# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex-1
_database_code_depnum_ccdc_archive 'CCDC 1527392'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;
_audit_creation_date             2017-03-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H48 N6 Ni O2, 2(Cl O4)'
_chemical_formula_sum            'C30 H48 Cl2 N6 Ni O10'
_chemical_formula_weight         782.35
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.9692(4)
_cell_length_b                   9.8140(4)
_cell_length_c                   20.2915(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.814(2)
_cell_angle_gamma                90
_cell_volume                     1748.30(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    410
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      3.15
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.051
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2817
_reflns_number_total             3589
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker Smart'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick,2013)'
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+1.7375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-O3 \\sim Cl2-O4 \\sim Cl2-O5 \\sim Cl2-O6
 with sigma of 0.02
 O3-O5 \\sim O4-O6 \\sim O3-O6 \\sim O4-O5 \\sim O3-O4 \\sim O5-O6
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O3 \\sim O4 \\sim O5 \\sim O6: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 Cl2, O3, O4, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C0AA, C1AA, C2AA, N4AA, C3AA, C14, C1AA, C0AA, C2AA, C1AA, N4AA, C2AA, N4AA,
 C3AA, N4AA, C14, N13A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N13B, C5AA, C7AA, C8AA, C0BA, N9AA, C6AA, N13B, C6AA, C7AA, C6AA, C8AA, C7AA,
 N9AA, C8AA, N9AA, C5AA, N9AA, C0BA, C5AA, C5AA, C5AA, C7AA, C7AA, C8AA, C0BA,
 C0BA, C0BA, C6AA, C6AA, N13B, C5AA, C8AA, C0BA, N9AA, C0BA, C5AA, N9AA, C0BA,
 N9AA, N13B, N13B, C8AA, N13B, N13B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: H12C(0.45) H12D(0.45) H12A(0.55) H12B(0.55) N13B(0.45) C0AA(0.55)
 H0AA(0.55) H0AB(0.55) C1AA(0.55) H1AA(0.55) H1AB(0.55) C2AA(0.55) H2AA(0.55)
 H2AB(0.55) N4AA(0.55) H4AA(0.55) C5AA(0.45) H5AA(0.45) H5AB(0.45) H5AC(0.45)
 C3AA(0.55) H3AA(0.55) H3AB(0.55) H3AC(0.55) C7AA(0.45) H7AA(0.45) H7AB(0.45)
 C8AA(0.45) H8AA(0.45) H8AB(0.45) C0BA(0.45) H0BA(0.45) H0BB(0.45) H0BC(0.45)
 N9AA(0.45) H9AA(0.45) C6AA(0.45) H6AA(0.45) H6AB(0.45) N13A(0.55) C14(0.55)
 H14A(0.55) H14B(0.55) H14C(0.55) Ni1A(0.45) Ni1(0.05)
6.a Ternary CH refined with riding coordinates:
 N4AA(H4AA), N9AA(H9AA)
6.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12C,H12D), C12(H12A,H12B), C0AA(H0AA,
 H0AB), C1AA(H1AA,H1AB), C2AA(H2AA,H2AB), C7AA(H7AA,H7AB), C8AA(H8AA,H8AB),
 C6AA(H6AA,H6AB)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8)
6.d Idealised Me refined as rotating group:
 C5AA(H5AA,H5AB,H5AC), C3AA(H3AA,H3AB,H3AC), C0BA(H0BA,H0BB,H0BC), C14(H14A,
 H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.4578(2) 0.0797(2) 0.08914(10) 0.0442(5) Uani 1 1 d . . . . .
C2 C 0.3510(3) 0.1747(3) 0.08621(14) 0.0379(6) Uani 1 1 d . . . . .
C3 C 0.2570(3) 0.1747(3) 0.13369(14) 0.0432(7) Uani 1 1 d . . . . .
H3 H 0.270251 0.106566 0.167665 0.052 Uiso 1 1 calc R . . . .
C4 C 0.1448(3) 0.2731(4) 0.13157(18) 0.0575(10) Uani 1 1 d . . . . .
H4 H 0.081778 0.270712 0.163917 0.069 Uiso 1 1 calc R . . . .
C5 C 0.1231(3) 0.3746(4) 0.08306(19) 0.0594(10) Uani 1 1 d . . . . .
H5 H 0.045560 0.441120 0.081718 0.071 Uiso 1 1 calc R . . . .
C6 C 0.2149(3) 0.3772(3) 0.03750(17) 0.0487(8) Uani 1 1 d . . . . .
H6 H 0.201654 0.447740 0.004734 0.058 Uiso 1 1 calc R . . . .
C7 C 0.3286(3) 0.2791(3) 0.03729(15) 0.0403(6) Uani 1 1 d . . . . .
C8 C 0.4229(3) 0.2938(3) -0.01255(16) 0.0476(7) Uani 1 1 d . . . . .
H8 H 0.427601 0.381353 -0.032022 0.057 Uiso 1 1 calc R . . . .
N9 N 0.4999(3) 0.1981(3) -0.03224(14) 0.0518(7) Uani 1 1 d . . . . .
C10 C 0.6035(3) 0.2343(3) -0.07724(16) 0.0520(8) Uani 1 1 d . . . . .
H10A H 0.575415 0.324530 -0.097846 0.062 Uiso 1 1 calc R . . . .
H10B H 0.594745 0.166164 -0.113835 0.062 Uiso 1 1 calc R . . . .
C11 C 0.7665(3) 0.2380(3) -0.03704(16) 0.0480(7) Uani 1 1 d . . . . .
H11A H 0.833579 0.269957 -0.067006 0.058 Uiso 1 1 calc R . . . .
H11B H 0.772433 0.305859 -0.000503 0.058 Uiso 1 1 calc R . . . .
C12 C 0.8279(3) 0.1031(3) -0.00600(14) 0.0405(6) Uani 1 1 d . . . . .
H12C H 0.926712 0.118491 0.025214 0.049 Uiso 0.45 1 calc R . . A 2
H12D H 0.845420 0.040588 -0.041961 0.049 Uiso 0.45 1 calc R . . A 2
H12A H 0.808100 0.031163 -0.040926 0.049 Uiso 0.55 1 calc R . . B 1
H12B H 0.939536 0.110462 0.009903 0.049 Uiso 0.55 1 calc R . . B 1
N13B N 0.7124(6) 0.0352(6) 0.0336(3) 0.0187(12) Uani 0.45 1 d . U . C 2
Cl2 Cl 0.79842(8) 0.53190(9) 0.17057(3) 0.0483(2) Uani 1 1 d D U . . .
O3 O 0.9098(4) 0.6155(3) 0.14979(16) 0.0822(9) Uani 1 1 d D U . . .
O4 O 0.8660(3) 0.4605(3) 0.23003(13) 0.0841(9) Uani 1 1 d D U . . .
O5 O 0.7385(3) 0.4347(3) 0.11931(11) 0.0711(7) Uani 1 1 d D U . . .
O6 O 0.6796(3) 0.6154(4) 0.18417(17) 0.1252(16) Uani 1 1 d D U . . .
C0AA C 0.8571(6) -0.0321(5) 0.0966(3) 0.0279(9) Uani 0.55 1 d . U . C 1
H0AA H 0.960521 0.007156 0.110331 0.033 Uiso 0.55 1 calc R . . C 1
H0AB H 0.866198 -0.118806 0.072793 0.033 Uiso 0.55 1 calc R . . C 1
C1AA C 0.7944(5) -0.0614(4) 0.1589(2) 0.0286(8) Uani 0.55 1 d . U . C 1
H1AA H 0.857623 -0.132794 0.185661 0.034 Uiso 0.55 1 calc R . . C 1
H1AB H 0.689779 -0.097968 0.144978 0.034 Uiso 0.55 1 calc R . . C 1
C2AA C 0.7902(7) 0.0631(5) 0.2035(3) 0.0328(9) Uani 0.55 1 d . U . C 1
H2AA H 0.864995 0.050735 0.246320 0.039 Uiso 0.55 1 calc R . . C 1
H2AB H 0.820560 0.144597 0.180738 0.039 Uiso 0.55 1 calc R . . C 1
N4AA N 0.6354(6) 0.0865(5) 0.2188(2) 0.0304(11) Uani 0.55 1 d . U . C 1
H4AA H 0.559710 0.084615 0.175138 0.036 Uiso 0.55 1 calc R . . C 1
C5AA C 0.6241(12) 0.2071(10) 0.2263(5) 0.0374(19) Uani 0.45 1 d . U . C 2
H5AA H 0.703150 0.238798 0.263899 0.056 Uiso 0.45 1 calc GR . . C 2
H5AB H 0.531342 0.185608 0.242628 0.056 Uiso 0.45 1 calc GR . . C 2
H5AC H 0.602149 0.278771 0.192016 0.056 Uiso 0.45 1 calc GR . . C 2
C3AA C 0.5946(7) -0.0240(5) 0.2619(3) 0.0434(12) Uani 0.55 1 d . U . C 1
H3AA H 0.605987 -0.112529 0.241121 0.065 Uiso 0.55 1 calc GR . . C 1
H3AB H 0.488790 -0.012441 0.266648 0.065 Uiso 0.55 1 calc GR . . C 1
H3AC H 0.662148 -0.020033 0.306439 0.065 Uiso 0.55 1 calc GR . . C 1
C7AA C 0.8960(7) -0.0050(6) 0.1431(3) 0.0326(11) Uani 0.45 1 d . U . C 2
H7AA H 0.988515 0.028694 0.128796 0.039 Uiso 0.45 1 calc R . . C 2
H7AB H 0.927952 -0.078086 0.176608 0.039 Uiso 0.45 1 calc R . . C 2
C8AA C 0.8280(7) 0.1120(6) 0.1773(3) 0.0317(11) Uani 0.45 1 d . U . C 2
H8AA H 0.902306 0.137972 0.218474 0.038 Uiso 0.45 1 calc R . . C 2
H8AB H 0.814935 0.191592 0.146663 0.038 Uiso 0.45 1 calc R . . C 2
C0BA C 0.6882(9) -0.0323(7) 0.2442(3) 0.0481(15) Uani 0.45 1 d . U . C 2
H0BA H 0.768802 -0.014182 0.283740 0.072 Uiso 0.45 1 calc GR . . C 2
H0BB H 0.711828 -0.116155 0.222193 0.072 Uiso 0.45 1 calc GR . . C 2
H0BC H 0.590647 -0.042753 0.258246 0.072 Uiso 0.45 1 calc GR . . C 2
N9AA N 0.6783(8) 0.0831(5) 0.1964(3) 0.0285(11) Uani 0.45 1 d . U . C 2
H9AA H 0.602435 0.059240 0.154599 0.034 Uiso 0.45 1 calc R . . C 2
C6AA C 0.7914(8) -0.0652(6) 0.0831(3) 0.0280(13) Uani 0.45 1 d . U . C 2
H6AA H 0.851151 -0.127242 0.060019 0.034 Uiso 0.45 1 calc R . . C 2
H6AB H 0.713762 -0.120827 0.099078 0.034 Uiso 0.45 1 calc R . . C 2
N13A N 0.7596(6) 0.0639(6) 0.0496(3) 0.0264(12) Uani 0.55 1 d . U . C 1
C14 C 0.6245(11) 0.2215(8) 0.2501(4) 0.047(2) Uani 0.55 1 d . U . C 1
H14A H 0.706195 0.230643 0.290111 0.071 Uiso 0.55 1 calc GR . . C 1
H14B H 0.525559 0.229726 0.263185 0.071 Uiso 0.55 1 calc GR . . C 1
H14C H 0.634421 0.293362 0.217771 0.071 Uiso 0.55 1 calc GR . . C 1
Ni1A Ni 0.52262(15) 0.01607(13) 0.01126(8) 0.0189(3) Uani 0.45 1 d . . . C 1
Ni1 Ni 0.500000 0.000000 0.000000 0.012(4) Uiso 0.1 2 d S T P C .


_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
O1 C2 1.329(3) . ?
O1 Ni1A 1.898(2) . ?
O1 Ni1A 2.283(3) 3_655 ?
O1 Ni1 2.075(2) . ?
C2 C3 1.404(4) . ?
C2 C7 1.412(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.358(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.404(4) . ?
C7 C8 1.452(4) . ?
C8 H8 0.9500 . ?
C8 N9 1.278(4) . ?
N9 C10 1.474(3) . ?
N9 Ni1A 1.984(2) . ?
N9 Ni1A 2.162(3) 3_655 ?
N9 Ni1 2.051(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.520(4) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 N13B 1.582(7) . ?
C12 N13A 1.442(7) . ?
N13B C6AA 1.480(7) . ?
N13B Ni1 1.919(5) . ?
Cl2 O3 1.422(3) . ?
Cl2 O4 1.419(2) . ?
Cl2 O5 1.432(2) . ?
Cl2 O6 1.416(3) . ?
C0AA H0AA 0.9900 . ?
C0AA H0AB 0.9900 . ?
C0AA C1AA 1.513(7) . ?
C0AA N13A 1.491(7) . ?
C1AA H1AA 0.9900 . ?
C1AA H1AB 0.9900 . ?
C1AA C2AA 1.526(6) . ?
C2AA H2AA 0.9900 . ?
C2AA H2AB 0.9900 . ?
C2AA N4AA 1.500(7) . ?
N4AA H4AA 1.0000 . ?
N4AA C3AA 1.486(6) . ?
N4AA C14 1.481(7) . ?
C5AA H5AA 0.9800 . ?
C5AA H5AB 0.9800 . ?
C5AA H5AC 0.9800 . ?
C5AA N9AA 1.485(9) . ?
C3AA H3AA 0.9800 . ?
C3AA H3AB 0.9800 . ?
C3AA H3AC 0.9800 . ?
C7AA H7AA 0.9900 . ?
C7AA H7AB 0.9900 . ?
C7AA C8AA 1.531(8) . ?
C7AA C6AA 1.497(8) . ?
C8AA H8AA 0.9900 . ?
C8AA H8AB 0.9900 . ?
C8AA N9AA 1.499(9) . ?
C0BA H0BA 0.9800 . ?
C0BA H0BB 0.9800 . ?
C0BA H0BC 0.9800 . ?
C0BA N9AA 1.482(8) . ?
N9AA H9AA 1.0000 . ?
C6AA H6AA 0.9900 . ?
C6AA H6AB 0.9900 . ?
N13A Ni1A 2.160(5) . ?
N13A Ni1 2.422(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
Ni1A Ni1A 0.630(4) 3_655 ?

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
C2 O1 Ni1A 122.30(18) . . ?
C2 O1 Ni1A 115.80(17) . 3_655 ?
C2 O1 Ni1 118.93(17) . . ?
Ni1A O1 Ni1A 13.76(8) . 3_655 ?
Ni1A O1 Ni1 7.52(5) . . ?
Ni1 O1 Ni1A 6.25(4) . 3_655 ?
O1 C2 C3 119.8(3) . . ?
O1 C2 C7 122.5(2) . . ?
C3 C2 C7 117.6(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.7(3) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 122.1(3) . . ?
C7 C6 H6 119.0 . . ?
C2 C7 C8 122.9(2) . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 C8 117.4(3) . . ?
C7 C8 H8 117.5 . . ?
N9 C8 C7 125.0(3) . . ?
N9 C8 H8 117.5 . . ?
C8 N9 C10 117.8(3) . . ?
C8 N9 Ni1A 122.4(2) . . ?
C8 N9 Ni1A 125.1(2) . 3_655 ?
C8 N9 Ni1 124.2(2) . . ?
C10 N9 Ni1A 118.16(18) . . ?
C10 N9 Ni1A 116.89(19) . 3_655 ?
C10 N9 Ni1 117.82(18) . . ?
Ni1A N9 Ni1A 16.78(10) . 3_655 ?
Ni1A N9 Ni1 8.75(5) . . ?
Ni1 N9 Ni1A 8.03(5) . 3_655 ?
N9 C10 H10A 109.8 . . ?
N9 C10 H10B 109.8 . . ?
N9 C10 C11 109.4(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.3(3) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C11 C12 H12C 109.4 . . ?
C11 C12 H12D 109.4 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C11 C12 N13B 111.0(3) . . ?
H12C C12 H12D 108.0 . . ?
H12A C12 H12B 107.9 . . ?
N13B C12 H12C 109.4 . . ?
N13B C12 H12D 109.4 . . ?
N13A C12 C11 112.4(3) . . ?
N13A C12 H12A 109.1 . . ?
N13A C12 H12B 109.1 . . ?
C12 N13B Ni1 126.9(4) . . ?
C6AA N13B C12 110.7(5) . . ?
C6AA N13B Ni1 115.1(4) . . ?
O3 Cl2 O5 110.56(18) . . ?
O4 Cl2 O3 109.49(18) . . ?
O4 Cl2 O5 108.65(17) . . ?
O6 Cl2 O3 109.0(2) . . ?
O6 Cl2 O4 109.1(2) . . ?
O6 Cl2 O5 109.97(17) . . ?
H0AA C0AA H0AB 107.8 . . ?
C1AA C0AA H0AA 109.1 . . ?
C1AA C0AA H0AB 109.1 . . ?
N13A C0AA H0AA 109.1 . . ?
N13A C0AA H0AB 109.1 . . ?
N13A C0AA C1AA 112.6(4) . . ?
C0AA C1AA H1AA 108.8 . . ?
C0AA C1AA H1AB 108.8 . . ?
C0AA C1AA C2AA 113.7(4) . . ?
H1AA C1AA H1AB 107.7 . . ?
C2AA C1AA H1AA 108.8 . . ?
C2AA C1AA H1AB 108.8 . . ?
C1AA C2AA H2AA 109.1 . . ?
C1AA C2AA H2AB 109.1 . . ?
H2AA C2AA H2AB 107.9 . . ?
N4AA C2AA C1AA 112.4(4) . . ?
N4AA C2AA H2AA 109.1 . . ?
N4AA C2AA H2AB 109.1 . . ?
C2AA N4AA H4AA 107.7 . . ?
C3AA N4AA C2AA 111.1(4) . . ?
C3AA N4AA H4AA 107.7 . . ?
C14 N4AA C2AA 111.8(5) . . ?
C14 N4AA H4AA 107.7 . . ?
C14 N4AA C3AA 110.7(5) . . ?
H5AA C5AA H5AB 109.5 . . ?
H5AA C5AA H5AC 109.5 . . ?
H5AB C5AA H5AC 109.5 . . ?
N9AA C5AA H5AA 109.5 . . ?
N9AA C5AA H5AB 109.5 . . ?
N9AA C5AA H5AC 109.5 . . ?
N4AA C3AA H3AA 109.5 . . ?
N4AA C3AA H3AB 109.5 . . ?
N4AA C3AA H3AC 109.5 . . ?
H3AA C3AA H3AB 109.5 . . ?
H3AA C3AA H3AC 109.5 . . ?
H3AB C3AA H3AC 109.5 . . ?
H7AA C7AA H7AB 107.5 . . ?
C8AA C7AA H7AA 108.5 . . ?
C8AA C7AA H7AB 108.5 . . ?
C6AA C7AA H7AA 108.5 . . ?
C6AA C7AA H7AB 108.5 . . ?
C6AA C7AA C8AA 115.0(5) . . ?
C7AA C8AA H8AA 108.3 . . ?
C7AA C8AA H8AB 108.3 . . ?
H8AA C8AA H8AB 107.4 . . ?
N9AA C8AA C7AA 115.9(5) . . ?
N9AA C8AA H8AA 108.3 . . ?
N9AA C8AA H8AB 108.3 . . ?
H0BA C0BA H0BB 109.5 . . ?
H0BA C0BA H0BC 109.5 . . ?
H0BB C0BA H0BC 109.5 . . ?
N9AA C0BA H0BA 109.5 . . ?
N9AA C0BA H0BB 109.5 . . ?
N9AA C0BA H0BC 109.5 . . ?
C5AA N9AA C8AA 109.6(5) . . ?
C5AA N9AA H9AA 108.4 . . ?
C8AA N9AA H9AA 108.4 . . ?
C0BA N9AA C5AA 109.8(6) . . ?
C0BA N9AA C8AA 112.1(6) . . ?
C0BA N9AA H9AA 108.4 . . ?
N13B C6AA C7AA 115.0(5) . . ?
N13B C6AA H6AA 108.5 . . ?
N13B C6AA H6AB 108.5 . . ?
C7AA C6AA H6AA 108.5 . . ?
C7AA C6AA H6AB 108.5 . . ?
H6AA C6AA H6AB 107.5 . . ?
C12 N13A C0AA 112.4(5) . . ?
C12 N13A Ni1A 108.7(3) . . ?
C12 N13A Ni1 105.6(3) . . ?
C0AA N13A Ni1A 119.9(4) . . ?
C0AA N13A Ni1 119.4(4) . . ?
Ni1A N13A Ni1 4.37(4) . . ?
N4AA C14 H14A 109.5 . . ?
N4AA C14 H14B 109.5 . . ?
N4AA C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 Ni1A O1 166.24(9) . 3_655 ?
O1 Ni1A N9 93.05(11) . . ?
O1 Ni1A N9 95.68(10) . 3_655 ?
O1 Ni1A N13A 94.3(2) . . ?
N9 Ni1A O1 89.61(11) . 3_655 ?
N9 Ni1A O1 78.64(10) 3_655 3_655 ?
N9 Ni1A N9 163.22(10) . 3_655 ?
N9 Ni1A N13A 88.20(17) . . ?
N13A Ni1A O1 99.28(18) . 3_655 ?
N13A Ni1A N9 105.36(17) . 3_655 ?
Ni1A Ni1A O1 120.5(2) 3_655 . ?
Ni1A Ni1A O1 45.78(19) 3_655 3_655 ?
Ni1A Ni1A N9 97.8(2) 3_655 . ?
Ni1A Ni1A N9 65.42(19) 3_655 3_655 ?
Ni1A Ni1A N13A 144.1(3) 3_655 . ?
O1 Ni1 O1 180.0 . 3_655 ?
O1 Ni1 N13A 82.62(16) 3_655 3_655 ?
O1 Ni1 N13A 97.38(16) . 3_655 ?
O1 Ni1 N13A 97.38(16) 3_655 . ?
O1 Ni1 N13A 82.62(16) . . ?
N9 Ni1 O1 86.14(9) 3_655 3_655 ?
N9 Ni1 O1 93.86(9) . 3_655 ?
N9 Ni1 O1 86.14(9) . . ?
N9 Ni1 O1 93.86(9) 3_655 . ?
N9 Ni1 N9 180.0 . 3_655 ?
N9 Ni1 N13A 79.92(15) 3_655 3_655 ?
N9 Ni1 N13A 100.08(15) 3_655 . ?
N9 Ni1 N13A 100.08(15) . 3_655 ?
N9 Ni1 N13A 79.92(15) . . ?
N13B Ni1 O1 91.9(2) 3_655 . ?
N13B Ni1 O1 88.1(2) . . ?
N13B Ni1 N9 83.0(2) . . ?
N13B Ni1 N9 97.0(2) 3_655 . ?
N13A Ni1 N13A 180.0 3_655 . ?
Ni1A Ni1 O1 52.0(2) 3_655 3_655 ?
Ni1A Ni1 O1 128.0(2) 3_655 . ?
Ni1A Ni1 N9 73.5(2) 3_655 3_655 ?
Ni1A Ni1 N9 106.5(2) 3_655 . ?
Ni1A Ni1 N13B 37.5(3) 3_655 3_655 ?
Ni1A Ni1 N13A 148.5(2) 3_655 . ?
Ni1A Ni1 N13A 31.5(2) 3_655 3_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound-2
_database_code_depnum_ccdc_archive 'CCDC 1527393'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N3 Ni O3'
_chemical_formula_weight         442.17

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   8.0642(2)
_cell_length_b                   15.4540(4)
_cell_length_c                   17.5161(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7440(10)
_cell_angle_gamma                90.00
_cell_volume                     2137.23(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    538
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      26.90

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             940
_exptl_absorpt_coefficient_mu    0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8350
_exptl_absorpt_correction_T_max  0.9635
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35679
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         29.17
_reflns_number_total             5749
_reflns_number_gt                4789
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick,2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick,2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)and Mercury (CCDC)'
_computing_publication_material  'SHELXL-2013 (Sheldrick,2013)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0327P)²+1.0851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5749
_refine_ls_number_parameters     268
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni Ni 0.63310(2) 0.262849(12) 0.234078(10) 0.01880(6) Uani 1 1 d . . .
O1 O 0.45004(14) 0.29673(7) 0.14320(6) 0.0276(2) Uani 1 1 d . . .
C2 C 0.35078(18) 0.36221(10) 0.14541(9) 0.0248(3) Uani 1 1 d . . .
C3 C 0.2920(2) 0.41178(11) 0.07725(10) 0.0326(4) Uani 1 1 d . . .
H3 H 0.3307 0.3978 0.0310 0.039 Uiso 1 1 calc R . .
C4 C 0.1805(2) 0.47958(11) 0.07589(11) 0.0382(4) Uani 1 1 d . . .
H4 H 0.1470 0.5125 0.0295 0.046 Uiso 1 1 calc R . .
C5 C 0.1162(2) 0.50065(11) 0.14143(12) 0.0398(4) Uani 1 1 d . . .
H5 H 0.0361 0.5461 0.1397 0.048 Uiso 1 1 calc R . .
C6 C 0.1711(2) 0.45418(11) 0.20879(11) 0.0325(4) Uani 1 1 d . . .
H6 H 0.1271 0.4679 0.2537 0.039 Uiso 1 1 calc R . .
C7 C 0.29067(19) 0.38684(10) 0.21344(9) 0.0257(3) Uani 1 1 d . . .
C8 C 0.34210(19) 0.34321(10) 0.28766(9) 0.0260(3) Uani 1 1 d . . .
H8 H 0.2762 0.3533 0.3260 0.031 Uiso 1 1 calc R . .
N9 N 0.46960(16) 0.29197(9) 0.30602(7) 0.0252(3) Uani 1 1 d . . .
C10 C 0.4978(2) 0.24981(12) 0.38222(9) 0.0323(4) Uani 1 1 d . . .
H10A H 0.4026 0.2635 0.4080 0.039 Uiso 1 1 calc R . .
H10B H 0.6031 0.2727 0.4153 0.039 Uiso 1 1 calc R . .
C11 C 0.5126(3) 0.15187(13) 0.37486(10) 0.0423(4) Uani 1 1 d . . .
H11A H 0.4510 0.1242 0.4118 0.051 Uiso 1 1 calc R . .
H11B H 0.6334 0.1357 0.3910 0.051 Uiso 1 1 calc R . .
C12 C 0.4450(2) 0.11459(12) 0.29365(10) 0.0342(4) Uani 1 1 d . . .
H12A H 0.4285 0.0514 0.2977 0.041 Uiso 1 1 calc R . .
H12B H 0.3337 0.1409 0.2715 0.041 Uiso 1 1 calc R . .
N13 N 0.56433(16) 0.13161(9) 0.24066(8) 0.0251(3) Uani 1 1 d D . .
C14 C 0.5020(2) 0.09010(11) 0.16503(10) 0.0322(4) Uani 1 1 d . . .
H14A H 0.4010 0.1218 0.1371 0.039 Uiso 1 1 calc R . .
H14B H 0.4665 0.0302 0.1738 0.039 Uiso 1 1 calc R . .
C15 C 0.6336(2) 0.08759(12) 0.11419(10) 0.0366(4) Uani 1 1 d . . .
H15A H 0.7361 0.0586 0.1440 0.044 Uiso 1 1 calc R . .
H15B H 0.5890 0.0511 0.0682 0.044 Uiso 1 1 calc R . .
C16 C 0.6864(2) 0.17373(12) 0.08548(9) 0.0326(4) Uani 1 1 d . . .
H16A H 0.7563 0.1624 0.0462 0.039 Uiso 1 1 calc R . .
H16B H 0.5831 0.2045 0.0587 0.039 Uiso 1 1 calc R . .
N17 N 0.78283(17) 0.23215(9) 0.14585(8) 0.0283(3) Uani 1 1 d . . .
C18 C 0.8112(3) 0.31337(12) 0.10575(11) 0.0410(4) Uani 1 1 d . . .
H18A H 0.8873 0.3510 0.1420 0.049 Uiso 1 1 calc R . .
H18B H 0.7027 0.3428 0.0877 0.049 Uiso 1 1 calc R . .
H18C H 0.8625 0.3001 0.0610 0.049 Uiso 1 1 calc R . .
C19 C 0.9495(2) 0.19343(14) 0.17931(11) 0.0401(4) Uani 1 1 d . . .
H19A H 1.0056 0.1761 0.1371 0.048 Uiso 1 1 calc R . .
H19B H 0.9335 0.1425 0.2104 0.048 Uiso 1 1 calc R . .
H19C H 1.0198 0.2360 0.2126 0.048 Uiso 1 1 calc R . .
O20 O 0.82963(13) 0.23340(7) 0.32240(6) 0.0233(2) Uani 1 1 d . . .
C21 C 0.92437(17) 0.28414(9) 0.37049(8) 0.0191(3) Uani 1 1 d . . .
C22 C 1.04228(19) 0.24842(10) 0.43508(8) 0.0227(3) Uani 1 1 d . . .
H22 H 1.0491 0.1874 0.4412 0.027 Uiso 1 1 calc R . .
C23 C 1.14564(19) 0.29988(11) 0.48838(8) 0.0256(3) Uani 1 1 d . . .
H23 H 1.2223 0.2737 0.5304 0.031 Uiso 1 1 calc R . .
C24 C 1.1406(2) 0.39037(11) 0.48211(9) 0.0284(3) Uani 1 1 d . . .
H24 H 1.2124 0.4254 0.5194 0.034 Uiso 1 1 calc R . .
C25 C 1.02972(19) 0.42712(10) 0.42105(9) 0.0254(3) Uani 1 1 d . . .
H25 H 1.0253 0.4884 0.4166 0.031 Uiso 1 1 calc R . .
C26 C 0.92181(17) 0.37661(9) 0.36459(8) 0.0204(3) Uani 1 1 d . . .
C27 C 0.81669(18) 0.42214(10) 0.30133(9) 0.0239(3) Uani 1 1 d . . .
H27 H 0.8267 0.4834 0.3030 0.029 Uiso 1 1 calc R . .
O28 O 0.71477(13) 0.39254(7) 0.24491(6) 0.0271(2) Uani 1 1 d . . .
H13 H 0.6646(16) 0.1056(12) 0.2595(11) 0.035(5) Uiso 1 1 d D . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni O1 2.0078(10) . ?
Ni O20 2.0284(10) . ?
Ni N9 2.0507(13) . ?
Ni O28 2.1062(11) . ?
Ni N13 2.1119(13) . ?
Ni N17 2.1979(13) . ?
O1 C2 1.2957(19) . ?
C2 C3 1.417(2) . ?
C2 C7 1.426(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.448(2) . ?
C8 N9 1.286(2) . ?
C8 H8 0.9500 . ?
N9 C10 1.461(2) . ?
C10 C11 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N13 1.490(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C14 1.466(2) . ?
N13 H13 0.903(9) . ?
C14 C15 1.518(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.514(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.484(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C18 1.479(2) . ?
N17 C19 1.479(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O20 C21 1.2830(17) . ?
C21 C26 1.432(2) . ?
C21 C22 1.432(2) . ?
C22 C23 1.372(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.403(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.412(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.435(2) . ?
C27 O28 1.2371(18) . ?
C27 H27 0.9500 . ?

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 Ni O20 175.98(5) . . ?
O1 Ni N9 88.22(5) . . ?
O20 Ni N9 94.63(5) . . ?
O1 Ni O28 89.38(4) . . ?
O20 Ni O28 87.90(4) . . ?
N9 Ni O28 87.95(5) . . ?
O1 Ni N13 97.75(5) . . ?
O20 Ni N13 85.18(5) . . ?
N9 Ni N13 88.19(5) . . ?
O28 Ni N13 171.77(5) . . ?
O1 Ni N17 85.37(5) . . ?
O20 Ni N17 91.84(5) . . ?
N9 Ni N17 173.40(5) . . ?
O28 Ni N17 93.57(5) . . ?
N13 Ni N17 91.09(5) . . ?
C2 O1 Ni 122.61(9) . . ?
O1 C2 C3 119.99(15) . . ?
O1 C2 C7 123.40(14) . . ?
C3 C2 C7 116.59(14) . . ?
C4 C3 C2 122.07(17) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 121.03(17) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.46(16) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C7 122.16(17) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 119.56(15) . . ?
C6 C7 C8 117.59(15) . . ?
C2 C7 C8 122.80(14) . . ?
N9 C8 C7 125.43(14) . . ?
N9 C8 H8 117.3 . . ?
C7 C8 H8 117.3 . . ?
C8 N9 C10 118.12(13) . . ?
C8 N9 Ni 124.25(11) . . ?
C10 N9 Ni 117.61(10) . . ?
N9 C10 C11 111.44(13) . . ?
N9 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 115.69(15) . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
N13 C12 C11 111.11(14) . . ?
N13 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N13 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 N13 C12 109.84(13) . . ?
C14 N13 Ni 114.62(10) . . ?
C12 N13 Ni 114.43(10) . . ?
C14 N13 H13 104.6(12) . . ?
C12 N13 H13 109.7(12) . . ?
Ni N13 H13 102.8(13) . . ?
N13 C14 C15 112.90(14) . . ?
N13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 116.72(14) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
N17 C16 C15 116.11(14) . . ?
N17 C16 H16A 108.3 . . ?
C15 C16 H16A 108.3 . . ?
N17 C16 H16B 108.3 . . ?
C15 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C18 N17 C19 108.40(14) . . ?
C18 N17 C16 106.69(13) . . ?
C19 N17 C16 109.78(14) . . ?
C18 N17 Ni 108.12(10) . . ?
C19 N17 Ni 113.19(10) . . ?
C16 N17 Ni 110.42(10) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 O20 Ni 129.20(9) . . ?
O20 C21 C26 124.36(13) . . ?
O20 C21 C22 119.60(13) . . ?
C26 C21 C22 116.04(13) . . ?
C23 C22 C21 121.87(14) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 121.38(14) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 118.58(14) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 C26 121.93(14) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C25 C26 C21 120.20(13) . . ?
C25 C26 C27 116.92(13) . . ?
C21 C26 C27 122.85(13) . . ?
O28 C27 C26 128.86(14) . . ?
O28 C27 H27 115.6 . . ?
C26 C27 H27 115.6 . . ?
C27 O28 Ni 124.65(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B O20 0.99 2.65 3.151(2) 111.8 .
C16 H16B O1 0.99 2.45 3.009(2) 115.0 .
C18 H18B O1 0.98 2.53 3.124(2) 118.7 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1527395'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H48 N8 Ni2 O4'
_chemical_formula_weight         726.20

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                   10.8271(7)
_cell_length_b                   15.8847(10)
_cell_length_c                   19.0150(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.578(2)
_cell_angle_gamma                90
_cell_volume                     3270.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    463
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.05

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   0.5401
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.202
_shelx_estimated_absorpt_T_min   0.795
_shelx_estimated_absorpt_T_max   0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38986
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.142
_diffrn_reflns_theta_max         27.155
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7233
_reflns_number_gt                4734
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick,2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick,2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)and Mercury (CCDC)'
_computing_publication_material  'SHELXL-2013 (Sheldrick,2013)'

_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)+(0.0937P)²+12.5201P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7233
_refine_ls_number_parameters     427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1972
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
NiA Ni 0.39680(6) 0.40510(4) 0.22714(3) 0.01947(18) Uani 1 1 d . . . . .
NiB Ni 0.12391(6) 0.34310(4) 0.28443(3) 0.01944(18) Uani 1 1 d . . . . .
O1A O 0.4672(3) 0.3455(2) 0.31240(18) 0.0225(7) Uani 1 1 d . . . . .
C2A C 0.5240(4) 0.3793(3) 0.3657(3) 0.0231(10) Uani 1 1 d . . . . .
C3A C 0.5505(5) 0.3303(3) 0.4263(3) 0.0249(10) Uani 1 1 d . . . . .
H3A H 0.5257 0.2729 0.4270 0.030 Uiso 1 1 calc R U . . .
C4A C 0.6108(5) 0.3627(4) 0.4842(3) 0.0333(12) Uani 1 1 d . . . . .
H4A H 0.6257 0.3277 0.5239 0.040 Uiso 1 1 calc R U . . .
C5A C 0.6506(5) 0.4467(3) 0.4854(3) 0.0308(12) Uani 1 1 d . . . . .
H5A H 0.6929 0.4688 0.5253 0.037 Uiso 1 1 calc R U . . .
C6A C 0.6270(5) 0.4959(3) 0.4279(3) 0.0271(11) Uani 1 1 d . . . . .
H6A H 0.6529 0.5531 0.4286 0.033 Uiso 1 1 calc R U . . .
C7A C 0.5656(4) 0.4649(3) 0.3677(3) 0.0232(10) Uani 1 1 d . . . . .
C8A C 0.5469(4) 0.5251(3) 0.3107(3) 0.0229(10) Uani 1 1 d . . . . .
H8A H 0.5792 0.5799 0.3184 0.028 Uiso 1 1 calc R U . . .
N9A N 0.4926(4) 0.5133(2) 0.2518(2) 0.0202(8) Uani 1 1 d . . . . .
C10A C 0.4866(5) 0.5863(3) 0.2048(3) 0.0252(11) Uani 1 1 d . . . . .
H10A H 0.5346 0.5740 0.1620 0.030 Uiso 1 1 calc R U . . .
H10B H 0.5258 0.6351 0.2286 0.030 Uiso 1 1 calc R U . . .
C11A C 0.3552(5) 0.6100(3) 0.1832(3) 0.0257(11) Uani 1 1 d . . . . .
H11A H 0.3013 0.6057 0.2248 0.031 Uiso 1 1 calc R U . . .
H11B H 0.3541 0.6693 0.1673 0.031 Uiso 1 1 calc R U . . .
C12A C 0.3031(5) 0.5547(3) 0.1250(3) 0.0290(11) Uani 1 1 d . . . . .
H12A H 0.2187 0.5747 0.1132 0.035 Uiso 1 1 calc R U . . .
H12B H 0.3544 0.5622 0.0827 0.035 Uiso 1 1 calc R U . . .
N13A N 0.2968(4) 0.4633(2) 0.1416(2) 0.0219(8) Uani 1 1 d . . . . .
H13A H 0.218(5) 0.455(3) 0.163(3) 0.019(13) Uiso 1 1 d . . . . .
C14A C 0.2982(5) 0.4143(3) 0.0745(3) 0.0253(10) Uani 1 1 d . . . . .
H14A H 0.2497 0.4448 0.0382 0.030 Uiso 1 1 calc R U . . .
H14B H 0.2584 0.3590 0.0821 0.030 Uiso 1 1 calc R U . . .
C15A C 0.4288(5) 0.4009(4) 0.0485(3) 0.0314(12) Uani 1 1 d . . . . .
H15A H 0.4752 0.4542 0.0538 0.038 Uiso 1 1 calc R U . . .
H15B H 0.4252 0.3872 -0.0022 0.038 Uiso 1 1 calc R U . . .
C16A C 0.4997(5) 0.3313(3) 0.0867(3) 0.0288(11) Uani 1 1 d . . . . .
H16A H 0.4462 0.2809 0.0890 0.035 Uiso 1 1 calc R U . . .
H16B H 0.5727 0.3163 0.0584 0.035 Uiso 1 1 calc R U . . .
N17A N 0.5423(4) 0.3521(2) 0.1591(2) 0.0243(9) Uani 1 1 d . . . . .
C18A C 0.5876(5) 0.2721(3) 0.1901(3) 0.0335(13) Uani 1 1 d . . . . .
H18A H 0.6528 0.2488 0.1604 0.040 Uiso 1 1 calc R U . . .
H18B H 0.5192 0.2318 0.1928 0.040 Uiso 1 1 calc R U . . .
H18C H 0.6207 0.2827 0.2374 0.040 Uiso 1 1 calc R U . . .
C19A C 0.6486(5) 0.4089(3) 0.1550(3) 0.0305(12) Uani 1 1 d . . . . .
H19A H 0.6747 0.4253 0.2026 0.037 Uiso 1 1 calc R U . . .
H19B H 0.6255 0.4593 0.1282 0.037 Uiso 1 1 calc R U . . .
H19C H 0.7169 0.3801 0.1316 0.037 Uiso 1 1 calc R U . . .
N20A N 0.2809(4) 0.2995(2) 0.2142(2) 0.0220(8) Uani 1 1 d . . . . .
C21A C 0.2647(5) 0.2413(3) 0.1755(3) 0.0237(10) Uani 1 1 d . . . . .
O22A O 0.2497(4) 0.1829(2) 0.1374(2) 0.0420(10) Uani 1 1 d . . . . .
O1B O 0.0563(3) 0.4045(2) 0.20030(18) 0.0229(7) Uani 1 1 d . . . . .
C2B C -0.0037(4) 0.3730(3) 0.1470(3) 0.0215(10) Uani 1 1 d . . . . .
C3B C -0.0299(5) 0.4265(3) 0.0886(3) 0.0262(11) Uani 1 1 d . . . . .
H3B H -0.0038 0.4836 0.0902 0.031 Uiso 1 1 calc R U . . .
C4B C -0.0927(5) 0.3974(3) 0.0296(3) 0.0299(12) Uani 1 1 d . . . . .
H4B H -0.1088 0.4348 -0.0084 0.036 Uiso 1 1 calc R U . . .
C5B C -0.1326(5) 0.3140(4) 0.0250(3) 0.0310(12) Uani 1 1 d . . . . .
H5B H -0.1753 0.2942 -0.0156 0.037 Uiso 1 1 calc R U . . .
C6B C -0.1083(5) 0.2606(3) 0.0814(3) 0.0259(11) Uani 1 1 d . . . . .
H6B H -0.1350 0.2037 0.0788 0.031 Uiso 1 1 calc R U . . .
C7B C -0.0454(4) 0.2882(3) 0.1422(3) 0.0215(10) Uani 1 1 d . . . . .
C8B C -0.0274(4) 0.2263(3) 0.1970(3) 0.0228(10) Uani 1 1 d . . . . .
H8B H -0.0599 0.1718 0.1878 0.027 Uiso 1 1 calc R U . . .
N9B N 0.0274(4) 0.2363(2) 0.2568(2) 0.0200(8) Uani 1 1 d . . . . .
C10B C 0.0335(5) 0.1605(3) 0.3021(3) 0.0271(11) Uani 1 1 d . . . . .
H10C H -0.0014 0.1119 0.2761 0.033 Uiso 1 1 calc R U . . .
H10D H -0.0177 0.1698 0.3443 0.033 Uiso 1 1 calc R U . . .
C11B C 0.1656(5) 0.1399(3) 0.3253(3) 0.0278(11) Uani 1 1 d . . . . .
H11C H 0.1695 0.0801 0.3397 0.033 Uiso 1 1 calc R U . . .
H11D H 0.2210 0.1472 0.2846 0.033 Uiso 1 1 calc R U . . .
C12B C 0.2119(5) 0.1939(3) 0.3852(3) 0.0327(12) Uani 1 1 d . . . . .
H12C H 0.1548 0.1877 0.4252 0.039 Uiso 1 1 calc R U . . .
H12D H 0.2937 0.1725 0.4007 0.039 Uiso 1 1 calc R U . . .
N13B N 0.2237(4) 0.2845(2) 0.3684(2) 0.0228(9) Uani 1 1 d . . . . .
H13B H 0.299(6) 0.291(3) 0.348(3) 0.027(15) Uiso 1 1 d . . . . .
C14B C 0.2290(5) 0.3343(3) 0.4353(3) 0.0291(11) Uani 1 1 d . . . . .
H14C H 0.2725 0.3881 0.4265 0.035 Uiso 1 1 calc R U . . .
H14D H 0.2775 0.3025 0.4708 0.035 Uiso 1 1 calc R U . . .
C15B C 0.1015(5) 0.3533(4) 0.4647(3) 0.0333(12) Uani 1 1 d . . . . .
H15C H 0.0527 0.3006 0.4646 0.040 Uiso 1 1 calc R U . . .
H15D H 0.1114 0.3716 0.5142 0.040 Uiso 1 1 calc R U . . .
C16B C 0.0292(5) 0.4201(3) 0.4250(3) 0.0306(12) Uani 1 1 d . . . . .
H16C H -0.0423 0.4366 0.4540 0.037 Uiso 1 1 calc R U . . .
H16D H 0.0825 0.4704 0.4204 0.037 Uiso 1 1 calc R U . . .
N17B N -0.0176(4) 0.3971(2) 0.3538(2) 0.0246(9) Uani 1 1 d . . . . .
C18B C -0.1229(5) 0.3391(3) 0.3609(3) 0.0309(12) Uani 1 1 d . . . . .
H18D H -0.0945 0.2863 0.3824 0.037 Uiso 1 1 calc R U . . .
H18E H -0.1586 0.3274 0.3144 0.037 Uiso 1 1 calc R U . . .
H18F H -0.1857 0.3649 0.3908 0.037 Uiso 1 1 calc R U . . .
C19B C -0.0678(5) 0.4752(3) 0.3214(3) 0.0327(12) Uani 1 1 d . . . . .
H19D H -0.1033 0.4620 0.2751 0.039 Uiso 1 1 calc R U . . .
H19E H -0.0012 0.5164 0.3162 0.039 Uiso 1 1 calc R U . . .
H19F H -0.1320 0.4986 0.3516 0.039 Uiso 1 1 calc R U . . .
N20B N 0.2423(4) 0.4481(2) 0.2963(2) 0.0204(8) Uani 1 1 d . . . . .
C21B C 0.2434(5) 0.5137(3) 0.3246(2) 0.0217(10) Uani 1 1 d . . . . .
O22B O 0.2441(4) 0.5812(2) 0.3526(2) 0.0369(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
NiA O1A 2.020(3) . ?
NiA N9A 2.059(4) . ?
NiA N20A 2.107(4) . ?
NiA N13A 2.154(4) . ?
NiA N17A 2.214(4) . ?
NiA N20B 2.244(4) . ?
NiB O1B 2.006(3) . ?
NiB N9B 2.057(4) . ?
NiB N20B 2.115(4) . ?
NiB N13B 2.132(4) . ?
NiB N17B 2.205(4) . ?
NiB N20A 2.280(4) . ?
O1A C2A 1.297(6) . ?
C2A C3A 1.418(7) . ?
C2A C7A 1.433(7) . ?
C3A C4A 1.373(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.402(8) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.367(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.407(7) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.457(7) . ?
C8A N9A 1.273(6) . ?
C8A H8A 0.9500 . ?
N9A C10A 1.466(6) . ?
C10A C11A 1.524(7) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.517(7) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A N13A 1.487(6) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
N13A C14A 1.494(6) . ?
N13A H13A 0.95(6) . ?
C14A C15A 1.519(7) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.525(7) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A N17A 1.485(7) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
N17A C19A 1.466(6) . ?
N17A C18A 1.482(6) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
N20A C21A 1.195(6) . ?
C21A O22A 1.186(6) . ?
O1B C2B 1.298(6) . ?
C2B C7B 1.423(7) . ?
C2B C3B 1.424(7) . ?
C3B C4B 1.386(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.396(8) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.389(7) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.406(7) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.445(7) . ?
C8B N9B 1.287(6) . ?
C8B H8B 0.9500 . ?
N9B C10B 1.483(6) . ?
C10B C11B 1.528(7) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.508(8) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B N13B 1.480(6) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
N13B C14B 1.499(6) . ?
N13B H13B 0.91(6) . ?
C14B C15B 1.525(7) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.516(8) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B N17B 1.487(7) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
N17B C18B 1.474(6) . ?
N17B C19B 1.485(7) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
N20B C21B 1.173(6) . ?
C21B O22B 1.196(6) . ?

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
O1A NiA N9A 91.32(14) . . ?
O1A NiA N20A 86.59(15) . . ?
N9A NiA N20A 171.42(16) . . ?
O1A NiA N13A 171.97(15) . . ?
N9A NiA N13A 93.54(15) . . ?
N20A NiA N13A 87.66(16) . . ?
O1A NiA N17A 91.48(14) . . ?
N9A NiA N17A 95.20(15) . . ?
N20A NiA N17A 93.18(15) . . ?
N13A NiA N17A 94.43(16) . . ?
O1A NiA N20B 87.12(14) . . ?
N9A NiA N20B 89.37(15) . . ?
N20A NiA N20B 82.22(15) . . ?
N13A NiA N20B 86.55(15) . . ?
N17A NiA N20B 175.26(14) . . ?
O1B NiB N9B 90.95(15) . . ?
O1B NiB N20B 85.26(14) . . ?
N9B NiB N20B 169.49(16) . . ?
O1B NiB N13B 170.92(16) . . ?
N9B NiB N13B 94.82(16) . . ?
N20B NiB N13B 87.85(15) . . ?
O1B NiB N17B 92.14(15) . . ?
N9B NiB N17B 96.86(15) . . ?
N20B NiB N17B 93.07(15) . . ?
N13B NiB N17B 94.13(16) . . ?
O1B NiB N20A 87.07(14) . . ?
N9B NiB N20A 88.84(15) . . ?
N20B NiB N20A 81.19(15) . . ?
N13B NiB N20A 86.04(16) . . ?
N17B NiB N20A 174.26(15) . . ?
C2A O1A NiA 127.3(3) . . ?
O1A C2A C3A 119.9(4) . . ?
O1A C2A C7A 124.0(4) . . ?
C3A C2A C7A 116.0(5) . . ?
C4A C3A C2A 122.4(5) . . ?
C4A C3A H3A 118.8 . . ?
C2A C3A H3A 118.8 . . ?
C3A C4A C5A 120.9(5) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C6A C5A C4A 118.4(5) . . ?
C6A C5A H5A 120.8 . . ?
C4A C5A H5A 120.8 . . ?
C5A C6A C7A 122.3(5) . . ?
C5A C6A H6A 118.9 . . ?
C7A C6A H6A 118.9 . . ?
C6A C7A C2A 119.9(4) . . ?
C6A C7A C8A 115.9(4) . . ?
C2A C7A C8A 124.1(5) . . ?
N9A C8A C7A 128.2(4) . . ?
N9A C8A H8A 115.9 . . ?
C7A C8A H8A 115.9 . . ?
C8A N9A C10A 115.9(4) . . ?
C8A N9A NiA 123.3(3) . . ?
C10A N9A NiA 120.2(3) . . ?
N9A C10A C11A 113.2(4) . . ?
N9A C10A H10A 108.9 . . ?
C11A C10A H10A 108.9 . . ?
N9A C10A H10B 108.9 . . ?
C11A C10A H10B 108.9 . . ?
H10A C10A H10B 107.7 . . ?
C12A C11A C10A 113.1(4) . . ?
C12A C11A H11A 108.9 . . ?
C10A C11A H11A 109.0 . . ?
C12A C11A H11B 109.0 . . ?
C10A C11A H11B 108.9 . . ?
H11A C11A H11B 107.8 . . ?
N13A C12A C11A 115.4(4) . . ?
N13A C12A H12A 108.4 . . ?
C11A C12A H12A 108.4 . . ?
N13A C12A H12B 108.4 . . ?
C11A C12A H12B 108.4 . . ?
H12A C12A H12B 107.5 . . ?
C12A N13A C14A 109.1(4) . . ?
C12A N13A NiA 123.7(3) . . ?
C14A N13A NiA 114.3(3) . . ?
C12A N13A H13A 105(3) . . ?
C14A N13A H13A 108(3) . . ?
NiA N13A H13A 94(3) . . ?
N13A C14A C15A 111.6(4) . . ?
N13A C14A H14A 109.3 . . ?
C15A C14A H14A 109.3 . . ?
N13A C14A H14B 109.3 . . ?
C15A C14A H14B 109.3 . . ?
H14A C14A H14B 108.0 . . ?
C14A C15A C16A 114.4(4) . . ?
C14A C15A H15A 108.7 . . ?
C16A C15A H15A 108.7 . . ?
C14A C15A H15B 108.7 . . ?
C16A C15A H15B 108.7 . . ?
H15A C15A H15B 107.6 . . ?
N17A C16A C15A 115.5(4) . . ?
N17A C16A H16A 108.4 . . ?
C15A C16A H16A 108.4 . . ?
N17A C16A H16B 108.4 . . ?
C15A C16A H16B 108.4 . . ?
H16A C16A H16B 107.5 . . ?
C19A N17A C18A 107.0(4) . . ?
C19A N17A C16A 108.9(4) . . ?
C18A N17A C16A 106.0(4) . . ?
C19A N17A NiA 111.2(3) . . ?
C18A N17A NiA 109.2(3) . . ?
C16A N17A NiA 114.2(3) . . ?
N17A C18A H18A 109.5 . . ?
N17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
N17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N17A C19A H19A 109.5 . . ?
N17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
N17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C21A N20A NiA 140.6(4) . . ?
C21A N20A NiB 119.4(4) . . ?
NiA N20A NiB 97.84(15) . . ?
O22A C21A N20A 179.3(6) . . ?
C2B O1B NiB 127.6(3) . . ?
O1B C2B C7B 124.8(4) . . ?
O1B C2B C3B 118.2(4) . . ?
C7B C2B C3B 117.0(5) . . ?
C4B C3B C2B 121.6(5) . . ?
C4B C3B H3B 119.2 . . ?
C2B C3B H3B 119.2 . . ?
C3B C4B C5B 121.1(5) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B H4B 119.5 . . ?
C6B C5B C4B 118.4(5) . . ?
C6B C5B H5B 120.8 . . ?
C4B C5B H5B 120.8 . . ?
C5B C6B C7B 122.0(5) . . ?
C5B C6B H6B 119.0 . . ?
C7B C6B H6B 119.0 . . ?
C6B C7B C2B 120.0(4) . . ?
C6B C7B C8B 116.2(4) . . ?
C2B C7B C8B 123.9(4) . . ?
N9B C8B C7B 127.6(4) . . ?
N9B C8B H8B 116.2 . . ?
C7B C8B H8B 116.2 . . ?
C8B N9B C10B 115.5(4) . . ?
C8B N9B NiB 123.8(3) . . ?
C10B N9B NiB 120.1(3) . . ?
N9B C10B C11B 112.2(4) . . ?
N9B C10B H10C 109.2 . . ?
C11B C10B H10C 109.2 . . ?
N9B C10B H10D 109.2 . . ?
C11B C10B H10D 109.2 . . ?
H10C C10B H10D 107.9 . . ?
C12B C11B C10B 113.5(4) . . ?
C12B C11B H11C 108.9 . . ?
C10B C11B H11C 108.9 . . ?
C12B C11B H11D 108.9 . . ?
C10B C11B H11D 108.9 . . ?
H11C C11B H11D 107.7 . . ?
N13B C12B C11B 114.7(4) . . ?
N13B C12B H12C 108.6 . . ?
C11B C12B H12C 108.6 . . ?
N13B C12B H12D 108.6 . . ?
C11B C12B H12D 108.6 . . ?
H12C C12B H12D 107.6 . . ?
C12B N13B C14B 109.4(4) . . ?
C12B N13B NiB 122.8(3) . . ?
C14B N13B NiB 114.8(3) . . ?
C12B N13B H13B 106(3) . . ?
C14B N13B H13B 106(4) . . ?
NiB N13B H13B 95(4) . . ?
N13B C14B C15B 112.9(4) . . ?
N13B C14B H14C 109.0 . . ?
C15B C14B H14C 109.0 . . ?
N13B C14B H14D 109.0 . . ?
C15B C14B H14D 109.0 . . ?
H14C C14B H14D 107.8 . . ?
C16B C15B C14B 114.9(5) . . ?
C16B C15B H15C 108.5 . . ?
C14B C15B H15C 108.5 . . ?
C16B C15B H15D 108.5 . . ?
C14B C15B H15D 108.5 . . ?
H15C C15B H15D 107.5 . . ?
N17B C16B C15B 116.8(4) . . ?
N17B C16B H16C 108.1 . . ?
C15B C16B H16C 108.1 . . ?
N17B C16B H16D 108.1 . . ?
C15B C16B H16D 108.1 . . ?
H16C C16B H16D 107.3 . . ?
C18B N17B C19B 106.3(4) . . ?
C18B N17B C16B 109.0(4) . . ?
C19B N17B C16B 107.0(4) . . ?
C18B N17B NiB 110.8(3) . . ?
C19B N17B NiB 109.3(3) . . ?
C16B N17B NiB 114.1(3) . . ?
N17B C18B H18D 109.5 . . ?
N17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
N17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
N17B C19B H19D 109.5 . . ?
N17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
N17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C21B N20B NiB 138.8(4) . . ?
C21B N20B NiA 122.4(4) . . ?
NiB N20B NiA 98.74(15) . . ?
N20B C21B O22B 179.1(6) . . ?

_refine_diff_density_max         3.200
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.150

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_compound-5
_database_code_depnum_ccdc_archive 'CCDC 1527396'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H50 N10 Ni2 O3 S4'
_chemical_formula_weight         904.51

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/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                   10.8625(3)
_cell_length_b                   12.3213(3)
_cell_length_c                   15.8254(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.3490(10)
_cell_angle_gamma                90
_cell_volume                     2052.00(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    520
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.20

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.169
_shelx_estimated_absorpt_T_min   0.721
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7205
_exptl_absorpt_correction_T_max  0.9123
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24860
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.935
_diffrn_reflns_theta_max         27.920
_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             4912
_reflns_number_gt                3789
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick,2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick,2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)and Mercury (CCDC)'
_computing_publication_material  'SHELXL-2013 (Sheldrick,2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=exp[0.0500(sinθ/λ)²)]/[σ²(Fo²)+(0.0305P)²+1.1724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4912
_refine_ls_number_parameters     257
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0773
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
O23 O 1.4923(13) 0.9474(12) 0.5191(11) 0.243(9) Uani 0.5 1 d D . P . .
C22 C 1.490(2) 1.0150(18) 0.5972(15) 0.243(9) Uani 0.5 1 d D . P . .
H17 H 1.175(2) 0.741(2) 0.4312(18) 0.043(8) Uiso 1 1 d . . . . .
Ni Ni 0.87597(2) 0.97536(2) 0.04225(2) 0.01876(8) Uani 1 1 d . . . . .
S1 S 1.24032(5) 1.09670(5) 0.23922(4) 0.03105(15) Uani 1 1 d . . . . .
S2 S 0.81025(6) 0.98226(6) 0.33278(4) 0.03630(16) Uani 1 1 d . . . . .
O1 O 0.80958(13) 1.12676(12) -0.00147(10) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.7078(2) 1.14381(18) -0.06724(14) 0.0220(5) Uani 1 1 d . . . . .
C3 C 0.6921(2) 1.24611(19) -0.10799(15) 0.0280(5) Uani 1 1 d . . . . .
H3 H 0.7552 1.3002 -0.0889 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5872(2) 1.2700(2) -0.17515(16) 0.0341(6) Uani 1 1 d . . . . .
H4 H 0.5789 1.3403 -0.2006 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4939(2) 1.1929(2) -0.20589(17) 0.0374(6) Uani 1 1 d . . . . .
H5 H 0.4227 1.2089 -0.2527 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5072(2) 1.0927(2) -0.16677(16) 0.0320(6) Uani 1 1 d . . . . .
H6 H 0.4434 1.0395 -0.1871 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6114(2) 1.06572(19) -0.09782(15) 0.0250(5) Uani 1 1 d . . . . .
C8 C 0.6094(2) 0.95893(19) -0.06051(16) 0.0278(5) Uani 1 1 d . . . . .
H8 H 0.5319 0.9198 -0.0779 0.033 Uiso 1 1 calc R U . . .
N9 N 0.70049(16) 0.91153(15) -0.00669(12) 0.0224(4) Uani 1 1 d . . . . .
C10 C 0.6749(2) 0.80760(18) 0.03040(16) 0.0285(5) Uani 1 1 d . . . . .
H10A H 0.5827 0.7922 0.0111 0.034 Uiso 1 1 calc R U . . .
H10B H 0.6973 0.8138 0.0948 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7480(2) 0.71210(19) 0.00469(16) 0.0307(5) Uani 1 1 d . . . . .
H11A H 0.7520 0.6532 0.0478 0.037 Uiso 1 1 calc R U . . .
H11B H 0.6997 0.6843 -0.0527 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8825(2) 0.73811(18) -0.00102(15) 0.0266(5) Uani 1 1 d . . . . .
H12A H 0.9314 0.6697 0.0036 0.032 Uiso 1 1 calc R U . . .
H12B H 0.8790 0.7701 -0.0590 0.032 Uiso 1 1 calc R U . . .
N13 N 0.95078(18) 0.81438(15) 0.06761(12) 0.0219(4) Uani 1 1 d . . . . .
C14 C 0.9692(2) 0.76276(19) 0.15422(15) 0.0266(5) Uani 1 1 d . . . . .
H14A H 0.9924 0.6857 0.1496 0.032 Uiso 1 1 calc R U . . .
H14B H 0.8877 0.7646 0.1715 0.032 Uiso 1 1 calc R U . . .
C15 C 1.0708(2) 0.81659(19) 0.22511(14) 0.0256(5) Uani 1 1 d . . . . .
H15A H 1.1548 0.8103 0.2116 0.031 Uiso 1 1 calc R U . . .
H15B H 1.0511 0.8945 0.2296 0.031 Uiso 1 1 calc R U . . .
C16 C 1.0723(2) 0.75890(19) 0.31000(15) 0.0257(5) Uani 1 1 d . . . . .
H16A H 0.9911 0.7740 0.3256 0.031 Uiso 1 1 calc R U . . .
H16B H 1.0765 0.6797 0.3005 0.031 Uiso 1 1 calc R U . . .
N17 N 1.17943(18) 0.79002(16) 0.38543(13) 0.0273(4) Uani 1 1 d . . . . .
C18 C 1.1665(3) 0.9032(2) 0.41503(17) 0.0362(6) Uani 1 1 d . . . . .
H18A H 1.2323 0.9174 0.4686 0.043 Uiso 1 1 calc R U . . .
H18B H 1.0825 0.9126 0.4264 0.043 Uiso 1 1 calc R U . . .
H18C H 1.1761 0.9541 0.3695 0.043 Uiso 1 1 calc R U . . .
C19 C 1.3064(2) 0.7718(2) 0.36812(18) 0.0423(7) Uani 1 1 d . . . . .
H19A H 1.3213 0.8264 0.3267 0.051 Uiso 1 1 calc R U . . .
H19B H 1.3093 0.6991 0.3435 0.051 Uiso 1 1 calc R U . . .
H19C H 1.3723 0.7779 0.4228 0.051 Uiso 1 1 calc R U . . .
N20 N 1.06446(16) 1.03623(14) 0.08631(12) 0.0215(4) Uani 1 1 d . . . . .
C21 C 1.13766(19) 1.06041(17) 0.15131(14) 0.0203(4) Uani 1 1 d . . . . .
N22 N 0.83673(18) 0.99275(15) 0.16170(13) 0.0266(4) Uani 1 1 d . . . . .
C23 C 0.8252(2) 0.98813(17) 0.23240(15) 0.0229(5) Uani 1 1 d . . . . .
H13 H 1.023(2) 0.8213(19) 0.0579(15) 0.023(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O23 O23 1.46(3) 3_876 ?
O23 C22 1.496(17) . ?
Ni N9 2.0298(17) . ?
Ni N22 2.050(2) . ?
Ni O1 2.0570(15) . ?
Ni N20 2.1291(17) . ?
Ni N13 2.1433(19) . ?
Ni N20 2.2871(19) 3_775 ?
S1 C21 1.616(2) . ?
S2 C23 1.638(2) . ?
O1 C2 1.334(2) . ?
C2 C3 1.407(3) . ?
C2 C7 1.416(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.445(3) . ?
C8 N9 1.276(3) . ?
C8 H8 0.9500 . ?
N9 C10 1.464(3) . ?
C10 C11 1.530(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N13 1.488(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
N13 C14 1.479(3) . ?
N13 H13 0.84(2) . ?
C14 C15 1.518(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.516(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N17 1.496(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C19 1.488(3) . ?
N17 C18 1.489(3) . ?
N17 H17 0.95(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N20 C21 1.172(3) . ?
N20 Ni 2.2871(19) 3_775 ?
N22 C23 1.158(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O23 O23 C22 82.8(18) 3_876 . ?
N9 Ni N22 90.12(7) . . ?
N9 Ni O1 90.30(7) . . ?
N22 Ni O1 94.57(7) . . ?
N9 Ni N20 175.84(7) . . ?
N22 Ni N20 93.67(7) . . ?
O1 Ni N20 91.10(6) . . ?
N9 Ni N13 89.40(7) . . ?
N22 Ni N13 94.58(7) . . ?
O1 Ni N13 170.84(7) . . ?
N20 Ni N13 88.60(7) . . ?
N9 Ni N20 94.73(7) . 3_775 ?
N22 Ni N20 175.12(7) . 3_775 ?
O1 Ni N20 84.86(6) . 3_775 ?
N20 Ni N20 81.50(7) . 3_775 ?
N13 Ni N20 86.05(7) . 3_775 ?
C2 O1 Ni 123.98(13) . . ?
O1 C2 C3 118.80(19) . . ?
O1 C2 C7 124.0(2) . . ?
C3 C2 C7 117.2(2) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C7 122.6(2) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C6 C7 C2 119.4(2) . . ?
C6 C7 C8 116.2(2) . . ?
C2 C7 C8 124.4(2) . . ?
N9 C8 C7 127.0(2) . . ?
N9 C8 H8 116.5 . . ?
C7 C8 H8 116.5 . . ?
C8 N9 C10 118.38(18) . . ?
C8 N9 Ni 125.24(16) . . ?
C10 N9 Ni 116.08(14) . . ?
N9 C10 C11 113.80(19) . . ?
N9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 115.06(19) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N13 C12 C11 113.74(19) . . ?
N13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
N13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 N13 C12 109.47(17) . . ?
C14 N13 Ni 121.96(14) . . ?
C12 N13 Ni 110.51(13) . . ?
C14 N13 H13 107.3(16) . . ?
C12 N13 H13 104.4(16) . . ?
Ni N13 H13 101.5(16) . . ?
N13 C14 C15 113.80(18) . . ?
N13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 107.22(18) . . ?
C16 C15 H15A 110.3 . . ?
C14 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C14 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
N17 C16 C15 114.97(18) . . ?
N17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
N17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C19 N17 C18 111.3(2) . . ?
C19 N17 C16 112.80(19) . . ?
C18 N17 C16 112.06(18) . . ?
C19 N17 H17 105.6(16) . . ?
C18 N17 H17 109.1(16) . . ?
C16 N17 H17 105.5(16) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 N20 Ni 139.92(16) . . ?
C21 N20 Ni 121.11(15) . 3_775 ?
Ni N20 Ni 98.50(7) . 3_775 ?
N20 C21 S1 178.2(2) . . ?
C23 N22 Ni 169.52(18) . . ?
N22 C23 S2 179.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B N20 0.99 2.53 3.205(3) 125.4 3_775
N13 H13 O1 0.84(2) 2.31(2) 3.122(2) 164(2) 3_775
C15 H15B N22 0.99 2.61 3.304(3) 127.4 .
C16 H16B N22 0.99 2.50 3.422(3) 154.0 2_745
C18 H18C S1 0.98 2.92 3.896(3) 172.3 .

_refine_diff_density_max         0.603
_refine_diff_density_min         -0.584
_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_f
_database_code_depnum_ccdc_archive 'CCDC 1527394'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H48 N12 Ni2 O2'
_chemical_formula_weight         726.22

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      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                   10.8264(6)
_cell_length_b                   15.9223(8)
_cell_length_c                   19.0138(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.451(2)
_cell_angle_gamma                90
_cell_volume                     3277.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    532
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      25.10

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   0.5675
_exptl_transmission_factor_max   0.7454
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.198
_shelx_estimated_absorpt_T_min   0.715
_shelx_estimated_absorpt_T_max   0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30691
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6717
_reflns_number_gt                4770
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick,2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick,2013)'
_computing_molecular_graphics    'Platon (Spek, 2008)and Mercury (CCDC)'
_computing_publication_material  'SHELXL-2013 (Sheldrick,2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+24.1566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6717
_refine_ls_number_parameters     427
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.1988
_refine_ls_wR_factor_gt          0.1799
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
NiA Ni 0.12304(7) 0.65679(5) 0.28509(4) 0.0214(2) Uani 1 1 d . . . . .
NiB Ni 0.40010(7) 0.59460(5) 0.22661(4) 0.0219(2) Uani 1 1 d . . . . .
O1A O 0.0569(4) 0.5952(3) 0.2009(2) 0.0263(10) Uani 1 1 d . . . . .
C2A C -0.0019(5) 0.6243(4) 0.1471(3) 0.0228(13) Uani 1 1 d . . . . .
C3A C -0.0307(6) 0.5713(5) 0.0896(4) 0.0295(15) Uani 1 1 d . . . . .
H3A H -0.0072 0.5138 0.0918 0.035 Uiso 1 1 calc R U . . .
C4A C -0.0908(6) 0.5998(5) 0.0311(4) 0.0362(17) Uani 1 1 d . . . . .
H4A H -0.1067 0.5621 -0.0066 0.043 Uiso 1 1 calc R U . . .
C5A C -0.1296(6) 0.6830(5) 0.0253(4) 0.0365(18) Uani 1 1 d . . . . .
H5A H -0.1715 0.7024 -0.0157 0.044 Uiso 1 1 calc R U . . .
C6A C -0.1054(6) 0.7368(5) 0.0811(4) 0.0310(16) Uani 1 1 d . . . . .
H6A H -0.1320 0.7935 0.0779 0.037 Uiso 1 1 calc R U . . .
C7A C -0.0432(5) 0.7104(4) 0.1419(3) 0.0247(14) Uani 1 1 d . . . . .
C8A C -0.0237(6) 0.7725(4) 0.1967(3) 0.0279(15) Uani 1 1 d . . . . .
H8A H -0.0534 0.8274 0.1868 0.033 Uiso 1 1 calc R U . . .
N9A N 0.0282(5) 0.7627(3) 0.2563(3) 0.0256(12) Uani 1 1 d . . . . .
C10A C 0.0357(6) 0.8387(4) 0.3009(4) 0.0328(16) Uani 1 1 d . . . . .
H10A H -0.0170 0.8307 0.3427 0.039 Uiso 1 1 calc R U . . .
H10B H 0.0026 0.8872 0.2741 0.039 Uiso 1 1 calc R U . . .
C11A C 0.1669(6) 0.8587(4) 0.3251(4) 0.0338(16) Uani 1 1 d . . . . .
H11A H 0.2236 0.8514 0.2850 0.041 Uiso 1 1 calc R U . . .
H11B H 0.1710 0.9182 0.3399 0.041 Uiso 1 1 calc R U . . .
C12A C 0.2102(7) 0.8037(4) 0.3853(4) 0.0375(17) Uani 1 1 d . . . . .
H12A H 0.2911 0.8249 0.4022 0.045 Uiso 1 1 calc R U . . .
H12B H 0.1511 0.8097 0.4245 0.045 Uiso 1 1 calc R U . . .
N13A N 0.2232(5) 0.7137(4) 0.3692(3) 0.0261(12) Uani 1 1 d D . . . .
H13A H 0.296(3) 0.707(4) 0.344(3) 0.018(16) Uiso 1 1 d D . . . .
C14A C 0.2283(6) 0.6642(5) 0.4348(4) 0.0323(16) Uani 1 1 d . . . . .
H14A H 0.2775 0.6955 0.4703 0.039 Uiso 1 1 calc R U . . .
H14B H 0.2714 0.6106 0.4255 0.039 Uiso 1 1 calc R U . . .
C15A C 0.1029(6) 0.6454(6) 0.4648(4) 0.0409(19) Uani 1 1 d . . . . .
H15A H 0.0539 0.6979 0.4651 0.049 Uiso 1 1 calc R U . . .
H15B H 0.1136 0.6271 0.5143 0.049 Uiso 1 1 calc R U . . .
C16A C 0.0298(6) 0.5783(5) 0.4253(4) 0.0340(17) Uani 1 1 d . . . . .
H16A H 0.0830 0.5281 0.4200 0.041 Uiso 1 1 calc R U . . .
H16B H -0.0416 0.5618 0.4544 0.041 Uiso 1 1 calc R U . . .
N17A N -0.0172(4) 0.6032(4) 0.3540(3) 0.0268(12) Uani 1 1 d . . . . .
C18A C -0.0675(6) 0.5253(5) 0.3216(4) 0.0366(17) Uani 1 1 d . . . . .
H18A H -0.1355 0.5039 0.3502 0.044 Uiso 1 1 calc R U . . .
H18B H -0.0022 0.4829 0.3190 0.044 Uiso 1 1 calc R U . . .
H18C H -0.0982 0.5378 0.2741 0.044 Uiso 1 1 calc R U . . .
C19A C -0.1227(6) 0.6611(5) 0.3615(4) 0.0386(18) Uani 1 1 d . . . . .
H19A H -0.1575 0.6738 0.3150 0.046 Uiso 1 1 calc R U . . .
H19B H -0.0946 0.7132 0.3839 0.046 Uiso 1 1 calc R U . . .
H19C H -0.1861 0.6347 0.3907 0.046 Uiso 1 1 calc R U . . .
N20A N 0.2783(4) 0.6993(3) 0.2177(3) 0.0236(11) Uani 1 1 d . . . . .
N21A N 0.2666(4) 0.7547(3) 0.1766(3) 0.0257(12) Uani 1 1 d . . . . .
N22A N 0.2542(6) 0.8098(4) 0.1371(4) 0.0428(16) Uani 1 1 d . . . . .
O1B O 0.4686(4) 0.6548(3) 0.3115(2) 0.0272(10) Uani 1 1 d . . . . .
C2B C 0.5263(5) 0.6205(4) 0.3650(3) 0.0257(14) Uani 1 1 d . . . . .
C3B C 0.5519(6) 0.6697(5) 0.4250(4) 0.0314(16) Uani 1 1 d . . . . .
H3B H 0.5276 0.7271 0.4253 0.038 Uiso 1 1 calc R U . . .
C4B C 0.6113(6) 0.6369(5) 0.4830(4) 0.0374(18) Uani 1 1 d . . . . .
H4B H 0.6274 0.6719 0.5224 0.045 Uiso 1 1 calc R U . . .
C5B C 0.6481(6) 0.5535(5) 0.4848(4) 0.0376(17) Uani 1 1 d . . . . .
H5B H 0.6884 0.5311 0.5252 0.045 Uiso 1 1 calc R U . . .
C6B C 0.6254(6) 0.5043(5) 0.4278(4) 0.0325(16) Uani 1 1 d . . . . .
H6B H 0.6511 0.4472 0.4288 0.039 Uiso 1 1 calc R U . . .
C7B C 0.5649(5) 0.5353(4) 0.3673(4) 0.0266(14) Uani 1 1 d . . . . .
C8B C 0.5463(6) 0.4750(4) 0.3113(4) 0.0273(14) Uani 1 1 d . . . . .
H8B H 0.5778 0.4202 0.3197 0.033 Uiso 1 1 calc R U . . .
N9B N 0.4930(4) 0.4863(3) 0.2523(3) 0.0237(12) Uani 1 1 d . . . . .
C10B C 0.4865(6) 0.4139(4) 0.2050(4) 0.0295(15) Uani 1 1 d . . . . .
H10C H 0.5241 0.3648 0.2289 0.035 Uiso 1 1 calc R U . . .
H10D H 0.5358 0.4260 0.1626 0.035 Uiso 1 1 calc R U . . .
C11B C 0.3546(6) 0.3916(4) 0.1825(4) 0.0317(15) Uani 1 1 d . . . . .
H11C H 0.3524 0.3324 0.1668 0.038 Uiso 1 1 calc R U . . .
H11D H 0.2995 0.3969 0.2236 0.038 Uiso 1 1 calc R U . . .
C12B C 0.3067(7) 0.4462(5) 0.1245(4) 0.0377(17) Uani 1 1 d . . . . .
H12C H 0.2230 0.4264 0.1111 0.045 Uiso 1 1 calc R U . . .
H12D H 0.3604 0.4389 0.0831 0.045 Uiso 1 1 calc R U . . .
N13B N 0.2995(5) 0.5378(3) 0.1415(3) 0.0249(12) Uani 1 1 d D . . . .
H13B H 0.223(3) 0.548(5) 0.163(3) 0.04(2) Uiso 1 1 d D . . . .
C14B C 0.2994(6) 0.5868(5) 0.0754(3) 0.0315(15) Uani 1 1 d . . . . .
H14C H 0.2590 0.6416 0.0836 0.038 Uiso 1 1 calc R U . . .
H14D H 0.2506 0.5564 0.0393 0.038 Uiso 1 1 calc R U . . .
C15B C 0.4299(7) 0.6016(6) 0.0480(4) 0.0407(18) Uani 1 1 d . . . . .
H15C H 0.4761 0.5481 0.0506 0.049 Uiso 1 1 calc R U . . .
H15D H 0.4242 0.6178 -0.0022 0.049 Uiso 1 1 calc R U . . .
C16B C 0.5021(7) 0.6676(5) 0.0865(4) 0.0387(18) Uani 1 1 d . . . . .
H16C H 0.5763 0.6808 0.0585 0.046 Uiso 1 1 calc R U . . .
H16D H 0.4511 0.7191 0.0881 0.046 Uiso 1 1 calc R U . . .
N17B N 0.5429(5) 0.6484(4) 0.1586(3) 0.0300(13) Uani 1 1 d . . . . .
C18B C 0.5873(7) 0.7275(5) 0.1891(5) 0.045(2) Uani 1 1 d . . . . .
H18D H 0.6242 0.7166 0.2354 0.054 Uiso 1 1 calc R U . . .
H18E H 0.5178 0.7665 0.1940 0.054 Uiso 1 1 calc R U . . .
H18F H 0.6494 0.7523 0.1582 0.054 Uiso 1 1 calc R U . . .
C19B C 0.6508(6) 0.5916(5) 0.1554(5) 0.0425(19) Uani 1 1 d . . . . .
H19D H 0.7181 0.6194 0.1302 0.051 Uiso 1 1 calc R U . . .
H19E H 0.6276 0.5399 0.1306 0.051 Uiso 1 1 calc R U . . .
H19F H 0.6783 0.5778 0.2033 0.051 Uiso 1 1 calc R U . . .
N20B N 0.2472(4) 0.5543(3) 0.2941(3) 0.0237(11) Uani 1 1 d . . . . .
N21B N 0.2428(4) 0.4884(3) 0.3237(3) 0.0237(11) Uani 1 1 d . . . . .
N22B N 0.2389(6) 0.4238(4) 0.3511(4) 0.0416(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
NiA O1A 2.005(4) . ?
NiA N9A 2.046(5) . ?
NiA N20B 2.121(5) . ?
NiA N13A 2.128(5) . ?
NiA N17A 2.186(5) . ?
NiA N20A 2.227(5) . ?
NiB O1B 2.014(4) . ?
NiB N9B 2.053(5) . ?
NiB N20A 2.132(5) . ?
NiB N13B 2.144(5) . ?
NiB N17B 2.198(5) . ?
NiB N20B 2.199(5) . ?
O1A C2A 1.287(7) . ?
C2A C3A 1.414(9) . ?
C2A C7A 1.445(9) . ?
C3A C4A 1.362(10) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.394(11) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.386(10) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.399(9) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.451(9) . ?
C8A N9A 1.271(8) . ?
C8A H8A 0.9500 . ?
N9A C10A 1.479(9) . ?
C10A C11A 1.524(9) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.514(10) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A N13A 1.473(9) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
N13A C14A 1.476(9) . ?
N13A H13A 0.937(10) . ?
C14A C15A 1.507(9) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.525(10) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A N17A 1.498(9) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
N17A C19A 1.476(8) . ?
N17A C18A 1.486(9) . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
N20A N21A 1.184(7) . ?
N21A N22A 1.162(8) . ?
O1B C2B 1.308(8) . ?
C2B C3B 1.410(9) . ?
C2B C7B 1.419(9) . ?
C3B C4B 1.376(10) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.387(11) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.358(10) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.409(9) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.447(9) . ?
C8B N9B 1.271(8) . ?
C8B H8B 0.9500 . ?
N9B C10B 1.463(8) . ?
C10B C11B 1.530(9) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.492(10) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B N13B 1.496(9) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
N13B C14B 1.479(9) . ?
N13B H13B 0.939(10) . ?
C14B C15B 1.528(9) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.497(11) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B N17B 1.468(9) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
N17B C18B 1.466(9) . ?
N17B C19B 1.479(8) . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
N20B N21B 1.192(7) . ?
N21B N22B 1.153(8) . ?

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
O1A NiA N9A 90.8(2) . . ?
O1A NiA N20B 84.86(19) . . ?
N9A NiA N20B 166.5(2) . . ?
O1A NiA N13A 170.13(19) . . ?
N9A NiA N13A 95.9(2) . . ?
N20B NiA N13A 87.0(2) . . ?
O1A NiA N17A 92.38(19) . . ?
N9A NiA N17A 97.6(2) . . ?
N20B NiA N17A 95.4(2) . . ?
N13A NiA N17A 93.9(2) . . ?
O1A NiA N20A 87.46(19) . . ?
N9A NiA N20A 88.6(2) . . ?
N20B NiA N20A 78.45(19) . . ?
N13A NiA N20A 85.5(2) . . ?
N17A NiA N20A 173.8(2) . . ?
O1B NiB N9B 91.8(2) . . ?
O1B NiB N20A 85.16(19) . . ?
N9B NiB N20A 167.8(2) . . ?
O1B NiB N13B 170.99(18) . . ?
N9B NiB N13B 94.0(2) . . ?
N20A NiB N13B 87.7(2) . . ?
O1B NiB N17B 91.7(2) . . ?
N9B NiB N17B 97.0(2) . . ?
N20A NiB N17B 94.9(2) . . ?
N13B NiB N17B 94.4(2) . . ?
O1B NiB N20B 86.85(19) . . ?
N9B NiB N20B 89.2(2) . . ?
N20A NiB N20B 78.86(19) . . ?
N13B NiB N20B 86.4(2) . . ?
N17B NiB N20B 173.7(2) . . ?
C2A O1A NiA 129.0(4) . . ?
O1A C2A C3A 120.3(6) . . ?
O1A C2A C7A 123.1(6) . . ?
C3A C2A C7A 116.6(6) . . ?
C4A C3A C2A 122.2(7) . . ?
C4A C3A H3A 118.9 . . ?
C2A C3A H3A 118.9 . . ?
C3A C4A C5A 121.6(7) . . ?
C3A C4A H4A 119.2 . . ?
C5A C4A H4A 119.2 . . ?
C6A C5A C4A 118.1(7) . . ?
C6A C5A H5A 120.9 . . ?
C4A C5A H5A 120.9 . . ?
C5A C6A C7A 122.3(7) . . ?
C5A C6A H6A 118.9 . . ?
C7A C6A H6A 118.9 . . ?
C6A C7A C2A 119.2(6) . . ?
C6A C7A C8A 117.1(6) . . ?
C2A C7A C8A 123.7(6) . . ?
N9A C8A C7A 128.1(6) . . ?
N9A C8A H8A 116.0 . . ?
C7A C8A H8A 116.0 . . ?
C8A N9A C10A 115.6(6) . . ?
C8A N9A NiA 123.9(5) . . ?
C10A N9A NiA 119.7(4) . . ?
N9A C10A C11A 113.0(5) . . ?
N9A C10A H10A 109.0 . . ?
C11A C10A H10A 109.0 . . ?
N9A C10A H10B 109.0 . . ?
C11A C10A H10B 109.0 . . ?
H10A C10A H10B 107.8 . . ?
C12A C11A C10A 113.0(6) . . ?
C12A C11A H11A 109.0 . . ?
C10A C11A H11A 109.0 . . ?
C12A C11A H11B 109.0 . . ?
C10A C11A H11B 109.0 . . ?
H11A C11A H11B 107.8 . . ?
N13A C12A C11A 115.8(6) . . ?
N13A C12A H12A 108.3 . . ?
C11A C12A H12A 108.3 . . ?
N13A C12A H12B 108.3 . . ?
C11A C12A H12B 108.3 . . ?
H12A C12A H12B 107.4 . . ?
C12A N13A C14A 110.3(5) . . ?
C12A N13A NiA 121.4(4) . . ?
C14A N13A NiA 115.1(4) . . ?
C12A N13A H13A 107(4) . . ?
C14A N13A H13A 111(4) . . ?
NiA N13A H13A 89(4) . . ?
N13A C14A C15A 113.5(6) . . ?
N13A C14A H14A 108.9 . . ?
C15A C14A H14A 108.9 . . ?
N13A C14A H14B 108.9 . . ?
C15A C14A H14B 108.9 . . ?
H14A C14A H14B 107.7 . . ?
C14A C15A C16A 114.7(6) . . ?
C14A C15A H15A 108.6 . . ?
C16A C15A H15A 108.6 . . ?
C14A C15A H15B 108.6 . . ?
C16A C15A H15B 108.6 . . ?
H15A C15A H15B 107.6 . . ?
N17A C16A C15A 115.6(6) . . ?
N17A C16A H16A 108.4 . . ?
C15A C16A H16A 108.4 . . ?
N17A C16A H16B 108.4 . . ?
C15A C16A H16B 108.4 . . ?
H16A C16A H16B 107.4 . . ?
C19A N17A C18A 106.3(5) . . ?
C19A N17A C16A 109.5(5) . . ?
C18A N17A C16A 106.0(5) . . ?
C19A N17A NiA 110.8(4) . . ?
C18A N17A NiA 109.4(4) . . ?
C16A N17A NiA 114.4(4) . . ?
N17A C18A H18A 109.5 . . ?
N17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
N17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N17A C19A H19A 109.5 . . ?
N17A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
N17A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
N21A N20A NiB 134.2(4) . . ?
N21A N20A NiA 122.0(4) . . ?
NiB N20A NiA 100.7(2) . . ?
N22A N21A N20A 178.8(7) . . ?
C2B O1B NiB 126.5(4) . . ?
O1B C2B C3B 119.1(6) . . ?
O1B C2B C7B 124.2(6) . . ?
C3B C2B C7B 116.8(6) . . ?
C4B C3B C2B 121.6(7) . . ?
C4B C3B H3B 119.2 . . ?
C2B C3B H3B 119.2 . . ?
C3B C4B C5B 121.2(7) . . ?
C3B C4B H4B 119.4 . . ?
C5B C4B H4B 119.4 . . ?
C6B C5B C4B 118.8(7) . . ?
C6B C5B H5B 120.6 . . ?
C4B C5B H5B 120.6 . . ?
C5B C6B C7B 122.0(7) . . ?
C5B C6B H6B 119.0 . . ?
C7B C6B H6B 119.0 . . ?
C6B C7B C2B 119.7(6) . . ?
C6B C7B C8B 115.4(6) . . ?
C2B C7B C8B 124.9(6) . . ?
N9B C8B C7B 128.0(6) . . ?
N9B C8B H8B 116.0 . . ?
C7B C8B H8B 116.0 . . ?
C8B N9B C10B 116.8(6) . . ?
C8B N9B NiB 123.2(4) . . ?
C10B N9B NiB 119.6(4) . . ?
N9B C10B C11B 113.3(5) . . ?
N9B C10B H10C 108.9 . . ?
C11B C10B H10C 108.9 . . ?
N9B C10B H10D 108.9 . . ?
C11B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C12B C11B C10B 113.0(6) . . ?
C12B C11B H11C 109.0 . . ?
C10B C11B H11C 109.0 . . ?
C12B C11B H11D 109.0 . . ?
C10B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
C11B C12B N13B 115.3(6) . . ?
C11B C12B H12C 108.5 . . ?
N13B C12B H12C 108.5 . . ?
C11B C12B H12D 108.5 . . ?
N13B C12B H12D 108.5 . . ?
H12C C12B H12D 107.5 . . ?
C14B N13B C12B 109.3(5) . . ?
C14B N13B NiB 114.6(4) . . ?
C12B N13B NiB 123.2(4) . . ?
C14B N13B H13B 106(5) . . ?
C12B N13B H13B 108(5) . . ?
NiB N13B H13B 92(5) . . ?
N13B C14B C15B 112.1(6) . . ?
N13B C14B H14C 109.2 . . ?
C15B C14B H14C 109.2 . . ?
N13B C14B H14D 109.2 . . ?
C15B C14B H14D 109.2 . . ?
H14C C14B H14D 107.9 . . ?
C16B C15B C14B 115.0(6) . . ?
C16B C15B H15C 108.5 . . ?
C14B C15B H15C 108.5 . . ?
C16B C15B H15D 108.5 . . ?
C14B C15B H15D 108.5 . . ?
H15C C15B H15D 107.5 . . ?
N17B C16B C15B 117.6(6) . . ?
N17B C16B H16C 107.9 . . ?
C15B C16B H16C 107.9 . . ?
N17B C16B H16D 107.9 . . ?
C15B C16B H16D 107.9 . . ?
H16C C16B H16D 107.2 . . ?
C18B N17B C16B 106.6(6) . . ?
C18B N17B C19B 106.6(6) . . ?
C16B N17B C19B 108.7(6) . . ?
C18B N17B NiB 109.4(4) . . ?
C16B N17B NiB 115.0(4) . . ?
C19B N17B NiB 110.2(4) . . ?
N17B C18B H18D 109.5 . . ?
N17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
N17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
N17B C19B H19D 109.5 . . ?
N17B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
N17B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
N21B N20B NiA 133.5(4) . . ?
N21B N20B NiB 124.5(4) . . ?
NiA N20B NiB 102.0(2) . . ?
N22B N21B N20B 178.6(7) . . ?

_refine_diff_density_max         1.512
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.128

_shelxl_version_number           2013-4

