# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_17ma160_sb380
_database_code_depnum_ccdc_archive 'CCDC 2004181'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2021-03-30 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-03-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 N4 Ni O2, 2(C H Cl3)'
_chemical_formula_sum            'C22 H20 Cl6 N4 Ni O2'
_chemical_formula_weight         643.83
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   15.0319(3)
_cell_length_b                   11.2984(2)
_cell_length_c                   16.0579(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.022(2)
_cell_angle_gamma                90
_cell_volume                     2607.74(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7500
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.217
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.526
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.507
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11375
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.150
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_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                2712
_reflns_number_total             2948
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.917
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+7.0737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl7-C1S
 1.75 with sigma of 0.02
 C1S-Cl1 \\sim C1S-Cl2 \\sim C1S-Cl3 \\sim C1S-Cl4 \\sim C1S-Cl5 \\sim C1S-Cl6
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3) \\sim Ueq, Uanis(Cl4)
\\sim Ueq, Uanis(Cl5) \\sim Ueq, Uanis(Cl6) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(Cl7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.002
4. Others
 1*[Sof(Cl2)]+1*[Sof(Cl5)]+1*[Sof(Cl7)]=1 with esd of 0.0001
 Sof(Cl4)=1-FVAR(1)
 Sof(Cl3)=FVAR(1)
 Sof(Cl6)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8)
5.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
C1 C 0.65114(17) 0.4512(2) 0.84212(14) 0.0299(5) Uani 1 1 d . . . . .
C2 C 0.6053(2) 0.5529(2) 0.80040(16) 0.0393(6) Uani 1 1 d . . . . .
H2 H 0.6230 0.6282 0.8263 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5349(2) 0.5461(2) 0.72265(16) 0.0405(6) Uani 1 1 d . . . . .
H3 H 0.5061 0.6165 0.6953 0.049 Uiso 1 1 calc R U . . .
C4 C 0.50625(18) 0.4377(3) 0.68427(16) 0.0399(6) Uani 1 1 d . . . . .
H4 H 0.4558 0.4332 0.6323 0.048 Uiso 1 1 calc R U . . .
C5 C 0.55138(16) 0.3361(2) 0.72198(15) 0.0315(5) Uani 1 1 d . . . . .
H5 H 0.5327 0.2614 0.6954 0.038 Uiso 1 1 calc R U . . .
C6 C 0.62429(15) 0.34286(19) 0.79905(13) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.68772(17) 0.1441(2) 0.78010(14) 0.0280(5) Uani 1 1 d . . . . .
H7 H 0.6536 0.1306 0.7210 0.034 Uiso 1 1 calc R U . . .
C8 C 0.75383(17) 0.0746(2) 0.83022(15) 0.0302(5) Uani 1 1 d . . . . .
H8 H 0.7755 0.0020 0.8134 0.036 Uiso 1 1 calc R U . . .
C9 C 0.73810(14) 0.23019(18) 0.91300(13) 0.0221(4) Uani 1 1 d . . . . .
C10 C 0.86104(17) 0.0800(2) 0.98168(16) 0.0359(5) Uani 1 1 d . . . . .
H10A H 0.8924 0.1445 1.0198 0.054 Uiso 1 1 calc R U . . .
H10B H 0.9056 0.0399 0.9573 0.054 Uiso 1 1 calc R U . . .
H10C H 0.8362 0.0232 1.0154 0.054 Uiso 1 1 calc R U . . .
N1 N 0.67846(12) 0.24011(16) 0.83100(11) 0.0225(4) Uani 1 1 d . . . . .
N2 N 0.78490(13) 0.12796(16) 0.91109(12) 0.0254(4) Uani 1 1 d . . . . .
Ni1 Ni 0.7500 0.34071(3) 1.0000 0.02330(13) Uani 1 2 d S T P . .
O1 O 0.71743(14) 0.46194(14) 0.91701(10) 0.0381(4) Uani 1 1 d . . . . .
C1S C 0.3751(3) 0.3551(3) 0.9374(2) 0.0796(14) Uani 1 1 d D . . . .
Cl1 Cl 0.38723(14) 0.37707(18) 0.84061(10) 0.0719(7) Uani 0.635(4) 1 d D U P A
1
Cl2 Cl 0.3253(2) 0.2361(2) 0.9662(3) 0.1107(13) Uani 0.470(3) 1 d D U P A 1
Cl3 Cl 0.50242(18) 0.3445(2) 1.01307(14) 0.0901(10) Uani 0.501(3) 1 d D U P A 1
Cl4 Cl 0.42444(17) 0.26533(19) 1.01216(12) 0.0733(8) Uani 0.499(3) 1 d D U P A
2
Cl5 Cl 0.3035(3) 0.2785(4) 0.8374(2) 0.120(2) Uani 0.364(3) 1 d D U P A 2
Cl6 Cl 0.4432(3) 0.4465(5) 0.8962(4) 0.117(2) Uani 0.365(4) 1 d D U P A 2
Cl7 Cl 0.2735(6) 0.2208(7) 0.8835(7) 0.088(2) Uani 0.166(3) 1 d D U P A 3
H1S H 0.341(3) 0.405(4) 0.953(3) 0.073(12) 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
C1 C2 1.405(3) . ?
C1 C6 1.406(3) . ?
C1 O1 1.324(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 N1 1.425(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.336(3) . ?
C7 N1 1.389(3) . ?
C8 H8 0.9500 . ?
C8 N2 1.383(3) . ?
C9 N1 1.363(3) . ?
C9 N2 1.357(3) . ?
C9 Ni1 1.843(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 N2 1.459(3) . ?
Ni1 C9 1.843(2) 2_657 ?
Ni1 O1 1.8735(16) . ?
Ni1 O1 1.8735(16) 2_657 ?
C1S Cl1 1.636(3) . ?
C1S Cl2 1.669(4) . ?
C1S Cl3 1.948(4) . ?
C1S Cl4 1.581(3) . ?
C1S Cl5 1.863(5) . ?
C1S Cl6 1.717(4) . ?
C1S Cl7 2.147(8) . ?
C1S H1S 0.85(4) . ?

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 C1 C6 116.6(2) . . ?
O1 C1 C2 119.5(2) . . ?
O1 C1 C6 123.9(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 N1 118.75(19) . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 N1 119.5(2) . . ?
C8 C7 H7 126.6 . . ?
C8 C7 N1 106.83(19) . . ?
N1 C7 H7 126.6 . . ?
C7 C8 H8 126.4 . . ?
C7 C8 N2 107.3(2) . . ?
N2 C8 H8 126.4 . . ?
N1 C9 Ni1 124.53(15) . . ?
N2 C9 N1 104.29(17) . . ?
N2 C9 Ni1 131.13(15) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
C7 N1 C6 124.71(18) . . ?
C9 N1 C6 124.04(18) . . ?
C9 N1 C7 110.68(18) . . ?
C8 N2 C10 122.7(2) . . ?
C9 N2 C8 110.93(18) . . ?
C9 N2 C10 126.33(19) . . ?
C9 Ni1 C9 94.70(12) . 2_657 ?
C9 Ni1 O1 90.51(8) 2_657 2_657 ?
C9 Ni1 O1 169.03(9) 2_657 . ?
C9 Ni1 O1 90.51(8) . . ?
C9 Ni1 O1 169.03(9) . 2_657 ?
O1 Ni1 O1 86.04(10) . 2_657 ?
C1 O1 Ni1 123.36(15) . . ?
Cl1 C1S Cl2 124.7(3) . . ?
Cl1 C1S Cl3 103.8(2) . . ?
Cl1 C1S H1S 115(3) . . ?
Cl2 C1S Cl3 102.5(2) . . ?
Cl2 C1S H1S 95(3) . . ?
Cl3 C1S H1S 115(3) . . ?
Cl4 C1S Cl5 112.4(3) . . ?
Cl4 C1S Cl6 118.6(3) . . ?
Cl4 C1S H1S 113(3) . . ?
Cl5 C1S H1S 108(3) . . ?
Cl6 C1S Cl5 102.0(4) . . ?
Cl6 C1S H1S 101(3) . . ?
Cl7 C1S H1S 99(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.3(4) . . . . ?
C1 C6 N1 C7 -151.2(2) . . . . ?
C1 C6 N1 C9 19.3(3) . . . . ?
C2 C1 C6 C5 -4.4(3) . . . . ?
C2 C1 C6 N1 169.9(2) . . . . ?
C2 C1 O1 Ni1 154.4(2) . . . . ?
C2 C3 C4 C5 -3.1(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 2.7(4) . . . . ?
C4 C5 C6 N1 -171.5(2) . . . . ?
C5 C6 N1 C7 23.2(3) . . . . ?
C5 C6 N1 C9 -166.3(2) . . . . ?
C6 C1 C2 C3 2.4(4) . . . . ?
C6 C1 O1 Ni1 -27.3(3) . . . . ?
C7 C8 N2 C9 0.8(3) . . . . ?
C7 C8 N2 C10 -176.7(2) . . . . ?
C8 C7 N1 C6 171.1(2) . . . . ?
C8 C7 N1 C9 -0.5(3) . . . . ?
C9 Ni1 O1 C1 40.4(2) . . . . ?
C9 Ni1 O1 C1 -78.0(5) 2_657 . . . ?
N1 C7 C8 N2 -0.2(3) . . . . ?
N1 C9 N2 C8 -1.1(2) . . . . ?
N1 C9 N2 C10 176.3(2) . . . . ?
N1 C9 Ni1 C9 140.3(2) . . . 2_657 ?
N1 C9 Ni1 O1 -101.6(4) . . . 2_657 ?
N1 C9 Ni1 O1 -30.04(19) . . . . ?
N2 C9 N1 C6 -170.72(19) . . . . ?
N2 C9 N1 C7 0.9(2) . . . . ?
N2 C9 Ni1 C9 -42.98(17) . . . 2_657 ?
N2 C9 Ni1 O1 75.1(5) . . . 2_657 ?
N2 C9 Ni1 O1 146.7(2) . . . . ?
Ni1 C9 N1 C6 6.7(3) . . . . ?
Ni1 C9 N1 C7 178.38(16) . . . . ?
Ni1 C9 N2 C8 -178.26(17) . . . . ?
Ni1 C9 N2 C10 -0.9(3) . . . . ?
O1 C1 C2 C3 -179.3(2) . . . . ?
O1 C1 C6 C5 177.4(2) . . . . ?
O1 C1 C6 N1 -8.4(4) . . . . ?
O1 Ni1 O1 C1 -150.0(2) 2_657 . . . ?

_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_19ma071c2_sb673
_database_code_depnum_ccdc_archive 'CCDC 2050372'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-12-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H64 N6 Ni O2'
_chemical_formula_sum            'C42 H64 N6 Ni O2'
_chemical_formula_weight         743.70
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.79520(10)
_cell_length_b                   18.38130(10)
_cell_length_c                   18.97510(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.0670(10)
_cell_angle_gamma                90
_cell_volume                     4217.96(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25406
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.5150
_cell_measurement_theta_min      3.6830
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.79555
_exptl_absorpt_correction_T_min  0.78641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.331
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.259
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33030
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.056
_diffrn_reflns_theta_min         4.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -90.00  -4.00   0.50    0.08    --  -18.75 -48.00  41.00  172
  2  ω    -23.00  51.00   0.50    0.08    --   47.95 -48.00  41.00  148
  3  ω     35.00 120.00   0.50    0.08    --   47.95  48.00-169.00  170
  4  ω     94.00 174.00   0.50    0.34    --  107.11  48.00-169.00  160
  5  ω    -66.00  -9.00   0.50    0.08    --  -18.75 125.00 -30.00  114
  6  ω    -31.00  54.00   0.50    0.08    --  -18.75  48.00-169.00  170
  7  ω    -26.00  23.00   0.50    0.08    --   47.95 -19.00 -90.00   98
  8  ω     91.00 174.00   0.50    0.34    --  107.11  61.00  90.00  166
  9  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00  30.00   66
 10  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00-120.00   66
 11  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00 120.00   66
 12  ω     95.00 174.00   0.50    0.34    --  107.11  45.00 120.00  158
 13  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00   0.00   66
 14  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00 -90.00   66
 15  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00  60.00   66
 16  ω     92.00 174.00   0.50    0.34    --  107.11 125.00  30.00  164
 17  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00 -30.00   66
 18  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00  90.00   66
 19  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00-180.00   66
 20  ω     95.00 174.00   0.50    0.34    --  107.11  30.00-180.00  158
 21  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00 -60.00   66
 22  ω     35.00  68.00   0.50    0.34    --  107.11 -61.00-150.00   66
 23  ω     26.00 120.00   0.50    0.08    --   47.95  77.00-120.00  188
 24  ω     -4.00  82.00   0.50    0.08    --   47.95 -99.00-150.00  172
 25  ω     33.00 120.00   0.50    0.08    --   47.95  57.00 -30.00  174
 26  ω     26.00 120.00   0.50    0.08    --   47.95  77.00 -30.00  188
 27  ω     26.00 120.00   0.50    0.08    --   47.95  77.00  90.00  188
 28  ω     33.00 120.00   0.50    0.08    --   47.95  57.00  60.00  174
 29  ω     94.00 174.00   0.50    0.34    --  107.11  15.00   0.00  160
 30  ω     95.00 174.00   0.50    0.34    --  107.11  30.00-120.00  158
 31  ω     35.00 109.00   0.50    0.34    --  107.11 -94.00   0.00  148
 32  ω     95.00 174.00   0.50    0.34    --  107.11  45.00 -60.00  158
 33  ω     35.00 117.00   0.50    0.34    --  107.11-125.00-150.00  164
 34  ω     94.00 174.00   0.50    0.34    --  107.11  15.00  60.00  160
 35  ω     95.00 145.00   0.50    0.34    --  107.11  45.00   0.00  100
 36  ω     95.00 174.00   0.50    0.34    --  107.11  30.00 -90.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1209425000
_diffrn_orient_matrix_UB_12      0.0218264000
_diffrn_orient_matrix_UB_13      0.0123954000
_diffrn_orient_matrix_UB_21      -0.0015500000
_diffrn_orient_matrix_UB_22      -0.0442076000
_diffrn_orient_matrix_UB_23      -0.0693153000
_diffrn_orient_matrix_UB_31      -0.0399174000
_diffrn_orient_matrix_UB_32      0.0677854000
_diffrn_orient_matrix_UB_33      -0.0491950000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4256
_reflns_number_total             4421
_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       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+3.7086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
 C14-C17 \\sim C14-C17A
 with sigma of 0.02
 C14-C16 \\sim C14-C16A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C15 \\sim C17 \\sim C16 \\sim C15A \\sim C16A \\sim C17A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C14, C15, C17, C16, C15A, C16A, C17A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16A)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9)
6.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C21(H21A,H21B,H21C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C16(H16A,
 H16B,H16C), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F), C17A(H17D,H17E,H17F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.750000 0.57213(2) 0.500000 0.03065(12) Uani 1 2 d S T P . .
O1 O 0.66005(9) 0.64544(5) 0.43914(5) 0.0353(2) Uani 1 1 d . . . . .
N1 N 0.51580(11) 0.41863(6) 0.42522(7) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.64532(13) 0.50310(7) 0.45606(8) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.49583(11) 0.45834(7) 0.36409(7) 0.0370(3) Uani 1 1 d . . . . .
C2 C 0.60320(13) 0.44272(8) 0.48259(8) 0.0352(3) Uani 1 1 d . . . . .
N3 N 0.57502(11) 0.50916(6) 0.38445(6) 0.0334(3) Uani 1 1 d . . . . .
C3 C 0.44244(15) 0.35720(8) 0.42260(10) 0.0433(4) Uani 1 1 d . . . . .
H3A H 0.371414 0.366568 0.386268 0.065 Uiso 1 1 calc GR . . . .
H3B H 0.434235 0.350684 0.470717 0.065 Uiso 1 1 calc GR . . . .
H3C H 0.473409 0.313931 0.409099 0.065 Uiso 1 1 calc GR . . . .
C4 C 0.57046(13) 0.56839(8) 0.33486(8) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.61066(12) 0.63646(8) 0.36660(8) 0.0326(3) Uani 1 1 d . . . . .
C6 C 0.59161(13) 0.69628(8) 0.31616(8) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.53870(14) 0.68311(9) 0.24031(8) 0.0406(3) Uani 1 1 d . . . . .
H7 H 0.527296 0.722455 0.207845 0.049 Uiso 1 1 calc R . . . .
C8 C 0.50177(15) 0.61486(9) 0.20991(8) 0.0438(4) Uani 1 1 d . . . . .
C9 C 0.51872(15) 0.55727(9) 0.25918(9) 0.0423(4) Uani 1 1 d . . . . .
H9 H 0.495316 0.510846 0.241484 0.051 Uiso 1 1 calc R . . . .
C10 C 0.62526(14) 0.77360(8) 0.34596(8) 0.0378(3) Uani 1 1 d . . . . .
C11 C 0.60364(18) 0.82992(9) 0.28296(10) 0.0528(5) Uani 1 1 d . . . . .
H11A H 0.645024 0.817078 0.250734 0.079 Uiso 1 1 calc GR . . . .
H11B H 0.626194 0.877178 0.303963 0.079 Uiso 1 1 calc GR . . . .
H11C H 0.526189 0.830683 0.254823 0.079 Uiso 1 1 calc GR . . . .
C12 C 0.55872(16) 0.79630(9) 0.39671(10) 0.0488(4) Uani 1 1 d . . . . .
H12A H 0.481402 0.797370 0.368264 0.073 Uiso 1 1 calc GR . . . .
H12B H 0.581948 0.843774 0.416846 0.073 Uiso 1 1 calc GR . . . .
H12C H 0.571253 0.761935 0.436720 0.073 Uiso 1 1 calc GR . . . .
C13 C 0.74914(14) 0.77739(9) 0.38978(9) 0.0435(4) Uani 1 1 d . . . . .
H13A H 0.766497 0.743477 0.430449 0.065 Uiso 1 1 calc GR . . . .
H13B H 0.767856 0.825725 0.408909 0.065 Uiso 1 1 calc GR . . . .
H13C H 0.790689 0.765352 0.357427 0.065 Uiso 1 1 calc GR . . . .
C18 C 0.63073(15) 0.41388(9) 0.56035(9) 0.0434(4) Uani 1 1 d . . . . .
H18A H 0.561868 0.406907 0.570506 0.052 Uiso 1 1 calc R . . . .
H18B H 0.672052 0.451142 0.594286 0.052 Uiso 1 1 calc R . . . .
C19 C 0.6962(2) 0.34339(11) 0.57932(12) 0.0615(5) Uani 1 1 d . . . . .
H19A H 0.766374 0.349361 0.570763 0.074 Uiso 1 1 calc R . . . .
H19B H 0.655576 0.304881 0.546877 0.074 Uiso 1 1 calc R . . . .
C20 C 0.7171(2) 0.32176(14) 0.66104(14) 0.0752(7) Uani 1 1 d . . . . .
H20A H 0.646649 0.313404 0.668557 0.090 Uiso 1 1 calc R . . . .
H20B H 0.758195 0.276447 0.671085 0.090 Uiso 1 1 calc R . . . .
C21 C 0.7809(2) 0.3790(2) 0.71604(15) 0.0991(10) Uani 1 1 d . . . . .
H21A H 0.738016 0.422912 0.709082 0.149 Uiso 1 1 calc GR . . . .
H21B H 0.849686 0.388807 0.707817 0.149 Uiso 1 1 calc GR . . . .
H21C H 0.795237 0.361561 0.766000 0.149 Uiso 1 1 calc GR . . . .
C14 C 0.4424(2) 0.60132(12) 0.12657(9) 0.0617(6) Uani 1 1 d D U . . .
C15 C 0.4326(3) 0.66937(15) 0.07942(11) 0.0662(8) Uani 0.862(4) 1 d D U . A 1
H15A H 0.391025 0.705567 0.095300 0.099 Uiso 0.862(4) 1 calc GR . . A 1
H15B H 0.395540 0.657710 0.027971 0.099 Uiso 0.862(4) 1 calc GR . . A 1
H15C H 0.505139 0.687840 0.085201 0.099 Uiso 0.862(4) 1 calc GR . . A 1
C17 C 0.3280(3) 0.5707(3) 0.11658(17) 0.1024(16) Uani 0.862(4) 1 d D U . A 1
H17A H 0.334890 0.527321 0.145942 0.154 Uiso 0.862(4) 1 calc GR . . A 1
H17B H 0.291683 0.559329 0.064968 0.154 Uiso 0.862(4) 1 calc GR . . A 1
H17C H 0.285338 0.606089 0.132545 0.154 Uiso 0.862(4) 1 calc GR . . A 1
C16 C 0.5122(4) 0.54605(17) 0.09932(15) 0.1016(14) Uani 0.862(4) 1 d D U . A 1
H16A H 0.585665 0.564795 0.109263 0.152 Uiso 0.862(4) 1 calc GR . . A 1
H16B H 0.478687 0.538362 0.046690 0.152 Uiso 0.862(4) 1 calc GR . . A 1
H16C H 0.515575 0.500745 0.125136 0.152 Uiso 0.862(4) 1 calc GR . . A 1
C15A C 0.3458(16) 0.6607(11) 0.0983(10) 0.088(5) Uani 0.138(4) 1 d D U . A 2
H15D H 0.285259 0.647483 0.115046 0.132 Uiso 0.138(4) 1 calc GR . . A 2
H15E H 0.320783 0.662678 0.044792 0.132 Uiso 0.138(4) 1 calc GR . . A 2
H15F H 0.373565 0.707577 0.118082 0.132 Uiso 0.138(4) 1 calc GR . . A 2
C16A C 0.5113(17) 0.6212(11) 0.0796(9) 0.081(4) Uani 0.138(4) 1 d D U . A 2
H16D H 0.540936 0.669181 0.092596 0.121 Uiso 0.138(4) 1 calc GR . . A 2
H16E H 0.466438 0.620250 0.027970 0.121 Uiso 0.138(4) 1 calc GR . . A 2
H16F H 0.570772 0.587000 0.087922 0.121 Uiso 0.138(4) 1 calc GR . . A 2
C17A C 0.3873(19) 0.5294(9) 0.1033(8) 0.068(4) Uani 0.138(4) 1 d D U . A 2
H17D H 0.441727 0.491472 0.116481 0.102 Uiso 0.138(4) 1 calc GR . . A 2
H17E H 0.350765 0.529265 0.050350 0.102 Uiso 0.138(4) 1 calc GR . . A 2
H17F H 0.333880 0.521450 0.128194 0.102 Uiso 0.138(4) 1 calc GR . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8989(10) 2_656 ?
Ni1 O1 1.8989(10) . ?
Ni1 C1 1.8356(15) . ?
Ni1 C1 1.8357(15) 2_656 ?
O1 C5 1.3241(16) . ?
N1 N2 1.3229(18) . ?
N1 C2 1.355(2) . ?
N1 C3 1.4587(19) . ?
C1 C2 1.398(2) . ?
C1 N3 1.3672(18) . ?
N2 N3 1.3390(17) . ?
C2 C18 1.497(2) . ?
N3 C4 1.4277(18) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.411(2) . ?
C4 C9 1.386(2) . ?
C5 C6 1.4256(19) . ?
C6 C7 1.397(2) . ?
C6 C10 1.538(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(2) . ?
C8 C9 1.382(2) . ?
C8 C14 1.535(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.537(2) . ?
C10 C12 1.537(2) . ?
C10 C13 1.532(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.521(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.537(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.519(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C14 C15 1.519(3) . ?
C14 C17 1.521(4) . ?
C14 C16 1.549(4) . ?
C14 C15A 1.605(15) . ?
C14 C16A 1.489(14) . ?
C14 C17A 1.495(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 0.9600 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
C17A H17D 0.9600 . ?
C17A H17E 0.9600 . ?
C17A H17F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 89.58(6) 2_656 . ?
C1 Ni1 O1 90.40(5) . . ?
C1 Ni1 O1 90.40(5) 2_656 2_656 ?
C1 Ni1 O1 166.94(6) . 2_656 ?
C1 Ni1 O1 166.94(6) 2_656 . ?
C1 Ni1 C1 92.54(9) . 2_656 ?
C5 O1 Ni1 122.16(9) . . ?
N2 N1 C2 113.35(12) . . ?
N2 N1 C3 117.35(13) . . ?
C2 N1 C3 129.29(13) . . ?
C2 C1 Ni1 134.06(11) . . ?
N3 C1 Ni1 122.72(10) . . ?
N3 C1 C2 102.52(13) . . ?
N1 N2 N3 102.75(11) . . ?
N1 C2 C1 106.52(13) . . ?
N1 C2 C18 122.86(14) . . ?
C1 C2 C18 129.92(14) . . ?
C1 N3 C4 126.10(12) . . ?
N2 N3 C1 114.84(12) . . ?
N2 N3 C4 118.53(12) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N3 117.65(12) . . ?
C9 C4 N3 118.25(13) . . ?
C9 C4 C5 123.87(13) . . ?
O1 C5 C4 122.56(12) . . ?
O1 C5 C6 121.37(13) . . ?
C4 C5 C6 116.03(12) . . ?
C5 C6 C10 120.00(12) . . ?
C7 C6 C5 118.49(13) . . ?
C7 C6 C10 121.47(13) . . ?
C6 C7 H7 117.8 . . ?
C6 C7 C8 124.45(14) . . ?
C8 C7 H7 117.8 . . ?
C7 C8 C14 123.91(15) . . ?
C9 C8 C7 116.84(14) . . ?
C9 C8 C14 119.24(15) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.28(14) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C6 112.26(13) . . ?
C11 C10 C12 107.99(14) . . ?
C12 C10 C6 109.59(13) . . ?
C13 C10 C6 110.93(12) . . ?
C13 C10 C11 106.44(14) . . ?
C13 C10 C12 109.53(13) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C18 H18A 107.8 . . ?
C2 C18 H18B 107.8 . . ?
C2 C18 C19 117.97(15) . . ?
H18A C18 H18B 107.2 . . ?
C19 C18 H18A 107.8 . . ?
C19 C18 H18B 107.8 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
C18 C19 C20 111.12(18) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 113.0(2) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 C14 C16 107.8(2) . . ?
C8 C14 C15A 107.6(7) . . ?
C15 C14 C8 113.03(16) . . ?
C15 C14 C17 109.9(2) . . ?
C15 C14 C16 106.8(2) . . ?
C17 C14 C8 108.70(19) . . ?
C17 C14 C16 110.6(3) . . ?
C16A C14 C8 112.7(7) . . ?
C16A C14 C15A 100.0(13) . . ?
C16A C14 C17A 110.8(10) . . ?
C17A C14 C8 118.3(6) . . ?
C17A C14 C15A 105.4(12) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C15A H15D 109.5 . . ?
C14 C15A H15E 109.5 . . ?
C14 C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C14 C16A H16D 109.5 . . ?
C14 C16A H16E 109.5 . . ?
C14 C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C14 C17A H17D 109.5 . . ?
C14 C17A H17E 109.5 . . ?
C14 C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?

_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_19MA083_SB653
_database_code_depnum_ccdc_archive 'CCDC 2050371'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-12-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H40 N6 Ni O2'
_chemical_formula_sum            'C30 H40 N6 Ni O2'
_chemical_formula_weight         575.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         c3h40n6Ni1O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.0724(2)
_cell_length_b                   10.2682(2)
_cell_length_c                   24.5315(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.0570(10)
_cell_angle_gamma                90
_cell_volume                     2973.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6107
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      73.7140
_cell_measurement_theta_min      3.6760
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14725
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.037
_diffrn_reflns_theta_min         3.685
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00 -90.00   98
  2  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00-150.00   98
  3  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00-120.00   98
  4  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00 -60.00   98
  5  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00  30.00   98
  6  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00  90.00   98
  7  ω    -26.00  23.00   0.50    1.03    --   47.95 -19.00 150.00   98
  8  ω     35.00 102.00   0.50    4.13    --  107.11 -77.00  30.00  134
  9  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00 -60.00   66
 10  ω     35.00 110.00   0.50    4.13    --  107.11-102.00-149.00  150
 11  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00 -30.00   66
 12  ω     35.00 102.00   0.50    4.13    --  107.11 -77.00 -90.00  134
 13  ω     35.00 102.00   0.50    4.13    --  107.11 -77.00-120.00  134
 14  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00-150.00   66
 15  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00-120.00   66
 16  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00-180.00   66
 17  ω      5.00  83.00   0.50    1.03    --   47.95-102.00-149.00  156
 18  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00   0.00   66
 19  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00  30.00   66
 20  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00  90.00   66
 21  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00 120.00   66
 22  ω     35.00  68.00   0.50    4.13    --  107.11 -61.00  60.00   66
 23  ω     95.00 174.00   0.50    4.13    --  107.11  45.00 120.00  158
 24  ω    104.00 174.00   0.50    4.13    --  107.11 102.00 -46.00  140
 25  ω     92.00 174.00   0.50    4.13    --  107.11 125.00 120.00  164
 26  ω     95.00 174.00   0.50    4.13    --  107.11  30.00-120.00  158
 27  ω     26.00 120.00   0.50    1.03    --   47.95  77.00-180.00  188
 28  ω    -53.00  18.00   0.50    1.03    --  -18.75 102.00 -46.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0792916000
_diffrn_orient_matrix_UB_12      0.0199969000
_diffrn_orient_matrix_UB_13      0.0573153000
_diffrn_orient_matrix_UB_21      0.0198148000
_diffrn_orient_matrix_UB_22      0.1422471000
_diffrn_orient_matrix_UB_23      -0.0154998000
_diffrn_orient_matrix_UB_31      -0.1017349000
_diffrn_orient_matrix_UB_32      0.0432962000
_diffrn_orient_matrix_UB_33      0.0244521000
_diffrn_oxdiff_digest_frames     
;
0109f7fa4619d9ba62b73721f59ed27b910203770e7
;
_diffrn_oxdiff_digest_hkl        
;
01c4b3aded1ea84a1cdaa41015447d90639a5e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2695
_reflns_number_total             3073
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.026
_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)+(0.0781P)²+1.7383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C7(H7A,H7B,H7C), C18(H18A,H18B,H18C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.5000 0.33536(4) 0.7500 0.03458(16) Uani 1 2 d S T P . .
O1 O 0.54461(13) 0.20038(13) 0.70703(6) 0.0416(3) Uani 1 1 d . . . . .
N9 N 0.58387(13) 0.43627(16) 0.65945(7) 0.0371(3) Uani 1 1 d . . . . .
N11 N 0.67338(13) 0.60744(17) 0.68215(7) 0.0410(4) Uani 1 1 d . . . . .
N10 N 0.64544(14) 0.52547(17) 0.63958(7) 0.0427(4) Uani 1 1 d . . . . .
C12 C 0.63240(16) 0.57205(19) 0.72741(8) 0.0390(4) Uani 1 1 d . . . . .
C13 C 0.57073(15) 0.45796(18) 0.71292(8) 0.0365(4) Uani 1 1 d . . . . .
C1 C 0.52131(16) 0.2130(2) 0.65235(8) 0.0383(4) Uani 1 1 d . . . . .
C6 C 0.53822(16) 0.32923(19) 0.62488(8) 0.0388(4) Uani 1 1 d . . . . .
C15 C 0.65354(18) 0.65007(19) 0.78036(9) 0.0432(5) Uani 1 1 d . . . . .
H15A H 0.5831 0.6910 0.7842 0.052 Uiso 1 1 calc R . . . .
H15B H 0.7071 0.7189 0.7774 0.052 Uiso 1 1 calc R . . . .
C16 C 0.69944(17) 0.5709(2) 0.83291(9) 0.0427(4) Uani 1 1 d . . . . .
H16A H 0.6573 0.4901 0.8315 0.051 Uiso 1 1 calc R . . . .
H16B H 0.7782 0.5492 0.8342 0.051 Uiso 1 1 calc R . . . .
C2 C 0.47654(18) 0.1066(2) 0.61836(9) 0.0444(5) Uani 1 1 d . . . . .
C5 C 0.5128(2) 0.3416(2) 0.56736(9) 0.0480(5) Uani 1 1 d . . . . .
H5 H 0.5266 0.4199 0.5509 0.058 Uiso 1 1 calc R . . . .
C14 C 0.7423(2) 0.7205(2) 0.67496(10) 0.0520(5) Uani 1 1 d . . . . .
H14A H 0.7635 0.7154 0.6394 0.078 Uiso 1 1 calc GR . . . .
H14B H 0.8092 0.7218 0.7040 0.078 Uiso 1 1 calc GR . . . .
H14C H 0.6995 0.7986 0.6767 0.078 Uiso 1 1 calc GR . . . .
C3 C 0.4499(2) 0.1214(2) 0.56104(10) 0.0535(5) Uani 1 1 d . . . . .
H3 H 0.4191 0.0508 0.5393 0.064 Uiso 1 1 calc R . . . .
C4 C 0.4670(2) 0.2378(2) 0.53436(9) 0.0557(6) Uani 1 1 d . . . . .
C17 C 0.6904(2) 0.6455(2) 0.88549(10) 0.0522(5) Uani 1 1 d . . . . .
H17A H 0.7308 0.7274 0.8862 0.063 Uiso 1 1 calc R . . . .
H17B H 0.6114 0.6654 0.8843 0.063 Uiso 1 1 calc R . . . .
C7 C 0.4567(2) -0.0197(2) 0.64609(11) 0.0552(6) Uani 1 1 d . . . . .
H7A H 0.5282 -0.0596 0.6618 0.083 Uiso 1 1 calc GR . . . .
H7B H 0.4129 -0.0772 0.6190 0.083 Uiso 1 1 calc GR . . . .
H7C H 0.4163 -0.0028 0.6752 0.083 Uiso 1 1 calc GR . . . .
C18 C 0.7380(2) 0.5707(3) 0.93859(11) 0.0683(7) Uani 1 1 d . . . . .
H18A H 0.7002 0.4882 0.9377 0.102 Uiso 1 1 calc GR . . . .
H18B H 0.7263 0.6198 0.9702 0.102 Uiso 1 1 calc GR . . . .
H18C H 0.8177 0.5567 0.9415 0.102 Uiso 1 1 calc GR . . . .
C8 C 0.4348(4) 0.2510(3) 0.47175(11) 0.0874(11) Uani 1 1 d . . . . .
H8A H 0.3601 0.2164 0.4586 0.131 Uiso 1 1 calc GR . . . .
H8B H 0.4879 0.2036 0.4551 0.131 Uiso 1 1 calc GR . . . .
H8C H 0.4360 0.3412 0.4617 0.131 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8866(14) 2_656 ?
Ni1 O1 1.8866(14) . ?
Ni1 C13 1.8616(19) . ?
Ni1 C13 1.8616(19) 2_656 ?
O1 C1 1.318(2) . ?
N9 N10 1.334(2) . ?
N9 C13 1.372(2) . ?
N9 C6 1.427(2) . ?
N11 N10 1.329(2) . ?
N11 C12 1.356(3) . ?
N11 C14 1.460(3) . ?
C12 C13 1.394(3) . ?
C12 C15 1.502(3) . ?
C1 C6 1.407(3) . ?
C1 C2 1.411(3) . ?
C6 C5 1.386(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.527(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.524(3) . ?
C2 C3 1.384(3) . ?
C2 C7 1.507(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.399(4) . ?
C4 C8 1.510(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.518(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 85.44(9) 2_656 . ?
C13 Ni1 O1 90.58(7) . . ?
C13 Ni1 O1 169.54(7) . 2_656 ?
C13 Ni1 O1 90.59(7) 2_656 2_656 ?
C13 Ni1 O1 169.54(7) 2_656 . ?
C13 Ni1 C13 94.90(12) . 2_656 ?
C1 O1 Ni1 118.13(12) . . ?
N10 N9 C13 114.98(16) . . ?
N10 N9 C6 119.16(16) . . ?
C13 N9 C6 125.86(16) . . ?
N10 N11 C12 113.43(16) . . ?
N10 N11 C14 117.78(17) . . ?
C12 N11 C14 128.79(18) . . ?
N11 N10 N9 102.54(15) . . ?
N11 C12 C13 106.45(17) . . ?
N11 C12 C15 122.68(18) . . ?
C13 C12 C15 130.86(18) . . ?
N9 C13 Ni1 120.92(14) . . ?
N9 C13 C12 102.59(16) . . ?
C12 C13 Ni1 135.96(15) . . ?
O1 C1 C6 123.31(18) . . ?
O1 C1 C2 119.97(18) . . ?
C6 C1 C2 116.72(18) . . ?
C1 C6 N9 116.48(17) . . ?
C5 C6 N9 120.69(18) . . ?
C5 C6 C1 122.83(19) . . ?
C12 C15 H15A 108.7 . . ?
C12 C15 H15B 108.7 . . ?
C12 C15 C16 114.34(17) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 C15 111.67(18) . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C1 C2 C7 118.47(19) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 121.8(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
N11 C14 H14A 109.5 . . ?
N11 C14 H14B 109.5 . . ?
N11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.9(2) . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 117.7(2) . . ?
C5 C4 C8 120.9(2) . . ?
C3 C4 C8 121.4(2) . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 113.0(2) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ni1 O1 C1 C6 44.3(2) . . . . ?
Ni1 O1 C1 C2 -135.43(16) . . . . ?
O1 Ni1 O1 C1 137.95(17) 2_656 . . . ?
O1 Ni1 C13 N9 94.8(4) 2_656 . . . ?
O1 Ni1 C13 N9 27.32(15) . . . . ?
O1 Ni1 C13 C12 -142.7(2) . . . . ?
O1 Ni1 C13 C12 -75.2(5) 2_656 . . . ?
O1 C1 C6 N9 0.5(3) . . . . ?
O1 C1 C6 C5 -179.6(2) . . . . ?
O1 C1 C2 C3 178.5(2) . . . . ?
O1 C1 C2 C7 -0.1(3) . . . . ?
N9 C6 C5 C4 -179.0(2) . . . . ?
N11 C12 C13 Ni1 172.28(16) . . . . ?
N11 C12 C13 N9 1.0(2) . . . . ?
N11 C12 C15 C16 -128.9(2) . . . . ?
N10 N9 C13 Ni1 -173.77(13) . . . . ?
N10 N9 C13 C12 -0.9(2) . . . . ?
N10 N9 C6 C1 151.67(18) . . . . ?
N10 N9 C6 C5 -28.2(3) . . . . ?
N10 N11 C12 C13 -1.0(2) . . . . ?
N10 N11 C12 C15 179.92(18) . . . . ?
C12 N11 N10 N9 0.4(2) . . . . ?
C12 C15 C16 C17 -165.27(18) . . . . ?
C13 Ni1 O1 C1 -51.74(15) . . . . ?
C13 Ni1 O1 C1 70.0(4) 2_656 . . . ?
C13 Ni1 C13 N9 -143.77(18) 2_656 . . . ?
C13 Ni1 C13 C12 46.21(18) 2_656 . . . ?
C13 N9 N10 N11 0.3(2) . . . . ?
C13 N9 C6 C1 -28.3(3) . . . . ?
C13 N9 C6 C5 151.8(2) . . . . ?
C13 C12 C15 C16 52.3(3) . . . . ?
C1 C6 C5 C4 1.1(3) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C6 N9 N10 N11 -179.69(16) . . . . ?
C6 N9 C13 Ni1 6.2(3) . . . . ?
C6 N9 C13 C12 179.12(17) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C6 C1 C2 C7 -179.78(19) . . . . ?
C6 C5 C4 C3 -1.1(4) . . . . ?
C6 C5 C4 C8 177.7(3) . . . . ?
C15 C12 C13 Ni1 -8.7(3) . . . . ?
C15 C12 C13 N9 -179.97(19) . . . . ?
C15 C16 C17 C18 -178.6(2) . . . . ?
C2 C1 C6 N9 -179.78(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 C3 C4 C8 -178.8(3) . . . . ?
C14 N11 N10 N9 -179.73(17) . . . . ?
C14 N11 C12 C13 179.2(2) . . . . ?
C14 N11 C12 C15 0.1(3) . . . . ?
C7 C2 C3 C4 179.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.340
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_17ma053_mm025
_database_code_depnum_ccdc_archive 'CCDC 2004182'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;

_audit_creation_date             2017-04-20T09:10:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C30 H24 N6 Ni O2'
_chemical_formula_moiety         'C30 H24 N6 Ni O2'
_chemical_formula_weight         559.26

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.78550(10)
_cell_length_b                   14.7244(2)
_cell_length_c                   22.1890(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.0320(10)
_cell_angle_gamma                90
_cell_volume                     2518.72(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10626
_cell_measurement_theta_min      2.293
_cell_measurement_theta_max      27.503

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.022
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1160
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0131
0 0 1 0.0091
-4 2 5 0.0721
5 -4 2 0.0566
-1 -5 1 0.1201
0 1 0 0.1209
4 5 -3 0.1416


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0879355
_diffrn_orient_matrix_ub_12      -0.0122957
_diffrn_orient_matrix_ub_13      -0.0003682
_diffrn_orient_matrix_ub_21      0.0142233
_diffrn_orient_matrix_ub_22      0.0006079
_diffrn_orient_matrix_ub_23      0.0322799
_diffrn_orient_matrix_ub_31      -0.0230618
_diffrn_orient_matrix_ub_32      -0.046563
_diffrn_orient_matrix_ub_33      0.0005114
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_number            27724
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.665
_diffrn_reflns_theta_max         28.204
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.93
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.93
_reflns_Friedel_coverage         0
_reflns_number_total             5771
_reflns_number_gt                4798
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+1.6360P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5771
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0817
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.3493(2) 0.18664(12) 0.33785(8) 0.0191(4) Uani 1 1 d . . . . .
C2 C 0.1805(2) 0.22057(12) 0.32502(8) 0.0208(4) Uani 1 1 d . . . . .
C3 C -0.0638(3) 0.23986(16) 0.39008(10) 0.0339(5) Uani 1 1 d . . . . .
H3A H -0.072202 0.305369 0.396915 0.051 Uiso 1 1 calc R U . . .
H3B H -0.088822 0.207031 0.426266 0.051 Uiso 1 1 calc R U . . .
H3C H -0.147754 0.222157 0.354954 0.051 Uiso 1 1 calc R U . . .
C4 C 0.0857(2) 0.25641(12) 0.26808(9) 0.0221(4) Uani 1 1 d . . . . .
C5 C -0.0065(3) 0.33774(13) 0.26710(10) 0.0277(4) Uani 1 1 d . . . . .
H5 H -0.015788 0.368434 0.304158 0.033 Uiso 1 1 calc R U . . .
C6 C -0.0844(3) 0.37405(15) 0.21257(11) 0.0354(5) Uani 1 1 d . . . . .
H6 H -0.144185 0.430334 0.212113 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0751(3) 0.32851(17) 0.15897(11) 0.0395(6) Uani 1 1 d . . . . .
H7 H -0.129652 0.353267 0.121602 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0132(3) 0.24687(16) 0.15910(10) 0.0358(5) Uani 1 1 d . . . . .
H8 H 0.017823 0.215356 0.122002 0.043 Uiso 1 1 calc R U . . .
C9 C 0.0949(3) 0.21121(13) 0.21352(9) 0.0261(4) Uani 1 1 d . . . . .
H9 H 0.157327 0.155772 0.213565 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5086(2) 0.12802(13) 0.43559(9) 0.0232(4) Uani 1 1 d . . . . .
C11 C 0.5294(3) 0.13955(15) 0.49834(9) 0.0317(5) Uani 1 1 d . . . . .
H11 H 0.451173 0.176913 0.516406 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6642(3) 0.09653(17) 0.53433(10) 0.0374(5) Uani 1 1 d . . . . .
H12 H 0.681067 0.104987 0.577198 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7749(3) 0.04058(16) 0.50695(10) 0.0350(5) Uani 1 1 d . . . . .
H13 H 0.865759 0.009339 0.531569 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7547(3) 0.02979(14) 0.44450(9) 0.0292(4) Uani 1 1 d . . . . .
H14 H 0.831486 -0.009241 0.427059 0.035 Uiso 1 1 calc R U . . .
C15 C 0.6225(2) 0.07541(12) 0.40596(8) 0.0231(4) Uani 1 1 d . . . . .
C16 C 0.4919(2) 0.26596(12) 0.24657(8) 0.0183(4) Uani 1 1 d . . . . .
C17 C 0.4648(2) 0.35712(12) 0.26019(8) 0.0189(4) Uani 1 1 d . . . . .
C18 C 0.4626(3) 0.50332(13) 0.19674(10) 0.0337(5) Uani 1 1 d . . . . .
H18A H 0.524435 0.518032 0.162442 0.05 Uiso 1 1 calc R U . . .
H18B H 0.516705 0.535407 0.233207 0.05 Uiso 1 1 calc R U . . .
H18C H 0.341085 0.522133 0.187164 0.05 Uiso 1 1 calc R U . . .
C19 C 0.4331(2) 0.39854(12) 0.31794(8) 0.0203(4) Uani 1 1 d . . . . .
C20 C 0.5203(2) 0.36444(13) 0.37246(9) 0.0242(4) Uani 1 1 d . . . . .
H20 H 0.605406 0.318448 0.371387 0.029 Uiso 1 1 calc R U . . .
C21 C 0.4851(3) 0.39645(15) 0.42799(9) 0.0326(5) Uani 1 1 d . . . . .
H21 H 0.543372 0.37152 0.464747 0.039 Uiso 1 1 calc R U . . .
C22 C 0.3641(3) 0.46513(15) 0.42975(10) 0.0368(5) Uani 1 1 d . . . . .
H22 H 0.33977 0.487531 0.467803 0.044 Uiso 1 1 calc R U . . .
C23 C 0.2791(3) 0.50100(14) 0.37636(10) 0.0329(5) Uani 1 1 d . . . . .
H23 H 0.19815 0.548974 0.377817 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3108(2) 0.46752(12) 0.32055(9) 0.0251(4) Uani 1 1 d . . . . .
H24 H 0.249424 0.491502 0.284002 0.03 Uiso 1 1 calc R U . . .
C25 C 0.5547(2) 0.19559(13) 0.14960(8) 0.0227(4) Uani 1 1 d . . . . .
C26 C 0.6372(2) 0.11955(13) 0.17999(9) 0.0233(4) Uani 1 1 d . . . . .
C27 C 0.6870(3) 0.05039(14) 0.14231(9) 0.0300(5) Uani 1 1 d . . . . .
H27 H 0.745021 -0.001668 0.160436 0.036 Uiso 1 1 calc R U . . .
C28 C 0.6540(3) 0.05617(15) 0.07975(10) 0.0381(5) Uani 1 1 d . . . . .
H28 H 0.688682 0.007969 0.055666 0.046 Uiso 1 1 calc R U . . .
C29 C 0.5707(3) 0.13141(16) 0.05139(10) 0.0423(6) Uani 1 1 d . . . . .
H29 H 0.547735 0.134505 0.008252 0.051 Uiso 1 1 calc R U . . .
C30 C 0.5217(3) 0.20177(15) 0.08660(9) 0.0336(5) Uani 1 1 d . . . . .
H30 H 0.465767 0.253947 0.067816 0.04 Uiso 1 1 calc R U . . .
N1 N 0.1113(2) 0.21756(11) 0.37828(7) 0.0240(3) Uani 1 1 d . . . . .
N2 N 0.2198(2) 0.18398(11) 0.42438(7) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.3618(2) 0.16629(10) 0.39886(7) 0.0211(3) Uani 1 1 d . . . . .
N4 N 0.4708(2) 0.40488(10) 0.20784(7) 0.0224(3) Uani 1 1 d . . . . .
N5 N 0.5008(2) 0.35299(10) 0.16187(7) 0.0242(3) Uani 1 1 d . . . . .
N6 N 0.51353(19) 0.26985(10) 0.18646(7) 0.0206(3) Uani 1 1 d . . . . .
Ni1 Ni 0.52476(3) 0.15998(2) 0.29220(2) 0.01848(7) Uani 1 1 d . . . . .
O1 O 0.61199(18) 0.06744(9) 0.34672(6) 0.0271(3) Uani 1 1 d . . . . .
O2 O 0.66893(17) 0.11082(9) 0.23945(6) 0.0263(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N3 1.377(2) . ?
C1 C2 1.398(2) . ?
C1 Ni1 1.8526(19) . ?
C2 N1 1.366(2) . ?
C2 C4 1.469(2) . ?
C3 N1 1.461(2) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C9 1.392(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.95 . ?
C6 C7 1.376(3) . ?
C6 H6 0.95 . ?
C7 C8 1.385(3) . ?
C7 H7 0.95 . ?
C8 C9 1.387(3) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
C10 C11 1.390(3) . ?
C10 C15 1.408(3) . ?
C10 N3 1.424(2) . ?
C11 C12 1.380(3) . ?
C11 H11 0.95 . ?
C12 C13 1.392(3) . ?
C12 H12 0.95 . ?
C13 C14 1.382(3) . ?
C13 H13 0.95 . ?
C14 C15 1.412(3) . ?
C14 H14 0.95 . ?
C15 O1 1.311(2) . ?
C16 N6 1.369(2) . ?
C16 C17 1.398(2) . ?
C16 Ni1 1.8583(18) . ?
C17 N4 1.365(2) . ?
C17 C19 1.471(3) . ?
C18 N4 1.470(2) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C20 1.395(3) . ?
C19 C24 1.399(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.95 . ?
C21 C22 1.386(3) . ?
C21 H21 0.95 . ?
C22 C23 1.379(3) . ?
C22 H22 0.95 . ?
C23 C24 1.387(3) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 C30 1.389(3) . ?
C25 C26 1.414(3) . ?
C25 N6 1.428(2) . ?
C26 O2 1.314(2) . ?
C26 C27 1.406(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.95 . ?
C28 C29 1.389(3) . ?
C28 H28 0.95 . ?
C29 C30 1.383(3) . ?
C29 H29 0.95 . ?
C30 H30 0.95 . ?
N1 N2 1.328(2) . ?
N2 N3 1.336(2) . ?
N4 N5 1.321(2) . ?
N5 N6 1.338(2) . ?
Ni1 O2 1.8763(13) . ?
Ni1 O1 1.8845(13) . ?

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
N3 C1 C2 102.30(16) . . ?
N3 C1 Ni1 122.38(13) . . ?
C2 C1 Ni1 135.11(14) . . ?
N1 C2 C1 106.57(16) . . ?
N1 C2 C4 122.97(16) . . ?
C1 C2 C4 130.43(17) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 C5 119.07(18) . . ?
C9 C4 C2 119.69(17) . . ?
C5 C4 C2 121.15(18) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 120.20(19) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?
C11 C10 C15 122.84(17) . . ?
C11 C10 N3 119.80(18) . . ?
C15 C10 N3 117.27(16) . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 121.00(19) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 121.58(19) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
O1 C15 C10 124.22(17) . . ?
O1 C15 C14 120.17(18) . . ?
C10 C15 C14 115.61(17) . . ?
N6 C16 C17 102.32(15) . . ?
N6 C16 Ni1 122.68(13) . . ?
C17 C16 Ni1 134.56(14) . . ?
N4 C17 C16 106.64(16) . . ?
N4 C17 C19 123.92(16) . . ?
C16 C17 C19 129.44(16) . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 118.49(17) . . ?
C20 C19 C17 119.04(16) . . ?
C24 C19 C17 122.36(17) . . ?
C21 C20 C19 121.13(19) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.6(2) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C23 C22 C21 120.13(19) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.16(19) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C30 C25 C26 122.68(18) . . ?
C30 C25 N6 120.09(17) . . ?
C26 C25 N6 117.15(16) . . ?
O2 C26 C27 119.81(17) . . ?
O2 C26 C25 124.43(17) . . ?
C27 C26 C25 115.75(17) . . ?
C28 C27 C26 121.72(19) . . ?
C28 C27 H27 119.1 . . ?
C26 C27 H27 119.1 . . ?
C27 C28 C29 121.0(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 119.3(2) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C29 C30 C25 119.51(19) . . ?
C29 C30 H30 120.2 . . ?
C25 C30 H30 120.2 . . ?
N2 N1 C2 113.16(15) . . ?
N2 N1 C3 117.06(16) . . ?
C2 N1 C3 129.64(16) . . ?
N1 N2 N3 102.78(14) . . ?
N2 N3 C1 115.18(15) . . ?
N2 N3 C10 118.69(15) . . ?
C1 N3 C10 126.12(16) . . ?
N5 N4 C17 112.96(15) . . ?
N5 N4 C18 116.69(15) . . ?
C17 N4 C18 130.16(16) . . ?
N4 N5 N6 103.02(14) . . ?
N5 N6 C16 115.05(15) . . ?
N5 N6 C25 118.46(15) . . ?
C16 N6 C25 126.42(15) . . ?
C1 Ni1 C16 93.68(8) . . ?
C1 Ni1 O2 166.85(7) . . ?
C16 Ni1 O2 91.88(7) . . ?
C1 Ni1 O1 91.68(7) . . ?
C16 Ni1 O1 165.17(7) . . ?
O2 Ni1 O1 85.88(6) . . ?
C15 O1 Ni1 123.05(12) . . ?
C26 O2 Ni1 122.92(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 N1 0.30(18) . . . . ?
Ni1 C1 C2 N1 174.95(14) . . . . ?
N3 C1 C2 C4 178.61(18) . . . . ?
Ni1 C1 C2 C4 -6.7(3) . . . . ?
N1 C2 C4 C9 -138.01(19) . . . . ?
C1 C2 C4 C9 43.9(3) . . . . ?
N1 C2 C4 C5 45.4(3) . . . . ?
C1 C2 C4 C5 -132.7(2) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C2 C4 C5 C6 175.20(18) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 C9 -0.8(3) . . . . ?
C7 C8 C9 C4 1.2(3) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C2 C4 C9 C8 -176.72(18) . . . . ?
C15 C10 C11 C12 -1.6(3) . . . . ?
N3 C10 C11 C12 174.91(19) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C11 C10 C15 O1 -175.97(19) . . . . ?
N3 C10 C15 O1 7.4(3) . . . . ?
C11 C10 C15 C14 3.8(3) . . . . ?
N3 C10 C15 C14 -172.75(17) . . . . ?
C13 C14 C15 O1 176.53(19) . . . . ?
C13 C14 C15 C10 -3.3(3) . . . . ?
N6 C16 C17 N4 0.66(19) . . . . ?
Ni1 C16 C17 N4 172.80(14) . . . . ?
N6 C16 C17 C19 179.98(17) . . . . ?
Ni1 C16 C17 C19 -7.9(3) . . . . ?
N4 C17 C19 C20 -143.36(18) . . . . ?
C16 C17 C19 C20 37.4(3) . . . . ?
N4 C17 C19 C24 40.5(3) . . . . ?
C16 C17 C19 C24 -138.7(2) . . . . ?
C24 C19 C20 C21 1.3(3) . . . . ?
C17 C19 C20 C21 -175.03(18) . . . . ?
C19 C20 C21 C22 -1.6(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 1.4(3) . . . . ?
C22 C23 C24 C19 -1.7(3) . . . . ?
C20 C19 C24 C23 0.4(3) . . . . ?
C17 C19 C24 C23 176.53(18) . . . . ?
C30 C25 C26 O2 -179.24(19) . . . . ?
N6 C25 C26 O2 4.1(3) . . . . ?
C30 C25 C26 C27 1.0(3) . . . . ?
N6 C25 C26 C27 -175.65(17) . . . . ?
O2 C26 C27 C28 179.0(2) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C29 0.5(4) . . . . ?
C27 C28 C29 C30 0.5(4) . . . . ?
C28 C29 C30 C25 -0.7(4) . . . . ?
C26 C25 C30 C29 -0.1(3) . . . . ?
N6 C25 C30 C29 176.5(2) . . . . ?
C1 C2 N1 N2 -0.5(2) . . . . ?
C4 C2 N1 N2 -179.01(16) . . . . ?
C1 C2 N1 C3 -176.10(19) . . . . ?
C4 C2 N1 C3 5.4(3) . . . . ?
C2 N1 N2 N3 0.5(2) . . . . ?
C3 N1 N2 N3 176.69(16) . . . . ?
N1 N2 N3 C1 -0.3(2) . . . . ?
N1 N2 N3 C10 -179.58(15) . . . . ?
C2 C1 N3 N2 0.0(2) . . . . ?
Ni1 C1 N3 N2 -175.52(13) . . . . ?
C2 C1 N3 C10 179.21(16) . . . . ?
Ni1 C1 N3 C10 3.7(2) . . . . ?
C11 C10 N3 N2 -23.2(3) . . . . ?
C15 C10 N3 N2 153.48(17) . . . . ?
C11 C10 N3 C1 157.62(18) . . . . ?
C15 C10 N3 C1 -25.7(3) . . . . ?
C16 C17 N4 N5 -0.5(2) . . . . ?
C19 C17 N4 N5 -179.91(16) . . . . ?
C16 C17 N4 C18 -175.32(19) . . . . ?
C19 C17 N4 C18 5.3(3) . . . . ?
C17 N4 N5 N6 0.1(2) . . . . ?
C18 N4 N5 N6 175.69(16) . . . . ?
N4 N5 N6 C16 0.3(2) . . . . ?
N4 N5 N6 C25 -177.07(15) . . . . ?
C17 C16 N6 N5 -0.6(2) . . . . ?
Ni1 C16 N6 N5 -173.98(12) . . . . ?
C17 C16 N6 C25 176.52(17) . . . . ?
Ni1 C16 N6 C25 3.2(2) . . . . ?
C30 C25 N6 N5 -22.6(3) . . . . ?
C26 C25 N6 N5 154.13(17) . . . . ?
C30 C25 N6 C16 160.30(19) . . . . ?
C26 C25 N6 C16 -22.9(3) . . . . ?
N3 C1 Ni1 C16 -142.62(15) . . . . ?
C2 C1 Ni1 C16 43.56(19) . . . . ?
N3 C1 Ni1 O2 102.6(3) . . . . ?
C2 C1 Ni1 O2 -71.2(4) . . . . ?
N3 C1 Ni1 O1 23.54(15) . . . . ?
C2 C1 Ni1 O1 -150.28(19) . . . . ?
N6 C16 Ni1 C1 -145.19(15) . . . . ?
C17 C16 Ni1 C1 43.95(19) . . . . ?
N6 C16 Ni1 O2 22.88(15) . . . . ?
C17 C16 Ni1 O2 -147.98(19) . . . . ?
N6 C16 Ni1 O1 103.9(3) . . . . ?
C17 C16 Ni1 O1 -67.0(4) . . . . ?
C10 C15 O1 Ni1 30.2(3) . . . . ?
C14 C15 O1 Ni1 -149.60(15) . . . . ?
C1 Ni1 O1 C15 -40.63(15) . . . . ?
C16 Ni1 O1 C15 70.5(3) . . . . ?
O2 Ni1 O1 C15 152.31(15) . . . . ?
C27 C26 O2 Ni1 -148.19(15) . . . . ?
C25 C26 O2 Ni1 32.1(3) . . . . ?
C1 Ni1 O2 C26 74.6(3) . . . . ?
C16 Ni1 O2 C26 -40.37(15) . . . . ?
O1 Ni1 O2 C26 154.31(15) . . . . ?
####################################################################### 
# 
# 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_17ma054_mm044
_database_code_depnum_ccdc_archive 'CCDC 2004183'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;

_audit_creation_date             2017-04-20T16:10:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H34 N6 Ni O3'
_chemical_formula_moiety         'C26 H32 N6 Ni O2, H2 O'
_chemical_formula_weight         537.3

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.88280(10)
_cell_length_b                   18.5259(2)
_cell_length_c                   22.3137(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.7980(10)
_cell_angle_gamma                90
_cell_volume                     5262.85(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    11833
_cell_measurement_theta_min      2.021
_cell_measurement_theta_max      28.048

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             2272
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0402
0 0 1 0.0402
0 1 0 0.0773
0 -1 0 0.0773
-5 1 -2 0.1598
1 0 -1 0.1542


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.943

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      173(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0965
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      -0.003358
_diffrn_orient_matrix_ub_12      -0.0066688
_diffrn_orient_matrix_ub_13      0.0309337
_diffrn_orient_matrix_ub_21      0.0045832
_diffrn_orient_matrix_ub_22      -0.0376131
_diffrn_orient_matrix_ub_23      -0.0049693
_diffrn_orient_matrix_ub_31      0.0554299
_diffrn_orient_matrix_ub_32      0.0027029
_diffrn_orient_matrix_ub_33      0.0072519
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.044
_diffrn_reflns_number            32666
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.901
_reflns_Friedel_coverage         0
_reflns_number_total             11659
_reflns_number_gt                9102
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+5.1994P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11659
_refine_ls_number_parameters     668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.66315(18) 0.74451(13) 0.32944(11) 0.0230(5) Uani 1 1 d . . . . .
C2 C 0.71085(18) 0.80851(13) 0.31478(11) 0.0253(5) Uani 1 1 d . . . . .
C3 C 0.8677(2) 0.88038(17) 0.36784(14) 0.0451(8) Uani 1 1 d . . . . .
H3A H 0.86421 0.906226 0.329262 0.068 Uiso 1 1 calc R U . . .
H3B H 0.938506 0.860725 0.379638 0.068 Uiso 1 1 calc R U . . .
H3C H 0.851516 0.913735 0.399222 0.068 Uiso 1 1 calc R U . . .
C4 C 0.68969(18) 0.85451(13) 0.25962(11) 0.0259(5) Uani 1 1 d . . . . .
H4A H 0.728945 0.90034 0.267428 0.031 Uiso 1 1 calc R U . . .
H4B H 0.613903 0.866401 0.251949 0.031 Uiso 1 1 calc R U . . .
C5 C 0.72006(19) 0.81946(14) 0.20266(11) 0.0267(5) Uani 1 1 d . . . . .
H5A H 0.797524 0.81608 0.206833 0.032 Uiso 1 1 calc R U . . .
H5B H 0.691236 0.769864 0.19855 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6790(2) 0.86224(15) 0.14627(12) 0.0326(6) Uani 1 1 d . . . . .
H6A H 0.704689 0.91253 0.151731 0.039 Uiso 1 1 calc R U . . .
H6B H 0.601329 0.863539 0.141414 0.039 Uiso 1 1 calc R U . . .
C7 C 0.7117(2) 0.83179(18) 0.08882(13) 0.0444(7) Uani 1 1 d . . . . .
H7A H 0.788248 0.834516 0.091628 0.067 Uiso 1 1 calc R U . . .
H7B H 0.678683 0.859881 0.053802 0.067 Uiso 1 1 calc R U . . .
H7C H 0.689236 0.781311 0.083927 0.067 Uiso 1 1 calc R U . . .
C8 C 0.71343(19) 0.66041(14) 0.41693(12) 0.0287(6) Uani 1 1 d . . . . .
C9 C 0.66887(19) 0.60015(14) 0.38439(11) 0.0279(6) Uani 1 1 d . . . . .
C10 C 0.6716(2) 0.53506(15) 0.41717(13) 0.0341(6) Uani 1 1 d . . . . .
H10 H 0.642932 0.492582 0.397277 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7149(2) 0.53171(17) 0.47746(13) 0.0419(7) Uani 1 1 d . . . . .
H11 H 0.71614 0.486891 0.498239 0.05 Uiso 1 1 calc R U . . .
C12 C 0.7567(2) 0.59251(18) 0.50842(13) 0.0449(8) Uani 1 1 d . . . . .
H12 H 0.785676 0.589582 0.550145 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7558(2) 0.65712(17) 0.47797(12) 0.0387(7) Uani 1 1 d . . . . .
H13 H 0.783957 0.699283 0.498581 0.046 Uiso 1 1 calc R U . . .
C14 C 0.48348(17) 0.75496(13) 0.24712(11) 0.0233(5) Uani 1 1 d . . . . .
C15 C 0.42540(19) 0.81101(13) 0.26768(12) 0.0280(5) Uani 1 1 d . . . . .
C16 C 0.2891(2) 0.89875(16) 0.21473(15) 0.0441(8) Uani 1 1 d . . . . .
H16A H 0.325433 0.945046 0.213266 0.066 Uiso 1 1 calc R U . . .
H16B H 0.253805 0.897388 0.250621 0.066 Uiso 1 1 calc R U . . .
H16C H 0.236952 0.89325 0.178143 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4231(2) 0.83739(15) 0.33043(13) 0.0353(6) Uani 1 1 d . . . . .
H17A H 0.450905 0.798918 0.359262 0.042 Uiso 1 1 calc R U . . .
H17B H 0.349014 0.845928 0.335451 0.042 Uiso 1 1 calc R U . . .
C18 C 0.4854(2) 0.90644(16) 0.34735(14) 0.0417(7) Uani 1 1 d . . . . .
H18A H 0.557713 0.900037 0.338277 0.05 Uiso 1 1 calc R U . . .
H18B H 0.452621 0.946564 0.321896 0.05 Uiso 1 1 calc R U . . .
C19 C 0.4908(3) 0.9268(2) 0.41367(16) 0.0594(10) Uani 1 1 d . . . . .
H19A H 0.420181 0.941822 0.421173 0.071 Uiso 1 1 calc R U . . .
H19B H 0.51186 0.883898 0.439149 0.071 Uiso 1 1 calc R U . . .
C20 C 0.5680(3) 0.9873(2) 0.43192(19) 0.0753(12) Uani 1 1 d . . . . .
H20A H 0.63811 0.972603 0.424642 0.113 Uiso 1 1 calc R U . . .
H20B H 0.570047 0.998139 0.475078 0.113 Uiso 1 1 calc R U . . .
H20C H 0.545992 1.030451 0.407872 0.113 Uiso 1 1 calc R U . . .
C21 C 0.47653(18) 0.70522(14) 0.14299(12) 0.0283(6) Uani 1 1 d . . . . .
C22 C 0.50201(18) 0.63518(14) 0.16533(12) 0.0274(5) Uani 1 1 d . . . . .
C23 C 0.51761(19) 0.58313(16) 0.12166(13) 0.0347(6) Uani 1 1 d . . . . .
H23 H 0.532981 0.534732 0.134013 0.042 Uiso 1 1 calc R U . . .
C24 C 0.5110(2) 0.60114(18) 0.06132(14) 0.0438(8) Uani 1 1 d . . . . .
H24 H 0.521141 0.564757 0.032777 0.053 Uiso 1 1 calc R U . . .
C25 C 0.4897(2) 0.67156(19) 0.04123(14) 0.0461(8) Uani 1 1 d . . . . .
H25 H 0.487423 0.683476 -0.000362 0.055 Uiso 1 1 calc R U . . .
C26 C 0.4719(2) 0.72362(16) 0.08247(12) 0.0362(6) Uani 1 1 d . . . . .
H26 H 0.45658 0.771831 0.069534 0.043 Uiso 1 1 calc R U . . .
C27 C 0.51855(17) 0.21439(13) 0.26036(11) 0.0228(5) Uani 1 1 d . . . . .
C28 C 0.57736(18) 0.15884(13) 0.23984(11) 0.0242(5) Uani 1 1 d . . . . .
C29 C 0.7177(2) 0.07416(15) 0.29296(14) 0.0389(7) Uani 1 1 d . . . . .
H29A H 0.683063 0.027001 0.292264 0.058 Uiso 1 1 calc R U . . .
H29B H 0.767502 0.079086 0.330586 0.058 Uiso 1 1 calc R U . . .
H29C H 0.755389 0.078093 0.258136 0.058 Uiso 1 1 calc R U . . .
C30 C 0.5807(2) 0.13168(14) 0.17748(12) 0.0305(6) Uani 1 1 d . . . . .
H30A H 0.655117 0.127027 0.171839 0.037 Uiso 1 1 calc R U . . .
H30B H 0.54784 0.168243 0.148202 0.037 Uiso 1 1 calc R U . . .
C31 C 0.5261(2) 0.05928(15) 0.16198(13) 0.0383(7) Uani 1 1 d . . . . .
H31A H 0.562632 0.021465 0.18863 0.046 Uiso 1 1 calc R U . . .
H31B H 0.452976 0.062324 0.170411 0.046 Uiso 1 1 calc R U . . .
C32 C 0.5244(2) 0.03713(18) 0.09597(13) 0.0458(8) Uani 1 1 d . . . . .
H32A H 0.597383 0.036028 0.087172 0.055 Uiso 1 1 calc R U . . .
H32B H 0.495572 -0.012356 0.090261 0.055 Uiso 1 1 calc R U . . .
C33 C 0.4606(3) 0.0865(2) 0.05157(16) 0.0753(13) Uani 1 1 d . . . . .
H33A H 0.389237 0.090198 0.061419 0.113 Uiso 1 1 calc R U . . .
H33B H 0.457749 0.06705 0.010492 0.113 Uiso 1 1 calc R U . . .
H33C H 0.493117 0.1344 0.053738 0.113 Uiso 1 1 calc R U . . .
C34 C 0.52394(18) 0.26506(13) 0.36393(11) 0.0262(5) Uani 1 1 d . . . . .
C35 C 0.49707(18) 0.33499(14) 0.34151(12) 0.0278(6) Uani 1 1 d . . . . .
C36 C 0.47891(19) 0.38663(16) 0.38472(13) 0.0358(6) Uani 1 1 d . . . . .
H36 H 0.462116 0.434763 0.372111 0.043 Uiso 1 1 calc R U . . .
C37 C 0.4850(2) 0.36870(18) 0.44551(14) 0.0443(8) Uani 1 1 d . . . . .
H37 H 0.472692 0.404768 0.473857 0.053 Uiso 1 1 calc R U . . .
C38 C 0.5088(2) 0.29916(18) 0.46549(13) 0.0425(7) Uani 1 1 d . . . . .
H38 H 0.511507 0.287326 0.507121 0.051 Uiso 1 1 calc R U . . .
C39 C 0.5287(2) 0.24710(16) 0.42459(12) 0.0343(6) Uani 1 1 d . . . . .
H39 H 0.545529 0.19921 0.437895 0.041 Uiso 1 1 calc R U . . .
C40 C 0.34176(17) 0.22428(13) 0.17639(11) 0.0223(5) Uani 1 1 d . . . . .
C41 C 0.29346(18) 0.15998(13) 0.18979(11) 0.0241(5) Uani 1 1 d . . . . .
C42 C 0.1405(2) 0.08730(16) 0.13245(14) 0.0413(7) Uani 1 1 d . . . . .
H42A H 0.152826 0.054016 0.166937 0.062 Uiso 0.5 1 calc R U P . .
H42B H 0.069118 0.106763 0.128807 0.062 Uiso 0.5 1 calc R U P . .
H42C H 0.148918 0.061444 0.095172 0.062 Uiso 0.5 1 calc R U P . .
H42D H 0.094415 0.094132 0.093674 0.062 Uiso 0.5 1 calc R U P . .
H42E H 0.178124 0.041385 0.131804 0.062 Uiso 0.5 1 calc R U P . .
H42F H 0.098324 0.086705 0.165438 0.062 Uiso 0.5 1 calc R U P . .
C43 C 0.31186(18) 0.11417(13) 0.24511(11) 0.0256(5) Uani 1 1 d . . . . .
H43A H 0.387299 0.101392 0.253567 0.031 Uiso 1 1 calc R U . . .
H43B H 0.271583 0.068776 0.237074 0.031 Uiso 1 1 calc R U . . .
C44 C 0.28043(19) 0.15028(14) 0.30164(11) 0.0285(5) Uani 1 1 d . . . . .
H44A H 0.308895 0.199987 0.30531 0.034 Uiso 1 1 calc R U . . .
H44B H 0.202918 0.153387 0.297225 0.034 Uiso 1 1 calc R U . . .
C45 C 0.3217(2) 0.10807(17) 0.35857(13) 0.0386(7) Uani 1 1 d . . . . .
H45A H 0.296564 0.057626 0.353374 0.046 Uiso 1 1 calc R U . . .
H45B H 0.399377 0.10713 0.363562 0.046 Uiso 1 1 calc R U . . .
C46 C 0.2886(2) 0.1386(2) 0.41568(14) 0.0528(9) Uani 1 1 d . . . . .
H46A H 0.308151 0.18968 0.419555 0.079 Uiso 1 1 calc R U . . .
H46B H 0.323874 0.111988 0.450986 0.079 Uiso 1 1 calc R U . . .
H46C H 0.212345 0.13383 0.413467 0.079 Uiso 1 1 calc R U . . .
C47 C 0.29499(18) 0.30843(13) 0.08864(11) 0.0247(5) Uani 1 1 d . . . . .
C48 C 0.33647(18) 0.36914(13) 0.12233(11) 0.0234(5) Uani 1 1 d . . . . .
C49 C 0.33294(19) 0.43463(14) 0.09022(12) 0.0290(6) Uani 1 1 d . . . . .
H49 H 0.358557 0.477333 0.110968 0.035 Uiso 1 1 calc R U . . .
C50 C 0.2932(2) 0.43828(15) 0.02939(12) 0.0346(6) Uani 1 1 d . . . . .
H50 H 0.291771 0.483428 0.009095 0.042 Uiso 1 1 calc R U . . .
C51 C 0.2553(2) 0.37733(16) -0.00282(12) 0.0375(7) Uani 1 1 d . . . . .
H51 H 0.229137 0.380304 -0.044932 0.045 Uiso 1 1 calc R U . . .
C52 C 0.2562(2) 0.31232(15) 0.02738(12) 0.0319(6) Uani 1 1 d . . . . .
H52 H 0.230037 0.27009 0.006065 0.038 Uiso 1 1 calc R U . . .
N1 N 0.79105(16) 0.82107(12) 0.36093(10) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.80017(17) 0.77126(13) 0.40388(10) 0.0338(5) Uani 1 1 d . . . . .
N3 N 0.72171(15) 0.72583(11) 0.38382(9) 0.0260(4) Uani 1 1 d . . . . .
N4 N 0.36577(16) 0.83961(11) 0.21795(10) 0.0302(5) Uani 1 1 d . . . . .
N5 N 0.37846(16) 0.80751(12) 0.16654(10) 0.0308(5) Uani 1 1 d . . . . .
N6 N 0.44993(15) 0.75670(11) 0.18573(9) 0.0244(4) Uani 1 1 d . . . . .
N7 N 0.63873(15) 0.13133(11) 0.28980(10) 0.0264(5) Uani 1 1 d . . . . .
N8 N 0.62545(16) 0.16418(11) 0.34085(10) 0.0280(5) Uani 1 1 d . . . . .
N9 N 0.55269(15) 0.21377(11) 0.32170(9) 0.0234(4) Uani 1 1 d . . . . .
N10 N 0.21646(16) 0.14665(11) 0.14205(10) 0.0274(5) Uani 1 1 d . . . . .
N11 N 0.20994(16) 0.19647(11) 0.09906(10) 0.0283(5) Uani 1 1 d . . . . .
N12 N 0.28613(15) 0.24302(11) 0.12111(9) 0.0233(4) Uani 1 1 d . . . . .
O1 O 0.62909(13) 0.60126(9) 0.32637(8) 0.0299(4) Uani 1 1 d . . . . .
O2 O 0.50904(13) 0.61679(9) 0.22321(8) 0.0303(4) Uani 1 1 d . . . . .
O3 O 0.49160(13) 0.35298(9) 0.28382(8) 0.0299(4) Uani 1 1 d . . . . .
O4 O 0.37366(13) 0.36756(9) 0.18064(8) 0.0275(4) Uani 1 1 d . . . . .
O5 O 0.62594(16) 0.46712(12) 0.25916(11) 0.0397(5) Uani 1 1 d . . . . .
O6 O 0.37506(16) 0.50225(11) 0.24347(10) 0.0383(5) Uani 1 1 d . . . . .
Ni1 Ni 0.56997(2) 0.68260(2) 0.28334(2) 0.02175(8) Uani 1 1 d . . . . .
Ni2 Ni 0.43250(2) 0.28660(2) 0.22362(2) 0.02062(8) Uani 1 1 d . . . . .
H5C H 0.615(2) 0.5027(16) 0.2738(13) 0.031 Uiso 1 1 d . U . . .
H5D H 0.582(2) 0.4396(16) 0.2675(13) 0.031 Uiso 1 1 d . U . . .
H6C H 0.418(2) 0.5320(16) 0.2391(13) 0.031 Uiso 1 1 d . U . . .
H6D H 0.389(2) 0.4631(16) 0.2293(13) 0.031 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N3 1.372(3) . ?
C1 C2 1.397(3) . ?
C1 Ni1 1.854(2) . ?
C2 N1 1.362(3) . ?
C2 C4 1.488(3) . ?
C3 N1 1.470(3) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C5 1.530(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.512(3) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C7 1.518(4) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C13 1.389(4) . ?
C8 C9 1.406(4) . ?
C8 N3 1.432(3) . ?
C9 O1 1.317(3) . ?
C9 C10 1.408(4) . ?
C10 C11 1.377(4) . ?
C10 H10 0.95 . ?
C11 C12 1.387(4) . ?
C11 H11 0.95 . ?
C12 C13 1.376(4) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 N6 1.372(3) . ?
C14 C15 1.398(3) . ?
C14 Ni1 1.848(2) . ?
C15 N4 1.357(3) . ?
C15 C17 1.488(4) . ?
C16 N4 1.469(3) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C18 1.527(4) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C19 1.518(4) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
C19 C20 1.514(5) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 C26 1.385(4) . ?
C21 C22 1.410(4) . ?
C21 N6 1.427(3) . ?
C22 O2 1.325(3) . ?
C22 C23 1.407(4) . ?
C23 C24 1.377(4) . ?
C23 H23 0.95 . ?
C24 C25 1.393(4) . ?
C24 H24 0.95 . ?
C25 C26 1.376(4) . ?
C25 H25 0.95 . ?
C26 H26 0.95 . ?
C27 N9 1.372(3) . ?
C27 C28 1.396(3) . ?
C27 Ni2 1.847(2) . ?
C28 N7 1.363(3) . ?
C28 C30 1.486(3) . ?
C29 N7 1.463(3) . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C30 C31 1.529(4) . ?
C30 H30A 0.99 . ?
C30 H30B 0.99 . ?
C31 C32 1.526(4) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 C33 1.497(5) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C34 C39 1.386(4) . ?
C34 C35 1.413(4) . ?
C34 N9 1.426(3) . ?
C35 O3 1.321(3) . ?
C35 C36 1.403(4) . ?
C36 C37 1.387(4) . ?
C36 H36 0.95 . ?
C37 C38 1.382(4) . ?
C37 H37 0.95 . ?
C38 C39 1.378(4) . ?
C38 H38 0.95 . ?
C39 H39 0.95 . ?
C40 N12 1.373(3) . ?
C40 C41 1.397(3) . ?
C40 Ni2 1.853(2) . ?
C41 N10 1.362(3) . ?
C41 C43 1.487(3) . ?
C42 N10 1.465(3) . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C42 H42D 0.98 . ?
C42 H42E 0.98 . ?
C42 H42F 0.98 . ?
C43 C44 1.536(3) . ?
C43 H43A 0.99 . ?
C43 H43B 0.99 . ?
C44 C45 1.517(4) . ?
C44 H44A 0.99 . ?
C44 H44B 0.99 . ?
C45 C46 1.514(4) . ?
C45 H45A 0.99 . ?
C45 H45B 0.99 . ?
C46 H46A 0.98 . ?
C46 H46B 0.98 . ?
C46 H46C 0.98 . ?
C47 C52 1.384(3) . ?
C47 C48 1.412(3) . ?
C47 N12 1.425(3) . ?
C48 O4 1.316(3) . ?
C48 C49 1.406(3) . ?
C49 C50 1.377(4) . ?
C49 H49 0.95 . ?
C50 C51 1.387(4) . ?
C50 H50 0.95 . ?
C51 C52 1.379(4) . ?
C51 H51 0.95 . ?
C52 H52 0.95 . ?
N1 N2 1.323(3) . ?
N2 N3 1.339(3) . ?
N4 N5 1.324(3) . ?
N5 N6 1.340(3) . ?
N7 N8 1.325(3) . ?
N8 N9 1.335(3) . ?
N10 N11 1.325(3) . ?
N11 N12 1.342(3) . ?
O1 Ni1 1.8838(17) . ?
O2 Ni1 1.8922(17) . ?
O3 Ni2 1.8930(17) . ?
O4 Ni2 1.8767(16) . ?
O5 H5C 0.76(3) . ?
O5 H5D 0.81(3) . ?
O6 H6C 0.79(3) . ?
O6 H6D 0.82(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
N3 C1 C2 102.7(2) . . ?
N3 C1 Ni1 123.82(18) . . ?
C2 C1 Ni1 131.75(19) . . ?
N1 C2 C1 106.1(2) . . ?
N1 C2 C4 123.3(2) . . ?
C1 C2 C4 130.4(2) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 C5 114.0(2) . . ?
C2 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C2 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.5(2) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108 . . ?
C5 C6 C7 113.6(2) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 122.7(3) . . ?
C13 C8 N3 119.6(2) . . ?
C9 C8 N3 117.5(2) . . ?
O1 C9 C8 124.2(2) . . ?
O1 C9 C10 119.9(2) . . ?
C8 C9 C10 115.8(2) . . ?
C11 C10 C9 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
N6 C14 C15 102.0(2) . . ?
N6 C14 Ni1 122.03(17) . . ?
C15 C14 Ni1 135.4(2) . . ?
N4 C15 C14 106.6(2) . . ?
N4 C15 C17 123.4(2) . . ?
C14 C15 C17 129.9(2) . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 C18 115.0(2) . . ?
C15 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
C15 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C19 C18 C17 113.1(3) . . ?
C19 C18 H18A 109 . . ?
C17 C18 H18A 109 . . ?
C19 C18 H18B 109 . . ?
C17 C18 H18B 109 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 112.1(3) . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 123.0(2) . . ?
C26 C21 N6 120.5(2) . . ?
C22 C21 N6 116.4(2) . . ?
O2 C22 C23 120.2(2) . . ?
O2 C22 C21 123.9(2) . . ?
C23 C22 C21 115.8(2) . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 121.4(3) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C26 C25 C24 119.1(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C25 C26 C21 119.5(3) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
N9 C27 C28 102.3(2) . . ?
N9 C27 Ni2 121.85(17) . . ?
C28 C27 Ni2 135.01(19) . . ?
N7 C28 C27 106.5(2) . . ?
N7 C28 C30 122.9(2) . . ?
C27 C28 C30 130.6(2) . . ?
N7 C29 H29A 109.5 . . ?
N7 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N7 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 C31 115.5(2) . . ?
C28 C30 H30A 108.4 . . ?
C31 C30 H30A 108.4 . . ?
C28 C30 H30B 108.4 . . ?
C31 C30 H30B 108.4 . . ?
H30A C30 H30B 107.5 . . ?
C32 C31 C30 113.1(2) . . ?
C32 C31 H31A 109 . . ?
C30 C31 H31A 109 . . ?
C32 C31 H31B 109 . . ?
C30 C31 H31B 109 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C31 113.6(3) . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32B 108.8 . . ?
C31 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C39 C34 C35 122.5(2) . . ?
C39 C34 N9 120.5(2) . . ?
C35 C34 N9 116.8(2) . . ?
O3 C35 C36 120.5(2) . . ?
O3 C35 C34 123.4(2) . . ?
C36 C35 C34 116.1(2) . . ?
C37 C36 C35 121.2(3) . . ?
C37 C36 H36 119.4 . . ?
C35 C36 H36 119.4 . . ?
C38 C37 C36 121.0(3) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C39 C38 C37 119.6(3) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C34 119.6(3) . . ?
C38 C39 H39 120.2 . . ?
C34 C39 H39 120.2 . . ?
N12 C40 C41 102.7(2) . . ?
N12 C40 Ni2 123.41(17) . . ?
C41 C40 Ni2 132.25(19) . . ?
N10 C41 C40 106.4(2) . . ?
N10 C41 C43 123.4(2) . . ?
C40 C41 C43 130.1(2) . . ?
N10 C42 H42A 109.5 . . ?
N10 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
N10 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N10 C42 H42D 109.5 . . ?
H42A C42 H42D 141.1 . . ?
H42B C42 H42D 56.3 . . ?
H42C C42 H42D 56.3 . . ?
N10 C42 H42E 109.5 . . ?
H42A C42 H42E 56.3 . . ?
H42B C42 H42E 141.1 . . ?
H42C C42 H42E 56.3 . . ?
H42D C42 H42E 109.5 . . ?
N10 C42 H42F 109.5 . . ?
H42A C42 H42F 56.3 . . ?
H42B C42 H42F 56.3 . . ?
H42C C42 H42F 141.1 . . ?
H42D C42 H42F 109.5 . . ?
H42E C42 H42F 109.5 . . ?
C41 C43 C44 113.9(2) . . ?
C41 C43 H43A 108.8 . . ?
C44 C43 H43A 108.8 . . ?
C41 C43 H43B 108.8 . . ?
C44 C43 H43B 108.8 . . ?
H43A C43 H43B 107.7 . . ?
C45 C44 C43 111.1(2) . . ?
C45 C44 H44A 109.4 . . ?
C43 C44 H44A 109.4 . . ?
C45 C44 H44B 109.4 . . ?
C43 C44 H44B 109.4 . . ?
H44A C44 H44B 108 . . ?
C46 C45 C44 113.9(2) . . ?
C46 C45 H45A 108.8 . . ?
C44 C45 H45A 108.8 . . ?
C46 C45 H45B 108.8 . . ?
C44 C45 H45B 108.8 . . ?
H45A C45 H45B 107.7 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C52 C47 C48 122.3(2) . . ?
C52 C47 N12 120.1(2) . . ?
C48 C47 N12 117.4(2) . . ?
O4 C48 C49 120.1(2) . . ?
O4 C48 C47 124.0(2) . . ?
C49 C48 C47 115.8(2) . . ?
C50 C49 C48 121.5(2) . . ?
C50 C49 H49 119.2 . . ?
C48 C49 H49 119.2 . . ?
C49 C50 C51 121.3(3) . . ?
C49 C50 H50 119.4 . . ?
C51 C50 H50 119.4 . . ?
C52 C51 C50 118.8(3) . . ?
C52 C51 H51 120.6 . . ?
C50 C51 H51 120.6 . . ?
C51 C52 C47 120.2(2) . . ?
C51 C52 H52 119.9 . . ?
C47 C52 H52 119.9 . . ?
N2 N1 C2 113.7(2) . . ?
N2 N1 C3 117.5(2) . . ?
C2 N1 C3 128.8(2) . . ?
N1 N2 N3 102.56(19) . . ?
N2 N3 C1 115.0(2) . . ?
N2 N3 C8 118.1(2) . . ?
C1 N3 C8 126.6(2) . . ?
N5 N4 C15 113.8(2) . . ?
N5 N4 C16 117.6(2) . . ?
C15 N4 C16 128.6(2) . . ?
N4 N5 N6 102.0(2) . . ?
N5 N6 C14 115.6(2) . . ?
N5 N6 C21 118.6(2) . . ?
C14 N6 C21 125.5(2) . . ?
N8 N7 C28 113.3(2) . . ?
N8 N7 C29 118.1(2) . . ?
C28 N7 C29 128.5(2) . . ?
N7 N8 N9 102.57(19) . . ?
N8 N9 C27 115.3(2) . . ?
N8 N9 C34 119.2(2) . . ?
C27 N9 C34 125.3(2) . . ?
N11 N10 C41 113.4(2) . . ?
N11 N10 C42 116.7(2) . . ?
C41 N10 C42 129.8(2) . . ?
N10 N11 N12 102.73(18) . . ?
N11 N12 C40 114.8(2) . . ?
N11 N12 C47 118.09(19) . . ?
C40 N12 C47 126.9(2) . . ?
C9 O1 Ni1 125.42(16) . . ?
C22 O2 Ni1 118.98(15) . . ?
C35 O3 Ni2 118.90(15) . . ?
C48 O4 Ni2 125.48(15) . . ?
H5C O5 H5D 105(3) . . ?
H6C O6 H6D 112(3) . . ?
C14 Ni1 C1 95.15(10) . . ?
C14 Ni1 O1 166.58(9) . . ?
C1 Ni1 O1 92.01(9) . . ?
C14 Ni1 O2 90.01(9) . . ?
C1 Ni1 O2 162.78(9) . . ?
O1 Ni1 O2 86.43(7) . . ?
C27 Ni2 C40 94.86(10) . . ?
C27 Ni2 O4 166.82(9) . . ?
C40 Ni2 O4 92.12(9) . . ?
C27 Ni2 O3 90.38(9) . . ?
C40 Ni2 O3 163.46(9) . . ?
O4 Ni2 O3 86.02(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C1 C2 N1 0.0(3) . . . . ?
Ni1 C1 C2 N1 -164.84(19) . . . . ?
N3 C1 C2 C4 175.8(2) . . . . ?
Ni1 C1 C2 C4 11.0(4) . . . . ?
N1 C2 C4 C5 106.5(3) . . . . ?
C1 C2 C4 C5 -68.8(3) . . . . ?
C2 C4 C5 C6 169.6(2) . . . . ?
C4 C5 C6 C7 177.1(2) . . . . ?
C13 C8 C9 O1 -179.2(2) . . . . ?
N3 C8 C9 O1 -4.0(4) . . . . ?
C13 C8 C9 C10 -1.3(4) . . . . ?
N3 C8 C9 C10 173.9(2) . . . . ?
O1 C9 C10 C11 178.4(2) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C8 -0.2(4) . . . . ?
C9 C8 C13 C12 1.2(4) . . . . ?
N3 C8 C13 C12 -173.9(2) . . . . ?
N6 C14 C15 N4 -0.4(2) . . . . ?
Ni1 C14 C15 N4 -171.44(19) . . . . ?
N6 C14 C15 C17 178.9(2) . . . . ?
Ni1 C14 C15 C17 7.9(4) . . . . ?
N4 C15 C17 C18 -78.8(3) . . . . ?
C14 C15 C17 C18 102.0(3) . . . . ?
C15 C17 C18 C19 -173.6(3) . . . . ?
C17 C18 C19 C20 170.0(3) . . . . ?
C26 C21 C22 O2 178.5(2) . . . . ?
N6 C21 C22 O2 -4.6(3) . . . . ?
C26 C21 C22 C23 -3.1(4) . . . . ?
N6 C21 C22 C23 173.8(2) . . . . ?
O2 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 C24 1.8(4) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C26 -1.9(4) . . . . ?
C24 C25 C26 C21 0.6(4) . . . . ?
C22 C21 C26 C25 2.0(4) . . . . ?
N6 C21 C26 C25 -174.8(2) . . . . ?
N9 C27 C28 N7 0.2(2) . . . . ?
Ni2 C27 C28 N7 169.63(19) . . . . ?
N9 C27 C28 C30 -178.5(2) . . . . ?
Ni2 C27 C28 C30 -9.1(4) . . . . ?
N7 C28 C30 C31 75.7(3) . . . . ?
C27 C28 C30 C31 -105.8(3) . . . . ?
C28 C30 C31 C32 175.4(2) . . . . ?
C30 C31 C32 C33 -65.0(4) . . . . ?
C39 C34 C35 O3 -179.6(2) . . . . ?
N9 C34 C35 O3 4.1(3) . . . . ?
C39 C34 C35 C36 2.2(4) . . . . ?
N9 C34 C35 C36 -174.0(2) . . . . ?
O3 C35 C36 C37 -179.6(2) . . . . ?
C34 C35 C36 C37 -1.4(4) . . . . ?
C35 C36 C37 C38 -0.3(4) . . . . ?
C36 C37 C38 C39 1.2(4) . . . . ?
C37 C38 C39 C34 -0.4(4) . . . . ?
C35 C34 C39 C38 -1.4(4) . . . . ?
N9 C34 C39 C38 174.7(2) . . . . ?
N12 C40 C41 N10 0.6(2) . . . . ?
Ni2 C40 C41 N10 165.81(18) . . . . ?
N12 C40 C41 C43 -175.6(2) . . . . ?
Ni2 C40 C41 C43 -10.5(4) . . . . ?
N10 C41 C43 C44 -108.8(3) . . . . ?
C40 C41 C43 C44 66.9(3) . . . . ?
C41 C43 C44 C45 -168.1(2) . . . . ?
C43 C44 C45 C46 -176.9(2) . . . . ?
C52 C47 C48 O4 179.7(2) . . . . ?
N12 C47 C48 O4 4.8(3) . . . . ?
C52 C47 C48 C49 1.9(3) . . . . ?
N12 C47 C48 C49 -173.0(2) . . . . ?
O4 C48 C49 C50 -179.1(2) . . . . ?
C47 C48 C49 C50 -1.3(4) . . . . ?
C48 C49 C50 C51 -0.2(4) . . . . ?
C49 C50 C51 C52 1.1(4) . . . . ?
C50 C51 C52 C47 -0.4(4) . . . . ?
C48 C47 C52 C51 -1.1(4) . . . . ?
N12 C47 C52 C51 173.6(2) . . . . ?
C1 C2 N1 N2 0.3(3) . . . . ?
C4 C2 N1 N2 -175.9(2) . . . . ?
C1 C2 N1 C3 178.7(3) . . . . ?
C4 C2 N1 C3 2.5(4) . . . . ?
C2 N1 N2 N3 -0.4(3) . . . . ?
C3 N1 N2 N3 -179.0(2) . . . . ?
N1 N2 N3 C1 0.4(3) . . . . ?
N1 N2 N3 C8 174.3(2) . . . . ?
C2 C1 N3 N2 -0.2(3) . . . . ?
Ni1 C1 N3 N2 166.17(17) . . . . ?
C2 C1 N3 C8 -173.6(2) . . . . ?
Ni1 C1 N3 C8 -7.2(3) . . . . ?
C13 C8 N3 N2 24.7(3) . . . . ?
C9 C8 N3 N2 -150.7(2) . . . . ?
C13 C8 N3 C1 -162.1(2) . . . . ?
C9 C8 N3 C1 22.5(4) . . . . ?
C14 C15 N4 N5 0.4(3) . . . . ?
C17 C15 N4 N5 -179.0(2) . . . . ?
C14 C15 N4 C16 178.5(2) . . . . ?
C17 C15 N4 C16 -0.8(4) . . . . ?
C15 N4 N5 N6 -0.2(3) . . . . ?
C16 N4 N5 N6 -178.6(2) . . . . ?
N4 N5 N6 C14 0.0(3) . . . . ?
N4 N5 N6 C21 173.7(2) . . . . ?
C15 C14 N6 N5 0.3(3) . . . . ?
Ni1 C14 N6 N5 172.88(16) . . . . ?
C15 C14 N6 C21 -173.0(2) . . . . ?
Ni1 C14 N6 C21 -0.4(3) . . . . ?
C26 C21 N6 N5 30.3(3) . . . . ?
C22 C21 N6 N5 -146.7(2) . . . . ?
C26 C21 N6 C14 -156.7(2) . . . . ?
C22 C21 N6 C14 26.4(3) . . . . ?
C27 C28 N7 N8 -0.3(3) . . . . ?
C30 C28 N7 N8 178.6(2) . . . . ?
C27 C28 N7 C29 -177.4(2) . . . . ?
C30 C28 N7 C29 1.4(4) . . . . ?
C28 N7 N8 N9 0.2(3) . . . . ?
C29 N7 N8 N9 177.7(2) . . . . ?
N7 N8 N9 C27 -0.1(3) . . . . ?
N7 N8 N9 C34 -174.4(2) . . . . ?
C28 C27 N9 N8 -0.1(3) . . . . ?
Ni2 C27 N9 N8 -171.28(16) . . . . ?
C28 C27 N9 C34 173.9(2) . . . . ?
Ni2 C27 N9 C34 2.7(3) . . . . ?
C39 C34 N9 N8 -30.3(3) . . . . ?
C35 C34 N9 N8 146.1(2) . . . . ?
C39 C34 N9 C27 156.0(2) . . . . ?
C35 C34 N9 C27 -27.7(3) . . . . ?
C40 C41 N10 N11 -0.3(3) . . . . ?
C43 C41 N10 N11 176.3(2) . . . . ?
C40 C41 N10 C42 -179.0(3) . . . . ?
C43 C41 N10 C42 -2.4(4) . . . . ?
C41 N10 N11 N12 -0.2(3) . . . . ?
C42 N10 N11 N12 178.7(2) . . . . ?
N10 N11 N12 C40 0.6(3) . . . . ?
N10 N11 N12 C47 -173.87(19) . . . . ?
C41 C40 N12 N11 -0.8(3) . . . . ?
Ni2 C40 N12 N11 -167.71(16) . . . . ?
C41 C40 N12 C47 173.1(2) . . . . ?
Ni2 C40 N12 C47 6.2(3) . . . . ?
C52 C47 N12 N11 -23.8(3) . . . . ?
C48 C47 N12 N11 151.2(2) . . . . ?
C52 C47 N12 C40 162.4(2) . . . . ?
C48 C47 N12 C40 -22.5(3) . . . . ?
C8 C9 O1 Ni1 -27.8(3) . . . . ?
C10 C9 O1 Ni1 154.34(18) . . . . ?
C23 C22 O2 Ni1 142.68(19) . . . . ?
C21 C22 O2 Ni1 -39.0(3) . . . . ?
C36 C35 O3 Ni2 -141.95(19) . . . . ?
C34 C35 O3 Ni2 40.0(3) . . . . ?
C49 C48 O4 Ni2 -154.89(18) . . . . ?
C47 C48 O4 Ni2 27.4(3) . . . . ?
N6 C14 Ni1 C1 132.47(19) . . . . ?
C15 C14 Ni1 C1 -57.8(3) . . . . ?
N6 C14 Ni1 O1 -105.6(4) . . . . ?
C15 C14 Ni1 O1 64.1(5) . . . . ?
N6 C14 Ni1 O2 -31.09(19) . . . . ?
C15 C14 Ni1 O2 138.6(3) . . . . ?
N3 C1 Ni1 C14 152.4(2) . . . . ?
C2 C1 Ni1 C14 -45.6(2) . . . . ?
N3 C1 Ni1 O1 -16.3(2) . . . . ?
C2 C1 Ni1 O1 145.8(2) . . . . ?
N3 C1 Ni1 O2 -100.7(3) . . . . ?
C2 C1 Ni1 O2 61.4(4) . . . . ?
C9 O1 Ni1 C14 -88.5(4) . . . . ?
C9 O1 Ni1 C1 33.7(2) . . . . ?
C9 O1 Ni1 O2 -163.43(19) . . . . ?
C22 O2 Ni1 C14 50.24(18) . . . . ?
C22 O2 Ni1 C1 -57.5(4) . . . . ?
C22 O2 Ni1 O1 -142.71(18) . . . . ?
N9 C27 Ni2 C40 -134.71(19) . . . . ?
C28 C27 Ni2 C40 57.5(3) . . . . ?
N9 C27 Ni2 O4 103.6(4) . . . . ?
C28 C27 Ni2 O4 -64.3(5) . . . . ?
N9 C27 Ni2 O3 29.59(19) . . . . ?
C28 C27 Ni2 O3 -138.2(2) . . . . ?
N12 C40 Ni2 C27 -151.4(2) . . . . ?
C41 C40 Ni2 C27 46.0(2) . . . . ?
N12 C40 Ni2 O4 17.4(2) . . . . ?
C41 C40 Ni2 O4 -145.2(2) . . . . ?
N12 C40 Ni2 O3 100.5(3) . . . . ?
C41 C40 Ni2 O3 -62.1(4) . . . . ?
C48 O4 Ni2 C27 87.7(4) . . . . ?
C48 O4 Ni2 C40 -34.28(19) . . . . ?
C48 O4 Ni2 O3 162.17(19) . . . . ?
C35 O3 Ni2 C27 -50.47(18) . . . . ?
C35 O3 Ni2 C40 58.2(4) . . . . ?
C35 O3 Ni2 O4 142.21(18) . . . . ?

####################################################################### 
# 
# 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_17ma116_SB279
_database_code_depnum_ccdc_archive 'CCDC 2004184'
loop_
_audit_author_name
_audit_author_address
'Simone Bertini'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-05-15 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2017-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 N6 Ni O2'
_chemical_formula_sum            'C36 H36 N6 Ni O2'
_chemical_formula_weight         643.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C36H36N6Ni1O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.11310(10)
_cell_length_b                   10.38960(10)
_cell_length_c                   14.69520(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.6340(10)
_cell_angle_gamma                90
_cell_volume                     1598.07(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14089
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.9970
_cell_measurement_theta_min      1.9880
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.007
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00 109.00   1.00    4.97    --   27.49  38.00 -30.00  137
  2  ω    -54.00  83.00   1.00    4.97    --   27.49 -38.00  30.00  137
  3  ω    -10.00 103.00   1.00    4.97    --   27.49  57.00   0.00  113
  4  ω    -16.00 112.00   1.00    4.97    --   27.49  77.00-180.00  128
  5  ω    -49.00  65.00   1.00    4.97    --   27.49 -57.00-180.00  114
  6  ω    -20.00  28.00   1.00    4.97    --  -23.50 -99.00 -60.00   48
  7  ω    -20.00  83.00   1.00    4.97    --   27.49 -99.00  60.00  103
  8  ω    -54.00  83.00   1.00    4.97    --   27.49 -38.00-120.00  137
  9  ω    -10.00 103.00   1.00    4.97    --   27.49  57.00 120.00  113
 10  ω     35.00 122.00   1.00    4.97    --   27.49 178.00  60.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0256630000
_diffrn_orient_matrix_UB_12      -0.0576975000
_diffrn_orient_matrix_UB_13      -0.0247453000
_diffrn_orient_matrix_UB_21      0.0615510000
_diffrn_orient_matrix_UB_22      -0.0178503000
_diffrn_orient_matrix_UB_23      -0.0001198000
_diffrn_orient_matrix_UB_31      0.0120234000
_diffrn_orient_matrix_UB_32      -0.0318363000
_diffrn_orient_matrix_UB_33      0.0448803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3269
_reflns_number_total             3647
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.073
_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)+(0.0433P)²+0.5772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C10(H10), C12(H12), C18(H18), C11(H11)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.5000 0.5000 0.5000 0.02092(9) Uani 1 2 d S T P . .
O1 O 0.44240(10) 0.43495(10) 0.59542(7) 0.0296(2) Uani 1 1 d . . . . .
N1 N 0.34444(11) 0.68949(11) 0.55457(8) 0.0238(2) Uani 1 1 d . . . . .
N3 N 0.27533(11) 0.82651(12) 0.44716(9) 0.0268(3) Uani 1 1 d . . . . .
N2 N 0.26777(12) 0.79256(12) 0.53155(9) 0.0288(3) Uani 1 1 d . . . . .
C5 C 0.40031(13) 0.65445(13) 0.48764(10) 0.0224(3) Uani 1 1 d . . . . .
C4 C 0.35308(13) 0.74891(13) 0.41643(10) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.35922(13) 0.62775(14) 0.64455(10) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.40545(14) 0.50067(13) 0.65782(11) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.36928(13) 0.78022(13) 0.32268(10) 0.0234(3) Uani 1 1 d . . . . .
C15 C 0.47446(13) 0.85313(13) 0.32051(10) 0.0252(3) Uani 1 1 d . . . . .
C9 C 0.40778(14) 0.44068(15) 0.74489(11) 0.0291(3) Uani 1 1 d . . . . .
H9 H 0.4339 0.3553 0.7559 0.035 Uiso 1 1 calc R . . . .
C13 C 0.27186(14) 0.74841(14) 0.23616(11) 0.0279(3) Uani 1 1 d . . . . .
C16 C 0.48167(14) 0.89107(14) 0.23169(11) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.5524 0.9376 0.2301 0.035 Uiso 1 1 calc R . . . .
C10 C 0.37226(16) 0.50552(15) 0.81402(12) 0.0306(3) Uani 1 1 d . . . . .
H10 H 0.3738 0.4630 0.8701 0.037 Uiso 1 1 calc R . . . .
C12 C 0.32666(15) 0.69429(15) 0.71542(11) 0.0306(3) Uani 1 1 d . . . . .
H12 H 0.2998 0.7795 0.7051 0.037 Uiso 1 1 calc R . . . .
C6 C 0.20015(16) 0.93763(15) 0.39773(12) 0.0358(4) Uani 1 1 d . . . . .
H6A H 0.1627 0.9793 0.4401 0.054 Uiso 1 1 calc GR . . . .
H6B H 0.1338 0.9091 0.3405 0.054 Uiso 1 1 calc GR . . . .
H6C H 0.2548 0.9971 0.3803 0.054 Uiso 1 1 calc GR . . . .
C17 C 0.38604(16) 0.86127(15) 0.14535(11) 0.0325(3) Uani 1 1 d . . . . .
C18 C 0.28183(15) 0.79065(15) 0.14922(11) 0.0322(3) Uani 1 1 d . . . . .
H18 H 0.2167 0.7710 0.0919 0.039 Uiso 1 1 calc R . . . .
C20 C 0.57952(15) 0.88851(17) 0.41204(11) 0.0345(3) Uani 1 1 d . . . . .
H20A H 0.5431 0.9168 0.4593 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.6299 0.9566 0.3991 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.6327 0.8148 0.4362 0.052 Uiso 1 1 calc GR . . . .
C11 C 0.33414(15) 0.63413(16) 0.80065(11) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.3141 0.6786 0.8486 0.040 Uiso 1 1 calc R . . . .
C19 C 0.15845(16) 0.66987(17) 0.23688(13) 0.0393(4) Uani 1 1 d . . . . .
H19A H 0.1872 0.5891 0.2685 0.059 Uiso 1 1 calc GR . . . .
H19B H 0.1039 0.6545 0.1717 0.059 Uiso 1 1 calc GR . . . .
H19C H 0.1119 0.7159 0.2710 0.059 Uiso 1 1 calc GR . . . .
C21 C 0.3953(2) 0.9059(2) 0.05037(13) 0.0522(5) Uani 1 1 d . . . . .
H21A H 0.4158 0.9960 0.0543 0.078 Uiso 1 1 calc GR . . . .
H21B H 0.3150 0.8920 0.0000 0.078 Uiso 1 1 calc GR . . . .
H21C H 0.4609 0.8583 0.0363 0.078 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 1.8536(10) . ?
Ni1 O1 1.8537(10) 3_666 ?
Ni1 C5 1.9236(13) . ?
Ni1 C5 1.9236(13) 3_666 ?
O1 C8 1.3148(17) . ?
N1 N2 1.3393(16) . ?
N1 C5 1.3769(17) . ?
N1 C7 1.4285(17) . ?
N3 N2 1.3188(17) . ?
N3 C4 1.3647(18) . ?
N3 C6 1.4665(18) . ?
C5 C4 1.4016(19) . ?
C4 C14 1.4844(19) . ?
C7 C8 1.4064(19) . ?
C7 C12 1.3953(19) . ?
C8 C9 1.416(2) . ?
C14 C15 1.402(2) . ?
C14 C13 1.405(2) . ?
C15 C16 1.391(2) . ?
C15 C20 1.501(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(2) . ?
C13 C18 1.390(2) . ?
C13 C19 1.504(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.377(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C17 C18 1.388(2) . ?
C17 C21 1.507(2) . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C11 H11 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.00(3) . 3_666 ?
O1 Ni1 C5 92.37(5) . . ?
O1 Ni1 C5 87.64(5) 3_666 . ?
O1 Ni1 C5 87.64(5) . 3_666 ?
O1 Ni1 C5 92.36(5) 3_666 3_666 ?
C5 Ni1 C5 180.0 . 3_666 ?
C8 O1 Ni1 127.33(9) . . ?
N2 N1 C5 115.61(11) . . ?
N2 N1 C7 117.28(11) . . ?
C5 N1 C7 127.10(11) . . ?
N2 N3 C4 113.61(11) . . ?
N2 N3 C6 118.07(12) . . ?
C4 N3 C6 128.31(12) . . ?
N3 N2 N1 102.43(11) . . ?
N1 C5 Ni1 122.46(10) . . ?
N1 C5 C4 101.68(11) . . ?
C4 C5 Ni1 135.56(10) . . ?
N3 C4 C5 106.65(12) . . ?
N3 C4 C14 117.74(12) . . ?
C5 C4 C14 135.61(12) . . ?
C8 C7 N1 118.23(12) . . ?
C12 C7 N1 119.37(13) . . ?
C12 C7 C8 122.40(13) . . ?
O1 C8 C7 125.16(13) . . ?
O1 C8 C9 119.11(12) . . ?
C7 C8 C9 115.70(13) . . ?
C15 C14 C4 120.10(13) . . ?
C15 C14 C13 120.10(13) . . ?
C13 C14 C4 119.44(13) . . ?
C14 C15 C20 121.03(13) . . ?
C16 C15 C14 119.05(13) . . ?
C16 C15 C20 119.91(13) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.77(14) . . ?
C10 C9 H9 119.1 . . ?
C14 C13 C19 120.94(14) . . ?
C18 C13 C14 118.84(14) . . ?
C18 C13 C19 120.22(14) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.75(14) . . ?
C17 C16 H16 119.1 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.75(14) . . ?
C11 C10 H10 119.6 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.16(14) . . ?
C11 C12 H12 119.9 . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C16 C17 C21 120.55(15) . . ?
C18 C17 C16 118.24(13) . . ?
C18 C17 C21 121.20(15) . . ?
C13 C18 H18 119.0 . . ?
C17 C18 C13 121.99(14) . . ?
C17 C18 H18 119.0 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.03(14) . . ?
C12 C11 H11 120.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.834
