C20 C21 H21A 119.4 . . ?
C21 C22 C23 119.50(16) . . ?
C21 C22 H22A 120.2 . . ?
C23 C22 H22A 120.2 . . ?
C24 C23 C22 119.83(15) . . ?
C24 C23 C26 119.83(16) . . ?
C22 C23 C26 120.34(16) . . ?
C25 C24 C23 120.08(16) . . ?
C25 C24 H24A 120.0 . . ?
C23 C24 H24A 120.0 . . ?
C24 C25 C20 120.97(16) . . ?
C24 C25 H25A 119.5 . . ?
C20 C25 H25A 119.5 . . ?
N4 C26 C23 178.8(2) . . ?
C19 C27 H27A 109.5 . . ?
C19 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C19 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C28 H28A 109.5 . . ?
C19 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C19 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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 O1 C1 C2 -12.0(2) . . . . ?
Ni1 O1 C1 C6 168.05(10) . . . . ?
O1 C1 C2 C3 2.8(3) . . . . ?
C6 C1 C2 C3 -177.19(15) . . . . ?
C5 N1 C3 O2 -3.9(2) . . . . ?
Ni1 N1 C3 O2 -175.78(10) . . . . ?
C5 N1 C3 C2 174.19(16) . . . . ?
Ni1 N1 C3 C2 2.3(3) . . . . ?
C4 O2 C3 N1 -0.13(19) . . . . ?
C4 O2 C3 C2 -178.45(14) . . . . ?
C1 C2 C3 N1 2.1(3) . . . . ?
C1 C2 C3 O2 -179.86(15) . . . . ?
C3 O2 C4 C5 3.86(17) . . . . ?
C3 N1 C5 C13 -113.34(15) . . . . ?
Ni1 N1 C5 C13 58.42(17) . . . . ?
C3 N1 C5 C14 124.60(15) . . . . ?
Ni1 N1 C5 C14 -63.65(17) . . . . ?
C3 N1 C5 C4 5.84(17) . . . . ?
Ni1 N1 C5 C4 177.59(11) . . . . ?
O2 C4 C5 N1 -5.69(16) . . . . ?
O2 C4 C5 C13 110.49(15) . . . . ?
O2 C4 C5 C14 -123.84(15) . . . . ?
O1 C1 C6 C11 9.5(2) . . . . ?
C2 C1 C6 C11 -170.44(16) . . . . ?
O1 C1 C6 C7 -167.93(16) . . . . ?
C2 C1 C6 C7 12.1(3) . . . . ?
C11 C6 C7 C8 1.1(3) . . . . ?
C1 C6 C7 C8 178.53(17) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C12 179.14(18) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C12 C9 C10 C11 -179.43(18) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C7 C6 C11 C10 -1.4(3) . . . . ?
C1 C6 C11 C10 -178.92(17) . . . . ?
Ni1 O3 C15 C16 -4.7(2) . . . . ?
Ni1 O3 C15 C20 174.33(10) . . . . ?
O3 C15 C16 C17 0.8(3) . . . . ?
C20 C15 C16 C17 -178.20(15) . . . . ?
C19 N3 C17 O4 2.9(2) . . . . ?
Ni1 N3 C17 O4 178.54(10) . . . . ?
C19 N3 C17 C16 -177.30(16) . . . . ?
Ni1 N3 C17 C16 -1.7(3) . . . . ?
C18 O4 C17 N3 10.38(19) . . . . ?
C18 O4 C17 C16 -169.41(15) . . . . ?
C15 C16 C17 N3 2.6(3) . . . . ?
C15 C16 C17 O4 -177.61(15) . . . . ?
C17 O4 C18 C19 -18.45(17) . . . . ?
C17 N3 C19 C27 -133.33(15) . . . . ?
Ni1 N3 C19 C27 51.15(18) . . . . ?
C17 N3 C19 C28 103.79(16) . . . . ?
Ni1 N3 C19 C28 -71.72(17) . . . . ?
C17 N3 C19 C18 -13.94(17) . . . . ?
Ni1 N3 C19 C18 170.55(11) . . . . ?
O4 C18 C19 N3 19.24(16) . . . . ?
O4 C18 C19 C27 136.50(14) . . . . ?
O4 C18 C19 C28 -95.91(16) . . . . ?
O3 C15 C20 C25 -176.03(15) . . . . ?
C16 C15 C20 C25 3.0(2) . . . . ?
O3 C15 C20 C21 2.7(2) . . . . ?
C16 C15 C20 C21 -178.23(16) . . . . ?
C25 C20 C21 C22 0.9(3) . . . . ?
C15 C20 C21 C22 -177.92(15) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C21 C22 C23 C26 178.78(16) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C26 C23 C24 C25 -178.57(16) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C21 C20 C25 C24 -0.6(3) . . . . ?
C15 C20 C25 C24 178.09(15) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_d1835_a
_database_code_depnum_ccdc_archive 'CCDC 1884794'
_audit_update_record             
;
2018-12-12 deposited with the CCDC.
2019-01-10 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         'C22 H24 N2 Ni O4 S2'
_chemical_formula_sum            'C22 H24 N2 Ni O4 S2'
_chemical_formula_weight         503.26

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'
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                   9.8995(5)
_cell_length_b                   14.7668(8)
_cell_length_c                   16.2988(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.652(2)
_cell_angle_gamma                90
_cell_volume                     2305.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.33

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.054
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7172
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31003
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.889
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5293
_reflns_number_gt                4401
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       APEX2
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0281P)²+1.2067P] 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         5293
_refine_ls_number_parameters     321
_refine_ls_number_restraints     180
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.054
_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 0.64319(2) 0.49164(2) 0.75594(2) 0.01888(6) Uani 1 1 d . . . . .
O1 O 0.64718(12) 0.52438(8) 0.64248(7) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.47211(13) 0.74561(8) 0.74598(7) 0.0272(3) Uani 1 1 d . . . . .
O3 O 0.56211(12) 0.39834(8) 0.81084(7) 0.0218(2) Uani 1 1 d . . . . .
O4 O 0.99467(12) 0.40623(8) 0.93140(8) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.55857(14) 0.60543(9) 0.77642(8) 0.0189(3) Uani 1 1 d . . . . .
N2 N 0.83178(14) 0.46706(9) 0.82372(9) 0.0194(3) Uani 1 1 d . . . . .
C1 C 0.52844(17) 0.67008(11) 0.72030(10) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.54402(17) 0.67018(11) 0.63637(10) 0.0206(3) Uani 1 1 d . . . . .
H2A H 0.515203 0.722115 0.601997 0.025 Uiso 1 1 calc R U . . .
C3 C 0.59930(16) 0.59798(11) 0.60271(10) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.4877(2) 0.73497(13) 0.83650(11) 0.0322(4) Uani 1 1 d . . . . .
H4A H 0.402158 0.754771 0.852368 0.039 Uiso 1 1 calc R U . . .
H4B H 0.567889 0.770723 0.869295 0.039 Uiso 1 1 calc R U . . .
C5 C 0.51281(18) 0.63330(12) 0.85285(10) 0.0236(4) Uani 1 1 d . . . . .
S1 S 0.70410(15) 0.52370(7) 0.47744(7) 0.0235(2) Uani 0.786(2) 1 d D U P A 1
C6 C 0.61001(17) 0.60194(11) 0.51420(10) 0.0204(3) Uani 0.786(2) 1 d D U P A 1
C7 C 0.5535(9) 0.6642(5) 0.4532(4) 0.0169(10) Uani 0.786(2) 1 d D U P A 1
H7A H 0.495471 0.712547 0.462025 0.020 Uiso 0.786(2) 1 calc R U P A 1
C8 C 0.5901(4) 0.6496(2) 0.3752(2) 0.0263(7) Uani 0.786(2) 1 d D U P A 1
H8A H 0.561275 0.687180 0.326639 0.032 Uiso 0.786(2) 1 calc R U P A 1
C9 C 0.6721(4) 0.5744(2) 0.37942(18) 0.0265(7) Uani 0.786(2) 1 d D U P A 1
H9 H 0.707131 0.552873 0.333865 0.032 Uiso 0.786(2) 1 calc R U P A 1
S1A S 0.5417(10) 0.6740(6) 0.4389(4) 0.0261(11) Uani 0.214(2) 1 d D U P A 2
C6A C 0.61001(17) 0.60194(11) 0.51420(10) 0.0204(3) Uani 0.214(2) 1 d D U P A 2
C7A C 0.687(2) 0.5360(10) 0.4854(8) 0.023(2) Uani 0.214(2) 1 d D U P A 2
H7AA H 0.727632 0.485442 0.518395 0.028 Uiso 0.214(2) 1 calc R U P A 2
C8A C 0.6969(14) 0.5524(8) 0.4007(6) 0.023(2) Uani 0.214(2) 1 d D U P A 2
H8AA H 0.750517 0.516738 0.372016 0.027 Uiso 0.214(2) 1 calc R U P A 2
C9A C 0.6202(14) 0.6253(8) 0.3670(6) 0.025(2) Uani 0.214(2) 1 d D U P A 2
H9A H 0.610986 0.646857 0.310966 0.030 Uiso 0.214(2) 1 calc R U P A 2
C10 C 0.6255(2) 0.61333(14) 0.93319(11) 0.0350(5) Uani 1 1 d . . . . .
H10A H 0.711547 0.645026 0.931162 0.053 Uiso 1 1 calc R U . . .
H10B H 0.643050 0.547982 0.937677 0.053 Uiso 1 1 calc R U . . .
H10C H 0.594524 0.634099 0.982567 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3769(2) 0.58438(15) 0.85293(13) 0.0386(5) Uani 1 1 d . . . . .
H11A H 0.392501 0.518801 0.854326 0.058 Uiso 1 1 calc R U . . .
H11B H 0.305165 0.600330 0.801528 0.058 Uiso 1 1 calc R U . . .
H11C H 0.345739 0.602619 0.902988 0.058 Uiso 1 1 calc R U . . .
C12 C 0.62525(17) 0.34869(10) 0.87477(9) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.76381(17) 0.35565(11) 0.91691(10) 0.0207(3) Uani 1 1 d . . . . .
H13A H 0.797563 0.321532 0.967355 0.025 Uiso 1 1 calc R U . . .
C14 C 0.85840(17) 0.41188(11) 0.88794(10) 0.0195(3) Uani 1 1 d . . . . .
C15 C 1.07252(19) 0.46518(14) 0.88951(13) 0.0323(4) Uani 1 1 d . . . . .
H15A H 1.140927 0.430005 0.867496 0.039 Uiso 1 1 calc R U . . .
H15B H 1.123342 0.511626 0.929368 0.039 Uiso 1 1 calc R U . . .
S2 S 0.36127(4) 0.27588(3) 0.84587(3) 0.02391(10) Uani 1 1 d D . . . .
C16 C 0.53550(16) 0.27998(11) 0.89997(10) 0.0184(3) Uani 1 1 d D . . . .
C17 C 0.56709(18) 0.21337(11) 0.96056(10) 0.0217(3) Uani 1 1 d D . . . .
H17A H 0.657640 0.204452 0.996849 0.026 Uiso 1 1 calc R U . . .
C18 C 0.44981(18) 0.15931(12) 0.96309(11) 0.0263(4) Uani 1 1 d D . . . .
H18A H 0.453262 0.110180 1.001188 0.032 Uiso 1 1 calc R U . . .
C19 C 0.33197(19) 0.18546(12) 0.90507(11) 0.0271(4) Uani 1 1 d D . . . .
H19 H 0.243731 0.156993 0.898126 0.032 Uiso 1 1 calc R U . . .
C20 C 0.96389(17) 0.51000(11) 0.81611(11) 0.0220(3) Uani 1 1 d . . . . .
C21 C 0.9900(2) 0.48803(15) 0.73029(12) 0.0359(5) Uani 1 1 d . . . . .
H21A H 0.913749 0.512489 0.685182 0.054 Uiso 1 1 calc R U . . .
H21B H 0.994660 0.422204 0.723863 0.054 Uiso 1 1 calc R U . . .
H21C H 1.078550 0.515245 0.726509 0.054 Uiso 1 1 calc R U . . .
C22 C 0.9561(2) 0.61174(13) 0.82843(16) 0.0416(5) Uani 1 1 d . . . . .
H22A H 0.880248 0.637061 0.783601 0.062 Uiso 1 1 calc R U . . .
H22B H 1.044793 0.639600 0.825803 0.062 Uiso 1 1 calc R U . . .
H22C H 0.938364 0.624149 0.883840 0.062 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 O1 1.9214(11) . ?
Ni1 O3 1.9253(11) . ?
Ni1 N1 1.9437(14) . ?
Ni1 N2 1.9479(14) . ?
O1 C3 1.2926(19) . ?
O2 C1 1.3596(19) . ?
O2 C4 1.453(2) . ?
O3 C12 1.2978(18) . ?
O4 C14 1.358(2) . ?
O4 C15 1.444(2) . ?
N1 C1 1.303(2) . ?
N1 C5 1.487(2) . ?
N2 C14 1.300(2) . ?
N2 C20 1.487(2) . ?
C1 C2 1.415(2) . ?
C2 C3 1.374(2) . ?
C2 H2A 0.9500 . ?
C3 C6A 1.474(2) . ?
C3 C6 1.474(2) . ?
C4 C5 1.534(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.519(2) . ?
C5 C11 1.528(3) . ?
S1 C6 1.6863(18) . ?
S1 C9 1.720(3) . ?
C6 C7 1.365(5) . ?
C7 C8 1.424(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.367(4) . ?
C8 H8A 0.9500 . ?
C9 H9 0.9500 . ?
S1A C6A 1.637(5) . ?
S1A C9A 1.719(7) . ?
C6A C7A 1.386(8) . ?
C7A C8A 1.430(8) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.352(8) . ?
C8A H8AA 0.9500 . ?
C9A H9A 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.374(2) . ?
C12 C16 1.474(2) . ?
C13 C14 1.419(2) . ?
C13 H13A 0.9500 . ?
C15 C20 1.541(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
S2 C19 1.7145(17) . ?
S2 C16 1.7282(16) . ?
C16 C17 1.373(2) . ?
C17 C18 1.418(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.359(2) . ?
C18 H18A 0.9500 . ?
C19 H19 0.9500 . ?
C20 C22 1.520(2) . ?
C20 C21 1.520(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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 O3 137.71(5) . . ?
O1 Ni1 N1 93.58(5) . . ?
O3 Ni1 N1 106.88(5) . . ?
O1 Ni1 N2 110.04(5) . . ?
O3 Ni1 N2 93.18(5) . . ?
N1 Ni1 N2 117.17(6) . . ?
C3 O1 Ni1 126.87(10) . . ?
C1 O2 C4 106.11(12) . . ?
C12 O3 Ni1 127.21(11) . . ?
C14 O4 C15 107.16(13) . . ?
C1 N1 C5 108.73(13) . . ?
C1 N1 Ni1 123.01(11) . . ?
C5 N1 Ni1 128.23(11) . . ?
C14 N2 C20 109.34(14) . . ?
C14 N2 Ni1 122.92(11) . . ?
C20 N2 Ni1 127.62(11) . . ?
N1 C1 O2 115.07(14) . . ?
N1 C1 C2 128.15(15) . . ?
O2 C1 C2 116.76(14) . . ?
C3 C2 C1 122.47(15) . . ?
C3 C2 H2A 118.8 . . ?
C1 C2 H2A 118.8 . . ?
O1 C3 C2 125.78(14) . . ?
O1 C3 C6A 114.58(14) . . ?
C2 C3 C6A 119.63(14) . . ?
O1 C3 C6 114.58(14) . . ?
C2 C3 C6 119.63(14) . . ?
O2 C4 C5 104.67(13) . . ?
O2 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
O2 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C10 110.83(14) . . ?
N1 C5 C11 108.96(14) . . ?
C10 C5 C11 111.25(16) . . ?
N1 C5 C4 101.28(13) . . ?
C10 C5 C4 113.03(16) . . ?
C11 C5 C4 111.03(16) . . ?
C6 S1 C9 92.49(13) . . ?
C7 C6 C3 128.4(3) . . ?
C7 C6 S1 111.4(3) . . ?
C3 C6 S1 120.23(12) . . ?
C6 C7 C8 113.5(4) . . ?
C6 C7 H7A 123.3 . . ?
C8 C7 H7A 123.3 . . ?
C9 C8 C7 111.1(3) . . ?
C9 C8 H8A 124.4 . . ?
C7 C8 H8A 124.4 . . ?
C8 C9 S1 111.6(2) . . ?
C8 C9 H9 124.2 . . ?
S1 C9 H9 124.2 . . ?
C6A S1A C9A 93.8(4) . . ?
C7A C6A C3 119.0(5) . . ?
C7A C6A S1A 111.1(5) . . ?
C3 C6A S1A 129.9(3) . . ?
C6A C7A C8A 112.8(7) . . ?
C6A C7A H7AA 123.6 . . ?
C8A C7A H7AA 123.6 . . ?
C9A C8A C7A 110.8(8) . . ?
C9A C8A H8AA 124.6 . . ?
C7A C8A H8AA 124.6 . . ?
C8A C9A S1A 111.2(7) . . ?
C8A C9A H9A 124.4 . . ?
S1A C9A H9A 124.4 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C13 125.19(14) . . ?
O3 C12 C16 114.26(14) . . ?
C13 C12 C16 120.55(14) . . ?
C12 C13 C14 122.48(15) . . ?
C12 C13 H13A 118.8 . . ?
C14 C13 H13A 118.8 . . ?
N2 C14 O4 115.51(14) . . ?
N2 C14 C13 128.20(15) . . ?
O4 C14 C13 116.27(14) . . ?
O4 C15 C20 105.95(14) . . ?
O4 C15 H15A 110.5 . . ?
C20 C15 H15A 110.5 . . ?
O4 C15 H15B 110.5 . . ?
C20 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
C19 S2 C16 91.67(8) . . ?
C17 C16 C12 130.55(15) . . ?
C17 C16 S2 110.99(12) . . ?
C12 C16 S2 118.43(12) . . ?
C16 C17 C18 112.65(15) . . ?
C16 C17 H17A 123.7 . . ?
C18 C17 H17A 123.7 . . ?
C19 C18 C17 112.64(15) . . ?
C19 C18 H18A 123.7 . . ?
C17 C18 H18A 123.7 . . ?
C18 C19 S2 112.04(13) . . ?
C18 C19 H19 124.0 . . ?
S2 C19 H19 124.0 . . ?
N2 C20 C22 109.61(14) . . ?
N2 C20 C21 110.11(14) . . ?
C22 C20 C21 111.00(16) . . ?
N2 C20 C15 102.00(13) . . ?
C22 C20 C15 111.74(16) . . ?
C21 C20 C15 112.01(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C5 N1 C1 O2 3.3(2) . . . . ?
Ni1 N1 C1 O2 -178.81(11) . . . . ?
C5 N1 C1 C2 -175.09(16) . . . . ?
Ni1 N1 C1 C2 2.8(2) . . . . ?
C4 O2 C1 N1 10.3(2) . . . . ?
C4 O2 C1 C2 -171.16(15) . . . . ?
N1 C1 C2 C3 -1.6(3) . . . . ?
O2 C1 C2 C3 -179.88(15) . . . . ?
Ni1 O1 C3 C2 4.6(2) . . . . ?
Ni1 O1 C3 C6A -176.68(10) . . . . ?
Ni1 O1 C3 C6 -176.68(10) . . . . ?
C1 C2 C3 O1 -2.5(3) . . . . ?
C1 C2 C3 C6A 178.81(15) . . . . ?
C1 C2 C3 C6 178.81(15) . . . . ?
C1 O2 C4 C5 -18.61(18) . . . . ?
C1 N1 C5 C10 -134.54(16) . . . . ?
Ni1 N1 C5 C10 47.7(2) . . . . ?
C1 N1 C5 C11 102.73(17) . . . . ?
Ni1 N1 C5 C11 -75.05(18) . . . . ?
C1 N1 C5 C4 -14.36(18) . . . . ?
Ni1 N1 C5 C4 167.87(12) . . . . ?
O2 C4 C5 N1 19.60(18) . . . . ?
O2 C4 C5 C10 138.21(15) . . . . ?
O2 C4 C5 C11 -95.97(17) . . . . ?
O1 C3 C6 C7 170.8(6) . . . . ?
C2 C3 C6 C7 -10.4(6) . . . . ?
O1 C3 C6 S1 -10.4(2) . . . . ?
C2 C3 C6 S1 168.45(14) . . . . ?
C9 S1 C6 C7 1.1(5) . . . . ?
C9 S1 C6 C3 -177.93(17) . . . . ?
C3 C6 C7 C8 177.4(4) . . . . ?
S1 C6 C7 C8 -1.5(9) . . . . ?
C6 C7 C8 C9 1.2(9) . . . . ?
C7 C8 C9 S1 -0.4(6) . . . . ?
C6 S1 C9 C8 -0.4(3) . . . . ?
O1 C3 C6A C7A -9.5(11) . . . . ?
C2 C3 C6A C7A 169.3(11) . . . . ?
O1 C3 C6A S1A 169.5(5) . . . . ?
C2 C3 C6A S1A -11.7(6) . . . . ?
C9A S1A C6A C7A -3.8(13) . . . . ?
C9A S1A C6A C3 177.1(5) . . . . ?
C3 C6A C7A C8A -175.4(11) . . . . ?
S1A C6A C7A C8A 5(2) . . . . ?
C6A C7A C8A C9A -4(2) . . . . ?
C7A C8A C9A S1A 1.6(19) . . . . ?
C6A S1A C9A C8A 1.2(13) . . . . ?
Ni1 O3 C12 C13 1.7(2) . . . . ?
Ni1 O3 C12 C16 -177.34(10) . . . . ?
O3 C12 C13 C14 -7.9(3) . . . . ?
C16 C12 C13 C14 171.15(15) . . . . ?
C20 N2 C14 O4 -0.06(19) . . . . ?
Ni1 N2 C14 O4 -176.40(10) . . . . ?
C20 N2 C14 C13 -178.51(16) . . . . ?
Ni1 N2 C14 C13 5.2(2) . . . . ?
C15 O4 C14 N2 -1.2(2) . . . . ?
C15 O4 C14 C13 177.47(15) . . . . ?
C12 C13 C14 N2 4.1(3) . . . . ?
C12 C13 C14 O4 -174.35(15) . . . . ?
C14 O4 C15 C20 1.81(19) . . . . ?
O3 C12 C16 C17 176.04(16) . . . . ?
C13 C12 C16 C17 -3.1(3) . . . . ?
O3 C12 C16 S2 -2.07(19) . . . . ?
C13 C12 C16 S2 178.80(12) . . . . ?
C19 S2 C16 C17 0.26(13) . . . . ?
C19 S2 C16 C12 178.72(13) . . . . ?
C12 C16 C17 C18 -178.36(16) . . . . ?
S2 C16 C17 C18 -0.14(18) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 S2 0.3(2) . . . . ?
C16 S2 C19 C18 -0.32(15) . . . . ?
C14 N2 C20 C22 -117.38(17) . . . . ?
Ni1 N2 C20 C22 58.73(19) . . . . ?
C14 N2 C20 C21 120.24(16) . . . . ?
Ni1 N2 C20 C21 -63.65(18) . . . . ?
C14 N2 C20 C15 1.16(18) . . . . ?
Ni1 N2 C20 C15 177.27(12) . . . . ?
O4 C15 C20 N2 -1.77(18) . . . . ?
O4 C15 C20 C22 115.24(17) . . . . ?
O4 C15 C20 C21 -119.49(16) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.054

